Shemale School Stories

106,125 results
Orientation
Length
Source
Infinite Scroll

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...

Trucker's Surprise

by Mymantoy999 on Apr 3, 2019
Transgender & Crossdressers

NOTE 1: First I would like to thank Silkstockingslover for granting me permission to use her name and story title as a background for my story. NOTE 2: This is my first attempt at fantasy, meaning other than the fact I am a truck driver and I do like the food at Petro truck Stops, none of this is factual in any way. NOTE 3: As stated above this is my fir...

Shemale city

by Ben18927e on Jun 17, 2020
Miscellaneous

I wake up to the sound of my alarm on blaring on my phone. After a couple of failed attempts to ignore it i finally get up and switch it off. Now that the alarm is no longer on, i slowly drag myself out of bed and start to get ready for the day. On the way downstairs i grab a towel, heading towards the bathroom. The water quickly comes on and i start to wash...

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Mommy's Slave

by Futafan567 on Dec 7, 2019
Transsexual

You are Jim. You are 18 years old and live in an average sized home with your mother Jennifer (Jen for short). Being homeschooled for most of your life, you never went outside very often. In fact your only “friends” are the two girls Amy and Mary who live across the street. You are really only friends with them because they live so close but you were never t...

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St. Herma School

by sofly on May 23, 2015
Fetish

A new home and a new school. Being the quiet, anti-social person that you are, your parents were fed up with you staying in your room all night and not socialising. They gave you chances but along with you not making any friends, your grades also dropped. That was the final straw. They were sending you away to live away at a private school called St. Herma,...

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Miss TallyWhacker's Academy for Futas!

by Sex-Shooter on Apr 13, 2020
Transsexual

As you know, Futanari are hyper sexual mostly female humans who have both cocks and vaginas. Because of their hyper-sexual, nymphomaniac natures, they are required to live in different areas far area from the general populace outside of work, especially for their education. Young futas are the most "dangerous" of futas given their developing minds,...

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Brazilian Shemale

by Thorsten007 on Dec 30, 2017
Transsexual

Rules: Needs to be a brazilian shemale with big tits, a fat cock and a nice round bubble butt! Feel free to continue and create new storylines.What's next? James Kingston Pablo What's next? James Kingston Pablo...

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Rebecca's Secret Ch. 02

by Wannabe Chick on Sep 12, 2017
Transsexuals & Crossdressers

Synopsis: This story is partly based on fact, partly a fantasy. It is the story of a young man on vacation with his girlfriend and the night they have sex for the first time. The girlfriend has, up to this point, been reluctant to try sex. The big night finally comes for the two of them and the young man realizes, at last, what has made her so hesitant to sh...

Showing Off For My Wife's Pleasure

by HotJennieh on Sep 19, 2017
Fetish

A first time effort based on real events. * There I was lying on my back, on the floor of a cheap adult bookstore. All I was wearing were 5" heels, black thighhighs, and a nipple chain. In one hand, I was jerking my throbbing shaved shaft while I was using my other hand to fuck my ass with a double headed dong. Cum was glistening on my face and chest and r...

Blossoming Shemale Ch. 03

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by tawnysuede's Reluctant Shemale: http://www.literotica.com/s/reluctant-shemale If you enjoyed it, I hope you'll enjoy this series. A note on political correctness: I have come to learn just a tiny bit about the transgender community, and by that I mean that I've learned that words such as shemale, transsexual and dickgirl are offensive...