Sissy Boss Literotica Stories

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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...

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...

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...

Sissy Joanne Parr Fantasy Fucking Ch. 01

by Sissy Adele Howells on Aug 18, 2017
Fetish

Joanne Parr was 26 years of age. She had an obsession with the Barbie doll . She wanted to look like Barbie, as well as dress like her. One day in the office, I was so jealous of her. How dare she wear pretty dresses, when they would look much better on me. I want to be the new Joanne Parr, but I needed help to allow my kinky fantasy to take place. Georgina...

Nancy and Her Boss Ch. 03

by MidniteSpanker on Sep 19, 2017
BDSM

Part 3 – The Weekend. The initial stories in this series Nancy Remembers Chap. 1 Nancy Remembers Chap. 2 Nancy Remembers Chap. 3 Other stories continuing in this series Nancy and her Boss Part 1 Nancy and her Boss Part 2 Nancy and her Boss Part 3 - The Weekend Nancy and her Boss Part 4 - More Weekend Then the following are separate but related stories...

Sissy

by rogue01 on Sep 19, 2017
Fetish

Sissy It happened at last that he was caught. His wife came home mid-afternoon with her friend Miriam and found him upstairs in the bedroom wearing a pair of her panties. Her reaction shocked him. In the hot instant of his overriding shame he was aghast to discover in her a persona he had not yet known existed. Him, a faintly domineering man, like so many...

Sissy Boy Secretary Ch. 08

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine knew that it was now time to implement her plan to bury her nearest competitor, Bill Andrews... You see Elaine's secretary arranged through the secretarial pool to make sure Tammy, the daughter from next door, got the job as Bill's secretary... As you already know Elaine has used Tammy's information to her advantage and now it seems that Bill was at h...