A Cuckold Story Ch. 29-30

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A visit from Chris and Brad returns to the picture.
13.3k words
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Part 9 of the 20 part series

Updated 06/10/2023
Created 03/23/2021
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Chapter 29

As so often happens with my wife, when it rains, it pours, and as her affair with Marcus heated up, so too did a couple of other relationships. One was with the Gym Guy who after calling Cheryl numerous times, apologizing for getting too serious and begging to see her again, was finally able to convince her to see him. On their date, the Gym Guy promised that he understood that Cheryl loved me and that she wasn't interested in jeopardizing her marriage. Cheryl had always liked the Gym Guy and she took him at his word and so after fucking several times that night they began to see each other regularly, this time unencumbered by the need to hide their affair from his wife.

The other new regular was none other than Brad who had cuckolded me so long ago but who now was back in the picture. It seems that Brad had just gone through a rather messy divorce and as part of getting his life back together, decided to move back to San Francisco to start over. Within days of his return, he called Cheryl and asked her to lunch and after a light meal, they headed to Brad's apartment where they picked up where they had left off after their last encounter.

Cheryl told me that Brad was still the masterful lover he'd always been, and she came numerous times that afternoon as they fucked. It was only two days later that Cheryl and I attended a party given by some of our friends to celebrate Brad's return and I found myself face to face with the man who had not only cuckolded me before my marriage but still had the ability to get my wife into bed with just a snap of his fingers. It was a little uncomfortable as Brad was still the same pompous jerk, I'd always considered him, but I had to admit he had kept himself in tip-top shape. And as we chatted, I couldn't help but be somewhat envious at how eager my wife had been to resume their relationship. It turned out that running into Brad became a common occurrence as we shared many of the same friends and over time I learned to put aside my nervousness and eventually became comfortable in engaging him in conversation, although I would have been hard pressed to consider him a friend.

With Brad, the Gym Guy and Marcus servicing my wife on a regular basis it's no surprise that my sex life was pretty much reduced to going down on Cheryl after her dates and masturbating to tales of her infidelities. Having been through this sort of sexual privation in the past, I made the best of it and took pleasure where I could find it. Given that my wife's trio of lovers were all divorced there was no need for them to sneak around and so it was the rare Friday and Saturday that Cheryl didn't have a date with one of her boyfriends. And although not on the scale of her "slut years", my wife's naughty adventures included numerous weekends spent with one or another of her boyfriends and even a week-long trip to Hawaii with the Gym Guy.

I suppose I should have been bothered by the fact that my wife was the consummate "booty-call" for her three lovers, but to be honest I think I had finally reached a point where I was at total peace with being Cheryl's cuckold husband. When we were together, Cheryl and I were still the same loving couple we'd always been and although penetrative sex was rarely on the agenda, we still walked hand in hand regularly, cuddled in bed and for the most part never gave any outward hints that our marriage was anything but normal.

With three handsome studs only a phone call away, Cheryl wasn't as prone to engage in random hook-ups as she had sometimes done in the past. That said, however, there were two notable exceptions to Cheryl's restricting herself to her three lovers. The first took place not soon after Cheryl had returned from her Hawaii trip with the Gym Guy. My wife and I were attending my company's Christmas party and as it turned out, Troy, my wife's former fling, had recently broken up with his girlfriend and was attending stag. Not surprisingly, Cheryl spent the evening brazenly flirting with Troy and after a particularly steamy dance together, she suggested they step outside for some fresh air and they were soon locked in a passionate embrace, anxious to explore each other's bodies once again. I'd surreptitiously watched as Cheryl and Troy had exited the ballroom and I suspected they might want an opportunity to get together and so when they returned, I pretended to be drunk, slurring my words and telling Cheryl that I needed to head up to the room we had booked in the hotel.

As I left the Christmas party, I could see Cheryl and Troy gathering up their coats and as I later learned, they headed immediately over to Troy's nearby apartment where they engaged in a nearly two-hour steamy fuck session. And when Cheryl eventually returned to our room, she immediately climbed up on the bed and straddled my face, grinding her freshly fucked pussy against my mouth as I struggled to devour every drop of Troy's come. This encounter was followed by additional get-togethers with my wife dating Troy for the several few months but like before, their relationship soon fizzled out.

The second time Cheryl strayed from her routine of fucking Marcus, Brad or the Gym Guy was, to me at least, my wife's most exciting sexual adventure to date. It all started when, out of the blue, Cheryl received a telephone call from Chris, the guy she'd fucked while on our Miami vacation. It turned out Chris was planning to be in San Francisco for business in two weeks and he was hoping to get together with Cheryl for a drink. Now, I'm sure a "drink" was not really what he had in mind, but Cheryl was more than happy to accept his invitation and she made plans to meet him at a downtown bar on the evening of his arrival. And that night after shaving my wife's pussy and watching her dress for her date, I offered to drive her in to San Francisco telling Cheryl that since Chris already knew I was aware of her infidelities, there would be no issues if he saw me dropping her off.

Cheryl loved the idea and so later that evening I found myself driving my wife to the city, continually glancing over at her, lustily admiring the tops of her stockings that peeked out under the hem of her short skirt. My wife was pretty certain she would be spending the night with Chris and so after dropping her off at the bar, I headed home, anxious to engage in a feverish masturbation session while picturing Cheryl and Chris together. And as predicted, Cheryl did, indeed, spend the night and I only heard from her the next day when she called me at work.

"Hey Baby, how are you?", cooed my wife when I picked up the phone.

My office door was wide open and so I didn't want to ask about my wife's night as I merely replied, "I'm good, Honey."

Cheryl then giggled, "I've got some great news, Mike. Chris said he can spend tonight and Saturday night at our house. Won't that be fun?"

I inadvertently shivered in apprehension as I made an effort to speak in a normal tone as I answered, "Uh, yeah. That sounds good, Honey." I then lowered my voice and whispered, "Should I go stay at a hotel?"

Cheryl just laughed, "No, Baby. Chris said it's okay if you're there. You can sleep in the guest room and Chris and I will take our room. It'll be fun, you'll see."

Despite my discomfort, my penis was beginning to stiffen as I envisioned Cheryl entertaining Chris in our home as I mumbled, "Uh okay."

Cheryl then told me to pick her and Chris up at his hotel after work before informing me that she was going to spend the afternoon shopping for a new outfit to wear that evening. And by the time I eventually hung up the phone my dick had formed a tent in my slacks, and I had to fight the urge to run to the restroom to jack off.

The remainder of the day was a blur and I'm quite certain I didn't get anything done at work as I anxiously counted down the hours before I was to pick up Cheryl and Chris. And as the clock struck 5:00, I grabbed my jacket and hurried down to the parking garage to retrieve my car. The drive over to Chris' hotel was uneventful although the entire time my heart was beating wildly in my chest and when I pulled up out front, my wife and Chris were nowhere to be seen. I was just about to text Cheryl to determine her whereabouts when I saw she and Chris exit the hotel. Chris was quite a bit taller than I remembered and with his broad shoulders and rugged, athletic physique he looked every bit the type of guy my wife enjoys when it comes to her sexual partners. Cheryl was wearing a short denim skirt that I'd never seen before and had paired it with a black, sleeveless turtleneck top, giving her a sexy, "city-girl" look. And on my wife's feet she wore the same black pumps she'd worn the night before and I marveled at how sexy Cheryl always dressed when with one of her boyfriends.

Chris tossed his suitcase along with Cheryl's overnight bag in the trunk of the car and opening the rear car door, he slipped into the backseat and exclaimed, "Hey Mikey! How's it going, Buddy?"

Before I could respond, Cheryl slipped into the backseat next to Chris as she giggled, "Thanks for picking us up, Sweetie."

"No problem", was my only response as Cheryl then asked me to drive up to Coit Tower.

"I want to show Chris the sights before it gets dark", explained Cheryl before telling me that she had made reservations for dinner at Bix. Now, Bix was a restaurant that my wife ate at frequently when out with a date. She liked the sexy atmosphere and proximity to downtown hotels, and it was only recently that my wife and I had dined at this restaurant. In fact, we had celebrated our anniversary there only a couple of months earlier and so I felt an unexpected pang of jealousy hearing that Cheryl wanted to dine with Chris at this very same restaurant. But my discomfort only increased when Cheryl added, "I hope it's okay Mike, but I made the reservation for two. I didn't think you'd want to join us."

"Uh yeah, that's fine. I don't want to be a third wheel", I stammered before adding, "Maybe I'll try that hamburger place over on Columbus. I've always wanted to try it."

Cheryl seemed oblivious to my unease as she turned her attention to Chris, chattered away as she acted the tour guide to San Francisco. Besides Coit Tower, Cheryl had me drive to the Golden Gate Bridge, Twin Peaks, Golden Gate Park and against my better judgement, Chris wanted to see Fisherman's Wharf. At each stop, Cheryl insisted I take a picture of her and Chris and I eventually had a dozen or so photographs of my wife and her lover posing in front of various San Francisco landmarks. Other than acting as the photographer and driver, for the most part, Chris and my wife ignored me as they cuddled in the backseat, chatting away as if I was a taxi driver rather than Cheryl's husband.

As I drove about, I realized that I was fulfilling one of my long-held fantasies. I had always wanted to be fly on the wall for one of my wife's dates and here I was doing just that. I had always envisioned my wife's dates as non-stop sexual marathons, but as I listened to Cheryl and Chris in animated conversation, I came to understand that my wife genuinely enjoyed the company of her lovers. To be sure, there was plenty of sexual innuendo and playful remarks between Cheryl and Chris, and more than once I caught them passionately kissing in the backseat with Chris' wandering hands copping a feel of my wife's tits or running his hand up her skirt. But at the same time, Chris and my wife chatted away about other things, acting every bit like two friends comfortable in each other's company.

Eventually after our whirlwind tour, I dropped off Chris and Cheryl at Bix before finding a parking spot and heading over to get my burger. I scarfed down my burger quickly and then headed back to the car to await Cheryl's text telling me to pick her up at the restaurant. It was almost two hours before I got the text and when I pulled up out front, I found Cheryl and Chris locked in a lusty embrace. It seems that they'd enjoyed two martinis each and were feeling no pain and as they tumbled into the backseat, Cheryl squealed, "Let's go home! I want to go to bed!"

Chris and Cheryl's inhibitions had definitely been lowered and as I drove home, they pawed each other with little regard for my presence. Moans and groans filled the car and I was finding it increasingly difficult to drive while simultaneously trying my best to sneak a peek of the action in the rear-view mirror. Eventually I heard the unmistakable sound of a zipper being lowered and when I glanced in the mirror, I saw Chris staring back at me with a shit-eating grin on his face as my wife was obviously sucking his cock right there in the backseat! I would have given anything to have been able to stop the car, unleash my throbbing penis and masturbate to the lusty scene taking place just feet from where I was sitting! But when Chris caught me looking, he snapped, "Keep your eyes on the road, Mikey" causing me to turn my attentions back to navigating back to our house.

After several minutes of listening to my wife's muffled moans and Chris' throaty groans of pleasure, I heard Chris say, "Okay, Babe, that's enough. I want to save this load for your sweet, little pussy." Cheryl let out a disappointed sigh as she reluctantly pulled her mouth off Chris' cock and sat up in her seat, giving me a sexy wink when she caught me glancing at her in the mirror.

The remainder of the drive was filled with tension as the sense of sexual urgency in both Cheryl and Chris was palpable. And when I pulled into our driveway, Cheryl and Chris quickly exited the car and began to kiss and caress each other right there in front of our house. My wife and her lover paid no attention to me as I watched them devour each other, Chris' hands reaching down to fondle my wife's shapely behind while his tongue probed her mouth. I was worried that our neighbors might see this wanton display and so after taking their bags from the trunk, I hurried to the front door, followed closely by my wife and Chris and as I fumbled with my key, Cheryl impatiently snapped, "C'mon, Mike! Hurry up! Open the door!"

As I opened the front door to our house, Cheryl and Chris pushed past me and practically ran up to our bedroom. And it was no more than a couple of minutes after the bedroom door had slammed shut that I began to hear the rhythmic squeak of the bedsprings punctuated by my wife's squeals of delight.

As the two lovers pleasured themselves, I realized that I, too, needed some relief after my sexually frustrating night. And so, I quickly made my way to the guest half-bath where I dropped my pants and began to masturbate. Unfortunately, I couldn't hear my wife and Chris in this room and so I exited the bathroom and stealthily crept upstairs until I was right outside our master bedroom. Here, I could clearly hear Cheryl and Chris in our bed and I then resumed stroking my dick, reveling in the fact that my wife and her lover were fucking right on the other side of the door.

I eventually dropped to my knees outside the door, continuing to fondle myself as I focused on every sound my wife was making. From her heated demands for Chris to fuck her harder to her lusty whimpers when he did just that, Cheryl was holding nothing back. I was in seventh heaven as I masturbated and it was a wonder I lasted as long as I did as I listened to Chris bring my wife to first one, and then two thunderous orgasms, her cries echoing around the house And as I heard my wife shriek and cry out in orgasmic bliss with her second climax, I couldn't help but come, my sticky load spewing out into my outstretched hand.

Once I'd come, I realized that the last thing I wanted was to be caught kneeling outside the master bedroom with my wilting dick in my right hand and a puddle of my semen in my left. And so, I quietly lifted myself up and headed back downstairs to clean up. As it turned out, I needn't have worried as Cheryl and Chris didn't leave the bedroom until late the next morning as they ended up fucking twice that evening before falling into a well-deserved sleep. I, meanwhile, masturbated to one more orgasm as I lay in the guest room, picturing Chris' thick shaft buried balls deep in my wife's juicy pussy, his balls bouncing off Cheryl's puckered asshole as he brought her to climax after climax.

Once I'd come for the second time that evening, self-doubts began creeping into my head. Was this truly what I wanted? Did I want to be openly cuckolded like this in my own home? Perhaps Cheryl had been right when she said she didn't want to tell Marcus that I was willingly allowing her to share his bed? And although Chris had barely said two words to me all evening, I could feel his lack of respect every time I caught his eye. Maybe it was best to continue to play the naïve cuckold husband where I could at least retain some semblance of dignity?

As I mused about these things, I realized that maybe being outed as a willing cuckold was a bit too much. To be sure, I'd accepted that Cheryl needed other men to achieve sexual satisfaction and I was even okay with her deriding my sexual skills and attributes when with these men. But for some reason it seemed less humiliating to be thought of as an unwitting cuckold, oblivious to my wife's adultery, than as a pathetic man who has acknowledged that he can't satisfy his wife and therefore grants her freedom to seek out other men. And when I thought of how I'd earlier knelt outside my own bedroom door, masturbating to the sounds of another man fucking my wife, I cringed in embarrassment. What if I'd been caught by Cheryl, or even worse, by Chris? Just the thought of it, sent shivers down my spine. It was one thing to be pleasuring myself when my wife was out on a date. This was something I'd done hundreds, or perhaps thousands, of times and other than the first few times, I'd never felt guilty or embarrassed. When I masturbate my thoughts are always centered on Cheryl and when she returns home, I always tell her exactly what I've done, describing in detail how many times I've jerked off and what I was fantasizing about. And those times when I masturbate before my wife, often with the taste of another man's seed still fresh on my lips, this always feels like an intimate act between husband and wife. It is me baring my soul to my wife and acknowledging through my actions that I love her and that I accept her need for other men. But eavesdropping outside the bedroom door and jerking myself off to the sounds of my wife and Chris somehow felt perverted and something to be ashamed of.

That night, I resolved to discuss my feelings with Cheryl once Chris was gone. Perhaps she could help me to understand why it seemed worse for her lovers to know I was a willing cuckold. And I also promised myself that I would refrain from masturbating for the remainder of Chris' stay since it was hard enough to face him as it was, much less after having gotten myself off over visions on him embedded in my wife's pussy! After making this decision, I slept well and when I awoke the next morning, I was feeling refreshed and confident I'd made the right choice.

I was up earlier than either Chris or Cheryl and I headed straight to the kitchen to brew a pot of coffee. Almost immediately after switching on the coffee maker I had reason to reconsider my decision to abstain from masturbating as I heard the faint sounds of laughter from the master bedroom, followed by the rhythmic squeak of the bedsprings. They were fucking again!

Cheryl has often told me that she likes to wake a man with a sensuous blowjob and that this typically leads to a full-blown fuck session. And while I can't remember the last time my wife provided me this treat, I've listened to plenty of explicit descriptions of my wife's morning trysts with other men and her frequent comment, "It's a great way to start the day!"