Sissy Halloween Stories

12,071 results
Orientation
Length
Source
Infinite Scroll

1, 2, 3.. As Easy as ABC Ch. 17

by boo_dreaux on Oct 8, 2019
Group Sex

They were alone now. They only had each other now. But, for Tess and Jo, it was enough, it was all they needed.... "Thank you, thank you for coming to say goodbye to them,....." the, almost, identical words flowing from the sibs' mouths as they bade the well-wishers farewell, thanking each and every one, a 'well attended service' the newspaper would say in...

Living the Good Life Ch. 01

by DickThePimp on Oct 8, 2019
Celebrities & Fan Fiction

"Where's my darling grandson?" "He's upstairs. He hasn't been feeling well. Bridgette is taking care of him." "I bet she is." (Grandmotherly giggling) "She does a great job for my baby." "Yes. She's a talented employee. I'm glad she can help my grandson feel better. I'm more than happy to do that myself though, dear." "I know you are mom... so am I. Don...

Have Trouble? Contact T. Rex

by imhapless on Mar 31, 2020
Loving Wives

All characters in a sexual situation are eighteen or older. ********* In the early-1930s in the United States a small pacifist Christian sect known as The Lord's Sheep established itself near Moab, Utah. The sect consisted of fourteen adults (seven couples betrothed to each other before God) and sixteen children. All married couples, except for childless...

The Robertson's Sissy Ch. 01

by Clite69 on Jul 31, 2019
Group Sex

*Being a long time reader I finally decided to try writing my first story. I plan to make this a longer series so this part is a build up of what is to come.* Summer was finally here and school was out! For me it wasn't just out for the summer, but it was out for good! Through all the years of working my way through the public education system I finally gra...

Futanari Academy Ch. 04

by TheOrcKing on Jun 5, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. Chapter 04 Bailey was surrounded by cocks. The smooth, girlish little twink was nude and on his knees in a soft ocean of satin pink pillows, com...

The Cruel Step-Mother Ch. 03

by Croony on May 13, 2020
Mature

'Good morning Timmy, how are you today? Did you sleep well?' asked Joanna, his step-mother as he walked into the kitchen. Timmy felt like telling her he would have slept a lot better if her mother had let him sleep. Joanna's mother Jean had been to his room after they had all gone to bed complaining she was horny and needed Timmy to do something about it....

Reformation on Couples Therapy

by Marriedkinkylife on Oct 10, 2018
Novels and Novellas

Authors note: This is a multi-part series following the sexual journey of two married couples, as they explore various fetishes and kink, including their own sexuality. Please read the story tags. You've been warned. * I was suddenly awoken from a deep sleep. The alarm hadn't gone off, yet. Fuzzy-headed, I started to sit up and as I was gathering my sense...

Pain of the Goblin

by justincbenedict on Sep 17, 2017
BDSM

10/24/05 As I write this, my left leg is cuffed to the chair. I haven't been to the bathroom in thirteen hours, and Miss Stephanie has insisted that I am not working hard enough on journaling her attentions! The misery is palpable, I must confess. She spent most of last night teasing my poor cock to near distraction..."Now that you keep web journals, dea...

The Job Fair

by BaronS on Sep 16, 2017
Fetish

PART I The newspaper was filled with the usual drama of the overnight affairs of the world and advertisers shouted out their customary diatribe of clichés. But deep in the classifieds section, a small ad caught her eye. A local company with an international base was looking for nurses. They were particularly interested in candidates who had practical experi...

Silver Moon: Bk. 02 Ch. 06

by maxd01 on Dec 24, 2019
NonHuman

Authors note: Thanks for the patients for this chapter. I thought I had posted it and then ended up in the infirmary with a severe skin infection of one leg and rather was out of it for a few days. In any case I am already partway done with the next chapter and will hopefully have it done by this weekend. As usual all relationships are 18+. ***** Pam slow...