My Transsexual Experience

I'm a 49 year old straight white male. Though I always have been told I look years younger. My sexual experiences has mainly been focused on women but my fantasies have been varied.

I have dated women over the years and have even been in love a few times. But never met anyone I wanted to spend my life with. It was easy for me to alone even when I was dating someone. One thing I don't like in relationship is when I am expected to be the source of entertainment. Where we eat or go is up to me to come up with.

Now to my fantasies. Now I masturbate like every guy, but my fantasies can get quite perverted. In my early twenties I came across the magazine Penthouse Letters. Out of curiosity I read some of the gay male stories. It was like that Seinfeld episode when George gets a massage from a man. "Jerry I think it moved". I found myself getting turned on by some of them, Mainly told from the view of the more submissive character.

Part of me was worried I might be gay. But I was pretty sure I wasn't as I didn't find men attractive. Pretty much every day I notice a cute girl or a woman with a nice chest or ass. But I never checked out men. But I still read stories about gay men.

One night in my early thirties after 3 or 4 beers I called one of those phone hookup/dating services. I talked to a guy in his mid to late twenties. Went to his place. With liquid courage in me we started out stroking each others cock. Problem was I was having a difficult time getting hard. So he went down on me for awhile which seemed to do the trick. I then went to suck on his maybe 5 inch thin cock that he said was 7 inches. Then he had me sit back so he could stroke our cocks together until we came.

Through my exploration through porn I found I found I was attracted to cock but not men. That's how my interest in trannies came about. Some are pretty masculine which doesn't really do anything for me. I then came across video chat sites where you can talk to trans women and masturbate with. Some of roleplay sessions can be quite fun depending on who you talk with. One the women a black, curvy trans with a big 10 inch cock got me to play with my asshole. I later then got a 6 inch toy to use on my ass when we talked. Then later moved on to a 8 inch one. I would either chat with women who were doms or trans women who were tops.

Now we come to my first experience with a tranny. During my porn searches for trannies was also escort sites. So I knew kind of what to expect when contacting one. I texted one who was about 25 or 26. She sent me her rate and location.

I was nervous on my drive to the motel. When she answered the door she taller than I expected about my height of 6 foot. She kind of had the girl next door look. We talked a bit. Despite my nerves I kissed her. Then my nervousness went away. Before I thought it might feel like kissing a guy. But it was just like kissing any other woman I have been with. We started making out removing our clothes. She had a small chest. She felt soft like any other woman and found myself getting turned on.

I then removed her panties to see what I would be dealing with. She seemed to be the same length as me at 6 inches. I then took her into my mouth and found her cock didn't have much a taste. It was different like when you go down on women. I have noticed they have more flavor and each tasted somewhat different. I kept sucking getting her nice and hard, She seemed to be enjoying it. Then I rubbed our cocks together as I kissed her.

I figured it was now or never. I asked her if she wanted to fuck me. I laid on my back and lifted my legs back as she lubed us up. She slowly pushed into me without a condom. I know I should have said something but in it went. It wasn't that difficult for me as I have had bigger toys. Her cock had a slightly upwards curve and felt good as she fucked me. Between that and my cock rubbing in-between our stomachs I was about to blow. As I was cumming she pulled out and came on my cock.

We chatted a bit as we cleaned up and dressed. I put her money on a dresser and kissed her goodbye. I found in a way it was no different than sex with any other woman I have been with. I asked myself if I would have sex with a tranny again. And the answer is yes. There are more things I want to explore with these unique women.

This was a true story. Like it or hate it. I don't really care. But maybe some of this was similar to your life experiences. Take what you will out of it.