At the beginning of our relationship everything was great. My boyfriend had told me that once he had sex with a cross dressing guy. He said that all they ever did was have sex & it only happened twice. Two years have gone by now & all of a sudden he's talking about being interested in transsexual & cross dressing guys again. I emailed him pretending to be a transsexual guy & we've been emailing back & forth for about a week now. I posed the question yesterday in the email asking him if "we" should meet & he said yes. I'm really at a loss for what to do. Do you think I should confront him & end the relationship or forgive him & ask that he never do this again? Any advice is very helpful now. Thanks!

You can ask him, but then he is not suppose to now anyway, ( if that is the type of relationship you have) Your really only choice is be OK with sharing or find a new boyfriend

If you are't into his sort of kink then I'd recommend putting some distance between the two of you. A lot. And most definitely use a condom and practice safe sex if you stay with him.

Not a good idea for a woman to have a boyfriend who has sex with men.

Backpedal your relationship to being just friends and look for a new boyfriend, is my opinion.

Have a great day! :)

Just one note in general about people: Don't count on the person changing because they very rarely do.

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Originally Posted by wondering1980

At the beginning of our relationship everything was great. My boyfriend had told me that once he had sex with a cross dressing guy. He said that all they ever did was have sex & it only happened twice. Two years have gone by now & all of a sudden hes talking about being interested in transsexual & cross dressing guys again. I emailed him pretending to be a transsexual guy & we've been emailing back & forth for about a week now. I posed the question yesterday in the email asking him if "we" should meet & he said yes. I'm really at a loss for what to do. Do you think I should confront him & end the relationship or forgive him & ask that he never do this again? Any advice is very helpful now. Thanks!

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Mine too

I think your being decietful was the wrong thing to do but now is the time to confront him about what has happened and what you did. Communication is the key you need to know what's going on with your man and cheating is still cheating no matter who its with. Ask yourself will you truly be able to trust him after this?

It sounds to me as though the issue is not so much about the sexuality -- but a general lack of trust and communication... I feel as though part of your sense of security has been trampled on, and your experiment proves some of your worst feelings. I definitely think you should talk to him, if he does a lot of dodging of the subject it should give you grounds for a bigger decision -- whether you should stick around or not. I would tell him very honestly about your feelings on the subject, and keep in mind that he probably told you about his sexual fantasies out of comfort and trust.

On some level, I would like to believe at least and for some peace of mind.. that it was not in fact another person, but you playing a role -- if you are not opposed to his kinks you might as well give yourself some credit for creatively tapping into his fantasies...

But do not give him so much room out of understanding that he can be deceitful and misuse your trust. Your happiness and health is really most what you should consider -- beyond any sexual fetish.

I think maybe putting some distance between you two is a good idea. The gay scene really is a place of meaninless sex and bed hopping [been there done that]. It's good that your okay with him being bisexual, but you shouldn't have to be put threw the hurt and anger of him wanting to be with another man. Talk to him about it, be calm and grown up, and for the love of god do not tell him that it's you who's been emailing him!
I hope you get threw this.

I don't think his bisexuality is the issue... Would you be asking the same question if he was having sex with other women behind your back? Cheating is cheating.

And the fact that you resorted to baiting him in chat rooms, rather than discuss the problem with him shows that you never trusted him to be honest with you. So even if he didn't/doesn't cheat, there is an underlying problem.

I would totally do the same kind of email thing too! But it is wrong I know, and you should confront him about it- and then BREAK UP WITH HIM. (unless you don't care if he messes around with men AND you)... cuase its obvious he would have cheated not just met up with soemone... but, I thing it is a horrible idea to date a gay man because for one, there is a higher risk for stds.. not to sound like a stereotype, but I mean its proven with stats...

I would talk to him about this issue. Tell him how you really feel. Is this something you would be interested in experimenting with him? My husband is bisexual, and wow... well, I'm bisexual myself, so we're both pretty open...

RUN as fast as you can to the nearest exit! While your at it be sure to get tested for AIDS. If he is having homosexual encounters the chances of him contracting a STD are greatly increased. Good luck and I sure hope you have not been having unprotected sex?

I have been there, done that. My x was Bi. When we moved in together, I caught him on a gay singles site. I spent a lot of time kidding myself that he only wanted me. After a flood forced us to use my folks computer, I found out he had a email he had hid from me, AND found an email to a local guy, wanting to meet after his college classes that day.

Unless your down with sharing him, or think you could trust him... just be done. There's nothing to save here.