The Bet

It took me exactly ten minutes to get to Sydney’s place. I waited in my car a few minutes before going to get Sydney. I got out of the car and wiped my sweaty palms on my pants. I was nervous, tonight was the closest thing Sydney and I had come to an actual date.

I knocked on the door. I waited for several minutes until I got to impatient and just reached for the doorknob. I pushed the door open and walked into the apartment.

“Sydney are you here?” I called out. I walked towards her room; I could hear her running around her room. I leaned against the door way and watched her. She had yet to notice me, so I just stood there watching her. She was really something. Her room was covered in all sorts of different posters; some were of bands, others of movies. Above her bed was a beautiful picture of the beach. Brent’s eyes scanned the room and landed on a shelf full of volleyball trophies.

“Holy shit,” Sydney gasped, “You scared the shit out of me.”

“I’m sorry,” I apologized. I looked her up and down taking her in. She looked amazing


We arrived at the restaurant and I was starting to panic. I had no idea how Sydney would get along with the team. I knew that she was a quiet person and I was worried they would scare her off. We walked inside and I immediately saw the team sitting around a large table, some of the other players girlfriends were there and I breathed a sigh of relief. Hopefully they would keep some of the guys in line. I quickly grabbed her hand and gave it a squeeze. She looked up at me a smiled.

“Seabsy I see you brought your lady friend.” Steeger called out. They had already ordered food and judging by how loud they had already ordered some drinks. I pulled out a chair for Sydney right next to Ladd. She said hello to Jon and sat down.

“Guys this is Sydney,” I told them as I took my seat next to her. They all said hello and I felt myself calming down.

“Can I get you guys anything?” the waitress asked. I ordered a beer and steak and waited for Sydney to order.

“Yeah I’ll take a Jack and Coke and the chicken alfredo.” She gave the menu to the waitress and turned her attention back to the table.

“Hey let me introduce you to everyone, this is Andrew and his wife Lindsay, Kris and his girlfriend Rachel.” I paused as she waved a hello, she didn’t seem uncomfortable which I took as a good sign. “That ugly beast over there is Adam Burish and next to him Patrick Sharp and his wife Abby and last but not least Dustin,” I finished patting Dustin on the back.

“Nice to meet you guys,” Sydney said taking a gulp of her drink. She seemed calm and I felt myself relax as well. I cut a big bite of my steak. I glanced at Sydney, she was smiling and laughing. Things were going great.


Sydney’s POV

I would have been lying if I said I hadn’t been nervous. When Brent called and asked if I wanted to hang out with him and the team I panicked, but things were going really well. Everyone was so nice and I didn’t feel out of place. I was starting to feel like my old self again, the way I was before Ian. It had been so long since I was had interacted with a big group of people like this.

“Sydney I think your phone is ringing.”

“What?” I asked, looking around. I had spaced out and missed what was going on. I heard a Ke$ha song playing and realized my phone was ringing. I pulled it out of my purse quickly. I saw the guys laughing at my ringtone and I damned myself to hell and back for not putting it on silent.

“Excuse me one second.” I got up from the table and went outside. I answered it before I could check the caller id and cringed when I heard my brother’s voice on the other end. I hadn’t spoken to him in month and I knew he would be pissed.

“Well look who finally decided to pick up the phone.”

“Daniel I’m sorry I have been busy with work and stuff,” I apologized.

“And stuff well I’m sorry to keep you from your stuff. It must be terrible to have a brother who is such a burden to you.”

“Shut up you asshole. I can’t talk I am right in the middle of dinner,” I said quickly trying to hurry the conversation.

“Well I don’t want to keep you I just wanted to see how you were doing and tell you that I am coming to Chicago in a couple weeks.”

“Oh my god that is so great! I’ll call you tomorrow,” I said hanging up the phone. I hurried back inside before the hypothermia set in. The weather in Chicago was cooling down and winter was getting closer.

“Hey is everything alright?” Brent asked. I nodded and told him it was just a family thing. I hadn’t spoken to him much this evening and it was nice of him to be concerned.

“Why the fuck is your ringtone Ke$ha?’ Adam asked bluntly. I felt my cheeks get red and everyone’s eyes on me.

“Uhh its sort of a joke between Chelsea and I,” I explained.

“Do tell,” Adam said leaning back, taking a sip of his drink.

“Alright well during our senior year in high school Chelsea and I went to a Ke$ha concert with some friends and before we did a little pre-gaming at my house. Someone brought over a box of Four Lokos, you know those energy drinks that have alcohol in them, and anyways I sort of had four of them and then a couple tequila shots. Then at the concerts we had some beers and I guess I sort of blacked out and ended up flashing a police officer.”

“Well damn didn’t anyone try and stop you?” Andrew asked.

“All my friends are bitches and they thought I knew what I was doing. Needless to say I haven’t had a Four Loko since,” I told him taking a big bite of pasta. I looked around at the table and noticed all the girls were eating salads. I slowly put down my fork embarrassed by my actions. Everyone had gone back to their own conversations. I turned to look at Brent and found that he was already looking at me.

He leaned over and whispered in my ear, “You are really something, you know that?” I smiled kissing him on the cheek.

“You are really sexy, you know that?” I whispered back. I pulled back and put my hand on his upper thigh. I saw him close his eyes and tense up. I moved my hand slowly Brent turned to face me and I winked at him. I’m not sure what it was but I was feeling very frisky tonight. Before I could do anything he pressed his lips to mine. It lasted no longer than a second but I was shocked. Brent always managed to catch me off guard.

“You guys are so cute,” Abby exclaimed breaking us out of our bubble. We quickly separated and I felt my face flush. Brent started fidgeting in his seat and I looked over at him, he got up and left the table. I shot him a confused look as he went towards the bathroom. I turned back to the table. I apologized for Brent and started talking to Abby.

“Sydney and I are going to go,” Brent informed the group. I turned to look at him so fast I probably gave myself whiplash. I had no idea what he was doing. He stood up from the table and I blindly followed him. Brent pulled out his wallet and tossed a few bills on the table to cover our meal. He grabbed my hand and handed me my purse.

“Hey Seabs before you go,” Adam spoke pulling out his own wallet and pulled out a condom. “You’ll thank me later.” Brent flipped him off and grabbed my hand, pulling me with him out of the restaurant.

“It was nice meet all you guys,” I called over my shoulder. I had no idea what was going on with Brent right now. He pulled me along with him through the parking lot. He didn’t stop until we reached his car.

“Brent what is going on?” I ask trying to figure out what had gotten into him. He dropped my hand and turned towards me. He didn’t say a word he just stared at me.

“Brent what is going on? I repeated. He took a step towards me.

“You are such a little tease,” He growled. He grabbed my waist and shoved me against the car. I gasped as Brent’s hands roamed up and down my body. “I can’t fucking take it anymore. I need you.” His lips hovered over my neck and his breath was hot against my neck.

“Brent,” I moaned.

His hand clamped over my mouth and he brought his mouth up to my ear. “Save it.” He took his hand off my mouth and moved away from me. I could see his raging hard-on in his pants, and felt my underwear getting soaked. Brent got into his car and I quickly followed him. I climbed into the big SUV and slammed the door shut. I reached over and grabbed Brent’s shirt and shoved my tongue down his throat. I was tired of him being the one who always kissed me. He wrapped his big arms around me and I basically melted. I don’t know what it is about Brent but every time he kissed me I felt something, I realized how cliché that was it had been so long since I felt anything like that.


This was possibly the longest car ride I had ever been in. The sexual tension was so strong I could practically feel it and I was dying. I had no idea what Brent was feeling or thinking because neither of us had spoken a word the entire ride. I assumed we were going to his place because I had no idea where we were. I was trying my best not to overthink what was going to happen and just focus on how good it would feel when he was slamming into me and how good he would look naked.

The car stopped and Brent got out, before I could even blink Brent was opening my door and helping me out. He seemed to have calmed down during the car ride. He led me up to his condo which was about 100 times nicer than my place. It was a classic bachelor pad, no color, very modern, and only had the essential furniture. There were video games and pizza boxes all of the coffee table and I didn’t even want the rest of the place looked like. I followed him into the bedroom and braced myself for what was about to happen.

Brent’s movements were slow and calculated like he was thinking about everything before he did it. He was walking towards me and I stood there like a moron not moving not doing anything, just waiting for him to touch me. I let my eyes close and waited. I waited for Brent’s touch but it never came. I opened one eye and saw Brent stand there smiling at me like a little fucker.

“Fuck you,” I huffed under my breath. The anticipation was killing me and I didn’t want to wait any longer. I threw myself at Brent and we fell back onto the bed. His arms wrapped around me and his hands started to wander. His mouth was hot and warm and my tongue was taking great pleasure in exploring it. I let my hands slid up his shirt and explore his muscular chest. I was so wet with anticipation my underwear was practically soaked through. I pulled away from him and ripped off his shirt. His hand found their way under my shirt and pulled it off quickly; he started to kiss a trail down my neck. He ended at my chest and quickly removed my chest. I moaned as his lips clamped down on my nipple and his hand massaged my other breast.

“Brent no more foreplay,” I panted. He looked up at me with big eyes like he was a five year old that found out Santa wasn’t real. “Fuck me god damn it” The words came out of my mouth and that was it. Brent flipped me over onto my back and took complete control. He undid his belt and removed his pants. His hard cock was even more noticeable with just his boxers covering him. I quickly removed my own pants and shoes. I felt Brent’s eyes examining and I started to squirm. He leaned down and kissed me while his hands removed my soaked panties. I gasped as his hands touched me.

“You are so beautiful,” he whispered as his fingers rubbed my clit. I was so close to coming and I thought I was about to lose it right there. He slipped two fingers in me and barely had to do anything before I exploded.

“Holy shit fuck,” I cussed as my orgasm coursed through my body. I opened my eyes and was greeted by Brent smirking at me, sucking on his fingers. I pushed Brent onto his back and climbed on top of him. He grabbed a condom out of his drawer and tore it open it with his teeth. I grabbed it from him and slid it over his hard cock before he could say anything. I slid down on him and we both moaned as he filled me up. He waited for me to adjust to his rather large size.


“Fuck Sydney,” he grunted as he slammed his cock into me. It was just as good as I had thought it would be. I was close to coming again and judging by the sounds coming out of Brent’s mouth so was he.

“I’m so close,” I moaned. Brent’s hands rubbed my clit and before I knew it my second orgasm of the night washed over me. Brent followed after me, emptying himself inside me. I fell back on the bed, exhausted from the activities we had just participated in. Brent reached over and pulled me closer to him, so that my head was on his chest. We were both breathing pretty hard and we lay there for a while listening to each other breathe.

“How long have you been a Hawks fan?” Brent asked. The question caught me off guard. This wasn’t a normal question to ask someone after sex.

“Uhh my whole life I guess. I'm from right outside Chicago and my mom grew up a fan so she raised my brother and I as fans."

“You have a brother?” I looked up at him and realized how little he knew about me.

“Yeah his name is Daniel, he’s coming down to visit in a few weeks.”

“That’s cool you should invite him to a game. Maybe one day your mom could come too.”

“Yeah Daniel would love that,” I told him not quite sure how to tell him about my mom. “Brent I should tell you something.”

“What?”

“My mom passed away when I was 15,” I blurted out.

“Oh my god Sydney I’m so sorry.” Brent apologized kissing my head. I felt better telling him about my mom, at least now he knew a little about my life.