A Cuckold Story Ch. 01-07

That summer Cheryl juggled Dave and Jerry with aplomb as she slept with each of them at least two nights a week. And when I arrived home to begin fall semester, Cheryl didn't skip a beat as she continued to fuck Jerry at his apartment and instead of entertaining Dave at our house, she would visit him at his fraternity where she would head upstairs to his bedroom to spend several hours with him between her legs.

Cheryl said she loved making Dave's fraternity brothers jealous and she would regularly show up at his frat wearing one of her provocative work outfits. Unlike the typical casual college attire worn by the girls these other guys dated, Cheryl would usually be dressed in one of her sexy business suits or dresses. And she would always be wearing her, now trademark, thigh high stockings and high heel pumps. Dave had learned early on that Cheryl enjoyed a glass of white wine before heading up to his room and they would sit on the large couch in the frat sipping their drinks while chatting with Dave's fraternity brothers. It never failed to excite Cheryl as she crossed and uncrossed her legs, giving all the guys brief glimpses of the lacy tops of her stockings and even the occasional peek of her panties as she teased them mercilessly. And when she and Dave finished their drinks and were headed to his room, she always left her skirt hiked up, savoring the attention as she felt all the guys' eyes on her legs and sexy behind as she strutted up the stairs with her lover.

When I eventually learned of Cheryl's cheating, I was amazed at how easy it was for her to rationalize her infidelities. If the roles had been reversed, I would have been wracked with guilt if I had ever slept with another girl. But for Cheryl, the fact that these guys sexually satisfied her in ways I could not made it all okay in her mind. And although she wasn't particularly happy with having to deceive me, she never once regretted her duplicity when she was in bed with one of her lovers, welcoming his thick cock into her pussy or mouth.

Chapter 6

As it turned out, Cheryl's frequent nights and weekends "out with friends" or "working late" allowed me to devote considerable energies to my studies. I had not been a great high school student, but as soon as I had started community college I had excelled in my classes and now, at university, I was at the top of my class. Since I was burning the candle at both ends by working and attending college, I was determined to graduate as soon as I could and after two years, I finally had enough credits to graduate. I had graduated with honors and subsequently received several job offers relatively quickly. And after Cheryl and I discussed the various offers, we both agreed we missed the Bay Area and wanted to return. Since I had received one offer from a firm in San Francisco, I chose that one and we were soon on our way back home. And once we had settled into our new apartment, Cheryl quickly found a job at another bank within just days of looking.

Cheryl later confided that she had grown somewhat bored with both Jerry and Dave and she was happy to start the next chapter of her life without having to juggle two lovers in addition to me. And so, for the first several years back in the Bay Area, Cheryl was relatively monogamous, only carrying on one, brief affair with a security guard at her office and a couple of random short-term affairs with guys she met at her gym. She did also head down to L.A. to see both Jerry and Dave several times during this period, telling me she was visiting friends, but as they were both now in relationships, coordinating their get-togethers wasn't as easy as it had been.

Cheryl's next true affair was with Brad, an acquaintance of ours who we had met through mutual friends. Like Cheryl's boyfriend, Jerry, in Los Angeles, Brad was older than Cheryl and me at around 30 years old and worked as an Associate at a large law firm in the City. Brad was quite the lady's man and when he wasn't escorting some new conquest on his arm, he was flirting with Cheryl, even to the extent of making suggestive remarks right in front of me. I'd always try to laugh off his risqué comments but inside I'd be fuming that he thought it was okay to flirt with Cheryl since she was clearly taken. Later, once Brad was gone, I'd complain to Cheryl that he was coming on to her, but she would ignore my concerns, telling me, "C'mon Mike, he's just joking around. He's not serious." Brad was tall and very handsome, but he was also cocky and arrogant, and Cheryl would frequently tell me, "He's so full of himself. No wonder he goes through so many girlfriends." But as I've come to learn, the same personality traits that Cheryl might find annoying or unappealing in a friend or husband, she also finds irresistible in a lover. And as I later discovered, Cheryl had harbored a secret crush on Brad from the very first time they met.

One day when I was in Chicago for a several-day training session, Cheryl ran into Brad on the train home from work. After telling him that I was out of town, they agreed to have a drink before heading home. In the back of her mind, I'm sure that Cheryl was excited to be joining Brad for a drink, but she insists to this day that her intentions were innocent. A couple of drinks later, however, Brad placed his hand on Cheryl's thigh and was thrilled to feel the outline of her garter clasps and the lacy tops of her stockings beneath the thin silk of her dress. You see, Cheryl had continued to dress as she had in Los Angeles and although her new company's dress code was significantly less uptight, she continued to wear skirts or dresses coupled with a garter belt and stockings or just thigh-high stockings to work. And when Brad realized that Cheryl was dressed in these sexy undergarments, he turned into an animal, pawing her at every opportunity while she halfheartedly tried to fend off his advances.

Cheryl said that it was a good thing they were in a secluded booth as Brad's hands were all over her and the hem of her dress had risen to reveal her creamy thighs above her stocking tops. Eventually, Cheryl gave in to her own desires and when Brad ran his hand beneath her dress to caress her panty covered pussy, she leaned over and kissed him full on the lips before whimpering, "Let's go back to my apartment." They left before they'd even finished their third drink and within minutes they were back at our apartment where they fucked and sucked pretty much all night long.

That first night with Brad, Cheryl was smitten. Brad was aggressive and confident in bed and he had Cheryl coming multiple times over the course of the night. Cheryl said that she knew almost as soon as they started fucking that this was not going to be a one-time event and before the evening was through, Cheryl had made plans to see Brad again the very next night.

That second night with Brad was even better than the first, with Cheryl welcoming him to our apartment wearing nothing but a pair of thigh-high stockings and high heel pumps. It seemed that Brad and Cheryl truly had sexual chemistry and they literally fucked for hours, stopping only to enjoy a light dinner that Cheryl cooked while Brad sat back and watched Cheryl busy herself in the kitchen, still naked with the exception of her stockings and shoes. And later that night, after fucking for a third time, Cheryl told Brad that she wanted to continue to get together with him, explaining that sex with him was the best she'd ever had.

Cheryl's affair with Brad lasted over two years and they would get together frequently, even right under my very nose. We saw Brad regularly as we had many common friends and we frequently hosted him at our apartment at various dinner parties. Cheryl told me that Brad was always teasing her at these events and whenever he could get away with it, he would grab a feel of her tits, or run his hand up her skirt to feel her moist pussy. And on one memorable occasion, Brad and Cheryl wandered off at a party given by one of our good friends and she sucked him off in the upstairs bathroom. Cheryl said that she could taste Brad's sperm the rest of the night and when we got home, she attacked me, reveling in the sheer naughtiness of what she'd done. All this time, however, I was completely oblivious to Cheryl's cheating and I never would have guessed that Brad and she were carrying on a torrid clandestine affair.

Brad lived not far from us and Cheryl would visit him at his apartment at least once or twice a week on her way home from work. Since I was no longer working at night as I had done during college, Cheryl would come up with elaborate excuses as to why she was coming home late. Cheryl regularly used the working late excuse and I bought into it hook, line and sinker as I merely assumed that she was trying to advance at her job. And never once did I notice that Cheryl always looked somewhat disheveled after "working late" at the office.

Brad was a somewhat more forceful lover than Cheryl had had in the past and he would often spank her ass while they fucked leaving her cheeks with a rosy red glow for several hours after their get-togethers. And on those nights, Cheryl told me she would have to hide her bottom from me as she undressed, fearful that I might catch a glimpse of her reddened behind. Arriving home, Cheryl would quickly strip off her clothes in her closet and then don one of her long flannel nightgowns. And if that dowdy attire wasn't enough to preclude any amorous overtures from me, Cheryl would invariably spurn my advances, telling she was too tired for sex.

Cheryl said that Brad really got off on treating her as his personal slut and after she'd greeted him wearing just stockings and heels on their second night together, Brad insisted that he wanted Cheryl dressed similarly whenever they got together. And so, when Cheryl would show up at Brad's apartment, she would immediately strip her down to just her stockings and shoes, leaving the rest of her clothes neatly folded on the table in his entry. They'd often have a glass of wine together or even a light dinner, and Cheryl said the sexual dynamic of being essentially naked while Brad remained fully clothed never failed to have her dripping with anticipation. Brad would often tease Cheryl that someday he'd invite several of his buddies over and they'd all take turns with her, and whenever she showed up at his apartment Cheryl would be nervous that there might be an entire group of horny guys waiting for her. And although she'd always half-heartedly tell Brad that she had no interest in fucking anyone but him, Cheryl said the thought of taking on a group of well-hung studs became one of her recurring fantasies. Alas, Cheryl had to leave that particular sexual experience as a fantasy as Brad never did follow through on his threat to include his friends in their escapades.

Like many of the other men who have cuckolded me over the years, Brad relished the fact that Cheryl was my girlfriend and he seemed to derive a special thrill in bedding another man's woman. And during their sessions, Brad was always goading Cheryl to tell him how much bigger he was than me, or how much better he fucked her. Now, the truth was, Brad's cock was at least twice the size of mine and he could fuck for hours while I was usually done in minutes. And so, while they fucked, Cheryl would spur him on, cooing, "Oh my God, your cock is so much bigger than Mike's. It feels so good. You fuck me so much better than Mike. I love it." Brad's reaction to Cheryl's flattering comparison of his sexual skills and attributes taught her to appreciate the innate power of competition that drives most men, particularly men with more alpha personalities. And from that point on, Cheryl would use these same lines to stimulate future lovers, telling them how she needed their big cocks because my penis was too small, or how they fucked her far better than I ever could. I must confess that when Cheryl first told me this, it was a blow to my ego, but she assured me that it was just "dirty talk" designed to arouse her lovers. And she added that whenever she and whomever she was with had finished fucking, she would always remind them that despite my sexual shortcomings, she loved me dearly and had no intentions of leaving me. This lessened the hurt to some degree and ironically, over time, I've learned to take pleasure in the reverse of these comments, becoming aroused when Cheryl tells me I'm so much smaller than her lovers or that she needs other men to truly satisfy her.

To this day, I suspect that Brad must have told some of our close friends about his affair with Cheryl. Brad was a notorious braggart and on more than one occasion I'd overheard him bragging to the guys about one of his recent conquests, describing all sorts of intimate details that left little to the imagination. Given Brad's typical boorish behavior, I can't imagine that he could have kept his long running affair with Cheryl to himself. And when I first learned of Brad's affair with Cheryl, I felt humiliated at the thought of him regaling our male friends with details of their trysts, or worse, telling them how Cheryl was cheating on me because of my tiny penis and lack of stamina. But over time I've grown comfortable with the fact that, at a minimum, some of our male friends likely knew of Brad and Cheryl's relationship. To be sure, this acceptance didn't come quickly or easily but, as I've embraced the fact that I'm a natural born cuckold, I've learned to accept my own sexual inadequacies. And, oddly enough, I've developed a certain sense of pride in Cheryl's uninhibited erotic adventures. And although we've never flaunted our unique relationship, if some of our friends and acquaintances have heard of Cheryl's escapades and are scandalized by her behavior, then so be it.

Brad eventually moved away and not long after that Cheryl and I decided to buy a house and move to the suburbs. It was a big decision for us and although we loved living in San Francisco, the prospect of having a home we could call our own convinced us that we needed to make the move. After several months of looking we eventually settled on a nice suburban ranch house that needed some updating but had a large yard and a swimming pool. For the first six months or so we worked on the house tirelessly and each evening we would sit around our pool toasting our good fortune.

Cheryl was relatively monogamous during this time although she did hook up with Brad twice when he arranged to come visit the area. Of course, I only learned of this much later, but I still get a thrill thinking about how I foolishly offered to let him stay the night after we hosted a small dinner party with friends. The very next day after I left for work, Cheryl called in sick and Brad and she spent the day fucking even going so far as to brazenly fuck outside around the pool where our neighbors might have seen them!

Now that we were living in a sunnier suburb, Cheryl began to dress in even skimpier clothing than she had in the past. Miniskirts and short shorts became standard attire and although she still occasionally wore stockings and thigh-highs, for the most part Cheryl went bare legged. Of course, this meant she made sure her legs were tanned, and Cheryl would spend a couple of hours each weekend sunning herself around the pool while I toiled in the garden. Because our yard was relatively private, Cheryl wore only thong bikinis around the pool and she soon developed the sexiest tan lines on her shapely rear end.

Since we were now homeowners, it was only a matter of time before I proposed to Cheryl and she agreed to marry me. I'll never forget the joy I felt as I slipped a ring on Cheryl's finger and we began to make plans to be married. Our engagement was to be several months long as we wanted to be married in the summer, but we soon set about planning for our wedding.

Cheryl had promised herself that once we were married her infidelities would be a thing of the past, but over the course of our engagement she was determined to enjoy her last remaining moments as a single girl. And over the three months preceding our wedding, she slept with a total of five different men. Three of them were guys she had lusted after for some time and she wanted to cross them off her list before we wedded. One was the husband of one of her friends from work. We had hosted Susan and her husband, Brian, at our new house on several occasions and although Brian and Cheryl got along well, I never noticed anything amiss. However, unbeknownst to me, Cheryl and Brian had been flirting incessantly whenever they had a chance and eventually Cheryl called Brian and asked him if he could meet her at local bar to "talk about investments." It seems that Brian was a stockbroker and when they met up, he and Cheryl spent only a couple of minutes talking about investments before he made his move and within no time at all, Cheryl found herself in a hotel room and she and Brian spent the next several hours screwing each other with abandon. Cheryl met up with Brian several more times in the months before our wedding, eventually telling him they needed to stop as she wanted to be faithful once she was married.

The second guy to screw my fiancé was a client at her firm that she had known for some time. Whenever this guy was in her office, he would always make a point to talk with Cheryl and their conversations were always flirtatious and filled with innuendo. When he noticed that Cheryl was now wearing an engagement ring, he offered to take her out for a drink after work to "celebrate her engagement." Cheryl accepted his offer and after several drinks at a local bar, they ended up in the back seat of his car where they had a boozy fuck lasting for almost an hour. Cheryl later told this guy that it was a one-time thing and from that point on she rebuffed his invitations to join him for another drink.

The third guy was, Ken, a guy she had met while working out at her gym. Ken was a weightlifter and with his rippling muscles and imposing physique, he reminded Cheryl of Dave, her lover in Los Angeles. Cheryl had quite the crush on Ken and she made a point to work out near him whenever she could. She eventually worked up the courage to ask him if he had any pointers on weightlifting as she was thinking that she might want to add that to her fitness routine. After that initial introduction, it was only one week later that Cheryl was lying on her back in Ken's apartment preparing to accept his thick cock into her sopping pussy. Ken and Cheryl fucked a couple times more before Cheryl told him they needed to break things off in anticipation of her upcoming wedding.

The fourth guy to sleep with my sexy fiancé before the wedding was none other than Brad whom we had invited to attend our wedding. At Cheryl's urging, he arrived into town four days early and booked a room at a hotel near our house. Cheryl had taken the week off from work before our wedding and each, and every, day, she would arrange to stop by Brad's hotel for several hours to enjoy a lusty session with her lover. Cheryl even arranged to spend an entire night in Brad's bed as she told me she was spending the night at the hotel room of her friend Ann from Los Angeles. Ann was a willing accomplice to this deception telling me later at our wedding reception that she and Cheryl had enjoyed "catching up" when, in fact, they had merely enjoyed a light lunch together, with my fiancé filling Ann in on all the juicy details of her affair, before she headed to Brad's hotel.

As much as she was enjoying sharing her charms with other men on the eve of our wedding, Cheryl had distinctly contrasting views when it came to me. In fact, when she learned that several friends were planning on hosting my bachelor party at a strip club, Cheryl threw a tantrum, insisting that she didn't want me ogling any strippers before our wedding. It took quite an effort to calm her down but eventually I was able to pacify Cheryl when I called each of my friends, sheepishly suggesting that we get together at a local sports bar instead. Of course, later that evening as I was drinking beers with my disappointed buddies, Cheryl was out partying with her bridesmaids, ultimately going home with a guy she met at a dance club. This was the fifth man to fuck my fiancé before our wedding and the fact that Cheryl's bridesmaids saw her leave with this guy and were privy to my cuckolding didn't seem to bother her in the slightest. That night, Cheryl didn't return home until the wee hours of the morning, telling me she had fallen asleep at Ann's hotel.