My boss' friends are always hounding me at work for free tattoos every free chance I have but yet they won't do a thing for me. My boss doesn't allow his buddies to get charged regular shop prices but yet he sends them to me. Please note that I pay for all my supplies and also give my boss 50%. I'm trying to show respect towards the owner by hooking his boys up ,but the more I help,the more freeloaders come around. How should I handle this? Finding another job at this moment is not an option.

I think you need to talk to him in real numbers about this and let him know you're losing too much money on this arrangement. Talk to him about your need to reduce the number of these discounted jobs to a certain number per month, or for him to take the hit on the discount given that you do pay your own expenses for operating. If he figures out how much money is being lost on this arrangement, he may rethink his decision.

The size discount he's giving sounds excessive to me for something so time consuming and custom as tatooing. My family own a business selling custom goods, and they normally only discount their profit margin, not the entire order, for friends and family. They cover their entire costs including any commissions that need to be paid to a sales person, which would be the same as your share. So, your 50% would be sacred, as would your bosses costs. He might end up giving a 25% discount instead of 50% but that's stll a hell of a deal, you make your money and he makes the same he's been making. He can simply tell his friends that due to the volume of friends and family tatoos, the shop cannot afford to give the same discount they have in the past because he needs to pay his people in full for the work.