Male Babysitter Stories

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Male Model Nude for Money and Sex

by MotherandSonTrueConfessions on Oct 7, 2019
Exhibitionist & Voyeur

After modeling naked for women that he knew, years later, modeling nude while in college brought back fond masturbation memories. Author's Note: This is a true story about Dave, a proud crossdresser who goes by the name of Kelly when he's dressed as a woman. A submissive male with a medium build and feminine features, at 5'6" tall, when dressed in drag, mo...

My Sex Story Ch. 01

by AlexGunther on Jun 2, 2020
Non-Erotic

What a great day I would have. I was in my room, laying in bed when my phone rang. I answered it. "Hello," I said. "Who is this?" "Hello Vinod," the caller said. "It's Aunty Manori." "Yes," I said. "I remember you. Naveduni's mom. What's up?" There was a brief pause before she proceeded with her statement. "So," Manori said. "I heard that you are looki...

She-Male Babysitter

by sirhugs on Sep 28, 2020
Transgender & Crossdressers

[Note to Readers: This is not a story with quick short sex scenes, so if that is your goal, it might not suit you. There are detailed sex scenes, or one long detailed sex scene, take your pick. The use of the infirmary apartment setting is an homage to John Irving's The World According to Garp, which otherwise shares nothing with this story. My thanks to Car...

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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Furthering My Education

by jimmysub on Sep 15, 2017
Fetish

Well I had to go back to Community College to take some child development courses as my wife and her lover are planning on having a child together. This is part one of the adventure. I really don't like this idea but what my wife says go. Her biological clock is ticking and she has been with the same lover, Mr. Steve for about 3 years. So Debbie is going to...

CFNM fight

by Kd34 on Dec 1, 2019
Fetish

A cfnm fight is mainly about clothed female fighting naked men as the only thing that the naked men wear is nothing most nothing but knee and elbow pads, wrist bands, ufc gloves or boxing groves as the female clothed opponents see them naked as they see penis,balls and pubic hair yes that genitalia. The females wear tight, sport bra, leotards, shorts or jean...

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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...

SMS: Single Mothers Servicing

by HotnHornyGuy on Jan 12, 2017
MILF

She arched her back and cried out as you thrust your cock into her pussy again and again. Your balls slapped off her thighs as you took the single mother from behind, admiring the fine peachy arse before you. You still could not believe how your life had changed to the point where you were now on a bed plowing your cock into a horny mother as part of a local...

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Driving the Sitter Home

by splitlapper on Sep 14, 2020
Erotic Couplings

My wife, Sheila was one of the best fucks that I had ever had, but male curiosity can keep us looking for new pleasures. She was still tight after the baby and she loved everything I did to her. Her favorite position was riding me, sometimes facing me and sometimes facing my feet. She always loved 69, especially if I paid enough attention to her clit. Someti...

Watching the Babysitter

by Boxlicker101 on Sep 12, 2017
Exhibitionist & Voyeur

Michael and Louise Herrick are doting parents of their six year old son, Justin, especially since he is an only child and expected to remain that way. Because of a low sperm count of Michael, Louise was impregnated in vitro, and it was such an expensive procedure they won't be able to afford to undergo it again. At one time they seldom left home at night and...