Sissy Secretary Stories

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A solution

by Seahawker on Apr 3, 2020
BDSM

Hello my name is Mark. I'm a 35 year old marketing accountant with my father's advertising agency. My wonderful wife, Stacy also works as an accountant at my fathers company. We have been happily married for 12 years. With our hectic schedules, children have just not been a real possibility and to be honest, neither one of us are in a hurry to become parents...

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Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

The Initiation Ceremony

by DrLuverotica on Oct 21, 2019
Transgender & Crossdressers

FRIDAY A.M "Don't forget I'm out at Carrie's hen party tonight." Jo said, as she was just leaving for work. "Carrie, your secretary?" "That's right, Carrie my very sexy secretary." "Will you kiss a girl and like it?" "You wish!" "A boy can fantasise." "Well let's hope Carrie's got some nice fantasy games lined up. Or a male stripper or two." And with...

The Settlement

by cathynylons on Sep 12, 2017
Transsexuals & Crossdressers

While my wife was away visiting her mother for a week I had a wild fling with Kate, the sexy new secretary at my office. A young tart about 22 yrs. old in tight skirts and spike heels. She drove me crazy and before I knew it we were doing it on my desk with our clothes mostly on. Then, at her place near the beach and then, on the beach at night. Wild times....

A New Life Ch. 04

by sissycinnamonswirl on Sep 18, 2017
Transsexuals & Crossdressers

The man's Skype camera was still showing black, but I could hear him breathing heavily as he watched me pulling the chains that attached to the clamps on my nipples. I was pulling hard enough and steady enough to begin stretching my titties...as mistress requires me to call them. It was extremely painful as the clamps themselves were little more than metal t...

April Fool Office Sissy

by lululuvsblack on Apr 10, 2018
Transsexuals & Crossdressers

"Dear Colleagues This week, in order to help with our efforts to raise money for charitable causes, we have decided to mix up our usual policy of dress down Fridays. This Friday we are instead instigating a "dress up Friday" in which staff are strongly encouraged to come to the office dressed in the office attire of the opposite gender (that's suits and tie...

Roxy house of xxx 2 the secretary pet

by Carterdruzba on Dec 31, 2020
Interracial

I onced worked at a porn shop called Roxy house of xxx until I met the love and goddess of my life Sandra or mistress Sandra she picked me as her new secretary a sissy secretary for her company and her big black cock I never had a better life than this get paid more and get fucked more by Sandra big black penis.What's next? How it all started...

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Sissy Boy Secretary Ch. 04

by Hotenuf4u on Sep 19, 2017
Fetish

Arriving at the office 15 minutes early, walking past three of the other secretaries, noticing them smiling and giggling when they glanced my way. Elaine must have told them of my secret desire to wear panties. Today's choice was the white lace thong pair, which felt good as they rubbed against me as I walked. Feeling my face turning red, I walked faster to...

Sissy Boy Secretary Ch. 08

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine knew that it was now time to implement her plan to bury her nearest competitor, Bill Andrews... You see Elaine's secretary arranged through the secretarial pool to make sure Tammy, the daughter from next door, got the job as Bill's secretary... As you already know Elaine has used Tammy's information to her advantage and now it seems that Bill was at h...

The Dragon Ring Ch. 04

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

The first days travel was wholly uneventful. We stopped to rest the equinininys mid morn; some people had brought snacks to eat while others including us took the air. My mistress declared that eating was bad for the digestion when one was thrown around on the track, which had turned to bare earth outside of the town. We stopped at an inn at lunch time t...