Shemale Surprise Babysitter Stories

137,690 results
Orientation
Length
Source
Infinite Scroll

The Albatros Chronicles Ch. 01

by DiminutiveDame on Sep 15, 2017
BDSM

This is a sequel series to Steam Powered Attraction, the first of hopefully many more. Nothing of the setting/story/ characters has changed, only the name. Thank you for reading, DD x ***** Heat was radiating in waves between Amelia's pale thighs, pulsating, burning, aching as she crawled on the bed, her slight form making neither sound nor movement on the...

Call Me They

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

"Call me they," said the diminutive, tomboyish, short-haired and curvy Native American gal as she looked me up and down from behind her desk, dripping with attitude. Snorting, I looked at her like she had two heads and they were both fucked up. Ever since I moved to the City of Winnipeg, Manitoba, from my hometown of Boston, Massachusetts, I'd seen and exper...

A subbie's Valentine's Day

by fired_up_subbie on Sep 14, 2017
BDSM

I'm rushing to get home, knowing You will be calling soon. Work ran late and I'm afraid I wont make it home on time. The phone is ringing as I walk through the door. I glance at the clock and notice I'm fifteen minutes late. I'm hoping you are too as I grab the cordless and head for the bedroom. "Hello." Almost out of breath, I'm rushing through the house....

One Room Away Ch. 02

by Darkness84 on Sep 13, 2017
Erotic Couplings

"Later can be whatever we want it to be." Those had been his words, but clearly the fates had conspired to make "later" more of a concept than a definitive time. After their meeting that night in his apartment, they had not gotten to see each other again for quite some time. He had made sure to get her number, however, and their brief messages to each other...

The Best Mistake I Ever Made

by SxxyLyssa on Sep 12, 2017
Erotic Couplings

The bed shifted and I slowly opened my eyes, blinking rapidly as the morning sun glared into my tender retinas. My boyfriend, Rob, was just getting off his shift as a firefighter and was lying down to go to sleep. "Sorry, baby," Rob whispered. "Didn't mean to wake you." I yawned. "It's ok, I have to get up anyway. How was work?" He scooted over and curled...

James and Dina Ch. 03

by freaknut on Sep 15, 2017
Erotic Couplings

*This is a work of fiction, meant to be read and enjoyed by adults. If adult material offends you or if you are not of consentable age to read such material, do not read any further.* Dina awoke the next morning, alone in the bed she shared with James. Rolling over, she felt a slight twinge of pain run from her groin down her legs. "Oh my God, she thought,...

The Upstairs Neighbor

by MrRobbur on Sep 13, 2017
Exhibitionist & Voyeur

After living in my apartment for about a year, the last six months were very quiet because of no upstairs tenants. My apartment is the mirror of the one above, consisting of a half flat. The other side had the same arrangement, but were not connected having four apartments total in my building. One day before leaving for work, I meet a great pair of legs car...

The Survivors Ch. 05

by millennium_bard on Sep 14, 2017
Sci-Fi & Fantasy

At first everyone was wary of Cindy of course. However they soon became used to having her around. Her friendly nature and polite behavior soon won them over and she became an accepted member of our community. Vicki was fast becoming a legend among the fighting men and women of our group, and I had to firmly quash the efforts of several who wanted to follow...

The Nixon Girls Ch. 01

by thelastenglishking on Sep 13, 2017
Erotic Couplings

I would start with a warning: Never, Never, NEVER! Allow your partner to have a computer memory stick which is the same as your own, no matter how good that "two for the price of one" offer appears to be! The frustration that you feel when you're a thousand miles from home and realise that you've got your wife's; is as nothing compared to the feeling of horr...

Now Swallow It

by aswpc on Sep 16, 2017
Group Sex

“Now swallow it”I told her. Dr. Virginia Patterson had just licked a big glob of my cum from the smooth shaven pussy of the beautiful coed sitting naked on my office couch. Just watching her tongue lick the cum from off her lips, was enough to make even my softened cock twitch a bit. Damn, she looked sexy. For that matter, Traci Townsend, the leader of our...