Wife fucked from lost bet and Lost chastity bet to bull

[ticklemang]

Anyone have stories about losing bets with their bulls and getting some sort of punishment for it?

I think the bet scenario is super hot and its happened twice to me where I lost the bets and faced the consequences. My wife is named Emily by the way

A few months ago, we were hanging out with a long time friend of Emily’s, a guy named Derek. They used to be friends with benefits before we dated, but at the time they were just friends. I never really asked Emily any of the details about their relationship, but I know it never went anywhere because she didn’t really like him that much in a relationship context since he was arrogant and kind of an asshole, but he was interested in dating her. They fucked for about 6 months until he ended up getting a girlfriend, and Emily called it off, even though he wanted to keep fucking her.

Anyway, we were all hanging out and drinking a little and he and I were playing smash on the switch. We were getting competitive and had been drinking a little bit and decided to do some bets on the outcomes of the games. At first it was like $20 or the loser had to go to the ground floor of our apartment and talk to the chatty receptionist for 10 minutes. Emily got in on some of them like the winner got to massage her feet, the winner got to see a sexy picture of her that nobody else had seen before.

Finally, we were pretty drunk and the bet escalated to one where if Derek won, he got to fuck Emily again, and if I won, I got to have a no safeword session with her where I tie her up and do whatever I want to her (it would be foot tickling for sure. I have a huge foot fetish and tickling fetish, and she’s super ticklish so she doesn’t really let me that often.

I probably wouldn’t have agreed to this, but like I said, we were all pretty drunk. So I had won most of the bets so far, except notably the one where Derek got to see the lingerie picture of Emily that she hadn’t shown me, and like one or two others, so I was feeling pretty confident.

But during the match, Emily had her hand in my pocket and was playing with my penis and balls, gently stroking them until I got hard, then basically jerking me off through my pocket. So my early advantage was lost, and I kept it even until about halfway through, when she started whispering things in my ear about how I better win, and think about all the fun I would be able to have with her, basically using my fantasies to get me even more horny. And then she started rubbing her bare feet on the inside of my thigh, and it was so distracting that I even glanced down in the middle of the game. So from that point on, I was behind and couldn’t recover and ended up losing.

So then Emily whispered in my ear that I wasn’t allowed to cum while she was with Derek, and he carried her off to the guest bedroom for them to fuck.

And basically he fucked Emily doggy style for like 30 minutes and made her cum like 5 or 6 times. She was super vocal and moaning the whole time, and according to her, he fucks her so good and she was already soaking wet before he even stuck it in her.


So that's the story of how Emily got her current fuckbuddy. The next time is probably more interesting to all of you guys. Basically Derek has been fucking her ever since, probably about once a week or so, and Emily says he brings her to earthshattering orgasms because it feels so naughty. Derek also has a foot fetish and likes to tickle her feet too, so that makes it even hotter for me. Emily also likes to play with orgasm denial for both me and her, but Derek is not into having his orgasms denied, so he’ll just do it to her while they fuck, holding out on making her cum until she’s begging him, and he just keeps teasing her clit with his dick, or he’ll be fucking her and then stop to worship her feet or make her suck his dick. A few times he’s even denied her until she cries from frustration, which I love doing to her as well.

When me and her have sex, we do similar things to each other, teasing and denying, she gives me long footjobs, I tie her up and eat her out for an hour straight, that kind of thing. My penis is a bit smaller at 4.5 inches, so I can’t fuck her as good but I can still pleasure the shit out of her, and she loves teasing me too.

Anyway, one thing about Derek is that he’s kind of a jerk and pretty competitive. Emily finds that attractive because she likes to see me compete over her, and its also a good match because it minimizes the chance of her actually falling in love with him.

But lately he’s been teasing her during their sex and saying he’s not going to let her cum until she agrees to deny letting me into her pussy. One time she was tied down and she begged to cum for 45 minutes, and the whole time he was saying he would only let her cum if she denied me her pussy, and she told me she had never been so frustrated in her life, because he would have her right on the edge and do 5 thrusts of his penis into her and then stop, and repeated that the whole time, even while she cried and begged to cum (she didn’t safeword though, she likes it) and then finally he made her cum.

But one idea Emily has had and wanted to try out, which I have said no to, especially since Derek came into the picture, was me getting locked in chastity. It sounded fun, but I am used to cumming every day, sometimes twice from my beautiful wife, and wasn’t going to give that up.

But one day while Emily was teasing me with her feet in my face, using a makeup brush to tease my penis, she told me that Derek had been speculatively talking shit about how long I could last in bed. That kind of pissed me off because I had no issues lasting in bed, and she told me he had challenged me to see who could last longer under Emily’s hands. I said I would take that bet for sure, but then she told me that she wanted it to be a real bet with real stakes, and here’s what she proposed.

If I won, I would get the opportunity for a no safeword session with her tied however I wanted for however long I wanted. I still haven’t ever done this, so this is an enticing offer for sure. But if I lost, I had to be locked in chastity, and she would decide when I got unlocked, and when I would get to cum.

I was hesitant to take the bet, but her feet were in my face and she started talking about how I could do whatever I wanted to them. That, combined with the fact she had been teasing me for like 30 minutes at this point, and she popped my penis in her mouth and started using her tongue to tease me. After a few more minutes of that, I agreed to the bet.

She asked me if I was sure, and said she would text Derek to confirm it. I hesitated for a second, but she started sucking me again and I agreed. She sent the text and then I exploded into her mouth a minute or so later. This was on Wednesday, and the bet was to take place on Saturday

Friday, I didn’t get to cum because while Emily was teasing me after I had gotten her off, she got what she told me was an important call and had to go, and she told me she would be back later to finish me off, but she got back too late and we both just ended up going to bed.

So Saturday, Emily and I spent the day together, and in hindsight, she was doing her best to tease me all day. She would rub her feet on my dick, she was wearing sexy lingerie, she even got on her knees in the middle of the kitchen and sucked my dick for a moment until I stopped her.

The time came for the bet to happen and Derek showed up at our place and made some comment about him definitely winning the bet, and I replied something about how he shouldn’t be so sure about that. Anyway, after that we got right down to business. The rules were, if you were going to cum, you had to announce it and whoever announced it first would lose. Emily took both of us into our bedroom, and we stripped and laid down on our backs on the bed, and Emily sat between us. Then she put coconut oil all over her hands and started stroking both of us until we were hard. That was the first time I saw Derek’s penis, and it was way bigger than mine. Apparently it's about 7 inches, and it's also about twice as thick as mine. I saw it and realized that it has been going into Emily for months now, and my jaw almost dropped but I kept it together because I didn’t want to show any weakness.

So then Em started stroking both of us, slowly at first, and then at a medium pace. We were both concentrating on not cumming under her soft hands. Since my penis was shorter I think she would stroke it more times at the same speed as Derek, and she also started adding in twists right under the head of my penis, which drives me absolutely crazy. We were both struggling a bit, moaning and thrusting into her hand after about 15 to 20 minutes. Then, I felt the sole of her foot rubbing on my face. I tried to turn away, but she put it on my chest and touched it to my mouth. Then she started adding more twists to her handjob and I felt myself about to cum, so I announced it and she stopped stroking both of us. Frustrated with the outcome, I claimed that Emily had cheated by putting her foot in my face and giving me a twist under the head of my penis.

She said I was being a sore loser, and she did the same to Derek, I just wasn’t looking at him, and Derek corroborated her story too. Then Em climbed on top of me and started grinding herself on my penis and making out with me, and she kept whispering in my ears how bad she was going to tease me and how Derek was going to get her pussy way more often than me now, which turned me on even more.

Then, she went into the closet and pulled out a box that had the chastity cage in it. She had already taken my measurements once before when she wanted to try out chastity and ordered a custom fitted one. It was metal and had spaces between the bars, which she said was perfect for teasing.

I asked her to at least let me cum before locking me up, and she gave me a teasing grin and said nope. Then she put the ring around my balls and pushed the top of it down on my penis, applying pressure until I went soft and then she closed it around me. Then she sucked it for a few minutes through the cage, which was super intense and I was trying to get hard the whole time but I couldn’t.

She told me that she was going to let me out every day for teasing, and on Saturdays, she would let me cum, and I tried to protest, but she grabbed Derek and took him to the guest bedroom to get fucked.

I listened to them fucking and the whole time my dick was trying to get hard in the cage and also leaking precum everywhere. They had their regular tease and denial sex for my wife, and Emily was super horny right at the start. After a while she started begging to cum, and he would deny her as usual, and then she started saying she his good girl over and over while she was begging to cum.

And after a while he asked her whos cum she was going to take the most and she said his, and then he made her say that big dicks get to cum on her and little ones stay denied. And then he let her cum, and he kept rubbing her clit all the way through, overstimulating her (she’s into that too) and she was basically screaming the whole time. Shortly after that, he came on her.

Then they got cleaned up and he left. After that, she and I had a TWO HOUR tease and denial session where she tied me up and took my cage off, and teased me with everything in her arsenal the whole time, before locking me back up.

And that week, she teased me every night for at least 30 minutes, and I was losing my mind with horniness. I absolutely could not take it, and she went to see Derek 3 times that week to get fucked, including on Saturday. Then she came back and teased me again on Saturday for about an hour.

She had her feet on my face and was teasing my penis while I was tied up, and she told me Derek loved that I was locked in chastity and he got to fuck her pussy more than me, which made me even hornier, and she also came clean that the chastity bet was his idea, which I had surmised at this point, but she had denied over and over.

She told me that one time he was fucking her and not letting her cum while she was tied up and she just couldn’t take it, and promised him that she would do her best to get me in chastity, since she wanted that too. Then she told me that she loved teasing me so much and while Derek was fucking her she would just think about how horny and frustrated I was for her. Then she said I could cum for her whenever I wanted to and started stroking me harder and faster.

And she told me about how good he fucked her that day, and how he came all over her feet, and that visual was too much for me and I exploded all over myself while she kept stroking me in the most intense orgasm I’ve ever had.

So the next week was the same thing, but the Saturday after she had me tied up and was teasing me with her makeup brush and feet for an hour again. And this time, she kept going so slow and was asking me “Do you want to cum for me baby, do you want to cum for me?”

And my cock was so swollen and twitchy and leaky and I just couldn’t take it anymore after the whole week of teasing by her. I kept saying yes and begging her to let me cum, but the brush just wouldn’t take me over the edge. And finally, she told me that she promised Derek she wouldn’t let me cum this week. She said he teased her too much and she couldn’t take it anymore and she just promised him.

My eyes opened wide and I begged her, please baby let me cum, I can’t go another week like this! You don’t have to keep the promise, he’ll never know!”

But she looked at me with a sympathetic smile and told me a promise is a promise and moved her feet so they were the only thing I could see. And after that she kept teasing me for so long, I was beside myself with frustration, and that’s the first time I actually cried from being so horny and frustrated.

She let me cum the week after, but the week after that she withheld my orgasm again.

Now she’s saying that Derek is trying to get her to agree to only let me cum when he says so. That idea is exciting but super scary to me too because Derek is definitely more sadistic than her and likes seeing that I’m frustrated and denied release.

When she told me that, I begged her not to agree to it, but she told me she wasn’t sure how long she could hold out. She said they might be able to come to a compromise, like changing my schedule to every 2 weeks or even every month. I begged her not to agree to that either, even though the idea is definitely exciting to both of us.

She just told me she’s not sure if she can resist his teasing forever, and I might have to come to terms with cumming less frequently and being more horny all the time.

[ticklemang]

But yeah post any stories you have (real or fictional) of cucks losing bets and getting some sort of like chastity punishment or something from it, that’s really getting me going right now. Emily even will read them to me sometimes while she teases me or have me read them to her while I’m teasing her

[NSEW1]

There is an entire novel including such scenarios called the Unwanted Houseguest - The Epic Cuckold Sequel.

[Cuckcuckgoose1]

Hot story but...who is Daniel?

[ticklemang]

Hot story but...who is Daniel?

Haha, sorry I switched the names for this story and couldn’t remember the D name I chose for a second. Changed it back

[user322]

Wow, your story is really excellent, I hope you will keep us informed!

[ticklemang]

The story is after my previous one, and it was on a Saturday. I hadn’t been allowed to cum for a week by Emily, who has tease and denial as one of her main fetishes. She loves doing it to me and she loved having it done to her as well. Like I said in the previous post, she’s always wanted to get me into chastity, but I was too scared to try it until I lost that bet and I had to. And since she’s gotten me locked up, she’s been edging me every day and only letting me cum on Saturday after even more edging.

A little more backstory is that last Saturday when they fucked, Derek got Emily to agree to not cum for the whole week until next time. Usually I edge her and make her cum every day, but for this week, I just edged her. I remember one time she was making me breakfast and not wearing any panties, and there was a drop of wetness just hanging out of her pussy she was so horny. So by the time Saturday rolled around, both she and I were insanely horny from a week of tease and denial. I was teasing her when Derek arrived, and she was soaking wet, literally leaking down her leg.

So then Derek shows up and she’s telling him to fuck her and get it over with already, saying she can’t take it anymore and she’s so horny, and Derek says he’s not going to fuck her unless she lets him tickle her feet while she’s tied up. And usually she refuses this request for both of us because her feet are so ticklish, and she just can’t take it, but that day she was so horny she just agreed to let him. When she agreed, my eyes were bugging out of my head and my cock was leaking and twitching in the cage just thinking about it. I love her perfect little feet and I always want to tickle them but she usually doesn’t let me, so it was an extra mind fuck.

He gets her tied down and starts fucking her slowly, not letting her cum, and shes going crazy, begging him to let her cum right away, but he just keeps going and since she’s tied up, theres nothing she can do to stop the edging on his cock. After about 20 minutes of listening to that, I hear him start tickling her, and she’s laughing her head off, begging him to stop and saying she can’t take it. I won’t go into too much detail here because not everyone has a tickling fetish but long story short it was super hot and I leaked everywhere listening to it.

So at the end of the tickling, she’s promising to do anything for him to stop it, and then they come to a whispered agreement that I can’t hear, and then it goes back to him edging her on his cock. After about 30 more minutes, he lets her cum, and then unties her and she finishes him with a footjob.

And after that, she comes out and climbs on top of me, making out with me and teasing me through the cage, and then she starts sucking my penis through the cage as well. And its one of the metal ones so you can feel everything between the gaps so she was driving me crazy.

And then she asks me if I want to cum for her after listening to that all happen, and I’m ravenous so of course I say yes, please make me cum I can’t take it any longer.

Then she tells me that in order to stop the tickling, she agreed to cancel my orgasm this week, and I’ll have to wait until next week. And I let out such a frustrated sound that Derek laughs (he’s an asshole so he loves convincing her to deny me so I have to be extra horny in my cage)

And of course I’m in such a horny state I can’t think straight and I’m trying to cut a deal and she takes the opportunity to ask me if I want to make another bet.

So I say yes and suggest whoever can take more edging before saying they can’t take it. And the stakes are if I win, I get to cum this week and if Derek wins, I don’t get to cum this week or the next week. And I was so sure I’d win because I get edged all the time, but I forgot to take into account how horny I was. I just spent the whole week in the cage getting edged every day and also listened to them fuck and her get tickled.

She takes me into our room and puts her feet on my face and starts giving me an intense handjob, much more than the usual light teasing she does to edge me. And she has this mischievous look on her face like she knows I’m going to lose and she’s going to do everything she can to make sure I lose. She’s using the technique I love where she twists her hand right under the head of my penis, and all the while she’s telling me about the ways he tickled her feet and how she was so helpless to stop him, and saying how horny that must have made me, and keeps talking about the tickling. And then she tells me to go ahead and tickle her feet a little bit, so I do, which only makes me more horny.

I just keep getting edged over and over from the combination, and she also keeps teasing me saying I better hang on, or else I won’t be able to cum for 2 more weeks, and she’s going to tease me so bad for those two weeks, and she’ll miss her little guy’s cumshots on her feet.

And with all the teasing she was doing, and me tickling her feet, I was only able to last about 30 minutes of edging before I was begging her to stop saying I was going to cum if she even touched me one more time. Then she re caged me and took Derek back into the guest bedroom and edged him for 30 minutes until he beat my time, and then they fucked again.

He left after that and she unlocked me again for more teasing, this time with a makeup brush, and I was begging her to let me cum but she didn’t. And so I stayed teased and denied for 2 more weeks after that, 3 weeks total, and at the end of the three weeks, I had the most intense orgasm from getting a tickling footjob from her.

[Dream Weaver]

Apparently it's about 7 inches. Well, you saw it right? Is that your guess? Or did you have another source?

The library is a good spot for story requests.

[ticklemang]

Apparently it's about 7 inches. Well, you saw it right? Is that your guess? Or did you have another source?

The library is a good spot for story requests.

7 inches is what Emily said, Derek claims it’s like 8.5. I’m not super good at telling size down to the inches, it looked about double mine, maybe a bit less, and I’m 4 inches rock solid

[ticklemang]

A while back, he got the idea somehow to make me wear a penis sleeve while fucking her. Apparently, he brought up the idea to her, but she said no to him at first, thinking it would be too cruel and there’s no point, since she can get a bigger dick whenever she wants from him. He told her it would be for if she needed a good fucking and he wasn’t available, so she didn’t think there was a point. But in reality, he just wanted her to make me use it so I couldn’t get the pleasure of fucking her.

But he went ahead and bought one that was the same size as his penis anyway. Next time he was going to have her come over and get tied up for an edging session, he told her to have me start it off by edging her with my mouth for about 30 minutes before she went over, so I did, getting her right there and holding her on the edge for a while until she had soaked all over our bed. Then at his place, he tied her up and continued it with his cock. Emily loves tease and denial, and Derek uses his cock, slowly thrusting it in and out of her, stopping when she’s right on the edge for a few seconds. This time, he edged her over and over, not letting her cum until she agreed to try it out, and if she liked it, then she would have to make me use it more often.

She says she held out for some time, like 30 to 40 minutes, but eventually she couldn’t take it anymore and agreed to try it out.. She didn’t even tell me this story until a few days later when she brought the sleeve out and had me try it on.

So anyway, after Derek convinced Emily to try it, she came home that night and didn’t say a word about it to me. Instead, she just teased me like usual. She unlocked my chastity cage, tied me down, and edged me with her feet and hands for an hour or so before locking me back up without letting me cum. It was not until a few days later, on a Saturday (which was usually my release day, but she had been denying me more often thanks to Derek's influence), that she finally brought it out.

We were in the bedroom, and she had already edged me for a bit with her makeup brush, getting me all worked up and leaky. My balls were full and aching after a week of denial, and I was begging her to let me inside her. That is when she pulled out the sleeve from the nightstand drawer. It was this clear, soft plastic, molded to look like a realistic cock. It was about 8 inches long and girthy, just like Derek's. She explained the whole story then. She told me how Derek had bought it, how he had edged until she agreed to make me use it, and how she was curious now if it would feel as good as the real thing.

I was humiliated just looking at it, knowing it was essentially Derek's way of making sure I could not even enjoy fucking my own wife properly. But I was so horny from the edging that I did not protest much. Emily had me slide my penis into the sleeve. It fit snugly around my 4 inches, but I only filled about half of it, leaving this big, empty extension. Additionally, it was way thicker than me, having a bunch of material on either side. These two factors combined made the size difference very clear. It was heavy, and pulled my erection downward, as my penis didn’t really have the leverage to keep it upright. The inside wasn’t textured at all, but it was designed so that once it was on, I could thrust, but couldn’t feel her warmth or tightness at all. It was like wearing a numb condom on steroids.

I protested against having to use it, but she told me she had promised him, and she didn’t like breaking her promises. She knelt in front of me, holding it in her hands, and told me it was heavier, just like his, before she had me lube it up and get ready to use it on her, teasing me about how much bigger it was than me.

She lay back on the bed, spreading her legs, and guided me in. As soon as the sleeve entered her, her eyes widened, and she let out this deep, throaty moan. "Oh fuck, baby, that's amazing," she gasped, her hips bucking up to meet it. I started thrusting, but I could not feel a damn thing. It was just the pressure of the sleeve around my own cock, but none of her pussy's grip or wetness directly on me, and my penis didn’t even slide around the inside of the sleeve. It was the ultimate mind fuck. Here I was, finally inside my wife after a week of denial, but I couldn’t feel anything at all. She was getting all the pleasure from this fake extension, and I was just the engine driving it, humiliated and frustrated.

Emily went absolutely crazy for it. She started writhing under me, her hands clutching the sheets, moaning louder than she ever does with me alone. "Yes, yes, fuck me with that big cock. It fills me up so good, just like Derek's." She would arch her back and grind against it, her pussy clenching around the sleeve in ways I could see but not feel. She came hard the first time after just a few minutes, screaming and shaking, her juices soaking the base of the sleeve. But she did not stop there. She begged me to keep going, to fuck her harder, deeper. "Don't stop, baby, make me cum again. This is what a real dick feels like." It was humiliating to hear her say that, knowing I was the one doing the work but getting zero sensation from it. My own cock was throbbing uselessly inside the sleeve, trapped and denied any real pleasure, while she was lost in ecstasy, cumming a second time even louder, her whole body convulsing.

Then, as she was riding the high of that orgasm, she lifted her legs up high, bracing them on my chest so her perfect, feet were right in my face. Her soft soles were inches from my mouth, toes spread teasingly. "Look at them, baby," she purred, her voice breathy from the pleasure. "You can look all you want, but no touching, no tickling. If only you were as big as Derek, you could play with them while you fuck me, just like he does every single time. He tickles my feet while he's balls deep in me, driving me insane, but your little guy just doesn't measure up. You'd have to stop thrusting to even try."

That did it. The combination of her words, the sight of her feet so close but forbidden, and the knowledge that Derek got to do all this for real, it was so arousing that even though I could not feel her pussy at all, I felt myself surging toward the edge. My cock twitched hard inside the sleeve, building up to what would have been an explosive orgasm. "Emily, I'm gonna cum," I gasped, my hips faltering.

Her eyes snapped open, and she immediately pushed me out of her with her hands on my chest. "You better not cum, because you're not allowed to," she said firmly, a wicked grin on her face. My penis kept twitching desperately in the empty sleeve, leaking precum, but without any friction or sensation, the orgasm faded away, leaving me panting and frustrated on the edge. I whimpered, begging her to let me back in, but she just laughed softly and made me wait until I was fully backed off from the brink.

Once I was not going to cum anymore, she pulled me back inside her with the sleeve and made me keep fucking her. I had to go through the whole thing again, thrusting mechanically while she went wild, cumming a third and fourth time, each one more intense than the last. She was a mess by the end, sweaty and satisfied, praising how "perfect" the sleeve felt, how it stretched her just right. Finally, after what felt like forever, she was done and pushed me off her.

She slipped the sleeve off my cock, which was still rock hard and throbbing, my balls heavy and full from the denial. "Aww, poor thing," she teased, tying my hands behind my back so I could not touch myself. Then she started the real torment: teasing and denying me with her hands and feet. She would stroke me slowly at first, building me up to the edge, then stop right as I was about to explode, letting my cock twitch in the air. "Not yet, baby," she would whisper, tracing just one finger along the underside of my shaft, from the base up to the head, then lightly circling my full, aching balls. It was maddening. The lightest touch kept me simmering but never over the top.

I would whimper and plead, "Please, Emily, let me cum. I need it so bad." But she would just giggle and start edging me again, faster this time, only to pull away at the last second. This went on for over an hour, edge after edge, her finger tracing those torturous paths on my cock and balls while I bucked and begged. My whole body was trembling, tears of frustration in my eyes, but she did not let me cum. Finally, she locked me back up.

Anyway, this was just the first time I had to use the sleeve a few months ago. Now, I haven’t even been inside her without it in almost as long. She makes me wear the sleeve every time we fuck now, before tying me up for an edging session after, and if I’m lucky, letting me cum or ruin with her feet in my face

[Centaure]

What a tease! Emily went expert on keeping you on the edge constantly.

[ticklemang]

What a tease! Emily went expert on keeping you on the edge constantly.

Yeah she has a tease and denial kink so she was already an expert at edging me before any of this happened

[TheHammer]

You should turn the tables a bit and buy a bigger sleeve and surprise your wife with it.