SPH-THEMED EROTICA STORIES

Chapters:

Part 1
Part 2
Part 3
Part 4
Part 5
Part 6
Part 7
Part 8
Part 9
Part 10
Part 11

*****

Part 1…

Jamie lingered in the kitchen as the morning sun shone through the window, landing on him as he stood frozen against the cool gray counter. His wife’s frantic search today had been echoing throughout their sleek one-bedroom apartment for the past hour, and the beige walls, dull and plain, now reverberated with her energy.

At first, the pitter-patter of Kelly’s bare feet sounded like gentle rain, deceptively calm. Then it was built. Coat hangers clattered. Drawers slammed with frustration and objects thudded to the floor: Kelly had turned into a blonde-haired hurricane, with every muffled curse sending a racing shiver down Jamie’s spine.

Yet beneath the fear, something else coiled around his lean body. Excitement. The reckless thrill of standing too close to something dangerous and unknown. He traced circles on the countertop with one finger, following an invisible line. One wrong step either side of the line and the hurricane would swallow him whole.

“Jamie, what’s the time?” Kelly asked from the bedroom.

“Eight-fifty.”

He could hear her groan with anxiety. If she were to make her flight, she’d need to leave soon, and he needed her on that plane now more than anything.

Months earlier, when Kelly first mentioned her best friend Becky’s bachelorette weekend in Miami, Jamie had begun counting down the days like a child awaiting Christmas. This would be another chance to live his secret. And now, every frantic step, every crash of something dropped, confirmed it had arrived: a whole weekend alone.

“Babe, your flight!” he beckoned.

His voice betrayed him, cracking on the last word and pitching upward into something softer, higher, and almost girlish. He winced, wondering: did she hear it too?

If she did, she gave no sign. Kelly had been obsessed with one crisis all morning: finding her favorite black strappy heels. She’d moaned and groaned about them while curling her hair between a hot iron, brushing her teeth, and packing all the while. Jamie knew exactly where they were. He’d worn them two nights ago while she showered, admiring in the full-length mirror how the thin leather straps hugged his ankles, how the height made his smooth legs look impossibly long. When the shower turned off, he scampered out of them and decided in the moment that this weekend, they were staying with him.

“Ugh! Where are my heels?” Kelly yelled from the bedroom, stomping her feet for emphasis. It snapped him out of the memory.

Jamie’s body tensed. A fight or flight reaction, he assumed, to confess or double down. Confessing wasn’t an option. No way! How could he admit such a secret: why would a man choose lace against his skin (even for a day or two) to the warmth of his wife’s body? And what kind of man shaved himself bare and slipped into her clothes when she wasn’t looking?

“Calm down,” he whispered to himself. His thoughts were racing as they often did when he was nervous. “You’re almost there.”

The old brass clock on the wall caught his reflection, showing a youthful face that could pass for eighteen or twenty-one. A delicate nose, high cheekbones, arched brows, and full lips that curved into a nervous half-smile. He was handsome, or better said, pretty. Twenty-nine years old, but forever boyish. Alexander the Great. Or in this case, Jamie the Lame, he thought bitterly. Secret crossdresser. Faux woman. Common whore. And now… heel thief.

He swallowed hard with guilt and shame, watched the minute hand crawl upward, striking nine o’clock, and realized she was cutting it dangerously close.

“Babe!” he tried again, brushing brown strands from his forehead.

Kelly emerged suddenly from the bedroom, cradling clothes in her arms and wearing a yellow sundress. She was beautiful, even when mad and exasperated, with her blonde hair bouncing and those green eyes wide with frenetic energy that always resurfaced when she was running late.

“Jamie!” she shouted. The hurricane finally turned its full force on him.

He replied with a teasing “yes, dear?” unable to resist; she always looked adorable when frustrated.

“I’m not in the mood for games. I need your help.”

She stuffed the handful of items from her arms into a plain, unzipped suitcase that sat on the living room couch. Bright colored bikini strings and skimpy dresses that would barely cover her body poked out from within.

“Have you seen my black heels? The strappy ones. I swear I packed them,” Kelly asked.

She flung a thong out of the suitcase. Then another, which landed on the floor next to the first.

Jamie’s stomach flipped. He recognized it immediately: black lace, he’d worn it last weekend while she was at brunch with friends.

The mug of insipid coffee trembled in his hand, and with the other, he held it still. He was hopeful, or perhaps desperate, that his voice wouldn’t betray him now, admitting he knew exactly where the heels were, and exactly why they wouldn’t be found.

“Jamie? The heels…”

He cleared his throat. “No, haven’t seen them,” he replied, silently urging her to give up and go.

Kelly dropped to her knees beside the open suitcase, muttering beneath her breath as she rummaged deeper. The modest yellow sundress crept up with each shift of her hips.

“I can’t believe I’m gonna miss my flight over a stupid pair of shoes,” she groaned. Then, abruptly: “I still don’t get why you didn’t want to come with me.”

“We talked about this, Kel,” Jamie laughed. “What would I do by myself at a bachelorette?”

“You could’ve rented your own place and enjoyed the beach. Isn’t that better than staying in cold New York? We could have had breakfast together. And you know the girls love you… I love you. Why would you want to stay here, alone?

Jamie twisted the wedding band on his finger, searching for a lie that fit. Instead, he deflected.

“Maybe next time. Hey, what’s so special about those heels anyway?” he asked. Kelly took the bait.

“Oh, they go with everything. You know the ones… You love them on me.”

That was an understatement. If only she knew, Jamie thought. He should feel guilty, and did, but he also knew his wife had plenty of other shoes. She wouldn’t really miss one pair that much, would she? Not enough to miss her flight, miss her best friend’s bachelorette weekend…

“You could buy a new pair in Miami,” he offered.

Kelly shot him a look. “You really want me gone, huh?”

“No! I’m just trying to help. You’re going to be late,” he insisted. Sweat beaded down his neck despite the chill.

“Stop rushing me.”

“I’m not.”

“Yes, you are. You’re rushing me!”

From the kitchen doorway, he watched as Kelly continued her futile search, her head buried in the suitcase. The yellow sundress she wore continued to ride up, inch by inch, to now reveal her toned thighs

Kelly’s legs were perfectly proportionate to the rest of her stunning body; the physique of a runner, despite the little running she ever did, was when she was late to an event. And as she dug deeper, she became oblivious to the way the hem of the fabric slid even higher, revealing the full curve of her plump ass. Then, her pink panties stretched taut. Showing the very clear and delicate outline of her vulva through its thin fabric.

Jamie knew any man would be lucky to have a wife like Kelly. Heck, any man would be happy to spend a night with Kelly. He also knew he should be sad to see her go, and that he should be dreading the empty apartment. He did, but not fully. He still loved her… just needed a few days to be someone else. To dress up in something more than a thong or heels, to instead go all the way: a complete transformation.

Kelly stood upright and blew a strand of hair out of her face. “I swear these floors eat up all my stuff,” she huffed. “I’ll have to find them when I get back.”

Relief flooded him so fast that his knees almost gave out. His wife looked over her bare shoulder at him, as if seeing her husband for the first time that morning.

“You sure you’re gonna be okay while I’m gone?” she asked, her eyelids softening with concern as she zipped up the suitcase. “You’re not gonna get up to too much trouble, right?”

Jamie met her look, and his heart seemed to skip a beat. He knew what she meant, and he knew what she didn’t know.

“I’ll be fine, it’s only a couple of days. I’ll survive.”

He smiled an even softer and warmer smile now, as if to plaster over the secret bubbling beneath the surface of his calm exterior.

Kelly moved into the kitchen on her tiptoes and slid her arms around his slim waist, pressing her face against his chest. He was only an inch taller than her; she fit perfectly against him, and her body was warm, soft in all the right places.

The fridge they embraced next to was dotted with photos. Their high school graduation, vacations up north, Thanksgiving with her family, who loved him like a son, Jamie’s twenty-ninth birthday a month ago, which Kelly organized as a surprise and lively night. All were laid bare. And he wondered now as he held her, when he had first started having these dreams, these desires that felt more and more like a betrayal—lace and silk and stockings and wigs.

“You’ll be fine, huh?” Kelly teased, adjusting the strap of her dress as she pulled away. “No wild parties or anything, Jamie-baby?”

Her tone was playful, but there was a glint in her eyes, a knowing look that made Jamie’s stomach twist and turn for just a moment. Did she suspect something? No, she couldn’t have. He’d been careful, always ever so careful during these rare weekends alone; always placing her clothes perfectly back in their spot, the lingerie washed and neatly folded. In another life, he might’ve been a thief or a criminal (and a successful one, too), given how well he covered his tracks. No–Kelly had no idea.

So he forced a laugh before pressing a kiss to her smooth forehead, and added, “I’ll probably just binge tv and eat too much pizza. You don’t have to worry about me.”

“Good,” Kelly said defiantly, pulling away while her smile lingered. She swiped her phone off the counter, a denim jacket that hung on a stool, and a floppy black hat that would suit Miami’s heat just fine.

“I don’t know where all that pizza goes on you anyway…” she said, her breath catching, her eyes searching over his slender frame and moving lower until they settled on his jutting hips. “Except for maybe here–”

Her hand darted out to deliver a quick and playful spank to his ass, and the sting shot straight to his cock, sharp and electric as the sound reverberated within the kitchen.

“Hey, hands off the goods!” Jamie replied, huffing laughter while she squeezed his cheek harder between her fingers now.

“You’re gonna miss your flight… you’re gonna miss your flight!” he yelped. His voice cracked again.

“But you’re such a bad girl,” she teased with a mischievous smile.

“A girl?!”

“Yeah… a naughty one, too.” Kelly grinned. “You’ve got the cutest butt. Seriously, better than half the girls I know.”

Heat rushed through him so fast he forgot to breathe. Kelly’s teasing had always hit nerves she didn’t realize existed, and now, she caught the growing outline in his pants. Her brows lifted.

“Someone’s awake.” She stepped closer, voice dropping. “Want a quick treat before I go?”

“What?” he muttered. His heart pounded; this wasn’t a part of his plans.

“Do you want a blowjob? A quick one,” she whispered, slipping her arms into the denim jacket. “I have time.”

“No, you don’t. You’ll miss your flight.”

“I’ve got eight minutes,” Kelly replied, looking at the brass clock. Her fingers brushed over him through the pants. “Come on. When’s the last time you came?”

He hadn’t, not since she’d ridden his face last weekend, grinding against his mouth until she shuddered and soaked his chin. He’d been saving it, unconsciously, for this weekend. For the release he really craved.

“Your Uber’s basically here,” he said, almost too fast. “If you miss Becky’s big weekend, she’ll kill you.”

Kelly narrowed her eyes at him and placed her hands on her hips. She flashed a look that said: ‘what man refuses head?’ before saying, “Are you trying to get rid of me?”

“No,” he lied. “I just want you to have fun.”

Jamie smiled.

She pouted. “You sure? I miss this pretty cock.”

Her fingers grasped at him through the fabric, stroking gently as a bead of precum soaked into his boxers. For a moment, he wavered. Seven days without release had left him aching, but he stepped back, letting her hand fall away.

“Go. Have fun. Becky won’t just kill you, she’ll take me out too if you’re late.”

Kelly studied him a second longer, suspicion flickering, then shrugged and stepped back. “Suit yourself. Text me when you miss me. And don’t let the apartment burn down either, pizza-boy.”

When she glanced at her buzzing phone, she exclaimed, “Uber’s here. Shit, I gotta go.” Jamie followed her to the door, rolling the suitcase despite her protests.

Outside, the sleek black sedan idled at the curb of their apartment building. The air was crisp, and the few remaining brown and dulled orange leaves held against a gentle breeze. Jamie heaved the luggage into the open trunk of the car a little too hurriedly before Kelly threw her arms around him one last time. Her floral perfume enveloped him while she placed a tender kiss on his lips. A kiss that spoke: ‘Be good while I’m gone.’

“I’ll text you when I land,” she said with her green eyes and blonde hair shining brighter in the morning sunlight as she slid into the backseat.

“Sorry if I was being mean this morning. Love you,” Kelly called out as she lowered the window.

“Love you too, Kel.”

“And let me know if you find my heels: black, leather, with little straps,” she explained.

Jamie responded in kind, with “don’t worry about the heels. They’ll turn up. Just try to have fun.” Then waved.

Kelly smiled and waved back. “And don’t forget: I’ll be back on Sunday, my flight lands at eleven…” she yelled as the car pulled away.

He stood on the sidewalk for a moment, watching as the car disappeared around the corner. And then, his high-school sweetheart, now loving wife, five years of marriage, Hurricane Kelly, with all her chaos and all her beauty, was finally gone.

*****

Part 2…

After a few hours had passed, Jamie moved to the closet. Kelly had only texted once, something about forgetting her wedding ring on the bathroom counter and asking if she should return to grab it, but since then, nothing. She was either still in the air or landing soon, he realized, and he was now safe to begin.

Buried beneath old sweaters and boxes filled with knick-knacks, he hauled out the old suitcase and set it onto the bed. Once there, he could hear Kelly’s voice say, ‘I swear these floors eat up all my stuff,’ as he unzipped the top and looked over everything inside. He’d been careful enough only to take items she wouldn’t notice missing, but the heels today had been the most daring thing yet, and he gulped as he pulled them out.

They were the kind worn when you wanted to appear sexy, to one of those fancy dinner parties, or… to a bachelorette trip in Miami.

It felt cool against his palm while the heel glinted in the light that poured through the bedroom window. Jamie measured it with his eyes: four-and-a-half-inches, as big as his manhood at its hardest, and his throat tightened with that familiar heat spreading through him. He turned his attention back to the suitcase.

Neatly folded at the top of the pile were two dresses. One black velvet, form-fitting and daringly short, the other a silver that caught reflections and bounced violet and light blues against the hardwood. Then, sets of lingerie: black and red lace. Thigh-high stockings, too, with a matching garter. A makeup bag containing all the essentials to transform his face, and at the bottom, a wig: long, dark chestnut brown, straight with bangs made from real hair. There were other items, too, like skirts and blouses, and yoga pants, but these drew his attention the most for now.

He told himself this was just a game, a harmless escape, but deep down he knew it was something more. This was the woman inside him coming out when the world wasn’t watching, the one who felt more real than he sometimes did. And each time he let her out, that woman wanted more, and more, and he knew this weekend would be no exception. But there were limits.

“No cheating,” he whispered to the empty room, as though saying it out loud would hold him accountable. “No matter what. Never.”

He would be the woman in this apartment, and that was it. No matter his fantasies, those confusing dreams involving men, hard and unraveling. He wouldn’t act on them. Hiding this secret life from Kelly was already bad enough, he realized. He couldn’t cheat on the woman he loved.

Jamie quickly stripped off his clothes, sliding down the sweatpants, a plain shirt still with Kelly’s scent on it, then the boxer briefs that he had leaked into from her touch. In the bedroom mirror, he gazed at the reflection of his lean, almost delicate body, with narrow shoulders and a waist that Kelly always teased was smaller than hers, sometimes enviously.

This was the first step. The shedding of Jamie-the-husband, Jamie-the-man, to make way for Jamie-the-woman.

He jumped into the shower and scrubbed slowly and deliberately, enjoying the pampering hands that lingered over his smooth skin under the hot, running water, imagining his body softer in some places, fuller in others. Then, shaved his face again with the razor; it made him look even younger and more feminine. The razor then passed over his entire body, from his chest down to his soles.

When he stepped out, the air was cool against his damp skin. He noticed Kelly’s wedding ring on the counter and carefully put it away in a safe spot. Then wrapped a towel around his waist and returned to the bedroom, where his phone vibrated.

‘Landed! Miami is HOT,’ Kelly’s text read. ‘Already sweating. Wish you were here.’

A photo followed with a selfie of her on the pavement outside the airport: her sunglasses perched on her nose, smile wide and carefree, that blonde hair shining golden in the tropical sun beneath the floppy hat. With her, Jamie spotted a few of the other women attending the bachelorette: a brunette and a redhead whose names he’d forgotten, women who were just as pretty as his wife.

‘Looks amazing,’ he typed back. ‘Glad you made it. Love you.’ He hesitated before hitting send with his thumb hovering over the screen. Love you. He did, didn’t he? So why was he doing this? Why wasn’t he telling her about this other side of him? They always told each other everything.

He buried the self-interrogation and set the phone down before turning back to the bed, where the dresses and lingerie sets waited.

The transformation was always a ritual with each step deliberate and calculated. He decided on the red lingerie for today and started with the panties first, sliding them up his legs. The fabric scratched his shaved skin ever so slightly. And all at once, a flush crept up his neck while he adjusted them, feeling how neatly his small, soft cock and balls tucked away inside, almost perfectly. He’d always been self-conscious about his size, though Kelly insisted she didn’t care.

The bra came next, and it was a little trickier with its hooks, but he’d practiced enough to manage. Jamie stuffed it with silicone inserts he’d ordered online, and the weight of them gave his chest a subtle curve, creating the illusion of having real breasts.

After spending an hour or so applying creams and drawing lines on his face, mesmerized by following makeup tutorials, the woman who stared back was equal parts glamorous and sexy. Her blue eyes shone bright above blush-kissed cheeks, the blended contours sculpted her pretty face into something even softer and more feminine, and her lips were full and inviting.

The wig settled onto his head and draped down to his new breasts, and he adjusted the strands of dark brown hair until they framed his face. Then he stepped into Kelly’s heels, and the click of the stilettos against the hardwood floor sent a shiver through him as he fastened the straps to his ankles. The heels did something wicked to his body, causing his lower back to arch involuntarily with a pose that screamed: ‘come fuck me,’ giving his hips a natural, inviting sway as he moved.

He could feel his heart beating hard against his chest now as he stood for a moment, standing there in the heels and red lingerie, savoring the image that stared back. The panties sat high on his hips, the bra cradled his tits, while his legs appeared longer with their shaved length. Finally, he slipped into the black velvet dress and ran the zipper up the back of his spine.

The mirror showed the complete transformation. Jamie was erased, and now something… or someone else, appeared in the bedroom where there was once a man.

His phone buzzed again.

‘Heading to the hotel now,’ Kelly wrote. Girls are already planning to hit the clubs tonight after dinner. Are you doing okay?’

He looked at his reflection again.

“What if she video-calls me?” Jamie thought out loud with a sudden panic, seeing his feminized face and body, the secret exposed. But he buried the idea; Kelly was too busy with her friends to worry about him.

‘All good here. Just chilling. Have fun at the clubs. Don’t do anything you might regret,’ he joked, then added a heart emoji before sending it off.

Kelly shot back with: ‘No promises,’ and a kissing face. He laughed softly, the sound high and light.

The guilt was still there, but quieter, drowned out by the thrill of being her, finally complete and transformed. And now, he realized, the weekend could truly begin.

*****

Part 3…

Jamie poured himself a glass of wine from the bottle that sat on the kitchen counter, and the red liquid caught the twilight of evening streetlights as he swirled it around. The first sip was sharp, warming his throat, loosening the last of his inhibitions. Then he moved to the living room, the stolen heels clicking with each step, putting on some music — light pop, then an electronic dance tune, which he involuntarily began to sway to.

He stopped mid-movement, staring at the living room shelf, suddenly unsettled with the sense of being watched crawling over his skin. It wasn’t anything new. On past solitary weekends, he’d sometimes freeze at a random noise outside, heart hammering, convinced Kelly was about to burst through the door and see him like this. Whatever ‘this’ was. Usually it was nothing: a neighbor’s car trunk slamming shut, garbage bins being rolled to the curb. But tonight felt different. More persistent, as if he was being watched, studied, and talked about by some silent observer.

His eyes scanned the shelf. It was plain, as it had always been: more photos of him and Kelly on vacation here, family members, potted plants, paperbacks. Jamie looked beneath the shelf and saw boxes of empty Amazon packages, and he made a mental note to clean up Kelly’s mess later. She undoubtedly bought too many things for this trip at the last minute, as she always did.

Jamie couldn’t help but smile at the thought of Kelly, as he sipped the wine again to calm his ever-flaring nerves. Seeing his reflection in the black of the television screen, he struck a few poses to have some fun; one hand cocked on his wide hip, the other lifting the wineglass to his full painted lips: the woman on the screen was bold, confident, someone who didn’t hide.

“Act more like her,” he told himself. “No one’s watching you.”

He looked at the shelf, then the living room window where the curtains were half-closed, and repeated, “No one.”

The wine buzzed through him, softening the edges of his thoughts, and so he opened the phone’s camera and decided to have even more fun by snapping a few photos. The first was with his lips parted, revealing a hint of his teeth; another with his head tilted back and the wig’s hair spilling over his shoulders and tickling down his nape. He looked stunning in each one. And every click of the camera felt like a step further from the Jamie who’d kissed Kelly goodbye and closer to that woman inside: the one with wants and needs he didn’t understand when he really sat down and thought hard about them.

Jamie scrolled through the photos, gasping at how real she looked. “I really look like a woman,” he said to himself, scanning over each one.

He decided to spend the next few moments watching his favorite videos on the television while stretched out on the couch; videos of crossdressers, sissies, transgender women, either way, being intimate with men. He never considered himself gay or even bisexual, but when tapping into this inner woman, that’s all he (or she) seemed to think about.

Men… their hard cocks, their toned bodies. He discovered he had a type: athletic guys, the bad boy type, the ones who would have casual sex every weekend back in college. And these were not gentle fantasies either; he entertained the idea of being submissive and subservient to them. Men who were bigger than him in every way. Dominant. Aggressive. Men who wanted to make him their bitch. Who wanted to treat him like a rented whore!

Jamie suddenly gasped at the words his mind flooded him with.

“What the fuck, Jamie,” he laughed nervously, voice high and breathy.

Arousal had been building all week; now, fueled by wine and the videos, it surged unbearably. He set the phone timer for more daring shots: capturing him bent over the couch arm, exposing the cheeks of his round ass, which was the largest thing on him. His butt is eating the fabric of the red lace hungrily.

Then he moved to his knees, with expressions of ‘come fuck me’ eyes as he stared into the camera. He bit his lip and let out a soft gasp. Slipping off the dress entirely, he took off more, only wearing the red lingerie. His legs begged to be touched in the photos, the petite bulge in his panties so small it could be confused for a puffy labia.

Then, the idea came suddenly, reckless and as intoxicating as the wine—a dating app. Just to see. Just to know what it would be like to be ‘her’ in the world, not just in this apartment.

“You said you wouldn’t cheat,” he said to himself, catching how feminine his voice suddenly sounded. “This is just some fun,” he replied with a wave of his small hand. “I’m not going to meet up with anyone.”

Jamie opened the app store, his fingers trembling as he downloaded one he’d heard of before. ‘For discreet dates and flirtatious encounters,’ it advertised.

He created a profile, hesitating for a moment about what name to choose. Considering ‘Josy,’ then ‘Jasmine,’ or even ‘Jade,’ but none felt right. ‘Jamie,’ felt right, so that’s what he went with.

He uploaded a photo, one he’d taken minutes ago, where his eyes beckoned, and his lips curved into a mischievous smile. Where his body looked tight and womanly in the black dress, with his cleavage pushed high and tight from the silicone inserts. For the second photo, a full body, showing off his natural curves and that bubble-butt Kelly was so enamoured with.

His heart raced as he typed a bio.

“What to say… what to say,” he muttered, tapping his chin with one finger.

‘Just here for a weekend adventure. Looking for someone who can keep up,’ he wrote and laughed a nervous giggle, laced with alcohol at the ridiculousness of it all, then hit save.

The wineglass felt cool against his palm as he waited and eased into the couch, twirling the heels on his feet. Light from the lampshade caught the smoothness of his legs with a soft reflection, and the apartment seemed to quiet further, but inside him, a storm was brewing: guilt, desire, and the unshakable need to know who he could be.

“I’m not going to cheat,” he reassured himself. “I wouldn’t do that to Kelly.” He took another sip of the wine and pressed play on the remote.

An hour passed. Video after video, and he felt his arousal surging to even more untenable levels. But the woman inside (or maybe the wine) told him it still wasn’t time. He just had to wait a little longer… for what, he couldn’t say.

The room was dark, and the television glared blue against the walls, showing a curvaceous trans woman with a dominant stud frozen on the screen. It was titled: ‘secret girl fucked for first time.’ Jamie looked at the frozen image. She was soft where the man was hard, small, and ready to be dominated at his hands, which curled around her neck, while her red nails dug into his back. Jamie’s breath quickened. He was about to hit play when he was suddenly interrupted by a glow emanating from the coffee table.

His phone was vibrating.

*****

Part 4…

‘You have a connection!’ the notification flashed, followed immediately by another: ‘New message from Adam.’

Jamie’s stomach slammed against his ribs. He set the wineglass down on the coffee table, next to the pile of Amazon boxes Kelly had left scattered under the shelf, and swiped open the app.

The profile picture loaded, showing a man who looked straight out of his fantasies. In his mid-thirties (probably five to eight years older than he), Adam sported dark, well-groomed hair, a handsome, clean-shaven face, and eyes that seemed warm yet dangerous—Bad-boy energy in every pixel. Jamie gulped as he scrolled through the uploaded photos. His body, beneath a crisp shirt, seemed athletic and toned; his smile, confident but not cocky; and his bio was brief, simply saying: ‘In town for the weekend, looking for someone to make it unforgettable.’

Jamie read the man’s information: six feet tall— taller than him—body type listed as athletic and muscular.

“Yeah, you can say that again,” he whispered into the room.

But there was more. The app allowed men, women, and everyone in between to specify what they offered and what they sought. Adam had taken the liberty to list himself as a ‘dominant top,’ and under size: ‘large.’ Jamie read the information the app provided and realized ‘size: large’ could range from 8 to 10 inches.

His heart raced. Adam was exactly the kind of man who’d turn heads in a Manhattan bar, the kind who’d make Kelly nudge him and whisper, “he’s your type, huh?” as a joke. Except this wasn’t a joke. This was getting to be too real.

He opened the message.

‘Hey Jamie, that photo of you in the dress is stunning. Bet you’d look even better with it unzipped and on the floor. Free tonight? I’m at the Hyatt near the Park. Could use some company.’

The words were simple, but they hit Jamie all at once with the force of a sobering slap. His fingers hovered over the virtual keyboard, nails catching the light from the lamp in the living room.

I should close the app, delete the profile, go back to being the Jamie who’d promised Kelly pizza and tv, he thought. Stay dressed, be the woman, but keep it to this apartment. He looked at the reflection of the television screen that stared back. The image of the trans woman with the man was still frozen on the screen, but another woman looked back, too… and her eyes dared him to be bold, to take a chance, to feel what it was like to be her outside of these walls.

He took another sip of the wine, and its warmth spread through his chest, loosening the knot of guilt.

“Just talk to him,” Jamie told himself. “It’s harmless. It’s not cheating if it’s just words.” The logic seemed wrong and selfish, but he went with it.

He typed back, his fingers trembling with nerves and excitement.

‘Hey Adam, thanks for the compliment! I might be free, but it depends on the company.’ He added a playful winking emoji and hit send before he could overthink it. His heart pounded frantically and felt as if it might burst out of his chest.

The response came almost instantly. ‘Oh, I think I can keep up,’ Adam replied. ‘What’s a woman like you looking for tonight?’

“Woman…” Jamie repeated. “He called me a woman.”

Jamie’s lips curved into a smile, and a flush crept up his neck. The wine was doing its job, blurring the edges of his hesitation, and he could feel the panties at his crotch begin to grow taut with excitement. All those videos replayed in his head now—all those fantasies involving men who looked just like Adam.

He stood and paced the living room. The click of the heels against the hardwood was a stilted rhythm, grounding him even as his thoughts spun. He glanced at the shelf again, and that strange feeling of being watched touched at the back of his neck. But he shook it off, blaming the alcohol, and sank back onto the couch, the dress riding up slightly as he crossed his legs.

He typed: ‘I’m looking for something new. Something exciting. I have a fantasy… something better explained in person. Are you in town for long?’

What he really wanted to say was: I want to be dominated. I want to be treated like a paid whore by a man. I want to be his bitch!

‘Here for a conference, but it’s boring as hell. You seem like the kind of trouble I need,’ Adam said, and Jamie laughed, the sound high and unfamiliar, almost like a woman’s, he realized.

‘Show me more of you,’ Adam commanded suddenly, and the authority of the text sent a shiver through Jamie’s core, causing his cock to harden even more in the red lace panties.

Jamie’s fingers trembled.

‘What do you want to see?’

‘Show me anything. Show me how much of a good girl you are, and how well you follow instructions.’

Those words were enough to make him act without thinking twice. Jamie propped the phone against the table lamp and set a timer for the camera to go off. Leaning back onto the couch, he stretched one leg and planted the other, hiking the velvet dress up to his waist, exposing his long legs and thighs, while his breathing grew shallow. The lace of his panties clung to his hips, showing the outline of his small, hard cock through the sheer fabric. And he spread his thighs wider, more inviting, as he arched his back to reveal the bottom of his two cheeks while parting his lips into a wet, teasing pout that begged for a kiss or maybe something more.

The camera timer began to count down, and with each second, his body trembled as he imagined Adam’s eyes on him, his hands ripping the dress aside completely, pinning him down with his toned body, cock pressing hard against his inadequate dick within the panties. The photo captured him in this exposed and vulnerable act, and Jamie’s fingers shook as he sent the photo, his erection pulsing into the panties, his breath ragged as he waited for Adam’s next command, craving the power in those words.

‘Fuck, Jamie! You’re such a naughty girl,’ Adam replied immediately. ‘So fucking hot. Why don’t you come by the hotel? Drinks are on me.’ A winking emoji followed, and Jamie’s stomach flipped. The invitation was real now, not just a game on a screen. Adam–a man, liked what he saw, and wanted all of him.

“I’m taking this too far,” Jamie said to himself. The thought sobered him suddenly.

He stood, lowering the hem of the dress and pacing again, the wineglass back in his hand. The apartment felt smaller, the beige walls closing in with the weight of what he was considering. Kelly’s face flashed in his mind; her smile in that Miami selfie, her teasing, ‘don’t get into too much trouble.’ Did she mean it? Was there a part of her that knew, that saw through him?

His phone buzzed again, not the man this time, but Kelly, as if she could hear his spiraling thoughts.

‘Finished dinner. At the hotel. This place is insane, ocean views and all. Wish you could see it! Never seen a view like this.’

Another photo came through; it was her, standing on the balcony of the hotel with palm trees frozen in their sway in the darkness of a Miami night. She’d changed out of the sundress and was in a skimpy micro-skirt that fluttered in the breeze now.

‘We’re going to go out to some clubs tonight,’ Kelly reminded him.

Jamie’s chest tightened. He typed back, ‘Looks like paradise. You having fun?’

He waited, staring at the screen, but no reply came. She was probably caught up with the girls, laughing, dancing, living her own adventure. About to go to the club. Why shouldn’t he have his own fun too? A simple drink with a man, and nothing more, he wondered, noticing the selfishness once more in the logic.

He returned to Adam’s message, the words glowed: ‘Why don’t you come by the hotel?’

Jamie could say no, delete the app, and spend the weekend alone as he always did when Kelly was gone; safe, with his secret hidden. But the woman in the mirror wasn’t safe. She was bold, reckless, alive in a way Jamie-the-husband never was. He thought of the years ahead, the marriage with Kelly stretching out, and the opportunities slipping away. What would happen when they had kids? There’d be no more weekends like this. If he didn’t do this now, would he ever? Would he spend the rest of his life wondering what it felt like to be her with someone who saw the real Jamie, just for a day? What it felt like to be the women in the videos he watched.

His fingers moved before his mind could catch up. ‘Hyatt, huh? Fancy. What time were you thinking of?’ he wrote back.

Adam’s reply was quick, sensing Jamie’s desire. ‘Come now,’ he said. ‘Room two-thirty. I look exactly like my photos.’

Adam then attached another image, and this showed him topless in the bathroom with his muscles bulging. His arms looked twice the size of Jamie’s, and his face was just as handsome as the other photos; he was the kind of man any woman would swoon over, and Jamie wondered how a man who looked like that could ever be into someone like him.

Jamie’s eyes continued to inspect. Beneath tight abs, dark trimmed pubes drew his eye downward, just out of frame, teasing what waited below. And now, Jamie realized he was growing hard again in the red panties.

He glanced at the clock; it was eight-fifteen. He had to decide, to prepare, to cross a line he couldn’t uncross if he went through with it. The wine buzzed in his veins, amplifying the thrill, dulling the guilt again. He drained the glass, the sharp taste lingering on his tongue, and set it down with a decisive clink.

He returned to the bedroom to check his reflection. The wig was perfect, the makeup flawless. He looked so passable that at first glance, he seemed like a natural-born woman. But he added another layer of lipstick, the red even bolder now, just to be safe.

He adjusted the dress, smoothing it over his hips, and slipped on a light jacket to cover the outfit.

His heart pounded as he grabbed a small purse Kelly hadn’t taken, tucked his phone into it, then added some cash. He opened the bedside table drawer to put away his wedding ring and suddenly saw the condoms. Staring at him with their plastic wrappers of blue. Kelly couldn’t take birth-control, something about a bad reaction she had told him about, and so the protection had become a necessity whenever they were intimate. But now they looked at him. Asking questions.

Jamie’s fingers closed around the condom’s slick wrapper, its blue sheen glinting as if a taunt. His heart raced, and he could feel his cock twitch within the lace panties. A slick of precum had already begun to pool out of him.

“Just in case,” he told himself with a shaky voice, slipping the condom into the purse. But the act sent a surge of raw need through him, and his mind spiralled to Adam’s image: that athletic body pressing against him, the latex condom stretched tight over a thick, pulsing cock way bigger than his own as it pushed into him, filling him in ways he’d only dreamed of. His breath quickened while his fingers lingered on the purse, imagining the tear of the wrapper, the rough thrust of a man claiming him as a woman.

The thought made his stomach lurch, but he pushed it aside. He wasn’t planning to go that far. Just drinks, just conversation, just a taste of what it could be like living as a woman for a night.

“Then why the condom, Jamie?” he asked himself. He didn’t have an answer and buried it as he zipped up the purse.

When he stepped into the living room, that watching feeling returned, stronger this time, he could imagine voices saying: ‘he’s actually doing it… where is he going…’

His eyes darted to the shelf, the Amazon boxes still cluttering the space below it. Then to the window. He shook his head, dismissing the thought and imagined voices. He was being paranoid; the wine was playing tricks on him, his conscience telling him this was wrong, because a part of him knew it was. This was so fucking wrong!

Jamie quickly ordered an Uber while standing in the living room, then grabbed his keys and headed for the door, the heels clicking with purpose now.

“I’m really doing this,” he told himself. “I’m really fucking doing this.”

When he made it to the sidewalk, the air outside was crisp, the New York night coming to life with lights and noise as the Uber pulled up. He opened the door and sat inside, keeping his head down. The jacket shielded him from the curious glances the driver threw his way as they began to move through the streets of New York.

His phone buzzed again with a message from the man that said, ‘can’t wait to meet you, Jamie.’ There was still nothing from Kelly.

Jamie’s lips curved into a nervous smile, his heart racing with fear and exhilaration. He was doing this. He was her, and for one night, he’d know what it felt like to be wanted as her.

But as the car rattled towards Central Park, Kelly’s face lingered in his mind. Her smile, her voice, her ‘I love you.’ He gripped the purse tighter; the condom inside was a quiet reminder of the line he was flirting with. He could turn back, go home, and delete the app. He could be the husband Kelly deserved. Or, he could keep going, step into the Hyatt, and let Jamie-the-woman take over.

The car came to a slow rolling stop, and the entrance to the hotel loomed outside the windows. Jamie took in a deep breath, steadying the heels beneath him. This is it, he thought to himself, as the door opened and he stepped out onto the sidewalk.

The decision was made. Adam was waiting, and tonight, he would be Jamie, the real Jamie.

*****

Part 5…

Jamie’s heels clacked and echoed loudly across the polished marble floor of the Hyatt’s lobby; it felt as if the entire hotel was listening. He kept his eyes forward, chin slightly lifted, the way he’d practiced in the mirror countless times before: feminine and full of confidence. A few heads from men sitting at the bar turned in his direction, a glance from a woman waiting for the elevator too, but no one stared for long enough to raise suspicions.

“I’m passing,” he whispered to himself excitedly.

By luck, the elevator ride was empty, so he didn’t have to masquerade around another person. He watched the numbers climb, heart hammering against the silicone in his bra, and when the doors opened onto the second floor, the hallway was quiet, carpeted, smelling faintly of expensive cleaner. He walked around, passing endless cream walls and following numbered signs until he came to a door that read: two-thirty. He paused and took one steadying breath. In an instant, he thought about running away before knocking softly on the door—three light taps, soft and weak.

“No going back now,” he whispered once more.

The door opened almost immediately.

A man stood there in a crisp white dress shirt, the sleeves rolled up to his elbows, revealing toned forearms, with dark jeans hugging his muscular legs and a pair of brown loafers. The photos hadn’t lied, Adam was unapologetically handsome! With warm brown eyes, a half-smile that carried quiet confidence, and his dark hair damp, as though he just showered. He towered above Jamie, even while in those strappy black heels.

Adam looked him over slowly with hunger in his eyes. “Jamie,” he said, his voice low and masculine, a bright smile on his face. “Damn, you’re even sexier in person.”

Jamie felt heat flood his cheeks. “Hi,” he managed, the word coming out softer, higher than he intended.

Adam stepped aside and said, “Come in.”

The room was spacious, with a king bed neatly made and a generic photo hanging above the headboard. The curtains had been drawn against the park view, and a bottle of red wine and two glasses already poured sat on a small table by the window. Jamie looked around: soft lighting with only one lamp on, no harsh overheads; dimmed and dark, ready for a certain kind of encounter. Adam had set the scene.

Jamie slipped off the jacket, letting it fall over the back of a plush armchair. The black velvet dress stuck tight to his body, short enough to show the full length of his legs in Kelly’s strappy heels and the round swell of his ass, too, and Adam’s eyes followed every movement.

“Wine?” he asked, already handing him a glass.

“Thank you.”

Jamie took it, his fingers brushing Adam’s for a second longer than necessary, and with it the touch sent a spark riding up his arm.

“Why don’t we sit and talk for a bit?” Adam offered. Jamie nodded; he was so nervous that his legs felt like jelly.

He sat on the edge of the bed, and Adam in the armchair nearby, close enough that their knees almost touched. They talked. At first, it was light: why Adam was in New York. It was for a conference he reiterated (tech sales, boring panels all day); then, how long Jamie had been in New York; and favorite bars in the city—nothing explicit or revealing as to why they, two strangers, were actually sitting there.

Jamie kept his voice soft and let the wine loosen his tongue, laughing at Adam’s dry jokes where appropriate. Adam listened when Jamie spoke, genuinely interested with his eyes never straying far from Jamie’s face, his lips, the curve of his neck beneath the brown strands of the wig.

“You’re nervous,” Adam said suddenly after a while, setting his finished glass down. It wasn’t a question.

“A little,” Jamie admitted, meeting his look. “This is… very new to me.”

Adam smiled, slow and knowing. “You don’t have to be nervous. We can go as slow or as fast as you want.” He paused, then added with his voice dropping, “But I’ve been thinking about you since that photo. One of you is on the couch.”

Jamie’s breath faltered as he felt the pulse between his legs thud; the lace was already damp. He couldn’t help but laugh nervously in response.

Adam leaned forward, elbows on his knees, and whispered, as if someone was listening, “Why don’t you stand up for me?”

It wasn’t loud, wasn’t harsh, just calm and certain. A certain command that expected obedience.

Jamie’s body responded before his mind caught up, telling him this was wrong, that he was only meant to be here for a chat and a drink. Nothing more. But what Adam was asking for was more than that. He set the glass aside and rose regardless, heels steady on the carpet. Adam’s eyes traveled all over him again, lingering on the swell of fake breasts, the flare of his hips, the way the dress stopped high on his smooth, shaven thighs.

“Now… take the dress off.”

Is this still harmless fun, Jamie thought, as those thin fingers of his trembled as they reached to find the zipper at his back. The sound of it coming down was loud in the quiet room, and Jamie let the velvet slide from his shoulders, down his arms, over his hips, until it pooled around his feet. He stepped out of it carefully, standing there in just the red lace bra and panties, and Kelly’s black heels. He shivered, unsure if he was cold, or nervous, or maybe just unquenchably aroused.

Adam exhaled and whispered, “fuck, look at you.”

Jamie felt exposed and vulnerable, yet also electric all at once. The lingerie hugged every curve he’d created: the padded bra giving the illusion of soft breasts, the panties barely containing his small, aching erection, framing his smooth thighs and round ass.

Adam stood. He was close now, close enough that Jamie could smell the cologne on his skin as Adam reached out, fingers brushing Jamie’s waist, tracing the lace edge of the panties.

“Beautiful,” he muttered.

His hands were large, undeniably masculine, and strong. Then, he pulled Jamie in.

Their bodies pressed together, Adam’s hard chest against the silicone swell, his strong arms wrapping around Jamie’s slim back, caressing. Jamie’s hands came up instinctively, resting on Adam’s shoulders. He could feel the heat of him, the solid muscle beneath the shirt. So much stronger and harder than him.

Adam tilted Jamie’s chin up with one finger and, without warning, kissed him.

It was the first time Jamie had ever kissed a man, and his mind spiraled with shame and arousal.

Adam’s lips were firm and deliberate. He tasted faintly of wine, and when his tongue slid against Jamie’s, Jamie opened for him without thinking, a soft sound escaping his throat as Adam deepened the kiss. One hand slid down to cup Jamie’s ass through the lace, squeezing possessively like he was owned. And Jamie melted into it with his head spinning, body on fire.

Then, he felt it: Adam’s cock, thick and heavy, pressing insistently against his hip through the denim. A large, undeniable bulge that made Jamie’s own twitch helplessly in the panties. It was bigger than anything he’d ever imagined up close, and the reality of it, hot, rigid, and wanting him, sent a dizzying rush of desire throughout his body.

Jamie’s hands clutched at Adam’s shirt. He wanted more. Wanted to drop to his knees, wanted Adam to push him onto the bed, wanted–

Her face flashed suddenly and sharply in his mind. Kelly. Her blonde hair catching the Miami sun, green eyes laughing on that hotel balcony, the selfie she’d sent just hours ago—the words she’d texted. Years of trust, promises, the life they’d built.

Guilt crashed over him with the force of a wave’s cold water.

He sprang his eyes open and pulled back abruptly, breaking the kiss, hands pushing lightly at Adam’s chest until he stumbled a few steps back. His breath came fast, lipstick surely smeared.

“I… I can’t,” Jamie stuttered, his voice shaking. “I’m sorry. I thought I could, but… I can’t do this.”

Adam didn’t grab him, didn’t push. He simply let go, stepping back a respectful half-step.

“Hey,” Adam said gently with his eyes searching Jamie’s face. “It’s okay. There’s no pressure. Really.”

Jamie bent quickly, grabbing the dress from the floor, clutching it to his chest as if it were a shield. Tears pricked at his eyes, perhaps embarrassment, or shame, leftover arousal all tangling together in one confusing mess.

“I’m married,” he blurted out, the confession spilling. He didn’t have to tell the man, but felt it would explain his actions; maybe he owed him that much. “I shouldn’t have come here. I’m so sorry,” he added.

Adam nodded slowly, no judgment in his expression, just understanding. “You don’t owe me anything, Jamie,” he said. “You’re allowed to change your mind. Anytime.”

Jamie swallowed hard while stepping into the dress, fumbling with the zipper. Adam offered to help, sliding the zip back up his back, then turned away politely, giving him space, pouring another inch of wine into his own glass like nothing had happened.

When Jamie had the dress back on, jacket over his arm, purse in hand, Adam walked him back to the door.

“You’re stunning,” Adam said quietly at the threshold. “And brave for showing up. If you ever want to talk, no strings, I’m around. My flight doesn’t leave until Monday.”

Jamie managed a watery smile. “Thank you. For… being kind about it,” he replied.

Adam brushed a stray strand of the wig from Jamie’s cheek, gentle, and said, “Take care of yourself, pretty girl.”

Then, the door closed softly behind Jamie.

He stood in the hallway for a long moment, no longer in the dark of a private room but under the bright lights, his heart still racing, his lips tingling from the kiss, his body aching with unspent need and crushing guilt. Moving over to the elevator, he pressed the button and stood with his heels silent now on the carpet.

But the ghost of Adam’s mouth still burned on his lips. His breath came shallow and uneven; the taste of the man, the wine, and the heat and faint stubble lingered. The lace panties were soaked now, clinging obscenely to his small, throbbing cock, and the wet spot spread with every pulse of blood. His thighs trembled, reminding him of how exposed he’d just been.

He pressed the elevator button again, harder this time, but when the doors didn’t open immediately, he leaned back against the wall, eyes fluttering shut as the memory hit him with a sudden rush.

Adam’s hand on his ass, firm, possessive, fingers kneading the soft flesh through red lace. The thick ridge of Adam’s cock grinding slowly against his hip, unmistakable even through denim: heavy, long, impossibly hard. How big was he, really? Jamie had felt it twitch when he whimpered into the kiss, felt the heat of it searing through fabric, promising to split him open. His own cock had leaked helplessly at the contact, a humiliating dribble of precum that now cooled sticky against his skin.

And he could still feel Adam’s tongue sliding against his. Slow and claiming. The faint scrape of evening stubble against his smooth cheek. The way Adam’s broad palm had slid up his back, thumb tracing the clasp of the bra as if debating whether to rip it off right there. It had happened so quick Jamie only remembered it now.

His hand drifted unconsciously to his chest, brushing over the silicone swell beneath the dress, nipples stiff under the lace and padding. A soft, involuntary moan escaped his mouth in the empty hallway as he imagined Adam pinning him to the door instead of letting him go. Isn’t that what he wanted, what he always wanted: to be dominated? He imagined that strong hand shoved between his thighs, cupping the soaked lace, the man laughing low when he found how desperate Jamie already was.

“Such a needy little thing,” Adam would’ve whispered against his ear, he imagined, those teeth grazing the lobe. “You’re dripping for it already.”

Jamie’s hips rolled forward into empty air, seeking friction that wasn’t there. His cock strained painfully against the delicate panties as the head pushed past the lace waistband, slick and flushed pink. Another bead of precum welled and slipped down the shaft, tracing the sensitive underside.

He forced his eyes open as the elevator finally dinged. Stepping inside, he caught his reflection again in the mirrored walls. The lipstick blurred into a bruised, fucked-out red; the wig was slightly mussed from Adam’s fingers, too; and the dress clung to damp skin. He looked exactly like what he’d almost become: a cheating wife in a hotel hallway, freshly kissed and aching to be used.

The doors closed. Alone now, Jamie let his hand slide down the front of the dress, cupping himself through velvet and lace. Just one stroke, slow and teasing, then another. He bit his lip hard to stifle the whine that wanted to escape, and the friction was maddening and not nearly enough. He could drop to his knees right here, hike the dress up, shove the panties aside, and jerk himself frantically to the memory of Adam’s cock pressed against him. Cum all over the elevator mirror while imagining that thick length forcing its way into his mouth, stretching his throat. But he didn’t.

He stopped his hand with effort as those fingers trembled, and watched the floor numbers descend. His cock bobbed angrily against the lace, begging. He’d leaked so much the wet patch was now visible even through the dark dress if anyone dared to look close enough.

When the elevator opened to the lobby, Jamie moved the jacket to cover his crotch and walked out on unsteady legs, head high despite the flush burning his cheeks. Every step rubbed the soaked panties against his sensitive skin, and it felt more like a clitoris than a cock at this moment; a constant reminder of how close he’d come. How much he still wanted it.

Outside, the cold night air hit him, tightening his nipples to aching points, making the wet lace feel icy against his overheated cock. He hailed a cab instead of another Uber; his hands were shaking too much to order one on the phone adequately. That, and he needed the anonymity of a stranger who wouldn’t remember his face.

In the back seat of the yellow cab, he sat carefully, thighs pressed together, feeling the slick slide of arousal with every bump in the road. He closed his eyes and let the fantasy run wild one last time: Adam bending him over the hotel bed now, the dress pulled up to his waist, panties yanked off to the side. That huge cock dragging through the wet mess Jamie had already made of himself, teasing his hole, pressing in slow and relentless until Jamie was sobbing into the sheets: begging to be filled and bred. Completely ruined.

He shifted in the seat, biting back another moan. The driver didn’t notice.

By the time the cab pulled up outside his apartment building, Jamie was shaking with unspent need. He paid quickly, heels clicking up the stairs as every muscle clenched around the throbbing emptiness between his legs.

Inside the apartment, he didn’t even bother turning on the lights. He just kicked the door shut, dropped the purse, and stumbled to the bedroom, straight to the full-length mirror.

There she was: the woman who he’d almost given everything away to tonight. He watched his reflection as he slowly peeled the dress off again, letting it fall. The bra next, undoing the hooks with shaking fingers until the silicone forms tumbled out. Then the panties, peeled down sticky thighs, his small cock springing free at last, angry red and slick, bouncing against his smooth stomach.

Jamie dropped to his knees in front of the mirror, legs spread wide in the heels he hadn’t removed, and finally let himself touch.

One hand wrapped around his aching length, all four and a half inches, stroking fast and desperate. The other reached back, fingers sliding between his smooth cheeks, pressing against his untouched hole, imagining it was Adam’s thick head instead, pushing in without mercy.

He came in under thirty seconds, harder than he ever had in his life. Ropes of cum splattered against the mirror and dripped down the reflection of his made-up face, while his open, moaning mouth froze in breathless orgasm.

When the aftershocks faded, he stayed there on the floor, panting and keeled over with his bare butt exposed, his cock now limp and smaller, only looking up to stare at the mess he’d made of himself and the mirror both.

Kelly’s forgotten black heels were still strapped to his ankles. And for the first time, the guilt didn’t come… only hunger. A deep, insatiable hunger for what he’d walked away from tonight, and the growing certainty that he wouldn’t be able to walk away from it a second time.

*****

Part 6…

Jamie groaned softly as he woke up on the couch, still in the red lace panties and with the wig askew on his head. The coffee table glass reflected his face, showing his makeup now smudged into dark rings around his eyes, and when he peered through one open eye, he saw Kelly’s black heels on the floor beside him, one tipped over. His body ached. Those thighs were still sticky, cock soft and spent against the lace, and the mirror in the bedroom still bore the dried streaks of his frantic release.

The morning light filtered weakly through the half-closed curtains, but felt as bright as a spotlight.

His head throbbed, a dull hammer from the wine he’d finished off after stumbling home. Too much. Way too much, he thought again and again. The empty bottle stared at him from the coffee table, next to the scattered Amazon boxes he hadn’t bothered to clean up beneath the shelf; somehow, in the day, the shelf didn’t feel as accusatory.

He sat up slowly, rubbing his temples as the memories crashed in waves: Adam’s mouth, firm and demanding; the thick press of that cock against his hip; the way he’d almost let it happen. Then the cab ride home, the desperate jerk-off in front of the mirror, coming so hard he nearly blacked out while imagining being fucked raw.

But there was still no guilt this morning. He had expected it, and instead it wasn’t here; just the hangover and a low, persistent throb between his legs at the thought of Adam.

Jamie stood on wobbly legs, the lace panties riding up into the crease of his ass as he padded to the kitchen. Coffee first, then cleanup, that was the plan. He needed to keep his hands busy, and his mind occupied, or he’d spiral right back to texting him again, he realized.

The coffee brewed, black and strong, and he sipped at it through a mug while surveying the mess. He found a wineglass in the sink, sat next to a second one with the stem broken off (he didn’t remember that happening). Hopefully, Kelly wouldn’t notice a missing glass. Then he looked past the living room and saw the dress crumpled on the bedroom floor, silicone inserts tossed on the dresser. Evidence was everywhere. So he started there, peeling off the lingerie, folding it carefully back into the hidden suitcase, then showered next. He scrubbed away the makeup, the dried cum, the scent of the man’s cologne that still clung faintly to his skin. And then shaved again, legs and face, the ritual somehow soothing in its familiarity.

By midday, the hangover had dulled to a manageable ache. He threw on loose sweats and a t-shirt, no underwear though, because the feel of fabric against his smooth skin was still too tempting. But the cleaning became a form of therapy, and soon the dishes were done, the counters wiped down, and the living room vacuumed, too. He tackled the pile of Amazon boxes under the shelf last, neatly stacking them for recycling later.

As he did so, one box shifted, and a small slip of paper fluttered out, landing face-up on the hardwood. Jamie bent over to pick it up.

It read: ‘Warranty Information: 2-Year Extended Protection Plan.’ No product name or description appeared, just a barcode and a customer service number. Odd, he thought, Kelly’s online shopping was legendary, but she usually tossed these things like this away immediately.

He shrugged, setting it on the counter to ask her about it later. Probably for some vibrator or lingerie she didn’t want him knowing about. The thought made him smirk: it was ironic, given his secrets.

His phone suddenly buzzed on the counter, and he jumped at the sound. When he peered at the screen, he saw that Kelly was video-calling him.

“Shit!” he muttered.

Jamie darted to the bathroom mirror: his face was clean, with no makeup residue. Then he tousled his hair boyishly. Thankfully, there had been no residual clues around the apartment, so he moved back into the living room and answered on the sixth ring, propping the phone against the coffee table as he resumed folding leftover laundry to look casual.

Kelly’s face filled the phone, looking sun-kissed and glowing with her blonde hair loose and wavy around her shoulders. She was poolside, reclining on a lounger in a tiny turquoise bikini that barely contained her curves, with a pair of oversized sunglasses perched on her head. Palm trees and glittering blue water framed her while Jamie heard laughter and splashes echoing in the background.

“Hey, Babe!” she beamed, waving. Then, she peered closer. “God, you look rough. Late night or something?”

Jamie forced a laugh, putting aside a folded shirt to rub the back of his neck. “Yeah, uh… too much wine and bad tv. My head is killing me.”

“Poor baby,” she cooed, pouting sympathetically. “Well, let me tell you about mine: we had the wildest night. Dinner turned into club-hopping until like four in the morning. These girls are animals. And Miami is insane, you’d love it here: perfect weather, killer drinks, and…”

She glanced sideways suddenly, lowering her voice with a mischievous grin. “…so many hot guys.”

Jamie blinked and dropped a pair of pants he was folding. A flush crept up his neck, and he said, “What do you mean?”

Kelly giggled, rolling her eyes. “Oh, I’m sorry, babe! I was just saying that to Becky, not you. She’s right here, being a total slut about it.”

The camera swung wildly as someone grabbed the phone. Then, Becky’s face appeared, flushed, tipsy even in daylight, with her brunette hair in a messy bun and a margarita in her free hand. She wore a white bikini top that strained against her full chest as she leaned in. Her blue eyes were sparkling.

“Hi, Jamie!” she sang, waving enthusiastically. “Miss you! Kelly’s not lying, South Beach is a buffet of man-candy, and they’re driving me insane!”

Jamie chuckled despite himself. “Hey, Bec. Are you having fun?”

“Too much,” she slurred happily. “Here, let me show you what we mean.”

She flipped the camera, panning across the pool deck where they were lounging. A group of shirtless guys was relaxing nearby: some tanned, most of them fit, while laughing over beers or mixed drinks. One had surfer blond hair and board shorts. Another man was dark-skinned and tall with tattoos curling over his shoulders. Then Becky zoomed in on a third: leaning against the bar, his dark hair wet and dripping from the pool, stubble shadowing a strong jaw, black swim trunks slung low on narrow hips—broad shoulders, defined abs, and possessing the kind of effortless bad-boy swagger that turned heads.

Jamie’s stomach dropped as he realized the man looked just like Adam! Same build, same dangerous smile as he chatted with a bartender. Absolute bad-boy. Becky lingered, zooming in shamelessly on the bulge in those trunks. There it was. A thick outline, heavy even at rest, the fabric clinging just enough to hint at what swung beneath.

“I wish I weren’t getting married,” Becky sighed dramatically, voice dripping with lust. “He looks like so much fun. What do you think, Jamie? Can I get away with some harmless flirting?”

Jamie’s mouth went dry. On the screen, he saw Kelly peek into the frame, biting her lip with amusement. His cock stirred traitorously in his sweats, remembering Adam’s press against him, the heat and weight of that large cock.

He gulped down nervous saliva. Becky’s face waited expectantly. “Uh… yeah, I think it’s fine,” he said. “As long as you don’t do anything you might regret.”

Kelly nodded, visible in the corner. “Exactly, flirt away, girl. Just no regrets tomorrow,” she added.

Becky squealed with delight. “See? This is why we all love Jamie! Best husband ever.” She blew a kiss at the camera before handing the phone back.

Kelly’s face returned, laughing. “Thanks for keeping her entertained, she’s already tipsy again. We’re recovering by the pool before hitting the clubs hard tonight. I might be a little MIA. Is that okay? You don’t have to wait up for me or be worried.”

“Got it,” Jamie said, voice steadier than he felt. He tried folding laundry again, but his hands trembled, so he stopped. He couldn’t stop thinking about that man, the Adam double. Then quickly added when he noticed a silence lingering: “Have fun, Kel. I won’t worry, just try to be safe. Those girls are wild.”

“Of course. You know me.”

Jamie turned his attention to the slip of paper he found and asked about it, trying to shift his mind from what he just seen.

“Oh, that warranty thing?” Kelly waved her hand. “Not important, just some boring protection plan. I’ll explain when I get home tomorrow.”

Jamie glanced at the slip still on the counter and nodded.

“Yeah, no rush. Love you.”

“Love you more,” she said, blowing a kiss. Then her brows furrowed, and she leaned in closer to the camera, whispering: “Is there anything you want to tell me, Jamie?”

He froze. His heart thudding against his chest. Did she know?

“What do you mean?”

Kelly paused and looked deep into his eyes. “Oh, I dunno, like…”

Jamie’s mind filled in the blank: ‘That you’re a crossdresser; that you met a man last night, that you want a big, hard, fucking cock inside you right now!’

But instead, she uttered: “I dunno, like… that you miss me.”

He laughed, half nerves, the other relief. “Oh, babe, you know I miss you,” Jamie said.

She giggled and said, “Okay,” before they exchanged “I love yous” s again. Then, the call ended.

The apartment fell silent again.

Jamie set the phone down slowly, staring at the blank screen. His mind replayed Becky’s video: that Adam-lookalike, the zoomed-in crotch with the casual outline of a thick cock that could ruin someone. Someone like him.

His own twitched fully hard now, tenting the loose sweats. He tried to resume cleaning, wiping shelves, and straightening photos, but his hands shook each time. Every swipe of the rag felt like stroking skin, and every bend at the waist to pick something up reminded him of how he wanted to spread his legs for Adam last night.

Jamie lasted twenty minutes. He rushed back to the bedroom and opened his phone with his thumb hovering over the dating app. Adam’s chat was still there with an unread message since the gentle rejection after their near-miss.

‘You okay after last night?’ Adam had written many hours ago now. ‘No hard feelings. The offer still stands if you change your mind. We don’t have to do anything you don’t want.’

Jamie gulped again with that same nervousness while he stared at the message, then at his reflection in the mirror. The streaks of dried cum had been cleaned. Now he was plain Jamie again, but when he looked closer, the hunger in those blue eyes was all hers. The blur between the separation of Jamie-the-man and Jamie-the-woman was dissolving.

He started typing, deleted, then started again.

Finally, he let his truth be heard and sent the message: ‘I can’t stop thinking about you.’

He hit send before the hangover, or the guilt, could stop him. Then he waited with his cock throbbing hard against his palm through the sweats, knowing he was already too far gone to turn back this time.

*****

Part 7…

The afternoon blurred into evening with the sun sinking lower and lower as Jamie sat cross-legged on the bed, the phone clutched in both hands. Adam’s replies came with no pressure, just warm interest that made Jamie’s stomach flutter each time the screen lit up.

‘Good. I haven’t stopped thinking about you either, pretty girl,’ he had replied. ‘You left me hard as hell last night. I leave tomorrow, but I’m still in town. Same room. Door’s open whenever you’re ready.’

They never veered into overt sexting; there was just enough heat to keep Jamie on edge, but with enough restraint to make him feel safe and wanted. By the time the streetlights flickered on outside, Jamie and Adam had settled on meeting again tonight, with no promises and no demands. Just a ‘come over if you want,’ from Adam. And God, did Jamie want it.

He stood in the bedroom now with the hidden suitcase open on the bed again. The red lace lingerie set lay folded in a heap. He peeled it away with a grimace: the panties were stiff with last night’s dried cum, and the bra was somehow faintly stained, too. He set them aside and reached for the black lingerie instead. It was sheer and delicate while being wickedly feminine: a lace balconette bra with underwire that would lift the silicone forms into soft, realistic cleavage. Then, the matching high-cut panties with a tiny satin bow at the front. And lastly, a garter belt in the same midnight black with sheer thigh-high stockings and lace tops that always made his legs look ever sexier.

Jamie moved through the ritual slowly this time, savoring every step; after all, he didn’t know when he’d ever get this opportunity again with Kelly back tomorrow.

The shower came first, with hot water gliding over his smooth skin, the razor moving carefully and slowly over his legs and ass again. He moisturized everywhere, the scent light and floral, Kelly’s favorite brand.

Then the panties when he was out: cool lace sliding up his thighs, settling high on his hips, the back dipping teasingly between his round cheeks. His cock was already half-hard just from the anticipation, nestled small and neat against the sheer front, with the outline visible if anyone looked close enough. The bra came next, hooks fastened with practiced ease, silicone inserts slipped in until the weight pulled gently down at his chest. He clipped the garter belt around his waist, slowly rolled the stockings up each leg, and fastened them with four soft snaps.

He paused in front of the mirror, turning to admire the effect. Black lace against pale skin, the garters outlining the curve of his large ass, stockings gleaming with their nylon. He looked expensive. Fuckable. Like a woman who knew exactly what she was offering.

Makeup came next. He decided on smoky eyes and a sharp contour, paired with a deep berry lipstick that made his mouth look wet and ready for anything. The wig last: those long chestnut strands brushed until they shone, bangs framing his face perfectly, stopping right at his arched brows.

He stepped into the other dress, the silver one that reflected light and was tight, short, and stretchy enough to hug every curve, and then, of course, Kelly’s strappy black heels—finally, a light coat over everything for the ride.

He was adjusting an earring when his phone buzzed on the dresser. It was a text from Kelly that said: ‘Getting ready for round two tonight! What do you think of this outfit?’

The photo loaded, and Jamie’s pulse spiked.

Kelly stood in what had to be the hotel bathroom mirror, phone held high. She wore a scrap of silver fabric that barely qualified as a dress: shimmering, skin-tight, with a plunging neckline that stopped just above her navel. It wasn’t a million miles away from what Jamie wore.

The hem skimmed the very tops of her thighs, riding up dangerously as she posed with one hip cocked. No bra, just her full breasts pressed against the thin material, nipples faintly visible through the metallic sheen. The dress stuck to every curve of her body: the dip of her waist, the swell of her hips, the round perfection of her ass. Her toned legs looked stunning in matching silver heels, her blonde hair tousled in beachy waves, and her lips painted cherry red to complete the picture.

She looked like pure sex. As if she was begging to be bent over the nearest surface and fucked senseless. Jamie’s cock twitched hard in the black lace, a fresh bead of precum soaked into the fabric as he swallowed thick saliva.

‘You look incredible,’ he typed back, thumbs shaking. ‘Absolutely stunning. Have an amazing night.’ He hit send.

Another buzz came almost immediately in his hands. There was a second photo.

‘One more for your collection,’ Kelly wrote, adding a winking emoji. ‘Don’t wait up…’

She was referring to a hidden folder he kept on his phone, one that Kelly often added to with daring images.

Kelly had turned around in the second image, bent forward over the marble counter, with the dress pulled up to her lower back. The silver fabric framed her round, plump ass perfectly. A tiny black thong disappeared between her cheeks, and she’d pulled the string aside with two fingers, exposing everything. Her smooth pussy lips glistening faintly, already wet, swollen, and pink. Above it, the tight image of her asshole, delicate and untouched. She looked back over her shoulder at the mirror, down to the camera with her lips parted, eyes sultry and knowing.

Jamie actually gulped out loud, a desperate, audible sound in the quiet bedroom.

He was dressed exactly like her: black lace thong pulled tight, the silver dress. Only the garters framing his own round ass, and the stockings too, hugging his thighs, were different. That, and what nestled beneath his panties: a small, leaking cock instead of that pretty, dripping pussy.

Heat flooded through his body with shame and lust mingling together. He zoomed in on the way her lips parted, the shine of arousal, the way her asshole clenched slightly as if winking at him. His own hole twitched in kind, aching to be filled the same way he suddenly wanted to fill hers.

But the thought that came now was worse: Adam seeing him like this. Bent over just like Kelly, dress hiked up, panties pulled aside, offering his own hole to that thick cock.

His fingers flew over the keyboard, and he wrote: ‘So sexy!’

He saved the photo immediately, dragging it into his hidden folder buried deep in the phone, the one already stuffed with dozens of others: Kelly in lingerie, Kelly touching herself, Kelly asleep with her legs spread. Jamie stared at the screen for a few more seconds with his chest heaving. Realizing now, he should have said more. Told her how he wanted to bury his face between her legs, lick her clean, fuck her until she screamed! That was what a husband would say, what a man would say.

But he didn’t. Because maybe, Jamie realized, he wasn’t exactly a man anymore. Something else entirely.

He locked the phone, slipped it into the purse, and headed for the door.

The Uber ride to the Hyatt was torture with every bump in the road shifting the lace against his cock, keeping him half-hard and leaking. He kept his coat closed tight, thighs pressed together, watching the lights of Brooklyn and Manhattan streak past. His mind replayed both photos in a loop: Kelly’s glistening pussy, his own black lace mirroring hers.

He chastised himself for not texting her anything else; he didn’t tell her he wanted to spread her open and ruin her. And especially didn’t tell her he was dressed just like her, on his way to let a man do things to him she’d never imagine.

By the time the car pulled up outside the luxury hotel, Jamie’s heart was thudding so hard he could practically hear it in his ears and feel it in his throat.

He stepped out into the cold night air and smoothed his coat down with trembling hands. This was one last chance to turn back, one last chance to not potentially ruin everything with the beautiful woman in the photos. The one in Miami was completely unaware of what was about to happen.

Jamie didn’t turn back.

*****

Part 8…

He stepped through the revolving doors and into the warm lobby, pausing just inside to smooth the hem of his coat with his heart still racing from the ride over. But before moving again towards the elevator with the heels giving him that extra sway he couldn’t quite control, he stopped short. Because he saw him.

Adam was standing close to one of the marble pillars near the concierge desk, his hands buried in the pockets of a tailored navy overcoat, dark jeans below. He looked effortlessly handsome, and brushed his hair the same way a man might before hitting on a woman; that same half-smile playing on his lips. Total bad-boy energy, Jamie thought.

“He’s even hotter than the guy in Miami,” Jamie said to himself. Turned on by his antics.

Adam’s eyes found Jamie, and he moved to close the distance between them with a few long, casual strides.

“You came,” he said quietly, voice low enough that only Jamie could hear it. His brown eyes traveled slowly across Jamie’s face, lingering on the berry lips, then down the line of the coat. “You look beautiful.”

Jamie’s cheeks burned. “Hi,” he managed once more, just like last night, as the word came out soft and breathy. “Guess I couldn’t stay away.”

Adam leaned in to peck him on the cheek, and Jamie’s eyes fluttered closed as the man’s smile deepened.

“I have a plan for tonight,” he said. “Something better than sitting in a hotel room. Do you trust me?”

Jamie hesitated for only a second. The hunger in him, that woman’s need to be seen, to be her, was louder than any fear he might’ve contemplated experiencing. So he nodded.

Adam offered his arm as if it were the most natural thing in the world, and Jamie slipped his hand right through it, fingers curling lightly around the strong bicep beneath the coat sleeve. He imagined it pinning him down and tried to steady himself, as they walked out together and into the cold night.

Central Park was only a short walk away, the paths lit by old-fashioned lamps that cast golden pools on the ground. The city noise faded behind them ever so slightly as they strolled beneath bare trees, their breath fogging the air. Jamie watched as a few joggers ran by, past some tourists mingling, too, and wondered if they suspected he was just a man in a dress. He held onto the arm tighter, and Adam didn’t rush. He asked gentle questions: how long Jamie had been dressing for, when it had started to feel more than just clothes.

“Years,” Jamie admitted quietly, heels clicking on the path. For some reason, he allowed himself to be honest. “It started with… curiosity. Then it felt like something else. Like this is the real version of me, it’s been hard to explain, and even harder to understand it myself.”

Adam listened without judgment, nodding along with his handsome face and asking follow-ups that made Jamie feel heard, not just seen.

“How many men have you met like this?”

Jamie laughed nervously. “None. You’re the first.”

Adam glanced sideways at him. “No way.”

“I’m serious, you’re the first guy I’ve ever met.”

Adam’s eyes softened, and he whispered, “That’s quite the honor.”

They found a horse-drawn carriage waiting near the southern edge of the park, close to Columbus Circle. A white horse that was straddled to a carriage with red velvet seats and fairy lights strung along the canopy, neighed in the night.

“How about a ride?” Adam asked.

Jamie protested weakly, before Adam with his confidence and ease promised it’d be fun. He helped him up first, hand warm and steady on his, then settled beside him, close enough that their thighs touched beneath the shared blanket the driver provided.

The carriage rolled slow through the park as the horse’s hooves clopped rhythmically. Jamie’s tension began to melt. His shoulders loosened and even his breath evened out without himself noticing. Adam’s arm draped casually along the back of the seat, fingers occasionally brushing the nape of Jamie’s neck, tracing the edge of the wig’s hairline. It felt like a real date. Like being courted, and it reminded Jamie of his first dates with his wife, all those years ago when they were just teens. Only now, the roles were reversed.

Jamie pulled out his phone under the blanket and texted Kelly: ‘Having fun at the clubs tonight? Miss you,’ he wrote. Maybe he was hoping for her to respond, and the guilt would make him go home, he thought.

But as he stared at the screen for a long time, all he could do was lock it when no reply came. She was probably dancing, laughing, and surrounded by all those girlfriends and music right now. Barely having time to look at a screen. So he tucked the phone away back into the purse and let himself lean a little closer into Adam, allowing his mind and body to accept its own need for an experience.

Adam talked too. About growing up in Chicago, a divorce a few years back, how he traveled constantly for work, and rarely let himself connect with women.

“I don’t judge people for wanting what they want,” he said quietly, fingers still stroking Jamie’s neck. “Marriage is complicated. And desire doesn’t always fit neatly inside vows sometimes. I don’t think you’re a bad person for needing this.”

Jamie swallowed, his eyes stung suddenly. “I love her. I do. But this part of me… she doesn’t know it exists. She’s the only person I’ve ever been with. The same for her with me.”

Adam’s hand settled warm on his shoulder. “Then tonight, you get to be exactly who you are. Who you want to be. There’s no shame in that.”

The ride ended not long after, and they left the park, walking a few blocks to The Polo Bar on East Fifty-Fifth. Warm wood paneling and low amber lights bouncing off the room’s deep green walls welcomed them inside. The space was cozy and intimate in all the right ways. Adam ordered for them both as they sat together: an old-fashioned for him, and a martini for Jamie.

“Why a martini?” Jamie asked as he sipped the strong liquor that came. He ate the olive flirtatiously.

“All the pretty girls drink martinis,” Adam replied, and Jamie smiled and giggled at the compliment.

Then another round. The alcohol loosened Jamie’s limbs, softened the edges of everything. The conversation drifted into flirtation with its effects, as Adam’s knee pressed deliberately against Jamie’s under the table, complimenting low and quiet about how the dress hugged Jamie’s hips just right as he let the coat slide off his shoulders; how the lipstick made him want to ruin it too. Jamie couldn’t help but gulp.

At one point, Adam leaned in, radiating heat and danger. “You mentioned a fantasy once,” he said, “when we texted. The one you were going to tell me about in person. What is it?”

Jamie began to sweat. He couldn’t admit it, but the alcohol made honesty feel easier. He stared into his glass, then met Adam’s eyes, deciding in the moment to speak his desire.

“I… I want to feel like a whore,” he whispered so no one could hear but them. His cheeks flamed red beneath the makeup; he could feel it. But he continued. “Like someone who’s paid for. I want to be used. Just… taken completely, by a dominant man.”

“Why that fantasy?” Adam asked with a wry smile.

Jamie thought about it. He never considered why, but said what felt right. “Maybe to stop me from backing out. To go through with it, like I can’t say no because that’s the role I’m in.”

Adam’s smile continued to spread slowly and approving. He reached across the table and brushed his thumb over Jamie’s lower lip, whispering, “good girl.”

Jamie grew so hard he nearly burst out of the black panties under the dress.

They lingered for another half hour, the air between them growing thicker with promise as Adam caressed the flesh of Jamie’s thigh beneath the stockings. Then, Adam paid for the check and led Jamie back out the door and into the night. The walk to the Hyatt was short, and Jamie realized he had only a few more minutes to decide whether this was actually what he wanted. Had this been enough, being treated like a woman on a date by a handsome man? Or, did she, that woman he was becoming, want more? There was a charged silence between them now, with only the sound of Kelly’s black heels clacking across the pavement, breaking through.

When they finally reached the hotel entrance, Adam stopped and turned towards him. His breath was steady, his arms solid as they touched Jamie.

“Would you like to come up?”

Jamie’s pulse thundered in his ears. Did he want this? What if Kelly found out? He had to make a choice as Adam looked at him: handsome and sexy and promising all the things Jamie desired most of all, exactly like all those men in his fantasies and videos. And so he made a decision, staring at Adam, because he didn’t know if it would ever be this perfect again. He nodded.

Adam’s smile grew wider, and he leaned closer, brushing Jamie’s ear with his lips to say: “The website I ordered you from said I paid for you to stay with me the whole night.”

Jamie froze, then caught on to the game. A rush of heat flooded him. Arousal so sharp it made his knees weak. He played along, responding in a breathy voice, “Oh, really?”

Adam’s hand settled possessively on the small of Jamie’s back, guiding him through the doors and into the lobby. “Mhmm. They also mentioned you’re their best whore. Said you even take it raw, no condoms. Is that true?”

Jamie’s cock throbbed hard against the black lace; a wet spot was already spreading. His mind spun, to Kelly somewhere in Miami now, probably still dancing, oblivious. The risk of Adam’s words, the wrongness, the sheer filthy thrill of it all crashed over him. The condom was still in his purse, that invisible line he didn’t dare cross.

But he hesitated for only a second, then looked up at Adam through mascaraed lashes. “What the website said… is true,” he whispered. “Only raw.”

Adam’s eyes darkened. He pressed the elevator button, his hand never leaving Jamie’s back.

“That’s what I thought. Good girl.”

The doors slid open, and then, they stepped inside.

*****

Part 9…

Inside the elevator, the mirrored surfaces reflected Jamie’s image at him from every angle. Those berry-stained lips slightly parted as his breath quickened; cheeks flushed; the silver dress clinging beneath the coat he wore. And Adam stood behind him, tall and imposing, with his hand still firm on Jamie’s lower back, the thumb now tracing slow circles that sent sparks straight down to his legs.

As the elevator began its ascent, Adam’s touch shifted lower, fingers tracing over the curve of Jamie’s ass, squeezing through the coat and dress. Jamie gasped softly. His small cock twitched in the black lace panties, already slicked wet with anticipation as Adam leaned in and brushed his mouth against Jamie’s ear.

“You’re going to be mine tonight, whore,” he said with his voice coming out in a low rumble. “Every inch of you.”

Jamie shivered, nodding mutely, his body leaning back into Adam’s heat without having a moment to think. The elevator dinged as they came to a stop on the second floor. With the doors opening to the quiet hallway, Jamie recalled it was the same hallway he’d run away from last night, but this time, there’d be no turning back.

Adam guided him out, hand still possessive and on his waist, leading him straight to room two-thirty. The keycard beeped, and the door swung open as they stepped inside.

The hotel room was dim, just like the night before, with the curtains drawn and a single table lamp lit. But now, Jamie noticed a bottle of lube and a towel already laid out on the bedside table, waiting; Adam had always known he’d be back tonight. The king bed dominated the space, with crisp white sheets ready to be rustled. And Adam now shut the door with a click that echoed in the room. A sound that repeated in Jamie’s mind that there was no going back as the lock latched.

Then, Adam turned away from the door. His eyes and face appeared dark in the room, but the unmistakable sense of hunger remained as he shrugged off his coat, revealing a dress shirt clinging to every toned part of his torso.

“Strip,” he commanded, voice laced with heat. He didn’t move closer yet, just watched.

Jamie’s fingers trembled as he slipped off his own coat, letting it drop to the floor with a thud. The silver dress came next, with the zipper tugging down his spine and the fabric sliding loose over his hips, until eventually pooling down to his heels. He stepped out of it carefully, standing there in the black lingerie: a balconette bra pushing up the silicone breasts, a garter belt framing his slim waist, stockings covering his long legs, and the sheer panties that did nothing to hide the small, hard outline of his cock or the wet spot at the tip. In the dark room, his smooth, pale skin looked even sexier against the black of the lingerie.

Adam’s breath quickened loudly within the room, and his eyes moved all over Jamie’s body in the outfit.

“Fuck,” he exclaimed. “Look at you, Jamie. All dressed up like a perfect little slut. Good thing I paid for you to be here.”

He closed the distance, slowly. Then the man was right in front of Jamie, tall and built solid, backing him against the wall with gentle but insistent pressure. One hand planted onto Jamie’s hip, and the other tilted his chin up. Adam’s body pressed close, the hard line of his erection already straining against his pants as he pushed it slowly against Jamie’s thigh, who was now pinned between the wall and the man.

“So you want to be my whore tonight, huh?”

Jamie’s heart slammed against his ribs as he looked up at the man now inches away from him through the bangs of the brown wig. The words ignited something deep and desperate inside him; this was the fantasy made real. And he wanted it so fucking bad.

“Yes,” he whispered, voice high with feminine need. Then desperately: “Please…”

Adam’s mouth crashed down on his, the kiss rough and claiming with his tongue thrusting in without warning, teeth nipping at the fat of Jamie’s lower lip. Jamie moaned into it while his hands started to clutch at Adam’s shirt, body arching off the wall with pure excitement. The taste of bourbon and man flooded him. It was overwhelming, but perfect. Adam’s free hand roamed, sliding down to squeeze a silicone breast and thumbing the lace-covered nipple beneath, then lower to grip both of Jamie’s hips, pulling him tighter against that insistent hardness that threatened to destroy him.

“Take off my shirt,” Adam demanded, breaking the kiss for a second to then nip at Jamie’s throat, and Jamie listened and obeyed. Using his trembling fingers to unbutton one after another. Revealing the warm skin of Adam’s broad shoulders, lower, to his toned chest dusted with hair, then finally, to show the hardness of his abs.

Adam spun Jamie around with one quick move and pinned him face-first to the wall. He grabbed Jamie’s wrists and guided them up to above his head and held them there against the wall with one large hand. Jamie could feel the man’s hardness resting against the plumpness of his butt.

“On your knees,” Adam growled with his faintly stubbled cheek against the smooth counterpart of Jamie’s, voice rough with want.

Jamie sank obediently as the heels made his descent graceful, despite the tremble in his legs. The carpet was soft against his knees, and the wall cool on his forehead as Adam kept Jamie’s hands pinned high. From this angle, Jamie could feel the power imbalance so acutely: he was small, submissive, and totally fucking exposed to a man who wanted to dominate every inch of him.

Adam’s other hand worked the belt of his pants open. Jamie could hear the sound of metal from behind, then the zipper coming down. He looked to his right and saw the jeans and boxers shoved down to his thighs in one fluid motion. Then, Adam turned Jamie around, now with his back pressed to the wall, but his hands still held firm against it. And there it was: his cock. A real man’s cock! It was thick, heavy, curved slightly upward, and massive, easily double the length of Jamie’s inadequate eight or nine inches. Veined and flushed dark with arousal in the dim room, the head already swollen.

Jamie stared, and his mouth instantly watered. A whimper escaped him because it looked even bigger up close, and it was as intimidating as it was irresistible. At the base, dark pubes framed the man’s dick, and there was the faint smell of what Jamie realized was the uniqueness of a male’s musk; full of testosterone and a burning need to conquer. But it didn’t make him turn away. In fact, he wanted to move closer.

“Suck it, my little whore,” Adam ordered, wrapping his hand around the base of his shaft and guiding the tip to Jamie’s lips. There were no more thoughts, only a deep craving and need from Jamie.

Jamie parted his mouth eagerly with his hands still held high, and darted his tongue out to taste the full head of the man’s impressive dick. It was his first taste of cock… he couldn’t believe he was doing this, kneeling in lingerie, hands pinned, about to blow a man while his wife partied oblivious in Miami. But it felt right, so achingly right as his tongue swirled around the large velvet head that bobbed expectantly.

He felt the cool of the stolen heels against his ass cheeks as he leaned forward, taking the head deeper into his mouth, lips stretching around the massive girth of his lover’s (and role-playing client’s) shaft. Adam groaned and rocked his hips gently as Jamie worked more in, tongue swirling all over, his cheeks hollowing with suction.

“Good girl,” Adam praised, his voice strained. “This definitely isn’t your first time. Take more. Show me how much you want it.”

Jamie did. He bobbed his head back and forth, relaxing his throat to accommodate the massive length. It came to him naturally, as saliva dripped down his chin, smearing his lipstick. But he didn’t care that it was ruining his makeup. The musky taste filled him, and the weight on his tongue was intoxicating. Heavy and thick. So much bigger than him in every way. Adam’s hand tightened around his pinned wrists, the other threading into the wig to guide his rhythm. Faster now, and deeper, until Jamie gagged more around him when Adam pushed too far.

“That’s it, baby. Deeper.”

Adam pushed more, and Jamie gagged louder with tears welling in his eyes. Every space in his mouth was filled with cock, though he only had maybe a quarter of the dick inside at the most, and he could feel the vein on Adam’s impressive manhood thud against his tongue.

At one point, he realized his hands had been released, and involuntarily, Jamie had placed both at Adam’s thighs. Holding onto his flexed muscles as his fingers threaded into his leg hair. He was doing this all on his own, without the need for Adam to force him down onto his cock. Sucking and occasionally gagging when he went too deep, as if it were the most natural thing in the world. Adam exhaled with approval.

After what felt like an eternity of wet, slurping sounds and Adam’s low moans, Adam finally pulled out with a pop. His cock appeared shiny and reflective in the dim room, and it was throbbing angrily. He rubbed it against Jamie’s lips with a sense of possession, marking him with a trail of sticky precum left in its wake and slapping him gently across the cheek with it, too.

“Get up,” he said. “And put yourself over the chair.”

Jamie rose on shaky legs, and Adam kept a hand on his back to steer him. The armchair by the window was wide and sturdy, and Adam bent him over the front of it with ease. There was no resistance as Jamie placed both hands on either side of the arms of the chair and pushed himself upright, presenting his ass high in the black lace and garters. He could feel his pulse spiral out of control.

“Knees too,” Adam ordered, spanking Jamie’s ass, and Jamie obliged, feeling his stocking-clad knees sink into the cushion of the chair, bending him over more into all-fours.

Adam stepped back for just a moment to admire the sight. “Look at that ass,” he whispered. “It’s practically begging for dick. Looks like it was made for it too.”

He caressed each cheek, and Jamie shivered at the touch, as the man then hooked a finger under the panties and tugged them aside, but not completely off, exposing Jamie’s smooth hole and taint. Shaved and ready, just like a girl. The snap of the lube bottle filled the room, and suddenly a cool slickness drizzled over Jamie’s entrance as Adam’s fingers circled, pressing in one, and then two, to gently open him up. Jamie let out a soft moan at the sudden and new feeling.

He looked up to face the window, and in the reflection, he could see Adam behind him. Completely nude now, with his muscular body tensed and ready to devour him.

“Only raw, are you sure about that, my little whore?” Adam asked, voice teasing but edged with seriousness, fingers curling inside to brush Jamie’s prostate. “Are you sure the website didn’t make a mistake when I ordered you?”

He pushed deeper, and Jamie arched his body against the feeling, moaning louder now, as his mind flashed to the condom wrapper still tucked in the purse on the floor. It was unused, but unneeded. He was so turned on that his cock was already leaking a steady drip of precum into the lace. Somehow, the risk and the idea that he was a whore about to be barebacked only heightened everything.

“Yes,” he gasped desperately. “They were right. I want it raw. Please, Adam… fuck me raw.”

Adam chuckled, then withdrew his fingers to lube his own cock, stroking it slowly. Jamie could hear the slicking back and forth as the man behind him readied his huge, aching cock, while his own remained hard within the panties: though he knew it was useless, he wouldn’t be penetrating anything tonight.

“Whores take it hard without complaining. Is that what you do?” Adam asked, slapping Jamie’s ass.

“Yes,” he whined in response, pushing back against nothing. “I’ll take it hard. No complaining.”

“Do you promise?”

“Yes…” Jamie moaned again.

Adam lined up his huge cock, placing the blunt head against Jamie’s hole, and whispered: “Good girl.”

He thrust in with one violent snap of his hips, burying half his length in a single stroke. Jamie cried out, and his body turned stiff all over. The burn was intense, unlike anything he’d ever felt before, and his hole clenched around the intrusion with a desperate need to make it stop. But Adam didn’t pause. He held onto Jamie and pulled his cock back before slamming in even harder, trying to force every inch inside Jamie’s tight virginal ass.

“Ugh!” Jamie wailed louder into the room. The pain was excruciating. He felt as though he had been split in half, and a part of him wanted to escape. To run away and admit he’d made a mistake. But somehow, the pain was also pleasurable… he couldn’t make sense of it, his mind was spinning, body trying to lock down as his hands clawed at the fabric of the seat for some kind of relief. But none was coming as Adam pulled out and thrust back in again.

“Good little girl,” Adam muttered. He pushed harder now, inch by excruciatingly painful inch, and Jamie’s heels kicked against the chair at the intensifying pain and pleasure. He screamed and felt as if he might weep openly as his hole began to stretch more around the large cock, tearing into him. Ruining him, maybe forever.

“You’re such a good whore, Jamie,” Adam added, giving words of encouragement as he slid even deeper, breaking down the last bits of Jamie’s resistance. All Jamie could do was tremble and cry out in pain; that seemed only to make Adam harder.

Adam pushed and pushed until finally, he was seated, all eight or nine inches, as his balls pressed firm against Jamie’s ass. Heavy and covered in musk. Now it’s Jamie to mark him as his own personal whore.

He held it for a moment, not moving, letting him feel owned, and Jamie whimpered, “Oh, God…” The fullness was overwhelming. It was stretching him to the absolute limit as every inch of that massive cock claimed him.

“Do you want me to stop, slut?” Adam asked.

Jamie held onto the seat. He wanted to scream ‘yes,’ but instead whispered, “no.”

Jamie realized he could no longer call himself a man, not anymore. Not after what he just let Adam do to him. And somehow, that idea felt right to him, because he felt more like a woman in this moment than he ever did before.

“Good girl,” Adam whispered in his ear, as if stroking that thought, sliding a hand up Jamie’s back and pressing down, bending him over even more. Jamie’s face became buried into the front of the chair now, humiliating as he realized his mouth was pressed where hundreds, if not others, had sat, and Adam said: “Now I’m going to fuck you like the whore you are.”

His hands gripped Jamie’s hips hard enough to bruise as he pulled him back and forth with each thrust. Adam’s pace was brutal. Jamie wailed a muffled moan, but Adam didn’t stop. The chair creaked under the force, and Jamie’s body jolted with every devastating impact as he felt his masculinity slowly erode. His cheeks jiggling and clapping from the sheer force with which Adam penetrated him.

“Fuck, you’re tight,” Adam grunted, pounding relentlessly. “Taking my cock like a pro. That’s it, squeeze around me, whore.”

Jamie kicked and screamed with pleasure as he felt his ass become nothing more than a used hole for a man’s needs.

His moans filled the room, high and feminine now as he placed the side of his cheek on the seat cushion, as his small cock bounced uselessly in the panties with each slam into him. Precum dripped even more steadily now, soaking the lace further, and Adam’s hips continued their slapping against his ass. The man behind him spread each round cheek apart, and the wet sounds were obscene, as lube squelched as he drove in deeper, angling to hit that spot that made stars explode behind Jamie’s eyes.

“Oh my God… fuck!” Jamie repeated. The pain was subsiding but still there, while pleasure began to overtake in greater intervals. He could feel his hole being destroyed.

“Such a filthy slut,” Adam growled, one hand sliding up to wrap around Jamie’s throat from behind, squeezing lightly. “Dressed like this, begging for raw cock. Your wife knows what a whore you are?”

Jamie whimpered, the words twisting shame and pleasure together. “N-no… oh God, harder…”

Adam obliged, and his thrusts turned savage, as he pulled almost all the way out before ramming back in to Jamie’s tight hole. Over and over again. Jamie felt as if a hard rod made out of iron was being pushed deep into him, as Adam’s balls thwacked audible against his taint with each thrust.

Adam reached around and shoved the panties aside to wrap a hand around Jamie’s dripping cock, small in his palm, stroking roughly in time with his fucking.

“Look at this tiny thing,” he barked. “No wonder you need a real man. After I use you, you’ll probably never want to fuck pussy again. Only cock in your ass from now on. In your pussy. Isn’t that right?”

Jamie moaned and threw his head back. “Yes,” he said breathlessly. The pain and pleasure were an intoxicating mix, and now Adam’s words were fuel to the fire raging in his body.

“Cum for me, whore. Show me how much you love being fucked,” Adam demanded. “Once I make you cum, you’re not using your little dick anymore tonight. Understood?”

Jamie nodded as the hand between his thighs kept stroking, and his hole continued to get ripped apart.

It built and built, causing him to shake all over, then he shuddered with an orgasm ripping through him without warning. He spilled over Adam’s fingers, ropes of cum splattering the chair seat, body convulsing around the cock still pounding into him. His hole clenched with each spurt, but Adam didn’t stop; he fucked him through it, causing more pain and prolonging the waves until Jamie was openly sobbing, oversensitive and trembling.

Only then did Adam slow, pulling out with a wet pop. His cock sprang upwards as it left his entrance, still hard and throbbing.

He spanked Jamie’s ass, hard, and the sting flowed through his body. Then another… and another, until Jamie could feel both cheeks were burning red. He moaned and whimpered, and Adam periodically spread Jamie’s cheeks apart, before striking again; the left, then the right.

“Not done yet,” Adam said, voice husky and breath erratic.

He hauled Jamie up from the chair, turned him around, and scooped him into his arms like he weighed nothing. Jamie wrapped his thighs and legs around Adam’s waist instinctively, the heels digging into his back, and draped his arms around his shoulders as Adam carried his limp body to the bed.

He lay him down on the mattress, on his back, facing the pale white ceiling. Then, Adam climbed on top with his weight shifting the bed down, and shoved Jamie’s thighs apart, hooking one stocking-clad leg over his broad shoulder. He tugged the panties down just enough to free Jamie’s spent cock, then lined up his huge dick and thrust back into Jamie’s hole, bottoming out in one smooth glide without a chance to rest.

“Eyes on me,” Adam commanded, starting a deep, grinding rhythm. “Watch me fuck you like the whore you are.”

Jamie obeyed, blue eyes locked on Adam’s as he was taken. The position was intimate, exposing, and Adam’s beautiful body was completely covered by his, as that big cock slid in and out in long, deliberate strokes that dragged over every sensitive nerve. Jamie realized that even if he wanted this to stop, he couldn’t. Adam, with his glistening muscular body, was so much stronger, and he was completely pinned down to the mattress.

Minutes stretched, sweat beading on both their skin as the bed creaked rhythmically.

“You feel that?” Adam muttered, five minutes in, his hips rolling slow and deep. “My cock owns you. Stretching that tight little hole. No condom, gonna fill you up soon, breed you like a bitch.”

Jamie moaned, hands clutching Adam’s shoulders, nails digging in. “Yes… breed me… please…” he whispered desperately.

Adam sped up gradually, and his thrusts turned sharper, hitting Jamie’s prostate with precision. At ten minutes, he heaved both stockinged legs over his shoulders and grunted: “Such a greedy whore. Look at you, legs spread, begging for cum. Your pussy’s made for this, isn’t it?”

Jamie’s head thrashed off the bed, fresh arousal building despite his recent orgasm. The idea that his ass was now a pussy turned him on, but he also felt right.

“It’s yours… all yours…” he yelped as Adam’s cock plunged deeper.

At fifteen minutes, Adam’s pace grew brutal again, sweat dripping from his brow onto Jamie’s chest. He leaned down, capturing Jamie’s mouth in a messy kiss, tongue fucking him in time with his cock. Jamie didn’t resist, instead he allowed his mouth to be dominated the same way he allowed Adam’s cock to dominant him too.

“Gonna ruin you for anyone else,” Adam whispered against his lips, breaking the kiss. “Every time you sit down, you’ll feel me.”

And then, something unexpected happened: Jamie came again, dry this time, his body clenching out of control around Adam’s manhood. His thighs quivered involuntarily and drew a deep guttural, feminine groan from his throat. He was cumming as hard as ever, but without a drip leaving his body, or his little dick erect; it was completely flaccid.

“That’s it, baby,” Adam whispered into his neck. “Keep cumming for me.”

Jamie’s gasps continued to come out in staccato-like shots, as his hole spasmed out of control.

At twenty minutes, Adam’s rhythm faltered, and his thrusts became more erratic now, deep and punishing. “Fuck… close… gonna cum inside you, whore. You want me to get you pregnant, huh?”

The words struck something deep inside Jamie, and he wrapped both legs around Adam’s hips, pulling him deeper. “Do it… cum in me…”

He demanded it, needed to feel a real man’s cum deep inside him more than anything else in the world right now.

“Fuck…” Adam panted.

He slammed in one last time, burying himself fully as he unloaded hot ropes, one after another, pulsing deep into Jamie’s ass, filling him until it leaked out around the base of his cock with nowhere else to go. Jamie moaned with his head arching off the bed, and Adam groaned long and low while his hips ground through the aftershocks as he marked Jamie completely. Owning him.

They collapsed together with Adam’s weight pinning Jamie to the bed, both panting. Jamie could feel warm cum trickling down his thighs as Adam softened inside him, still buried, and they stayed like that for a few minutes more. Adam’s hand stroked lazily through the wig, while Jamie’s arms wrapped around his man’s back, interlocked and intertwined.

Finally, Adam pulled out gently, a gush of cum followed the exit of his cock, and he kissed Jamie’s forehead, gentle and loving. “Be right back,” he said, rolling off to head to the bathroom.

Jamie lay there, his body still buzzing, sore and leaking and twitching even now as if a dying animal. He couldn’t stop panting. He leaned over the mattress and reached for the purse on the floor, fishing out his phone; the sight of the condom inside was a cruel reminder of the line he betrayed.

When he looked at his messages, there was no response from Kelly, and now he noticed the text he sent his wife earlier, the one about having fun at the club, showed up as ‘undelivered.’

How did he miss that? He frowned, checking the signal: full bars. Maybe her phone died, or she turned it off? Confused, he set it down with a flicker of worry cutting through his aroused mind and thought: what if she’s on an early flight back to New York right now? Somehow, having found out what he’d been up to.

A toilet flushed, the sound of running water, and then Adam returned, naked in the dim light with his hung cock soft but still impressive. Hanging with weight and bigger than Jamie’s own, even at his hardest. He slid back into the bed and pulled Jamie against his chest.

“You doing okay?” he asked.

Jamie smiled. “Yeah… just a little worried. About my wife,” he admitted.

Adam kissed him softly and said, “I’m sure she’ll be fine. Don’t worry so much.” The man paused, looking over Jamie, and asked again, “Are you doing okay after the sex, though? It might’ve been too much for you.”

Jamie thought for a moment and said, “I’ve never orgasmed like that before. Without touching myself.”

Adam brushed a strand of the wig’s bangs out of his eyes and whispered, “That’s your body finally realizing how it was always meant to cum. Like a woman, because that’s what you are, isn’t it?”

Then he kissed him deeper, on the lips now. “We’re not done,” he promised, voice dark and teasing, hand sliding down to cup Jamie’s round ass. “I’m keeping you here all night. Fucking you until you can’t walk straight, my perfect little whore. If that’s okay with you.”

Jamie shivered, pressing closer. “Yes… all night,” he repeated, burying his concerns about Kelly. It was just paranoia, he told himself.

As Adam’s fingers dipped between the wedge of Jamie’s backside, teasing the wet hole he’d already ruined once, Jamie closed his eyes and let himself sink into the man who now promised to claim him again and again. Not just as a whore for the night, but as a woman, forever.

*****

Part 10…

The first gray light of dawn crept through the gap in the hotel curtains, landing across the tangled sheets. It was just past six in the morning, and Adam was sprawled on his back with one arm flung above his head, chest rising and falling in the slow rhythm of a deep and satisfying sleep.

Jamie stirred carefully. He’d only slept for a few hours, and every muscle was protesting as he shifted. The room smelled of sex: that familiar cocktail of sweat and lube and cum intermingling together, and his body bore the memory of its actions; it felt battered in the best and worst ways possible. His thighs trembled, his ass throbbed with a deep, delicious ache as he sat up. It was the kind of pain that radiated with every small movement for good and bad.

Cum had leaked from him all night, drying in sticky trails down his inner thighs and crusting the black lace panties he’d never fully removed. Adam had fucked him relentlessly all night: missionary again until Jamie’s legs shook, then on all fours with the garters snapping against his skin. When he rode Adam’s erect dick with his fat ass bouncing up and down, his small cock flopped uselessly until he orgasmed untouched again. Screaming like a woman. Each time Adam had buried himself deep and unloaded, hot pulses flooded Jamie’s pussy until it overflowed, marking him inside and out. Four times. Maybe five. Jamie had lost count somewhere around the third orgasm, tears streaking his cheeks with mascara as he begged for more.

Now, in the quiet and afterglow, the reality settled in. He had to get home before Kelly returned from Miami.

He eased out of bed inch by inch, wincing as his sore hole clenched around nothing. It was so accustomed to being filled that it didn’t seem to know how to exist without a large throbbing cock inside it. That wasn’t the only issue: the stockings on Jamie’s legs had runs, one garter belt snapped completely, and the bra hung crooked with the silicone inserts shifted. He padded barefoot to the bathroom, the heels were somewhere on the floor, and closed the door softly so as not to wake Adam.

The mirror was unforgiving when he turned on the light. His lipstick was smeared into a bruised halo, the wig matted in parts and crooked in others, and the eyeliner was now a smudged black from tears and friction against the mattress. His ass, when he turned and bent slightly, was a sight: red from spanks and gripping hands, and his once pristine and tight virgin hole was now swollen and glistening with remnants of lube and cum. He looked thoroughly used, exactly like the whore he’d begged to be.

Jamie ran warm water and cleaned himself as gently as he could while wiping away dried cum from his thighs and chest and rinsing his mouth. The tenderness between his legs made him whimper, but the memory of how it got there sent a weak pulse of arousal through him anyway.

He pulled his phone from the purse on the counter. The screen lit up with a notification sent thirty minutes ago, when he was finally asleep after being fucked all night.

‘Sorry, babe, phone died last night,’ Kelly’s text read. ‘Heading to the airport now. The flight lands around eleven. Can’t wait to see you!!!’ A love heart emoji followed.

Relief flooded him, sharp and sweet: she was safe, and coming home. Then the guilt followed right behind it with its heavy and familiar twist in his gut. How could he have spent the night letting another man breed him raw while she danced in Miami, he wondered. Jamie stared at her message, fingers hovering, unsure what to reply. What could he say? Every word felt as if it could be an admission of guilt.

He suddenly remembered Kelly’s image from last night and opened the camera instead. For some reason, the same pose she’d sent him, bent over the marble counter in the Miami hotel, with the dress hiked up, panties tugged aside, made him want to remember this moment in the same way.

He angled the phone and captured it: his round ass framed by garters, the black lace pulled to one side, his used hole on full display in more vivid detail: it was pink, and no longer tight but swollen and partly open from abuse, glistening faintly with another man’s cum; he looked exactly like her filthy mirror image. Only used. He saved it to the same hidden folder, then stared at the thumbnail. The sight made his spent cock twitch weakly in the lace.

He had to leave. Now. Shower at home, clean the apartment, hide everything before she walks through the door. That much he knew.

So Jamie slipped back into the bedroom and gathered the silver dress and coat as quietly as possible. He was reaching for Kelly’s black strappy heels when the mattress creaked. And then, Adam yawned.

“Going somewhere, pretty girl?” he muttered in the dark of the room.

Adam’s voice was soft and sleepy, no longer the commanding growl of a role-playing client from last night, but warm and gentle. He propped himself on one elbow as the sheet pooled low around his hips and watched Jamie with adoring eyes.

Jamie froze, clutching the dress to his chest. “I… yeah. I have to get home. My wife’s flight lands soon,” he stammered.

Adam nodded, not with anger or possessiveness behind it, but just an understanding as to who Jamie really was. A husband and a man; or was he? Adam sat up slowly, and the sheet fell away to reveal his naked body. That broad chest, defined abs, cock soft, but still thick and long against his thigh, framed by dark pubes.

“Come here a second,” he whispered.

Jamie hesitated, unsure if he should, then walked over and perched himself on the edge of the bed, feeling his butt sink into the mattress. Adam reached out, brushing a stray strand of the wig from Jamie’s face.

“Did you get everything you hoped for last night?”

Jamie’s throat tightened. He nodded, and his voice came out small to say, “Yes. More than I hoped for. It was… perfect.”

Adam smiled, a genuine and kind one, and said, “Good. You deserved to feel that way.” Then he paused, and his eyes seemed to twinkle with leftover mischief from mere hours earlier. “But you’re forgetting one thing.”

Jamie blinked and responded in a hushed voice, “What?”

“You haven’t swallowed a man’s cum yet.”

Heat rushed through Jamie’s face so fast that the only way he could shake it was to glance at the hotel clock on the bedside table. It was six-fifty-seven.

“I… I want to. God, I do,” he muttered. “But I really have to go. My wife–”

“You’ve got time,” Adam said gently, already sliding out of the bed. His cock was half-hard just from waking, thickening as he stood. “One last thing, then I’ll let you go. Promise.”

Jamie’s resistance crumbled instantly at the sight of Adam’s hung member. He sank to his knees on the carpet without being told and looked up through his smudged lashes.

Adam stepped closer, muttering “good girl,” as his cock started lifting to its full hardness now, thick and familiar and oh so intimidating.

The scent hit Jamie first: musk, sex, and the faint tang of his own ass from last night, Adam hadn’t bothered to clean off; maybe savoring it as a spoil of his conquest. Adam stepped even closer now, and Jamie opened his mouth eagerly.

Adam fed it to him slowly, letting Jamie set the pace at first. Lips stretching wide, tongue swirling around the head, tasting the salty remnants of their night. Jamie moaned around him and the humiliation, taking more, hollowing his cheeks and bobbing with increasing hunger. Adam threaded his fingers gently through the wig, guiding him but not forcing the act.

“Don’t forget about the balls either, pretty girl,” Adam said.

Jamie held Adam’s huge dick up towards the man’s navel and began to lick at the heavy balls, allowing his nose to press in. He was flooded with an intoxicating aroma that made his knees weaken, and his little dick hardened. But it was not to be touched: it was only a spectator now. Maybe even forever.

Minutes passed, and the sky outside lightened from gray to pale gold as the sun began to creep above the park skyline visible through the curtains. Jamie’s jaw began to ache as he kept sucking Adam’s cock. Saliva was dripping down his chin again, but he didn’t stop; he couldn’t. The taste and weight and all those soft praises Adam murmured: “such a good girl;” “look at you, so greedy;” kept him going.

Adam reached for Jamie’s phone out of the purse and said, “I want to document this for you. Something to remember me by.”

He angled the camera down, recording the sight: Jamie on his knees in ruined lingerie, lips stretched around a thick cock with his eyes watering yet totally devoted. Jamie’s cock gave another weak twitch in the lace; he was turned on by it, by being filmed like this.

Adam’s voice stayed gentle, but the words turned filthy. “What would your wife think if she saw this, Jamie? Her husband, on his knees, swallowing cock like a pro,” he asked.

Jamie whimpered around the shaft, unsure, with his arousal spiking.

“Bet she’s gorgeous,” Adam continued.

Jamie, without thinking, grabbed the phone and unlocked it before handing it back. He pulled the cock out of his mouth for a second to breathe and admit: “Go to the hidden folder on my phone.”

He planted soft kisses along the shaft and sucked at his large head, while Adam found the hidden folder easily, scrolling through the dozens of photos of Kelly in bikinis, nude, and the bent-over mirror picture from last night. His breath grew shallow, and his cock started throbbing harder in Jamie’s mouth.

“Fuck… look at her. That ass. Those tits. She’s stunning.”

He zoomed in on the photo of Kelly exposing her wet pussy, and his voice was low and full of lust. “Bet she’d be shocked to see her pretty husband full of my cum right now. Or maybe… maybe she’d want to watch.”

Jamie moaned louder, sucking harder, the dirty commentary pushing him over the edge into pure submission.

“Don’t touch that little clit, baby,” Adam commanded.

“I wouldn’t dare,” Jamie responded, before putting the thick cock back into his mouth.

Adam kept scrolling, muttering appreciation. “God, look at that tight little body…” he said, then smirked and asked, “What airport is she landing at?”

“LaGuardia,” Jamie replied.

“Hmm, maybe I’ll run into her, Jamie. Tell her all about what you’ve been up to.”

Jamie sucked and moaned harder than before, and he could feel Adam’s thighs and groin tighten suddenly.

“Gonna cum, baby. Swallow it all.”

Adam held Jamie’s head gently and thrust deep, spilling hot and thick cum straight down his throat. Pulse after pulse, Jamie swallowed greedily, not spilling a drop, throat working around the head until Adam sighed and pulled out slowly, leaving a string of viscous white cum at the tip of his cock.

Jamie stayed on his knees, panting with his lips swollen and shiny.

“Stay right there, baby,” Adam said. He wasn’t finished and started stroking himself, still hard, while aiming at Jamie’s upturned face.

“Don’t move that pretty little face, Jamie. I’m going to mark you as my whore forever.”

Jamie obeyed and looked up from his vantage point, watching helplessly as Adam stroked his huge cock back and forth, right in front of him. Then, sudden and violently, a load shot out, covering his lips. The second load striped across his cheeks, lips, and forehead in one long burst. Warm ropes marked him like ownership, and Adam stroked every last drop out before regaining enough composure to snap a quick photo and send it to his own number.

“That’s for me to remember you by,” he said softly, helping Jamie to his feet. “And now you have my number. Text me if you’re ever in Chicago. My door’s always open for a pretty girl like you.”

Jamie nodded, dazed, tasting the cum on his tongue and feeling the warmth of Adam’s seed all over his face. He cleaned up quickly in the bathroom, fixed the wig as best he could, then touched up his makeup just enough not to draw too much attention on the way out. He slipped into the silver dress and coat and stumbled out of the bathroom. Finally ready to go home.

At the door to leave, he turned back. Adam pulled him in for one last gentle kiss, slow, tender, and nothing like the bruising ones from the night before. And somehow, it was hotter than anything else.

“Thank you,” Jamie whispered against his lips. “For everything.”

“Anytime, pretty girl.”

Adam slid his hands down, past Jamie’s waist and hips, and pushed the coat up and out of the way. Grabbing a fistful of both of Jamie’s cheeks through the sheer dress with his large hands.

“Next time I see you, I want to see this ass even fatter,” he quipped.

“Even fatter?!”

“Yeah,” Adam added with a sly smile, keeping his lips tight against Jamie’s and his hands firmly on that bubble butt. “So everyone can hear how loud it claps when I fuck you again.”

His left hand continued to hold onto one cheek, spreading it ever so slightly, while his right slid under the dress now, tugging the panties aside ever so carefully to place a finger at Jamie’s entrance.

Jamie forgot to breathe as Adam slid it into him with ease, now without any resistance from his once-tight hole. In some way, the feeling of it inside him dulled the ache he experienced, as it clenched down onto the intrusion with familiarity.

“Wow, someone still has a hungry pussy,” Adam said. He slid deeper inside, to the second knuckle now, and Jamie melted into the man, who he noticed had his cock hard again.

“Why don’t you stay for a little longer. Not as my paid whore, but as Jamie-the-woman, the girl you know you are.”

Jamie thought for a moment. He had to leave, but this feeling felt so right, too. Adam, sensing his weakness, added, “And I don’t want you using this little clit again. You’re going to make excuses to avoid sex with your wife. It’s only your pussy from now on.”

He slid deeper in, and Jamie accepted it, both his body and mind. He needed one last fuck, one last reminder of who he was now as Adam’s finger felt perfect inside him.

So he unbuttoned his coat and let it fall, as Adam smiled, scooping him into his arms. He walked back to the bed with his hard cock bouncing along the way.

By the time Jamie stepped out of the bedroom and into the hallway in Kelly’s black heels, with his hole now thoroughly destroyed and a fresh load leaking out of his torn pussy, the clock read nine-thirty. Kelly’s flight would land in about an hour. He had just enough time to get home, shower, hide the evidence, and pretend none of this had ever happened.

But as he stepped into the elevator on shaky legs and felt it begin to descend, he already knew he’d never delete Adam’s number. Or forget the cock that had so thoroughly conquered every part of him.

*****

Part 11…

Jamie returned to the apartment just after ten-fifteen, the door clicking shut behind him with a sound that felt too loud in the quiet space. He looked around. There were still the faint traces of last night’s wine and his own perfume, but the place looked untouched and exactly as he’d left it in his frantic rush yesterday.

He moved fast, body aching with every step. The silver dress came off in the bedroom, was carefully folded, and tucked deep into the hidden suitcase. The lingerie followed: panties stiff with dried cum, stockings rolled neatly, bra unhooked and silicone inserts removed; he didn’t have time to wash anything. He took off the wig and brushed it, then placed it back inside. Makeup wipes scrubbed away the last of the berry lipstick and smudged eyeliner until his face was boyish again, though pale and tired.

The hot water of the shower eased his sore muscles, but not the deeper throb between his legs, the constant reminder of Adam’s size, Adam’s weight, Adam’s cum still leaking slowly from him even now. And he noticed that the way he stood in the shower had changed. His natural stance felt more feminine, more like a woman, with his weight resting more heavily on one hip as he stood at ease.

Every motion brought flashes: Adam’s hand in his hair guiding him down, the stretch and burn of being filled again and again, the taste of himself on that thick cock this morning, the warmth of Adam’s release sliding down his throat, on his face, then deep in his pussy again. He wondered if he’d walk normally today. If Kelly would notice the way he flinched when he sat, or if the guilt and exhilaration that was warring in his chest would show up on his face.

After drying himself off, he dressed in loose sweats and a plain t-shirt, nothing that would cling to his body or remind him of what he had done. The suitcase went back into the closet, buried under those familiar sweaters.

The Amazon boxes beneath the shelf were stacked for recycling, and the counters were wiped down one last time, too. And finally… Kelly’s black strappy heels. He placed them on the bedroom floor, half-hidden under the bed as if they’d just been discovered and were there all along.

By eleven-forty, the apartment was spotless, every secret hidden again. It was as if nothing had ever happened.

The front door opened at seven minutes after twelve.

Kelly swept in with a rush of cold air and floral perfume, the suitcase rattling behind her. She was in a coat, a gray hoodie, and black yoga pants, and her beautiful blonde hair was windswept from the cab ride over, as her cheeks (despite being tanned) had become flushed from the New York chill. She dropped her bags the second she saw him and launched herself into his arms.

“God, I missed you,” she muttered against his neck, pressing a long, sweet kiss to his lips.

Jamie kissed her back automatically with his arms wrapped around her waist, but the moment their mouths met, his stomach twisted. Those same lips had just been stretched around Adam’s cock hours ago. That tongue had licked up every drop of cum. He tasted mint from brushing his teeth twice, but still felt filthy, and as if he could feel the lingering taste of the man’s seed in his mouth against Kelly’s.

She pulled back, green eyes bright. “You look wrecked,” she added with worry on her face. “And pale.”

“Yeah, I didn’t sleep much.”

“My poor baby,” she cooed. Kelly surveyed the apartment with a slow turn.

“Wow. It’s like you cleaned up a crime scene in here,” she exclaimed. A playful smile tugged at her lips as she said, “Are you sure you didn’t get up to anything bad while I was gone?”

“I just missed you,” Jamie forced a laugh before shrugging. “Wanted it to be nice for you when you got home.” Perhaps it was the tiredness of last night and being unable to overthink, but the lies seemed to come easily, and Kelly appeared unaware.

“Oh, how thoughtful!” she said.

As she stepped into the living room, still muttering “wow,” her eyes landed on the heels peeking out from under the bed. She rushed over and bent down to pick them up, turning one over in her hands. “You found them! Where were they?”

“Under the bed,” he lied smoothly. “Must’ve gotten kicked there when you were packing.”

“That’s funny, I looked under the bed.”

Jamie scratched the back of his neck and muttered, “They were pretty far back there.”

Kelly nodded, accepting the answer as she set them aside. Then she moved back into the living room and said, “well that hopefully shouldn’t be a problem anymore.”

She stood in front of the shelf, the one he’d felt watched by all weekend, and reached underneath, fingers closing around something small. Jamie watched the round swell of her butt in the yoga pants as she bent over, then the jiggle as she returned upright and turned to him.

“Speaking of things going missing…”

She pulled out a tiny black box that was no bigger than a matchbox, with a lens glinting in the afternoon light, and held it up for him. “This is what that warranty slip was for. It’s a camera, isn’t that neat?”

Jamie froze on the spot as she threw it into his hands.

“I ordered it a few weeks ago after my stuff kept disappearing,” Kelly continued. “Set it up right before I left and connected it to my phone so I’d get motion alerts. That way, I could see where I left things. Pretty smart, huh?”

Jamie’s blood turned to ice now, and his throat closed, and he felt as though he might pass out. “Alerts?” he replied weakly.

“Yeah, it pinged me all weekend,” she went on, voice light, almost conversational. “I think it’s too sensitive. Every time there was movement, I got a notification. New recordings saved to the cloud or something like that. I never had a chance to watch them because I was so busy with the girls, but…”

She tilted her head, studying his face with that knowing look he’d always been a little afraid of. The same one she had thrown his way before she left for the trip.

“Anything you want to tell me, babe?” she asked.

The room tilted. He saw it all in a flash: the camera capturing him in lingerie, posing, leaving for the hotel, coming back wrecked and desperate. Every transformation, every guilty moment preserved in high definition. Every image of him bent over with the camera held high for Adam, his cock straining with want.

He opened his mouth. Closed it. The truth sat heavy on his tongue, stuck and unable to come out.

Kelly’s smile softened. “Think about it. I’m gonna take a shower, this plane funk is real…” She kissed his cheek and headed for the bedroom, peeling off her coat as she went.

Jamie stood frozen with his mind racing. Delete the footage, or lie, or confess: how the hell was he getting out of this? For all his cunning and belief he’d get away with it all, this was now the end. Surely, he thought.

“Jamie?” she called from the bathroom, the water already running. “Can you grab my clothes for the hamper?”

He moved on autopilot while his thoughts spun out of control. The bathroom was steamy as he gathered the pile she’d left by the shower door: hoodie, yoga pants, bra… and finally the tiny black thong. The same one that was in the photo she’d sent of her bent over in the Miami hotel.

As he grabbed it, he dropped the thong out of shock… it was soaked, completely drenched, the fabric sagging heavily. The shower continued to run as he lifted it again off the floor, and the scent hit him: sex. It was unmistakable. Then he saw it as he looked inside. Thick, creamy white streaks all over the front gusset of the panties, still wet… it was unmistakably cum.

His breath got caught in his throat while the humid steam curled around him.

Kelly peeked around the shower curtain, water cascading over her bare shoulders and down those full breasts as a stream traced the curve of her hips and ass. She met his eyes with a calm look.

“Anything you want to tell me?” she asked again, softer this time with almost amusement in her voice.

Jamie stared at the panties in his hand, then at her body. She was glowing, flawless, the same way she always did after having sex. And he realized, she was marked by someone else just like he was. The parallel hit him.

There was nothing to say.

“No…” he said, quietly.

Kelly’s smile widened, slow and wicked. “Good.”

She nodded toward the pile of clothes. “Put those in the laundry, then go wait for me on the bed,” she grinned beneath the running water. “Naked. Just the heels, those black ones I wanted, the ones you stole from me. They looked good on you.”

Jamie’s heart slammed against his ribs.

She ducked back behind the curtain. “There are some deep parts of me this shower can’t reach,” she called, voice echoing off the tile. “I’m going to need your tongue for those.”

He stood there a moment longer with the cum-stained thong still dangling from his fingers, and the weekend flashed before his eyes: Adam’s cock down his throat, Adam’s load painting his face, Adam’s loads still deep inside him. Adam’s promise of Chicago, too. And now this… Kelly had experienced it all too, Jamie realized, because she had always known who he truly was, and what he was willing to do. The camera finally proved it. The only question was: how much of this trap was planned?

Before he could leave, Kelly poked her head out once more. “And Jamie,” she whispered as water ran down her face. “No more secrets.” Then, she ducked back in.

He walked slowly to the bedroom, dropped the clothes into the hamper, and stripped. Standing naked in front of the mirror, he no longer saw a man. He was still that woman from last night and this morning, even without the makeup and lingerie. Her image burned.

Leaning over in the nude, he placed the heels under his feet. They strapped on easily, the leather now familiar against his ankles. Then, he sat his bare butt onto the bed and fell back onto the cool sheets, naked except for the heels as they dug into the mattress, while his legs slightly parted and cock tried desperately to stir despite everything. But it couldn’t get hard. Instead, his hole twitched with the memory and a rewired need to be filled when aroused.

The ceiling stared down at him. He heard the shower shut off, and then the soft pad of wet feet before the rustle of a towel that fell to the floor. Jamie looked up from the bed.

Kelly appeared in the doorway, naked, with her golden hair damp while her skin flushed red from sunburn and the heat of the water. Her breasts bounced with a wet sheen as she moved to place the towel into the hamper, and during so, Jamie stared at the clear mark of a handprint imprinted onto her ass cheek. Then, he watched as a viscous trail of white ran down her inner thigh.

“How big was he?” she asked, calmly.

Jamie swallowed down his saliva and said, “Eight or nine inches.”

She smiled. “Mine too. Did it hurt?”

Jamie nodded.

“Good,” she whispered.

Kelly moved to her suitcase and began rummaging through it. “I got something in Miami for you. Thought it might help, and also go great with all those slutty outfits you wore.”

His heart continued to beat as fast as a drum as she pulled out a small bag, tied with a drawstring, and heavy.

Then she slowly climbed onto the bed, straddling his chest with her knees and pinning his arms to the mattress. Her scent enveloped him all at once. It was soap, arousal, and the faint musk of another man still there, hovering above his face. It was now an identifiable smell to Jamie because it, too, was still on him.

She smiled and threw a leg over his body, now facing away from him. Kelly began to untie the bag, and Jamie could hear the sound of plastic and metal, though his view was obstructed by her large ass, now coming closer to his face as she bent over. From this vantage point, he could see her pussy: wrecked and leaking even now, a steady amount of cum. And as she bent even lower to the point her asshole now rubbed against his face, he could breathe in her intoxicating aroma.

Her hands were clasped around his cock, still desperate to get hard but failing. He could feel her twist and contort his shaft and balls into an awkward position, then the sound of a loud snap.

When Kelly moved at his side to straddle him again, he looked down to see that his cock was now bound in a tiny, plastic, pink chastity cage. No bigger than an inch at the most.

Kelly dangled the key to the lock, then threw it into the hamper with the rest of the laundry. “There’s going to be some new rules around here,” she said with a smile, pinning his arms again with her thighs as she faced forward once more.

“Does your man live in New York?” she asked gently, stroking his hair between her thighs.

‘My man,’ Jamie thought. He shook his head.

“Where?”

“Um… Chicago,” he muttered, embarrassed.

“Well, we’re going to make sure you visit him again. At least once a month, a whole weekend just like this one.” She leaned in to kiss his lips and uttered, “Because I think we both want this again. Deal?”

Jamie thought for a moment. More sex with Adam, as rough as before, but now with his little clit bound in a cage. What would Adam think? He’d probably love it, Jamie realized; he’d probably rub his huge throbbing manhood all over the cage to put him in his place before fucking him just like he did last night. But Kelly… their marriage…

“What about us?” Jamie asked, the worry in his voice causing it to vibrato.

“I love you… You love me. We’ll still have sex, Jamie-baby, just not with your cock anymore. You’ve always been better with your tongue anyway.” She took in a deep breath. “You’re not the only one who hid a secret. I wanted to experience something big for a very, very, long time. I don’t think I can go back. Just like you can’t.”

Jamie understood. There would be no divorce, no messy fights, just an understanding of what they both were. No longer a secret: they were equally sluts for men with big, bad cocks. He nodded. “Deal.”

She looked down at him, her hands on her hips and green eyes glittering.

“Open,” she said simply.

Jamie parted his lips.

“Oh, how I wish I could’ve seen you with him in those cute little outfits…” Kelly moaned as she scooched closer.

Suddenly, filled with confidence, he told her to grab his phone. Her brows lifted, but she complied. Using his face to unlock the phone, Kelly followed his instructions and scrolled to the folder containing videos until he finally heard the audio play.

‘What would your wife think if she saw this, Jamie?’ the unmistakable voice of Adam said from the speaker above him. ‘Her husband on his knees, swallowing cock like a pro.’

“Wow,” Kelly breathed. “That’s a big dick. And look at your makeup!”

Jamie felt a strange sense of pride and watched as his wife slid a hand between her legs. He saw how her pussy grew wet as the sound of the recording played out: the gags of him from hours ago; the grunts of Adam. And now, the slicked sound of Kelly’s pussy too, wet with desire and cum.

As she lowered herself, closer and closer onto his waiting mouth, he realized, for the second time today, he was about to swallow another man’s load. He wrapped his hands around her thighs and pulled her closer; she squealed with laughter and let the phone tumble to the bed. It continued to play, as Adam’s voice said: ‘Such a good girl.’

This time, he didn’t feel a shred of guilt at all as he tasted the bitter saline thickness of cum, because he realized, neither did Kelly.

The End.

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