Sounds - good. I'd definitely do this if not for the fact my Wife is great and indulges me.
Firstly - get involved with a girl who is into transvestic fetishism cum clothing/satin paraphilias and or is used to working with cd'ers. You'd be surprised how many are. Even if you are not a CD'er yourself - she will already be aware of things that make them tick and this will help, and will certainly make you less nervy if you know she knows the 'scene'. I have spoken to many many women over the years who would definitely do this. Added to this, she may have a good collection of her own satin clothing, so could arrive dressed as you wish, with perhaps some nice satin nightwear with which she would be prepared to a) tease you with - maybe order you to dress in it, and 2) let you keep something as a memento - like perhaps, a nightie?
That bit sorted; whatever you do will be fun!!
I've got 5 minutes so here's something along the lines of what I'd do.... OK: after the niceties sorted and when comfy, we'd work on a couple of my fantasies, the first of which would be for my 'gal' to play a more domme role (not heavily, just the 'you naughty boy' sort of thing

). As I would have previously tried to ensure she was the right person for the job, and having discussed outfits she may have, she'd have arrived wearing a satin blouse and pencil skirt, with perhaps a satin camisole and satin bikini briefs beneath, and would be classilly(sp?) made up and would have great perfume, on. I'd have her undress me, and the start to tease me, slowly taking off the blouse, and then stroking me all over my face with it and finally, teasing my cock and balls with it too whilst telling me how much she liked hearing me moan because she had full power over me. I'd then, after some time doing that, have her leave her blouse covering my twitching cock and have her change into a long satin nightie. When she'd taken her satin cami off, she would leave it laying upon my face so I could smell her and feel the satin whilst watching finish slowly dressing in the long nightie, her blouse still laying upon my cock so I could do nothing but smell her and feel her worn satin clothing upon me, all the while telling me she was going to order me to cum all over her blouse when she was ready. Then, sitting back down on the bed next to me, I'd continue to have her rubbing my face with her cami, and her other using hand blouse to stroke me off, gently, begging me to cum for her, and tell me to cum all over her blouse (plenty of 'you naughty boy' would help no-end at this point, lol). Of course, I could do nothing but squirt all over her blouse as I felt the coolness of it rubbing my balls as she jacked me off in it.
For an interlude, I'd give her some good oral, by way of thanking her for the enjoyable Pt 1.
Then, I'd want to have us both dressed in the most amazing shiny prom dresses, complete with lots of satin underwear, stockings, heels, the lot, and have a 'lesbian' romp with some mind-blowing good fucking, her finishing me off, reverse cowgirl, whilst rubbing my balls with perhaps her panties or camisole from earlier.
That should kill a good 2 or 3 hours and I can think of plenty more things we'd do together. And as I said, I'd want to keep some of the clothing she arrived in/used, for more fun later. Oh, and I would DEFINITELY pay the extra £50 or so quid it costs here to film it all, too.
Basically - it's all about the right girl; talk about what you want to do, first, and you cannot go wrong!!!