Shemale Next Door Sex Stories Stories

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Infinite Scroll

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...

"A Shemale Submission": A Lust Story

by silkstockingslover on Dec 23, 2019
Illustrated

"A Shemale Submission": A Lust Story Summary: Author Jasmine falls for a hot new teacher with a big cock. Note: Thanks to hfernandez1983 for the many pictures used in this story. He spent weeks getting these perfect for the many different scenes I requested. If you like the pictures in this story, please feel free to read the multi-chaptered series Cheerle...

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...

An Orc's Slave Ch. 07

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

I feel like this story has been too much sex and too little advancement in the story, which is something I've mostly done to make any change come more naturally instead of feeling forced. But even I am getting bored of the characters just fucking around and not doing much, so in this chapter I tried to push the plot forward. Something must have gone wrong th...

Demonic Partnership Ch. 09

by warnos on Sep 26, 2017
Sci-Fi & Fantasy

In this chapter you will see Jess make her appearance in this story. Jess is the main character in my short stories titled Ring of Wishes and Ring of Wishes Ch.02: Jess's End. My reasoning in doing this is that I wanted to do something that probably hasn't been done on Literotica before as I am linking two stories together. This chapter is going to be shorte...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

New Moves for Hubby Ch. 02

by ndeavour on Feb 12, 2019
Group Sex

[Author's note: Thanks go to Mumbo700 for helping to shape this story. Her work can be found here on Literotica as well.] *** You may have read the first story in this series - my wife's account of the things that came to a head (pun intended) in our bedroom, with her friend Jayne and a couple of strap-ons. I'm not denying any of it, nor am I going to try...

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...

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:...

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...