Prissy Sissy Stories

7,690 results
Orientation
Length
Source
Infinite Scroll

Life With Miss Ida Ch. 03

by Sheermistress on Nov 30, 2017
Transsexuals & Crossdressers

After Miss Ida had calmed down from her orgasm and I had licked and sucked as much of her cum from her pantyhose as possible, I asked her to remove them. "But they're not that bad to wear Georgia and I know you love the feel of them so much, they're fine like they are, they're only a little torn, I can keep them on." "No Miss, I insist," I say, "Besides, I...

Robin and Jimmy Olsen - Sissies Ch. 01

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Note that this story stands separate from other stories I have posted. * "If you hunky men will excuse us for the moment, we girls have to go... powder our noses!" Robin said as she scootched around on the cushions of the private booth. Jamie rose and joined her. Their dates watched the two girls' rounded asses sway back and forth as the two sissies walked...

Life With Miss Ida Ch. 06

by Sheermistress on Dec 5, 2017
Transsexuals & Crossdressers

Life with Miss Ida – Part 6 - A New Development On most weekends Mistress and I would enjoy a nice wine or two with our evening meals however, on this particular Saturday, Mistress was enjoying more wine than she usually drinks – we had decided to do the twin, 'Schoolie-Slut' thing this evening, with both Mistress and I in matching, tartan mini-skirts, whi...

Letters from my Mistress 01

by Slava28 on Sep 16, 2017
BDSM

I text you to tell you that I am on my way and to be ready. You trim, you shave and by the time I arrive and let myself in, you are kneeling in the middle of your bedroom, head down, like a good slave. I go to your closet and go through your clothes. I pick out a tank top, a thong, a skirt and a pair of heels and tell you to dress. As you start to put on you...

Bedroom Surprise Ch. 02

by wylite on Sep 13, 2017
Fetish

I endured several more bedroom cleaning sessions; each time I wore my sissy pink dress and panties but I think Mandy and Beth had become bored with this routine. I had a definite feeling that they were cooking up something for me. I still wore the chastity devise but had received no more release from my pent up sexuality. A good solid hard on was not a luxur...

Aunty's Toys Ch. 03

by novelcriss on Feb 10, 2020
Transgender & Crossdressers

*Thank you for the votes and comments on parts one and two. Sorry I am so slow at this!* *** Simmy slowly came round. A fuzzy recollection of being carried to bed, spending the night half asleep, half aroused, snuggled between the two sexy plump women, hands stroking him throughout the night, feeling the slightly damp sheets where she had ... no he had or...

Another Submissive Slut

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

I have willing submitted to dominant couple as a sissy panty cum whore. I agreed to service both in any situation of their choosing and endure private and public humiliation at their hands. We meet for the first time after many phone contacts in a parking lot of a large mall complex in suburbia in her van. He is a short fat dweeb and she is a crass bottle bl...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Another Submissive Slut Ch. 11

by Stillherer on Sep 19, 2017
Transsexuals & Crossdressers

My land lady's knowing look held me transfixed. Quietly Mrs. Lehrer purred, "What are you?" A spasm of trembling shook my body before I could mew out, "I am a sub sissy slut, Mrs. Lehrer." "Hemmmmm," She hummed, "And what else are you slut?" Her voice was quiet, soothing, inquiring. "I am a wanton cum whore, Mrs. Lehrer," I admitted, blushing at such an a...

Relaxing

by Sissy_Desire on Jul 15, 2020
Toys & Masturbation

**This short story contains elements of solo sissy anal play and cum eating. If you are not comfortable with that, please check out another wonderful story from a different creator. If you choose to stay and read, thank you. You're my kind of kinky slut.** I always enjoy swinging by the local adult toy shop. I've been there a couple of times before, and the...