A Cuckold Story Ch. 21-22

Chapter 21

After Cheryl's affair with our friend Rich ended, she didn't immediately look to add another lover to her list. To be sure, she did continue to see the Gym Guy and the Stockbroker, but she typically only got together with each of these guys once a month or so. And although now my wife and I were making love on a somewhat regular basis, I couldn't help but miss the erotic thrill of coming home to an empty house, knowing my wife was with another man. Or savoring the intense arousal of waiting impatiently for her to return from a date with the prospect of devouring Cheryl's well fucked pussy causing me to salivate like Pavlov's dog.

It was somewhat of a surprise to me, but I had thoroughly enjoyed my wife's affair with Rich. There was something incredibly exciting about interacting with a man that was regularly fucking my wife and it had turned me on more than I'd expected. Sure, there were times where I'd felt unbelievably shamed, nervously making small talk with the man whose semen was dripping from my wife's cunt at that very moment, but even these events would later turn into mindboggling masturbatory fodder. It was against this backdrop that one night as Cheryl and I were enjoying a quiet night at home that I confessed that I missed her regular dating. And I added that I wanted her to have the freedom to be able to fuck any man she desired, no rules, no pre-conditions and most importantly, no need to ask my permission. I went on to tell Cheryl that she could fuck friends, coworkers, neighbors, whomever she wanted, and that I would remain 100% supportive of her infidelities.

As I said my piece, a wave of serenity washed over me. I was giving up any modicum of control I had over my wife's sex life, but instead of feeling uneasy, I felt supremely confident in my decision. I was taking the final step to becoming the obedient and loving cuckold husband that Cheryl deserved.

Although I was in high spirits as I entrusted my wife with sole control over her sexual activities, Cheryl was not so excited. Although she'd smiled lovingly as I gave my little speech, she immediately pooh-poohed my proposal, saying, "C'mon, Mike, you're just being silly. You're probably too tolerant as it is. Besides, it's not like I'm going to fuck all your friends. It was different with Rich."

I was still totally sure of my decision as I merely replied, "Okay. I get it. But I want you to know you can date whoever you want. You don't have to ask me first. And I won't complain, ever. I promise. I love you and I trust your decisions."

Cheryl's smiled at my comment as she giggled, "All right Mike, if that's the way you want it. But don't say I didn't warn you."

Cheryl and I didn't discuss our new arrangement after that night. And it may have been all in my mind, but I thought I could sense that my wife was now acting somewhat different when around our male friends. Cheryl has always been a flirt, but now she had no reservations about flirting with pretty much all our male friends and acquaintances, often causing me to blush bright red in embarrassment. To be honest, I loved my wife's new attitude and although she didn't pursue any of the several overtures she received, it served to stoke my cuckold angst in ways that kept me permanently aroused.

Chapter 22

As it turned out, the first time Cheryl acted on her new freedom was several months following my little speech. I had enjoyed a very successful year at my job and had been invited to the President's Club event in Maui where all the sales staff who had made their quotas were treated to a four-night stay at a luxury, beachfront hotel. Cheryl and I had never been to Hawaii before and we were anxiously looking forward to the event.

The very first night we joined the attendees at a casual buffet dinner down near the beach. The event was set up on the lawn near the beach and as we surveyed the scene both my wife and I were blown away at the beautiful setting. After dinner, we decided to head to the lounge where many of the attendees had congregated. Unfortunately, the bar was packed and there were no seats to be had and after surveying the raucous scene we decided to just head back to our room and enjoy a nightcap from the minibar. But just as we were leaving, Troy, from my office called out, "Hey Mike! C'mon over here and have a drink!"

When I looked in Troy's direction, I saw that he was sitting with two of the younger salesmen from my office along with several other people I had never met. Troy was our newest salesman and in just one short year he had set several sales records, despite being only twenty-seven years old. He was a handsome guy with the gift of gab, and he seemed to have a natural ability to close. His skills were not restricted to sales and it was rumored that he had bedded at least two of the younger women in the office during his short tenure.

When we made our way over to Troy, he immediately gave his seat to Cheryl in a chivalrous move that I could see she appreciated. He then poured out a beer for me from the pitcher on the table and ordered a white wine for Cheryl. I then introduced Cheryl to the folks I knew from my office and we also shook hands with the attendees who all worked in other regional offices. From that point on, I enjoyed a couple of beers while discussing several sales initiatives we were embarking upon over the next several months. At the same time, it seems that Troy was focusing his attention on Cheryl almost exclusively. I didn't really think too much about it and although my wife looked fantastic in her tropical print sundress and high heel sandals, I didn't think Troy would have any interest in a woman who was more than ten years his senior. When we eventually said our goodnights, I escorted my wife up to our room where we fell into a deep sleep almost immediately as a result of the time change.

The next morning, I had arranged to join several of my coworkers for a round of golf at the course adjacent to the hotel. Although not much of a golfer, I knew these events were more about team building and less about golf and so I dutifully headed out to the course, while Cheryl arranged a massage at the hotel spa.

The golf course was absolutely magnificent, and I thoroughly enjoyed myself as we played under the tropical sun, enjoying vistas of the ocean and the other islands. And after our game, I stuck around and had a beer with my coworkers, toasting our good fortune. By the time I got back to the hotel room it was almost three-o-clock and Cheryl was nowhere to be seen. This didn't seem unusual in the slightest as I assumed my wife was probably down at the pool, or even at the beach. I decided to head down and join her but after making three strolls around the pool and walking the beach in both directions, I didn't see any trace of Cheryl. And when I called her cell phone, my calls went unanswered. I wasn't too worried as Cheryl frequently didn't pick up her phone and so I decided to head back up to the room to await her return.

As I waited in the room for Cheryl, I remembered distinctly that I had told her we needed to be at the company luau at six-o-clock. The president of our company would be giving a speech that evening and after dinner the awards ceremony would be held. Although I was not going to be receiving any awards, it would be very poor form to miss this important event.

By five-o-clock I started to feel distinctly uneasy. Where was Cheryl? I had called her cell numerous times and each time my calls had gone unanswered. I wondered whether I should check with the front desk to see if she had caught a cab into Lahaina. We needed to leave for the luau by no later than 5:45pm and Cheryl would need some time to get dressed. I began to pace back and forth in the room and when I looked at the clock again, it was 5:30! Now, I really started to panic! Where could she possibly be? Just then, I heard a card key in the door and when the door opened, there was Cheryl wearing just her bikini and high heel slides. She had a naughty grin on her lips and I instantly knew she had been with another man.

"Where were you?", I screamed as my wife made her way to the closet and pulled out one of her sundresses.

I guess my anxiety at almost missing the luau caused my question to sound accusatory, as Cheryl developed a scowl on her face as she snapped, "I was with Troy."

Once again, I couldn't control myself as I screamed, "Troy? You were with Troy! Did you fuck him?"

This time my wife couldn't control her temper as she scolded, "I knew it! I knew you couldn't handle it! Yeah, I fucked Troy! You said I could fuck whoever I wanted. Well, I did!"

"But I didn't mean...", I stammered before Cheryl cut me short with a withering glare.

In an assertive tone that I rarely heard her use, my wife then declared, "Listen, Mike, you said I could fuck whoever I wanted. Well, I fucked Troy and it was incredible. And I'm going to fuck him again. Got that?"

We were already running late for the luau and I knew we needed to get going as soon as possible and so, I bit my tongue, telling Cheryl, "We can talk about this later. But we need to go. We're going to be late as it is."

"No, we're not going to talk about this later! We're going to talk about it right now! I need to know you're okay with me fucking Troy?", declared my wife while giving me a menacing glare.

In hindsight, I suppose I should have yielded at that point, and told Cheryl that she could fuck Troy if she wished, but I was still so shocked at having been cuckolded by my younger co-worker that, instead, I stated, "C'mon, Cheryl we need to go. I don't want to talk about it right now, okay?"

The minute the words were out of my mouth I knew I'd screwed up. Cheryl's face became bright red as she growled, "All right, then! I guess I'll just spend the rest of this vacation with Troy!" Cheryl then grabbed one of our suitcases and made a show of throwing various articles of clothing into it.

The thought of my wife spending the remainder of our trip with Troy and having all my co-workers privy to my cuckolding had me mortified as I began to apologize, telling Cheryl that she could fuck Troy whenever she wished and that I was sorry for my outburst.

Eventually, Cheryl ceased her packing telling me to find her yellow sundress and wedge heels while she got ready. Although my wife was clearly still incensed with me, I was relieved that she still intended to go to the luau and so I scurried to the closet to find my wife's clothes while she secluded herself in the bathroom to clean up.

When Cheryl emerged from the bathroom, she didn't speak a word to me as she slipped into her dress and when she was dressed, she merely sat on the edge of the bed and snapped, "Shoes!"

I knew what she meant as I dutifully knelt in front of my wife and slipped the tall wedge heels on to her feet and buckled the tiny straps around her ankles while Cheryl touched up her lipstick. Cheryl then strode out of the room and I followed several steps behind as I knew she was in no mood to talk right then.

To my great relief, Cheryl was cheerful and vivacious at the luau and although she was giving me the cold shoulder, she acted the role of the corporate spouse with aplomb. I noticed that several of my male coworkers at our table paid an inordinate amount of attention to Cheryl and I started to wonder if they could tell she had just recently had sex. Was she giving off pheromones like a bitch in heat or was it just her winning personality and sexy figure? Whatever it was, Cheryl was flirting with all the guys at the table and it was making me decidedly uncomfortable. Fortunately, Troy was seated at the awards table and although I saw Cheryl give him a friendly smile and a wave, he didn't make his way over to our table.

As we sat listening to the awards presentation and the brief speeches, I was mindful of the fact that my wife was still furious with me. And with the way Cheryl was flirting and carrying on, I knew I needed to get back into her good graces lest she publicly embarrass me by going too far. And so, as the luau was wrapping up, I ushered Cheryl off to the side and profusely apologized for my earlier behavior, telling her I had acted like an idiot. I had just finished my apologies when out of the corner of my eye I saw Troy striding over to us. He greeted Cheryl with a friendly hug and he then shook my hand. "Hey, Mike, sorry I missed you today. I ran into Cheryl down at the pool and I had a great time getting to know your wife."

"Uh, yeah. I was golfing", I stammered while reluctantly admiring the chutzpah Troy had to approach me after having just spent the afternoon fucking my wife.

"Yeah, I'm not much of a golfer. A little too boring for me. I'm more into surfing", laughed Troy.

Now it was Cheryl's turn to make me uncomfortable as she gushed, "Really, Troy, you surf? I'd love to learn to surf. Do you think you could teach me?"

Troy burst out into a broad grin as he looked at me and said, "Sure thing!" Troy then turned to me and asked, "You don't mind if I take Cheryl out surfing tomorrow, do you?"

The entire conversation was almost more than I could bear as I looked first at Cheryl and then at Troy and sheepishly replied, "Uh, no. That sounds like fun. I'm going to play golf again tomorrow with some of the guys from the office and it'll be great for Cheryl to have something to keep her busy."

"Great!", exclaimed Troy as he and Cheryl then made plans to meet down in the lobby at nine-o-clock in the morning.

I was emotionally exhausted by that time and when Troy finally said his goodbyes, I let out a sigh of relief. Cheryl and I then headed back to our room and once we had closed the door, I turned to my wife and once again, said I was sorry for my earlier outburst and begged for her forgiveness. I don't know whether it was my heartfelt apology or the prospect of seeing Troy again the next day, but Cheryl accepted my apology and even giggled, "I wasn't really going to move in with Troy."

"Yeah, I know, Sweetie", I immediately replied. Although I was not entirely sure that Cheryl's threat had been in jest, I was not about to argue with her as I was still shaken with the thought of it. And at the same time, I accepted the fact that I had been out of line. After all, it was I who had insisted that Cheryl could sleep with whomever she wished and then when she did so, I threw a hissy fit. That was no way to treat my wife and so I added, "I'm so sorry I acted like I did. I said you could fuck whoever you wanted, and I mean it. It just kind of caught me by surprise that you fucked Troy. I'm sorry I got so upset. He's a good guy and I hope you had fun."

Cheryl grinned at my apologetic tone as she giggled, "Do you want to hear what happened?"

My dick was instantly erect hearing this as I hurriedly pulled off my pants and lay on the bed while Cheryl lay beside me still fully clothed. "Okay, let me see, where should I start?", teased Cheryl as she saw that I had already begun to run my hand up and down my stiff penis.

Cheryl then began to tell me that she had run into Troy down at the pool and he had instantly commented on the thong tan line that showed above the more conservative bikini she had brought on the trip. Cheryl just laughed off Troy's comment, teasing, "I usually wear a thong. But Mike didn't want me showing off my ass to all the guys he works with. He can be such a prude sometimes."

That started a series of non-stop flirtatious comments between Troy and Cheryl and when Troy suggested they have a drink at the poolside bar, my wife readily agreed. One drink led to two and this only lessened Cheryl's inhibitions as she teased Troy mercilessly. Eventually, their flirtations became decidedly risqué and when Troy suggested they maybe she'd like to see the view from his room, Cheryl leaned over and gave him a wet kiss right there in the pool.

I shuddered to think that one of my coworkers might have seen this wanton display, but at the same time pre-come began to ooze from the tip of my dick and I had to pull my hand away to keep from coming. Cheryl then went on to tell me that the minute they entered Troy's room, he was all over her and they fucked three times over the course of the afternoon. In between sessions, they lay naked in his bed, the sliding glass door wide open as they talked softly while listening to the waves crashing on the beach. My wife told me that not only was Troy a skilled lover, but he was very well endowed and even though he was only twenty-seven, he certainly knew his way around a woman's body.

As Cheryl described her encounters with Troy, I began to masturbate furiously and as my wife told me how he had playfully spanked her ass, while pounding her from behind, I began to come. My sperm shot out of my dick, coating my stomach, as my wife continued her narration. Cheryl seemed pleased with my reaction to her story and when I had finished pumping out my come, she giggled, "Okay, that's enough for now. I'll have some more stories for you tomorrow."

That night we slept well as I held Cheryl close, continuing to apologize for my earlier behavior. The next morning, I was up before my wife and I showered, dressed and then headed down to the gift shop to pick up something for my wife to atone for my outburst of the day before. There wasn't much to choose from, but they did have a pukka shell necklace with a matching anklet that fit the bill and after paying for my purchase, I quickly made my way back to the room to find Cheryl had just woken up. I had ordered a light room service breakfast and within minutes after my return there was a knock on the door and the breakfast cart was wheeled into our room.

Cheryl and I ate breakfast in relative silence as we both were undoubtedly contemplating the day ahead. And it was only when we had finished that my wife cooed, "Honey, can you shave me before you leave."

For some reason, my wife's request had the effect of breaking the silence between us as I leapt to my task, shaving my wife's pussy until it was a smooth as silk. As I was shaving her, Cheryl was chatting amiably about her plans for the day, telling me she couldn't wait to see Troy again and was hoping for a repeat of the previous day. For my part, I was becoming more comfortable with the fact that my wife was fucking my younger coworker and I added my own comments, lamenting the fact that she had not brought one of her thong bikinis so that she could tease Troy throughout her surfing lessons.

When I had finished shaving my wife's pussy, she slipped into the shower to wash up and when she emerged from the bathroom, she had me apply coconut scented sunscreen over her entire body. Cheryl then put on her bikini and pulled a tiny, ass-hugging jean miniskirt over her bikini bottoms. Since they were headed to the beach, the high heel slides that my wife had worn around the pool wouldn't work but fortunately she had brought along a pair of platform flip-flop sandals that gave my wife the height she wanted and accentuated her shapely, toned legs.

Cheryl looked absolutely delicious and I told her that Troy would no doubt be pleased. It was then that I presented my wife with my gift, helping her put on the pukka shell necklace and then keeling down to attach the anklet around her ankle. Now, I know that there has always been rumors that if a married woman wears an anklet it means she is a hotwife, but to be honest, I've never really attributed much truth to these rumors. Nevertheless, as I stood back and admired my beautiful wife in all her glory, I realized that at some level I wanted everyone to know that Cheryl was free to fuck whomever she wanted. I was proud to be my wife's cuckold and if that meant some might disapprove, then I suppose I could live with it.

Time was running short by this time and so after giving Cheryl a quick kiss and wishing her well, I hurried down to the golf course to meet the other guys. Throughout the day, I was preoccupied with fantasizing about Cheryl and Troy and I'm afraid my golf game suffered because of it. In fact, as we finished the game and the guys suggested we grab a beer at the bar, I declined. Instead, I hurried back to our hotel room where I masturbated furiously, climaxing as I imagined Cheryl and Troy fucking in all manner of erotic positions.