A Cuckold Story Ch. 38-41

Chapter 38

Once Cheryl introduced me to chastity, it quickly became the rule rather than the exception. To be sure, my wife would typically let me masturbate after I'd licked and sucked her well fucked pussy and more than once my wife treated me to a kinky masturbation session while she teased me with her high heel shoes. But other than those brief moments, my dick was almost always secured in its pink plastic sleeve.

Although unaware of the concept when her lover first suggested it, Cheryl quickly embraced keeping me in chastity. She appreciated my willingness to remain chaste and she'd frequently reach down just to feel the plastic sleeve encasing my dick, reminding herself that I'd made this sincere commitment to her. My wife also enjoyed the effect that chastity had on me, frequently commenting, "Ever since we locked up your little dickie, you've been such a good little hubby. We should have done this a long time ago."

As emasculating as it was to be in chastity most every day, I adjusted to it relatively well. Although it seemed somewhat unfair that not only did the Oakland Guy have unfettered access to my wife's charms but that other men did as well, nevertheless I didn't complain. And even when Cheryl ran into a guy she'd slept with back in her "slut years" and ended up spending the night in his bed, I never uttered a word of protest. Ever the well behaved cuckold husband, I merely replied, "Have fun," to Cheryl's text letting me know she wouldn't be home that night. And the next evening when I returned home from work, I didn't whine about the unfairness of my plight. Instead, I just enjoyed a long overdue masturbation session while Cheryl described her trysts with a guy she called the Surfer Guy.

I must admit to being greatly relieved when Cheryl opted not to regularly advertise my key on her anklet as her friend Pam had suggested. When out and about my wife generally kept my chastity key in her pocketbook although occasionally, she'd attach it to one of her gold necklaces and I'd be on pins and needles, worried that someone might ask what it was for.

Whenever my wife was out with the Oakland Guy, however, she did make a point to proudly display my key on an anklet or necklace. Cheryl told me that her lover was adamant that I be locked in chastity whenever they were together and with my key dangling from my wife's anklet or necklace there was never any doubt that I was not going to be masturbating. Occasionally, while out with the Oakland Guy, someone would ask about the key and Cheryl would shock and amuse the enquirer by explaining that the key was to her husband's chastity device, telling them that I had a tendency to masturbate "too much" unless locked up.

In this new scenario, with me in semi-permanent chastity, Cheryl honed her skills as a true cuckoldress, and she routinely teased me until I would be literally begging for release. Helping Cheryl prep for her lover was exquisite torture knowing that later, as she and her boyfriend were enjoying a lusty, uninhibited sexual encounter, I would be unable to so much as stroke myself to visions of my beautiful wife's shameless behavior. And as I performed my pre-date tasks, naked with my hairless penis in its pink sleeve on full display, pre-come would frequently seep from the tip of my chastity device in what I've heard aptly described as "cuckold tears." And whenever Cheryl would see this evidence of my arousal at helping her prepare herself for another man, she'd giggle coquettishly, "You love this as much as I do, don't you?"

I could only imagine the thoughts running through my wife's head. Seeing my diminutive manhood, non-threatening and securely locked in chastity while I helped her prepare for her dates, seemed to stoke Cheryl's eager anticipation of the Oakland Guy's thick manly tool. In fact, my wife would frequently make comments contrasting my "little dickie" with her lover's much larger "cock" and I'd find myself telling Cheryl how happy I was that she'd found such an awesome lover. I'm sure most men would be horrified at this state of affairs, but for me, picturing Cheryl, her pussy freshly shaved and wearing the sexy shoes or lingerie I'd helped pick out for her as she welcomed her lover's thick cock into her pussy was gratifying in a way only a fellow cuckold could understand. And despite questioning my situation at times, I found that I generally took great pleasure in knowing that my wife was enjoying a sex life than most women could only dream about.

It was during this time that Cheryl dropped her pseudonym for the Oakland Guy, and I learned that his name was John. John was a former college football player and had continued to keep to his training regimen, assuring that he stayed in tip-top shape. And it turned out that John's best friend, Nate, lived no more than a mile from us. John and Nate had been teammates at Arizona State and had moved to the Bay Area together after college. For the past several years, John and Nate had a standing agreement that they'd get together every Saturday morning to work out. And so, when John opted to spend either Friday or Saturday night at our house, it was convenient for him to either meet his friend the next morning at the gym, or head over to our house after his workout. Although I wasn't keen on spending so many weekend nights away from home, I never uttered a word of complaint, as I was determined to make sure that Cheryl had ample opportunities to enjoy herself with her hunky boyfriend.

Over time, I grew somewhat accustomed to spending weekend nights away from home and even derived a certain perverse excitement in knowing that my wife was screwing her lover in the same bed in which she and I regularly slept. Even the fact that John now kept a toothbrush and several sets of clothes at our house didn't faze me and I always made sure that John's clothes were freshly laundered and folded whenever he came to visit my wife.

It was a little over a month after John had started staying over at our house that he had my wife place a framed naked photo of himself on her nightstand. It seemed that John had loved all the sexy photos I'd placed around the bedroom and in my wife's closet and he thought it would be fun to have one of himself as well. Cheryl did as he wished and every time I'd glance over at Cheryl in bed, I'd see the photo of my wife's hunky young lover standing proudly in our bedroom, his hands on his hips and an arrogant smile on his lips. John was sporting an enormous erection in the picture and as Cheryl told me many times, he'd put it to good use that day, fucking my wife to numerous orgasms over their lengthy sexual encounter. Seeing this picture on a day to day basis was a constant reminder that there was no way for me to compete with my wife's stud. John's six-pack abs, muscular build and large, thick cock were quite the contrast to my skinny build and hairless little penis and whenever I glanced at this picture, I'd instantly understand why I was in chastity and John was taking care of my wife's sexual needs.

Whenever Cheryl told me that John was planning to spend the night at our house, she'd always remind me that John continued to express an interest in meeting me, telling me I could sleep in the guest room like I'd done with Chris. Each time, however, I'd beg off, telling Cheryl that I was content with the way things were and that I wasn't interested in meeting her lover.

Truth be told, the past several months had only bolstered my decision to remain detached from my wife's relationship with John. Having been forbidden sexual contact with Cheryl from the very first and now regularly locked in chastity, the idea of meeting and interacting with the architect of these restrictions seemed like a bridge too far. How could I face the man who had unfettered access to my wife's charms knowing that he was also responsible for assuring that my sole source of sexual relief was via my own hand? And although I'd long since accepted that as Cheryl's cuckold husband, I needed to stand aside when she wished to share her bed with other men, the fact that John had insisted that I be denied sexual contact with my wife was especially humiliating. I guess I was trying to salvage one small shred of self-respect, pretending that by keeping my distance from Cheryl's lover, she could still see me as her loving husband and not the sniveling cuckold wimp I would undoubtedly become when in John's presence.

In addition to not wanting to subject myself to the shame and humiliation associated with meeting my wife's lover, I also was somewhat afraid of seeing my wife submit to her young stud. I'd heard enough firsthand accounts from Cheryl to know that she was completely under John's spell. It seemed that John merely had to snap his fingers and Cheryl would drop to her knees to suck his thick cock.

Cheryl freely admitted that John brought out the submissive side in her and there wasn't much of anything that my wife refused her lover. And whether it was John's penchant for frequently blowing his load on my wife's pretty face or his insistence that she offer up her tight little butthole at the drop of a hat, Cheryl had few boundaries when with John. Of course, I knew there was no way Cheryl would let me witness any of this debauchery, but I couldn't help but shake the feeling that even being in the same house while John was ravishing my wife might somehow tarnish the image I held of her.

In my eyes, Cheryl has always been my sweet bride who I love with all my heart, and the thought of hearing her willingly submit to John, or even seeing her dote on him, seemed too much for me.

Don't get me wrong, when Cheryl released me from chastity and I had my dick in my hand, I never had a problem masturbating to the tawdry stories Cheryl would tell me. But invariably after coming I'd feel guilty, thinking that perhaps John was pushing my wife too far and taking advantage of her eagerness to please her hunky, young lover. Keeping my distance from my wife's naughty adventures seemed a good idea and after each of John's visits to our home, when I'd hear about all the raunchy things he and Cheryl had done, my resolve to avoid meeting John grew stronger. Thankfully, Cheryl never truly pressed the issue and although I think she was disappointed in not delivering on one of John's requests, I think she, too, was somewhat nervous about me seeing her act the role of John's slutty girlfriend.

As much as I had adapted to my frequent weekend nights away from home, every time Cheryl told me that John joined his friend to work out, I would get a sinking feeling in the pit of my stomach. Although John had told Cheryl that Nate was happily married, I had no doubt that John bragged to his friend about the sexy wife he was fucking and the timid cuckold husband who not only put up with his wife's infidelity, but obediently cleared out of the house whenever he opted to visit. Of course, this sort of feeling wasn't new to me, I was used to suspecting that Cheryl and I were the subject of all sorts of locker room talk. After all, over the years, several friends, acquaintances and in Troy's case, even co-workers, had fucked my wife and there's no way they'd all kept quiet about their good fortune. But this was different, with John being fully aware that I knew of my wife's extramarital adventures, I could only imagine what he and his friend talked about.

The fact that I would willingly vacate my own house, allowing my wife to entertain her lover in our marital bed must have been a foreign thought to two guys steeped in the testosterone filled world of sports. But whenever my wife would text me the "all-clear" and I'd return home, the satisfied smile on my wife's face made everything worthwhile and the next time she'd tell me to book a room, I'd do so without a word of complaint.

In hindsight, I suppose it was inevitable, but one Saturday almost six months after Cheryl had started seeing John, he called her at around one-o-clock to say he was going to be a little late as he and Nate were going to grab a beer after their work out. It had been two weeks since my wife had last seen John and she was impatient to enjoy Saturday afternoon and evening with her lover. I had already reserved my hotel room for the night and had just finished zipping my wife into a sexy little sundress and was kneeling in front of her to place a pair of retro strappy, wooden heels on her feet when her phone rang. Cheryl immediately grabbed her phone off the nightstand and cooed, "Hey Baby. Are you almost done? I can't wait to see you."

I was busy buckling the straps on my wife's shoes, the key to my chastity cage on my wife's anklet glistening teasingly in the sunlight streaming into our bedroom. I could sense a certain tension in Cheryl and when I glanced up at her she had slight frown on her face. "Really? How long do you think you'll be?" questioned Cheryl as she seemed severely disappointed that John wouldn't be arriving at the planned time.

Cheryl was quiet for a while as John explained that he was going to get a beer with Nate when suddenly her face lit up and she exclaimed, "No, no, that would be great! It'll be fun to meet him!"

My heart skipped a beat as I had surmised by this time that John was with Nate. But I remained silent as Cheryl went on, telling John, "Don't worry. I'll have Mike run out and pick up some more if we don't have enough."

John was obviously bringing Nate over to our house as the next thing I heard was Cheryl gushing, "This'll be fun! I've been wanting to meet him! Okay, see you soon!"

I was still kneeling at my wife's feet and had just finished buckling the straps on her shoes as she jumped up and exclaimed, "John's bringing his friend Nate! Mike, can you go make sure we have enough beer? And make sure we have some snacks too."

I was still processing this new concept. My wife was going to be hosting not just John but his friend Nate as well! And if I had any doubts about whether John had told Nate about Cheryl and me, those uncertainties were certainly put to rest. Nevertheless, I was determined not to let my insecurities spoil Cheryl's mood as I merely replied, "Okay, Honey."

Before I could head down to the kitchen, Cheryl looked at me and posed what was a somewhat serious question. "What do you think, Mike? You know how John doesn't like me to wear panties? But with his friend here, maybe I should. This dress is so short that when I sit down you can see my pussy."

What should have been an easy question wasn't really that simple. John had pulled my wife over his knee and spanked her bare bottom on their second date after she had the temerity to wear panties and ever since, Cheryl had always kept her pussy uncovered and accessible when out with her demanding lover. But after mulling it over for a couple seconds, I answered, "I think you probably should wear them. You don't want John's friend getting the wrong idea. I think John will understand." And with that, I hurried downstairs to make sure we had the requisite beer and snacks for my wife's guests.

I'm glad I didn't have much forewarning of Nate's visit as I was a nervous wreck as I assembled an array of snacks for his and John's visit. I had become accustomed to having John stay over, but this was an entirely new scenario. Was John intending to share my wife with his friend? Cheryl hadn't mentioned anything about that, but then again, John had extraordinary sway with my wife. John had introduced Cheryl to swinging and they'd swapped with other couples several times now and it wouldn't be surprising if he thought it perfectly acceptable to lend my wife to his friend. As I pondered these thoughts, I was shaken out of my reverie as my wife called out, "You better get going Honey, they're on their way!" I was glad I'd already packed my bag as I quickly grabbed my suitcase before giving Cheryl a quick kiss and then literally running out to my car. I was not a moment too soon as I passed John's SUV as I drove down the street, followed closely by Nate's truck and I wondered whether they saw me, Cheryl's nervous cuckold husband making his harried exit so that his wife would have the house to herself as she entertained her lover and his friend.

While checking into the hotel I was literally shaking. What was I thinking leaving my wife with not one, but two horny men? Cheryl had looked so sexy in her skimpy sundress and wooden high heel sandals and I'd noticed that she'd applied quite a bit more makeup than usual. With hot pink lipstick, gobs of mascara and dark blue eyeshadow, Cheryl had erred on the side of looking slutty and I suppose that was appropriate given everything Nate had undoubtedly heard about her.

My wife had insisted that I wear my chastity device for the past week and when I thought about her flirting and carrying on with John and his friend, I felt the pinch of the plastic sleeve preventing any semblance of an erection. And with my key conspicuously dangling from Cheryl's anklet, my inability to masturbate was invariably going to be the subject of conversation. I could see it all clearly in my head, Nate and John laughing uproariously at the concept of a man who willingly grants his wife complete control over his penis while simultaneously enjoying the attentions of other men.

I lay there in my room for almost an hour before I realized I needed to get some fresh air, or I would go insane. And so, I decided to go on a hike, spending several hours at a local reginal park before returning to my hotel at around six-o-clock. I was getting hungry by this time, but I had little appetite to eat at a restaurant, the concept of seeing all the other patrons enjoying a Saturday evening dinner with their spouse or significant other making me self-conscious of my situation. And so, I merely picked up a submarine sandwich at a local sandwich shop and retreated to my hotel room where I watched television for the duration of the evening.

It was almost eleven-o-clock the next morning when I received a text from Cheryl telling me it was okay to head back home. My wife said that she and John were going out for lunch but that they were taking separate cars as John had to meet some friends later. "I'll be home around one-o-clock," noted Cheryl at the end of the text. My wife's message seemed somewhat perfunctory, and I was a little disappointed that she wouldn't be there when I got home, but when my phone chimed again, I read, "OMG, wait till you hear what I did yesterday! I was really naughty!!" My dick tried to stiffen in its plastic sleeve but to no avail. I knew I'd have to wait for Cheryl to return home to enjoy any relief and so I quickly grabbed my suitcase and checked out of the hotel, driving home as rapidly as I could.

When I arrived home, I found the house to be a complete disaster. Dinner dishes were still in the sink and glasses were left on the coffee table, some still containing wine or beer. What immediately caught my attention, however, was Cheryl's lacy panties lying conspicuously in the middle of the coffee table! I could only imagine the sequence of events that led up to my wife removing her panties in the living room! I then headed up to our bedroom, where it looked like a tornado had hit. The bed was un-made and pillows were scattered around the room. The sundress my wife had worn yesterday and the sexy wooden sandals I'd so reverently placed on her feet the day before were lying on the floor, tossed aside in the heat of the moment. On the nightstand was one of my wife's dildoes along with a tube of lube that had not been capped and when I looked closer at the bed, I saw dried spots of semen and smears of lube from what was, undoubtedly, a sexual encounter of epic proportions.

Cheryl wasn't due back from lunch for at least an hour and a half and so I immediately launched into cleaning the house. First, I made up the bed, putting fresh sheets on the mattress and then putting away my wife's clothes and shoes. I meticulously washed my wife's dildo, noting that it was smeared with lube and had clearly spent some time buried in my wife's tight pink asshole.