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."

Mike opened up the laptop and typed in the URL to his favourite site. Despite feeling a large unease at showing just how familiar he now was with looking up porn, he was quietly relieved that Sarah was willing to give him a chance. He was also conscious that he didn't want to overwhelm or upset Sarah, and so tried to be careful in which video he showed her, selecting one he remembered to be relatively tame.

As the clip begun, Sarah sat in silence as a white lady - probably in her early thirties like her - welcomed an older, slightly overweight black man into the room. As she led the man towards the bed, Mike closely watched his wife's face, looking for any sign of what she was thinking, and as the lady began undressing her guest, what he saw was a clear look of confusion.

"If this isn't a professional film," she began to ask, "who's recording?"

"Her husband," replied Mike hesitantly, still watching her face closely for a reaction.

"Bu... wh... why would her husband want to film, or even watch his wife having sex with another man?" she asked after a few moments, clearly bewildered.

"I guess this way he feels like he's taking control. You know, rather than her going behind his back, he'd rather he was part of it. Be involved in the enjoyment she gets from sleeping with other men..."

Sarah didn't respond, and despite an uncertain look on her face, continued to watch as the woman on the screen pulled the black man's trousers down and released his large member from his briefs.

Before she'd begun dating Mike, Sarah had spent a night with a man who was VERY well endowed, and whilst she remembered enjoying the sex, she never particularly felt an uncontrollable urge to experience it again. The woman on the screen, however, seemed to find the size of her guest's manhood irresistible, and was now practically worshipping it with her mouth.

For the next 15 minutes, Mike and Sarah sat there, watching as the cameraman's wife sucked, licked and stroked the older man's large black member, before she moved on to her back and was fucked rhythmically in the missionary position. Finally, after the woman appeared to orgasm, the man began to grunt as he came inside her vagina.

Mike looked at Sarah, and could immediately tell by the expression on her face that she still didn't understand. Turning back to the screen slightly dejected, Mike quickly felt his heart race as he saw the woman in the video using her fingers to spoon cum from her vagina and feed it into her mouth.

"Fuck!" cursed Mike in his head, quickly closing the laptop down.

Sarah sat quietly, not quite sure what to say.

"And this... helps you?" she finally asked, but in a less judgemental manner than Mike thought she might.

"Well... yeah..." he responded cautiously.

For a few seconds Sarah and Mike sat in uncomfortable silence until Sarah finally took a deep breath.

"OK..." she responded, "I... I still don't really understand, but if this is what you need to keep your insecurities under control, I'm OK with you watching these videos... but you need to realise that I'm not like these women. I don't feel the urge to have sex with other men. I'm happy with you, and I'm happy with our sex life. Just make sure you're honest with me. Don't keep secrets. Ok?"

Mike nodded and turned the screen off, pleased that his wife hadn't harshly judged him for his faults.

Over the next few months, Mike openly spoke with Sarah whenever his jealousy started to rise, often explaining how he'd seen a stranger, or sometimes one of their friends, staring at her. He'd even been able to convince her to watch some more videos with him, telling her that it helped him knowing that she was willing to support him.

Whenever she agreed, he initially ensured that the videos were pretty much more of the same, never too graphic or contentious. But over time, Mike became increasingly curious as to his wife's boundaries, and started selecting more adventurous clips. To his surprise, whether he chose a video involving anal, two or more men, or one that ended with the woman receiving one or multiple facials, Sarah would just sit there quietly, giving nothing away as to what she was thinking.

Finally, during the sixth or seventh video they watched together, Mike decided to really test the waters, and so, as the woman on the screen was getting unceremoniously fucked from behind whilst pleasuring another guy with her mouth, Mike slowly slid his hand onto his wife's lap. With little reaction either way, he slowly moved his fingers towards her until the only thing stopping him from entering her was the thin material of her shorts. Preparing himself for an angry reaction, Mike paused momentarily, but to his surprise, Sarah just sat there, letting him do it.

Growing more courageous, Mike manoeuvred his hand to the inside of his wife's shorts, spread her surprisingly damp labia apart with his middle finger, and used her juices to lubricate and gently massage her increasingly exposed clit, occasionally allowing a finger to push inside of her. He carried on, unopposed, for the next three or four minutes until finally the clip ended, and Sarah turned to face her husband. Without saying a word, she gently removed his hand from her shorts, pulled him to his feet, and led him to the bedroom where they had the best sex they'd had in months.

Afterwards, Mike was on cloud nine. It was clear from her actions that his gorgeous wife was slowly beginning to enjoy the movies she'd previously found so confusing, and after thinking of nothing else for the remainder of the day, he decided he would test the waters even further as soon as an opportunity presented itself.

This opportunity came a few days later when Sarah and Mike came home from a meal with friends and soon found themselves having sex on the front room carpet. As he started getting close, Mike, fuelled by alcohol, once again whispered in his wife's ear, "You want to be fucked by a big black cock don't you?" Unsure how she would react, Mike stayed quiet, preparing for her to get angry. But nothing. No reaction at all. Was that good or bad? Slightly confused, Mike carried on fucking his wife, eventually finishing by shooting his cum across her well toned stomach.

That evening, Mike waited anxiously for Sarah to bring his comment up, but she never did.

Over the next month or two, Mike and Sarah continued to watch the occasional amateur video together, often having sex after they'd finished. Having reasoned that it was during these moments that he'd most likely get a reaction from his wife, whenever watching a video led to sex, Mike again whispered about being fucked by a big black cock. As before, Sarah always remained quiet, until finally, on the fifth occasion, she responded.

"Uh huh" she murmured, biting her lip as her orgasm grew.

Surprised, Mike kept it going.

"You'd love it wouldn't you, having a big black cock stretching your tight white pussy."

"Uh huh" she again said as she began grinding her hips against Mike's.

"You want to be used by black cock don't you."

"Uh huh..."

"You want to be fucked like a black cock whore..."

Sarah's orgasm exploded though her body, and as her muscles began contracting she squeezed her breasts and pulled on her nipples, her screams of ecstasy filling the room and surprising Mike with their volume. Normally when she came, she'd be fairly subdued, almost holding it in before purring her satisfaction afterwards, but this time was completely different. This was easily the loudest Mike had ever heard his wife come.

As they lay there afterwards, Mike decided to again bring the subject up.

"Do you really want to be..."

Sarah, who had been waiting for him to ask, immediately cut him off. "Of course I don't. I was just playing the role," she said dismissively, hoping it would kill the conversation dead.

"Oh... ok," said Mike, careful not to push it. But he knew. He knew it was more than her simply 'playing the role' from how her body had reacted.

Over the next month the couple continued to watch more films together, and continued to enjoy a flourishing sex life. Each time they had sex, Mike would continue to whisper in Sarah's ear, and each time she would react until climaxing with an intense orgasm. Eventually Mike brought it up again.

"Are you sure you're just playing along honey?"

"I've told you Mike, I have no intention of cheating on you."

"But... but what if I was OK with it?"

Sarah stayed silent as Mike thought carefully before saying his next sentence.

"What if we arranged it together and I watched?"

To his surprise and concern, Sarah started to cry.

"Honey... why are you crying?"

"I love you Mike. I don't want to cheat on you..."

Mike felt guilty, worried that he'd finally found her boundary, and overstepped it.

"...but..." she continued after a few moments, surprising her husband, "but I'm confused. Since we've started watching these videos together, and since I've seen how much you enjoy it... how much they help you... I wonder... I wonder if us doing something like that would let you move past it and help us go back to how we used to be."

Mike couldn't believe it. He'd somehow managed to convince his loyal, faithful wife that it might be OK for her to have sex with another man so long as he could watch. Aware of the fragility of the situation, Mike momentarily held his wife in his arms before responding.

"I think it might..." he finally said, softly, hoping it would help ease her conflict.

Over the next few minutes the couple laid in silence until Sarah eventually sat up, and tried to shrug it off.

"It's insane," she said, laughing to herself as she moved to her feet. "There's no way me having sex with another man would help our marriage. No way! I mean... how would we ever get past something like that?"

As she went to start getting dressed, Mike grabbed her hand and gently pulled her around to look at him.

"Honey, I'm not sure our marriage will get past us not doing it."

Sarah stared down at him, her eyelashes still damp from her recent tears, and leant in to kiss him on the lips. Mike, realising that this was the point in which he would either cement the deal or have to let it go forever, pulled his beautiful wife towards him until she straddled his lap. He rolled her on to the bed, and began kissing her passionately as he once again entered her and they began making love. By the time they had finished, Mike had finally convinced her.

Over the next few days, Mike and Sarah tentatively began discussing how it might happen, and started to draw up a list of rules:

- Whoever they chose to take part in their plan MUST NOT be local - the last thing either of them wanted was for them to bump in to the person after the event, or especially for them to have some kind of link to their friends;

- It MUSN'T happen in the house - not only because they didn't want their neighbours asking questions, but because if it didn't pan out how they'd hoped, they didn't want whoever they'd chosen knowing where they lived;

- A condom MUST be worn at all times during intercourse - Aside from the potential health risks of having sex with a stranger, for years they'd been practising fertility awareness over the pill, and so both agreed that it was important not to take ANY risks;

- NO anal - When Sarah first allowed Mike to experience the pleasure of her near flawless ass, she'd confessed to him that he was the first - as far as Mike was concerned, he intended to remain the first and only;

- NO kissing - Oddly, although happy to watch Sarah have sex with another man, Mike did NOT want her kissing him. As far as he was concerned, kissing, particularly during sex, was an act of intimacy, something he didn't want anyone else to experience with his wife;

- NO filming or photography allowed - For the same reasons that it mustn't happen locally, Mike and Sarah wanted there to be zero chance that their indiscretion be discovered by friends and family; and, finally;

- Above anything else, the other person taking part MUST abide by their rules and accept Sarah's wishes - whilst Mike considered he would be willing to allow most things happen, both he and Sarah wanted her to feel completely comfortable with proceedings.

After a few days of consideration, Mike and Sarah both agreed that they were happy with the list of rules, and started talking about the next steps. As they discussed their options, Sarah confided in Mike that she was nervous, but when he asked if she was still happy to go ahead, she nodded timidly.

After getting his wife's go ahead, however hesitant, Mike set about putting an advert together for a website he'd found. The advert asked for a 'well hung black man, preferably aged between 25 - 35, who was willing to have sex with a married white woman whilst her husband watched'. No local applicants would be considered, and they must agree to the rules that Mike attached. The advert then asked for anyone interested to email a recently set up (and anonymous) account with pictures and a brief note about themselves. If selected they would be sent a fully dressed picture of Sarah (although her name wouldn't be given) so that they could decide whether she matched their criteria (something Mike was certain she would).

Over the next few days, Mike and Sarah read through the numerous replies, filtering most of them out fairly easy. In fact, as the end date for their agreed week long advertisement drew closer, Sarah had only selected one as a possible maybe, but, at 21 (12 years her junior), she thought he may be too young, and both Mike and her were also worried that he was perhaps too local, given that it was only half an hours drive between him and where they lived. As a result, they decided to keep looking, causing Mike to panic that the lack of choice may be giving Sarah second thoughts.

As the closing date finally passed, Mike and Sarah sat down to go through the final remaining applicants. As before, most of them were discarded immediately, either too old, young, unattractive, white etc., but one seemed to stand out.

"What about him?" Mike asked Sarah.

Sarah looked at the photo, and was immediately impressed by the stranger's ripped physique and handsome face. As they scrolled down, the photos changed from him being half naked in a pair of shorts, to completely unclothed, and, although they both hid it from each other, both Mike and Sarah were momentarily stunned as they saw the impressive size and girth of his penis for the first time.

The bio attached to the email said that he was 6"4, 30, and had taken part in several other trysts with married women and their partners. However, he assured them that he always had regular check ups to make sure he remained healthy, and had no qualms with abiding by the rules they'd set.

After she'd finished reading, Sarah turned to her husband.

"What do you think?" she asked hesitantly.

"He seems to fit the bill. What about you? Are you happy?"

"Uh huh," she responded, biting her bottom lip.

"Shall I email him your picture?"

"Uh huh," she responded again, beginning to rub Mike's crotch through his pants.

And so it was arranged.

At around mid-afternoon the following Saturday, Mike and Sarah arrived at the hotel, a place specifically chosen because it was situated a good hour's drive away from their house, and roughly about 2 hours from where their chosen applicant lived.

Once parked, Sarah got out of the car, picked up her small suitcase, and went with her husband to collect their room key from the young women on reception. The room itself was fairly basic, but perfect for their intended purpose.

After laying her dress out on the bed and putting her make-up bag on the bathroom counter, Sarah admitted to Mike that she was starting to feel nervous, and so Mike did his best to reassure her that they were doing the right thing for their marriage. After a few minutes of talking it through, Mike told Sarah to relax while he went to find her a drink for her nerves, kissing her on the lips before standing up and leaving the room.

When he returned 20 minutes later, Mike placed the bottle of brandy and the bottle of coke he'd just bought next to the bed, and made his way to the bathroom where he heard the shower running. Opening the door, he was about to knock to let Sarah know that he was back, when he was instead left entranced by the reflection of his wife washing her naked wet body in the mirror. Almost hypnotised by the sight of warm soapy water running down her sun-kissed porcelain skin, he instantly felt a twinge in his trousers, and simply watched without saying a word.

"What did you get me?" asked Sarah, turning the water off and gently squeezing excess water from her hair.

"Er... I err," stuttered Mike, a little embarrassed that his wife had clearly known he'd been standing there watching her, "I... got you a bottle of brandy and some coke. I hope that's OK?"

"Perfect," she replied, grabbing a towel and wrapping it around her breasts, "how about you pour me a glass."

"How about we work up a thirst before I do?" suggested Mike, moving toward his wife, hopeful that she would rid him of the erection now pressing against his shorts.

"Na-huh," she replied, smiling and shaking her head as she placed a hand against his chest. "I've just had a shower. We don't want you getting me all dirty again before our guest arrives do we? You'll just have to wait your turn..." she teased, lowering her hand to his rock hard crotch and giving it a small rub. "Now go and get me that drink."

Sarah winked at her husband and blew him a kiss before watching him walk away awkwardly.

Over the next hour Mike's cock continued to throb as he watched his stunningly attractive wife prepare herself for another man. First she finished drying herself before rubbing moisturiser in to every part of her flawless skin (he was certain she'd intentionally teased him when massaging it into her breasts, thighs and ass), then he watched her slip on a new pair of black French knickers and matching bra (the lacy material clinging perfectly to her firm curves), before stepping in to a delicate white summer dress decorated with small black dots. Next he watched as she began preparing her make up, first delicately painting her lips with a red wine coloured lipstick that matched the nail varnish she'd applied the evening before, and then framing her eyes with mascara and a small use of eye shadow. Finally, she finished styling her hair by adding subtle waves to her centre parted style, and then slipped on a pair of white dress sandals to complete her outfit.

"How do I look?" she asked nervously.

"Absolutely gorgeous," said Mike, genuinely taken aback by how beautiful his wife looked. "Are you sure you want to go through with this?"

Sarah slowly looked herself up and down, bit her lip and gently nodded, "Uh huh."

For the next 10 minutes Mike and Sarah sat in near silence as they both waited anxiously for their guest to arrive. Initially Mike's silence was due to the excitement of knowing that what he'd fantasised about for months was now only moments away from becoming a reality, but as the minutes slowly ticked by and he watched his gorgeous wife put on the earrings and necklace he'd bought her for their anniversary, he was suddenly overwhelmed by the thought that he was making the biggest mistake of his life.