Sissy First Stories

313,352 results
Orientation
Length
Source
Infinite Scroll

Punishment for the Boy

by novicewritermike on Sep 14, 2017
BDSM

The young sub looked to be in his early twenties. His blue eyes seemed to shine as he looked down at the floor. His hands were bound behind his back and his knees were visibly trembling. His name was Michael and he awaited his beloved Domme, Olivia. It was clear that he already felt sorry for what he had done. He understood that it was his responsibility to...

First Time Tales

by Sparky10 on Aug 18, 2017
First Time

I have always considered myself to be straight. However, at the end of a party at my brother's house the other night, we got talking about past sexual experiences/encounters. The majority of stories were tame but my sister in law Lisa's tale was quite horny. She relayed to all (about 10 close friends) the story of the first time a man came in her mouth. Sh...

The Wedding and Hilary

by story_lein on Aug 18, 2017
First Time

Here I was again at another boring wedding, knowing only a few of the guests, being the cousin of the groom. I have always hated weddings because most of the people there are either married or with a date and I am usually not. That feeling of being the odd one out and wishing that I could be with someone special too, is what I hate the most. It was hot and...

The Interview Ch. 01

by arlene548 on Aug 18, 2017
First Time

Recently we interviewed several young adults as part of a research project to determine trends of young women with sex and promiscuity. The results were very interesting and in some cases shocking. Number One#. Q. Your name? A. Deborah. Q. Your Age Deborah, or what do you prefer we call you? A. 20 and Deb is OK. Q. How do you mostly occupy your days? A....

Happy Anniversary: Janet vs. Anne

by gomez8 on Sep 14, 2017
Fetish

Janet and Anne, two of the first apartment wrestlers that came to public attention, had fought a brutal battle in 1974, leaving the defeated redhead, Anne, vowing never to fight again. Janet continued fighting, earning no small respect from the AHW crowd. With the tenth anniversary of that first publicized fight fast approaching it seemed like a god time to...

First Time as a Toilet Slave

by pantyslutpaul on Aug 18, 2017
Fetish

I lay on my back, the plastic sheet I was lying on felt sticky and clammy. I watched as the prostitute I was with pulled off her panties. Mistress Suzy was now naked. She was young and sort of plain, sort of pretty, slim with smallish breasts. Her bum was a bit bigger than the rest of her and it was her bum that she pushed towards my face as she squatted, le...

WAS a Virgin Bride

by luvs2watchher on Sep 14, 2017
Loving Wives

Kara and I were high school sweethearts from the very start, she was the pretty, sweet innocent looking girl that few guys dated because they figured that she would never put out. She was only barely 5 foot tall and was only 89 pounds, but oh did she have a nice body! When she dated though, the guys would always get her bra off of her petite 34 b tits and h...

Conditioning of a Scat Slave Ch. 01

by subtlesurrender on Sep 19, 2017
Fetish

With lots of time to dwell on a recently failed relationship and a love-life with little direction, Claudia inadvertently falls into perversions of scat persuasion. While allowing herself to get carried away in her newfound dark fetish, she finds her limits challenged when she reaches out to the scat world for someone to help fulfill her fantasy. * Part 1...

Monica Ch. 4

by billyt98366 on Sep 12, 2017
Mature

After Marie's call and dinner Monica and I sat on her bedroom floor and started talking about our pasts. I asked Monica how many boys she had had sex with she told me that I was the third person whom she had been with. Her first was about two years earlier when she was a sophomore and her boyfriend at the time was a senior. They and gone to a school dance an...

The Second Time I Cheated

by serendipitousP on Sep 16, 2017
Loving Wives

so i had been talking online to a very dominant but sensitive, thoughtful guy from dc named scott. we really hit it off, talked for endless hours in addition to having typed on compuserve forever, and i was finally ready to take a long drive down to visit, on a weekend his wife was to be elsewhere with family. i was very nervous during my drive down, trying...