Aunt Sissy Stories

18,612 results
Orientation
Length
Source
Infinite Scroll

Keeping My Sissy Secret

by VrijeVogel on Apr 24, 2019
Transgender & Crossdressers

YES! She really won't be home! I thought to myself as I cycled towards my house. My mother's car was missing from the driveway, meaning her plans for visiting a distant aunt hadn't been cancelled after all. Her wardrobe would be all mine for the entire weekend and I couldn't wait to try on her clothes. Aside from everyday clothes fit for a single mom, there...

Marketing 101

by marybethsanford on Sep 16, 2017
Fetish

Players: Mark McLuhan, (Cindy Sue) first year college student and marketing intern at Little Miss Muffin, Inc.; Ms. Helen Pennyworth, owner and president of Little Miss Muffin Inc.; Carol Winters Vice President of Marking for LLM; Susan Evans, Product Manager of LLM; Julie Pennyworth, sister to Helen and professional dominatrix and practicing nurse. Tracy Ma...

Aunt Pamela and Leslie Ch. 03

by fantaseeboy on Mar 2, 2020
Fetish

I spent the days after my second visit with Aunt Pamela trying to decide what I would wear on Friday. She told me to wear something feminine, but I didn't have anything really feminine. The girliest article of clothing I owned were the stretchy, velvet shorts I'd worn on Tuesday. And after doing poorly on a pop quiz in my History class, I knew I had to do...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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Birthday Wishes Ch. 01

by b_wishing on Sep 16, 2017
Transsexuals & Crossdressers

Everyone in this story is above the age of 18 and no one was harmed in the writing of this story. Look for me on Yahoo messenger as b_wishing for some kinky play like this story. Please like my story too. KISS KISS When I walked in the house I felt like this was my hideaway. Always so relaxed is the way Uncle Woody and Aunt Sandy's house is in the winte...

Caught In Pink Panties

by NikkiCD on Sep 13, 2017
Transsexuals & Crossdressers

I just got home from work at the local coffee shop; it's around 3 in the afternoon, about the same time I get home every day during the week. I recently graduated from high school and I'm working this job until I decide what I'm going to do next. I live alone with my mom, my father left us when I was 11 years old, and I'm 18 now. My memories of Dad are that...

Afro Stress Relief Ch. 06

by llts1970 on Dec 12, 2018
Transgender & Crossdressers

I was running a bit late after I'd overslept my alarm clock, my shift at Missy Bee's and the hard riding I got from Leroy must have tired me out more than I thought. I managed to get into work just on time, once there I rang Sarah. "Oh hi Johnny, sorry I mean Tina, wow it's early," Sarah lazily answered. "Hi Sarah, is Marci OK? I can pick her up this eveni...

Aunty's Toys Ch. 02

by novelcriss on Mar 25, 2019
Fetish

**Thank you everyone for reading and taking time to vote on Ch. 01. Do please feedback. I hope you like the evolution in Ch. 02. It has taken a lot longer to get going than planned!** ***** Simon stared at his phone in his office, not quite comprehending. Sally or Aunty as she'd told him to call her had sent him a text. "Simmy dear, don't forget your app...

A Sissy Saga Ch. 23

by Snurge on Sep 15, 2017
Novels and Novellas

Mrs Pardoe's heart pounded like steam-hammer as she made her way to her room. It had been such a long time since she'd had a young girl to herself, to take command of, to admire and to love, and she knew Mrs Amos's niece Lizzie was a real doll. On the way she passed the Joanna television-person ensconced with Gloria in the stair well of the third floor, bot...

It's Another Family Tradition

by Canadagander on Sep 13, 2017
Loving Wives

Copyright © 2004. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - -- - - - - Writer’s Note: This piece is a sequel to the previous story of Sam and the Powell women entitled “It’s A Family Tradition.” If you haven’t already read that one, I recommend that...