Not Quite - But Still a Fun Weekend

[Bobs52]

Sorry, long post but much hinges on the back story!

My wife had one hot wife experience, but that was sometime ago and now I feel like I’m back in the wannabe category. The hot wife fantasy is a constant for us in the bedroom, but I think she really does it more to satisfy my kink than getting her off, but she’s a real trooper with the fantasy.

This past weekend, we had a long time friend of both of ours spend the night with us out of our lake house. He is married, but his wife was out of town on another trip. We have known Tim for close to 20 years. Although he has never acted inappropriately around my wife, I could always tell that he fancied her. Moreover, when it comes to my wife actually taking the plunge again, Tim would be the most logical. She knows him well, is very comfortable with him, and is attracted to him. In fact we’ve been using him lately in our bedroom fantasies, and I recently got her to promise to have sex with him if the situation truly presented itself. Whether this was her feeding my fantasy or not, I didn’t really know and, frankly, didn’t want to know. She was very convincing, and I loved believing that she would do it.

After the three of us spent the day and a good portion of the night partying with friends and drinking, we went back to the cabin. We were having a nightcap on the deck and getting into some deep conversations. After a while, it was time to call it a night. My wife had a boob job a couple of years ago, shortly after his wife had one. In fact, my wife looked to his wife for advice and ultimately used the same surgeon. We had kidded around about having both of them display their boobs to us to compare the surgeon’s work. His wife is very proud of her body as is my wife, so there is no doubt that this will happen eventually. However we only had one of the two present - my wife. Not wanting to miss an opportunity though, I told her to show Tim her boobs. She didn’t hesitate for even a second and raised her shirt immediately. Not wearing a bra, her beautiful boobs were on display for Tim to enjoy, and although no physical touching took place, he certainly did enjoy them. We went inside and were cleaning up/putting things away, and not wanting the moment to pass said to my wife that it was too dark outside and that she should give Tim a better look with the light inside. Again, without hesitation, she raised her shirt to let Tim admire her boobs.

After that, Tim went to the upstairs bedroom to turn in. My wife and I went to the main floor bedroom and prepared for bed. As we’re getting ready to go to bed, I pleaded with her to strip down naked and go upstairs and crawl in Tim’s bed. Unfortunately, she was reluctant to do this saying she couldn’t do that to his wife, who is also our friend, although we have not known her nearly as long as Tim. Unfortunately that was the end of that opportunity.

Tim’s current wife is his second wife. His first wife got sick and ultimately passed away after a long illness. My wife used to comment on how hard it must be for Tim since he was not having sex during this time. I had encouraged her at the time to step in as a surrogate and take care of him. She was reluctant to do so. After his first wife’s death, I really saw no reason why she shouldn’t at that point. She was still hesitant to do so though, and the timing never seemed to work out. Ultimately, he remarried, and that put an end to my plan.

The next morning the three of us went for a walk. My wife wanted to walk further, so Tim and I returned to the cabin so I could make us some breakfast. In the cold light of day I didn’t bring up the boob display. Tim eventually did however saying it was a “fun boob night.” Now that it was out on the table, I told Tim he should have squeezed them or at least held them in his hands for comparison purposes. I assured him that my wife would not have objected. He must have thought I was kidding, because as he was going upstairs to get something he said, “or maybe I should have just had sex with her.” I shot back “hey I tried to send her up to you.” This was all in a light tone and I’m sure he thought we were joking around, even though I was serious. I chickened out though from laying my cards on the table and letting him know my wife really was available to him for sex. I’m not sure how he would have reacted however. His wife is pretty liberal and fun when it comes to sexual matters (she’s danced completely nude in a bar in Key West and once got pulled up on stage at a strip club and ended up completely naked In front of that crowd as well), but she can be insanely jealous if he does things in this regard without her. He got in trouble with her once in this regard for something relatively minor and still remembers the sting.

Instead, I took an indirect approach. I told him the part about me encouraging my wife to “help him out” with his no sex problem toward the end of his first marriage and shortly thereafter. He was interested in her reaction. I told him her absolute reluctance was moving to simple hesitancy and things seemed to be progressing, but then he fucked it up by getting married. This entire conversation felt a bit awkward however so it ended there.

My wife had not yet returned from her walk when I remembered something I had her explicit permission to do. My wife, happy with her body, lets me take all the naked pictures of her I want. In fact, we have a little tradition of anytime we stay in a hotel, she will walk out on the balcony (if we have one) completely nude except for some sexy heels and let me take all the pictures of her I want. If we don’t have a balcony she simply stands naked in front of the large windows and I snap away. I’m not sure how it came up but she once told me “I don’t mind if you show them to Tim.” In anticipation of such an opportunity, I had selected 5 of the best and saved them as favorites. As you might expect these were some of the most explicit shots. Her gorgeous pussy was on full display along with her wonderful boobs in some very seductive poses. Although I had her permission for this for some time, it was still awkward to bring up before now. What was I supposed to say? “Hey Tim, you want another beer and by the way, you want to see some naked pictures of my wife?” Awkward!

But now I had the perfect opportunity. Tim had said he enjoyed seeing her boobs, so I grabbed my iPad (larger viewing area) and said, “If you enjoyed seeing her boobs so much, you’re gonna love this” and proceeded to scroll through these tasteful, but explicit photos. I let him know that I had my wife’s absolute permission to show the photos, but only to him. He was somewhat speechless, but managed to inquire who’s idea it was to show him. Although it was really kinda a joint idea, I told him it was my wife’s. That was as far as it went in that my wife returned shortly after and the subject was dropped.

So here are my takeaways from the whole situation:
1. Out of respect for his marriage, I’m going to stop pushing for a fuck session between he and my wife. It’s just not worth risking his marriage over, but…
2. I got to watch my wife show him her beautiful boobs in person, and not just a quick flash.
3. I got to show him explicit nudes of her with a very clear shots of her beautiful bare pussy.
4. He knows I’m ok with him fucking my wife.
5. He probably thinks by virtue of my wife wanting him to see her nudes, that she probably WANTS to fuck him.
6. He is free to take any liberties he chooses with my wife with her permission, i.e. kissing her, squeezing her boobs, touching her anywhere.
7. I love knowing my wife would likely fuck him if he made the first move.

So all in all, a pretty good weekend!

[craven mohr]

Good luck to you sir!

Please keep us updated~

[Bobs52]

Ok, just got back to dinner with my wonderful wife. We drank and discussed some of this. She confirmed in no uncertain terms she WANTS to have sex with Tim and wants me to make it happen! Afterwards, sex was wonderful and we’re not changing due to post-nut clarity! I’m so happy! We decided I need to have a quiet discussion with Tim to find out if he wants to make this happen. Frankly, his relationship with his wife is his business. Who knows she may be a cuck queen.

We both acknowledged that it’s inevitable at this point. somehow, sometime, she’s fucking Tim! We’re both thrilled!

[Regit]

It must so hot feeling the chemistry and sexual tension growing between the three of you. I don't want to dampen your enthusiasm, but you said he his married and she is a friend of yours. I can't imagine this becoming a one time thing instead of a regular lover/bull for her. How do you want to avoid creating any drama other then involving his wife in this adventure?

[Fearlesspain]

I agree that I'd hate for ya'll to lose a friendship, but maybe some couple play could be an option. Since she's proud of her boobs as much as your wife, maybe let your wife take the lead with some talking and see if they can pull them out to compare and the get opinions.

Even if she never climbs on his cock, it's still exhilarating to know that she wants to and that Tim has seen your wife naked and he wants MORE!

[SilverStag]

Sorry to be a downer, but I think you need to reassess your priorities. First off, your wife has told you that she doesn't want to hurt his marriage (or her friend, his wife) plus you know pretty much how his wife would react (based on her previous reaction to him going it alone) and you say he is your friend, yet for your own prurient interest, you are still pushing them to act.

Sometimes fantasies are better than real life because there are no consequences in fantasies.

If anything, have a group chat with his wife and he at some opportunity and discuss your ideas. It's different when everyone is on the same page.

[Bloomincpl]

I think given the liberal nature of his wife, that you all need to have a frank discussion. Lay it all out there. If there's not open approval all around, put it to rest and let the friendship continue. There's also the possibility that this becomes a four way thing, and you swap spouses on a regular basis.

If you don't do this, and he instead cheats on his wife, he's going to screw up his marriage and you will both be responsible parties. Please, don't do this.

[Bobs52]

The advice here is good. Although I got carried away with my wife FINALLY getting to the point of admitting to me (and maybe more importantly herself) that she’d truly want to have sex with Tim, we’re really back at #1 in my takeaways above, ie not going to push it. The three of us pretty much know where everything stands, and even if that’s as far as things go, it still is pretty exciting for me.

Two follow ups:

Ever since I told my wife about showing her explicit pictures to Tim (recall with her full permission) I’ve been using that to get her off. When I showed Tim the pics, I was holding the iPad and just casually scrolled through them never really lingering on any one more than another. However, nothing says I can’t enhance the event a little for my wife’s benefit. I have her believing that Tim was in control of the iPad and was lingering on the more explicit photos showing her beautiful pussy. I told her I couldn’t really tell for sure, but that I believe Tim was getting hard looking at her pictures as he “adjusted himself” a couple of times. Finally I speculated that he likely masturbated a number of times that next week as he remembered the excitement of viewing naked pictures of a woman he has wanted for a long time. I’m telling her all this while rubbing her clit. As a result of all this she reaches an incredibly intense orgasm, literally screaming and shaking. I’ve enjoyed giving her orgasms over the years from oral and digital contact, but can’t really recall anything that intense! I LOVED it that she got off so hard on thinking of Tim masturbating to her naked pictures!

The other follow up addresses that some have suggested a swap might be a path forward. His wife is very attractive and she likes me. I’m just not sure how much and in what way. The four of us were at a friend’s party the other night. My wife and I arrived after Tim and his wife. When we walked into the room and started greeting people, Tim’s wife rushed over to me and declared “I get him first” and proceeded to give me a big hug and a “friendly” kiss on the lips. This isn’t really that big of deal in that everyone at the party are close friends and it’s not unusual to greet wives and husbands of others with a hug and a kiss. Some on the cheek and some are comfortable with a quick peck on the lips. No big deal really, but Tim’s wife and I are always flirty with each other. I think she senses that Tim has a bond with my wife by virtue of being friends for so long, and this might be her way of evening the playing field a bit. As the night ended, I found myself talking to Tim’s wife. I was pretty trashed so I don’t remember how this came about or what we were talking about but in the middle of the conversation I just stopped and said “do you mind if I kiss you?” “Not at all” she replied, so I did just that! The kiss was a little better than the friendly greeting one at the beginning of the night, but nothing too inappropriate, as we were in a room full of our friends including her husband.

It wasn’t anything seen as weird by either Tim or his wife apparently as due to my being a bit trashed I decided to leave my car there for the night and they drove my wife and I home. The conversation was normal and friendly during the trip.

Who knows where things go from here, if anywhere. I’m just enjoying the ride!

[UKhusband26]

Very hot! And you can dine off the current situation for a long time! Whether it goes further - who knows - but I’d love to have reached the point you have!

[Bobs52]

The latest update to this saga is we hosted Tim and his wife this weekend at our lake house. After attending a party at which we all had plenty to drink we ended up on our deck again for a nightcap. At one point Tim blurts out that the last time he was out at our place by himself, my wife showed him her boobs. As I wrote above Tim’s wife can be jealous when these types of things happen when she’s not present so I was very nervous that he just threw that out there. His wife looked a bit surprised so I immediately jumped in to claim responsibility saying that I talked my wife into doing that so he could compare them with hers (recall they both had boob jobs by the same surgeon). To my surprise, Tim’s wife did not overreact and in fact the conversation turned into a debate about who ended up with the bigger boobs. My wife and I thought Tim’s wife’s boobs were bigger and Tim and his wife thought my wife’s were bigger.

Of course clearly there was only one way to settle this, and next thing you know we had two beautiful women sitting next to each other lifting their shirts and bras exposing their beautiful breasts to us. What fun! Although it really didn’t matter it was judged a tie. But of course that really wasn’t the point now was it?

The next day Tim’s wife had to go back into town for something, but Tim stayed another night. After partying with some friends we came home and my wife slipped into some pajamas and we ended up in the kitchen late night snacking. Of course Tim asked to see my wife’s boobs again, and again with no hesitation she complied. Even though we all knew Tim was joking, he kept coming up with questions about my wife’s boobs so he had to see them again and again. Finally as my wife had her pajama top raised I told Tim the only way he could really evaluate them relative to his wife’s boobs was to feel them. When my wife didn’t object, he did just that, fondling them and giving them a little squeeze.

After my wife lowered her top Tim kept trying to come up with new questions just so my wife would show him her boobs again, and again although we were all in on the game he was playing and all having a good time, each time he asked, my wife would oblige. Finally he came up with a good question. He asked my wife if her nipples were any less sensitive as a result of the surgery. Not wanting to miss this great opportunity, I told Tim the only way to know that answer was to rub and massage her nipples. It was such a turn on for me to watch my wife standing there exposing her breasts to Tim and allowing him to gently massage her nipples! I’d like to say they got so turned on that it went further, but unfortunately that’s where it ended for the night. It was pretty late and my wife finally said she was tired and was going to bed. She went over to kiss Tim goodnight and of course he caressed her boobs as he kissed her.

I went to bed a short time later and unfortunately my wife was already asleep. I was pretty wound up still so I masturbated just so I could fall asleep. When we woke this morning I asked my wife if she was ok with everything that happened last night. She said “sure” and that she had fun. I confessed to her that I jacked off thinking about it and that if I had to guess so did Tim. She just smiled and rolled her eyes and said “men are so easy!”

When Tim awoke and came downstairs, everything just seemed normal. We made some passing references to how fun it was to play “naughty games” and how that it’s just a way to keep things fresh. He left and we went for a walk and then went back to town ourselves.

If I had just thought about it at the time I would have told Tim that it was unfair that he got to see my wife’s boobs and touch them and she got nothing in return. I would have told him that he needed to drop trou and let my wife squeeze and handle his junk so she could compare it with my dick the same way Tim was doing his supposed comparison with the wives boobs. These fun boob games will likely continue in the future and I’m definitely going to try to get my wife’s hand on Tim’s dick!

Not sure where this ends up and if Tim’s wife wants to play, but it’s been fun so far!

[Bloomincpl]

Where this is headed, like a racing steam train, is you two couples swapping spouses.

Let us know how it goes!

You won't be a wannabe for very much longer

[Bobs52]

You won't be a wannabe for very much longer

I hope you are right! Tim and his wife are scheduled to spend Labor Day weekend with us so we’ll see how on board his wife is with all of this.

My wife and I discussed this at dinner again tonight. I always want to make sure I am not misunderstanding anything she wants to do so I asked her specifically if I could have a low-key, private conversation with Tim and tell him in no uncertain terms that my wife is sexually available to him if, and whenever, he chooses. The choice is up to him. Her reply was “please do!”

Frankly as a result of this conversation I think the outcome will be one of the following:

1. He tells his wife and she is cool with it but uninvolved. (0%)
2. He sells “swapping” to his wife and we do that. (25%)
3. He keeps it to himself and fucks my wife at least once (25%)
4. He decides going any further is not a good idea (but still enjoys seeing my wife naked and fondling her boobs…and maybe even her pussy at some point stopping short of intercourse) (40%)
5. We stop playing these “naughty games” completely (10%)

I also asked my wife if she would be ok with me fucking Tim’s wife if necessary to make this happen (when I confessed my fantasy years ago I pledged my complete faithfulness no matter how many men she chose to have sex with). She hesitated a bit but then said “I guess so”. So although this is not my objective as I always found the one way nature of the arrangement hot as hell, if necessary I suppose I could take one for the team. His wife is also very hot!

I’ll report back what happens. Even if it doesn’t go forward, telling Tim that my wife will fuck him anytime he wants, and knowing that my wife WANTS to fuck him, is very exciting to me!

[Cherrybombslam06]

I’m glad you’ve made several comments about checking if his wife is onboard. Men are weak when it comes to sex and it’s not worth ruining a marriage.

[Bloomincpl]

I hope you are right! Tim and his wife are scheduled to spend Labor Day weekend with us so we’ll see how on board his wife is with all of this.

When I was going to bed last night, I was thinking about this thread and what all four of you did with breast comparison etc. I was thinking of a great way to break the ice even further on this. The wives get to control this... Both men get blindfolded; with no peaking possible. A pillow case over the head works well; breathable, but no way to see through it. The women remove their tops and bras. The men are seated, not standing, and situated such that the women can easily approach them without touching them. The men then hold up their hands in a position where they could fondle both breasts of one of the wives, and both wives let each husband fondle their breasts without touching any other part of the wife. The wives have to stay silent and give no clues as to their identity. The wives can't touch either husband in any way except with their breasts. Whichever wife goes first with one husband goes first with the other, so it's easy to keep track. After both husbands fondle the breasts of both wives, the husbands then have to guess which wife was which, based entirely on the feel of their breasts. You can decide beforehand what the prize is

Given that both husbands have seen both wives topless, this game isn't really all that much of a stretch, but it's a great way to step things in the direction you want to go.

Addendum: If things go well, you can even up the ante on this game after 'round 1' above is done. Same game, same setup, but this time instead of hands each husband kisses/tongues the breasts/nipples of each wife, without using their hands, and has to guess who was who. Can't use pillow cases for blindfolds in this case though, so you'd have to come up with something else.

My wife and I discussed this at dinner again tonight. I always want to make sure I am not misunderstanding anything she wants to do so I asked her specifically if I could have a low-key, private conversation with Tim and tell him in no uncertain terms that my wife is sexually available to him if, and whenever, he chooses. The choice is up to him. Her reply was “please do!”

This was very wise of you! And keep doing it!

Also; this response from her rather proves you're beyond a wannabe in a major sense; she's onboard 100%. The biggest hurdle is behind you. Now it's just the action part

I do hope it doesn't end up with Tim cheating to be with your wife. That's obvious bad outcomes of that, but also it means your wife would likely get to play with him only once or a handful of times.