I wouldn't do it, but I guess if that's what he wants to, go for it? I'm rather concerned with the whole "random girl thing." Just make sure you don't end up with a "random" std when you're done. I don't see why you you sexuality is something you can't share with your boyfriend alone, as outsiders may at times may promote relationship issues, random or not. But that's just me, for me sex is physical, emotional, and spiritual, even when it's sex with a stranger (and like some people try to say, "it's just sex") it's like you're giving yourself away to someone else. But that's just me. I wouldn't do it unless he's absolutely sure. O, and don't pick up a prostitute if you get desperate, it's against the low ^_~. But anyway, I'm sure someone *might* give advice on how to go about this.

*meant to say against the "law"...and again, I urge...don't pressure him into anything, or force convincing.

I think you have an unrealistic wish. You want to go on vacation, find a "random" girl and have a threesome. Are you really willing to risk your sexual and emotional health for one night of fantasy? Think about the type of girl who would go home with 2 complete strangers and have no qualms about screwing both of them. That's not the kind of person I'd want to exchange bodily fluids with.

I think you should give up the threesome idea and act out another safer, smarter fantasy of his or yours.

My boyfriend would KILL to be in your boyfriend's shoes right now.

But unfortunately, I'm going to have to agree with the ladies above. First of all, as my man always says "What gud fa eat nah gud fah talk" which is patois for "not everything you think should be said"... which means... while in your head it seems like an awesome idea, in reality.. you'll probably hate it. Just think about another woman's hands and mouth being all over your boyfriend... now think about HIS hands and HIS mouth all over another woman! To me, that makes me want to rip her hair our strand by strand... to you, maybe you're okay with it. If you are okay with it then you're still walking into a whole bunch of trouble.

Doing it on vacation is like reaching into a grab bag and pulling out hep-c or herpes or ghonnorea... it's just a lose lose situation. What I would suggest doing is either a) going to a bar together and hit on a couple of women and then invite them home.. it's just as many risks but at least you'll be closer to home so if the three of you really like it you can do it again or b) put an ad on craigslist, get to know the chick a bit, get her to show you proof of a clean health record and then use as much proection as humanly possible. Then she knows exactly what she's getting into. You get to know her a bit more and you have a change to make rules.

Rules is a whole other issue, you need to lay out strict guidelines for both you and your man. They can be anything from... he's not allowed to kiss her on the mouth to he must wear a condom at all times, etc etc. Set rules so that you both feel 100% comfortable and if any rules are broken or if you find you're just not into it... you are allowed to call it off.

My point is that I think you should do ALOT more research about this then just going online and asking a bunch of strangers for tips. A great source is Dan Savage the writed of Savage Love on thestranger.com. Alot of people have wrote in about this topic and he has some great advice. Do more research and realize that while this is supposed to be spontaneous and fun... it should also be VERY VERY safe. You're basically bringin a stray dog in and allowing it to touch your most private parts. Be very careful.

One more thing: if your boyfriend isnt comfortable with this then I think it might be a bad idea. You both need to be 100% into this or it will just end up being the breaking point in your relationship. He might have some very valid reasons for not wanting this to happen so I suggest having a very in depth conversation with him about it and make sure he is completely comfortable with every aspect of this endeavor. Be careful... I've seen threesomes ruin some of the strongest relationships.

Good luck

When you wrote you wouldn't use it against him, what about him using it against you. Do you feel it may change the way he will see you? Depending on how secure he is, there is a possibility he won't trust it will be a one time thing.

A lot of men base their masculinity on being able to sexually satisfy their partner. He could and might already be going there. Some people think it's a great fantasy to fulfill, but actually seeing their partner 'giving it' to someone could cause a freak out.

Picking up a random girl is risky and crazy. What will you do if you get a fatal STD? Then do you think your memories will be fun?

I still advise against it...STDs are on the rise (specially in NY which such a high number), and don't fool yourself into thinking condoms are going to protect you. They're already only 85% safe as it is and even with one on, there's still other risks...skin to skin contact, sores, cuts, etc. Aside from that...the emotional aspects of it are still risky...after you've had the sexual fun, hopefully you won't start regretting it at the end. Frankly, I'd be a bit uneasy about my gf being licked and fondled by some other chick (let alone I'd be rather pissed if it were a guy), and I sure as hell wouldn't feel comfortable pounding some other chick, in front of her...just seems disrespectful to me...especially if you were married, (wtf would be the point of saying vows then having orgys?). If you do it, don't regret it. And as drunk lady says a lot if not all men feel rather...saddened...when they can't sexually please their partners, and to suggest this would probably make it a bit worse if he's at that point...basically "I need another woman to please me cuz you're just not man enough for it." Anyway, happy STD shopping.

"Happy STD shopping" LMAO Gscott86.

Chicka, seriously, you need to reconsider because of the rise of STD, and if this is supposed to be a lady you're going to pick up during a vacation time, and she's that eager to jump into bed with you and your man (strangers), that doesn't sound like someone I'd want to have sex with...
You can't quite ask someone you just met to provide you with her health report 20 mins before going back to your hotel room.

Plus your bf sounds hesitant, you can't force someone to be comfortable with an idea that he's not too keen on.

I saw this segment on HBO looong time ago, try getting a live-doll to have fun with you guys, sure it's expensive but it can last for the longest time too. Seriously.

Aside from the obvious problems with this plan, (ie stds and such) while they are a great fantasy, threesomes are often times the kiss of death to a relationship. Many couples that experiment threesoms or orgies break up with in months of the deed. It screws with your head and creates insecurities between partners. "Is he/she better than me? etc". It just seams like a bad idea all around, random girl or otherwise.

So I really don't understand why the previous posters said what they did. The OP is not looking for advice on whether she should or should not have a threesome (she knows she does!) she is looking for advice on HOW to have a threesome. I think (and hope) I can be of some help to you. Early on in our relationship my boyfriend and I realized that we both wanted a threesome but were clueless as to how to go about it. I did as much research as possible on the subject and we talked about it extensively. We talked about who we would want to do it with, where we would do it, what we would do. We talked about coming up with a set of rules just like one of the other ladies said. Then we went on craigslist and we put a post up advertising that we were looking for someone to have a threesome with. We got a lot of bogus responses so we stopped looking for a while. Then a while later we started "the search" again. instead of us posting on the site we looked for other women and emailed them. It got very frustrating trying to communicate with someone who you had NO clue who they were and there was always the possibility they were just some horny perverted person on the other end. So once again we stopped looking. Finally, a few days before college graduation we went out to a bar crawl. I was talking to a girl who was in the same circle of friends as me and who I knew was bisexual. One thing lead to another and I asked her if she would want to have a threesome with me and my boyfriend and I pointed to my bf and then she said yes. I went over to my bf in the bar and said "let's go we're having a threesome" and we immediately went home. We were all a little drunk, which definitely helped, but everything was just natural. There was no discussion of who would put what where. It just happened and it just worked and it was a hell of a lot of fun. He used a condom while he had sex with her, but took it off while having sex with me. Yes you should use condoms but not the same one with two different people. We asked her if she was clean and she said yes and we said yes too and that was that. (Oh and we've been tested and it's now like 6 months later and we are both still clean) We did it at our apartment so after a couple hours it was getting late and she decided to go home. That was perfectly fine and left us to have our own fun. Honestly, it made our sex life so revved up. We kept having the best sex ever after that. We moved to VA from CT not long after and there was never an issue of if he had feelings for her or anything. So, I'm trying to tell you that you can't LOOK for a 3some, if it happens it will happen. I suggest flirting with women at bars. Oh and if you and your boyfriend have a loving, trusting, honest and open relationship then you will be fine- especially if this was your idea. If you want to chat please feel free to message me. Good luck and just HAVE FUN!