Virgin Loser Stories

50,650 results
Orientation
Length
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Infinite Scroll

Intense Cuckolding by Surprise

by CL702463 on Mar 3, 2020
BDSM

Yesterday, I experienced a very special evening. Excited to see my master, her beauty and hoping for an exciting game I arrived in a hotel room that features a wooden bed, wardrobe and oil paintings with a single dominant woman towering over the double bed. When she arrived, I was at ease. She seemed so happy & excited in spite of a tough day - a rare feat o...

Kelly's Quest Ch. 01

by The_Technician on Sep 19, 2017
BDSM

This is a story I wrote a few years back. It is about a woman who is addicted to pain and knows that it can destroy her, but still seeks the blissful "golden cocoon" that lies on the other side of the pain and humiliation. Her addiction controls her, but she finds help from an unexpected source- her Uncle Jack and her sister Tracey. She also finds out that s...

Inaugural Crossdress Sexfight

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

Hi everyone and welcome to the Crossdressers Sexfight League (CSL). My name is Dani and I'm the primary author as well as a regular participant in the league. The league title says it all. It's an erotic sexfight wrestling league for crossdressers of all ages where the loser is forced to service the winner of each match. It takes place in living rooms, bedr...

Boulevard of Broken Dreams

by Dar_Jisbo on Sep 14, 2017
Erotic Couplings

[Late 2007 -- The Pacific Northwest] Harp the bartender walked over to me. "Del, I heard a good one yesterday," he said. "How do you get virgin wool?" "I don't know, Harp," I said. Harp replied, "From ugly sheep." I groaned. "Bad, Harp," I said. "Slow day today. Only one other person here." "She's a regular," he said. "She looks down to me, man. Gets dr...

Sissy Powers Ch. 09

by ClarasBestFriend on Sep 29, 2020
Sci-Fi & Fantasy

When we made our way into the living room (with me back as Leah), Connor's eyes bugged out of his head. "MMM MMM NNN!" he screamed through his gag, a sock balled in his mouth and held in place by duct tape. "Oh, baby, sweety it's okay!" cooed Heather, moving over to him. "These wonderful people have shown me why our relationship is so bad! Good news, it's n...

Priya's Rejection Tutorial

by slave31 on Sep 14, 2017
BDSM

Kavya sat down on a small bench placed on top of the college building's terrace. "This is a wonderful, warm place to sit and think. Come, join me," she tapped the seat next to hers. "Wow, I've been in this college two years, never seen this spot before." Priya said. "So quiet and secluded." "And warm," Kavya said. "Check out the view from here. You can see...

Verna's Threesome

by biggiejimmi on Sep 17, 2017
Loving Wives

We had married very young and neither of us had ever been with another sexual partner. Verna was 24 yrs old, 5'4, 110 lbs, 34, 23, 32 very pretty, with brunette hair to the small of her back. She laid out often and had a deep bikini tan. My friends always commented how attractive she was, and I had been fantasizing about watching her with another man but whe...

Genuine Ch. 01

by shawnsgrl22 on Sep 15, 2017
First Time

Ever been in love with the school flirt? It sucks. This story is only partly true, and this is the first part. I intentionally left out character descriptions so you can use your imagination. I really hope it leaves you itching to read more. Please give me feedback, I'm not quite sure how to end it but any comments would be appreciated. * I met Cameron as...

College Wager

by the_dork_lord on Oct 1, 2005
BDSM

The five girls sat there in the café around the corner from campus discussing, or arguing in the case of Elissa & Louisa, about the exam they had taken only an hour ago. As usual Elissa & Louisa had found the exam easy; both girls normally got high marks with only a few percent separating their scores. The two girls were part of the lucky few: good l...

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Find the Cheerleader, Save the World

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It started with my brother Holt. A year younger than me he's...he's turned into a fucking cuck sissy faggot. I'm serious and I'm not just spouting off. Holt's always been a dense guy but this...he starts hanging with this loser from high school and I mean a loser. AV club, geek stuff, nothing in Holt's yearbook that said anything but loser, geek and loser...