Drowsy s*s

I've always been an extremely horny guy. I mean, even for a GUY I'm pretty ridiculous. But I always seem to get the most turned on at the most inconvenient times, like the middle of the night, when no girls are around. In my senior year of high school, when I was 19, I used to stay up late talking to people online. At 1 or 2 AM I would always suddenly become extremely horny, and I would find ways to get girls I was talking to online to talk dirty with me and help get me off. Sometime I even convinced some of them to send me pictures of themselves in their underwear, or less, but only when I was very lucky.

One night I was up talking to this girl, Sami, who was always good at telling stories about the two of us fucking, and had sent me pictures of her and her boyfriend having sex. I was extremely turned on, but found myself wanting more than pictures or a typed story. I pushed my chair away from the computer in frustration when suddenly it hit me. There was a perfect female specimen in my house, right across the hall from me.

My s****r Emily was 18, and one year behind me in school. I'd never really liked her, and found her annoying since all her friends were always over at our house bugging me and doing stupid teenage girl stuff. It didn't help that she was a platinum blond with long legs and perfect C cup breasts, so all my friends were constantly hitting on her, a major pain in the ass. But suddenly realizing that she was asl**p in a room across the hall made her seem much more likeable...

Without thinking, I put on some pajama pants and opened my door. I listened in the hallway to see if anyone was awake. Even though it was close to 2AM, you never could tell who would be awake in our house. Not hearing anything, I snuck down the hall to Emily's room and inched the door open. I listened briefly, and hearing her steady breathing, I opened the door open wide, spilling light from the hallway across her bed.

She was lying on her back with her head turned towards me, and I could tell she was in a deep sl**p. To my disappointment, she had the comforter pulled up to her chest, and I could tell she was wearing a top. Not knowing what my s****r wore to bed, I crept into her room to find out. When I was next to her bed, I crouched over her and whispered, "Emily? Are you awake?" Eliciting no response, I gently shook her shoulder to see if she would open her eyes. Again, no response.

With my inhibitions disappearing, and my arousal growing, I grabbed the top of her comforter and started folding it over itself to reveal my s****r's sl**ping form. As I brought it down over her chest, I saw she was wearing a white tank top with the superman logo across the chest. Looking at the straps, I realized she was not wearing a bra. Score number one!

I slid the comforter down further, glancing at my s****r's face for any sign of discomfort or change in her breathing. Finally, I reached her waist, and when the comforter moved further I realized I'd hit gold. My s****r was wearing a small, white, cotton thong. I tossed the comforter down to her ankles and gazed at her body. Her breasts made the tank top taught across her chest, and her legs were slightly parted, allowing me a view of her thong pressed snuggly up against her mound. I couldn't believe my luck. This was way better than any picture.

Not sure of what to do, I stood there for a good three or four minutes, my dick growing steadily in my pants. I reached into my underwear and gently stroked my hardon. I stared at my s****r's pantied crotch as I stoked myself, knowing what was just underneath that white material. I was about to cum, but then realized I could see more. At this point, all reason had been thrown out the window, and my dick was doing the thinking. I pulled my hand out of my pants, and placed my fingers at the bottom of Emily's tank top.

Ever so slowly, I inched the material upwards towards her head. Already she was looking better with her stomach exposed above those irresistible white panties. When I reached the mounds of her breasts I paused, checking her face again to see if she was waking. My hands were shaking at this point, and my knees felt ready to buckle. Taking a silent, deep breath, I tugged once more at her shirt pulling first one side, then the other up over her tits. The sight was incredible. My s****r's breasts were perfect melons with tiny little nipples topping them off, just the way I liked them. The cold air reached her skin and her nipples hardened. Inside my pants I hardened as well.

I wanted to touch her tits so bad I began reaching for them before I even realized it. Finally some self-restraint kicked in and I stopped myself for fear of waking her. I wanted to jack myself off right then and there and get the hell out of the room before she woke up, but I had to see more. With another hungry glance at her tits, I moved back down to my s****r's panties. These would be much more of a challenge. I grabbed the waistband on either side of her hips and began to tug them downwards. Suddenly my s****r moved! Without warning she rolled away from me, onto her side.

As frightened as I was that she was awake and knew what I was doing, I was also glad she had shifted because now her ass was in perfect viewing condition! I knelt down next to her bed to examine my s****r's ass. I memorized ever inch of it, tracing my eye's over the string of fabric that disappeared in her crack and then reappeared down between her legs again. I rested my chin on her bed, and with my nose 6 inches away from her ass, I was in heaven. But I knew I'd taken a lot of risks and had just about outstayed my welcome. I was just about to sneak back to my room to masturbate thinking about what I'd seen when my s****r shifted again, nearly giving me a heart attack in the process!

Emily rolled back onto her back and spread herself out, trying to get comfortable in her sl**p. In doing so, she'd thrown one arm clear of the edge of the bed, and let one leg dangle off it as well. This left her in a clearly exposed state, and I knew I wasn't going anywhere until I saw her pussy. Abandoning the idea of pulling her panties completely down for fear of making her shift again, I thought of just moving the crotch of her panties aside so I could view her treasure. I leaned over her body and gently slid one finger into the side of her panties near the top of her slit.

The back of my finger slid across her soft skin, making me grit my teeth in arousal. With a weary glance at my s****rs face, I gently but f***efully pulled the crotch of her panties down and to the side. It worked. In one swift motion I had uncovered the most beautiful, perfectly shaved 18 year old cunt I had ever seen. It was smooth and clean and on first instinct I wanted to lean down and devour it with my tongue. But I knew this had been my riskiest move of all, so I did nothing but stare at it. For a full five minutes I stood there with one shaking hand holding her panties aside, and the other hand stroking my cock through my pajama pants. Realizing what would happen if I was caught however, I finally released the material, covering her mound again, and snuck back to my room where I proceeded to masturbate to the biggest orgasm of my life.

The next morning I kept waiting for my s****r to confront me about being in her room, but she never did. She'd remained completely asl**p and I had gotten away with it! I masturbated every night for a week thinking about what I'd seen, getting off faster than I ever could before. But after a week, I started wanting more, and I made my plans to sneak into her room a second time.

On a Friday night, my s****r went out to babysit for a f****y that we knew. She told my parents that she wouldn't be back until after 2 AM or so. I thought this would be perfect since she'd go into a deep sl**p after being up so late. I watched her leave the house in a skirt that showed off her ass. I got hard watching her get into the car since I knew what that ass looked like without the skirt on it.

I spent that evening looking at porn online and talking to Sami, who was telling me she wanted me to lick and fuck her ass. Finally, after I thought I couldn't wait to cum anymore, I heard my s****r pull up in the driveway. I listened to her come in the front door, up the stairs, past my bedroom, and go into her room and close the door. Luckily, I didn't hear the lock click. I waited in anticipation for a half an hour so she could fall asl**p. Finally, I couldn't take it any longer and I headed to the door.

I followed my routine, checking the hallway for noise, and snuck down to her door. I knocked lightly, having no idea if shed fallen asl**p or not. No response. Holding my breath, I opened the door and walked in. I decided to close the door this time to give myself more security from anyone else in the house walking in. But with the door closed I had no light, so I was f***ed to turn on the over head light in Emily's room.

I turned to face Emily's bed and couldn't believe my luck! There on the floor in front of her bed was a pair of panties and a skirt. The same skirt she had been wearing earlier that evening when she left the house... I could only hope that she had been wearing those panties as well, and that she hadn't replaced them with anything. She was sl**ping on her back again, but this time, to my dismay, she had her arms out over the comforter. I wouldn't be able to pull it off of her without moving her arms first!

Reluctantly, I moved to her and prepared to move the arm closest to me clear of the covers. I gently placed my hand on either side of her wrist and picked it up. I met with absolutely no resistance at all! I moved her hand sideways and let go. Her arm now dangled off the side of the bed, clear of the covers. I couldn't believe it had been so easy. This gave me an idea. I stepped closer to the bed and pulled my pajama pants and boxers down to mid-thigh so that my dick was exposed, pointing straight at her. I moved to where her hand hung off the bed, palm up, and lowered myself down so she was cupping my balls. The feeling was incredible! I looked at my s****rs face and smiled. She had no idea what pleasure she was bringing to me my cupping my balls in her sl**p! I placed my hand around her own and manipulated her fingers so she fondled my testicles, I was so close to cumming I was shaking! But I wasn't done yet. I turned around and gently sat down on the edge of Emily's bed, careful not to wake her. I grabbed her wrist once again and placed it in my lap.

This took a little more manipulation, but once I had her fingers wrapped around my dick, she naturally gripped it lightly in her sl**p. With my hand on her wrist, I moved my s****rs hand up and down my cock, forcing her to jack me off in her sl**p. After a few strokes, I couldn't contain myself and I shot my load all over her carpet. I watched Emily's face to make sure she hadn't woken up and I was safe. I got off her bed and pulled my pants back up, but realized I hadn't even checked to see if she was naked under her blankets!

I moved her other hand off the comforter with little trouble and excitedly moved the blanket down her body. What I saw made me instantly hard again. My s****r was sl**ping completely nude! Her breasts were perky and looked better now that she had no shirt on, and her legs were slightly parted, allowing her perfect pussylips to naturally open a little. My dick had come fully back to life and I started stroking it immediately at this sight. Every inch of my body was screaming to jump on the bed and fuck her, but that would surely wake her up, and leave me in a load of trouble. But perhaps her sl**ping body could tolerate a small amount of touching...

Forgetting her tits, I focused on my s****r's pussy. Her thighs were hindering me slightly, so hoping to have the same effect as I did on her hands, I grabbed one of her ankles and slid it sideways. As I'd hoped, her other leg stayed where it was. In a minute I had her legs splayed wide open. Emily's little cunt was in plain sight and I moved between her legs to get a first class view. Her lips were puffy and smooth, just as I'd pictured them, and the smallest bit of pink showed at the center of her slit. But I wanted to see more.

I took a finger and ever so lightly brushed it in a circle above her pussy. She had the softest skin I'd ever felt. I checked her face to make sure she was still sl**ping soundly, and moved down to her lips. Touching my s****r's pussylips was the most incredible thing I've ever done. They were soft as silk and I wanted to rub them forever. I added another finger and gently parted her lips. They stuck together with the slightest bit of moisture but spread apart as I moved my fingers. I wanted to use my other hand to slide a finger up inside her, but again I was worried that I would wake her up.

Instead, I did something even riskier. I moved up closer so that my face was inches from her pussy. I could feel the heat from her cunt on my face. I couldn't believe I was this close to my s****rs twat and that it was so spread open for my enjoyment. I was in heaven, and before I knew it, I had opened my mouth wide and then closed it over my s****r's cunt. It was the first time I'd ever put my mouth on a girl's pussy, and I'll never forget it. I could feels those smooth pussylips inside my mouth and I wanted to slide my tongue up inside her as far as it would go, but I still feared that penetration would wake my s****r. Instead, I lightly sucked on her twat. Emily's entire pussy was enveloped by my mouth, and feeling bold I slid my tongue along the outside of her lips. I knew I'd gone as far as I could go without waking my s****r, so with my mouth still on her cunt, I jacked myself off and came on her carpet for a second time that night.

I covered Emily back up with her blanket and left her room, convinced that nothing hotter could ever happen to me. Little did I know what was to come.

I continued to masturbate nightly thinking about my s****r's naked, sl**ping body, and imagining my mouth on her cunt again. About two weeks after I had touched my s****r in her sl**p, I was awake in my room in the middle of the night, lying in my bed stroking my cock. I was just about to go to sl**p, so I was wearing only boxers. I was lying on my back, jacking off, when there came a very soft knock at my door. Surprised, I removed my hand from my dick, but didn't answer. The knock came again, but I didn't respond so that whoever it was would just go away. But to my chagrin I heard the door handle turn and the door creak open.

I feigned sl**p, not wanting to have to carry on a conversation with my dick in a semi-hard state. I expected whoever it was to just close the door and go away, but instead I heard a wisper.

"Eric? Are you asl**p?"

I was my s****r's voice! Hearing Emily's voice made me thinking of her pussy and I was instantly as hard as a rock. I wanted her to go away so I could picture her cunt and get off before I went to sl**p. I heard the door close and was about to open my eyes again when my bedroom light clicked on! She was still in the room! I couldn't figure out what on earth she was doing in my room this late at night. Maybe she was looking for a CD or something she thought I had? I heard her wisper again.

"Eric?"

I was NOT going to reply with a swollen dick, so I just lay there motionless. I sensed movement in the room and was surprised when I realized she was standing near my bed. I tensed suddenly, realized my rockhard dick was probably making a sizable lump in the covers over my body. I began to will it to soften, trying to make my arousal disappear, when I suddenly felt Emily's hands at my chest where the comforter was pulled up to my chin. What on earth...

I caught my breath as she slid the comforter down my chest, exposing my naked torso, and worried when I realized she would soon be uncovering my boxers that were surely tented by my cock. Curious as to where this was going however, I continued playing possum and allowed Emily to continue.

The comforter slid over my boxers, up over my dick, and down my legs, bunching down at my feet. I felt very exposed wearing only my boxers with a hard dick inside them, but I wanted to see what my s****r had in mind, so I continued to "sl**p." What happened next was better than I could have ever dreamed. My s****r reached down and grabbed the material of my boxers right over my dick. Touching only the material, she maneuvered it so that the opening in the front found the head of my dick. I felt the cold air hit the tip of my dick and I was hard as ever. Emily slid the rest of my dick through the opening of my boxers so that the material was all the way at the base of my shaft.

My entire hardon was sticking out the front of my boxers and I heard my s****r gasp lightly. I had never been so turned on in my life and I couldn't wait to see what she did next. I was hoping she would sit on my dick so I could just open my eyes and start fucking her, but I wasn't so lucky. I waited, but realized Emily was just as nervous as I had been, so she was merely viewing my cock. Finally, after a few minutes, I felt her fingers cautiously circle my dick. This felt infinitely better than when I had f***ed her hand around my shaft.

Unsure of what to do, Emily began to slide her hand up and down my cock. Her grip was loose, but firm and it felt like she really wanted to make me cum. If that's what she wanted, I was not going to disappointed her. I was just getting ready to shoot my load for her when she stopped! Was she chickening out? Was she going to go back to room and make me finish myself off? I had to know, so I took a chance and cracked one eye so I could finally see her. I peeked out and saw that she was wearing an oversized sweatshirt. With one hand she was gripping her breasts through the sweatshirt, and the other was moving up and down at her crotch, obviously sliding in and out of her pussy.

I cracked the other eye so I could watch my s****r finger fuck herself a bit better, but closed my eyes tight again when she shifted her head. I waited to see what would happen. Since I'd had my hands under the covers when she came in the room, they were now lying at my sides. I felt Emily take my hand that was closest to her and gently lift it off the bed. She moved it sideways so that it was perpendicular to my body, jutting out over the bed. Now I had an idea of what she had in mind. I felt something warm on my index finger and was confused for a moment. Then I realized that Emily was sucking on my finger! What for? I didn't want to open my eyes and give myself away, so I was going to have to wait and find out. She removed her mouth from my finger and I felt the cold air on it since it was now coated with her saliva.

The next thing I felt on my index finger was warm, like Emily's mouth, but didn't envelope it. Instead, it rested on top it and began sliding back and forth on it. I almost came when I realized my s****r was now straddling my hand and sliding her pussy over my finger. She had positioned herself so my finger was directly on her slit, parting her pussylips. The feeling was so sexy! I wanted desperately to curl my finger upwards to insert it deep inside my s****r, but I was enjoying letting her do all the work. She continued to slide over my finger and eventually, I felt some pressure on the underside of my digit.

Emily had reached between her legs and was now manipulating my finger so that it would stay straight. She was going to slide my finger up into her pussy! Emily slid forward on my finger so she could line it up with her opening. She attempted to slide back down onto it, but couldn't quite get the angle right. After three failed attempts, she had to slide her own finger up inside her along with mine. Once my finger was inside her, I tensed my hand slightly so she could ride it a little without having to do it herself. I hoped she didn't notice.

Emily grabbed my wrist and started bouncing up and down on my finger, sliding it deep into her pussy. I couldn't believe how wet she was and how good it felt to have her smooth lips envelope my finger. Eventually, Emily slid off of my finger, and I was afraid she was done, but then I felt a new sensation. My finger was now touching what felt like two mounds of flesh. I wondered what it could be, and finally realized Emily had turned around so she was now facing away from me. She had backed up to straddle my hand once more with her ass now facing me. I figured she wanted to feel my finger inside her cunt from behind and was ready to let her insert it into her pussy again, but she surprised me with what she did.

Instead of lining my finger up with her pussy again, Emily widened her stance and squatted down slightly, opening her asscheeks up. She reached around behind her to take my hand in hers and gently placed my still sopping index finger up against her asshole! I could feel the puckered skin of her asshole as Emily took my finger and rubbed it across the opening. I couldn't believe this, my own s****r liked her ass fingered! And now it was her b*****r's finger that was up against her hole.

A moan escaped my s****r's lips as she continued to rub my finger against her anus. I wanted to do more than just finger that cute little butt, but I was more turned on than I'd ever been so I just laid there. Emily took hold of just my index finger and straightened it out so she could insert it into her ass. Since I couldn't help, it was difficult for her to get the right angle, but finally succeeded in pushing the tip of my finger up her butt. Emily moaned again and turned so she could grab my dick once more. She stroked my cock again as she flexed and released her asscheeks, simulating me sliding my finger in and out of her ass.

I was about to cum harder than I ever had in my life, but Emily had the uncanny ability of stopping just before I came. She let go of my dick and pushed back one last time onto my finger, burying it up to the second knuckle in her ass. Emily paused for a minute with my finger deep in her butt, no doubt disappointed that she would soon have to return to her room. But she wasn't quite finished yet.

Emily pulled my finger out of her ass and turned to face me once more. I cracked my eyes again and watched as she slid her oversized sweatshirt up over her head. She was now fully nude. Next, she daintily placed one kneed on the bed next to my shoulder. With amazing dexterity she swung her other leg over me and onto the bed. She was now straddling my body facing down towards my dick. She scooted her legs up closer to my head and bent down placing weight onto both her hands. We were now in a 69 position! I could feel Emily's cunt inches away from my face.

I couldn't believe she was this bold, but I sure was glad she had the guts! With Emily facing away from me, focused on my dick, I could safely open my eyes all the way without being discovered. The view was unimaginable. Emily's cunt and ass were right in my face. Her pussylips were wet and glistening from her own juices, and her asshole was spread taught. I enjoyed this view of her anus since I'd only felt it with my finger before. I was dying to slide my tongue up her asshole and give my s****r some real pleasure, but I still didn't want to ruin the moment.

Fortunately some people sl**p with their mouths wide open so I could open my mouth and still believably be asl**p. I opened my mouth wide, hoping Emily would lower herself onto it. But instead, Emily suddenly enveloped my whole cock in her mouth. Instead of sliding up and down on it, as I would have expected, she kept her mouth in one place and just sucked inward, the feeling was incredible. By this point I could tell she was desperately trying to make me cum. I wanted to, but I was holding out until she placed her pussy in my mouth and I could lick those pussylips again.

Since my dick was still through the hole in my boxers, Emily had no access to my balls, but to remedy this, she reached down and slid a hand up the leg of my boxers. She found my sack and began squeezing and fondling my balls. I LOVE when girls do this. I was out of my mind. My s****r was straddling my face, sucking my cock, and playing with my balls. And one of her fingers kept sliding downwards and brushing lightly over my ass. Everything felt incredible. I was about to give in and cum when Emily suddenly lowered herself down onto my face. Without warning her cunt dropped right into my mouth.

Dropping all pretenses of sl**p, I began eating my s****r's cunt for all I was worth. I sucked hard on her clit and slid my tongue deep up inside her. Emily didn't miss a beat and sucked me harder and harder, squeezing my balls deliciously. I was about to cum and decided to give my s****r a treat before I did. I licked right up her slit to her exposed asshole and slid my tongue in. My s****r lost control and deepthroated my cock, her lips touching the material of my boxers. I continued to push my tongue deeper and deeper into Emily's ass, and when I could go no further, I felt my s****r slide her middle finger up my own ass.

I exploded into Emily's mouth and she began dripping her juices all over my face as we came together, my tongue in her ass and her finger in mine. We were shaking and tense as we both came down from our orgasms. I removed my tongue from her asshole but continued to lick it and suck on it lightly while she licked all the cum off my dick and continued to squeeze my balls. Finally, without a word, Emily got off the bed, put on her sweatshirt and walked to the door. Without looking back, she turned out the light, and walked out of my room. We'd never made eye-contact once. I guess next time it's her turn to sl**p...
95% (128/7)
 
Categories: Taboo
Posted by mommasbabyboy
1 year ago    Views: 12,750
Comments (23)
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1 year ago
so fucking hot! I want more
1 year ago
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1 year ago
AWESOME I loved it thanks for posting it for us
1 year ago
very hot, enojoyed it all, made me feel bad i didnt have the guts back then
1 year ago
hot story..thnx
1 year ago
had to jack off reading this. waiting for part two
1 year ago
amazing sister
1 year ago
awesome
1 year ago
That's one hot story
1 year ago
That is one great story ...got me very excitied reading it.thank you
1 year ago
hott
1 year ago
Wow - a really hot story that got me so hard I had to cum reading it for the second time.

What a great cum too - thank you - any chance of chapter two?
1 year ago
Fuck, that was HOT!!
1 year ago
That was so hot it had me beating off and spraying everywhere
1 year ago
Very hot story really enjoyed it
1 year ago
that was great, more please
1 year ago
hot i think she knew you had gone in there plase part to please
1 year ago
wow,,very hot indeed,,thanks
1 year ago
The family that cums together, stays together.
1 year ago
Very very hot. Got me so hard
1 year ago
Sexy... Waiting for part 2 !
1 year ago
HOT
1 year ago
very very hot