Janet was supposed to go on a weeklong vacation to a seaside resort with her husband, David. They had planned it after postponing so many times, and she was really looking forward to the break and some private time with her hubby. But as always seemed to happen, his job got in the way… again! One day before they were to leave, David told Janet that he could not go; the project he was working on was behind schedule, a major checkpoint was coming up, and he was key to getting it done.
She was upset. So many times this same thing had happened. Why couldn’t he plan things better so he could get away? Why was it always David who had to take care of things at work? Janet couldn’t understand and tried to win him over with promises of wonderful sex, but to no avail. David would not budge, asserting that keeping his job depended on it.
What was she to do? She could miss yet another vacation, or she could go without him, but it was too late to arrange for a girlfriend to join her. Should she go alone? What choice did she have if she wanted a break from their dull routine? She decided she’d go alone and make the best of it. David understood and agreed, reluctantly.
o o o
The next day, she headed to the airport, checked in, and boarded. The flight wasn’t that long, just to Bermuda. She enjoyed some wine on the plane and, upon arrival, caught a taxi to the resort. She checked in and was shown to her villa. David would have loved this place, if only he had made sure he could go… maybe next time.
That evening, there was a welcome dinner and party for new guests. Janet decided to go since it beat trying to find dinner on her own. She dressed in her ‘little black dress’, which was pretty sexy for her, even though it wasn’t very revealing. She was seated next to an empty chair at a table with two other couples. Before they introduced on another, a good-looking older gentleman came to the empty seat and asked Janet if he might join her. She was surprised, but he was kind, and she agreed.
The couples all introduced themselves, and small talk ensued. But Janet was fascinated by the new gentleman beside her. He said his name was Reginald, an Englishman, and he was employed by the resort to ensure women attending alone had a good time. Sometimes they were recent widows; sometimes they were divorced; sometimes their husbands couldn’t make it; and sometimes they were single and looking for fun. In any case, he was there to make sure they had fun.
After a fine dinner, Reginald asked Janet to stay and go to the party with him. She was torn; would this be cheating on David? After wrestling with it, she decided it was not cheating, remembering what George Costanza said on the “Seinfeld” TV show… “It’s not cheating if there’s no sex.” So as long as she didn’t sleep with Reginald, which would never happen, it was okay.
Janet went to the party with Reginald, had drinks, danced (for the first time in years!), laughed a lot, and had fun. Reginald was charming and knew how to talk with a new lady. He asked all the right questions and made all the right compliments! She was blown away and felt appreciated, and when he walked her to her villa after the party, she discovered she actually wanted to invite him in. And it wouldn’t be cheating if she didn’t have sex with him.
o o o
Janet invited Reginald to come into her villa. He said he’d get some wine for them and called room service to order it. Then he approached Janet and put his arm around her waist. He pulled her gently towards him and looked into her eyes.
“You may be happily married, sweet Janet, but your husband is not here. And you’re far too pretty a woman to be sent to a romantic resort on your own. May I kiss you?”
Janet didn’t know what to do. She could let Reginald kiss her if that was all there was to it. But would it be? While she thought, Reginald moved to kiss her without waiting for an answer. He touched his lips to hers, softly, and when she didn’t move away, he pressed into a full kiss.
It was magical what his lips did to her. She melted into him as he kissed her, distracting thoughts of David gone for the moment. And then he broke it off.
“Let’s sit on the sofa while we wait for the wine to arrive,” he said in his charming English accent.
“Okay”, she managed to say.
They sat on the sofa, and he kept his distance, asking about her life back in the States. Janet invented a home decorator’s life, thinking it sounded better than her housewife’s life, while wondering what he planned to do with her. She was getting mixed signals with the passionate kiss at the door, but now his sitting a distance away. Janet was confused.
The doorbell rang, and he got up and went to the door, got the wine and glasses, and returned. He poured two glasses of wine, handed her one, dinked his glass against hers as a sign of friendship, then took a sip and set his glass down. This time, when he sat on the sofa, he sat right next to her. He picked his glass up, took another sip, set the glass down, and put his arm around her. He leaned into her and kissed her on the neck. Shivers ran through Janet as his lips gently tickled her, and she lost herself in the moment as she bent her neck to accept his kiss, then turned toward him. He left her neck and put his lips on her mouth and kissed her deeply. Janet melted yet again, and this time she kissed him back.
How could she let a stranger two hours ago become so intimate so quickly, she wondered. But Janet knew the answer; David had left her to her own devices, trusting her when he should have known she would feel deprived of his love. So when the fast and sexy Reginald came along, she was primed to let him take her. She set her glass of wine down and focused on kissing Reginald. And she knew if he pressed things, she would cave.
Her predictive skills were right on, for with her slight encouragement, as evidenced by her kiss, Reginald did just that.
“Would the lady like to continue in the bedroom?” he asked with a smile.
It was the moment of truth for Janet, but she already knew the answer. David had sabotaged things once too often, and Reginald was her knight in shining armor.
“Why yes, I would,” she replied with a smile.
And so they walked to the master suite, and immediately after entering, Reginald kissed Janet once more, while his hands slipped the straps of her ‘little black dress’ off her shoulders. The dress fell to the floor, exposing her bare breasts and the black thong she wore. His hands were cupping her breasts in no time, and he complimented her on how fine they were before he kissed her nipples. He teased her nipples with his tongue and then moved his mouth away as he rolled her nipples between his thumb and fingers, giving Janet a shiver.
Janet was alive with forbidden desire, her pussy getting wet under her thong, and she had to let the energy out, so she kissed Reginald hard. He returned the kiss as he dropped a hand to her crotch and headed where no man other than David had gone before. He found her pussy, and pressed his hand against it. When the hand on her tits joined the other in reaching for the side straps of her thong, she was ecstatic. He pulled her thong down and over her hips, and it fell to join the dress below.
Standing naked before him, Reginald grabbed her and lifted her into his arms. He took her to the bed, pulled back the covers, and set he down gently. He leaned over and kissed her, then stood and undressed, seemingly in no hurry. Janet watched him expose his older body as she considered that she had willingly committed to this illicit sex and was about to fail the “Seinfeld” cheating test big time.
When he was naked, he climbed onto the bed with her, caressed her breasts and nipples again, to her delight, and then spread her knees apart and moved his head to her nether region. He licked her wet pussy, and used his tongue to delve into her and open her pussy lips. She jerked in reaction to his tongue as it touched nerves in a way David never had. She was wet to begin with, and now she was positively sopping, as he licked her clit and drove her wild. She squirmed in ecstasy as he ran his tongue over her most sensitive place, moaning in pleasure, and got so turned on that she was open to anything Reginald wanted to do.
He could tell how aroused she was, but he stopped and ran his hand between her legs, split her pussy lips again, and traced her slit’s length with his fingers. He probed her cunt and began to finger fuck her, letting his thumb graze her clit with each thrust, to her continued pleasure. She rocked with his insertions and felt her arousal nearing a climax.
Next, Reginald put on a condom, got on his knees, and aimed his erection at her pussy. She felt his penis head press against her opening, and soon he was pushing into her. His cock filled her empty cunt in such a wonderful way that she almost came instantly, but she denied herself to make the joyous feeling last. He fucked her for several minutes before he jerked and spasmed, filling the condom as he shot his load. She felt the warmth as he unloaded all he had, and with the pleasure of his clit play, it drove her over the edge. Janet came hard, the culmination of urges that had built since she left home, spilling her nectar over his cock and balls.
After their sex, Reginald held Janet for a tender moment, and then got off the bed and got dressed. He thanked her for a wonderful evening and then left. She knew what he did was essentially his job, and he was probably off to find another single woman at the bar, but still, she had enjoyed his gentlemanly way and his gentle and refined sex immensely.
After Reginald left, Janet slept beautifully all night long, remembering his soft touch and how turned on she had been. She forced herself to fight off the guilt she felt for cheating on David, helped by knowing David’s lack of planning had set it up.
o o o
In the morning, Janet showered and went to a late breakfast in the dining room. Reginald was there, saw her, and smiled at her, but he was already with another woman. She had hoped he might spend some more time with her; he was so charming, and good in the sack! But he seemed to move from woman to woman, making sure they all had ‘a good time’.
So, breakfast ended uneventfully, and Janet went back to her villa, read the news online, and then put her mini-kini on. It had a dark blue top and a thong that barely covered her pussy, and she was wearing it for the first time, so she was a bit self-conscious. It was just after noon when she walked to the pool, getting long looks from the male staff who were cleaning or working the grounds.
At the pool, she lay on a beach lounger, and a waiter came over. He, too, seemed to notice all the skin she was showing, but acted professionally in taking her order for a mai-tai and a ham and cheese sandwich for lunch.
After lunch, while she read a steamy novel and relaxed in the sun, a nice-looking black man in a Speedo swimsuit, who must have been ten years younger than her, came over and asked if he could sit with her for a bit. He seemed friendly, so she agreed. He introduced himself as Peter, a tourist from Canada. Janet gave him her name, and they shared a little about each other. They got along fine, and like Reginald, Peter was a perfect gentleman. He even helped put some suntan lotion on her, arousing her as he did her inner thighs with gentle hands. Her mind went to sexual thoughts in no time!
They talked about where they were from and what they did for a living, even as she could not stop thinking of fucking this hot black man. She again said she was a home decorator, a lie, and he said he was a realtor. After a while, he announced that he had to go, but asked if he could take her to dinner that evening. She quickly said, “Yes.”
o o o
After going back to her villa, she took a shower and got ready for dinner with Peter. She wore the little black dress again, since it worked so well the last time. He picked her up at her villa at seven, and they walked to the resort’s best restaurant.
During a fine dinner, they talked about why she was married but alone, and how he ended up there as a single man. He explained he was divorced and preferred it that way. When they were done with dinner, he mentioned something they might enjoy doing that evening.
“I hear there’s a pretty wild party tonight at the biggest villa; some rich guy is treating. Would you like to go with me?” Peter asked.
“Okay,” Janet quickly replied, thinking that her idea of fucking him later was progressing nicely.
“But can I go to my villa to freshen up, and meet you there?” she asked.
“Sure. I’ll meet you at the bar.”
“Great!. I’ll see you in a little bit.”
It was only the second day at the resort, but Janet realized she had already lost all of her inhibitions. She walked to her villa and, upon entering, she got the surprise of her life! There, sitting on the couch having a beer, was her husband, David!
“Wow, you’re here, David! How did you get away?” she asked, trying to hide her shock and guilt.
“I found the problem that was keeping us from passing the last test, and we worked out a solution, so I was able to join you,” David said.
“I’m so glad,” Janet managed to say.
“Did you have dinner already?” David asked.
“Yes. But I was about to go to a party that everyone is invited to. Maybe you’d like to go, and I’m sure they’ll have some food there,” Janet said, feigning a desire to have David join her, but really it was just an excuse so she could let Peter know what happened.
“Okay. Let me just change into something better,” David answered.
After a few minutes, they headed out. They found the rich man’s villa by simply following the sound of loud music, then the added din of talking and laughter as they got closer. The party was well underway, and they headed to the bar. Janet saw Peter there, but between her signal and his quick comprehension, he realized her husband had shown up, so their date was off. David got them drinks, and they drank them at the bar. Janet saw Reginald with another woman, apparently ‘working’ yet again; he nodded slightly to her, and David did not notice.
After David finished his beer, he surprised Janet by asking her to dance. He had not danced with her in years, but she was thrilled, and they took to the dance floor. Three dances later, they sat at a table, and David excused himself to hit the restroom and look for some food. While he was gone, Janet decided to go to the ladies’ restroom and then explore the elaborate villa, which seemed as large as a small hotel. She got up, and after the ladies’ room, she wandered the villa, and eventually headed down a hallway lined with multiple bedrooms. As she passed one of the bedroom doors, it opened, an arm reached out, grabbed her, and pulled the shocked Janet into the room.
o o o
She was quickly held with her hands behind her back and a hand over her mouth. There were three men in the room, all wearing ski masks, and two of them held her such that she could not scream, nor escape. Janet knew she should be afraid, but somehow, after last evening with Reginald and the desire she had for Peter, she wasn’t. She had read about consensual non-consensual experiences, and it seemed she was being given the chance to experience one. After some quick thinking about how liberating the first two days had been, she decided she would just enjoy whatever happened.
“We will let go of you if you promise not to scream or fight,” the third man, who was not holding her, said.
“I promise,” Janet muffled through the hand over her mouth.
The man nodded to the one covering her mouth, and he removed his hand, but the other man still held her arms behind her.
“What is this, boys?” she asked. “It looks like it could be fun! Are you guys looking for a little gang bang action, or what?”
“Something like that,” the third man said. She decided he must be the ‘boss’ of this group.
“Well, I’m up for it, boys! Just tell me what you want,” Janet said with enthusiasm.
The boss man told them to let her go, and Janet looked forward to a new-to-her group sex experience.
“Strip, lady,” the boss man told her.
Again, Janet cooperated and slipped her dress off. This freed her breasts since she wore no bra, and left her in her black thong. The boss man nodded that she should remove that too, so she did.
Then the two men who had held her earlier guided the naked Janet to the bed and onto her hands and knees so her rear and head were each near an edge of the bed. The boss man moved behind her and dropped his pants, while one of the other men moved to her head and undid his jeans. Janet knew what they were about to do… and was loving the idea! She found the thrill of being held captive, naked and helpless, to be a turn-on, and she was already wet. The men wasted no time in entering her, the boss man sliding his erection into her pussy while the other man put his cock at her lips; she took him in and sucked.
Just as they started to fuck her, there was a knock at the door. They ignored it, but then suddenly the door opened since the men had not bothered to lock it… and there stood David!!
The man who was not fucking Janet pulled David into the room. David was shocked at seeing his wife being spit-roasted by two men in ski masks. But Janet seemed to be handling it well; in fact, she seemed to be enjoying it! As he watched, she was rocking back and forth with the man fucking her from behind, and giving the other man a good blow job. He had no idea that his wife was so sexually adventurous that she would even entertain such a thing, but she was moaning in pleasure. And like a cuckold, he watched, and he started to enjoy it, knowing that Janet was in ecstasy.
Soon, the man at her head jerked and came, shooting his load into Janet’s mouth. She watched him pull out and put his jeans back on. She swallowed his cum, and then he switched places with the man standing by David, with the new man putting his cock in Janet’s mouth. All the while, the boss man continued to fuck her doggie style, and she continued to love it!
So, Janet was being spit-roasted, which was something new for her, and David was watching her, which was all new for him. But she was enjoying the sex, her pussy alive with arousal and leaking her juices as the men worked her over. David’s arousal grew as he watched his wife being fucked, and he got hard.
When the boss man suddenly increased his thrusts, then jerked and shot his load into her pussy, Janet felt the warmth and got a surge of arousal. She gasped as much as she could with a cock in her mouth, and came hard. Janet squirmed and moaned as her cunt reacted to how turned on she was, spewing her juices onto the boss man’s cock. Meanwhile, the man getting a blow job also shot his load, and Janet gagged a little before swallowing his cum.
Both men withdrew from her and pulled up their pants, leaving a load in Janet’s pussy to drip and run down her legs. Then, the boss man invited David to take a turn, and as turned on as he got watching his wife enjoy her orgasm, he got up and stood behind her. He undid his slacks and dropped his boxers, then pushed his erection into Janet’s wet and waiting cunt. He pushed deep, and she moaned in renewed arousal. He fucked her intensely, still turned on from watching her fuck the masked men, and she reacted by climaxing again, her orgasm rejuvenated by David’s thrusts. She moaned with the pleasure of a second orgasm as she leaked more of her juices onto his cock, and they fucked until he shook, jerked, and came. While they were fucking, the three masked men slipped out the door, unnoticed.
“You were so brave, my dear,” he told her. “And watching got me so hot for you!”
“I’m glad you found us! And glad you didn’t make a scene, but got turned on instead. Let’s make the best of the rest of the week here. I’ll make it worth your while!” Janet assured him.
o o o
So they dressed and left the party, returning to their villa, where Janet seductively stripped for him in the bedroom. Seeing his wife put on a strip show, and remembering how turned on he got watching earlier, renewed his erection. When she walked to him and undid his belt buckle, he let her take charge and undress him.
They got on the bed, and he took over, caressing her breasts, pinching her nipples, and finding her pussy. He spread her legs and teased her snatch with his fingers as he moved into position. He ate her pussy until she nearly screamed, then he pressed his dick into her. They made passionate love, with him thrusting wildly, appreciating her as he had not in a long time, and she enjoying his lovemaking skills again, after years of indifference.
They fucked each other every day and night for the rest of the week. And on returning home, David was a new man who initiated sex with his willing wife several times a week, and even showed an interest in swinging, if she wanted to. She said she’d like to try that!
It turned out that the week in the Bermudas, when Janet lost her sexual inhibitions and enjoyed sex more than ever before, and David’s interest was rekindled, was a turning point in their marriage.
