A Cuckold Story Ch. 01-07

Looking back on it, I suppose most people would be appalled that Cheryl so thoroughly cuckolded me during our engagement. But in her defense, Cheryl had been cheating on me from the outset of our relationship and I think she had grown accustomed to sleeping with other guys behind my back and didn't see the harm in continuing to do so prior to our marriage. I know Cheryl rationalized her engagement infidelities as getting it out of her system but, to be honest, I truly believe Cheryl loved playing the naughty fiancé, fucking other men during the lead up to our wedding. And I must admit, there is something so shameless, so incredibly naughty, about Cheryl's behavior during our engagement that when I eventually learned of it, rather than be angry I was overwhelmed with lust for my errant bride. Cheryl, unlike most brides, wasn't one to focus on the details of our wedding and so she had me take on the bulk of the arrangements. And, to this day, when I think that when I was meeting with the caterers, the florist or the wedding planner, my fiancé was enjoying lusty encounters with other men, I never fail be aroused and these events remain some of my favorite masturbation themes. Of course, at the time, I was unaware of any of this and I was bursting with love for my bride, thanking my lucky stars that I had met a woman as beautiful and wonderful as Cheryl.

The day of our wedding was like a whirlwind and with all the family members and guests in attendance, Cheryl and I spent the greater part of the day as performers, acting out the roles of bride and groom. I'm not ashamed to admit I cried as I said my vows and when Cheryl and I kissed, I was the happiest man alive. I can only imagine what Brad thought of watching Cheryl and me at the altar. He had spent several hours the previous day fucking my fiancé to numerous orgasms and now he was watching her joining me in in marriage. Had I known, I would have loved to see the smirk on his lips, the unconcealed gloating, as I kissed the same lips that had been wrapped around his cock just twenty-four hours earlier.

Later that day, at our reception, Brad had the unmitigated gall to suggest that Cheryl slip away for a moment to let him be the first to consummate our marriage. To Cheryl's credit, she spurned his overtures, insisting their relationship was finished just as she had told him the day before. And when I eventually learned that Brad had propositioned my bride at our reception, I had a brief flash of anger at his disrespect for Cheryl's and my special day. But, in retrospect I wish that Cheryl had taken him up on his offer. It would have been very fitting to have been cuckolded on my wedding day and later that night when Cheryl and I were consummating our marriage, it would have been apt for me to receive sloppy seconds from my new wife.

Chapter 7

Once we were married, Cheryl tried to remain faithful as she had promised herself. But her sexual hunger, or perhaps more accurately, my own sexual deficiencies, soon got the better of her and it was little more than three months following our wedding when Brad called her up to say he was in town for a couple of days. Cheryl said that with no second thoughts whatsoever, she rushed to his bed and they spent an entire day at a local hotel fucking and sucking themselves to the point of exhaustion. My wife later confessed that this event caused her to rethink her vow of fidelity. Cheryl's day-long session with Brad was, in her words, "incredible" and she realized that she needed the occasional unbridled sexual encounter to make her feel complete.

My wife had an opportunity to explore her new thoughts on adultery soon after her day with Brad as Ken, from her gym, who had been hoping to hook up once again, asked her out for a drink. He didn't seem to mind that Cheryl was now sporting a wedding ring on her finger and after only one drink at a nearby bar, she was lying on her back in his bed welcoming his cock into her juicy pussy. Although the sex was not on par with what she had enjoyed with Brad, it was still far better than with me and Cheryl knew that she could never be a faithful wife. And the next time one of the other guys from her gym asked her out, she repeated this scenario, enjoying a satisfying sexual encounter that earned him, too, a place in Cheryl's rotation.

For the next several years Cheryl engaged in occasional casual sex with probably a dozen or so different guys. Unlike her previous affairs, she didn't see any one guy too often and she typically had only one or maybe two encounters a month. Once or twice a year, Brad would come to town and Cheryl would invariably come up with some excuse to spend one, or sometimes two, nights in his bed. I guess I was just naïve, but I never once questioned Cheryl's pretexts for her late nights or occasional overnights at a "girlfriend's house." But then, Cheryl's job had become much more demanding and the pressures to meet quotas or to close deals was taking an increasingly large amount of her time. No longer were all her "late nights at the office" an excuse to spend time in bed with another man, but instead she truly was working late at the office on a regular basis.

As Cheryl's career took off, she eventually received a promotion to sales, and she started travelling for business once or twice a month. At first, Cheryl was assigned to attend seminars and conventions where she was the "booth babe", manning the desk to explain her firm's products. This meant that a constant stream of men engaged her in conversation and the boldest among them asked my wife to join them for drinks after dinner. Cheryl's wedding ring did little to dissuade this male attention as these conventions were rife with sexual liaisons, and with men typically outnumbered women by about four to one, my sexy little wife was regularly propositioned.

The first couple of conventions Cheryl tried to avoid any sort of extramarital relations, but eventually in New York when she was feeling especially lonely, she agreed to meet a handsome guy for drink after the obligatory rubber chicken dinner. It didn't take much for this guy to get Cheryl to go back to his room with him and she had a great time as he gave her several incredible orgasms over the course of the evening.

Cheryl's New York experience was so good that from that point on, she was open to further sexual encounters while travelling. And sure enough, Cheryl soon had boyfriends in quite a few different cities and when she would travel out of town, her nights would frequently consist of lusty sessions with her lovers.

Cheryl later explained that her out of town affairs were the perfect way for her to satisfy her need for sexual adventure and variety. During this time Cheryl ceased all contact with her local lovers preferring the distance and anonymity of affairs with men in these far-flung locales. And although she would occasionally feel a twinge of guilt for cheating on me, the fact that I would never meet nor interact with any of her boyfriends, kept her feelings in check.

Cheryl kept up her out-of-town liaisons for several years before I started to become increasingly suspicious of my wife when she was travelling. Late night or early morning telephone calls would frequently go unanswered and a couple of times I even thought I heard a man's voice in the background when I called her early in the morning. And before my wife left for a four-day conference in New York, I worked up the nerve to go through her suitcase, finding all manner of sexy underthings and a large supply of condoms in her toiletry bag. I was floored with my discovery, but rather than questioning Cheryl about her apparent infidelity, I kept quiet, anxious to avoid any confrontation.

I still remember that New York trip vividly. Cheryl had left for the airport early Monday morning and had given no indication she was headed to anything but a business conference. My wife was dressed casually for the flight and we both kissed and expressed out love for one another as we always did before one of Cheryl's trips. All day at work, however, I could not get the thought out of my mind that my wife was carrying on an affair. Why else would Cheryl be bringing condoms and a selection of her sexiest underwear and high heel shoes?

I did receive a call from Cheryl when she arrived at her hotel and nothing seemed amiss as my wife told me she was just going to get room service and watch TV. In fact, I began to think that maybe I'd overreacted. Maybe the condoms in my wife's suitcase had a perfectly reasonable explanation? After all, Cheryl had talked about going off the pill and maybe she had bought condoms with that in mind? And after I'd eaten dinner, I decided to call my wife, thinking that hearing her voice would dispel any concerns I had about her fidelity. When I called Cheryl, however, there was no answer and I then tried again some fifteen minutes later.

I called pretty much every fifteen minutes for the next couple of hours and with each unanswered call, I felt my anxiety increasing. Cheryl had told me she was going to just watch TV, but it was clear she wasn't in her room and as I pondered what my wife might be up to, I realized that perhaps my suspicions were not unfounded after all. And to my everlasting shame, I found that this thought caused my penis to stiffen in arousal!

It was just like with Paula and Monique those many years ago! Here I was contemplating my wife, the woman I loved with all my heart, out with another man but in addition to being angry and hurt, I was sporting an erection that just wouldn't quit! And after making another unanswered call at eleven-o-clock my time, knowing that it was 2:00am in New York, I couldn't help but reach down and begin to stroke my dick. As I later learned, my wife was at that very moment fucking a fellow conference attendee that she had slept with on her previous trip to New York. Ironically, my masturbatory fantasies weren't too far from the truth and as I ran my hand up and down my penis, I pictured Cheryl splayed out on the bed of some imaginary man, his thick veiny cock pumping in and out of my wife's sweet pussy as she cried out in orgasm. These thoughts triggered an intense orgasm and I was soon spurting out my load on to the tangled bedsheet around my waist.

Almost immediately, I felt a wave of shame and disgust wash over me. What kind of man masturbates to visions of his wife's infidelity? And with my arousal temporarily sated, the pain and hurt of my wife's betrayal became intense. How could she do this to me? I couldn't help but make one last attempt to reach Cheryl but like the other calls, this one went unanswered as well.

As might be expected, I didn't sleep much at all that night and by morning I was a wreck. But despite my distress, I must confess that twice more that night I masturbated to visions of my wife screwing another man. Each time, I'd be overwhelmed with remorse and self-loathing after I came but, inevitably, I'd find my hand reaching down to stroke my penis not long thereafter.

I didn't get in touch with Cheryl until the next day when she called me at work late that afternoon. Maybe it was because I'd jerked off so much the night before, but I couldn't find it in me to question her on her whereabouts. I merely listened to my wife happily describe her first day at the conference. And when Cheryl said that she was going out with some fellow attendees for drinks that evening, I wished her a good time, telling her how much I loved her. As I hung up the phone, I momentarily thought that maybe I was wrong. Maybe Cheryl wasn't having an affair after all. My wife had been so sweet and loving on the phone that it was hard to think she was cheating on me. That night, however, when I tried to call my wife at midnight New York time, she was nowhere to be found and it wasn't long before I had my penis in my hand masturbating once again to thoughts of my wife fucking and sucking another man.

Each of the four nights Cheryl was gone, I was unable to reach her and each night I would masturbate incessantly picturing her in in all manner of sexual debauchery. It was if I was powerless to resist pleasuring myself to thoughts of my wife's infidelity and I realized I was on the same slippery slope that I'd been on with Paula that summer after high school. But when Cheryl arrived home on Friday, I chose not to confront her, preferring to keep my suspicions to myself rather than risk hearing something I didn't want to hear.

For the next year or so, I continued to spy on my wife, sneaking looks in her suitcase before her trips, invariably finding sexy lingerie, men's phone numbers and a robust supply of condoms. I knew Cheryl was cheating on me, but the funny thing was, she was still the cheerful loving woman I had married whenever we were together. Cheryl gave no indication that she was dissatisfied with our marriage and, on the contrary, she was constantly telling me how much she loved me.

Although deeply hurt that my wife was apparently cheating on me, whenever she was out of town on one of her business trips, I masturbated incessantly. I spent many a night, my dick in my hand, as I pictured Cheryl fucking and sucking nameless studs, each of her imaginary lovers sporting enormous cocks and coaxing multiple orgasms from my sweet bride. Invariably, after I would come, I'd be filled with shame and guilt, hating the fact that I was aroused by my wife cheating on me just as I had been with Paula. Eventually, I knew I had to confront my wife about her infidelity as I knew that the constant deception would eventually eat away at me.

It was after one trip to Denver that I finally decided I needed to clear the air. I had been unable to reach Cheryl for two straight days, and so on her return home I screwed up my courage and demanded to know her whereabouts. To Cheryl's credit she didn't lie or try to make excuses, but instead she confessed she had been with a man she'd been seeing for almost a year. Although I already knew Cheryl had been cheating, I was unprepared to hear it from her own lips. I felt like I had been socked in the stomach and I immediately burst out crying. Cheryl, for her part, was genuinely sorry for what she had done to me and she, too, shed some tears that night.

The night Cheryl confessed her affair, I slept in the guest bedroom and throughout the night I would awaken thinking that everything had been just a bad dream only to realize that it was not a dream and that my wife really was cheating on me. The next morning, Cheryl and I didn't talk at all but when we returned home from work, we sat down to talk over a glass of wine.

Cheryl started off telling me she was going to be "brutally honest" about her past and she then proceeded to tell me how she had been cheating from the very beginning. She told me about Mark, Jerry, Dave, Brad and all the others as I sat there stunned thinking how stupid I must be to have not noticed that my wife had slept with literally dozens of guys since we'd been together. I knew that most guys would have already contacted a lawyer hearing this news, but I couldn't bear to think of losing the woman I loved. And when Cheryl moved over and sat next to me on the couch, putting her arm around me and saying, "But, Mike. I love you. Those guys don't mean anything to me", I started sobbing uncontrollably.

"I love you too", I sobbed as she consoled me by rubbing my back while continuing to assure me that she wasn't planning on leaving me and that she still loved me more than anything.

Eventually, I calmed down a bit and against my better judgement I asked why Cheryl had cheated on me. My wife hesitated for a moment before sheepishly replying, "I don't know how to say this without hurting your feelings, but...". And here she hesitated once again. Cheryl finally burst out, "You know, sex with some of these guys is really, really good. Sometimes I just need that."

Now the implication was that sex with me was not so good and upon hearing this I was devastated. I acted like a complete idiot, calling Cheryl a slut and worse as I stormed out of the house and checked into a nearby hotel. I spent the night contemplating my situation as I tried to decide what to do. On the one hand I still loved Cheryl and if she was to be believed, she loved me too. But on the other hand, she had deceived me all these years and now she was telling me that she had fucked all these other guys because I wasn't good enough in bed.

Cheryl's admission that her affairs were primarily about needing good sex triggered my insecurities in a way that surprised me. Frankly, I had always known that I was less than incredible in the bedroom and the fact that Cheryl had been with many different men before me only stoked my lack of confidence in my sexual prowess. But now, hearing directly from my wife that she needed to take lovers because my sexual performance wasn't up to snuff was a blow to my ego. And when I thought about Mark, Brad, Dave or Jerry, all guys that Cheryl had slept with and that I had met at one time or another, they all had similar traits. They were all tall, athletic, and handsome, their muscular builds in stark contrast to my slim, some might say skinny, physique. And personality wise, they all had the sort of cocky, almost arrogant, demeanor that Cheryl had always told me she disliked, but obviously enjoyed in the bedroom.

The more I thought about it, I realized that Cheryl was sexually attracted to "bad boys", the type of guys who bedded scores of women and who had the sexual skills to keep them coming back for more. I was the complete opposite from these sorts of guys and Cheryl had always told me that I was her best friend and that she loved me for my kindness and generosity. I felt much the same about Cheryl as she was undoubtedly my best friend and I loved being in her company, even if it was just accompanying her shopping for clothes or helping with the housework. And when we first started dating, I began to spend less and less time with my male friends, preferring Cheryl's company or, at most, joining other couples for nights out on the town. Cheryl, too, had few female friends and we had frequently referred to each other as "soulmates."

As I pondered this new revelation, I began to see things in a somewhat different light. Perhaps Cheryl's confession that she fucked these other guys because I wasn't satisfying her needs was a good sign? And maybe the fact that Cheryl had slept with so many other guys was some sort of sex addiction rather than dissatisfaction with me as her husband. After all Cheryl had been fucking other guys from the very start of our relationship and she hadn't left me yet. In fact, her lengthy affairs with Brad, Dave and Jerry had pre-dated our engagement and she still had readily agreed to marry me. Perhaps she truly did love me, and we had a chance to restart our marriage? Eventually I concluded that, at a minimum, I at least owed Cheryl a chance to redeem herself and so that morning I called her at her office and after apologizing for calling her a slut, we agreed to talk again that evening.

That very evening, Cheryl apologized repeatedly for her behavior and promised to be faithful from that point on. I knew Cheryl was sincere as tears were streaking her cheeks and she looked genuinely scared that I might leave her. And when she told me how much she loved me and how she couldn't bear to be without me, I believed her. Since Cheryl was being so contrite, I couldn't help but confess my own sordid history as I told her all about Paula and Monique and how I couldn't bear to go through anything like that again. And when I confessed that she was the only girl I'd ever been with, Cheryl giggled through her tears, "Sweetie, don't you think I know that?" Cheryl's admission that she knew I'd been a virgin was cathartic in a way that I didn't expect, and I felt a wave of relief wash over me as I realized that I would never have to keep any secrets from her ever again. After more tears from both of us, I agreed to forgive Cheryl on the condition that she never, ever, lie to me again.