Sissy Party Stories

84,300 results
Orientation
Length
Source
Infinite Scroll

Black Licorice

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

My name is Jamie. I am 19 years old. This is the story of what happened to me Halloween one year ago. It was the last week of October and the leaves had turned brilliant shades of orange, red and yellow. The nights were getting cooler. Everything you could imagine was pumpkin flavored. Usually I get psyched for this time of year but things were different f...

Linda

by ofloveandlust on Sep 16, 2017
Erotic Couplings

"How old were you at your first?" "Oh my god, you don't ask a woman something like that!" Linda elbowed him in the gut. It was flat and hard as a rock and she was probably more turned on by it than he was injured. "Vut? I can always Google it." His accent wasn't all that thick but from time to time it would be noticeable. That turned her on too. If they ha...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Sissy's Journey: The Cocktail Party

by IndianaSissySub on Jun 8, 2020
Transgender & Crossdressers

Brett was an attractive boy with a swimmer's build in his late twenties with short dirty blonde hair, clean cut in appearance with soft features and a chiseled, toned but slender body. He had been busting his ass since high school trying to make a name for himself as a musician, but as more time had passed without landing that elusive record deal, he began t...

A Gooner's Tale

by changoparati on Sep 16, 2017
Transsexuals & Crossdressers

While waiting for the party to start, she had me getting naked and jacking off for her while she talked about the many dicks she's had in her ass, pussy and mouth, and the technique she employed in each case to get cum from them, pumped into her slutty fuck holes as quickly as she wished, even proposing to show me how. While the 6 or 7 men she'd invited ove...

Kinky Dentist Sian And Sissy Rachel

by Sissy Adele Howells on Dec 12, 2018
Fetish

Most people hate going to the dentist, but I get a sexual pleasure every time my appointment comes around. That is because my dentist is the sexiest women, that I have ever set eyes on. Sian Harris is in her late thirties. She is of medium height with short, brown, mousy hair. Sian is very pretty, with a smile to melt any perverts heart. Sian's husband worke...

Mindy's Moving Day - CFNM Ch. 02

by BuckyDuckman on Sep 25, 2017
Interracial Love

Author's note: I think this works as a stand-alone. I get my lily white ass reamed by a big black bull in front of my wife, her friend and my swim team. Delicious humiliation! Mindy's moving day signaled a huge change in her life and the relationship I have with my wife, Debbie. That was the day we put on a real life show of me offering up my sissy ass wh...

Subliminal Obsessions Ch. 07

by Sissyhalo on May 28, 2018
Transsexuals & Crossdressers

*Before... But this, this is the big turning point because this, this as hot and as intense as it because it settled into lovemaking and being made love to by this amazing guy that honestly could have all the pussy he ever wants and he's with me. With me making love to me and it's so much more than sex to me right now. And honestly. Really fucking honest...

John Meets Sandra Ch. 5

by eeric on Sep 16, 2017
Interracial Love

If you have the time you can e-mail me and tell me what you thought. ***************************************** It has been a few months since I asked Sandra to marry me and she said yes. It was late in the afternoon and Sandra was getting ready to go to her bacholarette party. I didn't have that many friends so I wasn't having a stag party. When Sandra c...

The Making of a Mistress Pt. 06

by EiryCGar on Sep 14, 2020
BDSM

Author's note: 'All things must pass' and I feel that this series has reached a natural conclusion. As always, I must point out that all players in this fictional saga are aged 18 or older, and all sexual acts are consensual. The Making of a Mistress Chapter 6: Cwm Pechod's Cuckold Community The invitations to the party for the combined wedding anniversary...