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My girlfriend Cindy and I are 18 and soon to be 19. We are nearly done with High School, only a couple days left. We have played around before with me wearing some of her clothes before and it was sexy and fun. Over the last few months I have started to wear panties almost all the time at her suggestion, and I find it kind of exciting. We have gone shopping together and she has helped me buy feminine things to wear for her. Now she has said that she would like to get me a wig and do my makeup nice and take me out somewhere all dressed up. I am nervous but excited thinking about doing this. Where would be a good place to go for my first experience out as a girl? What do you think I should wear if I do decide to go through with this?

2007-06-11 07:09:07 · 18 answers · asked by Anonymous in Family & Relationships Singles & Dating

18 answers

noone wants to see some ugly dude dressed up like a girl
thats lame

2007-06-11 07:11:56 · answer #1 · answered by acadx 4 · 0 3

I think you are discovering a part of yourself that will be with you the rest of your life. And it sounds like you got a girl to accept that.

Take it slowly, read up online about cross dressers. I know a ton of them who are straight and some are even married! Its just an interesting fetish!

I would say go somewhere there arent alot of people at first. If you go to the mall or something, they make make fun of you or hurt your feelings.
Maybe a park?
If youre feeling really daring, Id suggest a gay bar. They will definately NOT make fun of you there.

Good luck! Have fun with it!

2007-06-11 07:14:10 · answer #2 · answered by Anonymous · 1 0

Satan has wormed out from under his glutinous rock and seeks to wrap himself around you in the form of a pretty girl with her shiny clothes. You need to go to church and pray and pray and pray and also throw out you panties and eyeliners and silky nylons and pretty little dresses and buy some overalls and a t-shirt. So my answer is Church in overalls with a t-shirt and socks and tennis shoes and definitely underwear.

Pray and pray and pray and I will pray for you also. You are on the cross roads of a terribly attractive but sinful journey and you must muster up the strength to reject the lipgloss and flirty clothes.

Be strong and feel the prayers flowing your way. Reject that wicked hussy in favor of salvation!

2007-06-11 08:13:04 · answer #3 · answered by Repent 1 · 1 1

Why don't you do some research on cross dressing and find out more about it, other's experiences, etc.

Where you go and what you wear, is up to you and what appeals to you. I once briefly dated a cross dresser who had an affinity for spandex.

2007-06-11 07:14:25 · answer #4 · answered by . 7 · 1 0

buy a nice A line dress if your going to shave your legs... if not slacks and a blouse. Go to a coffee house or a cafe... a place to go to be seen but where no one is likely to scrutinize.

2007-06-11 07:14:18 · answer #5 · answered by sterlingsight 2 · 1 0

Uhm...maybe a lesbain bar or something? I really don't know. You might should go to one of those websites for cross dressers for suggestions. Wear something that makes you feel good. Don't over do it though. Remeber that you are still a guy....

2007-06-11 07:12:52 · answer #6 · answered by Forever the Sickest Kim 5 · 0 1

I really don't understand. Is your gf gay? Why does she want you to look like a girl if she isn't gay? Personally, I like a man to look and act like a man, otherwise I go out with my female friends. I think you may have leaning towards being gay too if you're willing to put up with this.

2007-06-11 07:17:44 · answer #7 · answered by Sage 6 · 1 1

Well Steve if you do this you should go to a gay hangout. So if you get hit on you might not get beaten up by the guy when he finds out about you.

2007-06-11 07:15:40 · answer #8 · answered by Anonymous · 1 1

Public library, go with a layered look.

2007-06-11 07:11:59 · answer #9 · answered by Twoflowers 3 · 3 0

Sounds transsexual and your GF is helping you be a women. Kinda weird.

2007-06-11 07:13:20 · answer #10 · answered by divers_godeeper 5 · 2 1

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