Tag Archives: Teen!Chesters

Protest Line (Preview)

Started: 20.06.06

Finished: 20.12.26

Words: 527

Teen!Chesters, Cross-dressing

Originally written for the SPN Amino’s Pride Bingo 2020, for the Cross-dressing square.


“… Need any help?”

“No, it’s-” he heard another thump before the youngest let out a heavy sigh, “I… actually yeah. But you can’t tell anybody.”

What are you doing in there? Bobby scrubbed a hand down his face in worry and nodded, “Who would I tell?” He waited a moment, hand hovering over the door knob, “… Can I come in now?”

He heard some rustling, before another crash, and suddenly the youngests’ voice was closer to the door, “Promise you won’t tell Dad?”

Why do you sound… scared? Bobby barked out a laugh, “This may surprise you kid, but I don’t tell John everything.”

“O-okay,” he heard the lock on the door turn before it opened a sliver, youngest rushing back away from the door as Bobby entered. He turned as he saw Bobby enter and pointed, eyes wide, “Close the door!”

Bobby closed the door immediately and turned to survey the room. There was a broken lamp, clothes thrown all over and the youngest Winchester standing there in a pair of pantyhose that were sliding down his leg, and an ill-fitting evening gown hanging off his thin frame, looking like a deer in the headlights. Bobby took in a deep breath as his brain caught up to the situation, and he had to resist the urge to smile, “Well… I can see why you don’t want me to tell John.”


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(Red String of) Fate

Started:  19.02.01

Finished: 20.02.06

Words: 4,887

Destiel (teased), Sabriel (teased), Teen!Chesters, TW: Self-Harm (slightly graphic/mentioned), Abusive!Alcoholic!John (non-graphic)


He starred down at the red string tied around his wrist in annoyance, seriously? You had to pick this week? As if the blonde didn’t have enough to deal with, now his stupid ‘red string of fate’ chose to become brighter.

According to the lore, that meant he and his ‘true love’ were getting closer – the brighter it gets, the better chance you have of running into your fated other half. It could happen any time, any age, and was supposed to be a celebratory thing – you finally finding your other half out there in the big wide world.

Dean thought it was closer to a crock of shit then some fairytale. People were way too obsessed with finding their ‘love’, some would travel to every corner of the world they could in desperation, and the girls at school? They hooked up with pretty much any guy they could get their hands on – some of them thinking the fated love needed to be ‘activated’ – only to end up running around the room gathering their clothes, never to speak to the guy again when the strings didn’t glow intensely.

No, it was much better in Deans’ opinion to leave well enough alone and go about your own life – if the stories were true and you were fated to be together, you’d run into each other at some point, regardless of if you went searching for them, right?

“Dean!”

The shout from downstairs startled the blonde, and he quickly buttoned the sleeves on his shirt, no need making a big deal out of this.

He trooped downstairs to see John standing at the base, holding Sam by the collar.

“How many times do I have to tell you to keep an eye on your brother?”

“Sorry, Sir,” Dean grabbed his brother by the wrist – not missing the cut over his eye that was most definitely not there this morning – all but pulling him into the banister.

“I was in the middle of a fucking important job! Y’know, the kind that puts food on the table for your sorry asses!”

“It won’t happen again,” Dean roughly shoved his brother up the stairs, behind him.

“It better not,” the brunette turned on his heel, picking the half-drunk bottle of Jameson up from the coffee table, “He better have that homework done by the time I finish.”

“Yes, Sir,” Dean watched as his father collapsed on the couch before he turned back up the stairs, following his brother. Once they were in the privacy of their bedroom, he turned to his brother, “What happened?”

Sam sighed, deflating as he sat on his bed, “I was just trying to go out for a run,” he ran a hand through his hair, sleeve pulling down revealing his own red string, it was glowing too, “I didn’t turn the light on because I didn’t want to wake him. I got all the way to the door when I accidentally kicked over an empty bottle.”

The blonde let out a breath, running a hand through his hair as he swallowed down the lump in his throat, “They weren’t at the curb?”

“He said he needed to save them for a ‘project’,” he gave his brother a pointed look before flopping backward onto the bed, shirt lifting slightly revealing angry, red lines across his too-thin hips, those look fresh, “How much longer?”

“Not long,” Dean crossed the room, kneeling beside the bed to pull out the box of cash he’d been saving, “Just a few more weeks.”

“You’ve been saying that since I was 6, Dean.”

“Why do you think I never say a number?” He cocked an eyebrow at the upside-down smile his brother was giving him, “Just hang on a few more months. Once I’m 18 I can become your guardian and we can finally get outta here.” He replaced the lid and put the box in the closet, he made sure to keep it’s location rotating, just in case. He made his way over to the bed sitting beside his brother, tilting his head trying to get a better look at the cuts, “How much longer until you stop this, huh?”

Sam quickly pulled his shirt down and sat up in one fluid motion, sly smile on his face, “Not long. Just a few more weeks.”

Dean let out a dry chuckle and shook his head, “Deal.”


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