I agree with everyone that says "go for it". I would say that I would prefer a 3 way or group over a one on one in general. Of course it depends on the escorts involved but for the most part escorts will say they prefer to see clients one-on-one if they don't do well in 3 ways. As a matter of fact, a couple of the 3 ways I have done were with 2 escorts that I had seen separately before.
In one particular instance one of the escorts was a very hot guy with a football player build (not an ounce of fat on him) with a nice 7 inch thick cock. I had seen him twice and he was most comfortable being a submissive bottom. The other escort was totally versatile and had a true 9 x 7 inch cock that was rock hard from the get go every time I saw him. I had seen him before in a 3 way where I topped both escorts, they both topped me and they also flipped while I watched them pound the hell out of one another.
We started off the three way with the beefy guy bottoming for both us, first me then the escort with the 9 inches. I whispered into 9-incher's ear that I wanted to be in the middle. At that point I was so turned on that when he slipped that 9 inches into me there was no resistance at all - he went in with a single stroke, hit my prostate and we were off to the races - me pounding the beefy guy while I was getting battered with that 9 inch steel rod. Then 9-incher whispered in my ear "switch". I didn't realize that he had already lubed his ass up and after he went into the beefy guy I slid right into him with no resistance as well. Next thing I knew he was telling me to fuck as hard and has deep and as fast as I could. After about 10 minutes of that I needed a break.
I noticed the beefy bottom boy had a raging hard-on, was stroking himself to stay rock hard and then asked if he could top one of us. Since he had never topped in the other times I had seen him I told him that he got to choose who he wanted to top and the other person would top him - he'd be in the middle. I told the beefy guy that 9 incher was very talented when he bottomed (amazing muscle control) and then 9 incher told the beefy one that I was an excellent bottom as well and that he couldn't go wrong either way. He was having trouble deciding and I finally told him I knew he wanted to top 9 incher and to go for it. He got into 9 incher's ass and then I slid into beefy guy's ass and started railing him. The next thing out of 9 incher's mouth was "holy fuck - your cock is as hard as a steel pole". Then beefy guy moaned and said "I had no idea this would feel this amazing" - and he came while he was in the middle. Then he encouraged me to fuck the cum out of 9 incher which I gladly did - and we came at the same time (of course completely safe - this happened about 15 years ago). That was one of the best three ways ever because the other escort and I got a 99% bottom so turned on he wanted to be an aggressive top (and was) and because I knew that 9 incher was particularly adept at 3-ways.
About an hour after both of them left the phone rang and it was 9 incher asking if I had plans for the next day. I told him I hadn't setup any appointments with any other escorts yet and he told me he wanted to spend some one-on-one time with me the next evening and no money would be involved that it would be a "fuck buddy" evening rather than an escort/client session. I immediately agreed, he showed up at my hotel at about 8 pm the next evening and we went at one another for about 5 hours. We went through at least a dozen condoms and then I was awakened the next morning by a 9 inch "invader" and a very aggressive morning flip fuck. We went to breakfast, came back to my hotel room and fucked again. I had to rush to get the train back home from New York after then second fuck of the morning.
Next time in New York he actually arranged two other escorts he had worked with for a 4 way with me and him - and got them to lower their rate so it was the same cost to me as two escorts instead of three. The other two escorts were stunningly handsome as well (they evidently were a couple), both of them were totally versatile, one with 9 1/2 inches, the other with 10 inches. Everyone topped everyone and I ended up sore that evening - in part due to how aggressive the couple were - the evening ended up with me getting tag teamed by all three until I came - and I came buckets for the third time that evening.
When a 3 way is right it's fucking awesome so if this escort brought up a 3 way to you I would say to definitely go for it. My 4 way was incredible - and initiated and put together by an escort I had seen several times before.
