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My sister Carolyn and I had a typical relationship like any other siblings. Got along, had our typical fights, etc. We never fooled around which lead both of us to be quite vanilla. But as the years passed and Carolyn got more developed, I never realized how hot she was until I saw her in a bikini at a friends pool party. She usually wore sweats around the house so I didn’t see much at home. Her tits got bigger, she grew her hair out, got contacts, worked out regularly, her body, legs, ass, everything about her was driving me crazy. But I managed to control my urges. Carolyn has a bf(Jared) who’ve I’ve seen every now and then. Carolyn was happy and parents seemed okay with it. Carolyn usually spent her time at his place and spending the night over there couple days out of the week.

One time, as I got home from work, I saw Carolyn’s car in the driveway. Not caring I went up to my room and passed Carolyn’s room, I heard her crying. I knocked on her door, Carolyn said, “what do you want Jay?” I said, “I heard you crying. You okay?” I heard her door unlock as I walk in, she sits on the corner of her bed wiping her tears. “What’s wrong? Talk to me,” I said. “Jared cheated on me with his ex! But I still care about him,” she said sobbing. Hugging her, “oh, I’m so sorry. Just forget about him! Anyone who doesn’t realize what they have in you is insane.” Carolyn started to cry again, holding onto me. “If there’s anything I can do to help, let me know. You want me to stay? Keep you company?” She nodded no. “If you need me Carolyn or want to talk, I’ll be in my room,” I said.

After 2-3 weeks, Carolyn started sleeping in my bed as she said she was lonely. I didn’t mind. One night, as we both couldn’t sleep, we just chatted about life, work, and other general topics. She finally asked, “Jay, can I ask you something? But also promise not to freak out?” As she sat up. I replied, “hmm, this could either be really good or really bad. Okay, shoot.” After a long pause, Carolyn asked, “would you have sex with me?” Perplexed and shocked, “ugh what? Have sex? Are you serious?” She nodded. With nothing to say, she said, “Jared and I had sex like 2-3 times a week, but I haven’t had any sex in like 2-3 weeks and masturbating isn’t cutting it for me anymore. So will you?” I wondered to myself and said, “if this is a joke or some kinda prank? If it is, it’s not cool.” She nodded no. We talked some more about it, her birth control which she was on, I would wear a condom just in case, kinks/fetishes, rough or soft, lube, anal, positions, if she’s a screamer, and other things. We agreed tomorrow would work as our parents were asleep and Carolyn and I weren’t working tomorrow. I also said, “this is the most awkward conversation I had about sex.” She agreed and we both laughed and went to bed.

Tomorrow comes, I wake up and greeted my parents as they left for work. Carolyn was still asleep, I decided to eat breakfast and take a shower. I wasn’t sure how committed she was, so I didn’t mention anything when she woke up. I just began watching TV until Carolyn grabbed my hand and lead me to her room. I had to go to my room to grab lube and condoms. When I got back, she was undressing and got to her panties. “Wow, I don’t know if you know this, but you’re insanely hot. I’ve had fantasies about this for years,” I said. She smiled and blushed, sat me down on her bed pulling out my semi-hard dick. Carolyn began to stroke and suck my dick. As I got harder from her sucking, Carolyn said, “Holy shit! Your cock is big! Like I’ve never had one this big before.” (I’m almost 7 inches)I told her, “just do it the way you can.” As she continued, trying her best to fit it in her mouth, I was getting close to my climax. I told her, “Ah shit! I’m gonna cum soon!” Carolyn couldn’t take my full load as she gagged some of my cum out. Carolyn was about to ride me, but I picked her up and laid her on the bed. I showed her the condom, she forgot and as I put it on, I removed her panties and slid my cock into her pussy. She pleaded, “oh fuck it’s so big. Use some lube. Please be gentle.” As I lubed her pussy and my cock, she squealed as I fucked her slow. She winced in some pain while whimpering. Once Carolyn got used to the size, she wanted it faster and harder as she moaned louder and louder while I pumped her pussy. She screamed, “Ohh! Ahh it’s been so long! Fuck, I feel it in my stomach! Yeah, keep fucking that pussy! Oh it feels so good!” All that just spurred me on as I kept fucking her, when Carolyn wailed, “Oh right there! I’m gonna cum! Yes keep going, I’m gonna cum!” When she did cum, she started convulsing and shivered. Carolyn wanted to ride me, she guided my cock to her pussy and started riding, filling the house with her moans. As she got more into it riding hard, I picked her up, pinned her against the wall with her legs over my shoulders and kept slamming my cock into her pussy. I saw her eyes roll back as she was screaming out and whimpering moans, then pleaded me to stop as she started cumming all over my cock. After catching her breath, I then got behind her and fucked her some more until I came shooting my jizz on her back. Once we were done, Carolyn saw the lube. She asked, “you wanna use the lube again? Put it to good use?” I asked, “are you thinking anal?” As she nodded yes, I asked again, “you sure? It might hurt.” “I’ll be okay,” Carolyn said. I then used the lube over my cock and lubed her ass. I went in raw, she squealed out in pain, “Oh shit! Please, slowly go slowly!” I was about to hit my climax because her ass was so tight. Carolyn managed to go quite deep ass I fucked her ass. She told me to cum in her ass, I shot my load into her ass and saw the cum leak out. We were sweaty and exhausted afterwards.

We both took a shower together. We talked and thanked each other. We only did it a couple more times, making Carolyn scream throughout the house and making her cum multiple times was all the time great. But after about a month, we stopped because Carolyn got a new bf. But after having sex with him, Carolyn confessed to me saying, “I can’t cum when having sex with him. I just fake it because he doesn’t go that deep. His size doesn’t match up to yours.” I told her, “I respect your relationship, but I won’t say no if you ask and I’ll leave it at that.” Carolyn sat for a minute, thinking, then she left my room.

Fictional

NSFW: yes

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