I was a crossdresser for 6 months

Back-story aside…I decided on my late 20s to attempt to fulfill a fantasy. I always wondered what it would be like to be a female.

I got a few outfits, a set of fake boobs, saved my entire body, and I already had long hair. I was never great at make-up, but kept it simple. Honestly, I wasn’t bad looking and looked feminine-ish.

My first outing was to a country bar. I knew it was dark and everyone would be drunk. I sauntered in and set at the bar. Before I finished my first beer, a guy came up, started hitting on me and caressing my ass. He bought me a drink and one thing led to another. He was the first of 5 to fuck me that night. I sucked off another 7. 2 of each were simultaneous.

I wasn’t not expecting something sexual, but DEFINATELY wasn’t expecting as much.

Even more happened the very next night(Saturday). 4 guys pulled a train on my in one of the restroom stalls. When I sat to empty my ass and give it a brake, another 5 ran a train on my mouth. Before the night was over 6 more fucked my ass, 2 of which stroked me while fucking me. 8 more fucked my throat. I licked 2 women while getting buttfucked by their man. I fucked 3 women. 1 wan sucked me while I was getting fucked. Oh, and was spitroasted 4 times.

Every Friday and Saturday varied between 5-15 in my ass and usually 10-20 down my throat. 2-10 women were involved, even if just to watch their man fuck.

To pay bills, I started prostituting a few nights a week. Mostly Sunday, Tuesday, and Thursday. Friday and Saturday, after the bar closed, I would prostitute for a couple hours of I wasn’t too worn out.

Considering this was the late 90’s, I was making good money! $500 to over $1000 a week. A few times, I would be ‘hired’ for a group and paid $1000 for a few hours with them.

I had hundreds of cocks in each of my holes that 6 months, my bills were paid, and I was $ ahead!

That was lifetimes and 2 ex-wifes ago. I thank God I never caught anything and nothing terrible happened, other than getting beaten up a few times. I do miss almost everything about that time, to a point.