Shemale Fucks Male Stories

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Infinite Scroll

HypnoSissy: Educated to be Pegged

by silkstockingslover on Aug 13, 2019
Fetish

Summary: Cock sucker's training is advanced to hypno videos on anal sex. WARNING PLEASE READ: -This is a hypnosis story with potentially influential subliminal messages within it. -The story also contains hypnosis video scenes. -So if you begin behaving differently after reading this story and all your friends start pointing fingers, don't come crying to...

She-Male Chronicles Ch. 2

by Anal Slave on Sep 12, 2017
Loving Wives

Shemale Chronicles Pt. 2 Well here I am again bent over the edge of the bed while my wife fucks me with her strap-on dildo. I am grinding my ass down hard on her big toy and she is fucking me with force. My cock is limp and is swinging around like a big clit but I enjoy getting ass fucked and my wife loves to fuck me with her strap-on sometimes she will s...

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...

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...

"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...

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...

Babysitter Cupcake: MILF Cuckqueaned

by silkstockingslover on Feb 26, 2019
Fetish

Summary: College girl seduces wife and then fucks husband. Note 1: I have been asked by a number of people for a couple of years to write a cuckquean story (which made me look up what cuckquean means). I had begun attempts on one a couple of times over the past couple of years, but I set them aside when the plots didn't work. Then after a few more requests...

The Spider's Brothel

by Miles63 on Sep 13, 2017
Erotic Horror

Author's Note: Well, a chapter of a story I have been working on has been deleted as my external hard drive is bust! So I finished this story for the Halloween contest, a late late entry but enjoy. This has since been re-edited on 10/25/2013 as I feel the bad grammar mistakes have effected the rating of this story which is unfortunate as I'm very proud of t...

Danielle Ch. 06

by sexgundam666 on May 27, 2019
Sci-Fi & Fantasy

"Come on! It's my turn!" Casey whined. She leaned against the bathroom stall, watching and stroking herself to the scene before her. "Sorry, ahh, it's so good," Holly answered from her prized perch, though she didn't move from it. A train of complaints and insults danced between them, all while the albino bounced, swayed and clapped her body against a might...

Sissy/Cock Sucker Dictionary

by silkstockingslover on Jun 12, 2019
Reviews & Essays

Summary: A list of terms to aid in understanding the activities and nature of sissies and cock suckers. Note 1: The author's source material isn't Webster's Dictionary or anything similar, but is drawn from many years of interest in matters sexual and countless conversations, both spoken and online, with other perverts. Note 2: Thanks to Tex Beethoven and...