Anal Sissy Stories

51,035 results
Orientation
Length
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Infinite Scroll

Brookie

by bbkradwell on Sep 12, 2017
BDSM

I first met Brookie in the Autumn, just as classes were starting at the local University (the very same school where I'd met Melissa.) Brookie was working at the Campus Bookstore, a place I like to hang out, if only to look at all the hot co-eds in their Florida-Finest attire! (Actually, ANY place on that campus is a great place to see hot babes, scantily dr...

A Special Treatment for Karen

by margaret_jenkins on Oct 8, 2019
Fetish

Note to readers: I haven't posted anything or even written much for a long time but even now I sometimes get appreciative feedback, asking when I'll post again. A few days ago I was searching on another site for literature on one of my favourite fetishes, and I found a story which looked promising. Right away I thought, "Wow, another author with almost the s...

My Willing Transformation Surgery

by TammyPanty on May 13, 2020
Transgender & Crossdressers

Growing up the only child of a single mother I was born with male sex organs. But ever other physical characteristic I had was female. My penis was very tiny. I had sloped shoulders, not squared. My lips were naturally larger, just like a female. I had no scrotum "sack" just a round mound under my little penis that had even smaller testicles inside. I had tr...

Gilda Succumbs to Group Sex Ch. 06

by walterio on Mar 16, 2020
Group Sex

After a late lunch the two beauties went to Gilda's room and got in bed. Faith lay on her back next to Gilda and her hands went to her pussy. She started to finger herself. Faith did not notice Gilda get off the bed and leave the room. Her eyes were closed and she was furiously flicking her clit when Gilda returned. "Faith I have a surprise for you." Faith...

Business & Sex, a Great Combo Ch. 02

by walterio on Sep 24, 2019
Novels and Novellas

ANXIOUS FOR THE NEWS I flew home Thursday evening and I was anxious to hear how things went with Cathleen and Jane. I didn't get home until late and Cathleen was sleeping. Not wanting to wake her, I slept in the other bedroom. She was up before me on Friday morning and I woke up to the aroma of fresh coffee. We both showered, dressed and after breakfast hea...

For The Love of Botany Ch. 2

by Athena_e19 on Sep 11, 2017
NonHuman

When Sarah regained consciousness from the latest series of orgasms she felt the familiar feeling of the lush green plant life on her, in her, and around her. How long she had been down there she didn't know. Why no one had found her she didn't know. The only thing she did know was that every hour the plant entered her and fed off her juices. Lately, after...

My Girlfriend's Sex Slave Ch. 03

by subboy4821 on Sep 18, 2017
Transsexuals & Crossdressers

I lie on the bed, my ass sore from all the fucking my girlfriend gave me. I'm scared to think of how many people she comes back with, and what else they're gonna do to me. About an hour later, I hear the door opening and hear a multitude of female voices. Then they enter the bedroom. It's a total of 5 girls, 2 of them have black hair, 2 of them are blonde, a...

Bi Pantyhose Passion

by june613 on Sep 26, 2017
Transsexuals & Crossdressers

I've had a Pantyhose Fetish for over 30 years now, and love wearing them on a daily basis. But back in the summer of 1995, I suffered a heat stroke, and almost died, when I recovered, I vowed I would stop fantasizing, and live out these dreams and fantasies. I had been masturbating while dressed in Pantyhose for quite a long time. I progressed to "batjack...

Jessica's Anal Training

by rockbohunk on Sep 13, 2017
BDSM

Jessica was a young submissive with a lot to learn. Although she tried to please Rick, she had always refused his anal advances. Rick had heard enough of Jess's excuses, today was training day. Jessica completely undressed for Rick as he handed the leather wrist and ankle restraints to her. Jess strapped on her ankle restraints just like the many times t...

Husband's Anal Adventure Ch. 14

by Anal Slave on Sep 19, 2017
Fetish

My wife woke me up early this morning she wanted to go down to the market and get some fresh vegetables. We walked into the store and went to the produce department my wife looked at me and said do you want to do something kinky this afternoon? I said sure. She leaned over and picked up a big hand full of carrots, she said we need a few of these. Then she pi...