Penis "eye" Stretch

Yes it's possible. Sometimes it is medically necessary, other times people do it as BDSM play. On certain toy sites you can buy a thing called urethral sounds. Those are what you'd use but you'd have to be very very careful. You could do permanent damage.

http://www.stockroom.com/sec1101.htm#sec1101.3

That's a link to a toy site that has them. You might want to go to the BDSM thread here in the how to forum and ask anyone if they have experience with this sort of play.
 
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