Out of My League Ch. 03

At the end of our last chapter, I had shared another painfully hot encounter with a woman that I ended up entangled with for the better part of the rest of that year. I'd like to tell you that this post is about the first time that I actually, finally, got to have sex with her, but the truth is this - she was so bad at it. It's not that she wasn't trying; she had enthusiasm in spades. No, she was simply the most incredibly boring fuck that you could imagine, and I'd hate to bore you with the details of how I spent the next 8 months cycling between blue ball hell interrupted infrequently by 15 minutes of the same doggystyle sex each time.

I was bummed, because she was just way too hot to be that boring in bed, but I couldn't escape the fact that she was a far better tease than she was a lay. Don't get me wrong, she really was a grade-A cock tease, which remained fun for a long time. Over time though, jerking myself off after nights out with her started to get really stale, and my efforts to pick up my game at school were beginning to bear fruit. Leading into the summer term, I was up for a really prestigious internship that I'd been nominated for by a professor-turned-lifelong-friend. Though my first serious relationship and the yields on my hard work were beginning to show and mature into a more adult confidence, the prospect of interviewing for this internship had me in bits for weeks. I redoubled my efforts to prepare, finding time to leave the house only when I could no longer put off the breakup conversation that was long overdue.

The days ticked on by and the eve of the interview was upon me. I was a mess. I couldn't stomach a bite of food, sleep eluded me but for some cat naps in the library, and texting the ex for comfort started to look real appealing. Gladly, I was saved from near disaster that very evening, when I found myself, again, in class. I wasn't in any mood to pay attention, but I wouldn't allow my discipline slip, so I went.

That's when Kate sat beside me. I hadn't noticed her before, which struck me as odd, considering we were in the last few weeks of term. Another panicking student, turning up at the 11th hour to beg for clemency from a professor poised to record an F for her term, most likely.

She flopped her books down beside me, and told me she was Kate. I hadn't asked, or even looked her way frankly. But she was Kate and she stuck her hand out to shake the one that I was not actually offering. I took it anyway. It was nice to meet her.

She was small, and boyish. Pretty, if that matters, but the close cropped hair did give her the look of a teenage lad. She smelled too, I'm sorry to say, like stale beer, cigarettes, and faintly of vomit. On top of that, she was covered in the most random array of badly done tattoos that have ever been inked in any grungy basement by a rebuilt cassette deck tattoo gun. Are you horny yet? No, I don't suppose you are. And neither was I. I do sound like a horrendously judgey prick at the moment though, and I'm positive I came off that way at the time.

We chatted, class started, we chatted at the break again, class resumed, class ended, we chatted on the way out of the building, and she went off into the night. And I was smitten. We loved the same bands, drank the same shitty beer, spent our weekends in the same gross kinds of bars, and she was funny as all hell in a morbid way. I swore to myself that wouldn't be the end of things. She'd almost, but not entirely, forced the anxiety of the week out of my system. Since traces of it did linger on, I settled on meeting some friends at the pub to chase the rest away. I'd never do the same now, of course, but I was 20 and invincible.

I went home, cleaned up, and headed back out. Nearing the street most commonly frequented by the students looking to bar crawl, I saw my friends smoking outside our hole. Waving, I caught the briefest glimpse of Kate slipping inside a, shockingly, dumpier looking joint than even I spent time in.

Obviously I blew my friends off.

The interior of this particular establishment smelled like I imagine a Ted Nugent concert must, and the stains on the carpet were a thousand shades of brown that I had never seen before. This was a risky play, but I had to make it. It was a big place, but I spotted her quickly. She was alone at a booth in a corner. Brimming with pregamed confidence, I made my way over.

She laughed at me as I walked up, and asked if I came here often. No, but tonight seemed as good a time as any to start. It's a biker bar, she told me. That did explain the smell, but not so much why she was there. She was waiting for people, and the beer is impossibly cheap here. I bought her one. I don't think it's legal to sell it that cheap.

We chatted again, and I was delightfully unmotivated to continue doing so with any pretense to anything else happening; I just enjoyed her company. Her friends were at the hospital, according to a text; one of them had been drunk all day and needed to be pumped. She seemed unsurprised at the news, as if this was a regular occurrence. She asked if I'd shoot some pool. I'm so bad, but was keen to continue spending the time with her, and the drinks were pushing us both into flirtier waters. She put her hand on me as we walked over to the table, and I died a little.

She offered to rack, and bent to do so. You won't judge me, I hope, for shamelessly looking down her shirt as she did. The oversized tee had been playing a mean trick on me; she had surprisingly full boobs capped by pale, puffy nipples that sparkled with a bar piercing through each. Actually I think the one might have been a paperclip. I took too long trying to figure out what it was, and was caught looking. I was instructed to fuck off, said with incredulous laughter. I was sorry, I said, though I didn't mean it, and she knew it.

I'd instruct you to imagine a cliché game of pool with plenty of phallic symbology and steamy looks, but we barely played. She gave up after the first few shots, on account of wanting to shove her tongue in my mouth, evidently. It was as blunt as I'd come to expect from her, but weirdly soft. There was rather a lot of tongue, and the piercing there that came with it. She grabbed my hand and pulled me to the back. Bathroom sex sounded great, provided there was enough penicillin in the city to counter the setting.

We didn't go to the bathroom though, but another room altogether, at the top of a narrow staircase. She opened the door proudly. A dirty mattress on the ground, a small desk that had likely been stolen from a local primary school, and a pile of clothes spilling out of a bag. She lived here.

Extreme hesitance was blasted to bits as she ripped my shirt off me and pushed me to the floor mattress. Being quite tall, this was a long way down. My head hit the wall, the music from downstairs pounded, and she disrobed herself with the fervor of a feral animal. Shoes flew to one corner, the shirt to another, the pants jetted off toward the desk.

She stood over me in nothing but a pair of briefs, hands on hips, catching her breath and looking all too pleased with herself. She dipped a shoulder toward me coyly and asked what I thought. I thought the world of her. Her skin looked like the underside of a detention hall desk with all the doodled tattoos, but her body was no joke. Hippy, slightly busty, and with thighs that I wanted around my ears desperately, she was so much more than I expected. Again, judgy. I've grown.

She was on me like a hurricane, yanking my pants off quickly. I was half masting and leaking a shocking amount of precum as she pulled me out, and she wasted no time flat spitting all over it before swallowing it whole. She bounced her head up and down until she choked, coming up for air with a streamer of spit on her chin.

"Fuck my throat, please," she begged. She meant it, and I obliged. She bobbed down again and I thrust my hips up into her eager throat. She yelled a hearty "FUCK" as she came up from that and wiggled out of her briefs with a riotous laugh.

I stroked myself as she rolled around on the ground, wrestling out of her panties, realizing with a laugh of my own that she tucked and rolled into a textbook downward dog, hands out in front and face pressed to the ground, her ass on display like a prize peach. I knew what I needed to do.

I slipped in so easily, thoroughly soaked as she was, right to the base of my cock. I'd never been able to do that with anyone else, given my girth, but it was effortless with her, and she contentedly groaned and arched her back slightly. I was instructed to fuck her, and it had to be now.

I pounded her. There was no finesse in it, no art to work I put in. Her pussy greedily gobbled every inch of my cock without a hint of resistance and I was all too happy grope and slap at her rippling ass while I did so. She laughed like a mad woman as I did so, yelling to rival the volume of the bar downstairs and naming me to be a motherfucker the entire time. I was in a trance, undoubtedly drunk on questionable beer and lust for the woman impaled on my cock. I was growing closer to the edge, and let her know, so she rocked all the way forward and out my throbbing cock's reach. I moaned in protest while she rolled over and instructed me to straddle her across her body, just under her chest. I complied happily, and she looked right into my eyes as she reached up to wrap both hands around my slick shaft.

"Thank you so much, daddy."

She pumped with her two handed grip while she bit her lip, sweaty from the fucking, and stared directly at the head of my cock. I was told to give it to her. She wanted it. She jerked harder. I held on for dear life, refusing to let this end.

"Please, daddy."

She broke me. I began to cum, rocketing rope upon rope of the stuff over her face, chest, hair, shoulders. I drenched her. I absolutely slathered her. She appealed to the good lord as I did so, and I swear I nearly met him in that moment. She thanked me profusely, and genuinely, which very nearly sprung me to readiness again. Scooting up from between my legs, she took my face in her hands and kissed me, cum covered lips and all. It was so hot, and I smeared it all over her body with my hands while we kissed.

We fell back and lay laughing together a while about the whole riotous affair. She idly played with the cum on her tits for a few minutes until I had the good sense to pass her an already crusty towel. She was going to grab a shower and get to bed. I needed to get going anyway, with the interview in the morning and all. She kissed me, passionately again, before I left, and wished me luck.

After a night like that, how could I do anything other than succeed. And succeed I did, nailing the interview and securing the offer the very next day, all the while dreaming of the tomboy who drained me like a pro just hours before.