Sissy First Stories

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Orientation
Length
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Infinite Scroll

Special School Pt. 02

by neutrona on Sep 16, 2017
First Time

A/N: This is part 2 of a 6-part series. It helps to have read part 1 first. ***** As Monday came around, we were taken to a different room for our physical pleasure learning session. This time, there were round holes in the wall and soon, there were penises being pushed through these holes. It was our first introduction to penises. Though we had seen pictu...

My Reluctant Wife Private

by gsdej5378163 on Sep 12, 2017
Loving Wives

My Story begins like this: I am the husband of Edora a beautiful sexy lady whose sex life has been interrupted because of me and has been unfulfilled sexually for many years ever since I was diagnosed diabetic and which eventually culminated in me becoming impotent and unable to get an erection. Thus, for a number of years that we have been married there w...

Beastly

by Clark84 on Feb 6, 2018
First Time

Sorry for such a short story, but this is my first story ever so leave a comment down below, plus some ideas for a part two any I use will get a mention. ***************** "You think life as a monster is easy, well it isn't all sparkly vampires and hot girls, it's a life lies and deception, so where do I begin?" Amber eyes stared at me through the undergr...

Celebrating 3000

by JillyJenn on Dec 30, 2017
Group Sex

3000 Yesterday was a beautiful day at the beach... full sun, no wind, a welcome relief after several days of stormy rain, gusts and thunderstorms. Like countless other days, I awoke early, ran for 5 miles, went to the gym for a couple of hours, then returned home, put on my sheer Wicked Weasel 404s and hit the beach. It was hard not to be introspective and...

First Date

by crazyinohio on Sep 12, 2017
Erotic Couplings

I met Lisa through an internet dating service. After e-mailing back and forth for a few weeks and talking on the telephone, we both decided it was time to meet in person. We seemed to have a lot in common and maybe it was a relationship worth pursuing. She lived forty miles away and I drove there to meet her. When I first saw her I couldn’t believe it. I kn...

A Year Of First Times Ch. 04

by Theeeeee1 on Aug 30, 2017
First Time

Our sex life for the next two weeks was a little disappointing after our ‘extraordinary Friday date.’ We went parking and were intimate but not to the extent of my eating Torrie’ pussy. I had really enjoyed pleasing her with my mouth and was anxious to enjoy the taste of Torie again. On Sunday evening two weeks after our extraordinary date, Torrie and I wen...

Apartment 718: Welcome Home

by TheCowboy on Sep 14, 2017
BDSM

Sara i'm glad that the heat can be turned up before i get to the apartment, knowing i'd be spending the night completely naked, i turned the heat up from my iPhone on the drive up to the city. i'm also very glad that once i was trained that i'd purchased a nice rug to keep in the foyer of the apartment. It makes it much easier on my knees as i wait for Him....

I Remember Ch. 01

by Extreme Bohunk on Sep 13, 2017
Erotic Couplings

I remember the first time I saw you. Short, cutely rounded, your shoulder length dark hair. Your dark eyes. There was 'something about you'. We smiled. We hit it off. Later, we went to dinner, and saw a movie about dragons. It was cold in the theatre, we sat close and held hands. The movie was boring, I made fun of it under my breath. I remember you giggled...

Better Than Before: Charlie & Mike Ch. 02

by juanwildone on Sep 12, 2017
First Time

Michael was aware of many things, on many different levels. Physically, Charlie’s mouth was sliding slowly up and down the length of his cock as her tongue pushed against his glans. Her left hand was holding onto his right butt cheek and her right hand was cradling his balls. Mentally, mentally he was so fucking confused and overwhelmed that he couldn’t th...

Watched for Years Ch. 01

by thehungriest on Sep 17, 2017
BDSM

I watched her for years. We met at a professional conference. I remember how stunning she was. The perfect almond shape of her eyes, the half-moon of her hips, the brilliance of her face when she smiled. At first I couldn't place what was so special about her- I meet many beautiful women in my profession but rarely feel an attraction as strongly as what I f...