Sissy Boss Stories

46,032 results
Orientation
Length
Source
Infinite Scroll

Love, Guns, or Knives? Ch. 03

by FrenchescaDoll on Sep 15, 2017
Novels and Novellas

Chase felt lonely. Arinn had left to go get some lunch, and he couldn't help but hope that she would come back quickly. The more that he had talked to her over the two hours she had been there, that more that he could tell that he was falling in love with her. Before she left they had been talking and he had asked why her eyes were different colors. "Well a...

Educating Marri Ch. 06

by MarriPetX on Sep 14, 2017
Novels and Novellas

Wednesday was my day off and I decided to actually spend some time away from Torch. After classes, I spent the afternoon shopping and even met up with a couple of my friends for dinner. It was so nice not to have to worry about what I would be wearing, or how sore I'd be afterward. After dinner, I went back to the dorm and started packing my things into the...

A Shot in the Bathroom

by ChronicMB on Sep 16, 2017
Toys & Masturbation

Lickety Clit's tits bounced to and fro about two feet from me. They were clearly fake. Too round. Plus, if you looked close enough you could see the scar from the incision. This is probably why pornstars aren't so keen on shooting their movies in HD. All their scars are on display. I've got my cock in my right hand, raw. It's only the second time of the day...

On Dating a Topless Dancer

by Bakeboss on Aug 19, 2017
Exhibitionist & Voyeur

Many years ago, I was dating a topless dancer named Linda. She was not your stereotype idea of an exotic dancer; she was skinny as a rail with no ass and the flattest chest I'd ever seen on an adult woman. If she ever were to wear a bra, she would have easily fit into a preteen's training bra and yet her little tittys unfettered by underwear were always on d...

More Temporary Jobs

by vanessa.evans on Aug 19, 2017
Exhibitionist & Voyeur

Two more Temping jobs that I did recently that Jon told me to write about: - The first was at the offices of a large company where some of the staff come into contact with the public. As a result all staff have to wear a uniform. In some respects the men were lucky as they have to wear white shirts, tie and charcoal trousers. I say 'in some respects' becaus...

Joyce Ch. 02

by Jamesey on Sep 17, 2017
BDSM

Joyce 2 - Flatulent confession It was 6pm in the London offices of Clutterbuck Legal Publishers, Bell Yard, EC2. Manager Joyce Tipson was sitting in her office chatting to Julie, her secretary. The year was 1972 and the building was deserted because the employees had all gone home with the exception of Joyce, Julie and one other – your humble scribe, John...

Club Eros Pt. 03

by Undergroundz on Aug 31, 2017
Exhibitionist & Voyeur

Club Eros is a special club for adults who love exhibitionism. Each night ten couples enter. Each couple has fifteen minutes to live out a fantasy of their own making. The next number is ready to be called... Chet's bulge was obvious. Rose loved staring at it. She watched it grow like a tent being raised in his pants as they sat in the booth enjoying "per...

Farmers of Sien

by Capitan_Izaac on Nov 24, 2017
Sci-Fi & Fantasy

Becca sighed wishfully as another set of oversized breasts were plopped in front of her. "Hey Stevie, how's the orchard?" she asked as she started fondling and massaging the mammories before her. "Good! We cleared out about 30 trees. I think I've got two or three in here," she patted her bust as she spoke. Becca was always envious of the whopping melons she...

No Escape

by hellbound_heart on Sep 17, 2017
BDSM

She had lost everything but her looks. Sitting in the boat, she kicked herself as she went over the last few weeks in her mind. She had taken a so called friends advice, sold her house and depleted her bank account for a get rich quick scheme. It couldn't fail He said. But there was no scheme and her 'friend' had disappeared with everything she had. And no...

My Sexy Domineering Office Sir

by Ckisses1974 on Sep 14, 2017
BDSM

You were a demanding, and firm boss with exceptional work ethics and demanded nothing less from your staff. I had been your assistant for several months now. Most people were afraid and intimidated by you and I had received quite a few stares whenever you yelled my name to come to your office. Today was no different, luckily most people had already left for...