I was telling a dancer (that I get dances from OTC) about an escort I had had multiple "dates" with. Escort came across as very GFE and generally self-respecting. She allowed me to eat her pussy. No bad surprise, impeccable hygiene. She seemed to have a orgasm, but I, naturally, was dubious. But the dancer says "no she probably really had one." Me: "But I'm old, fat and ugly, how is she gonna cum?" Dancer: "She closed her eyes and thought about someone else, or she may be the type that just responds to the sensation with no context." (Or something like that not an exact quote probably.)
Now, this is a dancer who is not even willing/comfortable to dance all nude with me, let alone let me eat her pussy. So, why would she say this? She is far from dumb, I can't think it would not occur to her that this escort (her competition for my $$$) is more attractive to me if she can have a real orgasm with me.
Tangent: Gay male friends have told me that there are gay guys who are very turned on by the idea of blowing straight guys. Suppose there was a team of a gay guy and a hot female dancer who did not want any contact with your schlong. The guy blows you while you have the typical two-way but no extras contact with the chick. Any appeal? I would not be comfortable with it, but maybe that's just homophobia on my part. Seems like you could focus your thoughts on the beautiful women you were seeing and caressing, and ignore the source of the accompanying penial stimulation.
The last part of your pos escapes me, but back to your ordinal scenario. My ATF seldom experiences orgasm with me, but on two occasions I've watched her fuck young "hot" guys and on both occasions she was multi-orgasmic and she tells me when she's with a guy for choice she almost always cums. One time there was a porn movie on after I'd ejaculated and she was really into it, told me to come eat her and she came and came. Another time we both had dropped some Ecstacy and during vaginal intercourse she flooded the bed and me with nipples hardened, toes curled up and clearly had an orgasm. Last week at the club in VIP she told me she hadn't gotten laid in weeks and was really horny and once again during BBFS she clearly had an orgasm. I'm 67 and she's 27. She is one of the most beautiful women I've ever seen and I'm slightly overweight and as she very kindly tells me, maybe if I had danced more when I was younger, I might have better rhythm . We've fucked at least once a week for four years and there are feelings between us, but clearly, I'm not the young hot guy, she's used to. She never lies about orgasms and says, don't worry about it. I'm paying her to please me. I've explained that when she gets off, I feel pleased and like I've done a good job, too. There's another dancer I've seen OTC several times and she always fakes orgasms and I know it, but I still enjoy it. This dancer also gives the full GFE which my ATF doesn't. So, the bottom line for me is that honesty wins out. When she does get off I'm ecstatic, when she doesn't, she still works extra hard to get me where I want to be. I'll skip the weird threesome you posited.