Bring It On Keely Part 1

I had just started at a new high school. Private high school at that. During the summer my single mother got married. Almost like ‘The Brady Bunch’ our families merged and we moved into my rich step father’s big house.

My life couldn’t have been more turbulent. It was exciting and frightening at the same time.

Step dad was just as cold and distant as my mother had always been. Just like in junior high I didn’t take the bus home, instead I was picked up by Ms. Daria. I don’t know why I call her “Ms. Daria.” her name’s just Daria. I guess it’s because she’s so much older than me, in her 40s. She’s been my best friend in the whole world for many years. She’s single and lives alone. I guess I’m the daughter she never had. I spend every afternoon and weekend with her because we have so much fun together. As a grown up she can drive us to the mall, play music really really loud and even rent R rated DVDs.

I don’t think of her as the mother I never had, more like an older sister teaching me about growing up. She’s my best friend. We can talk about anything together. Anything. She bought me my first tampons and my first bra, and showed my how to properly stuff it so nothing fell out.

“Ms. Daria? I need you to buy me a gun.” I said jokingly. “I have to kill my new stepbrother Derek. He’s the biggest jerk in the universe. He doesn’t do his chores which means I have to do them. He doesn’t shower every day. He stinks and leaves his dirty discussing clothes all over the house. He steals the remote control and hogs the computer. He’s so stupid, he talks like he’s retarded, always stuttering. No wonder he was held back a year in school. He’s two years older than me and still in the same grade. Even worse he makes fun of me calling me terrible names like ‘ugly b-i-t-c-h.'”

Ms. Daria smiled a little in a way that worried me. “Derek’s a teenager? And he’s not popular in school?”

“No. He doesn’t have any friends, which makes me a social leper too. ‘The retard’s sister’ they call me. He’s such an embarrassment.”

She smiled again. “And your brother doesn’t have a girlfriend?”

“Get real! He’s never had a girlfriend. No one can stand him.”

Now Ms. Daria started chuckling.

“Its not funny!”

“Keely Keely Keely. I’m only laughing because your brother Derek has all the signs of sexual fustration.”

“Sexual frustration? What’s that?”

“Your brother’s a teenager. Having sex is all he thinks about all day long. In school, at dinner, always. And he has no way to relive that tension. It causes him to fail at everything and not even bother to try. It causes him to act out by being mean to you. Does Derek have his own room?”

“Yes. In our big house he and I each have our own bedrooms and bathrooms.”

“I bet Derek’s in the bathroom a lot isn’t he? When your mother calls him for dinner he says he’s in the bathroom? Right?”

“Yeah. So?”

“Keely, the reason your brother’s always saying he’s in the bathroom is because he’s masturbating. He probably masturbates several times a day every two or three hours. In the morning before school, at least once in boys’ room at school, as soon as he gets home, before dinner, and before bed.”

“Master..bait? You mean like playing with himself? Oh gross! No wonder he has problems!… Wait, how could you possibly know this?”

“Because I know he’s a teenager. This what all teenage boys do. It’s natural and normal.”

This was the phrase Ms. Daria used to describe a lot of things when we talked about sex. “Natural and normal.”

Ms. Daria continued her explanation. “But for Derek masturbation is not enough. He doesn’t have a girlfriend and never has. That’s why he’s acting out. You can help your brother. Derek will be a much better person and treat you like you should, if you can help him relieve his sexual frustration.”

“I can help him relieve his sexual frustration? But what can I do? I’m just his sister.”

For the next few hours Ms. Daria gave me very detailed instructions on what to do that night. It sounded crazy! But she gave me confidence.

“If you follow my instructions, you’ll see a real change in Derek overnight. Tomorrow I’ll pick you both up after school and the three of us will have a long talk.”

II

Ms. Daria had never steered me wrong before. No matter how crazy her plan seemed it just might work.

When mom called Derek for dinner he yelled down, “Hold on! I’m in the bathroom!” I smiled to myself now knowing what this meant.

After midnight I knocked on Derek’s door. He opened it with drowsy eyes. “Wh-wh-what the fu-fuck do you want?”

Without answering I simply passed by him into his room. “I had a nightmare. Can I sleep with you tonight.”

“Bu-bu-bullshit. Get th-the fuck ou-out you ugly bitch.”

“Please? Please? I’ll do your homework for a week.”

That got his attention. “We-well O-OK but if mom and da-dad catch us we-we’ll be grounded for a month.”

I’d done up my hair the best I could and was wearing only my very shortest white T shirt and lace panties. Unfortunately this part of Ms. Daria’s preparation had gone to waste as the room was very dark. I could barley make out the shape of his smelly queen size bed but I climbed in the left side. My brother climbed in the right and positioned himself as far away from me as possible.

Slowly, ever ever so slowly I guided my hand toward him. I reached his right leg and he seemed not to notice. Then I found the button fly of his flannel pajamas.

Now he was awake. “What the fu……” He never got to finish his sentence the moment my hand reached his organ. He was very erect. He was paralyzed, his whole body stiff. His eyes wide open staring up blindly at the ceiling, his breathing heavy.

Ms. Daria had prepared me well. She told me this is how my brother might react. Paralyzed by pleasure and fear. “Natural and normal.”

I was also prepared for what a penis would feel like as it was my first time touching one. Ms. Daria had several flesh like phalluses she let me handle. I had examined the finely exposed veins and contours. The difference between what Ms. Daria called, “bare back” and “gift wrapped.” Indeed Derek was circumcised.

My hand gently graced the smooth soft tip down to what remained of the ring foreskin and gently massaged it up and down in long even strokes just as Ms. Daria had taught me.

For about five minutes my brother lay there still paralyzed. Saliva started drooling out of his mouth uncontrollably and his gasping breaths grew more and more violent. “Natural and normal.” said Ms. Daria. “That’s why Shakespeare called orgasms “dying.” Because of the way the body reacts.”

Then his gasps became a moan and I felt his life explode all over my hand and his sheets. There were several long long bursts of streaming semen.

I slowed my strokes but never let go.

“Derek?” I kissed his cheek softly. “Derek?” His eyes were closed. The drool still spread across both his cheeks. He was asleep. Fainted from pleasure just as Ms. Daria said a virgin boy might.

I wiped my hand on his pajamas and returned to my room leaving the door unlocked in case my brother awoke later and wanted seconds. Ms. Daria had prepared me for that as well.