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wahmbulance [DON'T READ THIS IF YOU ARE DISTURBED BY "p***s, a**, a**s, and POO]WAIT!
I'm a bottom my self...
First, Mr. BOTTOM should go to the bathroom first. If there is waste in there, and I mean, real waste, your p***s will push it in and its going to be sadly painful.
Secondly, I recommend, like Zero Fail said, water based lubricant. KY is a real good one and that's the one I use myself.
Third, the right position is the key to un-painful penetration. Trust me, this wont hurt a bit if you use the right one. How do you define the right position? You will discover the right one with time BUT... try to be relax. I had THREE miss trials before goal. And yes, one missed trial is a total PAIN in the a**...literately.
This pain is... very...very horrible. You want to make yourself dust, and you torque your body with a lot of tension. So. When ever he says STOP!!!!!!.....DO. Cuz this is a hell of a dark pain.
So... after the first trial...with fair amount of lube, over your p***s and the bottoms a**s, try it again. You don't really need to finger if you don't want too. I never do; never hurts.
The best position..and is the one I highly recommend for the first time, which also could be the right position which wont hurt a bit.
Since I'm not good at describing, I made this for you:

I like this one for many reasons. First, its comfortable. Second, your body is curved in a way the forces your muscles to un-tense. Thirdly, you can kiss at the same time and play with the bottoms pee pee at the same time...
Humans can control the a**s sphincter, so tell him to un-tense it.. In other words, Tell him not to CLOSE his a**!
Really... This is totally painless and your p***s will go right into it with fair lube, relaxation and positioning. After the first position, you can try other variants since the door has been broken!
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Now, when in the action... Go on his command. Start pushing you p***s through. At first, you'll think it wont enter. But, it will slowly begin to enter and when its half in, just lean over and get close to him. It will go IN automatically. After its in, ask him if it hurts... and try to do some movement. Pushing too deep could make a slight uncomfortable feeling for him... so try not to....unless he screams for it, of course.
Hope this helps
blaugh You can PM me if you need some more tips or a more private talk. I'm very experienced in the matter. Well...at-least I'm a Pro PAINLESS-TRATION ASSOCIATION of the GAY COMMUNITY lmao.