Sissy Anal Training Stories

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Infinite Scroll

Shared Fantasy: Heather's Wish

by JamesSD on Sep 16, 2017
Anal

"I want to try anal sex." The six words were written in careful script on an otherwise empty page. The page was in the hands of Tom, a 22 year old college senior. It had recently been inside a blank envelope which Heather, Tom's girlfriend of eight months, had given to him. Tom was a bit surprised. Was Heather serious? Could real girls, those outside of po...

Never Say Never Pt. 04

by SunChris on Sep 14, 2017
Anal

So much to catch you up on during this long two plus year hiatus. Rachel surprised me. She has fully embraced anal sex and taken the lead in exploring new avenues of enjoyment. How's that you might ask? Read on my very soon to be titillated reader. We are kinky. Hopefully we have not delved too far into kinkiness for your tastes. You've been warned. Rachel...

Wrapped Around Her Finger

by lizthewizz2000 on Sep 13, 2017
Anal

Before I begin, I would like to thank all the fan e-mail I've received - I love encouragement! A lot of the e-mail I received had to do with the story "Veggie Tails", thus this (kind-of) sequel to that story. What I am about to relate to you is the story of the first time I ever experienced anal pleasure with another woman. Of course, I had grown up explorin...

Apartment 718: Nothing But Butt

by TheCowboy on Sep 14, 2017
Anal

Author's Note: This is another entry in my series Apartment 718. This is a series of two people who are in a Dominant/submissive relationship. The first entrant of the series is called Welcome Home and has some of the background information. From there the rest of the stories can be read in any order, there is no chronology to them. As an added note you will...

Why I Am an Anal Slut Ch. 01

by john_mcleod on Sep 18, 2017
BDSM

"Why would anyone want anal sex?" That is what friend of mine said recently, and as I lie here with my arms and legs tied to the corners of my bed, and my stretched asshole dripping with lube, it's an easy question to answer. I didn't always love anal, but I have always loved mind blowing orgasms, and who doesn't? It just happens that what makes me cum har...

Confirming Carter Bk. 04 Expansion Ch. 02

by RibaldWriter on Oct 31, 2017
Sci-Fi & Fantasy

It's been a while since I worked on this series, and I'm still trying to get a feel for the characters, so cut me some slack... This offering is very Tammy-centric, and she's having an up and down day... * * * * * Confirming Carter4 Expansion02 Interior-Col. Sheppard's Office, North Tower 0745 Hours "Sheppard, I need ten people with the ancient gene, a...

Knowledge is Power Ch. 3

by Ridinghoodswolf on Sep 16, 2017
Anal

I looked through Andy’s program and chose my first…well, victim. She was about thirty, kind of shy and a little mousy, judging by her picture. She worked as a secretary in a government office. I had access to her emails from home, as well as a list of every link she visited and when. I used this information to study her habits. As she was my first, I ended...

Hypnosis

by StickmanLt on Sep 16, 2017
Anal

I don't know where I got the idea, but whatever possessed me to try it was a godsend. You see, it's not so much that I'm a deviant or anything... but I've always had one little dirty obsession. I love the idea of anal sex. I love the thought of sticking my cock into a girl's tight ass and fucking her until I cum. But I also like making a girl moan. I love...

Ass Man and Ass Mom

by andtheend on Sep 16, 2017
Anal

Doctor has anal sex with a beauty queen. * She had the slim and trim figure of a dancer, the shapely legs of an ice skater, and the muscle tone of a gymnast. After kissing and kissing her, after fondling her ample breasts and feeling her round, firm ass through her clothes, he removed her bra and sucked her nipples, while she felt his cock through his pant...

My Wetsuited Fantasy

by OzSteamer on Sep 13, 2017
Fetish

Hi brotherbig1984 I would love to be dragged to the bottom of a shallow warm lagoon by a beautiful woman in a tight wetsuit. She will allow me occasional puffs on her respirator while she strokes my naked body all over. A mixture of fear and lust..........my lungs ache, but my cock grows harder........what will she do to me.....another gasp from the respira...