I Was Curious, So I Did It.

I was the middle child of three. I had an older sister and a younger brother. The house I grew up in had only one bathroom and I recall as a teen the many times I would see my sister's or mom's delicates hanging from the shower rod to dry. Nylons, pantihose and even a dress or blouse that had to be hand washed and air dried.

One afternoon I was sitting on the throne just staring at this jumper skirt my sister had left to dry. I recall seeing her wearing it and it would come to just above the knees and have these long straps that went over the shoulders (she would wear a button down blouse with it). So I just stared at it...wondering. Curious. "I wonder what it feels like?" "I wonder how it would look on...me?"

Well, after I cleaned up I ched the skirt and noticed it was pretty dry. I carefully removed it from the hanger, stepped into it and pulled it up and over my shoulders. Reaching behind me I was surprised to see that it would zip all the way up (my sister and I were both pretty slim and apparently the same size!). Looking down I expected to see some nice legs down there but just saw my own hairy guy legs. It actually looked a bit comedic. So, I shrugged my shoulders, took it off and hung it back up on the rod.

But the seed had been planted....

For days afterward, thoughts would run through my head. "I wonder if I tried on her underthings too? What would that feel like? And what about makeup? How does that work and could I do it? And heels too? How would it feel tobe totally dressed as a girl?"

I don't recall the circumstances - I was only thirteen at the time - but there did come a day when I was home completely alone. I was watching TV as I usually did when that voice screamed in my head: "Hey! No one is home! Aren't you curious to wear a dress and be a girl?" So, sith my heart pounding, I slowly got up and went and stood in the doorway to my sisters bedroom. I looked around and thogh I had been in there many times before with my sis, I never noticed just how feminine it was. I was shaking - nervous and excited at the same time over what I was about to do.

I walked over to her dresser and opened the top drawer that contained her dainty panties and pantihose. I selected a pink pair of panties and nude pantihose. The next drawer contained her slips and bras. I took out a half slip and white lacy bra. I set the dainties on her bed and began to *****.

I managed to figure out how to put all the smooth silky undies on mostly by watching commercials for those things on TV. I knew enough to be careful enough so as not to put a run in the hose. Once I had all her undies on I couldn't believe how awesome feeling those smooth lacy girly things felt against my skin. "So this is how a girl feels", I thought to myself. I was already feeling giddy and girlish, doing twirls just like a teenager. I padded over to the closet and began looking for just the right dress to try on.

Oh, it was such a different feeling - nothing at all like being a boy. I pretended I was a pretty teenaged girl looking for just the right dress for a date I would have later with a hunky boy from school. I came across my sister's homecoming dress and my eyes lit up. It was so pretty and feminine! I took it out and held it up to my sirlish body and looked in the mirror. I was giddy with excitement, I carefylly unzipped it from the hangar and slowly stepped into it - revelling in the feelings, knowing that this is exactly how a girl would feel stepping into a dress that pretty.

It was a pretty yellow satin dress with a sheer lace overlay that came to just above the knees. It had what I learned later was an Empire bodice, with a satin sash that went around just under the bustline and had a pretty bow in front. It had a sheer high ruffled neck that went down over my bust as well as sheer long sleeves with a ruffle at the wrist. Oh it was soooo pretty!

It took a little doing, but I figured out how to get it zipped all the way up and I was soooo pleasantly surprised that it fit me! I was completely in my first pretty dress! I looked in the mirror and couldnt believe my eyes! But there was something missing.

I went to her vanity and began combing my thick longish hair (it was the early 70's after all) into a bit of a feminine style and began the task of applying makeup, again recalling tose maybelline commercials I've seen on TV. I managed to get it all put together without looking like a clown. I slipped on a pair of her low heeled samdals - they were snug but not too tight - and slowly, as femininely as possible walked back to the full length mirror. WOW! I was now all girl! And I was even somewhat pretty (so I thought anyway).

Again I twirled and danced around the room, feeling so totally feminine! One thing I noiced is that my penis was also rock hard in my panties. I had tucked it under between my legs to prevent that unladylike bulge, but now it was as hard as ever! I sat on the end of the bed, facing the mirror, crossing and uncrossing my legs like a proper girl. I would squeeze my cockette and get jolts of electricity shooting through my slim little body.

I laid back on the bed, still squeezing my legs and dreaming. Imagining I was a pretty girl on a date. My boyfriend and I had just left the dance and he and I were alone in his car. We began kissing and petting. I tried to stop him but he kept feeling me up my pretty dress! I didn't want him to find out what I really was - I wanted to be his girl! But he wanted more. Oh my cockette was positively throbbing.

"Please!" I cried. "Please don't do this?" But he kept trying to get inside my panties until finally...he did! And he discovered my secret! And started calling me names like sissy and *** and girly boy and I wanted to run away and cry. Through this whole little fantasy something strange happened. My excitement built to a fever pitch and my cockette throbbed. I felt a sensation coarsing through my body from my head down to my nether regions until I felt my cockette begin to spasm and twitch and my panties began to get moist! I was panting and squeezing and shaking until finally it was over.

And I just laid there. OH MY GOD! What just happened? Was I OK? Did something inside me break? Am I ill? The warmth in my panties began to spread over my backside so I quickly stood up and began peeling everything off.

OH MY GOD! What was that!? I looked at the panties and saw a thick substance that had a funny odor n the crotch. What I figured out after a while was that I had orgasmed! I was 13 and hitting puberty and I had my first ******! But unlike most boys in my age range, it wasn't from stimulation from girlie magazines or **** videos or even from actually having sex with a girl. It dawned on me that my first ****** was not with a girl. It was AS a girl!

I was a pretty girl when I had my very first ******. And that is what set the stage. Since then, I have always dressed as a pretty girl at any and every opportunity. And as I did it more, I became more proficient at all things feminine. I learned about it all just like a real girl would learn it. And since then I yearned to feel soft, sexy, frilly and feminine at any opportunity.

I didn't have a name for my girl personna back then, but a few years ago I came up with Tiffany Anne Easton. My first and middle names after a pretty CD/TG girl on the net who is very creative in stories, captions and videos. I have tried my hand at TG fiction and wrote some stories as well. So, although I'm a guy to the rest of the world, inside I will always be that pretty young girl I was looking at in the mirror that fateful day so long ago.

TiffanyAnnette TiffanyAnnette
31-35, T
4 Responses Jan 12, 2013

A great story well written, I think most boys started dressing this way and all would eventually have *** in panties as it so exciting wearing a dress and slip.

What a wonderful story Tiffany, but after that first time dressing in your sister's clothes did you get caught?

Very nice first time dressing story, so similar to most of us. Once you let the urge out its hard to stop

this is fantastic! just wonderful!