I must confess, I am an asshole. I grew up as a morbidly obese kid, and as a result had no success with girls. I finally decided enough was enough, and after a year of Atkins, I was slim and brimming with new found confidence. And a desire to repay women for years of rejection. This will be a bit long, but I figure the background will offer a better connection to what happened.
I first met Kayla when I was 16 and she was 13. My parents, along with their car club, including Kayla's grandparents, went out of town for a weekend of river boating and to attend a classic car show. We were the only kids along for the trip, so we pretty much had to rely on each other for entertainment, which wasn't too bad considering she was really cute. After 2 days of swimming, wrestling, and staying up late together, it was time to head home. Kayla's grandparents offered me a ride back so that Kayla and I could keep each other company on the long ride home, and I eagerly accepted. For whatever reason, I was nervous and things were ridiculously awkward on the way back. I ended up spending nearly the whole trip staring out the window, wishing I had the balls to make some kind of a move. Finally, as we were nearing the end of the trip, I had enough of my bleeding vagina, reached over and grabbed Kayla's hand, and leaned in and kissed her, with her grandparents mere inches away in the front seat. She looked at me, shocked, and a few minutes later we pulled into my drive way. As I was getting out of the car, Kayla's grandmother mentioned that her and Kayla were going on a church white water rafting trip the following weekend, and invited me along. Sensing opportunity, I smiled at Kayla and told her grandmother that I'd love to come.
Now I won't titillate you too much and offer you guys some false hope that I ended up mounting Kayla on top of the church groups cross. The first night out, we found a quiet spot and she asked me why I had kissed her. I simply told her that I thought she was cute and liked her, which apparently is like Kryptonite to 13 year old girls, since we spent the next 4-5 hours making out. We got back to where my tent was later that night, but she told me she wasn't ready to go any further, and I didn't press the issue.
The next few weeks we called each other constantly and emailed, and went on a few dates. Unfortunately, her mother found out about our relationship and, being the frigid, bible-thumping bitch she was, forbid Kayla from seeing me anymore. I graduated a year later, and moved out of state, moving on with my life.
Fast forward a few years to when I was 22. I had just moved to a new state, where my parents were now living, and was staying with them until I could find some roommates I trusted in the area. A few months into living with my parents again, my mom told me that Kayla's grandmother was coming to visit for the weekend...and guess what? She was bringing Kayla along. I felt as if I had a chance for redemption. I was going to get a second chance.
The morning that Kayla and her grandmother flew in, I had to work until late afternoon. I rushed home from work, and met my mom in the kitchen, where she told me I should go change and get in the pool, as Kayla, her grandmother, and my step dad were swimming out back. Changing quickly, I hurried to the back gate and was greeted by what I can only describe as the most perfect 'Fast Times at Ridgemont High' moment, ever. Kayla was just walking up the steps out of the pool, dripping water and wearing a two piece black bathing suit that hugged her body in every right way possible. She was no longer the cute, 13 year old girl I had a crush on as a kid. Kayla was fucking hot. She was 5'3, short bleach blonde hair, brown eyes, with tan skin. I secretly thanked God for her not being an underdeveloped, magazine cover anorexic, as she had D sized breasts, a flat stomach, and a gorgeous, round ass. As my Hispanic buddy would say, "She was thicker than a Snickers".
I stood there, dumbfounded, and she turned from the pool and finally saw me. Letting out a small, shrill squeak, she ran at me and gave the most pleasantly wet hug a guy could get living in the hottest state in the union. All her wonderful curves clung to me, and I was on cloud nine. We walked over to her grandmother, who hugged me as well, and caught up on life. We chatted about surface things for a while, and then her grandmother dropped the bomb that my fragile heart had been so afraid to hear. Kayla had a boyfriend. Not just a casual one, a guy she had been dating for three years. Fuck me. Kayla's grandmother then mentioned how much her family disapproved of him, as he was a terrible influence on her, getting her into the party girl/drinking/smoking lifestyle, hence one reason Kayla had been invited to come along to visit us. Apparently her grandmother was under the impression that I was the same sweet, Christian boy that she had known when I was younger. Oh granny, how you have underestimated me.
We all got out of the pool to go to dinner and then to a local country music/theater production. Kayla and I continued to catch up and rebuild our old rapport, injecting some flirting and light touching into the night. We got back to my parents house, and my parents and Kayla's grandmother we're ready for bed after a long day out (they were all 55+, go figure). Kayla, however, was ready to go swimming again. I teased her about being part fish, but wasn't about to talk her out of getting half naked alone with me. We jumped in the pool and splashed, rough housed, and swam for a bit, all the while talking about our new lives. After a while I started to pry about her party lifestyle, and began teasing her that because she was a girl, she automatically was a light weight compared to me (you say stupid things to get a girl naked). She responded to my challenge by saying she could easily drink me under the table, and I told her "fat chance". We ran inside and I showed her my parents liquor cabinet, and she selected a bottle of Captain Morgan 100, and we went back outside and sat on the loungers by the pool.
We drank gulp for gulp, and I started questioning her about her boyfriend, who she was texting while we were drinking. To my surprise, he was in Vegas for the weekend for a buddies bachelor party. Aside from him having a gambling problem that she was worried about, she also suspected him of cheating on her in the past. Well, the Captain in me doesn't spit on opportunity when offered, and I began to harp on whether she was worried if her boyfriend was taking advantage of the weekend alone and banging everything on two legs; after all, it is Sin City. All the while that I was sewing the seeds of doubt into her mind about her boyfriend, I was watching her text her him from the corner of my eye, and to my absolute delight, she had elected not to tell him about who I was, let alone me even living there. She kept trying to reassure him that she was so bored there, all alone with no one her age, and I slowly stopped taking actual shots from the bottle and simply mimed each shot, letting her get drunker in the process.
I decided that all my pieces were lined up, and it was time to make my move. I slid over from sitting across from her on the opposite lounger, and sat next to her on hers. I began to rub her back slowly, to build up comfort with my touch, and gently trailed my finger down her back and over to her thigh. I turned and looked her in the eyes, and I could see the passion and desire building. Still maintaining eye contact, I slowly slid my hands under her bikini bottom and lightly began to rub her slit up and down, feeling her getting wetter by the second. I reached over with my other hand and pulled her in closer, kissing her deeply while still exploring her under her bikini. Her breathing intensified as I began to add more pressure on her young pussy, and she exhaled roughly as I sunk my fingers deep into her. As I continued to finger her, I decided it was time to let those glorious breasts breath, and with one swift tug of her bikini top string, let loose two of the most beautiful, round, perky breasts I had ever seen. I took her nipple into my mouth and pushed on her with my body to get her to lie down on the lounger. I suckled like a newborn until my shorts felt like they were ready to explode from pressure, and began kissing down her stomach to where I was still knuckle deep inside her. I undid one side of the bikini bottoms tie, and pulled them to the other side, exposing her glistening vagina. It was simply too much for me to see, and I immediately began to lick, kiss and suck on her pussy, not leaving a spot uncared for. Her hips bucked up and down as I teased her between her thighs, and she began to let out short, clipped moans of pleasure. Finally, she pushed my head back, flipped herself over, and pushed her ass back towards my hips, inviting me to partake in riding her. I ripped the velcro holding my shorts together, and pulled out my throbbing cock, ready to sink it into her. Unfortunately, I misjudged my position on the lounger, and with both of our weight on the left side of the chair, we flipped over onto the concrete and on our sides. I let out a little laugh, and she got back up on all fours and started to shuffle-crawl away. I grabbed her hips, but she turned and looked at me and started saying "No, no, no, this is wrong. I can't do this. I'm so sorry, I have a boyfriend."
Seriously, fuck me.
She had a bit of a drunken, emotional break down by the pool, and ended up swimming around, crying, while I tried to get her to calm down, reassuring her that nothing that bad had happened. She finally consented that I was right,and came out of the water, still naked as a jaybird, and I grabbed her a towel and told her to quiet down, I'd get her inside. I grabbed her bikini and started leading her inside, all the while the Captains grog started taking affect on me, making me a bit light-headed and loopy. We got to my room, where I told Kayla to hold her towel up and I would try to dress her. She went from being sad and hating herself, to giggly and flirty again about her being naked. I kept trying to fumble her clothes on, but my hands were no longer working right, and she broke into a case of the giggles, letting her towel drop and falling into me, thereby pushing us both on top of my bed. Her back was on my chest as she lay on top of me, with her butt lying spooned in my crotch, which stirred my arousal again. I started to push her up off of me and the bed, not wanting her to freak out again, but she felt my growing hardness under my shorts, and I shit you not, began to grind against my cock like she was competing in a twerking contest. I wasn't going to pass up a good thing, so I grabbed her, swung my hips out, and turned her onto the bed, so that I was on top. She reached down, undid my shorts, and wrapped her legs around me, pulling my cock into her. I looked down and kissed her lips, kissed her breasts, kissed everywhere I could reach and began to fuck her with the sexual tension that only six years of waiting can produce. I was fading in and out of sobriety as my blood pressure increased, but her hips rocked in motion with mine, keeping me in the game. I grabbed her shoulder with one hand and the back of her head with the other, tangling my fingers in her hair and began to fuck her harder and harder, letting every last bit of frustration out. Her breath was hot on my neck as I pumped faster and faster, and after a few minutes she began to pant in my ear "oh god, oh god" as her legs tightened like a vise around me and her nails dug down my back. Then, her whole body tensed and she let out one last strangled moan as I pumped one final time into her, pushing in as deep as I could, and cumming spurt after spurt into her little body.
We lay next to each other, rubbing each others backs and sides gently, until I looked over at the clock and realized it was 5:15 in the morning. I quickly got her dressed back in her bikini, and led her out of my room towards the guest room, only to feel my heart stop dead in my chest as I saw my step dad in the kitchen (which is right next to my room) pouring himself some coffee and getting ready for work. He looked up after hearing me walk in, glanced back at Kayla, and looked me straight in the eyes. Then he smirked, turned away, and walked out of the kitchen.
The rest of the weekend was right back to Kayla being a sad sack wreck over cheating on her boyfriend, all while still trying to figure out what the fuck feelings she still had for me that made her do what she did. She went back home, I told her that she should keep it between us if she wanted to still have a boyfriend, but guilt got the best of her and she told him a gentler version of the story where we only saw each other naked and touched each other a bit. He was pissed and threatened to kill me, I only laughed and told him thanks for lending me his girlfriend for the weekend.
I'm not a good guy. This was the first time I stopped being an Average Frustrated Chump, and started being a dominant, successful male. I've slowly turned into more and more of an asshole, but this was the starting point of it all, although not the first instance of me being a dick. Do I regret the choices I've made?
Fuck no.
