Can’t Please Her
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Gender: Pre-op Transgender
Jessica was taller than most women I knew, but more womanly than any other. Stacked, her height wasted no curve, giving her an amazing spankable, chubby butt. She had thick, luxurious hair that she wore in an impromptu bun of gold. All night her eyes allured me with a “come hither” quality. She had candy pink lips and a tongue made of promises.
We had the greatest of nights. We’d played some old video games for maybe two hours, sharing beers and old stories about hobbies, and mutually admiring our niche tastes in music. Already, we felt like an intimate couple, an incredible match. We shared an incredible dinner at this Thai restaurant she knew. We both had such identical tastes, even in curry, that I felt like I’d finally met a perfect match. Even just going out with her, and just holding her hand gave me a sort of tingly thrill all over. Her hands were way bigger than mine, but the two felt just right pressed together.
We were both pleasantly full of curry and loaded on Singha by the time we got back to her apartment. She told me to sit down and said she had a surprise for me. I did, and so she stood in front of me, towering over my short, skinny seated self.
“What’s the surprise?” I asked her. Somehow I sensed what was coming, though, like electricity in the air. My loins stirred to life like a science fiction creature, stiffening and rising, confined against my pant leg.
Jessica leaned in, her voice husky and promising with hot breath in my ear. “My roommates are out-of-town…”
I turned to make eye contact and we fell into a passionate lip lock. She straddled me, let her hair down, and thrust her round, feminine tush on top of my cock through both of our jeans. I grabbed her shoulders– more solid than most other women I’d been with, but all statues of goddesses are sculpted from stones heavy, firm, and beautiful. I held Jessica closer. She looked back, our eyes met, and her wet tongue slipped into my mouth.
When she pulled away, my hands slipped down from her shoulders across her back. I lingered at her hips for a second, shyly, while I felt her breathing in concert with me, then continued down to her butt where I squeezed and held tight. Her ass was amazing and so cushiony-big, like no woman I’d ever been with before. I pinched it.
My lover moaned eagerly and started grinding her hips down into mine. “Are you getting hard for me?” she asked.
I nodded. I was already completely rock hard. “Yeah, baby, yeah…”
This hot transwoman ground down on me hard and made some kind of bemused sound like she was laughing or scoffing that made me think she wanted it bad and was losing control. She lifted her butt up, turned around to dry hump me reverse cowgirl style right there on the couch. I gripped eagerly down on her plump booty meat in those jeans and spanked her with both hands as hard as I could, repeatedly, to encourage her. She moaned a little harder and rubbed her rear against me a little harder every time. Her booty jiggled deliciously under every strike of my palms on her pockets.
My erect cock throbbed against her. For a second I thought I was going to jizz in my pants, but I found a rhythm of deep breaths that made it work. With one hand I grabbed onto the waistband of her jeans and starting pulling down on them, bucking my hips up into her, and with the other I wound up for the mother of all spanks.
“Ooh!” she cried. She tried leaping up from my lap, but I pulled her back down from her waistband onto the throbbing lump in my pants.
“Oh, honey, oh honey…” she moaned, still squirming from the spank, still swirling her ass on me through our jeans. I felt it then, something hard like metal rub into me for a second. Jessica turned, grabbed my face and kissed me long and hard. I didn’t hear her undo her pants, but she stood up off me finally, rubbing her butt and shedding her jeans in the same motion.
There was her wide, beautiful butt in cute, semi-see through cheekies with a ruched back and tiny, pink bows at her left and right hip. I reached up to grab one of those gorgeous moons, but without looking back she swatted my hand away. I blinked and saw what it was that had pushed into me while she rode me: the end of a metal butt plug beneath her underwear. Wrists at her hips, she walked one step, two, out of her jeans, swaying her hips. I sat mesmerized with my hand on my groin watching that juicy booty wiggle ’til she reached a door and leaned on it.
Without turning around, standing to show off her incredible curves with her back arched, she asked, “You wanna see my bedroom?”
“Yes!” I shot up to my feet, clearly ready to plow into that.
She remained more controlled, opened the door slowly, and sashayed into her room saying simply, invitingly, “Take off your pants.”
My pants were already half down. I stumbled and stood in her doorway. Jessica was bent over her bed, pulling out her plug. It was a steel toy about the size of my cock, but visibly thicker, bulb-shaped. She set it on a nearby stand with a set of dildos whose size flabbergasted me. They must have all been anywhere from 8-11 inches. My todger flexed, but felt like it was cowering.
Jessica turned around to face me and her unfastened bra slid off, revealing her mountainous, proud bosom. She put her arms around my shoulders and looked down at me. Our eyes met. She made a little face and said matter-of-factly, “You’re short.”
I didn’t think this what how she meant it, but my eyes immediately darted to the little table of dildos twice my size and bigger. I blushed a little and giggled nervously. I tried to stay debonair and grabbed her by the hips to show my confidence. “It’s alright, I like tall women.”
She leaned down and whispered in my ear, “Touch me.”
I took one of her breasts in each of my hands, feeling first where they landed upon her hard nipples and caressing her sensitive areolae. I spread my fingertips their full span across her gorgeous flesh, and as I let them wander I stood on my toes to give her a kiss. Just beneath her bosom, my thumbs traced two entrancing bands of sacred, scarified flesh.
“You’re so fucking sexy,” I whispered. I ran my fingers through her gorgeous fucking hair and felt as much as heard her wanting sigh, like from the same lungs. Slowly, I lowered myself from her lips, breathing one controlled, slow exhale down Jessica’s neck, and started making out with one of her big, amazing tits.
Again, she moaned, louder. There was something in her need, something corrupting that spread like an erotic web of milky heat throughout my brain. My naked cock touched hers, standing out of her panties and erect, or getting there despite herself. Rubbing them together, hers was clearly bigger. I felt it dig in against me. I imagined thrusting my hips at her bountiful cleavage.
Holding her tight, I flicked my tongue quickly a thousand times like a serpent across her nipple. She went, “Mm, yes,” and I just about lost it. I had only enough restraint left to nibble rather than chomp on her teat. But I had to have more.
Her push at my shoulders interrupted, parted us. She looked down at me, stroking her bitten nipple and pursing her lips. “I know what you want,” she said.
Like she’d read my mind, she got down on her knees, pushed me against the wall, and took my hard length between her tits. Only, then something happened.
“Where’d it go?” Jessica asked. My entire hard length had disappeared between her massive mammaries. She spread her boobs apart and went, “Peekaboo!” Then closed them back together over my cock again laughed.
My heart dropped into my loins and the hot web in my brain spread throughout my entire body, making my toes and fingertips tingly. I trembled with lust and embarrassment. She had corrupted me completely. I thrust my hips, totally devoid of thought, entirely given to my carnal urges. Whenever I changed the angle and thrust hard enough the head of my dick peeked up, she swooped down and kissed it, trying to get her lips around it. There just wasn’t enough for her to suck like that.
I couldn’t take it anymore. I had to be inside her. I squirmed, trying to get out of her cleavage, then tapped and lifted at her armpits. She stood over me once more. She had gone soft, and her jewels dangled cutely between her legs.
“What is it?”
“Oh…” Jessica spun, wiggled her butt at me, and spanked it. “Does somebody want this ass?”
“Yes,” I said.
Demurely as possible, she asked, “Are you gonna fuck me hard?”
“Yes.” I had run out of words.
Jessica sprawled forward onto her bed, lying on one side, and picked a small bottle of lube off an end table. I shucked my underwear off my feet and laid down behind her, rubbing myself, trying and failing to control myself against her influence. She reached back and grabbed me, lubed up my cock like a mad woman with short, rapid pumps of a fist filled with cold and wet. There was this loud, squelching sound in her lubed-up palm every time her tight fist stroked just a little too long and slipped off my dick.
I pulled her body into mine and felt the heat of her tall buttcrack against my hard tool. In my excitement, I fumbled it at her ass, trying to get it in.
“Everything okay back there?” she asked.
I grunted with surprise and told her, “Sorry, I’m not used to–”
“It should slip right in.”
I blushed, then I spanked her again, even harder for all my want and frustration.
Jessica rose up, rubbing at her butt. “Ooh, honey… let’s… try another position.” I got out of bed with her as she stood at the edge of the bed and planted one foot on it, spreading her ass wide. “How do you like that view?”
“Very much,” was all I could say.
“Come and get it.”
Well, I tried. But for one thing, she was so tall that when she stood like that, her ass was very nearly pressed on my chest. No standing on my toes was going to help. I put a foot up on the edge of the bed, too, trying to get it in, but it was one of the most awkward positions I’ve been in. My cockhead poked at her behind and I managed to get it between her wide, wonderful ass cheeks, but little more. I tried grabbing her shoulders to pull myself into her, but it didn’t quite work. I tried to cover it up by turning it into a massage.
“What are you doing?” she asked.
“Just… Preparing.” I kneaded my thumbs into her upper back in a circular motion, to show I was serious about massage.
Jessica didn’t buy my bluff. She gave me a bemused, sceptical look. “Let’s try this.”
She laid down on the bed, flat on her stomach, and once more spread wide in anticipation. Her hole was already stretched out by her plug, and eagerly needed me. All my desire had built up inside of me, it was like a dam suddenly burst. I couldn’t hold back any longer. I got on top of her without a moment’s hesitation, pinned her down, picked my hips up, and dropped them down into her, burying my dick in her sweet, open hole. Her sphincter contracted around the head of my member, squeezing it tight. Her powerful ass flesh squeezed my entirety. I thrust in and out with abandon, closing my eyes, grunting, clenching my teeth, just letting her have it, letting loose that web of hot corruption she’d put in my brain for a few minutes, completely lost to the world in the act.
When I lifted my head from her back and looked, though, Jessica was busy playing a game on her phone. She bumped her butt back at me a couple of times, but then it was like she’d just given up trying to hump me. I knew I wasn’t exactly deep in her, barely past her sphincter if past at all, but could I have really been that bad? Then it hit me… with that plug, she’d basically had me inside of her all day without a problem. Maybe her plug was even bigger than I’d first guessed. She genuinely needed something bigger. Something the size of her toys… something more than twice my size.
“Did you get it in?” she asked, not even looking up from her game.
I clenched my teeth, tried my signature hip-drop, thrust as far and as hard as I could.
“Hurry up and finish.” Jessica sighed. “I got shit to do.”
Oh, shit. That did it. That hot, tingling web in my head, in my veins and body, was hers and I was her fly in it, helpless against the command in her voice. I felt a familiar, urgent twitch throughout my loins, pulled out, and came all over her lower back.
Jessica made some sort of noise I couldn’t identify and finally looked up from her phone at me, at her back. “That feels so weird… it’s so wet… y’know, you didn’t have to pull out. It’s not like you can get me pregnant.”
“S-sorry,” I stammered. “Old reflex.” I laid down on my back next to Jessica, spent and smiling despite myself. A bit of my semen dripped onto me.
My hot transsexual lover– perhaps no longer so in love with me– crawled forward a bit and grabbed a tissue from an end table. She tossed them at me, asking me to clean her up. I obeyed.
As soon as she was clean, Jessica got up, her hand covering over her own flaccid member, and grabbed her biggest toy from off the other table. I looked up at her pathetically. She gave me a wicked smirk and idly started sucking on the head of this big, black, basically foot long rubber dick. She deep throated it like only the last inch was a nuisance and came up for air, a strand of her saliva strung between its head and her lips.
My flaccid penis twitched with envy and impossibility.
“Good luck getting laid with that three-inch dick,” Jessica told me. “I mean, I shrank myself with oestrogen, and it’s still bigger than yours.”
The hot web all over my insides turned to a numbness. “W-will I ever see you again?”
“I’ll be honest,” said Jessica, still wildly horny and idly nuzzling at the giant dildo in her hand. “I don’t ever want to see you again.” She put an (I thought unnecessary) emphasis on YOU.
“W– w– I– can’t we just be friends?”
She made a patronizing frown. “I don’t wanna get your hopes up, little boy.” After a second she added, “Actually… I think I’ll just stick to women from now on.”
I tried to speak, but nothing came out. I thought I might cry.
“Here,” said Jessica. Before I could react, she threw a strap-on at me. “I think you need that more than I do. Now, excuse me… but you can go.”
Into the bathroom she went with her toy, closing and locking the door because, no, she did not want me to watch. I laid there in numb shock until she started moaning aloud with real pleasure, probably with the whole toy inside her, reaching places I could never hope to without… well, without the toy she had just given me. It was true.
I got dressed and decided to slink out as quietly and as quickly as possible, hiding her gift to me in a bag so nobody on the street would guess. The sound of her excitement followed me out the door and into the night. The erotic, hot, or numbing web passed out from my dizzied innards at the first touch of a chilly wind and shame rushed in to fill the gap. It had seemed like such a perfect night, with such a perfect woman, but my wishes and expectations had gone too far, let me dream too much, and now all I had imagined had come toppling down into another pile of romantic rubble. I guess we weren’t such a perfect fit after all.