I've always gotten a kick out of teasing my little brother. When we were little I used to tell him that I wanted to be his girlfriend and he would get so embarrassed he'd turn red and started to scream at me. As the years passed and I became more of a joker my teases would only get worse for him. Sometimes he would come home sad because he didn't get lucky and I would say something like,
"Oh, Tommy! I'm so sorry. Do you want me to give you little blow job?"
After that it was always the same. He'd say, "What's wrong with you?!"
And if I really wanted to mess with him I'd say, "I'm just kidding, bro. I don't like guys with small dicks."
There wasn't a single time that I didn't find his reaction hilarious. But as easy as he was to make fun of, he was actually a really sweet guy. He often opened up to me about things he didn't tell anyone else. Every time he broke up with someone, every time he didn't do well in class, every time anything went wrong I was the first one (and often the only one) he went to. Honestly, sometimes I felt like I teased him more than he deserved. That didn't stop me from doing it, of course, but I still felt bad about it.
He eventually went off to college and I only saw him occasionally when came to visit while on vacation. The day he left I told him I was very proud of him. He had much bigger aspirations than I did and managed to get accepted in a relatively respected university. Meanwhile, all I wanted to do was finish my studies as quick as I could so I could get a job, which is why I stayed in town and enrolled in our public university.
"When you graduate and make tons of money," I told him, "I hope you put a ring on my finger so I don't have to work."
And like that, he was off to do better things than getting tortured by his big sister.
I did miss him though. So, when he invited over to spend summer vacation in his dorm I didn't think twice about it. When the taxi dropped me off and I saw him standing there I ran towards him and gave him a huge hug.
"There's my favorite pencil-dick!" I said.
That first day, all we did was hang out in his dorm. It was a comfy place for two people. The common area had a small kitchen, a table, a couch and a TV. It was way too clean for a college dorm; I guess he cleaned up before I arrived. We cooked, ate and spent the rest of the night watching a movie. When we got tired he retired to his room and left me in the couch to sleep.
Thee following day I begged him to show me around his campus. Despite being summer, there were still some students around taking summer courses. I guess people in his university weren't used to pretty girls because I caught quite a few of the guys checking me out. I guess Tommy also noticed too. It was actually cute that he got jealous over me.
We ate out and got back later than we expected. We opened the door to his apartment and saw someone eating at the table. I glanced at Tommy and saw that he was just as surprised as I was to see him.
"Oh, hey! Tommy!" He said, "I leave and you finally bring a girl over?"
Tommy seemed annoyed to find him here. Later he explained that he's his roommate, Jack. He was supposed to go home for vacation but for some reason came back. Then he explained to Jack that I was actually his sister.
We al sat together at the table and the both of us started getting to know each other. His original statement got me curious, however, and provided a good opportunity to poke fun at Tommy.
"So," I asked Jack, "I take it he doesn't get lucky over here either."
"Are you kidding me?" He responded, "This guy can't get laid to save his life!"
We both laughed about it for quite some time. Eventually Jack got tired and went to sleep and as he usually did, Tommy started talking about his girl troubles. Apparently he had come close to closing the deal numerous times but for some reason fucked it up before it could happen.
I'm not sure why but I felt sorry for him. Maybe it was because I hadn't seen him in such a long time. Instead of teasing him, as I usually did, I tried to help.
"What you need is a good wingman," I told him, "and it just so happens that I'm the best one."
Before we went to bed I told him that tomorrow we were going to go to a bar and one way or another we were going to get him laid. When he protested I told him that it wasn't up to him. I was going to talk to John so he could take us to the best place he could think of.
And so it was. The following night the three of us walked to a nearby bar and started looking for girls. When I saw Tommy being shy we bought him drinks to loosen up.
"Look, Tommy," I told him. I directed his gaze at a particularly busty and dumb-looking college girl who was sitting alone at the other end of the bar. "She's perfect!"
