Ugly Duckling Stories

20,828 results
Orientation
Length
Source
Infinite Scroll

Finding Jenny

by kleve on Sep 12, 2017
Anal

Jenny was my best and oldest friend. And it was because of Jenny that Mark had left me. Some of my other friends claimed not to see why Jenny and I were so close. We had known each other since our first day in college. I had been wandering around the room on Freshers’ Day, wondering which if any of the idiotic-looking societies I should be joining, when I...

Sweet and Sour Shades of Sandra

by joeroberts on Sep 2, 2017
First Time

Early Seventies. Last of the Summer, just before the Autumn walks all over it. Mid Friday afternoon, storm coming, sky as sullen as my mood. Walking out the last of my high school days, did well in my last exams, just turned eighteen, ought to be as happy as a pig in shit but I'm not. Want to see Sandra, my tutor. Known her a long time and we click like a...

Jeffrey's First Time

by Anschul on Aug 31, 2017
First Time

Jeffrey was 19. At 6-2 and 225, he was, well, gawky. That was the kind description--gawky. Athleticism, coordination, strength, confidence, maturity--they had not yet caught up with his physical size. So he was...gawky. Uncomfortable in his skin. Felt like he stood out in a crowd. Like he was always bumping into things. Like he was a freak. Of course, this...

Adventures of Delmond: Let's Begin

by Delmond_Magnastone on Sep 13, 2017
First Time

To be honest, I was quite the explorative child, with a strong sense of interpretation and honesty of circumstances and intent. I never had the infamous "talk" with my parents; the culture and practice of sex was quite apparent and relevant to me. I remember once that my mother had attempted to convince my father that we should stop watching R rated movies a...

Cliffhanger

by sirhugs on Aug 18, 2017
First Time

Barry Harper had worked at WGC for nine months, having graduated college the previous spring with his diploma in computer network administration. A more worldly classmate had convinced Barry to do a European backpacking expedition as a graduation celebration. The experience of sharing hotel rooms, hostels, and occasionally barns with Emilio and the conques...

Back Seat Driver

by fogbank on Aug 31, 2017
First Time

I drove into Center Street Car Wash at 2:00 in the afternoon. Yes, I was skipping out of work. There were just a couple guys there, washing a big off-road truck. I pretended not to see them as I put my coins into the machine, and then took off my suit-jacket. I knew the guys were still watching me, no doubt hoping to see me get all soapy and wet as I washed...

A Spanking Good Time

by Quin on Sep 19, 2017
Fetish

I am a 36yr old housewife married for ten years and live in a quiet suburban area. This letter is about what happened just after I wed. I was very naïve about sex and had never done anything exciting although I seem to attract the attention of many men. I had then shoulder length blonde hair and a good figure with 36c bust which looked bigger because of my s...

More Than Just a Fairy Tale Ch. 11

by Jaisen on Sep 12, 2017
NonHuman

This chapter wrote itself in spite of continuing computer issues. For all of those readers who have been holding your breath, enjoy! I think the only reader more impatient to find out what happened next has been my partner. He's frothing over the next installment and hopes that my next bit of free time is spent writing. * Meg took the last curve at 75mph....

The Unwitting Guardian Ch. 08A

by Arraiga on Sep 26, 2017
Sci-Fi & Fantasy

This is a repost with a few minor changes that correct logic mistakes, and adds it to the series (the other one wasn't due to a name error) Enjoy, and please, please, leave comments with what you think!! * It took a month before Ryna's mistake came back to haunt him. To be fair, he had had more pressing matters on his mind, such as surviving Sensara's ang...

Furry Photo Shoot

by furryfan on Aug 18, 2017
Fetish

A story about a photographer searching for the everyday housewife. Please note the story title and the category that it was submitted in. .......... Chapter One: Looking for Mrs. Natural. I watched the woman get out of her car, a ratty looking old Mazda that had seen better days, and tentatively make her way up my driveway. She was moving very slowly, pro...