Ugly Duckling Stories

20,828 results
Orientation
Length
Source
Infinite Scroll

Adventures of Wiley Coyote Ch. 04

by wiley4377 on Sep 12, 2017
Group Sex

Pt 4--Three days earlier, Wiley met Joe and then Tony. Now, Wiley decides to join the party at Joe's.--- It was Saturday night and the Peachtree Bar was dull. There were no horny single women and the groups were all cliques. The women seemed to enjoy talking to each other more than the single guys. I felt like I had a big "L" branded on my forehead for los...

First Day of Summer Ch. 02

by fameahsky on Sep 14, 2017
First Time

Chapter 2 of a series. I'm not sure how fluid this story will be w/o having read the first... ...check out ch 1, now. Have a great day, Fameahsky * I cried myself to sleep that night. I awoke at noon, the next day. That gave me two and a half hours before Jason was supposed to get here -- we wanted to enjoy the warmth of the beach without heat stroke....

Just Across the Hall Pt. 05

by EROTICbearscribe on Aug 6, 2019
Transgender & Crossdressers

Chapter Six KYLIE The next months were truly magical. True to his words, Lonnie didn't try to turn me into a girl. He celebrated the panty-boy I was. I moved in with him and we began our new life together. The insurance settlement from the fire allowed me to quit my job and stay home and take care of all the cleaning and cooking and...other things....

The Making of Davina Ch. 01

by Timewarp10 on Oct 31, 2018
Transgender & Crossdressers

It was 1966, England had won the World Cup! The swinging sixties were in full swing. David had started working in the sale's office of Telford Safety Engineering Ltd. He held the grand title of Assistant to the Sales Manager, which meant in reality he was the office boy; he ran errands and made the tea. At eighteen, it wasn't his first job. Since leaving sch...

Funny Face

by Callicious on Sep 13, 2017
Non-Erotic

Nobody ever said she was a pretty baby, except for . . . well, the truth is, nobody ever said she was a pretty baby. She was born with a 'Port Wine Stain' on the right side of her face that started at her hairline and split her face almost evenly down the bridge of her nose, through the cleft of her upper lip and about a quarter of an inch below her bottom l...

Dry Valley Ch. 02

by WyldBreeze on Sep 12, 2017
Chain Stories

Dry Valley Ch. 02 ~ Bucked-tooth Bailey "Ringggg.......ringgggg....." Bailey heard the shrill tone of the phone as she struggled through the front door with two brown bags of groceries. Just as she made her way to the shining counter-top of her small kitchen and picked up the phone, one of the bags toppled over spilling its contents to the floor. "At least...

Who Needs Privacy Among Family?

by RedHatter76 on Sep 18, 2017
Toys & Masturbation

My name is Gabby. I have a twin sister named Holly and live-in cousin named Kendra, whom my mom took in when she was little, after her parents' drug addiction cost them their parental rights. Despite being a shy blonde surrounded by rather outspoken brunettes, Kendra never looks or, more importantly, feels out of place in our family. As for Holly and me, wel...

Meeting Kristy

by sprmbnk on Sep 1, 2017
Exhibitionist & Voyeur

Note from Author: this is my first time writing something like this. I would appreciate any and all comments or criticisms you may have concerning this story. * Scene One: I was sitting at my favorite bar nursing a beer, watching some sporting event on the T.V., when I felt a tapping on my shoulder. I looked up to see this stunning brunette smiling at me....

Grace: The Ugly Duckling

by papa319 on Dec 25, 2019
Erotic Couplings

I was taking a day off from work just relaxing alone by my pool for the first time this year, enjoying the sun on my body and the absence of the trials and tribulations that life seems to always be throwing my way. The cold beer in my hand, sweat pouring from the bottle, was the only thing keeping me from simply dozing off as I basked in the serenity you onl...

Adventures in Thailand Ch. 06

by thunderman999 on Sep 16, 2017
Interracial Love

Chapter 6: School Begins The next few weeks proved to be frustrating ones. While there were miles of female flesh in my classes, my lack of confidence in my teaching abilities kept me from making any moves on my female students. Slowly but surely, I became friends with Claire and Stacy. I thought I might have a chance with either one or both of them until I...