A Cuckold Story Ch 01 07

Chapter 1

I'm writing this true story to document my life as a cuckold. Just as some men as born to be leaders and some followers, likewise some men are born to be studs, pleasing and being pleased by women, while some men are born to be cuckolds, accepting their limitations and encouraging their wives and girlfriends to find sexual pleasure elsewhere. In my case, I think I was always destined to be a cuckold. And for anyone who pities the poor cuckold, wondering how any man could put up with an unfaithful wife or girlfriend, rest assured there are men like me who have embraced our role and are proud to be the supportive husband or boyfriend to a sexually liberated woman.

My story begins back in my sophomore year in high school when I bought my first Penthouse magazine. In it, were a multitude of stories that I would read while masturbating but one story, immediately became my favorite. It involved a husband and wife who were out dancing when a handsome friend of the husband showed up and ended up seducing the wife and fucking her outside, bent over the hood of their car, while her husband spied on the two lovers. This story hit a nerve with me not so much because of its cuckold nature but because the wife was so sexually uninhibited and shameless. I masturbated to this story incessantly, but rather than the hunky stud fucking the unfaithful, slutty wife, I identified with the husband, excitedly watching his wife surrender to his friend.

Soon, I was searching out similar stories and whether it was the husband who watched his wife seduced by a salesman in their living room, or the wife who takes on a series of male friends at a Christmas party, my best masturbation sessions always revolved around women who were unafraid to pursue their sexual desires, regardless of their marital status. I'd lay in bed almost every night, furiously masturbating to these stories and whenever a new Penthouse magazine came out, I'd scan the stories immediately hoping to find one or more that featured a slutty wife and a voyeuristic husband.

In retrospect, I believe my fascination with unfaithful wives stems from my own insecurities surrounding women. I'd always been shy and awkward around girls but at the same time I was intensely attracted to those girls that had reputations as being promiscuous or easy. Unlike me, the girls that were known to "put-out" were not afraid to embrace their sexuality and for a virgin like myself, they were mesmerizing. However, whenever I'd interact with any of these girls, I'd become tongue-tied and nervous, invariably acting like a complete fool.

Of course, my shyness around sexually experienced girls didn't stop me from featuring these very same girls in my masturbatory fantasies, imagining various girls from my school as the women in the stories I read in Penthouse. I'd picture these girls encouraging some faceless stud to fuck them senseless while their timid boyfriend watched helplessly. And every time I'd pleasure myself, I was never the one doing the fucking. I was always the boyfriend watching with my dick in my hand. Inevitably, when I'd come, I'd feel guilty and ashamed, vowing to throw away my Penthouse magazines and try to land a "nice girl" like many of my friends.

In my senior year, I finally overcame my shyness to some degree and eventually started dating Paula. Paula was an attractive brunette and although she was perhaps a tad bit overweight her ample breasts more than compensated for that. Paula wasn't caught up in any of the more popular cliques and although she was friends with quite a few of my classmates, she was something of a loner. I'd had a crush on Paula for at least a year and when she first seemed to take an interest in me, I felt like I'd died and gone to heaven. Paula and I shared the same musical tastes and we'd often get together after school to listen to various bands, each of us fond of English progressive bands like Yes or Genesis. And when Paula turned to me and kissed me for the first time as we listened to the album Close to the Edge by Yes, I knew I'd met the girl of my dreams.

After that first kiss, Paula and I agreed to date and for the first time in my life I felt like I was finally coming out of my shell. I even went so far as to throw out all my Penthouse magazines believing that it was time to concentrate my energies on a real girl and not some model or story about a slutty wife. But although we would frequently kiss and occasionally make-out, Paula always refused my feeble advances to take things further. She would push my hand away if I tried to cop a feel of her tits and anything below the waist was most certainly off-limits. And although just a quick feel of my girlfriend's charms would have been a godsend, I've always been the kind of guy who takes no to mean no and so I remained content to engage in occasional make-out sessions. I assumed, incorrectly as it turned out, that Paula was a virgin like me and that she was saving herself for marriage or at least until she went away to college.

It was on the night of our graduation from high school that I learned that my girlfriend was not so innocent after all. Paula and I had agreed to join several of our friends at a party at a local motel and we were really looking forward to blowing off some steam after finally finishing high school. One of the guys had rented a couple of adjoining rooms and had also procured plenty of beer and wine and so we gladly paid our portion of the cost with high hopes of celebrating our graduation in style. Paula looked stunning that night as she had not changed from the sexy silk dress and high heel shoes she had worn under her gown and I was proud as a peacock as I escorted her to the party. Both Paula and I had a couple of drinks before we even got to the party and once there it was one drink after another as we laughed and carried on with our friends until well past midnight.

Although it was late, when a couple of the guys asked if I wanted to step outside to the parking lot to smoke a joint, I agreed and although I wasn't really much of a stoner, I took a couple of puffs as we passed the joint between us. We stayed outside for at least a half-hour shooting the breeze before venturing back to the party.

When we got back to the room, Paula was nowhere to be seen and when I asked a couple of her friends where she'd gone, they both began giggling uncontrollably. I started to get kind of pissed off as I felt I was the butt of some sort of joke, when a buddy of mine took me aside and said that Paula was in the other room with Dan. The way he said it, I knew something was up, and when I started to head for the door, he put his arm on my shoulder and said, "I don't think you should go in there."

This was my first true cuckold moment and it was a doozy. It was obvious that Paula had hooked up with Dan and I knew that as her boyfriend, it was my duty to go in there and separate the two of them. However, try as I might I just couldn't bring myself to assert myself and so instead, I just grabbed another beer and sat down on the bed while pretending that I was cool with what was going on. The pot I'd smoked only amplified my paranoia as I could feel everyone stealing occasional glances over at me to see my reaction to my girlfriend's blatant infidelity.

It was no more than a couple of minutes later that we all heard the beginnings of a rhythmic thud of the bed against the wall as Dan was very obviously fucking Paula! I couldn't believe what was happening! Paula had steadfastly refused to grant me anything more than the occasional kiss and here she was fucking Dan where all our friends could hear!

I couldn't bring myself to even look at the others and the formerly raucous conversations were now more subdued with occasional scornful laughter from the guys or nervous giggles from the girls. The awkwardness of the situation put a damper on the party and soon enough, people started leaving. Craig, the guy who'd rented the rooms asked me to drop the keys off in the lobby when I left but everyone else pretty much ignored me as they gathered up their things and headed home. Soon I was sitting in the empty room alone, listening to the thump of the bed and occasional muffled squeals and whimpers from Paula and animalistic grunts from Dan.

As I sat there by myself, thoroughly humiliated and betrayed, I couldn't help but note that I had developed an erection that was straining against the front of my pants. In hindsight, I suppose this was a life changing moment for me, as I had to acknowledge that, despite my embarrassment, I was intensely aroused at listening to my girlfriend fuck another guy not ten feet from where I was sitting. To this day, I don't know why I did it, but after hearing Paula cry out in what I assumed was an orgasm, I unzipped my pants, pulled out my stiff penis and started to masturbate in time to the rhythmic pounding of the bed against the wall. Within less than a minute, I began to come, my sperm spewing from my dick as I desperately tried to keep from soiling my pants as I caught every drop in my left hand.

Once I'd come, I quickly made my way to the bathroom to clean up, nervous that Dan and Paula might finish and discover me washing semen from my hands after having jerked off listening to them fuck. As it turned out, I needn't have worried as once I'd cleaned up and was sitting back on the bed, I continued to listen to my girlfriend squeal in delight as Dan fucked her relentlessly for at least a half hour more. Of course, now that I had come, I was overwhelmed with feelings of shame, guilt and anger. How could Paula do this to me, much less in front of all our friends? Worse, what kind of guy masturbates listening to his girlfriend getting fucked? These shameful thoughts ran through my head as I waited for Dan and Paula to finish and it certainly didn't help that despite having come, my dick was once again pressing against the front of my pants as I listened to the two lovers.

Dan and Paula fucked for what seemed like hours but was probably no more than thirty minutes more before they emerged from the room to find me sitting by myself on the bed. I suppose I could have just headed home after having jerked off, but I'd driven Paula to the party and despite the circumstances, I didn't want to just abandon her there. Dan said something about being sorry before he quickly made his exit. Paula also apologized but I didn't respond as we made our way out to my car. After dropping off the room keys in the lobby of the motel, we drove back in silence and when I dropped Paula off at her house, I didn't even say goodnight. Later that night, however, as I lay in bed bemoaning my bad fortune, I felt an uncontrollable urge to masturbate again. When I'd jerked off at the motel, I had been nervous that I might be discovered, but now, back in my bed, I could take my time and focus on every detail.

As I lay there in my bed, my stiff penis in my hand, I pondered the events of the evening. I'd known Dan since elementary school, and although you couldn't characterize us as friends, we did have some history. Dan and I traveled in different social groups and he was part of the "jock" contingent at our school while I hung out with a group of friends who while not complete nerds, were certainly not part of the "in crowd." In my junior year, Dan and I both had gym class together and it was then that I had my first real run-in with him. Because Dan was so active in sports, Mr. Wright, the gym teacher, always picked him to be captain of one of the teams, whether softball, volleyball or soccer. And it seemed that I'd always end up on Dan's team, typically picked last or next to last and destined to be assigned a position where I'd do the least harm. I'd never been very good at sports and so I'd often find myself on the receiving end of one of Dan's harangues. Whether it was missing the open goal, or dropping the easy catch, it seemed that Dan never missed the opportunity to embarrass me in front of the other guys. I suppose, in today's world, Dan's behavior might be construed as bullying but at the time I think people just considered this sort of thing normal, the high school jock teasing the skinny geek. But rather than push back against Dan's barbs, I did what many other guys in my situation did, I tried to appease him, acting as if his mocking comments didn't sting and making a fruitless effort to befriend him.

Although Dan was typically not one to take his bullying to the physical level, there was one instance where he thoroughly humiliated me that will forever be etched in my memory. It happened that winter during the rainy season when our gym class transitioned to wrestling. Now wrestling was a sport I always hated and at which I was particularly bad, but amazingly, I was able to beat my first-round opponent. My elation was short-lived however, when I realized that for the second round I was matched up against Dan, the actual match a mere formality given the difference in athleticism between the two of us. I knew from the outset that I was going to be on the losing end of the match, but when Dan pinned me almost instantly, I felt truly emasculated.

Lying on the mat with Dan holding me firmly in place, I could hear cheers for Dan's victory as well as laughter at how quickly he defeated me. I guess Dan was feeling pretty cocky and when I stood up to join the rest of the class, Dan yanked down my gym shorts, leaving me standing there in my jock strap with my shorts around my ankles. Now, this wouldn't have been such a big deal, but that day we were sharing the Gym with the girl's gym class and from the other end of the Gym, I could hear the shrieks of amusement at seeing me standing there in my jock strap, my ass fully on display. Hearing the laughter from both the guys and the girls was humiliating and I turned beet red before pulling up my gym shorts and scurrying to join the other guys. Even Mr. Wright couldn't suppress a chuckle and although he made a half-hearted effort to chastise Dan for his juvenile behavior, I could tell that he thought Dan's prank was hilarious.

My embarrassment at having been "pantsed" was intense and word of the incident quickly spread throughout the school. Even my friends kidded me about it for the next week and I overheard more than one group of girls giggling about it behind my back. Eventually the furor died down, replaced by some other incident that caught the school's attention, but although I was reasonably sure Dan had little recollection of the event, my memory of it was still as fresh as the day it happened. Since then, Dan had continued to excel at sports and was one of the stars of the baseball team and a key player on the football team as well. He and I rarely interacted and frankly, I was surprised he'd even attended our little graduation after-party, but he'd mentioned earlier, he didn't want to go to any of the other parties as he was afraid to run into his girlfriend who he'd recently dumped. It was just my luck that Dan chose our party to attend and as I pictured him with Paula, I couldn't help but think that he had it out for me. First, he yanks down my shorts in gym class and now he fucks my girlfriend on graduation night! Was there any further insults Dan had in store for me?

As I lay in bed recalling the evening's events, I couldn't deny that I was aroused. From the moment I'd stripped off my clothes, my dick had remained stiff as a board and I'd been shamefully fondling myself the entire time as I pictured Dan sporting an enormous erection as he fucked my sweet little Paula. I still was in shock that Paula could do this to me. Paula knew all about how Dan had tormented me the previous year and yet she'd still welcomed him between her legs, granting him something she'd steadfastly denied me. My mind reeled with the embarrassment and humiliation of it all, but every time I'd imagine Dan, his muscular torso glistening with sweat as he pumped his thick shaft into my girlfriend, I'd begin to feverishly masturbate. And before the night was over, I jerked off three more times to this erotic vision. Each time I came, I would become filled with shame at having masturbated to thoughts of my girlfriend fucking Dan, but inevitably I would wake up later with another erection and begin pleasuring myself all over again.

Chapter 2

After having been thoroughly humiliated by Dan and my girlfriend on graduation night, I was glad that school was over for the year as I dreaded having to face my friends after that embarrassing experience. But, as it turned out, Paula called me the very next morning, apologizing and asking my forgiveness. I think it may have been my lingering shame at having masturbated while listening to her and Dan, but I ended up forgiving her and even agreed to take her to a movie that Friday night as that had been our practice over the past several months.

That summer I was working at a warehouse to save up for college and so the remainder of that week was filled with learning the ins and outs of my new job and so I tried not to dwell on what Paula had done. Thursday evening, however, as I was coming home from work, I ran into Dan. I'd just exited the bus when I saw him walking up the sidewalk towards me. I thought to turn around, but it was too late as he called out, "Hey Mike" and giving me a big smile, he then uttered a couple of apologetic words for getting together with Paula. When I didn't say much in response, he went on to explain that he didn't think I'd mind since "everyone knew" she slept around. This news hit me like a ton of bricks, but I was able to keep my composure, stammering, "Um, yeah, It's no big deal, Dan. It's cool." And then to try and mitigate my humiliation, I lied and hinted that we had an "open relationship."

My apparent acceptance of my girlfriend's infidelity put Dan at ease as he slapped me on the back, telling me, "That-a-boy. No hard feelings then, okay?"

"Uh, yeah, sure Dan", I mumbled in response as I tried desperately to extricate myself from this conversation.

I had just started to turn and head home when Dan snickered, "Yeah, maybe someday she'll let you have a turn too. You'd probably like to lose your cherry before college, eh Mike?"

Damn! I couldn't believe that Paula had told him that we hadn't had sex yet. I could feel my face reddening with shame as I muttered that I needed to go. And with that, I hurried home, embarrassed beyond belief that not only had my girlfriend been cheating on me, but she had been telling people that I was still a virgin.

Despite my feelings of betrayal, the next day Paula and I went out to dinner and a movie as we had planned. I suppose Paula took her earlier apologies as sufficient, since she never once mentioned the incident with Dan, nor did she confess that she'd slept with anyone else. Other than that, however, we had a great time as we talked about our plans for the summer. Paula was dressed in a light sundress with high heel clogs and as she sat across from me at dinner and beside me at the theater, I couldn't help but be proud to have such an attractive girlfriend. And as we walked out of the movie theater holding hands, I thought I'd made the right decision in forgiving Paula for her indiscretions.

However, my good humor was soon to be dashed when as soon as we were seated in my car, Paula asked me to drop her off at Dan's house. I guess that Dan and Paula must have discussed my seemingly open-minded acceptance of their tryst as Paula asked the question as if it were the most normal thing in the world. To be sure, she did make up some excuse about wanting to talk to Dan about their class together during summer school, but we both knew what was really going on. And what was worse was that Dan had mentioned on prom night that his parents frequently spent weekends at their Tahoe cabin and that he was going to have the house to himself most every weekend that summer. Nevertheless, I couldn't bring myself to utter a word of protest as I dutifully drove to Dan's house. And as I drove, I watched Paula out of the corner of my eye as she redid her makeup in the visor mirror, first touching up her blue eyeshadow before carefully brushing her eyelashes with mascara. And when I eventually pulled up in front of Dan's house, Paula continued her primping, first rubbing a dab of rouge to her cheeks and then applying a fresh coat of bright pink lipstick to her lips. I couldn't believe Paula could be so brazen as to her intentions, but instead of making a scene, I said nothing as I watched my girlfriend make herself sexy for Dan. And when Paula had assured herself that she looked perfect and told me she'd see me later, I just mumbled, "Goodnight, Paula. Say hi to Dan."