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On Halloween a guy I know said he wanted to dress as a girl. He asked if I would help him. I liked him and thought it would be fun. So I helped him get a costume and a wig. He came to my house and I put some makeup on him and did his hair, He actually looked cute. So I started putting more complete makeup on him and some earrings and jewelry. Now he really looked cute! So I got him to wear one of my bras and panties, and the stockings and hi heels we bought. I also put pink French press on nails him. I had fun making him look like a glam girl! He did look like real girl. Very pretty and feminine too. We went to a party and a club and had allot of fun.

Now we have become BF and GF! Today he asked me to dress him up as a girl again. So I did and we even went shopping and stuff. I thought it was allot of fun!

What do you think? Is this going too far? Have any suggestions or advice?

2007-11-09 21:48:08 · 24 answers · asked by prettiestgirliegirl 2 in Family & Relationships Friends

24 answers

Going too far? Probably not, you don;t mention how old you or he is. Cross dressing is basically harmless. You should consider yourself fortunate that he has trusted you enough to share this with you.


I had an ex that expressed just this desire. He had been cross dressing since he was 14 or so. The problem is that many women, especially younger ones are threatened by something like cross dressing. They believe that it means the boyfriend is gay or about to become. Nothing could be further from the truth. Most cross dressers are not gay, they are straight.

Because a male, of what ever age wants to wear clothing of the opposite sex, you need to realize first that it takes an increadable amount of trust to share that with someone. Most adult cross dressers have long standing and good marriages simply because of the openness and honesty. (Not all mind you, one of the biggest mistakes cross dressers make is trying to keep it a secret. Usually the wife finds out years later and feels betrayed. The loss of trust is very devistating and frequently ends the marriage.

There are many avenues of cross dressing. A frequent way to indulge is to wear panties, a bra, maybe small breast forms under otherwise normal clothing. Sometimes they can wear keds or other womens shoes. My ex never had a problem doing that.

Just because he wants to wear womens clothing does not lessen his value as a man. To reject that is simply immature.

Good luck, be yourself and be proud of who you are, but be careful, if you walk into a redneck bar wearing a tight little black or red dress and high heels, there is gonna be trouble and you will probably be on the receiving end.

On the other hand, there are many safe venues if you wish to cross dress. Use common sense!

2007-11-09 21:59:44 · answer #1 · answered by Clara Nett 4 · 5 0

It's OK to help your boyfriend dress-up as a girl, if he wants to dress as a girl more often, then he needs to learn how to dress-up himself as a girl. I don't think you've gone too far, I had a couple of girlfriends who actually wanted to dress me up as a girl & that was before they knew I like to crossdress. My wife is supportive & enjoys having a girlfriend around the house too. The best advice I can give you is to keep having fun & communicate with each other, now you can really start to have fun together. Now you can have slumber parties, makeover parties, girls night out, girls weekend away, the possibilities are endless. I wish you the best & I'm going to add some links for crossdressing & transformation services.

jk

2007-11-09 22:15:04 · answer #2 · answered by J 7 · 3 0

Honestly, there is NOTHING wrong with it, and there are many reasons why many men and women enjoy crossdressing, or helping their mate crossdress. Men for example, generally are looked apon by society as having to be dominant and strong, so they seek refuge sometimes, by making themselves look like females, causing them to relieve tension, because when they are like that, they dont have to be dominant or strong. I've actually tried crossdressing, its not quite my cup of tea, but I still do it on certain occasions, for example, my wife and I are going to gay pride this year with me crossdressed. Anyone who thinks that this is a problem is simply narrow minded, and should be ignored. I have friends that are currently undergoing the process of genital reassignment or in otherwords, working towards their sex changes. see, I am a straight male, But I do enjoy dressing up as a female, Just not going out into public like that, mainly because i live in a small city where everyone knows everyone. Anyways, I could talk for hours on this subject... hope i helped somehow.

2016-05-29 01:29:24 · answer #3 · answered by jennette 3 · 0 0

I can not believe the number of people here who answer these question and are so clueless. Just because a guy wants to dress in women's clothes, it does NOT mean he is gay. Try looking up the meaning of a word before you use it. Just because he wears women's clothing does not make him want to be with men. Many men wear some articles of ladies wear and NEVER have thought of the same sex. It just means he wants to wear soft silky clothing.
To answer your question, NO this is not going too far as long as both of you are OK with it. What two adults do is nobody's business. Enjoy yourselves!!!

2007-11-10 16:55:35 · answer #4 · answered by Sheerhose 4 · 2 0

Congratulations! I think it's great that you can both have fun with his crossdressing. He's lucky that you support him and help him to pass as a cute girl. Now you can have the best of both worlds, a boyfriend who is also your girlfriend who you can go shopping and clubbing with. If you're not the jealous type it might be fun to double date with him/her. Many CDs are bi or at least curious. Who knows, you might enjoy watching her go down on his date. It can be very erotic. Have fun and enjoy..

2007-11-10 14:28:30 · answer #5 · answered by debbysfemail 3 · 4 0

No such thing as going to far it's what you like. You can have A lot of fun dressing up....especially during eroti/intimate games.

2007-11-11 08:02:43 · answer #6 · answered by Anonymous · 0 0

Hay he might be better in bed! He'll know what a woman wants. Trust me on that...go with the flow.

PS you 2 will be a lot closer, secrets are never held

2007-11-10 06:16:49 · answer #7 · answered by Anonymous · 1 0

Hey - whatever he's into is OK for him - thing is are you into it too - think it through all the way. Would you introduce him in girl's clothes to your parents ? Or would it have to be a bed room secret?

Would you be happy with that?

2007-11-09 21:52:25 · answer #8 · answered by Wayne ahrRg 4 · 1 0

if your enjoying it and he is then go for it.

if your not enjoying it then no

also you have to think about what hes really after.

is he doing it just for fun, or is he doing it because he ultimately wants to transition to living as a female. and if its the later could you accept that and still be with him?

as long as its something you personally can live with and have fun with, then yes its ok!

2007-11-11 11:57:38 · answer #9 · answered by Arianna 3 · 0 0

good on the 2 of yous, this could be a shady scene if he kept it a secret. go to more parties and clubs, and shops and stay pretty

2007-11-10 00:43:58 · answer #10 · answered by m 2 · 0 0

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