Sissy Secretary Stories

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Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

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

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. 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...

Recruiting of a Sissy Maid Ch. 10

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Ten: Changes Continue for Chantel as Her Relationship with Carl Grows. Awake and having a great breakfast superbly made by Carl, Chantel enjoys her morning with him. He has her in one of his robes as they talk about things and their future together. After breakfast Carl says, "Put on a pair of my jeans with your white satin blouse, you can wear yo...

Simon Sissy Slave Ch. 02

by Timewarp10 on Jul 30, 2019
BDSM

Simon's arse remained sore for days, a constant reminder of his new role in life. Over the weekend the pain was severe, but the overwhelming feeling of his humiliation was compensation enough, and produced a warm glow through his body. His mind had been in turmoil all week-end. Sometimes the pain was unbearable, but he bought a cream at the pharmacy that rel...

Recruiting of a Sissy Maid Ch. 11

by Sissy_Chantel on Nov 23, 2017
Transsexuals & Crossdressers

Chapter Eleven: People Moving into New Roles and More. Chantel has made her way back to her club dorm room, enjoying the corrective measures of being a Domme over Biff and Marty. She is certain they will be much more mature and even though they still hold powers over the sissy girls like all other male minder/staff, they will better respect what these sissy...

Wife in Control Ch. 06

by wifetoy on Sep 25, 2017
Fetish

I will bring you your Magic Wand and Trigasm. And suck on your toes, while you enjoy every spasm. Your humiliated sissy in panties, tights, and stilettos. This is the sixth chapter of my wife's execution of the punishment poem I submitted to her suggesting ways to atone for my inability to control my orgasm. Please read the earlier chapters for the full...

Sissy Chantel, New Reality Ch. 07

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Seven: At 'The Agency' and I'm Off to a New Start In My Sissy Life. "Girls this is your new dorm mate, Sissy Chantel." one of the security staff says. The other staff member adds, "You shall take her into your group, help her set up her things and then take her around on a tour of the facilities and such. Report to the office after doing so, OK?"...

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...