Dylan Gets Luckier

I was right, of course.

I leaned in for a smooth, deep kiss. He was a decent kisser, at least, but then again a lot of high schoolers were. His tongue tasted faintly of marijuana, a fact I stored away for future use. I lavished extra attention on him, sweeping his teeth and making sure the kiss was nice and wet. I was not usually much of a kisser; I know a lot of women get all weak-kneed at the prospect of swapping spit with their men, but I've always just seen it as the least of all sex acts. And, thus, not very important.

Good thing Dylan took kisses more seriously, but then his hormones were probably so charged up at that point that a mere glance at my nipples would probably get him going. Whatever; his cock was firming in my hand. I gave him another sensual kiss. "Get that dick hard for my cunt, Dylan," I breathed in his ear. He sucked in a breath, no doubt astonished at my language. "I told you we're not done."

I shook his pole a bit, then gave it a squeeze before I stepped back to get naked. I could feel my neck and chest growing warm; I whipped my bra off, starting to breathe a little harder. My nipples, always embarrassingly long when I was aroused, felt tight and hard. He was still blinking at my tiny boobs when I paused and smiled pleasantly at him. "If you'd care to do the honor of taking down my panties," I said, "feel free." I stepped back toward him, his cock now waving halfway up, and raised my arms majestically.

"Wow, Mrs Torrey. Er, Gina. Just wow." He leaned forward and surprised me with a swift kiss to my bony cleavage before, with a shrug, beginning to gnaw on my nipples. I couldn't resist a low groan as his teeth closed around me, pulling hard.

"You trying to turn me into a B-cup, stud?" I laughed merrily. He was just so cute! His hands, meanwhile, had found my waistband and worked a finger into each side. The green panties came whisking down, not without a brief hangup as my moist crotch clung wetly to the liner, and I stood nude before him, my lace-topped stockings only slightly askew. I let him suckle a few moments longer, losing myself in my arousal, before pushing him back. He was, thank God, solid once more, his cock seeking my cunt already, the thing pulsing long and fat-headed toward the ceiling. I smiled, licked my lips, and reached high to take out my ponytail.

"You," I said, shaking out my hair, "need to make up your mind how you want me. Decide fast, though, or I'll make up your mind for you." I turned, letting him get his first look at my naked ass, then pranced away to stand on the floor beside my own desk, under the windows. "I figure the floor's good enough for today." I grinned. "Easy cleanup."

Dylan was shaking his head slowly. "This is fucking incredible," he announced. "I - uh, Gina, I..."

"Cat got your tongue?" I grinned wickedly and, my back still to him, folded my legs

and fell to my knees. "Let me help you decide," I purred, stretching my body as long as I could and laying my elbows on the floor. The dry air of the classroom was cold on my bare ass, raising goosebumps as it waited for him. My hair fell around me, brushing the floor and shutting out the light; I smiled to myself, bowing my head as I reached my right hand back, two fingers extended with the muscle memory of long practice, and pried open my cuntlips.

Well, after that it was only a matter of time.

Grown men can't resist a hot, skinny woman in stockings bent naked in front of them; a kid like him had no chance at all. For the second time in twenty minutes I heard Dylan Rotolo's feet smacking against the floor as he came to me with a hard, ready dick. I was breathing calmly and evenly, waiting as I had for many other men. My only concern was whether he'd understand that he'd need more than one try to get into me; I'm one tight bitch, and sometimes it takes awhile.

That's when I learned that Dylan was either very astute, or that he'd fucked a lot of other tight bitches. I heard him hawk up a large ball of phlegm as he approached, heard the slippery smacking noise as he licked his fingers, and then felt those slick fingers enter me, no longer shy at all; he pawed at me a few times, drying his fingers on my lips. I tried to keep from laughing out loud, I was so excited; his fingers wiped at my greasy snatch, pinching and rubbing, then I felt his big hands gripping the sides of my ass as he got his legs into position.

The air was thick and heavy with sex as he braced his knees outside mine, getting his pelvis low enough to drive into me. I kept my fingers helpfully where they were, and my whole body shuddered as I felt his touch on my cunt. With both hands on my hips, there was only one thing that could be poking me there.

For such a young man, Dylan showed remarkable restraint when he breached me. I'm not sure why, but the impression I'd gotten from Shannon was that he'd been barely more than a virgin, shy and bashful. But I begged to differ; there he was, grasping me firmly, pushing into me with confidence and skill, fully aware that his head was too big for my slit.

I caught my breath; even someone as jaded as me could appreciate that the moment of entry has a certain magic, no matter who's doing it. I put both hands on the dusty floor to brace myself, and eased back as he moved in. He withdrew from time to time, letting my little hole recover, but when he came back he always sank a bit deeper. I looked along my body, upside-down between my legs, gauging how many more thrusts it would take before his balls hit my clit. Five, maybe? I grinned as I counted down to see whether I was right.

Well, I was two off. Seven strokes brought him fully into me, his wide head pushing at my cervix while my tunnel recovered from its passage. It wasn't the most comfortable sensation in the world, but who was I fooling? I was getting rammed by my own student, in my own classroom, and that alone made my body scream with excitement. I giggled triumphantly as my hand returned to my cunt, feeling the shaft inside me, dancing over my own clit.

He pulled back one more time, then drove back into me, grunting. Oof. I'd need to limit the kid; I just wasn't going to stretch enough. I never minded being sore after a good, sweet fucking, but I didn't want that rampaging cock of his to do any permanent damage in there. I let him have a few more full strokes before I lowered myself, straightening my legs to go prone. That way, he could still fuck me from the rear while not getting all the way in. I kept my back arched and my elbows down, wincing as my whole body landed on the cold, hard floor.

Dylan didn't miss a beat. I was small enough that his hands fit all the way around my sides as his thumbs met near my spine, an incredibly submissive feeling. He was energetic enough that I didn't even bother shoving back, his thick head now spearing my clit and my g-spot. My motto is 'cum early and often,' and I didn't disappoint myself; I twitched and yelped a tad as my first mild orgasm swept across my overheated body.

My new guy turned into an animal, his hard legs and chunky ass driving his dick into me hard and fast, his saliva dripping onto my head as he groaned unintelligibly. My hair still obscured my face, but I kept up a steady stream of dirty talk. "Yeah," I hissed. "Drive that cock into my nasty cunt. You know you want to cum in me, you young stud. Keep on fucking." This was great, and a new plan was hatching in my fevered brain.

See, I hadn't planned on telling him I knew he'd fucked Shannon. Maybe later, but not now. But the irony was becoming delicious now, and I knew he had to be more excited by me than he had been with her; his hands were mauling my tiny body as his dick took its pleasure out of my cunt. He was nothing like what Shannon had described, an enthusiastic but generally polite boy with a nice penis. No, the guy on top of me was a rutting beast, trying hard to fuck me clear through the floor. He was muttering, too: "Take it, Gina, you slut," I heard, and my heart leapt. No way Shannon had heard anything like that.

I came again, more powerfully, moaning.

"Let me know before you cum, Dylan," I told him, thrilled at having made my decision. He'd never forget shooting in me, not after what I had to tell him. His strong hands were kneading my asscheeks now, and from his strangled gasps it probably wouldn't be long.

"Ohh, yeah," he chanted. His foul breath drifted around me like a cloud. "I'm fucking my math teacher!"

"Hell yes you are," I cried. "You're fucking me like a goddamn machine. Keep doing me, you bastard." I started to hear a squeaking noise; my sweaty body was sucking at the smooth floor as he moved me around with his dick.

"Shit," he spat. "Mrs Torrey... Gina... I'm about to cum..."

Perfect. I let him have a few more irregular strokes, enjoying the feel of his legs outside mine, of his thumbs clawing my butt open, before I lifted my head and tossed my hair back. He could finally see my face, a feral gleam in my eye as I stared back at him. "Tell me, Dylan," I asked in a low voice, the volume of my voice rising and falling in time with his thrusts, "does my pussy feel better than Ms Boyle's?"

Dylan's sudden gasp was very rewarding, his cock totally hard between my legs, still jammed into my cunt. I smiled gaily, laughing as he came. I could feel his semen splattering out of me, overflowing; I pushed my ass into the air one more time. "Mmm," I groaned. My stockings would be ruined, but whatever. He flopped over me a few more times, breathing harshly.

"What the... what the hell, Mrs Torrey?" he said at last, propping himself up with his arms. I could feel his skinny teenage abs against my butt. "How did you know Ms Boyle and I... had, um, fucked?"

I laughed at him, rolling myself half-over, his long cock flopping out of my snatch in a milky white flood. "Dylan, honey," I said, reaching up to lay my sweaty hand alongside his face, "Ms Boyle and I are good friends. We tell each other everything. Just about." I laughed again, still sunk in sexual exuberance, his face totally confused. His eyes were scanning my scrawny body, eventually fixing themselves on the sloppy puddle under my hips. I scooted my butt back, sliding through a floor slicked with cum and sweat. "It's okay, Dylan," I shrugged. "I don't mind. She's got better tits; I can see how you'd like her. If you want to fuck us both, I won't argue."

Which was true, now that I'd done him; I liked Shannon, and I wasn't usually the jealous type. I wasn't sure whether this thing with Dylan and I would become any kind of long-term operation; screwing your student is never, ever wise. But shit, I figured. If you've had sex once, what's wrong with twice?

Later, though. "Let's get cleaned up, honey. I've gotta go pick up my kids, and you... well, you've gotta do whatever you do."

He squatted, crablike, his cock dragging on the ground. "Gina," he said thoughtfully, still uncomfortable saying it, "do you think I can get a ride?"

"I just gave you one," I giggled, winking at him.

"No, I mean-"

"No, Dylan." I got to my feet and reached down to straighten my stockings. "No. We can't be seen together in my car, honey. You understand that?" I was trying to avoid the puddles. "This was fun and exciting, but I'll get fired if anyone finds out. You don't want that, Dylan."

"No!"

"No. So let's play it cool. Wipe yourself off, put your clothes back on, and walk back home." I was jamming a kleenex into my cunt, grateful yet again that I shaved. Cummy hair was a major pain.

* * *

Shannon looked over at me knowingly when I limped into the lunchroom the next day. She'd seen me walk like that several times. "Tough day at yoga?" she said, smirking.

"No, actually," I replied evenly, taking my usual seat. "I got fucked senseless by a long dick yesterday. Anyone want a tangerine? I've got extra."

Shannon laughed. Audrey Temple smiled wickedly. "Isn't Mike away on business?" she asked cattily. Poor Audrey. Nice girl, but she lived vicariously through women like me because she lacked the balls to cheat on her spouse. He didn't; I'd been fucking him off and on for a few months now.

"Yes, as a matter of fact. He is." I let her draw her own conclusions after that. Lucas was grinning in the corner, no doubt imagining me without any clothes. "Speaking of 'away on business,' Shan, isn't Leon heading out again on Thursday?"

"Yup." Shannon sighed. She didn't really love Leon, I knew, but she liked him. And she valued the way he gave her oral. Plus, their house was rented in his name, and she really liked the place. "Five weeks, minimum. Gulf of Mexico, this time; at least he'll be warm."

"Too bad you won't," I sniggered. "Your bed will be as cold as Audrey's."

"Fuck you, bitch," Audrey smiled.

"You first, bitch."

* * *

I was bored a couple weeks later, so I figured I'd go shopping with Shannon. She was always fun to do retail therapy with, as we had similar taste in underwear. It was a nice, lazy Saturday, and she wasn't answering her phone. Her house was on the way to the mall, so I figured I might as well swing by.

As soon as I turned down her street, I just about ran over that little whore Gretchen Barry, the fastest girl on the track team and, by all accounts, the biggest slut in the senior class. She paid me no attention as I swerved slightly, instead sprinting up the street with her stubby arms swinging in time with her oversized tits.

Whore.

There were other runners heading up toward me out of the salt marsh, so I slowed down and drove more carefully. Shannon's house was the last one on the left, a nice modern place with a big, spongy backyard that sometimes flooded. Her beaten-up Honda was skewed in the driveway; Shan was a poor parker. I pulled in behind her.

Then something struck me.

Runners, drifting exhausted out of the marsh: that was how Shannon said her torrid afternoon with Dylan had started. I took a closer look as the panting crowd came dribbling past. Hmm. Track and cross country had never been activities that drew any attention from me; I'd been a cheerleader, so any sport that didn't involve shoulder pads or at least jockstraps had never really been important to me or my friends. But a lot of these runners... well, they were pretty hot. Almost every one of them had a shirt off, the boys bare-chested and the girls in sports bras, all with long, graceful legs.

Why had I never noticed these people before? Shannon had been holding out on me...

And then my eyes went to her upstairs window, and I started to wonder why she hadn't answered her phone. I listened, and heard nothing but the rasping breaths of the passing runners. They were starting to recognize me now, a few of them openly staring in wonder that a math teacher would be arbitrarily standing out by the marsh, watching them thoughtfully on their Saturday training run.

I wondered.

The front door was locked, for Shannon Boyle was a canny woman. I'd been to her house many times, though, and I knew where she kept her key, but first I drifted around to her backyard to see if she was reading out there. No, but her Adirondack chair was out by the tree... and a book lay propped open on the footrest. My mouth fell open. No way. I swung my head toward the house, caught sight of an open sliding door with the screen door barely shut...

My eyes flickered up to her closed balcony door, a broad grin on my face now. Another runner came pumping past, sparing me an incredulous glance; it was Andrew Pereira, whom I'd awarded a D-minus last year out of the goodness of my heart. "Um... Mrs Torrey?"

"Keep it up, Andrew! You're doing great!" I had to get out of Shan's backyard, so I scuttled up onto the deck and through the screen door. I stood a moment, getting used to my surroundings; I was looking and listening for some very specific things, though, and soon I started picking them up: a damp athletic shirt in the middle of the room, a pair of battered old running shoes right next to where I was standing. Now I knew, and my grin turned into a soft laugh. Good for you, Shan!

There'd be some sweaty running shorts somewhere closer to her bedroom, I knew by then, and as I slunk across her living room I stepped over a pink tanktop, all tangled up with one of Shannon's 32B bras from Secret Whispers. I followed the trail, wrinkling my nose at a pair of nasty white socks of the kind Shannon would not be caught dead in. And then I reached the bottom of the stairs, and my straining ears starting picking up what I was expecting to hear.

A gasp, swallowing a little shriek that trailed off into a sigh.

I leaned against the bannister, trying to decide what I should do. The decent thing, naturally, would have been to leave, making sure the slider was shut and her place in the book out on the adirondack was marked, and let her have her fun. But wait; might there not be a way to give her even more fun? And have some of my own into the bargain?

She'd politely declined me when she was so, so horny last month and, in an excess of compassion, I'd offered to come over and get her off myself. And I would have done it: I'm not bi, but I love Shannon like a sister, and I'd been concerned about her. Now I started to think about that offer again, about my willingness to help her out sexually, and I decided to take a chance.

Besides, that shrieking, breathy gasp had gotten me horny with an immediacy that was, well, a little scary.

If things upstairs were what I thought they were, I'd be best off getting up there naked. And if not, well, then at least it would make a funny story in the lunchroom on Monday. So I slid quickly out of my clothes, adding them to the trail of cast-offs that went up the stairs. Mine I folded, though, and left in a neat pile at the bottom landing. While thus engaged, I heard another gaspy, moany noise from upstairs: definitely masculine. Cool. The only other possibility was that she'd been up there alone, taking care of business with the new vibe she'd bought last month. Now even that myth was debunked.

I strolled back across the room, stark naked, and calmly latched her sliding door. A runner coming out of the marsh probably saw me, but I didn't care very much. It was Jimmy Bielat, a freshman, so nobody would believe him. Then I shook my hair out and walked calmly up the stairs. Shannon would be freaked, probably even pissed, but whatever; I was betting she'd be pretty preoccupied soon enough.

Up the stairs, then, and I nearly stepped on his damp running shorts at the top landing. I investigated, pawing at them. They were the kind with the lining, Dylan's heavy male dick-smell strong, so I shouldn't see any more male clothing. I was still waiting on Shannon's shorts and panties. They'd have to be inside her bedroom, though. The door was just a few yards away.

The soft, subtle sounds of sex had been growing as I went up the steps, but I could tell they were trying to keep things a little bit quiet. Probably concerned about the runners outside hearing something. Still, there was no mistaking what had to be going on in Shannon Boyle's bedroom: low chuckles, more easy groans, an occasional very quiet slurping noise.

My grin grew as my cunt started to leak.

Just as I got to the door, I heard Shannon talk, low-voiced. "Doing fine now, baby; more of that." She ended on a whimpering, trailing moan, and there was her doorway; I saw her sensible cotton shorts right inside, with a pair of wicked sexy black panties just beyond. I nodded; with her coloring, Shannon would look dynamite in black lingerie.

Nothing for it now. I shook my hair out one more time, then sprang into her doorway.

Her king-size bed, of which I'd always been jealous, faced the door, so I got the full picture as soon as I showed myself. Shannon sat against the bleached wood headboard with her legs spread and thrashing. I'd never seen her naked before, and I was struck by the perfection of her body; she had outstanding breasts. Her lovely face was pointing down, her mouth open and her eyes closed; both arms wrestled with the object in her lap.