Olivia Stories

1,000 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2026 SmutMD.com

Olívia

by slide_g on Sep 12, 2017
Anal

Hello. I write to please, so any comments are well appreciated. Let me know your favorite parts and what could use work. If this story got you hard, wet, horny, or maybe even just breathing slightly heavily leave a comment. Happy fantasizing, - slide_g --- I It felt good to be alone. I was always so busy keeping up the bar, and while I enjoyed it, ever...

Olivia

by dani_boi on Sep 16, 2017
Transsexuals & Crossdressers

I had been talking with Olivia online for a while now and it looked like our "relationship" was progressing nicely. As a cross dresser I had not been attracted to other "CD's" but there was something about her when we talked. Then I saw her pictures and WOW! Olivia is my height 5'7" but a little heavier than my slight 140lbs. She is not fat at all, just a st...

Olivia

by tbonehunter on Sep 17, 2017
Non-Erotic

I hadn't intended to spend the evening sitting beside a beautiful young woman my daughter's age, shouting to be heard over the din in a crowded blues bar in Chicago. I was on the tail end of a two-week, 11-state fundraising tour, and by the time I finally started home I was so exhausted I didn't even know what day it was. Heading east from Iowa toward Indian...

Olivia

by Ha275 on Sep 13, 2017
BDSM

Olivia entered the big bright room with gold-plated decorations and no furniture which proved her suspicions that this photographer was someone who knew how to get the job done easy and quickly. She had heard so much about him. 'Mr. John Thorne' said his card which he had given to Olivia last night at a party when he had invited her to a private experimenta...

Olivia

by quietplease123 on Sep 15, 2017
BDSM

Master and i arranged to meet our new friend Olivia at the Cardinal's game. We had been talking to her for many many months. And i had come to like her a lot...Master too. It turned out there was very nice chemistry between the three of us. We were waiting in our seats catching up from not seeing each other for a long time..When Olivia arrived. She was mag...

Olivia

by FLACKMAN on Sep 17, 2017
Celebrities & Fan Fiction

I was on a short business trip to New York when I found myself witnessing a kidnapping. I had just exited an office building where I had been interviewing for a job with a major marketing company when I nearly collided with a young, pretty woman who was walking past. She nodded acknowledgement of my "excuse me, sorry" and continued walking. Since she was ver...

Olivia

by SecondChance on May 15, 2019
BDSM

(Author's note: chapters 1 and 2 of this have been previously published, so if you have read them already, feel free to skip to chapter 3) Chapter 1 -- Beginnings (note: this chapter starts slow, with a background story, if that doesn't interest you, skip to the stars ***) Hi. My name is Olivia. This is the story of how I went from secretary to slave to w...

Olivia Ch. 01

by SecondChance on Sep 11, 2017
BDSM

Note: this chapter starts slow, with a background story, if that doesn't interest you, skip to the stars. ***** Hi. My name is Olivia. This is the story of how I went from secretary to slave to wife. It all started about ten years ago, when I graduated from business school, and went to work for my fiancée Jimmy, and his partner Bill. The company was small...

Olivia Ch. 02

by SecondChance on Sep 17, 2017
BDSM

Chapter 2 -- The re-emergence of Jimmy Bill was the type of guy, that when he got into something, he had to learn all about. We joined a local club, and at first, we mostly just watched. As we became known as regulars, some of the other Masters introduced themselves to Jimmy. From them, Bill learned about hiring trainers. Bill wanted to try everything at l...

Olivia's Revenge

by OliviaFantasy on Sep 13, 2017
Erotic Couplings

This is not a multi-part story but it might have a sequel if people thought it could. It is my first on literotica so I hope you like it. ***** Olivia sat down at her desk stunned. Moments before she had expected to be given a promotion and made director. But she watched her boss name Sharon to the job. She liked Sharon, she was nice enough. But Sharon was...