Sissy Vacation Story Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com
Create your own smut fantasy with AI

Another Sissy Shopping Adventure

by sissysherry2 on Jul 18, 2018
BDSM

In my last story, I related a story about a mistress who gave me a sissy assignment several years ago. This involved going to a mall and getting a makeover and getting girly clothes. Like the other story in this topic, there's no sex just some good old fashioned humiliation. This is the latest adventure and I hope you enjoy it! ********************* I h...

Thailand Sissy

by Xxxdollxxx21 on Apr 22, 2025

I really just wanted a vacation away from my ex wife that I was divorcing, from my dead end job, and my annoying ass boss. This trip was supposed to be fun. Site seeing across Thailand, their rich, beautiful locations and religious temples. The beautiful scenery I had seen after I got off the flight and rode to my resort had vanished into these deep woods. T...

Sissy sublet

by Alexis88 on Apr 22, 2025

Hi I’m Alex and I’m a 21 year old orphan, my parents died while flying to our vacation home in Hawaii. Being wealthy I was left better off had a big home in the upper class part of San Diego Ca. Being the house was to big I asked our family lawyer to lease it for me and I would find something smaller for now . Our lawyer was a very attractive older lady arou...

Sissy Boy Secretary Ch. 09

by Hotenuf4u on Sep 19, 2017
Fetish

Elaine had enlisted the help of her neighbor's daughter, Tammy, to help in obtaining a big business edge for her company, now it was Tammy requesting her help. Tammy's mother was divorced from her husband after an unfortunate chain of events, some of which were Tammy's fault. It seems that Tammy's father was quite a jealous man when it came to her Mother, he...

The Vacation from Hell Pt. 02

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Anklet Adventure Pt. 04

by dometoo on Nov 27, 2018
Interracial Love

Editor's note: this story contains scenes of incest or incest content. *** The last time Lynda and I returned from our romantic getaway cruise, she came back black bred and knocked up, cuckolding me and keeping me in chastity much of the time. I'm now the proud father of a three-month-old black boy, Mark, her bull's namesake; with strong prospects of havin...

The Vacation from Hell Pt. 03

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Bill and Linda's Vacation Ch. 03

by pascofun1234 on Oct 12, 2020
Interracial Love

Recommend you read chapters 1 and 2 to get a feel of how we got to this point. This includes interracial play, mild domination by a woman and bisexual play. If this is not for you please move on to the next story. No need to berate this story because it includes themes that you don't enjoy. All involved are over 18 years old ======================== Lin...

Betty Finds My Story

by JackorJill on Sep 12, 2017
Fetish

The office was quiet at this time of the morning. I came in to get some paper work done. The phones never sounded better. I had put some coffee and stopped for a bagel. The applications on my desk had been piling up and that was a good thing. I never heard Betty until she was standing behind me. "Hey, you're early. Knock'em dead big guy." She was older then...

Elaine's Neighbors

by Hotenuf4u on Sep 14, 2017
Fetish

Elaine's Neighbors: Their Story Tammy's mother had divorced her father just over a year ago. It seems that his lack of trust got the best of him which ultimately led to his downfall. Tammy was home on a vacation from her college studies when she noticed a change around the house. It seems that now her father has turned into a workaholic which left Mom prett...