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Why do men cross dress?

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I should point out that I'm female, but the reasons why men crossdress has never been too complicated or hard to understand for me.

When I was a young child, I remember wanting to be a boy. I felt I related more with that gender in just about every way. I used to put socks in my shorts lol.

I was a serious tomboy until about 6th or 7th grade when I started going through puberty. I still liked mostly male-centric things including heavy metal/punk music but this is about the time where I discovered makeup and how much fun it can be. I always had short hair, usually only 2-3 inches long, I preferred it that way but always sort of felt I didn't look girlie enough compared to my peers. I remember during my eight grade graduation when I wore a floor length gown, I just felt akward like a guy in a dress.

It wasn't until the end of highschool that I actually wore a pair of high heels. Sure, I wore shoes that happened to have a heel, but these were sexy, strappy, black, stiletto heels that belonged to my sister and I was used to wearing doc martens. I was just trying them on with a skirt I owned but never wore and it was such an unexpectedly exciting moment. My legs looked long and sexy, my ass looked hot, I couldn't walk in them but I still felt like the sexiest girl in the world. It felt euphoric and I suddenly knew what the fuss was about. I felt comfortable in women's clothes and wearing them really boosted my confidence in myself.

I imagine for men, crossdressing is a lot of the same exciting feelings. Let's face it, being girlie can be a great amount of fun! It can make you feel desirable and confident and delicate all at once.

I think society's stance on gender roles is antiquated to say the least. Obviously, things can never be so black and white or should I say, blue and pink. "Male" and "female" characteristics shouldn't have to be mutually exclusive. It breaks my heart when something so harmless is so misunderstood and vilified on the basis that it isn't "normal". From what I understand, "being normal" seems pretty boring and restrictive to me and I don't want any part in it.

The fact that so many crossdressers live in shame or in fear that someone will find out about their secret is heartbreaking to me. I sincerely hope that they can make peace with themselves, and that maybe one day society will follow suit.

Stay strong, boys and girls.

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Jo, thanks for sharing - I'd never though of it like that. It's wonderful to hear this from your perspective as a women, who grew to love feminine clothes.

I can definitely vouch for my experience the thrill of looking good, feeling desirable and confident when wearing women's clothes. If I take it as a purely intellectual exercise it's somewhat absurd to think that it would be the case, but my experience and emotions tell me otherwise.

Thanks again for your support Jo - I hope to see you around crossdresser heaven again.

Hugs,
Vanessa

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Sophie, it's wonderful that you are strong enough to be who you are. The most important thing is to be true to yourself, even when others have different expectations on you.

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I never really delved into why I enjoy getting dressed up and in touch with my softer and more feminine side until finding this site.

I suppose it has a lot to do with the fact that in my everyday world,I am the aggressor and a 'take-charge' type guy. When I need a good balance and to destress....I will open up the two suitcases that allows me to relax and luxuriate in satin and silks. I also tend to become much more submissive when dressing and this is why I truly believe my crossdressing really balances out my persona both emotionally as well as spiritually.

I've always said..."If it makes you feel good and doesn't hurt anyone else....what's wrong with it?"

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Why do men cross dress?
Why do people smoke?
Why do people sky dive?
Why do people ...?

We do what is pleasing and feels good to us.

As has been repeated over and over again, females can wear masculine clothes and nobody bats an eye. But for a male to wear female clothes and he is ridiculed. But there is hope that this may change in a few years. Men can wear ear rings now in public without shame.

Also with the internet, this is getting more publicity and more men are wearing female clothes in public. I myself work out in my yard, front and back, in skirts and dresses. Every other week I cut the grass in my skirt or dress. The neighbors have seen me like this and have gotten use to it. They have come over to talk to me about other things while I am in my skirt or dress and they have not said anything. I even had one young woman selling steaks try to get me to buy some while I was outside in a dress. She did not say anything about my dress nor did she appear uncomfortable about it.

I did one time late at night go to the post office and purchased stamps while wearing a short denim skirt. Other customers in line did not say anything. I also purchased gas for my car while I was out and had to go inside to pay cash for it. The clerk and another person inside did not say anything.

Only if "everyone" starts going out in public in a skirt or dress will it become acceptable. It just takes being able to take criticism. I hope to get up more courage soon and go to the grocery store in my dress or skirt.

Being a single male living alone makes doing these things easy for me.

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G'day, I have been dressing up since 4yrs of age, playing dress up's with the girls across the road. 39 yrs later, I now wear lingerie everyday, and sleep in stockings or pantihose, with a nightie or babydoll. The wife does'nt like it but she no longer gets cranky. I too just feel more comfortable, when wearing womens clothes, although I sometimes paint my face as it were, that does not really matter. I buy all my own stuff, and always have, with never a problem, although a couple of salesgirls have blushed quite a bit when they finally twigged that I was buying for me and not wife! Just do as you please!

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Kayla, that's an interesting observation, that perhaps the more feminine side brings the whole being into better balance. You need to be careful who you ask your question to though, since I can imagine certain folks who would find something wrong with it 🙂 Here's hoping that society evolves past this prejudice as well.

William - I agree, the Internet has been a fantastic thing for the transgendered, and I deeply appreciate all the ladies online who have shared their stories. When you're alone and uncertain about what is happening inside you it's scary. With others we have a chance to realize that we're part of a community.

I see it as a tremendously positive thing that the next generation would have grown up on the Internet, and largely with less fear expressing themselves (if the videos I've seen on youtube are any indication 🙂 )

Those moments when we can be who we are and be accepted are heaven, aren't they?

I agree with you - if more of us started going out in public acceptance would come sooner. I wrote about this a few months back ( https://www.crossdresserheaven.com/a-call-to-crossdressing-action-its-not-just-the-transgendered-who-suffer/) - let me know what you think.

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hi all i have been crosdressing since i was about 12 yo am 50 now i was at a halloween party lost at a parlore game and had to don the clothing of oppositte sex. i was dressed totally from panties nylons garterbelrt reel frilly full petty cat and skirt.very nice stuffed bra and sweeter way too much make up also . well the reaction of all the boys and girls made me feel kind of strange in many ways . but i was and am completely addicted to dressing since that evening and always have found ways to dress and more as time goes on and now i raelize that i need more fem timethan i would have ever realized i would luv all cds and wish we all did not hide so much and came out to support and play with each other

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I have been donning women's clothing since I was a young man. I was lucky enough to find a woman who embraced my fetish and she allows me to endulge reguarly. I like the sturdier of undergarments. Full corsets with garters. I do have to say finding shoes I can walk in has been a real task. At my age, 67, I can hardly wear platform heels. I like the more comfortable shorter heel that has a peep toe. I enjoy painting my nails and wearing light cosmetics. I continue to dress in the privacy of my own home. Sometimes when the wife is home sometimes when she is not. I like to feel comfortable yet have some firm fabrics to hold in my midsection.
This year I intend to try some wigs. I always wanted to have long curly hair. I am looking at a wig catalog currently to try and see what I might choose. It is very nice to find a space to discuss these things with others.

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I am a gay man and I am 60 years old and considering getting into cross dressing. It's an idea I have thought of many times but never seriously considered until I met a guy online a few hours ago who told me about his desire to meet a cross dresser and how he wanted another guy to play the female role. I told him about my having a mustache and he said he couldn't handle that. When I offered to shave it off for him he told me more about being a "gurl" as he referred to it and I realized it was something I want to try. He sent me his picture and told me to get back when get my new look together. I feel excited by this and feel like I can start a new life even though I'm 60. I'm trying to find anyone who can give me advise. I'm shaving off the hair on my face before going to bed.

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Maria, thanks for sharing your comment - I can whole heartedly recommend crossdressing (though I'm a bit biased 🙂 ). Growing up in a less tolerant time, you're probably already used to the social cost of being different, which is the one caution I would give someone who was considering crossdressing as a choice.
Take a look around Crossdresser Heaven, I've got tips on everything from dressing to makeup to feminine deportment. Let me know if there are other areas you'd be interested in hearing more about.

Best wishes,
Vanessa

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Why do men crossdress? Well their brains are hard-wired for it.

About 50% of males will dress in women's clothes some time in their life. They will do it as a joke, to amuse others and have a laugh. They will not feel any emotional connection with the event. If you are in a war and capture some prisoners and make them wear feminine clothes, it will considered torture, and the world will be shocked. However, about 10% of normal, healthy, heterosexual men will say the whole idea is wonderfully pleasurable.

What is doing on with those men? Well, its in their brains. Their brains are hard-wired to release dopamine and other neurotransmitters when they feminize themselves. These neurotransmitters are powerful chemicals. They produce sensations of well-being, pleasure, sexual gratification, and self-identity. They affect the reward centers of the brain and thus mimic the addiction response. These men feel as if they NEED to crossdress.

Their crossdressing may begin as a small child who admire girls and feminine things. They may believe that girls have it better in life than boys. Their early crossdressing may be an attempt to pretend to live as their idols. Most crossdressers have their first experience during puberty. Their hormones are just beginning to flow, and their experience is very memorable. They may get an immediate errection, the may get goosebumps, and their body may quiver. It's like, WOW!! What was that!

In youth, crossdressing may be closely associated with sex and masturbation. As the crossdresser ages, it gets harder to generate the same stimulus. He may still find comfort and relief from stress by crossdressing. He may work harder at creating a female alter-ego. It's all part of an effort to increase the release of neurotransmitters.

Here is a simple experiment to determine the association of self-feminization with neurotransmitters. Dress up in your favorite feminine clothes. How do you feel? Wonderful? Good. Now masturbate. When you masturbate your brain releases a rush of neurotransmitters followed by a depletion of them. Immediately following your masturbation how do you feel about your feminine clothes? Most will admit they feel disgust with their crossdressing (for a few minutes). At this point these men are experiencing the same sensation to self-feminization as the other 90%.

Crossdressing is neither good nor bad. However, since it mimics the addiction response you need to keep things under control. If you do not control it, it will control you.

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DocChuck, that's awesome! You are truly blessed to find such a special woman.
Would your wife be willing to go to a beauty store with you to try on the wigs? That could be a fun, bonding experience for you girls.

Hugs,
Vanessa

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nervous

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I just wanted to say something along the lines of what Jo mentioned. I am a male, and cross dress, for what reasons I do not know. After reading what Jo mentioned though, I felt like she might be on to something. I thought about some things that help me, and about the way society is today. Well, I live in Japan, and the society was different here back in the past. The typical clothes in Japan were not much different for women and men. Long flowing silk dresses. I own both womens and mens kimonos, and have to say, that while I do get excited wearing womens kimonos, I actually feel much more comfortable and enjoy wearing mens kimonos better. A kimono is no boring ordinary thing. It takes a lot of time to put on (and take off 😉 feels great, and really makes you stand out. A mans kimono makes me feel confident and really seems to give me peace. They are still worn today in Japan, and it is an accepted attire. It might be something that others can look into. It might help. Or at least help you figure out some of your own feelings too. When both my girlfriend and I are wearing kimonos it is some of the most enjoyable times I ever have.

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Rain, that's an interesting observation - perhaps for some people it's not so much about the clothes being of the opposite gender, but the quality and extraordinarity (if that's a word) of the clothing. Boring, dull and scratchy is difficult to fall in love with. Sensuous, silky flowing gowns stand out and make you feel good - even if they're traditionally men's clothing.

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I am cd from my 15 years... iam unhappy to be a men.so i like to be women,so i wear sarees,chudis and i want to become a women.please help me.

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Another very happy girlfriend of a CD here. I loved dressing up and girly things like doing our nails and hair with my female friends when I was younger, and doing this with my boyfriend now brings back pleasant memories. It's still just as much fun. I love buying clothes, especially sexy panties, for him. Part of the fun in that is that he can wear much smaller sizes than I can, those sexy clothes for smaller-sized women, and I think I live vicariously through him a bit in that way. Having sex with him is a strange mixture of like/not like having sex with a different person, too, and I enjoy that as well. Now I'm not sure I'd ever want to have another boyfriend who DOESN'T crossdress.

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@Charity: Wonderful to hear from you love! My heart soars when I hear from women like yourself who have not only accepted their husband's/boyfriend's crossdressing, but rejoice in it. I think at times as crossdressers we find it so difficult to accept ourselves that the thought of another loving us not just in spite of this, but in some way because of it, is a powerful message!

@Chloe: Hon, I'm so happy to hear that you've found such a special person in your life who loves you for who you are!

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Ind Arts teacher for 30 years .... car nut.... took Pre engineering .... former Architectural Draftsman....

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I'm a 45 year old outdoorsy male in Idaho and Wyoming and I've crossdressed since I was about 9 or 10 when I found a pair of high heels in the garage that was going to be donated. Shoes are main thing but I also wear other things that enhance them: nail polish, pantyhose, toe rings, leather pants, skirts, most anything except wigs and makeup. I love women and have never been gay. It's just the feeling I get when I wear womens clothes and shoes (gotta have the shoes - heels, boots, clogs, or sandals) Yes, it's so fun to me and gets me really aroused. But, it's more than that. Most importantly is that the props of womens clothes and shoes help me get closer into the spirit of the sexy women I love so much. So I feel the the cross dressing helps me be more complete of a man, not less.

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Hi Will, so true - it's hard to define, and can't be captured by just a sexual feeling.
Tina - great advice! Do as you please, and be confident while you're doing it.

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So we ask why do we crossdress..? It is a question more of being who we are. I do because I fell right. I fell normal and natural. Do I like the guy in me most of the time. But do I like the girl in me, the one who has the eye for color and what looks good and casual. Yes!!!! But do I sexually enjoy it, No not to what you would consider sexual as per societies limited perception on gender and the roles we play.. I don't get off on the clothes I live for my clothes.. I enjoy being in as much women's clothing as I can to the comfort I fell when I am out doing things guy or girl... I want to pass more readily because shopping is easier but 24/7 I haven't comes to terms with yet.. Another battle and another time... But I dress to be me!!!!! Does it matter how I look or what my sexual orientation is? I enjoy me that is all that matters.. After that is is society that leaves me stranded.. Luv Janet

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I have been crossdressing since I was 12. I 1st got the urge to do it when I was watching a spanish movie with my parents where this guy put on his wifes panties on accident. Seeing that made something in my brain trigger. It seemed so naughty to me and the panties looked so pretty I jus had to try it! I have 3 sisters so it was easy for me to get a hold of some nice underwear. It was a pretty pair of pink bikini cut panties with a heart on the ass that said “cute” on them. I got an instant erection!! It was the naughtyness, the sexyness, and the fact thatI didn't have to sct tough that instantly made me love it!
Now I'm 31 and still do it. Although I'm still in the closet about my crossdressing I'm slowly reavealing my secret to my friends (all of them girls). I guess I'm scared that they might think I'm gay but truth be told I love women. I just also love dressing like them too. For Halloween I dressed up as Amy Winehouse and was out and about loving life!!! Now that I did this I'm absolutely gonna go out again all dolled up (I'm glad I live close to Hollywood where theres all kinds of drag clubs).
So to answer the question, I do it bacause I feel fabulous. pretty. fem. and I LOVE IT!!!!

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It's amazing the things that can trigger it - quite lucky to have such an abundance of clothes so close by 🙂
What a life affirming answer! I do because I feel fabulous. What a wonderful way to live every day of your life!

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firstly I would like to say thanks to everyone that has posted on this thread as it is comforting to think that I am not 'alone' in this world. I first began to dress when I was 12 or 13. I am now 37 and have been married for 8 years. My wife does not know and I do not think that she would be very supportive. I have tried to talk to her about it discreetly but I sensed that she sees the traditional male and female roles are necessary in the relationship for it to work and adding a third 'person' would cause an inbalance.

My mother is getting re-married later this year and my wife and sister will be bridesmaids for her. My mother sent a text message to me (as she did not have my wife's number) to confirm the date of the next dress fitting. This then led to a long tongue in cheek conversation that I wanted a dress fitting too including what under-garments I should wear. She said that she would arrange one for me but I dont think that it would have been a good idea to 'come out' in that manner.

I love my wife dearly and idolise women in general and have no 'gay' inclinations. I think that my desire to dress is borne from a love of all women and what they represent increasing my want to be part of their 'club'. I work in an industry that is gender generic as a travel software trainer and would love to go to a new client dressed but I think that would be some time away yet.

I found this site through a web search engine and will be keeping track of it as I am really thankful for the understanding that I have read so far.

Many thanks, Sam xx

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My dad is a crossdresser and even though I love him I do not understand why he would do this...

I am open to people choosing whatever life style suits them but can you please help me understand if you know you like to wear womens clothes why not choose a lifestyle that is suitable to your needs. Why would you involve a woman that wants to have a normal life and kids?

Even though you say you feel alone, have you all of you felt what this might to a family or to the children of that family? I think it is brave for those that seek their happiness without involving people that obviously do not want to share the same fantasy?

So why did you get married?

My dad hiding this from the family has caused such distrust in our family. Our relationship is toxic because he will be gone for days and we will not know where he is. He has spend money when we didnt have any so he could play with his fantasies. I think that any of you that are married and have children and do not tell your wives upfront before adding more people into your own selfish lifestyle just really makes me mad.

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I agree that it is completely selfish to not tell someone that you're a cross-dresser before getting married, or even engaged. In my mind, how can they know me if I'm hiding a major or even minor part of my life. I've lost relationships because of this, but I don't see them as losses, I see them as another chance to find the one that will accept me the way I am.

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My soon-to-be-ex-wife knew about my cross dressing, & barely tolerated it. I don't pretend to understand it myself, so why should I expect anyone else too? I'm just much happier as a woman. I don't hate being a man, I just need to be girly sometimes. I always thought "if I could only find a woman that liked my crossdressing, I'd be happy" Well now I have! I've found the perfect girl friend. It just does not get any better than playing dress up with her. We have such a great time together. Sometimes I'm a man, sometimes I'm a woman, but she always loves me. I no longer feel ashamed of what I am, and that is the greatest feeling in the world. So keep looking guys/girls. That special person is out there, just waiting to buy you some pretty panties!

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why do I crossdress?

I crossdress because I like the feeling of womens clothing on my body, it makes me feel so sexy. I feel like the women's body is the most beautiful thing in the world. I have never told my family of my fantasies of being dressed up all sexy like a women. My wife would surely not understand. I have a girlfriend though that understands fully. When we are together she even helps me dress up by applying my makeup and helping me find the right things to wear so that I look good in my outfits that I wear. I have gone out dressed up in the past. I am at the point in my relationship with her that we want to go out together as sisters. I have a feminine side in me and she loves to let me bring it out. One other thing, we have sex all the time when I am dressed up like a woman and the sex is the best I have ever had.

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Kevin said he likes to cross dress because "I have a feminine side..."

I like his answer and I think it is the main reason I like to do it as well. Most---if not all of us men---are part female, and to dress that way (at least occasionally) seems entirely natural to me.

And by the way, Deuteronomy 22:5, when properly translated, does NOT prohibit cross dressing, a fact I recently learned which causes me to love God more than ever!

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I dress because I love fine clothes and the highest of heels. I feel wonderful while wearing skirts and heels. I've shopped as a man for womens clothes and find most sales people are not too concerned. Some are just wonderful. I found the most wonderful shoe boutique about a year ago and it's my second home. The sales staff (my girls) are the sweetest things in the world. They have been so nice and accepting of me. I really think I've made an impact with them too. The more folks we show who we are and the more people that see us as real people the better for all of us. I actually went out for the first time in daylight today. So I had to go shoe shopping. I told her I would some day and you should have seen the smile on Grace's face when I walked in. I wish they had all been there. She did take a photo with her phone to show the others. I love them young ladies.

Don't be afraid to go out, Be who you are. Be beautiful and be proud. There are folks out there that are understanding and accepting of us all.
Love, Raechel

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I feel so relaxed when I dress as a woman. The feeling of pretty lingerie under a dress or skirt and blouse combo is unbelievable. I feel less stressed and can really relate to my feminine side. A woman is so lucky to be able to wear such pretty things, from undies to their outermost garments. I love wearing makeup and a pretty wig. Heels and stockings ( I prefer control tops over garter and stockings) are tremendous. Nothing like smooth sexy legs. I am completely hairless on my body with exception of one place. I practice being a woman all the time. Oh, I'm so jealous. I live alone and can dress up whenever I want. Patrice has her "girly" room and spends most of her time using that room rather than my guest room. My gg friends accept me as a "girl". They encourage me to bring my feminine side out as often as possible. I love hearing from other girls. Feel free to contact me at rjb7839@aol.com. Have a great "fem" day girls. I wish more woman (real ones) would dress as woman, sometimes they just put on jeans and blouse and sneakers....although so do I. I can see at end of day, for most girls, they feel great taking off their bras and getting relaxed in their own way. I prefer to wear a bra as long as I can everyday. As mentioned, to me it is relaxing. I also wear makeup, etc. regularly. Hugs to all.

Patrice

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@Patrice - it's wonderful to hear you have such a good experience expressing your feminine side. You truly are blessed to have so many wonderful girl friends who accept you as you are.

@Raechel - Wow! I've had salespeople be helpful, and sales people not really hassle so much, but WOW! That's wonderful girl! It's so true what you say - showing people the real you is a powerful and healing thing for both of you. We spend so much time these days pretending.

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to me crossdressing is more than just wearing the cloths and makeup. most of my life (and still going) i have felt that i am more like a stage actor playing a part. i play the part of the all american boy who played football, dated cheerleaders, and acted agressive. i also play the part of the good son who cares for his parents and is the dependable man everyone can turn to in need. but when i dress even if it is only a little makeup for 5 minutes to have a quick smoke i feel as if i am me. it feels like i am stripping away all those costumes and finally going off stage to relax. i am lucky enough to have a wonderful wife who knows all about my dressing and supports and loves me no matter what. just last month we went on a 3 day trip with me dressed for over half of it in downtown houston. we went sight seeing, shopping, out to eat, everywhere and you know what i got great responses from alot of people. granted there were a few bad ones such as when we went to the aquarium these 4 teen girls were making snide remarks about me but i say all in all it was a great outing. and next week im planning to goto the mall and were going to go walking round the mall window shopping and picking out things for me to buy. so i view myself as more female in mind than male and being the male role as a brilliant piece of acting but an act i hopefully one day can lay down for good. now this does not mean i plan to have SRS as i am very much atracted to my wife and plan to keep it that way lol. but i wouldnt mind FFS or breast augmentation one day but till then i will console myself with the knowledge thant i am me and i am theire view of me but i am still me weather in a dress or in pants and a shirt. as rupaul says "you got to love yourself first honey cause if you dont how the HELL you gonna love somebody else?"

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Honestly, I personally cross dress because I try to ignore sex and gender boundaries in life. Dresses, skirts and (for reasons I can't explain) high heels feel very loose and comfortable to me, certainly much more so than suits, so I wear them whenever I can (not very often, since I'm still a minor and my parents disapprove...) I also wear other general women's clothing, like pants and shirts. To answer the question more concisely, I cross dress because some pieces of women's clothing are just really awesome, and I would wear them if they were men's clothing instead. I am sort of tempted by the idea of trying to pass as a woman, although I have not yet tried it.

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Admin
(@cdh)
Joined: 13 years ago

Famed Member     Seattle, Washington, United States of America
Posts: 1461

@Daniel - congratulations for being willing to explore who you are while you're young! It's important that you're open to your feelings, and allow yourself to grow and learn. I'd be interested in what other folks think - would you wear woman's clothes even if fashion changed and they were actually men's clothes?

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Posts: 1
 Jo
Guest
(@Jo)
New Member
Joined: 16 years ago

Thank you! I'm not entirely sure what your question is asking, but of the gender of clothing switched (that is, currently male clothing people female clothing, and vice versa), I would wear both types of clothing, although then I would tend toward wearing the (newly) male clothing more often, again because my parents push for male clothing. Although honestly, I must say that I like currently female clothing better than currently male clothing, on average. It tends to be much more comfortable and colorful.

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 Jo
Guest
(@Jo)
Joined: 16 years ago

New Member
Posts: 1

Sorry, in my second sentence I accidentally typed 'people' instead of 'became'. No idea why... The parenthetical should read "(that is, currently male clothing became female clothing, and vice versa)". My mistake

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