For your first time being fucked I would:
1.) Get a guy who has bottomed before so that he knows what you will be experiencing the first time. (I find that most exclusive tops will insert their dicks in your ass too fast, which is painful if you are inexperienced.)
2.) Slowly insert a small dildo (smaller than his dick) or butt plug in your ass while the other guy is sucking your dick. By controlling the dildo insertion, you can start and stop to avoid pain. When you can get the dildo in without pain, then take it out and let the guy fuck you. This is also a good way to check that your are clean inside. (check other threads for cleaning tips). Be sure to have a tub of baby wipes or paper towels handy for any mess.
3.) If you are not too close to cumming, stroke your hard dick while the other guy slowly enters your ass. Some guys like to squat over the other guy and slowly lower their ass on the other guys dick. Once again, this allows you to control the speed of insertions. Personally, I like being on my back. Other guys like doggy style because it is the easiest way to enter.
4.) Use 10 times the amount of lube that you think is needed. Be sure to push some up inside with your finger and dildo before fucking.
5.) Be sure to cum while he is fucking you. Usually I have to jerk off (or have the other guy do it) to cum while being fucked. Sometimes, I cum without touching my dick while being fucked. It will blow your mind when this happens.
If it hurts, stop what you are doing and go slower. Being fucked does not have to hurt. You may experience a little short burst of pain when the cock head pops through your ass ring, but have him stop and stay still or pull back slightly until the pain goes away.
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