Preface

Day 30: Self Love
Posted originally on the Archive of Our Own at http://archiveofourown.org/works/59346946.

Rating:
Explicit
Archive Warning:
No Archive Warnings Apply
Category:
Gen
Fandom:
Supernatural (TV 2005)
Character:
Dean Winchester
Additional Tags:
Stanford Era (Supernatural), self deprecation, Humiliation, Masturbation, Internalized Transphobia, Trans Dean Winchester, Kinktober 2024
Language:
English
Series:
Part 11 of Dean Winchester's Boypussy, Part 35 of Kinktober 2024
Stats:
Published: 2024-10-30 Words: 388 Chapters: 1/1

Day 30: Self Love

Summary

Dean has always loved to push buttons, including his own. (Prompt: Self Deprecation/Humiliation)

Notes

This one was a bit painful to write, but I thought it made sense for Dean.

Day 30: Self Love

“You really think you’re a man?”

Dean rolled his fingers vigorously across his clit, rocking them back and forth in time with his frantic breathing. His other hand supported the underside of his thigh, held it in place while his other leg tensed and came close to spasming with each frenzied stroke of his clit.

“You’re a fucking disappointment is what you are,” he said gruffly in between panting fits, rolling his hips up into his flattened fingers. “You’re a mistake.”

The room was dark, the TV playing static after the nightly infomercials had ended. Dean’s hand had ventured into his pants during an ad for razors, long, smooth legs stirring a purely frenetic energy between his legs. His pace had only picked up when a wrestling movie came on afterwards, and now he was staring up at the ceiling, repeating cruel nothings to himself while he tried to wrench out a third orgasm.

“A joke, that’s what you are. Everybody sees through you, they’re just too polite to call you on your bullshit.”

His fingers were pruning, the sheets underneath him were soaked with come that he’d need to scrub off his skin in the morning. Dean clenched his thighs together, the muscles trembling like he was having a seizure from the waist down. He ground his fingertips into his clit and moaned, feeling a pang in his stomach at just how girlish it sounded.

“You should be glad Mom’s dead,” he breathed hard, his fingers jerking violently as he started to encircle a third orgasm he didn’t need, “it would’ve killed her seeing how you’ve ruined yourself.”

Dean moaned again, whined as a white-hot ball of arousal started to grow in his core. He moved his wrist desperately, thought of any horrible thing to say that’d tip him over the edge. When he found it, he crushed his hand against his clit.

“If you ever see Sammy again, he’ll laugh in your face. Stupid fucking girl, thinking you could be anything like him and Dad. Grow up, you ugly slut.”

Dean spread his legs far apart, took every ounce of pressure off of his abused clit and stared up at the ceiling. He didn’t know when he got in the habit of tearing himself just to get off, but he didn’t think it’d stop anytime soon.

Afterword

End Notes

If you have anything you'd like to say, please comment! Comments are massively encouraging and I appreciate every single one I get. ♡

Please drop by the Archive and comment to let the creator know if you enjoyed their work!