my boyfriend had sex with a tranny

[steh78]

Hello people,

I am new to this forum and even though I have been reading for a while, it took me a while to create an account. But now I have a problem that is eating me every day and I want to get rid of it.

 

Here the story:

 

I have been with a guy for almost 2 months. We started dating 3 and a half months ago, then we mutually broke it off for about a week. We have the same circle of friends and everybody was trying to break us apart, for which reason we both still don't know. It worked for a while, but we realized quickly that we had fallen for each other, and he asked for me back, and I said yes.

 

Ever since then its been really great. We have a lot of fun together, we have an amazing sex life, we spend almost 24/7 with each other, and we enjoy every bit of it.

 

Just a few weeks back I discovered something that shocked me.

One day he was checking his mail while I was sitting next to him and in his inbox I saw an email from craigslist that said "Edit/delete Post..." and the subject was something about playing dress up. I was super shocked, and said immediately "Playing dress up, eh?" and he said "Oh... yeah.. I have to tell you something... When we were broken up I got really lonely and I felt like shi*. So i went on craigslist and posted some stuff because I needed an ego boost!" He didn't meet anyone, he didn't even end up posting the ad, he just wrote it and didn't 'publish' it. So far okay, I told him I understand, we've all done that at some point (um.. yeah), and we were okay, although he seemed a little bit embarrassed.

He told me that he loved me and that he would never ever cheat on me and that he will do everything in his power for me to be happy.

I genuinely believe him because he is a good person with a great heart and I can tell that he cares about me deeply. I didn't even ask for that kind of speech and I told him that I fully trust him and I don't fear him cheating or anything, because I know how good we are for each other.

 

But I still couldn't get over the "playing dress up' thing. It wouldn't leave my head. And I know I shouldn't have done it but one time, when he went to the shower in the morning, I checked his Outbox (I felt so stupid doing this, because I do trust him, and I didn't try to find out if he was STILL doing stuff on craigslist, I just wanted to see what this "dress up" thing was about, it just gave me a weird vibe from beginning).

And there i saw emails he wrote with trannies. They were all dated far back before I even knew him, but it looked like he met up with one of those trannies to have sex with them.

I closed the browser and sat there in shock for a minute. He came back and he could tell something was wrong with me but I couldn't say anything. I knew if I said anything it would have been totally irrational and ever since then i've been thinking about it and it wont leave my head.

So what.. my boyfriend once slept with a tranny. Does that mean he is gay? Does that mean I am not 100 percent what he wants? Am I an excuse? Am I totally wrong when I interpret his love for me?

 

Once we played "Never Ever Have I" with our friends at a party, everybody was real drunk already, and somebody said "never ever have i had anal sex" and my boyfriend drank. All I could think of was him having anal sex with this tranny. I am unsure what to do.

I want to talk to him about this. I want to know if this is still a fantasy of his or if he was only experimenting at the time.

Was it something he wanted to try, tried and now is over with?

 

Please somebody give me some input, I am really losing it here, I just want to get this out of my head and talk it out with him, I have no idea how to approach him, though, and I don't know if it is worth it, or if I should let it be.

 

This is in my head for weeks already, I just want it out!

 

Thanks in advance.

[Philosoraptor]

Be honest and tell him you snooped, you're already in the fire. It will haunt your thoughts until you figure out what happened. At that point you can decide if it is a dealbreaker or not.

[Audrina]

To be honest, this would probably freak me out too. I'm very open sexually and understand experimentation but I believe that without you talking to him it's going to drive you insane.

 

I believe going through his outbox is wrong, and you may have to deal with the repercussions from doing that but I do think you have to have an open conversation about him and how this makes you feel. Just for peace of mind.

[sm1tten]

No one can really answer questions about your boyfriend's sexuality or feelings for you except for him... and although I think you are allowed to feel weird about finding out something like this, the fact that you violated his privacy to do so is a huge problem.

 

I once dated someone who, after a couple of months, confessed to some rather different sexual tastes than I had expected. I am open-minded and because I wanted to be with him, I tried to go along with it, and it honestly put a lot of strain on the relationship because eventually he could tell that I wasn't into it and that made it harder for him to enjoy. I guess my point is that you need to be honest with both him and yourself about what you are okay with.