Pegging Sissy Stories

7,509 results
Orientation
Length
Source
Infinite Scroll

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Sissy Sidney and Sister

by FemFreak on Apr 17, 2019
Transgender & Crossdressers

Summary: Sidney is reluctantly persuaded into submitting to Ellen's humiliating wishes. His sister is along for the ride and gets to humiliate him a bit as well. In the end, Sydney questions his identity. All characters are 18 or older. Tags include feminization, crossdressing, pegging, femdom, mff, incest. ~~~~~ Angie loved to bully her little brother Si...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

Coming Home, Coming Out Pt. 09

by EiryCGar on Jun 1, 2020
BDSM

Author's note. As this saga continues, aspects of sadism, slavery, cuckoldry, lesbianism, denial and general bdsm are explored. All characters are figments of the author's imagination, and all characters consent to every aspect of the activities described. As always, all characters are aged over 18. Chapter nine. Saturday morning dawned, and Sara slipped f...

Begging for a Pegging

by Cirkle7 on Oct 12, 2020
Fetish

I'd like to first apologize for my extended absence! I became frustrated by anonymous critics who would pick my stories apart. So if this story is in no way interesting to you, please do not read all of it and then anonymously comment on how bad you thought it was.. I appreciate feedback and criticism but if I do not know the source then how could I trust it...

Spiced-Up Marriage: A Big Surprise

by silkstockingslover on Feb 24, 2020
Fetish

Summary: Husband and wife explore same-sex curiosity together. Note 1: This is a 2020 Valentine's Day Story so please vote. Thanks to:Tex Beethoven and Robert for editing this story. Spiced-Up Marriage: A Big Surprise "Do I have a surprise for you later tonight," my wife smiled, as she rubbed her nylon-clad foot on my crotch under the table at a five-sta...

The Gentlemen's Panty Club Pt. 05 - Final

by joefelton on Aug 22, 2018
Fetish

Authors note: This is the fifth and final part of my story, and I believe I have saved the best for last. Thank you to those of you who've read the first four parts. For those readers who are new to The Gentlemen's Panty Club, I have included a short cheat sheet in this note, listing the major characters and a few significant details about them, that should...

Helping Jess Pt. 04

by mski on Sep 25, 2017
BDSM

I got into the house. Jess looked into my eyes and saw I was out of it. "I guess that was quite hard for you John, maybe too much too quickly." I nodded. My head was screwed, I didn't really know where I was. She gave me a kiss on the lips. "OK sleepy head. Let's get to bed. Up the stairs with you, and brush your teeth!" She watched me walk up, then cat-...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Women Enjoying Naked Men Ch. 03

by escriterra on Sep 13, 2017
Fetish

The muscles in her hips she had pressed into use as she fucked fantasy-Darrian the night before were actually sore the next morning as Taryn went through her gym routine. It was a delicious soreness. She looked forward to exercising those muscles so they wouldn't be sore. Taryn was ready. She just couldn't find a guy to peg. So it was good ol' dependab...