Free Rides

 "Hey, just relax and it won't hurt at all."

Squirting a line of lube down his twitching erection, Kainen watches the supposedly straight swim team captain lie naked on the beneath him, knees pulled up to his chest. Having bumped into him at a frat party, Kai noticed the swimmer was unable to pull his eyes away and eventually lured him into one of the empty bedrooms at the frat house. A quick grope and a handjob was all it took to get him naked and willing. 

"Just... don't tell my girlfriend, okay?" turning his head away, the jock bites his lip and whimpers in anticipation, dirty blonde hair falling across his face. 

"Of course not, now stay just like that." Kainen takes his phone and snaps a silent photo of his cock lined up with the swimmer's shiny lubed hole, making sure to get as much of the boy's face as possible. Tossing it onto the pile of clothes, he brings his attention back to the shivering mass before him. Kai places his hands under the swimmer's knees, pushing his legs back and leaning his body weight into the lean swim captain, the head of his cock meeting resistance. 

"Wait... I don't think it'll fit..." the boy's protest just spurs Kainen further, the tight ring barring entry slowly weakening  despite the cries otherwise. Kai  just smiles and moans under his breath as he feels the swimmer's hole finally stretching to accept him, each prod reaching deeper and deeper until the tip finally breaks through. Groaning in discomfort, the swimmer tenses reflexively around Kainen's shaft, unintentionally keeping him inside. 

"There you go, now try to relax. Don't fight it..." keeping the boy pinned, Kai lets him get used to the new feeling of being filled, the tight ring clenching and releasing in confusion around his shaft. 

"I'm... trying... It hurts..." 

"You're doing great, just breathe..." with another slow thrust, Kai forces himself deeper and grins at the low groan forced from the boy's mouth. Each inch that slips past the swimmer's constricting ring fills Kai with satisfaction, this popular, fit, athlete squirming on the end of his cock. Finally bottoming out, Kainen wiggles his hips in slow circles, letting his cock stretch the boy's insides. 

"You feel that? I'm all the way inside." letting the swimmer's leg fall, Kai runs a hand up the half hard cock lying flat against the boy's waist, fingers wrapping around and giving a slow tug. Hearing a soft whine in reply, Kai starts rolling his hips and properly fucking the tight hole wrapped around him. The music pounding up from the floor guides Kai's rhythm, the room filling with a mixture of heavy bass, skin slapping against skin, and reluctant moans. Holding the boy's leg up, Kainen rolls him onto his side and puts more weight into his thrusts, burying himself completely each time. 

"Hey, where's that huge dick all the girls keep chasing after?" gripping the base of the swimmer's soft cock, Kai wiggles it briefly with a laugh before digging deeper into the boy's insides. 

"I feel... I feel weird..." the swim captain pants heavily amid the mess of sweat and tangled sheets, his flaccid cock twitching from Kai's internal stimulation.

"Yeah? You gonna cum for me?" grinding steadily, Kainen makes sure to angle his hips properly to squeeze out a weak load from the boy's prostate, milky white liquid dripping slowly onto the bed "There it is... That's a good boy..."

Each new squirt makes the boy tense up again, massaging Kainen's cock as he drives forward. Kai spends the next few minutes milking his prey until he finally runs dry, cock twitching pathetically with a silver string of seed connecting the tip and the small puddle beside him.  

"You look so pretty right now, but it's missing something..." ramming faster, Kai gives a quiet grunt and pulls out, stroking himself over the swimmer before covering him with a healthy load of his own. Rope after rope lands on the boy's glistening skin, covering his midriff and chest. Taking his phone again, Kainen snaps a shot of the stained swimmer, messy hair in his eyes and too dazed to react. Throwing his clothes back on Kai leaves the swim captain naked on the bed, covered in cum, and makes his way back down to the party, taking a few shots before wandering back to his own pad and passing out in bed. 

*bzzzt* *bzzzt* *bzzzt*

A flood of texts shake Kainen awake, buzzing out of his pocket and onto the bed. Sitting up and rubbing his eyes, Kai searches blindly for his phone and grabs it, bringing up his texts. Not recognizing the number, he flips through the messages.

[What the fuck, Richie told me he saw you and my boyfriend go into a bedroom last night]

[Did you get him to fuck you when he was drunk, you faggot? He came home stinking like cum]

[Answer me you coward, what the fuck happened last night]

'Well, technically I kept my promise.' Kai thinks to himself, tapping a reply out on the screen.

[Yeah, I fucked him. But he's the one who bottomed.]

[BULLSHIT!! There's no fucking way he'd do that, even if he was plastered.]

[Sorry, he was sober and took it like a champ]

Licking his lips, Kai brings up the photo right before he took the swimmer's anal virginity and clicks send.

[Holy shit, is that your dick? He took that?]

Pulling up the aftermath photo, Kainen grins and sends that as well, 

[Hey, what are you doing tonight? My boyfriend's too embarrassed to see me and I could use something to do.]

Thinking about what to send in reply, Kai notices a photo pop onto the screen. Tapping to enlarge it, Kai laughs when he sees a selfie of a tanned girl in lacey underwear and fur lined boots, blonde hair falling past her shoulders.

[Yeah, sure. Come over and I can fuck you the same way I fucked your boyfriend]

Crawling out of bed, Kainen goes through the usual morning routine and checks his calendar. One class today, but still a few hours away, and it's a math class. Hooray. Kai yawns his way to the door and stumbles to the building elevator, shielding his eyes from the sun beaming through the glass as it carries him to the ground floor. Unfolding the sunglasses hanging off his collar, Kainen wanders into the campus grounds in search of something to eat. 

[Hey, I think I see you, you're by the breakfast cart!] checking his phone, Kai sees a text from the swimmer's girlfriend before a hand slips into his back pocket.

"You're even cuter than Richie's description, I can see how you got my boyfriend into bed..." the girl coos into Kai's ear from behind, squeezing his ass firmly.

"It really wasn't hard, uh, what's your name?" pulling the girl's hand from his pocket, Kainen turns around and looks her over. Black yoga pants, a loose hoodie, sandals and an iced coffee in hand, she's a basic white girl chic advertisement. 

"I'm Jessica, and I know your name already, Kainen." giggling and taking a sip from her cup, Jessica tugs on Kai's shirt "Wanna skip class and go to your place?"

The proposal makes Kainen pause and think a bit; the professor will probably get mad if he skips for a third time, on the other hand, math is boring.

"Sure, but I'm getting a burrito first." pulling away from Jessica, Kai walks over to the cart and places his order, heading back to his apartment once it's ready and in hand "Well? Are you coming?"

Hurrying over to Kainen's side, Jessica tries to sidle up and rub against his shoulder as he unwraps his burrito.

"What did you get? Extra... sausage?..." Jessica nudges his hips with her own, trying to flirt.

"Nyo, I'm a vegetarian." ignoring her advances, Kai takes a bite and walks on, letting her follow in his wake.

Finally back in his apartment, Kainen falls into his couch and lets the cushions swallow him, grabbing the remote and flipping on the TV. Jessica sits daintily next to him and paws at his sweater vest, pulling him closer and straddling his waist.

"So, have you ever been with a girl before? I bet you get a lot of attention with that cute face." pressing up against Kai's chest, Jessica drags her tongue up the side of his neck and grinds her hips in circles against his crotch. The TV flashes in the background as Kainen rolls his eyes, letting the girl live out her gay conversion fantasy.

"No, I've only ever slept with guys." he sighs, playing along and running his hands along her thighs and cupping her ass. 

"After you spend a night with me, you'll never go back to men." sliding down to kneel between Kainen's legs, Jessica slips her hands up the legs of his shorts, fondling his soft cock through his boxers until a visible bulge pokes through. Kai watches the girl play with his dick until the straining becomes uncomfortable, standing up to undo his belt and letting his cock flop onto Jessica's face.

"Wow, it's even bigger up close..." kissing along the underside, Jessica shifts back and takes Kai's length in her hand, letting the head rest on her tongue. A few strokes and a squeeze later, her lips wrap around the tip and slide towards the base, the shaft gliding along her tongue. Placing a hand on her head, Kai admits to himself that she feels pretty good, letting out a sigh as she pulls back and sucks eagerly. Jessica's blonde hair sways back and forth as her head bobs, saliva falling from her lips with each motion and staining the area rug below. Watching Jessica eagerly swallow his length, Kai bites his lip and focuses on the warm mouth surrounding his cock, tensing slightly as her tongue swirls over the tip.

"Hey, are you going to be long? I do still have other things on my schedule today." pulling the girl away from her work, Kai wipes a string of spit from her lip with his thumb. 

"I promise I'll have you cumming in no time." Jessica gives a grin and strokes the base of his cock, lapping up a drop of precum from Kai's head and sucking on the tip to draw out more. Wrapping her arms around Kai's waist, Jessica pulls him in as deep she can, the head of his cock sitting just inside her throat. Unable to pull away, Kainen feels her tongue wriggle along the underside and her throat closing around the tip to massage him. Every second of stimulation brings Kai closer to the finish line, though he does his best to stave it off. A slight groan and a shiver warn Jessica of Kai's impending orgasm, but she simply keeps her lips wrapped around the base of his cock, letting rope after rope of cum spill down her waiting throat. 

"Mmmf.. see?" swallowing the last bits of semen, Jessica kisses and licks Kai's cock clean, sucking on the head to pull out every last drop "I told you I could do it. Got enough left in the tank to go another round?"

Cupping his balls, Jessica gives a light squeeze and kisses his hip bone, looking up at her lunch replacement's face.

"Ah, not today. I have stuff to do, remember? Besides, I'm sure you'll find me at the frat party later."

"Hmmm, that's true. Though I might be a bit busy with some other gu- I mean my boyfriend. Alright, I'll hunt you down tonight!"

Pulling up his boxers, Kai leads Jessica out the door and gives a wave as she heads down, shutting the door behind her and heading back to the couch to lie down. Reaching for a baseball cap, he pulls it over his face to cover his eyes and quickly falls asleep, skipping class once again.

Stretching out and rolling over, Kai finds himself wrapped in a blanket and in an unknown room that feels like it's rolling every which way. Trying to stand, Kai falls as the room tumbles again, reaching out to a table for stability but it's deceptively far away and crashes to the floor.

"Oh, you're awake now? Stop moving, let me help you back onto the couch."

"Wh...whheeere am I?" shaking his head slowly, Kai forces the words out as his mouth fights his efforts.

"I picked you up after someone called me, they found you passed out naked in the middle of a bunch of guys. Pretty sure you were drugged, but you should be okay. Here, breathe through your nose." bringing a small bottle up to Kainen's nostrils, the man pinches one shut and watches Kai inhale deeply. The vapors shock Kai out of his stupor, everything becoming brighter and clearer as the new drugs counteract the ones in his system.

"Woah, that's better. What even happened? Last thing I remember, I was taking a nap in my place. Wait, Professor May?" rubbing his eyes, Kainen gets his bearings to see his math professor standing over him.

"Yeah, I'm the one who came, even though you haven't been to a class of mine in weeks. Here, breathe through your nose again." placing another small container to Kai's face, the professor pinches the same as before "That's right, deeeeeep breath..."

Breathing in long and slow, Kainen realizes that he's not wearing any clothes under the sheets before he feels his body flush with heat and relax, unable to read the label covered by the professor's fingers. 

"You see, Kai, I got those boys to help me teach you a lesson in responsibility. If you make a commitment and don't follow through, typically there are... consequences." standing up, Professor May undoes his belt as Kainen's eyes go wide, blood pumping faster and forcing an erection to rise through the sheets.

Tugging his pants and underwear down, the professor lets his half hard cock flop onto Kainen's upturned face, thick and heavy with a large head dripping clear pre. 

"Hey, professor, can't we... umm... talk this over?..." the smell of his teacher's sweat and precum fills Kai's head as he feebly protests, hands falling to his crotch to rub his own cock through the covers. Professor May doesn't answer, simply gripping Kainen by the ponytail and smearing his cock across his student's lips before prying his lips open with it. Kainen's eyelids flutter in a combination of arousal and frustration as his mouth is filled by the older man's meat stiffening on his tongue. Pulled forward roughly, Kai's lips stretch around the fat cock as it jams against the back of his throat, his head being controlled by the groaning professor.

"You know, you could have just come by and talked to me after classes, we could have worked something out. But I suppose you are the type to do things the hard way..." forcing Kainen's head back and forth, Professor May fucks the boy's mouth steadily, watching the mixture of saliva and precum fall from his lips. 

"You're one hell of a cocksucker, you know that? Shouldn't be surprised, rich kid like you would be nice and soft after all." pulling his cock free, the professor slaps it across Kainen's cheek and lets it rest against the boy's outstretched tongue "Hell, you're practically begging for it now. What a cute little slut you turned out to be."

Pulling the sheets free, Professor May undresses Kainen and admires the smooth body squirming beneath him before manhandling him onto his hands and knees. Pulling a jar of lube from a drawer, the professor dips a finger and runs it between Kainen's cheeks, circling around the tight hole and pushing in slowly but firmly. Kai lets out a gasp of discomfort from the intrusion, his ring clenching around the man's finger as it slides deeper. 

"Damn, you're tight. Don't worry, we'll work you open soon enough." reaching under Kainen, the professor strokes the student's twitching cock and watches a stream of precum fall from the head as he curves his finger inside "Yeah, that's what I like to see..."

The feeling of his professor's finger penetrating him combined with the hand around his cock sends Kainen's head swimming once again, his heart pounding in his chest. The finger finally pulls free of his bottom and Kai feels the professor shifting behind him, a weight smacking down on his lower back. 

"W-wait... Don't..." pulling at the sheets, Kainen tries to crawl forward but Professor May pulls the boy back by his waist, lining the head of his cock up against the waiting hole. Driving his hips in, the professor feels Kainen's hole still trying to keep him  out, but he keeps up the pressure. Groaning and shaking beneath him, Kai fights entry as long as possible but eventually loses out to the drugs and lube, the man's large head finally breaking through.

Kai screams into the mattress as his hole constricts around his professor's shaft, the bulbous head stretching him open to accept the rest.

"One way or another, it always fits. Feels like you're trying to squeeze my dick off, though." holding Kai by the hips, Professor May works his cock deeper, stretching the student's ass to accept his girth "There we go, all the way in..."

Sitting upright on the bed, the professor pulls Kainen onto his lap facing away, bouncing the boy slightly with his hips. Each thrust makes Kai's cock jump as the professor bottoms out inside him, unable to do more than stay impaled on the man's length. 

"Hey, don't worry, I'll make you cum too." reaching in front, Professor May catches Kainen's flopping dick as he bounces mindlessly, stroking slowly to milk the blonde boy's seed. Not long after, he feels something wet fall on his fingers and Kainen's hole clenches desperately around the base of his cock.

"Well, that didn't take long, did it? I know you have more in you, though." still rocking his hips, the professor keeps working his hand along Kainen's softening cock, coaxing out another weak load in record time. 

"I... I can't..." Kainen whines softly, coming down from his second orgasm and getting another whiff of the mysterious bottle in return. Another wave of heat pours over Kai's skin as his cock rises to attention, the professor's hand stroking it immediately. Rolling Kai onto his stomach, Professor May pins him to the bed and slams his hips down, driving his cock balls deep inside the helpless student. Every thrust draws a grunt from the boy underneath him, spurring him on to go harder until his own balls tense. Pushing Kainen's face into the sheets, Professor May holds his student in place and lets out a moan as he unloads his seed deep inside the boy's bowels, then falling flat, he wraps his arms tight around Kainen, still rocking his hips through the orgasm.

Trapped in the grip of his teacher, Kai can only shudder and groan as he's filled from behind, the fat cock head making sure it pours deep. A final spurt of cum releases from his own softened length as Professor May pulls out, landing uselessly on the bedsheets and mixing with the pool of sweat and seed. 

"You want to pass my class without having to go, right?"

"Uhh..."

"You're going to come see me once every two weeks for your 'special assignments', otherwise you're free to skip class as you want. Understood?"

Uhh.. huh..."

Still overwhelmed from the drugs and stimulation, Kai barely hears the professor but nods along anyway. No class? That's all that matters.

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