Boyfriend into Trannies??

Visitor (not verified)
anonymous user
Registered: 12-31-1969
Boyfriend into Trannies??
Thu, 08-23-2012 - 1:08pm

I am 25 years old and started dating this great 38 year old guy in October 2011.... he was cute, funny, good to me - almost perfect, except that there was something about him. He would always talk about how he had nothing to hide, and that he was open with me - even going as far as giving me his email passwords. Well one day in November (about a month later) I realized I was really falling for this guy, and in an effort to try to prepare myself for what was to come I decided to log into his email.

What I found was definitely not what I was expecting at all..... he had been emailing TRANNIES off of the casual encounters section on CRAIGSLIST. Apparently this has been going on for a while, and had even hooked up with some in the past. I confronted him about it (in January), and he was apologetic and begging for forgiveness. He said he was looking for something sexually, but that he was over it and that NOW he would only be with just me. It is now August and we have been "together" for about 10 months.....

Question is..... do I believe him? Can I try to be more sexually adventerous in the hopes that I will be enough for him? He refuses to discuss the trannies, and has had a hard time opening up to me in the bedroom about his fantasies now (now after I confronted him). I love him.... I want things to work, but I don't know if I can get past this.

iVillage Member
Registered: 11-28-1999
Fri, 08-24-2012 - 11:06am

Do you think that he is actually into cross dressing himself?  I know a woman who was married many years & had 2 kids and her DH only told her many years into the marriage about his secret cross dressing.  Now she thinks he may actually be gay--although literature will tell you that most cross dressing men aren't gay.  I think whatever sexual satisfaction he was getting from these encounters is something that you can't give him no matter how adventurous you are--it was either the secret illicit nature of the encounters that turned him on or he might be bisexual or gay.  I think if he is not willing to be honest about this it's a big problem.  he may stop for a time, but if that's what he really wants, he might also go back--hard to tell.