Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

The Prostate Exam Pt. 01

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

He finally booked into the doctors for the prostate examination. His wife had been nagging him for days, following one of their friends being diagnosed recently with prostate cancer. As he walked in to the Doctors he said he was here for an examination booked by his wife. The receptionist said no problem, your appointment is with Doctor Sutton. Pete sat i...

I Blush Too Damn Much Ch. 12

by bonnietaylor on Sep 19, 2017
Loving Wives

A few weeks went by and we sort of fell into a sexual routine. Bob would come home with pussy, Ann's pussy on his breath and sometimes a little cum on his shorts. He told me what Ann made him do each morning and afternoon. Each day, first thing in the morning Bob was called into her office for a meeting. He would remove his slacks and shorts so no cum would...

Appetitus Rationi Pareat Ch. 01

by HaddenIndustries on Sep 16, 2017
BDSM

*** In his four years here, never had Jeremy been in the principal's office. The amount of time Moe, on the other hand, spent here rivaled the amount of time he spent in class. Jeremy tried to surreptitiously glance over at Moe. There he was, slouched in the chair, hands shoved in his baggy jeans, chewing on a strand of his long hair. Moe had tormented Je...

Public Adventures of Mark Halloween

by rik581 on Sep 13, 2017
Transsexuals & Crossdressers

"The Public Adventures of Mark" Halloween Humiliation" Mark had asked all week about Cindy's plans for him on Halloween. She would not even give him a hint as to what she had in mind. All he knew was he going to walk the mall and parking lot with Cindy in the costume she had selected. "Don't you worry about it baby. I promise you it will be a night you wo...

Howling Roar: Fated Love Ch. 03

by DarkWolfKnight7 on Sep 13, 2017
NonHuman

For a while now I have been thinking about how to do chapter 4 and nothing has come to me. So after sitting down and rereading my first 3 chapters over and over, I felt many changes were needed to bring chapter 4 to life. One of the major changes was that I gave Sapphira more role within the story as I felt it was a little too focused on Lucian which left it...

Chasing Tail -- Neko Purr: Ch. 01

by BunnyHart on Sep 13, 2017
Sci-Fi & Fantasy

Chapter One Good Luck Kitty To my dear readers, comments are welcome and encouraged! Below is a short summary so you may discover if this story is relevant to your interests: Daisuke is an anime fan boy who wants to work in 'Tsuki no Sakura' anime megastore but is stuck working in the food court next door. He's single, clumsy, always tired and forever run...

Teen is Forced to Crossdress

by fun4all6969 on Sep 18, 2017
Transsexuals & Crossdressers

My first time with another man was when I was 18 back in the late 80's. My girlfriend was a virgin and the farthest we went was kissing and rubbing together with our clothes on. I would take my dirty magazines out behind where we lived in the woods and take off all my clothes and masturbate. I was out there every day there was nice weather masturbating and...

Amanda Adams becomes My Queen Ch. 06

by ShyDenZen on Sep 15, 2017
BDSM

I wake up in this strange-but-comfortable bed. A slight roll and I can feel the cage and it all comes tumbling back into my waking mind. As sunrise light pours into through the Eastern window, I suddenly worry if I've slept in too long. Or do I dare get up? This wasn't discussed... I have no orders that I can remember. What should I do? I stay put and try...

Seduced Into Submission Pt. 01

by tinycuck84 on Sep 25, 2017
Loving Wives

Ever wonder how your life can change in a single moment. Most instant changes are bad, but some can be good. Being a housewife with no children can be boring at times and this is one of those times. I reflect how my young marriage spiraled into a cuckolding relationship without the desire by Brett. It all started last year at the gym. My name is Mandi. I'm...

A Wife's Abused

by ARGEE on Sep 15, 2017
Loving Wives

This is my story about how I was used by my husband. At first I didn't have any idea he was using me and I simply did everything he asked me to do. I love my husband and I am sure I would do anything he asked me but he destroyed a little of my faith in him when I explain how this story unfolds. My name is Abby and I am 25 and Aldo and I have been married fo...