A teenage boy has the best time on vacation... with his sister
In the summer before 9th grade, my family took a vacation up to Boston to visit some family. After a ridiculously long car ride, my mom, step-dad, sister, and I arrived at our hotel. We got settled in and then went to my aunt's house. They took us out to eat and to see the city a little bit, before we all decided that we were tired from the long car ride and headed back for the hotel.
The sleeping arrangements for the hotel were my mom and step-dad in one bed, and me and my sister, Jenna, in the other. Jenna was 20 years old and a junior in college. It was just recently that I started to notice what kind of a package Jenna was. Her tits weren't the biggest (her bras said 34 A), but her ass was fantastic. It wasn't giant, but it was in no way small. It was nice and round, and very firm. She kept her body in great shape. I found myself masturbating to her quite a bit, and even stealing some of her panties and bras, too. Having her in the same bed as me was going to drive me nuts.
After we got back, everybody was dead tired. We turned on the TV and sat on the beds. Eventually, my mom and step-dad fell asleep, and my sister was under the sheets dozing off. The sheets fell on her gently, which made it easy to see all the curves of her body. She was flawless. She was fucking sexy. My imagination started running wild as thought about what was under those sheets. I climber in under the covers, and tried to get some sleep.
I woke up at what I think was about 4:30. Everybody was fast asleep. Jenna had rolled a lot in her sleep, and her ass was very close to me now. I had never really gotten this close of a look at it before. I realized that it was bigger than I originally thought. Damn, was it nice. As I thought about what I would do to it, my cock started to grow. I was lost in my thoughts when I felt my cock come to a halt. I looked down and saw that it was pressed up against her ass cheek. Holy shit. Afraid of waking her, I moved back. But then my hormones got the better of me. I reached my hand out, and slowed moved it closer to her. Keeping a close eye on her face, movements, and my hand, I started to rub her ass. I rubbed everywhere. I ran up her ass crack, across her ass cheeks, over her hips, and down to the bottom of her ass. I must have rubbed and lightly caressed her ass for an hour.
Eventually, the sun came up, and so did my mom. I pretended to be asleep as she got out of bed and went into the shower. I decided that I should probably try to get some sleep. So, I closed my eyes and gave Jenna one last squeeze.
Three hours later, everyone was up. We ate breakfast at some shitty restaurant that my aunt swore by, and went to see a little more of the city. After about 5 hours, we went to another restaurant, and then did the same shit. 10 more hours of walking around was ahead of me. I wanted to blow my brains out. Finally, they got tired, and we headed back to the hotel. We settled in just as we did the night before, leaving me as the only one awake. At about 1 AM, I crawled into bed next to Jenna. I was so excited to get another handful of Jenna's ass.
I waited until about 2 to make any kind of move. I went right for her ass. I moved my hand down her ass crack, all the way down to the bottom. I moved my hand a little further, and she suddenly twitched and turned over. Scared out of my mind, I pulled my hand away and closed my eyes. While I slowed down my heart rate, I figured out that I must have touched her pussy. This gave me an idea. Why just touch her ass? She had tits, too, right? After waiting about 10 minutes, I slipped my hand under the sheets and gently felt around for her tits. I laid my hand on the left one, and nearly jizzed right there. I rubbed them for a little bit, and then decided to give them a squeeze. I took the right one in my hand, and gently squeezed. They were firm, but soft. Although they weren't giant, they were still a handful. I kept on squeezing for another few minutes, when she turned over again. I pulled my hand away, and waited a little bit. Then, I get another idea. I reached out and felt around for her waist band. I very gently pulled it away from her body, and slipped hand in. They didn't stretch very far because of her ass. Still, I pushed my hand down as far as it would go, and felt every inch of bare ass I could. My goal was to get down to her asshole, but her ass wouldn't give enough space. So, I rubbed and squeezed her bare ass for a little longer.
Eventually, she turned over again. Her front was facing me, now. I felt up her tits a little bit, and got yet another idea. I moved my hand south and felt for her waist band. I pulled it away even slower this time, and slipped a hand in even gentler. I started to move a little bit. She was completely bald, not even a little stubble. Slowly, I moved lower. I could feel where her pussy started. I paused there and checked to make sure she was still fast asleep. I moved lower yet, and felt the two individual lips, and the heat coming from her hole. Suddenly, her eyes opened. She looked straight into mine. I felt her hand grab my wrist and pull it out of her pants and away from her. Then, she rolled over and went back to sleep. Scared, I did the same. I thought about how this would play out in the morning.
The next morning, everything seemed the same. I kept my mouth shut and didn't bring it up, and neither did she. She didn't even look at me differently. Maybe she didn't remember. Maybe I was in the clear.
We packed up our stuff and headed out of Boston. Our next stop was in Philadelphia. I was actually looking forward to this city. After another long car ride, we arrived at a shitty hotel. There was only one bed in each room, which meant that we'd have two separate rooms. Maybe Jenna was waiting until we got alone to talk to me. Or yell at me. Anyways, it was about 7 PM and we were all hungry. We went to a restaurant, and unlike Boston, I loved it. After we ate, we walked around the downtown area for about 3 hours. We started heading back to the hotel, and I started getting nervous. We arrived in our rooms, and I played it off like I wanted to get to bed as early as possible. Jenna said okay, much to my relief. I felt her crawl in about 45 minutes later. I didn't make one move, because of how scared I was. I fell asleep, and woke up the next morning to my mom calling my phone. We got up and out of the rooms by about 10:30.
After another day of walking around the city, eating at various restaurants, and taking in the sites, we headed back. This time, I wasn't nervous. We got into our room, and turned the TV on. I took a shower, and then came out and laid on the bed. Then Jenna got in. I took this chance to masturbate to the thoughts in my head that I had of my sister's ass, tits, and pussy. I jizzed in one of my dirty socks just as I heard the water turn off. A couple minutes later, Jenna walked out in nothing but a towel. She gathered some clothes, said, "Sorry" and walked back into the bathroom to put them on. Damn, did she look good in just a towel. She walked out and sat on the bed next to me while she brushed her hair.
She watched the TV and turned to me and said, "How come you didn't try to finger me last night?" My jaw dropped. I had nothing to say. "You think I don't remember?" I just sat there and looked at her. "Hahaha don't worry about it. I know how it is to be your age." she said. "I know exactly how it is." As she said this, she started to get on the floor. She kneeled down in front of me, and I looked at her in confusion. She started pulling down my pants, and I started getting a boner. She pulled out my cock and took it in her mouth. It was the best feeling I had ever felt. She sucked dick like a pro. She kept going for about 5 minutes. She pulled it out of her mouth and said, "Now fuck me!"
I tore off her shirt and pants, and then started to take off her underwear and bra. There she was, my sister, absolutely naked. I threw her on the bed and crawled between her legs. I lick her pussy, and then started to go in. After tonguing her for a few minutes, I pulled it out, and moved to her clit. I started licking her clit in a star pattern. Her thighs tightened around my head. She let moans out and started to buck her hips. I started to speed up and so did she. Her moans grew into shouts of pleasure, and her hips bucked faster. After a little bit more, she shoved my head away, and started shaking and yelling. It was the hottest thing I have ever seen.
After she calmed down, I put on a condom. She looked at it and said, "What the hell is that for?" I told her that I wanted to be safe and she laughed. "I'm on the pill, don't worry." I pulled it off and crawled over to her once more. I lined my dick up with her pussy, and slowly pushed it in. I had never had sex before, so this was the best feeling I ever had. I started pushing in deeper, and she started letting out little gasps. I shoved my dick as deep as I could and pulled almost all the way out. Then, I slammed it back in. We fucked her hard in this position for a few minutes, and was pushed away again. This time, she started to squirt. I had never seen anything like it. It was fantastic.
After she calmed down, she pushed me on the bed and kneeled over me. She started to grind her pussy on my dick. Then, she raised herself up, and lined her pussy up to my dick. She lowered slowly as I plunged into her. Her gasps turned into moans as she started to grind again. Then, she started to ride me. Her perky tits were bouncing up and down as she rode me. She pushed her hands on my chest to gain some balance and started to ride me harder. Then, she threw her head back and let out a yell. My balls started to grow tighter, and I knew that I was gonna cum soon. Just as I was about to blow my load, she hoped off and turned around. Her ass was facing me now. She started to bounce on my dick again. Each time her ass hit my stomach, her ass cheeks jiggled. It wasn't long until I started to feel my balls tightening again.
I started to let out groans, and she hopped off again. She then got on all fours on top of the bed. "Pound that big dick into me, little brother!" she said. I got up behind her, and immediately started fucking her pussy as hard as I could. I started moaning again. "Holy shit, Jenna! I'm gonna fucking cum!" I said. "You wanna cum in my fucking pussy?" she said between breaths. That was all I needed. I let out one final groan, and unloaded in her pussy. It felt like I was cumming for 5 minutes. After I was done, I pulled my dick out and watched the cum drip from her pussy lips. She stuck a finger in and started to finger herself. More cum came dripping out. I was so exhausted that I collapsed on the bed next to my sister who was finger the cum out of her pussy. Eventually she stopped and laid down next to me. She snuggled up close to me and shoved her ass in my crotch. "Just like the first night, huh?" she said. I smiled, and pulled her in closer. I wrapped her in my arms, keeping my dick in her ass crack, and my hand on her tits. We fell asleep like this and woke up the same way in the morning to my mom calling her phone.