My Halloween Transformation

Sitting at my mother's makeup table with the long dildo buried inside of me made me feel like a real woman. Every time my body moved or my weight shifted I was again reminded of the fake cock inside of me. I positioned my laptop on the table and pulled up a series of youtube videos designed to teach you how to apply makeup. I had never worn makeup before, but after 45 minutes of following along I was amazed at the transformation. I used a very light amount of makeup, but managed to highlight my cheeks and eyes in a much more feminine style. I even went as far as applying a pair of fake eyelashes.

I finished it off with a glossy pink lipstick that matched the pink acrylic nails that I found in a drawer. I searched through her jewelry hoping to find a pair of clip-on earrings, and though I came up short, I did manage to find a nice black silk choker that fit me perfectly, covering the tell-tale lump in my throat. The last thing that I did was pick out the most feminine smelling perfume I could and surrounded myself in a mist of floral scent.

My transformation was now complete. Before I could get up though, I found myself grinding my ass into the wooden bench that I was sitting on. The more pressure I applied, the further the dildo pushed into me. It felt like it had a mind of its own as it rocked back and forth inside of my body.

My mission was a simple one, which is how I felt so confident going out of the house fully dressed up as a woman. I just had to drive into town and drop off a package to be shipped. My mom already told me that it was addressed and had a shipping label on it. All I had to do was make sure I dropped it off in time. And since it was the day before Halloween, I knew that nobody would even think twice about seeing someone dressed up like I was, even if they suspected that I was really a guy.

On my way out of the house, I decided to keep the dildo inside of me for the ride over. I figured that nobody would know, and this way I wouldn't be wasting an hour that I would otherwise have spent at home jerking off. I grabbed the package and the keys to my mother's car. She drove a bright red two door sports car and I figured it would help me get into character.

Before leaving I ran back up to my mom's closet and grabbed a small black purse. Since I didn't have pockets, I figured I needed somewhere to put my driver's license. I also grabbed the bottle of lube, to help reinsert the dildo on my way home, and the lipstick.

Stepping out of the house made everything feel so real to me. The cool night air whipped up underneath my skirt and against the thin material that could only barely contain my cock. The breeze flowed across my bare ass and lifted my skirt around my hips as I walked out to the car. I gently lowered myself into the tiny leather seat, making sure to keep the dildo from sliding out, and then headed out on my first adventure as a woman enjoying every bump along the way.

The FedEx office is in a busy neighborhood so I took the first parking spot I found, which was several blocks away. After parking the car, I lifted myself up off the seat and with my hand between my legs I slowly fucked myself with my new pink friend before carefully pulling it out and hiding it under the seat. With my cock throbbing between my legs, I waited to catch my breath before finally getting out. I suddenly felt empty inside and wished that there was some way to keep the fake cock inside of me while I walked to the store.

For the first time in my life I noticed people watching me as I strutted down the street. I have to admit that I did look good. My long legs were proudly on display, with my short skirt and high heels, and my fake breast jiggled just enough to draw hungry stares with every step I took. I felt my confidence growing as I paraded my new body through town.

On the way to the FedEx office I passed one of the more popular clubs for local college kids. I had tried to get in with a fake ID a few months earlier, but was denied and lost my ID. Still feeling burned by the place, I noticed that the bouncer was eying me up as I passed by. He was a few inches shorter than me with a lean muscular build. He wore a black t-shirt, pulled tight against his chest, and a pair of black jeans.

"Hey." I heard him say as I approached.

I didn't respond, but I did turn towards him while I walked.

"We're having a costume party tonight, you should come in."

I couldn't believe it. He clearly thought I was a hot piece of ass, and on top of that he was prepared to let me into the club. I hadn't thought of it before, but it dawned on me that being dressed like a hot girl meant that I could probably get into any bar in town and drink for free.

I shrugged my shoulders at him.

"Come on, baby. We've got the hottest music in town, and with a body like that I know you want to dance."

I smiled at him as I passed, and I don't know what came over me but I also pouted my lips and gave him a little air kiss before he disappeared behind me.

"You're a little tease, huh? Well you can tease me anytime girl."

My heart was racing as I replayed the past few seconds again in my head. I had really gotten into my character and didn't even realize it.

The FedEx store was getting ready to close for the night and was staffed with a single employee. When I walked in, I felt his eyes burning through my body. I recognized him from one of my classes in high school, but clearly he didn't recognize me.

"Hi." His voice cracked. "How can I help you?"

Oh shit, was all I thought when I realized that I would actually have to say something.

My voice croaked as I responded in the most feminine voice I could.

"I'd like to mail this, please."

"N... no problem. Let me take that." The young man fumbled over his words.

"I handed him the box and watched his eyes dart back and forth from the box to my breasts. It was thrilling to know that he not only thought I was a woman, but also that I was turning him on. I knew that he was thinking about fucking me and I liked it.

"It looks like everything is all set with this. It should arrive in three days ma'am."

I was still in a daze; I never expected that people would really believe me as a woman.

"Thank you." I said as I turned to leave.

I noticed what looked like a hint of disappointment in his eyes as I walked away and decided to give him a cheap thrill before leaving. As I approached the door I stopped dead in my tracks and dropped my purse. I couldn't look back but I could see his reflection in the window. His eyes were glued to me. With my knees locked, I slowly bent over, letting my skirt ride up my thighs and then my ass as I lowered my body. I didn't know exactly how much he saw, but I do know that he enjoyed the show. As I reached for my purse I was able to see him through my legs, his face was frozen with wide eyes and a gaping mouth. I took my time standing back up and quickly fled the scene of the crime.

Back on the street I was thankful for the cool breeze. My face was flush and was heart was racing again. I just flashed some kid from my high school and he had no idea that I was a guy.

Walking back to my car, I passed the club again. From a distance I saw his eyes lock onto me. I couldn't help but be flattered at the attention and smiled back at him.

"I knew you couldn't stay away." I heard him grunt as he finished his sentence.

I wasn't interested in chatting, but I figured what the hell. I walked right towards him and stopped inches away, staring directly into his eyes.

"What do you say, baby? Do you want to party?"

I didn't respond. Instead I flashed him another smile and turned towards the door. He quickly jumped forward and pulled the door open for me. As I walked through, I felt his hand on the small of my back gently guiding me into the club.

"Have fun in there sexy."

His words sent a shiver through my body. Involuntarily, my cock twitched from both the attention and the intimate contact.

I scanned the club before heading to the bar. Even though it was early there was already a decent sized crowd. I walked up to the bar to wait my turn. Before I could get a drink I felt someone slide up next to me.

"Can I buy you a drink?"

I turned to him, surprised at how easy women had it.

"Sure." I felt more confident speaking since the music was so loud, but I still planned on keeping my words to a minimum.

"My name is Richard." He said while turning to me and extending his hand.

He looked like a typical college jock. Blonde hair, huge muscles, a shit eating grin, and his eyes glued to my chest. For a costume, he was wearing a white toga with a laurel wreath on his head.

"Hi Richard, I'm Eric..." I caught myself just in time. "Erica."

He took my hand in his. His skin felt warm against mine and suddenly I felt a butterflies in my stomach.

He ordered me something pink and sweet in a martini glass. We talked, or I should say he talked and I pretended to listen. It wasn't too hard because he didn't have much to say. After we worked through two drinks, he leaned into me and asked me something I never expected to hear.

"Can I kiss you?"

I stared up into his eyes, at a complete loss for words. Apparently he didn't need much encouragement and seconds later I felt his lips pressing against mine. The first thing I noticed was a thick smell of whiskey, and then I noticed him.

I felt my body going limp as his lips massaged mine. One of his hands came up and cupped my neck. His other hand moved to my hip and pulled me towards him. I couldn't pull away if I wanted to, and to my surprise I didn't. I submitted myself to him and tried my best not to fall over.

He kissed me for several of the longest seconds of my life. I didn't know what to do with myself, but found my hands reaching for his hips too. His costume was arranged in such a way that his left leg was partially exposed, and my right hand ended up right on his exposed leg. The heat from his body almost made me pull my hand away but something kept my hand pressed against him.

As we kissed I was getting hornier and hornier. His hand made circles on my hip as he caressed my body. My right hand mimicked his movements and eventually slid up under his toga. He was getting bolder and pushed his tongue into my unsuspecting mouth. By now, his hand had tilted my head so that I was positioned to allow him full access to my mouth. Our tongues met, sending a jolt through my spine, as he took what he wanted from me.

Lost in the moment, I didn't notice that my hand had moved from his hip across his boxer shorts. I guess I expected to eventually feel his penis through the boxers, but what I didn't expect is that his hard cock had pushed itself though the opening in the front of his underwear. My hand slid across his boxers until I made contact with his flesh. I felt his warm soft skin pressing against my hand between my thumb and index finger, my fingers willingly wrapped around the base of his shaft.

After years of touching myself, I still wasn't prepared for this. The warm velvety flesh of his hard cock in my hand was both familiar and foreign to me.

I felt him moan into my mouth as my hand grasped his cock. He abruptly pulled me into him. Our bodies crashed together in the dark crowded room. His hand had slowly pushed my skirt up around my waist, and my hand had pushed the opening of his toga to the side. My hand fell from his penis as we collided. His hard cock landed against my inner thigh. It felt like a hot steel shaft pressing against my soft skin.

I moaned into his mouth as I felt him rubbing his cock against my bare skin. After a few seconds, I managed to get my hand between us and held it over his cock, pressing it into my thigh. I didn't know what I was doing, but I couldn't stop. My hand stroked him while out tongues danced. The soft swollen head of his cock had pushed up into the elastic of my panties while I rubbed him. I was nervous at first that he would notice that his cock was now rubbing against my own, but he didn't seem to notice.

My head was swimming as the reality of what was happening crashed down around my. I was dressed up like a woman in a slutty Halloween costume while making out with a complete stranger in public. His hard cock was out in the open and rubbing against my leg while I jerked him off. Everything had happened so quickly that I never stopped to think about what I was doing.

I was in heaven.

My hand worked his cock until I heard his grunting get louder. I knew that he was about to cum. He pulled me closer to him as the first blast of his hot sticky cum shot from his cock and landed against the base of mine. His cream coated my cock, bathing it in his warm juice. I almost came myself as his cock flooded my panties with his cum and covered every inch of my manhood with his juices.

I slowly stroked him until he was soft and empty. After he got what he wanted, he stepped back and said thanks. He turned away and without making eye contact he disappeared into the crowd.

I stayed at the bar, trying to wrap my head around what I just did. I convinced myself that what I did wasn't gay. I had just jerked off another guy, in public no less, but I was just acting out the role of a woman. I felt empowered, just like I imagined all those naked women I used to jerk off to felt like.

I finished my drink and then went to the bathroom to fix my lipstick. In the bathroom, I didn't see myself in the mirror. I watched as a hot slut fixed her makeup right before my eyes.

Back in the club, I noticed two guys by the dance floor watching me. I made my way into the crowd, but noticed them following me. When I turned around I was face to face with one of them.

"Hi." He said while dancing with his chest against me.

"Hi." I replied, with as much sexiness as I could muster.

I took his lead and danced to the music. The dance floor was crowded and so there wasn't much room to anything but move from side to side. That was fine with me, because I didn't know the first thing about dancing, especially with heels on.

We danced for several songs until he worked up the courage to put his hands on me. He grabbed me with both hands on my waist. The heat from his hands passed right through my costume and into my skin. We continued to dance like this for a while when suddenly I felt another pair of hands on me. I turned my head and saw his friend behind me.

He didn't say a word as his hands slipped under my skirt and grabbed onto my bare hips. His rough fingertips scrapped across my soft skin as held me. Sandwiched between two men, our bodies moving in unison, felt incredible. My head rolled back, giving the guy behind me an opening. I felt his breath first, as my hair fell away from me, and then his warm moist mouth against my skin.

My cock throbbed, begging to be freed, as their hands rubbed my body. One of my hands made its way under the shirt of the guy in front of me while my other hand rubbed his hard cock through his pants. The hands on my hips moved around my back and cupped my bare ass while his mouth licked and sucked on my neck. I moaned loudly into the dark room when I felt a finger briefly slide between my ass cheeks. His hands didn't stay on my butt for long; they were soon tracing the elastic around my waist. His fingers inching towards my hard cock, I knew I needed to stop him.

I turned my head towards him and said. "We can't do this here."

"Follow me." He whispered, his fingers pulling away just as they were about to make contact with my penis.

My thighs felt cold and naked without his hands on me as he led me through the club. We left his friend behind, but I didn't even notice. He pushed open an unmarked door next to the emergency exit in the back of club and led me into a small office. The room had a large blacked out window set in the wall that offered a perfect view of the club, but prevented anyone from seeing into the office. Under the window was a small desk and a chair. The rest of the cramped room was filled up by filing cabinets.

He locked the door behind him and then swooped me up into his arms. His mouth found mine and his hands explored my body. I couldn't feel anything when he rubbed my fake breasts, but I still loved every second of it. In the heat of the moment I found myself unbuckling his belt and pushing his pants to the floor.

He kicked his pants to the side and stepped back, giving me my first good look at another man's cock. His penis was definitely larger than mine and bounced up and down as he panted. The tip of his cock glistened from his pre-cum. He looked like an animal ready to take its prey. He stepped forward and pushed me back into the chair. I fell back with a crash, my legs spread apart, giving him a brief glimpse of my panties.

He positioned himself between my legs and without giving me a choice he pushed my head down towards his waiting cock. I knew that jerking off a guy might be considered borderline, but there was no way I could convince myself that sucking another man's cock wasn't gay. In the instant that I had to think as his cock zoomed towards my mouth I decided that I was no different than any of the other drunken sluts in the club spreading their lips or legs for some guy they just met. And besides, I was just playing the part of a woman so it was only natural that I should be sucking some guy's cock.

As soon as the tip of his cock passed through my lips I felt my teeth rubbing against his skin. I quickly pushed my lips down to cover my teeth and give him a more accommodating mouth. I didn't even have a chance to consider whether or not his cock would fit in my mouth before I found out for myself. With his help, and by that I mean thanks to him forcing my head down onto his cock, I learned that I can fit a full cock in my mouth.

I started to gag when he first pressed against the back of my throat, but then readjusted my neck and learned to breathe through my nose which helped. After holding my head in place for what felt like an eternity, his grip softened and I found that I was able to move my head backwards and forwards.

As I slowly pulled my head back the first time I let my tongue slide along the length of his manhood. His penis was warm and both hard and soft at the same time. He tasted salty from a combination of sweat and his pre-cum which was leaking into my mouth. I opened my mouth slightly as the head of his cock slowly emerged and my movement was again restricted; he didn't allow me to move any further back once the tip of his cock was between my lips.

I paused for a moment while kissing the tip of his cock. My tongue circled his throbbing flesh rubbing his slick pre-cum against him. Despite the noise from the club, I could hear him moaning. Knowing that he was enjoying what I was doing was all I needed to know.

I slowly worked my face up and down his cock, slowly at first just a few inches at a time, while I started sucking. My tongue wrapped around the underside of his shaft as it slid back and forth in my mouth. I had watched enough porn in my life to have a few ideas of what to do next so I wrapped my hand around the base of his cock and started to stroke him while I sucked.

After a little while I noticed that his hands were only resting on my head and were no longer restraining me, but by that time there was nothing I wanted more than his cock in my mouth. After a few false starts, I was able to work myself into a good rhythm between my hand and my mouth. He seemed to be enjoying it too because he was grunting and thrusting his hips into my face.

When his thrusting became more forceful I suspected that he was getting ready to cum so I picked up my pace. My mouth was filling up with more and more of his pre-cum as he approached the edge. I moved my hand away and deepthroated him, pushing his pulsing cock into the back of my throat.