A Cuckold Story Ch. 52-55

Cheryl's face lit up into a smile as she said, "See. I knew you loved it. I know how you are. You're such a dirty little boy sometimes. You liked that Paula fucked another guy, but it was even hotter because it was Dan, right?"

My wife had hit the nail on the head. Cheryl knew that somewhere deep in my psyche, I craved the humiliation of surrendering my woman to a man that intimidated me. And when I thought about all the men who'd slept with Cheryl over the years, it was always the ones that were confident, alpha-males that were featured in my favorite memories. Brad, Chris, James, and even Ian, had all been men to which I instinctively deferred and whenever I'd picture one of these guys fucking my wife, I'd develop an instant erection.

Even with those men that I'd never met, like John, the Colorado Guy, or the Gym Guy, I knew enough from Cheryl's descriptions that I'd wilt in their very presence. They were all confident, assertive men who never even gave me a second thought when it came to fucking my wife. But strangely enough, the fact that these guys were so dismissive of me made it that much more exciting when they cuckolded me, just as I had gotten off on Dan fucking Paula on that fateful graduation night.

I guess I was lost in my thoughts as I heard Cheryl chirping, "Mike, what wrong?"

"Sorry Sweetie. I was just thinking. You know, I think you're right. When Dan fucked Paula, it was hotter because I was kind of scared of him," I confessed while keeping my eyes downcast.

There was another awkward silence before I added, "When Dan picked on me in my gym class, I never stood up to him. And when he fucked Paula, I didn't stop him either. I should have been pissed, but I was turned on instead. I don't know why, but I was."

Cheryl reached over and soothingly placed her hand on my thigh as she cooed, "Don't worry Baby, I think it's horny that you played with yourself that night."

I then blurted out, "I'm such a weirdo."

My face had turned bright red at my shameful confession as Cheryl consoled me, saying, "No, you're not a weirdo, Baby."

My wife then lifted her hand from my thigh and draped it over my shoulders, pulling me close. "Honey, you're a really great guy. Everybody thinks so," cooed Cheryl.

Cheryl's comforting words lifted my spirits and I replied, "Yeah, I suppose I should be grateful to Dan. It might not have worked out as well for me and you if I hadn't already learned to get off on Paula's cheating."

My wife smiled approvingly at my statement and I realized that she could see into my very soul. Cheryl knew that when Dan fucked Paula it had been a pivotal moment in my sexual evolution. And now, having confessed that it was even more arousing given that Dan had bested and humiliated me a year earlier, my wife was privy to my most intimate secrets.

But Cheryl didn't judge me for my unusual take on having been cuckolded by my nemesis. Instead, she encouraged me to talk about it and I found myself baring my deepest, most hidden feelings, telling my wife that the humiliation and embarrassment of that night had triggered something in me. I explained that at the time, I'd been ashamed and confused by my feelings, but I'd since learned that letting one's girlfriend, or wife, enjoy the attentions of other men, especially men that intimidated me, like Dan, is the ultimate thrill.

As I poured out my innermost secrets, I absentmindedly began to fondle my penis, ultimately unzipping my pants and masturbating as I described, once again, the full gamut of emotions that flowed through me when I masturbated listening to Dan fuck Paula on graduation night. It was a liberating moment and this time I left nothing out, telling my wife how I'd pictured Dan fucking my girlfriend while sporting the same arrogant smirk he'd had on his face when he yanked down my pants in gym class.

And when I admitted that the shame and humiliation of witnessing my girlfriend's infidelity had only stoked my passions, I felt a weight lifted off me. I now knew that the subject of my initial cuckolding was not something to be avoided and I could freely discuss my deepest, darkest desires with Cheryl without any reservations.

All this time, I continued to unashamedly work my penis, the exhilaration of openly exploring my first cuckold experience was intoxicating. Cheryl just watched me serenely through my masturbation session and when I came, she leaned over and kissed me on the cheek, cooing, "You still love thinking about how Dan screwed Paula, don't you? That's really cute."

I knew perfectly well where this was all headed. The more I thought about and discussed how Dan had fucked Paula, making me a cuckold well before I'd ever even heard of the term, the more I knew that deep down inside, I wanted him to fuck Cheryl.

My wife even began to add her own thoughts on the subject, telling me that she understood why Paula screwed Dan, claiming that most women, including herself, are naturally drawn to the biggest and strongest men. "Oh my God, of course Paula wanted Dan. I totally get it. She probably loved fucking one of the stars of the football team. That's how girls are", giggled Cheryl.

Of course, with Cheryl encouraging me to reminisce about my initial cuckolding and fueling my arousal with her own naughty comments, I found myself thinking of Dan and my wife almost continuously. And eventually, no more than a week following my gym class confession, over a romantic dinner with Cheryl at our favorite local restaurant, I blurted out, "Maybe you should call Dan."

My wife and I had been talking about the upcoming summer and what vacations we might want to take. And Cheryl had just suggested that maybe we should plan a weekend at a Mendocino hotel when I let slip my changing thoughts on her seeing Dan. And when she heard my statement, a broad smile formed on my wife's lips as she calmly asked, "Well, well, well, what made you change your mind about that?"

I then began a long rambling explanation of how Dan had been the first guy to cuckold me and how it'd been a hugely important event in my life. I told Cheryl that when Dan fucked Paula, I'd felt humiliated and ashamed but that now I realized that a good part of my arousal stemmed from the fact that Dan had bullied me and that it turned me on to then witness my girlfriend submitting to him.

"Like I told you the other day, Dan was a larger than life figure to me. So, when he fucked Paula it was like the hottest thing I'd ever experienced,", I confessed.

"So now you want me to fuck Dan. Right?", asked Cheryl, a mischievous smile gracing her lips.

The way my wife explicitly framed her question left me little room to maneuver as I said that whether she fucked Dan or not was entirely up to her. But I was giving Chery permission to join Dan for a drink and whatever happened afterwards was okay by me.

Cheryl listened with a sympathetic ear. She understood that I was coming to grips with the roots of my cuckold desires and she let me expound on how I wanted her to do whatever she wanted with whomever she wanted. "So, you wouldn't mind if I ended up fucking him?" queried Cheryl once again, this time giving me a look that indicated she wanted a firm answer.

"No, I wouldn't mind. I think it'd be hot."

It was fortunate that our table was in a secluded location as our conversation had taken a decidedly kinky direction. But when I said this, Cheryl leaned over and whispered, "Okay, Baby. This is going to be fun. I'll call Dan first thing tomorrow."

"Okay, but make sure he doesn't think that I know about everything. I don't know if I could deal with that."

My wife then giggled, "That shouldn't be a problem. I'll call Dan and tell him I'll take him up on his offer to get a drink. And then we'll see how things go."

My penis was already hard in my pants at the thought of my wife going out with Dan but at the same time I immediate began to develop misgivings. Dan seemed to still be in contact with a good number of my former classmates and I could easily picture him bragging about how he'd cuckolded me a second time!

I guess I started musing about all the potential pitfalls of Cheryl and Dan dating that I became lost in the clouds when my wife interrupted my thoughts. "Hey, Mike! What's wrong?" queried Cheryl as I then began sheepishly describing my concerns.

"Oh, c'mon Mike. Don't be silly, that's no big deal. Who cares if he tells anyone? Wouldn't that make it hotter if all your old friends knew that Dan was fucking your wife after he fucked your girlfriend back in high school?" laughed Cheryl.

To be honest, I felt my dick twitch involuntarily at the prospect of my former classmates knowing that Dan had cuckolded me once again. And although I wasn't truly on-board with everything, I told Cheryl I was okay with however things turned out so long as she was happy.

We left the restaurant soon after our conversation and the entire drive home, Cheryl gushed about how she couldn't wait to go out with Dan. My wife even confessed that she, too, was aroused by the notion of screwing the guy who'd first cuckolded me so many years ago. "And it doesn't hurt that Dan's a really good-looking guy," laughed Cheryl as she mused about what it was going to be like dating the guy who'd slept with my old girlfriend.

By the time we arrived home, I was rock hard, and I immediately attempted to coax my wife upstairs to the bedroom. Cheryl had other plans, however, as she sat down on the couch and reached up under the skirt to pull off her panties. Once my wife had maneuvered her frilly panties over her high heel sandals, she tossed them aside demanding that I lick her pussy.

This was hardly an unpleasant task and I immediately dropped to the floor in front of Cheryl and began to tongue her juicy opening as she moaned in appreciation. And as I continued to worship my wife's cunt, she began telling me that she wanted to fuck Dan to show him how much better she was than Paula. Cheryl then went on to say that when I masturbated, she wanted me thinking her and Dan, not Dan and "that bitch Paula."

This was the first time Cheryl had mentioned this motivation for wanting to hook up with Dan and I realized that there was more than a hint of jealousy in my wife's scheme. This insight was something of a turn-on to me and I picked up the pace on Cheryl's clit, teasing it with swipes of my tongue. It didn't take long before my wife was crying out in orgasm, shudders rippling through her body as I continued to run my tongue over her clit.

When my wife eventually recovered from her climax, I'd assumed it would now be my turn to get off, either by making love, or more likely, by masturbating. But as I started to shuck off my pants, my penis already standing at full attention, Cheryl wagged her finger exaggeratedly, giggling, "Nu-uh Baby, not tonight. You know the rules. I'm going to call Dan tomorrow and maybe he'll want to get together right away."

I must admit to being disappointed, but I did indeed know the rules. Cheryl was planning to see another man and that meant no sex for me and to prove the point, my wife then said, "Why don't you go upstairs and lock that little thing up. You can bring me the key when you're done."

I dutifully turned to head upstairs, but not before taking in the erotic sight of my wife lying back on the couch. Cheryl's legs were still splayed wide and her pretty, pink pussy was on full display, taunting me with the fact that it was off-limits to me. I suppose a real man would never have taken no for an answer in a situation such as this. But as I dutifully headed upstairs to the bedroom, I knew that I wasn't a real man, I was a cuckold. And as a cuckold I'd do exactly as my wife wished, securely locking my penis in chastity while she saved herself for Dan.

It took some time for my erection to subside, but I eventually slipped my dick into the chastity device before heading back downstairs to give my wife the key. "That's much better. I need to keep your little dickie locked up until after I see Dan. We don't want you having second thoughts about this," giggled Cheryl as she reached over grabbed her purse and placed my key in her pocketbook.

With me now in chastity, my wife patted the seat next to her on the couch and when I sat down, she leaned over and gave me a passionate kiss on the lips. "Oh my God, this is going to be so much fun Baby. I wonder what Dan will think when I call him tomorrow?" giggled Cheryl.

"I don't know. He'll probably think he's pretty lucky," I replied.

"Yeah, maybe. I don't think he thought I'd ever really call him. He'll probably think I'm kind of a slut."

I chuckled at my wife's reference to herself as a slut as I said, "Aren't you going to tell him what you tell all the guys? That I suck in bed?"

Now it was Cheryl's turn to chuckle as she sarcastically replied, "I don't tell them you suck in bed. I just say that you've got a tiny little dickie and you come way too fast." This statement stung a bit, but I'd heard it all before and so rather than take offence, I laughed and soon my wife and I were both giggling together at the thought of Cheryl telling Dan of my sexual shortcomings and musing about how Paula must have had some sort of sixth sense about these sorts of things.

By the time we slipped into bed that evening, Cheryl and I were talking and laughing like high school sweethearts. For whatever reason, the prospect of my wife dating and possibly fucking the man who first cuckolded me had me feeling like the virginal teenager I'd been when I first learned of Paula's infidelities. But now, rather than being overwhelmed with the sense of shame and embarrassment, I could more fully appreciate the erotic nuances of the situation. To be sure, I still felt some humiliation, but as any cuckold knows that's part of the excitement.

I was certainly anxious to hear about my wife's date with Dan. Maybe after all these years I'd finally get a chance to learn whether Dan really had the horse-sized cock that I'd always imagined when I would masturbate to thoughts of him fucking my girlfriend. And maybe my wife could learn more about all the other times Paula cheated on me. Surely, she'd slept with Dan more times than I knew about. And what about other guys? I knew that John had fucked Paula since I'd dropped her off at his house several times following our dates. But when he'd apologized, Dan had hinted there were others and I was curious as to just how many guys had slept with my girlfriend while my sexual advances were routinely rejected.

The next day at work I was on pins and needles wondering how my wife's call with Dan would go. I didn't call Cheryl all day long and when I arrived home, I fully expected to be put to work helping my wife get ready for a date. But when I walked in the door, Cheryl was outside lounging around the pool reading a magazine and when I asked her how the call went, she grinned and said, "I'm meeting Dan this Friday for drinks and dinner."

Although I was fully prepared to hear this, the reality suddenly dawned on me. My wife was going out with the man who first cuckolded me with Paula! I kept my anxiety in check, however, as I replied, "That's good Honey. So, the call went well?"

Cheryl giggled at my question as she answered, "Yeah. He said he knew I'd call." My wife's statement was like a punch to the stomach. What is it about some guys that they just know my wife will cheat on me? Was it me? Did I just give off the vibe that I was incapable of satisfying my wife? Or was it Cheryl? Did her appearance and flirtatious behavior advertise her availability? Either way, I had to admire Dan's confidence and I knew it was just this sort of self-confidence that had inspired my wife to lower her panties many, many times before.

That night and for the following two nights, Cheryl and I didn't speak much about her upcoming date with Dan. With me locked in chastity, I knew that discussing my wife's plans would only be an exercise in frustration and I think that Cheryl was letting me mull over the ramifications of what she was going to do without her usual teasing. On Friday, however, I rushed home from work to help my wife prep for her date and as I was shaving her sweet pussy, Cheryl asked, "So, Mike. I hope you're still sure about this. I want to know you're still on-board with me going out with Dan?"

I didn't have to think long on this subject as I immediately replied, "Yeah. I'm okay with it."

Cheryl then took a more serious tone as she said, "Are you just okay with it, or do you really want me to fuck him? I need to know."

This was a new one for me. My wife has never really asked for my permission to fuck other men and whether I want her to or not has never really been up for discussion. But as I continued to carefully shave the folds of my wife's vagina, I calmly replied, "I want you to fuck Dan. I want him to know that my wife is the sexiest, most beautiful woman in the world."

And as this statement was hanging in the air, I added, "You're the only woman I've ever had sex with and I'm proud of that. But this is my chance to come to terms with the first time I was cuckolded. Only this time it'll be with you instead of Paula and instead of imagining what Paula and Dan did, you can tell me all about it later. I can't wait to hear about you and Dan."

Cheryl smiled sweetly down at me as I said my piece and when I finished with my task, she jumped in the shower while I waited, sitting quietly on the bed. Cheryl and Dan were meeting at a bar and grill not far from my old high school and so my wife opted to dress somewhat casually. Carefully laid out on the bed were tight black ankle length jeans, a sparkly, low cut top and a pair of simple black pumps along with a skimpy black g-string.

When Cheryl emerged from the bathroom, she rummaged through her jewelry drawer and pulled out a pair of large silver hoop earrings and multiple silver bracelets. I watched silently as my wife dressed, marveling at how beautiful and sexy she looked and wondering just what Dan would think about getting the opportunity to cuckold me once again. And when I knelt before my wife, performing my pre-date ritual of helping ease her pretty feet into her high heel pumps, I looked up at Cheryl and sheepishly declared, "Cheryl, you are so beautiful, and I love you so much. I hope you have a great time tonight."

My wife smiled knowingly at my statement as she said she had a "good feeling" about her date with Dan. And Cheryl then did something that she rarely ever did, as she asked me if I wanted her to unlock my chastity cage so that I could "play with myself" while she was out. As tempting as it was to have the opportunity to masturbate, I opted to remain locked up, telling Cheryl that I wanted to save my masturbation session for when she returned home so that we could share the experience.

Cheryl left soon after this little exchange and as she headed out the door, she told me, "Don't wait up," a clear signal that if things went well, she might be spending the night in Dan's bed.

That night I tossed and turned for several hours before falling asleep. It turned out Cheryl did, indeed, spend the night with Dan and it was only mid-morning the next day when I heard her car in the driveway followed by the click of her heels on the walkway up to the house. It was a warm day and I had been out cleaning the pool when I heard my wife's car and I hurried into the house to greet her. "How'd it go?" I asked as I gazed at my wife, amazed that she looked so chipper after spending the night with a new man.

"It was fun. Dan's actually a really nice guy," replied Cheryl as she turned and headed upstairs to the bedroom. I followed behind closely and when my wife entered the room, she kicked off her shoes and then began stripping off her clothes.