Teen First Time Stories

351,254 results
Orientation
Length
Source
Infinite Scroll

Little Red Riding Hood

by gatorman on Sep 26, 2017
NonHuman

(A story by Bros. Grimm, slightly altered by Gatorman) I know . . . You've already heard the story of Little Red Riding-hood, when you were a little boy or girl yourself. Only remember: THAT story was translated to English from the German story compiled by the Brothers Grimm, along with a LOT of other similar German "Fairy Tales." When they compiled t...

The Breeder Pt. 09

by WednesdaysCoffin on Sep 28, 2020
Anal

Author's Note: This story contains three horny werewolves (FFM), breeding/impregnation, anal sex, and more. All characters are 18+. It is not necessary to have read the previous installments in this series, however, doing so may give you some background on repeat characters. ©WednesdaysCoffin2020. This story cannot be transferred to any other site besides Li...

Going Down... And Not In A Good Way

by WordWizard55 on Sep 13, 2017
Erotic Couplings

Kayla finally made it to her seat on the plane, releasing a large sigh she hadn't realized she had been holding it. 'Phew! That was quite the ordeal!' This was the 18 year old's first time flying, and getting through the airport had been... well, interesting. Her parents had divorced her junior year of high school, and so this was the first time the teenag...

Shemale Utopia

by Lewd_Ruby on Jun 15, 2016
Transsexual

*De-De-De-De-Deep* *De-De-De-De-Deep* *Click* I gently pressed the large red button atop my alarm clock to stop the annoying racket of those high pitched beeps. Sitting up I began to take a look around at my surroundings, Beige wallpaper spread across the walls, the odd video game poster stuck on lazily with some blu-tack. Letting out a small sigh I swung my...

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Claire's First Time Penetration Ch. 04

by ostinatobravado on Sep 12, 2017
First Time

Here is the 4th and last part of this story line. Recall that Claire is a 19 year old high school student so there is no underage content in my stories. ========= Claire's First Time (Part 4 and final) Claire lay motionless with her stomach flat on the principal's desk, her head facing to the side resting her cheek, tied at the wrists and blindfolded. She...

Office Teen Ch. 02

by MrPetersPenname on Sep 19, 2017
Erotic Couplings

My next encounter with Claire was about a month later. She had turned 19 since then and I had recommended her for a full-time job as a coordinator in a different department with our company. I'm told she had backed down on her college course load to work with us full-time. To the wise elders it looked as if she might go husband hunting instead of getting a l...

A Relentless Teen Mistress Ch. 06

by JackFrostFire on Sep 21, 2020
BDSM

Introduction This chapter (Chapter 6) won't make as much sense without reading Chapter 5 first. They are a single unit, but I split it into two chapters for length. In case you're wondering, the "exercise" was inspired by a trip I once made to Lithuania and not by a worldwide search for sex organs. At the END of Chapter 5, Susannah Rush, the Woodglen Hig...

Abandoned Paradise

by JohnLocke4 on Jul 13, 2018
Amateur

A rusted out, squeaking Gran Torino drove down a long private stretch of road just outside of Greenwall. Inside sat Kenneth Clark called Kenny or sometimes Ken by near everyone he knew and the very proud owner of the classic clunker. His thick brown hair was medium in length, yet short enough that he never needed to worry much about having a bad hair day, us...

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The Royal Cock Ch. 10

by sexgundam666 on Sep 26, 2017
Novels and Novellas

"You never said where you were taking me," Jess said as the car, driven by one of the royal family's many maids, journeyed through the city. The teen sat in the back, looking out of lightly tinted windows at the passing streets as people wandered about. Beside her was Kyodai, who had been uncharacteristically quiet since climbing into the vehicle. "Oh... uh...

Unintended Consequences

by Patchouli_girl on Sep 13, 2017
Loving Wives

Author's note: This is my first attempt at writing an erotic story. The story is inspired by true events that happened to me when I was 21 years old. As it is with movies, inspired by true events means that it didn't necessarily happen in this exact way, and that some parts may have been embellished for artistic effect. * Amy glanced across the room and g...