A Cuckold Story Ch. 31-32

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Chapter 31

Following my wife’s break-up with Brad, she became relatively monogamous for the next year or so. I say “relatively monogamous” as Cheryl did see the Gym Guy at least once every couple of months and she did engage in a torrid month-long affair with Gary, a former co-worker of my wife who she happened to bump into while out shopping. Gary and Cheryl had always had a thing for each other and when Gary suggested they grab a drink it didn’t take long before they found themselves back at his apartment. Gary and Cheryl’s relationship ran its course rather quickly but not before they enjoyed a number of clandestine get-togethers, fucking and sucking each other with abandon.

But besides these occasional encounters, it was generally up to me to keep my wife sexually satisfied. And at first, I enthusiastically embraced my new role and was happy to have my wife all to myself. But it didn’t take long for me to realize that despite my enthusiasm and genuine concern for my wife’s satisfaction, I wasn’t really up to the job. To be sure, I overcompensated for my smallish penis by always first getting my wife off with my tongue, eagerly licking and sucking her pussy until she climaxed. But our lovemaking sessions always took a turn for the worse when I would attempt to fuck my wife. Invariably I’d come much too soon, my little dick sputtering and spurting, sometimes even before I was able to even insert it into my wife’s pussy. It seemed that my already poor stamina had worsened over the years and I had to admit my sexual performance was pathetic.

Cheryl was a good sport about my sexual failings, and she would frequently console me after my premature ejaculation episodes, telling me I’d do better “next time.” But to make matters worse, as I fretted about my inability to control my orgasms, I began to develop periodic erectile dysfunction issues. Sometimes I failed to even get hard, and sometimes I would wilt in my wife’s hand just as she was preparing to insert my penis into her pussy, but either way it was apparent that I was utterly incapable of addressing Cheryl’s sexual needs.

It’s funny, but during the same time I was agonizing over my sexual inadequacies, I never once failed to develop an erection when masturbating to my wife’s descriptions of past dates or encounters. And when on my own, all I had to do was recall one of Cheryl’s sexy adventures and I’d become hard as a rock and could masturbate for hours, edging myself as I imagined my wife with one of her studs. Of course, all this paled when compared to my excitement and arousal when Cheryl would announce she was going on a date with the Gym Guy. In the days leading up to one of my wife’s dates it would be all I could do to keep my dick from popping a boner at the mere sight of my wife. And the fact that sex with my wife was forbidden before her dates seemed to inflame my desires like nothing else and I had to fight the urge to masturbate constantly.

I think Cheryl and I both knew where this was leading and towards the end of the year, I had started telling her that she needed to add a second lover to complement her occasional get-togethers with the Gym Guy. And whenever I’d come too soon, or worse, fail to get or maintain an erection, I’d suggest that Cheryl find a “real man” as I was clearly out of my league with a woman as sexy and beautiful as her. My wife, sweetheart that she is, would always say something like, “Don’t worry Mike. We’ll work on your problem,” or “It’s okay. Why don’t you just lick me.”

Eventually though, Cheryl reached the end of her patience and one night after I failed to get even the slightest bit hard, she exclaimed, “All right, I give up! I love you Mike, but this is ridiculous! I’m going to find a new boyfriend! I need to get fucked!”

Ironically, my wife’s statement caused my dick to stiffen but by then it was too late. My wife marched down to the den and spent a good two hours perusing various Personals websites looking for a new lover. I had tried to sleep as I had to work the next day, but I was still awake when Cheryl finally returned to bed and I sheepishly asked, “Did you see anyone you liked?”

“Yeah, a couple,” replied Cheryl before adding, “But I have another idea too. You know how we were planning to take a week at Tahoe next month? Instead, maybe we can go to New York and I can see Chris? What do you think?”

“You’ll probably want to clear it with him, but yeah, that would work,” I answered, intrigued with this new concept.

We both slept fitfully that night as both Cheryl and I were anxious to hear whether her planned New York vacation would work for Chris. And the next day when I returned home from work, Cheryl greeted me with a big kiss as she announced, “Okay, we’re all set! Chris said he can probably take a couple of days off from work and he’ll tell his wife he’s on a business trip. And he said he’ll be able to stop by our hotel on a couple of the other days on his way home from work.”

“That’ll görükle escort be great, Honey,” I replied as I was genuinely excited that my wife would be able to receive some much-needed sexual satisfaction.

That evening Cheryl had me book our trip and although reserving our flights was easy, the hotel reservations were a bit more complex. At first, I thought to book adjoining rooms so that Cheryl and Chris could have their privacy, but after looking at various hotels I opted to book a suite at a boutique hotel on the East Side. The room featured a private bedroom with a king bed and a living room with a pull-out couch. When Chris stayed the night, he and Cheryl could have the bedroom and I’d take the couch and on the other nights, Cheryl and I would share the king bed. This seemed like the perfect arrangement and Cheryl agreed, particularly after I showed her pictures of the spacious bathroom equipped with a spa tub.

Once we’d booked our New York vacation, Cheryl’s mood brightened considerably. My wife was truly anxious to see Chris again and although she did arrange dates with two guys from the Personals, both dates were duds. The first guy failed to show and the second clearly had misrepresented his age and had used an older picture of himself resulting in Cheryl blowing him off after just one drink at the bar where they met. As for me, I felt like my pathetic attempts to please her in bed would only be rebuffed now that she was looking forward to spending several lusty nights with Chris. And to be honest, with my recent bouts of erectile dysfunction I wanted Chris to be the next man to fuck my wife. With his big, thick, and most importantly, stiff cock, Chris was a “real man” and my wife deserved to receive the sort of pleasure that only someone like that could provide.

If Cheryl noticed we weren’t having sex, she didn’t say anything and pretty much every day she was texting Chris, telling him how she couldn’t wait to feel him inside her and how she missed his big cock.

In anticipation of this vacation, Cheryl wanted to lose a couple of pounds and so she was working out incessantly and each night when I arrived home from work, I’d find that we were having salad or steamed vegetables and brown rice for dinner. Weekends were spent with me accompanying my wife on various shopping expeditions and whether it was a sexy new dress, a new pair of heels or matching lingerie, Cheryl was insistent that she was going to have a sexy new wardrobe for entertaining Chris. I was happy to treat my wife to these new outfits and I felt that this was a good way to partially compensate for my lack of sexual prowess.

Eventually the fateful day arrived and as we sat at the gate in the airport, Cheryl leaned over and kissed me, saying, “This is going to be such a great vacation. I just know it.”

Our flight was uneventful and by the time we retrieved our luggage and caught a taxi to our hotel it was almost ten-o-clock. But being New York, it was no problem grabbing dinner and as we sat in the corner restaurant looking out the window at the passing cars and pedestrians, Cheryl sighed, “I love New York.” I readily agreed to my wife’s sentiments and when we were back in our hotel and slipping into bed, I embraced Cheryl telling her I loved her and wanted her to have the best vacation possible.

The next day we planned to just get acclimated to our new home for the next week and we ended up sleeping in before having brunch at the hotel. Cheryl ate light as Chris was planning to meet her that afternoon at three before heading home to his house in the suburbs. After brunch, Cheryl and I just strolled around before heading back to the hotel to prepare for Chris’ arrival. My wife immediately asked me to shave her pussy before she soaked in the jetted tub and when she emerged from the tub, I helped dry her off before applying perfumed lotion over her entire body.

Despite my recent erectile dysfunction issues, the act of oiling up my wife’s body resulted in me becoming as hard as a rock and I joked with Cheryl that I guess I was “too little, too late” with an emphasis on the “little.”

Cheryl wanted to wear one of her new lingerie sets for Chris and as I watched her slide the sheer black stockings up her legs and attach them to the garter straps dangling from the form-fitting bustier she was wearing, I couldn’t help but whimper, “Oh God, you’re so sexy.”

Cheryl smiled at my compliment as she replied, “You like?” My wife then pulled on a pair of matching black thong panties, before slipping her feet into a sexy pair of black patent pumps with a delicate strap around each ankle. “Honey, can you buckle the straps on my shoes?” cooed my wife as I leapt to the task, kneeling before Cheryl and fastening the tiny buckles on the ankle straps.

By this time, it was almost 2:45 and I stood up and announced to Cheryl that I’d better get going before Chris arrived. My wife got a troubled look on her face as she exclaimed, “But Mike, aren’t bursa merkez escort you going to stay and say hi to Chris first? He said he’s looking forward to seeing you again.”

Now, I’m sure Chris didn’t give a rat’s ass about seeing me, but nevertheless I didn’t want to upset Cheryl as I said, “Okay, I’ll say hi. But I’m sure you two will be busy so I’ll just head out afterwards to give you some privacy.”

“Perfect!” squealed Cheryl as she headed to the bathroom to finish her makeup.

At almost exactly three-o-clock, we heard a knock on the door and when I answered it, I saw Chris standing there wearing an expensive business suit. In his suit he looked even more handsome than I remembered, and Cheryl rushed to him, holding him in a passionate embrace as their tongues played in each other’s mouth. Seeing my wife so eager to devour her lover was decidedly uncomfortable for me and it didn’t help that she was dressed merely in her sexy bustier and little else


When the two lovers eventually broke apart, Chris looked over at me and thundered, “Hey Sport! Good to see you, Mikey!” Chris then took my hand in his, vigorously shaking my hand as he stared me down, openly gloating at the fact that he was there for the sole purpose of fucking my wife. There was no way I could hold Chris’ gaze and I lowered my eyes from his, instinctively assuming a submissive stance in his presence.

When Chris eventually released my hand from his forceful grip, I made to excuse myself as I stammered, “Well, I’d better get going. I’ll see you later.”

But as it turned out, Chris wasn’t letting me off that easy. It seems that he had done some research on cuckoldry and was anxious to see if some of the stories he’d read about were true. Not only that, but for the past month he and Cheryl had discussed some of my recent sexual troubles and Chris seemed interested to see how far he could push before I pushed back. And so, as I was readying to leave, Chris said, “So, Mikey. Cheryl tells me you and she haven’t had sex in over a month. That right?”

“Uh yeah,” I sheepishly confessed while slowly moving towards the door.

“Hey, c’mon Mikey, not so fast. I just want to talk with you a bit, okay?” declared Chris while giving Cheryl a conspiratorial wink.

“Uh okay,” was all I replied as I turned to face Chris and my wife.

“Cheryl told me you’ve been having some problems in the bedroom. You know, I’ve heard some guys have problems like that,” stated Chris while giving me an arrogant smile. Chris then added, “It must be tough. A sexy little wife like Cheryl and you can’t take care of business. That’s got to be the worst.”

Chris paused for a moment to let his words sink in before continuing, “But, you know, I’ve never had any issues with my equipment. Especially not with a woman as sexy as your wife.” Cheryl smiled at Chris’ compliment and he reached over and gave her a playful slap on her behind.

Chris then took a more serious tone as eyes bore down on me. “I’m going to do you a favor Mikey. I’m going to fuck your wife. So why don’t you take off Cheryl’s panties for me? Okay?” sneered Chris as he kept his eyes locked on mine.

At first, I was powerless to respond as I was literally shaking at this request. But one glance at Cheryl and seeing her hunger, her almost insatiable need to fuck Chris and I obediently knelt before my wife and grasping the waistband of her panties in each hand, I slowly lowered them down her legs. Cheryl reached out and placed a hand on my shoulder to steady herself and then lifted each high heeled foot in succession allowing me to remove her panties completely and as I stood up, I absentmindedly slipped them into my jacket pocket.

Cheryl was shifting back and forth on her feet and I could sense that my wife at any moment was going to attack Chris and so I stood up and turned to leave. However, as I made my way towards the door, I halted for just a second and turning to Chris I said, “Chris, please fuck my wife. She deserves to be satisfied.” I then scurried out the door while hearing muted giggles coming from both Chris and Cheryl.

Outside in the hotel hallway, I realized I was trembling with a combination of love, lust and embarrassment. I had just asked this man, a handsome athletic stud, to fuck my wife and not only that, I’d obediently removed her panties for him, an incredibly symbolic act! I’ve never felt more like a cuckold than I did at that very moment and as I slowly walked down the hall to the elevator, I had to pause twice just to catch my breath I was so caught up in my emotions.

With my wife in our hotel room with her lover and with Chris’ admonition not to return before seven-o-clock, I had several hours to kill. In my state I decided to take a long walk to clear my head and I strolled down towards Midtown taking in the sights while trying desperately not to dwell on all the naughty delights taking place in our hotel room.

I walked bursa sınırsız escort for a good two hours before I made it back up to Central Park and taking a seat on a park bench, I realized it was only a little past five. I still had almost two hours before I was to return to our hotel and as I sat there on the bench, I let my mind wander as to what Cheryl and Chris might be doing at that exact moment. Visions of my wife and her lover fucking in all manner of positions filled my brain and my penis started to twitch causing a distinct tent to form in the front of my pants. It was then that I realized that I still had my wife’s panties and furtively reaching into my jacket pocket, I pulled them out and glancing around to make sure nobody was watching, I lifted them up to my nose and inhaled the delicate scent of my wife’s pussy mixed with her distinctive perfume.

In retrospect, I think the earlier experience of removing my wife’s panties and asking Chris to fuck her had overwhelmed any sense of decorum I might have possessed. And with Cheryl’s skimpy thong panties grasped tightly in my left hand, I impulsively leapt up from the bench and briskly strode down a nearby paved trail until I saw a cluster of shrubs. Pushing into the shrubbery, I unzipped my pants and took my hard penis into my right hand and began to masturbate. Here I was masturbating in Central Park while at that very moment my wife was entertaining her lover in our hotel room! My actions were truly shameless and when I brought my wife’s panties back up to my face, opening my hand to gaze at the skimpy black triangle of fabric that once covered her pussy, I began to come, my sperm pouring out of my dick and on to the ground.

Once I’d come, I became acutely aware of my potentially humiliating situation and before the last drops of semen had oozed from my dick, I tucked my wilting member back into my pants and inconspicuously exited the shrubs. Fortunately, I don’t think I was noticed and before long I was sitting on a different park bench contemplating what I’d just done. As frightening as it was to think of what I would have done had I been caught, I don’t think I could have handled waiting any longer to masturbate. Chris had cuckolded me in a way that I’d never been before, and I was just too caught up in the sheer eroticism of the moment to have kept my hands off my dick. And now, having relieved some of my pent-up sexual frustration, I was able to think more clearly and to steel myself for whatever Cheryl and Chris might toss my way over the rest of our vacation.

I sat on the park bench until six-o-clock when I decided to take a leisurely walk back out hotel. Chris had been adamant that I not return until seven and so I waited across the street from the hotel for almost forty-five minutes until I saw him stride out. I didn’t want to run into Chris and when I saw him walk down the block, I hurried across the street and was soon standing in the elevator headed up to our room. Entering the room, I’d hoped to find Cheryl splayed out on the bed waiting for my soothing tongue, but to my disappointment she was in the shower. Not wanting to disturb Cheryl, I waited until she had exited the shower to say hi and my wife merely replied, “Oh hi Mike. Did you see Chris on the way out?”

“No, why?” I answered.

“He just wanted to make sure you were okay with how everything went down earlier. I told him you’d be fine, but he wasn’t sure since you looked so nervous when you left,” explained my wife while toweling herself off.

“I’m fine,” I assured Cheryl while gazing longingly at her petite body knowing that she was off-limits to me for the bulk of this vacation.

As Cheryl finished drying herself, she said, “You know Mike, Chris has been reading up about guys like you.”

“Guys like me? You mean cuckolds?”

Cheryl smiled as she went on. “Yeah, cuckolds. He said he’s trying to figure out why you like it when I’m with him. That’s where he came up with the idea about you taking off my panties. He read that on some website and thought it would be fun. You liked it didn’t you?”

It was my turn to embarrassed once again as my face grew red and I muttered, “Yeah, I did.”

My wife smiled again as she exclaimed, “I knew you would! That’s why when I talked to Chris last week and he brought it up, I just told him to go for it. And you don’t even know how turned on Chris got when you pulled off my panties and then asked him to fuck me! When you left, he was like an animal!”

I had started to absentmindedly fondle my penis through my pants as I sheepishly asked, “So it was good? Was Chris as good as you remembered?”

Cheryl giggled before exclaiming, “Oh my God, Mike! It was really, really, good! He was so big and really hard, I loved it! We fucked twice and I swear, each time he lasted an hour!”

My wife’s excitement was contagious, and I found myself congratulating her and assuring her that I’d be happy to let her see Chris as often as she wanted while in New York. Frankly, I’m not sure I had any say in my wife’s decision as to when she would see Chris, but she replied anyway, saying, “Thanks, Honey,” before telling me that she’d made reservations at a nearby restaurant that Chris had recommended.

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