Story First Experience With A Ladyboy 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

Business to Improve Sex Lives Ch. 05

by walterio on Oct 23, 2018
Novels and Novellas

MORE EROTIC TRAINING ON THE AGENDA Trace and Brittany woke up in a spoon position with his morning erection pressed into her curvy bottom. His hands encircled her upper body and fondled her lovely breasts. If they didn't have a client that day they would have made passionate love as they always enjoyed each other so much. "I really love your body and cares...

A Gift in Disguise Ch. 14

by Talespin on Apr 2, 2018
Novels and Novellas

"Murph really likes you, Tom," Bethany said softly while we walked hand-in-hand to her car. "He seems like a very nice guy," I answered. "And he obviously thinks the world of you, too." "He's a good judge of character," Bethany said as we approached her car. "Humble much?" I chided her laughingly. "I meant yours!" she responded with a good-natured punch...

The Camping Trip Pt. 06

by Tetris07828 on Sep 18, 2017
Group Sex

Saturday I woke up to find Tammy and Alice moving around the RV. Tina was still asleep. "Do you want me to make you guy's coffee or something?" I whispered. "No, we get that in the park but thanks." Tammy said. Alice blew me a kiss and went in the bathroom. Tammy carefully climbed on the bed to not wake Tina and started sucking me hard. She rolled a cond...

Inheritance Includes a Houseboy Ch. 04

by walterio on Sep 14, 2017
Novels and Novellas

AUTHOR'S NOTE: This story contains encounters involving gay sex, bi-sex and straight sex which is why it was categorized under Novels and Novellas. ***** BETSY'S WEEKEND Betsy arrived early Saturday morning as she wanted to get started early. She was accustomed to morning sex with me in the office so I wasn't surprised. When she arrived I introduced her...

What a Long, Strange Trip It's Been

by kurrginatorX on Feb 11, 2019
Romance

This is a Valentine's Day Contest entry. To vote, please click the stars at the end of the story. Thank you. ********************** Sunday evening I emailed Mrs. Sherman, my English instructor, with the following message: Mrs. Sherman, I know I have no right to ask this, but I need an extra week for my project. I have had one terrible incident after the...

Sugar and Cream

by BiBlond6FootFun on Sep 19, 2017
Group Sex

Waking up in a strange bedroom, my world alternating between brave, new, and what the hell are you thinking! It had so long been a fantasy of mine that I could scarcely believe it nor imagine how much the night's festivities might impact my life. Where should I begin? The wide aperture would take you to junior high when I expressed revulsion when I first h...

Auntie Mabel Ch. 26

by drsnip on Sep 13, 2017
Novels and Novellas

Mabel was feeling a bit down, the housewarming party was nearing it end. Everyone had said what a good time they had. Mabel had enjoyed the party, but sometimes when she heard about the sexual adventures of her friends, she realised that she was getting old. She had deduced, overheard or been told, that everyone at the party had sex with someone, except her...

Be Still Little-one

by highshine808 on Oct 3, 2018
NonHuman

All sentient creatures in this story are over 18 years old. ***** Priesterly drained the dregs of the Rat.Pac protein pod. Stakeout, on the edge of the Western Protectorate. Westerly had just dropped into his sleep shift, following the end of morning-twilight joint-observation hours. He had sent the morning report to Command before turning in for his 4 hou...

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...

Faith and the Thai episode

by gryphon_rock on Sep 13, 2017
BDSM

FAITH AND THE THAI EPISODE or Faith's Sexual awakening a novel by Nicoletta Sanchez Duran Faith and the Thai episode -- Part 1 This is the story of Faith Griffith, 30 year old Manhattan school teacher whose husband Greg Pope had died whilst on honeymoon in Thailand. What Faith had never told anyone was that Greg had been found in an abandoned shack...