A Hard Lesson

Jack was tired, exhausted, hungry, all the above. He was tired of searching community centers for food, or scraps in dumpsters behind restaurants. He's almost run out of options aside from prostituting himself, but he really didn't feel like risking his sexual health for a bit of food. Jack was slender, almost scrawny because of the lack of meals and nutrition, and he avoided the sun as much as possible although he's worked up quit the tan just from constantly roaming around for food during the day. At only 19 years old, Jack was considered homeless.

"Fuck," He searched the last nearby restaurant's dumpster, it was approaching 1 AM and he was starting to lose hope. As of today, he hasn't eaten anything for almost 72 hours. His stomach felt like it didn't exist, and his appetite was shit, except for the occasional feeling empty. Jack was nearing total exhaustion, his body slowly shutting down to preserve energy. Then, he saw a bright sign.

It was a sign that belonged to a convenience store. He didn't like pinching, but it seemed to be his last resort. And of course, he wouldn't dare do it off the bat, he would sit behind the building and conduct a scheme. But before he did, he would try his father's place, although they haven't spoken for year, he thought that there would be no way he'd let his own son starve, right?

Since the convenience store was 24/7, he started jog-walking towards his father's house. Except it was more of a mansion or manor rather than a house. Of course, his father was loaded, but he only recently got in touch with his son and barely made an attempt to reconnect. He was getting closer to his destination, and he made sure to always consider this a last resort. Though he's never had to ask his father for anything before.

Jack stared at the large house, or manor. He took a huge inhale and gathered his courage to knock on the door, softly. The lights were on, surely someone was awake. The door creaks open, a little girl about 7 or 8 years old opens the door. "Yes?"

But before Jack could speak, he heard a man yelling. "LEIGHA! How many times do I have to tell you not to open the god damn door! Especially not for strangers!"

"I'm sorry daddy, there's a man," She was looking back inside toward where the voice was coming from. The man approached the two of them.

"Go back upstairs and get in bed, honey," And she did quickly. A part of Jack started hurting when he saw her, about how his father left him at 3 years old but is raising a daughter now. "What do you want at this time of night?"

"Dad..-"

"Jack? What the hell. You have my contact info, why can't you text me rather than showing up suddenly-"

"I'm sorry- I just.. Wanted to talk." Jack's voice started to waver slightly, his father sighing and stepping outside while closing the door behind him.

"What is it? I'm very busy you know."

"Uhm.. So.." Jack was twiddling his thumbs in anxiousness, his sun-bleached hair fell past his eyes and ears, covering his face when he looked down. He mumbled but it was unintelligible for his dad to hear.

"What? Speak up, I haven't got time for this-"

"Sorry! I just wanted to know if you could spare a small amount of money for a meal, or just a sandwich or something. I haven't eaten in a while, and I hate asking you but-"

"Go home Jack. I'm not giving you money so you can blow it on drugs." He quickly replied with a harsh tone to his voice.

"No- no.. I'll take some food too-"

"No. Absolutely not. I know how you homeless sell food for money just to buy another score. Now leave before I call the police to escort you," He turned without looking back and shut the door.

Jack bit his lip while he struggled to hold back tears, a hard lump working its way up his throat. He didn't want to cry because he was hungry, he wanted to cry because his dad saw him as some homeless junkie stereotype while he raised another kid he was in their life for. Hiccups managed to work their way up and escape his lips, he quietly sobbed as he dragged his feet back in the direction of the convenience store.

He decided to check the dumpster before heading inside and initiating his pre-made plan, but once again, no food or drink. He made sure to get this done with, quickly and carefully. The cold breeze combed his hair, revealing his pale blue eyes and slim, kinda long-ish nose. His lips were also on the bigger side and could be considered what some call, 'DSL'. He had a slightly bigger ass but that was mainly due to genetics. It's also the reason he would consider escorting sometimes.

Jack once again, took a very deep inhale and pulled his hood over his head. Then pushed past the glass doors inside the store. He looked at the clerk and analyzed him thoroughly. Slightly older man but no visible gray hairs, jet black hair that was styled neatly, long on top and short on the sides and back. The top was held in place pushed back with gel, his nose was a bit fat but not very long. His lips were on the thinner side, but his body was actually kept in shape. Like if they got into a wrestling match, Jack would definitely lose. He wasn't like bodybuilder fit, but he had some impressive muscles for sure. Hell, probably anyone could overpower Jack with his body in the state that it's in.

That's why he knew he *needed* to grab the food and dash. The man displayed a warm smile at Jack, "Welcome," He said before Jack broke eye contact and made his way down the snack aisle, making sure to keep his face semi-hidden. Lots to choose from, but he'd only have space in his pockets for smaller snacks like a single bag of chips or a small bag of jerky. He looked at the cashier with only his eyes, and the cashier wasn't paying attention. He was restocking the lottery scratchers at the front desk. Jack swiftly and quietly started to fill his pockets with various snacks, like the small bag of chips and a few packs of crackers.

Jack took one last glance in the corner of his eyes, before making his way towards the door. "Wait!" Was what he heard when he stopped before exiting. He started to become terrified but made sure not to look obviously suspicious. He turned back around and tried to smile.

"Y..Yes?"

"I haven't seen you in the store before. Are you new to town?"

"Ah, no. I just... don't have a car so I don't need to go to gas stations." He tried his best to make his excuses sound convincing, and he hoped it was working.

"Mmm. I see." The cashier stepped out from the front desk, moving closer toward Jack. He got close enough where he could see his name tag. 'Manager | Mason' of course the cashier was also the manager. His smile slowly faded as he got closer, his arm extending out next to him against the wall. "So tell me," He waited for him to give his name.

"Jack," He picked up on it fairly quick.

"So tell me, Jack," his arm dropped, and he towered over him, the intimidation only growing further.

"Hm..?" Jack started to tremble somewhat, his eyes looking down to avoid feeling the guilt grow.

"Why is a first timer in my store stealing?" Jack immediately straightened his posture, his eyes widening and looking up at Mason. Mason presented a cocky smile. "Didn't think I'd find out huh? Y'all been stealing from my store for a while, but now I'm too aware of all the tricks." He grabbed and yanked Jack by the arm, Jack wincing as he pulled.

"Ow- sto-"

"Shut up." His tone was even more firm. It slightly scared Jack inside. He pulled him into the back office, where there were no cameras, and they couldn't be seen by customers. The man yanked Jack's hood down, revealing his malnourished complexion. "Yer' just a kid.." He stepped back and examined his face. "Strip."

"Wait.. What?" Jack was taken back by his request, so he had to ask just to clarify what he heard.

"You heard me. Strip down. I'm going to find everything you stole."

"It's just in my pockets, please-" But he was once again cut off, Mason's tone had snapped.

"I didn't ask. I said strip. Everything."

Before pulling off his jacket, he emptied his pockets. He laid out a small bag of chips, a bag of gummy worms, 2 half size packs of salted crackers, and a can of shredded beef jerky. Then he slid off his jacket, glancing up at the cashier a few times. His arms were folded while he watched with intense intent. Jack shuddered under his gaze but continued the task at hand. He slid his shirt off up over his arms, tossing it on top of the jacket. He finally unbuttoned his pants and tugged them off, kicking them to the side. He rubbed his arm nervously as Mason stared.

"Who told you to stop?"

"What?.. Underwear too?"

"Yes. Hurry up." Jack swallowed anxiously. He put his thumbs in his waistband and pulled them down to his ankles slowly. He was entirely exposed with no skin left to hide but his scalp. Mason smirked in delight. "Damn kid, yer' too slender. You should eat some more," Jack was taken back by the contradictive compliment. "Now turn around and get on all fours. Full cavity check."

Jack wanted to resist but knew he had no chance of fleeing. He did as he was told, but he felt his torso push down with the sole of a boot. "All the way, ass up," His chest was touching the ground now and his ass was in the air, out for Mason's view. Mason knelt down, stroking his chin as he examined Jack's puckered hole. Jack got extremely shy but didn't dare try to hide his body.

Mason placed both his hands on Jack's firm cheeks and spread, the smaller man gasping in surprise. Jack looked back over his shoulder, staring at the determined man's face. He finally let go and stood back up, stroking his chin again. Jack started to stand up but got pushed back down by Mason. "I didn't tell you to get up."

Jack whined very quietly, "But Mason I-"

"Hahaha. You saw my name tag huh? Except it's not Mason to you, from now on you call me 'master' until your punishment is over. No bad deed goes unpunished." Mason opened the top drawer in his office desk and retrieved an item. He sits down on the office chair, supported by wheels. He patted his lap and motioned Jack, "Come on, come sit in my lap little kitty."

Jack obliged, keeping his hands in his own lap. He felt an unknown material around his neck and reached up to touch it with his fingers. It felt like a leather collar. Jack lifted himself up just a bit to look in the mirror hanging on the wall, and he was correct. It was a black leather collar with a silver buckle and a silver circle ring dangle. "It suits you well." Mason flicked the dangle with his fingertips.

"Oh wait, one last thing," Mason clipped a leash to the ring, and yanked on it lightly, pulling Jack closer. "There we go. Lovely." Jack was still a little confused about what Mason had planned, he didn't expect to be in a collar and leash, let alone naked. Jack was instructed to stand up, which he did, holding his arm in nervous anticipation.

"Gotta be honest, out of all the low lives that come to steal from my store, you've got to be the cutest." He flicked his nipple with his index finger, causing a gasp and shudder from Jack. It made Mason snicker in a devious way. "The beginning of your punishment. Get down on your knees and suck my cock." Jack put on another astonished look. He had no experience, but he would have to try his damned best.

Jack made his way between the older man's legs, undoing his belt buckle and pants. He pulled back the underwear fabric, his half erect dick sprang free. "Make me fully hard," He demanded in a monotoned voice. Jack leaned down, subtly licking and suckling at the tip. He was looking up at Mason, hoping to get a reaction out of him, but Mason was like stone. "Hmm, here,"

Mason was back in his desk drawer, pulling out some kind of, what looked like, silk fabric. He pulled it around Jack's eyes, tying it behind his head, not too tight but not loose where it'd fall off. "Should help you ease your nerves." Jack returned to sucking on the rod in front of him, and it did in fact help him. His tongue was swirling circles under the ridge of the head, flicking his tongue off the top.

Jack finally eloped his mouth over Mason's cock, bobbing his head slowly while he tried to get Mason in the right mood. He tried to take more of Mason's inches in his mouth, nearly deep throating him. He felt his hips start to thrust a bit which meant he was doing at least a decent job. Jack started to moan on time with Mason's thrusting, and it must've turned him on more because he started to thrust faster. Jack nearly gagged at the sudden pick up on the pace. His nose kept getting tickled by Mason's pubic hair.

"Okay, that's enough. You don't need to make me finish," He used his fingers to grip Jack's chin and push his head away, Jack followed Mason's hand that guided him back on his lap. The blindfold was kept around his eyes, so he had to rely on Mason on where to go or what to do next. He wanted to take it off, but he already knew how'd that go. Jack felt something abruptly pressed against his lips and he flinched in surprise.

"Get them wet, suck," He pulled Jack's lip down with his thumb, pushing on his teeth. He opened his mouth just a bit, but Mason's finger invaded his mouth harshly. Jack nearly choked but he kept his composure as he allowed the man's fingers to thrust in and out of his mouth. Jack heard some kind of plastic wrinkling yet was unable to see what he was doing.

Mason had the bag of gummies that Jack planned to steal in his only free hand, using his teeth to tear open the pack of sweets. "There are 5 flavors in these pack of gummy worms. Cherry, Lemon, Strawberry, Blue raspberry and Grape. If you can guess the correct flavor, I'll give you a small reward." Right after, he spread his two fingers to make room for the gummy, pushing it inside past his lips and on his tongue.

Jack starts to chew slowly when Mason removed his fingers, a rope of spit following behind and breaking when it got too long. He cherished the delicious treat in his mouth, chewing slowly so he can identify the flavor of the sweet. "Umm.."

"Hmm. What did I tell you to call me?"

"Ah.. M-..Master.."

"Right," He re-adjusted his posture and wrapped his right arm around the younger man's waist. "Every time you speak you should address me by it." He snickered to himself.

"Mm... Sorry, Master.." He swallowed the remains of the gummy, thinking deeply to himself. "Tastes like... Cherry?"

"Good boy," He lifted Jack's hips up and forward, Jack using Mason's shirt and arm for support. He was confused for a brief moment before his rectum was being prodded at by a pair of thick, long fingers, Mason's fingers. He let out a sudden, surprised gasp. His toes curled up and clenched while Mason's fingers searched around his insides.

"Next," His other hand fetched another gummy, shoving it into Jack's mouth. Instinctively he started to chew slowly, struggling to swallow while his anus was being obstructed. "Come on," His fingers sped up and Jack started to whimper with the candy in his mouth. "What's the flavor?" Jack was having a hard time speaking, let alone chewing. His whimpering became louder as he tried to stifle them in Mason's neck. His hands gripped his shirt and arm tighter.

"Come on," His fingers ejected, and Jack relaxed his body finally. Then he felt a sting on his ass, Mason had induced a light spank. "Flavor?"

"Haa- Um.. I think, Strawberry? Master..." Jack shivered. He was unsure because of everything that was happening. He was hoping he was correct.

"Mm. Sorry, that was wrong. Now you get punished," Mason positioned Jack over his lap. Jack's heart started to race even faster, anxiously waiting for whatever is about to happen. He felt another smack on his ass, but harder than before. But he stopped before administering the next one. "Hm. Get back down on the floor, face down ass up."

Jack scrambled to get on the floor, doing exactly as he's told. Mason hovered over him, unbuckling his belt and sliding it out of his pants loops. He cracked it once before folding it in half. The sound made Jack shiver in both excitement and fear. "This might sting," And he smacks the belt across Jack's soft rear, leaving the belt imprint to burn on his skin. Jack felt both pain but pleasure, his cock hardening and twitching with each hit. He landed his belt on his ass again, and again, until he finally stopped after nearly his whole bottom was red and hot. The belt was tossed aside, Mason helping Jack up from the floor. He could barely hold himself up, so he relied on Mason's arms for support, his legs shaking ever so slightly.

"You did so good," Mason cooed in his ear, Jack turning his head up in the direction of his deep voice. He sat back down once again but made Jack wait so he could take his dick back out. Jack waited as he lubed his own cock, smirking at him as he stroked it. Jack couldn't make out what was going on, but he heard a wet noise over and over. He jumped in surprise when he felt someone grab his hand, and gently pulled him.

Before he could fully process what was happening next, he felt something big invade his rectum. He gasped in pleasure but winced in pain, Mason thrusted upward into him and caused a bigger reaction from Jack. "Relax, or you'll snap my dick off," Mason muttered into his ear, he rubbed his side and his back affectionately. Jack tried his best to relax and accept the whole 6.5 inches of Mason's rod, but it was easier said than done. It was a mixture of pain and pleasure.

Jack's shoulders and head slumped against Mason, exhaling a huge sigh when he finally was getting used to the feeling. He heard more crinkling, similar to the pack of gummy worms but it was less plastic sounding. "Open up," Mason said in a warm tone. Jack obliged; his mouth opened just a bit. He felt something shoved into his mouth between his lips and started to chew. It was a potato chip from the bag he tried to steal. The savory snack practically melted on his tongue, every taste bud metaphorically dancing.

"Mmh.. Thank you, Master." He swallowed the leftovers of the chip. Mason's hips started to thrust again, Jacks whole body moving in rhythm. Another chip entered his mouth carefully, Jack's hands resting on Mason's shoulders, and he tried to chew while getting pounded. The pace was slow, but it was still intense. "Mm.." Jack moaned out as he fought to chew his chip. Every pound was another moan or gasp from him, and it started to get faster. Jack slung his arm around Mason's neck and grabbed onto his shirt while his legs tried to close but couldn't because they were being held open by Mason's thighs.

A hand was wrapped around Jack's erection, and immediately started to stroke up and down. "Oh fuck-" Jack breathed out, his hips now eagerly bouncing up and down. His ass would ripple every time it made contact with Mason's thighs. Jack let his head fall back and his body enjoy the overwhelming euphoric feeling. As he starts to feel himself reach climax, all activities came to a halt. Jack was still in a dazed state when he asked, "Wh... Why'd you stop?.... Master... Haa.."

Mason had re-adjusted Jacks position, completely flipping him the other way and leaning him forward, Jacks hand against the desk. Mason leaned his body upward, right into Jack's ear, "Are you ready? I'm gonna take you to a place you've never been." This confused Jack, his head that was still blind-folded turned back to attempt and look 'over' his shoulder. Mason's hands had a firm grip on Jack's waist, and he promptly started to thrust once again, as fast as before.

Jack's moans could almost be qualified as whimpers as Mason searched around for Jack's sweet spot. He smiled as Jack's body tensed up and his head flung backwards, his mouth wide open from the ecstasy-like feeling. Mason knew he had found it and continued to use his dick to stab the same spot over and over. He stood all the way up so he could gain more momentum, and his dick could travel deeper inside Jack.