The Tailor's Assistant

All characters are 18+

This is a commission piece that I did for someone, but I wanted to share it here with you guys too.

Trigger warning: Some brief violence/bullying.

I was never a popular kid growing up. I guess it was mostly down to my families miserable financial situation. We were poor, and there was no other way to say it. My dad up and left the moment I was born, I suppose he never wanted to be a father, and so my mom had raised me herself. She did what she could, but I was the butt of most of the cruel childhood jokes in school.

I wore the same clothes until they literally fell from me, and if there was any life left in them at all, they'd be passed down to one of my two younger siblings, sometimes to the other one after that. Life sucked, but it was made all the worse by three people in particular.

Brent, Connor and Tyler were exactly the type of guys you'd expect three eighteen-year-old, cocky douchebags to be. It was no secret that Brent was the leader of their nasty little trio, and he made sure everybody knew it, too. Connor got his kicks out of making my life hell, almost as much as Brent did. Tyler wasn't particularly cruel, but he didn't do anything to stop his two buddies beating me senseless every other day, either.

I'd managed to survive school so far, which was impressive considering the gang had been targeting me since we were fourteen-years-old. I guess I realised I was gay around the same time that they realised I was gay, and they hadn't let me forget it since.

My only saving grace was Benson. You're probably thinking that Benson is a hot, muscular, jock type guy who I have a passionate secret relationship with. Well, Benson is a sixty-three-year-old man with grey hair and wrinkles, but it's not what you think.

I met Benson when I was sixteen. I learned pretty early on that in order to go to school with a full belly, my mom's salary just wasn't going to cut it, and so I began working at thirteen. I did odd jobs for people who knew that they could get as much work out of me as possible, for as little as possible, but when I walked into Benson's Suits and stammered and stuttered about how I'd work every hour that god sent, the man smiled at me, gave me a hot chocolate and chatted with me until closing time. He gave me fifty dollars just for that, and I'd been working there ever since. The man was like a father to me.

I suppose I should introduce myself before I tell you about the day that changed my life. My name is Liam, I'm not the best looking man on the planet, but I'm not the worst either. My hair is as black as midnight, something I must have gotten from my dad, because my moms a red head. My green eyes however, are definitely from her. I'm skinny, but not in a sickly sort of way. I suppose most people are skinny compared to the footballers and wrestlers that stroll around the school showing off.

The day that this story begins was a day like all the others. I found myself in the unfortunate situation of being surrounded by Brent, Connor and Tyler, just as the final bell sounded. Connor held me in place, forcing my arms down by my side as Brent used me as a human punching bag. I'd gotten used to it by now, but it still sucked, and even when I was thrown to the ground, the punches and stomps continued.

Tyler watched on like he always did. His eyes stayed on me as I winced and groaned through the attack, and for the briefest of moments, I almost thought he was going to help. He hunkered down beside me, smacked me firmly across the cheek and grinned.

"You're pathetic" he snarled in my ear, "fucking faggot".

When I got to my feet, I did so with tears in my eyes. It wasn't the pain, nor was it the vulgar slurs. I was simply tired.

Despite my exhaustion however, the ordeal had gone on far longer than usual, and when I checked my watch, I cursed under my breath, grabbed my backpack and ran from the school to Benson's.

As kind as the man was, he was stern too. Benson liked order, it was the reason that his shop had stood for generations, or that's what he told me, at least. Not only was I late, but I was late for one of the busiest shifts of the year.

Prom was a week away. Final orders were today, and as I rushed across the packed out parking lot, I felt a sinking feeling in my stomach. I hated letting Benson down. Hated it.

"Sorry, sorry, I got held up" I apologised profusely as I stripped from my jacket and donned the smart clothing that Benson insisted on.

The place was already theming with young men, all being fitted for suits for their special night, and one stern look from Benson told me to keep quiet and get to work. And that's exactly what I did.

Being a tailor was more exciting than I had ever expected it to be. Not that I really expected to ever be a tailor anyway. I guess it's not the type of vocation that young people pick when they're asked what they want to be when they grow up. Sure, altering, repairing, fitting, sewing and stitching were all interesting but that wasn't the only draw.

As a young gay man, having the chance to get up close and personal to handsome guys all day, measuring their arms, legs, chests and waists was the closest thing to heaven I could ask for. Naturally of course, I always remained professional, but a boy can certainly dream, and dream I did.

Dozens of young men came and went in the hours that I spent measuring that day. I was still exhausted, but it was almost time to go home, and the idea of falling onto my bed and sleeping until another miserable day dawned tomorrow, was actually quite nice.

"Another rough day?" Benson asked, when the shop had finally cleared out.

I nodded, my eyes falling to the floor. Benson knew about my struggles in school, he even volunteered to go and talk to them, but I refused. I couldn't imagine that the trio would go any easier on me if I got some old man to fight my battles.

"Is it that obvious?" I scoffed sadly.

"You look like you've gone twelve rounds with Mike Tyson, kid" he said sympathetically, and pointed to my eye.

I rushed toward the mirror and sighed. A dark bruise was already forming around my right eye, and now that I had a moment to think about it, it hurt like shit as well.

The bell over the door sounded, and both of us turned around.

"I'm so sorry" a woman groaned, beckoning someone inside, "I know we're late, but my son got delayed in school, would you be able to fit him in for a measurement?"

"Of course" Benson smiled warmly, "my assistant can get started on the measurements, and we can take a look at fabrics".

The woman looked relieved, and just as I collected up my tape, my eyes landed on the young man who walked inside.

Tyler looked just as unbothered as he always did. He had an infuriating arrogance about him, as though everyone was required to bow down around him. He was hot, and admittedly, I had been head over heels for him for quite a while until the relentless bullying had started. He was six foot two, or thereabouts, with a thick mop of chocolaty hair and the same colour eyes, but it was his perfect body that made people drool over him.

I thought back to the time when I was one of those drooling people, and how I was caught by his friends when my eyes had lingered on him a little too long. I never looked at him like that again.

"Shall we get started?" Benson beamed, leading the way, but Tyler's eyes had found mine, and the two of us glared at each other.

"I'm not going in there with him" he growled to his mother, who did a double take at her son.

"What?" She quipped, "don't be so silly Tyler, he's a tailor".

"He's a faggot" the young man snarled under his breath, but everybody, including Benson, had heard it.

Benson's head snapped toward me, I could tell instantly that the man had pieced my black eye and Tyler's nasty insult together, and without a moments hesitation he snapped.

"Out, get out of my shop".

Tyler's mother's eyes widened to the size of saucers. She opened her mouth to protest, but Benson looked angrier than I had ever seen him before.

"Take your son, take your money, and get out".

The woman's finger almost punched through Tyler's face, she held it so close. I could see the furious shake in her body, and then she slithered the words that every man, no matter his age, feared.

"Either you apologise this instant!" She snarled, "or your father will hear about this!"

Even I felt nervous as I watched the blood drain from Tyler's face. He stared at me with a look of bitter hatred in his eyes, and spat an apology at me.

"Oh no" she scoffed, "absolutely not! You go over there and you apologise to that boy like you mean it!"

His mother was clearly on the verge of smacking the taste out of his mouth, and Tyler knew it. His cheeks burned red, and his brow furrowed. He stormed toward me, and if I hadn't just heard his mother's threat, I would have expected a punch in the mouth.

"I'm sorry, Liam" he said, louder this time, "I shouldn't have called you a faggot" I knew that the last word was simply another insult, but I didn't really care. I'd been called it enough times over the years for it to have no real effect on me anymore.

"I am so sorry" his mom said to Benson, "I can pay extra for this, I really do apologise".

Benson ignored her and looked to me for approval. It felt quite good to be in control for once, though the idea of being locked in a room with Tyler was beginning to make me a little nervous. Regardless, I nodded and Benson walked in silence with the woman.

Tyler followed me into the fitting room. It was a small place, with only a podium and some mirrors. I closed the door when he got inside, and when I turned back to him, he was in my face in an instant.

"Don't get any ideas, you fucking queer" he spat, his jaw clenched and his eyes narrow, "or I'll give you a matching black eye, got it?"

I was about to nod my head, until I realised something. I didn't just have control outside with Benson, I had control here, too.

"Oh yeah?" I asked, my throat a bit too dry to be threatening, "then you can just go back out there and tell your mom that you've changed your mind, and that I am a faggot, and you can tell your dad the same thing when he gets home".

The look on Tyler's face was almost comical. He swallowed his aggression and had he been a dog, he would have growled.

"Just hurry up" he spat, and stepped onto the podium.

I could have had him measured and fitted in five minutes. I could have kept my mouth shut, been professional and gone about my day once he'd left. There were a lot of things I could have done. But there were lots of things that Tyler could have done too.

Tyler could have stopped his friends beating the shit out of me for the last few years. Tyler could have pulled my head out of the dirty toilet when it had been flushed down there because I looked at him for a second too long. Tyler could have shown the slightest bit of compassion, but he hadn't.

"Have you been measured before?" I asked him, and he shook his head.

I stood there and stared at him blankly. I wanted him to feel stupid.

"What?" He snarled.

"Uh... You're still dressed?" I scoffed, as though it should have been obvious, and that everyone was supposed to strip off to be measured.

His cheeks burned again, his hazel eyes darted around the small room as if looking for an escape route, and then he sighed.

He kept his eyes on mine, like he was waiting for me to drool or something. His fingers worked the buttons on his shirt, and slowly he slid it off him to reveal his impeccable physique. His abs were perfectly defined, his pecs too, and his arms were meaty and muscular. Part of me did want to drool.

"And your pants" I said, pointing to them.

Tyler's jaw clenched tighter, but reluctantly he unbuttoned them and pulled them off a moment later. I felt my dick swell in my underwear. Everything about him was perfect. His legs were thick with muscle, his thighs were too, and his tight boxer briefs hugged his crotch in the most sensual way.

Perhaps he realised that I was enjoying the sight, because he draped his hands over his package and stared at me angrily.

"Can we move this along?" He barked.

Despite the fact that I would have happily toyed with him for longer, I still had a job to do, and Benson wouldn't be happy with me if I didn't do it well. I took out the tape and began to measure.

Touching Tyler's mostly naked body was doing little to stem to aching boner in my pants. I ran my fingers across his thick biceps, wrapping the tape around it and noting the measurements. I did the same with his chest, lifting his arms and inhaling his musky aroma. God, this was hot.

I slid my hand between his thighs under the guise of professionalism, and brushed my arm across his junk.

"Watchit!" He hissed.

I took measurements of every conceivable part of his body. By the time I was done, I had numbers that I didn't even need, and yet I still looked around for more.

"Just your ass" I said, trying to hide the grin on my face.

"You're fucking with me?" He snapped, and I simply shrugged.

I wrapped the tape around his butt, closing it at the front, just an inch above his heavy looking package, and suddenly something happened. The bulge began to grow inside his underwear, slowly at first, but quicker the longer I remained in place. For a moment I pretended not to notice, but eventually it was impossible. Tyler's erection pushed against the fabric of his underwear, and I glanced up at him.

I considered doing nothing. Finishing up and allowing the young man to leave without ever mentioning this again, but when had he ever afforded me such kindness? Without thinking, I rubbed my hand across it.

I waited for a punch, or even a stern telling off, but Tyler remained silent. I did it again, firmer this time, and again, nothing.

Tyler shuffled on his feet. I was in awe. This macho, confident, cocky young stud had gotten hard, and not only that, but he'd gotten hard for me!

I stared up at him again, and finally he stared back. He looked uncomfortable, as though he wanted to punch himself for this humiliating accident, and then he said the words that I never imagined he'd say before.

"Suck it for me, will you?"

For a moment we just stared at each other. I guess I couldn't believe he'd said it, almost as much as he couldn't believe it.

After a minute in the awkward silence, Tyler hooked his fingers into the waistband of his boxer briefs and slid them down. His stubbled bush appeared first, and all I could do was watch the scene unfold, inches from my face.

The base of his cock appeared next, his erection was pressed down against his thigh, but more and more of it was revealed until it sprung out, almost hitting me in the chin, and bobbed in the air before me.

It was quite large, probably seven inches of thick, veiny cock. His low hanging balls flopped out and his underwear wrapped around his knees.

"Please?" He added.

Sucking my tormentors cock hadn't been on my to do list that day, but as his warm scent rushed up my nostrils, and my own cock continued to drool, I had no other choice.

I wrapped my hand around the base of it, feeling him gasp when I did, and squeezed as I slid my hand up his shaft. Tyler grunted as a thick bead of clear fluid spilled from his cumslit and dropped onto the platform below.

With my heart racing and my dick bulging, I leaned forward and pushed his thick cock between my lips. I tasted his pre-cum instantly, a sharp, salty, beautiful liquid that coated my tongue in his flavour. I tongued at his frenulum, feeling him tense up with every lick. Even from down here, I was still in control.

His cock slid across my tongue and pushed into my throat, making me gag slightly as it did. His breathing was heavier now, and his cock, harder.

I sucked it and jerked it at the same time. He added more pre-seed to my throat, and began thrusting slowly. His body was now covered in a fresh sheen of sweat, and his hand found it's way through my hair.

He pulled me deeper onto it, gasping as quietly as he could as he fucked my throat. My nose rubbed across his stubble, my chin, across his balls.

I could feel my underwear become wet in my own juices, and squeezed myself with my free hand. Anything further, and I would have blown my load there and then.

Tyler continued fucking my mouth, becoming more aggressive by the second. His heavy balls swung back and forth, hitting me with each stroke, until finally he gasped.

"Swallow it!" He demanded, his chest heaving, "swallow every drop!"

He didn't need to tell me twice. His pole swelled between my lips. His balls began to crawl upwards in their wrinkled sack, and he moaned as a thick splash of heavy cum burst into my mouth. I swallowed it, and my mouth flooded again. He was frantic now, bucking wildly as he drenched my throat with his sperm. It spilled down my chin, but the majority was sliding into my stomach with each large gulp.

When he'd emptied himself into me, his sweaty body went limp, and his wet prick slipped from my mouth. I suppose we were both in a state of shock, but I still fingered the trail of fresh cum from my chin, and sucked my thumb.

"You're pretty gay for a straight guy" I smirked, but the angry look on Tyler's face told me that he wasn't in the mood for jokes.

"If you ever tell anyone about this" he snarled, pointing his finger at me, "then this is never happening again".

I sighed for a moment, until I realised what he'd just said. I looked back up at him, my brow now furrowed, and he smirked.

"See you tomorrow, Liam".