Auntie Sissy Stories

8,340 results
Orientation
Length
Source
Infinite Scroll

Barbara's Binoculars

by CarrieQ on Mar 21, 2018
Transsexuals & Crossdressers

A bit about the house I grew up in. It was one among many rows of identical boxes built after the war; an anonymous place with no obvious character, in an estate on the outskirts of a town in sharp industrial decline. My favourite room was the attic! I'd climb up there and pull the ladder up behind me, guaranteeing I wouldn't be disturbed. Mother liked to...

I Begged Him To Kiss Me! Ch. 02

by abcuma77 on Sep 13, 2017
Transsexuals & Crossdressers

Still gazing into his hypnotic, commanding eyes, I pulled down the the speedo and liberated his cock from its tight lycra prison. His weighty, engorged member slapped my chin as I released it... making me flinch and eliciting an altogether too feminine gasp. "Where did that come from?" I vaguely remember questioning. My new master chuckled at my coy reactio...

A Look Into My Mind: Uncle Sissyboy Ch. 05

by rickiee_2002 on Aug 31, 2017
Fetish

Lori and Lauren led me into the bathroom. They were giggling and talking to each other so quietly, that I could not figure out what they were saying. My wife, Serena yelled to them as they walked me to the bathroom. "Girls, I bought a liquid depilatory at the drug store. It's in my purse." "We can spread the liquid all over his body and watch the hair just...

Sissy PRIDE!

by nancyvasquez on Aug 27, 2018
Transsexuals & Crossdressers

I'm just sitting around, painting my toenails, and thinking how blessed I am to have been born a sissy. Of course, it wasn't always that way – I wasted so much of my life trying to fight my reality. It wasn't until I went through puberty and I saw that I was not developing physically like the other guys my age that it really began to concern me. I saw them,...

Paige and Spalding

by justincbenedict on Jul 4, 2018
BDSM

Dear Mom, Thanks for the lemon bars. It'll help me stay awake during my property class. Tell Rylie that I'll bring back her mohair coat, don't have a cow. So you were asking me about how things are going with Spalding. I was so glad you and Dad liked him when you came up to school. I agree he's cute and has a good sense of humor, and Dad said Spal was obv...

Auntie

by sparty_party on Sep 15, 2017
Loving Wives

Being in an international marriage has its benefits and draw backs. The pros and cons of these arrangements are sometimes hard to decipher. One must carefully think of cultural differences as well as personality traits. An additional layer of complexity develops as both members of the marriage adjust to the other. Thus, the situation is usually relatively fl...

From Fire to Frying Pan

by mintabal3239 on Sep 16, 2017
Mature

FIRST MEETING: Roger first met Auntie on the way to the Laundromat one Saturday morning. The large overfilled cloth bag he was dragging along got stuck between banister railings, and Auntie who was coming from the other side of the corridor pulling an equally large bag administered a deft kick to release the bag. "Thanks Auntie," said Roger. "Welcome," sa...

Aunt Em Ch. 01

by Falling4U on Sep 13, 2017
First Time

This story is set in the summer of 1968. The events have remained a secret since that time but as the lady in question is now dead it feels right to make them public, although her name has been changed to respect her anonymity. * Auntie Em had never married and was an only child. I call her "Auntie" and did so for all my life ( except when we were alone t...

Ladies Smoking Fetish

by fantasyboy on Sep 11, 2017
Fetish

My first sexual feeling I can remember was watching an old black and white television programme in which a secretary was sitting on her bosses lap and smoking a cigarette. From that day on I have always associated females smoking with sex. My next association of sex and smoking was when I was at secondary school. I would go to collect a friend on the way t...

Li-Wen's Email Ch. 05

by redtoad on Sep 16, 2017
Letters & Transcripts

LEARNING FROM AUNTIE If I had not met with Li-Wen in person, I might have concluded from the next email that she did not exist. This email was written to someone she had been corresponding with and was copied to me. Li-Wen had told me she had an auntie living in Wuxi and she was very close to her. The auntie gave her solace during that difficult period of...