My Descent

a little rough, and she sometimes forced my head down on her shaft until I
was beyond gagging. It gave me much greater respect for chicks and guys
that can deep throat huge cocks in porno films. Well, I succeeded in my
mission of making that tool hard, and she flipped me over, put on a rubber,
greased me up, and plunged that monster into my ass. I thought I would
die. I can't really describe the feeling but I'll try. It's like having
to go to the bathroom for about an hour, but you keep holding it in and you
feel that tremendous pressure building inside you waiting to be expelled,
but kind of in reverse, and with rhythm. She did me for what seemed like
30 minutes, before flipping me over so that we were face to face, and
finishing me with her hand simultaneous with her own orgasm. I came so
hard I accidentlly squirted into my own mouth.

That was about 4 years ago. I finally understood why some men risk their
life for the sake of a good hard cock in the ass. Common sense said quit,
this is a dangerous game. I wish I could say that common sense was the
reason why I stopped, but the real reason was that I didn't think I could
ever have that intense a sexual experience again. Instead I began surfing
internet porn sites of every imaginable sort looking for my thrills that
way. I am a bit ashamed by what I have found turns me on, but then again,
humiliation seems to be part of my sexual persona since childhood.

Prologue

On a recent business trip, I could no longer resist the old urge. I had to
get fucked. I Googled "transsexual escorts" for the city I was visiting.
The first escort I called sounded like a totally stoned junkie, with a deep
man's voice. Not at all in keeping with the stunning picture provided. I
found another ad for a shemale who looked pretty nice in the photo. You
could tell the pic was real because she wasn't perfect. I could see that
her boobs were silicon, and she had sort of a big ass, like a Brazilian,
but her face was nice. I called her. She had a very feminine voice. I
asked her if she was a "top." She replied "Versatile." After a few
seconds she asked me "Do you want to get fucked?" I answered excitedly,
"Yes." Then she asked if I liked to suck dick too. Again, I answered
"Yes."