A Cuckold Story Ch. 01-07

I think that Paula was so caught up in her anticipation of seeing Dan that she wasn't really listening to me as she merely replied, "Oh yeah, sure." Paula then checked her face in the mirror one last time before innocently offering me her cheek for a kiss. I then watched enviously as Paula walked up to Dan's front door, her shapely ass swinging side to side in rhythm to the clip clop sound of her high heel clogs on the walkway. Always the gentleman, I waited until Dan had answered the door and when he saw me waiting out front in my car, he gave me a big smile and a wave before ushering Paula into his house.

That night I was furious with myself for acting like such a wimp. How could I take Paula out to dinner and a movie, paying for everything, and then drop her off at another guy's house? And coupled with my self-loathing, I was overcome with jealousy and humiliation at Paula's blatant infidelity. However, as I lay in bed feeling the surge of emotions flowing through me, I began to masturbate. That night I jerked off four times to visions of Paula and Dan. Each time, after I came, I would be filled with shame and remorse and would vow to break things off with Paula. But then, later, I would feel myself getting hard once again and I would soon have my dick in my hand, pumping away as I pictured Paula and Dan in all sorts of erotic positions.

By morning I was a complete physical and emotional wreck. I'd hardly slept at all and my dick was rubbed raw from my incessant masturbation sessions. Despite my distress, I dutifully called Paula later that day and we took a nice hike in the hills where we happily chatted about a variety of things with the glaring exception of the elephant in the room, her night with Dan. As we talked, I realized that I really did like Paula despite her cheating. She was the same cheery, intelligent, and pretty girl she had been before I learned of her infidelities and I enjoyed spending time with her. However, at the end of our walk when I attempted to place my hand on her behind while we kissed, Paula gently but firmly pulled away from me, telling me that she wanted me to take her home.

Since I hadn't made a scene when I dropped her off at Dan's house after our date, I guess Paula just assumed that I would passively accept her relationships with other guys. In fact, over the course of the summer my dates with Paula would frequently end with me dropping her off not only at Dan's house but at John's, another classmate of mine. On two separate occasions, Paula would have me drop her off at parties and I'd be left to wonder just who she'd end up going home with later that evening. One night, Paula even went so far as to call me to ask if I would come pick her up at 2:00am from an address in San Francisco, telling me she had gone out dancing with a friend and ended up back at some guy's place for a final "drink". True to form, I did go pick her up and once I dropped her off at her house, I spent the remainder of the night jerking off while recalling how incredibly sexy Paula had looked as she met me in front of this guy's apartment, hair all askew, barefoot in her rumpled dress and with her high heel shoes in her hand.

I suppose I should have broken things off with Paula, but I'd quickly become addicted to my masturbation sessions whenever I knew she was with another guy. Perhaps, having read all those wife watching stories in Penthouse, I was somewhat conditioned to believe that what Paula was doing wasn't entirely unusual. But whatever it was, never in my life had I ever jerked off as much as I did whenever I'd drop Paula off at another guy's house. Before I even knew the word cuckold, I was living the cuckold life to the fullest and I would lie in bed furiously jacking off while picturing my girlfriend spreading her legs for Dan, or John, or any number of other faceless guys. I even began to embellish my fantasies picturing Paula taking on several guys at a time, taking load after load into her pussy and mouth. After I would come, I would end up feeling ashamed of myself and vow to break things off with Paula, but the next day I would inevitably call her and ask to take her out to a movie or to dinner.

And although Paula seemed to have no issues with fucking Dan or, any of these other guys, she continued to rebuff my timid attempts to take things further. That entire summer I never got any further than tame make-out sessions with Paula and if I even tried to cop a feel of her ample breasts, she would shoot me down immediately. I suppose I should have been more forceful, perhaps even confronting Paula about her flagrant infidelities, but I think I'd resigned myself to the fact that Paula was never going to provide me any sexual favors. And as the summer ended and Paula went away to college, it was she who told me that we needed to break up as she didn't want a "long distance romance."

Chapter 3

After Paula and I broke up, I started at community college in the fall and I vowed to stay away from girls like her. It was clear that my first relationship was unusual to say the least and all I wanted was a faithful, loving girlfriend to call my own. However, the best laid plans sometimes go awry as a friend of Paula's, Monique, befriended me within the first couple of months. I'll never know whether Paula had told Monique of our oddball relationship, or not, but after running into her one day at college, she asked me out. Monique was a year older than me and had a Vietnamese mother and a French father and was very attractive in an exotic, foreign sort of way. Not wanting to turn down a date with such a pretty girl, I agreed to join her for dinner. We both had a great time and we were soon seeing each other on a regular basis.

From the outset Monique, unlike Paula, was straightforward with me and she made it clear our relationship would never be anything other than platonic. It's not that she came right out and said it, but if I tried to initiate anything more intimate than a kiss on the cheek, Monique would shoot me down immediately. Nevertheless, despite my vow to avoid women like Paula, I was happy to spend time with a beautiful girl like Monique who enjoyed many of the same things I did. And as I got to know Monique better, I learned that she had quite a reputation and had a constant parade of guys sharing her bed. In fact, when she and I would attend parties together, Monique would frequently end up going home with another guy while I was left to head home alone to engage in my inevitable masturbation sessions. All during this time, I had a sizeable crush on Monique and although she had friend-zoned me completely, she had replaced Paula as the central character in my masturbation fantasies.

In hindsight, I credit Monique with fine-tuning my cuckold sensibilities. She was a natural cuckoldress and she didn't try to spare my feelings whatsoever when she would leave a party with another guy or cancel our dates at the last second if some other guy asked her out. Monique made no excuses for her behavior and I have to say, her confident embrace of her own sexuality was a real eye-opener for a shy, introverted guy like me.

Monique was also well versed in dressing to attract male attention and she wore miniskirts and shorts that were typically much shorter than was the current fashion. And she always wore tops that showed off her ample cleavage, giving guys a peek at what they might enjoy if they played their cards right. But most of all she instilled a love in me for women wearing high heel shoes. At barely five feet tall, Monique was rarely, if ever, seen without a pair of tall, wooden, platform sandals on her pretty feet and I spent many a night with my dick in my hand picturing them draped over the shoulders of one of her many lovers.

After a couple of years, Monique moved on and our get-togethers became infrequent at best. This was fine with me as I had become increasingly uncomfortable with my unrequited feelings for Monique and I knew I needed to move on. And for the next year I concentrated on my studies and, with my job, I had little time to pursue romantic relationships.

Because I was working to support myself during my college years, I was unable to speedily complete my AA degree and so I found myself at age twenty-one, still in community college, and still a virgin. It was in my final semester that I met my beautiful, wife-to-be, Cheryl. She and I met at the campus coffee shop between classes and immediately hit it off. There was something about Cheryl that drew me in immediately and before long we were having coffee together pretty much every day.

Cheryl's bubbly personality was in stark contrast to my shy temperament and although we didn't share any common friends, it seemed we had much in common when it came to music, movies, and humor. With each passing day, my initial crush on Cheryl intensified and I found myself thinking of her incessantly. Cheryl was my dream girl with her slim physique, small but firm breasts and the most beautiful legs I had ever seen. Her long brown hair was her signature feature and you could immediately spot her in a crowd just by her hair alone. At only five feet tall, Cheryl was petite, and she compensated for this by wearing the same sort of wooden platform heels that Monique had always worn. Cheryl was dating a guy named Mark who I'd met only once and increasingly I found that my masturbation sessions involved Cheryl spreading her legs for Mark, his imaginary horse-sized cock plunging in and out of her sweet pussy.

By the time the semester ended, Cheryl and I had become very good friends and I had learned quite a bit more about her. It seems that she and Mark had a bit of a tumultuous relationship and they both repeatedly cheated on each other, always reconciling following their infidelities. In fact, one of the reasons that Cheryl gave for sharing so much personal information with me was that her best friend Katie had slept with Mark behind her back and although they had put that indiscretion behind them, Cheryl said she could never trust Katie again. With Katie no longer Cheryl's number one confidant, I took on that role, listening to Cheryl bitch about Mark or unashamedly confess that she occasionally dated other guys behind his back.

As Cheryl began to confide more and more to me, I found that my feelings for her grew stronger. She was my dream girl, smart, funny, and sexually uninhibited. I spent many a night masturbating to visions of Cheryl with other guys, but in an unusual twist, I also began to picture myself having sex with Cheryl, my strong feelings for her causing me to deviate from my standard practice o picturing myself as solely a voyeur. However, all during this time, I never once believed that Cheryl had any romantic feelings towards me. And the fact that Cheryl freely shared details of her relationship with Mark as well as other guys only confirmed to me that she considered me a friend and nothing more. But despite having been friend-zoned once again, I realized that the more time I spent with Cheryl, the more I was falling under her spell. And although our relationship was apparently doomed to remain platonic, I couldn't help but treasure every moment I spent with Cheryl.

As it turned out, Cheryl's interest in me wasn't entirely innocent and as the semester wound down, she invited me to go out with her to dinner and then to her house for a drink. I had assumed this was merely a platonic invitation but after a fantastic dinner at a restaurant, we went back to Cheryl's house where it happened that her roommates were out for the night. As we sat drinking wine, Cheryl leaned over and kissed me and before I knew it, we were making out passionately. This was the moment I had dreamed about from the moment I'd met Cheryl and I was in seventh heaven as we kissed.

After a bit, Cheryl reached down with her hand and unzipped my pants, freeing my penis and she then began to fondle me with her hand. When I didn't immediately stiffen in her grasp, Cheryl leaned over and began to suck my dick, but to my enduring shame I still couldn't get hard. I was so nervous that the feel of Cheryl's lips on my penis, rather than turning me on, caused my dick to shrink in fright and eventually she gave up, lifted her head and asked, "What's wrong, Mike?" Not wanting to admit that I was a virgin and scared, I told her that I had had too much to drink and that maybe we should take things more slowly.

Although disappointed in my failure to get hard, Cheryl said she understood, and we soon kissed goodbye as I headed on home. Not surprisingly, I got hard the minute I was back in my bed and I ended up masturbating only to feel guilty and ashamed after I came.

The next day at school Cheryl acted normally and even invited me out that upcoming weekend to a party she knew about. When I asked about Mark, Cheryl said that she planned to break up with him that evening. It seems that he had cheated on her once again and this time Cheryl said she'd had "enough." And that weekend we attended the party together and ended up making out in my car on the way back to Cheryl's house. When we went upstairs to her bedroom, I found myself unable to get an erection yet again, but this time Cheryl pulled off her skirt and basically demanded that I lick her pussy.

I'll never forget that moment as I gazed at Cheryl lying back on her bed. Cheryl's legs were parted ever so slightly and as I lay down on the bed, she spread her thighs giving me a bird-eye view of her pussy. This was the first time I had ever seen a woman's vagina in the flesh, and I was fascinated by the sight. Cheryl's slit was surrounded by downy brown hair and her lips protruded ever so slightly as I leaned in closer. I hesitatingly brought my mouth to her opening and as I did so I extended my tongue and very gently licked between her fleshly lips, tasting a woman's juices for the first time in my life. Cheryl's moan of appreciation inspired me to begin to lap at her pussy and soon her juices were flowing in earnest as she writhed on the bed. Although my technique was undoubtedly amateurish, I was still able to give Cheryl an orgasm and as she shuddered in climax, I felt an overwhelming sense of relief. Although unable to fuck Cheryl, at least I had been able to bring her to orgasm and at the very least, that was something. That night, we slept in each other's arms and although I was still mortified by my performance issues, I was increasingly falling for Cheryl.

Cheryl and I continued to date for several months before my anxiety began to ease. Cheryl and I would go out on regular dates, and at the end of the evening, I would inevitably find my tongue buried in the folds of her pussy, licking and sucking her to orgasm as she instructed me on how best to please her. Afterwards we would lie together, Cheryl always assuring me that it was okay that I was unable to get an erection and that we would continue to "work on it." Well, one night, after having brought Cheryl to orgasm while she rode my tongue, I developed an erection that didn't immediately wilt in her hand. And that night I finally lost my virginity as I fucked Cheryl for probably thirty seconds before I filled her with my load. Despite my lack of endurance, it was a profound relief to have finally popped my cherry and from that point on, we were insatiable. Cheryl and I fucked at least two to three times a week as our relationship blossomed. Although I was relieved that I was now able to get an erection, I knew I still needed to work on my stamina but with Cheryl's gentle tutelage I felt I was making strides to becoming a better lover. I genuinely believed that I had met the girl of my dreams and despite lingering doubts about whether I measured up to Cheryl's previous boyfriends, I was truly in seventh heaven.

I must admit I'll always be grateful that Cheryl was so patient with me during the initial stages of our relationship. There aren't many girls of that age who would have been content to continue dating a guy who suffered from erectile dysfunction and the fact that Cheryl was so gentle and understanding of my plight meant the world to me, even to this day.

It so happens, however, that Cheryl wasn't forced to go without penetrative sex while patiently waiting for me to work through my sexual anxieties. Unbeknownst to me, at the same time Cheryl and I were dating, she continued to see her ex, Mark, along with enjoying several other brief flings. Although she had developed feelings for me, Cheryl didn't really feel we had reached a point in our relationship where we should be exclusive to each other. And frankly, I'm not sure anyone could have blamed her for continuing to sleep with other men given my performance issues. In fact, it was after my second failed attempt to develop an erection that Cheryl called Mark and asked if he was interested in getting together the very next evening. And although Mark was now dating another girl, he immediately jumped at the opportunity and he and Cheryl spent the entire night fucking and sucking with abandon. When the truth eventually came out, Cheryl admitted that the sex with Mark was far better than it had been when they were in a relationship and after that first night, they got together regularly.

In hindsight, it seems that Cheryl and Mark, while not particularly well suited in many ways, were very compatible when it came to sex. Mark was tall, muscular and, as Cheryl later told me, was able to fuck for hours enabling Cheryl to enjoy numerous orgasms over the course of a single session. And now that Cheryl and Mark were getting together surreptitiously, the sexual dynamic was enhanced by the thrill of cheating, making their encounters that much more exciting.

Since Mark was now dating one of Cheryl's good friends, we would see him frequently and all the time I never suspected that he was still screwing my girlfriend. Cheryl also wasn't one to deny herself the opportunity to enjoy other guys and she continued to regularly date other men, never waiting till the second date to spread her legs for a handsome, virile, stud. In contemplating all this later, I suppose that with Cheryl's prior sexual experience, it was all but inevitable that she would seek out other men to provide her the sexual satisfaction to which she had become accustomed. But, at the time, I was oblivious to Cheryl's promiscuous behavior and was falling for her in a way that surprised even myself.

Chapter 4

It was almost six months after Cheryl, and I had first started officially dating that I received an acceptance letter to a prestigious university in Los Angeles. Although excited about the prospect of furthering my education, I was torn as to whether I should accept the offer. I had fallen deeply in love with Cheryl and I couldn't bear the thought of losing her by moving to Los Angeles. When I confessed my concerns to Cheryl, she leaned over to me, kissed me on the lips and said, "How about if I move down there with you? I'll work and help you finish college and then you can do the same for me."

I couldn't believe what I was hearing. Cheryl, the love of my life, was not only willing to move with me to Los Angeles, but she wanted to help me through college. My heart swelled with happiness as I said, "I love you Cheryl." This was the first time I'd said this and when Cheryl returned my sentiments, I thought I had died and gone to heaven. That night we made love and over the next several months we packed up our belongings, found a small apartment close to campus and settled into life in Los Angeles.

Cheryl later confessed that she had promised herself that she would remain faithful to me once we moved in together. And although she had spent the night before we drove down to Los Angeles with Mark, the two of them enjoying one last passionate evening together, Cheryl was committed to being faithful from that point on. But, as it turned out, Cheryl's plan to be monogamous was to be short-lived.