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Squilliam said:

So we were walking together, just chatting peacefully when my friend dropped the bomb.

Friend: "So, like, I was thinking of buying a DS lite for pokemon.

Me: "Say WHAAAAT"

Friend: "Yeah I want to be able to pull out a gaming system when im doing something boring like waiting around"

Me: "Get away from me you freak!"

Friend: "No, im serious I want to buy a DS Lite with pokemon from xxxxx (not be named) for $150, can you spot me a hundie"

Me: "And turn one of my best friends into a girl?"

Friend: "Well I'll take the tits but you can keep the vag."

...... AND SO ON.

So do I become a DS enabler and help my friend get a DS and possibly a set of tits to go with it or do I deny my friend and hope he forgets about it in a week or two?

This thread should be close to being locked.  It would save you from being embarrassed for one thing.  My thread asking about "Stupid Americans" buying the 360 over the PS3 got lock, and this should be considered here. 

The reality is, when it comes to videogame systems, the DS is probably the most mature of all the systems.  It has games REAL adults play, such as Dr. Lawton, and also puzzle stuff.  It has programs for cooking and tracking weight loss.  It has classic novels. 

So, I would say, it would be good to spot him a hundred... so he grows up.  One has to seriously question your maturity age, by calling people who like DS systems, "Girls".  Completely and totally pathetic on your part.  You are VERY disgraceful thinking this.  How about live and let live?

If you don't want to spot him a hundred, then don't.