Chapter 1

My name is Carter and I’m a rich kid. I suppose that’s a broad term. I’m not one of those guys that have an Instagram full of Bugatti’s and caviar. I don’t need to share my lifestyle with the world. I’m not a billionaire, but weekend ski trips on private planes, week long trips to the Bahamas and household staff is something I just grew up with. I never really had any concept of money.

So how did this happen? Well, I’m not really sure. What I had heard from one of my dad’s friends is that my grandfather owned a huge business and when he died, he left a ton of money to my dad and some corporate board position. I don’t really know since I rarely see my father. It seems that he has been a lifestyle like I am and never stopped. Unfortunately, somewhere along the way, I happened. For some reason, I ended up with him instead of my mother. Being stuck with a kid seemed to put a damper on his lifestyle, so he dumped me off onto a series of nanny’s and housekeepers while he takes off around the world. I’ll occasionally see him on holidays and on my birthday now and then, but since as long as I can remember, I’ve been raised by other people, or on my own.

Cry for me, sure. Hear my sob story and weep. Yes, poor me, all alone in a huge house in the hills of Southern California, with more money than God and a house full of staff that isn’t allowed to tell me no. I had every video game known to mankind and an entertainment system that rivaled movie theaters. I had a huge pool, hot tub, basketball court, on staff cooks and people to clean. The only obligation in life was school and even that was a joke. Well, I wasn’t entirely alone, but I’ll come back to that in a bit.

See, when you’re a rich kid, you go to school with other rich kids in a school built for rich kids. I call it a joke because no one in the school actually needed an education or a job. If we had to ‘work’ we were going to be given a position in a company that our parents owned, or a friend of our parents owned. If for some reason we decided to go to college, we were going to get in, regardless of our grades. Someone’s grandfather was on the board of directors and could push our application through. So, school was just another time sink and an excuse to get out and hang with your friends.

I had just entered high school to a rich, private school. It was one of those classic, textbook places you see in the movies. All of the guys were in suits and the girls were in skirts. How it was that the teachers dealt with hundreds of rich, spoiled kids day in and day out, I’ll never understand. I don’t really give a shit, I’m sure that they were very well paid baby sitters.

The school had a policy of matching up incoming freshman with a senior to ‘learn the ropes’ of the school and life and stuff. What this actually did was set up all of the incoming kids with networks and contacts to make it through the next four years and the rest of their lives. It was a pretty good system. The school called it the mentors program but privately we called it the Jedi system. It should have been called the Sith system for all the trouble we got into.

Regardless, my Jedi Master was named Robert. He was a cool enough guy. His father owned a national chain of car dealerships and so he came to school with a new vehicle pretty much every week. He tolerated me a lot better than other seniors did. Some freshmen told me that their mentors wouldn’t even bother to talk to them.

Robert seemed to liken me to a little brother. Annoying, but still family. We would hang out at lunch and he and his friends would give me the run down on what teachers were the biggest push overs, who would actually put their foot down on stuff and who not to piss off. The conversation would quickly move to more interesting things, like the best places to buy beer around town and the best vacation spots, as well as bars that would look the other way. All of his friends were Seniors, so they all had cars and could do what they wanted to. I had a driver on call pretty much 24-7, but I was a bit reluctant to push my driver to take me to the store to buy beer. Besides, I was still a pretty skinny freshman and didn’t think I could pull off 18, much less 21.

I nodded and played along, mentally taking notes of the things that they were discussing for the future. This would be my life for the next 4 years so I figured I needed to learn it now.

One day at lunch the Robert and his friends were all hunched over his phone. I sat down at the table.

“What’s going on?” I asked.

“Robert got a blowjob from Hailey over the weekend. He’s showing us the video.” one of his friends Brian.

“Seriously?” I asked. I was a teenage boy, so sex was certainly on my mind. But, growing up relatively sheltered, I had zero experience with girls and sex, other than my left hand and the internet.

“Yeah, wanna see?” Robert asked.

“Sure.”

Robert held out his huge IPhone to me and tapped a button. Sure enough on the screen was Hailey’s blond hair bobbing on and down on his dick. She pulled away and I could see her white button up shirt was open. Her bra was still on, but it could barely contain her huge tits. Hailey’s tits were a topic of great discussion around campus and were widely regarded to be the biggest and best in school.

In the video, Hailey pulled off of Robert’s dick and looked up into the camera.

“You’re not going to show this to anyone, are you?” She asked nervously.

“No baby, I won’t.” Robert’s voice replied.

“You promise?” She asked again.

“I promise baby. I love you. I won’t show anyone. Now, come on and do it more.” Robert said, his voice firm. I watched as he grabbed her head with his other hand and shoved her back down on his dick.

“I love you baby! How sweet!” Brian teased.

“Are you going to marry her or what?” Another one asked.

“Shit no. That’s the secret to getting girls to do what you want though. Tell them you love them and they will do anything you want.” Robert snickered.

“But you haven’t fucked her yet.” He replied.

“Not yet, but I will, I promise you.”

“Yeah, we’ll see. Word is that she’s an ice bitch saving it for marriage.”

“That’s because she’s not met me yet.” Robert replied.

“Prince charming huh?”

“Yeah, I’m gonna charm her panties right off.” Robert grinned.

I watched Hailey bob up and down on Robert’s cock some more. He finally pushed her off and grabbed his cock, stroking it quickly. Hailey closed her eyes in anticipation and Robert soon blasted her face with his jizz. The sticky mess rolled down her chin and in between her tits.

“Nice shot!” The table cheered as Robert put his phone back in his pocket.

“Thanks. Don’t worry, there is more video to come!” Robert announced.

“Still think you’re going to win?” Brian asked.

“Oh course I am.” Robert replied.

“Win what?” I asked.

“Me and the boys are having a sex tape contest. Guy with the best video wins.”

“Wins what?”

Robert shrugged.

“Don’t know. Bragging rights, 10 grand. Not sure yet. Doesn’t matter. It’s all about winning. You wanna play?”

There are defining moments in everyone’s life where you have to make a choice to set your mind to something. This was the first of those moments in my life.

“Yes, and I’m gonna win.” I said boldly.

Cheers and sounds of ‘Oh’ came up from the table. Robert looked at me and grinned.

“Cocky kid! I like it! You got balls. Now, let’s see if you can back it up!” Robert said, slapping me on the back.

The bell rang and we all got up to go back to class. Robert got up and then leaned back down to me.

“Piece of advice kid. Everyone has a weak spot. For some people its love. Some people it’s drugs, or booze. Or money. But, if you want something from someone, find out what their weak spot is and then go after it. Got it?”

I looked up at him and nodded, not entirely sure what that meant but I committed myself to learning it.

“Good job kid. Good luck.” Robert smiled and then walked off.

After that conversation at the lunch table, I began to be more aware of my surroundings. Specifically, the girls in school. Sure, I’d checked out the girls in the past and my friends and I compared notes as to who we thought was the most fuckable. But, as far as I knew all of my friends were virgins like I was, so it was all just big talk. But now, I scoped out every set of tits that walked past me, sizing them up like a hungry lion. The funny thing was, I had no idea where to begin. I had some female classmates that I had talked to, but in reality, I didn’t know know where to begin to talk to a girl, much less know how to seduce her.

My mind raced for the rest of the day and I barely heard a word that any of the teachers said. It didn’t matter, I knew I was going to graduate and this was all a formality. My eyes moved from female classmate to female classmate and I kept going over and over my verbal approach with each of them. I realized that not only did I not know how to talk to girls, but I didn’t really know anything about them, other than tits and tampons and even that was pretty vague.

I was in outer space the rest of the day and when the bell rang, I walked like a zombie out to the parking lot where my driver would pick me up. I slid into the back seat and the door shut behind me and we drove home in silence as usual. The car ride seemed to take forever, though it was only 30 minutes as I gazed out the window, wracking my brain as to how to win the contest. I walked up the steps and dropped my backpack in the hallway. I pulled off my jacket and dropped it alongside. Someone would be along later to pick it up, that wasn’t my problem. The housekeepers were milling about but I didn’t pay them any attention, I rarely did. I figured that if I made a mess, it would keep them employed cleaning it up.

I wandered up the stairs to my bedroom and dropped to my desk. For some reason, my young brain told me that if I watched some porn and jacked off, I’d magically solve the girl problem. Besides, at that age, jacking off seems like the best thing to do at any given time. Also, is there ever a reason not to jack off?

I flipped on my computer and the 32 inch monitor lit up. I browsed over to my favorite porn site and clicked on the first link. Ironically enough, it was one of those fake reality videos where a guy is trying to seduce his house cleaner. She was Hispanic, with long brown hair and big eyes. She wasn’t dressed very sexy, in a dirty t shirt and shorts, carrying around a bucket and sponge. I was about to skip ahead to the good part when something he was saying caught my attention.

“Come on. You don’t want me to call customs, do you?”

“No Sir, please don’t!” She pleased in the most fake voice I’d ever heard.

“Then do it.” the voice replied.

I watched as the girl set her bucket and sponge down and pull out the faceless cameraman’s cock and begin to suck it.

“That’s it girl. Suck it good and you can stay here.” the cameraman encouraged, putting his hand on her head. The wheels in my head slowly began to turn and though the girl was still dressed, my cock began to harden.

Life has a way of giving you gifts now and then. Now, you could say that my rich lifestyle was a gift in itself, but sometimes the universe just gives you things. I had just pulled my cock out of my slacks and began to stroke it when my bedroom door opened.

I spun around in my chair to see Lupe, one of the house keepers, standing in the door way, carrying a small trashcan and a duster. She froze, her eyes moving from my cock, to the screen behind me and then back to my cock.

“So sorry!” She called out and began to back up.

“Stop!” I yelled. Lupe froze. My eyes ran over her body. She was young, probably early 20s, with long dark hair and big brown eyes, just like the girl in the video.

“Come here!” I ordered. Lupe’s eyes opened bigger, but she didn’t move.

“Now! And shut the door!” I yelled. Lupe jumped. She closed the door behind her and took a few steps towards me.

“Oh yeah! You like that dick!” A voice came from behind me. I turned and looked over my shoulder to see that the man in the video had put the girl on the floor and was fucking her. I could see her big tits flopping around as he thrust into her. I turned back towards Lupe.

“Take off your shirt.” I ordered.

Lupe’s eyes got bigger.

“Sir?”

“Now!”

“Sir, no please!”

“You like your job?” I yelled.

She nodded quickly, tears filling her eyes.

“Then do it.”

Lupe stared at me for a moment and then set down the bucket. Looking at the floor, she grabbed the bottom of her shirt and pulled it off. I stared at her simple bra as she held her shirt in front of her chest.

“Bra too. Show me your tits.”

Tears began to run down Lupe’s face, but she reached behind her back and unhooked her bra and let it fall away. Her tits were small, but firm and I stared at my first set of live breasts.

“Come here.” I commanded. Lupe slowly walked towards me and I reached out and squeezed one of her breasts roughly.

“Owe!” She cried out. I had no point of reference as to how sensitive breasts were. I didn’t know that squeezing them like a wet sponge hurt. At that moment, I was touching tits for the first time and didn’t care. I rubbed and squeezed her tits. I pinched and pulled on her nipples. Her face clenched up in pain and discomfort but that only turned me on more. Finally I couldn’t take it any longer.

“Suck my dick!” I ordered. Lupe looked at me, her eyes pleading.

“Sir. No sir, please!” She begged.

“Now bitch, or get out!” I yelled.

With tears streaming down her face, Lupe got on her knees in front of me. I stared at her as she reached up, taking my cock into her hands. She leaned down and took it into her mouth, bobbing up and down slowly. Let me tell you, there’s nothing like the feeling of your first blowjob!

“Faster!” I demanded, putting my hand on the back of her head like I had seen Robert do to Hailey. I held her head and urged her up and down on my dick and she eventually picked up speed. The additional sensation on my dick was amazing and I could feel my balls swelling up.

“Yeah that’s it! Suck it! I’m gonna cum on your fucking face!” I yelled, forcing her head up and down on my shaft. As I reached the point of no return, I pushed her off and grabbed my dick, jerking it hard in front of her face. She closed her eyes like Hailey did and in no time I was spurting my cum all over her face like Robert had. She sat back on her knees, tears still running down her cheeks as she tried to clean the jizz off her face. I had no idea how short the process was, nor did I really care.

“Get out of her and back to work!” I ordered. She nodded and stood up, picking up her clothes and cleaning supplies and walking into my bathroom.

My first blowjob. My first orgasm from someone other than my left hand changed my life. I knew at that moment what all the fuss was about. I knew what power was, and sex was and I knew at that moment I wanted more of both. I knew from that moment my life was going to be consumed with sex and power and I relished the challenge.

Focused for the first time in my life, I began to study. I spent the rest of the night on every porn site I could think of. I watched everything I could. I saw bondage sex, group sex, fake incest sex, bisexual sex, cuckold sex, interracial sex. I watched gangbangs and gloryholes. I watched public sex, and webcam sex. I devoured everything I could find.

I didn’t stop, not for anything. Eventually the cook brought me up dinner to my room. I didn’t stop what I was doing when she arrived and she tried not to pay any attention to the 8 black men 1 white woman gangbang that was playing on my screen. I lost track of how many times I jacked off that night, calling the cook to bring me bottles of water and Gatorade to replenish my fluids as I drained them into socks. I eventually collapsed onto my desk around 4am, the sounds of moaning and screaming still filling my ears.

I was a wreck the next day from lack of sleep, but I was a changed man. It was like waking up from a deep sleep, though my body would argue. Every woman was now a target. As Robert had said, everyone had a weakness; it was just a matter of finding it. It was now a game, an eternal game, to locate that spot for everyone.

“You look like shit padawan.” Robert commented at lunch.

“Yeah, not a lot of sleep last night.” I replied.

“Poor baby. Too many video games?” He teased.

“No.” I replied.

“You look different though. Something happened yesterday?” He asked.

“Maybe.”

Robert and the other older boys sat up.

“What’s up kid? Did Jennifer smile at you yesterday in 4th period?” Brian teased.

“Not quite.” I replied.

“Then what is it?”

I stopped for a minute, pondering if I should tell them of my adventure with Lupe. I really wanted to. I was bursting inside and wanted to tell the whole world about my first blowjob. Then reality sunk in. I had gotten head from our maid. Not really a great accomplishment. She wasn’t much of a trophy to wave around in front of these older guys. Besides, I didn’t have a video to show to them, so they could just say that I was making it up. No, I was going to win their contest, with flying colors.

“Nothing. For now.” I said, forcing a grin.

“For now huh? You got something up your sleeve kid?” Robert asked, his eyebrows going up.

“Maybe.” I grinned.

“Maybe huh? This kid thinks he’s got game!” Brian exclaimed.

“Yeah? You got something to tell us?” Robert asked.

“I’ll have something to show you. Just not yet.” I replied, summoning more confidence than I had in my entire life.

“OOOhhs” and “Ahs” came up from the table and I glanced around at the older boys, who were all grinning at me.

“Big talker! Hope you can back it up kid!” Robert said, grinning at me.

“I will.” I said firmly.

The bell rang, signaling us to return to class. Robert walked around the table towards me.

“Just remember kid, if you’re going to talk big, make sure you can back it up. Unless you’re a master bull shitter. It’s actually pretty even as to which one is better. Someone who’s really good at bluffing can get a lot of shit done, but someone who can talk big and then back it up can rule the world. I’ll be keeping an eye on you kid. Good luck!” Robert said, patting me on the back and ruffling my hair.

I glazed through the rest of the day and practically ran out to the car. I dove into the back seat and urged the driver to move faster. Since the house was practically empty, it seemed silly that the cleaning crew came pretty much every day. I didn’t pay for it, so I didn’t care. I was just anxious to get home and continue my exploits with Lupe. I walked inside the house, dropping my backpack and jacket in the hallway as I always did. But this time, instead of going to my room, I searched through the house until I found her. She was outside, spraying off the pool furniture.

“Lupe!” I called out. She jumped and dropped the hose and then slowly turned around to look at me.

“Sir?” She said with a frightened tone in her voice.

“My room. Now!” I ordered.

“No sir. Please, no sir!” She pleaded.

“Ok, you can do it here.” I replied, reaching for my zipper. Her eyes shot open and she shook her head no.

“You want everyone to see? I don’t care.” I teased.

“No sir. Ok. Ok, I go to room.” She stammered, turning off the hose.

“Hurry up!” I demanded, turning around and marching up to my room. I jumped into the middle of my king sized bed and waited. Lupe came through my door a few minutes later and closed it behind her.

“Yes?” She asked, her eyes pleading.

“You know what to do.” I said, pointing at my crotch. Lupe nodded and crawled slowly onto the bed towards me.

“Shirt!” I demanded. Lupe nodded and pulled off her shirt and bra, letting her breasts swing free.

“Good. Now suck it!”

Lupe reached down and unzipped my slacks and tugged them down. I’ll never forget the feeling of having a girl take off my pants for the first time and I savored the look in her eye when my cock sprang free. I watched as Lupe leaned down and took my cock into her mouth. Being on my back for the first time meant that I was more relaxed and there was more length to my dick. I thrust upwards into Lupe’s mouth and relished in hearing her gag on it.

“Faster bitch!” I demanded, putting my hand on the back of her head and forcing her down on it. Lupe gagged but never stopped bobbing up and down on my shaft. I soon felt my balls swell up and based on the videos I had seen the night before, I knew what I wanted to do.

“I’m gonna cum in your fucking mouth and you’re going to eat it. Understand?” I called out. Lupe said nothing but continued to move her mouth up and down on my dick. I grabbed her head with my other hand and forced her down onto my crotch until her nose was pressed firmly into my pubes. She gagged a little bit but the feeling of her throat clenching around my dick was even better. I held her down there until my balls shot off and I blew my first load of cum down a girl’s throat.

“Yeah! That’s fucking great! Yes!” I yelled out, humping my hips upward against Lupe’s head as my pipes emptied into her throat. Eventually I felt my dick go soft and I let Lupe’s head go. She sat up, gagging a bit, drool, spit and jizz running down her face. She sat up and wiped off her mouth off with her shirt and then slowly stood up.

I lay there on the bed, my cock still hanging out of my pants I relax back into my bed and savored my post orgasm bliss. Lupe picked up her cleaning supplies and disappeared into my bathroom.

We continued like this for several days. I would come home, order her into my bedroom and make her blow me. I learned a lot about what I liked in a blowjob, mostly, rough throat fucking it was called. Lupe never fought me or complained. She would just take off her shirt and bra and service me. Sometimes I would play with her tits, sometimes I would just lean back and enjoy her mouth. Shooting your load down a girl’s throat was a feeling that couldn’t be beat. I preferred to make her eat it, but sometimes I’d cum on her face, or her tits. If I was feeling really mean, I’d jerk off in her hair, knowing that it would get stuck there.

Lupe always had that glazed over look in her eyes when she blew me, not that I blamed her. I told myself that it was all harmless. I got what I wanted; she got to keep her job, so everyone was happy. My improved mood showed at school too and my confidence level was picking up. People were beginning to notice. I carried myself taller now and wasn’t shy about eyeballing girls and winking at them here and there. There was one girl in particular, Jennifer, who caught my eye. Brian knew that I had made eyes at her before. She was a shy girl, thin, with long blond hair that she always kept in pigtails. We were lab partners in science class but never really talked about anything other than our assignment. She would never make eye contact with me for long, but when she did; her big blue eyes were always soft. I grinned and winked at her a few times and I always caught her blushing and quickly turning away. Her friends noticed her response and they would surround her afterwards, giving me looks over her shoulder.

I decided I needed more experience to go after Jennifer, so one afternoon when Lupe appeared in my room, I directed her to fully strip.

“Sir?” She asked.

“You heard me. Take off your pants.” I ordered, sitting on my bed and rubbing my dick through my slacks.

“Why?” She asked, obviously frightened.

“Because I fucking told you to!” I yelled.

Lupe jumped and moved her hands to her shorts, pushing them down her legs. She stood there in her plain panties, trying to cover her breasts with one hand and her crotch with the other.

“Those too!” I said, pointing to her crotch. Lupe hooked her thumbs through the top of her panties and stared at me. I nodded and she took a deep breath and then pushed them down. My eyes moved up and down her legs. Her crotch was covered with a thick black bush.

“Tonight, shave that!” I ordered, pointing at her pubic hair. I didn’t understand the draw of a shaved pussy at this time, but I’d seen a lot of porn and pretty much no girl had any hair on pussy. So, I figured that was how it was supposed to be.

She nodded at me slightly and then I motioned to my cock. She took a deep breath and crawled onto the bed and extracted my cock. As she had done a dozen times before, Lupe sank down onto my dick. Only this time she was at an angle to me and her body was within my reach. I reached up and ran my hand down her back to her thick ass, making her shudder as she slowly bobbed up and down on my dick. I moved my hand to her ass and gave it a hard smack, as I’d seen on countless porn videos. Surprisingly Lupe moaned when I hit her and pushed her mouth down harder on my dick.

“You like that huh?” I asked, slapping her ass again. Lupe didn’t answer, but her moans on my dick felt fantastic. I continued this, slapping her ass over and over again. Her mouth seemed to move in time with my hand, bouncing up and down on my shaft. I noticed that I could smell something new in the air. It was pungent, and sweet.

“What’s that smell?” I asked. Lupe glanced at me with an embarrassed look on her face.

“Did you do something?” I asked, my hand resting on her ass. She shook her head no. I sat up and my hand slid down her ass between her legs. I felt something wet on my hand.

“What’s that?” I asked, sitting all the way up and pulling my hand away. Lupe sat up, wiping her spit off her mouth. I looked at her and then looked down and noticed that the insides of her thighs were shining.

I reached between her legs and touched the insides of her thighs. I felt a girl’s pussy juice for the first time and moved my hand up her leg.

“So this is what it’s like? You’re turned on huh? This is what you are like when you get wet?” I asked, looking up at Lupe. Her cheeks were flushed with embarrassment, but she nodded a little.

“Wow. You like this huh?” I asked, incredulously.

“I like spanking.” Lupe stammered.

“Oh yeah?” I asked. She nodded.

“Ask me to do it and maybe I will.” I grinned.

Lupe stared at me.

“Please. Spank me.” She mumbled.

“What’s that?” I asked.

“Spank me. Please sir.” She replied. My dick hardened at the word Sir.

“Bend over.” I ordered. Lupe quickly dropped to her hands and knees on the bed and I moved behind her. Her ass was already red but I smacked it again. This time, Lupe moaned loudly.

“You like that huh?” I said, smacking her ass over and over again.

“Yes. I like spank! I like it lot!” Lupe yelled.

“Yeah? You like that you fucking slut?” I said, continuing to hit her ass.

“Yes!”

“Say it!” I demanded.

“I slut! I slut! I love spank! I slut!” She moaned over and over again. I paused for a moment and looked down to see that my cock was rock hard and sticking straight out towards Lupe’s ass. I grabbed my cock and pushed forward, not really knowing what I was doing. I felt something soft and wet push against the head of my cock and thrust forward and my cock was surrounded by a tight, wet grip. I instantly loved it.

“Fuck yes!” I yelled.

“What are you doing?” Lupe yelled, her head coming back.

“I’m fucking! I’m fucking you!” I yelled out, pushing my hips forward. This was sex! I was having sex! I knew the basic mechanics of sex from all of the porn that I had watched, so I grabbed her hips and thrust into her, bucking around like some sort of rabid dog. It’s impossible to describe the feeling of your first pussy and I humped Lupe with all of the energy that I had.

Lupe, it seemed, was quite conflicted. She wasn’t excited about the idea of me fucking her, but she was so turned on by my spanking and penetration that she simply dropped her head down onto the bed and took it. I fucked her for what seemed like hours but I’m sure was just a few minutes. I felt the familiar tingle of my balls filling up.

“Fuck yeah, gonna cum! Gonna cum!” I yelled.

“Not in me! No pill! No pill! Not in me!” Lupe pleaded, lifting her head up.

“Turn around!” I demanded, yanking my cock out of her pussy. Lupe quickly turned around, panting. I grabbed her head and thrust my cock into her mouth. I watched it disappear and then I held her down and unloaded my balls straight down her throat. My load was bigger than normal and Lupe’s eyes bulged out as I filled her stomach.

“Fuck yeah, that was awesome!” I called out, releasing her head and removing my cock from her mouth. Lupe fell onto her hands, coughing as my jizz backtracked up her throat.

“You need to get on the pill so I can shoot it in you next time.” I grinned.

“Can’t. Not allowed to have pill.” Lupe gasped.

“Well that sucks. Guess you’re just gonna have to eat it. Now, get out of here.” I said, dropping onto my bed. Lupe slowly crawled off the bed and picked up her clothes. I lay on my bed, staring at the ceiling, basking in the loss of my virginity.