Tag Archives: cross-dressing

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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