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The Tutor Fantasy

Category: Anal Sex
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It’s a late summer night, not too hot. The fan and the crickets compete for sound dominance. I’m tired, but I can’t sleep and I want to come. Dan is lying perfectly still next to me, hands folded neatly across his belly. I know he’s not asleep. He never falls asleep before me. I glance at the clock–six hours and we have to be up. If we fuck, we’ll be lucky to get five.

I roll over and kiss his jaw. He doesn’t move. He’s thinking the same thing I am–six hours–and he’s going to ignore me until I go away. I nibble his ear. I suck at his neck. My hand creeps down his belly. Nothing.

I nuzzle in closer to him, caressing his ear with my tongue. I whisper, “I know I’m failing geometry, and I know my parents only hired you to tutor me–but if you take the test for me, I would so totally suck you–” he groans, and I know I have him, but I add “–but you so couldn’t come in my mouth.”

With that, he’s on me. He pins me and shoves up my tank top and takes my tit in his mouth and sucks the nipple hard, so hard that I imagine it turning giant and purple, and then he’s grabbing my hair and whispering fiercely, “If I take the test for you, you’ll let me come in your mouth, your hair, your pussy, your ass–anywhere I want.”

I’m wet in an instant, just as he went hard in an instant, and we’re off.

We have to pull back for a moment, setting things up to make the fantasy work. He props himself up on his pillows, and I jump out of bed to switch on a nightlight so we can see something of what we’re doing without being blinded by a lamp. I slip into a pair of cotton panties and shorts, even put on a bra under my tank. I like to be undressed, I guess; not fetish-level, but it’s important to me. Dan doesn’t care so much, or maybe it was too hot to add more clothes. He’s in his underwear, anyway.

Now we’re ready.

I sit next to him on the bed, cross-legged, and put a finger childishly into my mouth. This bad-at-geometry girl–in my head I’ve named her Lee–regresses when she’s confronted by awkward situations. “I don’t know,” I say dubiously. “I don’t think that’s very fair, to ask me to do… all that.”

“What’s fair?” he asks off-handedly. He folds his arms behind his head and stares at the ceiling. “I mean, if you don’t care about what college you get into, I guess it doesn’t matter. I can just tutor you, take your parents’ money, and I haven’t really lost anything… But taking a test for you. That’s something else entirely. If I get caught, I want to at least be able to remember fucking you in the ass.”

My pussy is twitching, practically aching, and if he rolled me over and slipped his cock into me right now, I’d probably come on contact. But that would certainly ruin the fun, so I just continue to keep my finger hooked in my mouth and staring at him. “I can’t,” I whisper. “I’ve never done… any of that… with anyone… before.”

“You offered to suck my cock, and you’ve never done it before?”

I shake my head.

“What makes you think I want a rank amateur anywhere near my cock?”

“Maybe… you could teach me?”

He grunts, then reaches up and grabs my head, pulling it down to his cock. “Open your mouth,” he growls, and pulls his cock out of his underwear. He’s stone-hard, fully elongated, and I want him in my mouth so badly that I’m salivating. “Keep your jaws open wide–I don’t want your teeth on me–and close your lips around me. Move your mouth all the way down on my shaft until you meet the top of my fist. That way, you’ll know you’ve gone far enough, and you can pull back up.”

“Oh… kay,” I say shakily. In character, I’m dubious. In reality, I’m so ready, even though he’s bending me in half at the worst possible angle. I don’t know if Lee here is smart enough to protest or shift. She probably will be when I’m too stiff to continue in this position, though, I decide.

I decide to be as literal as possible, given Dan’s instructions, so I keep my jaw open as wide as I can, not touching his penis even the slightest bit as he pushes me down onto his shaft. My lips bump into the thumb and index finger curled around his penis; my downward movement stops, and I clamp down on his cock, full on suction. His body jumps, and he groans and thrusts at my mouth. I smile around his cock. Victory. I did it wrong but in character, and he still loves it.

He guides my head up and down on his shaft a few times, and I luxuriate in the feeling of the soft-hard tip of his cock stroking the back of my tongue. I don’t know what that’s all about, why that sensation feels so good to me. I don’t think that’s what the oral fixation is about, but maybe I’m wrong, and I’m just orally fixated. I just know I love it, and whether it’s a thumb or two fingers or a cock aiming at my throat, it’s almost as good as coming.

Lee catches on–she’s a faster learner than her geometry grades would indicate–and I’m bobbing up and down dutifully, hitting Dan’s knuckle with my upper lip each time I go down. My bottom lip is hitting the crook of his thumb, and sliding against it slightly, and I’m digging that, too. The roughness of the skin on his hand contrasted with the softness of the skin of his cock heightens the sensations around my mouth. My lips are tingling.

Then Dan fucks me over a bit–as I’m slurping on a downward stroke, Dan takes his hand away, and I keep descending, searching for that elusive circle of Dan’s thumb and index finger that will let me know that I can pull backwards. It’s not there! I press my mouth all the way down to scratchy pubic hair, practically gagging as Dan’s cock slides deep into my throat. The bastard got me to deep-throat him!

Lee wouldn’t know what to call it, but she surely wouldn’t like it. I pull back with a slurping pop and squawk, “What the hell was that?”

“Just getting you to do what you said you’d do,” Dan said, and pushed me back onto him.

I make some muffled protests around the meat in my mouth, but his hand is on the back of my head again, and I’m sucking and slurping up and down. I pick up the speed and increase my tongue-action, and Dan groans slightly, then more and deeper. “Oh, yeah,” he pants. “That’s the stuff.”

My cunt is an aching hole by this point, and I hope this won’t last much longer. I wiggle out of my hunched-over sitting position and make it to all fours. Since this deepens the throat action, Dan doesn’t complain, in character or out. I then wiggle my rear end around so that my ass is prominently displayed in Dan’s view–prelude to a sixty-nine, kind of, though that’s not exactly what I want at this point.

Dan obliges by reaching out a hand and caressing the globe of my ass, clutching at the flesh now and then as I hit a particularly sensitive spot with Lee’s studied lack of finesse. Soon enough, though, squeezing and caressing turns into the stroking of my crack, back and forth, forth and back, over the fabric of my shorts and panties. I whine and wriggle, and the friction increases, until he reaches out and cups my pussy, pressing against it. I push against his hand, rubbing myself semi-furiously–but this is not to be. I’ve stopped paying attention to the cock. Dan grabs my hair again and reminds me of my primary duty.

When I’m back on course, though, he returns to my ass and my crack. He slides two fingers under my shorts and begins running his fingers over the crotch of my panties. “Your underwear is wet,” he whispers. “You slut.”

I whimper into his balls, and continue pumping my head.

He slides two fingers now into my panties, and runs them up and down the actual crack of my flesh, and I tremble. He goes slowly. The way I’m presenting, my lips don’t open automatically–he’s going to have to work for it, and he’s going to make me wait, too. One stroke, two strokes, and he’s still only parting pubic hair; three strokes and he’s found the oozing seam. Four strokes, and he’s perhaps a centimeter in. Five strokes, and he’s parting the outer lips. Six strokes and he’s–oh, god. My clit.

I press all the way down on his cock and moan into him.

He stabs two fingers into my sheath, and I lift my head from his cock and cry out. “Ah! Ahhh! Ahhhhhh!”

“You’re very tight,” he whispers, and now that I am off of him, he flips me over, onto my back.

He crawls across my body until his cock presses up between my legs, stopped by the firm, wet fabric of my cotton underwear. He pulls aside the crotch and the head of his cock probes for my entrance. “Little rich bitch,” he whispers, “too busy running around town in short skirts and staring down her nose to learn any geometry… what are you learning today, hm?”

“I–I–” I gasp. He pushes with his hips, nosing his penis into my pussy, and I decide this is the point where Lee would really have second thoughts. “No, I can’t let you!” I cry, and attempt to wiggle away from him.

“Hold still,” he grunts, giving short little pushes until the head of his cock is engulfed by the entrance of my sheath. “I’m going to take that test for you, and you’re going to pay. It’s too late now. Too. Late.” And with that, he drives the length of his cock into me.

I cry out loudly, a mix of Lee’s protest and my ecstasy, but Dan crams two fingers that smell of my pussy into my mouth, stroking against the back of my tongue. He adds a third finger, and grinds his hips against mine. I buck against him and come.

“Holy fuck,” he says, and pulls out of me, leaving me to spasm on my own. He pants above me–recovering from the brink, I decide–but slides a hand down between us, to thrust a couple fingers into me to enjoy the last bit of my orgasm. My pussy clenches around those fingers, which waggle upwards to hit my g-spot, and my climax increases in intensity.

I am awash in lassitude when Dan leans down and tongues at my breasts swelling above my bra. Only when he slides up to whisper in my ear do I remember that we’re not actually done yet. He hasn’t come yet. “Up on your hands and knees, slut,” he growls, and I oblige.

It’s the same position as while I was blowing him, but this time, instead of pushing aside the crotch of my shorts and panties, and pushes them down around my knees, so they hobble me slightly. He strokes me with his fingers, and then with his cock, rubbing it up and down my pussy slit. He presses the cock against the opening to my pussy and pushes forward slowly. “I’m watching your pussy take my cock,” he informs me. “Your lips are so swollen and pink and wet.” He rocks his hips back and forth, pulling out nearly all the way and pushing deeply back in. I alternately sigh and squeal with the varying intensity.

He pulls out of me with a sucking sound. “You are so fucking wet,” he says. “Slick.” He scoops some of the liquid out of my pussy and rubs it around my asshole, then rubs my slickness into it. He pushes his cock back into my pussy again, rocking in and out, in and out, while his fingertip pushes at my wet asshole. “I don’t think you even need any lube!” he says, and slides his cock from my pussy to press the head of it against my anus. I moan at the sensation of stretching, and drop my face to my arms. He pauses. “You alright?”

“Yeah,” I say, but it’s nearly a whine. “Don’t stop!”

He is kind, and rests for a moment with just the head of his cock popped inside of my ass, waiting for my gasps and pants turned slowly to moans and whimpers. Then slowly he begins to force his way into my ass again. Doesn’t seem to matter how often we do this, I always feel like I’m being split open. Lee, poor deluded bad math student virgin, would probably feel even worse.

He is buried to the hilt now, and we’re resting again. Dan’s mouth is right above my left ear. “Your ass is so tight,” he murmurs. “So good. I love you, baby.” I’ve never felt closer to him. We rest there together. “So tight!” he exclaims again, and I can feel his cock pulsing inside me. He might be coming. He might just be really excited. “You ready to fuck?”

“Yeah,” I whisper.

He moves hesitantly at first, just a little in and out, and it’s so intense. “Oh, god, it’s so big,” I sob–not really crying, but it’s hard to control my voice, my emotions.

“You okay?” he asks.

“Yes. Yes! Fuck me, Dan.”

“Yeah. Yeah, I’ll fuck you.” He starts moving again, and I’m screaming into the mattress, and he’s murmuring sweet things and hot things and dirty things into my ear. My asshole still feels like a hard, tight ring to me, and I have to relax. My hand creeps down to my pussy, and I feel for my clit, which is swollen and ready again, and feels like it’s hanging hugely down. I soak my middle finger in my juices briefly, and then rub the pad of it over my clit, and I’m coming again, coming hard, hard, hard, as Dan saws in and out of my ass.

“Oh, yeah,” he mutters, and holds still, feeling the sensations of my orgasm as it spasms through my body. I think that surely this time he’ll come, but still he doesn’t. When the wave has passed, and I’m panting into the mattress, he extracts himself from my ass. Before I can ask what he’s doing or flip over or anything, I realize he’s straddled my back and his hand is on his cock. One–two–three strokes, and he’s coming. Warm semen lands on my cheek, on my ear, at my hairline.

“What–what are you doing?” I ask indignantly.

“Coming in your hair. As promised.” He shudders to a halt, done spewing on me finally. “Now, I’ll be happy to take that test for you,” he says, lying down beside me and taking me into his arms. We lie still together for a moment, utterly spent. I glance just once at the clock to see–four more hours to sleep before we have to be up–and then we’re asleep.

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