Sissy Hotel Stories

62,092 results
Orientation
Length
Source
Infinite Scroll

A Night For Romance

by maggie2002 on Sep 14, 2017
Romance

The night was beautiful as only spring nights can be when winter loosens its harsh hold and the soft winds blown and flowers grow. "Damn, I'm a poet and I didn't know it," laughed Sissy Littleton the Editor of the Littlestown News, as she sat at her computer trying to come up with a short story as filler for the Sunday Magazine. She had to be done by tomor...

The Chastity Trap Ch. 02

by slavemalcom on Mar 13, 2018
BDSM

Malcom rushed back through town to his house, all he wanted to do was get to his room and see what could be done about the chastity device trapping his cock. As soon as he opened the door however, Emma came rushing out of her room and looked down from the top of the stairs. "Lott...Oh it's you." She said. She didn't even try to hide the disappointment and d...

Afro Stress Relief Ch. 08

by llts1970 on Nov 11, 2019
Transgender & Crossdressers

It was Monday evening, again, and I hurried home from work to get ready for my shift at 'Babes With Asstitude' (BWA). My new Afro-boyfriend, Drake, rang to chat about our new venture as soon-to-be Brothel-keepers and tell me not to work 'too hard' on my shift as a whore at Drake's uncle, Leroy's, place, BWAs! Drake wanted to come over but I said I wouldn't b...

The Sexy Cuckold Couple Pt. 13

by cuckcpl4play on Sep 19, 2017
Fetish

Part 13 Vegas Arrival We quickly departed the plane and as expected, Master had a limousine waiting for all of us. Getting into the limo, Master asked his slut / my wife loudly enough for all of us to hear, "Is that stretched out pussy already tender and sore?" My wife immediately responded that it was hoping that Master might express some niceties or co...

Pimped Out Sissy Bitch

by Gemsissy on Jan 12, 2018
Fetish

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit. I glanced at the phone....

A Very Public Sissy Adventure

by DivinaTellsAll on Jun 4, 2019
BDSM

At Madame Vega's instruction I had spent the last hour edging myself. This is not always an easy task for a sissy who is not allowed to stroke her clitty. The edging was primarily accomplished by the use of a vibrating wand inserted in my fuck hole, and an Hitachi wand that I could rub my clitty on, as I teased my fuck hole deep inside. I had been banned fro...

Isabella's Reversion Pt. 06

by silverbackteddy on Sep 16, 2017
Fetish

Note from the Author: This is a story about ABDL. The first word being Adult. All sexual encounters center around Adults, above the age of 18. This story also contains BDSM, plushophilia, watersports, and various other fetishes. For those that are grammar freaks, please don't comment on my improper grammar use. I could care less. At least it doesn't have L...

Business Trip

by AnnaV on Sep 11, 2017
Transsexuals & Crossdressers

My boss had sent me to Brighton at short notice as she decided at the last minute that she didn't want to go. Apparently she had something better to do. The fact that it was my birthday didn't seem to bother her too much. I usually liked the chance to get away for a couple of days as I'd sneak in some of the wife's sexier things in my bags and spend my eveni...

Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Sissification 101: Ch. 05

by silkstockingslover on Aug 31, 2020
Interracial Love

Sissification 101 Ch 05 Summary: Erica practices taking BBC in both of her sissy holes. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught by a very supportive girlfriend in pantyho...