Sissy Princess Stories

21,927 results
Orientation
Length
Source
Infinite Scroll

Making of a Sissy Whore Ch. 03

by SecretAgentFun on Oct 21, 2019
Loving Wives

Pimped Out If you haven't read the first 2 chapters, it might be a good idea so that this makes more sense. Your call, and I hope you enjoy either way! *** Jeff stepped off the bus feeling defeated as he walked the five blocks back to Brad and Kayla's place. He couldn't even think of it as home now, since Kayla was sure to kick him out tomorrow. He was jo...

Keith's Caught in a Costume Pt. 03

by gaildaniels84 on Dec 24, 2019
Transgender & Crossdressers

Keith's alarm went off and he silently reached out a hand and silenced it. He'd hardly been able to sleep at all, tossing and turning with worries about what school would be like today. It had been less than a day since his life had turned into a nightmare - his incredible teacher had caught him rubbing himself in a cheer uniform and then he'd had to buy pan...

Wife in Control Ch. 01

by wifetoy on Sep 25, 2017
BDSM

I originally posted this story almost two years ago, but lost the other parts of the story when my computer crashed. I am reposting this part and will be posting the other parts of the story over the next few weeks as I finish retyping them. While I may post some fictional stories in the future, all of the events in this one and the other parts to follow are...

Reversing Rolls

by MyCuteCherry on Sep 16, 2017
Transsexuals & Crossdressers

"Wakey wakey sleepy-head." I hear as I wipe the sleep from my eyes. "Did you sleep well honey?" "Yes thanks Sophie. I always sleep well when it's by your side." "Aww. I do too. We should be getting along. It's 8am, and we have a meeting to attend to." Like a puppet on strings, jumping to Sophie's command, I promptly swung my legs out of bed - I know how...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Kasey's Confession Ch. 08

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

I woke up the next morning feeling incredibly sore all over. I was lying on the couch in Mr. Smith's living room, covered up with a blanket, with only vague memories of what had happened after Mr. Smith finished fucking me. I knew Pedro and Jake had taken turns with me as I had flashes of memory, almost like photographs, of them putting me in different posit...

Being My Roommate's Sissy Pt. 03

by SubTessa on Feb 6, 2018
Transsexuals & Crossdressers

SubTessa (Author): Sorry for the wait guys, University sort of made me forget about this entire thing. If you're new to this series and start here, I think it'll be ok. The last two are just the lead up to this day. I hope you enjoy it! You should also read these with a healthy level of self-esteem! ~~~~~~~~~~~~~~~~~~ I wake up, quickly forgetting what I...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Hero Losing Himself

by lol159 on Jan 8, 2019
BDSM

Since Mark was a kid he dreamt about being a hero. He wanted to be someone who did the job on his own. He wanted to be the macho just like his hero The Jaguar Man. He was the proudest man about himself. Having been grown up in an orphanage after his parents were both killed by a robber, he knew best that no kid deserved to lose his family. That's the reason...

A Sissy is Born Ch. 02

by gtanya on Oct 13, 2020
Transgender & Crossdressers

Author's note: This story is the second chapter of "A sissy is born" series. Please note that it is a very slow build up and if you are looking for some hardcore sex right away, it is not for you. Please leave your comments to help me improve. It was a fairly uncomfortable couple of hours of the train ride with the constant staring of Mr. King. His gaze som...