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. 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 an A type personality and extremely competitive and it appeared that she was taking this bet as a personal challenge. This was more than I bargained for but I really wanted to shut up Brent so I decided to go for it. Aimee was now 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 Jamey 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 as 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 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 later on.

On Halloween eve I went to Aimee’s place again 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 although I was still a little nervous. The next morning I went to the address she gave me and it was a nail/day spa filled with asian women working there. Once I gave my and Aimee’s 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 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 lying 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 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 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.

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

After that Aimee got in her own costume that was of a character from some anime show that she liked. Then she did her hair and 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 Jamey 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 Jamey” 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 there as well.

“Now you are 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 route. 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?” he 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 Jamey. 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 her 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 Jamey” 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 someone 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 from her 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 would 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 are 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 answer.

“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 would 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 as though I had 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.

“Well is he coming or did he get cold feet?” Brent asked Aimee.

“Don’t worry about that Brent. The question is do you have the money because you’re going to need it. Show yourself J” Aimee replied smugly.

“What are you talking about Aimee?” he asked while looking about in all directions with a confused expression.

Slowly I raised my hand as my eyes met his. He stared hard and as he did recognition came over his face. Brent shook his head slowly with the next thing he did was to remove his wallet. He handed me five twenty dollar bills silently at which time I smiled sweetly at him.

“You fucking got me is all I can say. Never in a million years did I think that was you.”

“Well thanks are in order to Aimee who did the makeup for me or I never could have fooled you” I said.

“You should work it Hollywood with your talent” he told her.

Soon after the parade started and for those who have never witnessed the parade let me tell you it is quite a spectacle especially the giant puppets. We were watching for awhile and I would have sworn on a few occasions that I caught Brent looking at me funny, almost as if he was checking me out. There was no way to be sure but I did get that vibe.

However since I was flush with cash and had a chance to possibly win more later I decided to be magnanimous and buy us all drinks. By now the bar was even more crowded with the parade in full swing and we literally had to fight our way through to the bar. After our second round Brent had to use the bathroom and as he passed me on the way his crotch rubbed against my ass. That was just too weird as even though the bar was packed if I was dressed like normal I don’t think it would have happened.

During our third drink I realized I was getting pretty drunk and I thought I should stop for a while. Right about that time Aimee received a text from Carol. Once she read it she told us that she was going to meet her and did we want to go with her or not. Brent said he was going to watch the end of the parade here and we could meet later.

“That is after Jamey buys me one more drink with my money.”

I reluctantly agreed and Aimee left after saying she would call one of us. After we finished the drink my head was spinning a little and I needed some air but I had to use the restroom first. I told Brent and he said he’d meet me outside. The bathrooms were off a small corridor by the back of the bar. When I reached them I had a moment of confusion that wasn’t helped by my blood alcohol level. Normally I would use the men’s room without thinking but due to my costumed appearance it seemed problematic.

As I stood there frozen by indecision the door to the men’s opened and a beefy fellow walked out. His eyes ran up and down my body making me feel repulsed yet attractive. But he decided my course for me as there was no way I could enter the men’s room in front of him.

“Excuse me” I said as I squeezed past his bulk after which I opened the ladies room door. Before I could step inside I felt a strong hand grab my ass hard. I whirled and he stood there defiantly grinning at me and as I watched he blew me a kiss. Slamming the door shut I could hear his laughter even through the door.

After relieving myself and washing my hands as well as throwing some cold water on my flushed face I stared at the mirror trying to steady my nerves. The hell with it I thought to myself. I’m just going to walk out of here with my head held high and if anyone said something I would respond in kind. The corridor was empty and there was no sign of the bastard when I left. The bathroom had been a cool respite from the heat of the bar which hit me even in the corridor.

Off to my right between the back of the bar and the kitchen I noticed an open door that led outside and I could feel the fresh air even from the distance so I managed to work myself to it. I stepped outside and filled my lungs with the refreshing October air. I was standing in an alley and the sounds of the parade and the watching crowd clearly came to my ears but because of a bend in the alley I couldn’t see the street.

At the time that didn’t bother me as I was just trying to clear my head and cool down but the next thing I knew a strong hand clamped over my mouth from behind. Dropping the purse my hands went up to try and pull it from me when I felt steel pressing against my neck and a voice in my ear.

“Don’t make a sound bitch if you know what is good for you” it hissed before the hand that was over my mouth moved lower and wrapped around my waist while the cold metal near my throat remained. Next I felt myself being dragged further back into the alley by a powerful figure. Since I was unused to wearing high heels I lost my footing but the man easily continued to move, half carrying me with him. The alley narrowed and there was another bend after which we reached the dead end.

I was pushed against the wall face first but not hard enough to hurt me any after which my hand was wrenched behind me. A piece of thin, hard plastic was wrapped around my wrist and tightened and then my other hand was treated in the same manner leaving me helplessly restrained. A leg pushed into the back of my knee while at the same time a large hand pushed down forcefully on my shoulder. In an instant I found myself kneeling on the concrete of the trash strewn alley ground.

“All right you can turn around now but keep quiet and remember I have a knife” the voice instructed me.

The hand remained on my shoulder and guided me as I twisted my body around to face the attacker. Standing there with a leer on his face was the man who had groped me in the bar. His hand was fumbling with his zipper and in seconds he managed to pull his semi-erect penis out where it was less than a foot from my face.

“You know I have a knife so what you are going to do is suck my cock. I don’t want to feel any teeth or you’ll regret it.”

To be honest I was scared, maybe not as much as I should have been, but scared nonetheless. However I had to do something to dissuade the man from this course of action and my clouded brain struggled to formulate a plan to accomplish this when he slapped my face.

“Are you deaf or stupid? I said suck it” he demanded belligerently.

“Wait please, I have to tell you something” I gasped out, my voice barely above a whisper.

“What the fuck is it and make it fast as my cock is waiting” he said and as he talked his hand ran up and down the length of his swollen erection.

“I’m… I’m in a costume. I’m not a girl but a guy dressed up like a girl” I managed to croak out.

“Are you fucking with me?” he demanded.

“N-n-no it’s true” I said as I shook my head.

He stared into my eyes for a moment before suddenly bending down while continuing to grip my shoulder tightly. His free hand reached under the short Supergirl skirt and grabbed my package. His eyes widened and he squeezed it hard enough to make me wince. He released me there and straightened up and his fingers rubbed his chin.

“Well I’ll be a monkey’s uncle you are telling the truth you little fag boy.”

“I’m not gay just in costume like I told you. Now will you let me go?” I pleaded.

“Hold on and let me think” he replied and as he stood there his hand started to absently stroke himself while he looked down on me.

“Sorry but my answer to you is no, I’m not going to let you go. At least not yet I’m not. We still have the problem that I’m hard and horny and you still look real sexy to me. Tell you what, if you do a good job blowing me I’ll let you go. If not I’ll fuck that cute ass of yours, cock or no cock. And to be honest from what I felt you don’t have much of one to begin with.”

My face turned red when he said that as truthfully I was kind of small in that department not that had to do with anything else going on but I always had been self conscious about it.

“Come on Supergirl and get started or I swear I’ll fuck you right here and now.”

Figuring that as bad as it was, a blowjob was the lesser of two evils under the circumstances. I reluctantly opened my mouth. As soon as I did the thug forced the head and half his shaft between my painted lips. He pushed more in until almost his full length was inside and he hit the entrance to my throat making me gag and choke. One hand grabbed my head holding it in place after which he moved his hips in a back and forth motion driving his erection in and out.

“Fuck yeah that hot mouth feels so good” he grunted as he worked his meat in my mouth.

It tasted like sweat and piss and some unknown taste to me and part of me wanted to retch. He didn’t seem to notice or care about that but continued face fucking me hard and fast. On more than one occasion I almost choked from him going too deep at which point he would not go as deep the next few thrusts. I didn’t think I could take much more when I felt him swell in my mouth and the next thing that happened was a thick glob of cum exploded from his cock followed by another.

As I choked from the white, creamy discharge he pulled his prick from my mouth and rapidly stroked his shooting organ as it spewed onto my face. His hand still held my head in place so I couldn’t move away as the last weak shots came from the hole and landed on me. Finally when he was through he released me while groaning with satisfaction.

My body bent over as I began spitting what cum I could from my mouth to the filthy pavement. As I did I heard him laughing above me.

“What’s the matter you didn’t like your Halloween treat” he told me while laughing “cause I sure liked giving it to you. But I’m afraid as well as the treat I’m also going to play a trick on you.”

Once he said that he knelt down beside me and pushed my face towards the ground while lifting the back of the skirt up revealing my red thong wearing ass. As he did I heard a low whistle of admiration from him followed by a firm smack on my bare left cheek.

“I know I told you if you blew me I would let you go but I lied. That ass is too fine and I gotta tap it. Let me tell you something, plenty of women I’ve fucked haven’t had such a cute butt and there is no way I’m not trying it. Don’t get any stupid ideas and you’ll go home tonight.”

His hand started rubbing my ass and as a finger slipped under the material I wracked my brain on how I could avoid this and I realized that maybe screaming was my best option when his hand yanked the thong down to my knees. Figuring it was now or never I called out “Help”.

Unfortunately due to the face fucking and my drunken dry mouth it didn’t come out very loud and before I could try again his hand clamped over my mouth tightly.

“What the fuck are you trying to pull bitch?” he growled at which point I feared for my life.

Just then I heard a voice call out from down the alley “Hey what’s going on over there? Let her go” and I could hear steps approaching. My attacker leaped to his feet quickly as I attempted to rise. Looking down the alley I saw Brent approaching with the fake pirate sword from his costume in his left hand. The rapist pushed his cock into his pants and ran down the alley managing to avoid Brent as he fled. Brent ignored him and rushed in my direction. He stood a foot away looking down at me with a very strange look on his face.

“Are you okay Jamey?” he asked.

“I think so but my hands are tied. Can you free them Brent?”

“He didn’t hurt you Jamey I hope.”

“Not really” I said.

There was a weird look in his brown eyes which made me nervous so I lowered my gaze from his face. Unfortunately when I did that and with me being on my knees his crotch was right at my eye level and I noticed two things right away. The first was that Brent’s zipper was open and the second was that his underwear covered cock was bulging its way out of the opened zipper. Hastily I looked back up at him. He just stood there not moving while staring at me.

“How did you find me Brent?” I asked him as I was curious plus I didn’t want to ask him about what I had just seen.

“To be honest I had to take a piss and I didn’t want to go back in the bar as it was so crowded so I decided to use the alley. I saw the purse you had been carrying on the ground and I thought that was suspicious.”

That was a good thing he saw it I realized as it held all my stuff that I had with me.

“Don’t worry Jamey I have it in my pocket” he continued talking in a slow almost mechanical fashion.
“so after I took my leak I thought I heard something so I went further up the alley when I saw you and that guy and he was fucking your face. It was hot.”

After he said that he smiled and his hand reached down and squeezed his large bulge.

“The guy had a knife Brent which he put to my throat when I came out in the alley for some air” I explained to him. He kind of ignored what I said before he started speaking again.

“I saw him cumming on your face and when I heard you call out help I realized he was going to fuck you and something clicked in me so I figured I should say something.”

“Well thank you Brent I really owe you one. Now can you free my hands?”

“I don’t know Jamey, that depends. Since you owe me maybe we can work something out.”

“What the hell are you talking about Brent?” I asked with trepidation as his mood was strange to say the least.

“You might not know it Jamey but I’ve always had a thing for shemales. Since I first saw a picture of one on the internet it’s always turned me on. When I saw you dressed like that I felt immediately attracted to you. Then when I saw what was happening with you and that guy it made me hard, the way his cock was going in your mouth. I couldn’t help it, I started to play with myself. See what you’ve done to me now Jamey, with cum on your face and your panties around your knees.”

I didn’t want to see but his hand touched my face and kind of pushed it down where I observed his erection was now free and sticking thru his fly. His other hand was stroking it, running up and down the long, thick shaft. The head was red and large and mushroom shaped and as I watched some clear pre-cum oozed out the hole. Suddenly he crouched down so he was at my level and the hand that had recently been touching my face reached out and stroked the skin on my ass.

“Your skin is nice and smooth Jamey and you look so sexy like that.”

“Please stop Brent. I don’t want to do whatever it is you want to do.”

“Have you ever tried Jamey? You might like it if you give it a chance.”

While he said this his finger was rubbing against my asshole which tickled me. He now moved his other hand between my legs and started to stroke my soft penis gently and before I knew it he leaned in and kissed my neck. I let out a moan as I felt goosebumps all over my body which I hoped were caused by the chill air on my bare flesh but I knew were from what he was doing.

As his hand continued stroking me I started to become erect. He sucked on his own fingers and when he forced his wet index finger into my virgin hole my semi-hard dick twitched in his hand.

“See at least your body likes it” he whispered in my ear.

“No please don’t Brent. It isn’t right what you are doing. I’m not a girl or gay so please stop.”

Instead of stopping his finger was now burrowing deeper in me when it touched somewhere that felt really good. It must have been my prostate I figured as when he touched it I just kept getting harder. His hand continued stroking me and soon he worked a second long finger inside and the two of them moved in and out making me moan. That galvanized him as he released my erection and moved his body behind me.

“Wait, stop” I pleaded as what he was planning to do was pretty obvious “if you need relief I can…”

That was all I got out before I felt his head poke me in the back of my leg as he withdrew his fingers only to then feel the head, slimy with pre-cum, push at my slightly distended opening. He pushed forward and the tip of the head worked inside me stretching the opening wider. His hand gripped my hip to hold me in place after which he drove deep into me making me cry out in pain.

“No Brent its way too big take it out” I managed to say before his other hand clamped over my mouth.

“Fuck you are so tight Jamey that I can’t help myself. Forgive me” he said before pushing deeper in me.

It felt like his shaft was halfway to my chest, it felt so big to me. Tears streamed from my eyes as Brent forced it all the way in until his heavy balls slapped my flesh. The hand that had held my hip resumed stroking my wilting dick as the rest of his body remained still. In spite of the ache in my ass the blood again flowed to my groin and in a minute I was rock hard again.

“That’s it Jamey, get it nice and hard. Your ass feels so good on my cock. I’m going to start fucking you so try to relax. They say it makes it easier that way.”

Slowly he pulled his cock back with my hole clinging to his thickness, seemingly resisting it leaving. Brent pulled almost all the way out leaving just the head in me before sliding it back in. He varied the depth of his thrusts, sometimes going partially in and other times burying his big erection to the hilt. His hand muffled my cries while his other hand stroked me in rhythm to his thrusts.

It was a mixture of pleasure and pain but his relentless pounding was stretching my hole out to more easily accommodate his girth. I was actually sucking on his fingers now as I felt myself getting close to orgasm. Brent’s hand was a blur between my legs pushing me closer and closer to release. When he increased the speed of his pumping hips I couldn’t last any longer. A low moan escaped my mouth past his fingers as I felt the cum flow from my balls.

It seemed more like a steady stream than a series of spurts as my cum exited me and made a white puddle on the dirty alleyway. My body tensed and every muscle tightened as a result of my mind blowing orgasm. I could hear Brent groan from the pleasure my hole was giving to his driving prick. He now grabbed my hips with both hands and commenced a series of balls deep thrusts. Before he reached ten thrusts I felt him stiffen even more inside me at which time he cried out.

“Fuck yeah baby! Your hot, tight ass is making me cum Jamey! Oh yes!”

His big prick exploded deep in me and his teeth clamped onto my neck as his climax overtook Brent. I could feel it spasm as his sperm coated my insides. It seemed to me that he came a lot but I really didn’t have much to compare it to but my own orgasms. As the last few drops trickled from Brent his hand pulled my head up after which his lips met mine for the first time.

He kissed me hungrily and surprisingly I found myself eagerly responding. After a couple of minutes kissing as he shrank inside my hole Brent broke our kiss as he regained his feet. When he stood his now diminished cock pulled free of my sheath leaving me empty. Brent assisted me in getting up as well. Since my hands were still restrained behind my back he pulled the thong up but before covering me he gently squeezed my now soft dick causing me to tremble.

“Wait here Jamey and I’ll get something to free you” he said before heading back down the alley.

In a few minutes he returned with an opened pocket tool with which he freed my hands. As I rubbed my wrists which had a thin red mark on them from the plastic restraint Brent went to return the tool to the bartender from whom he said he borrowed it. After he returned he just stood there silently and instead of looking at me his gaze was directed at the ground we had just fucked on. One could see the conflicting emotions playing out on his face before he spoke.

“Jamey first thing is I have to apologize…” he managed to say before I interrupted him.

“Wait Brent” I blurted out “and just answer me this first. Did you enjoy what we just did?”

“It was fucking awesome Jamey but…” was all he got out before I was kissing him with all my passion.

Brent responded to me enthusiastically and soon his warm hands were fondling my asscheeks as we kissed. When we finally stopped I could feel his erection had returned and was pressing into my midsection.

“Let’s go to your place Brent” I told him as I looked deep into his chocolate eyes.

He smiled in reply and took my hand as we headed down the alley. When we reached his room his roommate was out not that I really would have cared at the moment. If their had been a large crowd there it wouldn’t have dissuaded me a moment I was so turned on. Once Brent closed the door I was all over him, kissing and groping him until he pushed me to arm’s length.

“Wait up a minute Jamey, just let me use the bathroom first” he said. He disappeared into the bathroom for a few minutes and when he returned he was naked and sporting a major hard-on. It looked even more impressive when it wasn’t surrounded by clothing, standing proud and erect and surrounded by a thick nest of dark hair. I hurried into the bathroom and took a pee before cleaning up a little. The red thong was all I removed but I stayed in costume as Supergirl. When I came out I saw that Brent was sitting on the bed playing with his phone so I knelt between his hairy legs.

“Aimee texted me so I told her something came up” he told me as a way of explanation.

I giggled before answering as I took his thick shaft in my hand.

“Something sure has come up and in a very impressive fashion.”

After I said that I leaned in and gave the swollen mushroom head a kiss before opening my mouth wide and taking as much in me as I was able. Brent was leaking pre-cum which tasted salty to me as it met my taste buds. I pulled my mouth off him making him groan with disappointment so that I could wrap his impressive length with both of my hands. One hand gripped him at his base before there was a narrow gap of flesh above which my other hand held him still leaving some shaft as well as the head uncovered.

My mouth resumed sucking on him and I used my wet tongue on his sensitive underside causing him to thrust forward as he moaned in appreciation of my efforts. My jaw quickly ached from his girth but Brent wanted more than my mouth anyway. He pulled my head off him and stood up bringing me with him. Wrapping his arms around my waist he lifted me and sat me on a table next to his bed. He bent down and pushed the short skirt to my waist before kissing the skin on my thigh. His arms hooked under my knees and lifted them wide leaving me open to his further designs.

The head of Brent’s cock pushed against my hole while his hand held the shaft steady as he worked it in me. We gasped simultaneously from the feeling as he slid deep into me and Brent didn’t stop until his balls rubbed against my ass. It didn’t hurt like it did before as I was now used to his organ. He pumped his hips in a herky-jerky manner to start but as he continued the movement became smoother and faster.

“Put your arms around my neck Jamey” Brent said and once I did he lifted me from the table and lowered me to the bed.

His thick erection slid from me as he pushed me onto my back and knelt at the floor between my legs. Brent pushed his cock next to mine dwarfing it in size. After a moment he pulled it back and entered me again. Brent resumed his thrusting as I held my legs up in the air. His hand grasped my shaft and stroked it making it hard quickly while his pace didn’t slacken at all with his thrusting.

“Are you close Jamey?” Brent asked, the perspiration coating his face from his exertions.

“Yes baby I’m going to cum soon. Don’t stop what you’re doing.”

Not only didn’t he stop his movement he actually increased the speed of both his hips and hand. In less than a minute I was there as Brent’s hand was a blur stroking me. Spurts of white shot out of me and landed on my costume as he literally fucked the cum out of me as each thrust of his was matched by my release. Brent managed to clamber onto the bed after nothing remained in me, where he adjusted my body.

He slipped my legs over his shoulders then leant down allowing our lips to meet as my legs were pushed to my chest. His tongue slipped in my mouth as he pumped as fast as he could. This position allowed him to reach deeper in me than before as his hips slammed into me with each thrust. Before long Brent cried out as his body tensed and he swelled inside my tight hole.

“Fuck yes Jamey” he cried out as for the second time that night I felt him explode in my depths.

Once he recovered he pulled from me and cast himself on his back. Brent pulled my spent body against his and after all I had experienced blackness soon overtook me. When I awoke the next morning I was on my left side with Brent behind me and we were covered by a sheet. His lips were gently kissing the skin of my back while his hand was softly stroking my semi-erection.

“Morning Jamey” he whispered to me.

“Hi baby” I replied spreading my legs wider and giving Brent greater access to me.

“do you like that, you naughty slut.”

“Hmm yes baby.”

Right after that I was prodded by Brent’s morning wood working its way between my cheeks and it felt slippery as if it was coated in lube. He moved his hips until my hole was lined up with him, then he slowly started to work it in.

“Jamey I’m going to fuck you but try to keep it down as my roommate is sleeping” he hissed to me.

Looking across the room I saw a blanket covered figure on the bed across the room from us. Brent’s hand moved from pleasuring me to holding my hip as he sank his shaft deeper. Once he was past the halfway point Brent slowly thrust in and out using a short hip motion. This went on for quite some time as his deliberate rhythm prevented him from peaking fast.

However once his hand again found my erection I was soon at the height of pleasure which he pushed me past by forcing his cock balls deep into me for a few thrusts. It proved to be too much for my erect member as my cum shot onto Brent’s hand as well as the sheet I was wrapped in. This also had an effect on him as he now picked up the pace of his thrusting and I heard his breathing become harder.

Without warning he slid from me and then moved his whole body, managing to scramble from beneath the sheet and straddle my head. His hand gripped his engorged shaft just beneath the bulbous head and once he was over me he aimed it to my open mouth. Removing his hand he fired a thick rope of cum onto my waiting tongue followed by one after another.

Brent’s hand now stroked the shaft helping it to discharge the morning jism to my eager mouth. I managed to raise my head so that I was able to suck on his sensitive head making him moan louder than he intended. Luckily it didn’t disturb his roommate as I swallowed down every drop of his morning treat. Once he got off me I crept to the bathroom where I cleaned myself up as best I could before sliding the red thong back on. After leaving the room I retrieved the purse and Brent walked me to the door where he kissed me goodbye.

I had only reached the street a couple of minutes before when my cell went off. When I checked I saw it was a text from Brent.
[I would love to take “Jamey” to dinner sometime and perhaps dessert afterward. Brent]
After reading it I had to wait a minute before continuing on my way as the front of my skirt had been pushed out due to my excitement.

THE END by rutger5 (An original story 2011)

Comments are always welcomed and encouraged readers and votes are even better.

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