SometimesBi

The OP asks the question of IF the past incident should be brought up. It sounds like you really want to, regardless of suggestions or concerns others have replied with.
So then I submit that you should now be thinking of WHEN to bring it up. 
If you are truly attracted to him, I would NOT bring it up too early. Definitely not before meeting, and possibly not until the second or even the third date. Establish a connection, and if it is strong, then bring up a "...you know, I think I just realized something from the past..." type of conversation. 
Just remember, it will almost surely play out just like those romance movies, and could cause a rift in your friendship. If they aren't feeling a strong attraction to you before you bring this up, it could end things. This is dangerous territory. 
Good luck.

The OP asks the question of IF the past incident should be brought up. It sounds like you really want to, regardless of suggestions or concerns others have replied with.
So then I submit that you should now be thinking of WHEN to bring it up. 
If you are truly attracted to him, I would NOT bring it up too early. Definitely not before meeting, and possibly not until the second or even the third date. Establish a connection, and if it is strong, then bring up a "...you know, I think I just realized something from the past..." type of conversation. 
Just remember, it will almost surely play out just like those romance movies, and could cause a rift in your friendship. If they aren't feeling a strong attraction to you before you bring this up, it could end things. This is dangerous territory. 
Good luck.

Reporting from Spain. What a treat! 
We met yesterday morning at 10am (I know it feels early but my provider told me it works to keep stamina going as you are fresh) and we finished past 10pm when everybody went home. 
Thank you all for your advice! I followed all the tips and it worked like a charm. 
It was a very intense yet amazing experience and I’m still thinking about it. Once the session was over I ate something as I hadn’t eating in two days (only liquid diet with protein), took a shower and went to bed and slept like a baby for 9 hours straight. I was beat. Walking up now in Madrid and my hole is still pulsating from yesterday’s marathon but so proud of him because he did work out like a good boy. 
The guys arrived at 10am and all looking great. My provider was not lying. They are all friends and have a great rapport. We started getting naked and moving into the bedroom. I booked an Airbnb with a Cal King bed. They are not normal in Spain so I looked and looked until I found a place that worked for the five of us. We started making out with my provider being the ring leader (he told me he will take charge for a great experience). 
My provider knows that I love rimming so he instructed the guys to all go on their fours on the bed so I had a view of all their asses and I could go around rimming each of them. The guys were all in the bed making out with each other as I was eating one ass after another. I took some poppers and a viagra (so I didn’t lose my erection) and I went to town. Then a couple of them moved and starting sucking each other and the others turned around and put their legs up in the air so I could rim them and suck them at the same time. They grabbed me and started sucking me while I had a guy seating on my face. Then I noticed they raised my legs and started rimming me. It’s amazing to be rimmed while rimming someone else. My provider instructed the guys to take turns so I had one rimming me, one sucking me and one of them sitting on my face so I could rim him. And then they keep switching. They keep putting their fingers inside of me and opening me up. They gave me some poppers and I could send my ass opening up as I was in heaven with the attention. Then my main provider put a pillow under my back and the guys started lining up and the fuckfest begun. One after another starting giving me their dicks while my main provider fed me some poppers and his own dick. I used the pig snout for poppers and no spills which was great. One after the other they kept drilling my hole and I loved it. Then after don’t know how long they turned me around with my legs spread over the bed, my dick hanging out and my ass propped up. And one after the other gave fucking me as I was stroking my dick. I was a dog in heat. I don’t know why but the moment one of them took their dick out my ass was pulsating asking for more. I didn’t want them to stop. My dick was hard from the viagra and my main provider asked if I wanted to do some train fucking. We moved around and I buried my cock in my main provider’s ass while I had one of the guys fucking me from behind. I asked the others if they wanted to join and they agreed and we did a five man train fuck. The room had a large mirror so seeing the reflection of the train fuck was amazing. I don’t know what time it was but time was going fast. We had some sodas and protein bars and continued as my main provider was so kind not to let the party die down. We tried so many posturers. I went on the top of the bed grabbing to the bed frame with guy after guy drilling me from behind. The guys stood on the bed one next to each other and I went sitting in one guy to the next to the next. At one point my body was on the floor with my back against the side of the bed, my legs up in the air open wide and the guys entering from above. The more cock I got the more I wanted. It was pretty intense. I loved when they took turns fucking me on my fours while I was eating a guy’s ass. And then they kept taking turns so another guy to rim and another fucking me. By the time it was the last hour I was in bliss and it was time for release (they had been holding really well - one came at one point but recovered shortly after but the others are pros at regulating) so they put me once again with my legs spread on my fours with my cock hanging and my ass propped up and one after the other went to town in my ass until they came. I had all loads in me and they kept fucking me. They tuned me around and they all started sucking me and stroking me and fingering me until I blew a huge load. Fuck. That was insane. The guys showered, we chatted for a bit and they all left and I was left all spent and happy in bed. I went took a shower, left my children out (haha), ate something and onto bed. I just woken up and I won’t lie if I’m not a bit tired or sore but all pretty good and the memories will last a long time. Thank you all for your advice and for your help prepping for this session. I know it was a splurge but Spain is the place to do it as in the US that would have cost me 3 times as much. But it was pretty amazing. 

Gee, and here I was hoping this topic would have revealed the finger pic as a way for the provider to suggest he offers prostate massage 😏😁 

Maybe 5% grab my attention; 15% after applying filters. I too have been finding Austin enticing. When I’m at my place near Seattle, I make trips to Vancouver, where the selection is far superior to Seattle.

Maybe part of the confusion is that you posted your services on rentmen instead of rentmasseur. 

Ok, now I gotta ask: Do you really think that once you got going, that you could restrain yourself to just the 5 inch depth? I'd expect the urge would just be too strong for you to not, eventually, push all the way in. 😉 

While it’s true that plenty of clients skim ads and waste providers’ time with questions like “Can you host?” even when the answer is clearly stated, the frustration definitely goes both ways. Providers can be just as guilty, many ignore messages completely, don’t bother to read client profiles with key info like preferences or boundaries or reply with vague copy-paste responses that barely address what was asked. This kind of mutual negligence isn’t unique to this industry, it happens everywhere.
Here’s a typical scenario I’ve run into way too often. When I reach out to a provider for the first time, usually when they’re listed as “available” on the site, my message includes four simple questions: rates, whether they’re comfortable with my expectations for the session, their availability on a given date and, if they host, a general idea of their location.
What happens next? I might get partial answers to one or two questions usually a day or two later. So I follow up with the remaining questions. If another couple of days go by without a clear response, I move on. From their perspective, I’m now a “time waster” because I texted twice and didn’t book. From mine, they’re the time waster because I spent days just trying to get basic information. So… who’s really in the wrong here?

Wait, what? Is that a Russia thing, giving up your passports? Or were you just putting them in the hotel safe? 

One important question that I still don't know the correct answer for:
What is the proper way to measure your penis? 
And followup: how to translate the big lengths guys list in most ads. What to really expect when a guy says 10" 
 

One important question that I still don't know the correct answer for:
What is the proper way to measure your penis? 
And followup: how to translate the big lengths guys list in most ads. What to really expect when a guy says 10" 
 

One important question that I still don't know the correct answer for:
What is the proper way to measure your penis? 
And followup: how to translate the big lengths guys list in most ads. What to really expect when a guy says 10" 
 

Back to the OP, here's my suggestion. Set up the car wash/detail. But ALSO plan to be shirtless in shorts yourself (it'll be a hot day, right). Chat a bit as he's getting started on the car. Remember, he may have noticed your eyes wandering while he was talking to you last week. Watch to see if his eyes wander. An opportunity to have a more sexual conversation may present itself. Maybe you'll bring up RM, or maybe he will volunteer it himself (or even just let things develop all the way, and you get a freebie) 
He's on RM. He knows how to be discreet. It sounds like you are, too. I would not expect any complications with neighbors. 

Back to the OP, here's my suggestion. Set up the car wash/detail. But ALSO plan to be shirtless in shorts yourself (it'll be a hot day, right). Chat a bit as he's getting started on the car. Remember, he may have noticed your eyes wandering while he was talking to you last week. Watch to see if his eyes wander. An opportunity to have a more sexual conversation may present itself. Maybe you'll bring up RM, or maybe he will volunteer it himself (or even just let things develop all the way, and you get a freebie) 
He's on RM. He knows how to be discreet. It sounds like you are, too. I would not expect any complications with neighbors. 

Back to the OP, here's my suggestion. Set up the car wash/detail. But ALSO plan to be shirtless in shorts yourself (it'll be a hot day, right). Chat a bit as he's getting started on the car. Remember, he may have noticed your eyes wandering while he was talking to you last week. Watch to see if his eyes wander. An opportunity to have a more sexual conversation may present itself. Maybe you'll bring up RM, or maybe he will volunteer it himself (or even just let things develop all the way, and you get a freebie) 
He's on RM. He knows how to be discreet. It sounds like you are, too. I would not expect any complications with neighbors. 

The problem is, the provider charges more for 2 "clients" vs 1 client+1provider.
So contact the provider again, only this time say you'd like the 3way again, with a different additional provider, that you've already hired and will pay separately (that is what you did the first time?). Then the main provider's rate should go back to 300. 
Just be sure your friend role-plays his part in this.
 

Gee, and here I was hoping this topic would have revealed the finger pic as a way for the provider to suggest he offers prostate massage 😏😁 

Last month, finally hooked up with a friend acquaintance for the first time, after months of trying to align sschedules. Both of us are older, and that age kicked in. It was difficult for either of us to really get excited.
So I had this thought today, that maybe we could get together, and hire one provider to come service both of us.
Would a provider want/need to charge differently since there are two of us as clients, instead of just the usual one? Will we have difficulty even finding a provider that would have us both? 

Gee, and here I was hoping this topic would have revealed the finger pic as a way for the provider to suggest he offers prostate massage 😏😁 

Gee, and here I was hoping this topic would have revealed the finger pic as a way for the provider to suggest he offers prostate massage 😏😁 

Gee, and here I was hoping this topic would have revealed the finger pic as a way for the provider to suggest he offers prostate massage 😏😁 

Gee, and here I was hoping this topic would have revealed the finger pic as a way for the provider to suggest he offers prostate massage 😏😁 

Agree.  He might be able to select "side" from the drop down menu of choices, but he can elaborate in his ad copy. 
The ONLY way I would consider hiring escort with "side" only is if he was great at eating ass and and with finger penetration and stated so specifically in his ad copy.
I may not get his penis inside my anus; but, by golly, I need to feel some part of his body in there!

First I've heard of such a thing. So that begs a question: if the top does this, how does he thrust without them popping out? 

Hey it might not be a 3sum actually. Myself and another top bud once had a bottom over and just took a turn one on one in the bedroom with them while the other chilled in the living room. 😅