A Cuckold Story Ch. 13-16

Over the next week, Cheryl arranged to meet up with two of the guys who had responded. The first guy was about five years younger than Cheryl, but he had sent a nude photo that had piqued my wife's interest. And as Cheryl told me when she left for her Friday night date, "You probably shouldn't wait up. If he looks anything like his picture, I'll be spending the night." Now, as we had always done before, sexual contact between my wife and I had been put on hold before her date and so I had not had sex with Cheryl for over a week. But with my newfound enjoyment of masturbating in my wife's presence following her dates with the Gym Guy, I was reluctant to relieve my pent-up desires until my wife returned home. And so, that night, I lay in bed, my erection uncomfortably pressing against the sheets as I contemplated whether I should just get it over with and jerk off or, instead, wait for Cheryl to get home.

Fortunately, I didn't have to wait too long as it was no more than one-o-clock in the morning when I heard Cheryl's car in the driveway. After her earlier comment, I was surprised to see her home but when she entered the bedroom, it was obvious she had been fucked. But when I slipped out of bed and knelt before my wife to lick and suck her used pussy, Cheryl uncharacteristically motioned me away, telling me, "You don't need to do that, Honey. Anyway, we used condoms, so it'll probably taste funny."

This was very much unlike Cheryl and when I questioned whether she had had a good time, she shrugged and said, "Yeah, it was okay. But I don't know, he was kind of a jerk. I don't think I'm going to see him again." This was the first time since Cheryl had started cuckolding me openly that she had experienced a bad date. And that night, rather than reveling in my wife's naughty escapades while furiously pumping my dick, I spent almost an hour consoling her and telling her that there were plenty of other guys out there.

My wife's next date went much better and she spent several hours in bed with a guy I would come to know as the Fireman. Cheryl had always fantasized about fucking a fireman and when this guy responded to my wife's ad, she jumped at the chance to set up a date. It didn't hurt that this guy was 6'7" with muscles toned from daily workouts at the firehouse and when Cheryl returned home after her date, she gushed about how well she had been fucked and how "hot" this guy was. The two lovers had been so horny for each other that they had neglected to use condoms and so I was able to enjoy a sloppy creampie from my wife's pussy before engaging in a feverish masturbation session while Cheryl described her tryst.

After the Fireman, Cheryl continued to regularly date new guys while also enjoying repeats with men like the Fireman and the Gym Guy. At least once, but sometimes two or three times a week, Cheryl would go out on dates with other men and she thoroughly enjoyed playing the role of the naughty cheating wife when with her lovers. And although the bulk of Cheryl's dates resulted from her personals ad, she also amped up her flirting in day to day situations and ended up sleeping with a waiter from a restaurant we often frequented as well as the contractor we hired to put in several skylights in our living room. In both situations, Cheryl came to me before she did the deed and asked for my permission to break our previously agreed upon rule regarding friends or acquaintances. And, pushover that I am, I gave my wife the green light insisting only that she make sure they never learned that I was aware of her infidelities.

At first, I must admit that it was hard to face our contractor, or to eat at what had been one of my favorite restaurants, but I soon learned to take their smirks and condescending smiles in stride. I'm sure they both thought they were really pulling a fast one on me, fucking my wife behind my back. But, in fact I was fully complicit in my wife's affairs and, frankly, I kind of enjoyed playing the part of the naïve cuckold husband. And for the duration of our skylight project, Cheryl insisted I work late several times a week so that she could spend a good hour or two with the contractor, fucking and sucking him until his balls were drained completely. Not surprisingly, the skylight project took longer than anticipated and when the project eventually was completed, Cheryl insisted I give this guy a "performance bonus". And as I handed the check to our contractor and thanked him for his work, he and his assistant Miguel could barely conceal their laughter assuming I was completely unaware of his frequent dalliances with my wife.

It was also during this time that Cheryl and I agreed to disregard one other rule regarding her dates. It seemed that Cheryl missed the excitement of carrying on the occasional illicit affair and one night after she returned home missing her panties from a supposed "girls' night out", I questioned where she had really been. My wife confessed immediately, telling me she had been out with a lawyer she had met several weeks earlier through her personals ad. I suppose it seems silly that she would need to lie about her whereabouts given her freedom to date other men, but Cheryl went on to explain that she missed carrying on secretive affairs at times and that sometimes she enjoyed the thrill of sneaking around behind my back. Although I must confess, I was a little angry at being deceived, but the way Cheryl described her motives seemed genuine. And this, coupled with the fact that I was dying to lick and suck her well fucked pussy had me readily forgiving Cheryl for her transgression.

Later that night after I had masturbated to an incredible orgasm hearing about my wife's date, we agreed upon a new "don't ask, don't tell" policy. Cheryl would have free reign to have sexual relationships with other men without telling me and what's more, she would have no obligation to share any details unless she felt like it. Further, I was not to pry into any suspected affairs either. This didn't mean I would never be made aware of my wife's affairs. On the contrary, for the most part Cheryl would date as she had always done, telling me in advance, having me help her get dressed beforehand and licking her pussy upon her return home. But on occasion, Cheryl would carry on a weeks-long or sometimes, months-long affair, never providing any details to me until she felt the urge to confess.

Cheryl first took advantage of her new freedom not long after we'd come to the agreement that she could see other men without my knowledge. My wife had long been attracted to Thomas, one of her married co-workers and when they worked late one evening to finish up an important project, one thing led to another and Cheryl soon found herself sprawled out on the conference table, Thomas thrusting his impressive cock in and out of my wife's juicy pussy. Because we'd previously agreed that Cheryl would refrain from dating co-workers, my wife opted to keep this encounter secret and over the next couple of months she and Thomas would regularly meet up after work, fucking at a sleazy motel near their office.

I was completely oblivious to my wife's affair with Thomas and it was only a couple of days before Cheryl's company Christmas party that my wife confessed. It seems that Thomas' wife would not be attending the party and Cheryl asked me if it would be okay if I skipped the event so that she and her lover could hook up afterwards. At first, I was a little taken aback that my wife had violated our rule about dating co-workers, but seeing the look on Cheryl's face, her obvious desire to enjoy a sexy evening with Thomas, and I forgave her instantly. In addition, I readily agreed to my wife's request, even offering to take her shopping for a sexy new pair of shoes for the party. And on the evening of her Christmas party, I dutifully helped zip my wife into her sequined party dress, the hemline barely covering the tops of her thigh high stockings, before kneeling to place Cheryl's new strappy heels on her feet. Once my wife was dressed and ready to go, I drove her to the hotel in San Francisco where the party was to take place, allowing Cheryl to feel free to have as many drinks as she wished without worrying about having to drive home.

That night I masturbated twice to visions of my wife and her co-worker, my thoughts filled with visions of Cheryl's sexy dress bunched around her waist as Thomas thrust himself into her. I had met Thomas several times and I remembered him as a tall, handsome man of about our age and I could understand why my wife might find him attractive. It was almost 1:30AM when I eventually received a call from Cheryl and I immediately headed back to the city to pick her up outside of the hotel. I found my wife waiting out in front of the hotel, tipsy and disheveled while sporting a very satisfied smile. On the drive back home, Cheryl told me how Thomas had been all over her the entire evening and they'd ended up in a room at the hotel that another co-worker loaned to Thomas for an hour. My wife said it was kind of embarrassing for this other guy to learn that she was sleeping with Thomas, but when he handed the room key to her lover, she practically dragged Thomas up to the room, her sexual hunger prevailing over any sense of propriety.

Cheryl and Thomas fucked once in the hotel room and then after returning the key to their smirking colleague, they found themselves in the backseat of Thomas' car, where they fucked once again oblivious to the comings and goings of cars in the garage. Upon our arrival back home, I buried my face between my wife's legs, scouring out Thomas' loads before masturbating for a third time that evening while Cheryl described how Thomas had brazenly fingered her at one point during the party.

My wife's affair with Thomas ended not too long after the Christmas party, but over the next year or so, Cheryl utilized our new "don't ask, don't tell" policy on a regular basis. Once or twice a week my wife would return home from work late and I'd wonder whether she was just having drinks with her co-workers or fucking some hung stud with whom she was having an affair. My wife did keep me apprised of her dates with the Gym Guy and the Fireman but other than those two men, I was in the dark as to any other of my wife's lovers. To be honest, there was an erotic aspect to Cheryl's secretive behavior and more than once, I'd go down on my wife upon her return home only to find a freshly fucked pussy, evidence of my wife's infidelity. But with our new arrangement, I'd say nothing, pretending that I was unaware that Cheryl had been with another guy. Instead, I would dutifully cleanse my wife's pussy and then masturbate quietly once Cheryl had fallen asleep. And although I very much missed my participation in Cheryl's pre-date preparations and post-date welcome home, I was committed to letting my wife enjoy her clandestine affairs if that's what she really wanted.

Lo and behold, to my surprise and delight, Cheryl eventually seemed to grow tired of sneaking around and more and more she began keeping me in the loop. And late one Friday night after I had licked and sucked my wife's obviously well-fucked pussy, my wife giggled, "Do you want to know who I was with?"

*Yes!", I exclaimed as Cheryl told me that she'd had a date with a guy she'd been seeing for the past month. That night, my wife filled me in on all the naughty details of her date as I happily masturbated beside her. And when I eventually climaxed, Cheryl let me know that she missed sharing her dating life with me. Whether it was my doting attention during date preparation, or my furious masturbation sessions listening to her naughty tales, Cheryl had decided that sharing everything with me, was something she'd come to enjoy. And as we kissed and held each other tightly, my wife told me that while she still wanted to reserve the right to have future clandestine affairs, she wanted to go back to keeping me in the loop with respect to her dating.

If there was one thing that I had to adjust to during this stage of our marriage was that making love to Cheryl was not going to be a regular occurrence. Given my wife's steadfast rule regarding sexual contact before her dates and with Cheryl's frequent dating, I was essentially denied access to my wife's pussy. At first, it was frustrating to be seemingly the only man denied sexual intercourse with my wife and after several months with no sexual contact between Cheryl and me, I brought up the subject one night as we were preparing for bed. "Honey, you know it's been a while since we last had sex", I whined when I saw Cheryl pull on one of her old flannel nightgowns, my wife's choice of sleepwear when she clearly had no interest in romantic activities.

"What do you mean? We had sex two nights ago", replied Cheryl while giving me a surprised expression. Now, the "sex" we'd had two nights ago had consisted of me licking and sucking my wife's well fucked pussy upon her return home from a date with the Fireman, followed by my feverish masturbation session as Cheryl described her evening.

"No, I meant we haven't made love in months", I groaned as I looked at Cheryl hoping for some sort of recognition of my concerns.

'Aw, Mike. You don't think I'm neglecting you, do you?", cooed my wife as she reached over and laid her hand on my cheek.

I was anxious not to make a scene as I answered, "No, no, it's not that. I just thought that since you're my wife..." I let my statement hang there for a bit, hoping that Cheryl would understand that as husband and wife, she and I should at least make love occasionally.

My wife didn't seem to get what I was hinting at as she asked, "But I thought you liked playing with yourself?"

"I do. It's just that I thought that maybe you and I should make love sometimes."

Cheryl looked at me sympathetically, seemingly finally understanding my concerns. "Okay, I get it. But I've got a couple of dates lined up over the next week. How about next Sunday?"

Now I suppose I should have been offended that I had to make an appointment to make love to my own wife, but beggars can't be choosers as I enthusiastically agreed that we would set aside the following Sunday to make love. And that night I slept well, not so much because I knew Cheryl and I were planning to have sex, but more so because I'd finally voiced my concerns about our lack of traditional sexual contact.

As it turned out, Cheryl and I didn't make love that Sunday as she received a response to her ad from an out of town businessman who she described as "so handsome." This guy was only in town for a couple of nights and so I agreed to take a rain check on our planned encounter. Cheryl spent Sunday afternoon and night with this guy and then headed directly to work from his hotel room in the city. My wife returned home Monday evening and announced that she'd had a "great time" with the "Boston Guy."

Cheryl seemed tired that evening so I didn't pester her to make love but the very next evening I picked up some salmon and French Chablis on the way home from work intending to fix a romantic dinner, hopefully as a prelude to making love to my wife.

Dinner went off without a hitch and throughout our meal, Cheryl teased me with little tidbits of information about what she'd done with the Boston Guy. By the time I'd finished clearing the table, I was already sporting a semi-hard erection and when I joined my wife in the living room for a final glass of wine, I couldn't help but embrace her in a passionate kiss. After making out on the sofa for several minutes, I was soon escorting Cheryl up to the bedroom where I then undressed my wife and eased her onto the bed.

Cheryl looked so beautiful lying naked on our bed and I knew I had a decision to make. Should I go down on my wife, licking and sucking her delicious pussy, or should skip my standard prelude and slip my now, rock-hard penis into her pussy? I knew which of these options was most likely to give my wife an orgasm, but Cheryl seemed so aroused, so wanton, that I threw caution to the wind and lay down on top of her and eased my penis into her juicy pussy and began to thrust in and out.

Unlike the Boston Guy's marathon performance that Cheryl had described earlier during dinner, true to form I lasted no more than a minute before I blew my load. "I'm sorry, Sweetie", I whimpered as my wife consoled me, telling me that everything was okay and that she'd enjoyed herself even though she didn't get to come. And when I offered to lick her pussy, overcoming my typical reluctance to eat my own sperm from my wife, Cheryl said that she was fine, telling me she was kind of tired anyway. That night I realized that perhaps I should be primarily restricted to masturbation. And over the course of a very sleepless night I mulled over my predicament.

My mind was reeling all night long as I contemplated my pitiful sexual performance. When she first confessed that she'd been cheating on me, Cheryl had not tried to sugarcoat the fact that sex with most of her other lovers was far better than with me. And over the course of her relationship with the Colorado Guy, my wife had made no secret that he rocked her world in the bedroom in a way that I never could. Now, with Cheryl seeing a variety of different men, it seemed that pretty much all of them had the skills and attributes to provide my wife with the sexual satisfaction she clearly needed and deserved. I suppose that most men in my position might try and up their game in the bedroom, instinctive male competitiveness motivating them to try and outdo their wives' lovers. But for me, I guess I'm a natural cuckold since, instead, I resigned myself to the fact that sex between me and my wife would never be "incredible", "amazing", or "fantastic", but, instead, might be, on a good day, best described as "okay", or truthfully, "mediocre."

Over the course of the next several months, it truly sunk in that I could never compete with the likes of the men that Cheryl was dating and fucking. I knew that if my wife and I were to make our marriage work, I needed to learn to truly accept that I was not meant to be the kind of man who is confident and assertive in the bedroom and who can take a woman to the heights of pleasure. Instead, I was best suited to be a faithful cuckold husband, a man who accepts his sexual inadequacies and who supports and encourages his wife to obtain sexual satisfaction elsewhere. I can't say that accepting my innate cuckold nature came easily or quickly and even to this day, at times I still question why some men like me are naturally cuckolds and others studs, or "real men" as my wife often refers to them. But once I accepted that it was fruitless to try and measure up, both literally and figuratively, with Cheryl's lovers, I gained a sense of inner peace at the direction we'd taken in our marriage.

As I began to understand that I was destined to be a cuckold, my frequent masturbation sessions, fueled by my wife's scandalous tales, were essential in allowing me to realize that perhaps this unique lifestyle truly could work for Cheryl and me. Knowing that other, more capable men, were providing my wife sexual satisfaction was not just arousing, but also, in many ways, a welcome relief. I could ignore my insecurities regarding the size of my penis, my stamina or my sexual skills and instead be secure in the knowledge that my wife was enjoying a sex life that would be the envy of most women.

And as odd as it sounds, lying in bed next to Cheryl, the taste of her pussy and her lover's come still fresh in my mouth as I masturbated to tales of her exploits was surprisingly fulfilling. With no pressure to perform, I could revel in my wife's naughty stories and when I would eventually come, my semen spilling out on to my hand and stomach, I would invariably look to my wife who would be gazing at me with an approving smile. At those moments, my love for Cheryl knew no bounds and it was this love that carried me through many a lonely night and weekend when she was out with other men.