Spanking Sissy Stories

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Infinite Scroll

Transforming Brent Pt. 02

by sissymissyct on Jul 10, 2019
Loving Wives

Kept in Loving Wives to annoy the tiny dicked anonymous reviewers that love to trash everything they read (after they wank to it). *** I woke up Sunday morning with a painful erection in my chastity and the pumps still attached to my breasts. I reached down trying to find a way to ease the pain in my penis. Nothing seemed to help. Maybe Wendy will be up so...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Sissy Manners Classes Ch. 01

by fridaysissy on Sep 12, 2018
Transsexuals & Crossdressers

It was late night, I am 10 km away from my room waiting for sharing cab or auto service to reach my room at last I joined a sharing auto service with two members including me. The other passengers stop came early, and I remain alone in auto waiting for my stop to come. Driver said he is stopping the service and returning to his home and asked me to get down....

Clara Bow's Academy for Ladies Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Pepper returned to the room and sat on her new bed as she unpacked her things; Marie helped her stow things in a wardrobe and chest of draws allocated to her. The blonde smirked at the new girl as she blew on the brunettes nails she'd just completed; she would enjoy painting Pepper's nails. Pepper bounced softly on the large double bed; the plug felt so nice...

Thrift Store Encounter

by fantaseeboy on Mar 12, 2019
Transgender & Crossdressers

For several weeks, I'd stopped into the upscale thrift shop at different times on Saturdays and Mondays, my days off. I was trying to discover when the store was the least busy. Once the research was complete, I stepped into the store on Monday morning at 10:00 am. Aside from the familiar heavy set, middle-aged lady behind the counter, I was the only person...

Panty Posers Ch. 05

by EROTICbearscribe on Oct 5, 2020
Transgender & Crossdressers

I certainly wasn't in Kansas. I was dressed as a private school girl tease and standing in front of an adult bookstore superstore. What did my sissy sister have in mind? I tried to find some sort of hint but his poker face offered no clues. We were certainly dressed for more than just shopping for DVD's. So I didn't think we were there for the sales. We ha...

Sabbatical or Continuous Gang Bang? Ch. 02

by TonyaTV69 on Sep 12, 2017
Transsexuals & Crossdressers

I awoke several hours later still laying on top of Rick his arms holding me tight to him. His cock had gone flaccid as we slept and slipped out of me. I felt like I had run a marathon and my ass pussy felt like it had a marathon run through it. I slipped out of Ricks arms onto the bed and went into my bathroom to grab some aspirin and strip out of my damp cl...

Man Disciplines Sissy Ch. 04

by LanaBehave on Sep 25, 2018
Transsexuals & Crossdressers

The fitness-center shower area had three separate tiled shower stalls, with another plank-type bench stretching across their front. I stood between the bench and the middle shower, waiting for him. For Ray. For Daddy. I looked down at myself, and my little cock was hard. I was waiting for Daddy, and he was going to wash me, and show me something. Until t...

The Lady Next Door

by stories55 on Mar 6, 2018
Mature

I moved into a new suburban neighborhood. I'm not the real social type so I didn't go out of my way to meet the neighbors. I'm in my mid 50's and I noticed that I did have a lady living next door that was probably about my age, but she could have been a little older. I saw the young children that visited the house during the holidays, so she could have been...

An Evening in Red

by poule_mouillee on Aug 21, 2018
Transsexuals & Crossdressers

Jack was nervous. As a young man in his early twenties he had his fair share of fantasies, however this was going to be his first true time exploring them. And with what a woman to explore with! They had only just started dating, a few weeks all up, which wasn't enough when going around busy work schedules; but enough to know he was smitten. Victoria was som...