Sissy Spanking Stories

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Orientation
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Infinite Scroll

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Neighbourhood Terror to Sissy Pt. 14

by Fibaro on Dec 2, 2019
Transgender & Crossdressers

Chapter 16 The two women enjoyed looking at Mark as he had to swallow all the white goo he had just squirted. Just as if the way he had achieved his orgasm wasn't bad enough yet? This only added insult to injury. It was Linda who suddenly broke the silence. "It is good you have come here to learn how to handle a sissy and it is my pleasure guiding you int...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Introspection

by edibles123 on Sep 16, 2017
Transsexuals & Crossdressers

I pulled the black Chevy Suburban over to United arrivals lane at Bozeman Airport. I was late and she was already outside waiting with her two large brown suitcases and a smaller black one. Jesus, she brought a lot of gear for a short ski weekend. She was also shivering. Maddy was always cold. Her tall, skinny body and low body fat made her an easy target fo...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

A Mistress to Obey Ch. 05

by gbr2004 on Sep 12, 2017
BDSM

Continuation of this story that involves forced fem, forced bi, discipline, humiliation and submission. Not your thing, move on to another story. * We got back to her house and she opened the car door and let me out. I followed her into the house and she went and set down in her chair and I just stood there in front of her. 'Present sissy boy.' I droppe...

Dressing But Not Passing

by daisy2holes on Sep 14, 2017
Transsexuals & Crossdressers

It was a beautiful spring day and I had an errand to run that took me about an hour from home. The area is mostly rural with towns of five to ten thousand every 20 miles or so. Sometimes on these types of trips I get the incredible urge to dress and drive, but I didn't have any girly stuff with me except the panties I was wearing. After I picked up my packag...

Total Drama Island

by Yelawolf on Oct 12, 2019
Fan Fiction

(Every character in this story is 18+) You step off the boat last. You see all of your competition. Most of the chicks looked pretty damn hot. Especially the cool goth chick. The guys mostly seem like idiots besides a tough-looking dude with green hair and piercings. You walk on the dock seeing the poor condition of the island for the first time. You didn't...

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Sissy Comes Clean

by Cuckyboy3 on Oct 6, 2020
Fetish

Reflections after Mystic: On the scenic drive back home from a fall getaway vacation with my lovely wife, I pondered quietly how the excursion would be remembered as a first of a kind. I had begun the trip with the expectation of a quick and routine spanking followed the next day by an epic sex experience. Three days later, however, I emerged having not onl...

The Man That Owns Me Ch. 02

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

I feel a sharp slap on my left cheek. His strong hand comes down so hard across my butt it shakes the bed, it makes me cry out. A loud 'SMACK' reverberates off of the walls in my bedroom. "Please..." I hear my voice quiver, tremble as I look back over my shoulder at him. It's the fifth time he has hit my rear end hard letting each slap sink in before the...