Horny Student, Extreme Bet

He gave me a moment to catch my breath, then he straddled my chest, unzipped, and pulled his dick out. It was quite nice, although considering what he obviously planned next, perhaps a bit bigger than I prefer. He didn't do anything crass like grab my head and force his hard-on between my lips, but he quickly placed his tip, swollen, dark red, and glistening with pre-cum, right in front of my face.

Still telling myself that one more step would finish things, I opened my mouth and drew him in. The manic fluttering in my gut increased, now consuming my entire lower body, although I still stubbornly tried to ignore it. At first I just held his tip between my lips, not moving except for swirling my tongue on the underside. Then my competitive side took over -- if I was going to do this, I was going to do it well, dammit, and give him the same level of pleasure he gave me. I began bobbing my head forward and back, still sucking deeply. I intended to build up to long strokes, but he took over.

He thrust in and out of my mouth quite firmly, leaving me to suck, which I did as hard as I could. He plunged deeper with each entry, pulling out to where only the very tip remained between my lips. I fisted the base of his cock, twisting my hand in rhythm with his thrusting, adding friction, but also blocking him from penetrating my throat. He kept his stroking luxuriously slow, taking his time, enjoying the soft warmth of my lips and tongue, obviously confident he didn't need to hurry. My groin sizzled harder than ever, and my mind did flip flops, trying to comprehend that there I was, on a deck chair beside the pool in my back yard, sucking a student's cock. I couldn't bring myself to see if Chris was watching from her bedroom window, but I'm sure she was.

Brandon's thrusting became more urgent and uneven, almost awkward, and he began to sound out of breath. A couple of strokes later he pulsed stream after stream of warm goo onto my tonsils. He stroked my throat to make sure I swallowed. Looking back, it was the one thing he did that I resented -- I was going to swallow anyway, but he made me feel small, like he thought I was either an inexperienced teenybopper who had to be shown the basics, or a defiant little pet being difficult about taking her medicine.

He settled back on his haunches to catch his breath. I still thought, 'Okay, now that we got all that out of the way, we can proceed with tutoring.' Wrong again.

He parted my knees and dived between them again. The quivering I felt down there had grown so intense, I'd be surprised if he didn't see it. He surrounded my slit with his mouth, sucking all my soft fleshy bits between his lips. He set his mouth in heavenly motion, and in between tongue strokes, he moaned, "Damn, this is sweet -- I can't get enough!" He settled in for the long haul, although he took brief breaks to shed his shirt, then a bit later his pants, and finally his boxer briefs. What he did with his lips and tongue was pure magic. He was relentless, and although it took quite a while, his persistence won out and I came again, hard. He looked quite pleased with himself.

I guess I could have stopped him before he fucked me, probably should have stopped him before he fucked me, but my stubborn side didn't want to admit to Chris that I violated her rule. No, that's an excuse; by that point I needed him inside me so bad I couldn't see straight. I mean, I shouldn't have enjoyed any of this, but what Chris said earlier was right, not only that Brandon wanted to fuck me, but also that I had gone without for a while. What no one realized was how intuitively Brandon would do all the right things to me. I still wasn't sure I should be allowing any of this to happen, but my body overruled every reasonable thought I had about why not.

Brandon was utterly sure of himself. He knew exactly what he wanted, and being given an opportunity, even a reluctant one, he was taking it. And to be honest, once I accepted that I had lost this bet, and finally got my inner voice to shut up, I knew what I wanted, which was pretty much exactly what he was doing.

He graciously gave me a moment to recover from my O, gently kissing the hyper-energized skin around my slit, then he crawled up my body, licking, kissing, and sucking along the way. He carefully kept himself positioned between my knees, preventing me from closing them. He paid my boobs extra attention as he passed them, kissing them, nibbling on them, tickling the nipples with his tongue. He mumbled something, which might have been "Damn these are sweet."

When he got even with me, he tucked his chin into my neck and sighed heavily behind my ear -- he had noticed that my hairline is super-sensitive. Extra points for paying attention!

I was still soaring from the rush of his breath on my neck when I felt the tip of his cock nudging my nether lips apart. Okay, enough already, it was time to put a stop to this.

Shit, who am I fooling... I curled my legs around his, grabbed his butt, and slowly pulled him into me. I was so ready, he slid smoothly all the way to the hilt on the first push. He held there a moment, completely still, letting us both enjoy just how completely he filled me. He slowly rolled his hips, pressing the base of his cock tightly against the top of my opening, giving my clit a firm nudge.

He didn't pull any length out, he just reduced the direct pressure from his groin against mine, letting my clit feel its absence before he pushed back against it. He did that again, then he added a tiny amount of length, not really a thrust, just fully un-touching my clit before pressing back hard against it. I curled my hips up to meet his when he pushed back in, then when he pulled back I did also, increasing the difference between 'in' and 'out.' When he pressed tight against me, he rolled his hips in a slight circle, adding a bit of lateral friction to my clit -- it was heavenly.

At first he showed no pattern -- pressing against my clit then pulling slightly away, then pushing back in, all luxuriantly random. But it began to take on a recognizable tempo, slow and strong. I matched it, mini-thrust by mini-thrust. He added some depth, and I added a bit more. Before long, we fell deep into the throes of that ancient, primal human rhythm, fucking. Every time he was at the bottom of his stroke, he rolled his hips slightly sideways, and I rolled mine in the opposite direction, both of us making sure my clit got its extra little nudge. He stayed slow, but gradually abandoned soft and easy, stroking me long and hard. It was animalistic, fierce, crude, ferocious, fabulous, and perfect -- exactly what I needed.

He separated from me and I groaned -- I needed a dick in me,now. He flipped me over onto my knees and plunged back into me, taking me doggie. I'm not a fan of doggie, I've never been able to cum that way. I needn't have worried; he gave me everything I needed and more. For the very first time I saw how exciting being on all fours can be, how the animal crudeness adds an extra level of excitement.

He slammed into me relentlessly. He reached around my waist, cupped my boobs and massaged them. He pinched and twisted my nipples, and that finished me off -- I launched straight into orbit. I fell forward, pulling my tits out of his hands, my shoulders slumping down onto the deck chair. I lost my leverage for pushing back onto him, but he made up for it by grabbing my hips, pulling on them for power. He didn't miss a beat, his thighs slapping hard against mine. My orgasm went on and on and on, blissfully seeming like forever.

He finally slowed, and I began to float back down to earth. I was completely spent, but he hadn't cum. He had given me three powerful orgasms and only had one himself, so even as wasted as I was, I felt like I 'owed' him another one. I gathered my wits and turned around to face him, thinking maybe I'd finish him in my mouth, even though his dick would be covered in my juices and I prefer not to taste that.

He had other ideas. He pushed me onto my back and laid his middle finger on my lower lip. He said, barely whispering, "Cover it with saliva."

I gave his finger a mini-blowjob, leaving as much thick spittle on it as I could. He lifted my legs by the ankles with his other hand and placed the tip of his wet finger against my asshole. He pressed inward, wiggling to find the soft center, pushing until it began to slide in.

My thoughts clanged together like a multi-car accident on an icy street. Hold it right there, buddy... now you've gone too far. I don't do anal, end of story. I've been with a lot of guys who wanted to, and several of them convinced me that they knew the secret: do these things in this order, and it won't hurt. Wrong! It hurts to do it there, period. Every time, no matter who's doing it and what he claims to know. Brandon's free pass to my body was over... soon. In order to satisfy my stubborn streak, I needed to wait until it actually did hurt, then I could justify shutting him down. I wouldn't be breaking Chris's rule, because I never agreed to do anything painful. Besides, I doubted if even Chris expected me to allow him into all three holes -- a trifecta -- no, a tri-fuck-ta.

Something weird happened, though. He slowly, firmly pushed his finger further into me, deeper and deeper, knuckle by knuckle, until it was buried in me, and it didn't hurt. He pulled it out and pushed it back in, then again, slowly at first, then picking up a little speed, and before long he was finger-fucking my ass. And it still didn't hurt. WTF?

He lifted my ankles higher, pressing my thighs tight against my boobs, drooling more saliva onto his finger until it slid in and out as smoothly as if it had store-bought lube on it. I kept waiting for it to hurt, so I could stop him. The thing is, though, it didn't hurt. At all.

He moistened a second finger and eased it in beside the first one. Two fingers felt more than twice as big as one, but the pain I feared still wasn't there. He dribbled more 'lube' until both fingers were buried up my butt as far as they would go. He began to double-finger-fuck me, twisting the angle of his hand every few strokes to stretch me in all directions, drooling more saliva as needed.

Although it still didn't hurt, two fingers stretched my ass ring so tight they didn't slip in and out nearly as easily as one finger had. Brandon was far away in his own world, focusing on his conquest rather than my comfort, but even so, he sensed I was uncomfortable. "Relax," he said, helpfully.

"I don't think I can, that's not enough lube."

"You might be right." He pulled his fingers out and picked up the sunscreen, squinting at the fine print on the label. "Contains aloe," he said, "and no glycerine. Perfect." He slathered both fingers in oil, and pressed them back into my ass. It wasn't as bad as before. Actually, it not only didn't hurt, it wasn't even uncomfortable. To be honest, it felt good. I never imagined there was any way having someone's fingers up my butt could feel sensual, even erotic, but it did. Somehow the warm slipperiness of the oil made his fingers feel like they belonged, and it actually made the hair on my arms stand up.

He continued double finger fucking me, adding more oil not only to coat his fingers, but also leave a slippery glaze on the inside of my ass ring and inner channel.

My ass must have felt like it was loose enough. He pulled his fingers out, grasped my hips with both hands, and pulled me sideways so my butt hung half off the side of the deck chair. He knelt on the deck and lifted my feet up, placing them together on his shoulder.

He drizzled sunscreen onto his dick, and used my hand to smooth the oil around. When his dick was nice and slippery, he placed the tip at my entrance. He paused briefly. He might have been waiting for a 'yes' from me, but I wasn't going to start granting him permission at this late stage. However, I didn't say 'no' either -- damn you, Chris, damn your rule, and damn my stubborn streak.

He clearly took the lack of 'no' to mean 'yes,' and began to push his dick in. I tensed, certain that refusing to break Chris's stupid rule was a huge mistake -- this was going to hurt like hell. He pushed in slowly but firmly, and I braced for a tsunami of pain. As thoroughly lubed as his cock and my innards were, though, it slipped in easily. Painlessly. Sensually, even.

An inch or so in it met a slight resistance, and I stiffened -- now it was going to hurt. He paused briefly, then pushed past it -- no pain. He finally stopped when he was about half in and held still. I felt full but comfortable, my guts awash in a deep warmth. His cock seemed to radiate an exotic animal heat that felt almost magical. He slid out to the tip, paused, then pressed in again, going a little further this time. He held in place for another long moment before sliding back out. He did that several times: push in a bit further than before and hold in place for a long moment before pulling back. If his plan was to let me adapt to the intrusion bit by bit, adjusting to his size each time he paused, then to my amazement it worked -- it not only didn't hurt back there, but it felt lush and deeply satisfying. He continued going deeper and deeper until nearly his entire length was buried in me. He held for a long time, letting me feel his length, his girth, how firm he was, his glowing heat.

I couldn't believe I had a dick up my ass and it felt so wonderful. He began stroking, slow but firm. Out to the tip, in to within an inch of bottoming out. He picked up a little speed with each push, settling into a nice medium tempo, emphasizing the length and friction of the thrust over its power. It was sensual like regular fucking, but different. There's no clit back there, of course, but what I've read since is, there are millions of extremely sensitive nerves. Every one of them seemed happy to have his cock slide against it. On top of that, I felt an extra buzz from doing something that had always been so 'naughty,' so taboo -- didn't expect that!

Clearly the pain I expected wasn't going to happen. I pulled my ankles away from his shoulder and spread my knees, allowing his final inch into me. He picked up a little speed, drizzling more sunscreen on his cock every so often to keep everything nice and slick. Now that he was fully 'in,' there was no more need for gentleness, and he fucked me hard, slapping his thighs against my butt. I was amazed how good it felt, and it got even better when I began to stroke with him, meeting each of his thrusts, pulling back when he did. My clit may not have been getting any direct stimulation, but something was going on down there, and whatever it was felt freaking amazing.

Before that afternoon, if you had told me that I would not only tolerate being butt-fucked, but enjoy it, I would have laughed in your face. There we were, though, his dick, my ass, his length, his thickness, my depth, my smile -- unbelievable.

His breathing began to change -- he was about to cum. He thrust a little faster and pressed in a little harder. He moaned that he was cumming, and vibrated a finger across my clit. To my complete amazement, every muscle in my body pulled itself rigid in sexual ecstasy, every nerve in my body howled in pleasure; in other words, I came with him. I never knew it was possible to cum from anything anal. And I never knew I could cum four times! He groaned deeply; his jizz made my channel a little slicker, making his last few strokes smoother. His dick had to be ecstatic at how tight my ass was. I groaned deeply with him; he had done everything so well back there my ass was in heaven.

He slowed, and I gave him a body hug by crossing my ankles around his lower back. He kissed my lips, for the first time I realized. I kissed him back, but I wondered what it meant to him. Did it signal that his conquest was complete, another notch in his belt buckle, time to move on to the next target? Or was it a message from the painfully shy, inarticulate guy that Chris described, daring to express feelings that I had been oblivious to? Did he see this as a starting point, or was he just another guy who got his willie wet and would now focus on his next conquest?

I also wondered what it meant to me. On one hand, he had quite crassly used my body for his own satisfaction without much regard for my feelings. I should resent that -- deeply. On the other hand, what he did to me was freaking amazing. He introduced me to several sensations I didn't know existed, and left me with an almost overwhelming afterglow. What should I do -- continue to dismiss him as someone who didn't particularly matter, or begin to look at him differently, consider parlaying the killer sex into something deeper?

All that noise was my inner voice reawakening, and I told it to shut up. I would sort all that out later. All I wanted to do at that moment was bask in the double satisfaction I felt. First, I took everything he gave me without violating Chris's rule. She may have won the bet about his intentions, but not blocking him was a major battle in that war and I won it -- take that, Anti-Chris! And second, in one afternoon I enjoyed doggie, enjoyed butt sex, and came a mind-blowing four times, all for the first time.

While all those thoughts pinballed around in my head, his cock, still in my ass, slowly deflated, shrinking back to its normal at-rest size. He rested his head on my shoulder, his erection fading until his cock finally slipped out of my butt. His cum leaked out and dribbled down my crack.

Although I was so worn out I could barely focus my eyes, I noticed the drapes on the bedroom window rustle. I wondered how long the Anti-Chris had been watching -- probably the whole time, the pervert! I'm sure she was celebrating her victory with a huge grin on her face, and I predict I'll be hearing about this for a long time. When Brandon was looking the other way, I stuck out my tongue and flipped her the bird, which she told me later made her laugh.

Brandon stood, leaving my body disarrayed in a post-multi-orgasmic puddle on the deck chair. He pulled his clothes on, humming a simple, happy melody, but saying nothing. I heard him set something on the table, which I discovered later was an envelope containing my fee for the tutoring. "Best lesson ever, Ashley."

Standing over me, he leaned down, squeezed my tit, patted my racing stripe, and kissed my forehead. "Same time next week?"

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