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.
In 2016 I will turn 58 years old and now here is my life story as a crossdresser.
Renee’s Early Years
It was 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. The fact that most of my life I have always been slightly overweight to downright pretty heavy. I have always been blessed in the chest area; gynecomastia.
In fact as I was going through school I was teased a lot by other kids saying I needed to wear a bra. I started out trying on my sister’s bras before 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. This happened before I ever started trying on my sister’s bras.
My Teenage Years
These are my first memories of CDing (crossdressing). 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 also tried on her nylon panties now and then. I would also try on my sister’s dresses and blouses whenever I could, whenever I was home alone.
I can say that I did have a few close calls when someone did come home early but 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 hidden 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 with my 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 know if my mother bought it but the subject dropped.
I started about the time I was in my early teens whenever my mother took me out shopping with her to observed mature females and watch for bra and panty lines, knowing that I may in the future want to venture out myself wearing a bra and panty. I also notice what made it hard to figure out if they had a bra on or not. I came to the conclusion that a loose heavier weight top covered things well. In my early teenage years I do remember wearing a bra at times 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.
If the shirt was lighter weight I would just make sure I had on an undershirt. I remember once one of my schoolmates seen me out and about in the neighborhood, we 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. Because of my desire to wear a bra outside more often as I grew older, I became very good at watching girls and women, remember I started doing this as I was younger, and seeing if I could see the bra showing though and also watching for lines from their bra brand and straps in their tops. I taught myself what to wear that would hide the fact I had a bra on and to not have panty lines in my pants. Through my middle teenage years there were many of times when I did absolutely no crossdressing at all. This is normal for all crossdressers. 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 wearing my sister’s bras and panties.
In my late teens and into my 20s once I got a job and a car I did start buying my own bras and other female clothing. I had a suitcase that I would keep my crossdresser stuff in, and I also had a small box I kept in the trunk of my car. 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.
My first Bras
I remember the first bra I bought was a Platex Cross Your Heart wire free bra. I even got myself some nylon panties, a pair of pantyhose, a purse, and eventually a couple tops, a skirt and a dress. I also started buying and trying to use makeup a bit. 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 the chores that was too 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.
My Waterbed Closet
By then I had bought a waterbed with two sets of drawers underneath. Now I had a great hiding spot behind the drawers under my bed. Through these years I started to 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. By this time I grew my outerwear a bit up to 3-4 tops, a couple skirts, and a few different dresses.
My Laundromat Trips
By this time I was also venturing out wearing women’s outerwear now and then out in public. Of course now and then I would have to go to the Laundromat to wash my CD clothes. I would go dressed later at night when there were no one else there most of the time. I would wear a blouse and women’s slacks most of the time and of course a wig. I also had a couple dresses to wear in the house when home alone. As far as shoes I had some 3” heels and some 1” heels to wear as well as some casual shoes and also tennis shoes. As time went by I tried several different bra styles; non-padded bras, padded cups (which back then were not foam padding but was more of a cotton batting) and eventually tried underwire bras, and even push-up bras. With the underwire bra I was now in bra heaven. The underwire, when I pulled myself into the cups, held me there much better.
Loving My Underwire Bras
From the time I was in my mid twenties I wore only underwire 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, I was wearing a 36-38 C-cup bra in my late 20s if I remember right. As I grew in size and weight so did my boobs and time would come now and then to replenish my supplies to new sizes.
Well most of my old stuff went in a bag and dropped off at the Salvation Army’s drop box. I do remember whenever I went out to buy new women’s clothing I would go out dressed in women’s clothing being too embarrassed to be buying them as a male. 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. Then I figured out that with buying women’s outer wear it was easy to pass off those purchases to the sales clerks as presents for my sister.
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, I tried on her bra and thinking that I filled it out just as well as she did but I was jealous of how much more round and perky her breasts were and mine mostly just resembled more of flabby fat tissue.
Renee’s Crossdresser Purging Cycles
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 crossdresser I believe you are a Crossdresser for life. You can quit but you will eventually come back to it.
At Last On My Own
As I reached my thirties and finally did make the move out of my parents 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 crossdreser.
I would try doing makeup on a boring night at home every once in awhile. I eventually got to the point that I thought I was doing a good job. I learned to use a cover stick to cover my shadow areas, patting it on and then covering is with a powder. At this time I started to shave my legs, armpits and chest all the time. I found myself shopping more often en-femme when shopping for female clothing. I started sleeping only in nightgowns unless I had company. I started wearing mostly women’s nylon panties. I eventually grew fond of stretch silk panties. Them things are hard to find now.
The Web is Born
By now it was getting into the middle 90’s and hello internet. I got into some AOL Chat rooms for crossdressers. I actually found that crossdressing was far more common than I ever thought. I no longer felt that I was the only one around for miles. I learned that there were actually females that will accept crossdressers.
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, she did find a few of my bras and panties in one of my drawers under my bed and she freaked.
Finally Got Caught Crossdressing
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 out 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. Shortly after that though, through the CD Chatrooms on AOL I came across a wife of a crossdresser in my state about a 90 minute drive from me. She invited me down for a night out with her and her “girlfriend” husband. I just couldn’t resist. This is way before the internet was not such a safe place to meet someone.
Too Good to Resist
After a few trips down for a night out with the “girls” I was really getting comfortable in venturing out more in my own area, mainly in the evening. She did eventually tell me of a friend she had that was single and was wondering if I would be interested in meeting her. I told her sure as long as she knew ahead of time about my crossdressing. This put her in a bit of a spot since her friend didn’t know of her husband’s crossdressing. But she did eventually tell her and had set up a date for the four of us to go out to dinner. We, eventually, on
one of our double dates went out to a “Drag Club” (a bar that has female impersonators performing and lip-syncing where most patrons are crossdressers dressed up in the area.
Well eventually we did get married, but although my wife knows of and allows me to crossdress she does not participate in it with me as I would have hoped. Early in our marriage there were a few times when we would go to a support meeting but eventually that dropped off. I reverted back to wearing outer clothes mostly only in the house. Maybe only a couple times a year will I venture out in a stretch top and slacks or a dress and wearing makeup.
My 40’s and 50’s
As I got up in my 40s and 50s I found it easy to pass in public. That is as long as I didn’t talk much. I grew my hair out long and I have kept my fingernails a bit on the long side. In my natural male appearance, at times, people I come across will refer to me as ma’am.
Perfect example was recently I was in the store picking up some groceries; I was wearing male jeans, a male polo shirt and Croc shoes. Yes underneath I was wearing a bra and panty. Maybe my breasts area had a slight bump in my shirt, but nothing that was that noticeable. I was clean shaven but had on no make-up. Well when I went through the self checkout I had trouble with my brand new debit card. The attendant came over and tried to help me. We eventually tried to put it on the store credit card that I had. Well that didn’t work either, lack of use. So we went up to the customer service counter to reopen my store credit card. To my amusement both the lady who originally tried to help me and the lady at the service desk both referred to me as “she” as they talked back and forth. The first lady left and the other never said anything to me as an apology. I never knew if she ever realized I was male. My hair was back in a ponytail and even when up the ponytail my hair is over my shoulder. I find it amazing just how often I am referred to as ma’am when not even trying. I still do not venture out much dressed enfemme, but when I do I don’t ever see anyone taking a second look at all.
As I turned into my middle 40s I found CD shopping much easier. 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.
I recently 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. Wearing them several hours a day for a couple weeks and you will say goodbye to your flat or inverted nipple. I would suggest starting with a #1 if you are small nipple and eventually move up to using the #2 or #3 size of them.
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. 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.
The Pueraria Mirifica Factor
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 took Pueraria Marifica (PM) for a year hoping that it will firm up my breasts and also give them a more natural female shape. I can say this much that I did notice more of a firmness to my breast tissue (especially when I wash them it the shower) although I can’t say much if I gained any shape or not. I didn’t expect much because of my age of 56 – 57 at the time I was using PM. I was taking three a day and took as much as 4 a day during one month. I could feel the difference in soreness and tenderness more so when I was taking four a day than I could taking three a day.
I do have a few dresses, nothing that is fancy or sexy. I have several female polo tops that have a percentage of Spandex in them, and I have a few pairs of female jeans. I keep a pair of low heels to wear if I am going out to the drag bars, but mainly will wear flats or tennis shoes (male or female) if just out on a shopping trip. I have a one piece swimsuit that I do wear when I go swimming in our pool. I do have a male suit if using a public pool.
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 in all my pictures but didn’t. 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. Once in awhile when my wife and I go out to dinner at a local restaurant I would have on a long sleeve MALE polo shirt and male jeans, a pair of Croc shoes and wear my hair back in a ponytail. I usually have my normal bra and panty also. Sometimes the waitress or waiter that greets us will originally refer to us as ladies. I may get an apology after I start speaking but most times I don’t. I think it bugs my wife at times but to me I think “PASSED AGAIN” and I wasn’t even trying.
At last More Acceptance for Crossdressers
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 (thank you Caitlyn Jenner) and also some that are starting at a young age of being out of the closet. One thing I do know for sure is that even though there is very little acceptance of our inner feelings 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.
Renee’s Tips on How to Pass In Public
Although dressing up in fancy sexy dresses and long eyelashes and full blown make-up is fun and exciting it is not the way to pass in public. 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 when 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.
Also if you go too conservative you will have chances of being read but still may stand out as well. Stay in the middle of the dressing spectrum of where you plan to go. Do your research of the event of which you are going. If you plan to just go out shopping take notice when you go there before you go en-femme just what all the females are wearing. If you can develop a female style voice it will get you a long way also. That is something that I have not took the time to do. Also keep in mind that although large breast are desirable for the crossdresser, make sure that you don’t draw all the attention there. Try to keep it proportional to your size. If you are thin then you do not want to be sporting DD breasts. I know that there are some girls out there that are that blessed but it is far from the normal. Sticking with a C cup will keep you in the normal range. Even a C cup on a thin girl looks big but at least it is more close to normal.
I am 5’ 11’ and 270 pounds so my 42 DD – 44 D cup size does not stand out especially with a rounder stomach area. They do stand out if I am wearing a tummy tamer of some sort. But I very seldom will wear one, maybe if I go out to a drag bar or someplace where I know there will be many crossdressers.
Do some research of where you may want to go dressed up. Go there a few times dressed as a man and notice what the females are wearing. Keep in mind your age range also. If you are going to a fancy restaurant then a more formal dress and stilettos may be the norm. But a family restaurant a light summer dress to even just slacks and a top would be best. How about the movies? Just go as casual female.
For those times when you need to use the restroom, keep in mind just how busy that restroom is, if you feel comfortable in your ability to pass then don’t hesitate and go right to the women’s. If you are unsure then it’s best to stick to the men’s room. Look at it this way that if you are busted as a male using the women’s room you could end up in much more trouble than if you use the men’s room and get spotted or even if you don’t get spotted. A guy would be more accepting of a lady using the men’s room than what women would be of a man using theirs. Personally I only go out for the amount of time I can stay out of the restroom, unless I go out in full blown makeup or I find a lesser used small ladies room: such as a gas station.
Play Safe With Your Makeup
Makeup is another thing to pay attention to when researching. Just how much makeup are the women wearing and what are the latest colors, and how thick or natural looking are they looking. I generally found in my area that eye shadow and eyeliner is not very popular unless you are going to some type of formal event.
Go With The Flow
Although most crossdressers really enjoy going all out in a fancy maybe formal dress, really high heels, flashy application of makeup and using bright red lipstick and nail polish this is not the way to go out in most public places and expect to pass. Drag bars and support groups are reserved for going all out like that.
Keep in mind in most cases less is more. Meaning staying conservative and in the middle of the range of what you see other women wearing will get you by more often than you would think.
About the Author:Hi, I’m Marcy Simpson, founder and creator of Crossdresser Society. I have been a crossdresser for over 2 decades and I am also an author, photographer, entrepreneur, and admirer of the feminine realm. I currently work and live in Los Angeles, California.