First Time Cuckold Stories

351,145 results
Orientation
Length
Source
Infinite Scroll

Under Construction Ch. 04

by Dlinqnt on May 22, 2018
BDSM

Shawna awoke in Darren's bed naked, sore, and deeply content. Darren slept beside her, his sleeping vulnerability showing no trace of the secret man that lived inside him. That was one hell of a first date, she thought. It still is, I guess. At dinner, they had talked about what being a submissive meant to Darren and what was now required of her. Some thin...

Last Date

by Kinky Rachel on Sep 16, 2017
Romance

This was our last date. Our first and last date. The band played slowly, a waltz, and as we spiralled together, our hands clutched each other, defying our imminent separation, our closeness its cruellest reminder. This was our last date. We were in the same class at University, both studying English for wont of a more specific subject and, at first, this wa...

Pool Boy Gets Dressed Up Ch. 04

by tonyl65 on Sep 26, 2017
Transsexuals & Crossdressers

I used every skill Debra showed me in the last week to make Don happy. His cock was thicker than its replica, but more pliable. His precum tasted sweet and felt so good swirling around my mouth. I gently pulled on Don's balls forcing his cock to tighten and go further down my throat. I was very pleased with myself that I was able to take about seven inches d...

Catch and Release Ch. 05

by wilderness on Sep 11, 2017
Novels and Novellas

Tim poured charcoal briquettes into a battered, three-legged grill. "I remember when my dad bought this relic ten years ago. We came up here to get the place in shape for hunting season, and he decided to barbecue the deer we never shot." While squirting on a liberal amount of lighter fluid, he added, "I just turned 18. Dad gave me my first beer that nig...

Illusions

by Feshta on Jan 15, 2019
Non-Erotic

This story is based on the song of the same name by Cypress Hill. It's my interpretation of the song's meaning. I took poetic licence with the ending and used another of their songs, One Last Cigarette as an ending. There is no sex in this story but it's not for younger eyes due to the type of story it is. Inspiration for the story was very much in the vein...

Crazy College Memory

by JoeDreamer on Sep 12, 2017
Group Sex

"Shit!" I snapped quietly as I hid beneath Jenny's bed. I could see through the bed skirt well enough to make out two of her sorority sisters at the door, but not well enough to identify them. "Come on," one of the sister's was saying. "We're going on a road trip with the pledges." I knew that voice. Kristi was the current pledge mistress. She also happened...

Georgina's Daughter

by norfolklad on Sep 26, 2017
Erotic Couplings

I was unsure which category to place this story under. Some people will insist that it should come under 'Incest/Taboo' but by no means – even under the widest possible definitions of Incest – are the events described here incestuous. And Taboo is a wide open and fairly meaningless definition, 'Erotic Couplings' it had to be as the least worst choice. For...

XChange Seminar, X-change, X Change

by Grabenork on Oct 14, 2017
Transsexuals & Crossdressers

Author's note: If you search Literotica for "X-Change" (with a hyphen) stories, the search engine returns only "xchange" without the hyphen. To find story titles that have the hyphen, you must search "x change" with a space. Until Literotica has fixed this glitch, I have titled this story so that it can be more easily found under any alternate spelling. * *...

Of Rivers and Religion Ch. 01

by stfloyd56 on Sep 13, 2017
Mature

This is Part One of a two-part story. I can't say that it was love at first sight. I guess I'm not even sure I know what that means. But I think I do know what lust at first sight is, and I can't say that I felt that when I sat down for the first time in the front of Dave Heard's classroom for the opening session of the advent of my college career -- his Su...

My Unusual First Time Ch. 01

by djeroticon on Sep 13, 2017
First Time

It was the early 1960's in small-town Connecticut. I had just turned 18 and would graduate high school in a few months. Having the grades to go to Yale if I wanted to, and the parents that could finance it, what was missing was self-confidence. Part of it was my non- success with girls. The other was that I was 6 foot two and 165 pounds. Add to that skinny...