Teen Cuckold Stories

17,243 results
Orientation
Length
Source
Infinite Scroll

Being Kate

by xtcnymphette on Sep 12, 2017
First Time

A widower hires nineteen year-old Stephanie to baby-sit his daughter while he plays squash. Her uncanny resemblance to his late wife finds her entangled in a strange but passionate encounter with another kind of virginity. I was shopping with my younger sister Samantha and her friend Tania when I saw him in the busy mall. He was cute in a kind of 'Ben Harpe...

Couple's Night Out

by FurryFury on Sep 13, 2017
Anal

Michelle loved Joe with all her heart. He was a miracle in her life. Everyday she thought about how lucky she was to have him, how good he was to her, and she gave thanks to the powers that be. She and Joe had been together nearly fifteen years. The start had been passionate, but rough. She had already been married and pregnant when they got together. Her fi...

The Chauffeur

by kingleonidass on Sep 13, 2017
BDSM

Highway 101, five PM on a Friday. Got to love it. Fucking sucks. God dam traffic jams. "I hate this fuckin' place," she screams out her window. Eight lanes of traffic and not one car moving. People are getting out of their transportation and milling around waiting. For what? Something? Anything to move. Fuck! Sandra Livingston, age 33, professional driv...

Sleepless on the Sofa Ch. 01

by MoonCorgi on Sep 25, 2017
Erotic Couplings

Author's Note: This is an edited version of the original story. Big thank you to Secretsxywriter for editing and helping me to make it better. *** I paused the video game as the doorbell rang and darted up so fast, I hit my shoulder on the bookshelf. My reflection in the mirror by the front door seemed decent enough. Maybe I should have shaved? Glancing i...

The Dutchman's Knot - Grad School

by eymach on May 8, 2018
Erotic Couplings

SueAnn had just left Dr. Main's office with exciting news about her upcoming PhD research project. She could hardly wait to tell her step father. As she bounded down the path way, the gentle tropical breeze brushed her face and cooled her skin. The sun baked sand increased the heat felt between her toes. A bit of sexual excitement crept into her loins as the...

Maintaining Focus

by XXscribbler on May 29, 2018
Erotic Couplings

An autobiographical story by XXscribbler A five day meeting, and Edward was -- as usual- at the hotel's meeting room forty-five minutes early on day one. Two young staffers were setting out coffee and etceteras. The only other person in the room was at the nametag table: she was older, obviously in charge, and busily laying out agenda-and-background folders...

The Sidecar Tales 09 - Jenny 03

by TheKeith on Nov 25, 2017
NonHuman

After about eight weeks, Sophie, (Jenny within her) and I wound up back in New Mexico, leisurely riding north out of Albuquerque, up the old Turquoise Trail. Otherwise known as New Mexico State Route 14. We ate—well, Sophie ate and Jenny, inside her, appreciated it—lunch at Madrid (say it as MA-drid), and, bypassing Los Cerrillos, were looking for a sunny s...

Crossed Lines

by XtinaSmith2017 on Nov 26, 2017
Transsexuals & Crossdressers

Leo took a slow refreshing drink from a cup of now warm water, sitting at the edge of an intricately designed diagram drawn out with fine red chalk, his eyes scanning studiously over his magnum opus, checking it for errors or faults, knowing even a single smudged line could result in his downfall. Everything was perfect and exactly as the book had detailed,...

Strange Tales of the Deadslayer Ch. 01

by RavynsLand on Dec 10, 2017
Transsexuals & Crossdressers

"Allan? Honey you remembered to take your medication right?" "Just a second I gotta finish this dungeon!" I call back as I hear my mom's voice ring up from the floor below my room. Asthma can wait -- mythic keystone Black Rook Hold comes first, and my group's almost to the final boss. "Allan? The doctor said 8pm every night, you need to take them." "I'...

Now I Lay Her Down to Sleep Ch. 04

by storytyme on Sep 12, 2017
Romance

This is the last edition of my continuing story between a 36 year old man and Chelsey, a 19 year old girl. It is a little long, but I hope it is worth the read to you. I hope you enjoy. I woke up Tuesday morning and headed to work with a smile on my face that would not go away. The work day seemed to last forever. It was finally time to head home. I didn'...