A Cuckold Story Ch. 52-55

Chapter 52

In what was a recurring theme, after returning from her steamy London vacation with Ian, Cheryl was naturally disappointed that she no longer had any local boyfriends to turn to when she needed sexual satisfaction. And as for me, I missed the excitement of Cheryl's periodic dates with other men which included the erotic tension before her dates along with the sensuous reclaiming that followed. And when Ian met a woman his own age and first, reduced his texts and calls to Cheryl and then stopped corresponding altogether, I knew it was only a matter of time before my wife found a new lover.

It was against this backdrop that I came home one evening to find Cheryl holding an envelope with an excited grin on her lips. From the look on my wife's face I thought for certain she'd arranged a date of some sort but, instead, it turned out that my wife was excited that I'd received an invitation to my fortieth high school reunion.

Now, as anyone who has read my entire story will remember, my first introduction to cuckolding was when my high school girlfriend, Paula, fucked one of my classmates following graduation. That in and of itself was bad enough, but the fact that Paula's indiscretion was witnessed by a number of my friends had caused me to disassociate with the majority of my high school buddies. And so, when Cheryl showed me the invitation, I immediately insisted that I didn't want to go.

Despite my reluctance to attend my reunion, Cheryl had other thoughts on the matter. My wife said she wanted to meet all my fellow classmates but when I pressed her on it, she admitted that what she really wanted was to meet Paula. I cringed when she said it and my thoughts turned to Cheryl and Paula comparing notes on cuckolding me, but my wife assured me that wasn't her motivation at all. Instead, she said, my wife wanted to see for herself the only other woman, other than her, to have stolen my heart. Now, I must admit, I was somewhat interested in seeing Paula again and so I eventually agreed to attend the reunion, telling Cheryl that we'd just make a brief appearance and then leave.

Now, the reunion was several months out but you'd have thought it was imminent the way Cheryl started preparing. My wife was determined to show Paula that she'd missed out with me and she also wanted to make me proud at having landed such a sexy wife after my humiliating graduation experience. And as the night of the reunion drew near, I began to feel much better about things. Escorting my beautiful wife into the reunion would help to erase all the angst I still carried about my high school days and I began to look forward to the reunion as a chance to redeem my reputation.

I had no idea whether Paula would attend the reunion, but I truly did hope to see her again. Frankly, I wanted to show her that not only did I have a successful career but that 'd landed a sexy, beautiful wife. I'd long since forgiven Paula for having cuckolded me and in some ways, I guess I had her to thank for initiating me to the benefits of accepting one's destiny. Cheryl had cuckolded me from the outset, and I'd since come to understand that men like me are meant to stand aside when their wives or girlfriends seek out sexual satisfaction with other men.

But when I mentioned my thoughts on this to Cheryl, she was having none of it. "C'mon Mike, don't be silly. You just want to make Paula jealous, don't you," laughed my wife.

I couldn't help but laugh along with Cheryl as I admitted that yes, I did want to make her jealous. It was childish of me, I know, but then again, being openly cuckolded by your first true love leaves a pretty deep wound.

In the final month leading up to the reunion, Cheryl worked out constantly and coupled with a strict diet, she lost five pounds. In fact, my wife and I became co-conspirators in wanting to impress my former classmates and make my former girlfriend jealous. Cheryl wanted to look fabulous, so she and I spent several evenings at the mall to find the perfect dress, finally settling on a slinky, black dress that landed several inches above mid-thigh. My wife paired the dress with her Louboutin pumps and when she modeled the outfit all I could say is, "You look so incredible."

Not surprisingly, since Cheryl has always been jealous of me around other women, now that I might be seeing my former girlfriend, she became more possessive than ever before. I had to constantly remind my wife that Paula and I'd never had sex, but she would always reply that I'd wanted to fuck her, which was almost as bad. I tried to counter her jealousy by being extra attentive to Cheryl and even encouraged her to maybe try to arrange a date with one of her former lovers. I've always found that my wife's jealousy lessens somewhat after enjoying the attentions of another man and I was hoping this just might work. Unfortunately, instead of taking my suggestion seriously, Cheryl took an alternate tact, insisting that I lock myself in chastity exactly one week prior to the reunion, saying, "I know you won't be paying too much attention to Paula with your little dickie all locked up."

The day of the reunion, Cheryl was in a fabulous mood and I was hopeful that the night would turn out great for both of us. However, just as we were parking outside the hotel where the reunion was to be held, Cheryl turned to me and said, "Okay, Mike. I just want to make sure we're clear on a couple of things. I don't want you to hug or kiss any of the women tonight. And that goes double for Paula. And when you see Paula, you can talk with her, but I want to be there the whole time. I want her, and everyone else, to know that you're my husband and are off limits."

Now the last thing Cheryl ever has to worry about is me picking up on women and with my penis securely locked in chastity, I was feeling even more reserved than usual. And so, it was easy for me to agree to my wife's rules and we were soon making our way into the ballroom at the hotel.

When we entered the room, I noted several men stare openly at Cheryl as she was dressed far more provocatively than most of the other women. I scanned the room for familiar faces, and I was soon introducing Cheryl to several of my old friends as we made our way around the room. Suddenly, I saw Paula out of the corner of my eye, and I must admit I was somewhat shocked. No longer the attractive brunette that I'd known in high school, she looked like she had put on quite a bit of weight and had a matronly look about her that belied her slutty past.

I knew that Cheryl would be pleased as I escorted my wife over to Paula and her husband and extended my hand in greeting. I think Paula was a little taken aback by my formality, but nevertheless we shook hands and introduced our spouses to each other. I could tell that Paula's husband, Richard, found Cheryl very attractive and when we were joined by a couple of our other classmates, Cheryl leaned over and whispered to me, "Watch this."

Cheryl then started flirting outrageously with Richard, laughing at everything he said, touching his arm as he spoke and basically coming on to him right in front of everyone. From looking at Richard I knew he wasn't really Cheryl's type, but I must say that I loved the pay-back as Paula was positively seething with jealousy as her husband responded eagerly to Cheryl's flirtations. Eventually, Paula couldn't take any more as she grabbed Richard's hand and led him over to the bar.

Once they'd left, I looked over to see Cheryl grinning from ear to ear. "How did you like that, Mike? I gave Paula a taste of her own medicine, eh?" giggled Cheryl while leaning over to give me kiss on the cheek.

I laughed at Cheryl's little ploy but before I could respond to Cheryl, my friend Gabe approached us and after I introduced him to Cheryl we started reminiscing about old times. Cheryl took this as opportunity to mingle with my other classmates as she darted from group to group introducing herself as my wife.

Cheryl has always been something of a social butterfly and she is always in her element at parties or other large gatherings and before I knew it, she was introducing me to spouses of my classmates and even to some of my classmates themselves. This went on for a couple of hours as I noted that Cheryl was attracting quite a bit of attention from the single men. This attention only increased when the music started and Cheryl began to dance, first by herself, but later with an ever-changing variety of male partners.

As I stood by the side of the dancefloor watching my wife dance, I was filled with a strange mixture of fear and pride. Fear that one of men would pique her interest and I would be left to explain how my wife had disappeared with another man at my class reunion. But at the same time, I was proud of the fact that Cheryl was so sexy and desirable, and I knew that my stature amongst my classmates had undoubtedly increased ten-fold by her mere presence at this event.

My fascination with admiring my wife was suddenly interrupted when out of the blue, I heard, "There you are, Mikey. I was hoping I'd see you here." I turned to see, Dan, the man who had cuckolded me on graduation night and forever ingrained into me that I should meekly step aside when my woman chose to be with other, more masculine, men.

It's funny, but in all the lead-up to the reunion, I hadn't thought about Dan at all. I'd been so caught up in the idea of making Paula jealous that I'd completely ignored the fact that it wasn't just Paula that had participated in my first cuckolding. Dan had been conspicuously missing from the reunion and after our greeting, he explained that he'd been held up at a client appointment down in San Jose earlier that evening and couldn't make it back in time.

Neither Dan nor I mentioned his dalliances with Paula and instead we talked of our respective careers and I learned that he'd dropped out of college after only a year to work as a contractor. He now ran a good-sized business specializing in kitchen and bath remodels. I also learned that Dan was newly single, having divorced his second wife not more than three months before.

To be honest, I couldn't understand why Dan was even bothering to talk with me as we'd never been friends and only had Paula as a common connection. But after a bit, Dan said, "John said I'd want to meet your wife. Where is your better half anyway?"

Ah! So that was it. I instantly realized that John had probably told Dan about meeting Cheryl. My wife knew that John as well as Dan had fucked Paula back in high school and Cheryl had made an extra effort to flirt with John, likely trying to make me jealous. It hadn't really worked since John was now sporting a Dad body and looked as if he hadn't missed a meal in ages. But in answer to Dan's questions, I pointed out Cheryl on the dancefloor where she was shimmying to the upbeat music.

Seeing my wife, Dan did a double-take before slapping me on the back and saying, "Looks like you did well, Mikey. I can't wait to meet her."

I knew it was just a casual remark, but there was something in the way Dan phrased his statement that put me on guard. After all, Dan had always been a good-looking guy in high school and he'd clearly aged well. If anything, he was more buffed, no doubt keeping fit as part of his job, but it was also apparent he put in quite a bit of time in the gym.

I've always had a sixth sense about guys to whom Cheryl is attracted and Dan certainly fit the bill. Nevertheless, I tried to put my fears to rest as Dan and I kept up our conversation until the music momentarily stopped. This was Dan's cue and he abruptly said he was going to go meet my wife, striding over to Cheryl and introducing himself.

I watched Cheryl and Dan shake hands and then Cheryl leaned in close to Dan and whispered something in his ear. They both then started laughing before they made their way on to the dance floor and began to dance to the music. I later learned that Cheryl had told Dan that she'd heard all about him and that he had better keep his hands to himself since she wasn't as easy as Paula.

For the next hour or so I watched Cheryl dance with Dan as well as several of the other men at the reunion. It seemed as if Dan was still good friends with quite a few of my former classmates and in between dances, he introduced Cheryl to several additional classmates of mine from high school.

While I was keeping a careful eye on my wife, old friends would occasionally stop by and we would reminisce about our high school days but for a good part of the evening I just stood to the side and kept my focus on Cheryl.

To my great relief my wife didn't drink too much and was keeping her flirtations in check. That's not to say she was a prude, after all, Cheryl has always loved to tease men and she was flitting about among the single guys, dancing close and giving hugs at the conclusion of each dance. But nothing in her behavior indicated that she was sexually available but instead she merely looked like she was having a good time.

Eventually, the DJ announced the last song and after dancing the final dance with Dan, Cheryl bounded over to me with a happy smile and announced, "This has been so much fun."

I was happy for my wife and to be honest I'd had a great time too. And as we stood together saying our goodbyes to everyone, I felt that a great weight had been lifted from me. No longer was I the nerdy schoolboy cuckolded by my girlfriend, I was a successful man married to the sexiest woman at the reunion. My self-esteem was sky high that night and I was so grateful that Cheryl had helped me to restore my image amongst my classmates.

As we said our goodbyes, I was careful to remember Cheryl's earlier admonishments and I made it a point to shake hands with all the women rather than the more customary hug. Cheryl, on the other hand, gave all the guys a big hug while I stood next to her holding her purse. With several of the single guys the hugs lasted longer than would generally be considered appropriate and when she said goodbye to Dan, I noted that he placed his hands on the firm globes of Cheryl's ass as she offered him her lips as they kissed goodbye. For the most part, however, everything went off without a hitch and when Cheryl and I were finally seated in our car I thanked Cheryl profusely for making the reunion a resounding success.

"You made me so proud, sweetheart," I stated as I leaned over to give Cheryl a kiss.

Cheryl giggled hearing this as she responded, "Why? Cause I didn't run off with one of your friends?"

"Yes..., I mean no! That's not what I meant," I stammered.

"Good, because I wouldn't do that to you. I know this was a big deal to you and I didn't want to embarrass you in front of your friends," giggled Cheryl.

Cheryl reached over and placed her hand on my thigh before continuing, "But Dan did give me his number and said I should call him if I ever wanted to join him for a drink or something."

"What!" I exclaimed as a shudder went through my spine.

"Yeah, he made me take it even though I said I wasn't like Paula," giggled my wife.

"No, No, No, you can't go out with Dan," I pleaded while looking at Cheryl, anxious for some sign that she agreed with me.

My wife was obviously not wanting to upset me as she said, "Okay, I won't call him. But if you ever change your mind, let me know. He's really good looking. I can see why Paula had a thing for him."

My previous good mood instantly vanished and all I could think was did I have a sign on my back that read "I'm a cuckold. You can fuck my wife." And the nerve of Dan! He'd fucked my high school girlfriend on graduation night and made me the laughingstock of all my classmates and now he wanted to do the same with my wife! I was livid in anger but by this time, I thought it might be a good idea to start the car and head home before someone we knew noticed us still sitting in the car discussing how Dan had asked out my wife.

Once we arrived home we headed straight to bed where Cheryl basically demanded that I lick her pussy until she came before she would deign to unlock my chastity cage. It didn't take long for my wife to scream out in climax, her arousal stoked by having flirted with various guys all evening long.

And when I finally had unfettered access to my penis, my wife had me retell her the story of how Dan cuckolded me with Paula while I stroked my dick. As I detailed the shameful experience of masturbating while listening to Dan fuck Paula in the adjoining motel room, Cheryl egged me on, cooing, "Oh my God, Honey, that's so naughty. Do you think Dan knew you were listening to him fuck your girlfriend?"

That's all it took, and I was soon spurting out my load all over my hand and stomach as I relived that humiliating moment. Cheryl seemed particularly pleased with herself as I mopped up my come with a tissue and when I finished cleaning myself, she teased, "Any time you want me to call Dan, just let me know."

For the next several weeks Cheryl played her hand brilliantly. Not one word was said about Dan asking my wife out for a drink, but every time we had sex, it consisted of me licking Cheryl to climax before she allowed me to masturbate. But each, and every time, rather than Cheryl describing one of her many extramarital encounters, she'd have me recall one of the times that I'd jerked off after dropping Paula off at Dan's house.

My wife would have me first describe my date with Paula, where we went and what we did, before insisting that I tell her exactly what I fantasized about when I later had my dick in my hand. In some ways, these tell-all sessions were therapeutic. I would describe my deepest, darkest fantasies, telling my wife how I'd masturbate to visions of Dan fucking my sweet Paula, my girlfriend's blatant infidelity a powerful aphrodisiac to an innocent virgin like myself.

Cheryl would always interject her own probing questions, breathlessly moaning, "Do you think it was more of a turn-on because Dan is such a stud?" or "Why do you think Paula never wanted to have sex with you?"

I'd always try to answer my wife's questions truthfully, enjoying the chance to examine my own thoughts on this pivotal moment in my life. The entire time, I'd be pumping my dick but every time, after I'd come, I'd feel the same sense of shame and humiliation that I did forty years ago when Paula first cuckolded me.

All this time, I'd still not told Cheryl everything about Dan and how our history colored that fateful graduation night. But eventually I worked up the courage to tell Cheryl how it wasn't just that Dan had screwed my girlfriend, but that he'd repeatedly bullied me in gym class.

Cheryl tried to be sympathetic, but when I told her about how Dan had once yanked down my gym shorts in front of everyone, she couldn't help but giggle at the image of me standing in front of both the boys and girls gym classes in just my jock strap. Eventually, even I started chuckling at remembering this humiliating moment and I said, "Yeah, it probably was pretty funny. But I was so embarrassed."

Cheryl shook her head dismissively as she said, "Oh my God, Mike. That's no big deal. You were both kids."

"I know, I know. But he was always giving me a hard time, I just felt like he had it out for me."

Cheryl just smiled at my statement as she stated, "Aw, Mike. It sounds like Dan really got into your head, didn't he?"

I couldn't help but agree with my wife as I confessed that after having been humiliated in gym class, I'd tried to stay out of Dan's way. "But then he goes and fucks Paula," I sheepishly whined.

"But c'mon Mike, you played with yourself when he screwed your girlfriend. You must have liked some part of it."

My wife knew me too well as I tentatively replied, "Yeah, I know. I guess I did." And after a momentary silence, I admitted that as embarrassing as it'd been, Paula fucking Dan had been the most exciting thing that had ever happened to me at that point in my life.