Want my wife to cuckold me with my best friend.

For cuckoldresses and the men who serve them.
johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Sep 17, 2025 2:03 pm

john jasson wrote:
Tue Sep 16, 2025 10:03 am
Your wife is open minded about sexuality and that’s great.
Why not challenge yourself initially, rather than her?

Use the old dream gambit to put yourself out there. You find dressing in her underwear difficult. So tell her you had a wet dream and woke up at the edge of orgasm. Say that Greg was over and the 3 of you were naked, playing around in the bedroom, until she made you stand in the corner and put on her panties. Tell her you were embarrassed but excited as hell. That leaves plenty of loose ends for a conversation.
Good luck!
Thanks John. Always good to hear from another John! 😀
Yes, I've toyed around with the old "I had a dream..." ploy. Your version would certainly get the conversation going, that's for sure.
But I think I need to go for a slightly subtler approach.

But, as ever, ideas always welcome.

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Sep 17, 2025 2:29 pm

elina wrote:
Wed Sep 17, 2025 1:06 am
.......what I strongly reccommend for you is to in all communications with Lucy, tell Her how much you love and adore Her, and that the longer you are with Her, the more you understand that the most important thing to you is that She is happy. (From what I read on your post, I think this is the truth - if you don't currently fully agree, then think for a little while and see if you still don't agree).
Thank you Elina for your post. I've downloaded copies of the two books that you mentioned. I know they've been mentioned before, on here, but I've never bothered to look at them. But I will now, and I'm sure they will be an interesting read.

I don't think, for us, that me making Lucy my Goddess will really work. She is a feminist, but not a fanatical one. She is adamant that we should both be of equal importance in our relationship.

That's not to say that we have to adopt an attitude of equality 100% of the time.
The Dom/sub sessions are an opportunity to have a change from our normal roles, and explore a different attitude. Lucy does enjoy her time as the Dom. And I enjoy my time as the Sub.
But, outside of sex we turn back to being a fairly equal partnership.
Of course, some of that Dom/sub stuff does rub over into our 'normal' life. Sometimes, when we can't decide on something, or we each want different things, she might use her 'stern' voice, and overrule me. If it's not a major issue, then I might say "yes Mam", or similar. It's done as a bit of fun.
But I like that she is still being slightly dominant.

If I were to give in to her on everything then she would probably begin to wonder what had happened to me!

I've quoted the bit you posted about letting her know that I love and adore her.
I make a point of telling her that, whenever I can. I'm very lucky to be with a lovely lady. I'm a bit of a romantic, and regularly buy her little gifts, or flowers, and make little romantic gestures. It helps keep the love alive.

I wonder if she'll take an offer of letting another man fuck her, as a romantic gesture from me? 🤔

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Sep 17, 2025 3:16 pm

Sorry to be making a string of posts. But it's difficult, on a phone, to make a post combining quotes from multiple different people, and include my responses. The current 'bad gateway' and time out problems don't make it easy either.

But there has been a small development that might be of interest, that I thought I'd post about separately.

A fellow member pm'd me and we've had an interesting exchange of messages.
One thing he suggested was setting some 'dares' for me to do. I was curious, so asked him to suggest some. One that he came up with was to dare me to wear a pair of Lucy's panties when Greg, my friend, was next visiting us.
I thought this was easy enough to do, and might be interesting.
We did already have a visit from Greg planned for last Saturday evening.
But, in the meantime I thought it might be even more interesting if Lucy knew what I was doing.
So, on Friday evening I initiated a sex session, which I suggested should be a Dom/sub one. I made an excuse that I'd had a stressful day at work, and needed to 'detox'.
During that session I asked Lucy to 'make me' wear her used panties. Which she was delighted to do! She was actually quite surprised that I was initiating it, as I had always previously been reluctant to do it.
Anyway, when we'd both got rid of our frustrations (ok, we'd both cum) I kept her panties on while we chatted. Which she eventually remarked upon. I normally take them off at the first opportunity.
At which point I chanced saying to her, "What about I wear your panties, under my shorts, when Greg comes over tomorrow?"
This surprised her, but puzzled her. She asked me why I wanted to do that. I must admit, I hadn't really come up with a good answer for why. But just told her that the idea sort of thrilled me, in a kinky sort of way.
She wasn't sure initially, but eventually said, "If you want to. But do you want Greg to see them on you?" I immediately told her that no, that wasn't the intention, and that would be a bad idea.
Saturday, before Greg arrived, Lucy checked with me if I still intended to wear her panties under my shorts. I said I did. And she insisted that I wear the pair I'd had on, on Friday. Which hadn't been laundered, and had a rather 'used' gusset. Lucy had worn them all day Friday. She also insisted on watching me put them on, I think to make sure I was serious. I didn't tell her that this idea came about as part of a dare.

Greg's visit came and went, and we had a good evening. I did get worried a few times that Lucy was going to 'out' me. She put her hand on my bottom a few times and felt me up, discretely, giving me a wicked smile. Which got my heart racing!

So no great event. But on Sunday we did get chatting about it. Lucy was thinking that maybe I was wanting to let Greg know about my sub ideas, or even wanting to reveal our Dom/sub sessions. I assured her I wasn't. I think that's a step way too far at the moment.
We talked about it again on Monday, and Lucy was teasing me at one point, saying that Greg would love to see me wearing a cute pair of panties. I told her, "don't you dare say anything to him".
And then I just added, "I bet he'd love to see you in those panties!"
Which surprised her! She just said "Yeah, I bet he would!"
After which she went quiet.

Ok, not a huge leap forward. But it does possibly give me a chance to pick up the conversation again, and ask her about her reaction.
Fingers crossed that I can steer the chat in the right direction.

subtoall
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Re: Want my wife to cuckold me with my best friend.

Unread post by subtoall » Wed Sep 17, 2025 6:44 pm

Au contraire! I think fantasising about her being seen in her panties by another man is a huge leap forward. Especially given her reaction.

Johng1953
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Re: Want my wife to cuckold me with my best friend.

Unread post by Johng1953 » Wed Sep 17, 2025 10:42 pm

My fingers are crossed!

wannabecUKold
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Re: Want my wife to cuckold me with my best friend.

Unread post by wannabecUKold » Wed Sep 17, 2025 10:55 pm

When Greg next comes round, Lucy should stand in front of him and say “John has given me a dare….given both of us a dare. Up for it? ….I have to take my panties off in front of you, provided that you promise you will put them straight on.” I doubt Greg would have any problems being seen in them.

elina
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Re: Want my wife to cuckold me with my best friend.

Unread post by elina » Thu Sep 18, 2025 12:56 am

johnswan wrote:
Wed Sep 17, 2025 2:29 pm
elina wrote:
Wed Sep 17, 2025 1:06 am
.......what I strongly reccommend for you is to in all communications with Lucy, tell Her how much you love and adore Her, and that the longer you are with Her, the more you understand that the most important thing to you is that She is happy. (From what I read on your post, I think this is the truth - if you don't currently fully agree, then think for a little while and see if you still don't agree).
Thank you Elina for your post. I've downloaded copies of the two books that you mentioned. I know they've been mentioned before, on here, but I've never bothered to look at them. But I will now, and I'm sure they will be an interesting read.

I don't think, for us, that me making Lucy my Goddess will really work. She is a feminist, but not a fanatical one. She is adamant that we should both be of equal importance in our relationship.

That's not to say that we have to adopt an attitude of equality 100% of the time.
The Dom/sub sessions are an opportunity to have a change from our normal roles, and explore a different attitude. Lucy does enjoy her time as the Dom. And I enjoy my time as the Sub.
But, outside of sex we turn back to being a fairly equal partnership.
Of course, some of that Dom/sub stuff does rub over into our 'normal' life. Sometimes, when we can't decide on something, or we each want different things, she might use her 'stern' voice, and overrule me. If it's not a major issue, then I might say "yes Mam", or similar. It's done as a bit of fun.
But I like that she is still being slightly dominant.

If I were to give in to her on everything then she would probably begin to wonder what had happened to me!

I've quoted the bit you posted about letting her know that I love and adore her.
I make a point of telling her that, whenever I can. I'm very lucky to be with a lovely lady. I'm a bit of a romantic, and regularly buy her little gifts, or flowers, and make little romantic gestures. It helps keep the love alive.

I wonder if she'll take an offer of letting another man fuck her, as a romantic gesture from me? 🤔
Thanks for responding.

One of the key messages from Elise Sutton is that most females have a dormant Dominant side.
Given the opportunity and a husband who encourages this side to come forward, it will emerge, slowly but surely.

From your posts, also the ones you sent yesterday, it is very evident to me that your Wonderful Wife's dominant side is already emerging. Don't expect that reading these books will turn Her into a strict Dominatrix 100% of the time, the idea is more to grow together and evolve the relationship in a way which is mutually beneficial to both parties.

Also, a key insight from Elise Sutton is that the more submissive you act, the faster your Wife's dominant side will emerge, your experience with wearing Her panties while Greg was over clearly shows that. This does NOT mean that you cannot be romantig and buy Her gifts, that is just one way of showing Her how much you appreciate Her and loves Her. Neither does it mean that you cannot interact like any other couple at times, that is also typical. Your Wife wants a husband who adores Her, someone She is comfortable with going to restaurants and shows and visiting friends with as a normal loving couple. What it does mean is that you should not be surprised if your Wife starts snapping into a Dominat mode more frequently; the point is that this should happen whenever SHE wants to and you should always be happy to obey Her.

Good luck, I think you have found exactly the Lady you can love for life, regardless of how dominant She turns out to be, or not to be. If you suggest reading the books together, you should present this as a way for the two of you to explore what you both want, and not something that you need to try out and certainly NOT that this is your expectations for what will happen. It needs to evolve as She is comfortable with.

Sincerely
elina

sccuck
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Re: Want my wife to cuckold me with my best friend.

Unread post by sccuck » Thu Sep 18, 2025 1:41 am

Johnson, you’ve created your opening. Gift your bride a gorgeous two-piece lingerie set. Tell her it’s to replace the panties she let you wear, and you fantasize showing her off next time Greg visits. Tell her you want to see how far it goes and your ultimate fantasy is to watch him take her while you sit in corner wearing her panties.

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Fri Sep 19, 2025 12:12 am

subtoall wrote:
Wed Sep 17, 2025 6:44 pm
Au contraire! I think fantasising about her being seen in her panties by another man is a huge leap forward. Especially given her reaction.
Hi subtoall. Her response of "Yeah, I bet he would" was made in a tone of voice that implied that she knew he would like to see that, but it wasn't going to happen.
Having said that, in our subsequent discussions she pointed out to me that Greg has already seen her in a bikini.
We've been to the beach with him and whichever girlfriend he had at the time.
She said that Greg had seen her in her bikini and that I'd seen his girlfriend in hers. "So he's already seen me in the equivalent of panties".
But I pointed out to her the essential difference. Which was that at the beach it was a public situation. And bikinis etc were perfectly acceptable there. But her revealing her panties, at our house, with just him there, would be a different thing.
Which she conceded.
We did have a bit more discussion, but she was mostly wanting to understand why I wanted to wear her panties (albeit hidden under my shorts) while Greg was there.
I have struggled somewhat to explain my motivation. So I've just resorted to saying that it just seemed a bit 'kinky', or 'exciting'.
I wanted to get the conversation back to the idea of her revealing her panties to him, but the conversation moved elsewhere, and I didn't want to make myself sound obsessive about her 'flashing' herself.

I'm sure that there will be another opportunity to discuss things with her soon.

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Fri Sep 19, 2025 12:16 am

wannabecUKold wrote:
Wed Sep 17, 2025 10:55 pm
When Greg next comes round, Lucy should stand in front of him and say “John has given me a dare….given both of us a dare. Up for it? ….I have to take my panties off in front of you, provided that you promise you will put them straight on.” I doubt Greg would have any problems being seen in them.
"I doubt Greg would have any problems being seen in them"
Hmmm, I'm not so sure. Maybe he'd hand them to me, and say "No.....You put them on". Gulp!

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Fri Sep 19, 2025 12:36 am

I thought I'd add a little bit of background to how we got to our current situation of occasional Dom/sub sessions.

The Dom/sub sessions developed slowly. Not sure when we started referring to them as "sessions".
I think it originated from early days, when we'd lark about and have a bit of 'rough and tumble' before it would move on to sex.
In the rough and tumble stuff, sometimes I'd end up astride Lucy, sort of holding her down, and trying to get her clothes off, her resisting, both of us laughing. Sometimes she'd end up on top of me. A situation that I didn't try to hard to prevent.

I remember one time, we'd ended up naked during one of the rough and tumble sessions, and I'd subtly allowed Lucy to get on top of me, her astride my thighs/cock (but without me penetrating her). She was holding my wrists down with her hands. I think she was saying something like "do you give in?" And I kept saying "no!" But she didn't know how to press home her advantage, so we were at a bit of a stalemate. We were both breathing heavy and a little tired from our 'fighting'.

I wanted her to win, but didn't want her to think I was allowing her to do so. So, after a bit, I said to her "Do you know how to make a guy do whatever you want, when you are in that position?". She said "no". I said "move further up, on to my stomach". Which she did. Then I said "Now reach around and grab my balls.....gently!" She grinned and sat up enough to be able to reach behind her and find my balls. Very quickly, with just a slight bit of pressure (I told her immediately to not do it too hard!) she had me asking her to stop. Then she asked me again if I gave in.....little squeeze, ask again, slightly more pressure, until I said "I give in".

She must have known about this male vulnerability, I assume. But I'd maybe just given her permission to use it.

She started to use this tactic whenever we had a physical 'fight'. She really liked the power it gave her. We are both the competitive type, and now she knew she had the ultimate weapon to use against me.

She was getting off on being dominant, and she started to realise that I was getting off on being dominated. I remember her saying to me one time, "you really like this, don't you?", referring to her domming me. I just nodded.

From there it just evolved. Sometimes she'd end up on my back, me face down, and would slap my bum. Which evolved into her spanking me.

Then, one time, I suggested tying her up "As if I was raping you". She wasn't happy about the rape idea, and I got a bit of a lecture about male fantasy, violent men etc. So I just said, "It was only a fantasy thing. You can rape me if you like".

She just looked at me and said "Ok then". I quickly got very rigidly erect, you know, a real iron girder strength one! She tied my arms out to the corners of the bed and then climbed on me. She sank herself down on me really roughly, then looked at me. She said "My god.... you're so hard!" I couldn't deny it. She did her best to make it rough and aggressive, which only helped to stimulate her more. She was a bit of an animal, and didn't take long to make herself cum. I can't finish her off if I'm doing the work. She always has to use her fingers to climax. But not this time. She just used my cock instead. She fucked me.

That little experience got repeated quite a lot. I'd unlocked quite a little animal!

And I absolutely loved it! I loved that she was getting so excited 'using me'. And I felt so excited being used. It just ratcheted up the excitement level for both of us.

Then we found that there were times when one of us wasn't quite in the mood for the Dom/sub stuff as the other. So we talked about a way to let each other know how far we wanted that session to go. We came up with the idea of saying 'light', 'medium' or 'heavy', or 'soft', 'medium or 'hard'. We never defined what was what, but that changed over time anyway.
Heavy started out as more spanking, her saying humiliating things to me, SPH stuff, calling me a lousy fuck, and so on. These days I encourage her to push me, if she's in the mood. I like her to spank me, telling her to make me beg for her to stop. Sometimes she stops too soon, afraid she's hurting me. Which she is, a bit. But I remind her that, though it's painful at the time, it doesn't really last. An hour or so later any redness is gone and there's barely any remaining sensation, maybe a bit of tingling. That has reassured her, and she's gone a bit further sometimes, with me really having to beg her to stop. We don't have a safe word, but I think we both know when I'm at my limit.

For some reason, I'd love her to spank me hard enough to make me cry. And I mean, really blubbing, saying sorry to her, and me being 'defeated'. The thought of that gets me real hard! Which worries me a bit. But we aren't very close to that, and might never be.
I don't want to cry because of the pain, although that would be an element. But more because of the humiliation, her verbally demeaning me etc.

To initiate a session, either of us might suggest it, there and then, or in advance. I virtually always agree to what she wants. She isn't always in the mood for my 'heavy' requests, so I don't push it by nagging or getting pissed off about it. I suppose really, that she mainly controls the level.

It was during one of our heavy sessions, a few years ago, that she was struggling to think of a way to dom me. I wasn't tied up (not all heavy sessions involve bondage). We were in the bedroom, and I was already naked. She likes me naked, regardless of whether she is or not. She told me to go to her underwear drawer and choose a pair of her panties. I assumed they were for her to put on. I held them out to her, but she just said "No....you put them on".
I laughed but told her "No way...."
She got real stern and told me "Either you put them on, or we stop right now". I tried to make a joke of it, because I really didn't want to put them on. But she insisted. Then she said "Do as your told, and don't answer me back". She was real serious. 😳

I hesitated a bit more, hoping she'd let me off. Then I put them on.

The feeling of shame and humiliation that I had was real strong. But I had that same mix of fear and arousal as when I think of being cucked.
Lucy really loves the look on my face when she gets me to put stuff on. She knows I struggle with doing it. I'm not allowed to go off and put the things on. I have to stand, a bit away from her, like a naughty little boy, while she watches, smiling.

Sometimes she'll talk to me, for example, when I've finished, saying things like, "There, that wasn't too difficult was it?" When she talks to me like that I feel completely humiliated but intensely aroused. I just can't really explain why.

"Who's a good little boy then? Say 'thank you Miss, for allowing me to wear these pretty girly panties' "....
When she talks to me like that....OMG, I feel like I'm close to ejaculating hands free!😳

The majority of our sex sessions are pretty vanilla.

sandy691196
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Re: Want my wife to cuckold me with my best friend.

Unread post by sandy691196 » Fri Sep 19, 2025 3:18 am

johnswan wrote:
Fri Sep 19, 2025 12:12 am
subtoall wrote:
Wed Sep 17, 2025 6:44 pm
Au contraire! I think fantasising about her being seen in her panties by another man is a huge leap forward. Especially given her reaction.
Hi subtoall. Her response of "Yeah, I bet he would" was made in a tone of voice that implied that she knew he would like to see that, but it wasn't going to happen.
Having said that, in our subsequent discussions she pointed out to me that Greg has already seen her in a bikini.
We've been to the beach with him and whichever girlfriend he had at the time.
She said that Greg had seen her in her bikini and that I'd seen his girlfriend in hers. "So he's already seen me in the equivalent of panties".
But I pointed out to her the essential difference. Which was that at the beach it was a public situation. And bikinis etc were perfectly acceptable there. But her revealing her panties, at our house, with just him there, would be a different thing.
Which she conceded.
We did have a bit more discussion, but she was mostly wanting to understand why I wanted to wear her panties (albeit hidden under my shorts) while Greg was there.
I have struggled somewhat to explain my motivation. So I've just resorted to saying that it just seemed a bit 'kinky', or 'exciting'.
I wanted to get the conversation back to the idea of her revealing her panties to him, but the conversation moved elsewhere, and I didn't want to make myself sound obsessive about her 'flashing' herself.

I'm sure that there will be another opportunity to discuss things with her soon.

Hi..

The way you have described your wife and your dynamics, it might not be prudent to try the usual gag of "I had a dream!"

Also, keeping her guessing about your actual intentions while you push the "I find iṭ kinky to wear panties when Greg is around" might lead to unintended consequences. She might think you are a closet gay!

Why not be more honest and plausible with you apparently "accidentally coming across the LS on social media or internet sites.. the hotwife dynamics and how other subs find it exciting to see an alpha male have sex with their partners".. If she asks which site? You can always refer to good ol' OHW!

It might be advisable NOT to imply that you are already deep into this fantasy and would love to see her with another guy. You having nurtured this kink "behind her back" so to say- may cheeze her off somewhat!

So perhaps coming across as a sub hubby who is kinda intrigued by these vague thoughts and who is not sure what it all means for him.. would be a safer approach to take with her? Then you two would have a chance to think about this new kink together and whatever happens would be a collective exploration- not the hubby springing it on the wife, on the sly!

It is also advisable NOT to relate this to Greg initially. It might be better to explore this as a concept to start with. IF things arrive at the the point where people and logistics are discussed.. THEN Greg's name may be brought in as a convenient solution..

This way you can be sure that you are not spooking her and at the same time it would give you a fair shot at exploring this as a collaborative venture.. more in line with the DNA of your relationship..

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Fri Sep 19, 2025 10:39 pm

sandy691196 wrote:
Fri Sep 19, 2025 3:18 am
It might be advisable NOT to imply that you are already deep into this fantasy and would love to see her with another guy. You having nurtured this kink "behind her back" so to say- may cheeze her off somewhat!

So perhaps coming across as a sub hubby who is kinda intrigued by these vague thoughts and who is not sure what it all means for him.. would be a safer approach to take with her? Then you two would have a chance to think about this new kink together and whatever happens would be a collective exploration- not the hubby springing it on the wife, on the sly!

It is also advisable NOT to relate this to Greg initially. It might be better to explore this as a concept to start with. IF things arrive at the the point where people and logistics are discussed.. THEN Greg's name may be brought in as a convenient solution..

This way you can be sure that you are not spooking her and at the same time it would give you a fair shot at exploring this as a collaborative venture.. more in line with the DNA of your relationship..
Thanks sandy691196. You make some very sensible points there, of which I've quoted what I think is the most important.

I certainly don't intend to spring the whole cuckolding concept on her suddenly. I've had many years developing my thoughts and ideas on this subject, and there's no way I can expect her to understand it all within a very short time frame.

It's useful that she finds the Dom/sub thing a turn on. At least she is starting with a kinky mindset!
It's just a case of steering this part of our sexual life, so as to sort of 'collide' it with my cuckold desires.

As you say, it needs to be a collaborative thing. If I felt that she wasn't interested in going in a cuckolding direction I would ultimately have to drop it, difficult though that might be.

And I also agree about not letting Greg know of my desires at this stage. That's only going to be 'doable' once, or if, Lucy is on board with the general idea of another man in her life.

streetracer
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Re: Want my wife to cuckold me with my best friend.

Unread post by streetracer » Sat Sep 20, 2025 4:26 am

Hi Johnswan. I've been following your post since day one because we share a common interest. My best friend and I have been friends for almost 40 years. He fucked my first serious girlfriend right in front of me about 35 years ago. I became a cuckold before I even knew the word even existed. There's never been any weirdness between us over the years, so I will say to the naysayers on here that they have no idea what they're talking about. I am currently married to my second wife and she is now just starting to slowly embrace my desires. She is fully aware of my cuckold fantasies. She has known for several years, but has made it clear that she will never do anything. I accepted that and respected her wishes and don't bring it up unless she wants to talk about it. She recently has talked about a man she has met and finds him attracted. Out of the blue, she'll say one day that he said this, or he's done that, and enjoys watching me get horny. However, that's another story. This is the event you might find interesting. Last year, my best friend messaged me and asked me if I'd be ok if he asked my wife to go to a small event here in town. There was a meet and greet at a venue downtown where two stars of a very popular 80's show would be. I had never really been a fan of this particular show, but I knew he and my wife were huge fans. So I told him to message her and see if she'd want to go. Long story short, he took her out. After she returned home, she was very happy and told me about the event and said they had a wonderful time. When we were in bed later, she was laying beside me, brushing my arm with her fingers and she told me she kissed him. Oh my God! She said she kissed him! I had an instant erection and I had to start stroking. She laughed and was excited that her telling me that turned me on so much. She rubbed my leg and whispered in my ear that she felt she needed to give him a proper thank you because, after all, it was a date. I asked her if he thought it was a date. She said yes, she had made it clear to him that it was a date. And the proper thing to do at the end of a date is to kiss the gentleman. I came so hard and she laughed at me and told me to go to sleep. They haven't gone out ever since, but I can see to this day that she looks at him differently. But I know my place. I am not to push her or bring anything up. This is her adventure and I have to let her play it out her way on her terms. So, my advice to you is to not push anything. Enjoy the dom sub thing with your girlfriend and keep the banter about Greg there, but not pushy. However, you can't beat around the bush. She needs to know what you want, with no innuendos or misunderstood thoughts. Miscommunication kills a relationship. Be truthful and direct. She needs to see that you get excited when you talk to her about him in that way. The seed with your friend and girlfriend is obviously planted and there doesn't seem to be any negative feedback from her from I can see. It looks to me like she's waiting for a green light from you. I think if you keep showing yourself as submissive and showing him as more dominant than you, this will come to it's natural conclusion: your girlfriend orgasming on his cock. Good luck

johnswan
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Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Sat Sep 20, 2025 6:52 am

streetracer wrote:
Sat Sep 20, 2025 4:26 am
Hi Johnswan. I've been following your post since day one because we share a common interest. My best friend and I have been friends for almost 40 years. He fucked my first serious girlfriend right in front of me about 35 years ago. I became a cuckold before I even knew the word even existed. There's never been any weirdness between us over the years, so I will say to the naysayers on here that they have no idea what they're talking about.
Hey streetracer, 40 years with a best friend.... and 35 years ago he fucked your first serious girlfriend!
That's the kind of thing that could seriously damage a friendship, or finish it altogether. Great that you two continued your friendship. Presumably you enjoyed watching?

Was him fucking your girlfriend something that was pre arranged, or was it just a spontaneous thing? You say "serious girlfriend", but did you already have a sexual relationship with her? As in, had you already fucked her?
I'd love to hear more about that. Have you posted that story here somewhere? Any link?

You mentioned "naysayers", but if you are referring only to my thread, then to be fair, most posters have been supportive, and have offered advice.
Some of that advice wouldn't work for me or Lucy. But it's difficult to give people a full history of your life, your likes and dislikes and so on, in just a few posts. So inevitably some of the advice is not best suited.
To read posts from naysayers can also be valuable. Sometimes their motives are just to try to warn you of problems, which is fair enough.
But yeah, negative criticism isn't always good to receive.

But I will say that I've had some excellent PM's from people, and they've helped me a lot in getting my thoughts in a better order.
Plus I've had some horny exchanges too, so that's a real bonus! 😛

It's great that your second wife is starting to slowly embrace your desires.
Do you think she really considered her day out with your friend as a 'date'? Or was she doing it just to please you, to get the reaction you described?

Either way, things sound promising for you. And so hot that your long term friend is the one involved.
That must make things feel super hot for you.

I hope things progress for you. Keep us informed.
I always like to read about guys whose friends are cucking them.

Thanks for your advice and encouragement. It's much appreciated.

streetracer
Prepubescent
Posts: 8
Joined: Fri May 20, 2016 1:46 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by streetracer » Sun Sep 21, 2025 3:46 am

johnswan wrote:
Sat Sep 20, 2025 6:52 am

Hey streetracer, 40 years with a best friend.... and 35 years ago he fucked your first serious girlfriend!
That's the kind of thing that could seriously damage a friendship, or finish it altogether. Great that you two continued your friendship. Presumably you enjoyed watching?

Was him fucking your girlfriend something that was pre arranged, or was it just a spontaneous thing? You say "serious girlfriend", but did you already have a sexual relationship with her? As in, had you already fucked her?
I'd love to hear more about that. Have you posted that story here somewhere? Any link?

It's great that your second wife is starting to slowly embrace your desires.
Do you think she really considered her day out with your friend as a 'date'? Or was she doing it just to please you, to get the reaction you described?

I hope things progress for you. Keep us informed.
I always like to read about guys whose friends are cucking them.

Thanks for your advice and encouragement. It's much appreciated.
There never were any concerns about my friendship with my best friend [let's call him Jay] being damaged. There wasn't any awkwardness or tension between any of us. My girlfriend and I had been living together for about a year by that point, and the moment seemed right. It was spontaneous. It was something she wanted to do. She saw the moment, took it and there was no turning back. She didn't want me to participate, but she did want me to watch and masturbate. He got to finish inside her. I got to squirt on the floor. And I loved it. It opened a whole new world for her and she embraced it. We had several more adventures after that before our relationship eventually ended.

As for my current wife's outing with Jay, she was the one who decided to call it a date. To this day, sometimes she will bring her outing with him up in conversation with me, and always refers it to having been a date.

I don't enjoy posting on here, but I check in from time to time to see what's going on. I saw your post and thought I'd reach out. I hope it all works out for you. Take care

cuckhus715
Trainable
Posts: 64
Joined: Thu Dec 26, 2024 5:15 am

Re: Want my wife to cuckold me with my best friend.

Unread post by cuckhus715 » Tue Sep 23, 2025 4:49 am

My wife cuckolded me with a few of my friends. She dated my best friend Dave for a long time. My friends all love her. Amazing feeling sharing my wife

johnswan
Experienced
Posts: 157
Joined: Fri Aug 15, 2025 10:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Wed Sep 24, 2025 11:52 pm

cuckhus715 wrote:
Tue Sep 23, 2025 4:49 am
My wife cuckolded me with a few of my friends. She dated my best friend Dave for a long time. My friends all love her. Amazing feeling sharing my wife
Have you posted anywhere on here about those encounters? Would love to know some details...😛
Especially about Dave.

Kycouple
Player
Posts: 251
Joined: Mon Jan 25, 2021 8:56 am

Re: Want my wife to cuckold me with my best friend.

Unread post by Kycouple » Thu Sep 25, 2025 12:37 am

My wife has fucked my long time friend and still does to this day. Nothing has changed except her pussy and ass isn’t tight anymore. She likes him cause he always makes her squirt.

Bartleby
Pervert
Posts: 583
Joined: Sun Sep 10, 2017 3:47 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by Bartleby » Thu Sep 25, 2025 7:36 am

johnswan wrote:
Wed Sep 17, 2025 3:16 pm
Sorry to be making a string of posts. But it's difficult, on a phone, to make a post combining quotes from multiple different people, and include my responses. The current 'bad gateway' and time out problems don't make it easy either.

But there has been a small development that might be of interest, that I thought I'd post about separately.

A fellow member pm'd me and we've had an interesting exchange of messages.
One thing he suggested was setting some 'dares' for me to do. I was curious, so asked him to suggest some. One that he came up with was to dare me to wear a pair of Lucy's panties when Greg, my friend, was next visiting us.
I thought this was easy enough to do, and might be interesting.
We did already have a visit from Greg planned for last Saturday evening.
But, in the meantime I thought it might be even more interesting if Lucy knew what I was doing.
So, on Friday evening I initiated a sex session, which I suggested should be a Dom/sub one. I made an excuse that I'd had a stressful day at work, and needed to 'detox'.
During that session I asked Lucy to 'make me' wear her used panties. Which she was delighted to do! She was actually quite surprised that I was initiating it, as I had always previously been reluctant to do it.
Anyway, when we'd both got rid of our frustrations (ok, we'd both cum) I kept her panties on while we chatted. Which she eventually remarked upon. I normally take them off at the first opportunity.
At which point I chanced saying to her, "What about I wear your panties, under my shorts, when Greg comes over tomorrow?"
This surprised her, but puzzled her. She asked me why I wanted to do that. I must admit, I hadn't really come up with a good answer for why. But just told her that the idea sort of thrilled me, in a kinky sort of way.
She wasn't sure initially, but eventually said, "If you want to. But do you want Greg to see them on you?" I immediately told her that no, that wasn't the intention, and that would be a bad idea.
Saturday, before Greg arrived, Lucy checked with me if I still intended to wear her panties under my shorts. I said I did. And she insisted that I wear the pair I'd had on, on Friday. Which hadn't been laundered, and had a rather 'used' gusset. Lucy had worn them all day Friday. She also insisted on watching me put them on, I think to make sure I was serious. I didn't tell her that this idea came about as part of a dare.

Greg's visit came and went, and we had a good evening. I did get worried a few times that Lucy was going to 'out' me. She put her hand on my bottom a few times and felt me up, discretely, giving me a wicked smile. Which got my heart racing!

So no great event. But on Sunday we did get chatting about it. Lucy was thinking that maybe I was wanting to let Greg know about my sub ideas, or even wanting to reveal our Dom/sub sessions. I assured her I wasn't. I think that's a step way too far at the moment.
We talked about it again on Monday, and Lucy was teasing me at one point, saying that Greg would love to see me wearing a cute pair of panties. I told her, "don't you dare say anything to him".
And then I just added, "I bet he'd love to see you in those panties!"
Which surprised her! She just said "Yeah, I bet he would!"
After which she went quiet.

Ok, not a huge leap forward. But it does possibly give me a chance to pick up the conversation again, and ask her about her reaction.
Fingers crossed that I can steer the chat in the right direction.


The fact that your wife is open to dom play makes me believe she would be open to your ideas. Maybe not following through, but listening to them

You could explain to her what Greg means to you by talking about him helping you against bullies and then continuing that he fucked a girl you had a big crush on. She would understand why you wanted to wear panties with him in the house then. At that stage, it will probably dawn on her that you want her to have sex with him.

Which would be a wonderful thing imho and I hope it will happen. I have similar feelings and can complety understand you. I can imagine your wife will as well. Even if she does not want to spread her legs for him, I am sure she would not be angry with you for the proposal.

Also, give it a thought about them fucking without you being present. That could be a good start and from experience I can tell you that it feels wonderful as well.

johnswan
Experienced
Posts: 157
Joined: Fri Aug 15, 2025 10:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Fri Sep 26, 2025 11:18 pm

Bartleby wrote:
Thu Sep 25, 2025 7:36 am
The fact that your wife is open to dom play makes me believe she would be open to your ideas. Maybe not following through, but listening to them
Hi Bartleby. Yes, I think Lucy's dom play does provide an opening for me to talk to her about "another man".
This weekend we are free of any other commitments, so I'm hoping to start some discussions about some things. As well as having a good Dom/sub session. I feel the need for a strong (or Level 3) session. 😁

I've been in discussion via pm with an experienced cuck who has made some great suggestions. Also he has helped me to get some more clarity to some issues. It's funny sometimes, that being in the centre of things, you sometimes 'can't see the wood for the trees', as the saying goes. It often needs a more seasoned, experienced person to see things more clearly, from an outside perspective.
I won't detail anything more at the moment, but will update soon.

My thinking is that, for now, I will slowly move to talking about "another man", keeping Greg out of it. That way I won't have done any damage if she reacts badly to the general idea.

You mentioned about them fucking without me present. My preference is definitely to be there. But, if being absent makes things easier, then I'd accept that. But just hope to move things on to my being there, at a later date.

Thanks for your encouragement.

You said "from experience I can tell you that it feels wonderful as well".
Have you written anywhere on the forum about your experiences? Would love to read them.

cuckhus715
Trainable
Posts: 64
Joined: Thu Dec 26, 2024 5:15 am

Re: Want my wife to cuckold me with my best friend.

Unread post by cuckhus715 » Sat Sep 27, 2025 6:47 am

I haven't I can talk about it here or privately. I have pics too

Bartleby
Pervert
Posts: 583
Joined: Sun Sep 10, 2017 3:47 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by Bartleby » Mon Sep 29, 2025 9:31 pm

johnswan wrote:
Fri Sep 26, 2025 11:18 pm
Bartleby wrote:
Thu Sep 25, 2025 7:36 am
The fact that your wife is open to dom play makes me believe she would be open to your ideas. Maybe not following through, but listening to them
Hi Bartleby. Yes, I think Lucy's dom play does provide an opening for me to talk to her about "another man".
This weekend we are free of any other commitments, so I'm hoping to start some discussions about some things. As well as having a good Dom/sub session. I feel the need for a strong (or Level 3) session. 😁

I've been in discussion via pm with an experienced cuck who has made some great suggestions. Also he has helped me to get some more clarity to some issues. It's funny sometimes, that being in the centre of things, you sometimes 'can't see the wood for the trees', as the saying goes. It often needs a more seasoned, experienced person to see things more clearly, from an outside perspective.
I won't detail anything more at the moment, but will update soon.

My thinking is that, for now, I will slowly move to talking about "another man", keeping Greg out of it. That way I won't have done any damage if she reacts badly to the general idea.

You mentioned about them fucking without me present. My preference is definitely to be there. But, if being absent makes things easier, then I'd accept that. But just hope to move things on to my being there, at a later date.

Thanks for your encouragement.

You said "from experience I can tell you that it feels wonderful as well".
Have you written anywhere on the forum about your experiences? Would love to read them.
I believe that you make this is fear of your wife rejecting your proposal too big in your head. Your wife is open to sexual kinks so why should she take deep offense at your offer? She may reject it, but she will certainly not leave you just because you asked.

Chances are that she will be happy about it. The same goes for Greg. He is your best friend, so why not offer him such honour and joy as to have sex with your wife? He is unlikely to reject her, and if she rejects him, that probably will not lead to her taking offense with you. In that case, let her take a different lover. Just take the courage and let her know of your desires!

As for me: My wife had repeatedly asked me to open up our relationship so she could have sex with other men. I refused, it led her to cheat on me. Then I realised how joyful it is to be a cuckold and she has taken more lovers in the years after that. I have only been allowed to witness very little of her fornications, but she tells me of them which fills me with arousal and pride.

I have written about this a long time ago. There is a function in the forums that allows you to find all threads of users. That is probably the best way to learn about my story.

johnswan
Experienced
Posts: 157
Joined: Fri Aug 15, 2025 10:17 pm

Re: Want my wife to cuckold me with my best friend.

Unread post by johnswan » Mon Sep 29, 2025 11:36 pm

Bartleby wrote:
Mon Sep 29, 2025 9:31 pm
I believe that you make this is fear of your wife rejecting your proposal too big in your head. Your wife is open to sexual kinks so why should she take deep offense at your offer? She may reject it, but she will certainly not leave you just because you asked.
Thanks for your response.

The fact that my wife is open to certain sexual kinks doesn't mean that she's necessarily open to everything. She might not take deep offense at me suggesting another man to have sex with her.
And, you are right, she is unlikely to leave me, just because I suggest it.

But there is a thing called trust between a married couple. Well, at least there is between this married couple. And I don't think, at the moment, we are at the right point to put that trust at risk.

She knows nothing of my desires for her to have a lover, to cuckold me.
That is a far cry from having some kinky fun just between the two of us.
There is no way that I am going to risk breaking that trust that exists between us, until I feel the moment is right.
I am making moves towards that moment, but I don't feel we are there yet.

It does disturb me, a little, how people here are so keen for others to push on in their potential cuckolding adventure.
But it's not their relationship that they are risking.

I would say to any other readers, who are considering, or attempting, to go down a cuckolding path with a long term partner, "Go at a pace you are comfortable with. Do not try to satisfy the desires of people that are simply onlookers".

That's not to criticise people commenting here. I've been a lurker on the site for a long time before becoming a member.
I know how things go, how people comment, and the things they say.
So, to receive encouragement to push ahead comes as no surprise to me.

And, to be honest, one of the purposes of me posting about my journey was to pressurise myself, in some small way, to take the process forward.
But, it was not to give in to outside pressure, no matter how well intentioned.

If my journey isn't going fast enough for some people......tough.
You'll just have to be patient.

elina
OHW Addict
Posts: 1994
Joined: Sun Mar 05, 2023 1:29 am

Re: Want my wife to cuckold me with my best friend.

Unread post by elina » Mon Sep 29, 2025 11:46 pm

johnswan wrote:
Mon Sep 29, 2025 11:36 pm
.....
That's not to criticise people commenting here. I've been a lurker on the site for a long time before becoming a member.
I know how things go, how people comment, and the things they say.
So, to receive encouragement to push ahead comes as no surprise to me.

And, to be honest, one of the purposes of me posting about my journey was to pressurise myself, in some small way, to take the process forward.
But, it was not to give in to outside pressure, no matter how well intentioned.

If my journey isn't going fast enough for some people......tough.
You'll just have to be patient.
I agree with you, you are the one who live with your Wife and knows Her best,
Move at a pace you are comfortable with.

If you want to put pressure on your self and have progress, there is one way that I am confident no Woman will hold against you,
See if maybe adopting the following principles will (slowly?) get your Wife to move in the direction you want Her to:

1) Treat Her like a Queen, emphasize how much you love Her and that you more and more realize that Her happiness is the most important thing for you.
2) Buy Her flowers
3) Always focus on Her sexual needs and desires; eat Her pussy for as long as She would like,
only move to fucking Her when it is clear that this is what She wants,
Tell Her how happy you are when you experience that She is orgasming and ask Her if She can help you to become better at this
4) Take on more chores and never say No when She requests something....

See how it goes, the purpose is to build Her self confidence, and Her confidence in your loyalty to Her regardless of what She decides to do. If She indicates that She may consider flirting with other males, support Her, tell Her that you only want to see Her happy and tell Her to please be open about what She is doing....

Just my thoughts, see if this might work for you.
You can start small and gradually increase your efforts...

Sincerely
elina
(Submissive male)

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