A Cuckold Story Ch. 01-07

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Within only a couple of weeks, Cheryl was successful in landing a teller job at a downtown Los Angeles bank and, Jerry, the assistant manager of the branch set his sights on her almost immediately. At thirty years old, Jerry was older than Cheryl and me and when he made his move, Cheryl succumbed to his mature, masculine charm and tall, muscular physique. It didn't take much to get my sexy little girlfriend into bed and I still remember the Friday night that Cheryl said she was going out with some girls from the office. The truth was, Cheryl wasn't going out with the girls from her office, but, instead, had accepted Jerry's offer to take her to dinner. That night Cheryl called me at almost eleven-o-clock to tell me she'd had too much to drink and was going to spend the night at her female co-worker's apartment. When I offered to come pick her up, Cheryl refused, telling me she was headed to bed at that very moment. It turned out Cheryl wasn't lying about that, and when she hung up the phone, she headed straight back to Jerry's bed to find him already sporting an erection in anticipation of fucking my girlfriend for the second time that night.

When I later learned about Cheryl's infidelities, she didn't try and sugarcoat her motivations for yielding to Jerry's advances. Cheryl said that in addition to being very good-looking, Jerry had confident, some might say assertive, personality that she found irresistible. And when Cheryl eventually told me of her affair, Jerry was the first of her many lovers that she described as a "real man." First hearing this expression, I ascribed it to the fact that Jerry was older than Cheryl and me, but over the years I've come to understand it's much more than that. In Cheryl's view, a "real man" is a man who not only has the physical attributes she enjoys in a man such as a handsome face and a tall, muscular physique, but a "real man" is also confident in his masculinity and even thinks of himself as a "real man." To me, a much more sensitive man, many, if not most, of the men that Cheryl considers "real men" come across as arrogant and conceited and, in reflection, Cheryl oftentimes agrees with me on this. But, arrogant or not, when Cheryl meets a tall, handsome man who is confident in himself and his place in the world, there's always been a decent chance that a "real man" like this can entice her into his bed. Jerry was just such a man and on their very first night together, Jerry brought Cheryl to more orgasms than she'd had in over two months with me!

After thoroughly enjoying her passionate night at Jerry's apartment, for the next two years, Cheryl carried on a torrid affair with Jerry, fucking and sucking every chance they got. Jerry's apartment was only a couple of blocks from Cheryl's office and they would frequently enjoy quickies over lunch, and she would often stop by his place on her way home from work. Their affair was aided by the fact that I had landed a job on campus and my hours were from six to midnight four nights a week. This provided plenty of time for Cheryl and Jerry to get together and I remained completely oblivious to the fact that my girlfriend was fucking and sucking her handsome boss on a regular basis.

It was Jerry who first introduced Cheryl to the erotic nature of sexy lingerie and during this time Cheryl began wearing lacy bras and panties along with garter belts and stockings. And rather than the wooden platform shoes she'd habitually worn as a college student, in their place Cheryl started wearing stiletto pumps and high heel sandals giving her a decidedly more sophisticated appearance. I absolutely loved Cheryl's new wardrobe and I would frequently beg her to dress up in stockings and heels when we made love. Oddly enough, Cheryl was always reluctant to dress up for me and I could probably count the number of times she did so on one hand. However, Cheryl was not so reticent with her boyfriend, Jerry, and he always insisted she keep her stockings and heels on whenever they had sex.

The bank that Cheryl and Jerry worked for had an old-fashioned dress code and although it seems silly in today's world, they required that women wear skirts or dresses with nylons and men were required to wear a suit and tie. When I later learned of her affair, Cheryl told me that Jerry would frequently stop by her desk on the mornings of the days they planned to get together. He would then have her surreptitiously slide her panties down her legs and hand them to him while all the while pretending to carry on a professional conversation about work. Jerry would then slip the flimsy garment into his suit pocket and Cheryl knew that she'd only get them back after they fucked. Cheryl said it always gave her a naughty thrill to spend the day alongside her conservative co-workers knowing that one wrong move on her part might expose the lacy tops of her stockings, much less her bare pussy. And by the time she and Jerry made it to his apartment, Cheryl would be dripping with excitement and she would hike up her skirt and allow him to take her right then and there, fully clothed except for her panties. If their rendezvous was merely a lunchtime quickie, Jerry would then give Cheryl her underwear back and she would spend the remainder of the day in an equally excited state as his load seeped out of her and into her panties. If their get together was after work, Cheryl would spend the remainder of the evening in various stages of undress fucking and sucking Jerry until she'd earned her panties back.

Throughout Cheryl's affair with Jerry, I never suspected a thing. Cheryl and I were still the same loving couple we had always been and although I was frequently busy with school, we still had plenty of enjoyable times together. I suppose, in hindsight, I should be thankful that my girlfriend had someone to regularly see to her sexual needs and given Cheryl's libido, I now know that if it hadn't been Jerry, it would have been some other well-hung stud.

Chapter 5

Cheryl had one other lover during our time in Los Angeles and it turned out I was the one who indirectly introduced this guy to my girlfriend. Early in my first semester I had befriended several classmates who were in the same major as me. Cheryl and I spent quite a few evenings with these new friends and Cheryl ended up hitting it off with some of the girls who were part of that crowd. Cheryl became quite friendly with Ann and Mary and they started hanging out on a regular basis. They would go out in the evenings for "Girl's Night Out's" and they would hit the beach pretty much every weekend. With my work schedule, I typically needed to study on weekends and so I missed out on much of the fun, but there was usually a large group of friends who would join them for tanning, swimming, surfing, and volleyball. Often, the parties would extend into the evening where everyone would sit around beach fires and drink beer and wine.

Now, I knew that these beach parties were prime spots for casual romantic hook-ups, but I didn't think I had any reason to distrust Cheryl and she was always chaperoned by Ann and Mary. Besides, I'd attended my share and I knew most of the people attending either from my classes or indirectly, through friends. As I learned much later, Cheryl had fended off quite a few advances during this time and she had been sorely tempted on several occasions when one of the broad chested volleyball players or surfers would take an interest in her.

It so happened that during summer break, I had agreed to join two friends of mine in the Bay Area to paint a couple of homes in Marin county. We anticipated making quite a bit of money from these jobs and I couldn't pass up the opportunity. Although, I was reluctant to be without Cheryl for two months, we both agreed that the money was too good to pass up and so when the semester let out, I headed north for my job.

For the first week or so, Cheryl made up for missed opportunities and basically lived at Jerry's apartment. Although each evening the two of them fucked and sucked like long lost lovers, Cheryl eventually realized their attraction was purely physical and she wasn't really interested in waking up to him every morning, much less spending the day with him on weekends. She also missed her friends and so, after explaining that she needed to spend more time at home, Cheryl went back to her more manageable routine of seeing Jerry a couple of times a week after work.

Once Cheryl was back in our apartment, she called up Ann and Mary and they immediately planned to hit the beach that upcoming Saturday. And Cheryl was so excited to party with her friends that she went out that week and bought a skimpy new black bikini just for the occasion. That Saturday the weather was perfect and there was a particularly large group hanging out at the beach that day.

Cheryl and her friends spent much of the day lounging on the beach gossiping, reading fashion magazines, and basically just soaking up the sun. All this time, various acquaintances would stop by to chat but for the most part, the three girls kept to themselves. Late in the day, however, Mary exclaimed, "Hey Cheryl, there he is!" When Cheryl looked in the direction Mary had indicated, she saw Dave, one of the guys whose advances she had rebuffed a month or so before. Cheryl had told her friends about Dave's attempted seduction and, ever since, they all gossiped regularly about it.

As Ann and Mary kidded Cheryl about her admirer, Cheryl took her time surveying Dave as he joked around with his friends. Dave was tall, at least 6'3" or 6'4" if she had to guess. And Dave's broad muscular shoulders and six pack abs gave evidence to his regular workout routines. Cheryl had to admit Dave was a real stud and she found herself entertaining naughty thoughts as she gazed in his direction.

Although Cheryl liked what she saw when looking at Dave, she turned to her two friends and said, "I told you, I let him know that I didn't want to cheat on Mike."

The girls all laughed at this as Ann replied, "Yeah, but Mike's out of town for the summer. What he doesn't know won't hurt him, right? Are you telling me you don't want to see if the rumors are true?"

Now, Dave had bedded quite a few girls in our crowd and apparently there were rumors that he was packing one of the largest cocks any of them had ever seen. Cheryl just giggled at Ann's comment as she then reiterated that she wanted to be faithful to me. Ann and Mary both laughed at Cheryl's statement with Mary adding, "Mike's nice and all, but you're telling me you don't want to have a fling with a guy like Dave?"

Cheryl later told me that while she told her friends, "No", she was already fantasizing about what it would be like to spend the night with Dave, caressing his muscular shoulders as he thrust his manhood deep inside her juicy pussy.

Later that evening after the sun had set, the party began to get lively with beer and wine being opened and couples pairing off to sit away from the group and make out on the beach. The three girls decided to join the larger group that were sitting in the sand while several guys tended a fire. Ann and Mary had just left to go pee, when Cheryl felt someone sit next to her on the log and when she turned she saw Dave smiling at her with a large grin as he said, "Hey Cheryl, I see Mike's missing in action again tonight."

Cheryl explained that I was spending the summer working in the Bay Area, but that I would be returning for Fall semester. Dave developed an even broader smile at hearing this news as he offered Cheryl some wine from his cooler and, before long, the two of them were chatting like old friends. And when Ann and Mary returned from the bathroom, they sat elsewhere giving Cheryl conspiratorial smiles as they whispered amongst themselves.

As Dave continued to ply Cheryl with wine, she began to question why I'd always told her that he was a jerk. Although not close, Dave and I were in the same major and were frequently in the same classes. I never really liked Dave and he was the perfect example of the boorish, fraternity type who never applied himself to his studies but, instead, was more interested in getting drunk and picking up girls. And on one of the rare occasions when I had attended one of these beach parties, I had confided to Cheryl that I thought Dave was arrogant and condescending. But as she got increasingly tipsy, Cheryl began to think I was wrong, Dave wasn't a jerk at all, he was a nice guy and a very handsome one to boot.

As the evening wore on, it began to get chilly and with Cheryl wearing only her bikini and a thin cover-up she started to feel cold. This was a perfect opening for Dave and when Cheryl said she was getting cold, he pulled a blanket out of his bag and pulled it over the two of them, placing his arm around Cheryl and pulling her close. Cheryl later told me that when she felt Dave's muscular arm encircling her shoulders, she felt her pussy moisten at the thought of sleeping with him later that evening. All this time, Cheryl could see Ann and Mary sitting across from her snickering amongst themselves as they watched this seduction unfold.

It wasn't more than fifteen minutes or so later that Dave said he had to go pee and as he headed off to the bathroom, Mary made her way over to Cheryl and said, "It looks like you and Dave are really hitting it off."

And when Cheryl replied, "Yeah, he's really a nice guy. I think I may have been wrong about him", Mary just gave her a wicked smile while letting her know that she and Ann were heading out soon. The three of them had driven together in Mary's car and although disappointed that they had to leave, Cheryl started to get up, folding Dave's blanket and putting it back in his bag.

Just then Dave returned from the bathroom and as he made his way towards the girls, Cheryl said, "Let me just say goodbye to Dave first, okay?" She then walked over to Dave and after a brief conversation she headed back to Mary and Ann, telling them, "I think I'm going to stay a while longer. Dave said he can give me a ride home."

There were several snorts of laughter from the girls at hearing this, but after telling Cheryl they wanted a full recap the next day, they headed off towards the car leaving Cheryl and Dave to cuddle once more under his blanket. Within no more than ten minutes or so, Dave suggested that they leave and after gathering up his cooler and blanket the two of them walked towards his car. They didn't get far before Dave pulled Cheryl up into a secluded area of sea grass and driftwood, and laying down his blanket, he eased her down on the blanket and began to passionately kiss her lips. Cheryl loved Dave's assertive behavior and she returned his kisses with enthusiasm as the two of them made out on the beach.

Before Cheryl really had time to contemplate what was happening, Dave had removed her cover-up and bikini and when he stood up to lower his swim trunks, she saw that the rumors were indeed true. Dave was sporting a truly massive cock and Cheryl licked her lips in anticipation. He was already erect, and Cheryl immediately sat up, kneeling in front of Dave as she took his giant appendage into her mouth. No stranger to sucking cock, Cheryl bobbed her head up and down on his rod while teasing his heavy balls with her fingernails and running her other hand over his firm, muscular ass cheeks.

Cheryl kept up her oral worship of Dave's cock for several minutes, pausing only occasionally to remove his shaft from her mouth and to kiss and suck his hairy balls. When Cheryl began to sense that Dave was getting close to coming, she eased her mouth off his cock and lay back on the blanket, spreading her legs and begging him to fuck her. Not one to decline that sort of invitation, Dave moved into position and Cheryl hungrily grasped his penis and inserted into her already sopping pussy.

Cheryl said this was the first time she had ever been fucked on a beach and it was amazing. She could hear the waves crashing and she could even make out voices coming from the party they had just left and within no time at all, Cheryl began to orgasm, her body shuddering as Dave continued to impale her on his thick shaft. Dave was clearly an experienced lover as once Cheryl recovered from her orgasm, he flipped her over and began pummeling her from behind as he fucked her doggy style. Cheryl reached up between her legs and was fondling Dave's hairy balls when she sensed his impending orgasm. Anxious to climax simultaneously, Cheryl removed her hand from Dave's balls and began frigging her clit as they both roared out in orgasm together, their bodies joined as one.

When I eventually heard this story I had to admit, I was more than a little jealous. Dave had so expertly seduced my girlfriend and she had so eagerly submitted to his advances that I felt somewhat sick to my stomach. But at the time, I was completely oblivious to my girlfriend's cheating and while she was enjoying a world-class fuck, I was busy working my ass off to assure I had the funds to continue my college education.

After their incredible beach encounter, Cheryl and Dave went to our apartment where they enjoyed a more leisurely, but no less passionate, session in our bed. And after that, Cheryl and Dave got together regularly. Dave was living at his fraternity house and so for the remainder of the summer as well as occasionally during the school year when I was at work, they used our apartment as their love nest. Since we lived in a rather small apartment complex, I'm sure many of our neighbors saw Dave coming and going over the summer, but news of Cheryl's infidelities never reached my ears.

As promised, the next morning following her hook-up with Dave, Cheryl called both Ann and Mary. They were both anxiously waiting to hear what happened and so they all agreed to meet for lunch to hear all the juicy details. At lunch, when Cheryl described how she and Dave had fucked right there on the beach, both girls giggled with delight at Cheryl's naughty exploits. Cheryl freely admitted that not only were the rumors true, but that Dave was also a masterful lover, bringing her to several orgasms while he fucked her with his enormous cock.

It's always surprised me how graphic women can sometimes get when discussing their sex lives with close friends. And when I later learned that Cheryl had gone into explicit detail about her night with Dave, even favorably comparing his sexual skills and endowment to mine, I blushed in embarrassment. All of this "girl-talk" had Cheryl feeling emboldened and so she also confessed that she had been seeing Jerry for the better part of a year. To this day, I still get embarrassed when I think of how Ann and Mary knew all about Cheryl's sexual hijinks and I never once suspected a thing.

At first, Dave and Cheryl tried to hide their relationship to some degree, but since I was gone for the summer, they were not as discreet as they probably should have been. Whenever they attended parties together, they would leave arm in arm and more than once they were caught making out by various friends and acquaintances. Once, several weeks before the Fall semester was to begin, several of Dave's fraternity brothers inadvertently barged in on them as they were fucking in his bedroom and before Dave could shoo them out, each of them got an eyeful of Cheryl lying stark naked on his bed, her pussy still gaping open from Dave's large cock.

To this day, I'm surprised that I never caught on that Cheryl was cheating on me. Most of our friends clearly knew what was up, but I guess nobody wanted to tattle, thinking this was a matter that was purely between Cheryl and me. But, in hindsight, I recall that whenever I ran into Dave or any of his friends, they always had a smirk on their lips, and I would frequently see them chuckling as I walked by. I chalked this up to the fact that Dave and I didn't really get along, but I now recognize it as the reaction most men have when confronted with a cuckold. Whether they are doing the cuckolding themselves or not, most men have little, if any, respect for a cuckold and rather than feeling pity for a man whose wife or girlfriend is cheating on him, the cuckold is derided as being less than a man, someone to be treated with amusement and scorn. I don't know if it was the fact that I was head over heels in love, or maybe just that I was naïve, but I honestly think I was the only one who didn't know Cheryl was cheating on me during my college years.