I have done a number of double penetrations (2 penises in the same hole). The first time I did a double vaginal, I was amazed that the girl could handle both (she was 5'3", maybe 100lbs soaking wet). The other guy was longer than me by about 2", but not as thick. She loved the feel of one penis going deep while the other spread her out. After that, I used to hook up with a couple who really got off on 2 in her vagina. I've done 2 in the anus with both girls and guys, but with girls, it always seems harder to get them to open up. My favorite double anal was with an old girlfriend who was really into anal. I have to admit, her ass was on the loose side from all of the serious anal we did, but she would close back up after a few days. An ex of hers really really wanted to ass fuck her (they never did when they were together), and I told her I'd be up for it if she was. He was a nicely hung black guy who looked (and was hung like) Lexington Steel. Okay, his penis was only 9"+, but he was as thick as me. I let him ass fuck her for maybe an hour or so and then I suggested we do a DP. He thought I meant one in each hole, but I had him lay down; she got on top reverse cowgirl and then lay back on him. He was up her ass and then I forced it in along side his. It didn't go over his, it kinda went to the side and she was hanging on to me for dear life. We couldn't really do much fucking because when ever either of us would move, she would stop us and just tell us to stay still. From what she said, she was having a non-stop orgasm just from being spread open.