Office Sissy Stories

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The Office Sissy XX Ch. 02

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

CHAPTER 3 The smell of Dannie's pheromones was making me giddy. It had been so long since I had last tastes sissy clitty; too long. My mind flashes back to boarding school, Gloucestershire. I was young, under age by English law. It was just after the summer play, and James had decided we should change costumes; boys wear the Shakespearean dresses of the gir...

The Office Sissy XX

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

It had been one of those days where you wish you had chosen flats and support tights. But no, that wouldn't have felt appropriate for the new head of human resources. Impressions are everything in this business. Back to back meetings from nine am to seven pm had taken its toll on my calves, my back and for that matter my mood. It was one of those days I get...

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...

Ian's New Job

by SatinSlip on Nov 26, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex. ************ Wendy moaned as her husband slowly licked around her pussy. She grabbed the sheets in her ecstasy. An orgasm rising excruciatingly slowly in her. Ian was great at cunnilingus. He practiced often on his wife. Delighting in the way...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

Just the Job Ch. 01

by andyp7414 on Sep 13, 2017
Transsexuals & Crossdressers

It's ten minutes to nine in the morning and I stand outside the office, savouring a cigarette. With each eager gulp of smoke I remind myself not to smudge my scarlet lipstick. I have been punished for that before. The early morning breeze sends a shiver up my stocking clad legs and I glance over my shoulder to check my seams are straight. The chilly air run...

Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Sissy Jessica Kinky Office Shagging Ch. 03

by Sissy Adele Howells on Aug 18, 2017
Fetish

It was a lovely sensation to be a member of the Howells family. At 18 years of age, I was now the foster daughter of Adele Howells. Her gorgeous daughter Francesca was my sister, to play kinky games with. Also I had the added pleasure of Joanne Harper, who had been persuaded to join us for the evening. Having exactly the same blonde hairstyle as Joanne, made...

Sissy Jessica Kinky Office Shagging Ch. 02

by Sissy Adele Howells on Aug 18, 2017
Fetish

Hi again this is Sissy Jessica Howells , the kinky 0lchfa schoolgirl with an excited cock inside her navy, blue panties. At this moment my cock is inside Georgina Harris's mouth. Georgina, my 23 year old ginger girlfriend, has her head between my legs, giving me a fantastic blow job. Just feeling her long, red hair against my balls, gives me a weird sensatio...