The Halloween Parade Transformation

The Halloween Parade Transformation by rutger 5 (An original story 2011)




It all started over a bet but it ended very surprisingly and totally changed my life. I was a sophomore attending NYU in the heart of New York City when this occurred. Originally I came from Ohio and now in my second year of college I had really fallen in love with NYC and the whole city lifestyle. Back home I was from a small homogenized town which while being a safe and pleasant enough place to grow up always seemed to be lacking something I felt. 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 October afternoon when I unwittingly set the course that changed my life. Sitting in the booth with me were my best friend Aimee as well as 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 especially 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 one of these fancy costume places 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 one as he was obviously needling my background which made me want to prove him badly 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 twenties” I replied with a confidence I didn’t feel and we shook hands on it with the two girls as witnesses.


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


Now Aimee was my best friend but when I first met her I had tried to get her to date me as she was gorgeous. She was of asian descent with long, silky black hair and a tight little body and she favored wearing skirts that showed off her legs to best effect. Aimee was also fond of heels of three inches or higher which further accentuated her legs while at the same time making her appear taller. She had politely turned me down and informed me that 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 as I was only 5’5” tall and I was on the slight side. Back in high school I had run some track so while my lower body developed some I certainly wasn’t muscular. My hair was blond and sort of longish and at least my stomach was flat though I didn’t have a six pack or anything. Still we had hung out and in time we became very close friends. We talked about anything at all including our sex lives although to be honest I didn’t have much of one. Between school and work keeping me busy along with the fact that I was sick of being turned down by girls who dismissed me due to my size I dated infrequently.


Anyway we were enjoying a takeout dinner along with some wine. We were on our second bottle when suddenly Aimee asked me if I had come up with a costume idea that would beat Brent. When I admitted that I hadn’t even started looking yet 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. Standing there she looked at me with a funny look on her kewpie doll face.


“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 $500. But you would have to do as I say. I’m so confident that if you do it you’ll win 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. Lets say someone dresses as a ninja but when 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 are around the same size.”


I’m not sure why but my hands trembled as I took hold of the bag and 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. It dawned on me that it was a Supergirl costume.


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


“I said you wouldn’t like the idea but here me out. You wearing this costume alone isn’t going to 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 will win I’m convinced.”


No doubt my face betrayed the skepticism I was feeling at her idea and for a moment I wondered if she was drunk. 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 are good looking – but almost in a pretty way. I’ve always envied your eyelashes because they are so long and full.”


“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 up in the air in resignation.


“Come with me” Aimee told me as she headed 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 and 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 evident in 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 Jamey 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 really are 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.”


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 stand 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 Jamey, it will 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 Jamey, 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 Aimee continued her training of 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 Jamey. 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.