The Bet – How my cuckold marriage began

I have some inspiration from a recent post that received good feedback, so I’m trying a new story with similar themes. I hope you enjoy.

Kinks include: cuckolding, denial, chastity, submission, sharing

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My hookups are often curious how my husband and I got into cuckolding. I usually just say that we were always like that, which is true but that’s not the whole story. The most interesting part is that our relationship in fact started because of a bet.

Years ago we were just roommates sharing a small two bedroom apartment. People thought we were a couple or something but no, we were just roommates. Heck, we hardly ever saw each other back then. Neither of us seemed well suited for serious relationships, preferring instead casual sex with an endless rotation of one-night-stands or friends-with-benefits. We’d talk openly about who we hooked up with and occasionally bragged about a recent hookup. Funny enough we never actually had sex with each other until one day I complained about how frustrated I was that I hadn’t cum in weeks because my last few hookups all came too quickly. “Two weeks of sex without coming is nothing!” he laughed. We argued back and forth until finally I demanded he prove it.

The terms were simple. We’d have sex no more than once a day for 2 weeks where I could orgasm if I wanted but he couldn’t. He even offered to wear a chastity cage in between so I was sure he wouldn’t cheat. If he lasted the entire two weeks, I agreed to be his personal fuck toy for a whole week. Outfit, ropes, toys, on his command. I’d even buy myself outfits that he got to pick out. But if I won… If I won he had to stay locked and denied for an entire month. No sex, no masturbation, no orgasm. Total denial.

He bragged about his endurance and how easy this would be. He said he could EASILY have sex regularly for two weeks without finishing. I almost believed he could do it.

To be fair he handled the first few days pretty well. He was in great shape, he was a few years younger than me with an athletes physique. He was handsome, just out of school with a good job, and had an impressive sexual history for a guy. He was a little nerdy, and as I discovered, definitely on the smaller side. But I couldn’t deny his stamina was damn impressive. Sometimes I’d leave to go for a walk while things got intense with a girl he had over, and often they’d still be fucking when I got back. What he lacked in size he most certainly made up for in endurance. Plenty of his hookups came over several times so I figured he was doing something right.

He was confident the first few nights, and it was amazing to be with a guy who could take control and make me climax without needing to be told what to do. But after a few days his demeanor started to change, he seemed nervous and more serious. Near the end of the first week he was wincing and breathing heavy, barely holding back as I rode his cock to my 2nd orgasm. “You are so staying locked!” I boasted with a huge smile. At the end of the week I noticed he used a different condom, when I checked the wrapper it was one of those “endurance” condoms for premature ejaculators. We were only half way through and he was on the verge of loosing.

That’s when I decided to put him out of his misery and win that bet. I gave him a sporting chance, like a hunter letting his prey get a head start. For the next few nights I told him I wasn’t interested in fucking and he had the night off, he seemed relieved if anything. Then I made my move. A week and a half into our bet he came home to find me dressed in a skimpy Halloween costume I picked up on discount, a slutty maid outfit. I was pretending to clean the living room when he walked in. I pushed him to the sofa “I don’t have time right now” he tried to delay, but I insisted it be now and reminded him he already had a few nights off. He sat on the sofa and I undid his pants and helped him strip down to his caged manhood. I played with his desperate cock as I kissed his neck and rubbed my breasts against him before finally removing the lock and admiring how his cock jumped to attention like a well trained little soldier. I stood up and dropped my underwear as he pulled out a condom and rolled it on. Then I straddled him and reached down and wrapped my hand around his rock hard cock and peeled off his condom and sat myself down on his cock.

“What are you doing?” he exclaimed and held me still with him inside me. “Is something wrong?” I asked innocently. “I can’t… without a condom.” – “Oh?” In inquire “You always said how much you hated condoms and prefer not to use them.” He stumble on his words, not sure what to say as I start gyrating my hips. I feel him try to hold me still, he had a strained expression on his face. Then I lean in and whisper in his ear. “You loose…. just admit it. It’s been 10 days and you are about to explode like some overeager teen virgin.” I try to bounce on him and he does his best to hold me still.

“Okay.. okay OKAY! What do you want?” he asks as his whole body is tense. “What do I want?” I ask confused. Even now he’d rather concede than finally orgasm and give me the satisfaction of breaking him. “I just want you to admit you couldn’t do it, and admit I won.” He looked defeated, that cocky confident spirit I knew well had evaporated. It was kind of sad actually. “Okay fine. I can’t do it.” I feel him start to relax but the moment I go to move he holds me still again. Finally he releases his grip on me when he realizes I was going to climb off him and accept victory.

And that’s how his servitude to me started. It turns out he couldn’t even handle one month of denial. After another week he begged, BEGGED me to give him back the key and suggest another punishment, anything. Then one day I offered that he could cum, but in exchange he’d have to lock up for another 3 weeks afterwards. He agreed instantly, the opportunity to finally orgasm was too attractive. By that point he had already been denied almost 3 weeks, I don’t blame him honestly, but I was surprised. I released him and watched as he got hard and came almost instantly. The look of embarrassment on his face when I laughed at how quickly he came… I’ll never forget that.

He never did make it those 3 weeks and soon again begged for mercy and accepted yet another spell of denial in exchange for immediate release. This repeated for several more months until he was stuck in an endless cycle of desperation and denial, until finally I took pity and offered him a deal. I hadn’t had a good fucking in weeks, and he hadn’t had sex in almost 4 months. So I gave in and released him. “Unlock yourself, I just want a good fuck. Okay? It’s done.” and I gave him his key.

I’m not sure what happened afterwards, but when we went to have sex he came before we even started. He was so embarrassed and apologetic, and when we tried again the same thing happened. After that he was in a panic and it felt cruel to mention he didn’t even finish his last 2 weeks of denial. The next day he asked hesitantly if we could try again, but every 10-20 seconds he would stop while I would beg him to just keep going, he came after a minute. That superpower endurance he boasted about was destroyed “Nobody wants to fuck a tiny guy that cums quick” he admitted with total defeat almost in tears. When I saw him later that day he was caged again, voluntarily. “Your key is on the bathroom counter” he said sadly as he went to his bedroom.

After that we stayed really close. I kept seeing other men, and occasionally depending on my mood I’d give him his key so he could relieve himself. We never had sex again, but I know he would stay in his room and listen in when I had somebody over. We’d even sometimes discuss how it was and he even began to judge my hookups from the noises he heard from his room. One of my hookups though he was my cuckold boyfriend since he’s always around and seems to relish hearing about my sex life in the total absence of his own. We were already so close and we never really wanted a serious relationship, but our dynamic felt pretty perfect so we got married.

We’ve been married for 10 years now and we’ve never actually had sex as a married couple. I still surprise him his key every once in a while, but he long ago stopped asking to be let out. In fact, I think the last time he saw me fully naked was on our wedding night, I never wear less than underwear when he’s around.

How does that old saying go…. *You break it you bought it.* Well I broke it.

Source: reddit.com/r/eroticliterature/comments/t9hehf/the_bet_how_my_cuckold_marriage_began