Ugly Duckling Stories

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Ugly Duckling

by FinalStand on Sep 13, 2017
Mature

*Fire inspires Brilliant and consumes the Wicked* (Thanks once more to Frontma's patience and persistence) (This is not a rape story – trust me) My name is Waylon Fielding and I am married to a wonderful woman, my wife Celine Fielding. I would like to say that my life is perfect, or even good, but after two years of marriage I'm pretty freaking miserabl...

Ugly Duckling

by Jh_49 on Jan 14, 2016
Amateur

You had always been an ugly duckling. Growing up, your older sister was blessed with jackpot genes while you spent most of your high school evenings trying to figure out which Proactive treatments would work best on your face. Even your older brother didn't seem to have to ever worry about his looks. It was as if you happened to burdened with your looks due...

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Ugly Duckling

by novaguy2u on Nov 2, 2020
Erotic Couplings

Or: The Randy Tutor and the Reluctant Student Janie was a typical ugly duckling; at twelve years old she had been chubby and self-conscious, but in the ensuing five years she had developed, growing taller and her figure fining down, and at eighteen she was still a virgin, although her full and curvy figure attracted attention. She had big breasts with large...

Ugly Duckling

on Apr 22, 2025

Linda Summers, 21, was the biggest loser in her town. She hadn't once been molested, impregnated, kidnapped, or modded. Well, she was modded once when her father dragged her down to the mall for acne removal and liposuction, but those were bare minimum. Her family couldn't afford many mods and Linda's lack of users meant she was mainly natural. Linda wasn't...

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Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Ugly Duckling to Sissy Princess Ch. 06

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

I was terrified, yet part of me was aroused to have such beautiful girl and gurl touching my body. It felt as if they were preparing my body for a sacrifice. Vanessa and Bernice seemed to want to sync their attacks. I could feel the tip of Vanessa's cock at my back door and the tip of Bernice's strap-on cock on my lips. I looked straight into Bernice's eye...

Ugly Duckling to Sissy Princess Ch. 05

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

Bernice held my hand and pulled me out of the bathroom to her living room where there were five very pretty girls, sissies, I will use the word "gurls" to distinguish them from girls that were born with a pussy. I recognized a few of these gurls from the party at the mansion. The gurls' names Deborah, Jill, Vanessa, Shirley and Anne. Each of them was very...

Ugly Duckling to Sissy Princess Ch. 04

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Chapter 3) Several nights had passed after the party at the mansion and kissing Ted. Bernice called me Saturday and Sunday, but, both nights I told her I could not come by to see her. On Saturday, my girlfriend went to a party thrown by the basketball team. I knew she would end up fucking one of them, he would use her like a piece of meat,...

Ugly Duckling to Sissy Princess Ch. 03

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 2) Wow! The kiss! Wow! Before I knew it, I was sitting on Ted's lap straddling him and we were French kissing in the most passionate and intense kiss of my life! I don't even know how I got up here. Maybe I climbed on his lap or maybe he grabbed me and pulled me up here. I was in bliss! The kissing was so amazing that my whole body j...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...