Sissy Boy Stories

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Sissy Boy Secretary

by Hotenuf4u on Sep 19, 2017
Fetish

As I sit here in the outer office space of the company CO, I look like an ordinary male secretary. On the inside I'm wearing a pair of pink lace panties, at my bosses request. You see I'm really a sissy inside and my boss takes advantage of this at every possible opportunity. I've worked here for 2 years now and it wasn't always this way. My boss, Elaine, a...

Sissy Boy Secretary Ch. 09

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he...

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...

Sissy Boy Secretary Ch. 07

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine and Tammy had been friends before the unfortunate divorce and still now maintained a good friendship. After all, it was Elaine that helped her get a job as an executive secretary during all of her school breaks, including throughout the summer break. Tammy had known that the company Elaine got her the job at was also Elaine's biggest competitor in the...

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...

Sissy Boy Secretary Ch. 05

by Hotenuf4u on Sep 19, 2017
Fetish

The whole week was spent on completing the paperwork needed for our customers. There was a lot of work and I had worked through quite a few lunch breaks, but completed the work on time. Business was getting better each week and Elaine had said that I was one of the reasons that it was going so well. Although I still stripped to my panties while in Elaine's o...

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. 03

by Hotenuf4u on Sep 19, 2017
Fetish

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you! After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in...

Sissy Boy Secretary Ch. 02

by Hotenuf4u on Sep 19, 2017
Fetish

I got into the office 15 minutes early this morning, her panties cleaned and put on under my clothes, as instructed to do. The satiny lace felt good against my cock as I moved around the room. Just when the finishing details for the Scottsdale account were complete, she entered. She looked so sexy walking into the office, her ass swaying so nice. It looked l...

Sissy boy shock

on Apr 29, 2025

Story about sissy crossdressing and other good stuff. Milo was a small guy he stood 5foot 7 inches tall, he was always bullied for his feminine physique growing up. No matter what excerise he tried weight lifting, martial arts or sport he failed to gain any muscle mass. Except in one place he always had a perfectly shaped ass. He never did squats or even leg...