I am 18 and so is my girlfriend Cindy and we are in our last year of high school. She has asked me several times now to wear some panties and a skirt for her, because she thinks it would be sexy and fun, and she has promised to make it worth my while. On the one hand, I am very reluctant to give in to her request since I have never done anything like this, but on the other hand I do find the idea just a little bit stimulating. She said that she would take me shopping to get something to wear for her, as soon as I was ready. I like her a lot, and don't want to offend her and mess up our relationship, but I am also concerned about what else this may lead to, that could be very embarrasing for me.
What do you think I should do about this?
2006-12-27 06:34:25 · 24 answers · asked by Anonymous in Family & Relationships ➔ Singles & Dating
I have no idea why any woman would ask a guy to wear a skirt, that makes no sense to me at all. If i were you, no i wouldnt do it because thats not something you should have been asked to do to begin with and why embarass yourself your last year of high school for some girl? Seems a little fishy to me but that just me, or a few other ppl think so that have already answered, that should say something. My advice to you is, don't do it, it wont be worth it at all.
2006-12-27 06:49:50 · answer #1 · answered by JMan 3 · 1⤊ 2⤋
You lucky guy! This girl sounds like a lot of fun. Do it. No telling where it will lead. Anyway a skirt on a guy is no big thing and not cross dressing unless you are trying to look like a girl. It's likely skirts for guys will make a comeback and you could be leading the way. Don't get something frilly or girlie. Probably a denim mini with pockets and it will be practical to wear whenever! Enjoy the moment and don't pay attention to those who are obviously insecure with their own sexuality!
2006-12-30 16:50:58 · answer #2 · answered by Patagoniakidd 6 · 0⤊ 0⤋
As long as you don't find it to be wildly uncomfortable, go ahead and give it a shot. Flexibility is an important part of any relationship, and being willing to try something new for her may make her more willing to return the favor in the future! Just be ready to stand firm and draw the line if it *does* escalate to where you're uncomfortable with things!
2006-12-27 06:39:21 · answer #3 · answered by supererogatorysesquipedalian 1 · 1⤊ 0⤋
Some women are really into guys that crossdress. It has to do with the fact that crossdressing is considered taboo, so they find it exciting/arrousing.
Go ahead and do it if you think that you might like it. There is nothing wrong with experimenting and trying new things, as long you aren't hurting anyone. Afterall, that's how you find out what turns you and your partner on the most.
Personally, I say go for it. I think you might be suprised at how fun it can be.
2006-12-27 06:47:22 · answer #4 · answered by Ritz Grimarren 3 · 0⤊ 1⤋
if you are not being embarrassed I say go for it! it can't hurt. just make sure she isn't up to something and that this a legitimate request. Otherwise have fun with it! You can deal with other request as they come. Don't do anything that makes you feel uncomfortable or compromises you.
2006-12-27 06:40:49 · answer #5 · answered by Jan l 2 · 1⤊ 0⤋
well if its going to be just the 2 of you no pictures camcorders than it may be cool if you want to do it just for her maybe deep inside she wants to be with a woman and does not know how to go about it but if its something you want to do for her that would be cool but look out b/c us girls can be sneaky so make sure your at your house where you know there are no hidden items or people so think about Ange good luck with your decision but if you decide to say no and she gets upset or breaks up with you than you know that there was something up with that and she wasn't worth it anyway
2006-12-27 06:47:29 · answer #6 · answered by Lady Jay 2 · 0⤊ 0⤋
I would laugh so hard. Have you seen John Tucker Must Die?? Sounds like you are in his situation. I would never make my man do that. I make him do things with the same reward, but never a skirt and panties.
Have Fun!!LOL!!
Please send me a pic!
2006-12-27 06:38:55 · answer #7 · answered by Anonymous · 0⤊ 0⤋
Do Not Wear A Skirt, or anything else feminine. What if a picture were to surface of you in a skirt??????
2006-12-27 06:38:29 · answer #8 · answered by NAN G 6 · 0⤊ 2⤋
just be prepared if you do it to bend over and start taking it in the asss because clearly she wants to be the man
2006-12-27 06:37:56 · answer #9 · answered by gremlin 1 · 0⤊ 0⤋
just go for it. make sure u get something in return though. good luck and have a happy holidays.
2006-12-27 06:39:34 · answer #10 · answered by Joho 7 · 1⤊ 0⤋