No Repeats

During my freshman year of college, I had a roommate named Jim. I think we both paired together because we were older than the typical freshman coming in. He was twenty-two and I was twenty-one. We both worked and had a couple of years of community college. We had talked on the phone before meeting up at college and figured out what we needed to bring. When we met, I quickly discovered Jim was a player. He loved girls and he had an interesting proposal for our first year. "Let's have a bet to see how many different girls we can get into our beds!" Jim said with a devilish grin. Jim was better looking he was buffer than me. The only two things I had going for me was I looked so young and I happened to be much bigger between the legs than him. We made our wager.

Jim liked the bar scene. I wasn't as social at the time so he taught me a few things when picking up girls. Our first night out, he had managed to get a very pretty,shoulder length dark haired girl and her not so attractive friend to come back to our dorm room. Jim and the pretty girl were making out in front of this girl, Kim, and I. Kim was nice but she had below average looks, small tits, big ass, short dark hair and with brown eyes. We sat on my bed and gave each other looks. Jim was moving fast and clothes were flying off. Kim asked if we could step out because she didn't want to watch. We went into the hallway but they were so loud that we decided to go down the stairwell and take a walk.

I think the vibe Kim and I knew nothing was going to happen so we just talked. It was very vanilla chatting until I asked why she and her friend came back with us. Kim confessed that she and her pretty friend ,who was getting fucked by Jim, were just looking to have some fun and possible have sex. I had never heard a girl be so blatantly open about wanting to ge laid. I asked more wanting to know more how girls thought about casual hookups and Kim seemed open to share. It wasn't so much what someone looked like, but looks didn't hurt either, but there had to be a spark weather it was physical or mental. Attitude was everything, not too confident and not too weak. Kim gave her honest assessment of me. She told me I was cute but me being much more quiet than Jim was a turn off. She told me in that moment that since we got to talking she found me more appealing. I appreciated her honesty. She asked me what I thought about her. I lied telling Kim that I had found her attractive. I added that I struggled to talk to girls I found attractive...which was true. Kim stopped and confronted me. She asked if I really found her attractive. She was reading me by my eyes. I had become more attracted to her as we talked and sold myself on saying 'yes'. Kim smiled taking my hand. We walked in silence happy for a few moments. Then Kim said, "You know if you keep playing your cards right, you might get lucky!"

I sensed this was a good time to be playful and joked, "What do you mean 'if'?" Kim paused stopped to face me. We started to smiled and burst out laughing. Kim said that was a good one and liked that I had a sense of humor. We joked around more as we kept walking. Kim and I stopped in a nearby park shelter and sat on a picnic bench. Kim made a long sigh before asking herself under her breath how much longer Jim and her friend might be. She seemed bored that nothing had happened yet. I acted stupid asking Kim if she wanted to make out to kill some time. Kim didn't make eye contact me as she just stared out into the wooded area.

Then she coolly whispered, "Next time, just do it instead of suggest it." Kim had her hands in her lap acting put off by my dumb comment. I had missed an opportunity and we just sat there as I played through all the different ways I could of done it better. Kim picked up on me and told me to not over think it, most girls like a guy who takes charge. I decided to go for it and I leaned over to kiss Kim. She looked at me in disgust and said, "No way! You blew your chance!" then she called me a pussy, stood up and began to walk back to the dorms.

I followed after her by several steps. Confused and pissed off. I told Kim off in my mind and couldn't wait for her to be out of my life. I stopped following Kim, she knew the way back and so I decided to turn around and walk in the other direction. Kim had ticked me off, she could walk herself through the poorly lit park by herself. What I didn't expect was what happened next. Kim came back for me!!

Kim had turned around and noticed I wasn't following her. She didn't like the idea of walking by herself late at night in the park. She jogged and was out of breath when she called out to me. I turned around and stood there giving her a stern look. Kim asked me in a high pitched voice, "Why did you leave me?" I stood there looking through her not saying a word. "Something could of happened to me?" I sensed confusion and a bit of fear in her voice.

I spoke up in a flat tone stating, "You had decided to leave me first. I figured you wanted to be alone and so I let you go." Kim's whole prissy attitude went away, her fake facade of being tough washed away exposing her vulnerabilities.

Desperately Kim asked me to walk her back to the dorm. As much as I wanted to be a dick to her, I just couldn't abandon her. We walked back to my dorm room. Kim and I hardly spoke the whole way back. When we got back to the room, Jim had left s note that Kim's friend and him went out not saying where or when they would be back. His bed was in disarray. Kim sat down on my bed and I decided to pull out my desk chair. I began to wish this night was over because I was exhausted with Kim. Kim was in a powerless situation, her friend was her ride home. She had told me they lived in a small town thirty miles away. I wanted Kim to leave but since she wasn't going anywhere, I decided to offer her my bed and I would go crash on one of the couches in our commons. Not ideal but at least I could get some sleep. Kim didn't approve and suggested we try to sleep on my twin bed together. I didn't care if I offended Kim and boldly told her I slept in my underware and my cock had a mind of its own. Kim looked wide eyed at me. She knew I wasn't bullshitting her. Kim broke away smiling to herself. Kim swallowed hard and told me she was willing to risk it. I rolled my eyes and said I needed to take leak and told her she could get into the bed. I walked out.

When I returned, Kim was under my covers. She seemed very pleased with herself holding the covers up to he neck. I striped down to my underwear and sat down on the bed. Kim seemingly excited, asked if I was going to join her under the covers. I told her I would sleep on top. She asked again, this time dropping the sheets flashing her small breasts with nipples pointing in different directions. Kim smiled oddly me. I stood up and she revealed her naked body to me. Kim's pear shaped body looked sexy, she had very trimmed pussy hair, and a tattoo just under her belly button of two rainbow dolphins in the shape of a circle. My cock began to grow. I pulled down my underwear and kicked them under my bed. Kim's mouth opened when she saw the full extent of my extra thick seven inch cut cock. I slid in with Kim. She moved under me and opened her legs. She wanted me to kiss her but instead I grinded into her. Kim looked at me. I didn't say a word. She had to know what she was in for. Once I had found her hole. I pushed myself hard up inside Kim. She tried not to make too much noise but let out a grunt as if all the air in her lungs had escaped her. Kim's chest heaved as she gasped for breath. I was over her just pounding away. The covers slipped down below my ass. I took long heavy strokes. Our flesh smacking into each other. Kim tried to kiss me but I pushed her down on the bed. Holding her shoulders down. Kim moaned louder. I liked fucking her hard. Feeling powerful. I pulled out and flipped her over pushing her face down into the pillow. I hiked her wide hips up and stuffed myself into from behind. I made her ass ripple! I pounded and pounded into Kim's body relentlessly. I was angry and it made me want to fuck Kim harder. Kim was screaming into the pillow. Her fists clenched the railing of my bed. The bed squeaked and moved away from the wall due to the aggressive style I used to punish Kim. Just before I was about to cum, Jim and the pretty friend of Kim's walked in. Jim had an approving look on his face. Kim's friend had one of horror! Kim looked up at her friend. Kim's makeup was running from all the tears she had shed. I pulled my longsword out of Kim. Her friend stared in a stunned silence at what was attached to me. I stood up sweaty and let her admired my naked body. I was breathing heavy with my hands on my hips. Kim was sobbing. She moved gingerly off my bed. She sniffled and her friend rushed over to her. They gathered her clothes from under my bed. Her friend took the top sheet off my bed and wrapped it around Kim's naked weary body. They stood up and went into the bathroom. I put my underwear back on. Jim just smiled at me giving me a high five. We laughed. Then he blasted, "I guess the score is tied at one!"

Kim and her friend never returned. I found my bed sheet on the floor of our bathroom. We never saw Kim and her friend again! Jim later asked me if I knew how old Kim was? Then he said she was twenty-eight and her friend was twenty-seven. Supposedly they were both married and had taken off there rings wanting to hook up with college aged guys. I suppose they got exactly what they wanted.

My bet with Jim continued. ....