▲ 112 r/gaystories+1 crossposts

Boarding School Stories: Part 2

So glad you guys enjoyed my first story! If you missed Part 1, here it is!
Everyone in this story is above 18.

Oh fuck”, I say. “I think I’m cu-“ before I finish my sentence, I hear the lock on the door beep and Dylan stops thrusting as the door handle turns and Hayden walks inside.

Hayden flicks on the harsh bright light in the center of the room and his blue eyes bulge out of his eyes as he quickly slams the door behind him. “What the fuck…”, Hayden says in awe of the sight in front of him.

Dylan pulls out of my hole with a pop, and I suddenly feel so empty. “Oh. uh… wha- what are you doing back here,” Dylan stammers, clearly embarrassed.

“Our uh… Our tournament got cancelled because of… some… storm…”, Hayden says, evidently very distracted as he pushes his ginger hair off of his forehead. I didn’t even realize I was still propped up on the couch with my back arched until I saw Hayden staring at my ass. I get a little self-conscious and quickly turning around and sit on the floor in a ball with my back up against the futon.

“Is that MY lube??” Hayden says, as I see a tent forming in his lacrosse shorts.

“Yeah I uh, hope you don’t mind”, Dylan chuckles as his still rock hard dick bounces up and down. “Listen, I just really needed to get a good nut out. I haven’t even been able to sleep because i’m so fucking horny. And well uh…” Dylan looks over at me, “Max wanted to help out.”

The room lulled. No one said or moved an inch for what felt like an eternity. Hayden still paralyzed by the door, Dylan standing in the middle of the room, and me tucked in a little ball. Dylan jumps back in, “I mean dude you should try this thing”, talking about me like i’m just a toy for them to abuse, “I’ve never felt anything like it. You probably need it too. Don’t act like you’re not beating it every night in your bed. You haven’t been very slick about it recently.”

Hayden’s cheeks turn bright red. There’s now also a very evident wet spot on his orange game day shorts. I can see the contemplation in his eyes, “I don’t know man…”

“Well can he just finish me off at least?” Dylan pleads.

“Fine. Okay, just uh… make it quick.” Hayden turns the big light back off and drops his lacrosse bag. He sits at his desk, opens up his computer and puts on his headphones to finish some homework and try to ignore what was happening on the other side of the room.

Dylan guides me back to my initial position and immediately slams his entire length back into me, causing me to moan like a little bitch. He starts to re-establish a slow rhythm, thrusting in and out. Out of the corner of my eye, I keep seeing Hayden glance over at the sight of us, and his knee bouncing like an anxious spaz. I don’t know if it was the weed, my horniness, or just the overall situation, but I was feeling unusually bold. I reach my hand back and place it on Dylan’s torso to let him know to stop. He pulls out, and I begin to crawl over to Hayden’s desk.

I put my hand on his thigh, rotating him so he’s facing me. I pull at the bottom of his shorts, and he lifts up his ass to get them off easier, and that was all the assurance I needed. The computer screen illuminated his crotch, and I could see the wet spot on his boxer briefs that soaked through into his shorts. He starts to breathe more heavily as I place my hand on his bulge. He takes his headphones off of his head as I hook my fingers into the waistband of his underwear and slide that off too.

I didn’t even know gingers could be this hairy until I met Hayden. If it weren’t for us having to shave every morning for school, he could’ve easily grown a beard in a week. His legs were coated in thick ginger hair, and removing his underwear revealed the most luscious bush I had ever seen. Hayden was truly a beauty of a man. He had thighs the size of tree trunks from his time playing soccer, and huge forearms with a river of veins from lacrosse. His circumcised dick was just as beautiful as the rest of him. It was nowhere near as long as Dylan, but it was just as thick, if not thicker, with a beautiful bright pink head that glimmered in the computer screen light.

I hold his cock by the base, and take the head into my mouth, swirling my tongue around it like a lollipop.

Mmmmmm.” He lets out a low hum with his lips sealed tight and his eyes closed.

I work the jaw breaker into my mouth and down my throat. Dylan walks over, stroking his dick at the sight of his friend sucking his roommates dick.

Hayden suddenly stands up with his dick still in my mouth inadvertently causing me to deepthroat him. I pull of off him, and he walks and sits on the futon throwing off his shirt on the way, revealing his beautiful plump chest covered in red hair, and a thick happy trail that let down to his treasure chest of a bush.

I follow him and go right back to town. I cup his furry balls in my hand and give them a little tug, and I can feel his dick jump in my mouth. I back off his shaft a little bit, paying more attention to his beautiful pink helmet, swirling my tongue all around.

He lets out a groan that turns into a laugh, “Holyyyyy shitttt what the fuck dude,” I glance up at him and see the smile on his face. He looks at Dylan and says, “you weren’t joking. He-,” Hayden shudders, “He really is something else.”

He puts his hand on the back of my hand taking a fistful of hair and forcing me up and down on his shaft. He starts to lift his hips up too, getting more and more comfortable using me like a fleshlight.

Dylan seems to be getting a little fomo as he moves back behind me and shoves his tongue back in my ass. I moan around Hayden’s dick. “Fuckkk dude that’s hot,” Hayden says in between breaths.

after a couple of minutes I feel a little breeze on my hole, but not for long as Dylan shoves his cock back inside me. He grips my hips and starts to go to town on my hole. The room fills with slaps, claps, and slobbering sounds as we are all entranced in the moment. I start to feel drops of sweat land on my back, dripping off Dylan. I get the feeling I have to pee again, and I pull of of Hayden’s dick in front of me, resting my head on his hairy thigh.

“OHH MY FUCKING GOD”, I moan as I feel my hole pulsate as hot cum erupts from my dick.

Dylan starts busting out laughing, “Shit buddy!! did you just cum without even touching yourself?”

I’m to enthralled to even form a response as heave trying to catch my breath. It was unlike anything I had ever felt. And the best part? I was still horny, if not even more.

Dylan stops his powerful thrusts, “Dude your hole is literally squeezing cock right now.

“Can I try that?” Hayden asks very excitedly.

“Of course bro. It’s unreal!!” Dylan replies.

Dylan pulls out of me with a plop, and my asshole queefs and they both start laughing. They switch positions, and Dylan sits back in front of me. I go to put his dick back in my mouth, but he pushes me off, “Not yet, I’m way too close. I’ll just watch for now.” He man spreads and rest his arms on the top of the futon, revealing his sweaty pits.

I feel Hayden’s hand running up and down my ass crack, then he shoves two fingers in causing me to moan. he swirls them around in my hole before pulling them out. I hear the bottle of lube click, and the slick sound of him lubing up his cock. I feel his fat pink helmet pressing against my hole. I let out a high pitch moan, half pleasure half pain as it feels like he’s splitting me in half. Hayden definitely had the thicker cock. He slowly sinks into my hole until I feel his hairy balls against my taint. He stays there for a second allowing me to adjust.

“Fuck he’s so fucking tight,” Hayden says.

“Tell me about it!” Dylan replies.

Hayden starts to establish a rhythm, going in and out. In and out. I feel a hand on my hand as Hayden grabs my hair again forcing me to arch even more, and he picks up the pace going faster and faster and slapping my ass.

“This shit is insane” Hayden says. “I didn’t realize guys could have such fat asses.”

“I know right!” Dylan says, “It’s inhuman.”

Hayden lets go of my hair, and plants his hands on my hips. Dylans hand replaces his as he guides my head back onto his cock. I try my best to get as much of his cock down my throat as I can, but I’m so distracted by Hayden’s huge cockhead rubbing up against my prostate.

“Fuck yeah bro!” Dylan says as he leans forward and daps up Hayden. I was truly in heaven.

Hayden pauses for a second, planting one foot on the ground in a lunge position to get more leverage. He begins going to town again on my boy pussy. I’m not even sucking Dylans dick at this point, just holding it in my mouth as I moan.

I pull my dick out of his mouth as a familiar feeling floods my body, “ohhh fuckkkkkkk” I whine as I cum again, drenching the carpet in my boy seed.

“Fuck you’re gonna make me cum” Hayden pants as he slams into me. I feel his dick pulse as my floods my guts with his hot cum. he collapses on top of me and I feel his sweat soaked furry chest tickle my back.

After a couple of minutes, Hayden finally pulled his softening cock out of my hole.

“My turn!”, Dylan yells as he jumps up from the futon.

I come onto my knees as he grabs my hair and leads my mouth back onto his rock solid cock. I go up and down on his shaft, tracing his veins with my tongue. I start stroking my rigid cock while filling my mouth with Dylan’s monster. He puts his hands behind his head, and I feel Hayden’s hand on the back of my head shoving me down Dylan’s dick.

“Okay okay okay,” Dylan pants, “I’m gonna cum. like right now.”

A spurt shoots down my throat with insane force as he slides his dick out of my mouth and drenches my face and chest in hot cum. I lost count of how many spurts, but he had to be cumming for at least 45 seconds straight. That sends me over the edge as I orgasm and shoot blanks.

“Holy Shit! WOOHOO!!”, Dylan yells and laughs.

“Dude. You got cum on my foot,” Hayden says with disgust in his voice. His post-nut clarity must be kicking in.

“I’ve never cum like that bro,” Dylan pants, “that was incredible.” Dylan pats my cheek like he’s petting a dog getting his own cum on his hand.

“Glad I could help,” I say timidly.

Dylan grabs a tshirt from off of the floor and tosses it to me.

“I need a shower,” Hayden says.

We all need a shower,” Dylan laughs.

I hope you enjoyed! Let me know if you’re interested in this being a longer series.

reddit.com
u/Long_Piano6712 — 1 day ago
▲ 458 r/gaystories+1 crossposts

Boarding School Stories

This is my first time writing a story like this so I would love some feedback!
Based on a true story but mostly fantasy.

Everyone in this story is above 18.

I went to an all boys boarding school in the middle of nowhere. It was so in the middle of nowhere that the only restartunt within 10 miles was a McDonald’s. It is safe to say that after a while, boys stopped thinking with their head and started thinking with their dicks. There was always typical boy stuff going on in the dorm. I probably saw a pair of ass cheeks every other day from getting mooned. And as one of the only openly gay guys, it was a dream come true. Although I never hid my sexuality or was ashamed of it, most of the guys didn’t even know I was gay. I say that because they would always comment on how fat my ass was. Typical locker room talk, but I don’t think they would’ve been so comfortable about it if they knew they were talking about a gay guys ass.

My best friend dylan lived right across the hall from me with his roomate hayden. Dylan was a total goofball. He was tall, lanky, and awkward standing at about 6’ 3”. He had fair skin and shaggy light brown hair that would barely kiss his neck when he went too long without a haircut. He was basically the first straight guy I ever actually felt comfortable around. And he felt surprisingly comfortable around me considering he knew I was gay. He would tell me whenever he got with a girl over Christmas or spring break with great detail. Once he talked about how this girl gave him head, and he shot so much cum it landed at the top of the couch and on his forehead. I shot so many loads to the idea of him being a shooter.

Dylan, Hayden and I were all big stoners and would basically get high and watch cartoons every night. We always hung out in Dylan and Hayden’s room because he had the better setup. Both of their beds were lofted with their desks underneath and a futon in between the beds.
One Friday night, Hayden was gone on an overnight lacrosse trip so it was just dylan and I hanging out. We had taken some edibles and were watching march madness. Weed always makes me more horny. I was sitting in his desk chair while he was sprawled out across the futon wearing a grateful dead tshirt and a pair of basketball shorts.
“Are you feeling this shit yet dude?”, Dylan said.

“Oh yeah, definitely”, I respond as I can feel my toes start to tingle and rise up through my legs.

“Shit.”

A few seconds later, he stands up and says, “fuck it. I’m taking another”.

He reaches over me to get the bag from the top drawer of his dresser. All of a sudden, I feel something resting on my thigh. It took me a few seconds to register what it was. At first I thought it was his phone from how heavy it was, but it felt too soft and round to be a cell phone. That’s when I realized he was freeballing, and his huge balls was resting on my leg. I can feel my underwear get tighter and my ears get hot.

“Holy fuck”, I thought to myself.

“What?” Dylan says. And I realize I am way higher than I thought I was.

“Oh nothing-“ I stammer as I feel my cheeks get hot.

“they’re heavy aren’t they?” He says with a smirk on his face barely visible in the dark room illuminated by the orange LED lights.

“Ye- Yeah they are,” I stammer as the edible is making me unusually candid.

“I swear they’ve been getting heavier everyday. Jerking off in the shower isn’t cutting it anymore. I can’t get it all out.” As he says this, his eye contact is unusually firm, and it’s almost as if I can see a twinkle of hunger in his blue eyes.

The room lulls as I am too high to even process what’s going on. Then, he says, “Do you think you can help me out?”

At this point I am now fully hard sitting in the chair as dylan stands over me. “Sure,” I say trying to be as nonchalant as possible.

His eyes light up and he smiles, “Bet! thank you bro you’re a real one.”

He pulls down his basketball shorts to reveal to goose eggs and huge uncut cock that looks to be about 5 inches flaccid. My heart rate jumps as I realize that I am about to give my best friend head. I’m still in awe as I reach for his balls first. They’re so warm and heavy in my hand. I begin to massage them, lost in the moment rubbing one between my fingers. He groans loudly as the basketball game just becomes white noise. he begins to firm up, and I take his shaft into my hand. I had never seen an uncut cock in person before. I was enthralled by his foreskin. I stick my tongue under his foreskin and circle the head of his dick as he groans again, this time a higher pitch and his knees buckle. Now he’s fully hard at what looks to be 8.5” and thick. I begin to get a little intimidated because I had never sucked a cock this big, and for some reason I was thinking to myself, “I don’t want my best friend to think I’m shit at sucking dick”.

I finally take as much as I can into my mouth as I can getting about halfway down. I can feel his cock pulsing in my mouth as the blood keeps flowing to his huge cock head. I start to get into it more as my mouth pools with saliva and I try my best to hollow out my cheeks around this monster of a penis. I swirl my tongue along is dick, feeling every vein bulging out. He starts to hum, then groan, then to a full high pitch moan. I had no idea his voice could even go that high. This only makes me more eager and I pick up the pace. As my throat opens up more, I can fit more into my mouth, but still nowhere near the base.

I try to deepthroat it, but end up gagging, pushing his cock out my mouth and coughing hard. He looks down at me with a huge gleeful smile on his face.

“no one has ever gotten that far down,” he says.

This makes me proud as I smile back and get right back to work. He puts his hands on the back of my head. Just resting there at first, guiding me. But he gets more forceful, and eventually begins to full fuck my face like a pocket pussy. I’m glad that we do have the March Madness game on because the way he was moaning, George and Henry next door would’ve definitely heard us.

All of a sudden he pushes me off of him. “I don’t wanna cum yet.”

He takes off his t-shirt and sits down on the futon as I slide out of my chair and crawl to him like he’s a magnet and we get right back to it. I take a break from his dick to give his huge balls some attention, taking one into my mouth, sucking on it and rolling my tongue around it. I look up at him to see his head thrown back and him rolling his nipple between his thumb and pointer finger. I go back to sucking his cock. I play with his balls in one hand while rubbing myself through my shorts with the other.

I slide my hand down a little bit and start rubbing his taint. “Holy fuck. Holy fuck,” he says as his breath becomes more labored. I feel his cock get more engorged in my mouth and I pull off because now I’m so into it I don’t want him to cum yet either.

“Can I tell you a secret,” he says with his breath labored.

“Sure.”

“I’ve been watching a lot of anal porn recently and I want to try it. It seems so much tighter than a pussy.”

My dick pulses and I literally feel a huge drop of precum pump out of my cock and soak my underwear. “Are you asking to fuck me?”

“Can I?”, he says shyly and a little embarrassed.

“Yes,” I say a little too eagerly.

I stand up and start to take my clothes off and my cock springs from my pants. Dylan goes over to Hayden’s side of the room and pulls out a bottle of lube from the top drawer. I rest my elbows on the futon and put my knees on the ground waiting for him.

He comes around behind me. “Shit your ass really is fat”. he puts his hands on my has a rubs them around. “This shit moves like water!”

he spreads my cheeks, and I brace myself for the cold lube. But i’m surprised when I instead feel something warm and wet. I moan as I bury my head into a pillow on the futon. His tongue swirls around my puckering hole, and he licks up and down my crack. I feel like I won the lottery and I didn’t even have to buy a ticket. He shoves his tongue into my hole and I moan like a little bitch. I can feel Dylan laugh as his tongue vibrates.

He pulls his tongue out and I hear the lid on the lube click open as he pours some on my already wet hole. he slides one finger in and somehow immediately finds my prostate and my cock leaks onto the dorm room carpet. He puts another finger in and scissors me open. He really has been watching a lot of anal porn.

Finally, I hear him lube up his cock and I feel the head pressing at my hole. I bury my face into the pillow as he pushes his cock deep into my wet hole. It felt like he was halfway and he had only gotten the head in. I breathe deeply as he slides more in slowly, and the length of his cock rubs up against my prostate.

As I loosen up around his hole, he begins to thrust softly. “Fuck this is so tight. I’m about to cum already.” He stops and just sits in my hole and I feel the blood rushing through his dick. after a few seconds, he picks up the pace again, gripping his hands on my hips and pulling me back onto his cock. The room is hot and musky as I can hear him clapping my cheeks while his balls slam into my taint.

I feel like I’m about to piss myself, and I realize I’m gonna cum without even touching my dick. “Oh fuck”, I say. “I think I’m cu-“ before I finish my sentence, I hear the lock on the door beep and Dylan stops thrusting as the door handle turns and Hayden walks inside.

To be continued…

Please let me know if you enjoyed and if there’s anything I can improve on!

reddit.com
u/Long_Piano6712 — 3 days ago