This is a story of the sexual exploits of a particularly talented high school boy, and how he uses those talents for fun and money. This is pure fantasy, and nothing like this is likely to ever happen in real life.
This installment sets the background for our protagonist, and gives us a preview of the nasty fun to come. Hopefully inspiration for more of Peter's misadventures will come and he will appear again in many more installments!
All feedback is welcome. Please send to troythewriter@proton.me.
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The whoring life of Peter O'Malley
"Pete, you want a beer?"
"Mom, it's 7:00 am! I'm getting ready for school!"
"So that's a no?"
"NO mom! That is a definite no!"
"Jeez, OK, it's just a Coors light. What's the big deal... never mind."
Pete sighed. He loved his mom but she had absolutely no filter.
Pete was standing in the shower, about to rub out a load to make his chronically raging morning boner go down. He threw his head back and took a deep breath. He was going to have to work tonight, so he let go of his cock.
He finished his shower, leaving his cock to deflate. At 17 years old, Pete had remarkable control over his cock. Unlike other boys his age, he could will himself to get hard, get soft, and cum pretty much on demand. For him it was no more difficult than flexing a bicep. It didn't make the desire to orgasm any less, or the frustration of holding back go away, but it did give him control.
Drying himself off, he looked at his body in the shitty bathroom mirror. He knew that objectively he was good looking- hot, even. At 6'1" and 185 pounds, baseball kept him fit, but in reality, he knew he had hit the genetic lottery. You didn't get those eyes, that mouth, those muscles, and those cheekbones from exercise alone. No to mention his `biggest' asset..
"Don't get stuck staring at yourself." His mom had walked into his bathroom without him hearing and startled him. "It's not like you don't see it every day."
By "it', she clearly meant his cock. It was objectively magnificent. They were not shy around each other, so it was not the first time she had seen him naked- not even the first time that week. They had agreed that there were to be no exposed pubes outside the bedroom, but this was only loosely enforced. Living in a small single-wide trailer limited their individual privacy, but this was still the nicest place they'd ever had. They had no neighbors, so there was no need for blinds. Neither of them would have cared anyway- they were not the modest types.
"I know, but it's still nice to look at. You have to admit, it's awful pretty."
"Cocky little bastard. You're more like you father every day. He gave you that pretty pecker."
This sent a little stab through him. He had never met his father, but Pete's mom had told him how he had come to be.
Maryellen O'Malley was a whore. There was no way to sugar coat this fact, and she wore the label without shame. She worked in Tulsa during one of the many oil-boom cycles that city experienced, turning tricks for the oil field workers that made their way through the city seeking their fortune. Well into her late twenties, she had a reputation as being an enthusiastic partner who was up for just about anything. One day she made the conscious decision she was ready to have a baby, even knowing her lifestyle was not conducive to such a decision. She was as hard-headed and stubborn as any Irish woman ever born, and once she set her mind to something, by God nothing was stopping her. So she set about picking a man to knock her up.
One day, a fella named John showed up at the brothel where she was working. It was never clear if this was his real name, or if he was "John" in the same way as so many other customers. It didn't matter, because John by any other name was still sex on legs. He oozed charisma, with a boisterous confidence and a charming smile that showed perfect white teeth in face with high cheekbones, piercing blue eyes, and glorious mop of sandy blond hair. The man had big dick energy way before that was a thing.
He picked Maryellen from the bevy of pretty girls- in her telling she had psychically willed him to do so. In the bedroom, he had taken his time and expertly used his enormous cock to fuck her eight ways to Sunday. She came so many times she could barely sit up straight, and when he finally unloaded she ended up with what felt like a gallon of jizz dripping off of her face and in her hair. His spunk even tasted good.
John would boast to his buddies that he was so good with women the whores paid him- and Maryellen though `goddamn him, but he ain't wrong'. Then and there she decided to make John her baby daddy, and over the span of the next month she made it happen.
She knew John was an oil man and not long for Tulsa, so she had no designs on making him a part of her life. She was a whore, and actually had very little use for men outside of the bedroom. When she missed her first period she was not sad to learn that John was leaving the next week. She never did learn his last name.
Once her pregnancy started to show, she quit whoring, took her meager savings, and moved to a small town in Southern Oklahoma to have her baby. When Pete arrived, she was at first sad he was a boy, because what the hell did she know about boys other than how to make them cum? But then she fell in love with Pete and turned into a fierce momma bear.
They were poor- everyone in that podunk town was poor, so that wasn't unusual-and she had a hard time making the transition to "honest" work, but Maryellen O'Malley was nothing if not a survivor. She worked cleaning hotel rooms where the various oil field workers lived; she took shifts at a a fast food restaurant; and she occasionally went on a "date" with one of the roughnecks from the hotel to earn a little extra pocket money. Hey, she still had needs, but Pete was her number one priority, and she made sure he never went without.
When Pete was 15, the inevitable oil bust hit. If life for them was hard before, then Maryellen and Pete really started feeling the pinch. They lost their apartment and had to hit up the food bank every week, and even with the extra provisions, as a growing boy Pete was hungry most of the time. With honest work drying up, Maryellen turned back to the work she knew best. At 42, she was not as hot a commodity as she used to be, so she had to work extra hard to make the same money. Her place of business became their crappy one-bedroom flophouse hotel which they rented by the week.
Pete was witness to a parade of men coming through his house and heard plenty through the paper-thin walls. To him, it was just his mom doing her job, and he didn't judge her for it. At some point he started asking his mom about what it was like doing what she did. Maryellen would answer his questions honestly, and would describe in detail her encounters with her customers. Needless to say, he learned a lot about sex that year.
One day, the situation changed in a way that would change both their lives, but we'll tell that story in just a sec.
Pete dried and fixed his hair, then put on his loose boxers and one-size-too-big khaki shorts, followed by a slim-fitting tee shirt that showed off his lithe body. He had plans to tease someone today, and this outfit was a big part of his plan.
His mom had a pop-tart and orange juice ready for him as he headed out to catch the bus. "Hurry up boy, I ain't driving you if you miss that bus!" It was a half-mile walk to the school bus stop and he was at risk of being late, so he broke into a jog. He could feel his junk bouncing around in his shorts, so he knew his plan was going to work.
He arrived at the stop thirty seconds before the bus did, and was still breathing hard when he found his seat. His long legs didn't really fit, which he used as an excuse to manspread one leg into the aisle. He conspicuously reached up the leg of his shorts to adjust his genitals, setting his plan into motion.
His target today was Toby, a tenth grader who had a painfully obvious crush on Pete. He tried to be subtle, but Pete recognized the signs, and he enjoyed giving the poor kid some good material for his spank bank. Toby was cute enough, but Pete had much more fun toying with the boy than he would have had actually playing around with him.
On the long ride to school Pete pretended to nap in his seat, with his legs spread and the large leg holes of his boxers and shorts hanging open for Toby to get a good view of Pete's junk. Pete could tell Toby had been angling for such a view for a while, and he wanted to see how the kid would handle a glimpse of paradise. As he napped, he willed his cock to chub up a bit so it would give Toby a bigger target. He would occasionally peek through his "sleeping" eyes to see how the boy, two rows ahead him and across the aisle, would react.
He caught Toby sneaking his first look, as he pretended to casually crane his neck like he was trying to see something interesting out the window. Like it wasn't the same flat scrub and the same pump jacks that they saw every single damn day. He saw Toby's eyes go wide and his head snap back around once he saw the show Pete was putting on. Over the next ten minutes, Toby stood up to get something out of his backpack, dropped his pen, and made every excuse imaginable to turn around and get a chance to see Pete's monster meat. Pete never moved. Finally, Toby broke out his cell phone and snuck some pictures. Pete willed his cock a little bigger for the pics, then a few minutes later "woke up". He made eye contact with Toby as he adjusted himself, pretending to be embarrassed by his exposure but really just tucking the fabric in to emphasize the visible penis line in his shorts. Toby blushed pink and tried not to hyperventilate as he turned to face the front to the bus again, and Pete knew his plan had worked. He wondered if Toby would upload those pictures to some internet site, or keep them to himself. He got a thrill knowing the effect he was having.
When they unloaded at school, Pete gave Toby a friendly smack on the back and "said see you later man!", along with his most charming- and suggestive- smile. Toby was shocked, and could only mutter "umm, yeah, later I guess." Why would a Senior talk to him? Did he know how Toby felt?
Pete went through his usual mundane day. He was a solid B student and could easily have made the honor roll if he tried to apply himself even a little bit, but school was not his top priority.
For that matter, neither was baseball, but much like schoolwork it came easily and so he was a good-not-great player without really having to try very hard. The workouts and weightlifting certainly helped his physique though.
Today was a scrimmage in full uniform, getting ready for the upcoming game this Saturday. Pete loved wearing his uniform- the jockstrap and cup he had to wear were hot, and the uniform hugged his body like a latex glove.
Today, rather than shower with the team, he went home in his sweaty uniform after practice. Pete had to work tonight.
He had joined the family business when he was 15, and he had a client tonight.
Almost three years ago, when he and his mom were living rough in that rent-by-the-week flophouse, one day changed both their lives. One of Maryellen's new Johns came over after she'd already had a long day turning tricks, and she said she could only do a blowjob. He was disappointed until he saw Pete sitting on the couch. "If it's just a blowjob, what about him? I bet his lips would feel good on my cock."
"He's no whore, so leave him alone! It's me or it's nothing tonight" she said. Momma bear went into full protective mode.
"Too bad, I'd have paid extra" the guy said looking appraisingly in Pete's direction. "If you change your mind, call me at this number. I know some other fellas who'd be interested too- you could make some good money."
"Yeah, we're done. Time for you to leave mister."
Pete of course overheard all of this. It had been a slow week for his mom before today, and with the reduced rates she could get for each trick money would be short again this week. Pete's stomach growled knowing they were likely to skip dinner again that night.
Just then, as if on cue, the hotel manager banged on the door and yelled "rent's due. Pay up or get out Mary." She hated being called Mary.
"Yeah yeah, you'll get your bloody money you goddamn sheister. Get the fuck outa here! And the name is MaryEllen for the last flippin time!"
She put her back to the door and looked at Pete. "Sorry about that. The nerve of that bastard asking after you that way...". She shook her head in disgust.
"Um, mom?" Pete started. "Don't you think that `s a little hypocritical? Why am I too good to do what you do every day? Besides I'm hungry, and we need the money. How much do you think he'd pay?"
Maryellen looked at him horrified. She could not explain to him why it was OK for her but would be an absolute outrage to even think about such a thing for her baby boy. She sat there, mouth slightly agape, thinking about what to do. She went to the kitchenette and pulled out the bottle of cheap whiskey- she had started drinking more lately- and poured some into a juice glass.
They were in a bind. Not only was she an aging whore, she was now a cheap aging whore, and it was getting harder to ply her trade. Her son was growing up, and he certainly had the looks to attract just about anyone- male or female. If he received even one tenth of his father's sexual skill, he could make some serious money.
"Pete, I assume you've never sucked a dick before, right?"
"No, but how hard could it be, right?"
Maryellen grinned and chuckled at his naïveté. "Oh son, if you only knew."
"I'm sure you could teach me. Call that guy back and ask for 5 times as much as you'd charge for me to suck him off. I'll do it."
She struggled, unwilling to concede that their lives had come to this- that she was no longer able to provide for her son, and that she was putting him on the same treacherous path that she had taken. But she was out of options, and the boy was old enough to start making his own decisions.
She sighed in reluctant acceptance, then took a big belt from her whiskey. "OK Pete, let's do this. Go get that black dildo out of my nightstand and I'll give you blowjob lessons. I'll call back Mr. So-and-so and let him know our price."
Pete came back with the requested item- he knew his mom had sex toys, but he had never handled them before. It was a realistic-looking silicone dick complete with balls, but the size was a bit intimidating.
He came back into the main room just as Maryellen put down the phone. Without looking at her son she said "OK, he's coming over in an hour. I told him the rule was that he was never alone with you, and I could stop it at any time and for any reason and he wouldn't get his money back. Just a blowjob, and he couldn't touch you. He didn't think twice about the rules or the money, so maybe I should have asked for more."
She looked at her son holding the dildo, and her heart broke. But she also knew this was the life of a whore, and that degradation was the name of the game. She just wished she could have spared her son a little bit longer.
`Alright, let's teach you how to handle a cock."
Pete looked at the toy and asked "do you think he'll be this big?"
"Probably not, but this ain't that hard to handle. Hell, it's probably smaller than your dick."
Pete was shocked- both that his mother knew how big his dick was, and that he could be anywhere near the size he was holding. He started to grasp the dildo in his fist, comparing its dimensions how his own penis felt when he jerked off. He had to admit, it kind of felt about the same, maybe not even as thick around.
Maryellen proceeded to show the boy what to do, how to cover his teeth, what to do when you felt like you were going to gag, how to supplement his mouth with his hand, and how to pull on the guys balls and press on his taint to get him to cum faster.
"And whatever you do, don't let him cum in your mouth. Men love to see their jizz on your face, so use your hand at the end and have him shoot his load that way instead."
Pete practiced with his mouth on the rubber toy, and found he could pretty much swallow the whole thing without gagging.
His mother shook her head in awe but also in shame. "Shoulda known you'd be a natural, kid."
Pete thought to himself `what's the big deal here?' and continued to practice.
There came a knock on the door and mother and son were ready. They hid the dildo and Maryellen let the man in, who grinned at Pete like a vulture about to devour a carcass. As he was taught, Pete gave him a knowing smirk- don't give away too much, but let him know you're hot and he's about to have his mind blown.
"This here is Johnny" she said to the man, making up a fake name for Pete on the spot. "What should we call you?"
"You can just call me Percy."
"Well Percy, you're gonna be his first, so go easy on him and he'll give a blowjob you'll never forget."
"Hey Johnny, I can't wait" he said, smiling at the younger man.
`Johnny' proceeded to take him to the sofa and began rubbing on his crotch with his hand. "Ooh, nice big one Percy. This should be fun." With that he started unbuckling the man's belt and unbuttoning his jeans. He dropped to his knees and slid down the jeans, groping Percy's quickly hardening erection through his white briefs.
Maryellen looked on with a mixture of horror and pride. Her son was disturbingly good at this.
The man reached out and grabbed the top of Pete's head. Maryellen almost lunged across the room but Pete gently grabbed his wrist and said "let's go slow and enjoy it, OK? Also, remember, no touching, right? Just let me do the work here. You want to get what you're paying for!"
Percy relented but clearly wanted `Johnny' to get the party started.
Pete continued to fondle Percy thought his underwear before using his mouth to chew on his dick through the fabric. He hooked his fingers under the elastic band and pulled Percy's underwear down, letting them drop to his ankles. Percy's cock popped free and Pete grabbed it by the root and smiled up at Percy as he looked at it. It was maybe six inches long, cut, and not too thick. This would be way easier than the dildo, he thought.
"Dang Percy, you have a really nice dick" Pete said, and slapped his own face with it. "I don't know if I can take something this big." Maryellen had taught him how to stroke the guys ego while he was stroking his dick.
"Oh yeah kid, suck my big dick with that little mouth of yours"
Pete smiled up at him lasciviously, and slowly licked the underside of his shaft. "Mmmm.. you taste good" he grinned.
Pete slobbered on his dick until it was good and wet, then started to suck him, making a great show of "struggling" to take more than his head, and pretending to gag as he took the older man deeper and deeper into his throat. "Oh man, you're quite the mouthful Mr. Percy" Pete cooed.
"Damn, you're doing great Johnny. Now really go to town on me. I'm getting close!" Pete grabbed Percy's testicles and gave them a squeeze and a tug, which was a trick his mom showed him. It pulled the angle of Percy's dick down so that Pete could take him all the way into his throat, where Pete bobbed up and down to massage Percys head.
"Fuuuck kid. Nobody's ever sucked me like that before!" Percy started to reach for the boy's head but Pete intercepted his hands with the man's prick still buried in his throat. He made a swallowing action and was sure he got a glob of pre-cum as a reward. He looked up at Percy with his nose still buried in the guy's pubes, and managed to smile before coming off the man's raging prick. His cock was covered in slime which Pete used to jerk the man off using one hand while pulling on his balls with the other. "Yeah, shoot that load on my face mister!" Pete held out his tongue to receive the splooge.
Pete increased the speed of his stokes and the man's knees started to shake. "Oh god, I'm coming, I'm coming" he said with a hoarse breath. As the first rope erupted, his whole body shook and he reached for Pete's shoulders to keep from falling over. "Fuuck.. Fuuck.. Oh shit.." the man swore. He didn't shoot with a lot of force, but there was plenty of cum covering Pete's face and running down his chin by the end. Pete was holding Percy's spent prick with a firm grip at the base and gave the tip a swipe with his tongue to collect the last drops, looking up at Percy with a mischievous grin when the man shuddered and pulled back reflexively from the hypersensitive feeling.
The man collapsed back on the the ratty sofa, bare ass naked with his pants still around his ankles. He threw his arm over his eyes and waited for the breath to return to normal. His softening prick was still shiny with Pete's slobber and his own semen. Pete grabbed a rag from the kitchen and wiped off his face. "That was fun mister! Thanks!"
Maryellen was stunned. She had just watched her fifteen year old son give a truly expert blowjob to a complete stranger. She was both proud, ashamed, and a little aroused, which only increased her feelings of guilt.
"Alright mister Percy, I think it's time for you to clear out. I told you you were in for a blowjob you'd never forget. Didn't lie, did I!"
Percy had recovered enough to pull up his pants and button his shirt, but he was still shaky. "Lady, that boy is the best cocksucker I've ever had. I'd say he was worth every penny. Mind if I tell some friends?" He handed over the agreed upon sum, then peeled off another bill which he handed directly to Pete. "You keep that for yourself kid. Just...wow." He shook his head, composed himself, and left the squalid room.
Pete pulled up a chair at the dinette and sat down with a glass of water.
"So ma, how'd I do? That wasn't so bad. His dick was a lot smaller than that big rubber dildo you had. It was way easier to make him shoot than I thought it would be."
Maryellen poured herself another shot of whiskey and sat down with her son.
"Boy, that was one hell of a blowjob. It troubles me to say it, but you're a damn fine whore. I guess this means you're ready to join the family business?"
"If it means we can eat, then I'll say yeah."
Thus began the whoring life of Peter O'Malley.