Shemale Surprise Babysitter Stories

137,690 results
Orientation
Length
Source
Infinite Scroll

The Tomboy and Randy

by midnightfalcon on Aug 31, 2017
First Time

I had been riding for about two and a half hours and my stop was about three or so miles ahead. Since there was no major highway or paved road up to the lake, I'd have to walk the mile or so in. I didn't really mind, I enjoy the woods that surround the lake and it was early enough in the morning so it wouldn't be too hot. I had packed light. A sort of backp...

Awakening Michelle Ch. 02: After

by SeanEdward on Sep 16, 2017
Group Sex

I hope you are enjoying the journey of Mike and Michelle. I'm trying to keep these in nibble sized bits, please let me know if you'd like them more drawn out. As always your critique and criticism are appreciated as it is the only way we grow. Enjoy! ***** "Babe, I wish you would tell me what's wrong" Mike says from the driver's seat as we are heading home...

Ting Ch. 01

by oldfogey on Sep 19, 2017
Loving Wives

Tommy and Lauren I met my wife on Taiwan. She was the employee of a company that furnished supplies to us. At 25, she was alone in the world, her family still behind in mainland China despite her efforts to get them to Taiwan. I'm going to call her "Ting" for the purpose of this story, principally because I never learned how to pronounce her name in her o...

Steampunk Harlots Ch. 26

by RedFireBrand on Sep 18, 2017
Sci-Fi & Fantasy

Walking down the hall after finding Hannah's room empty, Liddy knocked on and opened the door to where Vile was supposed to be resting. Inside she found Vile on her knees, Inky grinding against the powerful red thigh while pleasuring one of the massive breasts, and one of her tails deep inside her lover. "Oh," Liddy stated. "I was going to ask if you knew w...

The Loners Ch. 12

by Ozma12533 on Sep 15, 2017
Sci-Fi & Fantasy

Katie was tossing and turning, finding it difficult to fall asleep. Finally, she had enough, and rose. She turned to see Alan was sound asleep next to her. Not surprising, since he didn't sleep in the car at all during the last leg of their drive here. It also might be the fact that the three of them just did finish a rather nice session of sex. What she wa...

The Sunshine Room: Nick + Bree

by barabajagal001 on Sep 14, 2017
BDSM

Author's Note: This is a series of stories based on actual experiences and observations at a local sex club. It's not a series; the stories can be read individually, but there are some recurring characters. ----- Some people are wealthy by birth, others by hard work and ingenuity. Then there are those from humble origins, who have great opportunities drop...

Bikini Christmas Carol

by Knickers on Sep 15, 2017
Exhibitionist & Voyeur

Disclaimer: The following story contains sex scenes and rude words. It's fairly tame, and I'm pretty broad-minded, but the decency laws in most states would require it not be read by persons under 18. Also, if you're offended by adult themes, you should probably leave now. More importantly, this tale features women presented as sexual objects. There is nothi...

I'm a Trucker

by B_Bailey on Sep 13, 2017
Romance

This is a story about a dirt poor farm boy that decided to turn his life around. He saved his money while growing up to take the truck driving school he would need to improve his life. Please enjoy. Please vote and leave comments as I do value your comments. ***** I'm A Trucker What is the difference between a sailor and a trucker? That answer is: The oce...

Finding True Love

by residentevil on Sep 16, 2017
Romance

"I can't believe that I'm in America," I thought to myself as I was exiting the plane from the long and boring trip. The last thing that I had seen before I went to sleep was the crystal clear blue beaches of FIJI. Now I was in America on holiday, and I was hoping to meet up with some friends I had made online. During my trip abroad, there was one special an...

From Scared to Dared to Bared: Friday Evening

by glendale22 on Sep 14, 2017
Exhibitionist & Voyeur

These friends had known each other for a couple years at least, since childhood in some cases. Jay met his roommate, Karl, at the branch campus in the city where they lived. Karl's girlfriend, Lilly, also went to school there, coming the year after the rest of them, and Jay had known her from the street where they both grew up. Jay met his girlfriend Kate at...