It's a Goddamn Arms Race

Before Spring Break, I did an incredibly stupid thing. Sadly, it isn't like fucking up is entirely out of character for me. I am a perpetual line stepper. My mouth inevitably runs roughshod over my thought processes and better judgment. I try to shut the fuck up, I really do, but my efforts haven't ever been overly successful. If there's a bet to be made, I make it. I love to win, but I really, really hate to lose. If there's a joke in there, I have to say it, even if it hurts someone's feelings. I'm not mean on purpose, but I know that I can be thoughtless. Damn the torpedoes, then kick myself later, that's my schtick.

I almost revel in being the comic relief. I've always been the class clown, the obnoxious "I don't care" kid. I think it comes from being an only child and a military brat. Hell, I went to six elementary schools, three middle schools, and four high schools. I had to distinguish myself somehow.

My mom is a Lieutenant Colonel in the United States army. Dana's a bad bitch, and she doesn't fuck around. When my mother says jump, it's not a request. (I call both my parents by their first names. I have no idea why; I just always have.) Dana joined the military because her family was power-regularly-turned-off-poor, food stamps, the whole deal. She went to college on Pell grants, made up the rest of her expenses with ROTC scholarships, then commissioned as an officer. That said, Dana's also a staunch Democrat, and she's always told me that the military is a tool. Just like anything else, it's all about how you use it. She'd smirk during that part of her lesson, then go on to say that I was a tool too (double entendre intended), and that with every decision, I had the option to either help a situation or do more harm.

My dad is an aging hippie type. Alex loves Jerry and the Dead. He day trades for money because my parents still move all the time. Also, he can't stand answering to a boss. My father is all about the grey area, a constructivist perspective, and finding your bliss. On paper, you'd never put my parents together, but somehow it works. They met in college, have been married for almost thirty years. Alex makes my mom laugh and loosen up. Dana gives my dad some necessary structure. Anyway, I learned by example very early on to never tell a woman what to do.

Honestly, I only approached Hannah at that party because Shaun bet me that I wouldn't. I'd been looking at her all night, and he finally got sick of my sad puppy eyes. He knew I wouldn't puss out if a wager was involved. So, I sauntered over, fully prepared to have to slink back to my chuckling buddies with my proverbial tail tucked between my legs.

When I reached her, I dropped my best line and chivalrously offered to pump her a beer from the keg. I was shocked when Hannah glowed up at me instead of immediately rejecting my pedestrian advances. I swear, my heart grew three sizes, just like the Grinch, and I melted under her warm smile.

We'd been hanging out for about three months; I had asked her to be exclusive after the first two weeks. For the first time in my life, I cared... a lot. Hannah was the whole package. She was funny without trying, so kind, achingly beautiful, and way, way out of my league.

My girlfriend had a chestnut pixie cut, a graceful neck, and these natural dick sucking lips that drove me crazy. Normally, short hair kind of turns me off, but on her... damn. Think Angelina Jolie after her role in Gia, effortlessly gorgeous with prominent collarbones. She had a nose stud and wore a lot of oversized, hanging black punk tank tops. Her big, wide blue eyes seemed to see right through me. Hannah was whip smart, pre-law. I had yet to win an argument with her, even a joking one.

Every time I embarked on a dumb joke, she naturally smoothed things over. When I fidgeted, she put her hand on top of mine. She made me laugh so hard that once I did an legit spit take. Hannah just got me, and I wanted her to feel like I got her too.

I mean, it isn't that I'm a troll. My grades aren't bad, and my business degree should net me a good job after graduation. I'm 5'10, perfectly average. (That said, the shrink at my third high school strongly suspected that I suffered from a Napoleon complex in conjunction with my ADHD.) My black hair is naturally stick straight, but I've learned to use pomade. I know how to dress. I take regular showers and manscape appropriately. However, even with all of the accoutrements, I'm still obnoxiously, depressingly basic.

It especially sucks because all of my friends are objectively great looking (some of them manage to rub it in by also being academic geniuses and/or having ridiculous emotional quotient). Seriously, they are all male model, leading man material. Compared to them, most girls wouldn't bother to pick me out of a line-up, let alone up at a bar.

Anyway, a week before we were scheduled to leave for Spring Break with my friends, Hannah and I were blissed out in her lofted bed after a marathon sex session. Her roommate was at the library, and we were enjoying having the place to ourselves.

Hannah's skin was bronzed from running cross country, and her sweat made her tight, petite body shine. I watched her bare chest rise and fall like it was a religious experience. Her light nipples were small and puckered. Her firm tits could have fit perfectly in one of those old-fashioned, wide champagne glasses. We were talking about everything and nothing, telling secrets, the way you do at the beginning of a relationship. She asked me why I hit on her, why I picked her up that first night.

Stupid with sex and happiness, I babbled. "Oh, you know, the usual. Shaun bet me that I couldn't get your number."

Hannah immediately pursed her lips, which made her sharp cheekbones even more angular. I could tell that she was pissed.

She bit off her words. "Let me get this straight, you picked me up for a bet?! You've been laughing at me behind my back with your friends this whole time! What did you get when I slept with you?! Is that why you asked me to be your girlfriend, were there extra points?! What is wrong with you?! Also, 'the usual'?! Is this something that you idiots do a lot?!"

I tried to cut her off, but all I could do was make this sputtering noise. I think it was the first time in my life that I had been at a loss for words.

Hannah was still spitting at me. "Apparently, this whole fucking relationship has been a lie, and worse, you've made me a cliche! Let's be clear, this is not She's All That, and I am not Rachael Leigh Cook! What the actual fuck, Seth?!"

When my mouth belatedly caught up to my brain, I couldn't apologize fast enough. "Hannah, no. It isn't like that at all. I just... you're so beautiful. Even from across the room, I could tell how smart and special you are. I was nervous, and the guys saw me looking at you all night. They were giving me shit. I didn't have the balls... Well, Shaun knew that if he bet me, I would have to take action."

Hannah rolled her eyes. "Oh, it was all so innocent... What did you win?"

I was confused. "What did I win?"

She glared at me. "When you got my number, what did you win?"

I was still flustered; my answer came out sounding like a question. "Bragging rights?"

It wasn't a lie, but it wasn't the whole truth either. I also got the right to slap Shaun in the face once, whenever I wanted. It was our established wager.

"Seth, I can't fucking believe this. We're going on vacation with these guys! You've all been laughing at me..."

I tried to apologize again. "Honey, please. I'm so sorry. It was totally innocent, I promise. No one is laughing at you. This, between us, is so special. You're so special to me."

Hannah glowered at me. "Prove it then. A bet for a bet. No sex until one of us caves. I don't want to feel cheap, Seth, and I know how seriously you take welching on a bet. Let's see if you can hold out. This one is for all the marbles."

I was taken aback. "What?! If I cave first, you're going to break up with me?!"

She nodded seriously. "You said that you love a challenge, and that you respect women, that I'm not just one of many. Let's see. Put your money where your mouth is."

I hedged, nervous. "What do I get if I win?"

Hannah smiled smugly, then said, "Me."

I bit my lower lip and thought about it. I knew that if I didn't agree, she would just break up with me right then, naked. It didn't seem like I had a lot of viable options, so I nodded and stuck out my hand.

"Okay, pussycat. If that's what you want, your wish is my command."

She grabbed my palm firmly and we shook on it, sealing our pact.

Hannah was serious about the bet. She spent all week teasing me, bending over in the frayed short shorts and tight skirts that I loved. She wore bright red lipstick and played with the straws in her drinks, drawing attention to her mouth every chance she got. Even though we hadn't been together long, Hannah already knew that her plush lips were my weakness.

One night, she took off all her clothes in a practiced striptease, showing off lacy, red, bad-girl lingerie. Then, when she was completely naked, Hannah masturbated in front of me for about an hour. I was fascinated, couldn't tear my eyes away, but I tried (and failed) to pretend that I was unfazed. I was completely at her mercy when she finally brought herself to an unrestrained, very vocal, squirting climax.

I was pent up as hell, but I had firmly resolved that I would not fold under any circumstances. Hannah was still sweet to me. Everything else went on as was typical between us, but she initiated all physical contact past hand-holding and fairly chaste kisses. The implied denial was actually kind of hot. I was solicitous, carefully aloof, feigning that I was above all her tricks.

The first night that we were at the shore, Hannah seemed really drunk, like, babbling, trying to crawl into my shirt, dropping shit, fucked up. I mean, she's tiny. I wasn't surprised that she had trouble holding her liquor. However, if she was going to be messed up, I didn't need to join her, so I cut myself off after two beers to keep an eye on her. Hours later, as the party wound down, when I picked Hannah up over my shoulder, she squealed, smacking me on the shoulder flirtatiously.

Once we got back to our room, Hannah was all over me. Now, I don't fuck drunk girls. I'm not above hooking up with a woman who has a mild buzz, but that's all. Never when women are sloppy, or in any way unaware. No matter how much I want it, there are some lines that I don't cross, period. Dana raised me right. Also, when she gave me my sex talk, during the very comprehensive section on consent, she told me a horrifying story about something that happened to her in college. Then, to pile on and add insult to injury, there were three more gross examples featuring guys that she served with over the years. Long story short, I never, ever want to be one of those guys.

That said, I was a little conflicted. I mean, I knew that I had to win the bet, but I still desperately wanted to be inside Hannah. That was kind of the whole point, the crux of the issue. Let's be real, I needed to get laid. I'm just a man, after all, and it had been a fucking long, sexually tense week. I hadn't even been able to find the time or privacy to jerk off, busy with midterms and everything else that I had going on.

Distracted as I wrestled with my conscience, Hannah worked my zipper, then pulled my dick gently through the hole. As soon as she touched me, I was rock hard. My cock is average, so normal that it could be featured in an anatomy textbook; you know, generic white guy phallus. I don't have a complex about my size, but I also won't whip my dick out without provocation like I'm a porn star either. None of the girls that I have been with have voiced any complaints. That said, less-than-evolved male that I am, I really loved that my uncircumcised six inches looked huge in Hannah's tiny, manicured hands.

I took her hand. "Hey, hey, babe. You're really fucked up. You don't need to do that right now. Let's get you into bed."

I lifted her from her knees, off the floor and onto the mattress. "Just be here with me, okay?"

Hannah pouted, undeterred and still trying to go for my penis. I held her hands, trying to keep her contained, but in a supremely skilled move, she twisted around me with her legs, and then flipped on top of me. I was surprised and suddenly confused. Her balance wasn't off at all!

She kissed me hard, and the only thing that I tasted on her lips was lime. As Hannah straddled me, I looked at her critically. Her eyes weren't bloodshot, and they were tracking every one of my movements. Her face wasn't flushed. I didn't smell any booze on her skin or her breath.

I had a new theory, so I taunted her. "Babe, I know you're sober. You're trying to prove that I'll take advantage of you, that I'm that fucking guy... Like, I don't give a shit, right? This is part of the bet?"

With that, I saw her brain working overtime. Her facade entirely slipped, and Hannah looked so immediately flummoxed and guilty that I could tell without any doubt that she was sober. That minx! She was faking! It was all a test!

I knew that I should have been pissed off about her manipulation, but I was actually kind of relieved. Turnabout is fair play. I had pulled something over on Hannah for months, so I practically deserved her ruse. I knew that we'd have to talk everything out later, but my body insisted that those details weren't immediately important.

I grabbed for Hannah's hips, but she slapped my hands away. Then, she leaned down and kissed me with tongue, grinding against my hard cock. When I tried to reciprocate and kiss back, she bit my bottom lip so hard that I groaned.

Hannah whispered in my ear, "It's so hot to know that you wanted to take care of me, that you actually feel something. I knew that I was right; we're special together. This is real. So, now that I know we're on the same page, I'm going to let you win the bet, but I'm going to control the pace. If you move, I win, and then I stop."

Hannah stripped my clothes off efficiently and just looked me over with hungry eyes. I was almost panting. I had never been used as someone's sex object before. It was surprisingly hot. I could hear Bryan fucking Allison through the wall, which made my blue balls feel so much more intense.

I lay there as Hannah pulled off her own clothes. Her nipples were hard. I could feel the heat radiating off her thighs and her pussy. She straddled me naked for a long time. I took a deep breath, and my erection twitched. Hannah grinned at me, coy and beautifully smug.

As I waited, it felt like my dick could bore through diamond. The temptation to touch her was terrible, but I was determined that I would not lose. I'd come too far. Also, the cat and mouse dance of practiced reluctance was really doing it for me.

Her pouting lips parted, and she said simply, "Beg."

I didn't know what to say.

Hannah raised her perfectly plucked eyebrow and said it again. "Beg me, Seth."

I leaned up and whispered in her ear. "Not touching, promise. See, my hands are still lying right next to your thighs. I want to fuck you, baby, but you're making all the choices here. Everything that happens here is up to you, Hannah. I'm your bitch."

Her eyes sparkled. "You're my bitch?"

I nodded resolutely, even as my balls throbbed; my cock was purple. It felt like it was bursting with trapped blood.

"Make yourself feel good. Use me like your dildo, pussycat. This is all for you. What I need doesn't matter at all. I just want to make you cum, princess."

With that, Hannah put her hands flat on my chest. She splayed her fingers and lifted her hips, carefully balancing her weight on her palms, then she dropped down on my cock in one long, slow, wet thrust. I could hear myself groaning loudly every time that she moved up and down, but I couldn't stop making the noises. It was all I could do to not flip her tiny body over with my hips and screw her senseless.

The view definitely didn't suck. Hannah's face and bare chest were flushed. I let her keep up her slow, steady pace. She purposefully ground her clit against my pubic bone every time I bottomed out. I gripped the sheets with my fingertips, staring up at her leisurely gyrating body in awe. Hannah was squeaking, moaning, and humming with every deliberate, practiced change of the angle.

I did okay with the ladies, had probably had more than my share of highly predictable dorm room sex, but I had never experienced anything like this agonizing, one-sided fucking. Every move felt torturously good. I was trying so hard not to thrust up, to follow her lead, that I am surprised I didn't rip right through the pilled fabric in frustrated ecstasy. Hannah kept going, using my body the way I told her to, clearly making herself feel good.

I focused on her every flex, controlling my breathing, closing my eyes and purposefully contracting my interior muscles whenever I felt myself getting too near the threshold. I was suddenly so glad for all the (supposedly wasted) time I had spent practicing edging to Cock Hero videos; those efforts were literally the only reason I managed to hold on.

When her strokes started getting faster, I could tell that Hannah was close. When she finally gasped for me to rub her clit, I knew she was going to cum. Following instructions like the good guy I was trying to be, I started massaging in little circles, using the pads of my fingertips to explore her dripping sex. It didn't take but about three rotations, and then Hannah's tight cunt was squeezing me from the inside out, like an anaconda compressing its prey, as though her vagina was trying to eject me.

With that first pulse, I unclenched and let a week's worth of backed up semen finally, finally move up, through my shaft. It felt so fucking good that I think a few tears escaped my eyes. I hoped that Hannah, seemingly lost in her shaking climax, wouldn't notice. It was such a relief, to be with her again, to know that we weren't prematurely over.

I thought that I was going to cum inside her (as was customary for us), but suddenly, Hannah pushed on my chest hard, like she was performing CPR. Before I could register exactly what was happening, she had flipped around and absolutely swallowed my cock. When her warm, wet mouth fully engulfed me and she started moving up and down on my stiff pole, all I saw was peaceful, perfectly flat white behind my closed eyelids. Her twat was in my face, and I could smell her sex. I was in heaven.

Still providing gentle, sucking pressure on the head of my shaft, Hannah squeezed my balls once. Then, she ran her fingers gently over them. It was the kind of touch that you wouldn't think would even register, but it somehow gave me the chills, and that was it. I immediately shot my wad.

There was so much cum, that I'm shocked she didn't choke on it. When Hannah released my dick, she flipped around and carefully opened her lips to show me my load. Her mouth was fucking full. Little drops of my semen ran down her chin. I was a little embarrassed by the sheer volume I had produced, but I was also kind of involuntarily proud of myself.

Hannah quirked an eyebrow and swallowed my cum like a shot. She cleaned up the drips in the corners, sucking them off her fingers exaggeratedly. My girlfriend opened her mouth again, teasingly displaying its new emptiness for my inspection. After that, Hannah theatrically licked her lips, smiling lasciviously at me as if I had given her a delicious treat.

Show apparently over, she unceremoniously snuggled deep into the crook of my arm. She fell asleep easily, but I was suddenly wide awake. I knew in that moment, without a shadow of a doubt, that Hannah was going to be the most important bet of my life.