Shemale Surprise Babysitter Stories

137,690 results
Orientation
Length
Source
Infinite Scroll

It Started In the Dairy Section

by trigudis on Jul 10, 2018
Romance

In the mid-point of the Obama administration, I was in my early thirties, that wonderful age when a single guy playing the field still has a wide range of age choices among women. Twenty-somethings, thirty-somethings and even sexy forty-somethings are fair game. Never been married, I was still looking for that "perfect" woman—or at least as close to perfect...

Awkward Church Games Pt. 03

by Speakingeasy on Mar 5, 2018
Loving Wives

My Situation Changes It was almost 9 am, when I awoke and I was not surprised to find him in my bed spooning me. I quietly pulled the covers up and looked back to see his junk resting nicely against my butt. I only had like four more hours of sleep and I was still tired, but the sight of him laying there naked next to my naked body shook me terribly. My mo...

April's Story Ch. 21

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the twenty-first episode in a series entitled "April's Story". If you have not read the previous twenty episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I strongly recomm...

Two Worlds Ch. 09

by vixenfurry on Sep 26, 2017
NonHuman

Author's note: Hi everyone! Just wanted to say a few things real quick. First off I know a few of you were confused by the fact that in the second chapter of this story Jess's ankle healed so quickly and I just wanted to tell you that I kind of explain it in this chapter. Second, I am working on another story and hope to have it out soon so you aren't all...

Fender Bender Ch. 05

by SissyAndi on Sep 14, 2017
Transsexuals & Crossdressers

Author's Note: The following is purely fiction and the property of the author. Any feed back would be greatly appreciated. * My name is Robert, but when I am dressed I call myself Vicki. I am 5'9" 160 pounds, blonde hair and blue eyes. I had just turned 18. Mom and my Step Dad were away on vacation leaving me home alone. The past several days I had been...

LOrd of VEgas Ch. 01

by PaulStevens on Sep 19, 2017
Sci-Fi & Fantasy

Edited by luvtaread Las Vegas, never was there a town where one's luck could change so quickly. It had the power to put you in heaven one minute and drop you into hell the next. It could raise the lowliest beggar and humble the richest tycoon. It was also where Lloyd Frank had called home for the past two years and where he would transform from a lowly work...

Canary Island Beach

by suelove58 on Sep 12, 2017
Mature

By SueLove58 (c) 2010 I decided to head off on holiday for a week and, being the winter, wanted to go somewhere where I would be able to soak up some sun. I discussed my idea with Lin and she suggested I try the Canary Islands. I had been to Tenerife 20+ years ago and had enjoyed myself but didn't really want to return there so I opted for Fuerteventura. T...

Wel-cum Home

by Therandy1 on Sep 14, 2017
Erotic Couplings

After spending 8 long months in the desert on my last deployment I was looking forward to a little R&R. I was lucky enough to get the chance to go home for a couple of weeks. Usually the married guys would get that option so I was pretty stoked! Two weeks may not seem like a long time back home but after eating nothing but sand and MRE's, (or meals ready to...

A Double-D Surprise

by Jonny Cakes on Sep 19, 2017
Group Sex

Thank God, it's Friday. It had been a long time since I had a week this busy, but at least I closed five of my fourteen open cases. It would take a lot to get me off the couch this weekend. Just as I finished packing for the day, the annoying sound of a ringing phone filled the room. "Fuck!" I almost didn't answer it. "Good afternoon, Jonny speaking." "Hey,...

Orbital Academy 13

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

Another chapter of the epic space opera Orbital Academy, thanks to the wonderful encouragement of all you guys! ************* Missy was surprised at how well she was holding up. During her first day at the Academy, on her first jog, she had collapsed in a heap after three minutes of steady running. Now here she was, on an uneven and dark jungle floor, and...