Getting my Brother Laid

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!"

Not too enthused by the proposition, Tommy walked over to her and they began talking. Meanwhile, Jack and I stayed together at the bar. As the night went on, we got closer and closer. He got confident and began flirting with me and as soon as I realized Tommy didn't need my help anymore I started flirting back.

At first he told me the usual cliché stuff.

"Tommy never told me he had such a sexy sister."

Then he got more risky.

"You have the best ass in the bar."

Then he got even riskier.

"So... are you a spitter or a swallower?"

"Oh, I swallow," I responded.

I was enjoying how direct he was and the whole taboo aspect of getting together with my brother's friend was getting me really excited. I felt like he was teasing me and I wanted to tease him back.

"What would Tommy say about you trying to get into his sister's pants?"

"Tommy?" He glanced at him all the way across the bar. He was making out with the girl from before. "I think he's a little busy to be thinking about us."

I sure hoped so. I was about ready to go.

"How about this?" Jack told me. "When we get back to the dorm I'll go to my room. Whenever you want, you can come in. I'll be waiting."

"Ok," I responded, "but first I want a sneak peak."

I ran my hand down his pants and felt his cock.

"Wow," I said. "Good for you... and good for me."

He smiled and I removed my hand.

He left me to go to the bathroom. After some time Tommy came back and I asked him how it went. It looked like it went well but he wasn't feeling well and wanted to go back, which was fine to me. The faster we went back the sooner I could sleep with Jack.

Call me stupid but although the thought excited me, I still felt guilty about sleeping with Tommy's roommate. I didn't want to do it if he didn't approve, so I straight up told him.

"You wouldn't mind if we fooled around, would you?" I asked him.

"I guess not..." he said hesitantly. "You tried to get me laid, I shouldn't cock block you."

He didn't seem very happy about it but it was enough for me.

The three of us went back up to their apartment and, as he said, Jack went straight to his room. Tommy and I talked briefly before I gave him the cue that it was time. I told him goodnight and walked towards the door. Before I could place my hand on the knob, however, I was interrupted.

"Wait." I heard Tommy say silently. "I... I change my mind. Please don't have sex with him."

I was confused, but most of all I was annoyed. I told him that he had already given me permission and he repeated that he changed his mind.

"Well, I don't really need your permission do I?" I was getting desperate. "Listen. The only way I'm not fucking Jack tonight is if someone with a bigger dick miraculously appears. And that's only if they don't want to have a threesome first."

I turned around again to face the door but was interrupted a second time. This time, by the sound of a belt hitting the floor. I turned my head and saw Tommy, pants down and cock out. It definitely was bigger.

But instead of admiring the size, I was lost in thought thinking why he didn't want me to go in there so badly. I mean, was it such a big deal that he felt he had to show me his cock?

"Why are you doing this?" I asked him.

"Because I love you, sis." He said. "All those times you bothered me... I always got mad because I felt like I could never have you."

Then it hit me. All those years I thought I was just doing childish pranks but really, I was actually hurting his feelings. The weight of everything I said laid heavily on my shoulders, I couldn't resist going to him and giving him a hug.

"I'm so sorry, Tommy..." I told him. "I promise I will never hurt you again."

We held that tender hug for a while, but eventually my gaze landed on his cock. I kissed him on the cheek.

"Well..." I said, "I was really looking forward to a dick tonight..."

I kissed him again, this time more gently.

"And I DID promise you I'd help you get lucky tonight..."

I kissed him one more time next to his ear. I lowered my hand down to his abs.

"And I also need to make it up to you for all that I made you go through..." I whispered softly in his ear.

He grabbed my face and pressed it against his. I felt his tongue enter my mouth. Our hands began to explore each other's face, our back, our ass... Eventually I got the nerve to hold his dick. It was already hard.

I went down and started sucking it. I struggled to get as much of it as inside as I could but it was too big. I heard moaning softly as I ran my tongue through the long journey from his base to his head. I needed it inside me.

I let go and walked to the couch, removing my top and bra on the way. I lied down and took off the rest of my clothes, inviting him to join me. I told him I wanted his cock but instead he started rubbing my clit with his fingers. With his free hand he gently alternated between massaging my boob and feeling my nipple. His hands were strong yet soft to the touch.

One more time, I begged him to fuck me. At this point it looked like he was getting back at me for teasing him all those years. But he had mercy. He positioned himself between my legs and began thrusting. As I feel his cock caress every inch of me I couldn't help but moan. I didn't care if Jack heard us. All I could think of was that for years I could have had this inside of me and I regretted every missed opportunity.

Just as we were both going to cum he pulled away and started masturbating, and I followed his lead. As he came into my stomach, I reached my climax. We kissed each other for a while before he pulled away.

"I love you, sis."

"I love you too, Tommy."

He took his clothes and headed to his room.

For a moment I laid there. I couldn't wait for tomorrow, for another chance to feel my brothers love. I looked down at my body and saw the pool of semen that had formed in my belly button. I scooped some of it and gave it a taste. I already missed him. What was left I spread around my body. I wanted to get dressed; I didn't want Jack to see me like this in the morning. My tired body didn't let me.

Before I fell asleep I thought, "Fuck Jack. I want Tommy to find me like this."