Babysitter Spanking Stories

25,290 results
Orientation
Length
Source
Infinite Scroll

Zoey's Punishment

by MsMarie on Feb 6, 2018
BDSM

Marie stalked towards Zoey. She was secured to the spanking bench with soft black leather cuffs attached to smooth silver chains that looped around the legs of the bench. Her breast dangled with her pierced nipples sporting hoops through them that had additional weights clipped on them pulling them as she panted both excited and nervous as she waited to see...

The Maid Pt. 03

by krstorm on Jan 30, 2018
BDSM

Missy froze. Mr. Nickerson had just thrust two fingers into her from behind. She had been on her knees, cleaning the floor in that ridiculous uniform. "Count," Mr. Nickerson said sternly. Missy swallowed. She felt him pull his fingers out of her, agonizingly slowly, and then furiously jut back in. "Ah! One sir," Missy said. He repeated the movement. "Ah...

Santa Daddy

by Bratty_Belle18 on Feb 12, 2019
BDSM

It was a few nights before Christmas. I was getting restless as I wanted to know what Daddy bought me for Christmas. Daddy had been working late this particular night and I was up waiting for him to get home. I must have drifted off at some point cause when I woke up to the front door being opened. I jumped up and quickly knelt on the carpet in the dining ro...

My Birthday Celebration

by lizipicka on Jul 17, 2018
Fetish

It was the summer and my birthday. I'd celebrated that afternoon by drinking a few glasses of wine with my girlfriend Melissa, her sister Lisa and their sexy cousin Emily Melissa told me that she had something special planned for my birthday and asked if I could stay for a while. "Sure, of course," I'd answered, not knowing just what I'd committed to. I gu...

Pet Ch. 05

by estelledarkbloom on Sep 14, 2017
BDSM

Elizabeth was gently stirred awake by a rhythmic rocking that she barely perceived. She tried to move, to stretch the stiffness of her muscles from the awkward tangle in which she'd slept, but quickly realized that she couldn't. Her eyes shot open and, lifting them upwards, she saw her wrists neatly secured, wrapped several times with medium cord, and locked...

Ms. Sandstrom's Assistant Pt. 02

by pinkysurprise on Nov 24, 2017
Erotic Couplings

I held my hands in front of me as I walked, trying to conceal the erection that was rather obviously tenting the front of my slacks. My heart was still pounding as I tried to slow my breathing and stop thinking about the interrupted blowjob from the secretary — Liz, I reminded myself. Don't forget her name! Despite my arousal, I needed to get my head straigh...

Young Mary Ch. 6

by Red Hugh on Sep 14, 2017
First Time

To avoid suspicion Bridgitte wasn't due back for a sleep over for three weeks. It also gave 'the pill' a chance to kick in. Some afternoons the girls would use the appartment after school for an hour to slake their lust. Mary of course had Ted but in Mary's absence Bridgitte only had her fingers or the handheld shower head at home for love. Ted had even wa...

Summer School Pt. 01 Ch. 01

by LilithDeVil on Oct 16, 2018
Novels and Novellas

Hello you naughty girls and boys! For those of you ready to settle in for a longer story I offer you this tale. It is about lessons learned and steps one must take to achieve a goal. It is also something of a favorite of mine. And there is a lot of naughtiness to enjoy. Many delicious themes will be covered and the cast is large. It is a story about Tom and...

Spanking of an Elf Priestess Ch. 05

by WriterOfRomance on Aug 14, 2018
Sci-Fi & Fantasy

Thomas Silvercloud, Captain of the King's Royal Guard, felt his body sink down to another level of relaxation and the growing hardness of his manhood. "You're welcome." Elanor Horne whispered, her breath was a gentle breeze caressing flower petals. The front of her white blouse had become soaked with water from his back when he had pressed against her. Lean...

BWC for Black Male Sissy

by Samuelx on Sep 12, 2018
Transsexuals & Crossdressers

Meet Bass, which is short for Bashir Malong, a six-foot-seven, dark-skinned and ruggedly handsome man originally from the nation of South Sudan. Bashir is definitely more than he seems, and that's just the tip of the iceberg. A lot of people, upon meeting the tall, handsome brother with the deep voice, wonder if he's some sort of professional athlete, and Ba...