Ladyboy Massage Stories

221 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

Makati Ch. 08

by massageaddict on Jul 15, 2020
Novels and Novellas

Chapter 8 I awoke early, having a busy day in front of me. After getting cleaned up and spending some time packing up my clothes and work items, I headed down to breakfast about 7:30am. I stopped off at the restaurant and ordered my coffee and an English breakfast and headed to my seat in the smoking area. When I rounded the corner, I was a little surprise...

Makati Ch. 05

by massageaddict on Jul 15, 2020
Novels and Novellas

I sat at my favorite table smoking when Lilly showed up to ask if I needed anything. I asked for a bottle of Perrier and she smiled and said "Right away Mr. Bob." I sent off a few emails, sent some pictures of the new place to my wife and then scrolled through my WeChat deleting all the whores wanting to connect then checked my Whatspp. I had a message from...

Makati Ch. 09

by massageaddict on Jul 15, 2020
Novels and Novellas

Chapter 9 At 7:45 I rode the elevator down to see that Sam had the car ready and was waiting for me. I motioned that I would be getting in the front seat and told her to go to the Hotel where we would be picking up Jack and Yomi. I looked down at Sam's long legs encased in her stockings and felt a stirring of my dick. Damn, I needed to get laid tonight. We...

The Reunion Ch. 02: Thai Massage

by Valtikka on Jul 15, 2020
Anal

"Krissy! Long time no see! It's so good to see you. You look great girl!" As soon as I get out of the Uber, Micky comes walking to me with wide open arms and gives me a big hug. "Come let me help you with your bags. You're the first one to arrive so you have first pick on the rooms. The rest of the gang will arrive tomorrow." Instead of the overalls I'm use...

28-year-old Bisexual Stepfather Ch. 12

by walterio on Mar 20, 2018
Anal

AUTHOR'S NOTE: This story contains straight sex, bisexual sex, gay sex and incest. *** A MASSAGE AND MORE Following brunch Ronnie and Dustin returned to her home. He had promised to give her a massage and she was looking forward to it. She took him downstairs to the lower level and it was the first time he was there. There was a massage table and a small...

Getting the GED

by turo69 on Sep 16, 2017
BDSM

Part One Well how did I get here? Bob Tucker, newly retired at 55, not buff but not quite squishy, fairly comfortable, never married and still a certifiable horn dog. An athlete through college and still pretty active, but with an overactive sex drive. My investments and real estate holdings together with a 20 year pension courtesy of our local school distr...

Business to Improve Sex Lives Ch. 08

by walterio on Dec 24, 2019
Novels and Novellas

ANAL TRAINING Trace and Brittany were eating a light practice after their customary morning sex. Trace asked, "Who do we have scheduled today?" "A young woman named Justine. She is interested in anal training." "Really, an anal virgin?" "Yes, she has a boyfriend who she dearly loves. He has tried to get to her ass several times but she refused. Now she...

Anal Anywhere, Anytime Ch. 01

by walterio on Jan 22, 2020
Anal

PRELUDE It was the first time that Charlotte had ever come to my place. We had fantastic anal sex on Friday night and we were up for more on Saturday morning. It was a rainy summer day and we were in no rush to get out of bed. She had ridden my cock until she orgasmed and now it was time for me to take that scrumptious ass again. I caressed her ass and tea...

Anal Anywhere, Anytime Ch. 02

by walterio on Jan 22, 2020
Anal

BEFORE CHARLOTTE As long as Walt could remember he had been drawn to a shapely female bottom. I didn't have sex until I was 18 but I had hundreds of boners from just looking at the outline of curvy buttocks contained in skirts and slacks. I found myself watching TV hoping to get a look at an actress's derriere. Even during commercials, I checked out a curvy...

The Tax Man Comes

by Stormysailor on Jul 20, 2020
Erotic Couplings

Ced (for Cedric) approached what was probably a hobby farm or small business at the end of an unpaved, narrow road. An odd assortment of noisy dogs raised the alarm and a man came out of an outbuilding. They stared at one another for a while until Ced broke the ice, "Ross, from high school?" "Cedric, what are you doing in this part of the world?" "Obviou...