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I have done this with a number of people in a number of different circumstances and situations, with regular "fuck buddies", with carefully screened "partiers" and with some men who were previously strangers to me, men who were brought as a friend of the other man. That's all I'm going to say about that issue.

Now, on the much more important issue of orgasm...
Usually I start having my own orgasms very quickly. This is an incredibly intense experience, there's lots of foreplay involved, so I am pretty far along towards cumming by the time we actually start. MY orgasms just get more and more intense, until the "big one " takes place.
My own orgasms often seem to trigger theirs. My muscle contractions, anal and vaginal, during this level of orgasm are very intense, and many men can't hold back.
When I have the "ultimate" orgasm, this often ends things for a long while, as none of the men I have done this with are into necrophilia, and I am am pretty much dead to the world at this point, and stay so for a while.

Most often the man in my ass orgasms first. It has been explained/suggested to me that this is due to the "novelty" of the act, i.e. a man is fulfilling a special, intense desire by having anal, as well as the position, (in a DP, the anal entry is almost always doggy style) and the "tightness" of my anus (I plan to keep it that way, thank you) together adding to the intensity of his experience. I am usually astride the vaginal partner is sort of a cowgirl position, and this usually helps delay his orgasm.

(If any men out there have anything to add to the above, please do so.)

Sometimes the man in my ass cums, pulls out, and stays nearby as I continue to ride the other while the first man is stroking my body, kissing me or playing with my boobs. Sometimes he cleans up and I take him orally while continuing to be fucked vaginally, or if he gets hard quickly he might take a turn fucking me vaginally while the other man enters me anally. I have switched before the first man comes, but not often as this requires a long pause as the "anal" man removes his condom, cleans up, and puts on a new one.
Remember this is a 3sum, so there's lots of other sexual interactions, such as oral, anal/oral, and oral/vaginal, taking place. Not every 3sum, or even most of them, in my experience has resulted in a DP, even when anal was part of the night.

Something I forgot to mention in my earlier post is the fun of a 4sum, as in being part of two MF couples. While I am being DP'd the other woman is very involved, and adds so much to the experience.

Every experience I have had with DP has been different, so any contradictions above are due to this variety.

Sisters, if you want to do this, be prepared for an amazing experience, but most of all BE PREPARED. Make sure you are "open", stretch your anus in advance as part of foreplay, use condoms, GOOD ones, maybe even double up, and lots and lots of lube. You CAN NOT use too much lube!
Know that vigorus anal fucking can HURT, and requires someone with control, and know you are going to be very worn and probably sore the next day or so.

Love,

WW