Sissy Secretary Stories

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Orientation
Length
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Infinite Scroll

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...

Pink Panties

by DrLuverotica on Mar 27, 2019
Transgender & Crossdressers

It all started with a pair of pink panties. It was sometime after midnight when Jo arrived home from being on-call at the local hospital. She'd received a phone call several hours earlier about a bleeder and had to rush in. Recently her workload had become almost unbearable, but we needed the money so she was working her sexy curvaceous ass off. By the ti...

Elaine's Neighbors

by Hotenuf4u on Sep 14, 2017
Fetish

Elaine's Neighbors: Their Story Tammy's mother had divorced her father just over a year ago. It seems that his lack of trust got the best of him which ultimately led to his downfall. Tammy was home on a vacation from her college studies when she noticed a change around the house. It seems that now her father has turned into a workaholic which left Mom prett...

Powerless

by siscuc on Sep 16, 2017
Transsexuals & Crossdressers

I was alone in the house, Tina was at work. It was 4 in the afternoon and i was looking over some pictures when the phone rang. It was Tina, "Hi Sweetheart" i said. The tone of her voice was harsh "Start getting ready, tonight you will be my sissy, you can choose to wear any of my clothes except the ones in the top drawer, I'll be wearing them." That was all...

It Only Gets Better

by ElderDirt on Sep 14, 2017
Romance

Author's Note: This is a story about how a chance meeting led to a much younger woman becoming an intrinsic part of an older bachelor's life. Readers be warned that if you are looking for raunchy and frequent sex, you will be disappointed. The sex that follows is just the spice added to the meat and potatoes of the love story This is my first venture into...

Close Shave

by Tomsparty on Sep 13, 2017
Transsexuals & Crossdressers

My sister, Sharon caught me naked, shaving my legs in the family bathroom. 'I thought you where in Court all afternoon.' I cried dropping the razor in surprise. My sister dressed in her smart black skirt, white blouse and black fitted jacket raised an arched eyebrow patronisingly. 'Obviously so, brother dear but my case finished early. I wasn't required f...

A First Time at the OBGYN

by sissypt on Oct 19, 2020
Transgender & Crossdressers

I had been feeling under the weather but since everything had started getting into the doctors office was not an easy task. I had been staying at a friends house since i got kicked out of my mom and step dads for not "following the rules" there was more to it but that's for another time... Having had a sore throat sucked and with all the covid scare my fri...

A Husband Named Cathy

by cathynylons on Sep 25, 2017
Transsexuals & Crossdressers

When my wife Jane first found out about my naughty little secret she flew into a rage and launched into a tirade calling me a lying, duplicitous, deviant, degenerate pervert sissy faggot. She stormed out of the house slamming the door behind her. About an hour later she returned and had calmed down. In a very apologetic tone she said that she was sorry and...

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...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...