15 comments/ 33691 views/ 48 favorites The Regretful Cuckold By: JAnonymous Mike and Sarah had been married for just shy of 10 years when it happened, but in truth the initial foundations had been laid a few years earlier. Whilst most women would probably consider Mike handsome, there was no doubt that his wife was absolutely stunning. With her all-round gorgeous looks matched by an infectious personality, just about every man who ever laid their eyes on Sarah immediately wanted to sleep with her. For years it didn't bother Mike when he'd catch other men (including close friends and colleagues) staring lustfully at Sarah as she walked through a room (oblivious to the attention she was drawing), but when the daily routine of married life had started to become increasingly familiar, those same looks slowly started sowing the seeds of paranoia, a paranoia that one day another man may tempt his wife with an excitement their marriage now seemed to lack. Desperate to prevent this growing fear from ever become reality, Mike privately vowed to freshen up their relationship, starting with the introduction of a weekly date night where all talk of work and other distractions were banned (or else the offender would face a forfeit from the 'special' box kept under the bed...). He even hired a personal trainer to help him add a bit of muscle to his already fit but trim physique, hoping that keeping his body in good shape would keep Sarah interested. And for the best part of a year, Mike's efforts worked well, gradually alleviating the unwarranted paranoia that his wife may someday be tempted to stray from the marital bed. However, as is inevitable with such things, what were once fresh ideas soon became part of the norm, and eventually life once again began getting in the way, work commitments from both sides leading to cancelled date nights etc. Coupled with two of Sarah's close friends separating from their husband's and increasingly dragging her out for girl only nights, it wasn't long before Mike's paranoia returned, this time more intense than ever. In fact, by the time Sarah and Mike entered their seventh year of marriage, whenever Sarah went out with her friends, Mike would sit at home worrying that it would finally be the night a stranger's efforts paid off, and his beautiful wife would finally succumb to another man's advances. He would constantly find himself staring at the clock, wondering what his wife was up to, and by the time it was nearing closing time at the bar, his imagination would torment him with visions of her dancing with a handsome stranger, kissing him passionately as their bodies pressed tightly together. To begin with this was as far as his visions went, and every time his wife walked through the front door, the warm smile on her beautiful face instantly told him that he'd had no reason to worry. But paranoia can be like a disease, and despite receiving zero encouragement from his wife's actions, it continued to grow, snowballing inside of him with every night out she had without him by her side. Indeed, when Sarah and her friends went away for Zoe's hen weekend later that year, Mike once again found himself sat uncomfortably on the settee, trying (but failing) to concentrate on a film he'd recorded earlier that week. Having naively hoped that downing a couple of beers would relax his mind and help him avoid the now familiar visions he'd been having, he grew increasingly exasperated when, within 20 minutes, he was yet again picturing Sarah kissing a handsome stranger while her friends urged her on. Desperate to shake the images from his head, Mike grabbed another beer, drinking it quickly as he rewound the film to try and re-watch the last scene. However, despite renewed efforts, it wasn't long before his concentration once again faltered, and for the first time since he'd started having the visions, he now pictured the strangers' hands wandering over his wife's body, slowly making their way towards the hemline of her dress. After picturing the strangers' fingertips grazing his wife's leg, Mike's angst grew as he watched them slide their way up the inside of her smooth thigh, stopping only when they touched the thin lacy material covering Sarah's soft mound. Swallowing hard as he tried and failed one last time to distract himself with the film, he went on to imagine two of the fingers easing their way inside his wife's knickers, spreading her moist labia apart with ease, and pressing through her entrance, coating themselves in her warm juices. Mike suddenly sat upright. Although the thought of his wife being fingered in the middle of a packed bar filled him with a painful mix of anxiety and jealousy, as the initial rush of anger began to ease, he was shocked to realise that he had subconsciously been stroking a rock hard erection that was now pressing uncomfortably against his shorts. Embarrassed and ashamed, Mike quickly removed his hand and again tried to understand what was happening in the film, only to find minutes later he was frantically stroking himself, quickly bringing himself to orgasm. Although unaware at the time, as he released a heavy load of warm cum into his hand, the seemingly insignificant act of marrying his fear of Sarah cheating on him with one of sexual pleasure turned out to be the beginning of events that would eventually change his marriage forever. The Regretful Cuckold "I still don't get it Mike!" Sarah said, more tears forming in her eyes. "Look... watch one with me... please..." begged Mike, desperately hoping that seeing one might help her understand. Sarah didn't know what to do. She loved her husband to pieces and was desperate for them to find a way of working their way through this, but she simply didn't understand how watching a clip of someone having sex would help. Eventually, despite her uncertainty, and after seeing the desperation in her husband's eyes, she quietly agreed. "Ok." The Regretful Cuckold "Hon..." he went to confess, but was interrupted by a knock on the door. "That must be him..." whispered Sarah, standing up and nervously straightening her dress. Mike was conflicted as he watched his wife walk over to the door, place an eye to the spy hole, and mouth to him that it was indeed their guest. He wanted to tell her that he was having second thoughts, but part of him was also still eager to see what happened, and so he remained silent as she opened the door and welcomed their guest in to the room with a small kiss on the cheek. "Wow. You're even more stunning than your picture..." admired the dark muscular stranger, staring Sarah up and down. "... sorry... I don't mean to be rude," he continued, noticing Mike forcing himself to his feet, "I'm Sam. Nice to meet you both." As Sam moved towards him with his hand held out politely, any remaining appetite to go ahead with their plan instantly left Mike. Aside from the fact that he was already having second thoughts, Sam was even bigger and darker than he expected. Mike knew that this last part shouldn't matter, and felt wrong for even thinking it, but the thought of his wife having sex with someone so strong and so dark now made him feel ill. Mike swallowed hard, and, rather limply, finally managed to shake Sam's hand. "Would you like a drink?" he asked, hoping to delay proceedings long enough to think of a way to call it off. "No thanks," replied Sam politely, "I had a bottle of water on the way here." The room went silent for a few seconds. "Are you sure you want to go through with this?" asked Mike, turning to his wife and hoping for all the world that she would say no. "Uh huh," she responded after momentarily taking another look at Sam. "How about you?" "Errr... well... actually, I'm not sure..." "Huh?" replied Sarah, confused. "I'm not sure we should do this..." "But I thought we were both agreed?" Mike turned to Sam. "I'm sorry, but I think we've made a mistake. It might be best that you leave. Here... take this," he said pulling some money from his wallet, "it should cover your costs and more." Sam was a bit taken aback, but allowed Mike to shove the money in to his hand. "Wait! Don't you think we should talk about this before you chuck Sam out? You were so certain before..." "If you could just leave now please," continued Mike, ushering Sam impatiently towards the door. "Wait a minute!" exclaimed Sarah, exasperated that her husband wasn't listening to her. "Please just go," he continued, opening the door and guiding Sam in to the corridor. As the door closed infront of him, Sam was lost for words. On the one hand he was furious that he'd just travelled a couple of hours for nothing, but on the other hand he now appeared to be holding at least a couple of hundred (maybe more) in his right hand for, again, doing nothing. For a few seconds he just stared at the money, swaying between whether he should be angry or pleased, before finally settling on the latter and calming down. "Well that was the easiest money I've ever earned," he thought as he began walking down the corridor, "although I would have loved to have fucked that white bitch..." The Regretful Cuckold "Hmmmm," Mike purred with a smile on his face. "Do I by any chance get a blowjob as part of my surprise?" he asked, his erection growing bigger by the second. Sarah slowly leant in to Mike's ear, still rubbing his crotch, and whispered, "YOU don't..." before removing her hand and walking away. Mike opened his eyes, confused by his wife's response, and watched as she walked over towards a tall dark figure in the corner of the room. As his eyes finally adjusted to the light, he suddenly realised that the dark figure he'd seen was in fact Sam, and Sarah was now pulling him by the hand towards where he sat. "What... what's going on???" he asked desperately. But Sarah didn't respond. Instead she placed one hand around the back of Sam's neck, pulled him in to her, and began passionately kissing him as her other hand started rubbing the crotch of Sam's jeans. "Don't do this Sarah! Stop!" But Sarah didn't stop, instead she continued kissing Sam whilst unbuckling his belt and unpopping the buttons on his fly. Mike quickly looked around the chair to see if there was any way of getting free, but quickly realised there wasn't. As he turned back, he watched his wife's soft white hand reach in to Sam's briefs, pull out his large dark semi-erect member, and gently start stroking it up and down, her wedding ring sparkling with each movement. "Please Sarah, PLEASE!" But plead as he did, Mike was forced to watch as his perfect wife continued to wank the large black member in her hand whilst swapping saliva with the chiselled stranger he was responsible for inviting in to their lives. He wanted to scream, but no words would come out. It was as if his voice was being held captive by a tiny piece of him that wanted to see what would happen. After a short while of having his dick stroked, Sam leant in to Sarah's ear and whispered something too quiet for Mike to hear. But all became clear when, after a brief look at each other, Sarah gave a small smile and gently lowered herself to her knees where she began to pull Sam's jeans and briefs down over his muscular thighs, causing his thick black member to spring from its confines and brush against her cheek. Mike was in shock, and watched speechlessly as Sam kicked his trousers into the corner, and peeled his t-shirt over his head to reveal his perfect physique, his 8 pack and pecs looking as if they were made of granite. Sarah placed her hand on his abs and trailed her newly manicured fingernails down each one until it once again wrapped around his shaft, and aimed it towards her red lips. "NOOOO!" shouted Mike, finally able to wrestle his voice away, "Don't do it Sarah! I'll change!" But, guided by the large hand on the back of her head, Sarah's painted lips continued their journey, parting as they made contact with the tip of Sam's member, and allowing him in to her warm moist mouth. This was it. This was Mike's nightmare coming true before his very eyes. After all those agonising visions of Sarah cheating on him, here she was, just feet away, with another man's member inside her beautiful, sweet mouth. Desperate, Mike once again struggled to try and get his hands loose from the chair. "Yeah, you'd best be watching motherfucker," thought Sam, noticing Mike wriggling in discomfort. "That's it. Suck my big black dick," urged Sam, purposefully gathering Sarah's hair from her face so that Mike could see his wife's lips sliding up and down his long black shaft. Sick to his stomach, Mike momentarily closed his eyes in an effort to shut out what was happening. But, almost as if there were strings pulling them open, they quickly reopened seconds later. Forced to watch, Mike looked on in agony as Sam used a handful of his wife's hair to guide her mouth up and down his thick cock, her saliva causing an increasing length of his shaft to glisten under the light. Desperate, Mike made one last effort to break free, but was forced to stop when he felt the cable cutting in to his skin. Realising that his efforts to free himself had once again proven futile, he slowly resigned himself to the fact that he was probably only minutes away from watching his wife get fucked by another man. A bigger man. A black man. A deep sense of hopelessness flowed through Mike, until a small moment of optimism emerged when Sarah removed Sam's thick member from her mouth, and he wondered whether she'd changed her mind and decided to call the whole thing off. "It's not too late is it? We can get past this right? Forget that it ever happened? I mean, she only had him in her mouth for 40 seconds at most. They never actually had sex..." But as he tried to convince himself that everything was going to be OK, all hopes that his nightmare was over quickly turned to despair when his wife didn't tell Sam that she'd changed her mind as he'd hoped, but instead pursed her dark red lips against the tip of his member, and released a thick glob of saliva. Mike's heart immediately sank, and he felt like crying as he watched as his wife's soft hands begin to stroke the length of Sam's member, fully lubricating him before placing him back in her mouth. The Regretful Cuckold "You've got yourself a deal white girl. Now stay there," ordered Sam as he walked over to his bag and pulled out a bottle of clear liquid. As he returned to the bed, his large member swaying with each step, Sam winked at Mike and flipped open the cap from the bottle. "Let's get this sexy white ass ready for a big black nigger dick," he smirked, pouring a generous amount of lubricant on to Sarah's puckered asshole, massaging it in and around her entrance with his large fingers. Once fully lubed up, Sam poured another generous amount of liquid in to his hand, and stroked it up and down his shaft before placing his large tip against Sarah's light brown sphincter. "This is it white girl," he warned, pushing his hips forward. Due to his size, it took Sam a couple of attempts to finally break through Sarah's tight wall, but it wasn't long before Mike watched his wife's precious asshole finally lose it's battle and slowly engulfing the entire head of his penis. "Are you good white girl?" asked Sam, allowing Sarah a few moments to get used to him stretching her ass. "Um huh," she replied, eyes and mouth both closed as she focused on relaxing and overcoming her discomfort. "Good," he said as he started to slowly ease her backwards and forwards by the hips, gradually increasing the depth he was inside her. "Have you ever had someone fuck your ass before?" "Um huh," she responded, breathing through the pain. "Has your husband fucked you up the ass before?" "Um huh." "How about anyone else? You ever had any other dicks in your ass before?" "Um huh," she replied automatically, focusing so much on blocking out the pain that she forgot she'd told her husband he'd been the only one. "What???" questioned Mike, instantly wondering if this meant she had cheated on him after all. Sam laughed. "Sounds like you've got some explaining to do white girl," joked Sam, now slowly fucking Sarah's ass with a gentle rhythm. "Once... before us..." she managed to force out before again focusing on blocking out the pain. Mike was stunned. He was fully aware that his wife had been no stranger to sex when they got together - I mean, with her looks and personality, he'd have been a fool to think otherwise - but for years she'd told him that he was the only one she'd ever allowed near there, and this had always given him an odd sense of pride that he was the one she'd chosen. Now, after all this time together, he found out that she'd been lying to him. As Mike spent the next couple of minutes questioning whether his wife had lied to him about anything else, Sam had orchestrated it so that he was now 6 inches deep inside Sarah's asshole, and was gradually increasing the pace of his thrusts. "Well white girl, regardless of how much cock you've had up here before, your ass is still a fantastic fuck." Sarah didn't respond. Whilst Sarah concentrated on trying to relax, Sam continued to use Sarah's hips to slide her asshole up and down his thick shaft, continuing to increase how much of his shaft he had inside her. By the time he managed to squeeze just over 7 inches inside her asshole, whilst still experiencing some discomfort, Sarah was also starting to find the sensation of being stretched oddly pleasurable, and tried her best to harness that feeling. "You're enjoying it now aren't you white girl?" said Sam, noticing that she seemed more relaxed. Again Sarah stayed silent while she focused on the pleasure over the pain. "I think your wife enjoys having a big black dick in her ass," mocked Sam, looking at Mike, "...but I promised I'd fuck her pussy some more, and if I keep doing this for much longer," he continued, removing himself from Sarah's passage, "her ass will be full up with my cum." Although he knew full well that it had been said out of spite, hearing Sam talk about cumming inside his wife, and watching her light brown asshole take a few moments to fully close, Mike's cock sprung back in to life, stirring the mess he'd made a short while earlier. "Turn over white girl," directed Sam, taking a small towel out of his bag and wiping his cock clean, "it's time for your reward." Sam walked back over to the bed and manoeuvred his large muscular physique back on top of Sarah's delicate white body, immediately kissing her as she grasped for his member, her wedding ring once again visible against his dark shaft as she placed it at her entrance. Despite all of the humiliation that had come before, as Sam pressed his hips forward and once again began fucking Sarah, Mike started to grow increasingly uncomfortable that, unlike earlier in the evening when he'd fucked her with an aggression... almost a spite, Sam was now much more gentle, making sure that Sarah was feeling every inch of his large member. For Mike, even though he had watched his wife have sex with another man for over half an hour now, this was torture. As he watched them kiss each other passionately, bodies intertwined, he considered that this was no longer just sex, to his eyes, this was more like making love. As he watched his wife's vagina wrap itself around the long dark shaft gently stroking in and out of it, his ears once again pricked at the satisfied sounds coming from his wife. "Fuck me Sam. Make me come again," she begged, momentarily breaking their kiss. Sam slowly increased the rhythm he'd built up, one hand cradling the back of Sarah's neck as they kissed, the other gently caressing the smooth skin on her side. Within a minute, a small build up of his wife's juices once again formed around the base of Sam's shaft, and Mike realised that it wouldn't be long before Sarah experienced her second orgasm at the hands, or more precisely, the cock, of another man. Gradually Sarah's moans became louder, only partially muffled by Sam's kiss, and her legs wrapped around his waist, encouraging his thrusts with their own. Sam continued to pump in and out of Sarah, and within a minute her feet were in the air, toes curling up in her shoes, an orgasm ripping through her body so ferociously that her ass lifted off the mattress and her hips began to buck. "FUCKKKK!" screamed Sarah, "Don't Stop!" she pleaded over and over, almost in tears as she rode the wave of her second orgasm. Sam continued to thrust until Sarah's pussy finally stopped twitching around his shaft and her body relaxed to normal. "Fuck you're good white girl... I'm almost done myself." warned Sam, breathing heavily. "Cum in me..." she responded, pulling him back on top of her and grinding her hips. Mike's heart skipped a beat, shocked at hearing his wife instruct this black stud to shoot his cum deep inside her unprotected womb, but by now Mike was so turned on that he made no attempt to object, and instead adjusted how he was sitting to try and ease the discomfort caused by his throbbing erection pressing against his trousers. Less than a minute later, Sam's thrusts became slower and more powerful, and he suddenly released a series of loud primal grunts as his large black member began pumping his thick seed deep inside Sarah. To Mike's surprise and concern, even after the final drop of cum had been released from his body, Sam remained inside Sarah and they both lay there kissing for what felt to Mike like minutes. When they finally stopped, and Sam removed his semi-erect cock from Sarah's well used pussy, a thick stream of cum oozed from her gaping hole, flowing over her asshole. "You've been one of the best so far..." said Sam, sweat running down his face, "yep... you've definitely been one of the best," he repeated as he begun to collect his belongings. As Sam got dressed, Sarah remained on the bed and looked directly at her husband as she slowly and gently began rubbing herself, dipping her fingers in to her open pussy and using Sam's cum as a lubricant. Mike simply watched, mesmerised, until a fully dressed Sam walked over and again kissed Sarah passionately before finally making his way to the door. "You're a good fuck white girl. Let me know if you want to do it again. No need to bring your husband next time..." With that, Sam left the room, leaving Sarah and Mike alone. Mike went to say something to his wife, but struggled to find any words. "Is that what you wanted honey?" purred Sarah, still rubbing herself. "Was it as good as you imagined?" Mike struggled for an answer. "You like the videos where the husband's humiliated don't you?" she sighed, removing her wedding ring from her finger. "And I could tell you liked it when he fucked me right infront of you earlier," she continued, dipping her ring in to Sam's warm semen. "Has this satisfied your desires?" she asked, slowly sitting up and pulling herself to her feet. "Has this got it out of your system?" she questioned, walking towards her husband, completely naked apart for her shoes, earrings, and another man's cum trickling down the inside of her thigh. Sarah stood infront of her watching husband and gently cleaned Sam's cum from her ring with her tongue. "Because I'm not sure it's out of mine..." she whispered quietly in his ear before kissing him, making sure his tongue met with her own. As she walked away towards the shower, Mike, still tied to the chair, closed his eyes and released a second pool of cum inside his linen trousers. Perhaps it wasn't out of his either.