I had it all prepared. With help from my older sister, who got a kick out of my idea. I was going to the prom, the last party before graduation. But not as Ronald, or Ron as most call me. I was going as Rhonda.

I was just going by myself. I'm sort of a loner, not that I don't have any friends, but none would go to a “stupid” prom. That's for girls and whomever they're dating at that moment. I wouldn't mind dating Veronica, going to the prom with her, but she never even acknowledged that I exist. Not that she has lots of friends, last thing I heard she was going by herself as well. Maybe if I had just asked….

So, I've done a bit of cross dressing, not that anyone but my sister knows. But I can handle walking in heels elegantly, up to two inches at least. I know how to handle skirts, how to sit in them, but I have also practiced dancing in a dress, and heels, and doing the girl moves. I know how to do makeup, thanks to my sister again, and with my wig and voice exercises I know I can fool any guy or girl, but more importantly, any teacher.

My sister, Marsha, is in college already, and she got me a decent drivers license, in the name of Rhonda Williamson, with my girl face on it. Apparently getting a fake license is fairly easy in college, so that students can consume alcohol before they're twenty-one. It did cost me extra however to get the name I wanted on it, and my own picture.

The hardest part really was my dress. Marsha told me I was on my own, and for a while I considered ordering something online. But there were some risks here. My parents could open the package, or they would annoy me to find out what's in it, and I don't need the extra attention. Plus, if the dress didn't fit I had no option to get that fixed.

So, a few weeks ago, when my parents were out, I got into my girl persona, nothing fancy, and drove the hour and a half to the state capital. I had a few shops on my list, but this turned out a lot harder than I had anticipated. And expensive. Do they just add an extra zero and make a 120 dollar dress a 1200 dollar prom dress?

Looking into the sections that I could afford I found nothing that I liked. You see, I would love to wear that dress a few more times after the prom, but most were designed with prom only in mind. I slowly started panicking. And understanding why so many girls in my class were stressed out. Not because of the last finals, but because they couldn't find the right dress.

I was running quickly out of shops that were on my list. The last one was a shop aimed at cross dressers, but they did not specifically have prom dresses. I knew that because I had called them the day before. But, by now I was thinking any nice dress would be okay.

The shop was not in any of the malls, but more in the outskirts of town, in a short shopping strip. And no convenient parking, so I had to walk by a number of shops. And one shop I passed was simply called “Second Hand”. Why had I not thought of checking out Goodwill's? So, I went in.

It wasn't like they had an enormous amount of prom dresses, but at least the extra zero was dropped here again. And most were still for prom use only. My guess is that the girl who wore these, or the mom, had realized that too, and tried to get some money back for it.

I still wasn't wowed, but I saw a few potential ones in my girl size. If nothing else I could try one of those, without breaking the bank. I didn't mind the fact they weren't new. Heck, most of my crossdressing outfits belonged to my sister at some point. And then, sort of hidden behind two other dresses, I saw it.

It probably should not be in this section, because it was not prom specific, but the bright red color drew my eyes, and that's probably why they put it here. When I touched it, a shiver went up my back. It was leather, probably not real, but a very good fake. And it was my size. I could see myself in it already, and I liked it. Not just for the prom.

So, that was really my problem suddenly. In a simple prom dress I could experience so much of what a regular, a real girl, would feel. Not standing out, but maybe getting a dance in once or twice. I didn't want to be prom queen for crying out loud. Just a few sweet hours, imagining I was a girl.

But, in this dress I would stand out. The bright red leather would scream out “SEX” in capitals. And, with no one knowing me, that's probably what people would think I was after, rather than a simple prom experience. And I was not ready for sex at all, although for some girls it would be the perfect prom finale. Not for me though, if a guy would find out what's under my dress, I would be lucky to come out alive.

I think I stood there for five minutes with the dress in my hands. Until I realized I was worrying too much, and maybe the dress wouldn't even fit me. So, I looked where the fitting rooms were, and found a free one.

I took my time, making sure that even when someone would barge in, they'd see a half naked girl and not a guy. Prom or not, once I had the dress on, I knew I wanted it. The skirt wasn't straight, on my left side it was around my ankle, so my heels would be on display, on my right side it was just under the knee, showing off half a leg. I would need stockings. Duh, I would need that anyway.

The bodice was a corset style that really shaped my figure. My neck could be bare or I could use the choker that would nicely hide my adam's apple. There was some skin in the shoulder area, but my arms were in half length sleeves, so I could show off some bangles. It was perfect, except…

Except that the original owner had been more voluptuous in the chest area. God, I wish I had breasts like that, but I was using quite some padding already. More padding would become obvious. I would need falsies.

And suddenly it hit me. Had I not been on my way to a shop for crossdressers? I could buy this dress, which was well within budget, and go to that shop and find a way to get fitting breasts. I forgot all about my original worries about sticking out and having to deal with potentially horny guys.

Instead I searched for matching shoes, which I found, in my size, though a bit higher than I've ever tried. Oh well, time enough to practice still. Even stockings that matched were right there. Would even stockings be second hand?

With all my purchases I found my original destination soon, and stepped into a fairly small shop. There were no customers and a pretty girl with a pleasant smile was clearly glad to see me. She looked me briefly over, then told me she thought I looked good. I guess that was a good way to soothe the nerves of a man dressed as a woman. It worked for me.

Because of her easy going I had soon told my whole prom story, and the perfect dress with just a tiny problem. She convinced me to put on all my new purchases, so she could see for herself. There were small rooms toward the back, but much bigger than the fitting room I was in earlier. She came in the room with me, after closing the shop “for lunch”.

She explained that she had “seen it all”, but she wanted to know what I'd be wearing under the dress, and I figured she would probably know better what to do than me. So, seconds later I stood there in my bra and panties, and she checked the “bump” in my crotch, and the amount of padding in my bra. She motioned for me to continue, so I first put on my new stockings, which looked even better than I had hoped.

Then I got the dress back on and my confidence increased again. Finally I stepped in my new shoes, wobbling a bit with the extra height, but complementing the dress perfectly. I could see how the girl licked her lips, nodding, then she started feeling the emptiness in my chest area.

In a way it was simple math. With my own padding I had created myself an A-cup. The dress needed a C-cup. And Annabelle, according to her name tag, could fix it. With breast forms. She had some cheap ones that fit my budget, but anyone wrapping their hands around my chest would probably realize they weren't real. Her top-quality ones were so realistic that I wouldn't want to take them off ever again. But they were more expensive than my dress.

She could clearly see the disappointment in my face, when I told her to get me the cheap ones. I saw her hesitate for a moment, then she said she had one expensive pair that was returned, virtually unused, but the size was somewhere between B and C. It may work with the dress, or I would still need a bra with a bit of extra padding. But, the price was under a hundred dollars.

The way I saw it was I had a second hand quality dress, I might as well have second hand quality breasts. Annabelle smiled, and soon came back with a box with two beautiful breasts. Even in the box they felt real and I knew I wanted them on me.

That wasn't that simple. Due to the weight these were not simple inserts in my bra, or the new one I would need. They would have to be glued to my chest, and they wouldn't come off unless you had the dissolvent. That was a scary thought.

But Annabelle showed me both bottles that came with it, good for at least fifty wears, and she would teach me how to put them on, and take them off. And she was right, a small indent would fit them over my real nipples, and all I had to make sure of was that they were straight. And after holding them tight for three minutes I felt the weight hanging down, and I was sold.

Bella, as she told me her friends called her, wanted to show me how to take them off again, but I let her explain it, as I didn't want to lose this feeling. Already I wondered what it would feel like to sleep with. She smiled, and told me how she had warned me.

I was surprised to see how the breasts stood out on my skin, like I had been wearing a bikini on the beach, without any visible seams or imperfections. Bella had a gorgeous bra for me that added just a bit to my breasts, and now the dress fit just perfectly. I couldn't stop watching myself in the mirror, and I enjoyed when Bella's hand softly rubbed my leather back.

Again I saw her hesitating, and I could feel there was something else. So I asked her what else she had for me. She made her decision and she explained that the person who had returned the breasts had also returned an artificial vagina. She wasn't sure how serious I was, but if I wanted it, I could get it heavily reduced as well. She didn't think it was ever used, but she couldn't put it back on the shelf.

I had never really considered that, but I was very conscious about tucking, because, you know, no one wants to see a bulge right? I didn't think I'd need a vagina, because as much as I wanted to look like a girl, I had no fantasies about dating a guy. A dance or two, yes, maybe a small kiss, but no sex, for sure!

But, as Bella explained, the contraption would keep my manhood out of sight, even in the tiniest bikinis, with no chance for accidents. And again, my own face gave me away, so she retrieved the box with “womanhood”.

I could see it right away, like my breasts, and it was so soft, I believed that even while having sex, people would not be able to tell. And just as I told her I wanted it, she told me the problem with it. I couldn't put it on by myself, like the breast forms, nor could I take it off again. Did I have someone I trusted to help me with this?

Having said that, I could wear it for days, weeks, months even, without anyone ever finding out, as long as I'd find a stall to pee, because I'd have to sit like a woman, even if I was in full boy-mode. Unless I did silly games with friends on who had the biggest dick, or if I went to bed with a girl, while having a pussy like her.

It scared me and thrilled me at the same time. I didn't play games like that with friends, and the only girl I considered having sex with had no interest in me. And I trusted my sister one hundred percent, I knew she'd help me both ways. And, Bella said, I could always come here and she would help me to put it on, or take it off.

It was her words that convinced me, as the college I was going to in the fall was right here in town. She really wouldn't have a problem with that? She laughed at that, she ran this shop with her sister, once her brother. So she had the experience, and her sister knew how to do it as well, so I was not to worry.

She took control of the situation and told me to take off my dress, and she'd show me how the vagina would fit. I watched in the mirror and it was the weirdest feeling to see this woman, whom I just met, hold my small dick and tuck it between the folds of the fake pussy. The prosthetic, as she called it now.

I saw how it could work, and even now, loose between my legs, it already looked female. Bella looked up at me through the mirror. “Want me to use the glue?”

And I calculated, a few weeks from the prom, I would be able to get used to it. Only after the prom would I think of removing it. So I nodded. And it took her less than five minutes to glue it tight.

I couldn't keep my eyes from it, the naked slit between my legs, with a tiny strip of hair. The landing strip I thought, if I were into that. Looking at the total picture I saw a woman, with a nice rack in a beautiful bra, still in stockings and heels, but no panties to hide her slit. And my breath caught in my throat.

I don't remember why I started cross dressing, I think it was my sister's idea, and it was all good fun. I never did it without her knowing, and she helped me get my own wardrobe. The fact that my parents never knew added a bit of mystery and it was a cherished secret between my sister and me. She took me out a few times, to hike in the woods or the beach, then to shop in the mall. We saw a few movies together, just two sisters going out. But it was never like I wanted to be a woman, it was just for fun.

And when one of my weird friends said that the prom was for girls, I wanted to know what it was, if he was right. When I talked it over with my sister, and I told her my plan, she nodded. The only way to find out for me was to experience it. She never shared her own prom experience with me, two years ago, but I remember her crying the day after.

But now it was all different from what I had planned. I had a female body now, and I liked what I saw. I would be sexy in my dress, and the thrill gave me goosebumps already. The thought of being Rhonda was suddenly not just a joke, it was a severe possibility.

It was like Bella could read my mind. “Pretty awesome right, being a girl?” I nodded. “I saw the same look on my brother's face, and it didn't take long before he chose permanent womanhood. That could happen to you as well.” I nodded again. “If it does, and you need advice, or just someone to talk to, you can always come here. I will help you, and so will Charlene.”

“Charlene?” I asked.

“My sister. She had to go through all this on her own. Well, I was there of course, but we were pretty clueless at the time. She loves to help anyone on this path. With a bit of luck you'll meet her, she should be here soon.”

She was right. By the time I had my regular clothes on again, and Bella talked me into a cute skirt, a pretty girl entered the shop with fiery red hair. I thought of a customer at first, until Bella introduced us. This was Charlene. And I was Rhonda, wearing breast forms and a vagina prosthetic for the first time.

Charlene looked me up and down with a cautious look, then smiled, and she said, “You're a natural.”

I guess there's no better way than that, to break the ice, and we soon started chatting, and I heard the story of her transformation, which had not been easy, but a lifesaver for her.

There were a surprising amount of similarities, the biggest one having a cool and understanding sister, Bella for her, and Marsha for me. But, the biggest difference was that she always knew that she wanted to be a girl, whereas I crossdressed for fun. For her, the breast forms were a game changer, and I had to confess that for me it made a true difference, compared with a padded bra. And somehow, with all the talking going on, I realized that the thought of having the breasts and pussy for a longer period of time was very attractive to me, whereas before it was a dress-up for an afternoon or a night.

The best advice she gave me was not to rush into anything. Think things over, consider your most intimate feelings. Then she continued to say how easily she had failed that very same advice. Because, once you make the decision to transition, then it simply can't go fast enough.

I think we talked for two hours, with Bella running the shop, and during breaks adding her part of the story. When I finally left, after paying for my new “body parts”, and the new bra and skirt, with a list of phone numbers of people that had helped them throughout the process, and both their numbers stored in my phone, I hugged them like I'd know them all my life. I walked with such a happy spring in my step to my car, that a group of guys wolf whistled after me. I could only smile.