Aunt Sissy Stories

18,612 results
Orientation
Length
Source
Infinite Scroll

Julie and Her Family Ch. 12

by Pretty_Sissy_Julie on May 4, 2020
Transgender & Crossdressers

My sister Becca and I were cuddled together in our nightgowns. Becca is 21 and I am 18. Becca is a beautiful and dominating woman. My name is Julie; I am her submissive sissy "sister." I have been living as a woman for weeks now since my Mum and sis decided I would look better as a woman and not my former life as a very effeminate man. At this point it wou...

Fringe Benefits

by puzziboi on Sep 16, 2017
Transsexuals & Crossdressers

Shawn showed his employee badge to the TSA agent and was waved through to the metal detector. He quickly slid off the lanyard placing it into small bin to take a ride down the conveyor belt. Once he was fully cleared, he collected his belongings and headed away from the security checkpoint to the Office of Physical Plant. He clocked in then spoke to his boss...

The Bargain Dress

by HeatherMaureen on Sep 25, 2017
Transsexuals & Crossdressers

I was in my late teens before I found out how submissive my dressed self was. I'd never really considered myself to be a submissive sissy crossdresser but was about to discover that I was one. I called an ad about women's dresses, heels and other things in the local bargain finder from a payphone. An older woman answered. She wasn't taken aback by my tellin...

The Roommate Pt. 03 - Miranda

by ValoryG on Sep 16, 2017
Transsexuals & Crossdressers

Author's note: I notice there are several other Literotica stories also using the title "The Roommate," so I decided to differentiate this series by adding "Miranda" to the title. Thanks for your comments; I enjoy reading them. ***** Miranda and Josh didn't see much of each other for a week and a half. She took off for a few days to visit relatives (drivi...

Mistress Starla Proves Her Point

by justincbenedict on Apr 16, 2018
BDSM

Porky was weeping bitterly, and at the same time, his dick was straining, and quite excited. Who was this girl? Starla was his friend Spalding's cousin, and he'd seen how she enslaved him--Olivarius, the school's intramural lacrosse coach had told Porky that Starla had taught him how to suck his own dick... Several young women of Porky's acquaintance foll...

Poker Night Substitute

by JustATale on Sep 13, 2017
Transsexuals & Crossdressers

I was an entry level accountant at a bank. The pay wasn't great but it was what I had studied at college and it was a start. To help with expenses I shared the house I rented with Todd, and Trish. Todd was an architect working as a draftsman until he could get something else. Trish was working as a cashier at a local store. We all got along great and the arr...

Laura Learns Her Husband's Secrets Ch. 02

by lesliejones on Sep 13, 2017
Fetish

I appreciate the feedback from many of you who asked me to resume this story and apologise for the delay in my so doing. My return to this story found me fascinated with the changes occurring in both Jack and Laura. * When Laura had discovered her husband Jack's penchant for surfing the web in search of naughty pictures and stories about women's intimate b...

Chuck

by wajawhiii on Jun 5, 2018
Erotic Couplings

My name is Marjerie. I'm thirty-nine years old. I was married to George when I was only twenty. He left when I was just twenty-three and Charles was only two. I got an uncontested divorce three years after he disappeared. Charles is the only thing George gave me and the best thing I've ever received. Charles is now eighteen and just graduated from high scho...

The Dragon Ring Ch. 03

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

Three Fool me once shame on me, fool you twice...? I awoke in the early dawn. The sun yet to broach the horizon, but casting its rosy glow high into the cloud speckled sky. Sissy was lying across me; her head nestled into my shoulder, her arm curled around my neck, her hips across mine and her foot wedged twixt my knees. I reached over and smoothed her...

Harry's Spring Break Ch. 3

by Sabledrake on Sep 15, 2017
Sci-Fi & Fantasy

"Fighting with your roommate, eh?" Harold Ethelbald Senior said, arching his iron-grey brows as he studied the sheet of parchment. "Is that all it says?" Harry reached, but his grandfather whisked the sheet away with a quickness that belied his age. "What else might it say?" "Nothing about ... girls?" "You had girls in your room?" "Let me see that!...