Ultimate Sissy Weekend Stories

84,140 results
Orientation
Length
Source
Infinite Scroll

Naked Speed Dating

by exquisit_taste on Sep 1, 2017
Group Sex

The magnificent ballroom of the exclusive Vegas hotel was reserved just for this unique occasion: Naked speed dating. My girl friend had been to this event once before, loved the experience and brought me along this time. The host and hostess of the event swung open the tall, wide ballroom doors dressed only in black top hat, bowtie, cuffs and polished sho...

Red Dragon's Pride

by AmethystMare on Oct 8, 2019
NonHuman

The ragged cliffs struck the sky, breaking it apart in a stormy, grey cloud that was said to herald one's ultimate demise. If it had been a true omen, ravens would have cawed and flapped across it, disturbing the dark glamour with their raggedness, but Xigfeldo was the true omen and portent of death on the face of the cliff, stones crumbling away as he hung...

Sissy Hubby Ch. 05

by buttboi on Sep 19, 2017
Transsexuals & Crossdressers

Thanks again for all of your comments and votes! Please keep it up! *** Stacy drove through our neighborhood finally picking up the highway and leaving behind the people who might recognize me. Being recognized didn't bother me, I was truly happy for first time. I was becoming what I was born to become. I sat silently beside my wife wearing my short, tight...

Shannon's Little Princess

by CarlyJennings on Sep 25, 2017
Transsexuals & Crossdressers

Cameron was sitting at his desk in his apartment, working on his thesis when his cell phone started ringing and vibrating across the desk. Happy for the interruption - the writing was not going well - he glanced at the phone and smiled when he saw that it was his girlfriend calling. He and Shannon had only been dating for a couple months, but things were goi...

Across the Tracks Ch. 04

by BigCoreySKR on Sep 13, 2017
Romance

Otis walked and Ariel's house and just stared. It was all he could do. There was so many beautiful things in the house that he could almost believe he was in a museum. He heard her talking, and followed the sound of her voice to what he thought was a kitchen, but may have been a small restaurant instead. About the time where he could get close enough to hear...

Steph and Giulia Ch. 01: The Betrayal

by BigHand32 on Sep 16, 2017
Fetish

Giulia was going to be at the party. Stephen still wanted to see her, even if she had betrayed him. Every day, he had given her a ride to school. Every day, he had been there for her. She laughed at his jokes. She smoked his weed. Now she had betrayed him, but when she invited him to the party, he couldn't help but go. A week ago, he had finally got her to...

A Christmas Party Ch. 05

by lannasage on Sep 18, 2017
Interracial Love

**Hey guys, thanks for previous comments. Hope you like this chapter, please drop your comments so I know how I'm doing so far** Donald 'Donny' Iliamson had always been self conscious. Since his childhood, he had never quite fit in with the crowd. While in elementary school, he had been one of the dullest students in class, and whatever he lacked i...

From a Husband to a Dutiful Sissy Ch. 13

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Chapter Thirteen: Boy oh Boy, a New Day and a New Relationship. I wake up, the sunlight streams through the hotel room window. I lay for a moment gathering my thoughts. I realize I have spent the night with Mikel. I roll over and I see him peacefully asleep and my feminine emotions are over joyed at such a wonderful sight. I quietly and gently get out of b...

The Marriage of Martin Hastings Ch. 14

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin walked down the walkway his heels clicking loudly as he moved quickly away from the house. He felt almost naked walking in the bikini that Leanne had seen fit for him to wear out today. Wearing 6" spiked heel sandals and his hair in curlers covered with a large white scarf tied under his chin, he walked with his head slightly bowed as he thought about...

Jesse's Journey Down a Rabbit Hole Ch. 18

by sadkins116 on Sep 14, 2017
Illustrated

I want to thank everyone for reading, voting and commenting on our story. I submitted the first six chapters, and Rebeccasm submitted chapter 6 through 12. I will be submitting chapters 12 through 18. We have both worked hard on this series and as such both deserve to share the postings. Hopefully you will visit both of us and enjoy the series. As I mention...