Sissy Friend Stories

145,580 results
Orientation
Length
Source
Infinite Scroll

Rooms for Rent

by johnhoftb on Jan 8, 2015
Erotic Couplings

It had been a year, a year since the death of your beloved Great Aunt Rachel. She had passed away quietly in her sleep and the funeral was beautiful. You had watched the memorial proceedings with tears in your eyes as you remembered the times you spent with her during the summer in her house just outside of her hometown. She never had children of her own, so...

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Naivety

by nymphette on Jun 4, 2018
Amateur

Alice Marie Fairborn opened her narrow cerulean eyes for the first time in 9 hours, her arms stretched in an energizing motion before leaping off her velvet-draped bed in happiness. She was finally out of high school! She had turned eighteen a week before, and spent it at the local church she and her parents attended every Sunday. Unlike most of her classmat...

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Time Manipulation

by IgnusObscuro on Mar 14, 2017
Science Fiction

Jessica broke up with you. Seemingly out of nowhere, one week she was excitedly talking in detail about what your wedding ceremony would be like, the next she was telling you she didn't have feelings for you, and she hadn't for a long time. You had kicked a lot of your old habits, but the depression brought them back in full force. You had begun masturbating...

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Hacking the Brain

by gamer8363 on Dec 18, 2016
Fetish

(I'm new to this, so if it's a little bad or has mistakes, sorry.) I woke up to my mother saying, "Eric Boil, get up, I'm going to be heading to the grocery and you need to help your sister with her homework, and your friend is in the living room." I got up and said as I started to get dressed for the day, "Alright, I'll be down in a minute.&q...

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The Appointment

by Father Dogma on Aug 23, 2005
BDSM

Lucy is the poster child for conservative. At 25 she runs a successful Ad agency. Yet she's never done anything wild. She has grey business pant suits and her glossy black hair that is always in a tight bun. Kara, her best friend keeps trying to help her loosen up. Finally she thinks she has the answer. There is a new BDSM salon that opened up "Ms Sarah...

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Futa Halloween Party

by DenomZero on Oct 31, 2020
Transsexual

This story includes very mild sexy themes and is mostly romance heavy. If any of you have any ideas or suggestions on the story I will seriously consider using them! What I enjoy most in this is the feedback, so don't be shy to give some :D Here's a link to the feedback forum: **https://forum.chyoa.com/threads/futa-halloween-story.3182/ Thank you so much for...

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Reservoir of Power Ch. 02

by SisterRobin on Sep 25, 2017
NonHuman

My great uncle Fergus used to pat me on the knee and he'd say, "Me boy, some thin's just smell right." I was just a lad, how was I to know that he didn't mean pie? ~ J. Milton O'Leary Reservoir of Power Chapter 2 Lena swatted at whatever was tickling her cheek. She growled in irritation and tried to reach out for her blankets, thinking to bury her head...

Good Friends

by javawarrior on Sep 12, 2017
First Time

AUTHOR'S NOTE: This is my submission to the "Winter Holidays" contest, so make sure to vote if you like what you read! I am also working on a companion story to my Summer contest submission, "What She Knows," so look for that if you liked either that story or this one. Thanks! * "I swear, I knew it would happen. He couldn't finish the last day of class wit...

"Uncle" Dominic

by ErosinaScarlett on Jun 11, 2019
Erotic Couplings

Libby stared, her lips slightly parted in lustful wonder. Her dad's friend; his hot, muscular DILF friend was standing before her in nothing but a towel reaching to his perfect strong hair matted calves. "Sorry," he chuckled, his toned damp shoulders shaking with his good humor. "I thought you'd be gone for the week. What happened to your friend?" Libby...

The Deepest Friend-Zone Ch. 06

by Vanttont on Sep 24, 2019
Erotic Couplings

This is the 6th installment of the story of how Connor became roommates with 7 college sluts. Connor has not been particularly involved since chapter 2, but comes back into the story more at this point. Make sure to read the past few chapters to learn a bit more about the girls Connor is getting involved with. Xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx Sarah had b...