Shemale Friend Stories

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Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...

Erin and the Wonder Bra

by kimberlykitten on Sep 12, 2017
Fetish

Erin was up late night, doing a little bit of studying. She had the television on, watching one of her favorite late night movies while studying. Suddenly, Gary Coleman pops up on the television wearing a business suit in front of shelves, stacked with bras. He began advertising for the Mega Wonder Bra. "For all the ladies out there with humongous breasts...

Amy Finally Lives Out Her Fantasies Ch. 03

by LuvAGoodPegging on Sep 12, 2017
Toys & Masturbation

(Author's note: Love feedback, and can appreciate constructive criticism, but if you don't like the idea of a man masturbating with anal toys, or with another man in the room, you'll probably want to skip this story. Thank you.) Amazing the things one finds when on their significant other's computer. Benjamin -- or should I call you "Kyle"? -- you really s...

When Sara Met Bob Ch. 05

by yellowfrog on Sep 14, 2017
Fetish

Bob remains the love of my life, the fountain of my admiration! Handsome beyond words, virile and composed, sexually insatiable in many ways, Bob has become what every woman wants - in addition to her own husband, of course. In the intimacy of our extra-marital affairs I enjoy massaging his prostate, deeply and slowly, my fingers moving very deliberately to...

Hotel Californication Ch. 02

by Many Feathers on Aug 30, 2017
Group Sex

Check in was at two o'clock. The resort was indeed rustic, situated in lush green foothills with breathtaking views. We were again given a handout of daily events and activities, dining hours and informed that there would be an initial welcoming party that evening at six. Interestingly, our thumb prints were then taken and would serve as the keys to our room...

Swinger's Paradise

by DickThePimp on Mar 26, 2019
Celebrities & Fan Fiction

Pure Depraved Hedonistic Sex Parody Hedonism is not for everyone. Open sexual boundaries lead to pure sexual bliss. This is a look into the world of sexual exploration with no rules. I'm a hedonist. I'm all about seeking out my pleasure, at all times. Join me and my perverted crew as we explore an open sexual world. Welcome to... Swinger's Paradise... "Bab...

When Sara Met Bob Ch. 03

by yellowfrog on Sep 14, 2017
Fetish

It is a standing joke at all nail salons. A woman that has nine long fingernails and one trimmed short is for-sure into prostate massaging her husband. I decided to go one step further. I went and enrolled Bob at the local community college in a six-week course for manicure and pedicure. from that day on, Bob and only Bob manicured my nails. After peeing in...

Control Ch. 04

by thisonelad on Jul 1, 2019
Sci-Fi & Fantasy

"So, I was just thinking, like why does she even like him, you know? They are like, so bad together..." Jesse said as she sipped on her caramel macchiato through its straw. "Uh huh." Emily said absentmindedly, taking a drink from her own coffee. Jesse was so boring. She'd wanted to spread into her, to shove a hot slimy slug into her dumb mouth and finally...

Shemale Funpark

by patrickstar1212 on Apr 22, 2025

You go to a Funpark in Miami, Florida where you are supposed to meet your Friends. You really like them and drove all the way out here just for them. Right as you enter the Funpark to get to the meeting point, your Friends call you in a groupchat. They tell you that their Car broke down a long time ago but their Phones had no Battery and they were in the mid...

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...