Sissy Party Stories

84,300 results
Orientation
Length
Source
Infinite Scroll

Choices Ch. 01

by pantiwaste on May 21, 2019
BDSM

Chapter 1 The Set-Up My little sexual, I don't know, perversions, fetishes, twists on the normal, has never been exposed, displayed, nor shared...period. It never hurts anyone or affects my interaction with daily life (though it probably has contributed to my difficulty developing relationships). It is one of the few absolute secrets I have kept from the w...

The Making of a White Sissy Slut

by AfroerotiK on Sep 18, 2017
Transsexuals & Crossdressers

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by sayi...

The Unsuspecting Candidate Ch. 03

by missvicky53 on Sep 11, 2017
Fetish

I awoke at 6:00 A.M. and set about preparing for my sissy's surprise. I opened the door to see him there on the bed, his ankles and wrists still cuffed to the four corners of the bed. His head was still encased in the bondage hood and he lifted it as I shut the door and approached the bed. "I trust my sissy slept well," I cooed as I began to release him fr...

The Making of a Mistress Pt. 04

by EiryCGar on Jul 13, 2020
BDSM

Author's note: The saga of Mistress-in-Training Marie and her sissy Charles has reached the point of their marriage. After the ceremony, Marie achieves her ambition and becomes a hotwife, making Charles a cuckold in the process As in all my fictional stories, all characters are over the age of eighteen, and all sexual practices described are performed conse...

The Anniversary Present

by DrLuverotica on Sep 15, 2017
Transsexuals & Crossdressers

My wife, Jo, is a very hot, very sexy 40 year old doctor. For the past few years I've found it really difficult to please her sexually. That all changed when I bought her a Rampant Rabbit vibrator from Ann Summers for our tenth wedding anniversary. When Jo unwrapped the box containing the 8 inch silicon black vibrator she was giddy with excitement. I was de...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

The Training of Sissy Paula Ch. 2

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress carolyn patted me on the head and said i did good. Then she sent me home. The chastity belt still on me, and the cucumber still in my bottom. I logged on line yet no e-mails from Mistress carolyn. It was 4 days before she sent me another e-mail. Hello my pet i bet you thought i had forgot about you. i replied with a yes Mistress i was be...

Attack of the Yellow Convertible

by 4glory6 on Sep 1, 2017
Group Sex

Gail nudged Sam's body off her stomach and to the side. He was lost to the world. She had about ten minutes she figured before he started to snore and she'd be forced to get up and go to the guest room. The mention of "guest room" got her off on the cryptic e-mail message she'd gotten from her cousin, Faye, earlier in the day: "Landed in PBurg. Docking soon...

Halloween Pool Party Pt. 02

by sissymissyct on Sep 15, 2017
Fetish

Maddy Returns I noticed Miss Maddy getting dropped off at the main house around 10 am. I did a quick final check of the pool room and my "pink" room just in case I forgot anything and around 11 Miss Maddy came in. She greeted me warmly with a light peck on the cheek and asked, "How's Ronnie doing today? I have missed our time here in the pool house". Why do...