Shemale Sex Story

2008-Jun-11 -

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2008-Jan-5 - Sex with shemale and a girl

This story was originally published at LadyboyFan Blog

As a female, I'd never considered having sex with a shemale in my life. I mean, why would I want to be with a chick with a dick when I could be with a guy? Then, on a trip to Brazil, everything changed. ... ... (more)

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2007-Apr-9 - Always Wanted A Shemale

This story was originally published at Shemale Sex Blog

I always wondered what it would be like to be with a girl with a dick. After spending years on the internet having internet sex, I finally found a black shemale. After hours of talking about how big her cock was and size double D tits, she finally agreed to meet with me for some fun.

... ... (more)
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2007-Apr-1 - My girl in threesome with two shemales

This story was originally published at Shemale Sex Blog

As I watched my girl on the dance floor bumping and grinding with her friends, I was wondering if I would get lucky tonight. Little did I know, I was in for a night of my life. My girl, Lisa was sandwiched between two of the most beatiful blondes alive. Their hips swayed from side to side and as they bounced their enormous tits shook under their white shirts. Sitting at that table my cock was so hard I thought I was going to cum in my pants.

... ... (more)
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2007-Jan-25 - Satisfied client

This story was originally published at Shemale Sex Blog

I still remember my first time with a shemale. It was a tall thin blonde that came into the office of our law company one day. I knew she was an attorney of one of our clients and I thought her boss, and my friend, sent her to express gratitude for the very good deal we helped him to close.

As I stood up from my chair to welcome her she pushed me down back into my chair and came around while opening her trench coat. There was nothing on underneath the trench coat but there was some equipment that I was not accustomed to, a cock! I knew her before but I had no idea she was a shemale! ... ... (more)

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2006-Dec-31 - "The Night Before" by tight_loose


Danielle was lying on her side under the covers in her bed. Through the haze
of half-sleep and the morning dar, she could just make out the LED light of
the alarm clock on the bedside. ... ... (more)

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2006-Dec-30 - "The Boutique" by DarkSeraph


When I began writing this story, I intended it as a one-off, but as it progressed, I became increasingly aware of the potential for another chapter or two. Anyone who thinks I should write a follow-up (or not), sound off and let me know. ... ... (more)

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2006-Dec-29 - "Army Slut" by Megan


New Guy Gets turned into Army Slut


This is my first story~

My name is Ray,16, I've always been into crossdressing as long as I can remember. Since I was about 11 or 12 if I could guess. (Started with sister's clothing) I am about 5'8, Skinny, Asian. I must say I look very cute dressed up. I would always call my self Megan When Dressed. ... ... (more)

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2006-Dec-28 - "The Extra Credit" by gamefreakjon


I'm sara, a 16 year old freak know by some people. to others im just a different type of person. I like to keep it to myself but in the showers im known to draw attention. My figure is growing as my age grows and so does my dick. In case you cant tell im a shemale also know by some people as a "chick with a dick." I was born like this and ive learned to deal with it. ... ... (more)

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2006-Dec-27 - "The Clinic" by Uosdwis R. Dewoh


Yet another losing Powerweapons contest story :) The Theme for this one is Shemale Nurses. ... ... (more)
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