Sissified Stories

213 results
Orientation
Length
Source
Infinite Scroll

Ladies That Lunch

by Effie100 on Sep 17, 2017
BDSM

Chapter 1. Simon's wife had always admired the ladies at their local tennis club. They were all of a certain age, and when they got together socially there was a quiet serenity in their companionship. Beautifully dressed, without exception, they met every Tuesday and Saturday for lunch in the Pavilion restaurant for a long, lazy lunch full of chatter and la...

Sheila and Penny

by Sheila_TSSub on Sep 19, 2017
Transsexuals & Crossdressers

Part 1 I had been upstairs that morning doing my chores. I was dressed in a cute little yellow summer dress and leather heels with 4" wedge heels. When I came downstairs I found Mistress Tina (my wife) and Princess Gina (our daughter) in the den. There was a man there that was unknown to me. "Come here." Tina commanded. I went in and knelt beside her cha...

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

Panty Posers Ch. 02

by EROTICbearscribe on Jul 6, 2020
Transgender & Crossdressers

NOTE: This is a work of fiction. The characters appearing in this series are consenting adults over the age of 18. Any reference to past experiences by any character appearing in this story are intended to define that character. * It was almost 3 when I woke up in my roommate's double bed. Sunlight streamed between the broken slats of his plastic blinds...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...

Pixie's Reward

by Salamando_Flames on Sep 26, 2017
Sci-Fi & Fantasy

ONE Duncan had been driving home from the factory in the wee hours of the morning when he encountered a pixie. It smacked against his windshield with a rather loud "THWAP!" as he idled at a stop light. The pixie groaned as her form splayed almost comically across the glass. Duncan frowned and observed the small creature with that perfect deadpan look only...

No One Could Beat My Life!

by maninconn on Sep 12, 2017
BDSM

No one could beat my life! No, really I am so serious. I was livin large. The investments I gambled on starting with paper route money I made in 7th grade were booming. Turns out with a little research, "high risk" was nothing but ink on a label, and a kid willing to study financial papers as much as his peers followed football could get pretty good at picki...

Young Sissy Ch. 01

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

Author's Note: This is a follow up to The Young Master series. You can start here if you aren't interested in Belle's misadventures as spoiled young man turned out by his own sissy slave and eventually enslaved by his step-father, but it does introduce a lot of characters you'll read about in this series. * I don't know how long I was under...days, weeks....

Lulu's Lockdown Diary

by lululuvsblack on Jul 6, 2020
Transgender & Crossdressers

Day 1 So, with this virus we've all been told to stay home and not have any physical contact with people outside, not get together in groups at all, and not even step out of the house if not completely essential. We're locked down. I guess it wasn't a great time to move in with a couple of guys I barely know, but there you go. There's nothing I can do about...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...