If you've never broached the subject with your boyfriend before, I wouldn't just jump in straight away and ask if he likes the idea. When I've been in relationships and have ended up having threesomes, whether it was with my girlfriend and another girl or another guy, I've always discussed it with her first in a 'fantasy' type way. For example, we'd be in bed fooling around, and I'd say something like "Have you ever thought about me and another guy f*cking you? the thought of it turns me on...". If they have been interested in the idea, then it's become something we've talked about in the bedroom, watched some p*rn showing it, that sort of thing...and one thing has led to another. If your guy is the jealous type, he probably wouldn't like it...and if this friend of his is a really close friend, it probably won't happen. In my experience, it tends to happen with 'acquaintances' rather than close friends, but other people's experience may be different. The other thing is to know how comfortable your guy would be being naked in front of another guy, and let's face it, it's pretty hard to avoid all physical contact...if he is squeamish about contact with another guy, even if accidental, he probably won't be up for it. If he is broad-minded and maybe even bi-curious, he could well be very happy to give it a try!
My girlfriend and I have spoken about having 3somes (both with another girl and another guy). We have a strong relationship (we have been together for 3.5 years) and the conclusions we came to are that if we do either first of all it would have to be with a stranger that we would never see again (even accidently so on holidays) and that we would want to sit down first with the 'stranger' and tell them the rules. For example I wouldn't let my girlfriend kiss another guy.
The reason why my girlfriend and I would want to have a 3some is not because we think someone else is hot but instead as a new experience for both of us to enjoy. My girlfriend wants to try double penetration (two d***s at once; one in her p**** and one in her ass) in particular.
I think instead of having a 3some with your boyfriend's friend it would be better to discuss it with him first about wanting to have a 3some with another guy, if he is keen on it discuss what can happen (ie is the other guy allowed to put his d*** inside you, do you want to have a double penetration) and then find a stranger while on holidays. I think in a relationship a 3some with a friend is a good way of destroying the relationship.
ROFL.....I came back to mention the rules, but here they are. Good answer.
You'd let him screw her, but not kiss her? Ha ha ha ha. ha ha ha.. hah ha ha ha.. so pathetic.
Eidahl, we all place different values on different things. I bet some of the things you find of value others would find pathetic as well. His answer is a very good one. Calling him pathetic only shows you haven't been around long. A mind is only working when it's open. Doesn't mean you have to agree.....but not acting the fool would help. The tens of thousands of swingers around the would would find you foolish as well. Laying out rules not matter what they are is critical to that lifestyle.
It would seem reasonable to think that if your boyfriend has been your boyfriend for some time now, that you would have some feeling as to what his perspective would be on the subject of helping or watching some other guy stick his penis in your vagina! If he deeply loves you my guess he would not want to head in the direction of a threesome, but if just boyfriend/girlfriend thing he might very well think it is hot and be totally up for the idea. Only you at this point would have a good idea where he stands on it. Then if the boyfriend is good with it, you have to find out whether the other guy is interested in f**king you with the boyfriend present.
I would be concerned about how your boyfriend would handle this. Jealousy and insecurity may arise. I would generalize and ask your boyfriend what he thinks of threesomes, before you move on. Also, this kind of thing although may be fun, can also plummet your relationship into disrespect, so be very careful.
Scroll Down to Read Other Opinions
What's Your Opinion? Sign Up Now!If this happens with his friend, it has a fair chance of creating big problems later. Seeing him is going to a constant reminder. Eventually it's going to get to him.
If he is down for this put an ad someplace like craigs list looking for NSA sane clean DD free guy for a one time thing with you and your guy. Specify it's about you. Require pic's so you can decide before contacting any of them. You can also ask to see a doctors clean bill of health. Yeah it might sound weird, but it's how lots of swingers do things. You can also mention they must come to you...put it as "We host". If you find a guy get a room someplace.
After you are going to need to spend a long time being all over him. Not to say thank you, but to ensure his ego is soothed.
Besides...if this happens and you do that, if you want something else later it's going to smooth the road.
Hope this helps you.
Just ask him how does he feel about threesomes and if he doesn't think its cool to have two guys and a gril he isn't going to go for it
if he is game then it should be simple to bring up his friend and asl for a thresome
Well since it was a joke can I get best answer just for the points
*vomit*
Sexual Relationships 
Sexual Health 
Most Helpful Guys