Ugly Woman Stories

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

Felicity Ch. 29

by jjcolejr on Sep 11, 2017
Novels and Novellas

Chapter 29: The Ugly Woman I was on the walking trail around my condo complex when a turn suddenly put me across the path of a seriously ugly woman. She was a tall, pale, with longish blonde hair that had not seen a brush in a while. She looked as disheveled as anyone I had ever seen. Her gym shorts and her sleeveless t-shirt were of clashing colors and to...

Hail Ch. 01

by gentlebutfirm on Sep 13, 2017
Exhibitionist & Voyeur

I'd been dropped at the convent by an ugly old woman who hadn't bothered to speak with me the whole trip, but then turned on me as we wheeled in the gate, and fixed me with her evil stare. "Miss, I hope you realise how lucky you are to be here. Most girls in your circumstances finish up on the street. You are guaranteed a warm bed, and meals every day. Make...

Ugly Pt. 01: Now What

by Adanaliyik on Aug 30, 2017
Erotic Couplings

About a year after the birth of our son, my wife pretty much lost all interest in having sex. So, when the lack of sex, and the fights that caused, got to a certain point, I turned cold and only talked to my wife if I had to. Of course, since women thrive on romance, my becoming cold had an immediate impact. And when she confronted me about it, rather than g...

Ugly Redhead Complete

by LordLoxley on Dec 24, 2019
Mature

Dear reader, just as with my other story, "The Time Spine," this story was originally released in serial form. I have decided to release it as a single volume for convenience sake. I hope you enjoy. All characters are 18 or older. ***** PART 1: Mike sighed as he shuffled through 6th period's papers. He only had a few more minutes until 7th period start...

The Interview

by obelisk666 on Sep 12, 2017
Interracial Love

Mark sat outside the office of the woman he was here to see about getting the job. He was ready to return to the world of security, and this was his first interview in several months. He was nervous beyond belief, hoping that he would get the job, but already setting himself up for failure. The sign outside her door read Leticia Desmond. An exotic sounding n...

Fat and/or Ugly

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

I saw a bumper sticker the other day that read, "I may be fat but you are ugly and I can always go on a diet." That bumper sticker made me realize that there are many not only fat but, also, ugly people out there. Sure, I see lots of fat and/or ugly people every day and everywhere I go. Fortunately, I am not fat or ugly. Thankfully, there go I before God, I...

Gurl Power

by Bakeboss on Sep 16, 2017
Transsexuals & Crossdressers

Rene hated that she was a woman trapped in a man's body but what she hated even more was that she was a homely woman in a man's body. Nothing thrilled her more than to play dress up, to release her hidden female side. Her frilly female under-things all bought on line made her wet on the inside and hard on the outside. Rene knew that she was far too wide to d...

Virgin!

by ksmybuttons on Sep 12, 2017
First Time

"Are you sure this is how you want to spend your vacation?" my friend Claire asked. She had taken me to the airport. "You are a beautiful woman and I am sure you can find a man who would want to be with you without spending all this money." "We've talked about this." I replied. "I am a 30-year-old virgin, Claire. I don't want to just lose it for the sake of...

Game Of Love Ch. 01

by crystal95 on Sep 18, 2017
Interracial Love

A/N: Hey guys this is my first story. I hope you guys like it. The first couple chapters aren't going to contain much sex (if any) because I'm going to try and build up to it. Comments welcomed! -C Melodi- 'I have no clue why I keep letting Trinity keep setting me up on these things' I thought to myself as I clutched my purse tighter to my chest as I wal...

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...