Poker Scenario

I played poker with some old friends last Wednesday and ended up with an interesting hand at the end of the night. We played a range of games during the night including pot limit Hold Em, Screw Thy Neighbor, Queen and the Follow, Baseball, Omaha and Auction. Near the end of the night as people started to get loopy so we played a bunch of hands of pot-limit hold 'em....and that's where it really got interesting.

In what turned out to be the last hand of the night, I got 6, 8 offsuit on the button.

It's a hand that I normally never play, but with the 25 cent ante and only needing to call an extra 50 cent raise, I kept the hand. And it turned out to be the right move as I got a great flop:

With four cards to a straight, I decided to play aggressively and when it was checked around to me, I bet $1 into the $1.75 pot. Everyone called my and then I caught my straight!

Once again, everyone checked around to me. This time, I wasn't shy about betting and put $5 into a $6.75 pot. Everyone folded except one of my friends who I hadn't played poker with in two years. He thought about it for 1-2 minutes and then decided to call my $5 bet.

I was hoping that the last card wouldn't be close to the ones currently on the board as I was worried about getting beat by a higher straight, but alas my fears were realized.

My friend thought about it for another minute and then went all-in with $14.50 of his money to make the pot more than $31 dollars. I had $29 left in front of me and was basically up $9 on the night. What could my friend possibly have? Should I call his $14.50 all-in? Did that Jack improve his hand? Was he holding A,K or K,Q to give him a better straight than me? Or did he have me beat all along and was I just basically throwing my money away?

What would you do in my position? Tune in tomorrow for the mind bending conclusion to my tale.