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Cuckolding single men
Posted: Wed Oct 15, 2025 11:04 pm
by firef503
I've been in this debate on other sites multiple times. There are the cuckold purest out there that believe it's not "real" cuckolding if it's not your wife or gf. I'm not sure if there's any hobby, interest, fetish or whatever else out there where critics don't exist, "It's not real hunting if you don't use a bow." "You arne't a real cowboy unless you ride bulls." "It's not a real sports care unless it's a manual transmission" (actually that last one i might agree with). Either way, who cares! There's not enough hours in the day to worry about what someone else is doing and call them out on it. If I guy has a foot fetish and prefers to call himself a cuckold, let it ride. Afterall we live in the "you do you" generation.
I've met some eager single cuckold men. They make me a list of women in their life that men something to them. Then I come along and try to have sex with them. It goes pretty well and it's an outlet for single men who have a desire to be cucked.
Re: Cuckolding single men
Posted: Thu Oct 16, 2025 3:21 am
by frank12
I'm right there with you on so many attempts to rigidly define the terms used to describe things that are so varied in practice.
But to the topic - some years ago I enjoyed several playtimes over a couple of years with a a woman and a friend she was occasionally "dating". Both had somewhat recently emerged from tumultuously ended marriages and he "swore" he would remain single. She too had been burned by the negatives in her marriage and divorce. But they were clearly thoroughly enjoying one another (and he was not seeing others but she and I played alone a few times). She thrilled to her freedom to indulge in sexual play especially while he watched, and he was equally thrilled to offer her to another man then passively watch and clean up before reclaiming her. Cuckold was a word neither used but themes were in play. I think they were both playing out alternatives to their previous relationships and it was fun and perhaps even therapeutic. It all ended with his job reassignment and at last communication neither had remarried.
Was that a cuckold relationship? No? Yes?
Re: Cuckolding single men
Posted: Thu Oct 16, 2025 6:59 am
by fk2546
Yes, it is not a real sports car if doesn't have a manual transmission. LOL
Re: Cuckolding single men
Posted: Thu Oct 16, 2025 8:32 am
by firef503
fk2546 wrote: ↑Thu Oct 16, 2025 6:59 am
Yes, it is not a real sports car if doesn't have a manual transmission. LOL
It's probably a bad example to use something that contradicts my own point. But I just had to throw that one in for fun........I always have fun getting in someone else's automatic car. I wait for them to ask me if I know how to drive their car and I say, "of course I do! Now which one of these pedals is the clutch?"
Re: Cuckolding single men
Posted: Fri Oct 17, 2025 6:27 am
by sml_peterBR
When I was younger, I had a few close female friends I was atracted to but haven't tried anything with them. During that time, I've seen multiple men date them, sometimes they where more open to share details. I remember that jealous feeling I felt can be similar to cuckold angst.
One thing that turns me on in a cuckolding dynamic is to know other men are enjoying women in ways that are not possible for me, and it applied to that situation.
It's not the same thing as a "real cuckolding" but I believe it's possible to adapt the situation and have some fun.
I like to help my wife to prepare for dates, that would not be possible if I was single. Instead, if you were dating a friend of mine in the situation you described, I could buy a lingerie set for you to give her as a gift, for example.
Re: Cuckolding single men
Posted: Sat Oct 18, 2025 3:49 am
by bltn1966
Marie and her friends would intentionally talk about their latest sexcapade, in graphic details, in front of a bartender. He would give them free drinks while listening to them. The bartender was short and pudgy. None of the ladies were sexually interested in him. They mostly flirted with him for the free drinks. One night Marie hung out with the young guy. Marie assured me this wasn’t a date and there wasn’t a chance in hell she was going to do anything with him. Somehow, the night ended with the young guy fucking Marie. Marie said his short fat cock drive her crazy. If you ever have sex with a multi-orgasmic lady who has body convulsing orgasms, you’re going to want to fuck here again and again and again. Unfortunately for him, it would be a long time before he get another chance with Marie.
Marie didn’t want her snobby friends to know she had sex with the short chubby bartender. Over the next year Marie and her friends would sit in front of him and talk about their latest FB. The poor guy had to listened to Marie talk about other guys. Marie said one time her and her friends talked about guys with big cocks. Marie told her friends big dicks are overrated. She winked at the bartender and said the best sex she ever had was with a guy that had a short super thick cock. She said she only had sex with him one time but she could see herself getting addicted to his super thick cock. The ladies wanted to know who she was talking about but Marie wouldn’t tell them it was the guy serving them their drinks.
The bartender would call and text Marie to go out with him again. For a long time Marie avoided his calls and texts. Then one night she unexpectedly saw him at a mutual friend’s birthday party. I was out of town at the time. Marie rebuffed him and played hard to get whenever the young guy tried hitting on her. Later on she told me she knew she was going to have sex with him the second she saw him at the party. That night the young guy gave Marie a second serving of the best sex she’s ever had.
Re: Cuckolding single men
Posted: Sat Oct 18, 2025 11:51 pm
by jratt85
I kind of wish I could be on the receiving end.. It'd be so nice to have a woman that wants me to think she's hot, even if she'll never date me/fuck me, and loves to tease me about all the things I'd do just for the chance to eat her out.. I had that once, twenty years ago, and it was pretty fucking hot. People badmouth Myspace all the time these days, but it was the only place/time I ever found women to talk to, some of them lasting ten years!
It'd be nice to have the attention of a pretty woman again, and maybe have her give me challenges and stuff to do for her in exchange for seeing pics/vids of her with other guys.. like making me wear a cage all day or making me have to take a massive toy in me or wear nipple clamps for X amount of time even while I walk around the house.. things like that. (showing my bit of a sub side lol)
Re: Cuckolding single men
Posted: Mon Oct 20, 2025 1:18 pm
by ucaneffher
Not sure if this is apples to apples but I think it comes relatively close. So as many here know, I was a cuckold for 7 years in my late teens and early 20s and have been wanting to return to that life but have not had much luck with any girlfriends after that first and only hot gf.
In efforts to at least relive the lifestyle or get close to it, I've often thought about ways to achieve it even if not truly achieving it. I traveled frequently to a country where there's a lot of sex tourism and while I've never hired a girl or been interested in hiring one for sex, a bright idea did come to mind of hiring one from the countless websites of beautiful girls available for play.
The idea was that I'd reach out, explain my cuckold fantasy and offer to pay her to spend one entire day with me as my "girlfriend" aight seeing and doing fun boyfriend/girlfriend activities but at night we go out to the bars and the clubs. At these venues she will be my girlfriend who will cuckold me with the man of her choice. She dances, flirts, drinks with him and eventually brings him to our table.
He will not know she is a sex worker and instead she will tell him I am her boyfriend and I like to watch her fuck other men. We take him back to our hotel and she gives him whatever he wants in bed as long as they let me watch. Anal, oral, vaginal, whatever and I will pay her for whatever sex she gives him and all I get out of this is jerking off while he fucks "my" girlfriend.
It's a win-win-win. She gets paid for an entire day with me,.she gets paid to fuck a man that she likes, he gets to fuck a hot girl in front of her boyfriend, and I get to live my fantasy of being a cuckold.
Hey, who knows, maybe her and I actually click during our entire day together and she realizes that she can be an escort and still have a man who would be more than happy to have her while she does that.
Re: Cuckolding single men
Posted: Fri Oct 31, 2025 9:54 am
by MartasBoy
I feel I was often cuckolded as a single guy. It is sort of where I got exposed to the feelings about that, and was conditioned and trained for eventually becoming a cuckolded husband.
I had a number of women who recognized that I would be easy to manipulate if they gave me a bit of attention, and let me think I might possibly have a chance with them. I got put in the friend zone often.
There were some really beautiful girls who let me do favors for them and hang out at their house. They let me keep them company when their boyfriend was busy.
There was one girl who realized that I loved being allowed to handle her clothing, so she let me do her laundry for her. I would take her laundry to the laundromat when I did mine. It made me feel titillated and important to be seen by other people, folding her bras and panties at the laundromat, and hanging up her dressy blouses and skirts on skirt hangers.
She may have figured out that I got to delete it from being able to handle her bras and panties, and she would allow me that titillation, to get her laundry done.
She let me stay over in her bed with her a few times when her boyfriend was away. But she made it very clear that I was not to think of us as being boyfriend and girlfriend, and I was never to tell anyone that she's my girlfriend, because she did not feel that way about me. She also made it clear that she was not interested in having sex with me. But one night she spit on her hand and gave me a handjob. I asked her why she did that, since she wasn't my girlfriend and did not want to have sex with me. She told me, "I did it because I feel sorry for you because I get the impression you haven't had a lot of action with very many girls in your life. But don't expect anything more than that, and don't get the idea that I am going to do that for you very often."
I had a number of relationships like that with girls when I was single, where they kept me in the friend zone, but let me do favors and chores for them, or work on their car, or do their laundry. But as soon as their boyfriend would call them, they would send me home and prepare to be with their boyfriend.
Re: Cuckolding single men
Posted: Sun Nov 02, 2025 3:23 am
by Thebestdays1
I've been divorced twice but for the past year I've been meeting my first wife behind her partner's back. We've also started meeting up, roughly once a month, with her elder sister and their nephew.
I did get to watch her suck her nephew off a few times, 4 years before we split up but had been unaware she was also meeting and fucking him behind my back during our last 4 years together and had foursomes with him, her elder sister and her partner. When the 4 of us meet up, my ex still feels like my wife and I still feel like she's cuckolding me when she fucks him. As a further twist, my ex SIL and I have become quite close and as I live at the complete opposite end of the country to them, I spend a few nights at her place.
On the monday morning after we've all met up, the nephew calls in on his way to work for a blowjob and she and I get on our knees and take turns in sucking him until he cums and then she and I have a lovely cummy kiss.
Although she and I haven't become anything official, the nephew calls in on her occasionally and then she'll text me to say he's just fucked her or he needed a blowjob and I feel just the same as I did every time my ex went with someone.
Re: Cuckolding single men
Posted: Thu Dec 04, 2025 7:31 am
by Tryagain
ucaneffher wrote: ↑Mon Oct 20, 2025 1:18 pm
Not sure if this is apples to apples but I think it comes relatively close. So as many here know, I was a cuckold for 7 years in my late teens and early 20s and have been wanting to return to that life but have not had much luck with any girlfriends after that first and only hot gf.
In efforts to at least relive the lifestyle or get close to it, I've often thought about ways to achieve it even if not truly achieving it. I traveled frequently to a country where there's a lot of sex tourism and while I've never hired a girl or been interested in hiring one for sex, a bright idea did come to mind of hiring one from the countless websites of beautiful girls available for play.
The idea was that I'd reach out, explain my cuckold fantasy and offer to pay her to spend one entire day with me as my "girlfriend" aight seeing and doing fun boyfriend/girlfriend activities but at night we go out to the bars and the clubs. At these venues she will be my girlfriend who will cuckold me with the man of her choice. She dances, flirts, drinks with him and eventually brings him to our table.
He will not know she is a sex worker and instead she will tell him I am her boyfriend and I like to watch her fuck other men. We take him back to our hotel and she gives him whatever he wants in bed as long as they let me watch. Anal, oral, vaginal, whatever and I will pay her for whatever sex she gives him and all I get out of this is jerking off while he fucks "my" girlfriend.
It's a win-win-win. She gets paid for an entire day with me,.she gets paid to fuck a man that she likes, he gets to fuck a hot girl in front of her boyfriend, and I get to live my fantasy of being a cuckold.
Hey, who knows, maybe her and I actually click during our entire day together and she realizes that she can be an escort and still have a man who would be more than happy to have her while she does that.
Much as i admire your effort, but how can that work at all? The whole point of cuckolding is for your precious wife or GF to be royally fucked in a way that you cannot. What feelings will you have watching the escort - whom you have no vested interest in, get fucked? Please save your money - must be very very expensive
Re: Cuckolding single men
Posted: Thu Dec 04, 2025 9:19 am
by joe_b
ucaneffher wrote: ↑Mon Oct 20, 2025 1:18 pm
Not sure if this is apples to apples but I think it comes relatively close. So as many here know, I was a cuckold for 7 years in my late teens and early 20s and have been wanting to return to that life but have not had much luck with any girlfriends after that first and only hot gf.
In efforts to at least relive the lifestyle or get close to it, I've often thought about ways to achieve it even if not truly achieving it. I traveled frequently to a country where there's a lot of sex tourism and while I've never hired a girl or been interested in hiring one for sex, a bright idea did come to mind of hiring one from the countless websites of beautiful girls available for play.
The idea was that I'd reach out, explain my cuckold fantasy and offer to pay her to spend one entire day with me as my "girlfriend" aight seeing and doing fun boyfriend/girlfriend activities but at night we go out to the bars and the clubs. At these venues she will be my girlfriend who will cuckold me with the man of her choice. She dances, flirts, drinks with him and eventually brings him to our table.
He will not know she is a sex worker and instead she will tell him I am her boyfriend and I like to watch her fuck other men. We take him back to our hotel and she gives him whatever he wants in bed as long as they let me watch. Anal, oral, vaginal, whatever and I will pay her for whatever sex she gives him and all I get out of this is jerking off while he fucks "my" girlfriend.
It's a win-win-win. She gets paid for an entire day with me,.she gets paid to fuck a man that she likes, he gets to fuck a hot girl in front of her boyfriend, and I get to live my fantasy of being a cuckold.
Hey, who knows, maybe her and I actually click during our entire day together and she realizes that she can be an escort and still have a man who would be more than happy to have her while she does that.
Not sure where you go, but I met mine in the Philippines. I visited several times before finding my wife who was very active with the foreign men who visited. We dated long distance and she did not slow down one bit once we got together. If you are already visiting, you should look for marriage or at the least a long term set up where she remains active but you are her steady. She is in the states with me now and still very active, but nothing like it was before.