Midlife Cuckold Chronicles 1
By Runtz3.
Allison always enjoyed the stolen glances at her large breasts from Devin when he was around, and today, he had given her extra attention, and it was obvious why. When Allison went to grab her swimsuit, the only one she could find was her thin white bikini with no padding. She had only worn it a couple of times before realizing how naughty it looked on her.
She had other swimsuits, but for the life of her, she couldn’t find them, and even considered not going out. Still, there was something in the back of her mind, almost compelling her to do it, a spike of adrenaline and euphoric pulse of endorphins at the thought of prancing around in her barely there swimsuit in front of her daughter’s handsome boyfriend was too much to ignore. She tied the top around her neck; even though it was dry, her large nipples were easily seen, but she knew that as soon as she got wet, it would become indecent for public use.
Devin couldn’t keep his eyes off of her, and she felt that twinge of naughtiness that made her feel young again. Allison was dangerously close to 50, but over the past several months, she had noticed an increase in her sexual appetite, a hunger she was painfully aware her husband was unable to satisfy.
Her lust kept her awake at night; she found herself reading trashy wine mom smut, and seeking out public sexual thrills by wearing tight tops, bending over seductively, leaving more buttons undone on her blouses, and wearing sexy panties and bras in her everyday life.
She tried to chalk it up to a premenopausal hormonal shift, but she knew that wasn’t the only factor; she could pinpoint the moment this fire began. Nearly a year ago, her husband texted asking her to email him a file from his home laptop. She wasn’t prepared for the flurry of tits, ass, and pussy that greeted her upon opening Ethan’s computer. But what burned in her psyche was the monstrous enormity of the cocks she saw. She knew men came in different sizes, but had no idea how big they could get, and compared to her husband’s handful, they seemed cartoonishly large.
She watched Ethan later that day plop down on the sofa and open his computer. His face went pale, and he quickly shut it down, looking over at his wife. They shared a knowing look and had a brief, yet profound conversation that ultimately opened them both up to their desires.
Devin and Sarah shared some hushed conversations. A few unsuccessful hidden glances in her direction. And a pained expression on Devin’s face. He was a striking young man, 23 years old, with an athletic build. He was the walking definition of tall, dark, and handsome. Allie noticed the bulge between his legs the first time they met, and then a few months ago, she saw him coming out of the pool. His baggy swimsuit clung to him, making Allison go weak in the knees and burn an undeniable image into her mind.
Allie allowed the flow of the pool and the low wisp of the wind to carry her float from one end to the other. Her large-brimmed hat and dark Chanel sunglasses shielded her eyes enough to give her a sense of freedom as she watched Devin incognito. Her top had gotten just wet enough to highlight her tits, her large natural breasts spread across her chest with a weight of mature sexuality. She glanced down, checking herself out. She could easily see the sensual bumps around her soda can-sized areolas and, for a moment, wondered if she had gone too far, too revealing, even in the privacy of their backyard, but that thought was quickly arrested.
“Who the fuck cares?” Allie whispered to herself; she was fully embracing her age, her desires, and her body.
Sarah giggled from across the pool, then made her way up the stairs, grabbed a towel, and took it to Devin, who quickly wrapped it around his waist as he stepped out. They both dried off a bit and dipped inside with a quick announcement and one final look from Devin.
Just minutes after Sarah and Devin had gone inside, Allison made her way over to her towel draped over a chair near the window to Sarah’s room, her 34-DD breasts jiggled and rippled with the motion. She caught her reflection in the window.
“Not bad, Allie.” She had worked hard to lose weight and get in shape over the past couple of years, dropping over 40 pounds. But, gone was the petite girl with c-cups of her youth; the person looking back at her was a voluptuous woman with soft double D’s. She blushed a little as her hands trailed up her body and she lifted her breasts high on her chest, remembering when they used to sit that high. She chuckled to herself, looking at how sheer her top had become.
She was lost in vanity when a movement caught her attention–something in Sarah’s room. The room on the other side of the window suddenly came into focus, and curiosity got the better of her. And what she saw shatter her world.
Sarah was on her knees in front of Devin, who sat on the edge of her bed, legs spread. Allison’s eyes widened as she took in the sight of Devin’s cock–massive, thick, and achingly hard–resting against Sarah’s lips like a summer sausage. Her daughter’s hand wrapped around the base, her mouth slowly enveloping the tip.
Sarah was a grown woman now, her 22nd birthday just a memory on Facebook. She and Devin had been dating for a while now, and Allison suspected it had become sexual, after all, Allison was the one who took her fit and trim daughter to get her a prescription for birth control when she first turned 18.
Allison always wanted an open relationship with her kids. She led the way by talking with them about their bodies, answering their questions directly, and having “the talk” with them at an age that made her husband a little uneasy.
Allison watched with excitement and a sense of pride, seeing how her daughter worked Devin’s cock. And still, she knew she should look away. This was wrong, but that made it even harder to leave.
Devin’s head tilted back, his mocha hand tangling in Sarah’s blond hair as she began to move, taking little more than his plum-sized head into her mouth. Devin lived in the area, and Allison knew his family; his mom is a gorgeous black woman who reminded her of Angela Bassett, and his father is a former NBA player of mixed ethnicity. Devin was more light-complexioned, like his father, with bronze skin, and stood at a tall 6’4.
The way Sarah’s lips stretched around his girth was hypnotic, and Allison found herself leaning closer, her eyes fixated on Devin’s girthy, veined cock. She watched as Sarah’s tongue swirled around the shaft, her hand stroking what her mouth couldn’t reach. Devin groaned loud enough she could hear it through the window; the sound sent a shiver through Allison, landing deep inside her womb.
“Damn baby, you’re so hard today.” Sarah praised. “She really turned you on, didn’t she?”
“Sorry, but damn, your mom is fine.” He confessed
Allison gasped, hearing them talk about her like that. A warmth built between her legs, a tingling sensation that made her shift uncomfortably, her nipples enlarged, and her hand toyed with the top of her bikini bottoms. She pressed her thighs together, trying to ignore it, but the image of Devin’s cock, so much larger than her husband’s little penis, was seared into her mind.
“I’m sorry, I’m not trying to frustrate you, just give me a little more time.” Sarah pulled back slightly, leaving a string of saliva connecting her lips to his tip. “It’s okay for you to think about her; she’s my mom, but she looks like a porn star.” Devin huffed as he sat up, watching Sarah slide her hands up his cock as she sucked his balls.
She grinned up at Devin, her voice soft but audible through the window. “You like that?”
“Fuck,” Devin growled, his voice heavy with desire. “You know I do.”
He grabbed her by the shoulders, pulling her up onto the bed with him. Allison’s heart raced as she watched them kiss passionately, Devin’s hands roaming over Sarah’s body, squeezing her breasts through her damp swimsuit. Sarah moaned into his mouth, her hips grinding against him. Allie’s eyes widened again, seeing Devin’s massive cock protruding up between Sarah’s legs, resting on her ass.
She had never seen a man like Devin in real life before, never imagined someone could be so… powerful. Her fingers tightened on the towel as she watched him yank Sarah’s top off, exposing her perky c-cup breasts. He wasted no time, his mouth closing over one nipple while his hand cupped the other.
Sarah’s head fell back, her chest rising and falling as Devin’s tongue worked its magic. “Devin. Please,” she gasped, her hand reached behind her pressing his cock between her bubble butt cheeks.
Allison’s nipples ached to be touched like that. She bit her lip, her mind racing with thoughts she shouldn’t be having. But the sight of Devin’s large hands on Sarah’s body, his thick cock pressing against her ass, “My god, he’s huge!” She thought. The scene was intoxicating.
Devin slid a hand between Sarah’s legs, his fingers teasing her through the damp fabric of her bikini bottoms. Sarah whimpered, her hips rocking against his touch. “I want to taste you,” he murmured.
He pushed her gently onto the bed, hooking his fingers into her bottoms and pulling them down in one swift motion. Allison’s face grew flushed as he dipped his head between Sarah’s legs, his tongue finding her in an instant. Sarah cried out, her back arching off the bed.
The heat between Allison’s legs was undeniable, her body quivering with lust. She couldn’t tear her eyes away as Devin devoured Sarah with youthful abandon, his large hand gripping her tits while he sucked her clit and slid a finger deep inside her. The sounds coming from the room were enough to make Allison wonder if they even cared she could hear them. Saarah’s moans and the creak of the bed as she writhed beneath him, she would have heard them even if she wasn’t right outside the window.
Allison’s hand crept under the fabric covering her sex, her fingers brushing against her sensitive clit. She shouldn’t be doing this; it was wrong on so many levels, but the sight of Devin’s strength, his raw masculinity, was too much to resist. Her fingers slipped further, parting her folds with a soft gasp.
“Devin! I’m so close!” Sarah panted.
He didn’t slow down, his tongue working faster, harder. Allison mirrored the rhythm with her own hand, her fingers circling her clit in tight, frantic motions. She was panting now, her body trembling with the force of her arousal.
Sarah whimpered, losing herself in the pleasure, her body convulsing as Devin lapped at her with relentless intensity. Allison’s pleasure crested her orgasm, washing over her, as she muffled a moan with her free hand, her orgasm dripping down her leg, shaking as she leaned against the wall for support.
Devin finally pulled back, smirking up at Sarah. “I want you, please let me put it in you. You’re so fucking hot, Sarah. Please, just the tip. I promise!” He pleaded with his girlfriend as he lifted the log standing hard from his body and rubbed her wet opening with his fat cock head.
“Just the tip,” She gave in. How could she keep from impaling herself on that thing? Her mother wondered. Allie watched with lust-drunk eyes as he rubbed his dick around her daughter’s clit and pussy. She nearly felt it as he pushed the fat head in Sarah’s cunt, and watched as her daughter’s eyes rolled back, followed by a grunt and pained expression.
“I…I can’t… It’s too big!” Sarah sighed, pushing away from him. “But, I’ll make it up to you.”
Allison watched as Sarah pushed Devin onto his back and sank, brushing her perky breasts across his thick cock. Devin gripped the sides of her breasts, thrusting his powerful dick fucking her c-cup tits.
Allison couldn’t stop herself from rubbing her pussy again; the sight of Sarah tit fucking Devin was driving her wild. She watched, imagining it was her on that bed, her large tits bouncing on that massive cock, feeling every inch of him, her mouth stretching to accommodate his huge head in her mouth.
Sarah’s breasts are much smaller than her mother’s. Devin easily spilled out the top, allowing her to suck his cock. He was getting close. He grabbed Sarah’s head fucking her mouth, but she couldn’t take him very far.
Allison had never seen a cock like this before. Watching this poor boy with this raging erection was stirring something inside her. His dick was throbbing and his balls achingly full awakened an instinct to help him, a motherly love to care for him. His cock was straining in a way that seemed like a medical emergency – his cock was so hard it was causing him physical pain.
“That’s it, a little more!” He grunted, grabbing the back of Sarah’s head and pressing himself deeper inside her throat. Allison shook as she watched, never having felt a cock in her throat like that; her husband’s little penis was far too small for such an invasion. Sarah gagged and tapped out. Devin pulled his cock out and stroked it till he finally erupted in a flow of thick white cum.
Allison couldn’t believe how much came out of him. His cum was thick and white, like a bottle of Elmer’s glue had been poured out on her daughter. So different than her husband’s teaspoon of watery, nearly clear cum she was used to seeing. His face showed signs of relief, but something in his eyes, the way his mouth curved into a slight frown, made Allison certain he needed something more; he needed a proper fuck.
Allison recomposed herself, ducked away from the window, and headed inside to her bathroom to freshen up.
Minutes later, Devin and Sarah had headed out, while Allison stood in the kitchen, having changed into some shorts and a t-shirt, her fingers trembling slightly as she poured herself another glass of wine. The bottle was nearly empty now–her third glass, maybe fourth? She wasn’t sure. Her mind was still racing, replaying the scene she’d just witnessed.
Devin’s massive cock, Sarah’s lips wrapped around it, the way Devin sucked her clit, and the way he throbbed. She was obsessed and couldn’t stop thinking about it. The heat between her legs hadn’t subsided since she’d touched herself earlier, and now, with the wine coursing through her veins, she felt uncontrollably alive.
“I… I did that to him,” She smiled, reveling in the idea that Devin found her sexy.
Maybe it wasn’t what she thought; maybe it was the angle, the lighting in Sarah’s room that made him seem so big. Obviously, he was much bigger than her husband, but he couldn’t really be THAT big, could he?
The sound of the garage door opening snapped her out of her thoughts. Ethan walked in, his face lighting up when he saw her.
“Well, hey there, hot stuff!” he said, leaning in to kiss her cheek. They’ve been together since their second year of college. Ethan was a staff accountant and did well financially; he was a good provider and was the stable one in the relationship. He wore khaki pants and a dress shirt with a character tie for a splash of whimsy. He quickly sensed something was off. “Is everything okay?”
She stepped back, her heart pounding. “Come with me,” she took him by the hand, leading him down the hall.
He raised an eyebrow, clearly confused, but followed her without question. She led him down past their bedroom and into Sarah’s room. The bed was neatly made, but Allison could still picture the scene that had unfolded there earlier.
“What are we doing?” Ethan asked.
“Take your pants off,” she demanded, leaving no room for argument.
“What? Why?” Ethan stammered, he blushed, and pushed his wife away as she reached for his belt.
“Please,” she pleaded. “Just… just do it. Ethan, I’ven’t asked for anything like this before. I know it’s weird, but please just do it and don’t ask questions.” Her body was trembling, just summoning the courage to be this forward was wreaking havoc on her. “If you do this for me, I’ll do that thing you’ve been wanting. The… free-use thing.”
That day, Allison found the porn on his laptop, and it pried open a new season of life for them. As Ethan looked over at his wife, they both knew what was going on. He sat frozen, unsure of what to say.
“It’s okay,” Allie calmed. “I honestly don’t care that you watch porn. I am not surprised, and I am not hurt that you do it.” She shared. “But, please don’t keep secrets from me.” Since that day, Ethan would hesitantly approach her, “Is it okay if I watch something?” He’d sheepishly ask every time like a child asking for a cookie. Allie would answer him with a cheerful, “Of course.” And he’d trod off to their bedroom.
At least up until three months ago, Allie started to enjoy the feeling of that power, the power to approve or deny her husband’s sexual desires. And then it happened one too many times in a row, they had sex, Ethan finished quickly, as usual, and didn’t even offer to do anything for her. So, in frustration and feeling empowered, the next day, Ethan asked if he could watch something, and with a stern, cold voice, she simply responded. “No.”
“No?” He kind of chuckled, assuming she was kidding.
“No. Not tonight.” She stated more firmly. “If you want to watch something, then do it here, with me.” She lectured. “Besides, if you show me what you like… I might just do it.” Hoping Ethan would reciprocate the offer. Ethan gingerly sat beside his wife and scrolled to a porn site. He was awkwardly aware she was watching him, not just the screen, and he just clicked on the first video, embarrassed to search for his usual flavor of smut, afraid she’d judge him. But, it just so happened to be a “free-use” scenario. And Ethan admitted he’d enjoy doing that, and, sitting there together, she took the laptop and ordered some dresses as shown in the videos.
“Really? You mean it? Will you wear that milkmaid dress and do your hair and makeup like a tradwife? You’ll let me take you anywhere and any time I want? You’ll really do it?” Ethan was excited.
She nodded yes, “All day tomorrow, I’ll dress up, and you can take me anytime you want. But you have to do this for me first.” Her pulse quickened as she watched him unbuckle his belt and slide his pants down his legs. Her eyes narrowed as he revealed himself, his small, thin dick standing at attention. It was nothing like Devin’s fat cock. Her excitement waned as she looked at his pitiable penis.
“No panties and no bra.” Ethan’s brain was tingling just thinking about it.
Allison huffed, her cheeks burning. “Fine, now I want you to sit on the bed and… touch yourself. I want to watch you jerk off while I watch through the window.” She finally told him.
Ethan hesitated for a moment, then shrugged. A voyeur fantasy is pretty common, he just didn’t know she was into that, he reasoned.
He sat on the bed tossing his Daffy Duck tie over his shoulder, and began stroking himself. His movements were awkward at first, but soon he fell into a rhythm that seemed natural to him. Allison watched for a few seconds, disappointed with her husband’s dick, before walking out of the room.
She hurried out the back door and to the window. Her focus was entirely on the show happening in the window to Sarah’s room. She tapped on the window, letting Ethan know she was in place.
Allison had never watched Ethan masturbate before; she had caught him a couple of times, but he quickly stopped once he saw her. But, this time she got a good look, and she giggled to herself, noting he was just using the tips of his pointer, middle finger, and thumb, and still his penis looked like a nub compared to the magnificent cock she had seen earlier.
He looked over, giving her a sly smile, his fingers moving steadily along his meager length. He closed his eyes and thought about his wife dressing in the milkmaid dress they had bought, getting more and more worked up.
But Allison was feeling something very different; it took her a moment to name it, and once she did, she couldn’t look at Ethan the same. The feeling was embarrassment; she was embarrassed by her husband’s dinky dick, and embarrassed at how little it did for her. She knocked on the window.
“Lean back, let me see you more.” She directed. Ethan kicked his shoes and pants off, pulled his shirt up, and leaned back against Mr. Panda, the massive stuffed panda bear Sarah got when she was just a kid. He did seem a little bigger now, but Ethan’s undersized dick is just a handful, even in her small hands.
She loved their life, and Ethan was sweet, silly at times, but the best word to describe her feelings towards him was comfortable. But watching him through the window, tugging at his little dick and looking over at her like he thought he was turning her on, he just seemed so pathetic, so willing to do whatever she asked just to get to fuck her.
Ethan’s a good guy, easy to get along with, but he never took much initiative in his life; he was passive in every way, including their sex life, frequently settling for a quick jerk in the shower when she denied his advances instead of claiming what was his. She knew he had unspoken sexual desires, but he’d never have the balls to tell her about them.
“WAIT!” She tapped on the window again. Several moments later, she was beside him, holding a large purple dildo he had purchased years ago for her. She said she didn’t like it, so they bought a vibrating bullet instead. Ethan didn’t even know she still had it.
“Hold this… hold this against you… You know, your penis.” She blushed, “You can keep playing with your little one if you want,” She said without a thought before leaving the room again.
Did she just call his penis Little? Ethan processed. He had never heard her talk like this before.
Now back outside the window, she knocked on the glass again. “Hold it against you.” Allison was shocked to see that even the large dildo seemed smaller than the cock she had seen her daughter handling. This was proof that what she saw was real. Devin’s cock was enormous, and her husband was not just average; he was small.
Allison scurried back inside and was quickly standing beside her confused and sexually charged husband.
“Ethan?” She heaved. “No questions, not yet.” She took the dildo from her husband, licking it, taking it as far in her mouth as she could to coat it with her saliva. Ethan watched as his wife sucked the fake dick, then pulled it out and easily slid it over his rigid nubby penis. He had forgotten the dildo was hollow. “Hold it, let me feel it.” She panted, peeling her shorts off and kicking them to the side.
Ethan was in shock as Allison reached between her legs, spreading her cunt. She straddled her husband and slowly lowered herself, sliding the thick cock inside her soaking wet pussy. She shuddered and gasped as she sank lower and lower, taking every inch.
“Fuck!’ She shook, “It’s so big. So big, Ethan.” She snorted as she rode that thick dong held by her husband’s hand, his small penis buried inside it, not feeling a thing. She was quickly moving her hips fucking the dong, fucking herself. Ethan was just a toy holder, nothing more.
“Oh, God. Oh, God!” Her voice whimpered. She pulled her tits out of her top, squeezing them. Ethan leaned in, sucking her nipple into his mouth. “YES!” She cried out furiously, humping the dildo. Allison’s nipples were always sensitive, but today they seemed to be directly connected to her clit.
Ethan watched in awe as his wife, who had always said she couldn’t orgasm from penetration creamed all over him, a frothy white fluid coated his hand holding the dildo as Allison’s orgasm flooded her body. Fully spent, Allison pulled herself off the purple dick and collapsed on the bed.
“What was that about?” Ethan laughed.
Allison sat up on the edge of the bed, her heart still pounding from the intensity of her orgasm. Her skin felt electric, her body still trembling with residual pleasure. She glanced at Ethan, who was staring at her with his pathetic penis sticking out and the dildo in his hand. She decided in that moment she wouldn’t lie – she wouldn’t keep the truth from Ethan, she was going to tell him everything and try to force him to have an honest conversation about sex.
“I saw Sarah and Devin in here earlier today,” she admitted, and told her husband how she accidentally saw them through the window. “Ethan.” She took a breath, “He’s… he’s huge. His cock is fucking huge.”
She got up, grabbed her shorts, and headed to their master bedroom. Ethan quickly scooped up his pants and followed, his penis tenting the hem of his shirt, bobbing with every step, as he fired off question after question.
“You watched them? What did you see? How long did you watch? Did they fuck? How… how big? How big was his penis? Was it like this?” He asked, holding up the dong. Allison thought it was funny that he asked that. Ethan wasn’t mad. He wasn’t upset at all; he just wanted to know more.
She nodded, her cheeks flushing as she recalled the sight of Devin’s thick, veined cock throbbing in Sarah’s hands. “I couldn’t look away. Don’t judge me, I know it was wrong, I know, but it was so… I’ve never seen anything like it.” She grabbed the dildo, “Ethan, he was bigger than this. So much bigger than you. I think I finally understand why you like porn.”
Ethan placed a hand on her thigh. “Babe, I don’t know what to say… I know I am not big…”
She cut him off, “It made me think about things… things I never let myself consider before.”
“I… I’m sorry,” Was he apologizing for having a small dick? “I’ve never seen you like this.”
“I’ve never felt like this.” Allison shook her head. “I’ve never…you know… I didn’t know I could cum like that, you didn’t even touch my clit, it was all…. fucking.” She was afraid she had said too much.
“God, Babe… I thought you said it was too big.” Ethan motioned to the dildo.
“I don’t think that’s what I said. If I remember right, I said it hurt – you were being rough with it, like jabbing me with it.” She could see the concern in his eyes.
“But… you’ll still do it, right? You’ll still be my free-use tradwife?” Ethan asked, his tone tinged with uncertainty.
“Yes, I made a promise. Tomorrow, though. Tomorrow I’ll dress up and be your free-use wife.” She assured herself as she slipped into the en-suite bathroom and turned on the shower.
To Be Continued…?
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