Sissy Hotel Stories

62,092 results
Orientation
Length
Source
Infinite Scroll

Playing the Part

by Sissysdream on Jan 20, 2020
Transgender & Crossdressers

All people in this story are above 18 or older. This is just a fast story I wrote and don't know if I will do any more on this story. *** My name is Tommy, but these days I go by Tammy. A few weeks ago, I was turned out by my high school bully during summer break and now I am a happy cum drinking sissy. I know I'm getting a bit ahead of myself here so let...

Sissy Hotel Play

by elliotsconfessed on Dec 24, 2018
Fetish

It was a Friday afternoon and I was feeling a little bored and some what curious... I had spent the last hour or so watching porn, but not just the usual straight type of porn I'd usually watch... For some reason I had an urge to watch men fuck other men and have guys dress up as girls and fuck themselves with toys! I was so turned on and a little confus...

Second Meeting with Master Gene

by sissysubTiffany on Jun 19, 2018
Transsexuals & Crossdressers

Friday evening comes finally as this was the slowest week of my life waiting for this day to get here as so looking forward to tonight even though I am still a little leery about becoming a sissy submissive of Master Gene's. I have shaved my entire body and sent pictures for proof as he demanded and now sitting in a pair of my pink with lavender lace bikini...

The Ex's New Toy Pt. 03

by Urtoy2be on Sep 15, 2017
Fetish

Wednesday afternoon and work was slowing down for the week. Sitting in my office bored staring blankly at my monitor waiting for 5:30 PM so I could cut out. I need a drink went through my mind. The weekend had been a blur. The events with my ex-wife and her new man had been crazy. Fantasies and thoughts had been awakened and now I was wondering who I really...

The Perfect Night

by transgendercharmander on Sep 16, 2017
Transsexuals & Crossdressers

It was finally happening! Mistress H arranged to meet up with me at a nice hotel to have some fun. She told me depending on my behavior; she may decide to move me in with her to be her full time slave. This was the opportunity I had been fantasizing over for months! I knew I would have to do my best to please her, so immediately upon hearing her orders to me...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...

Sissy_World 03

by JDBones on Sep 16, 2017
Transsexuals & Crossdressers

Billy rode in the front seat of the car, staring out the window, and watching the world go by. His mind swam and his body already hurt, but he knew better than to protest his pain to his Husband. If he did, he would be punished with a Bare ASS Spanking and he didn't want that. He stood at 5'6 and weighed maybe one hundred pounds soaking wet, but he doubted...

What Every Sissy Knows

by BelissimaSissy on Jul 31, 2018
Transsexuals & Crossdressers

Note: the following story is about 99% true with only minor embellishments. For example, there are no condoms in the story. In real life, protection is a must, but stories give us room to fantasize. Enjoy! ***** I was scared but it didn't matter. I pushed through it until my plump little dick poured out its hot seed onto my tummy. After that all I could he...

Sexy

by SweetOblivion on Sep 16, 2017
Transsexuals & Crossdressers

"Hi sexy," he grinned impishly out at her, blinking his eyes to adjust them to the bright sun, as he opened the front door to greet her. "Is Dora...?" She began and then did a double take: "What do you look like, Marcus?" "Don't you love the ice blue?" Lindsey looked the young man up and down and, smiled, despite the initial shock. He was wearing a pale...