tagTransgender & CrossdressersThe Halloween Parade Transformation

The Halloween Parade Transformation


Story is for Lit Halloween contest and contains themes of non-consensual sex and reluctance.

(An original story -- Copyright 2011)


It started over a bet but it ended in a most surprising way and totally changed my life. I was a sophomore attending NYU in the heart of New York City when it occurred. Originally I'd come from Ohio but by my second year of college I'd really fallen in love with NYC and the whole city lifestyle. 'Back home' was a small homogenized town, which though a safe and pleasant enough place to grow up in always seemed to be lacking something. It wasn't until I began college that I realized that I was made for the city.

There were four of us eating in the diner that fateful October afternoon when I unwittingly set the course that changed my life. Sitting in the booth with me was my best friend Aimee, her roommate Carol, and a classmate named Brent. We were discussing the upcoming Halloween Parade which takes place in Greenwich Village on Halloween evening. Since the school was close by we all planned on attending the parade before going to various parties later on. I thought it would be cool if we went in costume since many parties, as well as some neighborhood bars, had contests for the best costume with cash prizes. Brent said that he had a plan to easily win at least some prizes that night.

"If I go to a costume store and rent an expensive costume the odds will be good that I can win at least one prize. This isn't small town America," he said looking my way, "and you need more than a sheet with holes cut out for eyes as a costume."

Everyone at the table but me laughed at that as he was obviously needling my background which made me want to prove him wrong.

"Well," I answered, "you can get any type of costume you want but I guarantee that I can do a better job than you with less money besides. I might buy a costume but not at a fancy place and I'll make it much better than yours with some creativity."

"Care to put some money where your big mouth is? I'll bet you $100 that my costume will blow yours out of the water," Brent said with a smug expression.

"I prefer to be paid in twenties," I replied with a confidence I didn't feel as we shook hands on it with the two girls as witnesses.

Over the next few days I was so busy between classes and my part time job that I didn't even have a chance to think about the bet, let alone find time to look for a costume. Halloween was less than a week away and so far I'd gotten nowhere when one night Aimee and I were having dinner in her apartment. She and Carol rented one rather than living in a dorm as both their families had enough money that they could afford to live on their own.

By this time Aimee was like my best friend but when we'd first met I'd asked her out as she was gorgeous. She was of Asian descent having long, silky, black hair with a tight little body and she favored wearing skirts that showed off her legs to best effect. Aimee was also fond of heels three inches and higher which further accentuated her legs while also making her appear taller. She'd politely turned me down while informing me I just wasn't her type. Aimee preferred to date dark haired, preppy jocks, the taller the better as far as she was concerned.

That certainly didn't describe me for I was only 5'5" tall and on the slight side. Back in high school I'd run track so while my lower body had developed some I certainly wasn't muscular. My hair was blond and sort of longish and though my stomach was flat I didn't have a six pack or anything. Still we sometimes hung out together and in time we became very close. We talked about anything at all, including our sex lives, although to be honest I didn't have much of one. School and work kept me busy plus the fact that I'd gotten sick of being turned down by girls who dismissed me due to my size. So I dated infrequently at best.

Anyway that night we were enjoying a takeout dinner along with some wine. We were on our second bottle when suddenly Aimee asked me if I'd come up with a costume idea that would beat Brent. When I admitted that I hadn't even started looking she shook her head slowly.

"I know, I know, but I really haven't had the time. Tomorrow I'll go to a drug store and see what I can find there," I told her.

"Hold on a moment James because I think I have the solution. Now wait right here," she told me before hurrying to her room.

She came back in a few minutes with a bag in her hands and a big smile on her face. Standing there she looked at me with a funny look in her eyes.

"How bad do you want to win this bet? Because I have a brilliant idea but I don't think you'll like it."

"I want to win all right, just to show Brent up. The money will just be an added bonus."

"If you follow my plan not only will you beat Brent but I almost guarantee that you can win at least one contest and some of them have a first prize of five hundred dollars. But you'll have to do as I say. I'm so confident that if you lose to Brent then I'll pay him the money."

"That sounds good to me but what's your idea?"

"A costume within a costume," she said as if that answered everything.

"Huh, not sure what you mean."

"Okay, first an example but not the one for your costume. Let's say someone dresses as a ninja but if they remove the mask then they're a zombie underneath, so really they have on two costumes in a sense."

"I'm not sure a zombie ninja will win anything," I told her.

"I just used that as an example. I have your costume here," Aimee said as she placed the bag in front of me on the table, "it was an old one of mine and we're around the same size."

I'm not sure why but I felt butterflies in my stomach and my hands trembled as I took hold of the bag. Next I opened it and removed the contents. There was a blue top with an S on the chest as well as a short, red skirt and a cape. Suddenly it dawned on me that it was a Supergirl costume.

"Are you crazy Aimee? First off it's a girl's costume. Second how is this going to help me beat Brent let alone win a real contest," I said thinking she must be drunk from the wine.

"I said you wouldn't like the idea but hear me out. You wearing this costume on its own wouldn't win you anything even if you were a girl as it isn't unique or good enough. And if you just put it on you would look like a guy wearing a girl's costume. But if you follow my plan you'll win I'm convinced."

No doubt my face betrayed the skepticism I was feeling at her idea. Aimee didn't even seem to notice my mood but breathlessly continued with her plan.

"I don't mean this in a bad way but you're not the most masculine guy out there James. No one would accuse you of being a caveman even if you had a beard and a club. In fact you're good looking - but almost in a pretty way. I've always envied your eyelashes because they are so long and full."

"Gee, thanks about the eyelashes, I guess. But about the rest..."

"Trust me I know what I'm talking about James. Give me a half hour to prove my point and if you don't agree then I'll never mention it again - okay."

"Fine whatever," I answered throwing my hands in the air in resignation.

"Come with me," Aimee told me as she headed back towards her bedroom.

First I picked up the costume after which I followed her into her room. She patted a chair in front of her vanity and indicated I should sit.

"Just relax James and let me work. Maybe close your eyes as it will be easier for us both that way."

Sitting there I felt my apprehension grow especially as I felt what she was doing but I kept both my eyes and mouth closed. Aimee was humming softly as she worked her magic on me. Finally after what felt like forever she finished.

"Wait one minute I just have one finishing touch to make and I'm done," she said after which I heard Aimee rummaging in her closet and in a minute I felt her put something on my head.

"Okay James, open your eyes," she told me.

When I opened my eyes I was speechless for a minute. There staring back at me in the mirror appeared to be an attractive female face. Between the long blond wig, the makeup, and lipstick Aimee applied I almost didn't recognize myself. Don't get me wrong it was my blue eyes that looked back at me but with the mascara, eye liner, and other work she'd done my face resembled the sister I didn't have.

"Wow Aimee, if the whole shrink thing doesn't work out then you have a future as a professional makeup artist. I doubt anyone would recognize me."

Aimee's major was in psychiatry but she also had other talents I saw. She just stood there beaming as she beheld her handiwork. Then she went to her dresser and opened a drawer and fumbled around before removing some red fabric which she handed to me. It was a silky, red thong.

"Put it on James as well as the costume and come out. I'll be waiting in the living room," Aimee said as she left the room.

Still unable to get over the change in my facial appearance I removed my clothes and put on the costume. When I slipped the thong on the silky feel on my penis stimulated me and I started to harden. I ignored that and finished dressing. When I looked in the mirror I beheld a hot looking Supergirl staring back which inflamed my erection further. The bulge was actually pushing out my skirt so I stopped looking and tried to relax. After a minute my hard on subsided and I headed to the other room where Aimee greeted me by clapping her hands delightedly.

"I told you James, wait I think I'll call you Jamie if you look like that. Now you are Supergirl but your real costume is that you are dressed as and appear to be a girl. Two costumes in one. Well what do you think?"

"I had my doubts Aimee but you were right at least to a point. This might actually work."

"Well we still have some finishing touches to work on if we're going to pull it off, at least if you want to win some contests. We have to fool people into thinking you're really a girl but I know how to accomplish that. We also need to get you red boots for your costume but I think I have the answer. Wait here."

After saying that she disappeared into Carol's room as I waited. She returned shortly with a pair of short red, high heeled boots that looked big.

"Carol has big feet and yours are small for a guy so try these on," Aimee told me. They were tight but I managed to squeeze into them. I stood but when I attempted to move I almost lost my balance, causing Aimee to laugh.

"These boots won't work. They kind of fit but I can't walk in them."

"Stop being a baby Jamie; it'll take practice. Take my hands and I will lead and help you."

Aimee faced me and held my hands as I clumsily tried to walk. More than once I stumbled but Aimee kept drilling me until I could walk unassisted. Once that happened she started giving me pointers as she sat watching me.

"Come on Jamie, work it girl. Swing those hips and that cute, little butt. Remember you're trying to sell yourself to win the prize."

My eyes shot daggers at her but she only smiled in reply and continued to train me. She allowed me a few breaks but she worked me hard until while I wouldn't say I was a natural I wasn't bad. Truthfully it made me realize how much women go through to show their legs off to best effect.

"At least you're not standing out like a sore thumb now Jamie. The day before Halloween you have to come here and practice unless you want to borrow the boots and train yourself."

"No thanks, I think one more practice will be enough. Thanks Aimee."

"Your choice but practice makes perfect. I still have to call my place and make an appointment for you."

"An appointment? For what?"

"Duh, for grooming. You might pass in bad lighting but to win we have to do it right. Don't worry I'll set it all up. Plus we have to get you a bra and some silicone breast forms and you'll be set."

Aimee was very much a type A personality and extremely competitive and it appeared that she was taking the bet as a personal challenge. This was more than I'd bargained for but I really wanted to shut up Brent so I decided to go for it. Aimee was holding a tape measure and once I removed the top she took my chest measurement. Then she helped me remove the makeup and wig. She next made a phone call to complete the preparations.

"Okay Jamie you have an appointment for Halloween morning at 10:00 A.M. and here is the address. Just tell them your name and mention me and don't forget to come here to practice the night before. By the way you can keep the panties now. I don't think I'll be wearing them again."

"Gee thanks Aimee," I replied sarcastically.

I returned to her room to change but the silk felt so good on me that I pulled my own underwear over them instead of removing them. Once I'd dressed I said goodbye and headed back to my dorm. On the way the feel of the panties again aroused me though the feel of the thong separating my ass cheeks felt strange.

Once I arrived in my room I had to take care of my erection. To start I rubbed myself through the material but once I got close I pushed the fabric to the side and quickly stroked myself to an awesome orgasm. I came a lot as the silk felt so good to me that I honestly thought about buying myself some silk boxers for later on.

On Halloween eve I went to Aimee's place and she really drilled me on walking properly. By the time we were done I could 'walk like a lady or a slut' as she put it though I was still a little nervous. The next morning I went to the address she'd given me and it was a nail/day spa filled with Asian women working there. Once I mentioned our names the woman smiled like crazy and summoned some other women who led me off. They had me change into a robe and sat me down where they did both my fingernails and toenails in red. Next they gave me some kind of mud facial as well as using some kind of electronic device over the skin on my face.

Finally one woman led me off to a private room in back where she had me remove the robe. She shook her head when she saw I was still wearing my boxer-briefs and while she didn't seem to speak English she gestured for me to remove them before having me lie on a table. Between shaving and waxing she removed virtually all my body hair leaving only a small amount above my genitalia but removing all my leg, ass, chest and underarm hair. The woman also removed most of my pubic hair. When I tried to tell her no she just smiled, shook her head and continued what she was doing.

As I left the receptionist informed me Aimee had taken care of everything and to have a good time. With nothing else to do I headed for Aimee's to wait for the evening. It felt so weird to me as my clothes rustled against my now nearly hairless body. I hadn't been a hairy guy before my grooming but now being almost hairless gave me a good feeling like my skin was alive.

With Aimee's help I then got ready. First I changed into the costume and with the bra and silicone forms I now had a B-cup bust. Plus Aimee gave me a pair of blue stay up stockings and she had me again practice walking. As I sauntered past her Aimee raised the short skirt and slapped my now smooth ass with her hand.

"Jamie you are a naughty little girl, wearing a thong with that skirt so short. But it will help you to win a contest tonight. You just have to flash some skin," she said jokingly.

After that Aimee got into her own costume which was of a character from some anime show that she liked. Next she did her hair, fixed both of our makeup, and put the wig on me with a red headband to hold it in place. We stared at our reflection in her full length mirror and to be honest we looked like two hot chicks ready to go out and hit the town. In spite of that, or maybe because of it, I felt very nervous.

"Don't worry Jamie this will help you relax," Aimee told me handing me a glass with some vodka. We both had a shot and in fact I had two more at which point I felt great.

"You messed up your lipstick," she said as she applied a fresh coat of crimson to my full lips. "Here this is for you tonight Jamie," Aimee told me indicating a small blue clutch purse.

It had enough space in it for my cell, wallet, and keys and Aimee also put some tissues and a tube of lipstick in there as well.

"Now you're ready for a fun night out girlfriend," she told me making me glower at her, "I'm only kidding. Damn."

We left her place and headed out to the parade. We were all supposed to meet on 6th Avenue which is the parade route. As we traveled there we received plenty of glances and more than one man commented on what he would like to do to us. Aimee just laughed but I was shocked, especially about one comment directed my way.

"Hey Supergirl, I have some kryptonite in my pants. Do you want to see?" an older man bellowed out in a loud voice.

"Did you hear what he said? I don't know how you girls take it?" I said to Aimee.

"You have to learn to take it in stride Jamie. It's only temporary for you but I hear it all the time. By the way are you okay? Your face is really red."

"I'll be fine," I answered but I felt my cheeks burning from embarrassment.

We arrived at the meeting point but we were the first ones there. Aimee spotted a bar a few doors up so she took me by my arm and led me in its direction. She spoke to me in a low voice as we approached the entrance.

"There are some great things about being a girl though. You just wait and see."

There was a guy watching the door but he allowed us in without asking for ID although he did check us out.

"I think he liked you Jamie," Aimee said as we sipped our drinks.

"Shut up Aimee," was my only answer after which I downed my Stoli and cranberry in one gulp. We went back out but we still didn't see anyone we knew as we secured a good viewing spot. After around ten minutes Aimee elbowed me and had me look in the direction she indicated. Brent was walking in our direction dressed like a character from the Pirates of the Caribbean movies.

"Look away from me and act like you don't know me and we'll see if he recognizes you," Aimee whispered to me.

I followed her directions and turned my face partially away as he approached. The two of them greeted each other.

"Nice costume Aimee, are we the only ones here yet?" he asked.

"Carol texted me that she got stuck at work so she isn't sure what time she'll get here. You look good yourself. Make anyone walk the plank lately Captain?"

"No I haven't but I might make James if he doesn't pay up. Where is he hiding?"

"Oh he's around; I figured you'd see him. Besides did you guys work out how the winner would be decided. I'm willing to judge if you want."

"That's why I was hoping Carol would be here. Not saying you're not fair but you and James are close. I think that we could decide ourselves if it's not close as long as we're honest about it."

"Well how about if we ask someone else in the crowd for their opinion then?"

Brent shrugged nonchalantly in response.

"Why not, but either of us should be able to appeal if we disagree," was his response.

"Okay," Aimee said before tapping me on the shoulder. "Excuse me Miss, but two friends of mine are having a contest about their costume. Is there any chance you'd be willing to give your opinion to help out?"

It dawned on me what Aimee was attempting so I turned their way but I kept my face down somewhat. Since Brent was a little over six feet tall it wasn't like we were face to face but I saw he was looking at me waiting for an answer. This would be a tough test for though I'd practiced walking I certainly hadn't practiced talking like a woman. First I nodded an assent before attempting a verbal reply.

"I'd be glad to," I managed to squeak out. It didn't sound great but it didn't sound like me either.

"Thanks I appreciate it Miss," Brent answered at which point Aimee's face broke into a smirk. I turned away to keep from laughing at that point.

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