A Cuckold Story Ch. 52-55

My wife obviously had other ideas as before the waitress had even returned my credit card, she exclaimed, "Let's all go have a drink at the bar next door!" This suggestion was met with enthusiasm by Dan and Jim with Dan telling me that he'd pick up the tab after I'd generously paid for dinner.

Now the last thing I wanted was to extend this uncomfortable evening and I immediately launched into an excuse about how I needed to get to bed early as I had a big day at work the next day. Cheryl was having none of my excuse, however, and when I saw the mischievous twinkle in her eyes, I knew she had something up her sleeve. "Mike's always such a party-pooper. Maybe one of you guys can drive me home?" asked my wife, looking directly at Dan and giving him a suggestive smile.

It turns out that both Dan and Jim had driven to the restaurant separately, so Dan immediately agreed to drive Cheryl home after their "drink". "Perfect!" squealed my wife before turning to me and giggling, "Okay, Sleepyhead. You go on home and go to bed. Dan will make sure I get home safe and sound."

Now, this wasn't what I had in mind at all and I tried to change my mind telling Cheryl, "Well, maybe I could have one drink. I'll still get to bed early enough."

Cheryl cut me off immediately, this time taking a more humorless tone as she scolded, "No Mike. You've been acting tired all night. You go home and get some sleep. Don't worry about me."

Cheryl was very clearly dismissing me, and I could see both Jim and Dan look at each other as if to say, "Can you believe this guy let's his wife order him around like this?"

When I glanced at my wife, I could tell from the look on her face that I needed to go home, pronto. And so, I sheepishly replied, "All right, Sweetie. I'll leave the front lights on. Don't stay out too late." I then turned to Jim and Dan and said my goodbyes, even thanking Dan for agreeing to drive my wife home later.

I could palpably feel the disrespect in both men as I prepared to make my exit. Just then the waitress returned with my credit card and after putting my card back in my wallet, I filled out the tip line, leaving a generous tip to the pretty young girl hoping she was oblivious to what had just transpired. I then made my departure, scurrying off with my tail between my legs, leaving my wife in the company of her lover and his good friend.

Cheryl later told me that the three of them did, in fact, have a drink together where they rehashed just how pathetic it was for me to regularly drop my girlfriend off at Dan's house and to then spend the rest of the night masturbating. During their conversation, Dan did little to hide the fact that he was having an affair with my wife and he even said to Jim that he'd thought about just coming clean with me and telling me that he was going to continue to see Cheryl with or without my approval. Cheryl said that although she and Dan had socialized plenty of times with his friends, this was the first time he'd come out and made it clear that he and she were an item.

My wife told me that it was arousing to let Jim in on their little secret and she enjoyed playing the adulteress role to the hilt. And when Dan let on that Cheryl had an unsatisfying sex life at home, my wife then joked to Jim that after hearing about Dan and Paula, she'd wanted to find out what all the fuss was about.

Dan had his hands all over my wife from the minute I'd left and when Jim excused himself after their drink, Dan and Cheryl headed straight out to his car where they began to engage in a heated make-out session. And it wasn't long before my wife found herself sprawled out in the backseat of Dan's car as he pounded her with his stiff cock.

I, meanwhile, was waiting impatiently for Cheryl to return home. My wife's teasing disclosures before dinner had stung, to be sure, but I had to admit I felt a certain sense of closure knowing that the details of my initial cuckolding were now known to Dan.

Sure, it was humiliating for him to know I'd masturbated to the sounds of him fucking Paula, but truth be told, I had no legitimate reason to be embarrassed. It was Paula who was cheating on me, and Dan was the one fucking my girlfriend. If anything, they should be the ones ashamed of what they'd done. And as for me, sure, it was embarrassing to have those guys know that I'd spent that entire summer masturbating to thoughts of my girlfriend fucking other guys, but what choice did I have? Paula had refused even my most timid advances and I had to get my relief somehow, didn't I?

And as I recalled the earlier conversations, I realized that as cutting as some of my wife's teasing comments and disclosures had been, there was an element of affection that infused her words. Yes, my wife had stripped bare my adolescent masturbatory habits, but she'd also professed to love that I was a virgin when we met. It was cute in a way and showed that despite her own promiscuity, Cheryl had very different standards for me, standards to which I was more than happy to adhere.

When several days later, Cheryl apologized, telling me she should never have divulged all these intimate secrets of mine, I told her not to worry. In fact, I'd ruminated on this topic enough to know that I'd didn't really care if Dan and Jim, and probably others by then, knew that I'd spent my nights masturbating to Paula's infidelities. I knew that if I hadn't internalized my cuckolding, regularly fantasizing about Paula's infidelities, and then later, Monique's trysts, perhaps I'd never have found my soulmate in Cheryl. Maybe I'd have tried to meet another girl, or even have lost my virginity by the time I'd met Cheryl at the community college coffee shop.

As strange as it sounds, I shudder to think what my life might have been like had I not been cuckolded early on. Would Cheryl have even been willing to give me a chance had I not been an innocent virgin, so different from the hunky, experienced studs she regularly dated? Would Cheryl have seen in me the potential to be a loving, committed partner, a "one-woman man" who dotes on her like a princess? I know in my heart that no other woman could ever measure up to Cheryl and I wouldn't change a thing about my past that would potentially have rendered me unsuitable to be her husband. I'm committed to my wife, and to remaining faithful, and it's this commitment that helps Cheryl and I navigate our nontraditional approach to marriage.

Musing about our dinner conversation and the unusual path our marriage had taken, I couldn't help but start to develop an erection when I flashed on thoughts of Cheryl and Dan together at that very moment. And the fact that my dick was unencumbered by my chastity device, I had to fight the urge to masturbate as I waited for my wife's return.

Eventually, I heard a car pull up into our driveway and I peeked out around the curtains, seeing Cheryl and Dan in the front seat, my wife leaning over to kiss her lover. What I assumed would be a quick goodbye turned into a lengthy conversation with my wife remaining in Dan's car for almost twenty minutes, the two of them talking and occasionally kissing.

Watching Chery and Dan together I was reminded that my wife's relationships are more than just fucking and sucking, it appeared that they truly enjoyed each other's company. Although my wife's sexual escapades are the moments I typically crave to hear about, Cheryl and her lovers are almost always genuine friends and she enjoys conversing with her male friends both in and out of the bedroom.

Eventually, I finally saw the passenger side door open and my wife exit Dan's car, but to my utter dismay I also saw Dan open his door as he then escorted Cheryl up to the front door. I instantly rushed to the bedroom where I jumped into bed and feigned sleep. And when the front door opened, I heard hushed voices and my wife's unmistakable giggle as she and Dan headed down the hall to the guest bedroom.

I couldn't believe Cheryl was going to fuck Dan in our very house! My dick was rock hard at this turn of events and after waiting several minutes to let the two lovers think I was still very much asleep, I crept to the master bedroom doorway and craned my ear hoping to catch some snippets of Dan and my wife's escapades.

Unfortunately, all I could hear was some faint sounds emanating from the guest bedroom and so I quietly slipped down the stairs, my stockinged feet making no sound as I crept towards the guest room. As I got closer, I could hear my wife's sighs of pleasure along with Dan's deeper, masculine groans as it was obvious the two of them were engaged in a heated lovemaking session.

Listening to Cheryl and Dan was a symphony for the ears, and it took all my willpower not to pull my dick out of my pajamas and masturbate to these lusty sounds. But instead of pleasuring myself, I committed the sounds my wife was making to memory. I knew that Cheryl's sexy little whimpers as she approached orgasm, followed by her piercing squeal as she came on Dan's thick cock would fuel many a masturbation session and I wanted to remember everything.

Eventually, I knew I was playing with fire lurking outside the guest bedroom and so after hearing Cheryl cry out in orgasm for a second time, I began to quietly make my way back up to our bedroom.

Once ensconced back in our bedroom, I stripped down to await Cheryl. It was at least a half-hour before I heard hushed voices once again in the entry followed by the front door closing. No more than a couple of minutes later, I heard Cheryl ascend the stairs.

As Cheryl entered the bedroom, she turned on the light, illuminating my beautiful wife in all her well-fucked glory. Cheryl hadn't even bothered to dress and after giving me a naughty smile, she moved to the bed where she straddled my face without saying a word. I instantly went to work on my wife's freshly fucked pussy, scouring out Dan's creamy loads while she reached down with her right hand and took my penis in her grasp.

With my wife's thighs on each side of my head, my hearing was muffled but I could still make out Cheryl giggling, "That's it, there you go Baby. Suck all that come out of your naughty wife." And as she ground her juicy snatch against my face, Cheryl stroked my dick, manipulating my penis expertly.

After licking and sucking my wife's pussy for at least ten minutes, it became clear to me that I was not going to be able to get her off, so I gave in to my own selfish pleasures, savoring Cheryl's hand on my dick until I began spurting out my load. And as Cheryl continued to pull on my wilting member, I kept my mouth glued to her pussy assuring that no remnants of Dan's semen remained.

Perhaps it was hearing about how I'd always masturbated when Paula was unfaithful or maybe it was fucking Cheryl under our own roof, but after that night, Dan seemed convinced that I wouldn't be an obstacle to carrying on an affair with my wife. And it was not much over a week later that I arrived home from work to find Cheryl lying sprawled out in our bed, a satisfied expression on her face as she announced that Dan had just left, having spent the majority of the afternoon fucking my wife in our marital bed.

I, of course, orally cleansed my wife's tender opening before heading down to the kitchen to prepare dinner, making sure Cheryl was well fed after her earlier exertions.

And it wasn't just Dan's newfound penchant for screwing Cheryl in our home that showed his disregard about me discovering their budding affair. On Saturday following their "afternoon delight" in our bed, Cheryl announced that Dan had invited her to join him sailing on the Bay with some friends of his.

When my wife told me of her plans, she said Dan was picking her up at ten, telling her to dress warmly. Hearing this, I mentioned, "What kind of man invites another man's wife to go sailing with him for the day?"

Cheryl reminded me that, at dinner with Jim and Dan, I'd specifically said I was okay with her having male friends. "Well, I didn't really say that, I just agreed with you. But I get your point," I replied as I watched my wife prepare for her date, her jeans, sneakers, and sweatshirt covering one of her sexiest bar and panty sets.

Cheryl had me answer the door when Dan arrived and as I invited him into the house to wait for Cheryl, he casually mentioned, "It looks like it'll be a beautiful day out on the Bay."

I was trying desperately to act as if it was no big deal to have my wife head out for an all-day adventure with another man as I replied, "Yeah, I know. I was hoping to get out for a bit today, but Cheryl's got me really busy around here." I then jokingly added, "I've got to take care of my Honey-Do list."

Dan just grinned at my statement, his look one of utter amazement that a man could be this hen-pecked. Just then Cheryl made her appearance, strolling down the stairs from our bedroom. Although dressed for sailing, my wife didn't skimp on makeup and with her dark eyeshadow, full pink lips and large hoop earrings, Cheryl looked very alluring.

My wife was carrying what looked to be an overnight bag and not knowing what she'd planned, I was nervous to ask what was in the bag. But Dan obviously had an idea as he asked, "Hey Babe, did you make sure to bring clothes for afterwards?"

Cheryl flashed Dan her winning smile and giggled, "Yeah, of course. And I brought a bottle of Chardonnay too."

"Good thinking!" exclaimed Dan before indicating they'd better get going or they might be late.

"Okay, Sweetie, I'll see you later," chirped Cheryl before adding, "And don't forget, the bathrooms really need some extra attention. And I left some clothes in my hamper that need hand washing. It's mainly just the usual, you know, panties, bras, that kind of stuff, but there are a couple of blouses too. Be extra careful with those, okay?"

My wife didn't need to remind me of those tasks, but I think she was just trying to show Dan how much I was willing to cater to her every request. I tried to ignore the arrogant smirk that formed on Dan's lips as I replied, "Yes, Dear. I'll be sure to take care of everything." I then watched enviously as Dan and my wife headed out, animatedly discussing how much fun it was going to be to go sailing.

Cheryl hadn't bothered to put me in chastity, nor had she forbidden me from masturbating, but watching my wife heading out for what felt like a real date, I was somewhat uneasy. It was one thing for Dan to take my wife out for the sole purpose of getting into her panties, but this felt different.

But in thinking it over, I eventually let it go. Cheryl had been excited to go sailing and it truly was a beautiful day. And if I could vicariously enjoy my wife's extramarital sexual escapades, then I could certainly do the same with her more innocent adventures. It was with these pleasurable thoughts that I started in on my chores, first tackling the kitchen and bathrooms, before cleaning the pool, mowing the lawn, and tidying up the garage.

It was almost five-thirty when I finally turned my attention to the laundry and I'd just begun carefully washing Cheryl's delicate underthings when I received a text from my wife. "OMG, so much fun! I love sailing!" This was soon followed by another text that read, "We're all going out for drinks and dinner. See you later. XOXO"

Well at least my wife had the courtesy to let me know what she was doing, and even though I'd suspected she'd have dinner with Dan, I had a burst of cuckold angst, my wife's nonchalant attitude about blowing off dinner with me making me feel that I was being taken for granted. Nevertheless, I replied, "OK, have fun. Love you," before returning to my handwashing.

As I gently kneaded a lacy black panty, bra and garter belt set in the soapy water, I couldn't help but be reminded that this was what Cheryl had worn the previous Saturday when she spent a good portion of the day at Dan's house. I'd helped Cheryl prepare for her date and I vividly remembered kneeling before her to buckle the tiny straps on her Mary-Jane pumps, my wife's lingerie set causing my penis to swell in my chastity sleeve.

That evening, Cheryl had returned home to a late dinner that I'd meticulously prepared for the two of us. It had been a wonderful evening, with my wife and I toasting our life together and laughing about the unusual nature of our marriage.

And as I mused about that dinner, I had to smile. Cheryl might be unfaithful, but she and I had the best relationship of any couple I knew. It was amazing, but I'd gone from being mildly upset with Cheryl for telling me she was having dinner with Dan and his friends, to now, feeling overwhelmed with love for my sexy, little wife!

It took longer than I'd expected but I finally finished washing all my wife's delicate items. I then turned my attention to preparing my dinner, careful not to mess up my now, spotless kitchen.

By the time I'd finished dinner, it was now almost eight-thirty. Still no word from Cheryl but I knew she'd probably come in late, if at all. And as I settled in to watch some television, I couldn't help but flash on what my wife might be up to. Was she laughing and joking with Dan and his friends over dinner, or was Cheryl already flat on her back, her legs spread wide to welcome Dan's thick cock into her greedy little pussy?

These prurient thoughts had my unencumbered penis stiffening in my pants and eventually I gave in. Moving to the bedroom, I stripped off my clothes and laid back on the bed. Taking my dick in my hand I began to masturbate to visions of Dan fucking my wife, his rock-hard cock eliciting squeals of delight from my horny spouse. It didn't take long, and I was quickly spurting out my load, wondering if at that very moment Dan was doing the very same, albeit with his sperm finding a welcome home deep inside my wife, rather than the paper tissue I used to mop up mine.

After cleaning up, I once again tried to watch some television and it was only after finding that I just couldn't get into any of the programs that I decided to call it a night. Of course, it wasn't the quality of the television programming that had me distracted, and my attempts at sleep were no better. I tossed and turned for at least an hour before finally falling into a fitful sleep. I must have slept for at least a couple of hours when I was suddenly awakened by my phone ringing and when I answered the phone, I realized that it was Cheryl calling.

"Hey Honey, are you asleep?" asked my wife, her tipsy slur a dead give-away that she'd had quite a bit to drink.

"It's okay, I was just dozing."

"Oh, sorry. I just wanted to let you know that I won't be home tonight. We had too much to drink and Dan doesn't want to drive," explained Cheryl.

I couldn't help but offer to come pick her up, but Cheryl immediately shut me down, saying, "No, No, you don't need to do that, Honey. Dan's friend said we can sleep on his boat. Isn't that cool?"

"Oh, Okay," was all I could muster in response. The absurdity of a wife telling her husband she was going to spend the night with another man on what was undoubtedly a cramped sailboat seemed to be lost on Cheryl. But hearing the raucous voices in the background, I realized that alcohol might be clouding my wife's judgement and that she and Dan were probably past the point of trying to keep their relationship discreet from me or his friends.

"We're still at the bar right now. But we're about to head back to the boat and everyone else is taking Uber home. I just didn't want you to worry, Honey," cooed my wife.

Although I was still a bit uneasy that Cheryl now seemed to be flagrantly cuckolding me in front of Dan's friends, I was touched by her concern about me worrying. And not wanting to spoil Cheryl's evening I merely replied, "That sounds good, Sweetie. I'll see you in the morning."