Best Friend Dilemma

[patmoll]

Hi all,

Backstory is that I have wanted my wife to become a hotwife nearly our entire 20 year relationship. Back in 2015 I finally plucked up the courage to tell her about wanting her to become a hotwife. To my relief, she was not disgusted by my thoughts. She said she was intrigued and wanted to know more. After discussing it a bit she told me that she was not saying no, but that she did not want to do it right then but was not ruling it out for the future.

Fast forward to October 2019 and while out in a bar one night I decided to bring up the subject again. I told her that I believed that she fancied my best friend. She admitted that she did. That was the first time she openly admitted to fancying another guy. I asked her if she would like to fuck him and she said that she would. She also admitted to loving the attention of other guys and actually craving that attention. About 3 weeks later we went abroad for a weekend away and on the Saturday night she told me that she would fuck another guy that weekend. I asked her if she wanted to do that because I wanted her to do it or because she wanted to do it. She told me that it was because she wanted to do it. Unfortunately the opportunity never arose that weekend.

Needless to say, I was on cloud 9 as something I had wanted for about 13 years at that stage was finally going to happen. Little did I think that a global pandemic would put a stop to progressing but that is what happened. We never got a chance to start because of the lockdowns and covid precautions. Now, with covid firmly in the rear view mirror as regards lockdowns etc, I am at the point where I would like to bring up the subject again. My wife has not said that she is ready to play yet but I know if the opportunity to fuck my best friend was on the table that she would immediately be ready to play.

My question is; should I set up something with my best friend and my wife? I know that she fancies him and would love to fuck him. I also know that he would like to fuck her. He is a ladies man and has fucked over 150 women and has no problem separating sex from everything else, that is actually one of the things that attracts my wife to him - the fact that he can have any women he wants and wants to have her would be a massive confidence boost for her. I have not spoken to him about any of this and he does not know that my wife wants to fuck him. It is also something that I would love to happen. I have had years to think about them fucking and it does turn me on. My fear, however, is if that would be too close to home to be playing and the risks it could have on our friendship. If we were experienced in the lifestyle, then I would not be as worried but for a first time encounter - is it a good idea?

I would appreciate any opinions or experiences that people here have had with playing with a best friend, especially if it was their first time playing and how it all worked out for them.

[Long Lurker 34]

Hi all,

Backstory is that I have wanted my wife to become a hotwife nearly our entire 20 year relationship. Back in 2015 I finally plucked up the courage to tell her about wanting her to become a hotwife. To my relief, she was not disgusted by my thoughts. She said she was intrigued and wanted to know more. After discussing it a bit she told me that she was not saying no, but that she did not want to do it right then but was not ruling it out for the future.

Fast forward to October 2019 and while out in a bar one night I decided to bring up the subject again. I told her that I believed that she fancied my best friend. She admitted that she did. That was the first time she openly admitted to fancying another guy. I asked her if she would like to fuck him and she said that she would. She also admitted to loving the attention of other guys and actually craving that attention. About 3 weeks later we went abroad for a weekend away and on the Saturday night she told me that she would fuck another guy that weekend. I asked her if she wanted to do that because I wanted her to do it or because she wanted to do it. She told me that it was because she wanted to do it. Unfortunately the opportunity never arose that weekend.

Needless to say, I was on cloud 9 as something I had wanted for about 13 years at that stage was finally going to happen. Little did I think that a global pandemic would put a stop to progressing but that is what happened. We never got a chance to start because of the lockdowns and covid precautions. Now, with covid firmly in the rear view mirror as regards lockdowns etc, I am at the point where I would like to bring up the subject again. My wife has not said that she is ready to play yet but I know if the opportunity to fuck my best friend was on the table that she would immediately be ready to play.

My question is; should I set up something with my best friend and my wife? I know that she fancies him and would love to fuck him. I also know that he would like to fuck her. He is a ladies man and has fucked over 150 women and has no problem separating sex from everything else, that is actually one of the things that attracts my wife to him - the fact that he can have any women he wants and wants to have her would be a massive confidence boost for her. I have not spoken to him about any of this and he does not know that my wife wants to fuck him. It is also something that I would love to happen. I have had years to think about them fucking and it does turn me on. My fear, however, is if that would be too close to home to be playing and the risks it could have on our friendship. If we were experienced in the lifestyle, then I would not be as worried but for a first time encounter - is it a good idea?

I would appreciate any opinions or experiences that people here have had with playing with a best friend, especially if it was their first time playing and how it all worked out for them.

PM - Of the 150ish women that your friend as been with, how many were the wives of close friends? Or hit on?
- Point being if he has seemingly no issue going after friends wives then him bedding yours shouldn't be a problem. If there no rumours of him going after friends wives then this could be a hard self imposed limit.

[MarknSusan]

This question about having sex with friends is very common. Most people will tell you to stay away from friends, however for more than 30 years all of our relationships have been our good friends. It’s has created a special bond for us even after the sexual aspect of our friendship faded away.

There is another couple we know that had a one time sexual encounter with a couple that was also a business partner and it did not end well.

There’s a comfort level with having sex with someone we already know and safety is very important to us.

Wishing you the best in your sexual experiences together

[WatchinginNJ]

I've shared girls with friends in the past, and it's been fine. I would even say it's been better with friends that were skilled with the ladies. Like you said, an ability to separate love and sex? It's fun for all.

[Tryagain]

I think you have a perfect situation for a first time. Your wife really likes him already - no endless searching for a good guy. Second, he knows what he is doing and must be very potent - no worries about an inadequate lover. He is a friend who you can easily arrange subsequent meetings with - not a guy who can't make it back for a second time.

No doubt - do it with him.

[Iamgroot]

Our first time with her being shared was with my best friend who came to visit us. He was married, but it was a bad one. He has known my wife since I started dating her and he's like my brother, so she knew him well. We were in the hot tub and had some liquid courage as I let him feel her thigh and covered boob. I went to refill our drinks. When I came back out, she was riding him and he came inside her in the hot tub. It was magical and she was hooked. We played together the rest of his stay. She has since enjoyed 14 other cocks. Not bad for a very picky woman.

[patmoll]

PM - Of the 150ish women that your friend as been with, how many were the wives of close friends? Or hit on?
- Point being if he has seemingly no issue going after friends wives then him bedding yours shouldn't be a problem. If there no rumours of him going after friends wives then this could be a hard self imposed limit.

He has been with plenty of wives but I am not aware of him being with any of my or his close friends wives. I am also quite certain that none of the husbands knew he was with their wives. He has a reputation as a bit of a ladies man but I have not heard any rumours of any relationships breaking up because he was with the wife/GF.

He is not someone who goes around bragging about his conquests and is very discreet so I would have no concerns about that aspect of things.

[patmoll]

This question about having sex with friends is very common. Most people will tell you to stay away from friends, however for more than 30 years all of our relationships have been our good friends. It’s has created a special bond for us even after the sexual aspect of our friendship faded away.

There is another couple we know that had a one time sexual encounter with a couple that was also a business partner and it did not end well.

There’s a comfort level with having sex with someone we already know and safety is very important to us.

Wishing you the best in your sexual experiences together

Good to hear that all your experiences with friends are good. In truth, he is probably the only one of my friends that I would be ok with being with my wife. As for that other couple you knew who played with a business partner - there is a reason they say not to mix business with pleasure, I haven't heard any negative saying about mixing friendship and pleasure

Thanks for the best wishes.

[patmoll]

I've shared girls with friends in the past, and it's been fine. I would even say it's been better with friends that were skilled with the ladies. Like you said, an ability to separate love and sex? It's fun for all.

I think that is one of the things that attracts her to him (aside from the fact that he is a 6'4" ripped personal trainer ) She knows that he has been with that many women, she knows he is a ladies man, but she also knows that he goes after really good looking women and that if he went after her then it means that she is really good looking and attractive to a man who can have any woman he wants. She feels that I tell her she is beautiful and sexy because I have to as her husband (not the case, I tell her that she is beautiful and sexy because she is), whereas other guys say it because they want to. Subtle difference maybe, but that is how she thinks about compliments.

[patmoll]

I think you have a perfect situation for a first time. Your wife really likes him already - no endless searching for a good guy. Second, he knows what he is doing and must be very potent - no worries about an inadequate lover. He is a friend who you can easily arrange subsequent meetings with - not a guy who can't make it back for a second time.

No doubt - do it with him.

Those are a lot of the reasons why I am in favour of them being together. There are a lot of positives but I also need to weigh up the negatives as it is a big decision.

[patmoll]

Our first time with her being shared was with my best friend who came to visit us. He was married, but it was a bad one. He has known my wife since I started dating her and he's like my brother, so she knew him well. We were in the hot tub and had some liquid courage as I let him feel her thigh and covered boob. I went to refill our drinks. When I came back out, she was riding him and he came inside her in the hot tub. It was magical and she was hooked. We played together the rest of his stay. She has since enjoyed 14 other cocks. Not bad for a very picky woman.

That sounds like the perfect outcome that I would like from all this. Maybe I should invest in a hot tub

[leggysman]

If you've decided you'd like this to happen, I suggest starting by asking your wife whether you can start dropping hints or suggestions with your friend. If she says yes - full steam ahead! I understand that she has agreed in principle that it would be hot, but don't go behind her back putting things into motion. Always treat this as a team sport.

[tractorman2]

This is simular to an opportunity i had many years since,In my view i would mention this to your friend and sound him out,

Then if he is in agreement try creat an opportunity for him to come over one evening to see you both, relax and have a few drinks.

If its possible then i would look at leaving them together and see how it goes. For the longer then better.

Or arrange for him to come over when your due home but are then late and give them the opportunity...if necessary several times over a period.

You have told them both and know the attraction is there so if possible in your absence let them decide.

In my experience all you need to do is create an opportunity remembering that any inital chemistry between them is unlikely to occur in your presence.

This is how i created an opportunity for my then best friend, little did i know that having already told my young wife my friend fancied her, she soon after and unknown to me took the opportunity to take him as a lover, so i was planning something that was already happening.

Though on the plus side it did make her want me to know, knowing i would be receptive so whilst i did the above planning she had already arranged with him an evening where i could watch him seduce her for the "first time"

Her later admission that she was already having an affair with him and had, had a previous lover too made me a true cuck husband.

[luvwives999]

Hi all,

Backstory is that I have wanted my wife to become a hotwife nearly our entire 20 year relationship. Back in 2015 I finally plucked up the courage to tell her about wanting her to become a hotwife. To my relief, she was not disgusted by my thoughts. She said she was intrigued and wanted to know more. After discussing it a bit she told me that she was not saying no, but that she did not want to do it right then but was not ruling it out for the future.

Fast forward to October 2019 and while out in a bar one night I decided to bring up the subject again. I told her that I believed that she fancied my best friend. She admitted that she did. That was the first time she openly admitted to fancying another guy. I asked her if she would like to fuck him and she said that she would. She also admitted to loving the attention of other guys and actually craving that attention. About 3 weeks later we went abroad for a weekend away and on the Saturday night she told me that she would fuck another guy that weekend. I asked her if she wanted to do that because I wanted her to do it or because she wanted to do it. She told me that it was because she wanted to do it. Unfortunately the opportunity never arose that weekend.

Needless to say, I was on cloud 9 as something I had wanted for about 13 years at that stage was finally going to happen. Little did I think that a global pandemic would put a stop to progressing but that is what happened. We never got a chance to start because of the lockdowns and covid precautions. Now, with covid firmly in the rear view mirror as regards lockdowns etc, I am at the point where I would like to bring up the subject again. My wife has not said that she is ready to play yet but I know if the opportunity to fuck my best friend was on the table that she would immediately be ready to play.

My question is; should I set up something with my best friend and my wife? I know that she fancies him and would love to fuck him. I also know that he would like to fuck her. He is a ladies man and has fucked over 150 women and has no problem separating sex from everything else, that is actually one of the things that attracts my wife to him - the fact that he can have any women he wants and wants to have her would be a massive confidence boost for her. I have not spoken to him about any of this and he does not know that my wife wants to fuck him. It is also something that I would love to happen. I have had years to think about them fucking and it does turn me on. My fear, however, is if that would be too close to home to be playing and the risks it could have on our friendship. If we were experienced in the lifestyle, then I would not be as worried but for a first time encounter - is it a good idea?

I would appreciate any opinions or experiences that people here have had with playing with a best friend, especially if it was their first time playing and how it all worked out for them.

My wife fucked my best friend 3 months into our marriage. It was a wonderful experience, if you have the opportunity, I say go for it.

[Allinfun]

If SHE decides this is the route she wants to go, invite him to your home. Find a reason to have to leave. See if nature takes its course.

[leggysman]

You have told them both and know the attraction is there so if possible in your absence let them decide.

I don't read anywhere that the OP has talked to his friend about it. And his wife doesn't seem to have agreed to go forward (yet). All we seem to have is that the OP knows (or believes) that each is attracted to the other.

Seems to me like there's some communicating still to do. The OP's wife should first agree, and he should talk to his friend. If the friend doesn't know in advance that it's OK, it would amount to enticing him to do something he'll believe is a betrayal of the friendship. Not a good way to start.

Trying to skip the talking part, and just pushing them together and hoping something happens seems like a bad idea, and less likely to work anyway. Communicate! Don't manipulate!

[jw_kk]

This will be an experiential perspective inverse from your topic. My own wife KK has never had sex (that I know of) with any of my close friends.

In contrast, I’ve had two experiences with the wives of two very close friends. One is an ongoing, and positive thing, the other was a disaster that ended our friendship.

The disaster first: long story short, Danielle (my friend’s wife) and I had our first sexual encounter in her home, with Brad present and watching, but not participating. He was clearly uncomfortable with the experience (Dani’s idea). One thing led to another, with Dani seeing me for sex often, but without Brad present. Unsurprisingly, they’d had a huge fight after our first encounter - lots of emotion…

It turns out Dani was seeing me without Brad’s knowledge. In the end, it ruined their marriage, ending in divorce. Dani went totally downhill after, drugs, multiple DUI, a train wreck. Brad’s fine, remarried, but we’re no longer friends.

The ongoing positive experience is with Rebecca and Zeke. Both were totally bought into the idea of involving me sexually. The first time opportunity arose was during a weekend visit, beginning with an invitation to naked hot-tubbing.

Rebecca is totally hot, strawberry blonde, beautiful, little A-cup tits, pink, perky nipples, a tiny bubble butt, simply a goddess. I couldn’t say no. That hot-tub experience turned into a make-out session in the tub itself, followed by incredible cock-riding, Rebecca writhing and bouncing on my cock on the den sofa, while Zeke watched and jerked his cock.

We’ve been fucking since, about once every couple of months when I visit. Most of the time Zeke watches, other times Rebecca and I have privacy in the guest bedroom. She usually sleeps with me after sex.

So this can go either way, bliss, or disaster. I don’t have advice, other than this is another roll of the dice...

[patmoll]

You have told them both and know the attraction is there so if possible in your absence let them decide.

I don't read anywhere that the OP has talked to his friend about it. And his wife doesn't seem to have agreed to go forward (yet). All we seem to have is that the OP knows (or believes) that each is attracted to the other.

Seems to me like there's some communicating still to do. The OP's wife should first agree, and he should talk to his friend. If the friend doesn't know in advance that it's OK, it would amount to enticing him to do something he'll believe is a betrayal of the friendship. Not a good way to start.

Trying to skip the talking part, and just pushing them together and hoping something happens seems like a bad idea, and less likely to work anyway. Communicate! Don't manipulate!

There is no skipping the talking part or manipulation or pushing them together hoping something happens. As I said in my original message;

I am at the point where I would like to bring up the subject again. My wife has not said that she is ready to play yet but I know if the opportunity to fuck my best friend was on the table that she would immediately be ready to play.

As you can see, I said that I am at the point that I would like to bring up the subject again - ie communicate with my wife. I stated about the opportunity for her to be with my best friend being put on the table as I would not even bring up the subject with him without first discussing with my wife. Communication is something that is vitally important to us both so will never be neglected. It is about 8 years since I first discussed it with her and we have been moving at her pace as ultimately it is her decision. I would never manipulate my wife or even try to.

Also, I asked if I should set something up "with" my wife and best friend, not "for" them. I know it is only semantics but it is an important distinction.

I am sorry if you misinterpreted my original post or perhaps I was not clear in what I was trying to describe.

[patmoll]

This will be an experiential perspective inverse from your topic. My own wife KK has never had sex (that I know of) with any of my close friends.

In contrast, I’ve had two experiences with the wives of two very close friends. One is an ongoing, and positive thing, the other was a disaster that ended our friendship.

The disaster first: long story short, Danielle (my friend’s wife) and I had our first sexual encounter in her home, with Brad present and watching, but not participating. He was clearly uncomfortable with the experience (Dani’s idea). One thing led to another, with Dani seeing me for sex often, but without Brad present. Unsurprisingly, they’d had a huge fight after our first encounter - lots of emotion…

It turns out Dani was seeing me without Brad’s knowledge. In the end, it ruined their marriage, ending in divorce. Dani went totally downhill after, drugs, multiple DUI, a train wreck. Brad’s fine, remarried, but we’re no longer friends.

The ongoing positive experience is with Rebecca and Zeke. Both were totally bought into the idea of involving me sexually. The first time opportunity arose was during a weekend visit, beginning with an invitation to naked hot-tubbing.

Rebecca is totally hot, strawberry blonde, beautiful, little A-cup tits, pink, perky nipples, a tiny bubble butt, simply a goddess. I couldn’t say no. That hot-tub experience turned into a make-out session in the tub itself, followed by incredible cock-riding, Rebecca writhing and bouncing on my cock on the den sofa, while Zeke watched and jerked his cock.

We’ve been fucking since, about once every couple of months when I visit. Most of the time Zeke watches, other times Rebecca and I have privacy in the guest bedroom. She usually sleeps with me after sex.

So this can go either way, bliss, or disaster. I don’t have advice, other than this is another roll of the dice...

It appears to me that the difference between the 2 scenarios above is that in Danielle's case, her husband was not into this at all and it was Danielle's idea and not his so sounds like there were red flags from the start. In Rebecca's case, both she and Zeke were into the idea so a much higher chance of success.

Obviously in my case, I am into it so hopefully we would fall more into the Rebecca/Zeke stable than the Danielle/Brad stable.

[leggysman]

I am sorry if you misinterpreted my original post or perhaps I was not clear in what I was trying to describe.

But I wasn't replying to your original post, sir. I quoted someone else and was referring to some of the other comments/advice.

[patmoll]

I am sorry if you misinterpreted my original post or perhaps I was not clear in what I was trying to describe.

But I wasn't replying to your original post, sir. I quoted someone else and was referring to some of the other comments/advice.

I apologise, no offence was meant. I was just trying to clarify any ambiguity, and it turns out that I was the one who misunderstood.

[leggysman]

None taken, but thanks

Looking forward to hearing how this turns out!

[BT2]

I've followed this Forum back to when Bianca ran it. (Forget the 2007. That year there was a glitch and many if not most of us who were members prior to 2007 were inadvertently deleted from Membership and had to enroll again.) There have been many debates on whether or not you should involve friends in hotwife activities. "Back in the day", maybe three decades ago, a writer by the name of Clarke Kent (no, not that one) wrote an article on how to have a good hotwife experience. One of his strongest points was "never involve friends, relatives, nor co-workers..." However, a little earlier another author wrote that if two couples have strong marriages, and they have dinner, play golf, vacation, etc. with each other there is absolutely no reason by they can't also enjoy exchanging intimate sex including intercourse with those friends.

On this Forum I have read more than a few times that "lovers can become good friends, but seldom do good friends become good [long term] lovers. Yet, other people, as you can see from some of the responses to your question, have had good experience involving a close friend in hotwife activities and would recommend no other way. In my own experience, I have attempted or suggested sexual activity with only three friends which my wife and I were sure were up for it. In two instances it quickly ended the friendship even before any sexual activity took place. In the third instance, we had intimate sex with a woman who had been a friend of both my wife and me for over ten years. It was a great two or so years, but it eventually wound up proving Mr. Kent's advice.

Two things. First, since there is a good chance involving a friend in hotwife activities can end the friendship, you have to weigh the possibility of eventually losing a friend against the possibility of an exciting sexual fantasy coming true. Which of the two is really, in cold, sober thought, worth more? Second, many people on this Forum have written over the years that a hotwife activity has to be shared between a husband and a wife, that it can bring a husband and wife closer together, that it is not an activity for a poor marriage, that the husband and wife must respect one another, etc., so can you in good conscience arrange for your wife to be number 151?

[zorro]

Involving a close friend in sex with your wife can blow up if not done properly. The friend, if there hasn't been clear communication about the arrangement, may feel he is being used as a loyalty test by your wife, to see if he would betray you as his friend by fucking his nwife. Therefore, he needs to know beforehand if there is to be sex that he does not risk betraying you when he puts his cock in her mouth and/or pussy.
I don't know if it is better to you and he to have a discussion beforehand one-to-one or for the three of you to discuss it openly, perhaps with a little wine to contain excessive anxiety.
You might wish to bring up the topic of swinging or wife sharing to test out his values about that. You have reason to believe he likes to bed cheating wives, but he may not do as well with a wife who isn't cheating. Ironically, some men are more comfortable with a cheating than an openly shared wife. You may do well to esplore the issue before offering her up. The idea of fucking a wife who is not cheating may be a turn off for him. Go figure, but so it can be.

[tractorman2]

You have told them both and know the attraction is there so if possible in your absence let them decide.

I don't read anywhere that the OP has talked to his friend about it. And his wife doesn't seem to have agreed to go forward (yet). All we seem to have is that the OP knows (or believes) that each is attracted to the other.

Seems to me like there's some communicating still to do. The OP's wife should first agree, and he should talk to his friend. If the friend doesn't know in advance that it's OK, it would amount to enticing him to do something he'll believe is a betrayal of the friendship. Not a good way to start.

Trying to skip the talking part, and just pushing them together and hoping something happens seems like a bad idea, and less likely to work anyway. Communicate! Don't manipulate!

I agree thats why i suggested he needed to talk to his friend first, as to his wife agreeing, well he stated she had admitting fancying him, now i only suggested making an opportunity to chat, now if they took it any further than having a chat and brew then its down to them.