Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

I Meet a Well Endowed Shemale Milf Online

by Jamesw324 on Sep 13, 2018
Transsexual

I let out a long sigh as my computer began to boot up, "Well I guess I will check my messages again." Hello there my name is Alex and I am a high school graduate living at my moms house to take a break year. This year I need to find work and hopefully a girlfriend. It was at the start of this break when I stumbled upon this sight called: Shemale me...

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I was Scott Tenna

by tre34harr on Sep 19, 2017
Transsexuals & Crossdressers

If shemales aren't your thing don't read on; if they are please read enjoy and have your eyes opened. ***** "I hold my hand up and tell you truthfully that I used to be a guy; just like you or like any other guy you know or have met in your life time; into the normal thing a typical uni male student of his age would be; girls, drink, football and cars. H...

Zapp!

by The Dark Traveler on Jan 20, 2019
Science Fiction

You go to bed after a long day. You set your alarm as you have another long day tomorrow. You change into pyjamas, bush your teeth get into bed and try to sleep. You dream of your favourite sci-fi show. Then you dream you are in the show. Your dream shifts to another show also Sci-fi then your job. You dream of your friends your family. Then you dream of you...

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Agent Mari

by Ssrd33 on May 28, 2019
Transsexual

Ignacio was a very lonely man he just liked to share with his friends. On one occasion, after so much insistence his friends managed to get him out of the house. On that occasion they went to the outside of the city. In the middle of nowhere is the motel where they stayed. Agent Mari was in that place for her clumsiness but great determination and willingnes...

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Room service

by Rookiegag on Jan 10, 2015
Miscellaneous

You´ve been driving all day on the highway. Fear of flying has its massive downsides, like incredibly boring days spent driving to get to your aunt in Chicago for Christmas. You check the GPS app on your iPhone and it alerts you of a motel a few miles ahead. It´s not cheap but not expensive either. Feeling weary to the bone, you decide to get a bed for the...

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My Shemale Mother

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

I know there is a similar story similar to these but be assured, the other story only served its purpose as a catalyst for this one. This is a pure fantasy, the top fantasy that has been lingering in my mind for several years..here it is... I am 35 years old and had always been living with my mother, who is almost 50 since my father left us 20 years ago. I...

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....

A Secret Fetish Ch. 01

by margekershaw on Sep 13, 2017
Transsexuals & Crossdressers

When teaching a section of my favorite class, "Modern Erotic Literature", I noticed a guy in the back of the room acting strangely. He was in obvious discomfort, and I wondered why. It was during the lecture where I discuss fetish stories. Students find it a revelation. The first thing I usually do is define "shemale" tales: " 'Shemale' is a hardcore adu...

Conditioning of a Scat Slave Pt. 13

by subtlesurrender on Sep 19, 2017
Fetish

The Ultimate Punishment Alone again in a bathroom; chained to a toilet bowl. At least this time Claudia had ample shit at her disposal. Almost the entirety of her load lay on the floor, as did the overflow from Shitface's diarrhea; which was in itself substantial. This time she wanted to savor the moment and avoid being left with nothing to do again. Let's...

Pam's Shemale Experience Ch. 05

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

"Take it, slut, right down your throat!" "That's right, take it, fuck yes, choke on it!" "Fuck yes, babe, that feels so fucking good!" Pam swooned, kneeling subserviently as her temporary owner took her pleasure. "Fuck, Pam, your throat feels so good!" The lustful shemale was as usual in total control. One hand had a fistful of Pam's hair, while the oth...