Gay Sissy Spanking Stories

1,613 results
Orientation
Length
Source
Infinite Scroll

A Night at the Club

by keptsissy on Sep 16, 2017
Gay Male

"Did you make a mess in your panties? Let me see." I stand in front of him. He's seated at a table in the back of the bar. He smiles, a dirty ogle more accurately, toward the man seated to his right. He looks back at me, sees my nervous reaction. He shakes his head with a somewhat disgusted look on his face. He reaches out and takes the front of my short sh...

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...

Pretty Boy

by today_i_am26 on Jul 13, 2020
Gay Male

"Aren't you a pretty boy?" He said with a leering grin. I was on my second day of my new job and I had been tasked to drive the van to an industrial estate in the rougher end of town to collect some items and drop them off to the customer. I had walked through into the warehouse where I was confronted by a man in his late 40's with a strong accent, tattoos,...

Punished Asian Shoplifter Ch. 12

by asianspankee on Sep 19, 2017
Gay Male

After my oral submission to you, I'm left quietly in the corner to reflect on everything that's happened so far till now. Mrs. Jones leaves satisfied, having "conquered" yet another sissy boy with her obscene weapon. After ten minutes you call me back to your side and announces that next week will be my final punishment session. I feel both relieved and sad...

Turned into a Sissy

by drogon01 on Sep 14, 2017
Gay Male

I was 20 years old and had been going out with my girlfriend for about 9 months. Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and wanked over other men. So when my girlfriend told me that she wanted to fuck my arse with a strap on, I was interested. I was at university at the time but was home...

Sissy Sundays

by BlinkOneSomething on Apr 13, 2020
Gay Male

It was the summer of nineteen-ninety, I had just graduated high school and was partying like a rock star. Occasionally when my friends would drop me home late at night, I would walk the block or so to a nearby two lane highway that led out of Boston and stick my thumb out, not ready to end the night just yet. I had a massive libido but knew the chances of a...

Dr. James and His New Treatment

by Suferdude on Jul 11, 2018
Gay Male

James was a tall dark handsome man who worked as a part time Doctor within a rehab facility in San Francisco. He was 6 feet tall and had a gentle beard and soft brown eyes, people often thought him to be a gentle and kind-hearted person. And people would, for the most part be right. However, like everyone, Dr James had a darker side and his work at the expe...

Feminized by My Father

by YANKEE DAN on Aug 30, 2017
Gay Male

I opened my eyes, blinked, yawned, closed them again. I felt confused, disoriented in a way that was... strange. It wasn't like waking up was supposed to be, I wasn't half asleep. I can't remember getting in the bed, in fact I can't remember the last thing I remember. Where did consciousness end last? I was clueless. I tired to move my body and I found it...

Exploring my Sexuality

by alexis19901 on May 12, 2020
Gay Male

I'll just start by saying that I've never attended any sauna that may get mentioned in the story. No names that are mentioned are real people either. It's something I've purely put together based on fantasy alone. Thanks for reading! Today was finally the day. I'd been waiting months to go and push myself to try the closest sauna to me which was a short tr...

The Gentle Master and The New Slave

by eljayb on Apr 17, 2019
Gay Male

You are dressed in your stockings and a pair of very silky panties and lying on your back on the bed. Master enters the room and smiles. He approaches you and kneels beside you and gently kisses on nipple while one hand softly caresses your silky legs. Right down to the toes, under the foot and very slowly and gently up your calf. He cresses that tender spot...