Long time wannabe now faced with decision regarding her fucking my best friend...

[typerope77]

My wife Daisy has known about my fantasy to share her for about 4-5 years. In that time there have been many ups and downs. Plenty of times she has played along (dressing sexy in public, telling me about guys she caught staring, hot fantasy talk in bed of her taking 2 cocks, etc). And plenty of times when she thought it was all too much and wanted to pump the brakes, only to then bring it up again in bed herself without any prompting from me. One thing has always been constant, and that is that she does not want me messing around with other girls - no thinking, no looking, certainly no touching. I always reassure her that the fantasy for me centers around her being a shared Hotwife and me as her loving and supportive Stag.

Over time, she has progressed from extremely conservative and religious mom, into a hot busty MILF who dresses to kill and turning heads everywhere she goes. She has been working hard on herself too. Over the last year she's been seeing a sex-positive therapist to deconstruct some of the strict religious upbringing that forced her to believe things without question, as well as dealing with the feelings of shame and guilt that are so often used as a means to control other people in those environments. To say I'm proud of her is a massive understatement.

Our bedroom fantasies have been amazing for a while, but at some point this year (probably when her therapy started to take hold), she really ran with the hotwife sharing scenarios and opened up a lot about guys she thinks are hot outside of the bedroom (friends, neighbors, celebrities, etc) and has brought them into our bedroom fantasies. It started with a muscular tattooed guy she met at Walmart we aptly call "Walmart guy" and has just expanded from there. She wears her anklet all the time now. She loves fantasizing about other busty girls too. When we do watch porn, she almost always wants to see girl on girl and doesn't last more than 2 minutes before she's cumming.

Recently I took a gamble and booked us a trip to Temptation. I figured it could be a great way to force us to talk about boundaries and stick to them. As a true submissive, she has a hard time drawing lines only to find herself upset later if she feels like something went too far. So I told her that even though it's a topless resort, she should plan on keeping hers on the entire time. That way she doesn't feel pressured to once we are there. Come to find out (and dispite my constant denial) her biggest hangup was actually me looking at and flirting with other women. After some back and forth, and almost pulling the plug, it seems that we really are going to give it a shot and go. My goal is just to show her a good time and turn away any propositions from swingers so she can see that it's possible to be sexy around other sexy people without doing something regrettable. If we leave the trip with some FOMO that will be a win in my book, giving her plenty of "Oh I totally could have hooked up with that guy/girl" fodder for the bedroom back at home.

Since booking the trip, she is having a lot of fun shopping for risqué outfits and skimpy bikinis. Then things in the bedroom suddenly dialed to an 11 out of nowhere...

Four days ago during sex she confessed that sometimes she thinks about people we know when she cums. She felt naughty about it, but I reassured her it was sexy. Then she asked, "Who do you think?". I took a few guesses, but she kept saying "Who else?" until finally, it was the person I least expected: my best friend Jack. He's a muscular guy, tattoos, extremely respectful, heart of gold, and (according to stories we've heard) has a big dick. Honestly he ticks almost all the boxes for her (except tall, she has a thing for the 6' 6" Hulk types, which he isn't). But truthfully, I just did NOT see it coming since we are so close. Before I could even process it, she's calling me by his name and cumming all over my cock. Of course I immediately cum too and we both collapsed in pure bliss. She later tells me "that was my limit" and it was all "just fantasy talk" then we go about the next two days like nothing happened.

Then two nights ago we are fucking and she brings him up again. This time confessing that she's wanted his cum in her for 3 years now. She says she wants to send videos to him so he can get hard. She LOVES the idea of him getting hard for her. Then she starts fantasizing about watching videos of him cumming. Before you know it we are working out logistics, all while still fucking. We start talking about how often he comes over to fuck her, where I'm sitting watching while they fuck, how I should join in so we can fuck her together, whether his wife can watch too, what position he'll take her in first, how fast she will cum on his cock, how he will force her to things with him she can't imagine doing with me...

Now I can't stop thinking about them fucking. And I'm not sure what I think of it, mostly because I never imagined in 100 years it would be him. For some reason, in my mind I pictured her fucking some tall muscular stud we both barely knew, not my bestie where if things get weird it could ruin a 20 year friendship. At one point she said, "Well, I do already love him", and that is true. He and his wife are both best friends of ours, we genuinely love them, and say it out loud to each other. It dawned on me that because of our close relationship with them she must feel incredibly safe and that she can trust him, which makes a lot sense given how if anyone ever found out her fantasies she would be absolutely mortified. And in some ways I actually feel better about it being him too. What better way to ease in to seeing your wife fuck other people than with someone you completely trust who will stop when you say stop and respect your marriage.

There's a lot more to say, but I guess I'll leave it here. I'm not sure how to proceed because I can see pros/cons either way, and I haven't had much time to think about it. Because she is so willing and has become so awesome at fantasizing in the bedroom, I've grown content to think that's all it would ever be. But here I am with what appears to be a path to seeing it happen for real, but in the way I least expected it.

Has anyone here been in a similar situation?
How did it turn out for you?
What would you do differently if given the chance?

[afagehi7]

Welcome to OHW. Is Jack and his wife into swinging? If not wouldn't he be cheating? That's a dumpster fire waiting to happen. IMO unless he and his wife play that way you'd kill the friendship. His wife will get pissed and jealous and that's the end of that.

Why put such restrictions on the trip? Why not let her go topless or open the door for some play? Kind of like what happens in Vegas. If there are negative feelings about anything you do then you can leave them at the resort.

Personally I'd keep Jack off limits except for bedroom talk and open the door for vacation activities... but I'm certainly not a success story in my relationship so keep that in mind. I'm sure you're going to get some great advice and some terrible advice so do what is right for you and protect your marriage at all costs. We'd love to see some de-identified pics someday. She sounds like a smoke show!

Good luck amigo.

[newUK]

I’d suggest talking to your wife about Jack out of the bedroom. Al lot can be said in the heat of the moment and it’s all fantasy play.

Sit down in the living room with her with your clothes on and have a serious chat about if she wants to really progress with Jack.

I suspect she might say no but she could also admit she does want to. If so then great. That’s when you really need to start thinking how to progress with it. You can chat about how to mention it to Jack (and his wife?). Maybe she could do some subtle flirting. Maybe you have a beer and chat with him and ask him his thoughts on the lifestyle. Tell him you are thinking of giving it a go. He might warn you off it or he might cheekily volunteer himself :-)

Just be sure to talk about it and be sure :-)

[Cdncuck]

I would say it depends on the people involved. How do they interact with each other? How comfortable are they with each other? In our case, my wife has been with most of my friends. We had mfm things with some of them and she's seen some on her own. All of them were aware of our lifestyle before there was any interaction with them. All of them knew I'm comfortable with her seeing other men.

In our case, some of the relationships stayed the same. Some of the others are now as close to my wife as they are with me. We have not had a negative experience with friends.

Having said that, we know other couples who have played with friends and it didn't work out. You have to seriously evaluate the situation because there is no way to know beforehand how things will work out.

[isinlarsa]

I was working in a law office when a new attorney joined. We immediately hit it off and started socializing together with his wife and my girlfriend. Gradually we both disclosed we were in open relationships. It culminated when we were invited over for his 40th birthday dinner -- just the two couples. After dinner his wife said she had his birthday present. Then she announced his present was my girlfriend! The two women had cooked it up, and we men had no clue. He took my girlfriend into their bedroom to fuck her while his wife and I entertained each other in the living room.

We did occasionally switch, but he really had the hots for my girlfriend, so he would take her solo, or sometime his wife and I just watched them fuck. We would jest that he couldn't be left alone with my girlfriend without fucking her.

[typerope77]

Thanks for the replies.

Is Jack and his wife into swinging? If not wouldn't he be cheating? That's a dumpster fire waiting to happen. IMO unless he and his wife play that way you'd kill the friendship. His wife will get pissed and jealous and that's the end of that.

Jack and his wife Abi are fun and open minded people who talk openly about sex and their kinks quite a lot, like the sex swing in their bedroom, their new bondage ropes, how frequent they do it, etc. We used to wonder if they were swingers, but have since concluded they aren't because we've become so close and are confident if they were they would've told us by now. They both have a history of infidelity but have stuck it out and their relationship seems stronger than ever.

Occasionally they talk about some old friends of theirs who were swingers until their marriage fell apart. Jack also has a wealthy friend out of state who is an open swinger and hosts epic house parties. Abi showed us a photo of her kissing another girl at one of these parties and joked about how the other girl wanted to get with her so bad, but swears that kiss was all that happened. So yeah, they are by no means strangers to swinging circles.

Why put such restrictions on the trip? Why not let her go topless or open the door for some play? Kind of like what happens in Vegas. If there are negative feelings about anything you do then you can leave them at the resort.

There won’t be any complaints coming from me if she does go topless, but it will be her choice with no egging on from me. I’ve found she opens up so much better when the pressure is totally off. Also if you tell her “no” she will just want it 10x more. That is well known fact and a running joke between us. I’m pretty confident my approach here is correct. And the worst case is we come home with a little “unfinished business” which will all but ensure trip #2 not only happens, but is much wilder than trip #1.

I would say it depends on the people involved. How do they interact with each other? How comfortable are they with each other?

Jack has a wild party side and is always joking around about sex. He and I openly talk about how smoking hot Daisy and Abi both are and that we are lucky guys. If you throw him a softball he is going to make a dirty joke about Daisy’s nice ass or big tits every single time. One time we were at a pool party and Jack was being silly and picked Daisy up in her bikini and posed for a photo (which I took). Later she told me she could feel his dick rub up on her leg. At the time she sounded a little weirded out and I just laughed it off, but that was before I knew she secretly wants him to fuck her.

It’s well known between the four of us that Abi doesn’t do anal but Daisy does. Despite being a relatively shy person, Daisy always loves when I brag to Jack and my other buddies about how much she loves anal. This has always surprised me, but I love it because it’s sort of a way to share her using stories that will make other guys think about her and be jealous of me. But the other night during sex Daisy admitted she wishes Jack would take her ass because she knows he’s not getting it at home. I realized in that moment that the entire reason she likes it when I brag about it may be because she wants Jack to want her.

Abi talks about sex all the time, maybe even annoyingly so. Since Jack and Daisy have similar personalities and Abi and I have similar personalities she has made jokes about us couples swapping more than a few times. Once she even had us switch spouses in group photo as a joke. Again, everything comes across as a joke, but there's always a slightly serious undertone. She has made comments about being into my wife, and plenty of comments about being into me too (which Daisy is never thrilled about).

During our fantasy talk the other night I asked Daisy if she would be willing to have a threesome with Abi if that was only way she’d allow Jack play. She nodded and said, “Abi has wanted to get with me for a while and I’d hook up with her any day to get to Jack’s cock”. Again, this was during heated fantasy talk so I take it with a heaping grain of salt, but still she admitted that Abi has the hots for her and there must be more info there than I was originally privy to.

I’d suggest talking to your wife about Jack out of the bedroom. Al lot can be said in the heat of the moment and it’s all fantasy play.

Sit down in the living room with her with your clothes on and have a serious chat about if she wants to really progress with Jack.

You are absolutely right that for anything to proceed there would need to be a sober minded discussion. We have not talked about any of this outside of the bedroom, so for now we’re still firmly in fantasy land. I posted in this forum rather than Wannabes because it definitely felt like a new level of real than it has ever felt before with her bringing him up 2x in a row.

Daisy and I are going to Temptation alone later this year, but after the new year we will be going on a couples vacation with Jack and Abi. Something tells me that a lot could happen between now and then, which is why I’m sort of left with a decision of whether or not I want this to keep progressing or try to steer it elsewhere. As a true submissive, I believe Daisy would keep progressing if I encouraged but would stop and make it nothing more than a fantasy if I don’t.

It’s crazy how prior conversations I’ve had with Daisy make much more sense now that I know about her fantasies with Jack. A few weeks ago Daisy confessed to Abi that she has always wanted to go skinny dipping, and they concluded that it would be more fun to do that with friends you know rather than people you don’t know. I was surprised and told her I figured the opposite since people you may never see again seeing you naked seems like a lot less anxiety than showing your bits to your friends. But now I know the real reason why: she wants Jack to see her naked and she wants to get eyes on his cock.

[SilverStag]

Don't risk your friendship for sex. There are plenty of other opportunities for her. It's part of being an adult and being ethically non-monogamous. Don't screw up his marriage or yours.

Now, you need to get to therapy to discuss her jealousy issues. You have a ticking time bomb on your hands otherwise. Plus, there is the issue of reciprocation. Unresolved feelings of "what I did for you" or what is owed, spoken or not can build resentment. It may not seem to be there now, but later on it will most likely rear its head at a tense moment (and we all have those in our relationships) Besides, what is sauce for the goose is sauce for the gander....

[BT2]

Several years ago Clark Kent (no, not that one) wrote an article on how to have a good hotwife experience. One thing he wrote was never involve friends, coworkers nor relatives. I had for years fantasized about my wife having intimate sex with my best friend, but never acted on it. I did, however, experience for several years every husband's fantasy of having intimate sex with my wife's best girlfriend, sometimes as part of an FMF threesome. I was also a friend of this woman for near 20 years. It proved the wisdom of Mr. Kent's article, and it ultimately ended the friendship between this woman and I. So, I subscribe to the theory that it is better to wish you had, but didn't, than it is to do it and wish you hadn't.

Stated alternatively, I believe it better to leave your best friend out of it.

[typerope77]

After contemplating it more, and reading all the great advice here, I'm definitely not moving forward on this. Not only would it risk a friendship, I think it's also moving too fast. At this point it's pretty clear that if sharing does happen one day, Daisy would prefer to play with a girl for her first encounter. She mentions it often.

Don't risk your friendship for sex. There are plenty of other opportunities for her. It's part of being an adult and being ethically non-monogamous. Don't screw up his marriage or yours.

Now, you need to get to therapy to discuss her jealousy issues. You have a ticking time bomb on your hands otherwise. Plus, there is the issue of reciprocation. Unresolved feelings of "what I did for you" or what is owed, spoken or not can build resentment. It may not seem to be there now, but later on it will most likely rear its head at a tense moment (and we all have those in our relationships) Besides, what is sauce for the goose is sauce for the gander....

I appreciate your good advice. And I agree, it's something we should definitely bring up with our couples therapist. I will say that Daisy has grown leaps and bounds in this dept ever since her best friend got married last year to a dude with NIGHTMARE jealousy issues that is already destroying their marriage (I suspect they will be split up in a few months). By proxy, this has sparked many great convos between Daisy and I about how destructive jealousy is for a marriage and how it's actually counterproductive since her friend kind of wants to cheat now since he accuses her of it literally every day. As a result, I've seen tangible changes in Daisy which is great!

Several years ago Clark Kent (no, not that one) wrote an article on how to have a good hotwife experience. One thing he wrote was never involve friends, coworkers nor relatives. I had for years fantasized about my wife having intimate sex with my best friend, but never acted on it. I did, however, experience for several years every husband's fantasy of having intimate sex with my wife's best girlfriend, sometimes as part of an FMF threesome. I was also a friend of this woman for near 20 years. It proved the wisdom of Mr. Kent's article, and it ultimately ended the friendship between this woman and I. So, I subscribe to the theory that it is better to wish you had, but didn't, than it is to do it and wish you hadn't.

Stated alternatively, I believe it better to leave your best friend out of it.

Wow, exactly the advice I was hoping for. I've heard of swingers starting with sex and becoming close friends over time, but not really the other way around. I suppose there are different levels of friendships too, there are those 20+ year close friends, and 1-2 year acquaintances turned recent friends who you don't have tons of history with. The former is what I'm dealing with here, and I think it's safe to say it's a non-starter in real life but HOT AS HELL when she's calling me Jack in the bedroom! And I have zero problems with that if it gets her soaked and horny!

[daveandjan]

We involved out best friend, Rob. Cheating? Yeah, probabably on his end. It caused some guilt for Jan at first but now she we looks forward to his visits. He will be here this weekend and we, esdpecially Jan, can't wait. We have a thread around here somewhere explaining the deal. Is it a smart move? Probably not. Can it work? Damn sure can. I got nothing else but good luck and have fun.

[Cuck4Life]

My exwife was screwing my best friend when we started dating and she continued after we married. He even screwed her the night before we married so she had his swimmers in her when she walked down the isle.

[typerope77]

After several months of silence on this topic it has suddenly re-emerged. A few evenings ago we went out with my best friend, his wife, and two other couples for a little Christmas party. It was fun, just a simple gift exchange and lots of conversation that with this group usually revolves around sex and lighthearted humor.

When we got home Daisy was very horny so we started having fun in the bedroom. She started teasing that she had something on her mind I would probably love. After some prodding it was Jack. Something about him had turned her on and she couldn't stop thinking about him. I encouraged it further and before you know it I had assumed the role of Jack in her mind and she began moaning "I love you Jack... take my pussy... fill me up with your cum Jack". She came twice as I exploded inside her.

Normally I'd expect her to have at least some immediate regret, but not this night. We talked more about how hot it was, and I said how hot it is for me to think about my best friend cumming inside her. She said that for some reason hearing me say it like that was really hot for her, and that if she were to start fucking Jack she probably wouldn't be able to stop and would I be ok with that. I assured her I would. It seemed like she was admitting the possibility out loud to test my reaction.

The next morning she brought it up again, she talked about how hot it was thinking about fucking Jack, and as expected she reiterated that she could never actually do that in real life. I said of course. She said she wanted me again later and this time it would just be about us.

Later that evening she was again very horny, but to my surprise she brings Jack up again in bed. This time she wanted to think about both of us fucking her. We repeated much of the same fantasies as the night prior, only this time she was very vocal and descriptive about what his cock must be like (Abi brags often about how hung Jack is) and talked about fucking him on our upcoming couples vacation and how she wants to do things to him that Abi won't let him do. Things got very specific, how we would all end up in a room together, how her and Abi would show us their tits if us guys show them our cocks and how in that moment she would kneel down, not think twice, and take Jack in her mouth.

Last night she again wanted to fuck, this time she wanted it to be "just us" which I happily agree. But before we began she still managed to mention how it was Jack's forearms that turned her on the past several days (odd, but hot).

Overall the fantasy play about Jack has been very intense and hot. After the second night of cumming thinking about Jack Daisy wanted me to text him that I love him, which we occasionally both say because we are secure in our masculinity and genuinely do (so does she, apparently). So I did as she asked, and she wanted to read what he said back. I could tell she was turned on still thinking about my best friend having her. I've mentioned to Daisy how the fantasy is super hot for me because it feels safe since we are so close and we know he doesn't sleep around and is fixed so no chance of pregnancy.

For now, this is all still fantasy but I have to admit that each time these moments flare up they get increasingly hotter and Daisy seems more uninhibited. Time will tell where this goes. I am currently trying to talk her into letting me share photos with her in the Hotties section, so far she is resistant, but I'll keep gently trying.

[Ultimate Urge]

I think the first time wife swap often starts with close friends. You've probably "kidded" each other about sex with the other spouse, and one night, it actually happens. That was how my first wife and I started. We vacationed with another couple and had often kidded (the guys did) about "knocking up each other's wife". One year we were at a Hotel NY Eve party. My wife and I arrived early afternoon and had sex twice. He and his wife arrived later. She was feeling pretty bad--cold and flu stuff--and was going to stay in their room. They only came because they had hired several babysitters for everyone's kid--we had 10 couples attending the NY Eve party. He came to our room to pick up my wife and I on the way to dinner. My wife took both our hands and said "I could take you both on" and that's how it started.

[Whenwillshe]

Is it possible that she has already done Jack and wants to get it sanctioned after the fact?

[superb101]

Is it possible that she has already done Jack and wants to get it sanctioned after the fact?

I am wondering the same thing!

[luvwives999]

Hearing your wife tell you how badly she craves another man's cock is one of the hottest things I have ever experienced.

[Seekingmore12]

It certainly sounds like you should have a conversation the 4 of you…..I think a cards on the table discussion that at least you two are exploring the possibility of expanding your sex life to include other people….see where that goes….and not when you are under the influence.

[Ultimate Urge]

My first wife fucked my "bestie" so we have that thought in common. She had never had any other man except me and She was my first and only until several years after we married. Then I had a one night stand with a local divorcee (much older than me) but I loved the experience. About two years later another one night stand with a divorcee from work. Both bare, both FUN.

One time, on vacation, my wife and I were in bed and out of a blue, she asked me to tell her if I had ever fucked anyone else, and promised she wouldn't be "mad", but had to know. She literally almost begged me to tell her if I ever did. I think SHE was thinking about how it would be with another man....she was so hot and so insistant. So I told her. And true to her word, she didn't get upset at all.

She got insanely HORNY and wanted sex right then, and wanted me to tell her everything I did and how it felt. I am certain she was being a voyeur and imagining that "SHE" could be "the other woman." She had several massive orgasms, then as we cuddled and cooled down, she wanted me to tell her all the details again. And I did. And we had wild sex again. That happened 4 times that night.

Six months later at a hotel NY Eve party, we were with a group of friends. My "bestie" and his wife arrived late afternoon. We had arrived earlier and had sex twice. His wife was sick and was going to stay in their room and only came because they had hired babysitters for everyone's kids--at their house.

After dinner, my wife asked me for our room key. I knew she wanted to take him up and fuck him. Everyone else thought they were going to check on his wife. The table was getting empty, the band was starting and I headed to the bar KNOWING my wife was going to fuck my best friend. It was so "sad" in a way, because she could never go back, yet it was even more "hot" in another way because I was so turned on. The last thing I said as I handed her the key was "let him cum inside." And the next hour I had a massive boner thinking of my wife becoming a "hotwife." The urge for her to DO IT, was 10x more than my feeling that she should not. in the end, LUST wins every battle.

[FvilleAR]

Talk to him “offline” to see what he says. Just tell him the truth. You & Daisy have been considering pursuing some of both of your fantasies including a 3-some with another guy. His name consistently comes up because Daisy trusts him & finds him attractive. If the fantasy ever became a serious reality, would he be in to it or no?

Simple adult conversation. Lets not make it a bigger deal than it is

[typerope77]

The other night Daisy went there on her own. I was making some playful comments while fucking her about sharing her around with my guy friends (generic) and then went into some other fantasy until Daisy stopped me and wanted to go back to talking about being shared by a group of my guy friends as it was turning her on. Then she got a little quiet, which is usually the calm before the significant O-storm, then she began moaning "Oh Jack... I love you, Jack. Fill up my pussy with your cum. I love you so much, Jack. I've wanted your cum so bad for so long. Please fill me up. I love you. I love you. I love you. Oh Jaaaaaaaaack!" She came all over my cock professing her undying love and weeping his name. Obviously, I immediately came in her pussy as requested.

After I recovered and looked into her eyes and told her how madly insanely hot that was and how much I love and appreciate her for going there and having fun thinking about him. But within minutes, she was regretful. She went on about how she had crossed a line. That she has told herself from a young age that she would never get off thinking about her friends. If Jack or Abi ever thought these things about us, she not only wouldn't want to know, she wouldn't want them to. She felt as if it could make it weird between her and Jack and that she already struggles with male friendships due to her strict upbringing of being told never to be alone with a boy. She felt dirty in a bad way.

Throughout her speech I remained understanding and supportive. Then I mirrored her a bit and repeated back what she was saying just to get more from her on what she was really feeling in the moment. She never wanted to do that again. I told her I understood why she would want to be cautious, that's actually very mature and she should be proud of herself. I also reminded her that this is just fantasy and is all in in good fun, the moment it's not fun is absolutely an ok time to pump the brakes and make sure what you're choosing to do aligns with what you expect from yourself. That's healthy. Lastly, I shared that this was in fact the 5th or 6th time she's enjoyed a fantasy about Jack and I would know because they really turn me on. This seemed to only increase her anxiety about what had just happened, so I quickly backed off.

The next morning we talked about it briefly and she doubled-down on her feelings from the night prior. I told her that I think the reason it may feel different is because this was the first time that SHE initiated the fantasy. Every other time it's been me testing the waters and it working out maybe 50% of the time and the other times we just pivoted to another hot idea. This time it was Daisy that said his name first. And it was Daisy who went crazy with the L word whilst cumming to the thought of him thrusting into her from behind.

Since then things about Jack have been quiet. But she still loves to fantasize about more than one cock. Only now she doesn't use names. Two nights ago she wanted to think about being gangbanged by a group of guys I find for her, which resulted to pulling up some Hentai gangbang porn which had her cumming in merely a few minutes. She prefers Hentai because she feels guilty and wrong watching real people fuck. There is so much to unpack with this amazing woman but for now I continue to support her, enjoy the fun we are having, and learn about how she is feeling and where this journey might take us.