‘I Had Sex With A Transgender Woman’

For as long as I can remember, I’ve always wanted to have sex with a MILF. I’ve been watching porn for over a decade, and there’s something about MILF porn that’s always driven me wild. A hot older woman in her sexual prime that knows what she wants and what to do? I always hated the people I went to school with, so I think what was so tantalizing was the fact that these MILFs were the complete opposite of these shitty teenage girls sitting with me in the classroom that I was supposed to be attracted to. It was a fantasy. Still is.

But, as the years went by and I started hooking up with these shitty teenage girls, I realized that this fantasy was going to be tough one to fulfill. And at this point she didn’t even have to technically be a MILF, just much older than me. Then things like OkCupid and Tindr came on the scene, which was when I realized that I now had a much more realistic chance. There has to be an older woman out there craving a cub as much as I craved a cougar. So the search began, and really to no avail.


Until chance (Tindr) led me to a 41-year-old blonde with big breasts and tattoo. My cup of tea indeed.

Meeting was easy. It turned out we lived just five blocks from each other so we were able to meet close by. I’m not going to lie: it was kind of awkward. What the fk is a 41-year-old two-time divorcee going to talk to a 23-year-old guy about? Not a whole lot. She mostly talked about her dog in between the awkward silences and sips of beer. But I wasn’t after her personality and I still wanted to fk her. It’s the truth. So after the second drink I asked if she wanted to go back to her place. And we did.

During the walk to her apartment is when it all happened. “I don’t know if you already know this, but I was born a man.” No. I had no f**king clue. And, though I had to think about it for a moment, I ended up in her apartment anyway. She said she had all of her lady parts, and I thought she was attractive before, so what’s the problem? None. There’s a first time for anything, anyway. She rocked me and made me feel like a stud. She even cleaned my dick with a cold wet rag after I came. It was great. And then I left.

I never saw this woman again. Not because I felt dirty or ashamed, but because it was just a bit too out of my comfort zone, even after the fact. But I’m glad I did it. It gave me insight to the shit that some people go through that a heterosexual man like myself could never have fathomed. I don’t think she told me she was trans for my benefit, but for hers. She filled me in on previous experiences too, ones she had with men that didn’t end so well. And unfortunately, I wasn’t surprised. It made me sad to think about how her quest for pleasure often ended in violence and ridicule.

More so than anything else, it was this woman’s confidence and conspicuous femininity that really convinced me to go home with her that night. Oh, and her rack.