Sissy Plug Stories

24,564 results
Orientation
Length
Source
Infinite Scroll

My Fantasy

by livinfree on Sep 15, 2017
BDSM

"Hello?! I'm home!" I shouted as I threw my keys and purse on the counter. Taking a look around, I shook my head at the clutter that was scattered across the table and into the kitchen. Housework never ends, especially with two kids and two roommates that were just renting a room, and felt no more effort was needed. My husband? Well, he tries. In his own v...

Wheals of Fortune Ch. 02

by Calandria on Sep 16, 2017
Novels and Novellas

You'd better be over eighteen if you are about to read this – all of the characters in the store are. It follows on from part1, of course, and part 3 will be along later. I slept between my lovely satin sheets on my second night at the Gordons' Mansion, my back still sore from my whipping, my anus stretched and aching with the unfamiliar intrusion of the bu...

Power and Will

by kyrie1595 on Sep 12, 2017
BDSM

i stand, my arms outstretched, hands firmly planted against the rough wall, legs spread widely, ass out... waiting. i don't dare look over my shoulder to see what You're doing, though i'm desperate to do just that. i can feel You behind me, Your heat alone telling me You're still back there, watching every move, listening for every sound i might make. i ca...

A Visit to the North Ch. 06

by MadQuill on Sep 15, 2017
Transsexuals & Crossdressers

This is a mystery story of Annabelle's life and the changes she encounters. The characters are all fictional. Please read the earlier parts and leave your comments. ***** Mistress Donna had a splendid home with a view over the western city. There was light snow falling and someone had prepared a large fire. "Douglas please help our lovers feel comfortabl...

House Trained

by Rodwarrior on Sep 15, 2017
BDSM

It didn't last forever. It didn't even last a moment. . Before I could say anything Kelly put the ball gag back in my mouth. She pushed a button on a remote and I was watching a replay of Mercy and Doug on the television.. Kelly went about her business, going in and out of the room, glancing at the television occasionally. I just lay there trying not to thi...

Francis to Frances

by pietermocks on Sep 16, 2017
Transsexuals & Crossdressers

It was never my intention to go to live with Aunt Matilda and Aunt May, in New York state five hundred miles east of Arlsberg but when I was offered a place at Uni a short bus ride from their place that Dad suggested I should see if I could stay with them. Dad always referred to them as Aunt Matilda and Aunt May but actually Matilda is my dad's aunt and May...

Betsy's Birthday Party

by OneWhoKnows on Sep 1, 2017
Group Sex

Author's note: This is a sequel to the story, Pool Party turns into Threesome. Reading it will let you know how this birthday party came to be. Betsy had gone to Susie's, where there were four girls at a supposedly girls only, nude pool party. But Susie's boyfriend, Paul, had showed up. He had the pleasure of putting suntan lotion on all four girls. First t...

Roman Holiday - The Wager Ch. 03

by sw1tchm3up on Feb 12, 2019
BDSM

Scarlet's breath slows, and with the high of a climax receding, her body begins to issue a damage report. Her scalp aches from his grip in her hair, her throat is coarse. Her breasts feel swollen, and the throb between her legs is a painful one, unlike the hot need she's felt most of the night. Her neck is sore, and the weight of the collar feels heavier tha...

Dirty Talk, Clean Fun

by InventorSpurt on Mar 3, 2020
Anal

Hnnng I quietly groaned as I came, shooting a few ropes of cum into the toilet bowl. I closed Literotica on my browser's private mode and turned my phone's brightness all the way up. The bathroom was pitch black, but the phone's flashlight was too bright; it would shine under the door and disturb my wife. Putting the phone on the counter, screen up for th...

Surprise Hotel Submission

by Lifeinlingerie on Mar 2, 2020
Fetish

"Come into my parlour, said the spider to the fly." I knew I was trapped the moment she looked at me from across the bar and cocked her finger my way, commanding me to move her way as opposed to walking over to me. The hotel bar at W was busy that night, but I was sitting alone - hoping for something interesting to happen. The day had been a write-off, bu...