Auntie Sissy Stories

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Not Sick Maid In Heaven

by Tomsparty on Sep 16, 2017
Transsexuals & Crossdressers

Many years ago my Mum worked as a bridal consultant for a well-known wedding dress shop. One day to get off College so I could bunk rugby I complained of having a stomachache. The situation was ridiculous. I'm a young man of 19 who had volunteered to continue with my education and study accounts so why the authorities insisted I had to do Rugby as part of th...

A Look Into My Mind: Uncle Sissyboy Ch. 04

by rickiee_2002 on Sep 25, 2017
Fetish

I couldn't believe it ... I was finally going to be able to have sex with my niece. She is so gorgeous and sexy. She is everything I could want. Young, thin, tall, beautiful, full pubic busy, sexy ... WOW. I leaned forward and touched the tip of my tongue to her super wet pubic bush and then the tender small lips of her pussy. There was a white liquid oozin...

Forced to be Their Nephew

by fantasyboy on May 30, 2018
Transsexuals & Crossdressers

I met a lady online many years ago. She agreed to dress me in my sexy undies and we would have mutual oral sex with cum in mouth. She insisted that I had to be younger than 40 (I was mid 30s then). Her name was Kay and she said I had to call her auntie Kay. I arrived at her flat and had to use the intercom to get in and found the right number. I rang the do...

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...

Earning His Keep

by Compliant1 on Sep 19, 2017
BDSM

I punched in the code and waited. I knew that I was being charged $1.99 for each minute, but I didn't care. I listened to the recorded music until a woman's voice came over the phone. "Tell Mistress Monica, have you been a naughty little sissy?" "No, but apparently my husband has." There was a long pause on the other end. "I just spoke to the manager. He...

Made to Obey Ch. 08

by madetoobey on Jul 29, 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...

Sissy Jessica Kinky Office Shagging Ch. 03

by Sissy Adele Howells on Aug 18, 2017
Fetish

It was a lovely sensation to be a member of the Howells family. At 18 years of age, I was now the foster daughter of Adele Howells. Her gorgeous daughter Francesca was my sister, to play kinky games with. Also I had the added pleasure of Joanne Harper, who had been persuaded to join us for the evening. Having exactly the same blonde hairstyle as Joanne, made...

Seduced by Auntie Rita

by fantasyboy on Sep 14, 2017
Erotic Couplings

Seduced by my auntie Rita and uncle Peter I was 18 and started work as an apprentice. I lived in Kent and worked in London. Auntie Rita and uncle Peter lived in South London. They were keen 10 pin bowlers and asked if I wanted to join one evening which I quickly agreed to. After we had finished it was late and my parents agreed that it would be a good idea...

Nylon Femdom

by BlkNYLONS on Sep 18, 2017
Fetish

This took place in 1964... A time when the fashion called for women too wear girdles, garters, and shiny ultra sheer reinforced heel and toe stockings, spike heel pumps/mules daily! A time when my fetish for nylons was young and in full bloom! A FANTASY STORY.... As she stood in her bathroom she could almost still feel his presence. Joan would know just...

A Sissy's Joy in Being Fucked

by MissDeeLiscious on Sep 16, 2017
Transsexuals & Crossdressers

We were in the back room of our local drag club, "Miss Thing's", a very special place where only the seasoned and initiated drag queens and sissies are allowed after hours when the queens have finished performing. As one might imagine putting on an erotic performance going as far as the law will allow all painted up in all their glory makes them aroused in d...