Bob sat cross-legged on the bed, the shadows playing across his face as he carefully selected a lacy black thong from Cindy's drawer. The fabric was silky smooth, a stark contrast to the white briefs he usually wore. His eyes lit up with excitement and he could feel his heart racing as he slipped the garment over his already swollen member. The elastic snapped into place around his waist causing him to shiver slightly as his cock quivered at the illicit sensation of wearing something so feminine, so intimately connected with his wife.This story is an experiment both in content and creation. The named characters are real, much of the background leading up to the encounter described is real as well. The story turns me on, but I am not entirely sure if it is because I lived through much of what happened and have a personal connection, or if some sense of what I experienced has been successfully transferred to readers other than myself. This story may also be controversial in that it was created with the assistance of AI. I do not consider this story to have been written by AI, it required hundreds of prompts, paragraph by paragraph, with manual edits, and re-edits at every step. I may not have written every word, but it is the story I intended to tell. In my mind I take credit for the creative process in crafting this story, but readers will be the final judge.
The dark house was eerily quiet, the only sound the faint buzz of the air conditioning unit. Bob had not indulged in his secret fetish for years, not since his marriage to Cindy, but his brief four-year marriage was coming to an end. They shared a bed but that was all that they shared. By mutual agreement, it was only a matter of time until he could find an apartment and move out. The ring on his finger was a testament to false hope, however, it was clear from Cindy's nightly absences that she had already moved on. Bob knew he should feel guilty as he reached into the drawer again pulling out a pair of black stockings. He rolled the stockings over his legs feeling the nylon caress his skin as he stood to examine himself in the full-length mirror. The image staring back at him was almost comical, a bookish 36-year-old IT professional man dressed in his wife's most intimate apparel but in no way passible. It didn't matter, the sight of his bulging erection pushing against the delicate fabric made his pulse quicken. Taking another deep swallow from the half-empty bottle of vodka on the nightstand Bob laid on the bed to masturbate, it would be hours before she came home.
Bob's steady rhythm came to a sudden halt when he heard the front door slam shut, the sound of high heels echoing through the hallway. His heart pounded in his chest as he frantically began to remove the lingerie but it was too late. Cindy's voice floated into the bedroom followed by another deeper and unfamiliar, she had brought someone home from the bar. He froze, his heart racing, what would they think if they saw him like this. A dozen plans for escape flashed through his mind in an instant but in the end, he remained frozen like a deer in headlights. The door to the bedroom swung open revealing the silhouette of Cindy's small frame in the hallway light. Cindy's eyes narrowed into a vindictive smile as she took in the sight of her husband in her clothes. A tall, muscular stranger with a smug look on his face stood behind her, his eyes sweeping over Bob's ridiculous attire. "Well, well, well," declared Cindy, her speech slightly slurred, her Long Island accent thick with spite, "Looks like someone's been playing dress-up." Bob's cheeks burned with shame as Cindy sailed into the room her words as sharp as the heels of her shoes, "You always were a lousy lay, Bob. Maybe it's because you're more interested in this shit than real women."
The stranger, a dark-haired man with a cocky smirk, stepped into the room his eyes raking over Bob's half-dressed form, "Looks like we've caught ourselves a sissy," he chuckled his tone deep and mocking.
Cindy's eyes gleamed with malicious glee as she approached, grabbing his chin, forcing him to look at her. "You're pathetic," she spat releasing him with a disgusted shove, Bob stumbled back landing hard on the bed. The stranger took a step closer his hands on his hips, "Sit there," Cindy pointed to the corner of the bed her voice dripping with contempt, "You're gonna learn something tonight, Bob, you're gonna learn what a real man does to a woman."
The stranger, clearly enjoying the scene unfolding before him, sauntered over to Cindy and placed a hand on the small of her back, "You're right, babe," his voice a gruff purr, "I'll show him how it's done." Cindy let out a sigh of approval and leaned back against the stranger that towered over her, grinding her ass against his growing erection. Bob couldn't help but feel a strange mix of arousal and humiliation as he watched the man's hand glide up Cindy's body, cupping her small perky breasts through her tight dress. She arched her back pushing herself further into the stranger's touch. Bob's eyes were drawn to the way her nipples stood out hard as pebbles beneath the fabric. He felt a pang of jealousy but also an intense curiosity about what was happening between them. The stranger noticed Bob's erection his smirk growing wider, "Look at that," he pointed at Bob's tented underwear, "Your hubby's getting a little excited watching us, isn't he," he stepped closer, his eyes never leaving Bob's face, "What's the matter, Bob, can't get it up for your wife," His voice was a toxic blend of amusement and contempt, "Or is this what you like, watching her get fucked by a real man?"
Cindy giggled, her eyes glittering with spite. She turned to face the stranger pressing her breasts against his chest and looping her arms around his neck, "You want to watch, Bob," she taunted, her voice a siren's song of scorn, "Go ahead, get a good look, maybe you'll learn something."
Without waiting for a response Cindy and the stranger began to kiss passionately. Bob watched, his breath hitching in his throat as Cindy's hands fumbled with the man's belt. The stranger's hand slid down to cup her ass pulling her closer as their kisses grew more urgent. The sound of the zipper was like a gunshot in the silent room, Cindy's dress pooled around her ankles revealing the matching black lingerie she'd chosen for the night. The stranger's eyes never left Bob's face as he pushed Cindy onto the bed. She giggled and squirmed under him, her excitement palpable in the air. Bob could feel his cock straining against the confines of the lacy thong as it begged for release. Cindy looked at her husband, a twisted smirk playing on her lips as the stranger kissed a trail down her neck his hands roaming over her body, "You like watching, don't you," her voice a seductive whisper that sent a shiver down Bob's spine.
With trembling hands, Bob reached down and began to stroke his cock through the thong, now wet with his precum. He couldn't believe what was happening but he couldn't deny the rush of arousal that flooded his body as he watched his wife with another man. The stranger's muscular arms flexed as he reached behind Cindy, unclipping her bra with one deft move revealing her small but pert breasts, the sight made Bob's cock throb even more and he quickened his pace. Cindy's eyes remained locked on Bob's face, a smug smile playing on her lips as the stranger kissed and licked her neck. The stranger's hand slid down Cindy's body, his fingers disappearing into her panties, she gasped, her eyes rolling back in her head, "Look at her," the stranger said his voice thick with lust, "Look how much she wants it, how much she loves having a real man's hands on her," Bob's eyes darted from Cindy's face to her chest where the stranger's hand was now playing with her erect nipples, "You could never make her feel like this," his voice low and confident, "You could never satisfy her with that pathetic little dick. With a cock that small it's no wonder you dress like a girl."
Bob's face flushed with anger and embarrassment did not stop his hand's movement. The humiliation was a strange aphrodisiac mixed with the thrill of the forbidden. He watched as the stranger's hand slipped lower, sliding deeper into Cindy's panties and eliciting a moan from her. She bucked her hips, grinding herself against his palm. Bob felt a hot pulse of arousal shoot through his body as Cindy's eyes remained locked with his as the stranger's fingers worked their magic. Her pupils were dilated, her breath coming in quick, shallow gasps, she was wet and ready, her desire for this new dominant presence palpable. The frustration of four years of unsatisfactory sex with Bob was about to be released in a torrent of passion that she hadn't felt in a long time. The stranger's fingers played her expertly, teasing, and probing until she could no longer hold back, "Fuck me," she begged the stranger her voice a desperate whine, "Please, I need you inside me, now," her plea was raw and unfiltered a direct hit to Bob's ego who couldn't tear his eyes away. He watched as the stranger smirked taking his time, savoring the power he held over both of them.
The stranger looked at Bob, his eyes gleaming with mischief, "You heard her," he shrugged, his tone mocking, "Who am I to refuse," he winked a knowing look passing between them that spoke volumes about the twisted dynamics at play. With a swift movement, the stranger removed Cindy's panties, revealing her bare pussy glistening with anticipation. He stepped back freeing himself from his pants, revealing an erection that was everything Bob feared he wasn't, long, thick, and unapologetically powerful. Bob's cock twitched again in the confines of the thong, he couldn't help but feel a twinge of inadequacy.
The stranger's cock slid into Cindy with ease, her moan echoing through the room. Bob watched transfixed as Cindy's body responded to the stranger's touch in a way it never had to his. Her legs wrapped around the man's waist pulling him in deeper, her nails digging into his back as he began to thrust into her. Each movement was a silent taunt, a declaration that Bob could never give her what she truly craved. The stranger's rhythm grew more intense, each stroke a deliberate claim on Cindy's body. Bob's hand stilled on his rock, his breathing ragged as he watched the scene unfold. He felt like an intruder in his marriage, a voyeur to his wife's betrayal. Yet, he couldn't deny the dark thrill that coursed through him as he took in the sight of Cindy's face contorted with pleasure, her body writhing beneath the stranger's powerful thrusts.
Cindy's eyes rolled back as she let out a guttural cry as the stranger reached his climax pumping his seed deep inside her. Bob's mind was a tumult of emotions – anger, arousal, and a strange sense of satisfaction. The stranger pulled out, a trail of cum following his cock as it left Cindy's swollen pussy. He smirked at Bob who sat frozen in the corner the thong around his waist stained with his juices.
Cindy slid to the edge of the bed, her legs trembling with the aftershocks of pleasure. She looked at Bob, her eyes glinting with cruel amusement, "I believe you have a little clean-up to do," she pointed to the floor in front of her, her voice low and commanding, "Get on your hands and knees and lick me clean."
Bob hesitated his face a mask of humiliation and arousal. The stranger chuckled, watching the spectacle with a knowing smile, "Come on, Bob," his voice laced with condescension, "Show me how much you love your wife," Swallowing hard, Bob lowered himself to the floor, his knees hitting the soft carpet with a muffled thud. He leaned forward his eyes locked on the mess that was Cindy's pussy, a mix of the stranger's cum and her juices. Bob's cock was still hard, straining against the fabric as he took a deep breath and pressed his tongue tentatively to her folds. The taste was foreign and bitter but it was also strangely addictive. He began to lick, his movements tentative at first but gradually gaining confidence as the stranger's eyes bore into him.
The stranger leaned against the frame of the bedroom door, his cock still semi-hard, watching Bob with a mix of amusement and arousal. He took a swallow from the bottle of Vodka that was still on the nightstand, "That's it," he murmured, his voice thick with satisfaction, "Taste her, taste what you can't give her," his cock twitched, responding to the submissive display before him. Bob's tongue darted in and out of Cindy's pussy, his cheeks flaming with embarrassment as he cleaned her. Cindy's legs were spread wide giving him no escape from the intimate task she'd set for him. The stranger's cum tasted faintly salty, a stark reminder of his inadequacy. As Bob lapped at her, he heard the stranger's breath hitch and then he felt a hand on his shoulder followed suddenly by strong arms wrapping around him, pulling him backward, the thong was ripped aside, then before he could react the stranger's hard cock was pressing against his tight hole. Bob's eyes shot wide with shock and fear, the stranger's voice a low, seductive growl in his ear, "You liked watching," the stranger murmured, his breath hot against Bob's neck, "Now it's your turn to feel it," with one hand on the back of Bob's head keeping him in place the stranger's other hand gripped his hip and pushed in deep. The wetness of cum and Cindy's juices made it easier than Bob ever thought possible. He gasped, his eyes watering as the thickness filled him. The stranger didn't wait he started to fuck Bob with a steady rhythm that made the bed shake. Bob could feel the stranger's cock sliding in and out of him the friction sending sparks of pain and pleasure through his body. Cindy's legs tightened around him, her excitement building as she watched her husband being used by the man who had just fucked her. She reached down her hand finding Bob's face, her fingers clenching his hair as she pushed him harder against her pussy. The stranger's thrusts grew more erratic, his breathing heavy. Bob's tongue was a blur as he tried to keep up with the pace, his arousal growing with each push into his ass. The taste of the stranger's cum on his tongue mingled with the sweetness of Cindy's arousal. The stranger's hand moved from Bob's shoulder to the back of his head pushing him even closer to Cindy, "Make her come again," he grunted, his grip on Bob's hip tightening, "Show me how much you love the taste of her cunt."
Bob's tongue worked feverishly, his mind racing with a mix of horror and excitement. He could feel the stranger's cock growing harder with every stroke, the pressure building until it was unbearable. Cindy's legs began to quiver around him, her breath coming in short, sharp gasps. The scent of sex filled the room, a heady mix of sweat and arousal that only served to drive Bob's desire higher as the stranger's grunts grew louder, his thrusts more forceful as he approached his climax. Cindy's hands moved from Bob's head to her breasts, pinching and rolling her nipples as she watched her husband's humiliation. Bob's eyes watered with the effort of not gagging, but he knew that if he stopped the consequences would be far worse. His cock still trapped in the soiled thong throbbed painfully with every thrust, desperately seeking release. Then, with a final triumphant roar the stranger rammed his cock into Bob's ass one last time and pumped his seed deep into Bob's bowels.
Bob's body convulsed his eyes rolling back in his head as he felt the warmth spreading inside him. Cindy's legs tightened around his neck cutting off his air as he realized with a start that she was coming again her body shuddering with the power of her second orgasm of the night. The stranger stood and strode wordlessly to the bathroom, his cum dripping down the crack of Bob's ass, pooling on the carpet. Cindy sat up her body glowing with satisfaction as she looked at Bob kneeling before her and laughed cruelly, "You got me off," her voice dripping with sarcasm, "I guess there's a first time for everything."
Bob stumbled to his feet, his legs wobbly, he could feel the weight of the stranger's cum between his cheeks running coldly down his legs. Cindy giggled at the sight of cum dripping from the front and back of Bob's thong clear evidence he got off while being fucked. Bob reached down to pull the thong away from his sticky skin, the material clinging unpleasantly, "No," commanded Cindy, her voice a mix of amusement and disgust, "Leave them on, I don't want that gross thing back," she pointed to the bedroom door, her eyes gleaming with victory, "You can sleep on the couch tonight, I have plans."
Bob's cheeks burned with humiliation as he stumbled out of the room the thong sticking to his skin. The hallway spun around him as he made his way to the living room the smell of sex and the stranger's cum clinging to him like a thick fog. As he lay on the couch, the sounds of Cindy's laughter and the stranger's deep voice echoed from the bathroom. He could imagine them together in the shower, washing away the evidence of their betrayal, their bodies slick with soap and sweat, the thought made him sick. He hated himself for it but he couldn't deny the way his cock twitched at the thought of Cindy's pleasure.