Halloween Party

October 31st, Halloween night.

My favorite night of the year, even in my twenties. The fun didn't stop, when I wasn't able to go from door to door looking for candy anymore.

In fact to me, it actually became a lot more fun then it was back when I was a kid. Starting in high school Halloween became about going out with your friends and partying and getting drunk, much like it was for most teenagers. Now at 21 years of age, I was still having the fun that I always had back in high school.

This year, my girlfriend Kate and I had been invited to a party, at our friend Steven's apartment. It was going to be a lot of fun because the apartment wasn't really all that big and there were a shit load of people coming, but we always liked the bigger and more pact parties.

Plus, Steven's older brother owned the small duplex building and was apparently totally okay with us using the basement for extra space; he would probably even have some people upstairs, in his own apartment too.

The best part of all of this, was that it was a costume party. Now that didn't really interest me too much but I was a pretty big prankster and it gave me the room, to try and scare as many people as I wanted.

I had picked up this scary, demon looking mask with red eyes on it and was going to show up wearing that and my old, black and worn down hoodie and a pair of ripped and faded jeans.

I planned on popping up in random spots during the party and scaring the hell out of anyone that I could. Steven was of course, totally fine with this. He knew how I was and as long as I didn't give anyone a literal heart attack, he didn't care what I did.

That afternoon, I got home from work and made my way straight to the shower. Cleaned up nice and good, before throwing on some clothes. I decided to go a slightly different route with the costume and instead of wearing my old hoodie, I threw on the old and faded jeans and replaced the hoodie with a red flannel. Top it all off with the demon mask and I was good to go.

I stopped to pick up Kate before heading to the party. When I pulled up at my girlfriends house, she was sitting out front waiting for me with a big smile on her face. She was dressed as an angel, with the long white gown and a pair of fake wings that went along with the costume; she looked so fucking sexy.

The costume was a bit cliche for Halloween but I wasn't complaining.

"Ready to go babe?"

"As I'll ever be," she replied, with a smile.

On the way to the party, we stopped and picked up Kate's two friends; Ashley and Jamie.

Kate and Ashley had been best friends since 2nd grade and there was no sign of that changing, any time soon. I knew Ashley almost as well as I knew Kate, except for the sexual aspect of course. She was a good person and a good friend and very funny sometimes, too. Jamie on the other hand, was new to the group and was one of Kate's co-workers.

I had only met her a handful of times and really didn't know a whole lot about her, just that she didn't seem like too bad of a person really.

Just like Kate, Ashley and Jamie were both dressed as angels. Kate told me that they had planned on that though. The idea was to show up at the party, as three sexy angels. I laughed when Ashley asked me what I was going as and she screamed, when I grabbed my demon mask and threw it into the back seat for her to see.

"Shit," she yelled. "You're gonna scare some people real good, with a mask like that!"

"That's the plan," I laughed.

"He loves doing shit like that," Kate explained.

"He'll have a lot of fun tonight, between the alcohol and scaring everybody."

When we arrived at the party, I noticed a woman standing out front that I recognized but it took me a few moments to figure out who she was. She had black hair, pulled into a pony tail and green eyes that were mesmerizing. She was wearing a long red dress and had a fake pair of horns; obviously, dressed as the devil. Then I remembered who it was; Nikki.

Nikki was Steven's roommate and also a good friend of his cousin Rick. She was a couple of years older then we were, since she was technically from Rick's group of friends...about 26-years old to be exact, I think. The few times that I had met her, she always seemed like a pretty nice person but according to Steven, there was something about her that not a lot of guys were aware of.

Steven told me that Nikki was actually born a boy and lived as a woman; she was a transsexual. We walked up to the front door and Nikki looked up at us from her cigarette, smiling from ear to ear.

"Welcome," she said. "Good to see you, Ryan."

"Thanks Nikki. This is my girlfriend, Kate."

I motioned towards Kate, who stepped forward and looked back and forth between Nikki and I, with a look of unease on her face.

"Nice to meet you," Kate said.

"Likewise," Nikki replied. "You've got a very sexy boyfriend, you know that right Kate? You better be careful...I might have to steal him from you one day. After all, you're an angel but I'm the devil."

Her voice sounded so seductive as she said that, that I couldn't quite figure out if she was serious or not. She turned around and walked right back into the house and Kate looked over at me; she didn't look very happy about what Nikki had just said.

We brushed it off though and made our way inside. The party was already well underway, with a few people already seeming like they were relatively drunk. There was loud music, speakers attached to the walls in the living room were booming as people talked and laughed, while drinking and even smoking a bit of pot. That wasn't really my thing personally, though; I was more interested in the beer, then anything else.

Steven came out of the kitchen to greet us, throwing his arms around me and giving me a pat on the back.

"It's great to see you dude," he yelled over the music.

It had been a while since we had seen each other.

"Definitely brother; where's the beer?"

"Ha-Ha, follow me!"

He led Kate and I into the kitchen, handing a beer to both of us. Kate was still a little irritated by what Nikki had said outside, so she proceeded to pound down the beer that Steve handed to her and immediately cracked open a second one. We exchanged a brief kiss before she made her way downstairs to the basement, with Ashley and Jamie to watch a beer pong game taking place.

"So, what's good with you brother?" Steven asked.

"Not much dude, just been working. I'm looking forward to scaring the shit out of some people, tonight."

I held up the mask for him to see and Steven started laughing at the sight of it.

"Dude, it's gonna be a blast; put that shit on and let's go have some fucking fun!"

I slammed down the rest of my first beer and put the mask on. Steven had your typical Jason hockey mask, with a fake knife and he was wearing his work jump suit and a pair of heavy duty steel toe boots to go along with the costume. Together, we proceeded to make our way into the living room and scared the hell out of everyone in there, by jumping out and screaming.

After they were all done screaming in fear, they started laughing once they realized it was just me and Steven. We were off to a good start but nowhere near done.

We made our way down to the basement and got a good scare out of everyone down there; even Kate was impressed, with Steven and I and how good we were at scaring people.

There was a door in the basement, that led out into the driveway where some people were standing around smoking cigarettes and others were walking up the driveway, as they arrived for the party.

We managed to jump out from the door and scare a few of the smokers, also taking some of the new comers off guard too. After a good thirty minutes or so of all of this, we decided it was time to take a break and just have fun partying.

We joined in on the beer pong game and that's when the alcohol really started to flow, as we wound up in one of those long drawn out rounds. By this point, Kate was also pretty fucking drunk and honestly, I was pretty sure she was more drunk then I was. She had been drinking beer and taking shots of rum, so she was definitely further along then I was at this point.

I made my way back upstairs at one point, to grab another beer and found Kate in the kitchen smoking a cigarette and talking with Ashley. They stopped talking as I came into the kitchen and Ashley walked out, leaving the two of us alone.

"What's up?" I asked, glancing over at Kate as I reached into the fridge for another beer.

"Nothing," she said, slurring a bit. "I'm going to head home for the night, okay?"

"What? Really?"

"Yeah, look at me," she laughed. "I'm shit faced already and I have work early in the morning. I should call it a night, before I get any worse then I am right now and end up calling out tomorrow."

"Ugh, alright."

I pulled her in for a kiss and hugged her tight. Her friend Nicole was going to give her a ride home, since she was also leaving early.

"Be safe," I said, as I walked her to the door with Nicole.

"We will," Nicole replied.

"Wait, wait," Kate said laughing as she turned to face me again.

"Call me, when you get home...okay?"

"I will babe, don't worry about it."

We kissed one more time and out the door she went with Nicole. I shut the door and cracked my beer open, taking a long swig as I walked back into the kitchen area. Now it was time for me to really get my party on.

As I walked back into the kitchen, I found Steven, his cousin Rick and Nikki doing shots of Jack Daniels together.

"Don't forget about me," I laughed, grabbing a shot glass and joining in.

We took a couple shots of whiskey, before ending up in a beer shotgunning contest. Steven and I were the best, at this sort of thing. We were the only two in our group that loved to shotgun as much as we did and we were the only two, who could shotgun a 24oz can. Everyone else always fucked it up and spilled beer every where, after a few moments of chugging.

I jabbed a hole in the side of the can, raised the hole to my lips, popped the tab and let the ice cold fluid gush down my throat. I felt it almost instantly, the room spinning just a little as the alcohol filled my system much faster then normal. That was the point of a shotgun; to get fucked up, faster.

As I slammed it down, Nikki stood in the corner of the room smiling at me the whole time. I threw the can into the recycling bin and let out one of the loudest burps that I had ever released. Nikki started laughing and I chuckled, smiling over at her.

Maybe it was the beer, I wasn't sure...but I found myself thinking about how fucking hot she always was. I knew she had a cock but I didn't care, not at that particular moment anyway. I tried to brush it off though, not because she had a dick but because I had a girlfriend.

Apparently, Nikki wasn't as willing to let it go as I was though.

As the night progressed, I started to really feel pretty drunk. Around midnight I stumbled towards the bathroom to relieve my bladder and as I did, I found Nikki coming out of her bedroom at the same time. She smiled at me and leaned against the door frame, to her room.

"You look like you're having fun," she noted.

"Oh I am," I said, slurring. "I'm SO fucked up right now!"

"I can tell," she laughed.

She stepped towards me and suddenly, my back was against the wall and her face was just a few inches from mine.

"You know...I meant what I said earlier, in front of your girl."

"W-What? I don't...remember," I lied.

"About stealing you away from her? I was about as serious, as a fucking heart attack. You are just too damn cute."

"Oh...right. I'm not uh..."

"Gay? Bisexual? I know, you're not into girls like me. There's nothing gay about it though Ryan. I'm all woman."

As she said that last part, she grabbed my hand and turned just a little, placing my hand on her bubble shaped ass.

"See? If I weren't a girl, would I have an ass like this?"

I had to admit, she definitely had one hell of an ass. Somehow though, I had a feeling that it wouldn't be her, getting fucked in the ass if I went along with all of this.

"C'mon baby," she smiled. "Take a walk on the wild side."

Before I could reply, she stepped forward and kissed me on the lips. I was taken off guard but found myself kissing her back. Our tongues wrestled and she grabbed both of my hands and pulled me from the kitchen, straight into the bathroom across the hallway from the kitchen. The door slammed shut behind us and she quickly turned the lock, before sliding out of her dress and sitting down on the toilet lid.

She pulled her panties to the side and her cock popped right out, standing at full length. Nikki's cock was big, but not quite as big as mine. I had about eight inches and she was probably about an inch or so smaller...still, it was quite impressive. I don't know why but I went along, dropping slowly to my knees and leaning in close.

She grabbed my head and gave me a mouthful of cock, shoving it deep into my throat. I gagged, eyes welling up with tears as she fucked my throat, quite aggressively too.

She only kept this up for a few moments though, before pushing me away and standing up. She moved around behind me and pushed me up against the sink, reaching around and opening the medicine cabinet. Nikki pulled out a small tube of K.Y. Jelly and applied a generous amount, both to her cock and also to my ass. She stroked her cock, rubbing the lube in nice and good until it was good and slick and then smeared it all over my ass crack.

Two fingers forced their way into my tight hole and I gasped, biting my lower lip in a little bit of pain. It was temporary though, because she quickly withdrew her fingers and I felt the hot tip of her cock, pressing against my hole.

Tensing up some, I gripped the sink and bit my lip even harder. Nikki pushed forward and attempted to slide her cock into my ass...I was just way too tight. I felt the head of her dick probing, threatening to pop my anal cherry but it wouldn't give way.

"You're too tense," she whispered in my ear.

"Relax baby."

She started gently kissing me on the neck, running her hands up and down my chest in an attempt to sooth my nerves. It worked a little; I could feel myself relaxing some. As my nerves began to wind down, I felt the head of her cock poking my hole again and then suddenly there was this sharp, searing pain.

I practically screamed, Nikki's hand quickly covering my mouth and muffling the sounds as the tip of her cock slid right into my tight ass, with an audible popping sound.

It was only the head but it hurt so damn much, yet all I could do was stand there with shaking legs and try to keep myself standing up straight. Nikki on the other hand...she was loving it, so far. I was so tight that she must have been struggling not to cum right off the bat, because she hesitated for a few moments. I could hear her moaning softly and panting, as she stood there trying to get a grip.

After a few moments, she started pushing forward and inching her cock deeper into my hole. As she inched her way in, I tightened my grip on the sides of the sink and soon was gripping it so hard, I thought I might rip it from the wall.

I could feel my asshole stretching around Nikki's cock, stretching wider and wider with each passing moment. Finally, she bottomed bout and I could feel her pressing against me now.

With a low groan, Nikki remained still once again, holding onto me by the hips for a few moments before wrapping her arms around my waist and hugging me from behind.

"So...fucking tight," she whispered. "You feel so fucking good Ryan. God, I love your fucking ass right now."

I couldn't say a word in response; the pain was too much. I found myself really hoping that it would subside and maybe I would end up enjoying myself. Some part of me though, worried that I was just dreaming and that it wasn't going to bring me any pleasure at all.

That's when I decided, I didn't want to go through with this any further.

"S-Stop," I said, grunting in pain.

"What's the matter?"

"It fucking hurts...too much!"

"Mmm, relax baby...I know it hurts right now, but that's totally normal. You have to give it enough time and I promise it will start to feel real good. Here, let's use some more lube."

She pulled her cock about halfway out and as she withdrew, I felt like she was dragging my insides out along with her dick.

Nikki grabbed the lube again and poured some more onto her hand, removing her cock all the way now and smearing the lube all over my ass crack again. She applied more to her dick, pushing the head right back into me again and bottoming out almost immediately. I let out a sharp gasp, the air knocked right from my lungs as she slammed directly into me. She definitely went in MUCH easier then the first time, thanks to the extra amount of lubrication.

She waited a few moments again, then grabbed me by the hips and started slowly and gently thrusting.

I held my breath for a long time, feeling my cheeks flush as she slowly thrust in and out of my hole; it still hurt. It felt like she was shoving a pole up my ass and there wasn't much pleasure in that. Strangely enough though, my dick had swollen up to the point where it was harder then I could ever remember it being before.

I took note of an odd sensation, like I had to piss but nothing came of it; just more of the same.

Every thrust that Nikki delivered, was harder then the previous one and caused my body to jolt with every motion. Nikki gradually increased the pace, thrusting harder and faster, moaning in my ear. Until finally, she had stopped showing mercy and was going all out now.

She was pounding my ass, long and hard strokes that caused me to gasp for air. I clutched the sides of the sink and Nikki pushed my head down into it, turning on the sink and pouring warm water all over my head. I yelled out, startled by the water as it soaked my head.

"You dirty little slut," she moaned. "God, take my fucking dick!"

"Ohhh...ohhhhh....ohhhhhh!"

I was amazed at the sounds, that were coming from my mouth. I felt shamed...humiliated...yet somehow, those thoughts seemed to turn me on for some reason. I lifted my head from the sink and looked at my reflection in the mirror; what I saw staring back at me, was absolutely fucking crazy.

My hair was matted to my forehead from the water and sweat, my mouth was wide open and I was moaning and panting like a fucking whore. Behind me, Nikki continued to pound my ass, slamming in and out of me with such force that the sink shook underneath of me. Our bodies slapping together, the sound echoed throughout the bathroom and I was relieved that the music outside was so loud; otherwise, I was sure someone would hear what was going on and put two and two together.

The pain had not subsided, but oddly enough it wasn't as discouraging anymore. It still hurt...yet at the same time, my cock was still throbbing and even leaking pre-cum now. The occasional moan would slip past my lips, causing me to curse myself. Every time I made a sound that made Nikki think I was having fun, she would spank my ass...each time, harder then the last.

Then, I felt her cock start to swell up inside of me. As it grew, I felt my hole stretching wider along with it and I knew that Nikki was starting to get close.

"I'm gonna cum, bitch!" she warned me.

"I'm gonna fucking cum...where do you want it?"

"I...I....don't know," I groaned.

She slammed into me with great force, causing me to yell out. My back arched and I involuntarily shoved my ass back against her dick, my body spasming.

"Tell me where you fucking want it, before I pick it myself!"

"Ah-Ah, ohhh fuck...i-in my mouth!"

"Mm, good choice baby."

She quickly pulled her cock from my ass, yanked me from the sink and spun me around, shoving me onto the toilet. Stepping in front of me, Nikki began furiously jerking her hard cock right in my face. She started moaning, panting and shaking as she was seconds away from her orgasm.