Sissy Secretary Stories

20,580 results
Orientation
Length
Source
Infinite Scroll

Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

You Can Always Say No Ch. 06

by AngelCherysse on Sep 25, 2017
Transsexuals & Crossdressers

We pulled up in front of the professional building opposite the sprawling medical center. The intervening multi-story parking structure was well-lit, but sporadically populated with vehicles this long after business hours. "What are we doing here?" Angie questioned as we stepped out of the cab. "Baby, Faye and I have someone we want you to meet," I explain...

Cyber Sissy Ch. 05

by missvicky53 on Sep 25, 2017
Fetish

A fantasy by Miss Vicky Part 5 (The Last One) The rest of the evening passed with the two of us cuddling on the couch, each with a glass of wine. Megan had changed into a black floor length nightgown with a lace inset running diagonally across the front. This meant that with each movement of her body, I would catch a glimpse of various parts of her body. T...

Her Doll Ch. 02

by WickedDoll on Sep 16, 2017
Transsexuals & Crossdressers

Covers being pulled gently away from my naked body, soft lingering kisses warm the sculpted calves of my legs. Lips and long tendrils of silkened hair tease my skin, coaxing me awake. My body quivers with excitement as his tongue circles the back of my knee then traces up the inside of my thigh. Whether he caresses every inch of my long, smooth limbs with hi...

The Gynecomastia Kid Ch. 02

by Johnboy9 on Sep 16, 2017
Transsexuals & Crossdressers

It's been two weeks since I got out of the hospital and I was feeling better and better as each day passed. Having no income and no real money of my own, to speak of, I was forced to continue wearing the clothes that Crystal left me since I couldn't afford to go out and buy clothes of my own. I must say though I'm getting to like the soft, airy feeling of t...

Sissy Amy Loves Mummy Belinda Ch. 03

by Sissy Adele Howells on Sep 17, 2017
Fetish

Nurse Sue George sat opposite her best friend, Nurse Lynda Christopher. Both looked stunning in their royal, blue nurses uniforms. Lynda was a tall women in her middle forties, with dark, long hair, tied back in a bun. She wore glasses, but was attractive for her age. The best thing about Lynda Christopher, was that she sneezed frequently and enjoyed blowing...

Devoted Husband Learns a Lesson

by keptsissy on Sep 18, 2017
Loving Wives

PART ELEVEN: I was her houseboy-slave almost two years prior to her taking a lover. She took over my submissive fantasy, made it completely hers. At first it was talking dirty when I'd service her. She started 'expanding' on that, got very cruel, teasing and dominant. She started checking out dominatrix websites too. After about six months she was a complet...

Balls On The Line In City Trading Ch. 02

by gomorrah on Sep 16, 2017
Transsexuals & Crossdressers

So with much apprehension, I turned the handle on the blue door. Stepping through, I struggled to adjust my eyes to the brilliantly white light streaming out of the other side. I raised my hand to try and filter the glare, and heard the door click shut behind me, and then double-click again. Instinctively, I tried for the handle on my side, but there was no...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Steve to Stevie to ?? Ch. 08

by gbr2004 on Sep 19, 2017
Fetish

Ms Storm has exposed me to my boss, showing her that I'm nothing but a sissy faggot. It was so embarrassing. Then she watched as my Mistress took my virgin asshole. Ms Storm talked to my boss, Ms Hunter, telling her that she wanted her to keep me in line at work and make sure that I remembered my place while at work. She gave Ms Hunter permission to use me i...