OK, well, yeah, I had an interesting conversation with my boyfriend the other night which pretty much lead to him telling me he likes the idea of me dressing up in ladies clothes and wearing make up for us to, well, have some sexy time. See, I'm not a cross dresser at all, though I will admit to wearing make-up on occasion in my late teens early 20's, but then I idolised(still kinda do) the New Romantics from the early 80's and, well, kinda mixed it in with that. So anyway, I can't help but admit the idea of dressing up is really appealing to me BUT I don't have a single gosh darned clue about this developing idea(Note: I don't know that I would be a cross dresser in any meaningful sense, just occasionally for the purpose of fun time shenanigans). I mean, I don't want to just pick any old clothes and go from there, I believe if you're going to do something, you do it right(though I refuse to shave off my beard and moustache for it), so I was hoping for some tips and advice. Also, I was wondering if anyone knew of some decent online stores or even places in the UK/London that would cater to a) the larger person b) cross dressers. This is new territory for me but something I am keen to explore.
Well, I'm not a cross dresser either and frankly, it just doesn't appeal to me. Having said this though, I did went to a few parties where I dressed in woman's clothes as part of a costume or part of the theme (Went to one where the theme was opposites, kinda funny, but cool) The thing about woman's clothes, is it isn't the clothes that makes a woman, its the woman that makes the clothes. This basically boils down to body shape and personality. If you have a "voluptuous" shape, then you have to go for that kind of clothes to make the role that much more believable. Also the personality, like a '70's girl will always have something that reminds them of nature in the clothes they wear, where a strictly business woman will have none of that, opting for as little as possible pasterns to bring the attention to the face and not the body. So that means, it all depends on your body shape, what you are comfortable to wear and your personality you want "her" to have. This personality can be really fun for you both, like one day you can have "her" have a slutty personality, while other times you can change it. Doing any kind of cross-dressing, can help you escape your own personality for a while and become something else entirely. Of course I might be entirely wrong here, but I did grew up with sisters so I kinda know "their" world quite well.
Have been with a couple of crossdressers in my time. They were not passable but it was their attitude when they were dressed that made it a fun time. I wouldn't run out and buy a new wardrobe. Maybe hit up some used clothing stores and pick out something sexy. Maybe HE can pick out something sexy for you.
Very quickly, here's a link to an online store for crossdressers based in the UK, they've got physical stores too including I think one in London: Welcome To Transformation. Online shopping for Transvestites, Crossdresers and Transsexuals, Supplier of Female Hormones for men | Transformation I've never used them but I wouldn't recommend buying from them as you can get similar stuff much, much cheaper on places like ebay.
