Originally Posted by
sometimes_miss
Don't tell them quite yet. You need to do some damage control groundwork first, and I'll get to that. When you finally do tell them, don't just out and out tell a family member and leave it hanging there like a mushroom cloud in the room. Get prepared. Get some literature about it, either online or buy it at a bookstore. And don't tell your mom that you're wearing her stuff (see the other thread about women going ballistic when they find that one out); tell her you want to start 'occasionally' wearing cute girl clothes. They're first idea is that you are gay (which is o.k. if you are, but then you're probably dealing with other problems as well), and you're going to have a tough time if you try arguing against that idea all on your own. Have resources available; there are lots of places, here being one of them, for family members of crossdressers. There are even support groups out there for them (and you), if you're near a larger city. Now, I think that before you do any of this, you should slowly 'feel them out' about how they might respond, because there's no putting the toothpaste back into the tube once it's out. Relationships have been destroyed, families split apart over this, in large numbers. My advice is, wait a while. Maybe once every few weeks, bring home a dvd with a character that crossdresses and see how they respond. Don't start out with any where the characters are gay unless you are!. 'Some like it hot' is a real classic, and won't scare them. I know 'Tootsie' is a really good one because it portrays a perfectly straight guy who is really, really good at looking like, and acting like a woman without him being gay. You can even use that one, watch it one day, maybe rewind the scene where he's transforming himself (you can always say you're amazed at how someone can do that, and appear interested in the process more than the actual result), then a couple days later show up at home with some of your girl things (make sure they look like you just bought them!), trying them on, saying you got the idea from the movie (perhaps not true, but lots of society likes to blame the media on people's behavior, so let that concept work for you). Say it looked like fun so you wanted to try it out. Who knows, maybe mom will even help you with your makeup. Don't start out with a bra, that kind of makes it look like you want to be a woman (which is o.k, but not to let them know that too soon). Start with the 'metrosexual' look, eyeliner, nail polish, etc.. then you can slowly graduate to more female stuff, thongs, panties but 'boy shorts' style girl panties are the best to start with. You want to allow them to ease into this rather than just come home in a wig, make up and a wedding dress. If you are in the practice of bringing home magazines such as maxim, stuff, playboy, etc, continue to do so and make them an obvious part of your environment, it helps the image of heterosexuality being a constant even while you're slowly embracing your female image. For the moment, avoid having anything like Cosmo, Glamour or Vogue, and don't even consider Seventeen. You want it to appear that the female clothing is just something you are playing with. I'm sure a lot of others will chime in with their ideas. But take it slooooooooow.