Literotica First Time In A Shemale Bar Stories

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Father-In-Law Shemale Adventure

by greyhound_guy30 on Sep 16, 2017
Transsexuals & Crossdressers

My wife's parents were visiting LA from back east. We live in a small one-bedroom apartment in the valley. She wanted them to stay with us but we didn't have room. They got a room in West Hollywood. My wife and her mom had gone shopping for the day. I was supposed to be at work but at the last moment I decided to take the day off. Since the girls were out, I...

My First Shemale encounter.

by luv2getnaked on Apr 20, 2020
Transgender & Crossdressers

Only recently I had developed a strong desire to be with a hot looking shemale. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our firm in Las Vegas had experienced a server failure, and I was...

My First Shemale Sex

by available269 on Sep 26, 2017
Transsexuals & Crossdressers

I had developed a strong desire to be with a hot looking shemale for a long time. I really did not know how to make contact with anyone in the small city I lived in, and figured it would likely never happen to me. One day at work at my computer support job, I was informed that another branch of our firm in Las Vegas had experienced a server failure, and I wa...

Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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A Night Out

by Parkerjay77 on Sep 16, 2017
Transsexuals & Crossdressers

I have been a long time fan of Literotica but have never considered writing anything myself. This is my first story of any kind anywhere. I did not have anyone proof read it so sorry for any errors there may be. I was at the bar one Friday night after a long, long week at work. It was one of these weeks where at the end you tell yourself you need a drink....

Amanda and Me Ch. 01

by Tallnhard1 on Sep 25, 2017
Transsexuals & Crossdressers

I walked in the door of my one bedroom apartment and headed straight for the computer. Lately it seemed like I had the same boring routine everyday: get up early, work all day at my stressful IT job, go straight to the computer when I get home to look at porn and masterbate, then eat dinner and go to bed early. Unfortunately tonight was no exception. As I w...

Pounded Into Submission Ch. 02

by Jamesjones52 on Sep 12, 2017
Transsexuals & Crossdressers

*This is the prologue that leads up to Joe being "Pounded into Submission". Also, I read the comments about this being a repost. It is; I am the lonejackman. I got rid of my yahoo email account and couldn't get my password reset for here. * Two days ago Joseph was checking out porn like he usually did at his favorite site xhamster. A couple of BBW vids here...

Lust and Love with Leona

by cbachtland on Sep 17, 2017
Celebrities & Fan Fiction

This is a work of fiction. * The days after I fucked with Leona I spent alone. She has told me that she was going for shoot in the Bahamas for a week. I was a man who had everything in terms of material comforts, and there was not a girl I couldn't pull in a bar. But I found that I could not stop thinking of Leona and that I stayed at home fretting and loo...

When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...

First Shemale

by mac053 on Apr 27, 2020
Transgender & Crossdressers

Lately I've been thinking about sleeping with a shemale. I'm in my late 60's, look 10 year's younger and, for some reason, I'm really attracted to shemales. There are a two LGBTQ bars in my area and I found one that I thought might work. I had no idea what I would do once I got in the bar, but this was an itch that I had to scratch so I went for it. When I p...