Sissy Friend Stories

145,580 results
Orientation
Length
Source
Infinite Scroll

The Hardest Kind To Be Ch. 01

by Joe Wordsworth on Sep 16, 2017
First Time

In the offhand chance that you don't find the setting clear on the issue, all characters are eighteen and legal. This is also a madly different story genre than I'm used to writing, so be kind. . . .. ... ..... She hated her. Hated... though strong and dramatic, it was the only word that summed up their relationship. Nobody would have guessed it, but i...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

Chronicles of Heather Maureen Ch. 05

by HeatherMaureen on Sep 14, 2017
Transsexuals & Crossdressers

My Life with Marty I spent a lot of time at Marty's over the next couple of years. He explained to mom that his 'son' had trouble making any friends and he'd been so glad when I became 'Jason's' friend after meeting him at school. Thus Marty and mom got to know each other thru the frequent phone calls asking if I could stay over or spend a weekend, again. M...

A Weekend Away Ch. 01

by SluttyChrissy on Sep 21, 2020
Transgender & Crossdressers

My wife Tiffany had been hinting for a while about my birthday surprise. She wasn't great at keeping secrets, and I normally figured out her surprises in advance only to have to act surprised, but this time she was being super cagey. She asked if I would be able to leave work at noon that coming Friday so I figured we were going out of town for the long week...

Sissy Pantyhose Twins Ch. 01

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

Twice The Fun... Part One... My Slut had received her orders in the envelope which was always left on the kitchen counter before I left for work. She was to perform whatever was mentioned in this envelope, each day, without question -- either during the day if so asked, or to be ready for me when I get home. Whether it was a new outfit, a specific outfit,...

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...

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...

The Cock Clock Ch. 04

by HarveyMarcus on Sep 26, 2017
Erotic Couplings

WARNING: The following story is for the entertainment of ADULTS ONLY, and contains descriptions of explicit sex. If you are not an adult, or reading sex stories upset you, or you are offended by subjects of a sexual nature - do not read any further! This story is for entertainment only. It contains adult oriented material. This is a work of fiction. The a...

Exposed Sissy Slut

by MarkRoberts64 on Sep 16, 2017
Exhibitionist & Voyeur

I've always been turned on by exhibitionism, and especially by so-called "forced" exhibitionism. The last few years, I've noticed more and more that I love the game of taking risks in public, where I could possibly get caught being submissive, or slutty, or a sissy. I'm not interested in just exposing myself, or strutting around with a slave collar on. What...