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Question: I have a question about men being interested in watching transsexuals on a porn site and then having sexual dreams about penises. My boyfriend who is straight had a relationship with a tranny about six years ago and still keeps in contact by phone. This issue has come up as it's interrupting our sex life since he'd rather watch she-male porn on the internet and jerk-off than have sex with me. I'm attractive and have done porn in my past but nothing with trannies. I'm highly sexual, but having a threesome with one of these people just isn't in me. I want nothing to do with it. I'm just not sure if my boyfriend is bi or gay...and just hasn't come to terms with it. He's 41, so by now you'd think he'd know his sexual preference. He has late night conversations with this person, and I recently found out that they are always initiated by my boyfriend. We love each other, but I'm to the point where this just isn't working. Limited sex and all the jerking off and secretive phone calls. Ahhhhhhhh! What are your thoughts on this? Any help would be greatly appreciated!! ...Lindsey

Answer: Okay, first we have to clarify something: When you say your boyfriend had a relationship with a transsexual, I'm assuming you mean a sexual relationship. And based on your other comments, it sounds like this was a "pre-op" transsexual - meaning he still had his penis, making him a member of a group sometimes referred to in porn circles as "chicks with dicks." Let's start there: In general, straight men are only interested in being intimate with one penis - their own. No matter how hot a woman is, if she's "sporting wood" of her own, our sexual interest in her quickly departs. But apparently that's not the case with your boyfriend.  Not only did he have sex with someone else who had a penis, he also continues to fantasize about and masturbates to images of others who are similarly endowed.  I don't think, therefore, it would be much of a stretch to deduce that given this evidence, it is highly-likely that your beau is bi, or even possibly gay and living in denial.

Another issue you should look at is that your boyfriend continues to maintain an ongoing relationship with an old flame.  It also appears that he's the one who's doing the pursuing.  To me, it sounds like he's still involved in that relationship, if not sexually, then emotionally.  At the very least, this emotional umbilical cord to his past does not bode well for his relationship with you in the long run.  If he cannot disconnect from this previous liaison, ultimately it will doom any future the two of you might have together.

That said, do you really want a future with a guy who prefers fantasy women with penises over you with your decidedly more traditional feminine parts?  It seems to me that you deserve a man who actually desires to be intimate with you, and doesn't just occasionally "throw you one" to keep you hanging in there with him.  Perhaps it's time for both of you to take an honest look at your relationship, since it seems that neither of you are particularly satisfied with your situation.  Though you may truly love each other, it may still be necessary for you to go your separate ways so that you might both be free to openly pursue the male, female, or she-male of your respective dreams.

If you have any questions about men, relationships, dating or a related topic, please feel free to email them to me at: I will try to answer as many as I possibly can here in my column. If you are interested in a more comprehensive compendium of musings on the male mind, check out David's [Link Removed] 

(C) 2011 David M. Matthews.  All Rights Reserved.

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