PG Oh That First dress
a tale of how it all started
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OH! That First Dress

I guess like most of us little girls, I rarely give any though to when or even how I put on that first dress. Its something that happened a long time ago, in a land far away. But if you really think about it, you have to realize. That putting on that first dress, whenever, or however, it happened, it was a life-changing event.

I know must of you must remember the first time getting dressed, but do we really remember it? Do you think about how it all came about, and how you felt? The excitement of the moment as you put that dress on. What were you thinking or feeling, when that dress went over your head and you buttoned or zipped it up. How the fabric felt against your skin?

How did you end up dressing up that first time? Was it something you wanted to do, or wasit as a form of punishment for something you did wrong? Maybe it was because you wanted to see how you looked dressed like your sister or as girl? Maybe it was an idea of your sisters or she and a friend together talked you into dressing up as a girl for fun one day and you were hooked?

Then again could it have been a girlfriend who asked if she could dress you up for fun? OhI know maybe she or someone else suggested you dress as a girl for Halloween? We all started out some way didnt we? We all have our stories.

So there I sat one night dressed in one of my cutest little girl outfits, right down tothe tights, frilly rhumba panties and Mary-janes. I was sitting there holding onto my dolly, watching a Shirley Temple movie on DVD. I started to think back to that first time when I dressed up in a cute frilly party dress, like the one Shirley was wearing in the movie.

I was remembering how on that faithful day I ended up dressed. It all started coming back to me, like it happen yesterday.The more I thought about it the more I remembered. I started to remember how I was feelings andthe excitement I felt inside as I put that dress on. I remembered all the trills of the moment and how it all came about! Everything that happened that day was coming back to me. Even the part about how confused I felt, because Iliked wearing that dress, but why do I like wearing this dress ? Im a boy and boys dont wear dresses?

Wow it was like I went back in time to that very day. So let me take you back to yesteryear and how I ended up wearing my first dress.

First a little background, about me and the era I grew up in. It was a time when SEX was a bad word, and no one ever talked about it. Almost nobody knew what a transvestite or crossdresser was, and if they did they kept it quiet. No one ever heard of the words, Transgender, or Transsexual. The year was 1952 and Iwas 7-½ going on 8- years-old. I had asister who was turning 5 in three weeks.

Thats about when I realized that I was a little different. Just how different was I? Ifound out that for some strange reason, I like dressing up as a girl and wearing a pretty party dress. This was something that was so strange, new, and very confusing to me. I knew that as a boy; I just couldnt go around dressing up like a girl. So thats when I started my secret life, with all of its hiding, fear, and confusion.

Right up till then, you could say I was like any other normal boy. I was into baseball, catch, football, riding my bike, and of cause fishing. There was one drawback that I had at age 7 &1/2. I was kind of small for my age (not like now 6ft “2 inches tall and 210 lbs giggles). Like I said, I was on the small side back then,and I wasnt really that good at sports, but I did love to play them.

Being on the small side had its other problems too. I was always picked last for a team and always picked on a lot about my size. So I kind of had very few friends to play with. Most times I ended up playing with my sister & her friends.

I do remember for some reason every once in a while as I played with the girls, I would get that now & then though in my head, (Gee! girls really have pretty things to wear, why dont I?) But like most boys with sisters, I figured that was a normal feeling to have. So Ipaid little mind to it. Thats till that faithful day.

My story really starts out a week before I put on that dress. It was Saturday and I was on a shopping trip with mom and mysister. My sister was turning 5 in about three weeks. Mom had decided she needed to go shopping to get a new party dress for my sister. She figured my sister needed a new outfit for her all girl birthday party. So off to the Perth Amboy we when. Back then there were no shopping malls. You did your shopping in the towns that had the most shops; or maybe a place called Two Guys. We had already been to a couple of stores so far, but found nothing mom liked dress wise. So here we were at The Learners Dress Shop, which was a pretty popular store for the ladies and kids clothes.

Ah yes !Finally Mom seems to have found what she had been looking for. I must say, whenI looked at this dress I thought it was a real pretty dress. The dress was pink taffeta / satin and had those cute puffed type short little girl sleeves. The sleeves at the arm openings had elastic with white lace all around, and a cute little pink bow on each one. The dress its self was a flowing flare out skirtstyle that took a crinoline under it. You know the kind that all the little girls wore back in the early fifties. The dress had white lace trimmings, and pink & white bows all along the hem, and one large one just under the chin attached to the peter-pan collar. It also had a pink satin sash for a belt that tied in a big bow in back. The sash with the bow pulled the dress in around the waist and really made it look gorgeous.

We had already been to a couple of other stores in town, and mom had gotten everything else that she needed to go with this new outfit. Most of what she bought was on sale at the other stores. She had already picked up a full slip multi colored pink & lavender crinoline, a couple of pairs of lacey ankle socks. There were a number of rhumba panties too, about 4 pair, which my sister just loved.The panties all had row after row of lace on the front & rear, and some came with a little bow right in the center of the seat. Mom had already picked up a pair of black Patient leather Mary Janes and Black Patient pocket book to match the shoes.

The little girls department at Learners was down stairs, which I was glad about. I was worried that one of the guys might come along and see me in the girls department. You could bet if he did I would be picked on about that too. One of the reasons because I was now sitting in a chair near the changing room door holding on to the multi colored crinoline mom had handed me. I happened to look over in the large full wall mirror. I swear if any ofthe guys would have looked at me, it almost looked like I was wearing the crinoline, as it sat on my lap. All the other stuff mom had bought already were in bags setting 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 here. I just sat in the chair and watched. All my sister did was complain, that she didnt want to try on any more dresses. She wanted to go home and play with her dolls & her friends. I was trying to figure out what all the fuss was about. Im thinking to myself, Gees, thats a real pretty dress, put on this crinoline and the dress so mom can check it out. Come on all ready lets get the heck out of here, my friends were waiting for me too. What two friends I had.

Mom had just grabbed the crinoline from me and was finishing up getting my sister into it. She was now trying to put the dresson her. I guess it was about then that I had a chance to take a nice long lookat the dress for a couple seconds. Im thinking. WOW! The whole outfit is great looking and what a gorgeous looking dress its so pretty,

Thats when this strange thought popped into my head. I wondered how I would look in a pretty party dress like that. Youknow one of those passing things that pop into your head, when youre setting in a chair, in the little girls department of a store, bored to death. I got rid of that idea real quick and tried thinking of something else.

Mom finally got her way as always. My sister fussed, and complained, but she tried on the dress anyhow. I must say shelooked fabulous. Mom was happy, and my sister? Well, heck! Even I could tell she loved how she looked. I remember how she was spinning around, and giving one of those wiggling moves, you know what I mean. The kind where youve seen the little girls wiggle side to side with a twisting wiggle. All the time she was twisting & wiggling she was smiling and looking at herself in the mirror. You could tell she liked the dress. So Mom packed it up, plus all the rest of the stuff, and home we went.

The next Saturday Mom had to take my sister to the doctors for something or other, and then they were going food shopping. I was staying home with dad. Just after they left, Dad got a call from work. Dad was a truck driver and was gone over the road a lot. Sometimes up to four to five weeks at a time, but he was a great guy.

Well, it seems they needed him to take a truck out for a local delivery. We could always use the extra money, so dadsaid, he would be right there. He looked at me and told me to keep the doors locked and that mom would be home in about 2 hours. He told me if I had anytrouble to run next door to Mrs. Doyles house. He also said to tell mom he should be back by 6 oclock.

I said ok and he left for work, as I locked up all the doors. Back then if you had trouble you ran next door for help, and this wasnt the first time I was left home alone for an hour or two.

Anyhow here I was, alone in the house. 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 sisters room. I jumped into the room, rolled on the floor, and shot one of the bad guys. > BANG!

Thats when I saw it. There it was! THAT DRESS! It was hanging onthe closet door. The satiny taffeta was shining from the sunlight peeking in the window. I just stood their frozen in time looking at it. Something seemed to come over me; I felt this excitement building inside me. Im thinking, that dress looks so pretty, what would I look like in a dress that pretty?

Then I snapped out of that idea thinking, what the heck is wrong with you? Boys dont wear dresses!

I looked at the dress once again, with the satin and all that lace and the bows all around. I started to wonder how it would feel to wear something that gorgeous.Im not even sure why I wanted to try it on, I just did. I felt like the dress was calling to me Try Me On. Come on you know you want to Try Me On My head was spinning, as it was trying to tell me whats wrong with you NO dont put that dress on !

I Then started thinking why not > what the heck go ahead try it on. No one will be home for a while and the doors are locked. So why not go for it, try it on. See how it feels to wear a pretty dress like this.

I finally gave in, and saying to myself , YES I have to see how it feels.

One thing that was in my favor, my sister back then was a little lager then me. As I had said before, I was on the small size for my age. Okay lets put it this way; I was about the size of a 5-year-old in height and a little skinny. My sister was just a little taller and ssshhh, a little chubbier then me. She looked like she was almost 6 maybe 7.So I figured that the dress might just fit me.

I found a pair of older pink rhumba panties of my sisters in her draw. So I put them on over my regular underwear. Next came that multi colored full slip crinoline mom 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! The satin feel of the taffeta felt so silky that it gave me chills. I took it off the hanger and pulled it over my head and slid it down over the crinoline. Oh-My-Gosh! I remember it felt like I belonged in the dress my whole life. OH! Why cant 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 around the neck opening, then I tied the pink sash in a big bow in back.

Now it was time for the Mary Jane shoes. I was going to put them on, but first I needed some socks. Frilly ones if I can find them. I found a pair of older frilly socks in the draw and put them on.Then I put on the Mary Janes. They fit me just right. I was surprised that the shoes fit so well. Thats when I walked over to look in the mirror and almost died. Except for my hair, I looked like a girl about maybe 4 or 5 years old; OMG >>>I looked a lot like my sister!

I decided to go into the bathroom and find moms hairbrush. Once I had the brush; I brush & comb my hair down from the center of my head all around. My hair was combed down in front making nice looking bangs.

I remember I went back to my Sisters room and looked around. Yes thats what Im looking for. I found a hair bow in white to match the bows on the dress. So I clipped the cute bow into my hair near the center of my head above the bangs. I found my sisters doll and picked it up.Then back over to the full-length mirror again. I looked in the mirror while holding the doll like I seen my sister do so many times before.

I couldnt believe what I was looking at. Could this be me? NO-WAY! There in the mirror was a girl looking back at me and she looked beautiful & pretty. With my hair combed down in bangs, and the bow on top, holding the dolly. Wow! I was amazed at how much I looked like a 5 year-old little girl. My heart was pounding away because I thought I looked so cute & pretty.

Next I decided to whirl around and do two spins while watching in the mirror. You could see the skirt of the dress, and crinoline flare out showing off the rhumba panties. I was standing their wiggling side to side holding on to that doll, still looking in the mirror. OhI felt so good!

Then it hit me. Oh-My-Gosh! I remember thinking wow! Im doing the same thing my sister did at the store, when she looked at herself in the mirror. She gave the same little twisting side to side wiggles, while looking at herself. Now I knew why, because it felt so good seeing yourself all pretty, and dressed up so adorable looking. I felt like I was floating on a cloud and going up. Im thinking, is this how a girl feels all the time when she gets all dressed up? No wonder they love these party dresses. The feeling was like no other I have ever felt. The mirror was telling me This is the real you. Its kindof hard for me to explain or even understand.

Lets put it this way It was like I had found something I lost; Only I had no idea I even lost it, it was truly a great feeling.

So here I was all dressed up like a little girl. Feeling like I have never felt before. I was feeling so pretty and so over whelmed! Im think now what do I do? No way was I just going to take it all of this off, not just yet. Thats when I looked around for my sisters doll carriage. I started to play with her doll and the baby carriage. I was really into it and having so much fun. I played like I was the girl I felt like. This was my room, my dolly, and doll carriage.I was lost in my own world of girlish play, having such a great time.

Then I heard our dog barking down stairs, which could only mean that mom, was home. OH NO!

I was in a big panic and started get real worried; I looked out my sisters window. Yep there was moms car heading down the street for the driveway. I was lucky that the dog was in the house and I heard him. Oh gees! I started running around like chicken with its head cut off trying to take everything off while in a real panic.

I was trying to remember just where it all went. My heart was beating so fast. I had to get out of this outfit fast, put it all back where it belongs, and the get down stairs. I cant let mom or my sister catch me dressed like this. I was having a hard time undoing the buttons on the dressand was really panicking. Once the dress was off I was worried that I wasnt putting everything back where and how I had found it. I knew I was in a rush and panicky, but I believe I was able to get all the stuff off, and back away.I was just hoping it was all in the right places.

Once I was undressed and everything back in place I hurried to get dressed in my clothes. , thats when I heard mom & my sister comingin the back door, and put down lots of bags.

My heart was still pounding 20 miles an hour as I headed for the stairs as fast as I could. I started for the door of the room and looked inthe mirror. Dang I forgot the bow in my hair. So I grabbed it and throw it in one of the draws and then messed my hair up.

I was still shaking a little when I finally got downstairs. I was scared that mom might figure out what I did.

Mom asked me, whats the matter?

Are you ok?

I said yeah Im fine. Why?

Well youre all sweated up.

I told her I was just playing war and heard her & sis come in. So I came running down the stairs thats all. Im just a little out of breath from running around shooting the bad guys and then running down here I guess.

She felt my head and said well set down, and stop running around you feel warm.

(So far so good) !

I told mom where dad went and what time he should be home. I then told her that he said for me to wait for you with the doors locked.

She said all right. Wow Now I was feeling a little safer that mom had no idea what I was up to.

About an hour later I had to use the bathroom. As I pulled down my zipper and reached inside I had the shock of my life. It seems in my rush to get down stairs I left my sisters pink frilly rhumba panties on. So I quickly locked the bathroom door and took off my pants & the panties. I then got dressed and stuck the panties under my shirt. I opened the bathroom door checked to see if any one was around.Then I ran to my room and hid them under my mattress till I could get them back in my sisters room.

All the rest of that day and the next day, I was thinking of how good I felt wearing that dress, and how much fun it was to be dressed up playing with my sisters doll. I kept think about that dress and how I looked.

Yes I was now hooked I wanted so much to put that dress back on. I wanted totell mom about me wearing of that party dress. I could explain & show mom how I looked, and felt. I wanted to tell her how much I wanted to be dressed asa little girl. How I loved playing with my sisters dolls and all.

The One Big Problem! I just couldnt, something inside was stopping me. Something in the back of my head was saying> NO you cant tell! You know it was wrong to dress like that. Boys dont wear frilly dresses and play with dolls. If you tell you would be laughed at, and made fun of. Maybe worse they may think youre crazy and put you away in some Nut House. You will never see mom or anyone ever again. All of this went buzzing around in my head.

Dont forget I was only 7 & ½, what did Iknow? I was scared & confused.

All I knew was that, deep down inside it felt great to wear that pretty outfit. Iknew I had to do it again. Only I didnt know WHY I felt this way? All I knew was I had to get that great feeling back. I knew it wasnt 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 didnt know how or when? I would find a way to dress again in one of my sisters party dresses. It felt so good to be in that dress pretending I was a little girl. So now I was hooked for life.

Its now 2013 and Im still dressing up like a cute little girl or baby girl. What can I say I just love the look of a little girls party dress with a full crinoline and rhumba panties under it.

Okay girls! Thats the story of how. That first party dress change my life forever. I hope you enjoyed the trip back in time.

Big Hugs & Little Girls Baby Kisses to All:    

Little Jilly  

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I liked the story about your real life experience. Mine was both gf and mother, as they both worked on me for halloween, yes at the time i was embarassed.
The diapers well they came years earlier, as they were used as punishment for wetting and "acting like a baby." Like you i was small too, unlike you i didn't grow that
Lil Jilly please keep writing i enjoy your stories whether real life or fiction.
krystala's sissy baby

Thank you for sharing your story. I have a similar tale as you, sisters dress and hooked for life, I also did not dare to tell, and I still love my little girls dresses and diapers and always will :D




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