A Night of Firsts and Unexpected Surprises – Shemale Sex Stories

by Lonelyhusband (lonelyhusbandtom@yahoo.com)

***

A night in Japan with a hooker turns out differently
than expected. (MM, reluc, 1st-gay-expr, oral, anal)

***

I was traveling in Japan and had a free Saturday night
so I headed down to the area with all the night clubs.
I went into a couple before I found one that I liked.
There were naked girls dancing and other girls
wandering around flirting with you.

One girl caught my fancy, her name was Sindy. She was a
tall blond, I would guess from Eastern Europe or
Russian maybe. Sindy was topless and was rubbing my
crotch as I watched the girls and then asked me to go
into one of the private rooms.

We headed off and as soon as we were in there she had
my pants down to my ankles, pulled out a condom and
rolled it on my cock and with her mouth only sucked me
off until I came. Then she pulled the condom off and
poured the contents onto her breasts and had me lick
them clean. I had tasted my own cum a few times but
never like this.

I was hard again and Sindy suggested we go back to my
hotel for the rest of the night. Right before we were
leaving she whispered in my ear that she was not a girl
at all! She, he… had a cock!

At first I was shocked but then she said that we could
do whatever I wanted and it was up to me if she ever
took it out. By this time I was a pretty drunk and
already turned on so I said, “Let’s go.”

When we got to my room we started making out and she
got me naked and put a condom on me and again sucked me
off. This time she took the condom and poured the
contents right into my mouth. She then found the mini-
bar and suggested we have a drink to relax some.

We talked some and then she started playing with my
cock again getting me hard. Then she asked if I wanted
to see her cock. At first I said no and then curiosity
finally got me and I said ok. She stood up and started
doing a dance for me and slowly striped until she was
fully naked.

My cock is right at 6 inches and Cindy’s was basically
the same, maybe slightly smaller. Then she turned
around and handed me a condom and said, “Fuck me in the
ass, you know you want too.”

I put the condom on and then she handed me some
lubricant to put on the condom as she used the
lubricant to lube her hole. I slowly started to enter
her backdoor. Anal sex I only get every couple years so
this was a real turn on. Then she said, “Fuck me as
hard as you want.”

I did, I pounded her until I came in the condom buried
in her ass. I pulled out and got rid of the condom and
when I came back she was standing there with a very
stiff cock covered with a condom. Then she said, “You
want me to take care of this, or will you make a girl
happy?”

Then she grabbed my hand and put it on her cock and I
started to jack her off and then she said, “Go ahead
put it in your mouth.” I don’t know why I did it, but I
put it to my mouth and she shoved it in until I almost
started gagging.

Then she said, “Let me fuck your ass and make you my
woman.”

She got me down onto all fours and lubed up my ass with
her finger at first and then fucked my ass until she
came. I can’t belive I let her, but I was so turned on
by her smooth feminine body and her stiff slick dick,
that I didn’t protest even once.

Once she cummed in my ass, I was hard and about ready
to cum again. She kept her cock in my ass and reached
around and grabbed my cock and jerked me off until I
shot my load onto the sheets, while she continued to
fuck my rear.

I was pretty much spent and she said it was time for
her to go and I paid her the money I owed plus a little
extra and Sindy left.

END

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