A Cuckold Story Ch. 52-55

When Cheryl tugged off her pants, I noted that her g-string looked moist and if I had to guess, I would assume that she and Dan had fucked that very morning. My wife caught me staring at her crotch and smiled, giggling, "You want a taste, Baby?"

I was on the bed in a flash as my wife straddled my face and lowered her creamy pussy down over my mouth as I licked and sucked the residue from her earlier encounter with Dan.

All I could think as I cleaned my wife's pussy was that this was what I was meant to do even forty years ago with Paula. My role wasn't to be the alpha male, fucking women to multiple orgasms and making them cry out in ecstasy. My calling in life was to be the supportive partner of a woman who embraced her own sexuality. A man who forgives all indiscretions and who welcomes back his wayward wife with an indulgent smile and soothing tongue. And as I mused on these thoughts, I kept my tongue dancing over my wife's clit until she began to grind against my face and then cried out in climax, her pussy spasming in delight.

When Cheryl eventually rolled off my face, she looked down at me with a mischievous smile. "You liked that, huh?" My wife then got up off the bed and retrieved her purse and pulled out my key. "Go on, Baby. Show me how much you like me fucking Dan," teased Cheryl as she handed me my key.

Since I'd been cleaning the pool, all I had on was my Speedo and so after shucking off my bathing suit, I quickly unlocked my chastity cage and slipped the plastic sleeve off my dick. I then laid back on the bed while Cheryl lay beside me on her side watching me begin to fondle my penis. While I masturbated, Cheryl bragged, "Dan said I was much better than Paula," which caused me to pick up the pace of my strokes.

I guess I was anxious to hear more of my wife's encounter as I had to periodically remove my hand from my dick to keep from coming as Cheryl continued to tell me of her night. It seems that Dan just assumed that my wife's acceptance of his invitation for a drink meant he was getting laid since as soon as they finished dinner, he asked Cheryl to come back to his house.

Although my wife was a little surprised at Dan's presumption, she was also becoming more and more aroused at his manly good looks and confident demeanor. And so, Cheryl agreed to follow Dan back to his house in her car, pleased that he lived no more than a couple of minutes from the bar.

Once at Dan's house, he wasted no time in making his move and within no more than fifteen minutes my wife and Dan were making out on his couch. Over dinner, Dan had asked Cheryl why she'd agreed to meet him for drink and my wife explained that she was curious as to why Paula fucked him and not me. And so, when my wife unzipped Dan's pants and unleashed his cock, she licked her lips and exclaimed, "I guess this explains why Paula fucked you instead of Mike! You're so big! A lot bigger than Mike!"

Cheryl later told me that Dan wasn't enormous, certainly nothing like James had been, but he was a far sight bigger than me and, of course, he reveled in the comparison. And as my wife sucked Dan's cock, he kept up a running commentary on how he'd fucked my girlfriend in high school and now was going to fuck my wife.

Eventually, Cheryl removed Dan's cock from her mouth and pulled away, stripping off her jeans before laying back on the couch with her legs spread wide. "C'mon, Baby. Fuck Mike's wife," moaned my wife as Dan moved into position between my wife's legs and inserted his cock.

"Aww, that's it. That feels so good," sighed Cheryl as Dan buried his cock to the hilt in her juicy pussy.

I continued to stroke my dick as Cheryl described how Dan fucked her through first one, and then two, incredible orgasms. And all the while, Dan couldn't stop gloating about how he was now cuckolding me for a second time.

"You like this big cock, eh Cheryl? I'll bet Mikey's never fucked you this good," roared Dan as he continued to pound my wife, his cock churning in Cheryl's juicy pussy.

I suppose I should have felt ashamed when my wife told me she played along with Dan, telling him he was so much bigger and better than me, but with my hand furiously working my penis, my thoughts were entirely focused on my wife's lurid description of her tryst. And as Cheryl told me how Dan had rolled her over on top of him, slapping her ass as he roared, "Oh yeah! That's it! Ride that cock!" I couldn't hold off and I began to spurt out my load.

Cheryl watched me come with a mischievous smile on her lips. I had just masturbated to the tale of my wife's infidelity with the same man who'd cuckolded me with my high school girlfriend, and I felt as if my life had come full circle. Of course, I was still the odd man out, my pleasure coming via my own hand rather than from my wife or girlfriend. But hearing all the naughty details firsthand from Cheryl was a sublime pleasure and I knew from the way she had described her encounter with Dan, this was not going to be one-time experience.

Over the course of the next couple days Cheryl filled me in on additional details from her night with Dan. It seems my wife had pried quite a bit of information out of Dan regarding his relationship with Paula and I must admit hearing about how she had cuckolded me throughout our relationship was both hurtful and arousing.

Although I knew that graduation was not the first time Paula had cheated on me, it turned out that pretty much the entire high school knew that Paula was spreading her legs for other guys. And while I knew Dan and John had slept with Paula, what I didn't know was that several other classmates of mine had fucked my girlfriend, including my good friend Jason. Dan even told Cheryl that it was common knowledge that Paula hadn't slept with me and there were rumors that I might be gay since I'd never sealed the deal with my slutty girlfriend.

I must admit that dredging up all this baggage surrounding my first relationship was cathartic in some ways. And because Paula and I'd never had sex, Cheryl was happy to discuss my thoughts and emotions without her usual jealous reaction to the idea of me with another woman. In fact, after hearing about how Paula and Dan used to laugh about how I would obediently drop her off at Dan's house after our dates, I told Cheryl that I was glad Paula never let me have sex with her. "If I'd had sex with Paula, then you wouldn't have been my first. Or my one and only," I sheepishly told my wife.

"Aww, that's so sweet Mike. I love that you think that," cooed Cheryl as she leaned over and gave me a kiss.

On Sunday night following Cheryl's Friday night date with Dan, my wife received a text from Dan asking if she wanted to get together for dinner that Wednesday evening. My wife replied with an enthusiastic "Yes!" and after Cheryl sent her response, she had me sliding my chastity device back on to my penis in anticipation of her upcoming date. And over the next couple months, this sequence of events played itself out with Cheryl seeing Dan at least once, and sometimes, twice a week.

Of course, it's highly unusual for a married woman to have the freedom to spend that much time away from home. But when Dan asked Cheryl what I thought of her frequent absences, my wife merely told him the same thing she'd told James during their lengthy relationship. Cheryl explained to Dan that in our marriage, she'd made it clear to me at the outset that she needed her space, and that I wasn't to question her on her whereabouts or who she might be with.

"Man, that's some arrangement," laughed Dan before asking, "Do you think he suspects you're cheating on him?"

Cheryl just giggled, "Yeah, maybe? But Mike's not into confrontation. He's just not that kind of guy."

My wife then added in a somewhat cheeky statement, "You know, Mike's a really nice guy and a great husband, but like I told you, he sucks in bed. It's not his fault, I know that, but what am I supposed to do?" Like James, Dan was amazed that Cheryl could treat me this way without some sort of pushback, but in Dan's case, it was probably easier to understand as he'd already seen it firsthand, every time I'd obediently dropped Paula off at his house following our dates.

When Cheryl related this conversation to me, she'd just returned from an overnight stay at Dan's house. I'd attempted to coax my wife into the bedroom, perhaps licking and sucking her well-fucked pussy after what she'd described as an "incredible" night with Dan. But Cheryl put me off, telling me that she was tired and wanted merely to lounge around the house for the day. In fact, the only reason she'd brought up her conversation with Dan was because she was wondering whether it might just be easier to tell him I was aware she was dating him and was okay with it.

Now, when a wife says her husband "sucks in bed", I think most people would consider that a hurtful comment. But when Cheryl told me what she'd told Dan, I didn't take it that way at all. I've met or known enough of my wife's lovers to know that, at a minimum, physically I can't compete. Most all Cheryl's boyfriends have been tall athletic men and the way she describes their thick, girthy cocks and pendulous balls, I know she was long ago ruined for me.

And as to my sexual skills, let's just say that most women, let alone one as sexually experienced as Cheryl, would be greatly disappointed by my hair-trigger stamina and clumsy bedroom technique. No, I am perfectly capable of admitting my sexual deficiencies and when Cheryl told Dan that I "suck in bed," she was merely stating the truth as she'd done many times before with other lovers.

All of that said, when my wife suggested we let Dan in on the fact that I was a willing cuckold, I immediately recoiled from this notion.

Although I'd come to grips with the fact that Dan's high school bullying had been an integral part of the intense arousal I'd experienced when he fucked Paula, I still wasn't ready for this next step. Cheryl had told me enough to know that Dan hadn't changed all the much from high school. And although I loved hearing how Dan reveled in cuckolding me once again and I even shrugged off Dan's tendency to use my sexual failings as part of his verbal foreplay, I still couldn't imagine letting him know I was a willing cuckold.

After explaining my concerns to Cheryl, she agreed to continue to pretend to be cheating on me. My wife did say, however, that she was going to continue to spend nights at Dan's and that she didn't want to curtail her get-togethers with her new boyfriend just to keep up this pretense. I readily agreed to Cheryl's terms, telling her she was free to see Dan whenever she wished and that I'd just reprise my role as the gullible, cuckold husband, a role I'd played so many times before.

Chapter 53

Although Cheryl continued to maintain that she was cheating on me when with Dan, they would often meet up at the bar and grill where they'd had their first date. This bar was minutes from Dan's house, and my wife and he would typically meet there for a drink or two and then head back to his place.

And as it turned out, this bar was a regular hangout for many of Dan's friends, including quite a few of my former classmates. My wife said that more than once, she'd arrive at the bar to find Dan talking with friends, and if they were former classmates of mine, they'd remember Cheryl from the reunion. My wife and Dan maintained that they were "just friends," but with Cheryl all dolled up for the evening, her skimpy dresses and sky-high heels screaming "date night," it quickly became obvious to all that they were having an affair.

To be honest, knowing that Cheryl and Dan's affair was common knowledge wasn't as bad as I thought it might be. I hadn't really kept up with any of my former classmates after the graduation night incident and having them now know my wife was also cuckolding me with Dan gave me something of a kinky thrill. And when Cheryl would return home and tell me about the scandalized looks she'd receive or I'd imagine what sort of things were being said about us, I'd masturbate much like I did when Dan was fucking Paula, my embarrassment and shame only serving to stoke my arousal and making my orgasms that much more intense.

My tolerance for knowing that others were aware of my wife's affair, however, was put to the test when one night almost three months into Cheryl and Dan's affair, my wife and I ran into Dan while out at dinner. We'd just entered the restaurant and there, standing before us was Dan and Jim, another former classmate of mine.

Jim and Dan had been close friends back in high school and had obviously kept in touch. Jim, like Dan, had been one of the stars on the baseball team when we'd won the championship and I'd even wondered whether Jim might have slept with Paula back in the day. But Cheryl later told me that was just my imagination as Dan had given her a thorough accounting of all the guys who had been successful in bedding my girlfriend, and all though there were more than I suspected, Jim wasn't one of them.

Seeing Dan and Jim, who she'd met at the reunion, waiting for a table, Cheryl immediately shrieked, "Oh my God, look who's here," as she then gave them both big hugs while I stood stoically beside my wife, cursing our bad luck at running into those two.

I instantly suspected that maybe my wife had planned this meeting. But when I took note of Cheryl's attire, tight ankle jeans, a peasant blouse, and a pair of mid-height platform shoes, I realized that she hadn't dressed intending to see Dan. With Dan, or any of her previous lovers for that matter, my wife always dressed overtly provocative, miniskirts, tight tops and high heels were de rigueur. Cheryl is cognizant of the power of sexy clothing, and although her ensemble that night was attractive to be sure, she wasn't clad in her typical cock-hardening date night attire.

Even though I realized my initial thoughts had been incorrect and that this truly was a chance meeting, I still had an awful feeling in the pit of my stomach seeing my wife cozy up to these two guys. And when Cheryl insisted, "You guys have to join us for dinner," I felt like my world was about to be turned upside down.

Soon enough, the hostess had seated at our table and as the four of us sipped our drinks, I remained relatively quiet while Cheryl chattered away. To my relief, the conversation was innocuous, with my wife asking Jim about his wife and with her telling him and Dan that we'd been together since college.

Eventually, Cheryl brought up the reunion and told both guys that she'd had such a great time and loved meeting all my old friends. Suddenly, however, out of the blue Cheryl exclaimed, "I especially loved meeting Mike's old girlfriend, Paula." My wife then turned to Jim and casually asked, "You knew Dan screwed Paula on graduation night, didn't you?"

Jim and Dan chuckled as Jim replied, "Everyone heard that story."

I'd lowered my eyes at that point and was nervously folding and refolding the cocktail napkin that we'd received with our drinks when Cheryl teasingly giggled, "Dan, I can't believe you were so mean to Mike. He'd never even had sex with Paula." As my wife said this, she reached over and touched Dan's arm flirtatiously, her comment obviously in jest.

I briefly looked up from my now shredded napkin to see Dan's arrogant smile, as he replied, "It was Paula who wanted to make sure she got laid on graduation night. What was I supposed to do, turn her down?"

Both Jim and Cheryl laughed at Dan's statement while I continued to remain silent, wondering how in the hell did my graduation night cuckolding become the topic of conversation. Just then my wife said, "You know Mike could hear everything." Dan and Jim thought this exceedingly funny as I squirmed in my seat, nervously taking a gulp of my beer to try and ease my anxiety.

"Aw, man, you were listened to us?" chuckled Dan, his expression one of pride in his prowess rather than embarrassment at being overheard.

I was about to sheepishly admit that yes, I'd heard their lovemaking when Cheryl blurted out, "Yeah, Mike heard everything." My wife then lowered her voice to a degree before teasing, "I know something else about that night that I bet you guys don't know." I had no idea what my wife was getting at, but Dan and Jim were now intrigued as they pleaded with Cheryl to let them in on her little secret.

My wife coquettishly teased the guys for several minutes, giggling, "No, I probably shouldn't say. I'll get in trouble," but her refusal to divulge whatever secret she was keeping only goaded the guys to insist she tell them. I, meanwhile, was wracking my brain trying to think of what my wife knew that Dan, of all people, wasn't aware of. Eventually, however, Dan and Jim were successful in convincing my wife to let them in on her little secret, promising they wouldn't tell anyone.

"All right, but remember, you promised not to repeat this," cautioned my wife before lowering her voice and divulging, "Dan, you know when you were screwing Paula?" Well, Mike was so turned on that he ended up playing with himself. Isn't that dirty?"

Oh my God! Why did my wife tell these guys that! My face turned a bright red as both Dan and Jim started laughing uproariously while my wife giggled mischievously. I couldn't believe that Cheryl would divulge such an embarrassing, personal secret. But seemingly not content with just disclosing this humiliating piece of information, Cheryl went on to tell Dan and Jim that this was the first of numerous masturbation sessions focused on Dan and Paula. And my wife disclosed that I'd go home and masturbate each, and every, time I dropped Paula off at Dan's house following our dates!

I endured several minutes of ribbing from Dan and Jim, with Cheryl putting up a half-hearted defense on my behalf. Cheryl interceded then, lowering her voice, and telling the guys not to be "so mean." My wife then said, "I think Paula was sort of a bitch, but it's really sweet how Mike stayed devoted to her. There's not many guys who'd do that." Cheryl then gave me a sweet smile before adding, "And the really great part is that that Mike never had sex with Paula, or any other girl. He was still a virgin when we met!"

Oh my God, was nothing about me going to remain secret? This revelation resulted in additional teasing about my lack of sexual experience with both Dan and Jim amazed that I could have remained a virgin until the ripe old age of twenty-one. At the same time, Cheryl professed that she "loved" that I'd never slept with any other woman than her. "It's really kind of sweet, don't you think?" added Cheryl before flirtatiously giggling, "It's not like I was a virgin, though. I was kind of more like Paula back then."

I'd kept silent the entire time as my wife and our two dinner partners discussed my most private details. It was like I was in some sort of bad dream as they all laughed and joked about my sexual history. In a more serious moment, Cheryl explained that she knew it'd been hard on me at the time to witness Paula's infidelity, but it turned out to be a good thing. "Mike learned that jealousy can really wreck relationships,", stated my wife while giving Dan and Jim a sexy smile.

Cheryl then added, "I've always had lots of guy friends so it's a good thing Mike's not the jealous type. He trusts me, don't you Baby?" cooed my wife.

"Oh, uh, yeah," I stammered, caught off guard by my inclusion in the conversation.

Cheryl then turned to me and gave me a peck on the cheek as she coquettishly giggled, "Isn't he the best husband ever? Mike's such a sweetheart."

My face was red with shame and although I'd kept my eyes downcast during much of this conversation, I could see Dan smirking in satisfaction. Fortunately, dinner arrived at that moment and we set about eating our supper while the subject moved on to more innocent matters. By the time we finished our meal, I was beginning to think we'd dodged a bullet and would soon be on our way home. And as the waitress brought the check, I grabbed it, telling the two guys it was my treat, thinking we could leave immediately after I'd paid.