Playing matchmaker sometimes has unforeseen effects
Hi my name is Jane, and I have the worst luck getting dates. The few dates I have gotten have been duds. I've had no winners ever since really I started dating. I'm not looking for someone to marry right now and settle down with already, I'm only 27, but I still want a relationship that could lead to be something serious. I live with my brother Brad who is 31, we both are about 6 feet tall and have brown hair and eyes, but I have c-cup breasts though and he doesn't. We both live in an apartment and I came home one night from a date when I wasn't too happy.
“Judging from that look on your face, the date didn't go well?” Brad asked.
“Nope, I just gently implied that I might be interested in doing the deed, and then all of the sudden he has a girlfriend,” I replied.
So of course he put on his confused face and asked some follow up questions.
“He's not single?” Brad asked.
“According to him, no, I guess he just didn't find me all that attractive,” I replied.
"Bite your tongue, you are ravishing sis," Brad said.
"Thanks," I replied.
Like all men honestly, they listen, but always wanna jump to some solution to the problem.
“Well, I have an idea,” Brad said.
I just nodded and looked at him.
“Let me set you up, I have a friend I know who is single, he's funny and nice, interested at all?” Brad asked.
“Sure, I guess,” I replied in an unenthusiastic tone.
So he set me up with a friend of his, I didn't know if it was his best friend, a casual friend or whatever, but I said yes to the date. I went on the date with that guy the next night and we didn't meet each other until we got there, so it was a complete blind date. I showed up there about 10 minutes before the agreed upon time and he wasn't there. I waited for about an hour and I heard nothing from him or Brad for like an hour. Eventually Brad called me and told me that his friend had to cancel, so I came home rather pissed again.
“So just out of curiosity, did he give a reason?” I asked as I walked in the door.
“No he didn't, I'm sorry Jane, I feel bad,” Brad replied.
“Don't worry about it, shit happens,” I said as I sat down with him.
“Let me try again,” Brad replied.
Then I sighed for a minute and gave him a hug. He was certainly one not to go down without a fight, so he wasn't about to give up.
“Don't worry about it Brad, it'll happen when it happens. Maybe I shouldn't go looking for the right one and I should just let the right one find me,” I said.
“OK sis, I love you,” Brad replied as he hugged me back.
“I love you too Brad, you are the best brother in the world to set your sister up. I'm gonna go take a bath now,” I said.
“OK sis,” Brad replied.
I went to take a bathroom, got naked and got in bathtub. As the tub was full, then I knew if all signs were pointing to the date working out, I might be actually having sex then or at least doing something with him. I hadn't had sex in about 6 months at that point, so I had to rub one out. I spread out my pussy lips and stuck my fingers up in there. I let out a few soft moans and stuck my fingers inside my pussy as deep as I could.
Masturbating was always nice every now and then, but when I continued to masturbate, it just lost the pleasure I guess. I still managed to get myself off though, I breathed in and out slowly and came a bit in the tub. Then after that I just laid there and thought about things. I didn't wanna just masturbate by myself forever, I had to take as many shots as I could. So really without thinking, I just got out and ran out into the living room completely naked.
“Fuck it, set me up again, I gotta get laid bro,” I said.
Then he covered his eyes, but he was cheesing and trying not to laugh.
“You got it sis,” Brad replied.
“Thank you and sorry you had to see your sister naked,” I said.
I started walking back to the bathroom.
“But I've seen you naked a million times though,” Brad replied.
“Then sorry again,” I said from the bathroom.
He set me up again and we went out to another restaurant that I picked. This one actually showed up, but as the food came, I found out he was a vegetarian and couldn't stand to date someone that ate meat. So he had his salad boxed up and left, so I ate my steak alone. After that I went home to break the news.
“I'm sorry sis, I guess I'm just not a matchmaker I guess,” Brad said.
“It's alright. I don't get why he waited until the food came, he knew what I ordered and I really thought he was like just a fitness guy, but no, he's the 'V' word that doesn't like-, I'm sorry, I'm starting to rant. What are you watching?” I asked.
“Knocked up,” Brad replied.
“Really, I had no idea you like that movie,” I said.
“I've always liked it, and back there I have extra cheesecake, I know you love cheesecake sis,” Brad replied.
“So 2 for 2, movie and cheesecake, you are on a roll bro,” I said as I walked to the kitchen.
I got myself a piece of cheesecake and came back in the living room to sit down.
“And here's a blanket, I know the heat isn't working,” Brad said.
Wow, he was seriously on a roll, cheesecake, good movie, listened to me shit and shared the blanket. We watched the rest of the movie and spent some quality time together, but eventually the movie ended though.
“Well, that was nice of you bro,” I said.
“Let me try one more time. I can find someone that can make you laugh, likes to eat streak, likes movies like Knocked up and can treat you right,” Brad replied.
I just felt so loved by him, he was determined to find me a date that worked, but I think I found the perfect guy sitting right next to me, so I kissed him.
“Whoa sis, what are you doing?” Brad asked.
“You just described you. You can make me laugh, you like all cakes like I do. You like R rated comedies and you'd eat pork chops and steak for the rest of your life if you could. You tell me how pretty I'm all the time, and don't complain about shit, even when I bitch like 10 times a day about different shit. So why not you?” I asked.
I guess I flattered him.
“So what are you saying is you wanna date me?” Brad asked.
I could tell he was already sold, but I still broke out the big guns. No not those.
“Would you do that for me?” I asked in a very sweet voice as I gave him the sweetest look I could possibly give him.
He just looked at me and tried not to laugh.
“It's not like I can say no to that, how the hell do you expect to say no to that?” Brad asked.
“Thank you, I love you big brother,” I said as I gave him a big hug.
“I love you too sis, but you are still a pain in the ass,” Brad replied.
“But you love me, so I call that a win,” I said.
Then the next night, he took me on a date, and it was the best date ever. He listened to me, pulled out my chair and even drove me over there, unlike the other 2. So after the date, I was happy. When we got home, we both sat down on the couch and he turned the TV on, but I felt something was off.
“Brad, can we talk about something?” I asked.
“Sure, what is it?” Brad asked.
Call it me being determined to take advantage of a good thing when it's right in front of me, I kissed him once and put my hand on his cock.
“I want that inside me,” I replied.
“You wanna have sex?” Brad asked.
“Yes, after you go on a date you might get lucky, even on first dates, but I'm asking you in this case, will you fuck your sister?” I asked.
I guess he had to think about it for a minute, it was something more than a little weird that I was asking him for this favor.
“Well if I do this, I don't wanna hear any bitching that I don't do enough for you, ever,” Brad replied.
“You already do a lot for me, but deal,” I said.
Then I kissed him again and I leaned on top of him. We both wrapped our arms around each other tightly and made out for about 10 minutes, but then I broke the kiss.
“Well, can we move to my bedroom now?” I asked.
“Sure sis,” Brad.
I took his hand and we went into my bedroom. We stood right in front of the bed for a minute and made out passionately.
“Just tell me if you think it's going too far, but I wanna do this with you,” I said.
“OK sis,” Brad replied.
I put my hands on the bulge in his pants and he had a huge hard on.
“Can I suck on your cock?” I asked.
“Yes,” Brad replied.
I gave him a kiss and hugged him as tightly as I could.
“I love you Brad,” I whispered in his ear
“I love you too Jane,” Brad whispered back in mine.
I got down on my knees an took his cock out of his pants. He had a big one too, it was at least 8 inches long and it was thick too. I thought my eyes were gonna fall out, because I was so stunned as his pants and boxers fell to the floor. I took it in my right hand and stroked it a little as I looked up at him.
“You are the best brother, bar none,” I said.
“By time we're done I might change 'brother' to 'sister' when I say it to you,” Brad replied.
“You better do that,” I said.
I took his cock into my mouth. He immediately let out a small moan, so I knew he liked the physical pleasure, but I wanted to make him scream though. I sucked on his cock really passionately and he loved it.
“Holy shit Jane, you can take a dick,” Brad said.
I didn't reply to that, I just kept sucking on his cock like mad. I wanted to make him cum like none of his girlfriends ever did, not that I saw though. I looked up at him and he smiled at me, I'm not too sure he wanted this to happen, but as it was happening, he wasn't complaining. He of course put his hands on my head and made me suck a little harder, I sucked harder than I ever had before honestly. I really did this on a whim honestly, but I was loving it too. He mouthed 'I love you' to me several times, so as a reward for that, I went back as far as I could and began to deep throat him. I had his entire cock in my mouth and he really belted out some loud moans.
“Fuck me sideways!” Brad screamed.
Unfortunately, that got the attention of our neighbor though.
“Shut the fuck up over there,” Our neighbor said through the wall.
We both just stayed silent for a minute.
“Whoops,” I said.
I took his cock back into my mouth once again and put all my might into giving him a huge orgasm. I wanted him to cum a river for me, so I began to deep throat him once again and put my hands onto butt. I made sure he knew who was in charge of this sex session, it was me and I was not about to resign from that position. I looked up him again and he leaned his back which only meant that he was loving it and having trouble taking all the pleasure.
“Holy shit sis, I can't hold it anymore, I'm gonna cum now,” Brad said.
I backed up and watched him not quite cum a river on the floor, but it was still a lot to say the least. I stood up to ask another important question.
“Well would you say I'm the best sister yet?” I asked.
“We'll see sis, now let's get a little more comfortable,” Brad replied.
He got down on his knees and pulled down my skirt exposing my underwear.
“Baby blue, I like that sis, it's extra sexy,” Brad said.
He slowly pulled down my underwear to my knees.
“Do you mind if I eat you out sis?” Brad asked.
“What the fuck took you so long?” I asked.
My pussy was already really wet, but then it was just absolutely soaked in every sense of the word. He just got close first and gave my pussy a few gentle licks. I immediately loved it, maybe it was because it was him or it was just that I just hadn't had sex in awhile, but he made sure to make me feel good like a good older brother. He spread out my pussy lips a bit and stuck his tongue in there deep.
“Oh my Brad, you are something else than what I had you pegged for,” I said.
“I'm guessing that's good?” Brad asked.
“Yes, very good,” I replied.
Then he stood up, took off my shirt, threw it to the floor and he saw my matching bra I was wearing that went with my panties.
“Matching set, even more sexy sis,” Brad said as he took my bra off as well and threw it.
He took off my panties and just checked me out from head to toe, I know he especially liked my tits.
“Aren't you gonna tell me how sexy I'm Brad?” I asked.
“Sis, you give 'sexy' and 'beautiful' whole new meanings,” Brad replied.
“What about 'pretty' though?” I asked.
“That word too,” Brad replied as he pushed me to the bed.
He got on his knees and began eating me out once again. He began once again with a few gentle licks and then he started spreading out my pussy lips, but then he stuck in tongue in there just a little and I was already screaming.
“Shit!” I screamed.
“Hey remember, the neighbors can hear us,” Brad replied.
“Fuck them, I got the best brother in the world fucking me!” I screamed.
He stuck his fingers up into my pussy as well, that just made me wanna scream at the top of my lungs, but I tried my best to keep it down to a minimum. He wasn't making that easy either, I was breathing in and out slowly and just trying to keep my cool.
“Yes Brad, fuck me with that tongue, stick it in there as deep as you can and hit your sister's g-spot,” I said.
He hit it with flying colors and I screamed as loudly as I could.
“Shit!!” I screamed.
“Hey, keep it down!!” The neighbor yelled.
“We're not sorry!” I yelled back.
Then I reached over to my dresser and grabbed a condom as he climbed up on the bed with me.
“Now I want your cock inside me big brother,” I said.
“Well I can do that for my little sister,” Brad replied.
“But I wanna put it on you though,” I said.
He got on his back and I put it on his cock. I laid down on my back and he got on top of me. He inserted his cock into my pussy and immediately we both let out a couple moans.
“Wow sis, you have a tight pussy,” Brad said.
“Well I haven't had too many cocks in there lately, just fingers,” I replied.
We both laughed for a couple seconds and gave each other another kiss before he started thrusting his cock into me. I put my hands onto his shoulders and smiled. He smiled right back at me and kissed me once.
“I love you Brad, you are a saint for me doing for me,” I said.
“I know sis, I'd even take a bullet for you,” Brad replied.
“No, don't do that, I might need you again,” I said.
“You wanna have sex again?” Brad asked.
“We'll see, now I want you to shove your cock up into me as deep as you can,” I replied.
Then he started thrusting in and out of me a little rougher. It did hurt a bit, but it was the best fuck I think I ever had. His cock was in there completely and I let out a few more moans as he got as rough as he could.
“Oh yes Brad, but get rougher with me. You don't gotta be completely nice with my pussy, shove that cock in there and make me scream again so the neighbors bitch,” I said.
“Ask and you shall receive my lady,” Brad replied.
As I asked him too, he shoved it in there as deep as could rather quickly and made me moan some more. We both were getting pretty sweaty and my heart rate was racing faster than I think it ever did before. I was very excited and I thought I'd be cumming like a fountain in no time.
“Yes Brad, make me cum, I wanna cum for you Brad,” I said as I moaned.
He kissed me to try to muffle my moans, but unfortunately he had to start moaning as well. Then we were both moaning rather loudly, but I wanted to see it though.
“I wanna see you cum again big brother,” I said just before I came.
So he pulled out, ripped off the condom and he came on my stomach. Then we both laid there and tried to catch our breaths as we tried to grasp what had just happened. All that thinking didn't stop him from feeling my pussy though.
“Wow, can you do me a favor?” I asked.
“What?” Brad asked.
“Keep this time next week free for me,” I replied.
“What for sis?” Brad asked.
I kissed him once.
“I'm gonna wanna fuck you again,” I replied.
“I can do that for you,” Brad said.
Then we looked at each other for a minute in silence.
“So?” I asked.
“So what?” Brad asked.
I gave him a look.
“You are pretty?” Brad asked.
“No,” I replied.
Then I gave him another look.
“Fine, you are the best sister in the world,” Brad said.
“That's better, now give me another kiss,” I replied.
We kissed again and we cuddled for a few minutes.
“Well, it's getting late, we should go to bed, and your welcome sis. I'd love to do it again for you too,” Brad said as he got up and grabbed his clothes.
“Wait,” I replied.
“What?” Brad asked.
I grabbed my bra and underwear, got up, and walked over to him to kissed him once.
“I want you to keep my bra and underwear to fondly remember the first time you fucked your sister,” I said.
“Thank you, and you can keep my boxers sis. Be good to them though, they were my favorite pair,” Brad replied.
“So, in my bed same time next week then?” I asked.
“Can we at least alternate beds every week?” Brad asked.
“Well, if I do that for you, then you gotta do something for me,” I replied.
He gave me a look.
“What?” Brad asked.
“We have sex twice a week every week, what do you say?” I asked.
“Deal,” Brad replied.
Then he started walking to his room.
“But one more thing,” I said.
“Yes Jane?” Brad asked as he turned around.
“If you are uncomfortable, tell me, but on those nights, I want you to sleep with me too,” I replied.
Then he came over to me and kissed me again.
“You are lucky I love you,” Brad said.
“I know, I love you too,” I replied.
We slept together that night and every night we had sex. I know he'll do it for me for as long as I ask him to. I gotta say Brad is a saint for helping me out like that. He even took me out on a few dates after that as well, but not a lot though. He said didn't wanna have an incest relationship, but I think sooner or later he'll want it, I know it, after all, I think we are prefect for each other.