Shemale X Male Stories

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The Roommate Pt. 16 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

So now, Lori, the former Josh, intrepid college teacher and author, was again without a roommate and forced to scrimp to afford her apartment. After Miranda and Leigh Ann, the apartment felt quiet and empty, and she was unable to completely celebrate living as a woman. However, she could afford to shop used clothing stores -- looking, looking and looking to...

My Wife, the TOP ONLY Malay Shemale

by yarracuda on Sep 19, 2017
Transsexuals & Crossdressers

Hi all, my name is yarra (not my real name perverts!!) and I am a proudly married matured male, now 57 years old. My wife, 52 is a (or was a) biological female technically, been married to me for the past 24 years. Let me tell you my fantastic and totally out of this world story. Flashback to 24 years ago, that is the 1989, when i just reached my 30'ish a...

futapus complex

by redpulse0091 on Jan 28, 2019
Fetish

Erik walks up to the front door of his home and pulls out his keys from his backpack. Unlocking the door and walking inside he takes a moment to stretch. Feeling relieved that finals are over and he isn't going back to school for a while he starts walking to the kitchen to grab a snack. Grabbing a protein bar and an apple he continues to his room, turns on h...

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Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

Fun For The Powerful

by FEZBEE on Aug 5, 2019
Fantasy

An ancient entity without any name has decided to go into the human world and have some fun. In order to do this, the entity will be able to use all the powers at their disposal: -Electricity and Fire Manipulation And Generation -Superhuman Strength -Superhuman Durability -Superhuman Stamina -Super Speed -Shape Shifting -Teleportation -Healing Factor -Telepa...

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A Couple and a Shemale Encounter

by Vennessa on Sep 12, 2017
Transsexuals & Crossdressers

Not long ago I was sitting home alone on a Friday night with nothing much to do and feeling horny so I decided to go out. I showered, misted myself with my favorite perfume, put on a sexy black bra, rolled on a silky new pair of jet black sheer to waist pantyhose, slipped into a tight, very short, little black spandex dress and slid my nylon clad feet into a...

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...

Shrunken at home with Futanari Sisters

by starwarsalpha1 on Jan 22, 2021
Transsexual

With the blessing of Mr.z I am transferring his story "Shrunken at home with Shemale Sisters" to this site. First thing you may have noticed is I changed the name slightly. I just like Futanari better than Shemale personally. If you know the original then you know the ages where lower then what this site allows, so I've gone to the liberty of uppin...

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Mistress Melody's Wanton Evening

by RobinTVDaniels on Aug 18, 2017
Fetish

Mistress Melody had become my mistress recently and I was very deeply in love with her. Melody is not that tall but is a very sexy black woman with long braided hair. Her dominant personality was over six foot tall though. I was a transvestite submissive sissy and I was her total slave. We both knew my little 4 inch dick would never satisfy her so she had...

Made Up

by ChewToySub on Sep 15, 2017
Transsexuals & Crossdressers

My first story on Literotica! Hope you like x ***** For the longest time, I've crossdressed alone. I taught myself how to climb into girly clothes, how to roll on tights without tearing them, how to put on my wig without it looking like roadkill. It took time, but I slowly learned how to get myself ready to enter girl mode. But there's a few things I've ne...