Auntie Sissy Stories

8,340 results
Orientation
Length
Source
Infinite Scroll

Party Desire Ch. 03-04

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

Chapter 3 - A Party Surprise Downstairs Suzie and the other little girls were all running round the house excitedly playing 'pin the tail on the donkey'. Mrs Baxter calls Suzie over. 'Suzie I've a very special surprise for you. This is Molly. She's come to play with you.' I fiddle awkwardly with my ruffles and Suzie looks at me strangely some recognitio...

Kinky Dentist Sian And Sissy Rachel

by Sissy Adele Howells on Dec 12, 2018
Fetish

Most people hate going to the dentist, but I get a sexual pleasure every time my appointment comes around. That is because my dentist is the sexiest women, that I have ever set eyes on. Sian Harris is in her late thirties. She is of medium height with short, brown, mousy hair. Sian is very pretty, with a smile to melt any perverts heart. Sian's husband worke...

Such a Deal Ch. 03

by Angelscuck on Aug 31, 2017
Fetish

Mistress Ilene explained to Pam, "Punishment should be delivered swiftly so a man can remember what he is being punished for and administrated without anger." "The purpose is to teach the offender that he/she has acted improperly and you, the disciplinarian are enacting what is just and proper punishment, objectively without emotional involvement." My mis...

Auntie's Panties Ch. 03

by EasilyConfused on Sep 14, 2017
Transsexuals & Crossdressers

The air in the lounge was filled with both aromatic and visual sexual pleasures as Phoebe continued to enjoy the skill with which Anna ploughed her Mistress's slit with her tongue. Phoebe's hands were on Anna's head ensuring that the penetrations from the latest addition to her brood were deep and long. Anna made muffled sounds as she battled for air whilst...

Father Charles Goes Shopping for Panties Pt. 03

by joefelton on Mar 30, 2020
Fetish

Part Three Chapter 1, Laundry Day Mrs. Susan Madison trudged wearily up the stairs of the St. Joseph's rectory carrying a brown wicker laundry basket. Luckily for her back, today's load of washing was on the lighter side, consisting mostly of Father Charles' socks, undershirts and some brightly colored women's underwear, which she didn't recognize. Sadly,...

Such a Deal Ch. 02

by Angelscuck on Sep 13, 2017
Fetish

Her request made my cock hard. I couldn't have fantasized a better situation. I ordered the Lobster, she had the Prime Rib. I watched her skillfully dissect the meat and devour it like a female lioness eating a gazelle. She was magnificent! We made small talk throughout the meal, never alluding to the proposition we had just discussed. We were on an equa...

A Sissy Saga Ch. 17

by Snurge on Sep 15, 2017
Novels and Novellas

Titled people were a weakness with Miriam Hancock. She frequently spoke of them with harsh condescension, but the snob in her heart secretly rated them higher than wealthy businessmen, and so it was with some delight she agreed to the visit of the ennobled Marchioness of Wiggleswick. The delight had doubled when she discovered that in both Debrett's Distingu...

Kate's Mom Comes To Visit Ch. 05

by Catytheghost on Sep 16, 2017
Transsexuals & Crossdressers

Part 5 A wedding to plan Carmen OK, dinner was a total surprise for me, that's for sure: Ally and Kate getting married, and Mary putting the fear of the Gods into Maggie. Now that really was a shocker, as Mary gets along with everyone. I even asked her about Lady Jenna using me for her pleasure, and she said, "Honey, you just please her and all will be goo...

Dan's dreams come True Ch. 01

by JenniferTaylorTV on Jan 20, 2020
Transgender & Crossdressers

Dan felt the familiar tingle as he walked down the street. First there was the pub, then the little cafe with its pretty tables and the stationery store. And then the green door. The one he'd walked through many times but always got the wonderful, knot of expectation in his stomach. Looking straight ahead, he pushed it open and walked through. Once inside,...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...