I just had my first DP the other night, and I was on the receiving end.
My Boyfriend invited a friend over for a night of "hanging out" (I kinda knew what was going to happen) and asked him to pick out a movie. PORN was his chose, all fine and dandy with us, and fun started on the couch.
We went to the bedroom, couch was just not big enough for the 3 of us to crawl around on, and our friend proceeded to have me "sit on him." Next thing I am feeling a little more pressure back there. My BF has been wanting to try DPing me and I told him I would try, but our friend was enough alone and now my BF wanted in too, damn. I knew what he was wanting and so I attempted to make it possible for my BF to fit in too.
After a few failed attempts we did finally succeed in getting both of them in me. Yes we succeeded, and it hurt, but after I calmed myself and relaxed it really did start to feel good. ( I will have to say the best part was both of them cumming in me)
Lets put this into a little bit of perspective: My BF is 8.5 - 9 (9 when it has been a few days and he gets really excited) in length and 6 - 6.5 around (may not seem HUGE compared to some on LPSG but it is the biggest have ever been with) and our friend was 9 (if not longer, he did have a little more length than my BF) and about 7 - 8 around.
It worked out with our friend as the Bottom top, Me as the Middle Bottom, and my BF as the Top Top. It wasn't bad after the intial shock, but I made it very clear that it will not be a nightly thing and that the 3rd would have to be smaller (maybe). We do want to have one of our friends who is a "power bottom" take both of us. I do want to try and be on to giving end of this deal at least once, but if I have to play bottom everytime (NOT every night) I may not mind it.
So thats my story.