Shemale Surprise Babysitter Stories

137,690 results
Orientation
Length
Source
Infinite Scroll

The Broussard Sisters Ch. 11

by JimBob44 on Sep 18, 2017
Group Sex

*Author's Note: Any persons engaging in sexual activity are at least eighteen years of age. Chapter 101 Paul patted Barbara's back gently until the infant fell back to sleep; tummy full and diaper dry. Paulie was still asleep; the two year old toddler would probably sleep until Aunt Pam came to get him for his breakfast. Candy was also still asleep; it w...

By My Side

by BurntRedstone on Sep 25, 2017
Romance

Author's Notes: 'By My Side' is a sweet little story that was intended to be a stand-alone short story. I had no luck in keeping it short. Now I'm thinking of sequels... if time allows. All characters engaging in sexual relationships or activities are 18 years old or older. ******** Chapter 1 "Hurry up in there!" Gary barked through the bathroom door....

A Family Affair Ch. 03

by duke1951 on Sep 14, 2017
Erotic Couplings

Authors Note - Please note that this is Adult Fiction, so should only be read by those who qualify! This is the third part of this little mini-series, and is probably best looked at after reading episodes 1&2, but for those who can't wait, here's a little précis of events so far... Paolo Wharton has a hot experience that he'd only ever dreamed of whilst...

Angels Who Called Me Snowballs

by onwardbob on Sep 1, 2017
Group Sex

Try to picture it; and trust me, you're going to want to! Bob, and that would be me, is sitting naked in the hot bubbling water of a backyard Jacuzzi. I've got my hands tangled in curly, shoulder length hair. The only reason I knew it was a dark chestnut brown, was because that's how Dana described it. Actually, and you really do need to know this, it was he...

Sprung Ch. 11

by jmmj5 on Feb 11, 2019
Loving Wives

I looked for the last time at my reflection in the mirror. Could I do it? Could I really get away with this? Could the forty-year old, not beautiful but also not plain, housewife who has never done anything remotely like this, have one extramarital adventure with no repercussions at all? I took in my reflection. The person looking back at me would have to w...

Aunt Jenny's Perverted Futa-Cock

by jenny_clara_doubletit on Sep 25, 2017
Transsexuals & Crossdressers

I wrote this and wanted to share it. This seemed like the right place, I hope? Contains incest, an Aunt with a large futa-cock, cock-milking, some impregnation talk. No cock-sucking or ass-play. Hope y'all enjoy. ***** Sex has always been a taboo topic in my family. My Mom, Judy, was strict about enforcing a 'No Pornography' ban in the house, and on the ra...

Lori Ch. 08

by LoriisaDirtyGirl on Aug 29, 2017
Erotic Couplings

I woke up as Lori returned to bed and kissed my cheek. "Time to get up. You need to brush your teeth and get back in here, I'm not walking funny." I flew out of bed and scrubbed my mouth and was back between Lori's legs in a flash. She was learning to control her volume so we only had to use the pillow twice but the rest of the time she quietly urged me on...

School Girl Smoking Fetish Ch. 03

by sophiewilliams on Sep 11, 2017
Fetish

As I sat on the toilet leaking Dave's cum into the pan I looked down at the piece of paper he had handed me. I opened it and smiled as I read his number in my head. I didn't want to call him, but deep down inside I knew I would. Dave had ignited something within in me that I was too young and inexperienced too understand. He had created a hunger, a feeling...

Oral Exam Ch. 03

by gradprof on Sep 12, 2017
Group Sex

A woman's tongue gently caressing my balls: that is an extraordinary feeling! To me, the wet licks and swirls are always a surprise. They comprise a moment that I always experience anew, since I can never seem to hold that sensation permanently to my mind. It is too startling and spontaneous; the memory is inevitably washed away by greater pleasures. And it...

Husband Encourages Wife Ch. 02

by xleglover on Sep 13, 2017
Loving Wives

"You haven't touched your lunch," Tina said after she finished telling Jen about her latest date with Jason. "I'm sorry," Jen said. "I guess I'm distracted." Tina reached over and grabbed her friend's hand. "What's wrong? Are you and Michael okay?" Jen looked up in surprise. "How did you know?" "Jen, we've been friends since high school," Tina said, conc...