Babysitter Anal Stories

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My Babysitter

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I could feel the warm cock in my mouth, it throbbing between my lips. It tasted so good I never wanted it to end. Of course it did, however. Just like every other morning I awoke my fantastic dream to my bed with my hand in my pants, partly dissatisfied because I had another homoerotic dream, and partly dissatisfied because it wasn't real. I really liked the...

Blissful Ignorance

by sindermann on Mar 31, 2017
Miscellaneous

For most people, familiarity inevitably leads to a blissful ignorance of what the other party is doing. The husband fails to notice as his wife bats her eyes at the stranger in the restaurant, the wife begins to ignore the overtures her husband is making toward the cute babysitter, and the father trusts his friends not to be forward with his offspring. Somet...

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Vacation

by MetropolitanDenial on Dec 6, 2017
Erotic Couplings

Rose and Owen Harper saved up all year for their big family vacation. This year, they'd be taking their four children - 20-year-old Dean, 18-year-old Finn, and 15-year-old twins Lucy and Lily - to Florida. They were thrilled at the idea of taking the kids to the central Florida theme parks, spending time at the beach, and, most importantly, having some roman...

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The Babysitter Has A Dick

by mr.z on Feb 29, 2020
Transsexual

Ricky Sampson is your average 18 year old boy. He lives with his parents and baby brother in a house in Nevada where he goes to school and works part time at a water park, it's Nevada the town gets really hot all year round. Ricky looks like a typical computer science nerd, with his glasses, black hair and pasty white skin but he wants to be anything but a s...

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The Ethical Slutmaker Ch. 10

by KrisCherita on Sep 14, 2017
Anal

Chapter 10 A Perfect Bottom Dan read through the email a second time, glad that he had a private office and could hide the tent in his pants under his desk, and wishing Andrea had tagged the text NSFW. "Dear Tammi and Dan "Robyn enjoyed babysitting for you last week, and hopes you enjoyed your evening out. She's now decided that she likes and trusts you...

Anal Punishment for Cheating Lovers

by libidinal on Sep 12, 2017
Anal

I had been waiting at the airport for hours when I finally heard the announcement that my flight had been cancelled and there wouldn't be another one until the next day. I was going to visit my sister in California but now my departure would have to wait until tomorrow. So I headed to the parking garage for my car and headed home. When I opened the front d...

Babysitter Revisited

by johnnieblue44 on Sep 13, 2017
Mature

Having just recently celebrated my forty-eighth birthday, I wasn't used to having a comely young woman about half my age appear to be checking me out as I stood at the counter of Panera Bread, waiting for my lunch order. Granted, it may have been my imagination or wishful thinking on my part. However, as I shifted my body around to face her, it seemed she...

The Babysitter Gets Caught

by Jay142 on Aug 8, 2018
Exhibitionist & Voyeur

Dan and Leslie had been married just over seven years when their marriage hit some bumps in the road. They both worked full time jobs, and now had two young boys. The pressure of work, marriage and children put a stress on their lives and had a similar effect on their sex lives. What was once a hot, romantic sex life with some spice of kinkiness had now turn...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Sharing My Wife Amanda Ch. 14

by Syzoth on Feb 26, 2019
Group Sex

This story follows Chapter 13 as well as "The Hot Babysitter 1". *************************************** "Hurry, Piper! Amanda will be home soon!" The 19 year-old's long blonde hair tossed in the air as she rode me wildly like a crazed cowgirl. From the flat on my back, I reached up to grope her firm breasts, squeezing them hard and mashing them together....