Shemale School Stories

702 results
Orientation
Length
Category
Source
Infinite Scroll

"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...

Show & Tell Ch. 28

by murphtsurf on Oct 31, 2017
Erotic Couplings

This is a long chapter, really two, that needed to be told at the same time so the reader could follow how it all actually happened. I hope you have/take the time to read it all at once... and enjoy how erotic it all turned out. Thank you ***** Show & Tell Chapter 28 After our weekend in New York, and the time it took both of us to recuperate, I...

Sally: His Perfect Shemale Partner Ch. 1

by PunkFan on Sep 16, 2017
Fetish

I am in senior year of school and anyone who has been to school at 18 will know it is not a pleasant time to be working when your friends are all out drinking and enjoying themselves but I needed to go back to school to go the university I wanted to go to. I am a tall fairly muscular straight guy who has had a few sexual experiences before this chapter in my...

Shemale city

by Ben18927e on Jun 17, 2020
Miscellaneous

I wake up to the sound of my alarm on blaring on my phone. After a couple of failed attempts to ignore it i finally get up and switch it off. Now that the alarm is no longer on, i slowly drag myself out of bed and start to get ready for the day. On the way downstairs i grab a towel, heading towards the bathroom. The water quickly comes on and i start to wash...

Shemale submission

by wendals on Jul 18, 2010
Fetish

You wake up with your head throbbing like you've been hit over the head with a bat and you can barely see as you struggle to open your eyes. After a minute or two your vision slightly clears up and you notice that you're in a bedroom, your arms and legs are tied to the bedposts and you're dressed in nothing but a pair of pink panties. You scream out for hel...

A Shemale Shock: A MILF Falls

by silkstockingslover on Sep 25, 2017
Illustrated

Summary: Mom catches her daughter with a teenage shemale and.... Note 1: This is a Nude Day 2017 Contest Story so please vote. Note 2: Thanks to Tex Beethoven, Robert, and David for editing this story. I was having a bad day. I'd spilt coffee on myself on the drive to work. I'd gotten a rip in my nylons. And I'd forgotten my notes for tonight's intervi...

Transformed Into A Shemale

by girlboybootsie on Sep 13, 2017
Fetish

I was 18 when I first had sex with a man. This is the story.... I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6'1," 180lbs, with a tan athletic body and a 7" beautiful cock. I have be...

Shemale Tales: The Christmas Party

by silkstockingslover on Sep 2, 2017
Illustrated

Summary: Young woman discovers the perfect man... a woman with a dick. Note 1: This is a Christmas 2016 Contest Story so please vote. Note 2: Thanks to TexBeethoven, Robert, Dave, and Wayne for editing. Shemale Tales: The Christmas Party I'd been working at the firm for only a couple of weeks and originally wasn't planning on attending the staff Christ...

Omnipotence

by PervertedKatharina on Mar 18, 2020
Fantasy

Character description: Larry (18): Our main character. He still goes to school and has always been kind of an unpopular kid. He recently got together with a girl though. He's somewhat of a nerd and will soon be granted with godlike powers. Madison (49): Larry's mother. She's a very caring woman who raised 5 children after her husband died a few years after L...

Shemale Trouble

by Braids on Mar 11, 2007
Fetish

You were at a bar when it happened. You were just having a drink when a hot girl started hitting on you. You had nothing else better to do and you didn’t want to pass up an easy lay so you offered to take her back to your place for a little fun. She agreed without a question, but as you were walking out of the bar, you felt something hit the back of your hea...