HI! My feminine name is Jillian, and I have been a male crossdresser since I was about 7-years-Old. I’m now older than dirt, but still very young at heart. Just the other day I started thinking about that first time I ever put anything girlish or feminine on. I know it happened a long time ago, and it feels like it was in a land far, far, away. I guess like the rest of us I don’t think about how it all really started anymore. It’s something that just happened, but if you really think about it. That act of putting on that first dress, or maybe just some panties & bra. Whatever it might have been, and whenever it was? You would have to agree about one thing. It was a life-changing event. It could have happened at age 6, 12 or even 24, but when you realized that you liked looking cute & feeling feminine. Your life was changed forever wasn’t it?

Do you ever think back about how it all came together that faithful day? How you felt, while wearing the items you decided to put on? What about the whole excitement of that moment? What you were thinking and feeling, when you put on those clothes that you stole or had hidden away? No matter what it was. Maybe it was just panties and a nightgown, but you just had to see how it felt to wear them. How did you end up dressing that first time? Was it something you wanted to do, or maybe it was a form of punishment for something you did wrong? Then again it could have been that you wanted to see how you looked dressed like your sister. Maybe you just wanted to see how you would look as a cute girl? Was it your sister, or your sister & one of her friend’s who talked you into dressing up for fun one day? Or it could have been a girlfriend, who asked just for fun to dress for her? Maybe someone suggested that you dress as a girl for Halloween? We all started out some way, some how, didn’t we? We all have our own stories.

So here I sat in front of my computer one day. I was writing an E-mail to a lady friend, who knows that I dress. She had asked me how & why I had dressed that very first time? That’s when I started remembering how on that faithful day I ended up dressed. It all started coming back to me, like it happen yesterday. So I stopped my E-mail to her, and I decided instead I was going to write it all down. Everything I could remember that happened that very first time. The more I remembered, and was writing down, the more came back to me, with all the feelings and the excitement. Not only did I remember the excitement, but I also remembered the thrill, fear, and also guilt of the moment. Yes I was remembering how it all started! Wow it was like I went back in time to that very day. That’s when I decide I would put the whole story down on paper. I would write it down just as I remembered it, and send it in as a story. This way others could see & feel how I felt. So here are my memories of the first time I ever put on a dress.

First off let me give you a little background about myself, and the era I grew up in. It was back when “SEX” was a “BAD” word, and no one ever talked about it. Almost no body knew what a Transvestite was. Heck back then no one ever heard of the words, Transgender, or Transsexual yet. The year was 1952; I was 7-years-old. I had a sister turning 5 in just a few weeks. That’s about when I guess you could say I realized that I was a little different. Just how different was I? I found out that for some strange reason, I liked dressing up as a girl. This was something that was so strange, new, exciting, and very confusing to me. I knew that as a boy; I felt like a boy, and I loved doing guy things. I knew boys just didn’t go around putting on dresses trying to look like a girl, but that’s just what I wanted to do. That’s when I started my secret life, with all of its hiding, fear, guilt, shame and confusion. Right up till that time, you could say I was like any other normal 7-year-old guy. I was into baseball, baseball cards, catch, football, biking, fishing, and of cause teasing girls. All the things boys my age were doing, which I still wanted to do. But I also wanted to wear all those cute pretty outfits girls wore. Talk about being confused?

There was one thing about me that made me stand out just a little from the other guys. You see even though I was 7-years-old, going on 8. I was kind of small & skinny for my age. I didn’t have a big growth spell till I was maybe about 10 or so. That’s when I took off in height and boy did I grow. Like I said, I loved to play sports, but I wasn’t really that good at any one sport. Being on the small, skinny side also had its other problems. I was always picked last for any team or game, and the other guys always picked on me for my size. I had very few friends, matter of fact I had maybe one really good friend, and guess what? She was a girl! So I had to be careful, because if the guys found out. Look out I would be picked on for hang out, and playing with a girl. Most times at any of the ball games if I wasn’t picked. I would end up setting on the sidelines watching the game, and wishing I could play. That happened a lot unless they really needed me, because one of the other guys didn’t show. Sometimes I would end up going home, and maybe playing around the house. Sometimes I ended up playing with my sister, and her friends. Then again I might see if my best friend was home, who happened to be the girl next door. If I played with my sister & her friend’s, we would play board games, hide & seek, or maybe house. If they were playing house I would always end up playing the daddy. I always try to go over to Lynn’s first, in hopes that she would be home and we could hang together? At her house at lease we could talk and maybe play cards or some board game. You see on our block Lynn & I were the oldest. We were both about the same age, and in the same class at school. We became friends because our mom’s were good friends, and we had played together since the 1st grade. All the other kids on the block were my sisters age or younger. I do remember sometimes, or a lease every once in a while, as I would be playing with Lynn or the other girls. I would get that now & then though, (Gee! girls really have pretty things to wear, why don’t I?) But like most boys with sisters, I figured that was a normal feeling to have. So I paid little mind to it. That’s till that faithful day.

My story really starts out a week before I put on that dress. I was on a shopping trip with mom and my sister. My sister was turning 5 in couple of weeks. Mom had decided she needed to go shopping for a new party dress. Hey back in the fifties that was the thing. Girls just had to have a cute party dresses to wear to your birthday party. Mom figured my sister needed a completely new outfit, from head to toe. Remember this was the early fifties. The time of little girl’s fancy party dresses, with tons of lace & bows. Oh yes and don’t forget the crinolines, and rumba panties. The crinolines held the skirts of those dresses standing up & out. So as the little girls walked along with her dress bouncing from the starched crinoline. You got a good look at her rumba panties under her dress. Oh yes gone are those days of cute frilly party dresses & crinolines forever.

As I was saying we were all out this one Saturday looking for that one of a kind, special party dress for my sister. We had already been to a couple of stores, but found nothing that Mom or Sis really liked. So here we were at yet another store, with my sister trying on yet more outfits. Ah wait a minute here we go! Mom seems to have found what she had been looking for. I must say, when I looked at this dress I thought to myself. WOW! That really is a pretty party dress. I can still see it as if it was yesterday. The dress was lavender taffeta / satin and had those cute puffed up type satin short little girl sleeves. Then at the arm openings of the sleeves there was elastic ribbon, with white lace attached to it all around, and cute little lavender bows on the lace of each sleeve. The dress it self was pulled in at the waist, and with a flowing flare out skirt style. You know the kind that little girls wore back in the early fifties. The dress also had white lace trimmings around the bottom hem, which seemed to gather up a little, where each bow rested on the hem. Giving the hem a nice look, with a white & lavender bow attached all along the hem about every 6 inches. It also had a lavender satin ribbon belt to help pull the waist in. The belt was made of a wide lavender satin ribbon that tied in the back in a big bow. There was a white fancy pinafore that came with the dress, which really made the dress look gorgeous. For those reading this who are a lot younger then I. A pinafore is a cute frilly protection apron that the little girls wore over the dresses to help protect the dress back in the fifties. This pinafore had lavender lace trimming it and matching lavender bows in just the right spots on the pinafore to make it & the dress it covered look oh so cute.

Like I said we had already been to a couple of other stores, and mom had gotten a lot of the other items she needed on sale. She already had a new full slip puffy crinoline; couple pair of lacey ankle socks in different colors. Mom also bought sis two or three pair of rumba panties in different colors. One of the panties was really fancy, and had row after row of lace on the front & rear, with a little white bow right in the center of the seat, which my sister just loved. Mom had also picked up a pair of black patient leather Mary Jane’s and a little girls pocket book to match the shoes. As I sat there in a chair near the changing room, all this stuff was in bags setting there in the chair next to me. As far as I could tell my sister had her whole outfit. All she had to do was try on this dang dress and we were out of there. I just sat in the chair at the store and watched. It seemed that all my sister wanted to do was complain. She didn’t want to try on any more dresses. She wanted to go home and play with her friends. I was setting there wondering, what’s all the fuss about. I’m thinking to myself. That’s a really pretty dress, try it on so mom can check it out, and let’s get the heck out of here; I also have things I want to do at home too.

It was then that I had a real good chance to take a nice long look at the dress. I’m thinking. WOW! That is some gorgeous party dress. It looks so lacey & pretty that I would think any girl would just love to wear it. That’s about when I got this strange idea in my head. I started wondering how I would look in a dress that gorgeous & pretty? You know one of those passing thoughts that pop into your head, when you’re setting in a chair, in a dress shop, bored to death. I never planned on putting on that dress. Hey I’m a guy why would I want to do that? It was just an idea that came to me out of nowhere at that time. Mom finally got her way as always. My sister fussed, but she tried on the dress. She looked fabulous. Mom was happy, and my sister? Well, heck! Even I could tell she loved how she looked in the dress. I remember how she was spinning around, and giving that wiggling move, you know what I mean. She was doing one of those side-to-side twisting wiggles. The kind that gets the skirt of the dress swishing back & forth, side to side, while all the time my sister was smiling and looking in the mirror at her self. She was watching how the dress wiggled on her. You could tell that she really liked the dress. So Mom paid for the dress, packed it up, plus all the rest of the stuff we had, and home we went. Man it was about time because I was really getting bored.

The next Saturday Mom had to take my sister to the doctor’s for something or other, and then food shopping. I was going to be staying home with dad. Just after she left, Dad got a call from where he worked. Dad was a truck driver and was gone over the road a lot. Sometimes up to four weeks at a time, but he was a great guy. I loved him till the day he died. Well, it seems they needed him to take a truck out for a local delivery. We could always use the extra money. So dad said, he would be right there. He told me I had to stay home, because they didn’t allow anyone to ride with the drivers. He said for me to be good & to keep all the doors locked. That he had talked to Mrs. Miller next door. So if there was any problem that Mrs. Miller is home and to go next door to her. He explained to me that mom should be home in about an hour or two. He said to tell mom he should be back by 6 o’clock. I said ok and he left for work as I locked all the doors. Back then you could do things like that. Heck we left our doors unlocked, as you knew all of the neighbors, and if there was a problem you could run to the house next door for help

Okay here I am, alone in the house try to find something to do. TV was not really big back then, but it was Saturday, and they had lots of kid’s shows to watch on the 3 or 4 channels we had at that time. I gave a quick look, but there was nothing good on TV. So to entertain my self I found my toy guns and started to play cops & robbers. I was shooting the bad guys all over the house, when I got to my sister’s room. I jumped into the room, rolled on the floor, and shot one of the bad guys. BANG! That’s when I seen it. There it was! “That Gorgeous Dress”! It was hanging on the closet door. The satiny taffeta was shining from the sunlight peeking in the window. I just stood their frozen looking at it. Something seemed to come over me; I felt this excitement building inside me. I’m thinking, that dress looks so pretty.

That’s when that idea came back to me, “what would I look like in a dress that pretty”? Then I’m thinking, what is wrong with you, are you crazy? Boys don’t wear dresses! I looked at the dress again, in its satin splendor, covered in all that lace and the bows. I wondered how it would feel to just put something that pretty on, and wear it for just a little bit? I’m not even sure why I wanted to try that dress on? I just did. I felt like the dress was calling to me > “TRY ME ON > go ahead you know you want too! So come on “TRY ME ON”. My head was spinning, and my mind was telling me > “NO” don’t!” “You’re a boy silly, what’s a matter with you, are you crazy”? “Boys don’t wear dresses”. Then I’m telling myself “Yes” it’s all right. Go ahead try it on, no one will know. See what it feels like, mom & sis aren’t due home for a while. The doors are locked, why not go for it, “TRY IT ON”, I finally gave in, and said, “YES”. One thing that was in my favor, my sister was a little lager then I was. As I had said before, I was on the small & skinny size for my age. Lets put it this way I was about the size of a 5-year-old. My sister was taller and ssssshhh a little chubbier then I was at the time. Grins. She looked like she was about 6 or maybe even 7. So I figured that maybe the dress might just fit me.

I found some older frilly rumba panties, with lavender lace, in one of my sister’s dresser draws. So I put them on over my briefs. Next came that full slip crinoline mom had just got her. I pulled it over my head and smoothed it out. The netting stood out all around me. Then I finally went up to the dress. OH! WOW! “THAT DRESS”, I touched it! Oh my! Touching the satin taffeta felt so silky that it gave me chills. I was so excited as I took it off the hanger and pulled it over my head. I slid it down so slow over the crinoline. Oh-My-Gosh! I remember I felt like I belonged in the dress all my life. OH! Why can’t this be my dress? It felt so great wearing it that I was shaking with delight & excitement. I did have some trouble with the buttons up the back. So I only did some of them the best that I could. Then I did one at the very top around my neck. That was so the dress hung right on me. I tied the ribbon belt in a bow in back. Next thing I was going to put on was the pinafore that hung on the door with the dress & crinoline. I decided not to, as it would hide the pretty dress, which I loved. The dress just stood out from the big crinoline that was pushing up on it. I figured why not go all the way, with a pair of Mary Jane shoes. I knew I had to put them on to look right, but first I needed some socks. Frilly ones if I can find them. I found a pair of older frilly socks in one of the draw and put them on. Then I put on the Mary Jane’s. Wow they fit me! I was surprised that the shoes fit so well. That’s when I walked over to look in the large wall mirror and almost died. Except for my hair, I looked like a girl about 4 maybe 5 years old; O-M-G, I looked a lot like my sister!

I decided to go into the bathroom and find mom’s hairbrush. I brush & comb my hair down from the center of my head all around. My hair was just a little on the long side, but not really long. I then combed it down in front try to make what looked like nice bangs. I do remember I went back to my sister’s room and looked around, because I needed to find one more thing. I needed a hair bow in white to match the bows on the dress. Ah yes there it is. I clipped the cute bow into my hair near the center of my head just above the bangs. I found my sister’s doll and picked it up. Then back over to the full-length mirror in her room again. I looked in the mirror, while holding the doll like I seen my sister do so many times before. I couldn’t believe what I was looking at. Could this be me? NO-WAY! There in the mirror was this little girl looking back at me and she looked so cute & pretty. With my hair combed down all around, and the bangs, plus the bow on top, holding the dolly. Wow! I was amazed at how much I looked like a 5 yr.-old little girl. My heart was pounding away. I really looked pretty.

I whirled around and did two spins while watching in the mirror. You could see the skirt of the dress, and crinoline flare out showing off the rumba panties. I was standing their wiggling side to side holding on to my dolly, still looking in the mirror. Oh I felt so good! Then it hit me. I remember thinking Oh Wow! I’m doing the same thing my sister did at the store, when she looked at her self in the mirror. She gave that little twisting side to side wiggles, so the skirt would swish back & forth, while looking a her-self. Now I knew why, because it felt so good seeing your self all pretty, and dressed up. I felt like I was floating on a cloud and going up. I’m thinking, wow is this how a girl feels all the time when dressed up? No wonder they love these pretty party dresses. The feeling was like no other I have ever felt. The mirror was telling me “This Is The Real you”. It was like I had found something I had lost. Only I didn’t even know it was lost till now. I just felt so good inside. It was like finding a new ME.

So here I was all dressed up looking like a cute little girl. Feeling like I have never felt before. I was feeling so pretty and so over whelmed! I’m thinking now what do I do? “No way was I just going to take all of this off, not just yet”. Not the way I was feeling. That’s when I looked around for my sister’s doll carriage. I started to play with her doll and the baby carriage, while watching myself in the mirror every chance I had. I was really into playing with the baby doll and having so much fun. I played like I was the little girl I felt like. This was my room, my doll, & my doll carriage. I was lost in my own world of girlish play, having such a great time. Then I heard the dog barking down stairs, which could only mean that mom, was home. OH NO! I looked out my sister’s window. Yep there was mom’s car heading down the street for the driveway. I was lucky that the dog was in the house and heard moms car.

Oh gees! What the heck am I going to do now? I knew I had to get everything off & back away fast. I was in a sweat and a big panic; I started running around like a nut taking everything off as fast as I could. I was trying to remember just where everything went. My heart was beating so fast. I had to get out of this outfit before I was caught, and then back down stairs. I couldn’t let mom or my sister catch me dressed like this. No Way! I was in such a state that my heart was beating out of my chest, and I was sweating like crazy. I was now worried that I didn’t put everything back where, and how I had found it. Is the doll where she left it, how about the carriage, I was in such a rush, but I was able to get everything off, and I was pretty sure I put it all back away in the right places. At lease I hoped all in the right places. I got dressed in my clothes, just as I heard mom & my sister coming in the back door, and putting down lots of bags. I heard mom go back out for more stuff, which gave me a couple of more minutes to check things over. My heart was still pounding over 90 miles an hour as I headed down stairs as fast as I could, trying to mess my hair up on the way down so you couldn’t tell how it was combed.

I was still shaking a little when I got down stairs. I was scared that mom might figure out what I had been doing. Mom asked me, what’s the matter? Are you ok? I said yeah I’m fine. Why? Well your all sweated up. I told her I was just running around the house playing war, when I heard you & sis come in. So I stopped I came running down the stairs that’s all. I’m just a little out of breath from playing, and running around I guess. She felt my head and said well set down, and stop running around you feel warm. (So far so good!) Where’s dad she asked. So I told mom where dad went and what time he would be home. I told her that he said for me to wait for her with the doors locked, and if I had a problem to go next door to Mrs. Miller’s. Mom said all right. Now come & help us put things away. I felt a little safe that mom had no idea what I had done.

All the rest of that day and the next, all I could think about was how I felt, and looked in that pretty dress. Plus how much fun it was to be dressed playing with my sisters doll. I kept think about that dress and how I looked so pretty in it. >”I guess you could say, “I WAS HOOKED”. I wanted so much to put that dress back on. I also wanted to tell mom all about my wearing of that dress. Maybe I could explain & show mom how I looked, and felt. I wanted to tell her how much I wanted to be dressed as a little girl. How I loved playing with my sister’s dolls and all. But there was “one big problem”! I just couldn’t! Something was stopping me. Something in the back of my head was saying. “NO!” “Are you crazy”? You can’t tell anyone! You know it was wrong to dress like that. Boys don’t wear frilly dresses and play with dolls. If you tell you could be laughed at, and made fun of. Maybe worse they may think you’re’ crazy and put you away in some Nut House. Do you want them to put you away? All of this went buzzing around in my head. Don’t forget I was only 7 years old at the time. What did I know? I was scared & confused, and had no idea of why I wanted to dress that way.

All I knew was that, deep down inside it felt great to wear That Dress. I knew I had to do it again. WHY? I didn’t know! I just knew I had to get that feeling back. I knew it wasn’t the normal thing for a boy to do, and that I had to keep it the biggest secret ever, by hiding and telling no one. I also knew that pretty soon, I didn’t know how or when? I would fine a way to dress up again in one of my sister’s party dresses. It felt so good to be dressed up so pretty, and pretending I was a little girl. I was hooked for life. That was over 50 years ago. I’m still dressing, only I’m married now, and my wife knows about my little hobby. She is ok with my dressing and even helps me with outfits sometimes. The both of us belong to a support group called TRI-ESS, which means I get to go out dressed at lease once a month to meetings.

That’s my story of how it went with the trying on & wearing of “THAT FIRST DRESS”, which you could say started my life of hiding, fear, guilt, shame, and confusion, but also a lot of FUN. I hope you enjoyed & learned something from my trip back in time.

PS: To this day I sometimes wish I had told my mom that day. Told her about putting that dress on, and playing as if I were a girl. Maybe things might have been just a little different in my life, who knows? Mom now knows about “Jillian”, I told mom all about Jillian about 8 years ago, and she has even seen me dressed. But guess what? MOM still loves me, and she thinks I looked kind of cute all dressed up. GRINS. Matter of fact she said I looked a lot like her, when she was younger. But that’s how Mom’s are; they will always love you “No Matter what”.

Magical Hugs & Little Girl’s Kisses:
JILLIAN