The Conquest Club Files 01

A/N: Originally published to Literotica.Com on 12/23/14 under my other screen name of DieselJester.

*****

Hunter File # 0001a: Kim

Age: 18

Height: 5'3"

Figure/Stats: Petite/30B-24-30

Hair: Light Brown that goes down to her ass.

Eyes: Blue

Trophy Taken: One piece pink swimsuit cut high on the thigh and low in the cleavage and down the back.

*

"The Conquest Club," I roll the idea around my mouth and to this day I still can't believe that it's gotten as big as it has. We're to the point nowadays that we have to require a written waiver, require membership dues, provide upkeep on a fixed location, get monthly check ups, check members in good standing, yadda, yadda, et cetera, et cetera. These files are, or will be at any rate, broken up between Hunter and Prey files. Hunters, obviously, being us guys (and occasionally some girls) that go out to our selected Prey; the ladies.

But I'm getting ahead of myself here.

I guess that I should start at the beginning. As much as we members of the club like to go out and do each other, a lot of us like to read about it as well. Sometimes it helps with the mood, or so I'm told. Anyway, that's why my wife urged me, and by proxy everyone else, to start doing these little write up files on each one of our 'conquests.' So let me go all the way back to the beginning.

My name is Michael Weston and I used to be a spy...

Damn kids... One moment while I go and tell them to turn down the Burn Notice reruns. Then again, the sentiment kind of fits in this case when one considers all of the sneaking and prowling around that I've done in the course of this club...

Okay, now that that's settled, let's get down to it, shall we?

I guess it all started back in the summer after my Junior Year of college. I was back home for the summer visiting and I'd done the customary drop in on the old gang, visit with the relatives, and meet with the neighbors and all of that fun stuff. I finally got the opportunity to spend some time with my girlfriend as she was going to a college different from mine so we only got to see each other from time to time. Like during holidays and summers. Long distance relationships are a bitch and more than likely ours was strained, if not broken, at this point.

No, Kim was not my girlfriend. Don't get ahead of the story.

My on again, off again girlfriend was Elizabeth. We'd known each other since elementary school and dated off and on through high school but being away from each other during college was taking its toll on both of us. This past year when we were officially a couple again I'd stayed faithful to her the entire time to her despite hearing rumors that she'd slept her way through half of the varsity football team and half of the cheerleading squad from her college (seriously, you can't make this shit up).

Anyway, so it's Friday night and I'm knocking on the door to Liz's house. I'd been by a couple of times already since the semester ended. We have a 'in-house' date since her parents are going out for the night. Her mom opens the door and smiles at me. "Hi Gerry, come on in and make yourself at home while you wait. We were just leaving."

"Thanks Missus C," I say, "Uh, wait?"

"Elizabeth went out with some friends earlier but she said that she would be back in time," she said with a smile. "Come on in. Kimmy is in the back swimming her laps so she shouldn't be a bother." I always did like Mrs. C. She and Mr. C always treated me like family. Not to mention if I ever had a chance to pound her, even to this day, I would do so in a heartbeat. Mrs. C, in my opinion, always epitomized the concept of the MILF. Memo to me; delete this part of the recording. If Mr. C ever finds out, he'll probably kill me. Ah fuck it.

Mr. and Mrs. C left, but not before Mr. C gave me a once over customary threat in jest about treating his daughter like a lady and all that jazz, but we both knew otherwise. Once Mrs. C was out of earshot, he told me to stay as long as I liked to and told me where he had condoms at in the house. "I'm already covered, but thanks Mr. C," I told him, pulling the small 3 pack box from my back pocket. I smiled at them both, thanked them profusely, and closed the door behind them before settling down on the couch and started channel surfing.

I think that I was about a couple of innings into a baseball game when Kim walked, well... sauntered in actually, in from the back yard one slender leg in front of the other. 'Kimmy', as we called her, is Liz's younger sister and she'd just graduated from High School this past year. She was wearing a very sexy pink one piece swimsuit and was in the process of wrapping her long hair up in a towel to dry. "Heya Gerry!" she said brightly once she saw me. She frowned as she came into the living room from the kitchen in the back of the house. "Liz still not back yet?"

"'Fraid not," I shrugged.

"How long have you been here for?"

"Long enough to know that I picked the right sport when I chose football over baseball," I quipped. Baseball, while fun to play, was really boring for me to watch. Football was awesome to watch and play. I grabbed the remote and shut the TV off. "What've you been up to?"

Now it was her turn to shrug. "Same old, same old." she plopped down onto the couch right next to me and I couldn't help but compare her to her sister. Liz was a bit curvier than Kim. Kim had the slender swimmers/gymnast body that I liked. Liz used to be like that when we were fresh out of high school but stopped working out for some odd reason. Now she was just about average all around with a slightly fuller bust than Kimmy.

Now don't get me wrong, Kim had a nice body and just enough of a chest for me to really enjoy. From petite like Kim to curvy like Liz all the way up to full figured and plus sized women; let no man accuse me of breast discrimination.

Kim was also slightly shorter than her older sister but had longer legs, proportionately speaking of course, one of which she was stretching out now to prop up on the coffee table. Her swimsuit was cut high on her thigh and I let out an involuntary groan as my cock stirred in my pants.

Did I mention that I have a thing for swimmers?

"Well, mind if we watch something while we wait for your...'date'?" Kim asked. I couldn't help but wonder at the sarcastic tilt she put on that last word.

"Yeah, sure, knock yerself out." I handed the remote over to her.

"We got all of Star Wars in our On Demand library." She said, turning the TV back on and flipping it to the right channel. Ah, a girl after my own heart. Liz never got into Sci-Fi like I did.

We settled down into the couch to watch Luke, Han, and the others fight it out against the forces of the evil Empire. We were at the Cantina scene watching Han blow Gredo away (for the record; Han shot first and it was in self-defense) when Kim crossed her arms and leaned up against me, putting her head on my shoulder. I glanced down at her with a sideways grin. "Think that's wise with your sister about to come home at any minute?"

Kim snorted and snuggled closer. "She went out with all of her friends right after dinner. If she even remembered that you were coming over tonight, I'd be shocked," she said. "I bet you anything that she's out getting plastered and screwing anything that moves. She's been like that ever since she turned twenty-one."

I frowned. I really didn't like having my suspicions confirmed. "I'm sure she'd tell me that she's sleeping with someone else. We said that we could do that while we're at college."

"Oh come on, Gerry. You can't be THAT dense, can you?" Kim scowled up at me. "Believe me, she's playing you for a sap and it ain't right," she said. When I arched my eyebrow at her, she narrowed her eyes. "Trust me, I've read her diary. You can do better than her."

"Like you?" I gave her a wan smile.

"Well," Kimmy gave me a half shrug and looked back at the TV. "I am available and I'm pretty sure that you're going to be too after tonight."

"Whatever happened to that guy that I heard that you went to prom with a few months back? What was his name? Marco? Marcus?"

"Mark, and dumped me for some bleach blonde floozy on the cheerleading squad. The fucking bastard," Kim grumbled. "Anyway, he really couldn't do it for me in bed."

I nearly choked. Here's the little sister of my girlfriend and I sitting on the couch watching a movie and talking about our respective love lives. I really didn't know what to say to that so I just focused on the movie. We'd got up to the part where the good guys got reeled into the Death Star by the bad guys when Kim shifted next to me. I'd had my arms splayed out across the back of the couch at this time so she wound up knocking my right arm off. Not even paying attention, my arm wound up falling across her shoulders with my hand dropping down to brush her right breast ever so slightly. I felt her nipple harden under the swimsuit in response to my touch.

No, trust me, I'm not that smooth. I really wish I could say that I had planned that.

I actually froze up for a moment, unsure as to what to do or say. My mind was a jumbled mess. On one hand I was still, albeit technically, going out with Liz. On the other hand, I have Kim here who seems to be interested in me. My hand reflexively closed around her tit. It was slightly more than a handful for me and it was nice feel through her swimsuit; firm yet just supple enough to not be classified as total muscle tissue underneath.

Kim then stirred and let out a soft moan. She rolled her head towards me a bit, closed her eyes and let out a little gasp. Then she just said softly "No."

"Right, sorry," I mumbled, putting my hand back up on the back of the couch. "Sorry about that."

Kim glared up at me, but said nothing and I put my hands up in a quick apologetic gesture. She let out a huff of breath, reached up, and undid her hair from the towel. Her light brown hair cascaded down over her shoulders and she took a moment to put it all behind her back before leaning back up against me. I frowned, trying to figure out what just happened. She sat there for a moment with my hand over her breast but then told me no when I squeezed? Something wasn't right here.

On the screen Han and Chewie were shooting up the detention bay area while Luke went in search of Leia. Kim let out a moan when she saw the doors open to show Leia sprawled out on the bed inside the cell. "The only thing that could make that picture better would be if she were in her slave getup from Return of the Jedi," Kim said. "Chains, manacles, and all."

"Yeah, tell me about it." I agreed with a nod before it hit me what she'd said. "Wait, what?"

"I've always wanted to try bondage. I always think that Leia is lucky to get such a slinky outfit." My jaw dropped at her admission to that.

Kim shifted again, this time driving her shoulder back into the couch hard and dislodging my arm again. Just like before my hand dropped to her tit and she allowed it to stay there for a moment before she leaned into me again and let out a long, breathless "Noooo..." I yank my hand back while shuffling away from her and she straightened up in the couch. We then spend the next moment glaring at each other. I'm wondering what the hell her game is tonight. Is she teasing me like this on purpose or something?

We were spared from saying anything to each other when headlights suddenly shined into the windows. Outside a car screeched to a halt in the driveway and I heard multiple voices laughing, shouting, and generally having a good time. I left Kim on the on the couch and opened the front door. Liz was finally back with her little clique from High School plus a few others. Two of the local jocks were in the front seat while all the girls were stuffed in the back seat of an SUV. I saw Liz clamber out from the back, walk (well, drunkenly stagger actually) around to the driver's side of the SUV, and plant a big passionate kiss on the driver. The driver reached out to feel Liz's tits up while they made out for a whole minute it seems. I glanced over at Kim who just gave me a shrug that said 'See, I told you so'.

Yeah, it was a blow to receive confirmation about all the rumors that I'd heard. Yeah, it was hard watching my girlfriend, or soon to be ex-girlfriend I should say, stand there and watch her blatantly throw our relationship out the window. Truth be told, it wasn't as devastating a blow as I thought that it would be. I actually felt relieved to have it come out finally.

"I'll see you all tomorrow night!" Liz said, finally breaking away from her new boy toy. She waved at them all while she stumbled towards the house.

I rushed out and grabbed her to hold her up so she wouldn't fall. As I guided her back towards the house the SUV honked and I heard a "Hey, it's Gerry! Looks like I got your girl now, dude. How's the big college football star feel about that?" Fuck, it was Marcus. He was my rival back in High School and I see that his maturity hasn't changed much.

"Great considering I got the full ride scholarship and you didn't, asshole!" I flipped him the middle finger and got Liz into the house. Once I got the door kicked closed behind me I could smell the reek of alcohol coming off of her. She wasn't just drunk; she was fucking plastered. "Good God, Liz, did you leave anything at the bar for others to drink?"

"Gerry, what are you doing here?" Liz asked, surprised that I was there. "Did we have a date tonight? Shit, I totally forgot about that," her words were slurring. "What time is it?"

"Late," I said. Kim had got up off of the couch by this time and put herself under Liz's other arm. Together, we lugged Liz's dead weight up the stairs to her room.

"I told you she'd be like this," Kim said.

"Yeah, yeah," I mumbled. I don't know what I hated more at this point; Liz's unfaithfulness and unwillingness to stick to our rules or the fact that I'd been so blind that I couldn't see it.

"You two been talkin' about me?" Liz asked as we walked her down the hall and through her doorway. "Fuck you both!"

"I think that you've been doing enough fucking for the both of us." I said evenly. I wanted to yell. I wanted to scream, rant, and rave at her. Instead, I took the moral high ground and kept my cool. "How long have you been screwing Marcus?" I asked as Kim and I unceremoniously flopped her onto her bed.

"Long enough to know that his size DOES matter!" Liz giggled. Kim rolled her eyes and I shared in her disgust. Moments later Liz was snoring soundly in her bed in her drunken stupor. My eyes darted over to her end table and I ripped open the drawer. Inside I found her diary. I'd told her many times in the past that she shouldn't keep one and if she did keep one that she should lock it up. Kimmy, being the typical little sister, would of course read it when she had the chance. I know I would if I were in her position.

Hell, I'm doing it now; flipping through the pages rapidly and skimming the entries. I got through a few and it had more than enough information than I needed. Written in her own words was her admission that she'd been sleeping around and that she only kept me on the hook in the event I ever got drafted for the NFL. Yeah, I was good at football but I never once thought that I'd be good enough to get drafted despite what everyone around me was telling me. I flipped the diary back a few years and I pegged it just about right that we started drifting apart during our first year being away from each other. That was when we had started going our own separate ways.

Would've been nice for her to tell me earlier, the bitch.

I slam the diary close and throw it disgustedly back into the drawer. I hear a soft "I'm sorry, Gerry," behind me and I remember that Kim is there watching me.

"Sad part is, I'm not all that surprised or upset about it," I admit as I walk out of Liz's room. As the saying went there were many fish in the sea and my prospects for a good catch were phenomenal.

"So then you're, uhm, free tonight?" Kim asked as she closes the door behind us.

I pause in the hallway and look back at her. I do have to admit that I have fantasied about screwing Kim in the past, more so now that she was out of High School, ready, and (apparently) willing even though she's been sending me mixed signals all night long. There had been many a time where I've pictured her while jacking off. Now here she was standing in front of me in nothing more than a bathing suit asking me my plans. Turning in place, I regard her with curiosity as I try to figure out her hot then cold demeanor towards me tonight.

The next thing that I know I'm walking towards her and she's backing up against the wall. Soon there's nowhere for her to go to as I placed both hands on either side of her on the wall. I had her pretty much pinned and I was looking down into her pretty blue eyes. She looked back up at me shyly looking vulnerable and sexy all at once. Damn, it was such a turn-on that I got hard fast. My cock bulged in my pants and strained against her smooth belly. Kim raised her chin slightly and her lips parted in invitation. Reaching down a bit, I cupped her chin and her jaw in my hand and continued looking at her while I went in. Our lips met and I probed my tongue deep into her mouth.

Kim let out this sweet little whimpering moan that seemed to resonate and awaken some primal urge deep within me. Her body slackened a bit as if she were surrendering herself to me. It just made me want her even more. We broke the passionate kissing long enough for me to start suckling on the side of her neck as I made my way down to her collar bone. She twisted her head to the side and let out a desperate, breathy, "No."

What. The. Fuck.

"Seriously?" I growled. I'd had just about enough of this shit and decided that we were going to get things straightened out here and now. I came back up and looked her dead in the eye. This time it was a hard glare instead of the open lust that'd been there moments before. "What the fuck are you playing at?"

"Ugh...men," Kim rolled her eyes in irritation. "You need everything spelled out for you." She grabbed one of my hands and placed it right on her pert little tit, squeezing my hand over top of it. I arched my eyebrow at her as I tried to figure her out. Kim continued kneading herself via my hand while she gave me a hurt little look and let out a "No, please sir, don't." I continued to eye her suspiciously. The way she switched gears made me wonder if she really wanted what I thought she was wanting.

To test my theory, since it was obvious she wasn't about to come out and say anything; I dropped my hand down right to the crotch of her swimsuit and slid my hand right across her pussy. Her eyes went wide with surprise but there was just a hint of a smile there as she let out an "Oh, God, please don't!" while pressing herself right up against my hand.

Playacting a rape fantasy? Alright, I'm game. I like it rough.

I smiled wickedly at her and she gave me a quick smile and a nod to signal her approval, finally happy that the proverbial light bulb went off in my head. I brought a hand back up and grabbed her by the back of her neck. She let out a squeak as I hauled her down the hallway to her room. I shoved her towards her bed hard enough to get her to trip over the side and fall down onto it but not hard enough to hurt her. My other hand swept back to slam the door closed, not caring if Liz came out of her drunken stupor long enough to hear it.

Kim had rolled onto her back and sat up just in time for me to close the distance between us. I pushed her back down onto the bed and straddled her hips. She opened her mouth to say something and I clamped a hand over her mouth. Kim closed her eyes and let out a little moan while gyrating up against me. I reached up with my free hand and yanked off one shoulder strap of her swimsuit, and then the other. Then I grabbed it at her modest cleavage and yanked down to her ankles, exposing her pert little breast to me. Her soft, pink little nipples were already hard nubs.