Personally I’ve never thought of paid for sex as being nasty in any way. But hey if that’s someone else’s hang up then they can think what they like. As for awkwardness………. Well I’m a mish kind of guy so I’ll let you lot who go through Karma Sutra positions answer that one

I’ve got one or two mates who know about my interests so to speak. Met them through the more fetish inclined forums and events etc. There is more of a buddy kind of feeling within BDSM, kink folk I think.
As opposed to the more solitary style of your sexual only punt chap.
As for broaching the subject.
I’ve been in that kind of company where you get the comments,
“You’d never get me paying for it”
Load of tossers, wankers and idiots who are almost certainly liars. Or most probably ‘A’ sexual.
Jeez I must have paid for it in one way or another other in civvy street…… if you catch my drift.
As a 24 year old living in the smoke I had about four months with a cockney lass who cost me an arm and a leg cos little miss Fauntleroy liked only fizzy alcohol and had to be driven everywhere……….,. And still shagged in that frozen position where the girl looks up at the ceiling and every so often says things like,
“Oh that hurt”
Or
“Hurry up will you”
Not forgetting,
“Mind my hair”
Still makes me wake up screaming when I think about it. I could have spent that coin on decent paid fur sex. 😂