Twice I have done three women at the same time. The first time it was slightly planned, the second time was not. Both times, OMG, it kicked my ass. I am not sure if I would want to do it again nor add anymore.
When I was younger, it sounded like an awesome thing. It was a fantasy. Then the first time it happened . . . the fantasy did not match the reality. You have to make sure that the women do not get bored. You have to be cognitive of the women who are not getting attention. Then you have to judge who you go to next . . .
The first time was interesting. My wife and I were at a swing club. It was couples night on Saturday. We were sitting at the bar looking out at the people. Two beautiful black women walk by and they do not look happy at all. The smart ass that I am went up to them. I said, "Here you are, two beautiful women in a sex club and you aren't smiling!" One of them said that they were there the night before. I responded, "Oh, you must have liked it to come back the next day." Her friend said, "No. No one fucked us last night. They wouldn't talk to us." I said, "Well, those guys were idiots. I'd talk to you and fuck you." They looked at each other and said, "Ok, let's go." Holy shit . . . my terrible pickup line worked! My wife and I went to the changing room with these two other women. After we got into towels and were looking for a private room, one of the girls said, "We have an issue." I thought, ok, here it comes, one of them is a guy, or something. She said, "She is my best friend and we grew up together. Would it be ok if you fuck her and then when you are done with her, I will come in and you can fuck me?" No problem! I can do that.
So we get into a private room. Now it is my wife, one of the women and me. We go at it. I cum and the girl kisses me and steps out. A minute later her friend is in there. I start thinking . . . omg . . . be 15, be 15! NO DOWNTIME! I get hard and start fucking the woman. I cum. About 10 seconds after I came, the first girl wants back in. She comes into the room and says, she doesn't care she wants to be together, all of us. I am now getting religious and praying for my dick to get hard! I have three women who want me. It works! Now I have to figure out how to balance attention amongst the three women. We go at it again and I finally cum again, this time with the first woman. After that, I was dead to the world! My wife and I headed home and I got to hear how I fucked up and didn't give my wife any cum. That was the big clue that I needed to stay awake, get hard and cum for her. I told her you may get about 1/2 of a drop! She said she'd take it. We fucked and I did cum. I think I fell asleep within 20 seconds :)
It was nice to have this happen, but it was a lot of work.