Go slow and start small. Make sure you click with the dude. Don't want somebody to start pounding away if your having a hard time taking it. Need to trust him and communicate well. Oh, and get to where you enjoy it and you'll make a killing. I don't think it's a big deal but plenty of dudes do. Have fun - I hope to visit your other two fun zones soon.
The best positions (imo) are when your thighs are at a 90 degree angle with your body.
The calmer you are the better. Start slow. You can use toys or a finger to get started. Always use a lot of lube made for THAT type of play. It will hurt a little at first no matter what but it starts to feel good after you relax. I would start with someone you know well and communicate well with. An enema an hour or two before is also a good idea. I do use a plug (sometimes) to get ready for Greek appointments. Hope that helps!
Bite down on a stick or a rolled up cloth. But really, the ladies seem to tolerate it when you take slow. Inch by inch until you find a stroke you can handle. What's the fun it that (for me)? I wouldn't consider the extra donation unless you could take it all and enjoy.