I was babysitting Emily one night. Well, she's 13 and I'm 15 so it's not really babysitting like when we were younger but I was still "in charge" I guess. It was just past 10, Emily's bed time, so I told her to go get ready for bed. She gave me a bit of a pout but I didn't give in so off she went. A few minutes later she came back into the living room looking cute as hell. She had her hair up in pigtails (she often has a ponytail, but rarely does the pigtail look) and had a baby blue t-shirt on. The shirt came down to the middle of her tush and I could see she was wearing white, boy-cut panties. Her long and slender legs are my favorite feature and I couldn't help looking them over. She has very small boobs but even so I could see her nipples pushing at the fabric of her thin t-shirt. She walked over and sat on the other end of the couch from me. She pulled her knees up to her chest and pulled the shirt over her legs. She stretched the shirt down so just her manicured toes were peeking out.

After a few minutes it was pretty clear she wasn't going to volunteer to go to bed, so I told her it was time for her to hit the hay. She scooted across the couch and grabbed my arm. "Please let me stay up. I'm not tired or anything. Just another half hour??" She gave me her best pout with those sweet, soft lips and batted her eyelashes at me. I glanced down at her toned legs and then back to her sweet young face. My hesitation must have given her hope as she went for broke. She threw her arms around me and rested her head on my shoulder. "You'd be the bestest brother in the world if you say yes. And you'd make your little sister so happy and thankful!" She smelled so good and as she nuzzled into me I could feel the warmth of her lips and breath on my neck.

"Okay, another half hour but you owe me big time." I finally said, my mind already racing.

"Thank you Adam! You're the greatest big brother ever!" she squealed as she gave me another big hug, this time also giving me a big kiss on my cheek. She curled up beside me and settled in to watch the rest of her show. I looked down on her sweet young face as I considered my options. In the summer months she gets the faintest hint of freckles on her cheeks and nose. She has long eyelashes that make her blue eyes adorable. She had one hand on my shoulder and I noticed how tiny she still is. She's a little over 5 feet now but still not curvy yet at all. If you looked at her chest or her face you'd think she was still just 10 or 11 but her legs and tush might make you think she was 15 or 16. Though sometimes when she's got makeup on and had her nails done you can tell she's going to break a lot of hearts when she's older.

After the show ended and her extra half hour was up I could tell she was just waiting for me to send her to bed, probably hoping I'd forget so she could stay up longer. I had my plan ready to go though so I said "Your extra half hour is up kiddo." She reluctantly stood up and despite her earlier claims I could tell she was getting sleepy. She slowly started to shuffle across the room and I watched her cute little tush as she did. Just as she got to the door I stopped her "Wait one second."

She turned around and looked at me quizzically. "Remember I said you'd owe me?" She nodded, looking a little less sleepy suddenly. "Come over here." I said. She made her way over to the couch and stood beside me. I stood up beside her. She's quite a bit shorter than me and she looked so adorable looking up at me. I took her by the wrist and she tensed up a little bit. I turned her hand and put against the front of my boxers where I was already starting to get hard with anticipation. She let out a little gasp of surprise as she looked down at her hand now cupping my cock through my boxers. She looked up with wide eyes but said nothing. I guided her hand to begin gently rubbing the outside of my boxers. At first her hand was mostly limp but as I guided her she would squeeze gently as she started stroking my hardening cock. I let go of her hand and let her continue on her own, watching as her little hand massaged my cock until it was completely hard and straining at my boxers. I lifted her hand away and she looked up at me and smiled that cute, crooked smile of hers.

I'm not sure if she thought she was done but she looked very surprised when I pulled my boxers down and stepped out of them. Her eyes flitted between my hard cock and my eyes as she waited to see what was next. I took her hand in mine and at first she resisted but after a second let me guide it towards my cock. When her hand was less than an inch from my exposed cock I could see her fingers stretching a little towards it - she clearly was eager to know how it felt even if she was mostly scared of what we were doing. I stopped her hand before she could touch my cock and she looked up at me with surprise. There was a tiny bit of relief in her eyes but I saw plenty of disappointment as well. "You have to be very gentle" I said. She nodded at me as I let go of her hand. She looked back down to my cock and slowly let her fingertips each make contact with the head of my cock. She looked up at me for approval and I nodded for her to continue.

She moved her fingertips up and down the shaft of my cock now, each time wrapping them around a bit more until she had her fingers completely wrapped around and was stroking my cock from base to tip. I was watching my little sister's hand move up and down my cock and watching her blue eyes follow the motion of her hand as she did so. Her mouth was slightly open and I caught a glimpse of her tongue as she wet them sliglthy.

"Okay, now, get on your knees." I said. She looked up at me with her eyes wide. "It's okay Emily," I said, "you owe me remember?" She nodded slowly and then I guided her around in front of me. She slowly got down on her knees so that she was at eye level with my throbbing cock. "Now stay still." I said and she nodded slightly, moving her eyes back and forth between my eyes and the throbbing cock barely an inch away.

I took my cock in my hand by the base and directed the tip of it to her face. She flinched a little bit as the hot skin of my cock head made contact with her left cheek. She righted herself and didn't flinch as I touched my cock to her face again. I gently caressed her face with my cock as she looked up at my face. I couldn't believe how excited I was! Rubbing my hard cock from one cheek to another of my little sister's sweet face. Then I took the head of my cock and very gently drew it across her slightly parted lips. He lower lip quivered a little bit - I wasn't sure if it was excitement or nervousness as I could see some of both in her eyes. "Lick your lips" I said and she complied immediately. I moved the head of my cock across her now wet lips, this time pushing against them a bit more. I had to control my breathing as I wanted this to last for a while, though I was so excited I was pretty sure I could have cum right then and there. I moved my cock back and forth over her mouth, sometimes pressing the head against her lips, sometimes letting the head touch the tip of her nose as I moved the shaft across her moist mouth. After a moment or two, she had relaxed her mouth and was getting into the rhythm with me, applying a little pressure with her lips at each pass and keeping them wet. A couple of times her tongue would touch my shaft as she wet her lips and each time my cock would throb with pleasure. She must have noticed this as she clearly tried a few times to lick her lips a bit extra to watch my reaction as her tongue ran over the tip of my cock.

I pulled my cock back and moved a little back from her. She had clearly gotten more comfortable with this new contact because as I pulled back she followed my a little bit before opening her eyes to look up at me.

"You need to take off your shirt" I said. She barely hesitated this time (always a bit of an exhibitionist anyway) and pulled her shirt off over her head. I drank her in. Her boobs are very small but her nipples are very pronounced and were hard as little rocks. Her stomach is flat and toned, her shoulders soft and tan as the tips of her pigtails tickled at them. She settled back to her half crouch and looked up at me while she wetted her lips. "Now," I said, "you have to be very careful not to let your teeth touch my cock." She swallowed noticeably and her eyes were wide again with surprise - though I think she had anticipated this as she nodded, licked her lips again and opened her mouth.

I rested the head of my cock on her lower lip and slowly moved it up so that it was touching her top lip. She kept her mouth still as I pressed my cock against her parted lips. I moved it back and forth a few times, allowing her wet lips to get my cock nice and wet then very gently pushed the head of my cock into her mouth. I could feel her tongue on the tip of my cock as the head disappeared between her lips. I pulled my cock back out and she took a deep breath and licked her lips again as she looked up at me with those sweet, innocent blue eyes. I could tell that she was in conflict. Part of her was scared about the idea of sitting in her panties while her brother pushed his hard cock in her mouth, but part of her was clearly excited about doing something so naughty. Whatever she did next would dictate my next move. I held my cock still, just an inch from her mouth while she looked up at me. Her eyes dropped to my cock and my heart seemed to have stopped as I waited for the longest two seconds of my life. Then she leaned forward and took the head of my cock back between her young lips.

I rested one hand on her shoulder and the other very gently on the top of her head. She rested one hand on my hip and wrapped the other around the base of my cock. She mostly kept her head still while I moved my hips back and forth gently, but after a moment she began to move in rhythm with me. She couldn't take much more than the head of my cock into her mouth before I could feel her tongue against the tip. I could feel my balls tightening and a huge orgasm building as my little sister continued to suck me off. She paused for a minute to catch her breath and I guided her hand to the head of my cock which was wet with her saliva. I closed my hand around hers and guided it from the head of my cock to the shaft and back a few times until my entire cock was now moist. She continued stroking my shaft as she took the head of my cock in her mouth again. She let her lips move back and forth over the ridge of my cockhead, applying more pressure each time. Her eyes kept moving between my cock and looking up at my eyes for approval.

I could feel my orgasm building so I took one hand and held the base of my cock and my other hand held the back of her head so I could dictate the pace. She put both hands on my hips as I built towards a huge climax. My breathing was getting faster and I was groaning at this point as I imagined cumming in my little sister's mouth. Emily looked up at me with her sweet blue eyes as her wet lips moved over the head of my cock. Seeing her sweet, red lips sliding over the ridge of my cock set me over the edge and I shot a huge spurt deep in her mouth. She instinctively pulled back but I held her head close as the second stream of cum shot over her head, leaving a white streak on the side of her face. She was breathing heavily and her face showed so many emotions. She was clearly nervous still, but she was also amazed at what she was seeing and also very clearly turned on. She looked back down at my cock as a third explosion erupted from it, hitting her shoulder and chest as I stroked out the last few drops onto her and running my hot, throbbing cock around one nipple.

I fell back onto the couch exhausted and trembling but with a huge smile on my face. Emily sat back and looked at my cock as it slowly lost its hardness, then wiped the cum off her face and inspected it in her fingers. She giggled as she rubbed the cum onto her other nipple. She looked up at me while rubbing both nipples gently and smiled.

"Wow, I dunno what would have happened if I asked for an extra hour." She got up and as she did I noticed that she had to pull her panties back up a bit from the middle of her thighs where they had somehow ended up. She turned and I watched her tight little bum as she walked out of the room. I pulled on my boxers and picked her tshirt up off the floor. As I took a deep inhale of her scent from her shirt I heard her turning on the shower upstairs as she cleaned up before going to bed.