I have a bit of a lingerie fetish probably acquired from too many hours looking at the lingerie section of the kays catalogue in my teens, so yes I get off on a nice quality set of lingerie on a beautiful woman. I like the choosing and buying process and then seeing how the girl looks in and out of it. It's fun for me.
I've never gotten to the stage of doing the lingerie shopping trip with an escort. It's more of a fantasy. I've never gotten into discussions with an SP about how payment for time spent on the shopping expedition would work. I think it could be fun. Older man with young girl in lingerie shop. The shop assistants would give is funny looks but that would all be part of the experience. As I say it's just a fantasy that is unlikely to ever turn into reality.
I've done this, sort of by accident. I don't think it would be that hard to arrange as long as it's with a regular who's built up some trust. At least with the sort of WG's I've got most experience with (Brothel lasses) I doubt they'd want paying for their time, as long as you buy the lingerie and let them chose. Perhaps it's different with the more enterprising WGs you get on AW.
So this happened a few years back, before I joined the forum. I'd moved to a new apartment & wanted an outcall, as it's nice to have some sexual memories in the place where you sleep. Normally I'd use an agency, but I had a brothel reg who I got on well with so asked her if she'd like to come over for a couple of hours on one of her days off. She really admired my new quilt cover & its matching pillows, so as she'd given me great sex for only £200, I said I could buy her her own set. (Id got it from John Lewis, from a Westfield only a few stops away on the tube.) She was going in that direction anyway.
After we got the bedding set, she wanted to look round the Westfield for a bit, and chose to go in the Ann Summers. I'd only really intended to buy her the quilt, so was careful to just give her another £40 and be clear that I wasn't going to go with her to the till, so she knew she'd have to use her own money for anything more costly. Anyway we were there for 20 mins with her sometimes asking for my opinion on various outfits she was buying for work. Not an experience I'd want to repeat, but it was interesting at the time.