Spanking Sissy Stories

28,144 results
Orientation
Length
Source
Infinite Scroll

Sissy Prince: Origin Ch. 03

by SatinSlip on Feb 13, 2018
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** Olivia pulled off his scratchy wool tunic. It had covered him to just below his cute girly ass. It was uncomfortable to wear, made by Orcs. Yet for some reason it turned him on. His tiny sissy bump was now revealed to the world. It was erect, yet not quite two inches long. He...

Finding Her Secret Emails Ch. 03

by Quietoldie on Sep 26, 2017
Transsexuals & Crossdressers

Our sex life continues as before and I'm very happy about it. Occasionally Carol lies on her back and asks me to mount her or suggests we do it doggy fashion with her kneeling and me taking her from behind. This usually coincides with my badminton night so I assume she's pretending that it's Mr Police Person fucking her. If I'm behind her I pretend to be all...

Yesterday Afternoon

by allourdesires on Jun 10, 2019
Transgender & Crossdressers

A lunchtime call; I was to leave work immediately. Once home I would find everything laid out on the bed: nightie, bralette, cotton panties, hold-ups, lipstick, silver choker and...a blindfold? When I was ready I rang her as ordered, covered my eyes and began to toy with my nipples in anticipation of what was to come. My little clitty jumped inside my panti...

Please Take Baby Steps

by bawdybloke on Sep 15, 2017
Humor & Satire

She sighed at me, perusing my choice of items from the sex exhibition in the paper bag. "Why?" "Because they are all awesome," I cried excitedly. "I've read about this and ..." "Yes, I know you've read about it," my lover muttered calmly and ran her hands through her flowing red hair. "We discussed this and ..." "Come sit down," she cooed, calmly. I felt...

BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...

Melody the Maid

by nohbdy88 on Sep 14, 2017
Transsexuals & Crossdressers

Melvin had been out of work for six months now. After being let go from his previous job, he had promised his wife Susan he'd find new work soon, but soon fell into lazily living off of Susan's income. At her request, Melvin had started helping out with the housework even more. One day, a package arrived in the mail for Susan. "Honey, I have a gift for you...

Behavior Modification Institute Ch. 05

by NancyPan on Sep 12, 2017
Fetish

"I am so proud of you, Tom," Ms Jensen said warmly, approaching me and taking my hands in hers, "It will help you so much to accept this about yourself, Tom. We will help you turn the fantasy of being a sissy into the reality of sissy life. Ms. Panington will be pleased with this progress, and I am quite sure that Kelli will be pleased as well. Let's get you...

Chronicles of Heather Maureen Ch. 05

by HeatherMaureen on Sep 14, 2017
Transsexuals & Crossdressers

My Life with Marty I spent a lot of time at Marty's over the next couple of years. He explained to mom that his 'son' had trouble making any friends and he'd been so glad when I became 'Jason's' friend after meeting him at school. Thus Marty and mom got to know each other thru the frequent phone calls asking if I could stay over or spend a weekend, again. M...

The Descent Ch. 02 - A Slow Glide

by pantywriter on Sep 28, 2020
Transgender & Crossdressers

I sat up, the dried remnants of last night's orgasm sticking uncomfortably to my body. I looked down at my...clitty, I reminded myself. My clitty. To something akin to horror I felt the familiar lurch in the organ, and the equally familiar sensation of tightening in my balls. My clitty rose, slowly at first, but soon to its fullest extent. It began to pulse,...

Jacki's Bitches

by reddbunnz on Sep 15, 2017
BDSM

Chapter One: Carol's Parents Return Carol was sitting in the parlor of her Uncle Rob's home awaiting the arrival of her parents. Carol, an 18 year old high school senior, was staying with her Uncle and his girlfriend, Joy, in order to finish high school while her parents were on an extended, three-month long European vacation. Carol was not only wanted to s...