Lesbian Babysitter Stories

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Infinite Scroll

Fall of the Philandering Teacher

by GymTeacherYouDeserve on Oct 14, 2017
Humor & Satire

Jerry Clikeman was weird. If he wasn't behaving abnormally quiet and anti-social, he was usually making a spectacle of himself. Jerry was otherwise a typical 18 year old senior. He attended F.W. Harmony High School in Thatcher Blake, made good grades, and was in the ROTC. But when Jerry was not at school, he was something else entirely. The Clikeman family b...

Downfall Ch. 01: Makeout Point

by Dawi on Feb 5, 2018
Sci-Fi & Fantasy

When she stood before her family's congregation at the beginning of the year dressed all in white and swore that she would save herself for the man she would marry along with some of the other girls her age, Lisa had meant it. But right now, with her body on fire, she looked back on that moment and wondered what she was thinking. Would she have made the same...

Magic Dress - Yvette Pt. 05

by SlightlyRude on Mar 26, 2019
Transgender & Crossdressers

I was feeling really happy. It was a nice day, and I was wearing my favourite dress, swishing along in heels through town with my best friend Kathy. Kathy who is also my wife, and the person who had helped me on my journey to being a woman. I was revelling in my femininity, when the spell was suddenly broken. Coming towards us was the last person in the wor...

A Wild Widow and Widower Ch. 03

by ljprockhard on Mar 26, 2019
Erotic Couplings

Characters: Len -- 64 -- widowed 3 years ago (traffic accident) Tammi -- Len calls her "T" -- 56 - Len's next door neighbor -- widowed 18 months ago (pancreatic cancer) Jami -- 49 -- Tammi's sister Kaili -- 18 -- Jami's daughter Previously: (Chapters 1 & 2.) Over happy hour drinks one day Len had proposed to T that they try a "mutually rewarding physic...

Teaching the Cub Ch. 05 - Date Pt. 02

by sthsth on Apr 9, 2019
First Time

As I drove us to the theater, I was starting to freak out about what I just did. "I can't believe I just had sex in a back alley with a near total stranger." "My little man is growing up." Tina teased. "Not yet, but he probably will be when we get to the movie." I joked. Tina laughed and asked, "What are we going to see by the way?" "A documentary about...

The Resort-Initiation

by jimhawkins on Dec 4, 2017
BDSM

This is a different sort of story. Please let me know if you like it. If you do a sequel may follow. Two owners of the resort were talking. "The new waitress Jenny is even more of a promiscuous slut than I hoped. Last night she fucked 2 men. Jason from the band stood her against the storeroom wall during interval, one of their roadies had her in the men's...

Agnes Dourville Ch. 14

by ValoryG on Oct 12, 2017
Transsexuals & Crossdressers

The Gauss family, Anton and Suzy, become an increasingly important part of my young life. Anton and I keep our little (big) secret at work, and no one seems the wiser. We carefully maintain our distance (even though I sneak looks at his fly and buns from time to time) and he grants me no favoritism. After our time in bed (with Suzy away), I return to the dai...

Poli-Dicking

by Rallynoangels on Nov 27, 2017
Group Sex

All characters are 18 or older. All characters are original, and any similarities between them and actual people is not intended. This story includes group sex, lesbian sex, humiliation, voyerism, strapons, oral, anal, vaginal sex, rough sex, deep throating, and everything else that should be included in modern political discourse. ***** President Nora cou...

Free Use Ch. 06: Home Sweet Home

by free_use_world on Nov 9, 2017
BDSM

Home Sweet Home The rest of my morning seems to fly by, signing paperwork, fielding phone calls from the accountant, taking care of little business things that came up while I was picking out my new lease girls. Luckily we finished just in time for lunch, and Evan took the opportunity to swing out to lunch with me, so we could shoot the shit for a bit. May...

Magic Dress Pt. 03

by SlightlyRude on Feb 11, 2019
Transgender & Crossdressers

I had been wearing dresses at home for quite a while now, with my wife's encouragement. The first one I tried was very special and we called it The Dress. It just made me happy. On Wednesdays I was sucked off while wearing it. On Fridays I dress up as Sexy Sally and fuck her. On Saturdays, for her entertainment not mine, she would dress me in various outfits...