Sissy Friends Stories

149,788 results
Orientation
Length
Source
Infinite Scroll

Sissy Cuckold Husband

by bisissystephenie on Sep 16, 2017
Fetish

If you don't like sissy, cuckold, bisexual men stories, then please don't read it only to complain. You look stupid! ***** Like many husbands, I've wanted to see my wife fuck other men. I like the idea of being a cuckold. I had thought my wife Pam had been fucking a man but I had never seen it. One afternoon a friend of ours came over while my wife was at...

Sissy Boy Chuck Becomes Just Sissy

by Krazy35 on Sep 14, 2017
Transsexuals & Crossdressers

A long time ago, I realized that I had a thing for women's clothing. I used to sneak into my sister, Jessica's room and get all dolled up in her clothes. She was a year older than me, but we were practically the same size. I got an incredible hard-on looking at myself in her full length mirror. I quickly undressed, put everything back the way I found it, the...

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...

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...

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...

Miss Guided Pt. 03

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

That evening I went to dinner at Donna's house. Donna opened the door and was beautiful in her little black dress. She wore impeccable makeup, stiletto heels, black nylons. I felt like a frump in my plain outfit. She explained that her husband Mary Lou just got home from work and was upstairs changing. We talked and drank daiquiris for about a half hour...

Revenge?

by magmaman on Sep 15, 2017
Loving Wives

When a young man is barely 19 years old, hormones rage. It's just the way of life. Ricky was that way, having discovered the joys of sex just a few days earlier. He decided he really did like that. That one time had been in his old Chevy Camaro and it was not all that easy to do. The beach party earlier had been a kick, Ricky spent most of the evening dan...

The Training of Sissy Paula Ch. 5

by submissive~pet~ on Sep 14, 2017
Fetish

After the fuckings I had gotten from Max my asshole was so stretched, I had to wear diapers all the time. Mistress Carolyn used this to her advantage. She had a few men that liked sissy babies. The men would bring me all sorts of little sissy clothes. Dress me up and have me nurse their cocks as if they were bottles of milk. One day a new man showed up, he w...

Another Submissive Slut - Ms Shawna

by Stillherer on Sep 19, 2017
Fetish

Ms Shawna had rung. I had been summoned. As expected I was dressed as ordered and waiting nervously in front of the building when her taxi arrived, late. Ms Shawna was excessively infusive in greeting me as I climbed awkwardly into the back of the cab with her. The driver was a leering foreigner, with a manic smile who was far more interested in sneaking a l...

Master Gene's Email Response

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Back at home that night I kept thinking of what had transpired that morning with Master Gene while still wearing my cum stained panties as Master had told me I could only remove them to shower. Otherwise the pink thong panties that had been soaked in cum would remain on at all times until I was told I could switch to other panties of mine. Was this a sign Ma...