It had been a week since I had had my first hookup in Chicago. And it was a week from hell. Nothing was going right at work; the AC in my one-bedroom apartment broke, and Will, the guy I hooked up with, wouldn't leave me alone. By that Friday, I was ready to be done and just wanted to forget about everything.
A few of the girls that I work with, knowing my frustrations, invited me to go clubbing that night, and I gladly accepted, telling them that I wanted to get drunk and to get laid. As I got dressed after work that day, I picked what I hoped was my sluttiest outfit.
I left my black hair loose around my face but put on more make-up than usual, including a red lip stick. I picked out a white crop top with a low "V" cut in it, plus a push-up bra. Between the bra and shirt, my B-cup-sized breasts were being pushed up and together to look bigger and like they were ready to pop out of the top.
I thought about going without underwear, but decided on a pink thong at the last second. As I looked at different skirts or pants to wear, I was dancing around to some music and looking at myself in the full-length mirror I kept in my room. As I looked at my tan skin, long legs, and breasts being pushed up, I grabbed my phone and snapped a photo of myself.
I started to send it to Danny but changed at the last second and sent it to Jessica, saying, "I know this is probably a little strange, but I've been thinking about you a lot lately. I hope you're doing well, and I miss you!"
I finally decided on a white, pleated mini-skirt that barely covered my groin. I moved around a few times, bending over and such, trying to see what I could and couldn't do to not flash people. I finished off the outfit with a pair of three-inch heels, pushing me taller than my normal six-foot height.
Jessica texted me back right before I left, telling me that I looked hot and she missed me too. I jumped into the Uber my friends from work were already in with a smile on my face and butterflies in my stomach.
At the first club we went to, I went right up to the bar, ordered myself a shot, and drank it. We went out on the dance floor, and I was almost instantly surrounded by a group of guys, all trying to grind on me. I danced for a few songs before stepping off and going for another shot.
One of my friends wasn't liking the vibe of that club, so we left after another song, walking down the road to another club. That one seemed better, as all three of us had drinks bought for us as soon as we walked up to the bar. I went back to dancing, finding another group of guys to surround myself with.
After dancing and taking shots for the next hour, I found myself a little tipsy and went to sit down at a table. One of my friends came to find me after a few minutes, making sure I was OK. After I said I was, she told me, "There's a guy at the bar that keeps looking at you, if you're still looking to get fucked. He's pretty hot."
She pointed him out to me, and I instantly recognized him. I didn't know his name, but he was at the same bar I was at last week, had hit on me, and I found out later that he was Will's brother. Drinking always made me horny, and I was ready for something to happen, so I walked over to the bar to an open spot next to him.
"Hi, I'm Kourtney," I said to him as I sat down next to where he stood.
"I'm Chad," he said, sticking out his hand to shake mine.
"Well, Chad, do you want to buy me a drink?" I asked him.
He signaled to the bartender to bring me a shot, and he asked, "Do you remember me?"
I laughed and said, "You're Will's brother."
He confirmed he was as I took the shot and said, "He told me what happened last week and that you've been ignoring him ever since."
"Yeah, I did kind of use him, didn't I?" I said this as I looked Chad up and down.
He was as tall as I was wearing heels, looked like he went to the gym often, and was dressed in a preppy style. Before he said anything back, I asked him, "Do you want to use me to get back for him?"
"My place or yours?" He said this, flashing a smile that was actually pretty cute.
"How about out back?" I said, getting up off the stool and placing my hand on his groin. He tried to stammer out an answer as I rubbed up and down and felt him starting to grow in his jeans.
"Follow me. Or should I find somebody else again?" I teased him as I turned to walk away. I soon felt his hand on my hip as he guided me to the back of the club, past a ton of people, and out the back door to an alleyway. We looked around for a minute before walking over to a pole next to the building and going around it to try to stay hidden.
I wrapped my arms around his neck, leaning in to begin kissing him. His arms wrapped around my waist, and as he kissed me back, his hands roughly grabbed my ass. He reached under my skirt, placing his hands on my bare buttcheeks, and started to squeeze them. At the same time, he pushed his groin into me, grinding his growing cock onto me.
After making out for a few minutes, I ended the kiss and squatted down in front of Chad. I undid his belt and his pants, opening them up just enough to reach into his boxers and pull out his cock. I was expecting something like what Will had, but was presently surprised to see that Chad was at least seven inches and fairly thick. I held his cock straight out and swirled my tongue around the tip of it, licking up his precum.
I looked up at him with my hazel eyes as I wrapped my lips around his tip. He moaned as I slid my mouth down his cock, and his eyes went wide as I took him deep down my throat. I held myself there for a few seconds before I started to bob my head up and down his thick cock. As I did so, I used my hand wrapped around his shaft to pump it up and down.
"Oh fuck, you're so fucking hot," I heard Chad say as he reached behind my head and put his big hand on the back of it. He started to push me down his cock, making me swallow more and more of it every time I moved down it. I continued blowing him for a few minutes until I pulled him out of my mouth, gave his tip a kiss, and stood up.
As I stood up, I reached up my skirt, in between my legs, and pulled my thong down to my knees. Chad was licking his lips, his hand on his cock, as I turned around and placed my hands on the pole hiding us. I felt my skirt moving up as Chad lifted it, and I felt the night air on my now exposed, clean-shaven vagina. Chad put one of his hands on my hip while he inserted his cock with his other hand.
His thick cock was stretching out my vagina, so I spread my legs a little farther apart. I moaned as he pushed deep inside me. With both of his hands on my hips now, Chad started to roughly fuck me. His cock slid in and out of my wet pussy, over and over, harder and faster as I moaned my encouragement.
"Oh yeah, you like that, don't you? You're just a little slut, aren't you?" Chad said as he continued to pound into me. I moaned that I was a slut, and he said, "Yes. You are. I knew it from the moment I laid eyes on you."
I started to push back against him as he slammed his cock into me, moaning every time his cock filled me up. He continued to talk dirty to me, but I zoned it out as I enjoyed the feeling of getting fucked.
"So, where does the little slut want my cum?" I snapped out of my zone and focused on what he said. I told him, "On my face, Daddy."
He pulled out of my vagina and took a step back as I turned around. This time, as I squatted back down, I pulled my breasts out of my crop top and watched as his eyes went right to my nipples. I felt them harden in the night sky, and I pinched them before reaching out with my hand and wrapping it around his cock.
I pumped his cock a few times before I felt it twitch in my hand. I aimed his tip at my face as the first shot of cum came flying out and landed on my chin. I continued to rub his shaft up and down as I moved his cock around my face, covering my cheeks and my nose.
When he was done, I stood back up, licking off the cum I could reach with my tongue, wiping the rest onto my fingers, and licking it off them. He watched me as I cleaned his cum off, with my breasts still exposed and my thong still around my knees.
I quickly pulled my thong back up, tucked my breasts away, and said bye to Chad before turning around and walking back into the club. I quickly found my friends who were ready to go to another club. I told them that I was getting tired, thought I had drunk too much, and should go home. I had an Uber ordered for me and said goodbye to them when it arrived.
I woke up the next day with a pounding headache. I was lying on top of the blanket on my bed, my head on one corner and my feet on the other end. I had somehow managed to get my bra off but was still wearing my skirt and thong. I rolled over and found my phone lying next to me. I unlocked it to see that it was nearly noon and I had a bunch of text messages.
The first few were from my friends, some telling me that they were home, and two of them checking in on me this morning. I had one text from Will that said, "You fucked my brother!? You whore. Fuck you." I guess I didn't have to worry about him anymore.
Chad also texted me, wanting to know when I wanted to hook up again.
The last text was from Jessica, asking how the night before went. As I read it, the light from the screen was making my head hurt even more, so I put my phone down before responding to anyone. I managed to roll over onto my back a few seconds later and slowly sit up in bed. I felt something coming up from my stomach, so I quickly ran to the bathroom, lifted up the toilet seat, and threw up into the toilet.
After I was done puking, I pulled off my clothes, turned on the shower, and climbed into it. I kept the water cold, and as it hit me, memories from the night before came flooding back, mixed with other memories.
