Sean - A puffter in Boston

Boston is a weird place to grow up and be gay. Growing up an Irish Catholic in Boston made it difficult to tell what guys were “just drunk” and who was actually into you on a sexual level.

My uncle owns a pub just on the edge of the city and the suburbs and because, “family helps family,” I’ve been working there since I was about twelve years old, unpaid of course. I didn’t start getting paid to work there until I was sixteen. That was when the drinking age went from 18 to 21 in the US, but my uncle “didn’t give two shits” how old a paying customer was.

He was old-school Irish. My grandparents immigrated from Ireland when my uncle was just three years old, my mother was born a year later here in the US. So I grew up hearing all the curse words, seeing guys get into fist fights over sports on TV, and then hang all over each other confessing how much they love one another a few beers later.

In 1981 when I turned 18 my uncle gave me the night off. It was also a Wednesday and I still had school, so I wouldn’t be working anyway, but he made a show of giving me the day off. That Friday night I was celebrated at the bar by a lot of the regular customers. They bought me shots and beers and some a combo of the two.

By midnight I was a little too drunk to keep working. I wasn’t falling over drunk, nothing like that. I was just being too social with people and not getting any work done. My uncle got pretty annoyed with me and told me to take the rest of the night off.

“And do what? It’s already midnight, all my friends are home already,” I told him.

“I don’t care what trouble you land yourself in, just take it outta here before I call your pops to come get you. And I better not hear it from your mother in the morning about you being trouble either,” he bellowed.

I stumbled out of the bar and started walking. It was late April so the weather was decent and I didn’t want to go home. So I walked about twenty blocks when I realized I walked right by a gay bar. The guys standing outside were a dead giveaway, but the nearly 7’ tall drag queen who walked in really had me convinced.

I walked up to a handsome guy with a Freddy Mercury mustache who was smoking a cigarette. “Can I bum a smoke?” I asked, trying to act like I was not drunk.

He smiled, “Sure kid,” he held his pack out to me. I took one and he lit it up for me.

“I don’t think I’ve seen you around here, I’m Finn,” he said, flicking the ash off his cigarette. He was a few inches taller than me, thin and his pale Irish skin kind of glowed in the moonlight. His hair was a darker red than mine and slightly longer to the point that it was starting to curl at the ends. I was instantly attracted to his thin lips and the way his eyes smiled when his lips curled up into a grin.

“Oh I’m Sean,” I told him, shaking his hand. “I come here often, I just have been out of town,” I said confidently, “on business,” I added, rocking up on my toes as I smoked.

“Oh yeah,” he grinned, almost laughing at me, “what business is that? You’re not one of those rent boys are you?”

“A what?” I had never heard the term.

“Never mind,” He smiled at me and took another drag, then tossed the last of it on the ground and stepped it out. “I’m going back in, are you coming?”

I glanced over at the bouncer, “I umm…yeah,” I tossed my cigarette on the ground and stepped on it. My heart was racing, I had never been in a gay bar before, but I had heard stories from the drunks at my uncle's bar, about the “puffters getting bent” at places like this. I had never been “bent” before, but man I had wanked off a thousand times thinking about it and how good it must feel.

“Hold it,” the bouncer's massive arm came down in front of my chest, stopping me from walking in with my new friend. “How old are you?” He asked.

My new friend turned to look at him, then me, “You don’t know my buddy Sean here?” He said, with a grin.

“Sorry Finn, but I’ve got to see his ID, the kid doesn’t look like he can shave,” the bouncer held his hand at my chest.

“I, umm,” I looked at Finn, then the bouncer, reached for my wallet, pulled out my ID, and handed it to him.

He chuckled, “Finn, he’s barely 18,” he shoved my ID back at me. “Get outta here kid, I’m not getting in trouble because you want to get your dick wet,” he growled.

I took my ID, shoved it back in my wallet, and stormed off. I got about two blocks away from the bar when Finn caught up to me. “Heading back to work?” He asked.

I shoved my hands in my pockets, “No,” I looked off in the distance, knowing home was a half-hour walk at least.

He offered me another cigarette and lit it for me, then kept walking and I followed, “So, it’s your birthday huh?” He asked.

“Kind of. I turned 18 a couple days ago,” I confessed.

“Woh, the big one - eight,” he acted as if that was an accomplishment.

It made me laugh, “Yeah, I guess,” I shrugged.

“Did you get anything nice for your birthday?” He asked, turning down another street.

“Not really. My parents got me some clothes, my sister got me a book signed by my favorite author,” I said.

“That’s nice, what’s the book?” He asked, then walked down another block.

“It’s called Cujo,” I said. “It’s about a…”

“I know what it’s about,” he chuckled. “You wanted a terrifying book about a rabid dog for your 18th birthday?” He asked, suddenly stopping walking and leaning on a fence.

“I guess, I mean, it was a nice gift,” I said.

“But you would’ve rathered something else?” He said, taking a step closer to me, getting uncomfortably close and putting a hand on my hip, hooking his finger into my belt loop.

I felt my heart start beating fast and I swallowed hard, “I can think of a few things I would’ve liked more,” I couldn’t help but stare at his lips. I could smell the alcohol and cigarettes on his breath as he leaned in and kissed me. I took it in for just a second, I had never kissed a guy before, and it was everything I wanted it to be. So much more firm and rougher compared to the girls I’ve kissed. He wrapped his arm around my waist and the other up my back, pulling me tight to him as his tongue slipped into my mouth and started to dance with mine.

I let out a soft moan and then broke our kiss and pushed him off me. Looking around to make sure no one else was on the block, I wasn’t trying to get beat up tonight.

He grinned at me, then nodded to the building behind him, “This is me if you want to come in.” He unlocked the gate, leaving it open for me to walk through.

I looked up and down the block again, thinking I should run, but my dick was already hard in my pants, there was no way I could leave. I quickly caught up to him, pushing the gate closed behind me as I made it to his door just as he unlocked it and walked in.

He closed the door behind me, pushing me hard against the wall and his lips pressed firm on mine as we made out in the hallway of the building for a few minutes, his hands exploring my body as he did. My hands stayed on his hips, too scared to move until he broke the kiss, “come on,” he said, walking to the end of the first floor and unlocked the door to his apartment.

He quickly locked it behind us and started pulling his clothes off. His chest was smooth, not a hair visible until just above his underwear waistband a thin line of hair went from his belly button down into his jeans. He left the chain on around his neck that held his crucifix as he quickly tugged off his pants, his red and blue briefs were barely containing his hard dick as he stepped over to me and started to pull my flannel shirt over my head without unbuttoning it. My pale white skin was on display, and my thin but somewhat defined body was also smooth with very little hair anywhere. He started to pull at the belt holding up my pants and leaned in for another tongue-filled kiss. I couldn’t help but moan as I felt my pants come undone and his hand slipped in to rub the front of my briefs, my hard dick nearly blasted off from the first touch of another man.

He pulled me towards the bed in the middle of the studio apartment, pushing me back until I fell. He wasted no time in reaching down to yank my tighty whities off, my hard dick sprang free. The angry redhead and my red pubic hair matched in color. I couldn’t help but grin, knowing my dick is 7” cut and on the thicker side, I’ve seen the other boys jealous in the showers at school and expected Finn to be impressed. His eyes smiled at me, and he dropped down, his mouth taking me in with little effort. He moaned on my dick and my eyes rolled into the back of my head.

“Oh God that feels good,” I popped up onto my elbows so I could watch him work my dick and try my best to memorize every nanosecond of this encounter. I quickly got close to cumming and warned him, “Oh man, I’m…umm,” I tried to say something but then it turned into, “Oh…ungh,” as my dick twitched, my abs tightened, and my balls convulsed as I shot my spunk into his mouth. He swallowed every drop and let my dick go soft in his mouth as I fell back onto the bed.

I suddenly felt guilty. The room was spinning and I was well aware that I had no idea where I was in the city, I had read enough horror stories to know that even though this guy just gave me my first blow job, he could also murder me and wear my face as a hat. As these thoughts were running through my head, Finn stood back up and pulled a basket out from under the bed. He pulled out a jar of Vaseline and quickly started dabbing at it with his fingers, then brought those fingers to my ass, smearing the creme between my ass cheeks and focusing on my hole.

“Umm, Finn?” I questioned.

He smiled, “My turn,” he pushed his underwear down to the floor and scooped more of the lubricant onto his fingers, smearing it all over his dick which was at least as big as mine but uncircumcised. “Roll over,” he said, using a hand towel to wipe the extra grease off his hand.

“I don’t think I can do this,” I said, nervously rolling onto my stomach, presenting my ass to him.

“Sure you can, just take a deep breath and relax,” he said, climbing on top of me and running his lubed dick up and down my crack.

The feeling of his manhood gliding across my greased-up hole did feel good and I knew I wanted to do this, so I shut out my thoughts of worry and took a deep breath. Telling myself it’s now or never, I may never meet another sexy guy that wants to have sex with me again, so take a deep breath and relax like he told you.

I breathed in dramatically deep and blew the air out just as dramatically. He slipped a finger into my hole, which was incredibly tight and stung like a bitch. “Ah, geez,” I groaned.

“It will loosen up, I promise,” He told me, wiggling his finger around inside me.

I had fingered myself before, and while I didn’t really get the pleasure I had hoped for, it didn’t sting like this. He slid his finger out, then slipped it back in with his middle finger, stretching my hole twice as much. “Ah, damn man, is it supposed to sting like that?” I asked with clenched teeth.

“Is this your first time?” He asked as he started to make more gentle movements with his fingers.

I put my face into my elbow and groaned, “Yeah man, Jesus,” I huffed.

“Don’t worry Seany boy, I’m going to take care of you,” he said, gently sliding his fingers out and quickly placing the head of his cock at my hole. He leaned forward, placing a hand on the bed to the side of my shoulders, I felt his cross dangle between my shoulder blades as he rubbed his dick harder on my hole.

“I don’t know Finn, maybe we could just,” then I felt him push before I could finish my sentence, the head popped into my hole and a searing hot pain shot through my anal cavity up into my guts, “aww, fuck,” I groaned, and pound the mattress with my fist. Feeling tears well into my eyes, I couldn’t think, the burn of my asshole stretching to make room for his rock-hard dick was so intense. “Wait, no, I can’t,” I groaned.

“Shhh, yes you can, take a deep breath,” he whispered, slowly pushing more and more of his rod into me until his pubes were brushing against my ass cheeks.

“Fuck Finn,” I groaned, “It hurts too much…I can’t,” I tossed my head back and forth, clenching my hands into tight fists. I was in a ton of pain but he had me in a position where I was unable to get him to stop even if I tried, plus the alcohol from earlier had me blurry and unable to focus or argue with his orders like "Just keep breathing and it will feel better soon,” as he rocked his hips on my ass and grind his pelvis into my ass.

He slid his hands under my arms, hooking them up to my shoulders so he could pull himself into me as he pushed hard into me. “God I love a cherry ass, it’s so tight,” he moaned, thrusting balls deep into me.

“Ahh, shit, it still hurts man,” I groaned, feeling him hit deeper with every thrust.

He kissed the back of my neck, laying flat on my back as he humped into me, moaning into my ear, “Sean, you’re too tight, I’m not going to last long,” he said, pulling himself into me even harder. He used his legs to spread my legs wider, He grunted and gasped for air as he fucked the virginity out of me.

Something about the combination of his moaning and the knowledge that he was getting so much pleasure out of my ass had flipped a switch inside me and I was finally starting to enjoy it.

“That’s it, baby, let me in, feels so good doesn’t it?” he nibbled on my shoulder as he fucked me faster.

“Uh-huh,” I moaned, my breathing being interrupted by his harder thrusts.

“Oh God, I’m about to shoot,” he moaned, then gripped me tighter. “Out or in?” He whispered in my ear.

“Huh?” I didn’t understand, and his thrusting was now giving me pleasure on the inside I had never felt before.

“You want it out or in you?” He said louder, with a bit of a growl, thrusting and digging deep into me.

“Umm…” I realized he meant he wanted to shoot his spunk inside me, “uh, out?” I tried to say with authority and failed.

He thrust and slammed into me, “Unh, too late, mmmm,” he moaned and I felt him shooting his hot load inside my ass. The added liquid was putting out the burning sensation from him fucking me so hard, it felt so good as he gave a few more thrusts as he left every drop of his semen inside me, and finally pulled out as his dick was softening. “Mmmmm,” he grumbled and rolled onto his back next to me, huffing and catching his breath.

I don’t know what came over me but I went into a bit of a panic mode. It might have been a religious moment or something, but I felt incredibly guilty all of a sudden. I felt dirty and used and could only think about how what I had just done was wrong. I quickly got up and pulled my underwear on from the foot of the bed.

“Are you ok?” he asked, propping himself up on his elbows.

I nodded ‘yes’ as I quickly sorted my clothes from his on the floor and dressed haphazardly, nearly falling over as I slipped my shoes on with my pants still unzipped and unbuttoned. “I just have to get home, it’s late,” I told him, pulling on my shirt.

“Ok,” he smiled at me and watched as I basically ran out of his apartment, fumbling with the locks until I got the combination correct and was able to get out.

Once outside, I zipped up my jeans and took in a breath of the crisp night air. I ran for about twenty blocks until I couldn’t breathe anymore and had to walk the rest of the way home. The further I was from Finn’s apartment, the better I felt about the experience.

When I got home, I snuck into my room and undressed. Feeling safe in a familiar place, I stripped back down to my underwear, catching myself in the mirror. I can’t prove it, but I swear I looked and felt more like a man. I turned off the light and lay on my bed. The images of Finn sucking my dick flashed through my head and my dick quickly got hard again. I pulled my cock and balls over the waistband like I had a thousand times before and started stroking myself. Picturing Finn’s reddish blond hair bobbing up and down as he sucked my dick. Then my thoughts turned to how much pleasure he got from sliding his dick into me and my fingers slipped down to my lubed hole and gently grazed my sore ass lips remembering that he had an orgasm from fucking me, that he emptied his balls inside me and I blasted my second load of the night all over my abs.

I quickly used my underwear to clean off the mess and tossed them into the corner of my room and drifted off to sleep.

The next morning I was slightly hungover, mostly just tired and sore.

“You got in late,” My dad said, looking up from his newspaper at breakfast.

“Yeah,” shrugged.

“You’re Uncle doesn’t pay you enough to be getting home so late,” my Mom added.

I smiled, thinking if they knew what I was actually doing last night their heads would pop off their shoulders. Breakfast was probably the best I’d ever had.