I first started dating when I was 16. I never had sex until I first met my brothers friend Sam, when I was 18 and he was 19. Hi. I'm Jill. I'm about 5 ft 3 in, and I have B-cups. One day my brother Jack, and his friend Sam, were in his room. I passed by and I noticed they were looking at Playboys. They always looked at Playboys for some reason. I just peaked in for a couple seconds.
“Uh Jack, mom wants to know if Sam is gonna stay for dinner?” I asked.
“Yes, I think so, is that OK if he does?” Jack asked.
“Yes I think so, otherwise, I don't think she'd have me ask you,” I replied.
“Funny,” Jack said.
Then I headed back out to the kitchen where my mom was.
“So is Sam eating with us?" My mom, Whitney, asked.
“Yes,” I replied.
“OK then. Well, dinner should be ready in an hour,” Whitney said.
About an hour later my mom sent me to tell them that dinner was ready and they could come eat with us. We were having Spaghetti. My mom always made really good spaghetti. So we all sat down and started eating.
“Well Sam, how has school been?” Whitney asked.
“It's been good. There are a lot of ladies there at school. So how could it not be good?” Sam asked.
“I don't know. But you are focusing on your school work too, right?” Whitney asked.
“Yes, of course I am. What about you, Jill?” Sam asked.
“Uh, school has been fine I guess. And there are a lot of guys at school,” I replied.
“Yes, I know but maybe you need to focus on school work though. Right, Whitney?” Sam asked.
“Well, I'm doing pretty good in school. I never got a referral before and the teachers have nothing but good things to say about me,” I replied.
“Well, I wasn't saying you were flunking out or anything that. I was just giving you a hard time,” Sam said.
“What? Are you nervous, man?” Jack asked.
“No I'm OK, I'm just chit-chatting with your sister, that's all,” Sam replied.
“OK, man. Just make sure it stays at chatting,” Jack said.
“Yeah, no kidding. She is really fragile and we don't need her doing anything she'll regret," Whitney replied.
“OK mom, I think I'll be fine though,” I said.
Then we were all done eating. We all took our plates into the kitchen and they went back into Jack's room. I wondered what Jack meant when he to make sure we just talk, and to make sure nothing else happens. Did he think we were gonna have sex? I didn't know. About an hour after dinner was over, my mom was in the living room and sent me in to tell Jack she wanted him for something. So I went into his room for a second.
“Jack, mom needs you for something,” I said.
“OK, sis,” Jack replied.
Then he went into the living room where my mom was. I didn't know why she wanted to talk to him, but I didn't care, honestly. So I went into Jack's room where Sam was. I came in as Sam tried to hide the Playboy.
“Hey Sam. How are you doing?” I asked.
“I've been good. How are you doing?” Sam asked.
“I'm good, very good in fact. Can I ask you something?" I asked.
“Sure I guess,” Sam replied.
“Well, what do you think Jack meant when he said to make sure we just talk and nothing else happens?” I asked.
“Well, I don't know. I guess he's just protective over you and doesn't want anything to happen to you. I can respect him a lot for that. He's just your protective brother, I wouldn't worry about it too much, honestly,” Sam replied.
“Well, yeah, but I'm a junior in high school and I can take care of myself,” I said
“Well that's good to hear. A woman doesn't always need to be protected like that,” Sam replied.
“That's true. Can I ask, do you think I'm a sexy woman?” I asked.
He was a surprised by the question. He wasn't sure why I asked it. He stammered a little bit.
“Well, yes I guess you are sexy. But it's weird that you are asking; you are my best friend's sister,” Sam said.
“Well I know. But do you think I'm as sexy as all the women in that magazine?” I replied.
Then, being surprised still, he pulled out the magazine.
“Well I guess so. But they are naked,” Sam said.
“Well, would you need to see me naked for you to really make the call?” I asked.
He really started getting a little nervous once again. Was I really turning him on, and did he really like me?
“Well, I guess in theory I would have to see you naked to really make that call, but again you're my best friend's sister. That would be really weird,” Sam replied.
“I know, but no one would ever have to find out. It'll be our little secret. Does that sound good?” I asked.
Then he got a little sweaty, too.
“Well I guess, but Jack could come back in at any minute and if he saw that, it would probably end our friendship. And I don't wanna sacrifice that,” Sam replied.
“Well, I'll close and lock the door. And it'll just take a minute,” I said.
“Well OK, if you really want me to make this call,” Sam replied hesitantly.
“Yes, I really want to know if you think I'm truly sexy as those models in there showing off their tits and everything else,” I said.
Then I began to undress. I only got down to my bra and underwear and he stopped me.
“Yeah, you are as sexy as these women, trust me,” Sam said.
“You don't wanna see me completely nude though?” I asked.
“Well yes, but after I see you naked, is it gonna be weird between us?” Sam asked.
“No, I don't think so. I've known you for a couple years now, I don't think this will mess anything up honestly, unless you think so. Do you?” I asked.
Then I think he was just horny and he couldn't help it.
“No, I don't think so. But no one ever finds out about this, right?” Sam asked.
“Absolutely no one will ever find out, I promise,” I replied.
“Well OK. Take off your bra and underwear,” Sam said.
Then I took off my bra, and underwear, too. He just looked at me for a minute, as I was completely naked. I think he was stunned by how sexy I was. Or maybe it was because I was his best friend's sister. But either way, I noticed the bulge in his pants; he had a big hard on.
“As I said a minute ago: You are sexy. Sexier in fact," Sam said.
“You really think so? You are not just saying that?” I asked
“Absolutely not. You are very sexy, I just wish you weren't my best friend's sister,” Sam replied.
Whether he was baiting me or not, I came towards him and sat down next to him while still completely naked.
“If I wasn't your best friend's sister, then would you be interested in me?” I asked.
“Well I don't know exactly, but I think I would be very interested,”
Then I took his hand and put it on my left breast.
“Is this turning you on Sam?” I asked.
He could barely answer. He was very turned on.
“Yes, it is,” Sam replied.
“I noticed that you have a pretty big hard on. Are you horny because of me?” I asked.
He was very nervous and he was stammering.
“Yes. But this is wrong, I couldn't do this to Jack,” Sam said.
“Well he's out there talking to my mom for who knows how long. They've been at it for like 15 minutes now. We know that you are very turned on right now. We can do this and no one ever has to find out about it,” I replied.
Then I began grabbing the bulge in his pants. It was so hard, I couldn't believe how hard it was, honestly.
“Well can I see it?” I asked.
He knew exactly what I was talking about but he couldn't have been more nervous. Then there was a knock at the door.
“Hey Sam? My mom and I gotta run out for like an hour. I just need to get something real quick. But my sister is around here somewhere. So she may pop in at some point. Anyway I gotta go, but I'll be back soon,” Jack said through the door
“OK. See you soon,” Sam replied.
Then both my mom and Jack left. Neither one of us had any idea where they were going, but of course we didn't care. Then we were completely alone.
“Well, can I see it now?” I asked.
“Uh sure,” Sam replied.
Then he began unbuttoning his pants and he showed me his big dick. It was like 7 to 8 inches and it was really hard, too. I began stroking it a little. It felt so good in my hand as I stroked it very slowly.
“Are you OK with this?” I asked.
“Sure I guess. Can I touch your...?” Sam asked.
“My pussy?” I asked.
“Yes. Can I touch it?” Sam asked.
“Yes, if you want to,” I replied.
Then he touch me there and began fingering me a bit. It felt so good.
“You know Sam, I'm virgin. And I've thought about having sex with you before. Would you be interested in that?” I asked.
Then without reply he just attacked me. He climbed on top of me and began kissing me fiercely all over my body. It was quite an experience. I really had thought of having sex with him before, that was true. Then a minute later, I thought he wanted to officially take my virginity.
“Are you sure you want this? I mean you can only give your virginity to one person and that's it. So are you 100% sure?” Sam asked.
It was a good question. But was I just horny, was he just horny, or we were we both just horny? Was it just lust we felt for each other? Or did this topic of conversation just get out of hand a little bit? But at that moment I didn't care.
“Yes, I want you to take it. Now. Take it for your own,” I replied.
He got naked in about 10 seconds and got on top of me. Then he stuck his erect cock inside me, slowly and cautiously. I thanked him for that. If he just broke my hymen right away I think it would have hurt a lot more than it did. But after a minute, he did break it and I screamed.
“Oh fuck, that hurts!” I screamed.
“I'm sorry, but it was gonna break, Jill. Do you wanna stop now?” Sam asked.
“No, keep going Sam. Make me moan and cum before they come back,” I replied.
Then he kissed me once and put his arms underneath me. He held me really close and planted kisses all over my face.
“Wow Jill, I never knew you could be feisty, my lady,” Sam said.
“Well I never knew you'd fuck me if I asked you to. But I'm glad you are fucking me now,” I replied.
Then he just kept thrusting his nice cock in and out of me slowly; he didn't wanna be too rough since he had just popped my cherry. Then I started moaning.
“Holy shit Sam, your dick is so damn big. I'm not sure I can take all of it,” I said.
“Well I'm being nice with your pussy. I won't be too rough with you. I do want you to like the sex,” Sam replied.
“Are you saying you wanna do it again sometime?” I asked.
“Yes I do Jill. I wanna put my dick into your tight pussy a lot more. But I also really like you too though,” Sam replied.
Then we kissed once again and we turned over. He held me down with him with both of his arms, and my boobs were pressing against him nicely. Then he took his left hand off my back and put it on my right boob. I never ever had anyone squeeze my boobs, and I liked it when he squeezed my tit. I felt titillated for the very first time in my life.
“Yes, that feels good Sam. Squeeze my boob and make me moan some more,” I said.
Then we switched to cowgirl style and I began bouncing up and down. I rode him like mad until he couldn't take it anymore. He shot his load into me without a condom. Neither one of us really thought about it until after he came.
“Oh shit, I just came inside you,” Sam said.
Then I got down with him and gave him a kiss.
“Well if I'm pregnant, we'll figure something out,” I replied.
Then all of the sudden the bedroom door opened.
“What the fuck is going on here?” Jack asked.
We both didn't know what to say. Jack looked really pissed.
“Dude, what the fuck man? You had to do this with my sister of all people? You couldn't just fuck some other chick? You had to fuck my sister?” Jack asked.
“Well, it just happened and we have chemistry, Jack,” Sam replied.
“And he might have just got me pregnant too,” I said.
“What? You fucking got my sister pregnant?” Jack asked.
“Maybe, but I love her,” Sam replied.
Then I kissed him once.
“You love me?” I asked.
“Yes. I think I have for years now; ever since I saw you getting out of the shower once,” Sam replied.
So Jack wasn't happy about this at all. And he went to tell our mom, too. She wasn't too happy about it either. So we both moved into an apartment. So, that did destroy their friendship. But he wasn't all that sorry, though. We both got jobs, but about 7 weeks later after we moved in, we received some news: I was pregnant.
“You are pregnant?” Sam asked.
“Yes, it's positive,” I replied.
Then we both gave each other a hug. We had delivered the news to my Jack and my mom. They weren't in love with the idea, but they still invited us to move in to their house. Then we slept in my old room. Then, after the baby was born, Jack really started to warm up to us. He was happy to be an uncle. And we were even happier to be parents. I think I got pregnant from that first time. But I still found someone that loves me and cares about me. So I'm not sorry either, that Jack had a problem with us.
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