Sissy Office Stories

94,002 results
Orientation
Length
Source
Infinite Scroll

Mistress Kate Pt. 01

by corduroysissy on Feb 7, 2018
Transsexuals & Crossdressers

L. Jordan Bains wasn't sure of what to expect when he stepped into the large wood paneled office, but he knew whatever it was it wouldn't be good. He was in a lot of trouble, the Leprechaun wasn't known for having a forgiving nature. Jordan had never seen him, he only knew him by reputation, when you hung around the poker tables of Waller City you heard all...

Sharing Ch. 02

by thetoy on Sep 12, 2017
Fetish

Neither Miranda nor I referenced her plan until Monday morning as we were having coffee prior to her leaving for work. (I worked a sort of early second shift most of the week; she was a nine-to-five middle manager at a major corporation.) I was in jeans and a sweatshirt, barefoot, she in her work attire--sharp trousered women's suit, navy with a wide pinstri...

The Dominatrix Order Pt. 04 Ch. 02

by Jwwsmith on Apr 9, 2019
Fetish

Sissy Slut was the only one of Isabella's slaves who had not yet fallen ill. And as such, Sissy Slut was the only slave in healthy enough condition for Isabella to play with. He enjoyed receiving so much of her attention, and she teased and tormented her tease and denial slut unrelentingly. Twenty five days before the next supply of Medication 42 was due to...

Escapism: Nightingale

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

I slobber on the thick, veiny cock in front of me. I slurp away like it's an ice-pop on the hottest day of summer. I'm dressed in a red plaid skirt, a white shirt with a matching plaid badge that reads 'head girl', the neckline just low enough to reveal my leopard print bra. The skirt is riding high enough to reveal the matching thong and floral patterned...

Aztec Art - The Path to Submission Ch. 05

by Sputnik57 on Dec 23, 2017
BDSM

Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

Dinner Date with Mommy Pt. 04

by SissyStoryTime on Dec 3, 2018
Transgender & Crossdressers

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude. If these themes do not interest you, then this story isn't for you, sweetheart. For everyone else... This is it. What you've waited for. Th...

Like a Dream

by Scotsdude on Oct 15, 2017
Fetish

As I arrived at work that Monday, I knew that it would not be a normal day. My throbbing head was a distinct reminder of how my weekend had been. Saturday night was a blinder. It was my friend Kevin's 30th birthday, and as such, we decided to make it a bit of a blinder. It started out with paintball, went on to karting, dinner, and a strip club. Prague's st...

Suspected Affair

by 69Jance on Apr 21, 2020
Transgender & Crossdressers

I had suspected for a while but recently found confirmation, not that I would blame her. I know we loved each other but I also knew there were needs the other could not fill. I found evidence she was having that need I could not meet, met by someone else. I was a bit jealous but in a strange way. There was no anger but a bit of arousal as I imagined her love...

You Got the Part! Ch. 03

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

I would like to thank Mr_Owlow for all his assistance with editing this story. In typical Riley fashion I was in a bit of a situation. GiGi's T.V. show was a complete success and we were picked up for a second season. America was in love with the cast especially GiGi and myself. We were making the rounds on talk shows and late night. We were doing endorse...

My Master

by SissyKaty on Mar 26, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** I pulled into the driveway to my house and I was disappointed to see my future mother-in-law's car in the driveway. "Oh great" I think sarcastically. I'm not looking forward to interacting with her so soon after getting off work. I had just come from a long day working in IT for...