Want my wife to cuckold me with my best friend.

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

Post by johnswan » Thu Oct 30, 2025 3:01 pm

coastalkid wrote:
Thu Oct 30, 2025 9:59 am
It sounds like Lucy isn't sure or convinced that there won't be some negative results of what you want. She may be thinking about how this may change things in your "non-sexual" relationship (ie the greater part of your time together). She may be concerned that changes that occur will be permanent and cause her to lose the man she loves now. She might be thinking that she doesn't want it in real life because it would involve a "third party" that comes with all the unknowns that she can't anticipate or prepare for. All of this is nothing more than speculation on my part. You'd have to ask her yourself. I'm just going by what I read, think and feel.
You've pretty much nailed it.
The conversation we had was much more detailed than the summary I posted earlier. And in that conversation we talked about all of the concerns you mentioned, plus some more.

When Lucy first told me that she preferred to keep things at a fantasy level, at least for now, I was disappointed.
But later, as I thought about it, I was quite pleased. Because, if she'd have enthusiasticly taken the opportunity to fuck someone else, I might have had concerns about the strength of our relationship.
Or the quality of our sex life!

One thing I am learning, is that it's difficult to anticipate the consequences of our actions, even when we try to think ahead.

For example, I hadn't anticipated quite the level of discomfort that having your pubes and bum hair shaved entails! And Lucy doesn't like my chest hair stubble scratching against her bare boobs.
It seemed like the only solution would've been to shave daily. But that's a non-starter, due to lack of time.

A quick bit of research shows that waxing might be the best option. There's some pain involved, but things stay smoother, longer.

But more about that later.

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

Post by coastalkid » Thu Oct 30, 2025 4:11 pm

I keep myself shaved down below. I do it in the shower. One time I shaved my chest just to see. My wife didn't like it but she does love that I keep myself shaved. She much prefers giving me oral without all that hair around. Of course she doesn't like shaving herself or keeping her pubic hair short. So obviously I have that on a bucket list that may never be checked off.

I give you credit for considering the implications of Lucy being too enthusiastic. Dwell on the fact that you were pleased by her decision. I get the disappointment too. I think you're on the right track. Once some issues get sorted the two of your will have the confidence to play your game. Those little (or big) insecurities are a double edged sword. They bring that edge, that excitement, but they can also bring anxiety and darker feelings.
Hope is not a strategy but it's still good to have! Especially if you don't have a strategy!
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Re: Want my wife to cuckold me with my best friend.

Post by Coolcalm » Thu Oct 30, 2025 6:24 pm

johnswan wrote:
Thu Oct 30, 2025 3:01 pm
coastalkid wrote:
Thu Oct 30, 2025 9:59 am
It sounds like Lucy isn't sure or convinced that there won't be some negative results of what you want. She may be thinking about how this may change things in your "non-sexual" relationship (ie the greater part of your time together). She may be concerned that changes that occur will be permanent and cause her to lose the man she loves now. She might be thinking that she doesn't want it in real life because it would involve a "third party" that comes with all the unknowns that she can't anticipate or prepare for. All of this is nothing more than speculation on my part. You'd have to ask her yourself. I'm just going by what I read, think and feel.
You've pretty much nailed it.
The conversation we had was much more detailed than the summary I posted earlier. And in that conversation we talked about all of the concerns you mentioned, plus some more.

When Lucy first told me that she preferred to keep things at a fantasy level, at least for now, I was disappointed.
But later, as I thought about it, I was quite pleased. Because, if she'd have enthusiasticly taken the opportunity to fuck someone else, I might have had concerns about the strength of our relationship.
Or the quality of our sex life!

One thing I am learning, is that it's difficult to anticipate the consequences of our actions, even when we try to think ahead.

For example, I hadn't anticipated quite the level of discomfort that having your pubes and bum hair shaved entails! And Lucy doesn't like my chest hair stubble scratching against her bare boobs.
It seemed like the only solution would've been to shave daily. But that's a non-starter, due to lack of time.

A quick bit of research shows that waxing might be the best option. There's some pain involved, but things stay smoother, longer.

But more about that later.



Also keep in mind that you don’t have to allow them to have a relationship, or private time together. Having her fuck someone else can be had but if you control the connection/plans/conversations and the meetups then they won’t be able to get together apart from you.
Sometimes it seems the problem is when the husband (BF, etc…) allows a relationship , apart from him, to start building. Now this is only if you just want to see her fuck another man. If part of your deal is the angst of having her being possibly taken from you then that’s a whole other deal.

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

Post by Dream Weaver » Thu Oct 30, 2025 10:04 pm

I've been following this off and on, your situation has so much potential. You were worried about bringing it up way back at the beginning of the thread, and now she knows. The good news, she didn't bite your head of. The bad news, she's hesitant, didn't jump in head first, haha. But that's rare.

I'd consider giving her very small bites, not "the whole enchilada", as they say. Small bites designed to "make you squirm".

Tell her it's VERY HOT and she will definitely make you squirm by doing the little things. Letting a guy giver her his number. A girl's night out. Striking up a conversation on holiday. Setting up a dating profile for kicks. Considering how long you've been together, she might be curious just because it's such an overtly "i want sex" thing to do that society finds acceptable. But she doesn't have to use it. Tell her not to use it at all. Hell, she could get dolled up and go out on an innocent little dinner and drinks date with Greg with him being clued in. Nothing big. No romance. Just look like a couple. Just make you squirm.

And of course if she does any of these little things, she MUST tell you about it. Otherwise, there's no point.

The jumping into bed conversation is done, you did it. She knows. She gave you the "escalation" pushback, i.e., "but what if the guy I chat up wants to fuck me in the ass while I'm tied up at the carnival by circus midgets, would you be okay with that?" That wasn't a serious request to do more, but a defense mechanism that kicked in subconsciously. Another way of saying "you're fucking crazy", but being nice about it.

You're trying to pick a lock here. There are some bull types here who definitely give good advice in p.m.'s I'm sure, but this is my 2 cents. I also met my at college age. I was successful, eventually, but I think I made the mistake of being too pushy about "the whole thing" early on. I'm glad you two seem to communicate so well.

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

Post by johnswan » Fri Oct 31, 2025 11:55 pm

Coolcalm wrote:
Thu Oct 30, 2025 6:24 pm
If part of your deal is the angst of having her being possibly taken from you then that’s a whole other deal.
Having her being possibly taken from me is definitely not on my agenda.

I know there are a few people on here who like that idea, but it's not for me.

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

Post by johnswan » Sat Nov 01, 2025 12:06 am

Dream Weaver wrote:
Thu Oct 30, 2025 10:04 pm

I'd consider giving her very small bites, not "the whole enchilada", as they say. Small bites designed to "make you squirm".

You're trying to pick a lock here. There are some bull types here who definitely give good advice in p.m.'s I'm sure, but this is my 2 cents. I also met my at college age. I was successful, eventually, but I think I made the mistake of being too pushy about "the whole thing" early on. I'm glad you two seem to communicate so well.
I'm sure you are right about the "small bites" approach. The 'making me squirm' thing I do find quite exciting, but at the time embarrassing or even slightly humiliating. Which Lucy finds very amusing.

Good to know that you were successful, eventually.

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

Post by sandy691196 » Sat Nov 01, 2025 2:54 am

johnswan wrote:
Thu Oct 30, 2025 3:01 pm
coastalkid wrote:
Thu Oct 30, 2025 9:59 am
It sounds like Lucy isn't sure or convinced that there won't be some negative results of what you want. She may be thinking about how this may change things in your "non-sexual" relationship (ie the greater part of your time together). She may be concerned that changes that occur will be permanent and cause her to lose the man she loves now. She might be thinking that she doesn't want it in real life because it would involve a "third party" that comes with all the unknowns that she can't anticipate or prepare for. All of this is nothing more than speculation on my part. You'd have to ask her yourself. I'm just going by what I read, think and feel.
You've pretty much nailed it.
The conversation we had was much more detailed than the summary I posted earlier. And in that conversation we talked about all of the concerns you mentioned, plus some more.

When Lucy first told me that she preferred to keep things at a fantasy level, at least for now, I was disappointed.
But later, as I thought about it, I was quite pleased. Because, if she'd have enthusiasticly taken the opportunity to fuck someone else, I might have had concerns about the strength of our relationship.
Or the quality of our sex life!

One thing I am learning, is that it's difficult to anticipate the consequences of our actions, even when we try to think ahead.

For example, I hadn't anticipated quite the level of discomfort that having your pubes and bum hair shaved entails! And Lucy doesn't like my chest hair stubble scratching against her bare boobs.
It seemed like the only solution would've been to shave daily. But that's a non-starter, due to lack of time.

A quick bit of research shows that waxing might be the best option. There's some pain involved, but things stay smoother, longer.

But more about that later.
I fully emotionally empathise and intellectually resonate with the concerns you and Lucy have raised. My bet is that Lucy, being a deep girl, actually imagined the whole thing in her head with a real person as the imagined lover. She checked herself out, so to say.. She discovered a ton of negative possibilities that can emerge even from a successful MFM or even a solo session.
She worked out the aftermath in a simulation-modelling exercise in her mind. Girl has got depth and wisdom!
She concluded that the risks outweigh the benefits and the nature of the risks is such that certain things can't be undone and may spiral and get out of hand.. Emotions, broken trust, temptations, awkwardness, spin offs.. a whole lot of possibilities.

There is one narrow ray of "hope" though. If factors like the aftermath, spin offs, spiralling emotions and undoable damage are the primary concerns.. then an organic play out of home range may be considered. Where stuff can just be cut off at the location and in the moment. No scope for spin offs and carry forwards.
Of course the basic fact that a 3d person joined you two (or her alone) in bed can't be undone. But all the rest of it can just be dumped at that location before returning home.

Worth a thought? Why I am saying this is that this kink, once it has excited you in the head, keeps coming back again and again till resolved one way or the other..

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

Post by johnswan » Sat Nov 01, 2025 11:33 pm

sandy691196 wrote:
Sat Nov 01, 2025 2:54 am
There is one narrow ray of "hope" though. If factors like the aftermath, spin offs, spiralling emotions and undoable damage are the primary concerns.. then an organic play out of home range may be considered. Where stuff can just be cut off at the location and in the moment. No scope for spin offs and carry forwards.
Of course the basic fact that a 3d person joined you two (or her alone) in bed can't be undone. But all the rest of it can just be dumped at that location before returning home.

Worth a thought? Why I am saying this is that this kink, once it has excited you in the head, keeps coming back again and again till resolved one way or the other..
Thanks sandy691196.

That's a good idea. A sort of holiday romance, a one off thing, where the other man goes his own way afterwards, and we go ours.
The main difficulty there would be that he would be a stranger, and we'd know nothing much about him. One problem could be worries about std's. Although use of a condom could alleviate that. Which is something that Lucy wouldn't be keen on.

But, it needn't lead to full sex. It could just be an opportunity for Lucy to sort of practice being seduced, maybe just going as far as a hand job for the guy.

It's an idea that I'll have to work on, maybe tell her a fantasy or two with that scenario, and gauge her reaction.

I'm planning a weekend away for sometime soon, away from where we might be known, for Lucy to fulfill my wish for her to dress sluttishly in public.
Could be a good opportunity for her to get chatted up, seduced and more.

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

Post by sandy691196 » Sun Nov 02, 2025 12:52 am

johnswan wrote:
Sat Nov 01, 2025 11:33 pm
sandy691196 wrote:
Sat Nov 01, 2025 2:54 am
There is one narrow ray of "hope" though. If factors like the aftermath, spin offs, spiralling emotions and undoable damage are the primary concerns.. then an organic play out of home range may be considered. Where stuff can just be cut off at the location and in the moment. No scope for spin offs and carry forwards.
Of course the basic fact that a 3d person joined you two (or her alone) in bed can't be undone. But all the rest of it can just be dumped at that location before returning home.

Worth a thought? Why I am saying this is that this kink, once it has excited you in the head, keeps coming back again and again till resolved one way or the other..
Thanks sandy691196.

That's a good idea. A sort of holiday romance, a one off thing, where the other man goes his own way afterwards, and we go ours.
The main difficulty there would be that he would be a stranger, and we'd know nothing much about him. One problem could be worries about std's. Although use of a condom could alleviate that. Which is something that Lucy wouldn't be keen on.

But, it needn't lead to full sex. It could just be an opportunity for Lucy to sort of practice being seduced, maybe just going as far as a hand job for the guy.

It's an idea that I'll have to work on, maybe tell her a fantasy or two with that scenario, and gauge her reaction.

I'm planning a weekend away for sometime soon, away from where we might be known, for Lucy to fulfill my wish for her to dress sluttishly in public.
Could be a good opportunity for her to get chatted up, seduced and more.
An organic hook up is the best. In a bar, strip club.. there are sex clubs too. You need to plan it well so that when the opportunity arises in the moment, you don't bungle it .

You need to role play it beforehand. Flashing to be successful, needs to be practiced. All the different scenarios that can develop from flashing in a bar need to be worked out in advance. Will she be a cheating wife on the prowl awa from home base? Can she carry that off?
Will she say that she is a hotwife and hubby is on board? Many guys would run from that unless they are familiar with the LS.
A married man might be safer std wise? Like one meets couples on cruises or tours. The hubby can be seduced. Major adrenaline rush and competitive victory for her!

Even if its limited to her giving a bar pick up a HJ in a car.. and he sucking her pussy off.. it will break the barrier and make her a successful HW.
From there it can build up. Next time a guy can be found in advance on a site who can produce a clean bill of health.. in a town where you plan to visit.

Hey! Have you guys thought of business travellers visiting your city? They too are like sailors passing through ports and having a girl in each port.
They too aint locals with baggage and "tomorrows"..
Accomplished businessmen who can show her a good time for the evening while she shows 'em a good time in bed?

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

Post by allways » Mon Nov 03, 2025 3:58 am

johnswan wrote:
Mon Aug 18, 2025 3:20 pm
Now, all my fantasies revolve around Greg fucking my wife.
Would he? He'd try to resist, and I'm sure he wouldn't do it behind my back. He could have tried before now, but hasn't. But if I gave him the green light I don't think his moral compass would guide him for too long.
Would Lucy be up for it? If asked straight out, she'd say "No way". But, she is quite open minded and sexually is ok with trying different things. I think she could be persuaded.
Hi johnswain wow have you progressed since I gave you my view in August on you both being young and it is a journey and you have plenty of time. It took us ten years before it happened and it is been ongoing with the same man for 27 years. Lucy's response of her concern with reality and your relationship makes Greg the ideal candidate. Lucy may be like my wife and only ever want the one stud. However unlike my wife's lover who is happily married and had had a vasectomy Greg is single. I also assume you would want Greg and Lucy to play bare back.

For your ages you have played this phenomenally well in getting Lucy's juices perculating. Normally couples are in their late 30's early 40's before exploring this as the vanilla sex no longer satisfying. Your risk is when Greg mounts your pretty wife you may find she may not leave you but you had better get use to wearing the cage semi permenantly. :oops:

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

Post by johnswan » Tue Nov 04, 2025 8:54 am

allways wrote:
Mon Nov 03, 2025 3:58 am
Hi johnswain wow have you progressed since I gave you my view in August on you both being young and it is a journey and you have plenty of time. It took us ten years before it happened and it is been ongoing with the same man for 27 years. Lucy's response of her concern with reality and your relationship makes Greg the ideal candidate. Lucy may be like my wife and only ever want the one stud. However unlike my wife's lover who is happily married and had had a vasectomy Greg is single. I also assume you would want Greg and Lucy to play bare back.

For your ages you have played this phenomenally well in getting Lucy's juices perculating. Normally couples are in their late 30's early 40's before exploring this as the vanilla sex no longer satisfying. Your risk is when Greg moun ts your pretty wife you may find she may not leave you but you had better get use to wearing the cage semi permenantly. :oops:
Thanks for your your post.

"The same man for 27 years"
Wow, that's quite an amazing run. Glad that it's working out for you. Have things changed much over those 27 years?

Greg and Lucy playing bareback would be my ideal. The only problem I can see, in that situation, is that he doesn't keep a girlfriend for that long. So if he was also wanting to carry on with his girlfriends, we'd have to be careful about std's. He's never mentioned anything to me about catching anything, but maybe I'll try to find out what he does in terms of him protecting himself. But that's something to think about for the future, should things progress in that direction.

I understand what you say about the vanilla sex possibly becoming routine and unsatisfying. I've always tried to vary what we do, where we do it, etc, so as to avoid that. Plus, with our Dom/sub stuff and the things added from our wishlists, which we're slowly working through, we've got lots of variations to explore.

".....you had better get use to wearing the cage semi permenantly"

I've just ordered a cage, which should arrive tomorrow. Another thing to explore! 😀
But wearing it semi permanently would be a daunting prospect! 😲

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

Post by coastalkid » Tue Nov 04, 2025 11:53 am

I think you're doing a good job of balancing your cravings for your kink and your need for security and comfort. So often men that are obsessed with the hot wife/cuckold kink seem desperate, like they were hit with the Martian Slut Ray that women (supposedly) get when they embrace their sexuality/freedom. They'll do anything, make compromises, whatever just to have it happen.

Both you and Lucy seem to be less gripped by urgency and more focused on functionality. You seem to understand (even though you may be too young to know it) the old adage of, "An ounce of prevention is worth a pound of cure". It's a tricky thing you're trying to do. It involves different personalities and different emotions.

While many may not like your more cautious approach I do. I think you'll be much more satisfied and prepared, Lucy too. I imagine there are people that would advise you to just do it, you'll never be more ready than you are right now! They'll say, just do it, you'll wonder why you didn't start this a long time ago! They also have the luxury of NOT having to be there when things don't go quite as planned.

As to the semi-permanent chastity, I'm not so sure or sold on. For short periods of time maybe. Something I know I'll NEVER say on my death bed is, "I wish I had spent LESS time fucking!" Sure, I can see the thrill of being denied for a while, but words like "permanent" or "never" are showstoppers! Full stop! The fun just ended!
Hope is not a strategy but it's still good to have! Especially if you don't have a strategy!
I get my denial the old fashion way, I married vanilla!

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

Post by johnswan » Tue Nov 04, 2025 10:43 pm

coastalkid wrote:
Tue Nov 04, 2025 11:53 am
While many may not like your more cautious approach I do. I think you'll be much more satisfied and prepared, Lucy too. I imagine there are people that would advise you to just do it, you'll never be more ready than you are right now! They'll say, just do it, you'll wonder why you didn't start this a long time ago! They also have the luxury of NOT having to be there when things don't go quite as planned.
Another perceptive post from you. Thanks!

The bit I've quoted I think is relevant to anyone starting out on this adventure, be it hot wife or cuckold. Especially relevant is what you say about them not having to be there when things get out of control.

I like the adage you quote...."An ounce of prevention is worth a pound of cure". I've not come across that one before.

The semi permanent chastity is not something I really want. And I don't think Lucy would want either.
In my wishlist I said...."I want to try out a chastity cage, but not full time. Just for play, and maybe a bit more."
I'm not totally convinced about using a cage. The idea sounds hot. But there's a potential problem, in that if Lucy was to want me to wear it for too long a period, I can see the 'hotness' of it soon turning into resentment or annoyance. It's like when, as a child, you lusted after a new toy or something, but were told you can't have it, maybe because it was too expensive. Your desire for it, or lust, would possibly increase.
But, if you were told that you could never have it then you'd probably get upset and resentful.

It's going to need some experimentation. Of course, it might just turn out to be one of those toys that you thought were going to be great, but quickly end up at the back of a cupboard.

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

Post by chastity_boi » Wed Nov 05, 2025 4:51 am

Of course the longer you’re locked up the more desperate and willing Lucy may be to get cock elsewhere…

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

Post by johnswan » Wed Nov 05, 2025 8:58 am

chastity_boi wrote:
Wed Nov 05, 2025 4:51 am
Of course the longer you’re locked up the more desperate and willing Lucy may be to get cock elsewhere…
That's possible, I suppose. But a bit of a risky route to take.
I'm happy for Lucy to take the lead in the use of the cock cage. But I'd still have to retain a veto on her decisions. After all, I don't think it would be good for me to deny myself regular sexual relief! 😲

The cage will be more of a fun thing, for some added spice. We'll see.

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

Post by bradisalpha » Thu Nov 06, 2025 2:04 pm

johnswan wrote:
Wed Nov 05, 2025 8:58 am
chastity_boi wrote:
Wed Nov 05, 2025 4:51 am
Of course the longer you’re locked up the more desperate and willing Lucy may be to get cock elsewhere…
That's possible, I suppose. But a bit of a risky route to take.
I'm happy for Lucy to take the lead in the use of the cock cage. But I'd still have to retain a veto on her decisions. After all, I don't think it would be good for me to deny myself regular sexual relief! 😲

The cage will be more of a fun thing, for some added spice. We'll see.
It always seems funny to me that a husband wants his wife to become dominant in the relationship, but then still retains veto on her decisions. How freely dominant do you expect her to become with you retaining veto power if you don’t like something ??

You also mentioned in a post a few back on this page that she was hesitant and you wish she would not hold back as much… but then in the next sentence, you said you were glad she didn’t want to dive right in because you would wonder how deep her love for you is. What does that have to do with the risk factor of becoming a hot wife ?? That should be a non-issue before even approaching this lifestyle.

I guess maybe I am more for a commitment to the lifestyle and the dominant/submissive roles the wife and husband usually assume… I guess you could say more “hardcore”. I just thought I would point out that living the fantasy in reality might be pushing too far.

Just my thoughts….

Brad
Brad.. from the beginning.. viewtopic.php?f=8&t=45313
Sissy Cuckold Club.. viewtopic.php?f=8&t=45930

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

Post by johnswan » Thu Nov 06, 2025 11:28 pm

bradisalpha wrote:
Thu Nov 06, 2025 2:04 pm
johnswan wrote:
Wed Nov 05, 2025 8:58 am
I'm happy for Lucy to take the lead in the use of the cock cage. But I'd still have to retain a veto on her decisions. After all, I don't think it would be good for me to deny myself regular sexual relief! 😲
It always seems funny to me that a husband wants his wife to become dominant in the relationship, but then still retains veto on her decisions. How freely dominant do you expect her to become with you retaining veto power if you don’t like something ??
What seems funny to you seems perfectly sensible to me. I don't want my wife to become dominant in our relationship. In our day to day life we both prefer a roughly equal status. Same in our vanilla sex life. In our non-vanilla sex life I'm happy for her to be more dominant, and she likes that too.
But, handing over complete control doesn't seem to me to be a sensible decision. That's just a recipe for allowing resentment to build.
With regard to using a cock cage, this is a new area for us. And I've also pointed out that I see it mainly as being something to add a different spice to some sessions. Lucy might see it slightly differently, but I'd be surprised if she wanted me to wear it long term. And it just seems sensible to me to retain a veto in an area where I might not be totally in agreement.

It seems to me that you think that she should be totally dominant, with no say for me.
That might suit some people. But it wouldn't suit us.
So, "How freely dominant do you expect her to become?"..... I don't expect her to be 'freely' dominant. Perhaps her being freely dominant appeals to your 'bull' sensitivities?
bradisalpha wrote:
Thu Nov 06, 2025 2:04 pm
You also mentioned in a post a few back on this page that she was hesitant and you wish she would not hold back as much… but then in the next sentence, you said you were glad she didn’t want to dive right in because you would wonder how deep her love for you is. What does that have to do with the risk factor of becoming a hot wife ?? That should be a non-issue before even approaching this lifestyle.

I guess maybe I am more for a commitment to the lifestyle and the dominant/submissive roles the wife and husband usually assume… I guess you could say more “hardcore”. I just thought I would point out that living the fantasy in reality might be pushing too far.

Just my thoughts….

Brad
"What does that have to do with the risk factor of becoming a hot wife ?? That should be a non-issue before even approaching this lifestyle."
Nope, sorry, don't understand this bit at all.

"maybe I am more for a commitment to the lifestyle"

It would seem so. You seem to be of the opinion that a cuck and his wife should be 'full on', 100% committed. Fair enough. That's your opinion.
But, firstly, we aren't even at the stage of being a cuckold couple. And I'm not of the attitude that I must be cuckolded or our relationship will die. If Lucy doesn't want to cuckold me then so be it. I'd be disappointed, and would still try to encourage her to do it. But I won't unduly pressure her.
But I hope we can have some fun trying.

"you said you were glad she didn’t want to dive right in...."

It seems to be the expectation here, by a lot of people, that as soon as the husband/boyfriend tells the wife/girlfriend that she has the freedom to have sex with other men, that the wife/girlfriend immediately rushes out and gets fucked by whatever man or men she desires. Which begs the question of the strength of that relationship. If the wife was that keen, with such pent up desires, she'd probably be already having affairs with other men, regardless of what her partner wanted.

I'd suggest that in the majority of cases the transition from 'permission to stray', to actually straying, is quite a gradual one.
But, who knows? It's only a few weeks since I had that conversation with Lucy. She might surprise me yet!

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

Post by coastalkid » Fri Nov 07, 2025 9:32 am

You're going to get a lot of mixed messaging here. There are those that will say, "You're just topping from the bottom!" They'll say, "You just have to accept whatever your wife/gf wants doesn't require your input!" They'll say, "Obviously you're not cut out for this lifestyle if you have a problem with your wife's/gf's freedom!"

Most people can only project THEIR lifestyle onto you and claim it is the ONE way that this lifestyle works. There are "absolutists" that ONLY know THEIR way and discount ANY other approach. To them, they believe they have discovered the "magic formula" that fits for everyone. They believe that since it worked for them it should work for anyone and everyone.

Those people have based their results on what their very specific circumstances are. Then they assume it is a baseline that fits all people/couples. They only know the personalities, the histories of, and the behaviors of the people they have spent time they are closely associated with in accumulating that knowledge. This doesn't account for the myriad of differences in other people's personality types. If your specific circumstances don't fit theirs then they will claim, "You're just not cut out for this lifestyle!" Their "magic formula" ends up working ONLY for them and they only know what works for them.

I have no doubt that these people have had THEIR own success. Sex, emotions, personalities, economic security, self-esteem make for an ENDLESS potential of combinations with a vast possibility or variations in people. In spite of this clearly obvious fact there will still be those that insist that their way works for them and TO THEM it's the only way it works.

This is only my opinion. I'm not so full of myself to believe I'm right about anything or everything. I think what slips by in most of these discussions is the truly important part and that is the sex part is actually easier to achieve than the making it work part. Making it work is the critical part because of the unique and distinct individual parameters.

That doesn't mean that you can't agree with parts that DO fit your desires. This may sound convoluted, but I think you SHOULD do it THEIR way, which is to find what works for you YOUR own way. Isn't that what they did?
Hope is not a strategy but it's still good to have! Especially if you don't have a strategy!
I get my denial the old fashion way, I married vanilla!

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

Post by wannabecUKold » Fri Nov 07, 2025 11:53 am

bradisalpha wrote:
Thu Nov 06, 2025 2:04 pm
you said you were glad she didn’t want to dive right in because you would wonder how deep her love for you is. What does that have to do with the risk factor of becoming a hot wife ?? That should be a non-issue before even approaching this lifestyle.
JS: you said you did not understand what Brad meant by this.

May I give you my suggested interpretation of his words:

The "that" in "What does that" refers (I believe) to the words in bold, the depth of her love for you. The next "That" refers to it also.

Brad is saying you should and must have complete certainty that Lucy loves you deeply. If you are in any doubt about that then don't enter the lifestyle, he is saying. If you know she loves you deeply, you can let her take control without you needing a veto. She will take you a long way along this path, and it might be difficult for you but you will have the assurance and fulfilment of knowing that she is doing what is best for you and her in your marriage.

If you are not sure if her love is deep and strong, do not enter, he is saying.

In your position you might reasonably have doubts and fears about the strength of Lucy's love: you two are young, not married so long, and may still have realistic fears that, if you overdo it, the bond between the pair of you might break. That is why so many couples on here have been married for decades: their commitment to each other and their knowledge of each other is so strong that they are sure of the strength of their eternal life bond, and it will hold.

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

Post by johnswan » Fri Nov 07, 2025 11:09 pm

wannabecUKold wrote:
Fri Nov 07, 2025 11:53 am
If you are not sure if her love is deep and strong, do not enter, he is saying.
This is what I originally said.... "if she'd have enthusiasticly taken the opportunity to fuck someone else, I might have had concerns about the strength of our relationship".


But she didn't.
So therefore I have no concerns.

In other news.....

Earlier this week I received a cock cage that I'd ordered. I waited until Lucy and I were together before opening the package.
She was keen to see it on me. After some fiddling we got it comfortable. And I gave her the lock to insert.

It's a surprisingly comfortable fit. It's metal, but lightweight, almost like it was made of resin. It has a thin strap that goes through the base ring and then behind me, to help keep it in place and not pull against my balls.
Lucy loved the appearance, especially in my shaved state.

I kept it on until we went to bed. Lucy wanted to see what happened when I tried to get erect. She did things that she knew would arouse me. The cage did it's job, in that I wasn't able to get fully erect. The cage was being strained and my cock felt like it was being tightly gripped.
Lucy was slightly concerned. She said it looked uncomfortable. Which it was, but not so much that I wanted it immediately taking off.

Lucy then asked me to tell her a fantasy, while she started to masturbate in front of me. I'd been thinking of different variations of a fantasy where Lucy would encounter another man, but where I would be involved too. I thought this scenario might have a safer feel for her.

So I told her what might happen at a wedding reception that we are going to next month.
I told her that she'd be dancing with another guy, and that he'd told her that he was staying at the hotel for the night, and would she like to join him in his room for a quiet drink. She told him that she was with me, her husband. She intimated to him that I was open minded and not jealous of her being with other men.
I continued the story, telling Lucy that we went upstairs to this guys room. I asked her to describe the guy, assuming she would choose to describe someone of similar age, toned, muscular etc. Her normal preference of a 'fit' guy.
But she surprised me by describing an older man..."maybe in his 40's or even 50's". She explained that there was a man she liked, that was a previous colleague of hers, who had been very helpful to her. She emphasised that he'd never made any sexual moves with her. But she had thought about what it would be like to have sex with him, or someone like him.
So I had to quickly adjust my fantasy. I told her that she'd sit on the edge of the bed with him, me sat in a chair close by. And that he would turn and kiss her. I'd watch. I asked her what would happen next. She told me that they would kiss a lot, very passionately. And she'd eventually take her top off, to encourage him. We got into a bit of a question and answer session, with me feeding Lucy questions to try to direct the action. But I wanted her to give the responses. She said that soon she was naked with the guy, laying on the bed. I asked her what I'd be doing. She said that I'd stripped off too. I asked her if I'd join them on the bed. But she said, "No. You'd have your cock cage on. You'd just have to watch".
Which really did catch me by surprise!
Anyway, we carried on the fantasy, of Lucy being fucked by an older man, right in front of me.

She brought herself to orgasm. By this time my cock was getting very uncomfortable! I asked Lucy for the key, which she'd placed on her bedside table. She could see that I was in discomfort, so gave me the key. It was quite a relief to take the cage off.
After I'd got comfortable again, I laid back while Lucy knelt over my outstretched legs, and she started to wank me. I was very aroused by the turns she had chosen in our fantasy. An older man fucking her has been a hot fantasy of mine.

So an interesting session. For a change, she chose an older man. But someone she already knew. So she was still playing fairly safe. But the biggest surprise to me was that she was happy for me to stay locked, and just watch! Much more 'cucky' than I had expected.
I was quite pleased. 😀

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

Post by Dream Weaver » Fri Nov 07, 2025 11:14 pm

Great update! I can't help but wonder if she's thinking about a real guy. Not that there's anything wrong with that! :evil:

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

Post by Wantsomefunto » Sat Nov 08, 2025 4:13 am

Great progress! Is it time to get her together with your friend you want her to fuck? Or at least tell her you have a fantasy she fucks him?

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

Post by Paulypippa » Sat Nov 08, 2025 5:00 am

Wantsomefunto wrote:
Sat Nov 08, 2025 4:13 am
Great progress! Is it time to get her together with your friend you want her to fuck? Or at least tell her you have a fantasy she fucks him?
Yeah I tend to agree that he has to be played in somehow and let her know what he has to offer a lady. That can possibly provide the spark needed

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

Post by joel68 » Sat Nov 08, 2025 5:42 am

Yeah, now that you have planted the seed and have had some positive feedback, maybe talk about guts you know. Them possibly mention your friend.

Just a thought.

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

Post by johnswan » Sun Nov 09, 2025 11:15 pm

Thank you to Dream Weaver, Wantsomefunto, Paullypippa and joel68 for your encouragement.

Yes, there is definite progress. Lucy does now seem comfortable with the general idea of sex with another man. But, as she has already said, she's only comfortable with it as a fantasy.
So, it's still got to be slow and gentle encouragement from me.
I'm trying not to push fantasies on her too often, with an 'another man' element, so that she doesn't think I'm obsessed with the idea. And also so that she doesn't feel that she's being pushed in that direction, and then get resentful about it. It's just a case of, when the time and circumstances are right, I'll try to offer up a new variation of these type of fantasies.

I'm going to have to try to get her to tell me more about her interest in an 'older man'. This might only be this one particular guy, or it might be a more general interest. I'm not sure, because she's never expressed any interest in that direction. She has mentioned this particular guy before, but only as a work colleague who was helpful to her. And no, not 'helpful' in that way!

Also, I was surprised and encouraged that she stated that, in my fantasy, I'd be locked in my cage!
Okay, I was sat directly in front of her, at the time, with the cage on for the first time, so that might have inspired her. My idea with the fantasy I had in mind, was that I'd go with her to this guys hotel room. Which I thought might be something that she'd find safer to do. And I was going to tell her that we'd both have sex with her. And see if she liked that idea.
But when she said "No. You'd have your cock cage on. You'd just have to watch"., I was rather caught by surprise, and had to continue the fantasy with me just watching!

One thing I introduced this time, was to ask her more questions as I told her the fantasy. I'd say things like "what did he do next?", or "what did you do next?", and so on, so as to get more ideas of what she wanted to happen, rather than me directing it all. Only thing with that approach is that I have to be quick to change the direction of the fantasy!

I'm hoping that soon she will have a fantasy of her own to tell me, on the same theme. In the past though, she's always wanted me to tell a fantasy, if that was the spark needed for some sex.

I've got a little story to tell, about our waxing session, on Saturday evening, that a friend/'colleague' of hers volunteered to do for us.
Nothing super sexy or cucky to it. But there were erotic elements! Inevitable I suppose, when you and your wife are naked and handled by another woman!

But I've no time today to add that, so I'll post it later.

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