The Halloween Parade Transformation

"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 Jamie," 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 while 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 in Hollywood with your talent," he told her.

Soon afterwards the parade started and for those who've never witnessed it let me tell you it is quite a spectacle, especially the giant puppets. We were watching for a while 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 with a chance to win more later I decided to be magnanimous and buy us all drinks. By this time 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 for even though the bar was packed I don't think it would have happened if I'd been dressed normal.

During our third drink I realized I was pretty drunk and thought I should stop for a while. Right about that time Aimee received a text from Carol. Once she'd 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 up later.

"That is after Jamie buys me one more drink with my money."

I reluctantly agreed and Aimee left after saying she'd 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. After informing Brent 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'd 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 room 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. When I whirled around 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 I washed my hands then threw some cold water on my flushed face. I stared at the mirror while trying to steady my nerves. The hell with it I thought to myself. I'm just going to walk out of 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 metal pressing against my neck and a voice in my ear.

"Don't make a sound bitch if you know what's 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 a 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, flexible plastic was wrapped around my wrist and tightened 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.

"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 cuz 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 gasp out.

"Are you fucking with me?" he questioned.

"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; then straightened up as his fingers rubbed his chin.

"Well I'll be a monkey's uncle. You are telling the truth, you little sissy boy."

"I'm not gay, just in a 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 at me.

"Sorry but the answer 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 for I was very small in that department, not that it had to do with anything else going on but I'd always been self-conscious about it.

"Come on Supergirl and get started or I swear I'll ass fuck you right here and now."

Figuring, 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 of 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, piss, and some unknown flavor 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 far 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 slit to land 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 below. 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 clad 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 nice ass 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 cried 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.

"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," followed by the sound of footsteps approaching.

My attacker leaped to his feet 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 while managing to avoid Brent as he fled. Brent ignored him and instead rushed in my direction. He stood around a foot away while looking down at me with a very strange look on his face.

"Are you okay Jamie?" he asked.

"I think so, but my hands are tied. Can you free them Brent?"

"He didn't hurt you, 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 with me being on my knees his crotch was right at my eye level where 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 because I was curious plus I didn't want to ask him about what I'd just seen.

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

It was a good thing he'd seen it I realized for it contained all my stuff that I'd been carrying with me.

"Don't worry Jamie 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.

"That 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 but he kind of ignored what I'd said before he started speaking again.

"I saw him coming on your face and when I heard you call out for help I realized he was going to fuck you and something clicked in me so I figured I should do something."

"Well thanks again Brent; I really owe you one. Now can you please free my hands?"

"I don't know Jamie; 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 Jamie 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 Jamie, 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, large, and mushroom shaped and as I watched some clear pre-cum oozed out the slit. 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 Jamie and you look so sexy like that."

"Please stop Brent. I don't want to do whatever it is you want to do. Just let me go."

"Have you ever tried Jamie? 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 night air on my bare flesh but I knew they 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 inside me when it touched somewhere that felt really good. It must have been my prostate I figured for 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 mine.

"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, it's way too big. Take it out," I managed to say before his other hand clamped over my mouth.

"Fuck, you are so tight Jamie that I can't help myself. Forgive me," he said before pushing deeper inside me.

It felt like his shaft was halfway to my chest, it felt so big. 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 Jamie, 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 its 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. One 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 cum start to flow from my balls.

It seemed more like a steady trickle 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 as it tightened on him. He then 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 Jamie! Oh yes!"

His big prick exploded deep in me and his teeth clamped onto my neck as his climax overtook him. 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 with 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 to my surprise 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 then 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 Jamie 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 used to free my hands. As I rubbed my wrists which now had a thin red mark on them from the plastic restraint Brent went to return the tool to the bartender from whom he'd borrowed it. After he'd 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.

"Jamie first thing is I have to apologize..." he managed to say before I interrupted him.