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Shelley Dennis (Brief Breasts) in Grey Skies (2010)

Sasha Grey challenge, the best I could find. Very brief but I'm pretty sure he gets a least his head in.

Grey AC briefs

Grey joe boxer briefs hanging wedgie

Grey briefs never miss

[M] Losing Control in Grey Boxer Briefs

Grey Tommy briefs (18m) dms open

Precum in grey briefs

Sporting men's boxer briefs better than most men do