Siss Stories

22 results
Orientation
Length
Source
Infinite Scroll

Siss the Bride

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

I was nervous. I mean, of course I was, how could I not be? Everyone is nervous on their wedding day, it's a big day, a commitment, especially when you're 26. I mean, it's not like I'm afraid of commitment, many of my boyfriends in the past would be able to tell you that; I wasn't exactly the type of person who would be reserved when it came to going all out...

Danny to Danielle - Beverly Awakened Pt. 02

by Deviana on Apr 13, 2020
Transgender & Crossdressers

Chapter 4 I read her note. They were all coming here- Beverly and her new girlfriends- and men. The man she was with, and others. Then a pic from her showed up. It was of her, the large earrings, and Maurice, kissing her neck. I had opened Pandora's Box and both she and I were now deep within its confines. Was there any way out? Would she want out, even i...

Siss the Bride Ch. 03

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Every marriage has its problems, even mine, which is a huge problem considering I'm a guy who gave up every semblance of a normal life to follow hidden fantasies on a spur of whimsy induced by my hot older brother. My life during my marriage to my brother has been built upon submission, only natural when you are a sissy crossdresser and when he has the perfe...

Service Day 01: Sissy's Breakfast

by SissyHubbyD on Aug 7, 2019
Transgender & Crossdressers

His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today. Today is Service Day, and he couldn't be happier about it. He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...

Kimmy's Discovery Ch. 07

by Deviana on Dec 17, 2018
Transgender & Crossdressers

--- closing Chapter 6 ... Kimmy's lips had become quite full, her hair longer and more lush and any hint of boi hair on her body had vanished. They were all very pleased with the arrangements and the results. ---- Chapter 7 Dougie tried his best to not pay too much attention to Kimmy when their work schedules matched up. Of course, there were the polit...

Sissy's First Gangbang

by TaykenByDaddy on Sep 12, 2017
Transsexuals & Crossdressers

I had been seeing Daddy Larry for over a year at this point. He was the third cock I ever sucked and the one to claim my sissy virginity by being the first to fuck my ass. He was exactly my type; early 50s, stocky hairy build with a small gut and over seven thick inches of manmeat that wanted nothing more than a younger guy to drain his load. The more femini...

Temptations

by magmaman on Sep 16, 2017
Romance

"I am really sorry, Millie. We just have no other choice, sales are down and with all of the new costs piling up....?" Ben Carter appeared sad as he gave her the bad news. Millicent did understand but it still hurt. After nearly six months on the new job that had taken her a full two months to find, she had barely gotten her feet back under herself again....

The Sexorcist

by Kingmaker711 on Sep 25, 2017
Erotic Horror

NOTE: All characters in this story are 18 and above. ***** Sally extended her arms as wide as possible and fell back on her bed. It had been so long. It seemed just yesterday she left home and now... it was as familiar as an old shoe. The drive down had been long, and even now, she could hear her little sister, giggling downstairs as her mom pulled out pla...

Finnegan's Awakening

by LetMeTypeInElvishDamnYou on Sep 13, 2017
Letters & Transcripts

She spent the better part of the hour running her fingers over the top of the envelope, feeling the rough edge scrape her fingers over and over.It was an envelope he'd licked; an envelope he'd stuffed just as surely as one day he would lick and stuff her. He'd eve promised to send her one of his manuscripts. Heart pounding, breath ragged, she could no longer...

My New Life

by cuckytoher on Aug 18, 2017
Fetish

Snow was falling heavily as I rushed to get home from work and start my weekend. This weekend however, would be like none I had ever spent before. It was my last day at my job and I had been recently laid off due to cutbacks and restructuring. That morning when I arrived at work I had been a handsomely paid executive bringing in a six figure salary, and that...