First time tips. how painfull, and im not even sure i will know how to start... :S?

It will depend on how small you are and how large he is, as to how much pian there will be. You can help your self by streatching your self with your fingers. Start one at a time and work up to where you can insert 3 finger. That will help reduce the pain when he inters you. Make sure you use pleanty of and are realy wet before you start. It may be wise to get a small tube of KY gel to help lubricrate your self before he tries to enter you. That will also help reduce any pain. With doing those two thing it will keep the pain to a mimimum. There is still going to be some pain but it will not be real bad. Make sure that he uses a condom for protedtion. Do not expect to much the very first time. It will not last very long but it will get better the more you do it and the pain will go away. Good Luck and have fun and be safe.