Shemale School Stories

106,125 results
Orientation
Length
Source
Infinite Scroll

Por que

by Ssrd33 on Apr 22, 2019
Transsexual

We're all super, for some reason my mouth felt tired and had a taste, my ass hurt, the other night we were having a great time on a record. It's the only thing I remembered from the other night. Suddenly the teacher said that a new student was going to enter. We were excited by a new student, fresh meat. The teacher said that his name was Melany, for some re...

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Healthy Behavior

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

Yes, it's a new series, fans of mine. I know you like Marilyn, but she's on hiatus. Deal. Anyway, I do have something interesting for you. It's an unusual tale, but then again, my writing tastes have proven to be a bit unusual. I'm about as mainstream as N'Sync is underground. So without further ado, let's get started. Oh, and yadda yadda yadda over 18 to re...

Pam's Shemale Experience Ch. 09

by majicman21 on Aug 7, 2019
Transgender & Crossdressers

It was Tuesday morning, the second day of the weeklong teacher's conference, and almost the entire room was paying close attention to the speaker, one Martin Greenman, forty-seven-year veteran of the classroom and expert in educational theory. The only one not paying attention was Pam. She was in the front row, doing her best to listen and sit still. Next...

Pam's Shemale Experience Ch. 12

by majicman21 on Oct 12, 2020
Transgender & Crossdressers

Pam and Alex sat together on the bed, the former watching television, the latter on her phone. It was their last night at the hotel. Some of the teachers at the conference had organized a group outing earlier in the night to a nearby restaurant for dinner and drinks, as a farewell of sorts. Pam had gone along, but Tanya had been unable to. "I have a date,...

A Shemale Vacation Ch. 01

by britneyfan on Sep 12, 2017
Transsexuals & Crossdressers

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn't exactly familiar with. I was s...

The Sexiest Shemales Ch. 03

by cleanly_shaven on Sep 13, 2017
Transsexuals & Crossdressers

I woke up laying on Daisy's inner thigh. Her cock was lying right in front of my face. It smelled so good. It smelled like sweet perfume and cum from our previous romp. I smelled it and began rubbing the tip of my nose on it and then slowly I began kissing it. Daisy began to slowly wake up and did her cock. It grew more and more as I continued to kiss it and...

Hot Massage

by william125 on Sep 26, 2017
Transsexual

It's been a busy day at the spa. You decided to stay on working at the spa in your university town over the summer break rather than move back in with your parents. The spa offered an excellent training program for new starters and you found you were a natural. You quickly went from collecting used towels to massaging regular clients. As you wash the oil fro...

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My Journey Ch. 01

by npanxx on Sep 19, 2017
Transsexuals & Crossdressers

I found myself in a midsized college town working on a problem that didn't want to be resolved. With assistance from my co-workers two and a half hours away I was finally able to correct the issue, and system operation was restored. It was late, I was more than three hours from home, and decided I did not want to make the drive. Instead I chose to spend the...

A Transforming Invention

by TransforMaster on Jun 1, 2016
Humor & Satire

In this story, somebody comes across a transformation device. This device allows the user to transform themselves or anybody else into anybody and everything. First choice is... What situation does this story start out with?What's next? Sara, a 24-year old student Sexy girl on a sofa! Two naked women(?) in bed Kate and Her Iffy Shapeshifting Chamber You are...

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Alpha Gamma's Secret Ch. 2

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. Molly smiled and looked over at Gina – her girlfriend, lesbian lover...