A desperate teen goes to his step sister to ask for help.
It was a Saturday night at the house, I just finish a game with my friend Jake when I got up to look out the door of my room to see who was still up. My brother Richard was asleep on the couch and Dad and Elizabeth were in bed, I saw that Shelby’s light was still on. It was not like her to be up this late; she usually went to bed around ten. I went downstairs to turn off the lights and TV because I knew that no one else would. As I made my way back to my room, I looked at Shelby’s light again.
“Should I go in and see what she’s doing?” I thought to myself.
I always had a small crush on Shelby and sometimes wondered if she ever felt the same way, I always figured that she did not and instead thought of me as a brother. Mainly because she called me, her brother but I never considered her or any step family real relatives. Shelby had natural dirty blonde hair that hung down to her shoulders and always wore cute outfits and pretty revealing ones too, I used to think she was trying to tease me but I doubt that she would have that low of standards. I was staring at Shelby’s door for minutes before I realized that I had no clue what I was trying to decide. I guess that I wanted to go in there and tell her how I felt but I knew that she would take it the wrong way and think I was sick for being “in love” with my “sister”.
Then another idea found its way into my head. Shelby has confessed to me several times that she and her ex boyfriend had sex and fucked pretty often. I had but that is a different fucking story that she did not know and it was awhile back. I was desperate for some kind of physical contact, could I beg Shelby for some kind of relief? I decided that I was going to walk over to her door and listen in. I walked down the short flight of stairs to the balcony that Shelby’s bedroom door was on. I pressed my ear against the door and did not hear anything except the tapping of her fingers on her smartphone. It was clear that she must have been bored and could not go to sleep, I thought now would be a good a time as any.
I knocked on the door twice and then heard her bed squeak as she got up. She opened the door and asked
“Hey, what’s up?”
“Nothing just bored and wondered what you were doing”
“I’m just texting, want to come in and talk?”
“Yeah sure” I said as I walked in through the arch of her door. I sat down on her bed that faced the door as Shelby sat in the chair across from me.
“So who are you texting?” I asked.
“Alex” she answered shyly. Alex was Shelby’s ex boyfriend who had broken up with her a few months ago.
“Why are you texting that dick? You know you will just make yourself miserable.”
“I know but its hard to quit someone who you were with for a long time” She said
“Yeah I guess. Do you ever miss some of the other benefits about dating Alex.” I asked trying to start my plan.
“What do you mean?” She asked
“I mean like…sex and stuff,” I blurted out.
“Oh ha-ha yeah I do but he probably misses it more” She said and laughed
I think now was the time to finally say it.
“Ha-ha yeah I bet, but I know how he feels.”
“Nick you could get laid if you found someone”
“Well actually that’s kind of why I am here. I know were step siblings and all but could you maybe help me relive some of my “stress?” I asked
“What!” She yelled. However, it was not loud enough to wake anyone.
“Nick we couldn't have sex our parents are married and it would be too weird because we’re so close” she said.
“I never said actual sex, just something to help me get off. And is it not better to have sex with someone who you're close with then a stranger?”
There was a pause in the air.
“Like what did you have in mind to get off?” she asked
“Whatever you were willing and comfortable to do,” I said with hope.
“Well I sense you're still a virgin I could just jerk you off. I mean if you want your sister to make you cum then you must be pretty desperate.” She thought out loud.
“How about I give you a hand job but nothing else,” She demanded
I was shocked that it actually worked, I felt cocky and thought about how far I could push it.
“Ok. You’re the best sister ever!”
“Damn right I am. Now sit back on the bed.”
I did as she got out of the chair and started to walk over. I decided to try to push it.
“One more thing. Do you think you could take your shirt off?” I asked
“Nick, this is already fucking weird.”
“I know but it will really help. Please best sister ever” I ask begging.
“Ok fine but you're going to owe me.” Shelby said.
She stood for a moment and started to take off the yellow tank top she had on and revealed her 34C cup breasts. She had on a lacy black bra that took my breath away.
“Yeah I guess you could call it that,” I said joking.
She got down on her knees in front of the bed so she was eye level with my zipper; Shelby unbuttoned my pants and unzipped my fly, then slowly started to pull down my pants. Once they were around my ankles, she grabbed the rim of my boxers and brought them down to my knees. My 8-inch dick sprung out from them like an animal trapped in a cage.
“Oh, well that’s surprising.” Shelby said while staring at my cock.
“What?” I asked worried.
“Its just I didn't expect you to be this big. No offence.”
“Thanks...i guess” I said
Shelby grabbed my cock and slowly started to jerk me off. Her hands were so soft and felt amazing on my skin, her left hand start rubbing my inner thigh. Her boobs were beautiful and started to jiggle slight while in her bra, I tried to touch them but she slapped my hand away and said no. I was begging to start moaning kinda loudly and she seemed to notice.
“Be quite! Rachel is right next door, remember?” Shelby said.
While she jerked me off, she gathered a lot of speed and looked me in the eye, which made it even better. I began to rest my hand on her shoulder and rubbed the smooth tan skin that made her look like she lived on the coast. The way she stared at me in the eyes with this lustful sexy and innocent look. I lasted about five minutes before I could not hold back any longer and said that I was cumming. Shelby started to press her breasts up against my cock. However, kept going at her fast pace.
That is what sent me over the edge, i started bucking my hips she moved my cock downward so I did not shoot the load of cum all over her face. I cummed all over her tits and bra, she looked upset but kept pumping my cock until I was completely drained.
“Goddamnit Nick! I’m going to have to wash this now” she said while pumping the last few seconds of my orgasm.
“Sorry but god that was amazing! Thank you so much for doing this.
“Your welcome but you can tell no one about this ok?”
“I promise I won't” And I meant that.
“OK, well pull up your pants and get to bed I have to clean up.”
“Goodnight” I said. As I made my way to the door. I went back to my room and sat down on my bed just realizing how exhausted I was.