Why I Crossdress

[Larissa Cassandra]

After many years of wondering why I'm so different from most other men, I think I've finally figured out why I've been drawn to crossdressing and why I enjoy it so much. It's actually fairly simple, and there are only two parts to it.

1. As I've mentioned in other posts, I'm almost certain my mother would have preferred to have a girl as her second child (though she never told me that). She'd had a miscarriage and my older brother before me. She always talked "baby talk" to me, even just "kidding around" after I'd grown up. She was quite the girly girl herself, always in dresses and heels, with full makeup and always perfume (I remember Heaven Sent and Wind Song). I suspect she might have dressed me up in girls' clothes when I was a baby or toddler, but I don't have any specific memories. If she were still alive, I would ask her, but I missed that opportunity.

My mother left my father, brother and me for another man when I was only 11 years old, so I lost her feminine presence in our household. Everything was manly and macho all the time. My father was great in taking care of us, but he was the old-school John Wayne-type man's man. So missing exposure to anything feminine has made me quite curious about girls and women, and later when I could try clothes and makeup, it was a lot of fun and opened a whole new world to me.

2. About a year or so after my mother left, I started going through puberty and paying a LOT of attention to girls. I had several girlfriends throughout high school, but never any of the "high maintenance" girls, like the ones in all the slick magazine ads and TV commercials. Those were the ones who were the sexiest, according to the advertising industry, so of course I found them very alluring. So when I was able to wear the few female things I'd obtained (that could be another thread!) and put on makeup, it was a substitute for the sexy young women in the ads, and the "hottest" girls in school. I was very shy as a teenager, and those "hot" girls just weren't my type anyway, personality-wise. BUT, the image of the ultra-feminine woman dressed in a beautiful dress with jewelry, makeup, long flowing hair, heels, and (I imagined) sweet-smelling perfume was very attractive to me. So when I was able to imitate some of that look on myself, it was a big turn on.

So, to summarize, missing out on a feminine presence in my home, and then going through puberty with my increased curiosity and the erotic images in my mind, seem to have cemented in my mind a love of everything feminine and a desire to emulate a feminine persona. But the strong male influences from those years living with my father and brother, then 4 years in the military, make it difficult to enjoy my feminine side without feeling some shame and embarrassment. This is why I don't dress as often as I would like to, even though I have a very accepting and supporting wife.

Anyone have similar experiences or think there might have been other influences in my life that you had, which may have contributed to my crossdressing desires?

Hugs,
Larissa

[Heather76]

I can't say with any certainty what may have given me the desire to CD. Two things come to mind that may, in hindsight, have been indications I would enjoy CDing. The first, and I still remember quite vividly, is how disappointed I was when my dad came home from the hospital and told me I had a new baby brother. I was 4 1/2 at the time and I wanted a sister named Susan. To say I cried at this news would be an understatement. I had an older brother so why a sister? Could it have been so I could play with her and her dolls? I've no idea. I never did play with feminine toys growing up and don't recall ever have such desires. I grew up as a typical athletic, adventure seeking guy. The other thing was of a sexual nature. From the time I was a preteen until sometime in my 40s or 50s, I would very often tuck myself while bathing in the tub to see what I might look like "down there" as a woman. Haven't done that in 25 - 30 years, but, I did for a long time.

[Kris Burton]

HI Larissa - this post is very insightful on your part, and no doubt required a lot of soul searching. We don't have too much in common with our backgrounds - I was an only child from a very stable family, and the notion of trying on any of my mothers things did not even cross my mind. I was also a very shy kid and teen, but we link up where the attraction to women and what they wore was a big turn on for me. I did not feel shame, but was very embarrassed by my feelings and hid them away. Not until I was married (at 29) and had access and close proximity to these clothes and femininity was I able to even visualize putting them on, enjoying them myself, participating in the fun!

At this point, I think I can say that my early shyness and repression more than anything fueled my curiosity of all things feminine. It probably plays no small role in why I crossdress now and feel such satisfaction on so many levels. It's almost like I'm making up for what I missed.

[franlee]

Maybe my CDing was caused from poetic justice. I always had a preference for Girl that dressed in clothes that I liked, short dresses and skirt suits and skirts, oxford type female shirts, turtle necks, sweaters, shorts and of course hot-pants.And then throw in heels or high boots and I would admire those Girls and date them, but if a Girl dressed in something that didn't turn me on that was the end of that. Well my Girlfriend dressed perfectly to my taste without a hint from me, and I mean all the time. So when I made a stupid bet that I could fit in her clothes one night she took me up on it. I couldn't back down, that was not an option for me back then and not to much even to this day. So we swapped and I won! Well I won more than the bet, I couldn't get it out of my mind how good it felt and it STUCK! From that time of being a fetish until now that is a therapeutic relief as well as the left over fetish/fantasy days back when I turned 16. And that is the reason, I enjoyed it and still do.

[CarleyR]

I agree with Larissa. I think the love of ultra-feminine things, which our more practical wives rarely use, creates a situation where CDing gets us closer toward that attractive "image of the ultra-feminine woman dressed in a beautiful dress with jewelry, makeup, long flowing hair, heels, and (I imagined) sweet-smelling perfume."

[DianeT]

That turn on we experience when trying to emulate the looks of girls we find attractive is probably what started my crossdressing, a year or two before puberty. But "turn on" doesn't really capture the essence of the thing, which is (at least in my opinion) of a transcendental nature, a metamorphosis of some kind. Yes there is turn on. But it's more a byproduct than the core of it. Grown up women appeared to me like super beings when I was a child, and the effect they had on me a mystery I wanted to crack. Crossdressing was one of my attempts at solving it (there were others, such as drawing heroines in comics or writing erotic stories). Born from attraction, but fueled by the magic of almost touching their skies for a fleeting moment.

[alwayshave]

Larissa, While I had a brother and father, I also had my mother, grandmother, grand aunt and 4 sisters in my house. It wasn't the lack of femininity in my home that caused me to crossdress. Perhaps the opposite.

[GretchenM]

Very insightful, Larissa, and I suspect you have identified a major factor in your present priorities. It is possible for CDing to be an acquired characteristic and it is widely assumed that CDs are distinguished from Trans in that the CD behavior is acquired. Problem is that conclusion is frequently found to be wrong after a shrink starts nosing around in your brain. However, the very fact that this memory is apparently so vivid in your memory indicates that these experiences made a huge impact on you. Otherwise they would not be so vivid. Memories that are not important to the big picture often fade and eventually are lost or severely distorted.

So, I am not so sure that this is THE CAUSE. But it is certainly a major defining factor that represents your way of adapting to the experiences that your brain concluded made sense in the larger neurological context. In combination with some degree of genetic configurations that create a bit of a sizeable propensity toward gender reversal may be at the root and your experiences simply triggered those genes into action which triggered a perspective that recognizes a bit of girl in you in addition to a larger amount of boy in you. That can then set off a process of prioritization where your brain decides the girl part really works nice in collaboration with the boy part. Your brain then adapts to that perspective and what comes out of those hundred billion neurons is who you are today. Smile! You are you, but that "you" is still changing as your brain incorporates new experiences and tweaks the formula a bit this way and that. It is a journey. Enjoy it. If you happen to go too far, alarms will go off in your brain, you will feel discomfort (dysphoria) and you will know that you shouldn't go into that forest, at least not yet. But once you detect that forest you will want to explore it - cautiously. Do so, but it might not be for you. We are always growing and changing.

[AmeeJo]

My crossdressing journey began when I was 12. I was fascinated with the female body and tight clothing like bathing suits and leotards just looked so pretty to me. As soon as I had the opportunity to, I tried some on. I was hooked. I quickly moved up to bras and panties as well as a really cute tennis dress my Mom had. Wearing them just made me feel so good. Once I got older and had money from working, I started shopping for myself. I still remember the first time I went to Victoria's Secret. I bought a really sexy teddy with garters and matching stockings. The first time I saw myself in it, I was blown away how wonderful I felt. I have been slowly continuing my journey ever since. So, nothing really happened to me to trigger my attraction to all things femme, I just thing I have a strong feminine side and she wanted out. I'm still in the closet with my dressing but, it's funny, my wife has said many times that I have a tendency to lean towards my feminine side. I'm working on a plan to come out to her in the near future. We'll see....

[Sabine Janus]

Older sister dress me very young as her baby doll, but I don't recall it.

I do recall having this urge to be someone else, but more in an explorer/adventuring way, not in an escape. Costumes weren't available and the most "Other" thing I could find was en femme. The clothes felt amazing and totally different from boy mode. PLUS I grew up with strong present women, so I didn't have the idea in my head that women were somehow "less". I DID catch on quickly that dressing as one was not acceptable so I kept it to myself.

[Cheryl T]

I can't say for sure and I don't really believe any of us can.
Personally I believe it's genetic. I say this based on my family history. Not that anyone else in the family is CD, but because of other things. I don't want to go into a long story about it, but I'm fairly certain these factors are actually why I am who I am and also that I may be more than just CD. That part is still being investigated.

[Bea_]

I dress because, when I look in the mirror or at photos of myself in the feminine items I choose, I feel a sense of specialness that I don't feel at all in drab. Even if it's just an awareness of wearing panties under my jeans, or looking down and seeing my pink toenails, it just feels special. That's about as far as I can go in the analysis.

[JulieC]

I'm quite certain I was born with it. One of my earliest memories centered on crossdressing. I don't think anything brought it on per se, just getting to an age where I could try on my mother's things without her knowing, and progressing from there.

[Diane P]

I'm new here, but I'd have to say in my case it's that dresses and other women's clothing, nightgowns, bikini underwear, shorts and tops, feels right and natural when I'm wearing them. I do remeber my mom telling me that when I was a baby and my mom would tell peole I was a boy their response was usally something along the lines of "he's too cute to be a boy, he should have been a girl". I'm 64 and loving wearing all the dresses and everything else I have bought myself in the last month.

[Jessica Secret]

For me it's pretty simple - I developed a love of beautiful/romantic lingerie at a young age seeing and feeling how sensual it was, I was quickly hooked and have never looked back since. The sight of it, the smell of it, the fabrics, seeing photos of women wearing it and feeling jealous, walking through lingerie departments and shops, all of that made it intoxicating and I became obsessed and had to wear it.

[Natalie5004]

I have mentioned before that my sisters were my influence growing up.

Just today I went out to buy some ciggies. I had a "Thank you Hon" from the clerk and a gentleman held the door for me on the way out. I loved it.

Natalie

[kimmy p]

I like the clothes better. Much more variety of styles. More colors are acceptable. And with the addition of wigs and make-up my entire look can change. And truth be told... I have been informed by a few people that I look better as a lady. And I happen to agree with them.

[Jane G]

That turn on we experience when trying to emulate the looks of girls we find attractive is probably what started my crossdressing, a year or two before puberty. But "turn on" doesn't really capture the essence of the thing, which is (at least in my opinion) of a transcendental nature, a metamorphosis of some kind. Yes there is turn on. But it's more a byproduct than the core of it. Grown up women appeared to me like super beings when I was a child, and the effect they had on me a mystery I wanted to crack. Crossdressing was one of my attempts at solving it (there were others, such as drawing heroines in comics or writing erotic stories). Born from attraction, but fueled by the magic of almost touching their skies for a fleeting moment.

Possibly this. I was surounded by female role models as a young boy. I never once had a male role model if I am honest. Loved my dad to bits mostly, but never once wanted to be like him. My wife is forever telling me to dial it back, when I start acting/speaking like my mum. While I don't even register that I am doing it.

[Christina89]

Growing up it was just my mother and I. And most of the time the only real male models I had in my life were my grandfather and a neighbor who I consider my second father. Other than that I was surrounded by females. We would always go to the mall together around back to school to get new clothes and with being the only male in the group majority of the time I had to wait for them to finish getting their stuff before I could get mine. I was always fascinated by the fashion they had to choose from. And at times hated what I had. I remember moments when it would be my mother and I watching TV and there would be adds for girls clothing from different stores on TV I would sometimes ask my mother "why can't I wear those?" She would respond with "cause you're a boy" and that hurt. It wasn't till I was 12 or 13 that I finally did get to 'wear those' when I tried on my mother's clothes. As time went on I thought I wore them as a fetish, but in reality I wore them cause I felt safe and less stressed. I escaped this reality and entered another one.

[Lacey New]

For me it was a sexual fetish. In my early teens, like many boys, I became interested in girls. I saw them develop bumps,on their chests and nice curves to their bodies. Back then, most of the girls wore skirts so a flash of panties was not unusual. Well, one day after school I was alone in the house and there was a pair of nylon panties hanging out of the hamper. I don?t know or remember if they were my mothers or sisters, but it does not matter. Well, I put them on and you know what happened. It felt great. So, I sought out opportunities to repeat as often as possible. Then one day, I found a bra in the hamper as well and I figured if panties felt good, then panties and a bra were even better. And it was. Eventually I added pantyhose and finally after college living on my own, I started my own collection. And so it was

[Brianne_bc]

I crossdress because its part of my being on the autism spectrum. I was grateful to finally have the answers to why I dress up and other traits that come with being on the autism spectrum. For me its a form of stimming and wearing lingerie daily under my boy things just makes life so much grander. And being hypertactile the feel of satins and silky things is exponential.

[Joanne108]

Why? I like to see myself in the mirror as the image of a woman.

[Beano980]

Larissa, I'm so impressed that you figured out your "why". A few years back, I saw a therapist for several years. She was a great therapist and very insightful. But, we never pinned down a definitive "why". We did however identify some things that felt right for me. Primarily that its been there since I was a very young child, and it seems to be centered around the special attention that females get and feeling desirable. There was no single incident that led me down this road. More of an inclination that has always been there. Dressing fem from time to time lets me immerse into that space of feeling desirable.

[Larissa Cassandra]

Thanks Brooke, but since I haven't run these by a therapist, I can't be sure there's not more to my story. But I'm satisfied with what I've come up with. It's true for me too that some things just feel right - like wearing a silky nightie and panties to bed, putting a little lipstick on just being around the house, wearing a short skirt on a hot day, spritzing with fragrance mist in the morning, and I could go on and on!! So since these feelings started when I was very young, there might also be a genetic component, as some others have suggested. That could be part of your story too.

Hugs,
Larissa

[April Rose]

My feeling of being drawn to the feminine side of life has been there for as far back as I can remember. It has morphed and changed so many times that I can't attribute any one thing or situation as a cause.

Really it just seems to be the way I have always been.

[Monique65]

I gave up tying to figure out why years ago. I just accept it and enjoy the experience.

[Lucy B]

During my many years of dressing about twice a year, or even not at all for years, it was just a sexual fantasy really.
When the urge to dress much more often developed about a year ago it changed into not being particularly sexual at all really, it just feels much better to be dressed.
I just love it.

[Claire M]

Why I crossdress? This the $64,000 question looking for the $1 million answer. Larisa's original post delved into the cause of why she dresses. My mom took one of those no-longer-used 50s pregnancy drugs that might have had some effect. When she was pregnant with me she was 100% sure I would be born a girl ... so sure, my parents didn't have a boys name to put on my birth certificate. I grew up with 3 older brothers and 1 sister so it definitely wasn't lack of male influence. To the best of my recollection, I wasn't abused or forced to wear girls clothes. Just an average, 1950s/60s midwest catholic middle class family.

So I posed this question to my first therapist. He told me "You're just wired that way". Since I was looking for a cure, I decided he was a quack and never went back. Twenty years later, I posed the same question to my second therapist. Her answer was "What does it matter? Instead of worrying about why you do it why not work on how you can cope with it and maybe incorporate it into your life?" I had given up on "being cured" by then so I continued working with her for several years.

What drew me to crossdress? Just wired that way I guess!!! I can say that I distinctly remember the first time I slipped into a pair of my sister's panties I had an overwhelming urge just to see what wearing them would feel like. Why I still continue to dress? I like the feel of the clothes. I like how I look in clothes an makeup and it just feels natural.

To put crossdressing in the same perspective as home brewing beer one can worry about hundreds of details in the process but the best advice - Relax.. have a homebrew! Or in the case of crossdressing ... Relax .. slip into something pretty!!

[christine55]

As a kid I stuttered as a kid and had a low self image. Began to envy the pretty girls

[Debs]

I Xdress because my X Y chromosomes are not right, cant help it, not running away from it, but it predicts how I am in society these days.

[NancySue]

After many years of deep thought including a college degree in motivational psychology, I?ve thrown in the towel and just accept my enjoyment of the feelings, both physically and emotionally, I experience by wearing women?s clothes. I don?t give it a second thought. I just really don?t care what people think. The beauty of having a wonderful, supportive wife is irreplaceable. I wear panties, bra, thigh highs women?s shorts and tops most days. If we run an errand, I always leave my panties, bra and hose on. I?m not sure we?re so unusual. I?d bet the farm, there are many men, who in the secrecy and privacy of their homes have opened their wife?s lingerie drawers.

[Izaria]

Why I crossdress?
To put it simply, ladies clothes are so much sexier with such a better range of items to wear.
I first tried on a pair of ladies knickers I had bought for my girlfriend at the time and was immediately taken by how nice they felt, much nicer than my plain boxer shorts. When I married many years later I wore my wife's knickers but only did this a couple of times during sex and once I wore a pair all day.
Now I am divorced I have bought myself some clothes in the correct size and intend to buy more and eventually wear them out somewhere.

[Jade P]

Not sure why, but I now accept and love being genderfluid. When I dress in feminine clothing I feel and I see the real me. If family and society were more accepting than I would probably dress like woman dress most of the time. I just find time in my bedroom or underdress in public and that is working out okay. Divorce is a strong possibility because my wife is very unaccepting. If that happens I probably will live more of my life as a woman.

[abby054]

My reasons for cross dressing are threefold.
1. Fashion is fun. The range of garments, colors, textures, styles, materials, cosmetics, ? are great for creativity, fab appearance, sexiness, to name a few inputs and outcomes. Expressions are endless. I carefully study several fashion websites that take the fundamentals seriously and produce a well reasoned, valuable art form. Female fashion is far more varied, has far more opportunities than male fashion in my culture. I have felt this all my life. It is why I asked my aunt, who I lived with at age five, why can I not dress so pretty as you and my girl classmates do. Why should I be left out when women have most of the fun?
2. In my lifetime, a shift in individual importance and power dynamics has occurred in my culture. When I was young, my culture was a patriarchy. Men ruled. Today, my culture has become an obvious matriarchy. Women dominate, particularly in my chosen workspace, academia. I have lost out on promotions and good jobs because I am not the right woman for the job. And the people doing the promoting and hiring are not shy about saying so. I cannot become a woman without losing what little I have left, but I can look like one for a few hours and join their society temporarily. If you cannot beat them, as the old saying goes, join them, even if briefly.
3. Escape. I work in an office supervising many people and making many decisions. The politics is brutal. Silly me. I chose to work in academia, in the federal government, and in churches. Any high pressure politics in those places? I thrive but from time to time, I want an escape. I want to be someone else entirely different for a little while. There are few, if any, changes that I can conveniently make for a few hours to gain a different identity and lifestyle than to change my gender presentation. And escape. My wife, though breathing death on my cross dressing, picked up on this quickly when I told her that I enjoy cross dressing. Her first question was to ask why I do not want to be who and what I am. I need to escape from time to time. This does it quickly, conveniently, and well with a lot of fun.

[ShirleyN]

[QUOTE=Crossdressong Kev;4614316]Why I crossdress?
To put it simply, ladies clothes are so much sexier with such a better range of items to wear.
I first tried on a pair of ladies knickers I had bought for my girlfriend at the time and was immediately taken by how nice they felt, much nicer than my plain boxer shorts.". Absolutely agreed 100% with both of these points. I've always been fascinated with the level of variety with women's clothes as well as the amount of interesting designs and patterns.

[Stephanie47]

I gave up trying to rationalize "The Why." It makes no sense to me that a young man would endure the shame and self-hatred associated with wearing women's clothing. I always view the "How I Feel" differently that the "Why?" I cannot put a finger on what started this need. I grew up in a household of mom, dad and older brother (15 months difference). I was and tumble. I played all the sports and rolled in the dirt. No sisters or female cousins to dress me up for fun or punishment. Why? There is no answer. There were periods of time when wearing women's attire was not possible, but also I had no thoughts to do it. That's where a counselor's thoughts come in. She is my combat related PTSD counselor. Her opinion is each man and woman has some dna of the opposite sex in his or her dna. In some it is more than others. While I was in the macho military combat situation there were no thoughts, other than keeping alive. I suppose the male dna totally dominated me for the moment. Later, when those PTSD issues arose emulating a woman probably could be a means of escaping. I have guys in my support group who delved into alcohol and drugs to escape. They are all classified as "recovering" and sober. I find it interesting that society will accept to some extent somebody who sought relief in a bottle, but will not accept a man who find escape in wearing women's clothing.

I am of the opinion that my expression is secondary to the why. I shun women's pants. It is dresses and heels. I figure that is an influence of the times of my initial discovery; 1950's and 1960's. I loved art as a child and love growing flowers for their colors. So, it makes sense my favorite dresses are floral prints. I love the feel of the nylon fabric of my full slips.

Life would have been a lot less stressful if I did not have this quirk. My problems now are dealing with problems others may have of a man who needs to wear women's clothing.

[JustagirlAtheart]

I totally agree with ShirleyN.
Ladies clothes feel amazing, I first tried on pantyhose.
They felt electric, is all I can say.
I discovered satin panties a few years later, the feel is again amazing.
I bought a few items from Goodwill recently, and a white
t-shirt fit me so well, I was amazed.
It hugged my chest, It actually looked like I had little bitty titties.
OMG, womens jeans, also fit me very well
Bottom line for me, all women's clothing is comfortable.
Satin nighties, are to die for.

Rachael

[BLUE ORCHID]

It is just who I Am, And it's just what I Do.

[JohnH]

Why do I.cross dress? Simple: I.am bored with the mandatory coat.and.tie.for men's formal wear. For church I alternate between a man's coat and tie, and a dress and heels. I feel.on Sunday morning I should be in my.Sunday best, as I'm sick and tired of men and women showing up in jeans and sneakers.

[Jeanettew]

I crossdress because i think many women look amazing and have plenty of verity where male cloths are just boring and there is nothing like the feel of stockings on shaved legs and the freedom you feel in a skirt or a dress, then the feel of nice ace undies is amazing

[PantyBoots]

To get in touch with my feminine side. Being in lingerie makes me feel that way.

[Pantyfan]

I started around 11-12, I knew I liked panties so I started there then went to bras, skirts, etc. If my brother had a baseball game or whatever I would be home dressed in panties/bra/denim skirt. It definitely had a sexual aspect to it, but to to tabboo part of not getting caught, and liking the girls my age at school. Never got caught, was careful to not be risky.

I dont fully dress, I could if I wanted, but with a short beard I?m not close to passing and thats ok. Respect to those who do, no right answer there. I do love leggings and skirts, and wear both in public. I havent had the guts to fly in a skirt, but have in leggings many times. Thinking more about it I dress for comfort, style, look and feel. I have one friend who knows about my dressing and underdressing. I dont bring it up much because I dont want it to be awkward or potentially sexual conversation.

[Lisa516]

I get a thrill out of it, and a sexual turn on .