Sissy Aunt Stories

18,612 results
Orientation
Length
Source
Infinite Scroll

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

Jason's Secrets Exposed Ch. 12

by jlenil on Jan 8, 2018
BDSM

The reader is strongly encouraged to read the first 11 installments before reading this chapter. ***** Lillie's trip had been extremely fruitful, both in pleasure and in new ideas. Ariana, being extremely rich and extremely evil, had decided to embark on a new adventure. She would be expanding her slave endeavor to America. This would entail a lot of prepa...

Letter From St. Louis

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom... I must write you about my tenant, Portia. She seems to have taken over the house...she's 23 and a hellion! I gritted my teeth, kneeling on hands and knees on the kitchen table as Portia's thick razor strop crashed against my tender bottom. She swung again, and it landed once again, and tears spurted out of my clenched lids. Can I be...

Candy's Day

by daisyboi_sissy on Sep 13, 2017
Transsexuals & Crossdressers

This contains Sissy porn and sex acts. Leave now if you should....everyone here is above 18 years old. Love ya! * I have always loved the feeling of something lacy or sexy on my body. I call it a passion of some sorts, wearing these things made me feel very special and desirable. I was raised by my mom and the closest family we had was my Aunt Trish and h...

Nicole Desired Ch. 01

by NicoleAlldredge on Sep 13, 2017
Transsexuals & Crossdressers

Helen and her two daughters enjoyed themselves as the private lingerie fashion show introduced them to the latest fashions. Helen had always shopped at Lydia's lingerie as there was no better place to find exquisitely sexy lingerie. At the end of the show the women handed the head clerk the order sheets they had filled out. The orders were retrieved by the...

Panty Boy Ch. 03

by AussieKev1 on Mar 17, 2020
Fetish

Author's note. As with all my stories, they are largely based on fact, with some embellishments to make them, hopefully, enjoyable reading. A very kind critic proposed that I had written myself into a corner in this series and I thank them for their constructive criticism, however when writing largely based on truth you are bound by that truth. Please...

The Unsuspecting Candidate Ch. 01

by missvicky53 on Sep 11, 2017
Fetish

I had been told what to expect and there he was, my next candidate! Even if I hadn't been told about this one, I would have recognized the potential he exhibited. How did I know this? I can't really explain it in mere words. All I can tell you is I knew this one would be susceptible to what I had in mind. I had been watching him watch me for more than ten mi...

Panty Posers

by EROTICbearscribe on Jun 1, 2020
Transgender & Crossdressers

PRIVATE PANTY SESSIONS Ch. 01 "Wait! What? Say that again." Doug, my roommate of two years, closed his eyes and took a deep breath. Tension hung heavy in the air. I allowed him to take all the time he needed to explain even though my mind was racing the way it does when your entire world has been turned upside down. I could see he was struggling. It look...

A Sissy Saga Ch. 11

by Snurge on Sep 15, 2017
Novels and Novellas

"Your financial accounting is abysmal, Miss Hancock." said the man from the Department of Inland Revenue. "Some of the necessary records are incomplete and others are totally missing. How can you hope to complete a Tax Return for your business without appropriate qualifying evidence?" Miriam Hancock eyed him with some malevolence as he poked the documents i...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...