im just glad you posted first ha ha and i dont think it was too vague.
first time trying it was with a bf and he asked while we were doing it and i was like yeah okay ill try it. it hurt really really bad although he didnt ease into it so after that i was turned off by it. so anyways next guy who im dating now asked if we could try it and i was a little cautious but i gave in and tried it again (im not a quitter ha!) and with him it was a whole different experience. i think it hurts the most when he is first in you, after the first initial thrust it gets better in my opinion. i think ive asked for it like once or twice. never done the dp, only thing close would be him fingering me while getting anal.