Sissy Boss Stories

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My sissy boss.

by mally01 on Apr 22, 2025

Craig was in his office at Lingerie International watching the wall clock his left drifting under his shirt stroking his soft hairless skin. He was waiting for five thirty knock-off time to come. His secretary Charlotte came in and asked if he needed anything else, and he gruffly replied that she could leave for the day. After he had witnessed Chantelle get...

Manning the Yard Sale

by AntaeusQ on Aug 18, 2017
Fetish

[Generously edited by CopyCarver from Literotica.] * My wife Susan spent all Friday getting ready for the yard sale. She painted the signs, typed up the Craigslist ad, and alerted her Facebook friends. She has a couple hundred of those, most her age, and a fair number recent mothers or pregnant. I used to give her grief about all the time she spent online,...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

My Wife's Sexual Awakening.

by wunderboi on Jun 3, 2019
Interracial Love

My wife and I had been married for six years and we had recently moved to Hawksville a bigger town or small city in the south and were finding it hard to establish friends in our new location. Other than that, life was the usual routine of work for us both, looking forward to the weekends when we could drive to the beach, or just hang by our pool. I had mar...

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...

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...

Thailand Sissy

by Xxxdollxxx21 on Apr 22, 2025

I really just wanted a vacation away from my ex wife that I was divorcing, from my dead end job, and my annoying ass boss. This trip was supposed to be fun. Site seeing across Thailand, their rich, beautiful locations and religious temples. The beautiful scenery I had seen after I got off the flight and rode to my resort had vanished into these deep woods. T...

Indian Wife & Boss Ch. 04

by tantrik721 on Sep 25, 2017
BDSM

Ravi felt guilty as he blamed himself for everything. Meena showed no pity on him rather creates situations where he feels even more remorseful. He was more caring, more loving towards Meena. He took care of most of the household chores and stopped bugging her for being late from office. Meena was enjoying this new found freedom. Kripa called her the next...

A Sissy Saga Ch. 19

by Snurge on Sep 15, 2017
Novels and Novellas

It came as a surprise. When Abigail received a message from his sister telling him to go to her room he was astonished. He never went into the family apartments until recess, so such a demand was abnormal. Bossy bitch, Abigail thought as he made his way there, but he didn't say it. His relationship with his sister had never been one of close kinship, they'd...