2008-Mar-30 - My First Shemale Encounter

I remember the first time I found myself in bed with a shemale.

I had just broken up with my girlfriend. I was lonely, I was horny, and I had zero intention of finding myself in another relationship with a woman.

When I told my buddy, Bob, he told me he knew just where to take me to solve this. So he took me to this club over in West Hollywood. The place was FULL of gorgeous women. My head was swimming - they were almost all slender and dressed in very sexy attire. Short skirts and sheer nylons everywhere.

“Wow!” I told Bob. “These chicks are all drop-dead gorgeous. What’s the catch? Are they all hookers?”

Bob grinned and shook his head. “No, Phil” he told me, continuing to smile. “All these girls are shemales”.

I must have looked confused, because he explained further. “These are women that started out as men. Most of them still have their dicks. But I’ll tell you what, this is a great place to get a gorgeous babe to give you a no-strings blowjob. These chicks never want you to fall in love with them - they just want sex with a straight dude!”

Well, my first thought was “Fuck this - I don’t do guys!”. But I looked around at these fucking super-model quality babes. Great makeup, great bodies, they smelled good. They sure looked like chicks to me - high class chicks, at that! What the hell. It wasn’t like I was going to suck anyone’s dick, but I’d check these “ladies” out.

So that’s how I found myself in bed with a shemale named Tricia. She took one look at me, took me home, and took me right to bed.

She played with my balls and teased my cock, licked my chest, and made all the right moves.Her boobs were great! They were big, shapely, and not hard like I was afraid they’d be. She moaned when I sucked on her nipples, and moved around real sexy. And her legs - her long, shapely legs - looked unbelievable in a black garterbelt and stockings.

Her face was perfect. I had never been out with a real girl half this gorgeous. I mean, you just couldn’t tell. And when I found myself looking down at this beautiful face with my cock in her mouth, her looking up at me, all the while sucking and licking me enthusiastically, I decided shemales were it!

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