Crossdressing Strapon Stories

2,832 results
Orientation
Length
Source
Infinite Scroll

"Sissified": 12 Days of Sissy-mas

by silkstockingslover on Jan 7, 2019
Transgender & Crossdressers

Summary: Straight man is turned into a submissive sissy by.... Note 1: This is my 400th story release. To mark the occasion, I thought I would try something longer... mixing many of my themes into one long, complex story. Thus be warned that with over 40,000 words, this story is a marathon not a sprint, and it includes a variety of themes including: cross d...

The Camping Trip Pt. 03

by Tetris07828 on Sep 18, 2017
Group Sex

Warning: You might discover typos, grammatical errors, misspellings, and other flaws in the following writing. If this offends you or you feel the need to feel superior and point out every error please stop reading now. Thank you. ***** Wednesday We woke up about the same time. Ann looked into my eyes and said, "Morning lover. Know what time it is?" I th...

Cruel FemDom Fitness Training Camp

by Dungeon_V on Sep 26, 2017
BDSM

PROLOGUE The lights in the dungeon were dim, but the acrylic cane She whipped through the air was black light reactive, creating a fearful streak of light through the air an instant before the inside of my right thigh seared with pain. The sound of my sudden gasp could not block out the snap from skilled administration of a punishment stroke. I felt I had b...

Isabella's Reversion Pt. 02

by silverbackteddy on Sep 16, 2017
BDSM

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. I do my best with spell an...

Highlights from a Lodge Xmas Party

by KeyesLodge on Jan 7, 2020
Celebrities & Fan Fiction

December 2019 "Let's go-oooo..." Anya Taylor-Joy told me in a sing-song voice as she leaned her head to the side. "What for?" I asked, only pausing long enough to say it. Then I went right back to kissing her along the neck. "Because the party has already started," Anya said while looking up at the ceiling, desperately trying to resist the urge to get bac...

Seasonal Job Security

by Voboy on Dec 2, 2019
Mature

Ahhh, Christmastime at the underwear store... Make sure you read all the Holiday Contest entries and vote on your favorites! * * * There's nothing quite like driving along the sea on a nice, warm day, windows down, smelling the salt and letting the sandy sun soak into the car, driving out the smells of stale coffee and old fast-food wrappers. Today was a...

Strippers and Prostitutes Ch. 11

by Scorpius1945 on Sep 14, 2017
Novels and Novellas

Author's notes: 1. This story follows on from my previous story 'Mixed Emotions' in which the characters are introduced and developed. It is strongly recommended that 'Mixed Emotions' is read first. 2. This is a work of fiction. The activities and practices described in this series are neither condoned nor recommended. If you choose to do anything describe...

More Than Skin Deep

by Couture on Sep 11, 2017
Fetish

Lawrence's deep-set frown was illuminated harshly by the cold blue light of his computer monitor. He didn't like what he was seeing on his monitor. Didn't like it one bit. At nineteen, he would have watched it eagerly. At fifty, he knew he should turn it off, but he couldn't bring himself to do it. And the more he watched, the angrier he became. On the othe...

The Run

by Colleen Thomas on Sep 12, 2017
Sci-Fi & Fantasy

Wednesday 1900 hours She moved across the crowded bar with a feline fluidity that would have been called graceful or elegant on a pretty woman. With Margo the word most often used to describe her movements was lethal. She was a mountain of a woman; nearly six foot one and she packed nearly two hundred pounds of muscle on that frame. Her legs were long and h...

Amanda's Seventh Slave

by glossophile on Oct 9, 2018
BDSM

He was chosen the moment I saw him on the street that hot summer night. Tall, dark and handsome to say the least, and a young thing, surely of age, but no more than 20, I guessed, a tender and succulent morsel for seasoned predator like me. The wet warmth and pulsing tingle I felt between my thighs told me he was the one. I followed him at a discreet distan...