Sissy Office Stories

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Virginia's Luxurious Evening

by JonathanStone on Sep 16, 2017
Transsexuals & Crossdressers

West Palm Beach didn't have many cold snaps, but when one did rake the city the weather seemed twice as frigid as it actually was. Virginia Stanton sat alone in her office on the third floor of Prism Design's building overlooking the Intra-coastal Waterway. She had been chilly all day, mainly because of the dampness in the air; Forty-eight degrees outside wa...

Erin's Fantasies: The Schoolgirl

by petmyhead on Sep 17, 2017
BDSM

Erin Sommerset did her best to look much like your typical public high school principal. Her hair was always in a tight bun, her glasses had a thick black frame, and her makeup always leaned towards severe rather than cute or sexy. She wore professional clothing-suit pants, plain blouses, and matching blazers-and even if everything she wore fit well, it did...

Whitemailed Ch. 01

by Stardog Champion on Sep 12, 2017
Erotic Couplings

"SHIT," Caroline Jarrett spat out loud when her left tennis shoe clipped the coffee table in the middle of her claustrophobic living room. "At least you didn't do it with your sandals on like the other day," she chided herself, trying to rub the pain from her foot as she fought the overwhelming urge to kick over the 4-legged nuisance in front of her. "You l...

Lynn, Rita & Me

by louienohio on Sep 14, 2017
Exhibitionist & Voyeur

Which was it? ---------------- My gal Lynn was stopping by my law office, after 5:00. It had been only a few months since Lynn and I started seeing each other and our passion was very hot. The evening's plan was that we would go out after work and drink wine, probably to an upscale restaurant in downtown Columbus. My secretary and our mutual friend Rita wo...

Lust for Ma'am

by markdlover on Sep 17, 2017
Loving Wives

I always viewed Maria as an extremely attractive woman. Not a single man in our workplace would disregard her physically good looks. She also possessed the intelligence that could mesmerize an executive. She graduated with the honor magna cum laude in her college class finishing business management. She would always wear stimulating clothes that you might...

Mom & Me Ch. 37

by Yechesem on Apr 20, 2020
Romance

Planning & Preparing For The Fall Dance While I was walking toward the school, it occurred to me that the Fall Dance was only two weeks away. I need to talking with all my girlfriends, and Ginny, to make sure I'll be able to dance at least a couple of times with each one of them. I needed to know if they were going to go as someone's date or just show up by...

The Office Team-Building Day Ch. 03

by thewhitestripe on Sep 18, 2017
Exhibitionist & Voyeur

"Get your cock out." I was sitting in Carmen's office early on Friday morning. She had requested this meeting--an hour before our official start time--the day before; an appointment I had been dreading. I had gone immediately to her office to tell her I would be there in a minute, but she's asked me in. She hadn't even given me the chance to take off my su...

Confessions of a Mailgirl Ch. 06

by Seahawk76 on Sep 26, 2017
Exhibitionist & Voyeur

A MOMENT OF TRUTH The employees on the ninth floor of the tower paid little attention to me as I exited the elevator and walked toward Barbara's office. As far as they were concerned I was just another DDE employee wearing business attire on my way to a meeting somewhere. I'm not even sure some of them would have recognized me with my clothes on even if the...

Cheating Boss

by GeorgeTasker on Sep 25, 2017
Erotic Couplings

Steven Harper groaned as he slammed his hand down on the snooze button of his alarm clock. Another day had begun. The twenty two year old climbed reluctantly out of bed and headed for the bathroom to get ready for work. Steven was average in almost every way. Average looking, average height (if you were generous) and average personality. He worked for a con...

Lesbian Takes To Anal From A Guy

by walterio on Sep 19, 2017
Anal

PRELUDE Cathleen walked into my office and as she had so many times, she closed and locked the door and then put the door brace in place. This was so no one would walk in on us unexpectedly. I looked at her and smiled but I reminded her of my schedule. "I have to go to President's Council in 30 minutes," I told her. "I know I saw it on your calendar. We...