Gay Sissy School Stories

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Orientation
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Infinite Scroll

BBC: Like Son, Like Father

by silkstockingslover on Jul 9, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. Summary: Father catches son sucking BBC & gets very curious. Note 1: This is a NUDE DAY 2019 story so please vote. Note 2: All participants are at least 18-years-old. Note 3: Thanks to Tex Beethoven and Robert for editing this story I'd just gotten home from work and was in the k...

30-Days of House Arrest Ch. 02

by bjmichaels on Dec 4, 2017
Gay Male

It was hard to concentrate on washing the breakfast dishes and cleaning the kitchen. Mister G was in one of his playful moods and couldn't seem to keep his hands off me. He massaged my shoulders and back and occasionally a hand would slip beneath the waistband of my shorts and claim possession of a buttock, squeezing and pinching it. Needless to say, I wou...

That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

University Discoveries Ch. 04

by fantasyhunter2 on Sep 14, 2017
Gay Male

I am continuing this long dormant story of male discovery by request. Saturday morning I woke up early. The anticipation and resulting anxiety of that night's date had invaded my usual easy slumber. I sat on the edge of my bed trying to decide what to do. Greg was in his own bed snoring away. As had become our habit he was sleeping in the nude. Since the w...

Converted to Gay

by bart_allen on Sep 14, 2017
Gay Male

This story is partly inspired by messages from fans, with slight adjustments. Thank you for reading. ***** I wanted to share with you one of my current projects. A twenty five year old male by the name of Eric. Nothing too special in the looks department, but not too shabby either. He was neither heavy or slim, perhaps a slight softness to him. His eyes we...

House Rules Ch. 07

by EROTICbearscribe on Aug 7, 2019
Gay Male

WALKING THE WALK "We're going to have a visitor today," Daddy announced during breakfast one morning. He was wearing a suit because he had a business meeting. He looked very sharp. My daddy was so handsome. I was such a lucky sissy. When I asked him who was coming, he told me it was Miss Marguerite. "Miss Marguerite from The Beauty Mark?" I asked. L...

Caught with My Pants Down

by Cumfusion on Aug 18, 2017
Gay Male

The early morning sun shone into my student apartment that beautiful May morning. First Year exams were finished, there was no more revising to do, it was relaxation at last. 'Nothing to do. This is going to be my freedom.' I thought. I would often wake up with a hard on but that morning I felt like doing something really sexy. Just lying in bed and masturb...

Discovering my Talent Pt. 01

by DRobbie06 on Aug 24, 2020
Gay Male

I had just turned 18 a few days earlier. I was over a friends house (Brian) playing cards with several guys including my friend's dad and one of his coworkers. Over about 3 or 4 hours, one by one, guys would leave when they were out of cash. With only myself, Brian, his dad (Nick), and his dad's coworker (John) left we decided to call it a night. I didn't h...

Juera

by nancyvasquez on Aug 18, 2017
Gay Male

My name is Kevin Jean Bardot and, yes, I am a sissy. Most guys of my age had matured to where they had begun to look and act like men. I was small and skinny and had no body hair to speak of other than a few sparse, very blonde hairs on my pubis. I had sex with another person for the first time when I went into the navy and was stationed in a small city...