📚 building a life in chicago Part 5 of 10
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Building A Life In Chicago Ch 05

Building A Life In Chicago Ch 05

by pooer87
16 min read
4.71 (2000 views)
adultfiction
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I couldn't believe it. My best friends from Utah, the guy I was in love with, and the only two people I felt like I could really trust flew to Chicago to be with me. After hanging up the phone with Danny, I glanced around at my apartment. Since getting in a fight with Rachel the weekend before and having her stomp out, I had let myself go. Dirty dishes and clothes were everywhere. Trash was covering the kitchen counters. The bathroom was a disaster. I wiped away a tear and started to clean, knowing I only had a short time before Jessica and Danny would be at my apartment.

I quickly threw all the garbage into a bag, stuffed clothes into a laundry basket, wiped down the kitchen and the bathroom, and was just putting the last dish into the dishwasher when somebody knocked on my door. I skipped over to the door, looked through the peekhole to see Danny and Jessica, and opened the door for them.

Danny, ever the gentleman, let Jessica in first, and I gave her a hug as he walked in and closed the door behind him. Letting go of Jessica, I threw my arms around Danny's neck, his arms went around my waist, and we held each other tight. As I felt his loving embrace, I started to cry, and Jessica started to rub my back, asking if I was OK.

Letting go of Danny, I wiped the tears from my eyes and said, "I am now that you guys are here. It's been a really hard week."

Jessica grabbed my hand and let me into my living room, where we all sat down, me and Jessica on one couch, Danny on the other. "What happened?" Jessica asked me. "You seemed so happy last week, and now you're not."

"I got in a fight with Rachel, the girl I was seeing. I accused her of using me. She acted like she was doing me a favor with the things she was doing with me. So, I told her to leave, and I haven't heard from her since," I explained to them.

"Dang it, Kourtney, I'm sorry," Jessica said as she wrapped her arms around me and pulled me close to her.

"Yeah, that really does suck," I heard Danny as I laid my head down on Jessica's shoulder.

I looked over at Danny, my former brother-in-law that I've had a crush on ever since my sister first brought him home when I was sixteen. He was thirty-six years old, almost thirty-seven. With dirty blonde hair that he kept shaggy, just long enough to cover his forehead, he had a full beard, along with the brightest, cutest blue eyes you've ever seen.

He was a few inches shorter than I was, standing around five feet, nine inches tall. He had always been skinny and enjoyed going to the gym, mostly to ride a bike or walk on a treadmill. He always knew how to make somebody laugh, and you always knew that he truly, deeply cared for you.

Jessica, on the other hand, was a full foot shorter than me at only five feet tall. She had long brown hair that was pulled back into a ponytail, C-cup-sized breasts that I could just see a hint of cleavage with the tanktop she had on, and an amazing ass that I had been dreaming about.

She used to be married to my brother, and, honestly, I would have gladly traded him for her. She's been a great friend of mine for nearly a decade.

"Thanks. I don't know what I was thinking. I thought I really had something with her, but now, I think it was just a rebound thing," I told them.

"What about that one guy you slept with?" Jessica asked me.

"Yeah, you seemed to really like him," Danny joined in with.

"Owen? I actually saw him the day me and Rachel fought. I wanted to get somebody off, so I drove to his house, gave him a blowjob, and left. I should probably give him more of my time, but I just don't know anymore," I said.

"Lucky guy," Danny said.

"Yeah, Danny has missed your blowjobs," Jessica said.

"Really?" I asked, looking over at Danny and glancing down at his groin, remembering what he had packed away in his shorts.

"Yeah. I was giving him one this morning before we left, and I know he misses somebody taking him all the way in," Jessica said, making us all laugh.

"Well, I guess that I had better cheer up than if that's your expectations this weekend," I said, getting them both to say that they had no plans and just wanted to be with me. "Whatever, don't lie to me. I know, at least in Danny's case, that he's not flying all the way to Chicago and not leaving without a blowjob and more."

"It's true," Danny said. "I told Jessica that my two main goals for this weekend are to get a blowjob and watch you two make out."

"I like the sound of both of those," I said, smiling up at Danny.

"Well, as much fun as those would be, I really think that for tonight, maybe we should just get some food and relax," Jessica said, letting go of me as I sat up on the couch.

"I like that idea," Danny said. "What's good around her, Kourtney? Should we go somewhere or order in?"

"Definitely go. There's a good little restaurant just down the road you two will love," I said, standing up off the couch.

We left my apartment, and I drove us over to the restaurant. We were quickly seated and had our order placed within minutes. They started to ask me my favorite things about Chicago and what else I had been up to since moving here. I asked them about Utah and the like.

We continued the conversation as the food came and we ate it. As we waited for the check, Jessica asked, "So, one thing we didn't really consider, but what do you think will be the best sleeping arrangements while we are here?"

"All of us in one bed together," Danny immediately answered.

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We laughed, and I said, "I'm fine to sleep on the couch so you two can have the bed."

"And here I was thinking that you two should have the bed so you could do whatever you've missed doing together without me being in the middle," Jessica said.

"But, what if we want you in the middle?" Danny asked.

"Yeah, what if we want you in the middle?" I said as well, as we all laughed.

"Yeah, in the middle, on the side, top, bottom, we want you all over us," Danny continued.

"But, seriously, I'm cool with whatever you guys want. It can even change every night if we need it too," I said.

We paid our bill a few minutes later and left the restaurant. Once back at my apartment, we settled down on my couches, continuing our conversation and sharing stories. A few hours later, Danny announced that he was exhausted and starting to fall asleep. I told them that they should take the bed tonight, since it would help with the jet lag and get a good nights rest.

After Danny got up, kissed both mine and Jessica's foreheads as he said goodnight, I looked over at Jessica, and said, "I still can't believe you guys are here."

"Me either," Jessica responded. "But, when we saw your text, we knew we had to get out here as soon as we could."

We talked a little bit longer until Jessica started to fall asleep. She went into the bathroom as I quietly went into my bedroom to get a blanket and pillow. When I came back out, Jessica was in the living room, having changed from her leggings into shorts and taken off her bra.

"You should go sleep with Danny and surprise him with a blowjob tomorrow morning," she said as she looked at me.

"Really?" I asked her.

"Yes. He'll love it," she told me, taking the blanket and pillow from me.

I said, "OK," and started to walk back to my room, but turned around before getting there. I walked back up to Jessica and wrapped my arms around her, as she did to me. Without saying a word, I looked down over the much shorter girl. I waited for her to look up, and when she did, I planted a quick kiss on her lips before turning and walking into my room and crawling into bed next to a sleeping Danny.

When I woke up the next morning, I could feel Danny pressing against me. He had one arm wrapped around my midsection, and I could feel his morning wood against my butt. I grinded my butt against him, trying to wake him up, but it didn't work. Instead, I pushed hard against him, and he rolled over onto his back.

I lifted up the covers, saw that Danny was wearing a pair of boxers with the tip of his hard cock poking through the flap, and I crawled under them, letting them fall over me as I reached his groin. His body jumped as I put my hand on his cock and started to rub it up and down.

I pulled the opening of his boxers apart and pulled out the rest of his cock, smiling as I saw his six-inch-long shaft and head for the first time in a few months. I've slept with guys with bigger dicks than Danny, but there's just something about his that I will always crave. It's not super long, it's thick, and I just love it.

I wrapped my hand around his shaft, my fingers barely able to touch each other, and slowly pumped up and down. Holding his cock straight up, I felt his body shudder as I licked from the bottom of his shaft, up to his tip, and back down again. Danny moaned when I wrapped my lips around his tip and slowly slid down him with my mouth.

I felt the blanket lifting up off me when I bottomed out on Danny's cock, and I looked up to see him staring down at me. "I had a feeling that wasn't Jessica down there," he said as I started to bob my head up and down his shaft. I smiled as he continued to moan.

I still had my hand wrapped around his shaft, and I started to bring it up as my head went up and down as my head went down. Danny threw the blanket off me, and I glanced up at him as he closed his eyes and laid his head back on the pillow. I started to only suck on his tip and took only the first couple inches of him into my mouth, leaving the rest of his shaft for my hand to work up and down.

I heard Danny beginning to moan and knew it wouldn't be long until he started to orgasm. He moved his hand down and put it on the back of my head and started to push down. On response, I moved my hand down to the bottom of his shaft, opened up my throat, and swallowed his cock whole.

Danny's hips pushed up, shoving his cock deeper into me as I felt his cum shooting out the tip of his cock and hitting my throat. I swallowed as quick as I could until Danny lowered his hips and moved his hand off my head. I then moved my mouth back up to his tip, and I pumped up and, with my hand, got every last drop of cum from him.

When he was done, I removed my lips from him and used my tongue to lick the cum off his tip and from around his shaft. As he started to go lip, I looked up at Danny, who was looking down at me. He smiled and laughed as he watched me lick my lips and said, "Good morning. Have you been in bed with me all night?"

"Yes," I answered, scooting back up to lay down next to him. "It was Jessica's idea."

"Remind me I need to thank her later," he said.

"How long did it take you to realize that it was me and not her?" I asked, generally curious.

"When you go down farther than she can," he explained.

He wrapped his arm around me and pulled me close to him. I put my hand on his chest and laid my head down on his shoulder, closing my eyes and enjoying his cuddles.

I was just feeling like I could fall back asleep when I heard a knock at the door. I opened my eyes to see Jessica poking her head in and asking, "Are you guys awake? Can I come in? Or am I interrupting something?"

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"We're awake. You can come in," Danny said.

I smiled at Jessica and said, "Five minutes earlier and you would have interrupted something."

"I thought I heard some moaning when I woke up. Did you wake him up with a blowjob?" Jessica asked as she came into the room and sat down on the edge of the bed, next to Danny.

"Yes, I did. He thought I was you until I deep throated him," I told her.

"That's funny. Maybe later tonight we'll have to blindfold him and see if he can tell the difference between us without taking him all the way in," Jessica said.

"I like that idea. We could have lots of fun with him blindfolded," I said, thinking of the possibilities.

"Why wait until tonight? We can start now," Danny asked, getting excited.

"Because we have all weekend to do that kind of stuff. But I've never been to Chicago, and I want Kourtney to show us around," Jessica said. "So, get up, and let's get go out!"

Jessica got up off the bed and turned to walk out of the room. As she left, me and Danny watched her go, and I said, "God, she has a nice butt."

"Yes, she does," Danny said.

"We're going to have so much fun later. Do you really think she's going to do something with me?" I asked.

Before Danny could answer, Jessica said from outside the bedroom, "I can hear you! I'm not going to do anything with anybody if you don't get up now!"

We got up, and all three of us got ready, with each of us trying to sneak a peek at the other undressing or getting dressed. After eating a quick breakfast, we loaded into my car, Jessica sitting in the front with me and Danny in the back. Kourtney showed us some of her favorite places, where she worked, where she was going to go to school, and we ate lunch at her favorite cafe.

After visiting a few more sights, we ended our trip around Chicago by picking up a frozen pizza and headed back to my apartment.

Once back there, I had a sudden desire for Jessica. I had been keeping my eyes on her all day, staring at her butt in the tight jean shorts she had on or glancing down her loose tank top at her breasts whenever I could. I had gotten a glimpse of her pulling on a pink thong that morning, and I was hoping to take it off for her.

We sat down in the living room to eat our pizza, me on one couch and Jessica and Danny on another. I could feel my vagina getting wet as I watched them eat, dirty thoughts about what could happen filling my mind. I was tempted to just jump one of them as we finished eating, but instead, I took their plates from them, put them in the sink, and went to the bathroom.

When I came back out, Danny and Jessica were cuddling together on the couch, whispering to each other and watching me as I sat down across from them. "What?" I asked them as they giggled together.

I watched as Jessica untangled herself from Danny and sat up straight on the couch. She cleared her throat and asked, "Do you remember this morning when you asked Danny if I really was going to do something with you?"

"Yes," I answered her as she stood up from the couch and walked towards me. I leaned back on the couch as Jessica climbed onto me, her legs straddling my lap. She wrapped her arms around my neck and leaned down, her head tilting to the side as she pressed her lips against mine and kissed me.

I pushed back and returned the kiss as her lips lingered on mine. We lost our inhibitions and started to make out like teenagers, our heads twisting and turning, our tongues pushing against our lips and swirling together, pushing back and forth into each of our mouths. My arms wrapped around her back, rubbing her as her body moved up and down, grinding our groins together.

Jessica pulled away a few minutes later, and I opened my eyes to see Danny watching us. Jessica slipped her body off mine and kneeled on the floor in front of me, in between my legs. She put her fingers into the hem of the maroon leggings I had on, and I lifted my hips off the couch as she pulled them down, leaving them at my ankles. I moaned as Jessica's hand brushed against my vagina as she reached for my underwear and pulled them down.

She kissed around my clean-shaven pussy but, seemingly unsure of what to do, she brought her hand up, and inserted a finger into me. I moaned as she pulled the finger out and pushed it back in. I looked up to see Danny watching us intently, his cock starting to show in the shorts he had on.

Jessica continued to kiss and lick around my vagina as she kept fingering me. When her lips brushed against my clit, I moaned louder, and she went back to kissing it more often.

"Sorry if I'm not very good. This is my first time," Jessica said as she kept pleasuring me.

"You're doing good," I breathlessly told her. "Kept kissing my clit and I'm going to cum soon."

Jessica quickly found my clit again and put her lips on it. She flicked her tongue against it and started to suck on it. I was staring at Danny as I felt my orgasm coming. I put my hands on the back of Jessica's head, pushed up my hips, and started to grind my groin on her face.

"Oh, fuck," I moaned as my body stiffened up before releasing a massive orgasm. My eyes slammed shut as I felt my juices flowing out, and Jessica attempted to suck them up. "Oh my God, oh yes! Yes! Oh fuck," I moaned.

As I came down from my orgasm, my body relaxed, and I moved my hands away from Jessica's head. I was breathing deeply as I watched Jessica stand up, walk over to Danny, and lean down to passionately kiss him, sharing my cum with him.

When she ended the kiss, she turned around to me and asked, "How did I do for my first time?"

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