A Cuckold Story Ch. 27-28

Chapter 27

Upon our return from France, Cheryl immediately resumed her occasional dates with the Gym Guy and the L.A. Guy. And although she had intended to begin a job search upon her return from France, Cheryl didn't seem overly interested in pursuing leads and was content to spend her days working out at the Gym or shopping. To be honest, I didn't mind Cheryl's unemployed status and aside from her delegation of chores when she headed out on a date, she took on more of the household tasks allowing me to spend more time on my career.

It was almost a year following our return from France that Cheryl hinted that she wanted to go on a vacation. My wife had recently spent several days with the L.A. Guy in Las Vegas where he was attending a conference and the days spent lounging around the pool and nights filled with passionate sex had Cheryl longing to experience another vacation like she'd enjoyed in France, Mexico and Hawaii. I had been working around the clock for several months without a break and so when I saw an opening in my schedule, we booked a trip to Miami, as much for its reputation as a party town as for the warm weather and beaches.

In the two weeks leading up to our trip, Cheryl engaged in her typical behavior of trying on pretty much all her clothes in an effort to assemble a sexy, alluring wardrobe for South Beach. I have to say, I didn't mind in the slightest as each evening I would be treated to what we both called a "fashion show" as my wife would model various combinations of dresses and shoes with the goal of selecting outfits that would attract the maximum male attention. And as had become customary before one of my wife's escapades I was denied sexual contact with Cheryl the entire time and so I would sit on the bed with my erection pressing against my pants a she flaunted her charms in all manner of sexy outfits. On two occasions, I couldn't resist the urge to masturbate and I took my erection in my hand and jerked off while Cheryl teased me with comments about wanting to find a sexy, hung stud while in Miami.

After a very frustrating two weeks, Cheryl and I found ourselves catching an early morning flight to Miami where we then took a cab to South Beach. And once we checked into our art deco hotel, we headed out to stroll down the beachfront street, marveling at all the beautiful people sitting at the sidewalk cafes. "Oh my God, Mike! It's so beautiful here! And look at everyone, it looks like they're all models!", gushed Cheryl as she surveyed the scene.

We walked for about an hour before I suggested that maybe we should have a drink. The sun had just set, and neon lights were illuminating the buildings giving everything a wonderful, sexy aura. But after asking whether Cheryl wanted a drink, she immediately replied, "No, I need to change first. I look terrible."

Now, my wife never looks terrible to me and with her shorts, tank top and platform Keds, I thought she looked positively adorable. But never one to argue, I suggested we head back to the hotel for Cheryl to change. Once in our room, Cheryl donned a very sexy white miniskirt, a black tube top and a pair of black strappy high heel sandals. I, too, changed into something a little more appropriate and we were soon strolling down the street together looking for a good place to get a drink. We eventually settled on a casual streetside bar but rather than take a table, Cheryl wanted to sit at the bar as she was already hoping to strike up a conversation with one of the numerous good-looking single guys crowded around the open-air bar.

After finding the last two seats available at the bar we ordered a round of drinks and as we sipped out cocktails, I couldn't help but notice that my wife was making every effort to attract the attention of a group of three guys nearby. She was constantly looking in their direction and had arranged her seat so that her legs were on full display and she was making a point to twirl her high heel clad foot in a not so subtle flirtatious gesture. Alas, Cheryl's efforts were for naught as other than several lecherous glances in my wife's direction the three guys remained standoffish and after about fifteen minutes, they were joined by three attractive young women who were obviously their girlfriends. Seeing the girls join the three guys, Cheryl sighed in disappointment and then reluctantly shifted her attention back to me while occasionally surveying the bar for any handsome single men.

We ended up having two drinks at this bar before we decided to get some dinner and after asking the bartender for a recommendation, we headed down the street to a Mediterranean restaurant where we were seated after only a slight wait. We studied the menu for at least ten minutes and were getting increasingly impatient with the fact that we had yet to have our server so much as fill our water glasses when suddenly we were approached by our waiter. Diego apologized profusely for making us wait and as he recited the specials for the day, I couldn't help but see that Cheryl was staring at him with unconcealed lust. I had to admit, Diego was very handsome, and it was obvious he worked out regularly as his muscles rippled beneath his tight white shirt. I could only imagine my wife's pussy moistening at the thought of bedding this good-looking stud and when he finally finished his spiel and made his way to the next table, Cheryl sighed, "Oh my God, did you see how handsome he is?"

When I agreed that Diego was extremely good-looking, Cheryl said, "I wonder when he gets off work? Maybe he'd like to have a drink with me."

I quickly realized that my wife had set her sights on this guy as I agreed to make myself scarce after dinner so that she would have the opportunity to work her wiles on Diego. And from that point on, throughout dinner Cheryl flirted non-stop with Diego as I played the familiar role of pussy-whipped husband. And after paying the check, I excused myself to go to the restroom where I then took my time giving Cheryl the chance to ask Diego if he wanted to have a drink with her when he got off his shift.

As I walked back to our table, I could tell that Diego had agreed to join my wife for a drink as she was beaming from ear to ear. And as I escorted Cheryl out of the restaurant, Diego gave me a condescending smirk as he thanked me for the generous tip. Once out on the street, Cheryl leaned close to me and whispered, "He said he can get off work early and he'll meet me in thirty minutes right here in front of the restaurant. I'm so excited. This is going to be so much fun."

After telling Cheryl I was happy for her, I offered to buy her another drink while we waited but she refused, telling me she didn't want to be too drunk for her date. Instead, we headed to a nearby pharmacy where Cheryl purchased condoms "just in case." By the time we had returned to the restaurant, it was almost time for her to meet Diego and after saying our goodbyes we parted, with me heading back to our room while Cheryl waited anxiously for her date.

When I got back to our room, I stripped down and immediately slipped into bed. Although my dick was rock hard at the thought of my wife with Diego, I didn't masturbate right away. Instead, I pondered my situation, marveling how at that very moment my wife was enjoying a drink with another man while, I, her loving husband was lying alone in our hotel bed. But rather than being upset with the situation, I was happy that Cheryl was enjoying herself and I hoped that she and Diego would hit it off and end up pleasuring each other in a lusty sexual encounter. Cheryl was the love of my life and I wanted her to have the most exciting and satisfying sexual life possible and if that meant other men needed to be involved, then so be it.

I lay in bed for over an hour with these thoughts in my head until I eventually broke down and began to masturbate. It didn't take long and before I knew it, I was spurting out my load into my hand as I imagined Cheryl taking Diego's thick cock deep into her pussy. After cleaning myself off, I tried to sleep but I found it difficult and after another hour of fruitlessly trying to fall asleep I found myself yet again with my dick in my hand as I began to masturbate for the second time that evening. I had just started to work my erection when I heard the key in the door, and I saw Cheryl sheepishly entering the room with a sexy smile on her lips.

"Hi Hon", was all Cheryl said as she headed straight to the bathroom before stripping off her clothes and climbing into bed next to me. And as my wife snuggled up against me, I couldn't help but ask how her date had gone

.

"Oh, God, it was really fun Mike. We had a drink but then we got a room at a hotel near here. Diego didn't have enough money, so I had to pay. I hope you don't mind", explained Cheryl while reaching down to fondle my still hard penis.

My wife's hand on my penis felt like heaven itself and after assuring Cheryl that I was fine with her paying for a room, she went on to tell me how she and Diego had fucked twice before he said he had to get home to his girlfriend. "He was really good, Baby. His cock was so thick", sighed Cheryl while she continued to work my dick. My wife kept pumping my dick for the next several minutes while filling me in all the nasty details of her encounter until I could no longer hold out and I began to come, my load oozing out of my penis and soaking the sheets.

Once I had washed up after my orgasm, I rejoined my wife in bed and we both soon fell into a satisfying sleep. The next day we acted like any other loving couple as we swam in the ocean and Cheryl worked on her tan. We were both surprised that so many women on the beach wore thongs and went topless and seeing this, Cheryl donned the skimpiest thong she'd brought and over the course of the day, I watched as many, many men ogled my wife's shapely bottom and bare tits.

Earlier that day, Cheryl told me that Diego had asked how she'd so easily ditched me the previous evening. My wife said that she was unprepared for the question as he'd posed it soon after he'd first slipped his thick cock into her juicy pussy. And so rather than coming up with some sort of white lie, she merely said that I allowed her to sleep with other men. Cheryl said that while this concept was foreign to Diego, he didn't miss a beat as he demanded to know whether he was bigger and better than me in the bed. Of course, Cheryl told him he was much bigger and that she'd withhold judgement as to whether he was better until after they'd finished fucking. As is par for the course, this only encouraged Diego to make an extra effort to expertly fuck my wife until she was crying out in orgasm. And later when they were both lying side by side in the bed, savoring the afterglow of their orgasms, Cheryl sensuously whispered to Diego, "You're so much better than my husband. And a lot bigger too."

After a night like that it was no question whether Cheryl would be seeing Diego again and around noon, my wife received a call from Diego with him telling her he had arranged to get off work at 10:00 that evening. Cheryl and I had already discussed the fact that she was going to fuck Diego again and so rather than getting another hotel room, I offered to let her use our room while I waited in the bar. My wife loved that idea and so when Diego called her, she told him to meet her at our hotel when he got off work.

After spending the day on the beach, I was regretting my offer to give up our room as I was extremely tired. Nevertheless, after grabbing a light dinner with Cheryl I found myself watching my wife dress for her date with Diego with a raging erection. Given that Diego was meeting her at our room there was no need for Cheryl to dress in anything whatsoever, but my wife has always enjoyed the erotic nature of sexy clothing and so she rummaged through her suitcase until she found the perfect outfit.

I watched in awe as Cheryl slid sheer black stockings up her legs, attaching them to the lacy black garter belt she had previously fastened around her waist. My wife's freshly shaved pussy looked so inviting and I couldn't help but massage my crotch as I knelt in front of Cheryl and slid her feet into the pair of black high heel pumps she'd picked out. The only other item of clothing my wife chose to wear was a sheer black baby doll nightgown that barely reached her waist. Cheryl looked absolutely delicious and I was just about to ask if I could masturbate before leaving, when we were startled by a knock on the door. It was only 9:30 and so I didn't think it would be Diego, but when I looked through the peephole, there he was in all his masculine glory.

This was embarrassing in the extreme. I'd hoped to leave before Diego arrived but here I was still in our room, obviously complicit in my wife's preparation for their date. I hesitated for a moment not knowing what to do, but when Cheryl asked who was at the door and I told her it was Diego, she snapped, "Well, let him in! What's wrong with you?" My wife's eagerness to see her lover and her obvious annoyance with my dithering overcame my fears as I nervously opened the door to greet Diego. Diego seemed surprised to see me and although I couldn't look him in the eye, I mumbled something about needing to be going and grabbing my phone off the dresser, I headed out. Before I left, however, Cheryl teasingly giggled, "Mike, remember what I told you. Don't come back until I call you, okay?"

My wife then moved to Diego, embracing him passionately as I sheepishly replied, "Yes, Dear. I'll wait till you call", before closing the door to our room.

Although thoroughly humiliated at being dismissed so casually, I was also intensely aroused. My dick had formed a tent in my pants, and I waited outside in the hallway for several minutes for my erection to subside before heading down to the lobby.

That night I wandered around South Beach for an hour or so until I eventually grew tired of watching the revelers out on the town. I then headed back to our hotel where I waited in the lobby bar, nursing a drink until I finally heard my phone ring and answering it, Cheryl told me to come back to our room. I threw a twenty-dollar bill down to pay my tab and then hurried out but as I rounded the corner, I ran directly into Diego leaving the hotel. He had a self-satisfied grin on his face and when he saw me, he chuckled slightly under his breath before giving me a nod of acknowledgement. In response I merely gave him a sheepish smile before quickly hurrying up to our room to find Cheryl lounging in bed, still wearing her garter belt and stockings.

Seeing my wife seductively lying in bed, my dick became immediately erect and I hurriedly stripped off my clothes and climbed onto the mattress where I crouched on all fours between my wife's legs. As I gazed at my wife, I couldn't help but think she was the most beautiful woman I'd ever seen. Cheryl looked so completely satisfied, her lips curled in a sexy smile that both warmed my heart and caused my dick to twitch in arousal. And unlike her first encounter with Diego, Cheryl had obviously not bothered with condoms and when I glanced between her legs, I saw a stream of semen leaking from her well-fucked pussy. When Cheryl saw me staring at her juicy opening, she teased, "Why don't you give it a kiss."

I didn't need to be asked twice as I dove in, licking and sucking my wife's juicy opening as she moaned in appreciation. Diego had left quite a sizeable load in Cheryl's pussy and I spent almost twenty minutes scouring out every drop of his come as my wife urged me on. Eventually I could sense the familiar signs of my wife's impending orgasm and I then reached back between my legs and grasped my penis and began to masturbate. I then concentrated my oral attentions to my wife's clit and as she began coming, I stroked my dick furiously so that I, too, climaxed at the exact same moment. It was an incredible experience and later as we lay together in bed, Cheryl admitted that she hadn't come this good with me in quite some time. Hearing this was music to my ears and when my wife told me that Diego wouldn't be able to see her for a couple of days, I resolved to spend every night with my face buried between my wife's legs giving her the orgasms she so richly deserved.

The next morning Cheryl told me that she wanted to go out dancing that evening and so after a late breakfast, I accompanied my wife on a shopping trip to find a new dress and shoes. As is typically the case, Cheryl teased me mercilessly as she tried on various sexy dresses, parading out of the dressing room as if she was headed out on a hot date. My wife always left me waiting outside the dressing room holding her purse and as she posed in each outfit, she'd ask, "Do you think this'll get the attention of guys at the club?" or "If you saw me wearing this at a club, would you think I was hot?" I think that being out of town and having just enjoyed two lusty nights with Diego had loosened my wife's inhibitions and she had no qualms about teasing me like this in front of the salesgirls and other patrons at the shops. I must confess, though, I did take some sort of perverse enjoyment at the pitying looks I received, and I would invariably tell Cheryl she looked gorgeous and that she'd receive lots of male attention.

Eventually Cheryl decided upon a white spandex mini-dress that hugged her body like a second skin and as we left the shop, she quipped, "I'll wear this when I see Diego in a couple of days too." I assured my wife that Diego would no doubt think she looked great in her new dress as Cheryl then turned her attention to finding a new pair of high heels. We traipsed in and out of several shoe stores until Cheryl eventually found a pair of retro tan wooden heels with a matching purse. Seeing these sexy shoes on my wife's feet, I was instantly reminded of Monique, the girl who had befriended me in college and who had routinely worn similar wooden high heel shoes. And since Monique had never opened up to me about her frequent sexual escapades, I was already anticipating Cheryl giving me a blow by blow description of these sexy shoes draped over Diego's broad shoulders.

Later that evening as we were preparing to go out, Cheryl had me shave her pussy and as I was carefully shaving around her lips, I couldn't help but ask, "Uh, Honey? I know you're not going to see Diego for a couple of nights, are you thinking you might try to hook-up with someone else tonight?" The minute the words were out of my mouth, I regretted asking my wife about her plans. We'd long since established that I was not to question Cheryl's intentions with respect to other men and I knew I'd overstepped my boundaries. But to my surprise, Cheryl didn't chastise me but instead just casually stated that she wasn't planning on getting picked up that evening, but if some handsome stud should happen to come on to her, she wanted to be prepared. Hearing my wife's explanation, I just said, "Oh, yeah, okay. That makes sense", as I finished up my task.

Later as I escorted my wife out to dinner and then to the club, I was proud of all the envious looks I received from other men. Cheryl looked gorgeous and everywhere we went men would turn and stare at her sexy legs and trim figure. When we entered the club, I noted that there were at least two men for every woman, and I knew that my wife would receive her fair share of attention. It didn't take long for Cheryl to get hit on and as I was getting our drinks, a guy standing at the bar asked her to dance and when I turned to hand my wife her drink, she said, "Honey, can you hold my purse for a minute. I'm going to go dance." I then watched my wife being led out to the dance floor where she and her partner danced to the lively music. When the song ended, Cheryl returned to the bar where she then sipped her drink while surveying the many handsome men in the club.