This kid likes cross dressing? Does he realize Miltons is the store for men?

Time to reload the Miltons machine. Send all sob stories to pimpmylook@barstoolsports.com or pimpmydate@barstoolsports.com and help us help you. And you need to send pictures! If you sent an email without a picture resend with one to be considered.

Today’s Contestant

 

Reader Email

Pres,
 
This is my friend Will Moore, or as we call him Propwash. He got this nickname because he got ran over by a boat. Yes, ran over by a boat. He fell off the bow, hit the propellor, and came out the other side. You will not find a funnier kid but he’s sort of that kid that everyone just hates on for fun. So, basically the situation is that when he’s not wearing the same clothes for days straight without showering he’s wearing clothes left by our friends (most of which are females). The dude sleeps in our buddies boat house and will go days on end in the same flannel and pair of jeans. Haircuts are out of the question and shaving is just not a priority. This is more of an intervention because his sanitation and fashion habits are getting out of hand. The dudes got a girlfriend and something needs to be done before she realizes the severity of his cross-dressing infatuation and his complete disregard for personal hygiene. He’s about to go off to school and were all rooting for him but we fear if he leaves without changing his wardrobe he’ll just have zero friends. Help a bro out.