Sissy Office Stories

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Orientation
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Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Owning The Girl Next Door

by Frognut on Sep 11, 2018
Sci-Fi & Fantasy

Chapter 1 The Beginning It started one afternoon after I had gotten off work with my Dad, I was tinkering with my car in the driveway when I hear my name being called. I looked down the street and a friend of mines girlfriend was walking to me, I said hey Sherry what's up? she asked what I was doing tonight? I said going to cruse the beach for a couple...

Outed and Married Ch. 04

by keptsissy on Apr 23, 2018
Transsexuals & Crossdressers

I feel the cool air all over me. I'm in his warehouse. It's a huge facility and I'm naked and restrained in the middle of the football field sized room, surrounded by floor to ceiling full shelves of his adult sex toy products. Two other men that stand and watch stare impassionately. One of the men says something to the other man, points to rear end. The bot...

XChange Seminar, X-change, X Change Ch. 02

by Grabenork on Feb 6, 2018
Transsexuals & Crossdressers

"Good morning, everyone! I am Dr. Welcott, and I am very happy to welcome you to X-Change Technologies, Inc. You are all here because you attended one of our X-Change Seminars run by Dr. Brewer at the Comstock Institute. He reports that you all participated in the seminar enthusiastically and then signed a list to volunteer to become future demonstrators at...

Mistress Commands Me in the Office Pt. 04

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Continuing Cast of characters: Bob, or Robert, or Dick (or whatever Mistress decides to call me): Me Rick: My boss Brad: An office co-worker, loves to get on my case Sharon: A pretty co-worker Jim: another co-worker, very cocky and arrogant David: another co-worker, pretty suave, the women all like him Rod: Office co-worker in an adjacent cubical, ver...

Getting Help Ch. 01

by azkelkel on Sep 16, 2017
Transsexuals & Crossdressers

I nervously sat in the waiting room for my 1:00 p.m. appointment with the therapist/psychologist. I found her through online searches, as I guess we do all things nowadays, where her credentials and location were most important to me. She received her various degrees from decent universities and chose to open up her practice in an area just far enough away f...

Natalie on Sunday

by natalieukcd on Oct 19, 2020
Transgender & Crossdressers

Lewis had fucked me after i had ridden him to my orgasm. I was no longer horny but he had fucked me anyway and although i wasn't really Natalie in my head during that, I still enjoyed having him behind me, holding my hips and telling me to keep my head down or lift it up. I loved the feelings of his cock inside me and he told me what a sexy fuck i was. I bel...

Alt. Queen of the Left-hand Turns

by maxdname on Sep 16, 2017
Romance

See that beautiful girl in the poster? When I first met her she was a simple hillbilly girl from Appalachia sleeping with stock car drivers in order to get a pit pass. Look at her now: she's a blond and a model with her own TV show that earns her more in a year than most stock car drivers will earn in a lifetime on the circuit. A national racing magazine i...

Moving To Louisiana Ch. 3

by eeric on Sep 14, 2017
Interracial Love

If you have the time you can e-mail me at the email address in my profile and tell me what you thought. * * * * * Over the past weeks Helen has become more open about her love for black men. She has been out to clubs and danced with both Ty and James, although never with both of them together. Then she has had me lick and suck her pussy when she gets home...

The Truth is Known

by desireethtttv on Sep 16, 2017
Transsexuals & Crossdressers

While my wife of 16 years has known of my fancy for cross dressing, she really didn't realize how far I delved into the realm of womanhood. That is until yesterday, when I forgot to lock my office door. It all came to a head, in more ways than one, when she burst into my office and found Desiree, "The Hot to Trot Transvestite" busy with one cock in her ass a...