Sissy Princess Stories

21,927 results
Orientation
Length
Source
Infinite Scroll

Amazon Sissy Jock

by Sissyhalo on Mar 21, 2018
Transsexuals & Crossdressers

All parties involved are over 18 years of age. *** It started me going to a party. Now that's not unusual because I'm popular, I've always been popular like ever since junior high. I shot up like a weed getting tall and my dad worked me out while I was going through my growth spurts and had me in lots of stuff like to round me out before I got into footba...

Kelly, the Sweet Slave Ch. 01

by HumiliatrixEnigma on Sep 2, 2017
Novels and Novellas

Act 1 No one has any recollection of her even having parents. An extravagantly rich couple in their early thirties found her, completely unclothed, lying by the side of their man-made lake. Mr. Smith, a naturally observant man, instantly noticed her while he and Mrs. Smith were out on an early morning stroll. As the couple neared her, both man and woman wer...

A Sissy (S)exercise Fantasy

by darkheathyr on Sep 16, 2017
Transsexuals & Crossdressers

The following tale of sexual depravity contains adult material. If you are under the legal age for your area (generally 18 or 21), or object to explicit sex, stop reading NOW. Otherwise, if erotic situations and taboo acts turn you on, then please enjoy yourself. The characters and situations are, of course, completely fictitious. Feel free to post or archi...

The Writer's Secret Ch. 07-08

by AnnMichelle on Sep 16, 2017
Transsexuals & Crossdressers

Synopsis: Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor did he realize how eagerly his wife Stephanie would embrace the idea of feminizing her husband. How far would they go? Chapter 7: Laura Buys Shoes. . . Lots of Shoes Loren rolled out of bed the following morning. He yawned. Despite having sex w...

Mistress Marisa's Estate Pt. 04

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... ********************************* "Butt's up ladies." She walks behind us, feel her slap my rear as she goes by. Muffled sound of her hand being brought up...

Winning Big in Las Vegas

by marykay9 on Feb 6, 2018
Transsexuals & Crossdressers

I was in Las Vegas staying at one of the "lesser" hotels, playing the slots to kill time waiting for a "Shemale" show to take place. I thought that the review would attract other transvestites like myself and hoped that I might get up the nerve to wear my feminine clothes and mingle with other genetically challenged ladies. Unfortunately, a normal crowd surr...

At The Movies

by hardinmypanties on Sep 17, 2017
BDSM

Mistress decided to take her little princess out for some fun. She let him wear his icky boy clothes, but made him wear a hot pink thong and bra underneath them. Mistress looked stunning in a long black dress and high leather boots. She led him to her car, and drove to an adult theater. This theater was known as a place where men went to meet men. “Oh no Mi...

The Captive Prince

by PrinceCai on Apr 3, 2020
Fantasy

Marcus was reading in bed when his kingdom fell. It was over an hour past his bedtime, but the young prince wanted to stay up and finish his book by candelight. It was way too exciting a story to put down, all about a brave and noble lady knight who saved a peasant boy from the clutches of an evil sorceress. He had his heart in his mouth at the thrilling act...

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Dressing Room Punishment

by bluesbirds on Jun 1, 2020
Transgender & Crossdressers

I immediately knew I wanted the plain black sweater on the closest rack to the left. It was cut off at the belly button, but it looked warm and cozy. It clung tightly to the mannequin, the breasts noticeably perky under the fuzzy fabric and highlighting the curves inward to the hips. Tight sleeves came down about halfway to the elbow. It wasn't particularly...

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...