Gay School Stories

116,911 results
Orientation
Length
Source
Infinite Scroll

The Path to Happiness

by brendachaplin2000 on Sep 23, 2019
Transgender & Crossdressers

Author's note, none of the characters are below the age of consent. *** Here I was staring into a full-length mirror, seeing myself glowing in my wedding dress. At 44 years old I never thought the day would come when I would be a blushing bride. As I stared my mind wonders back to my childhood. I was born a boy, Brian Cole. From an early age I knew I was d...

School Gets Different Ch. 03

by cool_person on Sep 12, 2017
Erotic Couplings

Proofread by fellow literotica writer, TalenaBaby. _______________ As I stood staring into the mirror I couldn't help but be amazed at the places my life had taken me recently. To all outwards appearances I was the same Ben I had always been. I still had the poorly styled honey-blonde hair, and my cheeks were still a bit red from my lack of skill at shavin...

Charlie's Way

by Curious_Chick007 on Sep 1, 2017
First Time

If there was one thing you could say about Charlie, it was she loved doing things her way. My name is Al, and I guess you could call me Charlie's boyfriend...although we've never actually been on what you'd call a "real" date. Charlie and I had been dating for the last three years, and I can't remember one instance when we were on a real "date." Charlie...

A Venture into Uncharted Waters

by walterio on Jul 10, 2018
Novels and Novellas

THE BREAKUP Stan and Cora had been dating two years and had often discussed living together but it never happened. Recently he had been offered a prestigious teaching position with a small private elite college in New England. He and Cora were teachers in the San Diego County area and they both loved California. Stan accepted the position and head tried to...

A Culture Clash?

by Emhdtats on Sep 12, 2017
Erotic Couplings

"Dude, that man is wearing a skirt! Why is he wearing a skirt?" The voice appeared at my elbow. I looked to my left, and there was a cute little blonde, late teens, maybe 4'8 or 4'10". Fun size. Proportionate. Miniature legs that went all the way up to where her tight tee shirt met her tight leggings. No panty line, no bra line. She was with a boy, obvious...

A Charming Trickster

by Samuelx on Sep 14, 2017
Erotic Couplings

I think deep down, everyone walking on this planet has a very freaky side. They may not show it but it's definitely there. My name is Adam and I am a freaky kind of man, the kind who doesn't hide who he is or what he's into. I've always been different from other people. Oh, it's not something you can see. I'm a tall young Black man with dark brown skin and p...

My Friend June

by wife2hotblk on Sep 16, 2017
Transsexuals & Crossdressers

I met June at the local support group for women with mental health issues. She is a transsexual woman in her late fifties. Of course, June was the type to stand out, so I had seen her around our neighborhood for some time. Like most people, I admit I was curious. But unlike others, who taunted and tormented her, I was too polite to inquire. But over the week...

Transsexual Sisters Ch. 04

by SplitLicker69 on Sep 14, 2017
Transsexuals & Crossdressers

Part 4: A date with men goes terribly wrong. Note: this is part four in the series about Michelle and Nicole; Michelle and Nicole first experience with males had been a revelation. They learned to accept lesbians and gay men as equally pleasurable though in obviously different ways. Dawn was the first to notice the change in their attitude toward males and...

Me and Corey

by evergreen1288 on Aug 18, 2017
First Time

I'm only 18 and the bipolar pills seemed to be working. And then one day I woke up and something was wrong. My morning wood was gone. I suddenly realized it had been two weeks since I jacked off. I felt bad. I felt like the lowest of the low because it was, I don't know, somehow wrong. It was awful. Days going by and I couldn't get it up and I didn't even ca...

Aaralon's Discoveries

by Sixth on Apr 18, 2002
Fantasy

Aaralon was nervous; he was not only disobeying conventional wisdom by attempting a summons but he was flaunting the strict rules of the boarding school by doing so. He was twenty years old and had been in College of Light Shadow for the last fifteen of them, he couldn't really remember what his parents looked like and all that really seemed to matter about...

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