Cuckold First Stories

313,271 results
Orientation
Length
Source
Infinite Scroll

The Red Penguin

by Jimmie Blakesong on Sep 17, 2017
Non-Erotic

I’ve been looking for this place for most of my life. Well, at least half of it. I started thinking about it when I turned twenty-five, you start to wonder at that quarter-century mark just what the hell you’ll be doing when you get old, when you retire. I mean you want to be where you want to be, and I wanna die happy. I’ve been lucky, I’ll turn fifty-two...

My First Threesome with My Neighbor

by Indianaboy6555 on Jan 22, 2019
First Time

I was 20 when this happened. It was a wonderful Summer day, but as usual in my small town, I was bored. That ended when my phone rang. It was my neighbor Tammy. Obviously she was bored too. Long story short; she invited me over for a while. I was intrigued by the invitation, so I accepted. I'd known Tammy for years, but nothing had ever happened between us...

Sarah Meets a Naughty Sex Buddy

by SarahCD on Nov 27, 2018
Transgender & Crossdressers

I first published this story a few years ago. Since then my writing skills have improved a little. While I cannot change what actually happened to me, I have added some more detail and corrected some mistakes. *** I was feeling really horny and wanted some naughty girly playtime. I posted a listing on Craig's List for a "cum buddy". I explained that I am...

His Lucky Day

by literot on Apr 9, 2019
First Time

This is a true story as told to me. Lucky boy! *** As experienced with sex as I am, and with all the lovers I manage to fit into my busy life, there's something special about helping a young, good-looking lad to become a man. At eighteen, Lee is almost an aging virgin these days, but at twenty-nine, I'm definitely 'the older woman.' Knowing what the day...

Heavenly Aromas

by andbfn on Jul 31, 2019
First Time

I was a twenty two year old virgin. I thought myself attractive, but very shy. She was twenty eight. She lived with her sister. She had been engaged, but broke it off just before the wedding. Then she had been in another long term relationship that he broke off. She was devastated. Though she always acted and dressed conservatively I always wondered how ex...

Alone in the Glade

by jcstroker on Dec 24, 2019
Toys & Masturbation

It was a brutally hot summer day, and I had spent the morning irrigating the property. After watering the small heavily forested acre on the property, I turned the big sprinklers off and was surprised by how cool the air was out among the dripping trees. I stripped off my shirt. The slight breeze was cool and moist against my skin. Drops from the trees high...

How I Became Her Cuck Pt. 01

by BiCuckLoser on May 12, 2020
Group Sex

Note: This story is autobiographical. It's here because I'm often asked about how I became the way I am and it's too long and complicated for a quick text chat. If you're the kind of reader who just likes the sex bits you might want to skim the first couple of paragraphs! Growing up where I did wasn't exactly easy for someone who had always been bi-curious....

Treality Stories Vol. 01 Pt. 08

by RocketmaninOz on Apr 14, 2020
Erotic Couplings

A modern love in the making - Our first Roadtrip to Adelaide All characters are well over 18 years old and include 'Rocket Man', his cock 'Mojo', 'Sparkling Red' and her 'Genie' who first met online a few years ago as their alter egos 'Jardine Man' and 'Mimbabe'. These are their stories mostly written by Rocket Man from both their perspectives - often of t...

Skirts

by TonyDowse on Aug 19, 2017
Exhibitionist & Voyeur

Chapter 1 Skirts What man hasn't at some time been stirred by just the sight of a skirt swirling around a pair of long, shapely legs? She me one and I'll show you a blind man! Let's be honest and admit it, a skirt, one that's neither too long, nor somewhat perversely, too ridiculously short, is one thing a woman with even reasonably good legs can wear an...

Hard Laced Ch. 04

by Learningfast on Sep 19, 2017
Fetish

Their first telephone conversation could not have foretold better the honesty and simplicity of the relationship which was to develop. Sophie knew what she wanted. He knew immediately that he could provide what she wanted and that he would enjoy making his contribution. Hers was the fourth of the calls arising from his advertisement "Is that Christian who a...