starting crossdressing?

Question

i have come to terms that, i wanna crossdress in the future, as a 16 year old, straight male, i need to know how to start off as i dont want to do it in public, but i wanna have fun at the same time

thanks very much
x

Answer 1

If you want to start cross-dressing, then start, you need to go shopping & get yourself some new clothes. If you don't want to go shopping, there are plenty of places on-line that can help you get what you need. And even if you don't go out in public when you're dressed as a girl, you'll still be able to have plenty of fun. You should at least try & go out on Halloween dressed as a girl, that's the best time & you would have even more fun.

Below are some links that you might find useful:

Answer 2

How to start? Interesting... OK - think to yourself what first attracted you to the idea of cross-dressing then work from there.

For me, the initial fascination was the dress - so I started there.

Your choice of outfit depends very much on your build
* If you're well built you'll not want to show off your muscles so wear a loose blouse with sleeves and a longer skirt. A-line and gypsy skirts can give an impression of hips!
* If you're slim, you can wear almost anything. Try a nice halter-neck dress or a mini-skirt with layered top.

But you have to have the total experience
* Shave arms, legs etc
* A thong won't work, so go for panties
* Of course, a bra. Tissue sort of works, but balloons filled with jell-o (jelly if you're in the UK), or rice works better as you'll get some idea of weight and your breasts will bounce a bit too.
* Don't forget the pantyhose
* Wear a pair of heels

If you've short hair, you'll probably need a wig

Don't forget to your make-up - that includes nails (get some stick-ons if yours are short)!!, and a purse (wallet, phone, keys etc plus hairbrush, hair ties, makeup)
Get your own makeup though - sharing can cause skin complaints.

For best effect, look at what girls of your age, build, height and culture wear every day. You may be really lucky and find a sympathetic female friend who'll go shopping with you.

Check out stores' returns policies just in case what you buy doesn't fit.

And with Haloween coming you could even make a complete day of it...

Wear 'standard' girl clothes during the day; jumper, skirt, boots (it'll be cold) and then change for parties in the evening.

I've tried to put together some different characters with a halloweeen / magic theme for the parties...

* Morticia Adams - she's quite skinny in the films, but the dress gives you a chance to cover up if necessary

* Sabrina (the teenage witch). Great if you've got the legs as mini skirt required for this one!

* Hermione Granger or Ginny Weasly from the Harry Potter films. More a 'schoolgirl' theme here but still Haloween associated - grey pleated skirt, blouse and sweater. Add a gown or cape for 'school robes' and a pointed hat if you want
(Henrietta (the Worst Witch) also comes in this catagory)

* The Bride of Frankenstein - wedding dresses can be a great experience.

ENJOY

Answer 3

Goodness, what a lot of hostile answers.

Hun, if crossdressing makes you happy, go for it. It's not illegal, it doesn't hurt anyone, and it doesn't 'make you gay'.
Some advice; be very careful about 'borrowing your mother's/sister's/girlfriend's clothes; women can tell when someone's been in their wardrobe, and you WILL get caught. And no-one likes someone else wearing their underwear, so DON'T; buy your own. You can always buy online if you're shy about going into shops.
Don't go out in public until you're confident, and try not to go on your own even then; nervousness is a giveaway, and some people will take offence (goodness knows why).
You might want to join a TV support group; there are several on the 'Net, and there's probably at least one local to you. They'll be able to give you advice and support, and maybe even help you obtain the things you're going to need, and many of them have meetings in 'safe' venues so that you can meet other crossdressers (and they won't make fun of you for being a 'beginner')

Good luck, and have fun ;)

Answer 4

Really proud of you for coming to terms with it - I was cross dressing from 4 years old and only accepted myself at 24 - I think you need to start off small, buy a few things - you can do it online or some shops are helpful, as a young transvestite I had many experience swhere I thought buy buying a bra the floor would open up and I would get battered for daring to buy womens things, for me. I love and respect women, and love this part of myself too.

What I am saying is take care, be careful, but have fun. You will have fun just by dressing at home or at a friends house who coudl support you? I don't know, mine was a lonely time, but I tell you, I loved every second. CROSS DRESSING RULES !!!

Answer 5

Well I'm a year older then you and a straight male and I still have not fully come to terms. I guess you shouldn't 'borrow' your mom or sister stuff a lot try to buy your own stuff. I'm still learning so i don't know to much.

Answer 6

Wow, a lot of hate in here. Don't listen to most of these losers. I would start out by visiting some thrift shops in outlying towns away from anyone who may know you. Don't feel nervous about buying clothes from them, they have seen plenty on guys buying women's clothes, trust me. Don't borrow your mom's or sister's stuff unless your are POSITIVE you won't stretch them out. They will know if you do. There is nothing wrong with experimenting to see if this is a road you really want to travel. Have fun with it! Best of luck to you.

Answer 7

Most of us start with our mothers or sisters clothes then go on and buy mags published for transvesties which have adverts for companies and people who will supply the clothes and teach you how to wear them but those places are expensive. You can also find adverts for clubs and events for transvesites. However at 16 I don't this way is wise or really open to you. Most clubs want you to be 18. You can of course buy your own undies and other items of clothing from local shops and charity shops. Do not be shy about buying. Shop assistants are not interested in why you are buying or who for they just want the sale

Answer 8

I have pretty long hair, I like them but I actually think I would have them slice short in about some two yrs

Answer 9

Long nails can be harbingers for bacteria, particularly if they are artificial, but they are good for scratching and opening those little foil wrapped containers that are so hard to get into.

Answer 10

Well trying it at home will definitely lead to questions from the folks so you may want to be careful with that if your concerned what they may think, you're obviously worried about the public. I think the central question is why would you want to do that if you are straight? Maybe your having a gender identity issue. Do some research on that topic and maybe that can lead to some answers. I think if you break into it slowly you should be able to get into it in public. Good luck.