Building A Life In Chicago Ch 02

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.

Taking a shot with my friends was followed by me blowing Chad in the alleyway. My mind then switched over to the first time I saw Jessica naked, bent over a bed, and fucked by Danny. I then remembered Chad calling me a slut and how it made me feel. I was starting to feel my vagina getting wet as I thought about Jessica riding Danny. I slowly moved my hand down to my groin as I thought about making Will cum.

As I continued to think about some of the sexual experiences I've had in my life, I began to rub my clit with my finger. I slipped my finger into my wet, clean-shaven pussy and started to pull it in and out, a second finger soon following it.

"Oh yes," I quietly moan, getting more and more turned on as I remember back to the first time that Danny fucked me. That first night was soon followed by me, him, and Jessica meeting at a hotel and having a near-three-way, just without me and Jessica doing much touching. Next was riding Will the week before.

I started to rub my clit as I thought about Danny fucking me while Jessica watched and played with herself. As the memory of me being covered in cum filled my mind, I orgasmed, having to grab the wall next to me to hold myself steady.

I finished washing my body off, breathing deeply, before I got out of the shower. Dirty thoughts still occupied my brain as I grabbed my phone and laid down in bed, still naked. I hurried and texted my friends, letting them know I was OK, home safe, and just overslept with a hangover.

I raised the phone high above my body and snapped a naked selfie. I almost sent it to Chad, instead sending it to Jessica and saying, "Last night was good. I woke up hungover and horny."

At the last second, I sent it to Will and said, "It would have been you if you were there."

I thought about texting Chad, but I really didn't want to talk to him anymore. Maybe I'd run into him at another club, but I would cross that bridge if it came to it. Instead, I nervously opened up the Tinder app on my phone.

I had downloaded it and set up a profile when I first moved to Chicago. Outside of the initial setup, the app had remained unused on my phone until now. I swiped through some profiles that came up, mostly swiping left but right on a few.

On a whim, I changed my settings to say I was interested in females as well as males. As I went back to swiping, none of the females stood out to me, but I swiped right on a few just to see if any matched me.

After about twenty minutes of swiping, I put my phone down because my stomach was starting to grumble. I stood up from the bed, opted not to get dressed, and went into my kitchen. I made myself a sandwich and ate it at the counter, listening to pings coming from my phone in the otherwise quiet apartment.

Going back into my phone, I had a text waiting from Jessica that said, "I'm glad you had a good night. Too bad Danny isn't around to help you out."

I texted her back to say, "Or you."

I also had my first match on Tinder. The guy had already sent me a message to say hi and introduce himself. I quickly looked at his profile again and saw that his name was Owen; he lived just outside of Chicago, worked in sales, and was pretty good-looking. I sent a message back saying hi in return.

He started asking questions about me, and I answered a few before I said, "Listen, I'm going to be honest. I'm completely naked right now. I'm extremely horny. I'm just looking for somebody to come and fuck me. So, I don't care about anything else but, How big is your dick?"

I didn't have to wait long before I received a picture back from him. Standing in front of a mirror, he had unbuttoned his pants and was holding his cock in his hands. It appeared to be about six inches long and thick. I quickly sent him my address.

I didn't have to wait long until I heard a knock on the door. I got up and looked through the peep hole to confirm that it was Owen, and I opened the door for him. He was a few inches taller than I am, had dark brown shaggy hair, and had a bit of a belly to him. He wore glasses on his eyes, but he had a killer smile. He stared at my naked body as I invited him in and closed the door behind him.

"You're even hotter in person than your pictures are," he told me.

"I've already told you I'm going to fuck you, so you don't have to keep buttering me up," I told him as I walked him towards my bedroom.

"I know," he said. "Just stating a fact."

I smiled as I dropped to my knees and started to pull on his pants and boxers. I wrapped my hand around his growing cock, looked up at him, and asked, "How long can you stay?"

"For you, I'm free all day," he said, as I flicked my tongue across the head of his cock. I wrapped my lips around it and slowly slid half way down, using my hand to rub the bottom half of his shaft. I started to bob my head up and down, only taking half of him. Looking down at me, he asked, "Is that really all you can take of me? I don't believe it."

I took him out of my mouth, used my tongue to lick up and down all over his shaft, and said, "Maybe I just need some encouragement."

I got his cock back in my mouth as he put his hand on the back of my head and started to push down. I easily swallowed his cock whole and started to bob my head up and down his full length. I kept one hand wrapped around his shaft, moving in sync with my head, while I grabbed his balls with my free hand and held them up.

"Oh fuck," I heard him moan. "If you want to fuck, you better stop."

I removed my mouth from him again and said, "Or, if you really can stay, you can cum down my throat or on my tits, and we can fuck later."

"Oh, fuck," he said. "Oh, fuck, fuck, fuck!"

I felt his cock twitching in my hand as I jacked him off. I pointed his tip at my chest as the first rope of cum shot out, landing just above my right nipple. I moved it so the next shot landed on my left nipple, before wrapping my lips around his cock, and pumping the rest of his cum into my mouth, where I quickly swallowed it down.

When he started to go limp, I took him out of my mouth again and licked my lips clean. He sat down on the bed and watched as I wiped his cum off my breasts with my fingers before sucking them dry. I stood up and said, "I'll go clean off my tits with some water so you can suck on them."

As I walked into my bathroom, I could feel his eyes watching me. I quickly cleaned myself off before going back to him. As I approached him, Owen took his shirt off, leaving him naked as well. I climbed onto his lap, wrapping my arms around his neck and leaning towards him to kiss his lips. As he returned my kiss, he wrapped his arms around my waist and pulled me closer to him.

I felt my nipples rubbing on his chest as we made out. Almost immediately, Owen tried to push his tongue into my mouth. Instead of letting him, I broke the kiss and started to push his head down and toward my chest. Knowing what I wanted, Owen wrapped his lips around my right nipple and used his tongue to lick around it. He reached one of his hands in between us, took my left breast in it, and squeezed over and over.

With my hands still on his head, I moved him over to my left breast, moaning as he licked around that nipple and sucked it into his mouth. I let go of his head, and Owen spent the next few minutes sucking on my nipples, licking them, squeezing my breasts with his hands, and rubbing my nipples with his fingers.

The more he played with my B-cup-sized breasts, the more turned on I got. As I felt my vagina getting wet, I started to grind on his groin, feeling his limp cock on me. Owen moved his head back up and kissed my lips. He again tried to push his tongue into my mouth, but I pulled back and said, "Do you want to know something that really turns me on?" He asked what it was, and I said, "Tasting myself on a guy's tongue."

Once again getting the hint, Owen rolled us over, laid down on the bed, and immediately moved down to my groin. I spread my legs as he examined my clean shaven pussy. He tentatively stuck his tongue out and ran it up my slit, making me moan. He kissed around my pussy lips and clit, before sliding his tongue between my lips and into my pussy.

I moved my hands down to his head, wrapped my fingers in his hair, and kept his face on my groin as he started to dart his tongue in and out of me. I continued to moan, telling him how good it felt, as he flicked his tongue all over my pussy, inside and outside it, against my clit.

When I let go of his head, I moved my arms behind me, propping myself up on my forearms and giving him a bit of a different angle. Owen responded by bringing one of his arms up and sliding two of his fingers inside my pussy. As he pulled and pushed them in and out, he used his mouth and tongue to continue to lick and kiss everywhere else.

At the same time, he raised his other arm up, used his hand to squeeze my breasts, alternating between the two, and used his fingers to rub my nipples.

"Oh fuck, that feels so good," I moaned as he continued to eat me out. He wrapped his lips around my clit, using his tongue to flick it as his fingers went in and out of me, and started to hum with his lips. My breath got shorter, my legs squeezed around his head, and I pushed up with my hips as I started to orgasm. "Oh, fuck yes!" I said as I laid my head down, my eyes rolling into the back of my head, and my face scrunched up as I felt my juices flowing out. Owen quickly started to lick all around my pussy, getting as much on his tongue as possible.

As I came down from my orgasm, Owen moved up my body, keeping his fingers going in my pussy. I saw a smile on his face as he came even with mine. I wrapped my arms around his neck, pulling him down as I began to kiss him. This time, I used my tongue to open his mouth, tasting myself on his lips and his tongue. He eagerly kissed me back, his tongue swirling around mine, pushing back and forth between our mouths.

As we made out, I felt another orgasm building up and broke our kiss. "Oh yes, yes, yes!" I moaned, staring him in the eyes until mine closed shut, his fingers bringing me to another orgasm. This time, as I came down from it, he pulled his fingers out of me. I smiled as I opened my eyes and said, "That felt amazing. I can count on one hand how many guys have been able to make me orgasm twice in a row like that."