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Threesome dilemma, with a friend or with a stranger?

Tagged as: Big Questions, Dating, Friends, Sex<< Previous question   Next question >>
Question - (7 March 2011) 1 Answers - (Newest, 8 March 2011)
A female United States age 30-35, anonymous writes:

Here the background info: I have a boyfriend of over 4 years, we are very close, have lived together for about 4 years, and are doing very well. We both want to get married but are waiting until I am at least finished with my schooling for financial reasons. We are also about 10 years apart in age, him being the older one.

As I am attracted to women, I think a threesome would be something fun to try (I initiated the idea many times over the years). Naturally, so does he. However we can't agree on whether it should be a with friend or with someone we wont have to deal with again. He has labeled this "case-closed" and says it will never happen, which I dont want to be the case. I would really love to at least try this. I dont want to make it a regular part of our life but occasionally it could spice things up and be fun.

In my opinion, I think the woman should be someone we dont know and dont have to deal with in our daily lives because that way it leads to less potential for harming our relationship. I dont want any emotional attachment developing from this on EITHER of our parts. In his opinion, it should be a friend we know well as to avoid all the possible issues with sleeping with someone you dont know, such as STDs.

I understand where he is coming from because that is a very valid concern. However, I think if we use proper protection and dont go looking for someone desperate or trashy, then it shouldnt be any different than the multiple one night stands he has had that no harm has come from. Im not talking strippers or hookers or anything, just going out to nice clubs and seeing if anyone perks up our interest and talking to them or whatever and seeing where it goes. (I really have no clue how to initiate this either once we do agree)

I have seen more than one friend lose their relationship over involving a friend into their bedroom. Even my mother went through a similar experience when she was younger. As much as I really want to do this, I just wouldnt be comfortable with a friend. Not to mention, I have had serious relationships with women previous to my boyfriend. I dont want to end up losing (or damaging) a friendship or my relationship with my boyfriend because one of us develops feelings for this extra woman.

Im not sure where to go with this anymore because he refuses unless it is a friend and I refuse unless it isnt. Id like to find a compromise but Im not sure how to do that. And there isnt any hurry on this, just it would be nice for us both to enjoy another woman even if only once.

Any advice?

View related questions: escort, one night stand, std, stripper, threesome

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A male reader, anonymous, writes (8 March 2011):

As far as it goes... if you can't come to an agreement, or a compromise... it's best to leave the idea in your heads as a fantasy.

Most threesomes are best left in the head as 98 percent of the time it ends badly for those in the relationship.

Flynn 24

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