A fascinating and revealing real life story of Renee’s crossdressing journey!

My story as a crossdresser started as I was very young!

Probably when I was in the age range of 8 to 11 years old. I am now 56 years old crossdresser!

But before I get into my crossdressing journey let me go over how I define some of the words associated with transgendered people and a few other ideas. I am not a psychiatrist or anything like that these are just my perceptions.

What is my definition of a crossdresser?

Simply a crossdresser is someone (generally a heterosexual male) that will wear clothing of the opposite sex. They can have a fetish to certain parts of a women’s wardrobe. Mine personally have been a bra and also panties. Some other fetishes that I know of are pantyhose or nylon stockings, some people like stilettos heels, and other like dresses and like make-up. A lot of crossdressers (CDs) with a fetish for female undergarments will often wear them daily and even when at work; depending on the type of work they do. As I said earlier most CDs are NOT gay but there are a small percentage that are gay. Also a CD will only occasionally go out in public dressed as a female, more often if they have an established safe place to go frequent such as a Drag Queen bar, yet probably the vast majority of CDs only do this in the comfort of their own home and have never ventured out in public en-femme. Known as in the closet or closeted.
How this differs in my opinion from a Transvestite (TV) is that a TV is more often either gay or bisexual. Also transvestites also generally prefer to in public dressed en-femme more often than CDs. Transvestites will often over state their femininity wearing more elaborate outfits and generally overdoing their make-up. More often than not you can easily spot a TV because they will look great but is over done with their feminine appearance. Versus a CD if polished will blend in much better and pass as a female very well. A CD that has not going out but a few times are easy to spot too because some of those also will over do themselves for the surroundings they are in. Or they just may be too nervous and give themselves away that way. A TV is very seldomly closeted. A gay TV will use his attribute to find male dates, where a CD will keep more to themselves.
Transgendered is just a blanket term for CDs TVs and also Transsexuals either pre-op or post-op. Compared to my early years there is so much more resources available to transgendered people. I believe this is because of the internet as there are a lot more people in the news as transgendered especially when they are starting at a young age of being out of the closet.
Last of all the terms crossdresser and transvestite are used for males wanting to be perceived as females I do not want to exclude females that have gender identity desires. Although I do not know of any terms use for our female counterparts but I do know that in general terms such as a “butch” female or just a “tranny” (short for transsexual) have been used with our female counterparts.
One thing I do know for sure is that even though there is very little acceptance of our inner feeling and desires, it is for more accepted now than when I was growing up. How nice it would be to go out all dressed up en-femme and not having to worry about if you looked good enough to pass as a female or if you sounded female.
I have found that the best way to pass out in public as female is to be conservative in your make-up, jewelry, and most importantly the choice of your clothes you wear on the outside. For example do not wear a dress and especially a flashy dress wear all the other women are wearing jeans and a T-shirt. If polo style shirts are the norm then don’t wear a frilly blouse. If you stand out in the crowd you will be read (spotted as a crossdressed male) in a second.

Ok, let’s start getting into my life story as a crossdresser.

Back into the middle to late 60s when I was in my late single digit age or pre-teenage years and when my next older sister started going through puberty and started wearing a bra I found myself trying on her bras when I was home by myself.
I am the youngest of five kids having two older brothers and two older sisters. The fact that most of my life I have always been overweight I have always been blessed in the chest area. In fact as I was going through school I was teased a lot by other kids saying I needed to wear a bra.
I cannot really say if I started out trying on my sister’s bras before or after I was being teased by my schoolmates. I also remember a time when I was real young, maybe before I was ever in school, I had a crush on one of my neighbors that was around my same age.
She was having a party (maybe a birthday party) but only girls were invited. Because I begged my sister to take me along she would only do it if I wore a dress. I did. These are my first memories of CDing. As I aged through my teenage years I still was trying on and even wearing my sister’s bras now and then and with my fatty chest tissue I would pull myself into the bra cups as much as possible.
I would do this as often as I could get away with it. I even stole one of my sister’s bras and kept it his inside of my pillow. Who would guess (when I was real young) that mother would actually wash pillow cases. She found my hidden bra and asked me about it. I was very embarrassed but quick thinking I told her I wanted a more padded pillow and that was the only thing I found to add more padding. I don’t think my mother bought it but the subject dropped.
In my early teenage years I do remember wearing a bra at time out at night in the neighborhood. I would wear my shirt loose at that time and had my parents buy my clothes that way with the idea I was still growing and that way I could wear the same shirts for a longer period of time without having to waste money buying new shirts as I grew.
I remember one time one of my schoolmates seen me out and about in the neighborhood, talked a bit and then he gave me a friendly punch between my breasts. I remember being worried if he could tell by his punch if I had a bra on. He never said anything so that was my first test passed. I would also try on my sisters dresses and blouses whenever I could, mainly when home alone. I can say that I did have a few close calls when someone did come home early.
Because of my desire to wear a bra outside more often as I grew older, I became very good at watching girls and women and seeing if I could see the lines in their tops of the lines of the bands of a bra and also I would see if I could see if their bra showed through or not. I taught myself what to wear that would hide the fact I had a bra on. Through my middle and later teenage years there were many of times when I did absolutely no CDing at all.
Then there were times when I wore a bra out several times a week for my evening activities. I did not wear one when out with my friends when I knew that we were going to be playing hard, either sports or other activities. Most of the time I was out by myself either biking, or at the Little League field or something where I did not have to worry about close contact. At this time I was still stealing and wearing my sister’s bras and panties.

In my late teens and into my 20s I did start buying my own bra. Again there were times that I did nothing at all but these times were not as long as they were when I was a teenager. I remember the first bra I bought was a Platex Cross Your Heart wire free bra. As I got to the age when most young adults moved out of the nest for some reason I never did. Part of the reason is some health issues of both my parents I convinced myself that I need to be home with them to help out with chores that was hard for them to do. The other part is I was too cheap to spend the money to live in an apartment and took advantage of a good thing.
Through these years I did wear a bra very often always pulling my fatty chest tissue into the bra cup. I also enjoyed wearing a dress and also frilly blouses now and then. As time went by I tried several different bra styles; non-padded bras, padded cups which back then were not foam padded but was more of a cotton batting, and eventually tried under wire bras, and even push-up bras. With the under wire bra I was now in bra heaven. The under wire, when I pulled myself into the cups, held me there much better.
From the time I was in my mid-twenties I wore only under wire bras, always pulling myself into the bra cups as much as possible. I do not know if it was because of this and starting at a young age of wearing a bra or if it just simple genetics (both my sisters and also my mother have larger breast than average) that has blessed me with larger man-boobs to the tune that at that time I was wearing a C-cup bra and if I remember right a band size of 36 or 38. By this time I also ventures into wearing women’s outerwear now and then out in public.
A blouse and women’s slacks most of the time and of course a wig but I do remember having a dress to wear in the house when home alone. I do remember whenever I went out to buy a new women’s clothing I would go out dressed in women’s clothing being too embarrassed to be buying them as a male.

Until I figured out that with the women’s outer wear it was easy to pass off those purchases to the sales clerks as presents for my sister. I am sure I was noticed back then being inexperienced, but I figure with a wig on and make-up that people would not be able to tell who I was. I even took the time to go into the next city to do my purchasing of my outfits.
When I had my first real girlfriend I remember one time as she was in a shower, after a night of renting a motel room, trying on her bra and thinking that I filled it out just as well as she did but I was jealous of how more round and perky her breasts were and mine just resembled more of an extra roll of fat tissue. There were times when I purged (getting rid of all the CD clothing) throughout these years but eventually came back to it as I could not bury it behind me. If you are a CDer I believe you are a CDer for life. You can quit but you will eventually come back to it.
As I reached my thirties and finally did make the move out of my parent’s house I almost exclusively wore women’s clothing when in my own place. It was during these times I really progressed into being a true CDer. At this time I started to shave my legs, armpits and chest all the time. I found myself shopping more often en-femme and always when shopping for female clothing. I started to only sleep in nightgowns unless I had company.
As far as girlfriends I had only a few and obviously kept my CDing a secret. But the last girlfriend I had, before I met my wife, did find my clothes and she freaked. She first thought I was cheating on her since we lived 70 miles apart. But I did tell her about my desire to wear women’s clothing now and then. I figured since she was a country bumpkin type of girl and came across as a fun loving simple person that she would accept this part of me and would enjoy going as girls now and then having fun together as girlfriends. I could not have been more wrong. Her words to me were something like this: When she came home at night she only wanted to come home to a man.

What a blow to my ego.
As I turned into my middle 30s I found the internet and CD chat rooms. I also found a way to correct my flat and inverted nipples by purchasing a fake nipple and areola product online. I cannot remember where I got them from anymore. This spring I have found a better option, that option is called Supple Nipps which are thimble size suction cups you put over your nipple and areola and give it a squeeze and watch them protrude outwards.
Wear them several hours a day for a couple weeks and say goodbye to your flat or inverted nipple. I would suggest using the #2 or #3 size of them. It was on the internet I came across a wife of a CDer in a different part of the state that I live in that was more than an hour away. In the area they lived in there is a Drag Queen bar. If you don’t know what a Drag bar is it is one where Drag Queens either TVS or CDS would perform on a stage as a women. They mainly lip-sync song by female artists. This bar is known as a hangout for people who like to crossdress and just hang out and also transvestites who would look to pick up guys. Hence my perceptions earlier of the differences between a CD and a TV. Eventually the wife of this couple convinced me to make the trip to their town and go out to this bar.
After a few visits over several months she told me about her best friend and asked if I would be interested in meeting her. I told her I would under two conditions, one being that she knew of my CDing ahead of time, and the other is that she had to have bigger boobs than I had. By then I had progressed into a D cup bra. Well the second part was not a problem but the first part put her in a bit of a spot since not any of her friends knew her husband was a CDer. She did eventually spill the beans to her best friend with the assurance of her holding in confidence her husband’s secret.

We went out a few times double dating once to dinner and couple times to the Drag bar.
We started going on our own dates and all the time I would be wearing a bra and panty and she knew that. At the end of the 90s we did get married and as time has gone by I find myself not as often wearing women’s outerwear as often. I do wear a bra and panty daily just as any woman would and even more so than they do. I do not take my bra off when I get home from work. There are times I even sleep in my bra. I do sleep in a nightgown. I do have women’s tops that have around 5% spandex in them to hug my body and show off my breast shape.
Throughout most of my life I worked in either the restaurant business or retail business where having long hair is not allowed on males. So I did have a few cheap wigs to wear when I did go out dressed en-femme. At the time I met my wife though I was working my own business having an installation business and far the couple years before that I had a manufacturing job where I could let my hair grow long and not having to wear a wig at all.
After installations were not paying well anymore I found myself working in retail and long hair although was frowned upon there was a couple of us that did have long hair. I worked a total of about 15 years in retail and worked for the same boss all those years. As I was able to keep my long hair I also grew my fingernails longer than most.
My boss always the kidding type every once in a while would through out there in front of my coworkers asking me if I like to wear women’s clothing at home. Of course I always denied it. But, if he only knew the truth. Eventually though, that did get more scrutinized in that company and they watch your sales numbers more so it became easier work wise to comply with a “professional look”. By then though, I no longer had the desire to go out in public en-femme as my wife was accepting of my CDing whenever I wanted.
To this day I only have female panties and have probably two dozen bras that I wear. All my bras are Bali Flower bras. These are underwire and unpadded. They are very supportive and give a good shape making me look more perky and youthful. I have recently come across a product called Pueraria Mirifica that will help develop breasts even in males after taking it for a period of time. I would suggest at least six months to even a year or more depending on the size you desire to be. In my Bali bra I am now wearing a DD cup bra, but in other brands I would still be a D cup.
I am now hoping that while I am taking Pueraria Marifica (PM) that it will firm up my breasts and also give them a more natural female shape. If I gain a bit more size then I would look at that as a bonus.

In the photo of me in the red top this is a female polo shirt that has 5% spandex in it so that it will hug the body better and show of my breasts shape better. I have a touch of make-up on a natural pinkish lipstick and just a slight coating over my whole facial area. I really should have done a better job on the make-up but didn’t know I was out of foundation.

Finally I put a curl in my hair. I will say this much that you would not believe how often I get call ma’am when I go out to a restaurant or in the grocery store with none of that done; just my long hair and shapely chest and clean shaven gets me by a lot.