The Tailor's Assistant - Part 2

All characters are 18+

This is the second part of a commission piece.

Isn't it so unfortunate when you've been having the hottest thoughts, or watching the best porn and after a minute or two of sheer, toe curling pleasure, the mere idea of the whole thing makes you cringe? Well that's what I expected to happen between Tyler and I.

I was under no illusion. I had strategically coerced one of my long-time bullies into stripping to his underwear which ultimately led to an admittedly beautiful moment in which he fed me his delicious load. Sure, he hinted that it would happen again, but I wasn't naïve.

Tyler was as straight as they come, at least that's what he had led everyone to believe for as long as I'd known him. There was no doubt in my mind that the moment he left Benson's, the only things running through his brain, were the ways in which he'd brutally humiliate me for tricking him like that.

When the following day came around, I did my best to hide from him. In Benson's I had to power, but in the concrete jungle of the schoolyard, Tyler and the rest of his gang reigned supreme. Did I expect to be cornered by Tyler at lunchtime? No. Did I expect him to growl a simple set of words at me? No. Did I expect to suck his perfect cock under the bleachers until he dumped his load in my throat a second time? No, and did I expect that to continue every single day for over a month? You bet I didn't.

I became my bullies personal fleshlight. Every single day without fail, Tyler would sneak off and wait under the bleachers, and I would come along and drain him. Without fail, also, once the deed was done, he would remind me yet again that this was to stay between us.

I want to make something clear. I never expected it to go any further than the magical evening in Bensons. Of course, I was happy that it had, but dropping to my knees every afternoon and sucking dick like it was my job, was beginning to wear thin.

"Those boys giving you trouble again?" Benson asked me as I slouched over the counter.

I shook my head, but it wasn't entirely true. Brent and Connor still hated me, and the cruel torment hadn't stopped just because I was secretly sucking off their best friend. Tyler of course, maintained his uselessness and stood around whilst they took turns beating me up. It wasn't that, that was making me miserable though.

"So what's with the long face?" The old man asked, leaning on the counter next to me.

"It's nothing" I sighed. Whether Benson had his suspicions about me, especially after what Tyler had said, I was unsure, but even if he knew and somehow didn't mind the fact that I was gay, he certainly wouldn't understand my situation in the slightest.

"It's that boy, isn't it?" He asked, and I knew he was referring to Tyler.

"He apologised, it's forgotten about" I shrugged.

"Not the name" Benson scoffed, "I've watched you argue with the meanest of customers, names don't hurt you". He clapped my shoulder with his hand, and leaned forward. "You're in love with him".

The words felt like an electric shock. I jerked my head to the side and stared at him nervously.

"You're like a son to me, Liam" he smiled warmly, "and you're really not that great at hiding things either" he laughed.

I couldn't believe my ears. Benson had known all this time, and yet he'd never even commented on it. My heart raced, but all I wanted to do was hug him.

"I could tell you that he's not worth your time" the man continued, sewing a button onto a suit jacket, "but you wouldn't listen to me if I did", he chuckled and stared back at me, "talk to him, tell him how you feel and if you get nothing back..." he shrugged, "then you've dodged a bullet, kid".

The next day at lunchtime, just like it always did, my phone buzzed in my pocket. I pulled it out and read the intricate, detailed, descriptive message from Tyler:

Bleachers.

I rolled my eyes, but Benson's wise words rang in my mind. I didn't want this to end, but I did want it to be a bit more than what it was. I hurried off, determined to set things straight once and for all.

Tyler stood buried under the bleachers, out of sight of everyone. He always looked nervous when we met here, perhaps he was worried that somebody would find us, and his dirty secret would be revealed to the school. The idea made me smirk.

"You're late" he growled, and began to undo his pants.

I rolled my eyes again, something I was becoming used to as he pulled out his delicious cock and held it there, waiting.

"Well come on" he snapped, waving it, "suck it".

I stared at it. Admittedly, I considered sucking it and then confronting Tyler, but I had to stick with the plan in my mind.

"No" I shrugged, and his eyes narrowed to slits.

"What?" He asked, clearly shocked.

"I said no, I won't suck it".

His jaw clenched, and his dick began to soften.

"Why the fuck not?" He barked.

"Because you treat me like shit, Tyler!" I yelled, and he dragged his pants back up and pushed his finger to his lips, his eyes shooting around the yard.

"You act like I don't exist whenever you see me, and the only time you treat me even remotely decent is when you're sticking your dick in my mouth!"

Tyler's face had turned red now.

"What do you want?" He snarled, "you want to go on fucking dates? Hold hands through the hall? I'm not a fucking faggot, Liam!"

His face dropped when he realised what he'd said. I shook my head and turned to walk away, but he called me back instantly.

"Wait! I'm sorry" he growled, "I... I just–"

"Forget it" I sighed, and continued walking, until I felt his hand around my arm, and he spun me back around to him.

"What do you want, Liam?" He asked seriously.

I hadn't worked that part out yet. I stared at him, and he stared back. God, he was beautiful.

"I want you to treat me like I'm more than just a mouth" I said seriously, "I don't expect you to announce it to the school, but you could at least invite me over to hang out at yours or do something else that's private".

Tyler laughed, and then stopped and stared.

"Oh, you're serious?" He asked, concerned, "listen, bro, I don't know if you've realised this, but I can't be seen with you at all".

I felt my heart drop as he spoke.

"Sorry" I nodded, "I forgot I was such an inconvenience".

I turned around again and walked away.

"God, you're such a fucking dipshit" I heard him sigh, and once again I was flipped back around, and the handsome jock stood inches from me.

I glared at him angrily as he sighed and shook his head.

"My folks are out of town tonight" he said, "after my baseball game, come over and we can... I don't know, get pizza or something".

"Get pizza?" I smirked, and he tried to contain his own grin.

"You know what I mean" he said, nudging me, "you're not like... A vegan or anything, are you?"

I scoffed. "No, I'm not a vegan, Tyler".

The stunning young man nodded, and pulled his dick back out of his pants.

"Alright" he said, "well hurry up then, I need to get to my next class".

I stared down at his fleshy pole, and got down on one knee. I slowly wrapped my fingers around his shaft and listened as he sighed contently from above. When I slid it back inside his pants and stood up, Tyler glared at me angrily.

"See you tonight, Tyler" I smiled, and this time I did walk away.

Tyler text me his address later that afternoon, and by seven, I found myself standing outside a house that dwarfed my own one. It was huge, and it made me no less nervous as I travelled up his long, winding drive and knocked anxiously at his door.

I always knew Tyler's family were wealthy, but I didn't know they were rich. The door opened, and so did my eyes.

The young man stood before me wearing only a pair of tight black briefs. I stared down at his large bulge, before he smirked.

"Come on you fucking nerd" he scoffed, grabbing my wrist and pulling me inside his mansion.

I could have stared around the stunning hallway, but my eyes remained firmly on his beautiful fat ass. He led me up the stairs, my mouth watering and my cock already becoming stiff, until we reached his bedroom, and he closed the door behind me.

Three pizzas sat on the desk, a bottle of wine and an assortment of snacks next to them. Further up the desk, a six pack of beer.

"I know you gay guys like wine" he shrugged, "but I'm not that gay".

I grinned as he stood before me.

"You're more than a mouth to me, you dumbass" he whispered, and brought my hand to his crotch. "I don't know what you are, but it's more than a mouth".

I felt his pole swell in my grasp. Being this close to Tyler in his own bedroom was making me feel things I'd never felt before. His free hand slid up my chest until he lifted my chin and brushed his lips across mine.

The scent of him made me shiver. I could smell the fresh sweat from his recent game, and the lingering aroma of his deodorant. His lips touched mine again, longer this time, before he pulled away.

"Yeah" he laughed, "I'm gonna' have to get used to that".

I smiled again.

"I have an idea" he smirked, and I could tell that he was tensing his body as his muscles began to bulge, making my cock bulge too.

"I'm pretty sore after my game" he told me in a seductive whisper, "and I know you're like, in love with me or whatever, so how about a massage?"

"And what's in it for me?" I scoffed.

Tyler slid his fingers into the waistband of his underwear and slowly lowered them down over his large, curled cock.

"What's in it for you is..." he whispered, squeezing his shaft, "you can rub whatever part of this body that your little heart desires".

He stepped out of his underwear and turned toward his bed to reveal his perfectly plump ass. Tyler spread his stunning body out on the sheets, spreading his thick muscular thighs apart and leaving me drooling.

"And when you're done" he groaned, burying his face into a pillow, "you're not going to suck my dick... I'm going to fuck you".

I wasted no time. Seeing the hot young hunk laying there so vulnerable and perfect made me weak. I reached out, squeezed his buns in my hands, and he yelped.

"Fuck" Tyler laughed, "that was quick".

I laughed too, but kept my hands in place, kneading his cheeks as he relaxed back into the bed.

The more I massaged Tyler's bubble butt, the harder my cock became. I ran my hands up his chiselled back, hearing him groan and sigh as I worked his muscles. He mumbled as I returned back to his ass. I couldn't contain myself, each time I spread his cheeks apart, his opening became visible. I ran my finger gently across his most sensitive area.

"Don't even think about it" Tyler growled.

I laughed as his cheeks clenched, and then the young man flipped over, and his large cock lay across his groin, the tip, slick with juices.

"I think something else needs attention" he smirked, and tensed so that his cock danced. "Lubes in the drawer".

I almost jumped for it. My heart was racing faster than it ever had before, and when I returned to the bed with the lube in hand, Tyler laughed.

"Are you gonna do it with your clothes on?" The jock smirked, and in my excitement, I'd almost forgotten.

Tyler hadn't seen me naked yet, and part of me was worried that when he realised that I wasn't as perfect as he was, the game would be up. I awkwardly fumbled with my t-shirt, until he sat up and dragged it over my head.

I waited for him to laugh at my skinniness, or make a comment about my lack of bulging muscle, but he didn't say a word as he pulled down my trousers.

His hand rubbed against my throbbing erection, and with the flick of his wrist, my boxer briefs came down, and I stepped out of them, naked.

His eyes trailed my nudity, taking in every inch as I shivered nervously. Being naked with him felt amazing, yet terrifying at the same time.

Finally he looked up at me and grinned.

"Well?" He said, "what are you waiting for?"

A grin lit my face. I grabbed the lube once more, squirting it onto my hand before grasping his large cock. He slid his hands behind his head and watched with a smirk as I lathered the lube onto his boner.

My own cock drooled as he sighed with relief. His balls were heavy and full, and everything about the young man was amazing.

I squirted more lube onto my hand, and slid it over my virgin hole.

"Show me" he breathed, sliding his fist up and down his cock as I turned to show him my wet, pink hole.

"Fuck yeah, finger it".

I pushed a finger inside, playing with myself whilst Tyler beat off to the sight. It was hotter than I could have ever imagined it would be.

I continued fingering my tight ring, first with one finger, then with two, and Tyler's breathing became deeper.

"Sit on it" he demanded, and I couldn't have held off, even if I tried.

I straddled his waist, staring directly into his eyes as I felt his slippery cock head slide against my opening.

I winced slightly as it pushed inside, but it wasn't painful. Tyler's eyes closed for a moment as he basked in the pleasure, until I sat further down and felt him enter me fully.

His muscular chest rose and fell, his hands held my waist, and suddenly I was being fucked by the hottest guy I had ever known.

The wet clapping noise of sex filled his room. I moaned loudly, not fearing that anybody would hear us, and Tyler grunted and gasped as he impaled me on his cock.

It was magical. More magical than the first evening at Benson's, or the first time I swallowed his cock under the bleachers. This was different.

His body was slick with sweat. His white teeth bit down on his bottom lip, and each perfect stroke made me shiver with ecstasy. His cock angled perfectly, punching against my prostate with each gliding thrust.

My fingers rain through my hair as Tyler drilled deep. Our eyes connected again, seductive and narrow, our breathing became one, and the burning orgasm approached.

A flurry of electrifying pulses rushed through my groin, it wasn't like a normal orgasm. It felt heavenly. He grunted, his fingers dug deeper into my flesh, and finally it happened.

Wisps of thick sperm exploded from my throbbing erection. It splashed across his pecs, doused his mouth and chin, drooled down his six pack and spilled down my own shaft. He gasped again, moaning roughly as he began to expel his cum into my bowels.

I felt him filling me up, each stroke sending more hot fluid into my hole until it was over, and the two of us stared at each other breathlessly.

"I think" he said, trying to catch his breath, "I can probably get used to this".