📚 building a life in chicago Part 1 of 10
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Building A Life In Chicago Ch 01

Building A Life In Chicago Ch 01

by pooer87
19 min read
4.5 (4900 views)
adultfiction
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Note: hi all, welcome to the start of a new series. The characters from this are first featured in another series, "Pleasing My Sister-in-law." I suggest reading that first before starting here. Thanks for reading! Thoughts and comments are always welcomed!

I'll never forget the night that would cause entire life to change, but I didn't know it at the time. I was down in Las Vegas for my sister's wedding and staying at an AirBNB with my husband, sister, her husband and kids, my brother and his wife and kids, and my parents. It was the last night we would be there before leaving the next day.

I had just gotten done taking a shower with my husband. He immediately fell asleep while I was combing my long, brown hair, and I was still wide awake. After putting on some clothes, I decided to get some fresh air, and I stepped out onto the balcony overlooking the backyard of our AirBNB.

As I breathed in the night air, I all of a sudden could hear moaning. I looked over to the side of the house, where the swimming pool and hot tub were. I instantly recognized the moaning as coming from my sister-in-law, Jessica. I saw her bent over the edge of the hot tub with her husband, my brother, pounding into her from behind.

I was confused as I watched them for a few seconds, as I knew it was not like my brother to do something so bold and brazen like fuck his wife outside in a pool, but quickly shook my head and went to turn back around to go inside. But then I heard Jessica going from moaning to saying, "Yes. Yes. Oh, Danny, this feels so good."

Danny? That is not my brother's name. Danny is married to my oldest sister. What was he doing with Jessica? How? I turned back around and watched them again, as Danny pounded Jessica from behind. When Danny finished by cumming inside her, I finally turned and went back inside. I quickly walked back to my room, which was next to the room Danny was staying in, and jumped into bed. I felt my pussy getting wet as the memory of what I just witnessed replayed in my head over and over.

My husband, Gary, and I woke up early the next morning to leave for home. I wasn't sure what I would do or say if I saw Danny or Jessica, but we luckily left before anybody else woke up. I made Gary drive because I just had to talk to Jessica. Knowing that Jack, her husband, read all of her text messages, I hopped on Facebook and sent her a message.

"Hey, first off, I want you to know that I'm not mad. But, I did see you and Danny in the hot tub last night. I just want to know how it started and how long it has been going on."

Jessica responded back faster than I thought she would and told me that it just started that weekend. She made me promise not to tell anybody, and I agreed.

Jessica was one of the few people that knew that I had a massive crush on Danny. I was just fifteen when he started to date my sister, and it wasn't long before I was developing feelings for him.

Growing up in a sheltered LDS home in Northern Utah, I started to rebel as soon as I started to notice boys. By the time I was fifteen and Danny came into my sister's life, I was already hiding secret meetups with boys from my parents. In high school, I was known as the school bicycle. I never let anybody get too far, but if they wanted a blowjob or to finger me, who was I to say no?

So, I spent many nights dreaming and fantasizing about Danny. Five feet, nine inches tall, with shaggy brown hair and piercing blue eyes, he was skinny and fit and could make anybody laugh. Over the next decade plus, I watched as he and Kathy grew together, got married, and had kids.

I still remember their wedding day. After their sealing ceremony at the LDS temple, Danny and Kathy went back to their house, and Danny took Kathy's virginity. Kathy started to bleed and, in a moment of panic, called me for help. I quickly got to their house to calm her down and get her cleaned up. While there, I hinted to Danny that I went through the same thing, but I'm not sure if he got the hint or not.

While Jessica did know about my crush, she didn't know that I had a bit of an open relationship with my husband. A few years into our marriage, he got really sick, and it killed his testosterone. We talked it out, and, due to my high sex drive, he was OK with me sleeping around some, as long as I always came home to him.

And that's how I found myself the day after coming home from Vegas, texting Danny, telling him I wanted to sleep with him, and figuring out a day when.

I was hoping that it would be just a one time thing, but as soon as I felt his six-inch-long cock inside me, I knew I needed Danny more. Jessica couldn't stay away from him either, and that's how we found ourselves sharing him in an affair.

That affair is what would cost me everything. First, Jessica divorced her husband. Then I confessed everything to my husband, and he left me. I got drunk and told Kathy everything, causing her to kick Danny out. Danny and Jessica recovered as nobody but me knew about them. They got into a relationship with each other and moved in together. I kept arguing with my parents to the point I wanted to go without contact with them and, after applying to tons of dental school, found myself moving to Chicago to go to school.

I wanted Danny to move to Chicago with me, but he wanted to stay with Jessica. I was mad at Danny for a short time after he told me no, but I got over it and lived with him and Jessica for a month before moving to Chicago.

I officially moved to Chicago in April, despite not starting school until the fall. I started a job at a dental office a week after arriving and moved into a one-bedroom apartment two weeks after that.

As I settled into my new life, I was getting to a point where I wanted to get out and make new friends, see new sights, and discover who I was away from my family. I had gone out a few times with some girls from my new office, but they were all in relationships or had drama going on. I needed a night out to myself and to just loose control for a night.

I was standing in my bathroom on a Friday night, staring at myself in the mirror above the sink. I had just gotten out of the shower, and my hair, now dyed black and hanging just below my shoulders, was still wet. My height at six feet tall did leave me towering over a lot of people, but I loved it.

I had always wished my breasts were bigger than the B-cup I have, but they fit my body well. My stomach wasn't as flat as it normally was since I hadn't been to the gym since moving to Chicago, but it was still skinny. I was blessed to have some Native American ancestors that left me with tan skin all year long. While in the shower, I had shaved my vagina, leaving it nice and smooth, along with my long legs.

I grabbed my phone sitting on the counter and took a selfie of me in the mirror. I sent it to Danny, who was home alone that night, telling him I wish I was with him.

After combing my hair and leaving it loose around my head, I walked into my bedroom and started to look through my drawers for something to wear. I knew I was going to a bar that night that was just down the road from my apartment, but I wasn't sure what I wanted. Did I want to find a man to bring home? Did I just want to drink? Was I hoping to find a friend? Did I just want to eat and laugh, listen to some music, maybe dance a little?

I first grabbed a blue thong and pulled it up my legs, adjusting it so the string was in my ass and it covered my vagina. I opted for a black sports bra to cover my breasts. Figuring I should at least show off some of my body, I picked a tight, white belly shirt. On top of that, I randomly pulled out a tan pair of overall shorts.

After pulling them on. I took a couple more pictures and sent them to Danny, who told me I was beautiful. I missed him.

I grabbed my keys and phone, left my apartment, locking it behind me, and made the five-minute walk to the bar. It was still early in the night as I sat down at the bar, ordering a margarita and a sandwich. After I ate, I sipped my drink while watching the crowd pour in. A few guys tried hitting on me, but they weren't my type, and I easily brushed them away.

When the music started, I got up and danced a little, trying to get some attention, but it seemed everybody was already paired up, annoying, or avoiding me. As I walked back to my seat at the bar, I spotted a man sitting at a table with a group of friends. A few of his friends had hit on me, but he seemed the complete opposite of them. I ordered another drink as I sat down and watched him.

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His friends were laughing and joking, getting up to dance, get more drinks, or go hit on a girl, but he just stayed at the table, sometimes smiling, usually just sipping on his drink. I watched him for a few minutes until his friends got up and went off to dance and drink.

I walked towards him, sliding into a seat next to him after making eye contact. "Hi," I said. "I'm Kourtney."

"Hi, Kourtney. I'm Will," he replied back.

"What's your story, Will? You're not partying with all your friends?" I asked him.

"They're not my friends. It's my brother and his friends. They only brought me along to drive them home," he explained to me.

"I see. Well, they keep hitting on me," I said.

"I'm sorry. They're hitting on everybody in here," he said. "I'm kind of hoping they'll all find another ride home so I don't have to worry about it."

"How about you? Are you looking for anybody to hit on?" I asked him, leaning over the table, trying to catch him looking down my shirt.

"It would be nice, but I am getting paid to make sure they get home, and I have no idea how long they'll be out," Will said.

I saw his phone laying open on the table, and I grabbed it from him. I quickly typed in my number and said, "Well, when you're done, I'm only five minutes from here, give me a call and I'll be waiting."

I put the phone down before standing up and walking away. I went back to my seat, changing my drink to water, and wondered if he would call.

It was about thirty minutes later, and I was ready to give up for the night, go home, and wait to see if Will would call, when I saw him come walking towards me. Sitting down at the bar stool next to me, he asked, "Are you really only five minutes from here?" I confirmed that I was, and he said, "These guys will never notice me leaving for a little bit if your offer still stands."

I told him it did, and I quickly paid off my tab, and we left the bar together. Once outside of the loud bar, he said, "I looked up your area code. Are you from Utah? What are you doing in Chicago?"

"Yes, I'm from Utah. I'm going to school here in the fall," I told him.

"Are you Mormon?" He asked me.

"I was, but not any more," I said as we walked.

"Can I ask why not?" He asked.

"Will, are you wanting to get to know me or just get laid?" I said, walking a little faster.

When we arrived at my apartment, I let him into my apartment. I shut and locked the door before turning to face him. He was a little shorter than I am, had his blonde hair cut short, was skinny but not too skinny, and seemed like he wasn't sure what to do.

I walked up close to him and asked, "Will, are you nervous? Is this your first time?"

"It's my first time having a random hookup. I was with my first girlfriend for five years," he said.

"Have you been with anybody since?" I asked, standing right in front of him, our bodies so close to each other.

Will started to stammer out an answer, but before he could get it out, I leaned down and started to kiss him. He hesitated at first to kiss me back, but he started to as I pushed my body up against his. I briefly broke the kiss as I tugged on Will's shirt and pulled it up over his head, revealing a hairy chest with a bit of fat to his stomach. I kissed him again as I rubbed my hand on his chest.

Will finally wrapped his arms around my waist and started to move his hands up and down my back, resting them on my ass and squeezing my cheeks. I moaned into his mouth to show him my pleasure. Still kissing, I moved my hand down his chest, over his stomach, and put it on his groin. I felt his hard cock through his pants and began to rub it.

Breaking the kiss, I asked him, "Did your ex give you blowjobs?"

"Yeah," Will said breathlessly as I rubbed him. "But they didn't last long. She wasn't a big fan."

"I am," I said as I kneeled on the floor in front of him. I looked up at Will as I unbuttoned and unzipped his pants before pulling them and his boxers down to his ankles. His cock popped out at me, about five inches long. I easily wrapped my fingers around it and started to rub up and down. I flicked my tongue against his tip before I opened up my mouth, wrapped my lips around his cock, and slid down his shaft, taking him all the way in and burying my nose in his groin.

"Oh my God!" I heard Will say as I started to bob my head up and down. After doing that a few times, I pulled him out of my mouth when I heard him breathing deep and said, "You're not close, are you?"

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"Sorry, I've just never had anybody do that before. I'm good," he said. "Can we maybe go to your bed?" He asked shyly.

I stood up and grabbed his hand, leading him into my bedroom. I told him to lay down on the bed and started to take off my overalls as he watched. I pulled off my white crop top before crawling onto the bed with him. We started to kiss again as Will slid his hand under my bra and onto my breast. I moaned again as he squeezed me and felt my nipple growing hard against his palm.

Will stopped kissing my lips, moving down to my neck. I reached up and pulled my bra off, and Will instantly started to suck on my nipples with his mouth while his hand started to squeeze whatever breast his mouth wasn't on.

I threw my leg over his body and straddled his lap. He continued to suck on my nipples while I rubbed my thong on his hard cock. He reached one of his hands around my back and down to my ass again, grabbing it and pulling me closer to him. Will grabbed at my thong and started to pull it down as I lifted my hips up and helped him. When it was off, I rested my clean-shaven vagina on his hard cock and started to rock back and forth.

"Fuck, I've never been with somebody without hair on their pussy," he said.

"Do you like it?" I asked him.

"Yes," he responded, pushing his hips up and trying to get inside me.

"Show me," I said as I rolled off him and laid down on my back with my legs spread open. I was hoping that he would go down on me, but instead, he rolled over on top of me and used his hand to slide his cock into my waiting vagina. He pushed in as deep as his five-inch cock would go.

I moaned as Will started to thrust back and forth. Unfortunately, he started to moan and grunt, and after just a few thrusts with his hips, I felt his cock twitching inside me as his cum started to squirt out the tip of his cock. "Oh fuck, shit, fuck! I'm sorry!" He moaned as he continued to thrust in and out of me, until he couldn't last any longer and started to go limp.

"Oh my God, I can't believe that just happened. I'm so sorry," Will said as he rolled off me and laid down next to me.

"It's OK," I lied to him, completely disappointed.

'"I can keep going if you want. You're just so fucking hot, I couldn't help it. I'm sure I can get hard again," he said.

"No, it's OK. I still enjoyed it. Maybe another night?" I told him.

"Yeah, definitely. I promise it'll be better next time," he said.

We lay together in silence for a few minutes before Will moved to get up. As he went to grab his clothes, he said, "I'm sorry, but I need to get back to my brother. Are you sure I can call you again?"

"Of course," I said as I got up and walked him to my door after he got dressed. Before he walked through it, he turned to me, looked my naked body up and down, and said, "Oh shit, I didn't even think to ask you about birth control."

"I'm not on the pill," I told him.

"Oh good," he said. "Can I call you tomorrow?" I told him yes, and he said goodbye before turning and walking away.

Shutting the door behind him, I locked it and went into my bathroom. I cleaned up a little before staring at myself in the mirror. My nipples were still hard from him sucking on them. My hair was messy from the short time he fucked me. And my pussy lips were still engorged.

I wanted to at least get myself off, even though I was frustrated, so I went back into my room and lay down on the bed. I reached over to open a drawer on my nightstand, and I pulled out my seven-inch long, thick, veiny, black dildo. I smiled as I looked at it. I brought it down to my groin and rubbed the tip against my pussy.

I hiked my knees up so they were bent, used one hand to pull my pussy lips apart, and I pushed the tip into myself. I moaned loudly as I pushed it in deep and filled myself up. I started to pull it in and out, moaning every time it went back in.

I picked up my phone and thought about calling Danny. Instead, I went to a hidden folder on my phone, found a certain video, and started to play it. In the video, I was naked, kneeling on the floor, and Danny was standing in front of me. I had my hands on his cock, jacking him off, until he started to cum, and he covered my face. As the video ended, I was rubbing his cock all over my face.

I swiped to the next video, which was me bent over, on my hands and knees, while Danny pounded his six-inch-long, thick cock into me. I continued to fuck myself with the dildo as I watched Danny deep inside me and moaning as he orgasmed. The next video was one of him and Jessica, with Jessica riding him. The video was shot from Danny's point of view and I watched as Jessica slid her pussy up and down Danny's cock.

Danny moved the video up, and I pushed and pulled the dildo in and out of me as Jessica's C-cup-sized breasts bounced and swayed up and down. Danny reached up with his free hand and grabbed at her breasts, squeezing them and pinching her nipples.

I became transfixed by Jessica's breasts, and I felt my orgasm building up as I watched them. Watching them move up and down as Jessica rode Danny, seeing her nipples pinched and rubbed by his fingers, I thought back to the time that Danny covered Jessica's nipples with his cum, and I licked and sucked it off. As I thought about what her nipples felt like in my mouth, I started to cum.

My legs clamped shut around my arm as I pushed the thick dildo deep inside me. My hips came up off the bed as I orgasmed. I covered my mouth with my free hand to stifle my loud moan, and I laid my head down on the pillow, closed my eyes, and enjoyed the intense feeling of relief wash over my body.

When I was done, I put my legs down and opened them so I could pull the dildo out. I brought it up to my mouth and sucked off my cum before sitting it up on the dresser. I took a few deep breaths as I recovered, amazed at the orgasm I just gave myself while thinking about another woman's breasts.

And as I thought about it, I realized that I wanted more of them.

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