Sissy Secretary Stories

20,580 results
Orientation
Length
Source
Infinite Scroll

Becoming Sarah Pt. 01

by sissy_sarah_09 on Jul 31, 2019
Transgender & Crossdressers

I used to write these on Tumblr, now on Fetlife, so I have a few to post quickly, then I'll be adding new ones as I write them * Walking up the drive from work, I put the key in the door and pulled the post from the inside of the door. It had been a long day, but it was finally the weekend and I was ready to relax. I always got home before my wife, Katie,...

Slave Chavis

by justincbenedict on Sep 17, 2017
BDSM

Chavis crouched in the quite cramped dog-cage, and willed himself not to pee on the newspaper. His bladder was killing him, and he'd been in the cage for three hours, ever since Miss Hooks had gone out shopping. What if someone broke in, and saw him, a naked preppie, locked in a small dog cage? The burglar or whoever, would laugh his ass off, really. Final...

Sexual Harassment Ch. 01

by Cute Little Thing on Sep 18, 2017
Transsexuals & Crossdressers

The story is so familiar I hardly need to repeat it. I'm talking about layoffs of course and today it was my companies turn. It started this morning, rumors started right away and by lunch it was clear what was going on - our company had been purchased by a competitor, and they were liquidating half the staff by sundown. Anyone judged to be redundant was gon...

St. Andrews College Ch. 06

by Dr_And_Mrs on Dec 2, 2019
BDSM

WARNING: This is a FANTASY story. It may contain themes of consensual non-consent, slavery, dominance/submission, and/or extreme pain. Please do not try any of this at home. Do not try ANY fantasy with ANYONE unless you've discussed it in detail with them beforehand. Informed consent is fucking mandatory. * It was Friday night, and my wife and I had a doub...

Tricked Into Love

by bluegiraffe on Sep 14, 2017
Erotic Couplings

I was looking through the internet personals to pass the time, although deep inside, I was actually desperate for a date. My name is Mike, and I was a 21 year old guy in college studying sociology. I wasn't bad looking or anything but just a little shy. Usually, the personals were just full of kids putting fake postings or unattractive women who couldn't ge...

The Hairdresser

by justincbenedict on Sep 17, 2017
BDSM

JULY 2001 "Can't I cum, just once, Jenise...it's been 139 days and counting!" But Seifert knew what would happen to him if he bugged his wife again! THWACK! Jenise Quynlan thwacked her husband in the side of the neck as he scurried to the back of the Buttermilk Beauty Bazaar. Yes, and then she tugged on the chains that were locked through the hoops on his...

His Sissy Bitch Ch. 06

by keptsissy on Sep 18, 2017
Transsexuals & Crossdressers

I think about it all the way home, makes me so hot I want to masturbate right there in the back seat of the cab. I can feel the wet spot on the end of my little thing, feel it against my inner thighs, feel my small baby like penis slide around tucked up under my butt, pushed down and held between my legs as we ride toward my house. I try to keep my penis tuc...

My Toy Nancy Ch. 03

by NiceNastyMann on Sep 19, 2017
Fetish

I overhear Nancy ordering Mark around, telling him to make sure he has his car keys and wallet. She takes great delight in reminding him of the consequences if he embarrasses her in public. The two of them head out of the apartment and on the way to their shopping trip. After they're gone I get my phone and dial Marge, an old friend of mine. After a few rin...

The Bradfords Ch. 01

by Erotictales4u on Oct 13, 2017
Transsexuals & Crossdressers

All characters in this story are over 21 years old. This is a fictional fantasy that contains elements of both femdom and transsexual/cross-dressers niche, it is focused on humiliation. This is the first of a new series. I would love your feedback. ***** "What the fuck is the meaning of this Tim!" screamed Tim's wife Jane as she ran her hand through her lo...

Kitty's AssKissing LegBoy Pt. 01

by KittyZateez on Aug 28, 2018
Fetish

My LegBoy has been tending to my sexy legs and high heels for several weeks now during repeated teasing and denial sessions. During that time, we have had many delicious and stimulating evenings together, and I am absolutely adoring the way he has been responding to my specialized erotic training! He is just so interested in me, so willing to obey my whims...