Correcting Tommy After terrorizing a condo, a bad boy meets a former resident
The Lanai was typical of southern California because its twelve free-standing housing modules ringed its perimeter. The complex was unusual because of its size, which occupied about a third of a square block, and the exceptional attention to detail and expense devoted to making The Lanai an oasis of botanical beauty and lush tropical tranquility.
Units at The Lani ranged in size from one-bedroom up to two-storied, three-bedroom apartments with cathedral ceilings and loft bedrooms. Every unit had a balcony and a fireplace. Lavish, thick, almost rainforest-like landscaping grew taller than the buildings around, between, and throughout the complex. A gym, a steam room and sauna, a large swimming pool with deck areas offering both sun and shade and a group-sized hot tub were only some of the amenities.
As nice as The Lani was, I knew I wouldn't be there long. Shortly after settling in, I started looking for a permanent home in the hills above Sunset Blvd. I first visited Los Angeles as a twenty-one-year-old but didn't stay long. Even then, I was smart enough to know I couldn't stay without becoming a washout, drug addict, or some other kind of loser. I left knowing I wanted to eventually live in Los Angeles, but not until I could do so comfortably in a house in its hills away from the craziness below.
I lived at The Lanai for eighteen months while the house I bought in Nichols Canyon underwent extensive remodeling. Besides being beautiful and pleasant, The Lanai was populated by friendly people of diverse ages, races, backgrounds, and cultures. Life at The Lani was relaxed, enjoyable, and even fun. Everyone helped make it so. Everyone except one disruptive to the point of being nasty teenage boy. His name was Tommy. Tommy, who I estimated to be about sixteen when I first encountered him, lived with his father and a brother who looked to be about a year or two younger. I never saw any evidence of a mother being present.
Tommy made life unpleasant for just about everyone. He put dye in the hot tub. No one could prove he did that, but we all knew it was him. Several times, weights and other equipment in the gym had jam or jelly smeared on them to the extent that it was obviously done intentionally. Again, not something that could be proven to have been done by Tommy, but no one doubted he was the guilty one. The complex had secure underground parking. On several occasions, cars, including my Benz SL, were broken into.
Complex management and residents talked with Tommy's dad, but there was no improvement in the disruptive boy's behavior.
What angered me most was that Tommy seemed to take particular pleasure in inviting friends to the pool and then, when he knew there were LGBTQ residents present, inciting his friends to loudly tell homophobic jokes and use such slurs to torment nearby people.
I had heard about this but was never around to personally experience it until one afternoon when I happened to be at the pool when Tommy and four of his friends arrived. There were a lot of people around the pool, only a few of whom I knew to be gay. Even so, it was only minutes before Tommy loudly launched into the telling of what he thought to be a hilarious "gay" joke. His buddies chimed in, and an ugly but thankfully short bout of homophobic humor ensued.
To anyone watching, as Tommy and his friends carried on, I lay on a lounge reading a book. Behind the lenses of my Ray Bans, my eyes never wavered from Tommy. He was definitely a young punk who thought he was bad-assed. But he was also a hot young guy acting up and screaming for attention. I suspected he would probably get attention in ways he didn't enjoy someday.
I eventually found the house I wanted, bought it and began extensive remodeling. Eighteen months after moving in at The Lani, I moved to my home on Astral Drive. Life was good. When the lease on my Benz expired, I flipped it for one on a Porsche Boxter S.
Late one night on my way home from an enjoyable and profitable evening spent with other Beverly Hills - Bel Air Poker Club members, I was stopped at a traffic signal on Santa Monica Blvd. at N. Sweetzer St., just a block or so from The Lani.
As I listened to music, I glanced at a young guy who looked about eighteen or nineteen years old and was standing on the corner to my right, obviously hustling. It took a couple of seconds for me to recognize him because he had matured quite a bit, and when I did, I almost laughed out loud. Right in front of me on a Santa Monica Boulevard meat rack corner stood straight bad boy Tommy peddling his ass, or at least his dick.
Before that thought cleared my brain, he noticed me looking at him. "Nice car," he yelled to me, smiling.
Interesting, I thought. It's been a year, at least, since I moved from The Lanai. Karma put Tommy on this corner tonight. He has to be at least eighteen now and has no idea who I am because I have a different car.
"Nice boy," I yelled back through the open window, smiling back at him.
"You want to give me a ride?" he asked?
"You may not be going where I am," I teased.
"I could be," he grinned.
"Sure, get in," I said as the light changed.
He practically leaped from the sidewalk onto the passenger seat.
"Damn," He said as his little butt settled down into the leather bucket. "How fast will this go?"
I threw the Porsche into first gear and gunned it enough to force him back against the seat.
"Fast," I replied, looking straight ahead.
As we drove east on Santa Monica, he told me his name was Tommy. Yes, I thought, it certainly is. I did give him a couple points for not lying. That surprised me. He also informed me he was hustling. I love it when a boy assures me he is not a rocket scientist. He told me he needed to get that out of the way before we got too far away from "his corner" in case I decided I didn't want to pay or drive him back. I assured him that I understood.
I told Tommy I didn't mind paying, but I wanted to know how much and what I got for my money.
Tommy was about as good a hustler as he was a thug. His first give was that I could suck his dick for forty bucks.
Forty dollars, I thought, so that's what street trade was selling itself for nowadays.
I knew Ron, my long-time "Boy" and partner, was staying at his girlfriend's place. The cards had favored me that night. Why not treat myself to an evening of having Tommy pay for his years of misdeeds? I would do that, but I wanted to haggle with him first.
I got Tommy down to thirty dollars. Although he was straight and had never done so before, he would suck my cock thirty bucks, but I couldn't cum in his mouth, and I could do whatever I wanted to him except fuck his ass, he said.
I assured him that I'd pull out of his virgin mouth long before shooting my load. Tommy, the young horny, cash-strapped guy that he was, actually believed me.
"Okay, Tommy, great. Before we head to my house, I want to be sure we have a deal. So let me hear you tell me what you're gonna do when we get up to my place," I said as I turned off Hollywood Blvd. onto Nichols Canyon. I wanted to hear straight Tommy tell me he was going to suck my cock.
"Yeah, sure, man, I'll suck your cock, but you promise not to cum in my mouth, right? Tommy replied.
"Good boy, Tommy, and right, I won't shoot my load in your mouth unless you ask me to," I replied, turning to give him a big smile. "I knew when I saw you standing on that corner that you and I would have a memorable night."
Without looking at Tommy, while turning onto Astral Drive, I casually mentioned that when we got to my home, I wanted him to strip naked as soon as we entered the house. I said he should fold his clothing and place everything in a neat pile on the floor next to the door.
When we arrived, as soon as we entered through the front door, I stopped and waited while Tommy stripped for me. I was familiar with his body, having seen everything but his package and ass at the pool at The Lanai.
Tommy was beginning to develop nicely when I last saw him. Now, at almost nineteen, he had the muscular, well-defined body of a budding young man. His ass, verging on a bubble butt when he was younger, was firm and dimpled. What really surprised me was Tommy's cock. I expected it to be average. Although not yet fully hard, what I saw arcing out over my bad boy's big balls was a thick, five-inch tube of uncut meat with a head so big its hoodie couldn't slide forward all the way over it.
Nothing in the social etiquette manual even hinted that I was required to provide a nineteen-year-old street hustler and former condo terrorist with a house tour before having him begin performing for me. Being a nice guy, I walked Tommy around my home's living level, showing him the game room and video room and taking him out by the pool before returning us to the video room.
During the tour, my right palm was alternately massaging the back of Tommy's neck or his bare shoulders, sliding up and down his smooth muscular back, or caressing, cupping, and squeezing his firm left buttcheek. By the time we returned to the video room, straight Tommy's throbbingly hard uncut cock was standing up almost against his firm tummy with its big head tapping against his navel, and its hoodie was fully retracted. That's when I put Tommy on his knees.
I didn't bother to get undressed. That would come later. It was time to introduce myself to Tommy, and I was dressed fine for that.
He tried to touch his dick as I was opening my jeans, but I reached out and knocked his arm away before his fingers wrapped around its shaft.
"Oh no, none of that. You don't get to play with that big thing," I said.
"What? Why not?" he stammered, confused.
"Well, we had an agreement. I'm paying you thirty bucks for you to suck my dick. There's nothing about you jacking off," I said.
"But why can't I? Dude, that's not fair," he whined.
"Look, we haven't even started. If you want to make a different arrangement, we can do that. How about you pay me five bucks for me, letting you jack off for me? We'll just take it off the thirty, so I'll owe you twenty-five for sucking my cock. How's that sound?" I asked, struggling hard not to laugh.
Tommy knelt naked at my feet, holding my hard cock while he pondered my offer.
While living at The Lanai, I thought Tommy and his friends were stoners. I thought now that poor Tommy had smoked a bit too much bud.
Tommy's voice brought me back to the present.
"Cool, man. Thanks." That was all Tommy said before his lips pressed to the underside of my shaft.
I stood there looking down, smiling as bad boy Tommy knelt naked at my feet, sitting back on his heels, eyes wide open, looking up into mine, blissfully pumping his big, hard uncut nineteen-year-old cock.
While stroking his big cock with his right fist, Tommy leaned his face to the left. Still looking up at me, he started jerking my cock off with his pressed-together lips, sliding them up and down the underside of my thick shaft from my balls to the big leaking head.
When I felt he was ready, I reached down and gripped the back of his head. As his lips slid up my cock and reached its head, I told him to stop.
"That's right. Keep your mouth right there. Don't move, Tommy," I commanded. He stopped and remained totally still.
"Part your lips and tickle my cock with the tip of your tongue," I instructed.
There was no hesitation at all. I instantly felt tongue tip press against the underside of my shaft and wiggle.
"Hold my cock and keep your lips pressed to it," I directed as I grabbed the bottom hem of my Polo shirt and peeled the shirt up over my torso, and tossed it onto a nearby chair.
"Good boy, Tommy, you keep looking up into my eyes and make sure your mouth stays on that big fucking cock," I reminded him as I unbuckled my belt, opened the button at the top of my jeans fly.
"Now, here's the challenge. I want you to stay on my cock while you reach up and slide off my jeans, Tommy," I said. "Take your time. Make sure your lips don't leave my dick."
A moment later, my jeans were on the floor beside us. Tommy was precisely as he had been, on his knees, sitting back on his heels, looking up into my eyes with his lips pressed against the underside of my dick, except now his lips had my cock pressed against my belly. My right hand was on the back of his head, with my fingers woven deep into his thick blond curls.
"Do I look familiar, Tommy?" I asked softly as I rocked my pelvis just a bit, causing the underside of my hard leaking cock to thrust against Tommy's rapidly moistening lips. He couldn't speak, but I saw his forehead wrinkle a bit, and he made a grunting sound.
"Let me give you a hint. We used to see each other quite often at The Lani. I always noticed you. I had a different car then, a blue SL," I smiled after saying that.
I knew mentioning the car would refresh Tommy's memory, and it did. His eyes opened wide, and I felt his soft lips move so tantalizingly against the underside of my cock.
"Oh yeah, that does feel good. Keep talking, boy. I do love the feel of your lips moving like that. Good to know you remember me. I certainly remember you," I ground my cock against his mouth again, dragging its leaking head back, smearing pre on his lips. At long last, Tommy and I had finally been properly introduced.
"Tommy, it's so fitting that you're where you are now. You were such an asshole, such a punk. You really do deserve to be naked on your knees with your filth-spewing mouth pressed against the hard leaking cock you will soon be sucking."
Releasing the hair on the back of Tommy's head, gripped by my right hand, I reached down with my left to the top of his head and again weaved my fingers deep into his long, thick blond curls. His eyes did not waver, and he did not utter a sound as I gripped what I was sure was a painful fistful of hair and yanked up on it, forcing Tommy to lift his lips off my cock and open his mouth.
We continued looking into each other's eyes as I towered over him, holding his head by his hair and his young, handsome face tilted slightly. As the big leaking head of my long, thick, steel-hard cock hovered about three inches away from his wide open mouth, I clenched my groin muscles, making that big leaking mushroom-like cockhead snap up and down, hitting his top lip and then his bottom.
I held Tommy like that was for a time, on his knees, looking up at me, gripping him by his hair with the head of my cock snapping up and down between his wide-open lips, slapping them. Then, when I was sure he understood, I tightened my grip on his hair and pulled his open mouth slowly over the big leaking spit-shined head of my cock until it disappeared into his mouth.
Bad boy Tommy looked so cute, almost littleboyish sitting back on his heels with his mouth wide open and the head of my cock in it resting on his tongue while I looked down into his eyes. I saw what I was looking for.
"You have been a very, very bad boy, Thomas. I think you know that."
Tommy knew no denial was possible. His mouth remained wide open as he looked up at me and sighed.
"So many people wanted, still want to punish you, and you deserve to be punished so badly," I said.
I almost laughed as he tried to talk without removing his mouth from my cock.
I slid it out until only its head rested against his lips.
"Go on, speak," I told him.
"Fuck! I'm sorry...I...I was a fuck up. I'm sorry I did those things...What will you do to me? Please don't hurt me!"
The sensation of Tommy's soft wet lips fluttering against the tip of my cock as he spoke was amazing. And, it seemed that the more frightened bad boy Tommy got, the harder and more leaky his nine-inch boner became.
"You do understand that you deserve to be punished, don't you?" I asked, holding him by his hair and looking into his eyes as I slid my cock back between his lips, letting its head dance on his soft, moist, tantalizingly rough tongue again.
"I'm going to spank your ass, Thomas. You've needed a good hard spanking for a long, long time," I told him softly as I withdrew my cock from his mouth and, still gripping him by his unruly mop of curly blond curls, dragged him, more correctly made him quickly crawl or lose some of his hair, to a nearby chair.
The oversized chair I selected was perfect for spanking a guy wheel barrel style, which is what I had in mind for Tommy. The wide seat allowed me to position him with his hands spread wide apart on the floor, his legs also spread wide apart with his knees resting on the chair's seat on either side of my thighs.
Having Tommy face down with his legs wide spread, his muscular back concavely arched from his uplifted ass to his similarly lifted shoulders presented a delightful view. His two hairless muscular butt cheeks were as if on a pedestal awaiting abuse. What I liked most of all was that below Tommy's presented butt and exposed taint, his large, nearly hairless balls and huge, hard, uncut cock hung offered as handles with which to hold him still during his spanking.
I took my time spanking Tommy. At first, I used both hands, alternately slapping his right butt cheek, then the left, then the right, then the left, over and over. That went on until Tommy was moaning, and both cheeks were a deep shade of rose. I was impressed that he never complained or asked me to stop.
After that, I reached down between Tommy's spread thighs and gripped him by his balls, using his nuts to hold his ass up high in the air while I spanked him with a ten-inch long, three-inch wide, stiff leather strap-like paddle. He only received ten wacks with that. That was probably best because Tommy got quite vocal during the last three strikes of that strap to his tender bottom, yelling, screaming, wiggling his lovely little red striped straight ass around in my face, promising to always be a very good boy.
Finally, while tenderizing Tommy's cheeks and the backs of his upper thighs with a small, soft leather flogger, I occupied my time tracing, massaging, tickling, and teasingly probing Tommy's constantly pouting and clenching tight little virginal asshole with the tip of my left index finger.
I couldn't help but smile at Tommy's near-complete metamorphosis. I sense a difference even earlier between the boy I picked on on Santa Monica Blvd. and the one I knew from my time at The Lani. The Tommy I picked up this evening had less of a chip on his shoulder. The naked, spanked young man spread before me seemed almost resigned to and welcoming of what he had to know lay ahead.
A few minutes later, Tommy gave me the head he had promised. I had him stop occasionally. When I did, he would remain where he was curled up on the floor between my legs in front of the chair and stroke his big cock and mine while he told me one of the homophobic jokes he and his buddies used to tell each other at the pool at The Lani. When he was done, I'd push his mouth back down on my cock so he could get back to being the obedient, well-trained cocksucker he was learning to be.
Eventually, I let Tommy get me off, mainly because it was getting so late. I was tired, and I could tell he was too.
I had him on the sofa, sort of kneeling, kinda laying to my right, as I laid back with my left hand on his head, my fingers deep in his curls, guiding his mouth up and down the underside of my cock. I like to talk to a boy while we fuck, guide him, encourage him, instruct him, and I was whispering all sorts of things to Tommy. I could tell early on that my doing so turned him on as much as it did me.
He was stroking his big cock while he licked and sucked on mine, and my right hand was all over his shoulders, his back, and his perfect, muscular ass that he kept clenching.
I had been reaching under him and scooping up his pre for quite some time and spreading it onto his tight little asshole. I knew I would need more than pre to finger Tommy's tight hole the way I intended to. Suddenly, with no warning at all, I lifted his mouth off my cock by his hair. While looking into his eyes, I brought my right hand up to his face and scooped a big gob of drool out of his mouth with three of its fingers. Before Tommy could do more than gasp, I pushed him back down on my cock and slid my right "fuck" finger all the way up into his hot, clutching asshole until I felt its tip hit the button to his cum pump.
I always know when I've hit a guy's switch by the way his mouth begins to hum on my dick. Tommy's mouth, good from the moment his lips wrapped around my cock, fell in love with my dick the instant my fingertip touched his prostate. All I could do was lay back and smile while the fingers of my left hand played with Tommy's hair and scalp, and the one on my right hand buried deep up his tight ass, pumped, rubbed, and punched his hard and growing g-spot.
Tommy was enraptured. His eyes were closed. Both his hands were wrapped around my long thick cock at its base and around my balls. His face twirled as his lips moved up and down my shaft. Drool seeped from the corners of his mouth. His fist alternately pumped his nine-inch cock like a jackhammer, and his precoated palm polished its big throbbing leaking head.
When it was time, I leaned forward and whispered loudly enough to be sure that Tommy would hear through his sex-crazed daze, "Tommy, you may cum when I do. When you feel me cum, I want you to cum. Nod if you understand." No wait or hesitation. Tommy was nodding on my cock almost before I stopped talking.
"I told you I would not cum in your mouth unless you ask me, Tommy. Nod again to ask me to cum in your mouth." I held my breath as Tommy's mouth and tongue continued to torment. And then, as I looked down, Tommy's curls began to bob up and down.
I tightened my grip on Tommy's hair. As I did so, my fingertip began to rotate around his prostate, outlining it, caressing it.
A low, deep moan wafted up softly from the boy below me as he sucked harder on my cock as if trying to suck the cum out of me.
Then, I knew I could hold back no longer. I began to ride Tommy's prostate with my finger, slid in a second finger, and stroked it as if fucking it as I pulled his mouth down my cock and held him there, and I exploded.
The first massive ribbon of cum that cannoned out of my cock splashed against the back of the opening to Tommy's throat. He physically bucked beneath me as if he had been hit by something. Before the second blast of jizz was out of my dick, he was already cumming and swallowing. His sperm shot all the inside of my left calf, all over it.
That was just the beginning. We both kept cumming. I fed him six big thick wads, all of which he swallowed down and stayed on my dick, licking, sucking, and kissing my cock until I eased him off it long after I was done.
I later learned that Tommy unloaded a three-day load on me and the floor. I kept my fingers in his ass through it all. He never asked me to remove them.
After showers, when I asked Tommy if he wanted me to drop him off at The Lani, without looking at me, he said he didn't live there anymore. He told me dropping him anywhere in West Hollywood would be okay.
That raised my curiosity. I eventually learned that Tommy's father had moved away. Because Tommy was now over eighteen and legally an adult, his dad left him in Los Angeles to fend for himself. Bad boy Tommy, who now seemed more pathetic than bad, was homeless.
I told Tommy I would make him another deal since he had nowhere to go or sleep that night. He could stay with me, but since I didn't really know him enough to trust him fully, there would be a condition. Not being totally stupid, Tommy wanted to know what that was.
"I'm going to lock that big dick of yours up in a chastity device. If you leave during the night -- specifically if you sneak off and take anything with you -- you won't be able to touch your big horny cock without coming back up here to have me free it from its cage."
I could see that Tommy was thinking.
"Of course, you might not want to stay..." I didn't get to finish.
"No, I do. I want to. It's just I've never had anyone put me in one of those things," Tommy said thoughtfully as he absentmindedly reached down to hold his junk.
Considering the size and, more to the point, the thickness of Tommy's penis, it took a trial-and-error approach. Still, I finally got Tommy's cock locked up in a Caged Bird-style steel cage. Although he didn't know it yet, bad boy Tommy who still had a lot of amends to make to me and to others, would not be handling his cock again without my permission.
Cock locked, showered, and fed; once I got him cleaned up and took a good look at him, I could tell Tommy hadn't eaten, certainly since much earlier that day; he slept with me for what remained of that night and until late the following day.
While we slept, Tommy woke me twice, intentionally or not, I don't know. He did not resist or complain either time when I pushed him under the covers and down on my cock. Nor did he resist or complain either time when I fed him my loads, which he quietly swallowed before going back to sleep.
I was in my office working when a chime alerted me to Tommy being up and moving about in my bedroom. Rather than simply talking to him via my home's audio system, which I knew would startle him, I got up and went to my bedroom.
"Hi, did you sleep well?" I asked as I entered the room.
"Oh, hey, yeah, great, thanks," Tommy replied from by the window wall. "You really have an awesome view."
"Yes, the view was one of the reasons I bought this house. You've probably been looking for your clothes. They're being washed. I hoped they'd be done before you woke up, but, oh well," I explained, Shrugging my shoulders and grinning.
"Hey, thanks. Yeah, they were pretty dirty," Tommy agreed.
"Look, there's breakfast stuff in the kitchen, coffee, cereal, eggs, that kind of thing. If you want, that is," I said. "I can make you something, or you can help yourself. Up to you. By the way, how's the cage feel? Any problem?"
"Ugh, no, the cage is fine. Better than I thought," Tommy almost gasped out quickly. "You're okay with me just fucking around in the kitchen?"
"Sure, as long as you don't burn the place down," I laughed. "And good about the cage. I want to talk to you about some things after you eat. Come find me in my office."
"You want me to cook you breakfast?" He asked as I turned to leave.
"Sure, that would be great. Bacon and eggs. Any way you like 'em will be fine with me," I said.
Tommy didn't burn my house down. I didn't wait for him to come find me. The scent of coffee and bacon frying drew me to the kitchen fifteen minutes or so later. I saw things orderly, and Tommy was about halfway through preparing what looked like a well-put-together bacon and fried egg breakfast, complete with English Muffins and fresh coffee.
"Hope you don't mind me borrowing these clothes," he said, waving a hand holding a spatula while looking over his shoulder as I entered the room.
I shook my head no, thinking, I prefer you wearing only your cage, but I understand the hazard of hot bacon grease.
While Tommy and I sat at the breakfast bar enjoying the fine meal he had prepared, I questioned him about his life since the man who wasn't his father had left L.A. and him. As I suspected, he'd been hustling and staying with friends when he could, shacking up with a girl or one of his customers, like me, when necessary.
I occasionally came into contact with people who presented me with investment opportunities. One such person was Anthony Martine, a bisexual guy in his early thirties I met through friends who owned a small Burbank shop that serviced high-end, mostly specialty vehicles. Anthony and I became close friends. When he wanted to expand his business into previously owned specialty vehicle sales, seeing a market and that his reputation provided an edge to fill it, I invested.
Ron works at Dreamrods Specialty Auto full-time, handling the front end of the business and the sales end. Anthony took care of the service and parts departments, as always. Every so often, when I had a young man who needed to work and thought would enhance the business, I would send him over to have Anthony and Ron check him out. Chris and Mark, two guys Ron and I got to know after we moved to L.A., also work at Dreamrods.
I explained all this to Tommy and said if he wanted to stop selling himself to random men on the street, I'd hook him up with a job working for Anthony so he had a steady income and a place to live, at least a room. I also told him that although he considered himself straight, I wanted him to suck my cock from now on whenever I wanted. Wanting to be completely honest with Tommy so he couldn't say later that I hadn't been, I gave young Tommy one final thing to ponder.
"And Tommy, while you're deciding whether you're going to become my boy, my straight cocksucker, I want you to know that if you do, that big horny dick of yours will always be caged unless I release it to allow you to masturbate for me or if you have been a particularly good boy and pleased me exceptionally well, I decide to let you have pussy."
Other stories you might enjoy include:
Training Chris and Mark (Eight individual chapters) available at:
Literotica https://www.literotica.com/s/training-chris-and-mark-ch-01 Nifty Archive https://www.nifty.org/nifty/gay/authoritarian/training-chris-and-mark/
A Guy Named Ron
Literotica https://www.literotica.com/s/a-guy-named-ron Nifty Archive https://www.nifty.org/nifty/gay/authoritarian/a-guy-named-ron