"I love to dress guys as girls!"

[Jill]

So last night I was on a date, and this was a first date with someone that I met online. We went to a little halloween party but didn't have costumes. Naturally the costume subject came up and so did the subject of guys dressing in drag on halloween. And straight from her mouth she said: "I love to dress guys as girls!" And she continued to tell me about how she had dressed other guys up as girls, like her brother. Considering how conservative Utah is, this is a potential dream come true. If I get to know her better, I am highly considering approaching her about my secret or at least try to get her to dress me up sometime just for fun and then come out with it. I am putting this up here because I am hoping that some of you have ideas, thoughts or suggestions about this matter.

[Virtue]

That sounds really cool, what are the chances of meeting some like that randomly?! lol. Good luck :)

[windycissy]

Are you kidding? This is like a dream come true. Don't screw around with it - next time you see her, remind her of the conversation and tell her you've thought about it and decided it would be a hoot, but only if she dresses you from head to toe and teaches you about makeup, etc so you don't look like a fool. Even if you have to play a little dumb about what she's teaching you - that's something real girls are real good at, after all. Go for it!

[babe4life]

Jill, no ideas spring readily to mind, but it sounds kind of fantastic! LOL. Good luck and let us know how it pans out. I love juicy gossip ;)

Love,
Vicky

[Abraxas]

There seem to be a few Utahns around this site. Maybe it's not so conservative around here as they'd like us to think!
Maybe we should all get together and hang out sometime.

As for the makeup thing, I wouldn't sweat it. She'd probably think it was real cool you're up for it.

[carolynhcd]

She probably gets off on the power that comes from making guys over into girls. My advice is to seem curious but not enthusiastic. Let her feel like she is controlling things and seem shy and embarrassed and give her her thrills about transforming you. If you make it seem like your idea, it will rob her of her power and make it much less hot for her. Just my opinion. Love, Carolyn

[Fiona K]

Hey Jill,
No advice but to say take it slow then lie back and enjoy!!
LoL
Fiona

[Wenda]

I am a prairie girl who believes that u don't need oceans, mountains, or trees to satisfy your viewing expectations. Place your expectations before us. wenda

[Cami]

Wow, thats kinda how I got started doing this. I was 13 and my only friend was a 13 year old neighbor girl. We did everything together. when she got her first bra's from her mom, she brought me over and asked me if she could put one on me. I said yes and she did. Her mom walked in and was freaked out and told my parents. They didnt care for some reason. When things cooled down, she gave me one of her bra's and one of her panties to keep. The only condition was I had to let her dress me up whenever she wanted to.
She said she loved to dress me up. That's what made me reply to your post.
I would have been a CD even if I never met her I think. Its in my dna I like to think.

[Sharon]

She's the one who brought it up! Maybe she was feeling you out on the idea. My late wife helped me dress occassionally, and I have to tell you that lovin' was never better, although I was often careful to wait for her to suggest it to me, rather than me always making the suggestion.

[Sweet Susan]

I see it as an opportunity. Take it while it is there. You never know how well she will respond to, and she may like dressing guys up as girls more than she realizes. She could have a dominant streak in her, as well, and that can work well for a cd.

[sissy stacy]

(curtsey)

I have had a few GFs over the years:

Tell me they liked to dress up guys as girls

Ask me if I would wear their panties, bras, nighties, other lingerie when we went to bed.

Ask me what I thought of guys who dressed as girls.

Ask me would I get upset if a GF asked me to dress up as a girl.

I always let them know in less than ten minutes that I liked to dress up like a girl, particularly the underwear. They were always happy and wanted to rip off my drab immediately and get me in drag.

Later, I would show them my collection of lingerie and dresses. They were amazed, a usual comment was 'yours are nicer than mine!'.

They all liked my little girl party dresses and petticoats, many had not seen such in years.

I would say let her know.

(curtsey)

[BiOpi]

Personally, I would challenge her to dress me up, and then when she did, state that you like and see how she felt about it and go from there. That way it's not thrusted upon her and you can either ease her into the idea or at least not be exposed negatively. Does that make sense?

[Jill]

Thanks everyone for your insights, you have given me some good ones and some stuff to think about. It's true that she was the one that brought it up initially. I also agree that maybe this is her way of feeling like she is in control, which is fine to me cause the whole things just sounds really fun. I agree with you Carolyn, I should seem curious but not eager at first and then see her reaction once it's done.
I guess my next question is, now that Halloween is over, and really there's no valid excuse to bring up a costume subject, or something that would lead the discussion toward dressing me up. Anyone have any ideas of how to bring it up fairly casually which would hopefully result in her dressing me up? I was thinking maybe I could ask her how her Halloween saturday was and if she got to dress up any guys as girls. Anyone else have any clever ideas?

[Nikki A.]

hey why not ask her how she thinks you would look all dressed up. That should get the ball rolling. From there take t slow and easy. She would probably jump at the chance and you are on the way. Lucky you I'm jealous

[mchelle]

everyone should have someone to help them dress.
i hope to have someone like that..
good luck w talking to her again

[jessicadiane]

I guess my next question is, now that Halloween is over, and really there's no valid excuse to bring up a costume subject, or something that would lead the discussion toward dressing me up. Anyone have any ideas of how to bring it up fairly casually which would hopefully result in her dressing me up? I was thinking maybe I could ask her how her Halloween saturday was and if she got to dress up any guys as girls. Anyone else have any clever ideas?

That sounds like a good idea Jill or you could do the "I have a friend who heard you dress guys like girls and he would be interested" routine and maybe see what her reaction is.Good luck with whatever you do. We are here for you if you need any other suggestions

[Wenda]

JILL!!! LISTEN TO THE GIRLS!!! WHY ARE YOU STILL SITTING HERE???? GO..GO..GO!! ONCE IN A LIFETIME OPPORTUNITY!!!!! wenda.

[Jill]

I guess the thing that I am the most afraid of, my biggest thing that is holding me back is that I was thinking that just because she likes to dress guys as girls, doesn't mean she would be comfortable with someone who actually likes it and wants to do it too. Maybe she's not ok with crossdressers? Is that stupid? Does that even sound possible? Do I sound like I am being paranoid or does anyone think that could be a possibility? Cause if that were true, I certainly would not want to just jump at her and say let's do it, then it would scare her off and freak her out. Am I being too worried?

[Wenda]

I think there is some good advice in the earlier postings. I would raise her comment with her, and tell her that it is also something that you have thought about, and would be interested to play along with her. I wouldn't spring the whole thing on her, or show up completely dressed. Ask her what you should buy or bring. She will probably say nothing, and use her makeup. Let her lead the project, and reveal more and more of your wardrobe and interest as the situation allows. She will think she has created you. Good luck. It is normal to be nervous. Just proceed thoughtfully and see where it leads. wenda.

[Julie]

Jill, that has been my concern from the time you posted this thread for the exact reasons you've just stated.

Worst case scenario is that she might see your CD'ing as something directly opposed to what she might want to achieve. By that I mean does she like dressing men as women because she feels this embarrasses them and this whole thing on her part is a power kick.

Best case scenario is that you and I are wrong and you're in for a real wild time.

Julie J

[Kaye_martin]

I guess the thing that I am the most afraid of, my biggest thing that is holding me back is that I was thinking that just because she likes to dress guys as girls, doesn't mean she would be comfortable with someone who actually likes it and wants to do it too. Maybe she's not ok with crossdressers?

Jill: She raised the subject, so why not just go for it :)

Kaye

[jade lee]

Marry her, you will never find anybody like that again!!!!!!!!!!!!!!!!!!!!!!!!

[softandsmooth]

Hi,

Personally, I think that this would be a great opportunity. Perhaps you just happened upon one of the rare few that can not only tolerate, but encourage and appreciate men who like womens clothes.

Perhaps she does see this as a control type thing. It is possible. For some of us that may also provide a sense of relief and solace. Does that make sense? That we don't want to always be the ones "in charge", and that dressing relieves us of that burden for a short while?

ANyway - I am blathering. I would go with the "curious but not eager at first" idea. See if you can bring it up in conversation (private) if you can. IF not, throw a costume party and invite her over - to dress you up.

I seem to remember some room mate issues from a while back, so maybe some other costume party at the University.

Charlotte