first time insertion today! (yay!)

[tryonce1]

I posted a long time ago about thinking about having my first experience with a tgirl. Well, I still have not had the guts to go that far yet but I did something else today for the first time ever! I was penetrated by a lady (escort) with a strap-on dildo!

I was really scared, I will admit. The mistress did NOT know what she was doing and was trying to insert it into my anus in such a sloppy manner. But finally I took the dildo from her while she massaged my penis and I inserted it myself into my anus. I got it in about 4-5 inches. It felt really good and I kept doing my butt until she finished me off. I was shaking when I finally came.

My butt does ache a bit now but I do feel it was totally worth it. I wanted a true tgirl but I am just too afraid of diseases. I am so happy that I finally got penetrated even if it was only by a dildo but at the same time I am depressed. I hate paying for any kind of intimacy in the manner that I did. As far as I have experienced, it just is not genuine and therefore not authentic to me. And since I have a girlfriend I don't think I will be able to have meaningful sex with either a tranny or get penetrated with a dom female that really likes me and enjoys penetrating me for me. (if that makes sense...)