Shemale School Stories

106,125 results
Orientation
Length
Source
Infinite Scroll

The Head Girl

by Touch_Me_Eat_Me on Sep 16, 2017
Novels and Novellas

Prologue - Miss Kitten The one thing that most makes my 18 year old body happy is to orgasm. I love to shave my little pussy smooth with foam and a sharp razor and then moisturise my inner pink cunt lips all over my mound so that it's so soft to touch. When you run your fingers down my stomach towards and over my vagina it feels like silk. I take such pleas...

A Demon's Love Ch. 01

by TheDemonMostFoul on Mar 12, 2019
NonHuman

A small preface to the story at hand. Nicolas, the demon within this story, is not a demon born and raised in hell. Instead, his parents came to the surface of earth to raise him among mortals in the modern age, and as such he is not an uncaring beast of primeval nightmare. He looks very much like a human, albeit with bright blue hair, golden-orange eyes, tw...

Bosom Buddies Epilogue

by bosombuddies on Nov 18, 2019
Group Sex

EPILOGUE: The ugly truth of any long-distance relationship is, it sucks. Much as your young heart may try to romanticize all the effort and the sacrifice involved, at the end of the day you're still miserable. Eventually, you start to feel a bit like the widow who lives out her days celibate, still in love with her dead husband. It was the hardest thing I'...

Tapestry Ch. 01

by HLD on Sep 12, 2017
Novels and Novellas

Chapter 01: A New Love The relationships we have are threads in a tapestry, each woven together to show the life we have lived and connections we have with one another. This is the first of an open-ended series that will feature characters from some of my past stories, and introduce some new friends for us to get to know. It picks up right after "McKayla's...

A Game of Basketball Pt. 08

by phoenixcinders on Mar 12, 2019
Transgender & Crossdressers

If you couldn't tell, this is part 8 of an ongoing series. The story contains a male 18 year old topping a transgender 18 year old girl. You did read that correctly. This story contains anal. If you don't like that, don't read it. It is a really emotion heavy chapter. And really long. Hope you enjoy. ***** After The Santa Barbara Tournament After we got...

Minister's Wife Plays The Organ

by walterio on Sep 13, 2017
Loving Wives

This story is completely fictional and contains encounters suggested by some readers. All characters are at least 18 years of age. Your feedback is welcome as always. Enjoy the story! INTRODUCTION Sarah Harper has been married to Reverend Thomas Harper for 25 years. She plays the organ at Sunday service in the Mountain Creek church which is affiliated with...

Gypsy

by Gumbo25 on Dec 14, 2020
Loving Wives

We came to a stop sign, I looked sideways at my wife Beth. My quick glance was to gauge her mood. We hadn't spoken so far during the car ride. We were on our way to my families Saturday night dinner. I know, most families have their big dinners on Sunday, but my family was a little different. My fathers family had moved to the US from Romania during the tim...

18-year-old Designed for SIN!

by showguy on Sep 25, 2017
Group Sex

If you enjoy this story please revisit my last two submissions: Naughty High Class Mom parts 1&2. Thank You, hotteeat60. I would like to express my thanks to istanbulnoir for helping edit this feature. Background In The White Trash Trailer Park: The following story is an account of the wild experiences that a friend of mine had fucking my trailer par...

Miranda, Wanton Parole Officer Ch. 05

by Yogakay on Sep 15, 2017
Anal

The Sponsor * Readers, I want to thank you for following Miranda on her sexual journey. I hope you will enjoy this latest installment. kisses, Yogakay ***** The water running down Miranda's body was almost too hot but that was how the blonde parole officer liked it. Her fair skin quickly changed to red as she massaged a vanilla scented body wash into h...

Jogging Memories Ch. 06

by Spencerfiction on Sep 19, 2017
Novels and Novellas

CHAPTER ELEVEN: Lost Jennifer Morris had thought long and hard over the nearly thirty-minute car journey home through relatively quiet roads from the hospital on Monday night. She really wanted to talk to someone, anyone, about all the confusing thoughts and hopes and wishes, desires even, which filled her head with the tumult of conflicting indices. She b...