My parents found out that I crossdress and want to see me dressed. What should I wear?

Question

My parents found out that I crossdress from my girlfriend and now want to see me completely dressed. I am ok with doing this, but I don't know whether to be more conservative or to be a little more daring. Some advice would really help in this matter.

One problem is that I don't want to spend too much money and all I have are short skirts and 5" heels. Should I invest in a dress or something.

Answer 1

Since your girlfriend let the cat out of the bag, you should get her to help you & let you borrow some clothes. At first I was going to say be conservative, but the more I thought about it, I think you should be a little more daring. You should wear your best mini-skirt and 5" high heels, dress-up sexy, but classy. Now remember your folks wanted to see you crossdressed, so wear something that makes you feel comfortable.

Answer 2

That is the same problem which many of us had with their parents. During my childhood I had to dress secretly, e.g. when my parents were out and I had enough time to do so. I always had my girlish clothes in one of the old suitcases under the roof, carefully hidden, so nobody would find it. And sometimes I took my stuff and went into the forest by bike to spend some hours dressed as a girl. I even dressed and went to cinema in the neighbouring city one day. An exciting adventure ! It could be helpful to look for a girlfriend who could help you, possibly somebody whose parents would allow her to dress up her boyfriend in their own four walls. My own experience: It remains difficult if you cannot open up to your parents. And you should always be prepared for the case they once find out what is happening. Think about what you will tell them ! Later on, after you´ll have left your parents´ home, perhaps beginning your studies, having your own flat, your time will come to explore freely your inner feminine side. Be confident ! Jennie´s time will come. If you lived somewhere around here ( We are living in Europe!), we would invite you to come for a few days (some kind of vacations) to be the girl you want to be.

Answer 3

Treat this as if you are meeting the parents for the first time. You want them to see your style, yet you don't want to go too overboard. If short skirts and heels are what you usually wear, and are comfortable in, then that is what you should wear.
Look your best, and let your parents get to know the girl inside. No doubt there will be plenty of questions. Be as open and honest as you can be. It sounds like they may be willing to accept this part of you.
Good luck!

Answer 4

Let a professional handle this.

Everybody stand back. Give him some air. Let him breathe.

That's wonderful! It's thrilling when your parents want to participate in your hobbies.

Do not wear anything conservative. Put on your favorite short skirt and your best pair of heels and let them see the legs that they gave you.

Enjoy it. Enjoy the beauty of the dress and how it caresses your skin.

Be yourself and love yourself.

Answer 5

Your best impression would be something conservative that presents you as a LADY. Something in a nice dress such as one would wear to church would be most appropriate for a first time viewing. A nicely styled wig near your own hair color is preferable if you have access to one. Properly applied makeup (not too heavy), with a complimentary nail color, fashionable shoes with heels that aren't too high, and minimal jewelry would be your best bet to make a good impression and show them that you know how to dress with style.

Answer 6

i say get a dress you don't want to make your parents think that you are dressing up like a tramp or anything. but when you are with who ever you are with that is cool with it do what ever. when you parents get more used to it then start putting on stuff that is a little more risque. but nothing too out there, the first time. the fact that they want to see you dress that way might be a sign they are ok with it. but some like that the first time might scare them and make them not like the idea of you doing it.

Answer 7

Go to either Craigslist, Target or even a Resale shop and get some clothes.

I would go conservative and let them know this is you dressed, however you have been known to be daring. Based on their response, they might ask you to see what you mean by daring.

Answer 8

Is this for real? Can you describe the situation in further detail? You should invest in a dress anyway it's the most feminine feeling article of clothing around.

Answer 9

All I can say is that, if your parents, want to see you dressed up, then you should wear what you feel is you, don't go over the top, just be yourself.

Answer 10

no, just wear what you usually do. i mean, if they've asked to see you they're (hopefully) fine with it and probably won't mind what you're wearing. don't feel that you have to change in order show them. just be you. but then again, if you want to go get a dress, it doesn't necesarily have to be expensive, just flattering.