Shemale Dating Sex Stories Stories

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Infinite Scroll

Pam's Gangbang Experience

by majicman21 on Oct 14, 2017
Group Sex

Author's Note #1: This is a continuation of 'Pam's Shemale Experience' from the Transsexuals/Crossdressers category. Although reading those stories is not necessary to appreciate this one, it will enhance the experience. Either way, enjoy. ***** The splashing in the hotel pool provided an aural backdrop as John read his Kindle, learning about the history...

Shemale Stories: A MILF Fucked

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Lonely MILF walks in on teen girl masturbating and.... Note 1: Thanks to Hernandez for doing the photos for this story as well as the plot bunny that led to the final story. Note 2: This is a 2017 April Fool's Day Contest story so please vote. Note 3: Thanks Tex Beethoven, Robert, goamz, With my daughter Simone away at band camp as a counsello...

Genie Chronicles - Make a Wish 03

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

A big thanks goes to Joe Brolly for the original Genie Chronicles. As many people have done, I'm simply taking his original story format and giving it a twist. Fair warning, lesbian and futa (shemale) sex will feature heavily in this storyline. Thanks to Ultrafem, Stickymon, NinjaKitty, and Anasheya for drawing pictures that inspired these stories. Milla Jov...

Don't Lie Ch. 01

by Scribler on Sep 13, 2017
BDSM

All I can say is don't lie to you wife. If I didn't I wouldn't be in the situation I found myself in. It really wasn't that big of a lie but it was enough as far as my wife was concerned. It started a few weeks before we got married, five years ago. My wife Dawn decided that she wanted to tell me everything about her sex life before we got married. She sai...

Sprung Ch. 12

by jmmj5 on Feb 11, 2019
Loving Wives

For those of you that provided feedback, even negative, on the previous two Sprung endings. Thank you. I do appreciate that. Since this one is longer than either of the other two, I'm going to give a very short preview, so no one wastes their time on something they won't enjoy. Having said that, this is NOT a RaaC. While Sarah does have her affair and is pu...

Awakening: 7 Slutty Blackmail Tasks

by silkstockingslover on Mar 20, 2018
Illustrated

Summary: MILF's sexual awakening by being forced to do 7 slutty tasks. Note 1: This is an April Fool's Day 2018 Contest Story so please vote. Note 2: Thanks to DARKBREEZLY for collaborating with me and creating all the illustrations that bring this story to life. Note 3: Thanks to: Tex Beethoven, thor_p, Robert, and Wayne for editing. Note 4: A warning:...

Open Your Mind to Something New

by Dazman on Nov 4, 2019
Fetish

Open minds create amazing experiences This experience had its genesis in my early twenties when I unexpectedly began exploring my bi-side with my childhood buddy, Lyndon while both of us were studying at university (refer to my story Friends Satisfying Each Other for background context). This story takes place over a weekend, Friday evening to Sunday after...

Monster Fever

by Armphid on Sep 25, 2017
NonHuman

A cool wind blew over the parking lot high atop the sharply sloped hill; curling around the repeating pattern buildings that made up the suites of off campus student housing and bearing with it the crisp scent that promised a fine October evening. The buildings were sharp and clean looking and for the most part, uniform and static. But here and there, hung...

Rain and Sunny

by panther1282 on Sep 16, 2017
Sci-Fi & Fantasy

1 The sun rose and shined its beautiful light upon the campus town of The University of Texas. It was a Saturday, an elegant one at that where the neighbors of the school were walking their dogs, mowing their lawns, tending to their houses, and among others working out in the nice, warm, sun. Among the residence who took advantage of the nice, warm, weat...

From the Ashes

by panther1282 on Sep 14, 2017
Sci-Fi & Fantasy

1 The night was beautiful. A combination of warm and cool. Many people were out on the street partying, living it up as if it was their last. One particular woman was walking the street with her hair as dark as the night flowing down her back. Her dark brown eyes were like the color of almonds. And her skin was nicely tanned with a tag of red blush on he...