Boss And Secretary Stories

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Orientation
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Office Casual

by al_Ussa on Sep 13, 2017
Transsexuals & Crossdressers

"Good morning Ms. Anderson," Karen said as her boss walked past her desk station and into her office. "Good morning Karen," Ms. Anderson said, not even stopping to make eye contact, "I'm going to be very busy today, so I'll need you to let me know if you get any mail for me." "Will do," Karen said as she tried to look busy behind her computer. Karen conti...

A Story for Kong5

by alanstewart262 on Sep 17, 2017
Loving Wives

I was traveling on business and found myself in a local bar watching the Thursday night football game. Started chatting with the guy beside me and at some point the conversation turned to sex. I mentioned that I'd been away from my sexy sweet hotwife for too long and was tired of pulling on my own dick. He stated that everyday he gets some, but not from his...

Mommy Adriana Makes Greta Become...

by Gretatv on Sep 13, 2017
Transsexuals & Crossdressers

Dear Readers, it took me a while because reality caught up with me, but now the next chapter is ready. I simply hope you don't get bored and enjoy also the 6th installment of my little story. * Finally I lay in bed. I heard Mommy Adriana was sound asleep while I tossed and turned. I simply couldn't sleep after today's events. I would never be the same man...

Mature Woman New Job for Family Ch. 03

by Marriedandneedingmore on Sep 19, 2017
Loving Wives

This story is the third part of my story about a mature married woman who has to become the family breadwinner after her husband has an accident. She becomes a Secretary for her Husband's Boss. Please read the previous chapters first as this will tell you the background to how we have got to here. If you're expecting loads of sex, it ain't happening yet!!...

Secretary - Day after Day

by AluminumDaisy on Sep 16, 2017
Novels and Novellas

Monday – Giraffe on Rollerskates There are a million "secretary" stories and fantasies out there. I have often used varying scenarios to help myself cum. Here is the beginning of one... (there will be more as I've completed Tuesday and Wednesday) She had just started the new job. A secretary. Well below her station, but the unemployment was running out, th...

Best Secretary A Man Ever Had

by magmaman on Sep 12, 2017
Romance

"Just fucking great." I thought to myself as Henrietta left my office to go back to her desk. This had to be Frank Johnson's idea of a joke again. He was the main boss for our section and handled personel also, I had been slowly climbing the corporate ladder and had gotten to the point of actually having a secretary. Vice President the sign read, with my n...

Island Discipline Ch. 07

by Cyberdiva68 on Sep 14, 2017
BDSM

As she drove home, the blouse rubbed against her sensitised nipples causing them to stand out proud. The tightness of her skirt kept the butt plug securely in place and the movement of the car over the road's surface caused it to vibrate the butt plug up and down inside her back passage. The combination of the two different sensations had her pussy dripping...

Eustace Johnson's Private Secretary

by andtheend on Sep 19, 2017
Interracial Love

Susan's first job was working for a powerful, wealthy, albeit perverted, black man. Oblivious to the horde of Christmas shoppers in his store below and with the music of Nat King Cole's Chestnuts Roasting on an Open Fire playing so much like elevator Muzak in the background of his private office, Eustace Johnson, a big, black man, had enough of his new, whi...

Dirty Office Fucking

by KatieBoobs on Jul 15, 2020
Group Sex

A cold gust of wind swept into the room from the open window behind my desk. My boss, Charles, sat across from me, tapping his fingers impatiently on his arm rest. There was silence between the two of us and the only sound in the room was that of my chiming clock. My office looked like something out of the 1950s complete with an old mahogany desk, large boo...

Victoria, Goddess of CFNM Pt. 11

by Jreforma on Oct 7, 2019
Fetish

Having just returned to her hometown of Liberty, Sarah met with her friend Jennifer for dinner. During the dinner, Jennifer, who was a secretary at a local law office, was complaining that her boss, Lance, was a creep. When she was at her desk working, he would go around and pretend to look at her documents, but once she had looked up at him, and his eyes ha...