From the Bottom to the Top

Author's note: This is the first chapter of a much longer story. It contains a lot of background information for characters that do not factor in until later chapters.

Looking back, I realize how fortunate I was to be the outsider of the family. I would not have said that growing up though. You see, I come from a family of extremes social climbing obsessed people, and I was not.

As a kid I just didn't fit in. I always felt out of place and didn't have any friends. I was not interested in sports, and my hobbies were all of the solitary nature.

My dad used to say there was no way a boy like me could be his kid, and that my mother must have cheated on him to produce me. Things like that alienated me from my father and cultivated a strong sense of hatred towards him from a young age.

My name is Tom, but no one in my family really used it, they just called me fatty. The real kicker that isolated me the most was that of my parent’s five children, I was the youngest and the only one without a twin.

In contrast my father, Rick or Richard Brooks V, at the beginning of this story, was a 44-year-old who looked 34, 6 foot tall, classically handsome guy from old money. He still had a full head of dark brown hair and blue eyes and an athletic body from daily workouts and cardio.

With looks like his, he could have easily been an A list actor, but instead he worked at my grandfather’s real estate holding company, which was built by my great great grandfather and basically ran itself. My Grandfather, Richard IV, who everyone calls Dick, looked much younger than his 73 years, more like he looked in his 50’s, but had silver hair.

For my grandfather and father, it was not really work, they paid people to run things, it was more of spending time at the country club and having “business” meetings over drinks. My Grandfather ignored me entirely, while at the same time he regularly met with my siblings for dinner and was an active participant in their lives.

He seemed obsessed with the image the family projected to the world. He was the family patriarch and had control over all the money and assets, so even my father made sure not to cross him. That Dad feared him made me fear him even more than anyone, and I began to see him as the monster the monsters were afraid of though he had never so much as spoke to me before.

Luckily for me, I was only around my grandfather on holidays at his home, and he never visited ours, preferring to summon family members to him when he wanted to see them. My father was rarely home, preferring to spend time at the country club, traveling, or at nightclubs and casinos. In a way it was like he only stopped by occasionally to keep up the pretense that he lived with his family, but he really did not.

My Grandmother had died shortly before I was born, and my grandfather never remarried, which I found odd considering his looks and his wealth. I often wondered if he was different before her death, that losing her was the reason he was so cold.

My mother, Allison was 38 but did not look a day older than 30. She is petite, at only 5’7’’ but has a great set of 34 D breasts and a nice firm bubble butt. She has long blonde hair that goes to just above the small of her back and flawless skin that she keeps perfectly tan year-round.

For me though, her most beautiful feature is her face, with pink full lips that are the textbook definition of DSLs, beautiful and bright blue eyes, all set symmetrically. When she was young, she, and her fraternal twin sister were both gymnasts, but gave it up when they both got married.

When she was 18 she met my father at a nightclub, and ended up pregnant. For appearance’s sake, my grandfather made my father marry her pretty much immediately, with the threat of disinheriting him to back it up, which my mother didn’t mind, because she was looking to trap my father so she could marry into money.

My Mother was very maternal with my siblings, and even my cousins, but with me she always treated me as a disappointment. She never engaged actively with verbal abuse and ridicule, but when she looked at me, I could see a sense of shame and disappointment in her eyes.

She never showed the type of affection for me, with hugs and kisses, and never spoke about me with pride for my accomplishments like she did with my sisters and brother. To her they could do no wrong, and I just was wrong. This is always what hurt the most growing up, the sense that my mother didn’t love me.

The only physical differences between my mother and my Aunt Jennifer, her fraternal twin sister, is that my aunt has blood red hair, slightly bigger breasts at 36 DD, has alabaster skin and does not tan, and is 5’9”. She was dating Chris, my father’s best friend, for lack of a better term as he was more like his minion, when my mother got pregnant.

As they generally do things at the same time, she got pregnant by Chris, and they married as well. My father always called Chris, Chrissy, and sometimes Chrissy the Sissy, and Chrissy is definitely a beta male. Chrissy works for the family business, and actual runs the company. Everyone treats him like crap, either like a slave, or like a dog, and he continues to try to please them.

I would have felt sorry for him had he not treated me worse than they treated him, but I guess since I was the only one lower than him in the family hierarchy, he let out his frustrations on me. Aunt Jennifer was clearly the dominant one in their marriage, and Chrissy just lapped up the abuse.

She constantly belittled him about how she had to work as a bartender to keep them afloat, which for some reason she never showed any resentment over this to my father who could clearly pay him more if he wanted. She treated me about the same, but mostly she ignored my existence.

My oldest siblings are identical twins Kathryn and Katrina, 20 years old and they could almost be said to be younger versions of Mom except shorter at 5’6” and C cup breasts. Kathryn plays soccer at university, and Katrina is a cheerleader there as well. Both have modelling contracts as well, not they need the money, they do it for the status.

Kathryn has this whole, my body is a temple thing, so she doesn’t drink, use drugs, or eat anything except fruits and vegetables, but Katrina is best described as a party girl, a big fan of drinking, cocaine, and MDMA. Despite their differences, they are thick as thieves though, and delighted at torturing me when we were in school together.

Kathryn specifically was the worst; she is the reason all my troubles at school began in kindergarten. She was a second grader and told everyone I was a bed wetter (I wet the bed until I was 8 probably from the emotional abuse I took at home from my family for as long as I remember). She even coined the nickname that stuck with me, BWF, Bed Wetter Fatty.

My other siblings, Richard VI, who everyone calls Ricky and Alana, are 19 but are Seniors in high school with me. Ricky was always my chief tormentor, because as cruel as Dad was to me, he was rarely around, whereas Ricky always was and made a sport out of humiliating and degrading me.

Think of the stereotypical starting Quarterback with blond hair and blue eyes standing at 6’0” with a lean but muscular frame and that’s Ricky. Also think of the meanest bully you can imagine, because that’s him. He enjoys humiliating and hurting people, and not just me. He even does it to his “friends” like starting wide receiver and Alana’s boyfriend Jimmy.

At the top of the high school food chain he sits, with Abby also 19, his “Queen.” Abby, at 5’8”, with her 34 DD breasts, perfect ass, long wavy auburn hair, and green eyes, is the hottest and most popular girl in school. It isn’t just her looks, it is that and the way she oozed sexual energy and charisma. She is also cruel to me for no reason I could gather.

There were times she went out of her way to create some humiliation for me at school, and insisted I be called BWF. Despite this, I always thought deep down, she might have a heart, had she not been so caught up in Ricky’s orbit.

In contrast my sister, Alana, is 5’11” tall with legs for miles. Her ass must be the best I have ever seen anywhere, including actresses and porn, her 34 D breasts perfectly match her figure, and her blue eyes and blonde hair leave men and boys drooling in her wake. She is the kind of hot that lets her get away with anything, but she stays above the fray and exemplifies the miss perfect image.

She is class president and head of the varsity cheerleaders, and Abby is her right hand. Alana never tortured me or humiliated me and was one of the few people to use my name when speaking to me, which was only at home, at school she just ignored my existence. She was a pretty good student as well though not as good as me, being first in the class GPA wise.

In a way Ricky and Alana were two very different kinds of people, Ricky being a sadistic narcissist and Alana being the benevolent dictator. From my viewpoint, Alana was the only person in my family I truly felt affection for and I wished we had a closer relationship.

My aunt had two sets of twins, all girls. The oldest pair, Jill and Janey, are 20 years old and both have brown hair. They are not identical, Janey has brown eyes, tanned skin, and 34 B breasts. She is very petite at just 5’4” and works at the country club as a lifeguard and bartender.

Jill is a redhead, with blue eyes 36 C breasts, alabaster skin, and is slightly taller at 5’6”. She works for my family at the company with her dad, basically as an assistant. They couldn’t afford to go to college as she didn’t have a scholarship and although my aunt and mom are close, the situation was more like my father and mother handing out scraps to Chrissy and Jennifer.

For example, Chrissy had a job, but the pay was not what it should have been by a long shot, and they got to live in the guest house for free (which was bigger than most people’s homes) but they didn’t own a house. Jennifer was always trying to keep up with my mom as far as clothes, shoes, and accessories, so they spent every penny they had and didn’t save for things like college.

Roxanne, who everyone calls Roxy, and Maria, are 18 years old and were born about two weeks after I was. They are clearly not Chrissy’s daughters, as they are Latina. Jennifer claims not to know their father, that he had raped her one night after work in the parking garage.

They are identical and drop dead gorgeous with black hair, light brown skin and brown eyes, standing at 5’7”. They both have 36 DD breasts and the type of curves that scream, “ready to fuck”. While they are part of Alana’s inner circle, they are clearly minions and though they are family, they rank below Abby and the other cheerleaders.

All my cousins treated me like everyone else, with ridicule and insults, but their hearts were not in it. I could tell they hated doing it but did it to survive and maintain the good graces of my siblings. The difference was in the eyes, there was no enjoyment there, only pity and regret.

But this is not a story of my torturous childhood. That simply gives you the background of how things were before this story began. This story starts the beginning of Senior year. I turned 18 back in April of Junior year, but went through somewhat of a transformation at camp over the summer. I had a growth spurt, shooting up to 6’2” from just 5’6” and my body went from fat to lean.

That summer I had taken a job as a youth camp counselor at a sleep away science camp and had been gone for three months. I shaved my head to make it easier to see ticks, but realized it really improved my looks, so I kept it that way. I was far from the perfect Adonis that Ricky was, but I could reasonably be called attractive by the end of the summer.

Most fortunately was the size of my cock. When hard, it is as thick as a can of soda and 14 inches long. The transformation of my body had a profound effect on my mind as well. I was shy, introverted, lacking confidence, and generally lacked machismo of any kind. I avoided people and spent my time reading, playing video games, or writing computer code.

For my family, social climbing and accumulating status was what they were good at and what they valued, what I excelled at was school, being the top of my class GPA wise, computer programming, and problem solving. Years of being bullied had taught me how to avoid conflict and avoid being noticed. But now I had all that coupled with a newfound confidence due to my physical transformation.

That summer I had also had my first girlfriend and lost my virginity. Her name was Kim, and she was another camp counselor there, and we hit it off quickly as we were both nerds with a big love of computers. We were both 18 years old and about to start our senior year at our respective schools.

She did not compare to my female family members in the looks department, but she was not ugly. She had a pink hair in a pixie cut, small breasts and a petite frame.

Like me, she was just shy and coming into her own. It was the first time for both of us when it happened towards the end of summer. We went out to our normal make out spot by the lake, and the kissing and groping was getting us both hot.

Breaking off the kiss to get some air she said, “I am going to miss spending time with you so much when we go home tomorrow.”

“I know, meeting you has been the best thing to ever happen to me.” I said, painfully aware of her hand rubbing my cock through my shorts. As she rubbed it the leg of my shorts bunched up, and the head and about three inches were sticking out of the leg.

“Since this is our last night together, I want it to be special, I want to umm, you know, try a blowjob and maybe you can try to lick me.”

“Uh we could do that, if you…” I was cut off by her lips against mine as she resumed our make out session. Her hand briefly stopped rubbing my cock as she pulled down my shorts and boxers. As soon as they were off her hand was back, and then a second as she vigorously jacked my cock with both hands.

“Oh God that feels good, don’t stop Kimmy, ugggnh”

“Its so hard and so big, I don’t know if it will fit in my mouth, but here let me try” she said as she slid down my body. Looking down it was an incredibly erotic sight with her two small hands sliding up and down my cock and seeing the look of wonder in her eyes.

I let out another moan and thanked my lucky stars that I spent so much time jerking off over the years. Otherwise, I am sure I would have cum right then.
Just when I thought things were as good as they could get, she started planting kisses up and down my cock, first on the head then the shaft, I could feel her lips and tongue moving all over my cock, the whole time letting out “MMMMMs” like she was savoring her favorite food.

I reveled in the feeling. For all the masturbatory fantasies I ever had, and the hottest porn I ever watched, nothing held a candle to the reality of Kim kissing and licking up and down my cock. It was like she was making out with my cock, and I was feeling jolts of pleasure course through my body with every swirl of the tongue and every sucking sensation from her lips.

Time slowed down, and what seemed like an eternity to me was only a few minutes. Then she pulled back and said “Now let’s see if I can fit it in my mouth”

She opened her mouth and placed the head of my cock in her mouth, and I yelled “Oh my God that feel good!”

I was answered by a sexy purr that vibrated her mouth around my cock head. She could only get down about three of my fourteen inches, but she started working up and down that three inches like she was sick and had to suck the cure out of my cock.

She had no clue what she was doing, and since then I have been with some talented cock suckers, but the passion and enthusiasm was as high as it could be and as my first blowjob, it was like heaven.

While she sucked the head of my cock, she had one hand stroking the shaft. Meanwhile, she had moved the other hand down to her shorts and started rubbing her pussy. She started moaning more and more, and her mouth was sucking my cock head like a Hoover vacuum. It was all so hot, and the sensation so pleasurable, that I knew I was about to blow.

“Kim I am going to cum, pull out or I am going to come in your mouth”

“MMMMMMMM” was all she did as she sucked me hard into her mouth.

“Uggghhhhhhh ughhhhh” The first shot felt like a rocket launching out of my cock, but she took it like a champ and pulled off so just the tip of my cock was between her lips.

“MMMMMMMMmmMMMMMM” and shot after shot came jumping from my cock straight into her mouth.

I guess her mouth was full, so she pulled off and pursed her lips and jacked off three more shots onto her face. When I was spent, I felt like the life had been sucked out of me, but it was the best feeling I had every had in my life.

“MMMMMmmmMMMM” and then she opened her mouth and showed me the pool of cum she still hadn’t swallowed, then she closed her mouth and gulped it down.

“Oh my God your cum tastes so good! I wonder if all cum tastes this good or just some guys?” she said as she started scooping up my cum from her face and sucking it off her fingers.

The sight of her eating my cum and moaning like it was the food of the Gods, had my cock staying hard as a rock.

“Let’s switch and let me do you now” I felt like I needed to focus on something else or I might cum again, so I figured it would be good to shift the focus on her.

“Yes! Do that!” Like a cat she sprung up off her knees and got back up on the bench. I moved to face her and started kissing her neck and sucking on her ear. This elicited a moan and she started running her hands all over my shoulders and back.

Slowly I worked my way down until I got to her breasts. I started kissing them, while using my hands to grope them as well. She was still moaning when I got to her nipple when she let out a “Uhhh yeah suck my nipple Tommy”

I had watched a ridiculous amount of porn and read a ridiculous amount of erotica in the years since I got my first hard on, so I knew it was about more than just sucking. I used my tongue to flitter against her hard nub, while rolling the nipple of her left breast in my fingers, then I switched. I alternated between her breasts using my mouth, hands, and tongue to stimulate her the best I could.

The moans and gasps she was making let me know I was on the right track, as well as how she was gyrating her hips to rub her pussy on my chest. Suddenly she put her hands on my head and said “Lower, oh God please lick my pussy!”

I took the suggestion to heart and moved down kissing my way across the flat tummy until I was right above her pussy. Then I kissed my way around it, until I finally got to her labia.

“Stop teasing me please, I need you to lick me” With that I decided to tease her some more, rubbing my finger up and down her slit while I kissed all around her bush.

“Oh please, lick my clit Tom, I need it sooooo bad” So I decided to wrap my lips around her nub and suck. I let my tongue roll around it, and then switched to flicking it.

That got a “Oh God yes just like that!” followed by “UGHHHH UHHHH YES!”

Her hips started rising off the bench and she began humping my face, which was making it hard to stay with sucking her clit, so I put two fingers in her pussy and started finger fucking her. I was able to control her movements a little better this way and she was obviously enjoying the penetration.

“Oh YES DO ME WITH YOUR FINGERS! FUCK YES!”

I started curling my fingers up, and immediately she screamed “OH GOD IM CUMMMMINGGGGGGG” and she started to squirt a strong stream of fluid all over my hand, arm, and chest.

The whole time I kept sucking on her clit and using my fingers like a claw in her pussy. It was like my face was riding a bucking bronco, but I was not about to let go. “UH OH UH UH UGNHHH!”