Building a Life in Chicago

After Danny and Jessica left and flew back to Utah, I knew I had to make a change in my life. I moved to Chicago to be happy, to be free, and to grow as a person. But all I had done so far was be a slut, get used, and get depressed.

The day after they left, I woke up determined to change. As I got ready for work, a random thought came to my mind, and I texted Owen, the salesman that lived just outside of Chicago that I had hooked up with a few times. This time, I said, "Hey Owen, how are you? I know this may be weird, but could I take you out on a date this weekend?"

I didn't have to wait long until he replied back, "No, but I'll happily take you out for a date." Perfect, I told him, and we started making plans.

The other big change I wanted to make was to get back to going to the gym. In Utah, I was going at least once, usually twice a week, but I hadn't gone since moving to Chicago. I spent a lot of the morning researching gyms before settling on a few I would like to try.

Getting to work that day, I was happy that people noticed a change right away, with the dentist I worked for saying, "Kourtney, you seem really happy this morning. You must have had a good weekend."

I smiled, telling him that I did, while I thought about getting fucked by Danny and sleeping with Jessica.

After work, I drove back home, quickly changed into my workout clothes, and left to drive to the first gym on my list. I instantly didn't like it upon arriving and left to go to my second choice. It was a little bit farther from my house, but as soon as I walked in and was greeted by a cute little blonde at the desk, I didn't want to leave. I quickly signed through the membership paperwork and walked to the locker room.

Not wanting to push myself too hard that first day back, I mostly walked on the treadmill. I went back again the next day, again getting a smile from the cute blonde as she welcomed me back.

I was halfway through a workout with the free weights when a guy came up and started using the weights next to me. I caught him staring at me in the mirror a few times, and so I grabbed a weight, turned around, put one of my knees and one hand up on a bench, and started doing arm lifts with them. I looked back to see him looking at my ass in the mirror and smiled to myself.

After switching arms, I turned to put the weight away, took off my headphones as I looked at him, and said, "Hi, I'm Kourtney."

He smiled and said, "Hi, I'm Vance. You must be new here."

Vance was as tall as I was and pretty muscular. He had blue eyes, a shaved head, and both of his arms were covered in tattoos. "Yes, I am. Just joined yesterday," I told him.

"Oh awesome. Thanks for joining," he said. "You don't sound like you're from Chicago."

"I'm not. I'm from Utah, actually. I moved here to go to dental school," I said as we both sat down, grabbing our water bottles and taking a drink.

"That's cool. So, are you working at a dental office now?" He asked me.

"Yeah, I am," I said and gave him the name of the office I work at. "What about you? What do you do?"

"I'm a gym owner. I own this gym and three others around the city and state," he told me with a smile.

"Oh, I'm sorry, I had no idea," I said with a laugh.

"I used to have a welcome letter with my picture on it. I would give it to new members but had to take it out when too many were coming up to me while I tried to work out. Now, I only tell the cute ones," he said with a smile.

I felt my stomach starting to get butterflies before saying, "Only the cute ones?" I looked around the gym and said, "You must tell lots of people."

He laughed and said, "OK, OK, let me rephrase that. I only tell the cute ones that see me staring and turn around and flaunt their ass in the mirror."

I pretended to be shocked and said, "Are you serious? And here I thought this was a good gym that I could be safe and respected at."

He laughed again and said, "I'm sorry. Let me make it up to you by taking you out to dinner this weekend."

I smiled as I stood up and said, "I'm already busy this weekend; try again next week." I could feel his eyes on me as I walked away.

That night, after getting home from the gym, taking a shower, and eating some dinner, I was laying in bed, doom scrolling on social media, when Vance popped into my head. I started to look for his socials, found the gym's, and finally his private Facebook page. Going over to Instagram, I typed in his name and found both a private page and what appeared to be a workout page.

As I scrolled through the page, it was all pictures and videos of Vance, either working out, at a competition, or just talking. I didn't watch any of his videos, but I could feel myself getting turned on as I looked at his tattooed, muscled body.

Setting my phone down, I looked around my bedroom for some reason before I pulled down the pajama shorts I had put on after showering. I didn't put on any underwear, so my clean-shaven pussy was bare as I moved my hand down to it and started to rub my juices around. I closed my eyes as I touched my slit, pushing a finger past my lips and into my pussy.

I tried to imagine what it would be like to sleep with somebody as built as Vance is, wondering how big his cock was, and dreaming of him just throwing me around. I pushed and pulled my finger in and out of my pussy while I used my other hand to pull up the tank top I had on. I squeezed my B-cup-sized breasts one at a time and pinched my nipples.

"Oh, fuck," I moaned as I inserted a second finger into my vagina and moved it back and forth. After pinching my nipples, I moved my other hand down and used my thumb to put pressure on my clit. Not feeling like it was enough, I reached over to my nightstand, opened up the drawer on it, and pulled out my vibrator.

I turned it on, watching myself as I lowered it down, and moaned as I touched it to my clit. I left it on there as I worked my fingers in and out of myself. Closing my eyes again, I enjoyed the feeling of pleasure coursing through my body. "Oh shit," I moan. "Fuck."

As I imagined Vance slamming his hopefully big cock into me over and over, I started to cum, a massive orgasm washing over my body. I pulled my fingers out of my pussy, somehow kept the vibrator on my clit, and bucked up hips up and down, moaning throughout my orgasm.

After I was done, I turned off the vibrator and put it on the nightstand. I reached down to fill my bedsheets, making sure I didn't soak them. When I couldn't feel anything, I laid my head back and let out a sign of relief.

I grabbed my phone, closing out of Instagram and the picture of Vance I had been looking at. I saw a text message notification, so I opened it up. It was from Owen and said, "Hey, Kourtney, I'm sure you're already asleep, but I just wanted to tell you how excited I am to take you on a date this weekend. I almost wish we had started with a date, as great as sex is with you, and progressed to a sexual relationship. But I'll take it this way too!"

I laughed at his message, thought about texting him back, but decided to do it in the morning. I got myself redressed and fell asleep soon after.

That weekend, Owen took me out to dinner, and we followed it up by walking around a local art exhibit. I surprised him by holding his hand as we walked, and I smiled as I felt his hand get sweaty as I gripped his hand in mine. Afterwards, as he drove me back to my apartment, I really thought about letting him inside and sleeping with him. But, remembering that I wanted to be better, I made him settle for a kiss at my door, much to his disappointment.

Hoping he wasn't mad at me, I texted Owen next morning and said, "Hey, thank you for the great day last night. It was a ton of fun, and I can't wait to hopefully go out again. I'm sorry it didn't end the way you wanted it to. I agree with what you said the other night about wishing we had dated first, and I think that was a great first step."

He quickly texted me back, saying that he agreed and asking when he could take me out again. We made plans for that next weekend.

I missed going to the gym that Monday, but found myself back there on Tuesday. As I walked on the treadmill, I saw Vance walking around, talking to random people, giving tips, making them laugh, and cleaning up his gym as he went. He really did have a cute smile, I noticed.

I took off my headphones as he came up to me and said, "Hey, Kourtney. How was your date this weekend?"

"It was really good," I told him with a smile. "He's taking me out again this weekend."

"Really now? He's one lucky man," Vance responded, and I felt a little pang of guilt for him. I nodded my head yes, and he said, "Well, I'm still glad to see you here. If you need anything, please feel free to ask."

He started to walk away but quickly turned back when I called his name and said, "You know, it's not like I'm exclusively dating this guy."

"Yeah, so, when are you available?" He asked me.

I turned off the treadmill and got off it. I stood up in front of him and said, "I'm available now."

"But, I'm at work," he said. "I own the gym, and it wouldn't look good for my employees if I left when I said I would be here."

"So, you own the gym," I said, rubbing his muscles on his arm with my hand. "That must mean you have your own office, right?"

Vance looked around at the gym floor, putting his hands on his hips. He then looked down at my body and said, "Follow me."

Grabbing my water bottle, I followed him off the gym floor and into the reception area. Looking at the cute blonde receptionist, he said, "Anna, I'll be in my office for a little bit."

"Ok, boss," I heard Anna say as we walked past her, and I could feel her eyes on me.

Vance led me through a door that opened to a staircase. Up the stairs we went, turning down a hallway and to another door that he opened up to reveal his office.

As he shut and locked the door behind me, I said, "Your girl back there kind of acted like this isn't the first time you've brought a girl up here."

Vance laughed and said, "It's maybe happened once or twice."

"With her?" I asked as I walked up to him and wrapped my arms around his neck.

"I tried, but she's a lesbian," he said as he wrapped his muscular arms around my skinny body. As we started to kiss, he very easily picked me and walked me backwards to his desk and sat me down on it. His hands started to pull up on the tank top I was wearing, and I lifted my arms in the air as he pulled it and my sports bra off.

He began to kiss my neck, and his hands grabbed at my B-cup-sized breasts, his fingers pinching my nipples, as I pulled the drawstring on his shorts and slipped my hand inside them. His cock was already semi-hard as I wrapped my hand around it and started to rub it up and down.

He kissed down to my nipples, wrapping his lips around one and sucking it into his mouth as he continued to rub my other nipple. I could feel my vagina getting wetter and wetter as he touched me and his cock growing bigger and bigger as I jacked him off.

I used my free hand to pull his shorts down, and I got my first look at his cock. It had to be at least eight inches long and thick. I smiled and said, "I'm glad to see it's not only your arms that are big."

He laughed as he moved his hands to my shorts, yanking them down to my ankles, where I kicked them off. "No underwear?" He asked. "Is that an every-day thing, or were you hoping for this to happen?"

"A little of both," I told him as I felt his fingers on my pussy, rubbing up and down my slit, brushing against my clit, and sliding two of them inside me. He roughly pulled them in and out of me as I moaned, my hand never leaving his cock.

When he finally pulled them out of me, I started to slide off the desk, kneeling in front of him. I happily eyed his cock and started to lick the sides of it. Still rubbing it up and down, I wrapped my lips around his tip, tasting his precum, and started to slide my mouth down his shaft.

I looked up at him, making eye contact as I continued to slide down his shaft. I felt his thickness bursting against my cheeks and going down my throat. As I got him deeper and deeper into my throat, I saw his eyes going wide, and I held myself as I buried my nose into his groin. After a few seconds, I started to bob my head up and down the entire length of his cock.

"Oh, fuck, it's pretty rare when a girl can take all of me in like that," he said as I kept blowing him, adding my hand back into the mix.

"Fuck," he said again as I deep throated him over and over, bringing my other hand up to cup his balls. "OK, fuck, get up here so I can fuck you."

I pulled my mouth off him and gave his tip a kiss before I stood up and climbed back onto his desk. I wrapped my legs around him, spreading them wide, as he stepped forward and expertly guided his tip into my vagina. I leaned backwards on the desk, using my hands behind me to support myself, as I watched his thick cock stretch out my pussy.

"Do you like it rough?" He asked me.

"The rougher the better," I told him. "Don't be scared."

"Good," he said as he pushed his entire cock into my pussy, making me moan loudly. He grabbed onto my hips and started to buck his hips back and forth, sliding his cock in and out of me.

"Yes. Oh yes. Fuck, fuck me harder," I moaned, switching my gaze back and forth between watching his cock sliding in and out and his face. "Harder, baby, fuck me harder."

He was slamming into me over and over, as hard as he could, using his powerful legs to push himself up off the floor and ramming his cock into me. "If I go any harder, I'll break my desk."

"I guess next time we'll have to go to your house," I said, pushing my hips up into him.

"Definitely. I'll fuck you as hard as you want," he said.

"Will you tie me up, blindfold me, and choke me?" I asked him as he pounded into me.

"Fuck yes," he said, pushing me into the desk and making it rock.

"Will you fuck my ass?" I asked, gripping the side of the desk to hold myself on.

"No girl has ever been able to take my dick in their ass," he said, moving his hands to my ass and grabbing my cheeks to pull me up into him.

"I can," I told him.

"FUCK!" He yelled out as he pushed in deep and exploded inside me. As I felt his cum shooting deep inside me, I started to orgasm as well, my pussy clenching around his cock, milking out all his cum as he pumped in and out of me.

I wrapped my legs around his body and pulled his groin into mine. At the same time, I wrapped my arms around his neck and pulled him down to passionately kiss him. Our tongues swirled together as he lifted me off the desk, and I humped his cock until I felt it go flaccid and slip out of my pussy.

He gently set me down on the floor, making sure my legs could hold before letting me go. "Fuck, that was amazing," he said as he pulled up his shorts and I searched for my clothes.

"Yeah," I said, feeling both a great amount of pleasure and a great amount of guilt. As I came, my mind went to Owen, wondering if he would get pissed at what I just did.

"Are you OK?" He asked me as I pulled my shorts up my legs.

I put my bra on before walking up to him. I kissed his lips and said, "Yes, of course. That was amazing."

After I finished getting dressed, he opened the door for me to walk out, following behind me as I did so. He put his arm around my waist as we walked down the hallway, squeezing my butt when we got to the bottom of the stairs. Before he could open the door for me, I wrapped my arms around his neck and pulled him down for another passionate kiss.

He opened the door, and I immediately made eye contact with Anna as I walked out. I smiled at her, wondering if she could hear us, and went out to the gym floor to finish my workout.

That weekend, Owen said that he had a surprise for our date. He knocked on my apartment door, handing me a bouquet of flowers as I opened it. I quickly put the flowers in a vase, and we walked to his car, where he opened the door for me. He had told me to dress in clothes that I could be active in, so I had on a gray tank top and black basketball shorts.

I kept asking what we were doing, but he refused to tell me. As he drove through the city, I started to think that the roads were looking familiar, like I had been there before.

He told me that we were starting to get close, and I knew I had driven these same roads but couldn't remember why. As he made the last turn, I started to recognize some of the buildings and felt my stomach drop as he pulled into a parking lot, announcing that we were here.

It was the dance studio that Rachel, the girl that broke my heart, taught dance at.