Denying that I am a pre-op transgender woman

Posted on August 23, 2019
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Lying is a bad idea most of the time and sometimes, I find it as a safe action to resort to when I need to buy time for an instance such as…

Well… this guy that I really like and had sex with (anal) doesn’t know that I’m still a pre-op transgender.  He is a former schoolmate and I had sex with him around 8 years ago.  How do I know that he doesn’t have a problem with anal?  We did 2 rounds and he didn’t want to leave my apartment but I had to kick him out because he was still in college at that time and I didn’t want him skipping school lol.  So right after the sex, he was adamant about getting to know me better but I was at the point of my life when I was switching between daddies (escorting days) and he was like a side entertainment.

In our chats, he tends to tell me stories about the post-op transgender women he had sex with and how he thoroughly enjoyed entering the neovagina. So much so that he asked me to promise him that he’d be the first one to enter mine if I ever get one.  Little did he know, I stopped the plan of getting a sexual reassignment surgery after I got my breasts done.

Fast forward to years later… he wanted to know how I was doing and asked me if I got a sex change operation and I kind of told this guy that I’m a post-op now and he’s VERY curious to see it and actually wants to be the first to try the non-existent “it” lol.

Why did I lie?

Ugh, this would’ve been so much easier if I met him through a transgender dating site.  We don’t really see each other after the sex but we still chat from time to time and recently… he had a SERIOUS glow-up!  He was already very handsome, to begin with, but this time, his dad died and he inherited a STEEL BUSINESS.

Fast-forward to my dilemma, I kind of crushed his dream and told him that I got the surgery together when I had my breasts done and he will not be the first one anymore because I’ve already been using it for the past years lol.  I know he’s pissed because he didn’t reply and left me seen-zoned.  I really like him but I am sure that I don’t have a future with him because he’s just into me because of sex.  If he’s still into me relationship-wise, he’d be talking about different things with me that are beyond the surface.  I’m not sure if I will come clean to him because I think I owe him that but I’m kind of ashamed about the real status of my genitals.

I know I shouldn’t be afraid of who I am and what I have but… I don’t know, I’m pretty sure I’ll get a new crush next week so that is THAT.

Ahh, the joys of transgender dating lol!