Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

Love One Another

by Skippy47 on Mar 30, 2020
Transgender & Crossdressers

LOVE ONE ANOTHER It had been a fairly long dry spell for me, Arnie Spellman. I was just not in the mood for another one-night stand. In reviewing what I really wanted, I decided that it was time for a long-term relationship even if it meant having to get married. My old drinking buddies had been taken off the market for the most part. I was 25 years old and...

Gender Bender

by ManoLenta on Jul 8, 2019
Sci-Fi & Fantasy

"Where were you last night?" I rolled onto my side and a headache thunder-clapped through my skull. A nude woman occupied with me a bed so broad it seemed a landscape of satin sheets. "Where did you go last night?" she asked again. Whoever she was, she was royalty. A holo-tattoo of the Imperial Dragon coiled around the pupil of her left eye, shimmering i...

Backdoor Man Ch. 12-13

by SevMax2 on Jul 14, 2020
Group Sex

Chapter 12 I awoke just a bit hungover, of course, on the hideaway bed, and I wasn't alone. It took me a moment to realize who it was next to me, and ... it was Natalie! I shook myself a bit, especially as I discovered that I was naked and my hard cock had been pressed against her butt-crack. I started to get up, a bit panicked at the realization that I mig...

Katie and Rex Ch. 01

by EmeraldSolitaire on Aug 24, 2020
BDSM

Katie DuMont is a beautiful, passionate, and intelligent woman. She has always considered herself an alpha female and a committed feminist from the early age she could see how patriarchy and the way it promoted false so-called "traditional gender roles" has caused so much harm and the most for the men who found themselves the losers of life, especially amon...

Bartender Ch. 01

by windwriter on Sep 16, 2017
Group Sex

The city is a place that you can see or do most anything you want. It took me a while to get used to this since I grew up in a small town. One evening I was out at a club and went to find the bathroom. In the process I stumbled across a guy and girl getting it on in the back room. When I opened the wrong door and realized what happened my first instinct was...

Training Him to Take Dick Ch. 01

by magic_tantra on Sep 19, 2017
Fetish

Training My Stud Boyfriend to Take Dick! Ch. 01 My name is Belinda I am a college coed who loves sex with both girls and guys. I am a hot brunette with long black hair down to my butt crack with ivory white skin and piercing blue eyes. I have a nice shapely body and love my real 36 C breasts with strawberry sized nipples. I have a clitoris that protrudes fr...

Caught on Camera Ch. 02

by interqueen on Jul 24, 2018
Interracial Love

So, I waited and, at the time appointed, my patience paid off. Kind of. I went to work early on the appointed day and cleared all the important stuff I had to as quickly as I could, meaning I could watch the feed from my home in relative peace and quiet. I look back and think about how crazy this all was - spying on my wife and so on. But back then... I had...

Road Trip Rogue Ch. 07

by Strawberry_2051 on Sep 12, 2017
Erotic Couplings

Ch. 7: Bite Therapy The rest of the evening at Ozzie and Paula's was uneventful. Ellen was pretty drunk when we left the party; and we hadn't gotten halfway home before she made it damn clear she wanted to have sex. When we got to the house I had to zip my pants up just to get out of the car and go inside. The phone was ringing as we opened the front door...

Sandra and Stevie Ch. 35

by Goodhusband on Sep 19, 2017
Loving Wives

Note: This story is the thirty-fifth installment in a series entitled "Sandra and Stevie". If you have not read the previous thirty-four episodes of this series, I encourage you do so before beginning this chapter. This is a dominant wife humiliates submissive husband story. That is the kind of story I write. If you do not enjoy these types of stories, I st...

Cuckold Story - Christina's Revenge

by cuckcreampielover on Sep 12, 2017
Loving Wives

Cuckold Story 3 – Christina's Revenge Disclaimer: This story may contain bisexual activity, cuckoldry and humiliation. If this offends you please move on to another story. Otherwise, enjoy. Recently, after a night of creampie cuckold humiliation, I somehow got lucky enough to blow my load in my wife's best friend Christina (see my previous story for deta...