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http://nnbrooklyn.livejournal.com/ ([identity profile] nnbrooklyn.livejournal.com) wrote in [community profile] spnstoryfinders on April 16th, 2016 at 10:24 am
Pretty Enough Series
http://archiveofourown.org/series/27074

"Jensen has been hurt, and he is not about to put his trust in anyone, ever again. Things might change around the school however, when a new student arrives. But will Jensen allow the change or will the nightmares from his past ruin his last year in high school?"

Maybe this? I remember few things from that series that fit your description so I hope you'll like it :)
 
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