Gay You Are A Sissy Stories

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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...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...

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...

Sissy Dream Come True

by Sjen451 on Oct 6, 2020
Gay Male

It was Friday and I had one job left before I could start my weekend. I didn't have much planned other than watching some of my favorite sissy porn and playing with a few of my larger dildos. Not too exciting, but it's how I spend most of my weekends when I don't have other plans. Today I wore my red lace panties under a pair of black break-away running pa...

Brother/Sister/Slave

by brownmonkk on Aug 18, 2017
Gay Male

Brother / "Sister" " TML", November. 1970 A Monk's monk or two virgins in the monastery; "Good loving & Good Scourging "Sissy" does her magic. WOW, "it" finally happened!!! I had had my first sex, and it was with a fellow brother monk in the monastery. It was great. I was a 20-year-old virgin and had fantasized about lots of women. I distinctly remember...

From Brother to Bitch Ch. 02

by Mixedwritings1993 on Aug 29, 2017
Gay Male

James was sleeping soundly, around 8 o'clock still sucking his thumb like a baby. At that time, the alarm went off, waking him up instantly. The sleep wasn't such a deep one because he woke up too many times while finding himself in the middle of various nightmares. He sat up on the bed, rubbing his eyes. His entire face was wet from the baby like drooling...

The New Gym Member

by exaucer on Sep 14, 2017
Gay Male

Wanting to get in to better shape I decided to join a nearby gym. Moreover I was feeling the need to look at other men naked. With your experience you will know the type of young man I am. I am the one who spends longer than is necessary in the shower, stealing looks at other men's cocks. I am the young man who is slow to get changed, sitting there pretendin...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

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...

The Backpacking Trip Ch. 01

by lockedinsteel on Nov 21, 2017
Gay Male

"It's what I want for you baby," said Jamie. Her husband, Daniel, was still a little uneasy with the idea. "I know you've wanted to explore that for years and I think that if you get the opportunity you should. In fact, I'm giving you an order. Do it if you get the chance. Promise me!" she told him. "Okay, Okay I get it. I promise, my love," he replied....