Welcome to Crossdresser Heaven, a safe and welcoming place for everyone in the crossdresser community.
Join Crossdresser Heaven today to participate in the forums.
I previously posted a write up on how I was in a sense introduced into wearing first girls and then women’s clothing. This posting however will be an attempt by me to analyze how dressing took hold in me.
As I stated previously my first time wearing girls clothing was when my sister dressed me up in one of her outfits. To this day I believe that had that not happened I would not have developed the part in me who dresses up.
First off at the age I was at the time, about six, I was still pretty innocent to the world around me. When my sister had me put on her blouse, skirt, and saddle shoes it was confusing. While I didn’t know why boys and girls wore different clothes I did know they did. Inherently I also knew, without anyone telling me, that boys don’t wear dresses, or skirts, ever. But as my sister gently guided me from my boy clothes to her cast offs she was nothing but sweet and caring. I guess as innocent as I was at the time I must have set my fears or preconceived notions aside and just went along. At no time did she laugh, grin, or try embarrassing me. She carefully explained how everything went on and in what order. I was dressed completely from the skin out. All of my boy clothes sat on the end of her bed neatly folded.
Once dressed she had me stand and walk towards her floor length mirror. There I saw myself for the very first time ever wearing girls clothes. I remember starting to feel I shouldn’t be doing this but my sister said everything is ok and just calm down.
she had me feel the blouse I was wearing and how soft it was. She asked me if I could tell if it was softer than my boy shirts. I told her yes it is much softer. She asked if it felt bad or good. I replied it felt good.
I think really unbeknownst to her or me she was getting my guard down and I let it happen.
She moved to the skirt and said how special it is to wear a skirt or dress. She said my legs are more free to move around than in pants. She had me take a few steps and said to notice the skirt brushing on my legs. Boy’s pants don’t do that. I agreed. She asked me how it felt. I told her ok.
Next she directed my attention to the saddle shoes she had me put on. While this was the mid sixties at the time and girls did wear them it wasn’t like it was in the fifties. She then told me that only a few years ago both boys and girls wore saddles shoes. I told her I didn’t know that.
Once that short discussion occurred she lead me out for my mother and brother (who she already dressed up) to see.
When it was time to change back to my boy clothes my sister once again questioned me how the clothes felt on my skin. Did it feel rough or soft, and so on.
Without saying a word to anyone for the few hours my brother and I wear dressed as girls I felt something I had never felt. When I’d feel the skirt I’d get a twitching feeling in my neither regions. I got that same feeling when I walked past a mirror and saw myself, or looked at the shoes I was wearing.
When she asked me if it felt good or bad I remember saying it didn’t feel bad. She then asked if it didn’t feel bad then it felt good? I was embarrassed when I said it but I told her it felt good.
When I said that she gave me a big hug and asked me if I’d dress up for her again some day. I said ok. I changed back into my boy clothes and left.
From that very first time my sister dressed me up everything changed, I mean everything.
I noticed that I was noticing not only girls more but what they were wearing. I had memories on how good it all felt from that very first time and as I saw a girl wearing something else I wondered how it would feel to wear that.
Finally a few months later my dad and brother were going away on a scouting weekend camping trip. They were going to be gone Friday through Sunday.
As they drive off my sister had me follow her into her room.
There on the bed was red dress. She looked at me and said that since I was ok dressing again someday that today was going to be that day.
This time along with the red dress she had me try on a pair of red kitten heeled pumps.
As this was all happening I had that twitching feeling return. Once out of the room my mother seemed ok with how I was dressed.
she then told me that when she was pregnant with all three of us kids she had a boy’s name and a girl’s name picked out. She told me my girl’s name would have been Brenda.
From that day onward whenever I dressed up my sister and mother called me Brenda. I just accepted it.
At this point in life I was as I said earlier innocent and so with that I innocence came acceptance. They dressed me as a girl and I got a really pleasant feeling below. Not realizing there was anything such as sexual desire or feelings what I think happened was I liked the feeling I got, and only got, dressing as a girl. Nobody sad dressing was bad so it had to be good. Sure I knew it was something I really didn’t want to share with my friends, brother or father but it just made me feel really good.
As time went on the dressing continued. Rather than signing me up for scouts my mother kept me out of it. I think she did it so we would have periodic weekends away from my father and brother.
eventually I caught up to my sister’s current sizes and finally surpassed her. Everything started to be too tight.
My mother resolved that by buying clothes in my size.
Shoes were a different story. Back then you bought shoes at full service shoe stores. There were no self service stores yet.
So one weekend after my Dad and brother left for the weekend my mother loaded my sister and I in the car and drove off.
Today all of the larger and smaller cities have grown into one large metro area but back then it wasn’t the case.
We went one town over and parked. I followed my mother and sister not really realizing what was going to happen.
My mother turned on the sidewalk and walked into a shoe store. Stores back then had displays along the side walls, and seating in the middle, facing both sides.
she wakes up to the only person in the store, the sales lady and started talking to her. The sales lady looked at me then back to my mother. They came over and the sales lady had me take my shoes off.
She measured my feet then talked again to my mother. She went in back and came out with a few shoe boxes.
She asked for one of my feet and then removed my sock. She then put on a very thin footsie kind of thing and opened the first box.
She pulled out a black pump with about a two inch heel. She saw me get really nervous. She put her hand on my shoulder and said there’s nothing to fear and I wasn’t the only special boy she’s helped. At that moment with those words I realized there were other boys out there that sometimes wore girls clothing.
it didn’t occur the next that there was even a name for boys like me.
She put one shoe on, then the other. Then holding both of my hands helped me up and assisted me taking a few steps. Honestly I got that same feeling below, which by now I associated with meaning whatever was happening was good.
In all my mother bought two pairs of shoes. The pumps, and second a pair of girls saddle shoes. I ended up wearing the saddle shoes with my jeans and t-shirt out of the store.
From there we went home. My sister and mother helped me learn how to properly walk in heels. Over the years that followed, up to graduating high school, the styles I wore followed my age.
Upon graduating high school I could walk with ease in a five inch high heel.
Even though saddle shoes never came back in fashion as they were in the 50’s they’ve had come backs every five or ten years. I keep a few pair in my closet (two tone brown, and black and white).
My father passed away right after I graduated high school. My brother joined the service and made it his career, mostly living overseas.
I thought it best not to dress when I went to college but of course that didn’t last.
Being so exposed to dressing as a girl and a woman mainly by my sister and of course with my mother’s assistance and approval, my “staying away from it” didn’t last.
All of the memories of dressing up as I grew up were never far from my conscience thought.
Also I still looked at woman as well as what they wore. Sexually that part messed with me a lot. I knew beyond a doubt that I did not have sexual desires for a man so I wasn’t gay. But I was very shy around woman. I feared slipping up somehow in something I said or did and they would guess I did what I did.
In a rare instance if a conversation somehow ever touched on the subject of men dressing as women I kept my mouth shut.
About all I would say would be that everyone deserves to be happy and as long as it’s legal I’m the last person anyone has to worry about. Nice, simple, generic reply that pretty much took the focus off of me in an otherwise uncomfortable conversation, as far as I was concerned.
As I talked briefly in my previous posting I am married and yes she does know all about “Brenda” and the entire history of “her”.
My wife actually knew I was a crossdresser before she and I knew each other.
She worked at a second hand clothing store for women in the city where I went to college.
A man coming in the store to look through the racks practically sets off alarm bells and spit lights saying “crossdresser shopping”. Actually it’s not like that, no alarms or spotlights but trust me there’s no question as to why a guy is shopping there.
When my break from dressing had reached its limits I decided I needed to buy a few things. Rather than going to a mall and shopping new I took the second hand route if for any reason it was because I was a nearly broke college student.
What I did was use the yellow pages and called a few of the second hand clothing stores for women. I came right out asking if it was ok for me to come shopping there for something for myself. Anyone on the phone knew I was a male by my voice.
All were at least respectful in their responses. Some obviously didn’t feel great about it but said come in anytime.
One store I got the owner. She said I was more than welcome to come shop and suggested a few different days and times when the store is pretty much empty.
So I started shopping there and stayed a regular shopper throughout my time at college.
Where my wife fit in was she got a part time job there after I had been shopping there for a while. She normally worked evenings and I shopping mid week mornings. But on a few occasions our paths crossed.
It was in my last year at school that we had a class together. She came up to me after class and introduced herself then in a quiet voice told me where she had worked.
I asked her not to tell anyone. She grabbed one of my wrists and said no need to worry my secret was safe with her.
From that meeting after class we became friends, then close friends, and finally a couple. She’s been the only woman I’ve ever dated and will be the only one.
While we were getting to know each other of course my dressing had to be discussed. She knows all the history behind it and if fine.
I have read where others wished their wives would accept it. In our case she knows about it, some times sees me dressed, even assists me. But I don’t make it the center of our relationship at all. What I do if anything is make sure she knows that above all else I love her more than anything, even crossdressing.
Knowing the history of it with me she understands that to a point my crossdressing was induced in me by my sister’s and to a lesser extent mother’s actions. It’s not anything that’s ever going away but it’s also something private and she’s ok.
As I said before my one brother lives overseas so he’s mostly out of the picture. My mother passed away so it’s really only my sister left that I see on a regular basis.
My wife and sister have discussed my crossdressing. My sister at times has said she feels guilty that she did this to me. I’ve told her it is what it is. I have said I likely would not have become a crossdresser without what her involvement was. And yes to some extent it has affected my life but that I survived it and am in a happy place.
If anything it kept me trim while others my own age have grown outward so there’s nothing wrong with that.
And I told her that I really believe that I became attracted to or addicted to, whatever, that very first time she dressed me.
On rare occasions when she’s coming over for a visit rather than her brother she gets to visit with my wife and Brenda.
Though for me I do limit my time to dressing up. I know I could get away with more but I have a strong relationship with my wife that’s more important to me.
Prior to that I had zero interest to dress up. Had no desire to sneak into my sister’s room and try on her clothes.
Brenda , Great story on how you became introduced into the cross dressing world. I am sure many of would have loved to be in your shoes (and dresses) as you grew up. It was a very safe and happy environment and was supported and encouraged by both your sister and your mom.
I do agree with you, that I do not think you would have started to dress without the assistance and persistence of your sister. Many of us, including myself, always ask the question, how did I start and why? You, it is pretty obvious.
It is very nice that you wife knew before she was actually introduced you and is very supportive. Something we all wish and hope for .
Take care!
A lovely story and an experience of which I am very envious and I have to agree with Celeste that you would have become a crossdresser eventually, without the influence of your sister and mother.</p>
<p style="text-align: left;">The feeling that you recall that you had when you first dressed and that were repeated over and over again as you grew up are a certain indication that the desire to dress feminine is part of your nature and would have arisen at some point in your life.</p>
The fact that you learned that Crossdressing was enjoyable and accepted by your sister, mother and most importantly by yourself before people tried to tell you that it was something evil and unacceptable to 'their' standards, which you should not do, most likely saved you from the years of fear, self loathing and anguish, experienced by nearly all CD/TG's who discover this side of themselves later in life.
I sincerely think that your late mother and your sister deserve every accolade you can bestow on them for their recognition and fostering of your feminine character from such an early age.</p>
Hugs
<p style="text-align: left;">A lovely story and an experience of which I am very envious and I have to agree with Celeste that you would have become a crossdresser eventually, without the influence of your sister and mother.</p>
The feeling that you recall that you had when you first dressed and that were repeated over and over again as you grow up are a certain indication that the desire to dress feminine is part of your nature and would have arisen at some point in your life.
The fact that you learned that Crossdressing was enjoyable and accepted by your sister, mother and most importantly by yourself before people tried to tell you that it was something evil and unacceptable to 'their' standards which you should not do, most likely saved you from the years of fear, self loathing and anguish, experienced by nearly all CD/TG's who discover this side of themselves later in life.
<p style="text-align: left;">I sincerely think that your late mother and your sister deserve every accolade you can bestow on them for their recognition and fostering of your feminine character at such an early age.</p>
Hugs
I disagree in that the feelings I got were of a pre-pubescent sexual reaction. It’s something that happens to all boys growing up for one reason or another. In my case it was for more than just what I wore but the whole situation. Lately I’ve come up with a scenario that one day could be possible to test. If I was cloned and all copies were allowed to grow up in differing life circumstances would each copy end up a crossdresser? I doubt it since a part of who we are today is a product of our life’s experiences as well as our nature. Early on it was intense feelings of being dressed but not by my sling for it. True once it started I became somewhat depended on it to repeat that “feeling”.
Not only after the first time my sister dressed me up but even after several more occasions, I had zero interest in doing it with her let alone by myself. For me it was in a sense being forced to dress up, and my innocence responding to a confusing situation. Crossdressing absolutely can be in a sense induced. We are a product of our experiences. In my case I gave up trying to resist. My sister took that to mean my acceptance. Eventually I did come to at first at least not fight it anymore since I realized it wasn’t going to stop. I don’t necessarily consider what my sister did to her younger brother, me, necessarily cruel. But it wasn’t by my doing that it started or continued. Eventually I have up resisting which then slowly turned into some form of acceptance. My mother learned early on what was happening but rather putting a stop to it let it continued and at times assisted my sister. It was my mother who started taking me shopping, though my sister came along mostly. Eventually I gave up and accepted what was going on which fead into more of it happening. I absolutely know had my sister and mother not done what they had I wouldn’t have tried anything on my own. Psychologically it became a sort of crutch for my sexual development. I have come to terms with everything that’s happened. Even with the forcing that happened I did eventually become addicted to the act of dressing up and in my mid teens started on my own. Before then in the years prior you have to understand that I wasn’t dressed up every once in a while. It was all the time. Almost daily after school as I waked in the door I was made to change. Weekends as well. My mother’s sister was let in on the secret and made no bones about the fact she thought it was cute and whenever we visited I no longer dressed as a boy. My sister had a school trip one summer that my mother went as a chaperone. I was placed in my aunts care while they were gone. Once I was dropped off I never was allowed to wear boy clothes. In fact none wear packed.
Brenda;
I really don't know what to make of this addition. Part of me is so concerned that this was done 'to you' and part of me is thinking 'how lucky!'. Thanks for sharing it with us.
Do you feel that without this external start you would never have crossdressed? Or do you think that you may have just come to it later in life? (given that your original text seems to indicate it was addictive on the first time)
Did you ever get a chance to ask your mother why she and your aunt behaved the way they did? I ask because I had an event where my mother had enrolled me in dancing when I was young and I carried around a thought that it was her idea for years and suddenly thought I'd ask her why she did it, only to be told that I'd asked for it some months before she did it... I didn't remember that, but it certainly shifted my understanding of the motivation. Did her answer surprise you?
-Molly
My mother passed away in my early 20’s. By the time I had thought about a discussion with her she already was gone. My father was never in the picture so looking back I think maybe whatever she did was in spite of home. Can’t say much about my aunt either. I tried to talk to her a few times but she never allowed the conversation to go anywheres. I can say without a doubt in my case it was a learned behavior and really do feel that had it all not occurred I never would have found myself a crossdresser. Even though now I know better it’s too ingrained in my to stop. I have an attraction to wearing women’s clothing that is both enjoyable and not. Perhaps had it developed in me without all the “help” I’d feel different about it but that’s not what happened. I myself came to terms with it a long time ago. I know it’ll be there for the rest of my life. That’s just the way it goes. It’s been more of a double edged sword. My sister’s motivation was originally for her to have fun. She has admitted to me that she quickly realized that I became more passive with her which she liked. As time went in I think for her it turned into normal behavior on her part. As an adult she does tend to be more domineering than passive.
A lovely story, Brenda.
Brenda;
Thanks for sharing with us. I'm in awe of the depth of feeling in this story, and I'm so sorry you haven't had the pleasure of a relationship with your mother as a mature adult.
I'd be disappointed with the lack of discussion from your aunt, but I've seen enough to know there are those who feel that not mentioning something is the best way of handling it.
I'm glad you've found peace with it, and I've got to say being able to hear stories from others who share the desire to dress something most valuable, and your story is somewhat unique in that you feel that it may not have come to pass with your sisters actions, so it's doubly valuable in being a unique perspective.
Thanks, and wishing you all the best
-Molly
I think you were very lucky.
Everyone comes to it in a different way, but yours came in supportive, non-judgemental environment which I would have treasured when I was younger. I was conflicted about how I felt in my childhood and youth, not least because I not only fancied girls but also their clothes
I've remained heterosexual, but never stopped wanting to dress... I guess I'm not alone in that.