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Thread: Advice?

  1. #1

    Default Advice?

    So a good friend of mine is very much into Lolita, and as she knows about the little girl side of myself, she's offered to have me wear some of her clothes around her. Now, I know very well that cross-dressing is a "thing" for me, at least in my head, and that I eventually want to try it out just to confirm that I get the same feelings in real life as I do in my head. However, I got really flustered when we started talking about this over the phone, as if knowing that actually wearing clothes like that around someone else could very well happen within the next few weeks just kinda overloaded my mind. It was too much for me to handle, so I told her that I needed to think some things over before deciding on anything concrete. In truth, I'm not too much into Lolita (I'm a firm believer in simplicity being the cutest quality in clothing, and the outfits I've seen her wear are nowhere near simple), so I don't know how willing I'd be to just jump straight to wearing that kind of thing...I feel like I need to test the water first, like dip my toe in before diving. I feel like I'm rambling at this point, so here's the point: What's a good first step in deciding to cross-dress around another person? To help with my mental image without shaving anything, would knee-socks be all that helpful in covering up leg hair? Any other advice you can give for a first timer? Thanks in advance.

  2. #2


    Simplicity eh? Think the first outfit I ever put on was black tights, black summer skirt, plain jane girl's top, 4 inch heels and some jewelry. Hell you could even opt out of the skirt and just do girl's jeans if she's got some that fit you. That Gothic Lolita look takes a few hours to get on and right that I wouldn't be doing it myself.

    So I'd get full length tights as knee socks aren't going to cover everything, Plain jane girls top, shoes, and a couple accessories. I have a somewhat androgynous hairstyle where bows and headbands work for me. Try those out if they suit you or go for a wig.

    You end up wanting to paint your nails half-way in. Do only one light coat if you plan on taking it off. I take it off next day before work. Little bit of eye shadow and little bit of mascara is also fun once you feel comfy.

  3. #3


    I don't cross dress except that I enjoy wearing the pink Baby Pants training pants. I think you should only do that which makes you comfortable. Yeah, the Lolita look may be well over the top. Explain that to your friend and if she can't or doesn't want to work with that, then say no. It took me years to say "no", but now I say it very well.

  4. #4


    Well, if she's interested in seeing you with Lolita clothing, she'll definitely be ok with something less over the top. I'd tell her that you want to start slow. She'd probably love to help you out, give you tips, while letting you ease into it. Maybe just ask her for some things you could try on by yourself first.

    Honestly, you're lucky you've got a friend who's so open. The part where you should worry about her finding out and judging you is over, so be glad you've found a person who's open to you sharing that part of yourself.

  5. #5


    Speaking of nail polish, if any of y'all are interested, you can buy little girl nail polish and it is "peelable". Meaning very easy to get off when you need to, and generally without leaving any residue on your finger nails. You can scrape it off with another fingernail for the most part. Now, this also means it doesn't hold up well in daily activities, but the convenience of not having to deal with nail polish remover etc is great. Example:


  6. #6


    Cross-dressing in front of another person is a big mental barrier. My girlfriend knew I was an LG right from the beginning, and we'd done some text-only roleplays, but I was still completely petrified to show myself in girls' clothes in front of her. I get the feeling you're going through!

    The most helpful thing for me, honestly, was just diving in. One night we were talking on webcam, and she saw how nervous I was just at the subject, and encouraged me to put on one of my dresses. Well, I started mentally preparing for her to hate me after, but I did it anyway. She was completely supportive! Having her see me dressed up, and tell me I was cute instead of horrifying, lifted a huge weight in my heart. (I know I wasn't cute; I was 100% a guy in a dress, no makeup or anything!) But that show of support made me accept myself far more, and feel more at home with my LG side. It was really life-changing.

    I think the most important question is whether you 100% trust this girl to keep your secret and accept you. If you do (which it sounds like from your post), then my best advice would be to just do it. The fluster you're feeling sounds like mine, which was a fear of sudden rejection and being hated. If she's willing to offer, though, and she's not a duplicitous person, she's probably trustworthy. Most people aren't going to try and trap you! She knows what cross-dressing means for you, and she knows how vulnerable it is to share this part of yourself. If she's your true friend, then it may actually be really beneficial to you to try this out.

    In the end, the most important thing with being an LG is how you feel about yourself. If you love yourself, it's not a burden to carry, but something you can delight in. Being uniquely yourself and knowing you're OK. If you trust this girl, then take her up on the offer and give it a try. Even if it's for thirty seconds. To know that you're a good and accepted person, even all dressed up, is n invaluable gift.

    (By the way, if you don't want frilly dresses, send them my way! Seriously, if she's very accepting, perhaps you can get ahold of a dress that appeals to you more and she can look after it for you. See how it goes! Good luck!)

  7. #7


    Thanks so much for all of the helpful advice! I really appreciate it.

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