Virgin Loser Stories

1,000 results
Orientation
Length
Source
Infinite Scroll

Myron's Microdick

by Jacobins3000 on Apr 29, 2025

Myron is the biggest dork at Green Valey High. He has no friends and he is a total loser. Myron has never been on a date, and he's never kissed a girl. It sucks being such a pathetic virgin loser. But the worst part of the whole thing is that Myron has a micropenis. A pathetic one inch baby dick. Myron managed to hide his "little" secret through al...

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Ms. Demeter

by austin_morris on Sep 13, 2017
First Time

Still living at home with my parents at 21 was not exactly ideal. Even less ideal was the fact that I was still a virgin. I was working hard to save up money and move out by working shifts in a warehouse, lugging boxes around. It was laborious, boring work but it came with two advantages. Firstly, the physical effort was good excercise, keeping me fit and t...

Ella Cucks Her Patient Ch. 01

by CuckFantasy69 on Apr 9, 2019
Exhibitionist & Voyeur

*** WARNING*** This story is completely made up and contains heavy cuckolding, sensual humiliation, and submissive slave domination. It's also my very first story for publication of ANY kind so leave feedback and I do apologize if my writing is sub-par. ****************************** I'm an average looking guy with an average build in my early twenties. I...

Ella Cucks Her Patient Ch. 07

by CuckFantasy69 on Oct 6, 2020
Exhibitionist & Voyeur

I knocked on the door and used the waiting time to catch my breath as I jolted to Ella's place right after work. I waited for a minute and let myself in after I realised the door was open. I looked around but couldn't find anybody. Just when I was wondering what was going on Ella was behind me and said "Ah, you're here, good. I had a realisation yesterday an...

Stroke Slut: Goddess' Cuckold

by StrokeSlut on Oct 19, 2020
BDSM

"Well don't just stand there drooling on the doormat, come on in." The black hood had come off Stroke-Slut's head, the sudden burst of sunlight that hit his eyes was nothing compared to the radiant beauty that stood before him. Despite hours of jacking off to her on the internet, not the mention their previous sessions, he never seized to be amazed at the si...

Birthday Wish

by Transmigrator on Apr 22, 2025

Adrian brushed his teeth and gazed into the mirror at the soft face and blue eyes looking back at him. Long eyelashes, soft bone structure, silky blonde hair that draped to his shoulders. And subtly pouted lips glazed with a creamy froth from the current activity. The blonde boy spit out the toothpaste, rinsing it in the sink while he stood on the tips of hi...

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Birthdays Suck

by Sean Renaud on Sep 13, 2017
First Time

It was raining hard when Lance got off work. It was like buckets of water being dropped from the sky. It had started out as a light drizzle the morning of his twenty fifth birthday and it had just rained harder and harder as the day progressed. It was fitting weather. It matched his increasingly black mood as it became more and more obvious that nobody was g...

Danielle's Legacy

by PurpleMonkeyDishwash on Oct 13, 2020
Fetish

Disclaimer: I don't agree with any of the faux-feminism in this story. There is also no incest in this story, despite it being about a mother and a son. All my stories are like that. Also, there is some forced bi, and some bleaker aspects of humiliation. It's all in good fun, however, even if it seems dark. I hope you find it as sexy and fun as I did writing...

Crippling Lust

by yent on Apr 29, 2025

Welcome! This first chapter serves as an optional primer to the world of Crippling Lust! If you'd like to skip to choosing a story, go right ahead! If not, stick around and learn a bit about this strange world we're going to explore together... (The bones of this are copped, with permission, from a roleplay prompt I found on r/dirtypenpals) Also, I love hear...

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My First Girlfriend

by tonerboner91 on Sep 15, 2017
First Time

"Ive never done this before. God I'm so nervous. What if I mess up? What if she says no? Oh God I'm going to make a fool of myself, I just know it. If it wasn't for Chris, I wouldn't be doing this, I'd be in my room studying as I do every Thursday. He had to drag me out to this party. This is the first college party I've ever been to. Hell, in my 20 years of...