Long finger nails are not conducive to certain physical acts, particularly digital penetration. The old joke goes, “How can you tell that the women in the girl-on-girl scenes in straight male porn are not really lesbians? They all have long finger nails.”
Yes, long fingernails hurt. Quite a bit. To the point that I’ll turn the light on, get the fingernail clippers and cut them off. (of myself - I’d be more tolerant of a lover)
False nails I’d imagine would hurt more - but short nails can still be pretty when painted 
(don’t use a red nail paint as it can stain your cuticles.)
Well, I guess it just depends on the person. As long as my girlfriend remembers that she’s wearing the fake nails, I love how they look and feel.
Hmmm… food for thought. I still like the suggestion and am leaning towards going with them. Besides being part of the “look” I think they will further the goal of making me be more unrecognizable as “me.” And I think they can look sexy on a girl, so I would imagine they’d fit into her fantasy that much more. But, of course, I did ask for the advice and don’t want to stick with something just because.
Here are a few thoughts. Feel free to let me know if this doesn’t add up:
Yes:
No:
So it seems like as long as I’m careful and avoid certain acts that aren’t all that necessary…
And eventually, when she wants to wear a strap on and make you the woman for awhile are you onboard with that too? Might want to get the big picture worked out upfront. 
EEK!!! That is NOT a direction I considered. That would be a test of my dedication, wouldn’t it. Hmmmmmm… Since getting the ‘meet her in the park’ idea into my head I’ve been thinking this would be quite the surprise. (Not the total freak-out kind of surprise, but the “holy cow I didn’t expect this tonight, weeee!” kind of surprise.) I don’t quite know how to casually bring that up over dinner.
Glad to get the heads up on that. That may be a bridge I’ll have to run the risk of crossing. Wasn’t there a thread a looonnng time ago on that subject or something similar? Something by Satan, I think. If anyone remembers and can find it, it may turn out helpful. Or maybe I’ll have another interesting OP.
Wow, you’re awesome. Most guys would flip out at the thought of cross-dressing and bolt for the door. It’s so cool that you really care about pulling this off. Um, I don’t know what kids of clothes to get, I just wanted to say that you rock! But then again, I’m fascinated by drag queens. Woohoo.
Wow, indeed.
Ya know I had a thing for Binkley when the strip was out (is it ok to have a thing for a little boy if he’s a cartoon character? Well, anyway I was a little girl at the time). And beyond that, you’re impressively sexually adventurous and managed to work Aristotle’s Ethics into a post about kinky sex…
Sorry to hear about that girlfriend. Lucky girl!
I’m betting there are tons of places you can order women’s clothes and shoes in large sizes (aka meant for men). So you wouldn’t have to deal with sales people. There are cross-dressing magazines that would have ads. But then you have to be seen buying a crossdressing magazine…
Oh, if she goes the route astro mentioned, I hear “Bend Over, Boyfriend” is and excellent movie on the subject.
You realize we’re all going to want to hear how this goes?
Just shaving the wrong way might do the trick.
Don’t ask me too many questions about how I know all this…
Shaving is a must. Shave your chest, legs- everything- as close to possible as to when she meets you. Heavy make-up is your only real solution to your shadow, unless you want to go to the extreme of plucking out your beard, which looks great but is increadably painful and can lead to ingrown hairs.
I’m not all that knowledgable about make-up (as a girl, I wear excluseivly glittery eye shadow and candy-flavored lip gloss). Find a good referece and follow their advice. As this is a romantic encounter, it is a really good idea to get some extended wear lipstick. You can buy it at the drug store and it comes with two tubes- one of a paint like substance and one of gloss. I forget the brand names. This stuff won’t come off while kissing and won’t come off on glasses and the like. Regular lipstick is far too much hassel if you are not used to using it, and it is ill-suited for romance. Practice your make up a couple times before the big night if you can. Keep the lights low and you’ll look fantastic.
I’m not sure how much of an investment you want to make, but a corset will make all the difference in the world about your shape. A good one will run you way too much money (in the eighty dollar range) but you can find decent ones online for forty or so dollars. You’ll need something good and sturdy because you will be changeing your shape a bit. You can wind some packing tape around your chest to create some cleaveage if you have anything to spare up there. Then put on a bra, stuffed with some or another. Then put on a corset if you have one. If you do get a corset, wear it around a bit so that you can get somewhat comfortable in it.
You can also look into making some hip/thigh/butt padding with foam and bicycle shorts to make your dress hang right.
I don’t know how happy you are with the wig you have, but there is a person names HongKongColor (who I have nothing to do with) who sells beautiful wigs on Yahoo auctions for around twenty dollars. Use a skull cap of some sort before you put on your wig to keep it on.
Ross is a good place for larger shoes. Opt for chunky heels instead of pointy ones. Practice walking around in them- it’s hard. I can’t even do it. You ought to be able to fit into larger women’s regular clothes without too many problems. Just buy what looks good, try it on at home, and return what you don’t end up fitting into. Look for things that have a little bit of shape and structure to them- tailored shirts and the like- not things that are too thin or skimpy. A skirt and a shirt will have a better chance of fitting than a dress. A jacket of some sort can also do wonders for an outfit.
I hate to say this, but I’d be pretty careful if you go out in public. You might end up with unwanted attention and it could get uncomfortable. People suck. Have you considered picking her up in a car?
But you rock! Good luck!!! You guys are going to have so much fun!
grrrr post didnt work last time… luckily i copied it just in case
uhhh are astro and i the only ones who are really thinking about the long term? what happens when you go through this whole tranformation, for however long you decide to fulfill her fantasies (one night, forever…), and she then realizes she likes the whole being with a “woman” even more? hopefully it’s just a one time thing or something, but what if she does decide to try being with a real woman and leave you? or the strap thing like mentioned previously? how far are you willing to go? hmm… pretty far i guess if you’re seriously considering being a cross-dresser. anywho, more power to ya… i hope it works out for you in the end.
btw here’s a link to do your makeup
Plenty of excellent advice already given but this is to respond to maybelze05’s post.
If those urges are already there, it’s best to discover them asap since they’re not going to go away and repression is most likely only going to make them stronger or express themselves in worse ways.
http://www.interlog.com/~lis/cd/transformation_contents.html
That should be everything not covered previously.
An additional problem with press-on nails is that most brands you’ll find at the grocery store come with their own adhesive pads. They don’t work. You might drop a nail in a…in a place where it would be awkward to retrieve. Regular nail glue is probably a little more heavy-duty than you’d want for a single night or just for the weekend.
My suggestion: head to your local strip mall nail salon and get a manicure. Guys get them all the time at the salon I go to. It’ll run you about $10. Your nails and cuticles will be even and look nice and you can apply the polish at home.
As for the lipstick, go with the stay-on liquid lip sticks. They work much better than the other ones. I, personally, have noticed that the Cover Girl 8-hour lipgloss doesn’t last through a long make-out session; however, that might have been because the time I tried that particular brand out was the day that I saw my SO (at the time) for the first time in weeks and also due to the fact that my teenage hormones were raging. Another thing to be taken into consideration is the fact that these lipsticks can be very drying- after wearing them, you may want to have a moisturizing lip gloss or chapstick around for awhile.
It is about three here, but I am a bit toasted from the evening. Thought I’d pop in and throw out an update (assuming there’s still interest).
First off, I gotta admit I’m a bit on the fence about something. Part of me wants to swagger a bit in this thread and be all macho – “HA,” I would say. I’d like to go on and feed my ego about how great I appear, how considerate, how confident I must be in my sexuality… la la la la. But I think that would be somewhat false modesty.
OK, so maybe some of the above is true, maybe most guys would run from the room, maybe this is just a little above and beyond the call of duty. Well, some of it definitely is, I’ll get to that later. But for now, honesty (or maybe it’s all the beer) dictates that I come out and say it – it’s all about the sex. Ugh, sorry to deflate anyone’s image of me as a nice, gentle, sensitive-new-age-guy[sup]*[/sup] but it all comes down to the sex.
Consider this. If the OP came about because she wanted me to dress up as a pirate, some might think it’s sexy, but no one would raise an eyebrow and tell me she’s lucky. What about a fireman? No problem. I’d normally run from a fire (was in one once, and boy did I run!) and have no claim to the laudable bravado needed for the job. Same thing with a policeman. Doctor? Shepherd? Construction worker? Well, I think you begin to get the point. This is pretty much just a costume. I hope that if she wanted me to dress up as a pizza delivery man I wouldn’t hesitate, nor would I worry that the next time we order pizza I should keep an eye out.
And it’s not as if she is merely asking me to wear that green turtleneck out tonight because she likes it so much. Sure, I’d do that because she’d think I looked a wee bit better, but I wouldn’t find that much of a need to, not that much of a benefit. But now? Based on the things she’s said and the reactions she’s had when we’ve talked about it, by indulging this corner of her secret urges she will be consumed by the very essence of prurience. And the thought of that puts me in a state where I can… well, break plates. Make sense to any sober people reading this? So sure, I am taking some risks, doing things I certainly wouldn’t want anyone outside of anonymity to know about, but all in all I’m doing this all for two simple words: great sex.
Anyway, now that I have that off my chest (of course it may not seem too coherent a thought in the morning) here was my day and my thoughts on tomorrow –
I appreciate the suggestions of 'net-stores to get things from, but for whatever reason I got it in my head to do this Sunday evening. (Mind you, just because I’m doing this for base reasons doesn’t mean I am completely confident in it, and don’t recognize the risk of chickening out.) So whereas I don’t want to rush into it, I don’t want to loose the momentum.
So I headed out today to a local Adult Specialty Shop. I was thinking of hitting the local Fredrick’s or Victoria’s, but found this ad and liked how it read. Women owned, seemed very proud of their helpful staff. Sounded like I’d be more comfortable there than with some retail-mall-worker. So away I went, and I am soooo glad I did.
Ok, another confession to make. I lied. I couldn’t quite bring myself to tell them what my real motivations were (though after a while I realized I could have) so I told them I lost a bet with her and I was looking for an outfit for a costume party. Whatever, small thing, they were very friendly and helpful and made this a lot easier and more fun than had I grabbed stuff off the rack and split as soon as possible.
No, these great folks took their time with me, showing me allll sorts of things. I am definitely heading back there with her to get some more traditionally sized outfits. I was surprised at how nice some of their stuff was, and had to remember who I was ‘shopping’ for.
To make a long story short, after looking at several things, getting into a lot of detail on the style I was looking for, what she liked, etc. I ended up with a cincher-thingamajig. They had really nice looking corsets for 250 – 300, well above any laughable reach of what I was looking to spend. The great thing is that the cincher (that’s what they kept calling it – I’m not sure what the difference between that and a corset was, but there you go.) is small enough that with enough tightening of the strings it will fit her. So no real waste there. Same thing with this dress they had. It is shearish with light dragons on it, open in the back, long slit up the leg.
It was a bit weird picking things out. I couldn’t tell what part of my brain was working on the choice. What would look good on her, what would I want to be in, both have to do with my taste, yet from very different angles. Weird, I tell you. But you can probably imagine.
So these unbelievably helpful salespeople (all three working that day were helping, we had a good time over the hour or so I was there) helped pick out those two basic items after very patiently showing me lots of different options. They had this great idea to throw the cincher thing on over the dress and throw on a blazer or sweater (those from a basic discount store) over the top so my arms will be covered when I’m out (and I won’t freeze). So get this… how good were the salesfolk? How nice and reassuring were they? Good enough to convince me to try them on in the store!. Yep, I never in a million years would have thought I’d do that, but there you go. Great folk. Really felt comfortable, and had lots of fun – like I said above, very similar to putting together a Halloween costume. Oh, by the way, you know what? I’m one hell of an ugly woman. Yikes!
So I’m once again out on the fence about meeting her anywhere but in the confines of the house. We’ll see, tomorrow afternoon I should have everything I need, and I can try it on and let her know where to meet me at the last minute.
So far I have the chingerything, a dress, stockings, garter and a wig (went better with the dress than the blonde one from Halloween). Tomorrow I’m hitting the stores for a cheap pair of shoes, some bangles, some perfume and the makeup/ nails. All with the suggestions from this thread in mind. (I’ve already spent around 130 on this so far (told you some of this was above and beyond) and hope not to spend too much more. If things work out she’ll be able to inherit the dress/ chingerama, but we’ll see.
I’d post pictures of what I got if anyone is interested, but though I have a camera, I don’t have any web space to put them on. If anyone wants to see them and knows of a free place to drop them, let me know. I’d have to imagine if you got this far in my buzzed ramblings you still have * some * interest.
I’ll also post ideas on how to set up the evening, and encourage anyone out there with any thoughts to do the same. Only thing I’ve come up with so far (based on me not leaving) is to go out and pick up six or so roses during the afternoon. Darken the house, light a fire (in the fireplace) and set out some candles. I’ll leave the flowers in a trail from the front door to the back of the place. To each a small card will be attached, each with a separate word: tonight – set – inhibition – aside – indulge – yourself. What do you think? Too cheesy? Reads that way, doesn’t it. Oh well, I hope I can think of a way, or hope to use on of your ideas.
I have a looong day ahead of me, don’t I? I should go and get some sleep.
Sorry for posting drunk, btw.
[sup]* Well, I do like a Christine Lavin, but I’m not sure that really says much of anything.[/sup]
Another quick suggestion: Watch how women walk. Try to copy. The heels will help this a bit, since high heels change a person’s entire walking motion (do wear these around the house when she’s not home, as one looks infinitely better in heels when one knows how to walk in them).
One of the quickest giveaways for many crossdressers is the walk, because men and women are built much differently hipwise, and their weight shifts differently. When I’m cross-dressing as a man, for example, I have to concentrate on not moving my hips at all, and it’s not as easy as it sounds.
Subtle motions can really make an illusion. The way [most] women flip their hair over their shoulders, the things they do with their lips when they think, the way they stand, the way they sit … things like that.
I’d also like to echo that you are an awesome boyfriend to do something that most guys would see as a threat to their masculinity. Good luck!
Too many cross-dressers dress like their mothers or grandmothers, with fussy, matronly clothes, makeup and hair. It’s the rare cross-dresser who dresses like today’s women really do.
Boy, the reason everyone thinks you’re so considerate and wonderful is the attention to detail, and how you’re determined to get it right! I’d feel the same if you were so determined to get a pirate or firefighter costume “just so”. If it was really ALL about the sex, you’d dig up some stuff at Goodwill, slap on some lipstick, and enjoy the "appreciation’ sex that would definitely follow. No, you really want to get it right, and that shows a level of caring that I’d venture to say more people wished their relationships had.
People are recommending you shave your arms, but how dark is your arm hair? If it’s fair/thin and you’re wearing a long-sleeved outfit, you could get away with leaving it in place. Almost every woman I know leaves her arm hair alone.
And another warning - when your shaven hair grows back in, be prepared for itching. Lots and lots of itching. You have no idea.
If you use any depilatories on your face, get the version made specifically for use on the face, and regardless of where you use the stuff, be sure to first do a “patch test” (the bottle will give instructions). Don’t expect miracles either - my experience has been that it still leaves some hair behind.
Consider getting some good-quality disposable razors to do your leg shaving; from what I’ve heard, you really don’t want to be using the same razor on your face as on your legs, as I guess it is rough on the blade.