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Sorry if this is a long post. The story is true and ongoing. I hope this is the right place to share it.
I (25TF) was a wannabe cuck for years before my wife (26F) and I met, but none of my previous partners were interested. When my wife and I started dating, I made it clear that I was 100% cool with her flirting with, kissing, dating, and fucking other people outside of our relationship, and that she had no obligation to include me, reciprocate, share any details, or even tell me about it at all. I said this mostly because it’s a reflection of my real views about monogamy and sex, but I’d be lying if I said there wasn’t a part of me that was excited about the prospect of finally being with someone who might enjoy cucking me after fantasizing about it for so long. However, she made it clear that she didn’t really have any interest in sleeping with other people. I’m obviously not upset that my smoking hot wife only wants to have sex with me, but I relegated my intense cuck fetish to the realm of fantasy and assumed that any scenario involving my wife and other people would never come to fruition. It was an easy decision to make because I love my wife, but my kinks for cucking, humiliation, cum eating, and premature ejaculation never went away. In fact, they only got stronger as we dated for longer and I started having more vivid, detailed fantasies about her.
My wife is the hottest person anyone I know knows. She’s a 5’4″ kinky bisexual alternative asian woman with tattoos and piercings and a gorgeous face and an ass that makes peoples’ heads turn whenever we go out. One time she stood up and walked out of the room in her medical scrubs and a group of our mutual friends went silent before looking at me like I’d won the lottery or something. It honestly feels like I have. She’s funny and personable, generous and kind, always the best dressed person in the room, frequently wearing clothes she made herself. She’s the coolest. I love her so much. She considered camming before and I seriously believe that she could have genuine success as a porn star if she wanted, not just because of her looks and abilities in bed but because of her vibrant personality, work ethic, and business savvy. Her best friend of several years once asked if she could watch us have sex, and several of her and my friends have privately expressed to me how hot they think she is. She’s also (like me) a giant tabletop and board games nerd, which will become important shortly.
I’m pretty well endowed, girthy, and I’m good looking and give great head, so my wife never found herself in want of a more satisfying sexual partner. I’ve seen people say before that you can get your wife interested in cuckolding by orgasming early or being bad at sex on purpose to make her desperate, but that always seemed deceptive and cruel to me. I want my wife to cum. I work very hard to make her cum as often as possible and take pride in the fact that we have amazing sex. I don’t want her to have a bad time with me – I just happen to believe that she could be having even more fun if she expanded her pool of sexual partners beyond just me. The first time we ever hooked up she told me that I had the biggest dick of anyone she’d ever been with, and frequently mentions during sex how much she enjoys the size of my penis. I have a slightly above average cock, but it’s nowhere near as big as they can get, and the fact that my normal size dick turns her on so much makes me wonder how much of a size queen she might become if she started experimenting with larger dicks.
I hadn’t mentioned the subject of her sleeping with other people for about four years, assuming the standing orders from the start of our relationship still applied, but I brought it up again a few months ago because I started taking feminizing hormones and presenting in a more female way as part of my transition. Estrogen can make your penis smaller, prevent erections, and reduce the production of semen and sperm. Given that my wife is a burgeoning size queen with a breeding kink, I wondered if she might be interested in finding other people to fill that hole, so to speak, in case I couldn’t fuck or cum inside her the way I’ve been doing ever since our first date. For the first time ever, she told me that she’d genuinely consider it instead of giving a flat rejection. She left the room and I creamed my pants about ten seconds later.
The thing is, my wife wasn’t interested in finding a random stranger on the apps. She didn’t want to have to shop around and go through talking stages in order to find someone to fuck; it seemed like too much work just to get some good dick from a nice person. But just as I was starting to lose hope once again, my wife made a new friend.
We recently started a new D&D campaign with some strangers at a local bar. I was running the game and felt nervous about my wife getting along with people in a new social setting, and was thrilled to see that the whole group got along tremendously well, and that my wife was getting along especially well with one particular person. He’s tall, looks and behaves a little bit like me when I was still identifying as a man, but much larger in stature and build. Hot features, quick witted, friendly, mature, considerate, a real sweetheart but with a super cocky arrogant streak that I find really hot. I’m no psychologist but I know a brat tamer dom when I see one, and my wife loves acting like a brat for fun. I knew right away that they’d make a great match. He and my wife immediately made a corner of the table their ‘spot’, and I would frequently look over to see them smiling or laughing at a private joke together. They got along like a house on fire! It was a huge relief to see my wife enjoying herself, and the guy in question also happened to be lovely, sensitive, sweet, and constantly making dumb sexual innuendos which happen to be my wife’s favorite type of humor. I saw them hit it off immediately, but a few weeks later I mentioned to her that they seemed to be getting along really well and my wife basically shrugged it off, saying that she thought he was getting along like that with everybody in our group. I suspected otherwise but didn’t push it further.
After a couple months we starting hanging out with our new friend and some others at different events. We attended one particular show where my wife dressed up in a revealing outfit, and I thought it might be a good time to experiment with some very tame social engineering. When we got to the venue, I had my wife go ahead of me in line so that when we got to our seats she was seated between him and myself. They spent the whole show hanging out and giggling to themselves, and I could tell that they were both starting to crush on each other, even if my wife hadn’t realized it consciously yet. She starting bringing him up in random conversations out of nowhere, telling me about jokes he made. One time recently she was struggling to hear what I was saying over the phone, and when I told her what letter the word I was saying started with, instead of saying “oh, like M for mouse,” she said “Oh! Like M for [Mark]!” Whenever we were in large groups together, I’d watch where they looked when someone said something funny. He would always look right at her, and she would always look right at him. Having since heard both of their confessions about this time period, I’m pretty sure I knew they wanted to fuck each other before either of them did, and I gently began nudging them both in each other’s direction, talking to her about what a nice and helpful guy he was, thanking him for taking such good care of her during our games, and so forth. I kept it subtle. I knew it wouldn’t take much.
There was also the icing on the perfect bull cake: my wife recently took a new job that has her working from home almost exclusively, while I leave for work before she wakes up and frequently don’t get home until after nightfall. And what is our new friend’s job? He works a high-paying stable gig, completely remotely for a company in a different state. He works out of his apartment every single day – and his apartment is a ten minute walk from ours. It was like the stars were aligning, the fates letting me know that I was about to see the fantasies I’d been playing out in my head finally become reality whether I liked it or not.
I got nervous really fast as it finally sank in that my wife might seriously start taking the idea of fucking someone else seriously after so many years of devoted monogamy with me, that she might fuck him in our bed, and that she might really enjoy it. After years of jerking off to the thought of my wife cucking me in the most intense and depraved ways I could imagine without risk, all of a sudden I started to feel a genuine pit in my stomach every time I saw them spend time together. I wasn’t jealous or upset, just nervous/excited. I had butterflies in my stomach like the first time you pluck up the courage to ask out a crush.
On Christmas Eve a couple weeks ago, I finally asked my wife if she had been flirting with him on purpose, and if she had noticed that he was flirting with her back. She expressed surprise again, saying that she liked him but hadn’t been trying to flirt, and seemed incredulous of the idea that he might have been flirting with her. I insisted that he was (which he has since confirmed) but she still wasn’t sure.
I asked how the prospect of him flirting with her made her feel. She told me she liked it. I jokingly asked her, “so just to confirm… you haven’t been trying to seduce him on purpose?” She laughed and said “no, not intentionally…….it’s not like I wouldn’t though.”
We both laughed and I tried not to give away the fact that my dick had rocked up to half mast in the space of about three seconds. I pressed her further and asked if she would be interested in having sex with him. She nodded, and told me she would be open to trying it. I affirmed once again that this was 100% cool and that I was completely on board with whatever she wanted to do, trying really hard not to seem overly eager or to give away how badly I wanted her to do it. She started joking about flirting with him on purpose so he’d drive her to pick up ebay purchases around the city in his truck. I said she could offer to repay him by sucking his dick. She thought that was a fun idea.
Later that night we were having sex, and I made her confess to me that she did – despite her protestations – enjoy a larger penis. After four years of moaning into my ear about how much she loved my big dick it would have been tough for her to deny, even though she told me that she’d still enjoy sex even if my cock got smaller and couldn’t get hard. As I got closer to orgasm, I whispered in her ear and told her that I’d love to see her get fucked by a huge hard cock one day. I heard her breath quicken and I emptied my balls into her as she started whispering back, saying she’d love to fuck a bigger cock in front of me, that she’d make me watch, denying me the ability to touch myself, just sitting still and watching her get railed by a bigger dick than mine, knowing there was nothing I could do about it other than stare. In all the hundreds of times we’ve had sex over the years, I’d never cum so hard as I did when she said that to me with a giggle and a shit-eating grin. It was like a dream come true. My only regret was cumming so fast she didn’t get to describe more of the fantasy.
She has, independently of the rest of this, taken an interest recently in trying to make me cum prematurely. I’m not mad about it. Sometimes I think about how embarrassing it would be if we invited someone over for a threesome and I came super early, which depending on the situation would either mean disappointing two women at once or having to sit down and watch another cock fuck my wife while I desperately try to get hard again. Usually fantasizing about that is enough to make me cum pretty quick anyway. I think my wife would laugh out loud if that ever happened in real life too, which of course makes it even hotter to think about.
We finally saw our new friend recently after a few weeks out of town, and we went clubbing at a local gay bar with some friends. I was hanging out with him when we noticed my wife had disappeared. He and I went exploring and discovered her making out with a lesbian who pulled her aside at the bar. Our friend looked over at me in shock, and when I responded by nodding sagely he put 2 and 2 together and asked if we were in an open relationship. When I said yes, he said “that answers that question.” I asked him who was asking what question, and he confessed that it was something he’d been pondering privately.
Fast forward to yesterday. My wife and I are hosting a party, and our new friend offers to drive her around town to pick up supplies. She says yes. Contrary to our previous discussion she does not suck his dick, not because she didn’t want to but because she has now realized on some level that she has a genuine crush on this guy and is enjoying the slow burn of flirting with him on purpose. The party is a huge success, I kissed a couple of our other friends in front of everybody, and my wife is flirting really heavily with our friend. He stays longer than anybody else, but eventually has to leave because his friends are too tired and drunk to stay and he has to take them home. After everybody left, I asked my wife how she thought things had gone. She said she was incredibly happy with the event, and then floated the idea of inviting him back over for a three-way. As it so happened (another little bit of manipulation on my part), me and some of his other friends had stolen miscellaneous items from his house the previous week to surprise him with as a prank, and despite noticing a piece of his property sitting in our kitchen, he’d forgotten to take it home with him. My wife was exhausted and opted to go to bed instead, but if she’d been even a little bit more sober I think she would have used it as an excuse to invite him back. As if she needed an excuse.
The next morning, I ask her how she feels about the prospect of having sex with him sincerely. She admits that she thinks it would be fun. I ask if she’s interested in him having sex with both of us together or just by herself. She says both of us together, but seems open to other ideas. She tells me that she’s enjoying the slow build up and that she might not fuck him for a while. I nod with maturity and empathy and try to obscure all the blood rushing from one head to another. We have a lovely, chilled-out day clearing up after the party. Then, in the evening, I went out to the grocery store for an hour or so. When I get home, my wife is laying in bed wearing only her shirt, her pants and underwear strewn across the floor. It turns out she’d been testing a new sex toy I bought for her recently. She tells me that she came several times, and then looks at me with fuck-me eyes and tells me I need to read some texts from this evening between her and our friend.
She hands me her phone and starts touching herself again as I lay down and start reading pages and pages of discord messages they’d sent each other in the space of an hour. It started out innocent, with him saying how much of a great time he had at our party, before my wife immediately escalated the tone by telling him that we almost invited him back over after the party ended.
I was shocked. “What happened to enjoying the slow burn? Taking it easy? Savoring the build up?!”
She shrugs at me and starts fingering herself. “I was horny. It doesn’t mean I’m going to fuck him immediately!”
I keep reading. He responds to her comment with surprise and gets all shy. He asks her what she meant by that. She tells him to guess. He says she’s being cruel and she sends him a ” 😉 “. Their conversation gets hot and heavy fast, and he confesses that he’s had an interest in her ever since that first show where I sat them next to each other. She tells him the feeling is mutual. He asks if I’m also interested, and she confesses on my behalf that I am. I pretend to get mad at her and she laughs at me, and I insist that it would have been hotter if she’d forced him to ask me directly. She agrees that would have been hotter. He messages her back saying that he can’t help but be attracted to her, because he’s always had a thing for alternative girls. She texts him back saying “Poor you!” and puts her phone away to concentrate on masturbating. Knowing him, I’m certain this will have driven him wild.
I asked my wife if she wanted any head, but she’d already cum several times with her new toy. She asked me how fast I could cum inside her right now. I told her the truth, which was pretty fucking fast.
I went to slide my cock inside her and she started teasing me, grabbing my cock and only letting the tip penetrate her for a couple minutes. She immediately started teasing me and dirty talking, playing with my nipples as she asked me how badly I wanted to see her fuck someone, and if I wanted to watch her fuck him specifically. I was begging and whimpering and pleading just to let me watch.
She smirked at me and said she was pretty sure based on his attitude and personality that he must have a gigantic cock. I asked her why she thought that, and she said that it was because of the way he carried himself, the way he treated people. She said he had the energy and vibe of someone with a cobra in his pants. I told her she could get him to send a picture if she wanted, and she told me she was sure she could, but said “I think it’ll be more fun to find out how big it is when he slaps me in the face with it for the first time.”
I started pounding into her as hard as I could, more turned on that I’d been in years and desperate to cum after only a minute or so. Between moans I managed to tell her that it would be exciting to fuck a bigger cock because there were positions they could achieve that she couldn’t do with me. I’ve always wanted to fuck her in the spooning position, but I’m not quite big enough for it to reach around. She went bright red in the face and started moaning desperately. I could tell she was loving the dirty talk. I told her that he would probably be able to fuck her standing up, something I’ve never had the strength to do, and she almost came on my cock right there and then. I privately wondered if he might be big enough to make her cum from penetration alone, something I’ve only been able to achieve once out of hundreds of attempts.
After years of only hinting at it, I finally started confessing how badly I wanted to watch her fuck someone in front of me. She asked me how I’d feel if she was interested in having sex with him separately without me there. My jaw dropped and I nearly came inside her, but pulled myself back down from the edge so she wouldn’t stop talking. I told her I really, really liked that idea. She talked about walking over to his apartment to fuck him. I talked about how much fun it would be to have both of us fucking her at once. I said we could pull off an Eiffel Tower and she agreed. I asked what holes she’d like us to fill at the same time and she said she wanted to practice her oral skills by giving both of us head at once. She said she likes anal sex, something she’s never confessed to me before, and I started to get lightheaded thinking about watching someone else fuck my wife in the ass before I ever got the chance to.
She teased me, saying that if I didn’t put a load in her soon she could take a stroll down the street and get filled up by him instead. I told her I wanted to eat his cum out of her pussy, that she could walk back over from a hook up and sit on my face. She grinned at me, twisted my nipples, and said she wanted to make me cum inside her after he did, and then push my head down and force me to eat both of our loads out of her pussy at once. After years of specifically seeking it out in porn but never telling her, I finally told her about the position I’d always fantasized about – the 69 position with me on the bottom, and another cock fucking her in doggy right above my face so I can lick her clit from below, get an up-close view of his cock stretching out her pussy, and let his cum drip down onto my face and into my mouth after he finishes. She looked up at me, staring me dead in the eyes, and told me that she loved that idea. That if she ever gets the chance, she’ll put me in that position and feed his cum to me. I let out a pathetic wail and came harder inside my wife than I’d ever cum before for the second time in two weeks.
Finally, for the first time since I had my cuck awakening ten years ago, it looks like I’m finally going to get cucked in real life. Cucked hard, no less, and not with a stranger from the internet but from a close and intimate friend with whom we now share multiple social circles. Both he and my wife are gossips who like to brag, too, so I’m certain if it actually happens all of my friends will know about it within a matter of days. It makes me so horny I get dizzy just thinking about the fact that all of our friends will know I’m getting cucked by the dude who’s been sitting next to my wife at game night every week for months. I can’t stop thinking about it.
After we had sex, I asked my wife how likely it would be to happen for real after she sent those messages to him. She said she’s almost certainly going to fuck him for real if I’m ok with that, and she hasn’t decided if she wants me to be there when it happens or not. I asked her that if they decided to fuck together privately and both parties were willing, whether she’d be down to make a home movie with him for me. I know she likes being filmed, and she said yes immediately.
She’s asleep now, and I don’t know if they continued to message each other later into the evening or not. Outside of our game night we have multiple events scheduled with him in the near future. If things continue to escalate in the manner they have been, I wouldn’t be surprised if they end up fucking in some shape or form within the next two weeks, or even within the next few days.
I spent years praying that an opportunity like this might come around one day, and I always promised myself that even if I started getting cold feet that I’d push through and avoid the urge to back out. At long last, the fantasy I’ve been jerking off to every single day for a decade might finally become a reality. I set this course in motion on purpose, and now I have to live with the consequences one way or another. My cucking is inevitable now, and I owe it to my wife and to myself to let it happen. There’s a real chance I might regret it when I see the expression on her face as he slips his cock inside her for the first time, but by then it will be too late. There’s a chance our sex life might change forever. Even if she doesn’t have a good time fucking him (and I suspect she will), the cat is firmly out of the bag now. She’s going to find a big dick to satisfy her one way or another. She still enjoys having sex with me, but I can feel the hunger she has for someone bigger, who can last longer and toss her around in ways that I can’t. It’s dizzying and exhilarating to think that at this present moment, it is more likely than not that the next time my wife has sex, it will be with him instead of me. I’m not a betting girl, but I’d place good money on him getting to fuck my wife in the ass after only knowing her for a few months, when I’ve never been allowed to put anything in there besides my tongue over the course of our entire relationship.
There’s even a world in which she enjoys having sex with other people so much she might not be interested in fucking me ever again. Even in such an extreme scenario, I know in my heart of hearts that if she told me to beg her on my hands and knees to make me pussy free I would do it without question. I’ve been dreaming for years about all the depraved ways she could humiliate, degrade, and cuck me. Now that it’s finally here on my doorstep, I’m determined not to mess it up.
If things go any further, and I think they will, then I’ll post a follow up with all the juicy details. Watch this space and wish me luck.
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