Arranging a threesome with my boyfriend. 

No, that’s not fraught with danger.

When I finally agreed to be exclusive with Fox (we had the exclusivity conversation twice), I had one condition: that he be open to occasionally playing with others, together. He accepted that condition with some reservations.

He was worried first about how often I might want it. When I reassured him it was probably a once every couple of months thing, if that, he felt better.

But then, a more serious issue surfaced – what if he tried it and couldn’t perform, or it really bothered him? He was (is?) worried I may not want to continue dating him.

He’s also been worried he isn’t dominant / aggressive enough for me. We’ve had numerous conversations on this front and I’ve reassured him he’s doing just fine and I’m quite satisfied. I don’t need to be dating a Dom. I’m sure he’ll be worried about that piece until experience tells him otherwise.

But the “playing with others” issue is very real and very current. So much so that a few weeks ago he wondered aloud whether we should try it before I met his daughter Maria. He was worried I would break up with him if it didn’t work out.

Again, I reiterated we would sort it out. I also told him I don’t think he can really know until he’s in the moment how he will actually respond. It’s happened to my partners a few times; even those were convinced they could perform in that situation. I also told him it was all still a theory for me: while I’ve had threesomes, it’s never been with a boyfriend. I may not like watching him with someone else either!

Now he wants to act on it. He’s been fantasizing about me with two men, watched threesome porn, and started to get his head around it.

He brought it up again on Sunday after we got back from dropping Liam off at his Dad’s, and relieved our built up sexual tension. So I asked him whether he would be more comfortable at my place, or at a sex club – and started talking through the pros and cons of each, and he started to look a little freaked out. He told me he was anxious thinking about making those decisions and he’d rather I just sorted it out.

Which I’m fine to do, but it’s hard when the outcome is difficult to predict.

Here are the things I need to consider:

The second “M”.

It really has to be someone I trust. Essentially, they need to know that Fox is my primary partner. They need to be aware enough of the situation to gauge if Fox is uncomfortable and be willing to bow out silently and gracefully if it’s not working.

Jason has proven his capability in this regard. During a failed threesome last year, when it was obvious my then-boyfriend wasn’t into it, Jason whispered in my ear “I’m going to leave you two alone; I will show myself out”, and that’s exactly what he did. There was no drama, I didn’t have to ask him, there was no additional embarrassment.

I also think my choice of person needs to be relatively non-threatening to Fox. Could you imagine if I invited Lewis (not that I would) and he showed up all muscular with his huge cock? No, I don’t think that would make Fox feel so good. If the roles were reversed I sure as hell would be intimidated.

Ideally, it would also be someone who I know can take some (respectful) control. I’m not sure if Fox will be confident enough the first time to direct traffic. I’ve proven to not be the best at that when I’m cumming. The gangbang night was a good example.

I don’t exactly have a large list of candidates that meet those criteria. Jason would be my top choice. Fox also knows about my history with Jason, including why we never ended up dating. I’m not sure if that makes it better or worse, but I think the benefits above outweigh any concern on that front.

Jason isn’t free this Friday night. But he’s keen to join us should the timing work.

The other candidate is the Dom. He definitely has experience and I trust him. But I’ve never had sex with him before so not sure that’s such a good idea. He’s also not free on Friday but says he’s still open to playing with me.

There’s a dark horse candidate; my ex boyfriend (aka #14). He’s been exploring his own sexual boundaries and I know he’d love to join us. But he has no threesome experience and I do think that trumps comfort and availability.

What about Tony?

Kidding.

Location

Option one would be my house. Fox is comfortable here and if things go awry, there’s no public embarrassment. However, if it doesn’t go well, he may always remember that we tried a threesome in my bedroom. I don’t want him having any bad memories tied to my bedroom!

Option two would be one of the local sex clubs. It could be that a sexual environment turns him on. But we don’t know how he’ll react, so it could be very good, or very awkward. He’s been to one before but didn’t engage with anyone (he went alone; he was curious) and didn’t see anything sexual happen.

::

Given the various choices we have, I think the best thing would be to take him to a sex club on Friday night to see how he likes it. Maybe he’ll hate it, and it rules out a club as a threesome venue. Or maybe it will be a real turn on. There’s really no risk with taking him to see what happens. I feel no urgency to make anything happen, but all this talk of threesomes does have me wanting another one. We can walk in, and walk right back out.

Either way, he’s wanted to go to a club with me. It doesn’t have to be explicitly in regards to a threesome. Maybe it will be crazy hot.

I think I have a plan. Anything I’ve missed?

37 thoughts on “Arranging a threesome with my boyfriend. 

  1. You have a comfort level at the sex club, but I can’t imagine being Fox and trying to have his first threesome in that setting. What about setting it up with someone you trust (I vote for Jason) and get a hotel room for that night? It gives you privacy, no chance of contaminating your house with bad memories, and once the guy leaves, you and Fox have the rest of the night and morning to yourselves in the room. That’s what my boyfriend and I did for our first threesome and I’m really glad it was in a hotel room.

  2. It’s common for the guy to have problems the first time in a group situation and that’s nothing for him to be worried about. It will rapidly fix itself and not to worry about the first time.

      • Initially in a room where you are alone so he’s not trying to perform in a crowd. If you notice that he can’t get it up then either suck him or have him kiss you or suck your tits. Get his mind off of it. Don’t tell him that it’s common for guys to have performance issues at first until it happens. If you forewarn him then he will not perform for sure. We guys have fragile egos and for some reason it’s tough. I know it took a while before I could get an erection around a group of people but you get over it. I’ve seen it happen to every new guy almost without fail. Of course it goes without saying that you need to support him as he will get over it. Plus I’m sure there is some anxiety about sharing you with another guy. Take it slow and don’t push it. I’m sure you can find things to entertain him with until he gets a woody.

  3. While I hesitate to comment here, having zero experience in this particular arena, I think your plan is well thought out. I agree with Holly’s suggestion of the hotel room. I also think taking him to a club first to observe and if the mood strikes him to engage with just you and you with just him (is that something people do in those places? I have NO clue) is a good idea for starters. And, as IF there’s any room for decisions – I vote Jason. =D

      • Thank you! I think I’ve read most of them, and have enjoyed living vicariously through you (just don’t always retain all the info – a terrible side effect of sleep deprivation and being over 40). I guess I shouldn’t say “zero” experience – I’ve had some (in my 20s) but it was always with friends and never anywhere but at someone’s home. My bf at the time was really open to anything, which was great for experimentation but not when he started experimenting without me.

  4. V and I have been swinging/swapping/etc for 7+ years. I admit it, there are times when for whatever reason, I get some performance anxiety and things don’t go well. In fact, it happened the very first time that V and I tried to play at a party. It was just she and I, but the presence of others in the room watching us had a negative effect on me and I couldn’t perform with my wife of (then) 15 years. Hopefully things will go well for him but if they don’t, Fox should know that he’s not alone.

    Oh, and I’d volunteer to be your third, but I’m too far away…

  5. I second the hotel room idea. It’s private so there’s no added pressure of an audience, and it’s detached from yours and Fox’ personal lives and locations, which makes it easier for him to compartmentalize it, and maybe even view it as a “what happens in Vegas” type of vibe which can be easier to let himself go and enjoy it more.

  6. Just throwing this out there…What about the third being a “F” for the first time? It might really relax the situation for him.

    I vote hotel also…

  7. One more suggestion. I recall early in your dating with Fox he got Viagra to help out with some potential erection issues. I’d suggest having him take one before the threesome, that way he won’t have any performance issues even if he has anxiety about it, and therefore the only thing you’ll have to watch out for is any emotional issues that crop up during or afterward. At least it’ll be one less thing for you and him to worry about.

  8. How about at your house on the couch?

    My husband and I have had 2 threesomes (mmf), and foursome (another couple) and it didn’t work out quite right any times.

    Fingers crossed for you two, how exciting!

  9. I’d also support the hotel as a safe venue for this adventure. I’ve never had a group scene with someone that I’m in a relationship with. Being a man, I’m virtually certain that I’d be 1000% ok with my female partner and any attractive female. But I’m really not sure about how I’d feel about them with another man. That’s more about my insecurity than anything, but it also is a little possessive jealousy.
    Having been involved in more than one attempted MFM threesome that didn’t happen, I’d say tread lightly and be prepared for failure. It may work out perfectly, but the fact that you talk about him looking weirded out or anxious is a little bit of a warning. LOTS of men (and women) fantasize about sharing their partner but then when they get to, or get close to the reality of it, it becomes a whole different thing.
    My advice, for what it is worth: take him to a sex club, with no expectations first. Let him see what it’s all about, and who all is there. Play a little publicly, and if he’s feeling comfortable you could invite a little audience participation. Or you could invite one of your potential partners to join you there, and if it works out ok at the club, then you could move on to the hotel room for the serious play.
    From what you say Fox is definitely feeling pressure to do this and is afraid of losing you if it doesn’t go well. Make him as comfortable as you can before you go ahead. There is no rush. And…you didn’t mention this in the post, but I have a suspicion that Fox may be a little bi curious. Not all submissives/switches are bi, but it really isn’t a stretch to find a guy with submissive inclinations also having some bi curiosity or fantasy. If you’re cool with that, and you think he might swing that way, let him know that before you go ahead as it may make a difference in his comfort level or interest.
    Have fun!

What do you think?