A Cuckold Story Ch. 57-59

Chapter 57

As it happened, almost a month following the end of Cheryl's affair with Tom, she received a call from Tim, her investment banker boyfriend who'd relocated to London. It seems he had to be in San Francisco for a couple of days and when Cheryl told me he called, I encouraged her to spend two nights in the city with her well-hung former lover. My wife then began to excitedly plan her stay, telling me she wanted me to drop her off at Tim's hotel, and that she'd then meet me at my office later in the week when he left.

In the lead up to my wife's reunion with Tim, she had me help her find a sexy new dress. And late morning on the day I was to deliver her to her lover, I watched enviously as Cheryl shimmied into her form-fitting black dress.

Underneath her dress, Cheryl was wearing a pair of thigh-high stockings and nothing else, the implication being that there was no need for underwear of any kind to get in the way. Black patent leather pumps completed the outfit and as I slid them on my wife's feet, she asked me to fetch her gold anklet and to attach my chastity key to it.

Cheryl had locked me in chastity several days earlier and I nervously agreed to her request as I pulled the gold anklet out of my wife's jewelry box and then attached the small chastity key to the thin gold chain. Kneeling before my wife, I attached the delicate chain around my wife's ankle as a sexy smile lit up her face.

Tim had known from the outset that I was a cuckold and Cheryl had also made sure he knew that whenever she was with him, I was regularly locked in chastity. But other than the time he'd stayed at our house, my wife had been reluctant to flaunt my key and I couldn't help but ask why she was doing it now.

A naughty grin formed on Cheryl's lips as she replied, "Well..., when you drop me off today, I was thinking maybe it'd be fun if I introduce you to Tim."

My wife let her statement sink in for a moment before giggling, "Tim reminded me the other day that I always kept you locked up when I saw him. He said he still couldn't believe you'd let me do that. So, I think it'd be fun to let him meet my precious little hubby. He can see for himself how you love that I keep that little dickie of yours all locked up when I'm out."

I cringed hearing my wife's request, and I think she might have been subconsciously trying to get back at me for insisting she break up with Tom. That, and she was probably catering to my increasingly vocal requests for her to feel free to strike up a new relationship, even if it might be embarrassing or humiliating for me. You see, now that I felt more secure in our marriage, the more I felt comfortable in letting Cheryl push my boundaries.

I knew it would be excruciating to meet Tim, knowing that he was fully aware that I'd known all along that he'd been sleeping with my wife. But that was exactly what Cheryl had in mind when she asked me to do it. To hand my wife over to another man for the express intent of fucking her for two nights was indescribably naughty, almost unbearable, but Cheryl knew I'd relish every dirty detail. And so, I agreed to my wife's suggestion. I'd let her introduce me to her lover and then head home, the consummate cuckold husband.

Later that day as we were driving to the hotel, both Cheryl and I remained silent. My wife was obviously very much looking forward to her reunion with Tim and I'm sure she couldn't wait to have him all to herself for two consecutive nights. As for me, I was as nervous as a schoolboy on his first day of class. Although I'd met plenty of my wife's lovers over the years, it never got easier and even though Cheryl had said Tim was a "nice guy", I never knew how things might go.

Entering the hotel, Cheryl instantly spotted Tim seated in the lobby. My wife immediately rushed to her lover and embraced him while I followed timidly behind, trailing Cheryl's suitcase. After holding each other for quite some time, Tim broke away from my wife and turned to me, casually remarking, "It's nice to finally meet you Mike."

I stammered something about it being nice to meet him as well when I realized that Tim had extended his hand in greeting. I nervously grasped Tim's large hand and as we shook hands, I couldn't help but feel the pinch of the sleeve encasing my penis as I withered under this confident smile.

Dressed casually, Tim was a very handsome man in his slacks, and expensive black shirt and he looked very much the sophisticated stud that Cheryl had always described. At well over six feet, Tim towered over both me and Cheryl and I was reminded that my wife had said that he had an impressive cock as well, extra thick, with a large mushroom shaped head.

Cheryl was giggling nervously the entire time and when, after shaking hands with me, Tim turned back to my wife, taking her in his arms and passionately embracing her once again, I just about fainted. I'm not sure whether Tim noticed my chastity key dangling from my wife's anklet, but I had little doubt he'd see it later, most likely while lifting my wife's legs and placing them over his shoulders as he inserted his thick cock into her sopping pussy.

I was just about to make my exit when Tim asked, "So Mike, do you want to join Cheryl and me for a drink before you leave?"

I started to stammer something about needing to go but before the words could leave my mouth, Cheryl exclaimed, "No! I want to go up to the room, right now!"

Tim laughed at my wife's impatience to get started on what would likely be a marathon sexual encounter. He then said, "Well, I guess I shouldn't keep the lady waiting."

I quickly said my goodbyes as Tim took my wife's suitcase from my hand and then escorted her to the elevator. Knowing that Cheryl was naked as the day she was born beneath her dress only added to my intense arousal and seeing my chastity key dangling provocatively from my wife's anklet, I knew it was going to be a frustrating couple of nights for me. Nevertheless, as I made my way out of the hotel and headed to the parking garage, I was filled with an odd feeling of satisfaction and happiness.

Cheryl was going to be spending the next couple of days enjoying the attentions of a handsome charming man, not some arrogant loudmouth like Tom. And although I certainly didn't feel the same sense of physical intimidation that I did with Tom, there was no doubt that between Tim and I, he was the alpha-male. And as the alpha-male he would soon be enjoying his just rewards, my wife would see to his sexual needs and desires while I, the beta-male, headed home to clean the house and perform my cuckold chores.

Cheryl's visit with Tim proved to be just the thing to lift her mood and allow her to forget all about her break-up with Tom. And when she waltzed into my office three days later, my wife looked positively radiant.

Cheryl later told me that she'd forgotten how great it was to spend time with a lover that was both sexually gifted, and charming and sophisticated. Although this was just the sort of statement that had, in the past, tweaked feelings of jealousy, I now merely told my wife that I was happy for her and that I wished Tim lived closer so that she would see him more often.

After Tim's visit, my wife was relatively faithful and on only two instances did she step out. The first was an impromptu visit by Chris, Cheryl's married New York boyfriend who was travelling for business and stayed two nights at an airport hotel. My wife spent both nights with Chris at his hotel and the two of them had an enjoyable get-together, fucking and sucking several times each night.

The second time occurred when Cheryl ran into her former boyfriend John while out having a happy hour drink with one of her girlfriends from the gym. John was meeting Nate at that same bar and when he showed up, the two girls along with John and Nate enjoyed a drink together before Nate said he had to get home to his wife and Cheryl's friend headed home to her husband.

That left John and my wife reminiscing about old times and when one thing led to another, Cheryl found herself accompanying John back to his house where the two of them fucked all night. I only learned of this the next day as Cheryl merely sent me a text at around ten-o-clock telling me she wasn't going to make it home that night and I then spent the night masturbating wondering what my naughty little wife was up to. To my relief, Cheryl, and John both agreed that this was a one-time encounter and as it turned out, my wife never saw him again after that.

Although Cheryl did not immediately jump into another relationship, I think after her affairs with Dan and Tom, I could never think of myself as anything but a cuckold. There was something about the way both these guys had flaunted their relationships with Cheryl that permanently etched my soul. It didn't help that whenever I'd run into one of our neighbors or former classmates, I'd be on the receiving end of derisive or scandalized looks for having the temerity to stick with my adulteress wife.

My wife and I talked about this frequently and I had to admit to Cheryl that although it had been difficult for me at times, I had no regrets whatsoever that I'd given her the go-ahead to date Dan or Tom. And if it wasn't before, it now felt like it was apparent to everyone that other stronger and more powerful men were destined to fuck my wife while I was destined to later masturbate to accounts of their encounters. And with so many others fully aware of my cuckolding, I had no choice but to face that reality head on, to hold my head high and to continue to publicly express my love and devotion to my beautiful wife.

Eventually, Cheryl began seeing a guy she met through mutual friends of ours. Kevin was somewhat younger than Cheryl and me, but that didn't stop my wife from pulling out all the stops when she'd met him at a small party to celebrate our friends' anniversary. I could easily tell that my wife was smitten with this guy and before we left for home, Cheryl slipped him her telephone number and the very next week my wife and Kevin hooked up, fucking twice at his apartment in San Francisco.

Cheryl dated Kevin for several months, but their get-togethers were not always frequent and in my wife's words, Kevin wasn't "aggressive" enough in the bedroom for her taste. To make matters worse, Kevin had qualms about carrying on a sexual relationship with a married woman and even when Cheryl told him that I was okay with her infidelities, he still couldn't get comfortable with the concept. Finally, they both agreed to end things, leaving my wife, once again, without a lover to keep her sexual satisfied.

Cheryl's next true relationship with another man began a little more than a year following her breakup with Tom. We were attending the wedding of a co-worker of mine and as usual, Cheryl was adamant that she wanted to look "hot" for the wedding. My wife and I'd spent a good portion of the prior weekend searching for an appropriate dress and Cheryl had eventually decided upon a very sexy sundress in red with white buttons down the front. The dress was very short and came to mid-thigh to show off my wife's shapely legs and Cheryl paired this sundress with some tall, red sling-back pumps that elongated her legs even further.

Seeing my wife primp for the wedding that morning I was exceedingly glad that Troy no longer worked for my firm as I could easily picture him and Cheryl picking up where they left off last. And as titillating as that sounded, I really didn't want to risk having my cuckold status become as well known by my co-workers as it now was by my neighbors.

The wedding was held at a winery in Napa and as Cheryl and I watched the couple say their vows, I teared up as I typically do when hearing two people express their undying love for one another. And as my wife and I walked across to the reception that was being held in the tasting room, we held hands in an expression of our own love for one another.

The reception was a lively affair and given that it was held a winery, the wine flowed freely. Cheryl was her usual bubbly self and as she flitted from table to table, I could see even some of my younger co-workers checking out my wife. By the time the music started playing, my wife had consumed quite a few glasses of wine and she was certainly feeling no pain as she danced with a succession of men while I sat at a table to the side keeping an eye on her purse.

After almost an hour of dancing to pretty much every song, I noticed Cheryl was paying particular attention to a tall handsome guy who I didn't recognize whatsoever. She and he danced several songs in a row and when one particularly lively number ended, they both headed to the bar to grab a drink together.

As I watched my wife and this guy at the bar, I was suddenly interrupted by the groom, Dave, who sat down at my table and thanked me for coming before telling me all about his honeymoon plans. It seemed that Dave and his new bride where headed to Paris for their honeymoon and Dave asked me for tips and restaurant recommendations given that all my coworkers knew that Cheryl and I had visited Paris several times.

When Dave finally got up from his seat and headed over to another table, I turned to look back where I had last seen Cheryl and she was nowhere to be seen. I scanned the dance floor and I didn't see her there either and when I stood up and looked around the reception, my wife was conspicuously absent.

At first, I assumed that perhaps my wife had needed to use the restroom but as five minutes turned to ten and then to twenty, I started to get concerned. It didn't help that I'd not seen the tall guy she had been dancing with either and I started to get worried that he and my wife had snuck off somewhere and at that very moment were groping each other or worse.

I would have gone looking for Cheryl but with her purse sitting at the table I couldn't very well leave it there unattended and so I continued to wait for almost an hour until I saw my wife headed towards me through the crowd. Seeing my wife's guilty smile and the way her dress now looked wrinkled and disheveled, I knew immediately that she'd been up to no good. And when she reached the table, I noted that one of the buttons on the front of Cheryl dress was undone, leading me to exclaim, "Where were you?"

Cheryl just giggled, "I was with my new friend Jack," before she sat down and grabbed her purse, pulling out her lipstick and applying a thick coat of red gloss to her lips.

"Who is Jack?" I questioned as I couldn't help but be miffed by my wife's flippant response.

Cheryl either didn't notice that I was perturbed, or, more likely, she didn't care as she explained that Jack was an old friend of Dave's and she and he had taken a walk around the winery. I couldn't help but question just what sort of "walk" my wife had taken and when I pointed out that one of her buttons was undone, she giggled, "Oops I guess I missed that one," before reaching down to button her dress.

Just then, Cheryl spotted Jack over near the bar as she stood up and said, "C'mon Mike. I want you to meet Jack."

All I could think was, is this really happening? Nevertheless, I stood up and accompanied my wife over to meet "Jack" and as introductions were made, I shook Jack's hand, thinking that that same hand had probably already become intimately familiar with my wife's warm pussy.

I stood there awkwardly for several minutes as Cheryl told me how Jack lived down in San Jose and had known Dave since high school. I tried my best to act nonchalant, pretending not to notice that my wife was clearly smitten with this guy and when I saw an opportunity to join a group of my co-workers, I took it, leaving my wife and Jack to finish their conversation.

Out of the corner of my eye, I watched Jack and Cheryl continue talking. Cheryl was pulling out all the stops, frequently touching Jack's arm and running her hand through her hair and I hoped that I was the only one noticing this shameless display. But when Jack pulled out his phone and I saw Cheryl giving him her number, I knew this was not to be a one-off encounter.

I had to admit, I could see why my wife was attracted to this guy. He was tall (6'5" I was to later learn) and he looked to be somewhat younger than Cheryl and me. But what was most striking about Jack was how handsome he was. Even as a man, I could appreciate that Jack was an extremely good-looking guy and with his rugged, bearded face, full head of hair and broad muscular shoulders, he looked like a taller version of Bradley Cooper.

I watched Jack and Cheryl for a good twenty minutes or so, trying my best to keep up with my co-worker's conversation while simultaneously keeping a watchful eye on my wife. Eventually, I saw Jack embrace Cheryl, their lips locking in what appeared to be more than just a friendly kiss before he then went over to the bride and groom to say goodbye.

Cheryl then headed to the restroom and as I saw Jack and Dave talking together, I prayed he didn't mention his brief encounter with my wife. And just as I saw Jack make his exit, Cheryl returned to my side saying that it was probably time to go. After saying our goodbyes to my co-workers, my wife and I made our way to Dave and his bride, thanking them for inviting us to the wedding and wishing them a great honeymoon.

Walking to the car, Cheryl was giddy with excitement. Her encounter with Jack had awoken something in my wife and she was giggling away non-stop, seemingly proud of herself for having seduced such a handsome guy so easily. When we got to the car, my wife grabbed me and kissed me passionately, cooing, "Kiss your naughty wife."

I did as Cheryl asked and when we got in the car and began to drive off, my wife started telling me how she and Jack had fucked on one of the picnic tables out in the vineyard. "Oh my God, I haven't done anything that naughty in a long time! We were right out in the open! Anyone could have seen us!" exclaimed Cheryl.

I winced when I heard this as I could just imagine the office gossip if one of my co-workers had spied my wife with Jack. But as nervous as I felt at hearing about Cheryl's open-air tryst, I couldn't help but develop a raging erection as my wife told me how she'd initiated things by kissing Jack and then reaching down and fondling his cock through his slacks. But then Jack took full control of the situation as he forcefully unbuttoned Cheryl's dress and then ripped her panties off, pushing her back on the table and mounting her without any foreplay whatsoever.

As Cheryl told me of her encounter, she began to unbutton her dress, reaching under the hem to massage her bare pussy. Eventually, she'd completely unbuttoned her dress and was naked except for her sling-back pumps and I was having a hard time keeping my attention on the road as I continually glanced over at my horny exhibitionist wife.

Cheryl's earlier encounter with Jack had clearly not quenched the fire burning in her loins and when she saw a dirt road heading off the main highway, she exclaimed, "Pull off there, Mike!" I pulled off the road and drove for several hundred feet up this rutted road until we came to a small clearing, Cheryl then opened her door and jumped in the backseat where she basically screamed at me to lick her pussy.

I hurriedly exited the car and ran to my wife's side where I knelt outside the door and began eating her pussy while she squirmed around on the backseat. Cheryl was so aroused that it didn't take long for me to get her off and as she cried out in orgasm, Jack's semen and my wife's juices flooded my mouth, forcing me to swallow twice to get it all down. I kept my mouth glued on Cheryl's pussy for several minutes more before I felt her hands on my head pushing me away.

Seeing Cheryl sprawled out on the backseat of our car, wearing solely her high heel shoes, was the most erotic sight I'd seen in some time and I unzipped my pants thinking I would quickly masturbate to this beautiful vision. But Cheryl had other plans as she moaned, "Fuck your naughty wife," and so I moved between her legs and inserted my dick into my wife's pussy. I didn't last more than a minute in the velvety confines of my wife's vagina but when I came it was like an explosion. I buried my penis in my wife and spurted out my load, marveling at how lucky I was to be married to such an incredibly sexy and adventurous woman.