Ultimate Sissy Weekend Stories

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Kitty Kat Nip Ch. 01: Mile High Sissy

by FoxTrap on Sep 14, 2017
Transsexuals & Crossdressers

Kyle couldn't imagine a more boring graduation gift. While everyone else was headed to Cabo or Europe for a quick backpacking summer trip with friends, the family decided to rent a resort condo in the Dominican Republic for 3 weeks. This could have been bearable if it weren't the fact that they only afforded this trip by inviting every conceivable member of...

Lost Kingdoms Ch. 02

by LillyStyle on Sep 15, 2017
Sci-Fi & Fantasy

Thank you for the feedback and yes this story was inspired by SAO. I watch A LOT of anime and really enjoy almost everyone I see. While I watched SAO when it first appeared I really didn't think up this story till recently. No I will not be copying SAO in the fact that you are shoved into a game you cannot log out of and if you die in the game you die in rea...

Living Out Linda's Fantasy

by joeuser691 on Sep 15, 2017
Fetish

Saturday afternoon, Linda drew a bath for me. It had jasmine scented oil, and was just right. I stripped off my clothes and sank into the warm, refreshing water. As I relaxed, Linda got naked. I thought she was going to join me, but she grabbed the shaving cream and a razor. She told me to relax while she shaved my legs. I lifted one leg up and let her get t...

Kerry

by ThomasMagica on Aug 18, 2017
First Time

Everybody remembers their first time. Losing one's virginity is a milestone in anyone's life. Sometimes the memory is pleasant, and sometimes not so much. Either way, it isn't likely to be forgotten. I won't say I remember my first time like it was yesterday, because, frankly, many of the details have faded over time, but I do, however, remember enough of it...

Saturday Afternoon At Claire's

by curious_writer on Sep 11, 2017
Fetish

My story was going nowhere. I'd been working on it at night for several weeks, writing a page or two at a time, deleting most, keeping only a fraction of what I started with. But I was having a lot of trouble writing the female character. I just couldn't get into her mindset. I wasn't proud of what I was doing, but I was working on an adult fiction story fo...

Remembering Valentine’s Day

by sophist801 on Sep 16, 2017
Loving Wives

"Hello, my name if Frank. I'm an alcoholic and I've been sober for thirteen years, two months and sixteen days." I was shaking as I spoke. It has been exactly one year since I returned to my AA group. Throughout the last year I'd gone to no more than a handful of groups but knew today was a day I would not miss. No, I could not miss today; my life depended o...

A Matter Of Attitude

by luvpsy on Sep 17, 2017
Loving Wives

My wife, Pat, is a wonderful and sexy woman. I love her dearly and if I wasn't sure before, I am sure now that she truly loves me and I will never need to feel insecure about our relationship again. Loving my wife as much as I do, I wanted her to have the best of sex. Unfortunately, I was born with only an average penis. I wasn't an athlete or a body build...

Biker Bitch Ch. 01

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter One: Cassie Cassie woke up feeling hungover, hungry, thirsty, beaten and abused. She was still chained to the billiard table in the Beasts of Burden Motorcycle Club clubhouse. She rubbed her ankle where the chain was manacled to her leg. Her nylon stocking had worn through and her skin was red and bleeding. Had it really been four days? Cassie s...

First Date with Diwata

by diegoroyo on Sep 14, 2017
Erotic Couplings

Tomas has been surprised when the little Asian flower had addressed him in Spanish. "I am Diwata. Most call me Di. Hello? You want haircut?" She looked every bit a small, Asian Hispanic girl. Tanned skin, long black hair, brown eyes, but not the Native American mix he had come to know. She was very much Asian. He held her small hand out to shake with his,...

College Crossdressing Confessions Ch. 03

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. This is the third in a series in which I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true. Please read the first two installments for context. *...