Dumb Jock Roommate Ch. 05

Story Info
Jon’s big cock gets stuck in Theo’s hole by accident.
4.8k words
4.82
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Part 5 of the 6 part series

Updated 11/14/2023
Created 11/06/2023
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This is what Jon saw as soon as he left our tiny, shared bathroom:

A big, fat, smooth, bubble butt, all spread out, wet and shiny, with lube dripping down the exposed crack, where a pinprick, soft pink and extremely tight hole was desperately winking at him like the mouth of a hungry baby bird.

I was on all fours directly across him, and my head was so far down Jon's bed it looked like I was simple retrieving something from underneath it, if it wasn't for my very naked, very sexual state.

Just like a slut presenting himself for fucking and breeding.

I had just taken a break from fingering my ass open, thinking about Teddy's fat cock stretching me inside out, when I heard the door to our bathroom open and Jon's sudden pause as he stopped right there, taking in the scene of me all exposed for him. I had both hands now in front of my face for balance. My ass was up and my was face down, like a cat stretching.

The rocky motion of my fingers inside my hole, trying to find the sweet, glorious spot that would make everything go white had made my already tired body from our morning run even more tired, and I was taking deep breaths as I got ready for a new round of finger banging my sweet, jock pussy.

But I had overestimated how much time I had, or maybe I was just so freaking clouded by lust I didn't see it pass: here Jon was, finished with his shower and finding me in a very compromising position, and I still hadn't cum.

Shit. I needed to stop that now and go shower, Teddy is going to be waiting for us at the cafeteria for breakfast!

I was pushing my torso up and out from behind Jon's bed when my wonderfully dumb jock roommate misunderstood the entire situation.

"Fuck, Theo, you got stuck! How did that happen, man? Are you alright under there? Don't worry: I'm gonna help you. I've seen this once before in a movie so I know just what to do to get you out of this predicament, bud" he said, chirping as I heard him walking towards me.

Next thing I felt was Jon's massive, powerful body right behind me as he kneeled down, spread my already spread legs even more, grabbed me by the hips (making my ass cheeks spread even more in the process) and plastered his front entirely to my back, his fat, soft cock jamming against my ass crack and his strong hips pressed tightly against me.

His huge, soft dick was hot dogged inside my wet asscrack; I had used so much lube the pearly liquid was dripping in and out of my spasming hole and coating the entire shaft of his mega jock dong. Jon seemed entirely oblivious to the absolutely obscene compromising position we were in, of how it would look if someone entered our dorm room right that second.

Thinking wasn't Jon's strongest talent, anyways.

I was absolutely stunned, and couldn't form any words to warn Jon I wasn't actually stuck: the feeling of his horse dick tightly pressed against my ass had me devoid of any reaction. His fat cock head tapped insistently against my tiny, pink hole, and every time that happened I had to suppress loud moans.

"Hold on, Theo, I'm getting you out of this right now, man. When I say push, you just thrust that big ass against me as I'll try to push you out, ok? 1, 2, 3, PUSH!" Jon commanded, just as he thrusted his crotch against me, banging my ass hard with his now surely hardening dick and not doing anything to actually get me "unstuck".

"Again dude, come on, 1, 2, 3, PUSH!" He thrusted against my ass again, cock now more than at half-mast.

"Oh, o-h, fuck, FUCK!" I mumbled, delirious with the feeling of my dream stud thrusting against my ass like I've always wanted to, even if he wasn't penetrating me yet.

"Come on bro, this the one where I get you loose, come on, oh just a sec here, all of this exercise made me rock hard bro, I'm like granite here. Let me position this dick so you don't break it in half when we push" he chuckled, thinking this was so funny.

I felt him taking his crotch off of my ass for a while, just to then feel his big, fat cock head slapping forcefully against my super wet jock pussy as he "readjusted" his position; for a while it seemed like he was positioning his monster cock exactly against my open, gushing wet and relaxed hole, but then I realized he was actually pointing it downwards, probably wishing to just push that 10 inch column of jock flesh in the gap in between my thighs, where it would slide smoothly as he thrusted.

I held my breath as he groped my hips strongly once more, getting ready to thrust, and I spread my legs even wider in anticipation for how hard he would push me now. "This is it bud, here it comes, you're getting loose, you're getting loose, 1, 2, 3, PUSH! FUCK!!!"

Jon was the one who screamed, but I felt my soul leave my body at that exact moment.

The moment where Jon rammed 10 thick inches of jock cock inside my wet, hungry hole.

"Oh, FUCK!" I screamed, more from the surprise of being stretched so wide and (finally) feeling so full of dick than from any pain. My hole was always extremely tight, but at that point I had stretched and lubed myself enough that Jon's wet fuckstick slided right in without any trouble.

I felt the strength leaving my body and my shoulders falling down on the floor, the right side of my face pressed against the ground as my hips and ass stayed up in my all fours position. I took deep breaths and felt my hole spasming and constricting around Jon's huge, meaty cock, my mind going blank from the inexplicable pleasure I was having from finally getting my hot jock roomie's cock inside my pussy.

Jon was strangely silent, his large hands still gripping my waist tightly as I got used to his cock all the way up my big, firm ass. The silence went on for a few more seconds as I felt Jon's ripped, veiny groin touching my back and his large balls slapping lightly against my ass.

Suddenly, Jon's hands pushed me all the way out from beneath his bed, while I was still impaled on his cock; the result was his massive cockhead smashed the exact place that made anal sex so freaking pleasurable to me, and my eyes rolled behind my head as his dick kept hitting my prostate repeatedly while Joan maneuvered me to the center of our dorm room, gently leaving me on all fours, with my head now facing the door.

"J-on?" I stuttered as I turned my head around to look at the big dumb stud.

The sight was simply spectacular: Jon, in all his naked glory, balls deep inside my hole, his granite abs and chest expanding and deflating with adrenaline as he felt what I'm sure was the tightest, juiciest boypussy of his life. He was looking down on my ass with his mouth open, eyes large and wide, droplets of water from his recent shower still dripping from his hair onto his chiseled body. His biceps looked absolutely huge and veiny as he still gripped my waist strongly.

If Jon always looked like sex on legs, he now looked absolutely demonic, as if he was a demon of lust put on this earth to satisfy my deepest, kinkiest sexual desires.

"J-, J-on..." I whined again, still unable to be coherent with so much cock inside of me.

"Theo, dude... I'm sorry. This is all my fault..." He said in a low voice.

His fault? What?

"It seems that, in my haste and clumsiness to get you unstuck from down the bed, I ended up pushing my entire monster cock inside your hot ass, bud... I just can't believe that actually happened. I'm so embarrassed right now you don't even know. How can I look you in the face ever again, man? I just fucking hate how I'm always so horny and hard that my dick keeps entering holes it's not supposed to enter, man!" He said angrily.

What the fuck?

"And now this huge cock is STUCK inside you ass, bro. Yeah, I know, it's stuck! How do I know it's stuck? I just know, buddy, look how big it is, your hole is just too tiny and tight and my fat cockhead is so deep inside your sweet ass canal it just won't come off while it's still hard like this. It's just like the situation of me getting this dick down your throat all over again, instead it's worse, because it's your ass! And it's super tight, man. Oh, God, why is my cock always hard?" Jon pleaded so sincerely I pitied him.

"Jon, it's okay, really. Yours is not the first cock I had in my ass, I'm gay, remember buddy? I had plenty of jock dicks there before. Yours is just so... huge and thick and it's giving me the chills cause it keeps massaging my most special place deep down inside. But we will get through this, okay?" I assured the big stud looking directly at his eyes, which were already tearing up from his self-perceived embarrassment.

"It will?" He asked softly, looking like a lost little boy.

"Yeah, yeah, it's like you said, it's stuck and it won't come out while it's still rock hard like this. Remember what we do every time your hard cock gets stuck inside my slutty little mouth?" My voice tone was getting huskier as I saw my opportunity and seized it.

"Yeah... I fuck your slutty little mouth super hard until I cum all over your face and down your throat" he fired up quickly, getting excited again with my solution to our problem.

"Exactly, you fuck my mouth nice and hard till you empty your balls down my throat so that cock can finally get soft" I said shaking my ass against his cock.

"So you're saying..." he looked doubtful for a moment.

"Jon, I'm saying you should fuck my ass like a whore till you cum inside my pussy" I stated firmly.

"Oh, I can do that! You're a genius, Theo!" he answered, and then I almost regretted asking him to fuck me like a whore.

Whores don't get fucked this hard.

It started slow, at first, with Jon feeling his way and thrusting all the way inside until he bottomed out, just to them push his cock all the way back almost until it left my hole, to then smash right in so powerfully I banged my face on the ground.

When he got to a good rhythm, Jon once again showed me what a true sexual animal he was. He started pounding my ass hard, the speed and strength of his thrusts increasing as his balls slapped against my ass by the second. I started crying his name out loud non stop, moaning "Jon, Jon, Jon, Jon, Jon, Jon!" as drool spilled from my mouth onto the floor. I was in bliss. I was Jon's whore.

"What, buddy?" He asked innocently as he grabbed both my asscheeks and spread them open even more, just so he could see his massive cock going in and out of my wet hole as squelching sounds dominated the room as he fucked me hard.

"Jon, this is just - AH! AH! AH! Ah, this is just what I neededz..." I moaned in a high pitched voice.

"I know, right? You needed to get fucked so we can finally get unstuck!" He replied, obvious to my meaning.

Jon pistoned his fat, 10 inch cock in and out of my hole non-stop, maintaining a strong and fast pace as he brutalized my tiny hole with his perfect fuckstick. His cock was stretching me so good I wondered how I went this long without Jon fucking me. I wanted that cock inside my ass smashing my hole and prostate every day, all the time. There was no other purpose in life for me other than being a slutty fuck toy for Jon, my sexy, perfect, dumb jock roommate.

Jon's stamina was insane. He never let down on his crazy fuck rhythm, the sounds of SLAP SLAP SLAP SLAP as his groin and balls hit my ass the only sounds in the room, well, except my high pitched moaning, of course. Every powerful jab of Jon's giant cock inside my ass hit my prostate perfectly, and I was in a state of blissful euphoria.

I don't know how long Jon fucked me, but it was a good fifteen minutes before his hands left my hips to grab both my pulses, as the big dumb jock brought my arms towards him, forcing me into an even sluttier, spread out all fours position. The new angle was perfect for fucking, and Jon even incresead the speed of his thrusts as he growled and huffed behing me.

Jon showed no signs of stopping or cumming: the jock seemed like he could go on fucking me forever. But at some point, we both raised our heads up as we heard the distinct click of the door lock turning around and opening.

"Hey dudes, did something happen? I already showered and waited so long for you down at the cafeteria and you still haven't shown up for breakfast... OH HOLY SHIT!"

TEDDY!

The big blonde backup quarterback was in our doorstep, jaw opened as he took in the sight of me getting brutally and wonderfully fucked by my dumb jock roommate. Oh fuck, how long have we been fucking? How could we forget Teddy was downstairs waiting for us?

Teddy looked cuddly and warm, freshly showered and wearing just a skimpy white tank top that didn't cover his delicious nipples and beige, small shorts with no underwear in sight: the flimsy fabric did nothing to hide his massive muscled legs and the fucking python snaking down on his crotch. His damm dick print was so huge and evident I could see the clear shape of his thick shaft and thick cockhead. Fuck if he didn't look yummy. He had a confused expression on his face.

"Bros, what the hell is going on?" he asked. Jon hadn't stopped fucking me for a second, and I couldn't speak from how hard I was getting pounded. Teddy closed the door behind him.

"Teddy! Bro, you won't believe this man! My big dick got stuck inside Theo's tight ass and now I'm trying to get it free, bro. It's really difficult cause although his hole is juicy and wet it's also super tight, it's gripping my cock so good, bro! FUCK!" Jon let out as he increased his speed against my jock booty, releasing my arms and now pushing me down on his cock by my shoulders, one of his hands gripping my hair.

"No way! I can't believe it!" Teddy looked astounded, but I was alarmed when I noticed the massive bulge on his shorts starting to increase in size.

Jon then started the whole tale from the beginning, seemingly getting more and more excited as he went on, if the speed of his pounding was any indication. He kept fucking me harder and harder as he told Teddy everything that had happened since he left the bathroom. Teddy interjected here and there with questions that only made Jon's tale longer, and during one particularly powerful thrust, Jon forced my torso forward so hard my arms went out and when they came down, they latched on the first thing they gripped on, and that was Teddy's beige shorts.

To everyone's horror, I pushed Teddy's shorts all the way down to his ankles, leaving his crotch bare and releasing an absolute behemoth of a cock. Teddy's dick, as I had suspected all along, was FREAKING HUGE, both in length and thickness; in that last department, it was even thicker than Jon's, which was already a bat club of a cock. Teddy's cock was already hard and dripping precum from Jon's sexy, crazy tale, and also from the live porn show Teddy was watching at that exact same moment.

His dick was seemingly only a little shorter than Jon's, and if I had to bet, it must've been around 9 inches, but even thicker, like I said. The head was a perfect rosy pink, like Teddy's own kissable lips, and the blonde backup quarterback had only a little patch of trimmed pubes on his clean, veiny crotch, that led upwards to a cobbled 8 pack abdomen that looked like it belonged to a Greek god.

Teddy's huge cock and bull balls throbbed in front of my face as we all gasped and looked large eyed at the terrible accident in front of us, Teddy seemingly the most surprised of us all. Jon immediately started apologizing for the confusion, knowing it was his fault that I had disrobed Teddy in such a lewd way when he pistoned my ass so hard my body had plunged forward. To compensate for his mistake, he pushed me back towards him, impaling me even further on his cock and making me see stars.

His other mistake was that he didn't realize my hands were still gripping the waistband of Teddy's shorts.

It all happened pretty fast: Jon pushed me back on his cock; I brought Teddy down with me by his shorts; Teddy lost his balance and went to his knees, moving his powerful arms to steady his fall by holding my head; just like that I had all of Teddy's 9 inches of SUPER THICK quarterback meat down my throat.

"Oh, fuck, Jon, I can't believe it dude, look at this! You not only got your dick inside Theo's ass but now mine is stuck down his throat too!" the big dumb blonde moaned, not able to resist the pleasure my spasming throat was giving his massive dong.

"Oh, oh, fuck, Teddy, don't worry dude, this is pretty normal! I get my dick stuck inside Theo's throat at least twice a day!" Jon moaned as he pistoned his chiseled hips harder against my ass. My eyes were rolling inside my head from having two huge cocks stretching me from both ends. I was in heaven.

"Uh, what?" Teddy looked confused as his fat cock twitched inside my hungry mouth. I was slobbering all over his thick piece of jock meat and drenching it with spit.

"Yeah, man, it's true! It's usual for horny jocks like us, who basically walk around with a hard on all the time, to get our dicks accidentally stuck inside someone's hot, wet mouth! This has happened to me tons of times, dude, it's no big deal! Or are you going to tell me you never got that mega jock dong of yours stuck inside someone's sweet mouth?" Jon increased his speed as he tried to convince his football bro of how "normal" this situation was, the SLAP SLAP SLAP sounds of him pounding my overly stretched ass filling the room.

"Now that you mentioned, Jon... I guess I did have an accident like that with one of my friends from tennis once... but it was an accident, I swear! I never meant to shove my entire cock down his throat like that!" Teddy exclaimed, sounding earnest and wholesome.

"Dude, how come?" Jon asked him.

"Well, you know, we were about to have a tennis practice, just the two of us, and the country club was pretty deserted at the time, so I thought it would be funny to joke around. I put one of the tennis balls inside my shorts and showed it to him, saying I had three balls underneath my dangling cock, but I guess he didn't think it was funny. He got pretty red on the face and looked upset. So he rampaged towards me, got down on his knees and made a play to push his hands inside my shorts to retrieve the tennis ball so we could finally start playing, and I obviously tried to stop him. We wrestled like that for a while, him groping my bulge to try and take the tennis ball out and me trying to stop him, and before I could do anything I had my shorts down my ankles and my hard, fat cock ended up all the way down my bro's gullet! It was his fault, I only got hard from how bad he was groping my dick in the first place."

As Teddy was recounting his tale, the hard pounding I was getting from Jon was pushing my throat so far down Teddy's big cock that I smashed my entire face on his trimmed pubes, my nose pressing against his veined crotch as I practically deepthroated him.

"See, dude? I told you this was super normal. And when hung jocks like us get our big dicks stuck inside someone's unsuspecting mouth..." Started Jon...

"... the only thing we can do to take it out..." Teddy continued...

"It's to fuck their faces until we dump a load and get soft!" They both screamed in unison, sounding like two kids that had just solved a profound enigma.

"Bro!" Exclaimed Jon.

"Bro!" Shouted Teddy.

Then they high-fived and really started doing a number on me.

They both focused their entire energy and attention on fucking me so hard I had trouble thinking where my body started and where it ended.

From one side, Teddy's fat, 9 inch cock stretched my mouth to its limits, but I was a professional slut and a talented cocksucker, with no gag reflex whatsoever. He grabbed my head with both of his monster hands and started pistoning his huge cock in and out, thrusting his hips up and slapping his bull balls against my chin with every jab of his super jock dong. I looked up to see him and almost came on the spot, seeing his titanic, muscular jock physique hovering above me, big pecs heaving with power and his huge, muscular arms pumped as he skullfucked me and using his hands to push even more of his dick inside. His handsome, All-american face and blonde, boyish looks made my knees weak with lust, especially because of how empty and dumb his beautiful blue eyes looked. Teddy was as much a fuck machine as Jon was, and equally oblivious.

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