Sister Sucks Sleeping Sibling

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He gets to know his sexy sisters.
  • November 2001 monthly contest
7.4k words
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My sisters: Jill is 24, tall, slender, brunette, dark brown eyes, wears her hair very long and straight; she's got beautiful mid-sized but pointed tits and large puffy nipples. She has a tattoo on the small of her back and one around her navel. She may not be hot in a 'centerfold' sense, but all of my friends think she's the hottest girl in town. They're probably right. She's smart, in college, and has a very serious relationship going with another student. Jenna is 18, short dirty blonde hair, blue eyes, short and petite, with small, rounded titties and an absolutely perfect ass. She's a real tight package and a real troublemaker who loves to party.

How do I know all this about my sisters' physical attributes? Read on...

Last spring, my sister Jill came back home during her school's spring break. She had shared a bedroom with Jenna and had simply moved back in for the month. All 3 of us partied together alot those first few days; I had just turned 21 and could now drink legally in the bars with my big sister. We would get together with a bunch of friends and go barhopping until the wee hours. Unfortunately Jen wasn't old enough to go out on the town with us yet. We used to come home after closing the last club just before dawn and I would immediately crash. Jill was in college and had a few more years of heavy duty drinking on me; I tried to keep up with her but usually failed miserably.

One morning after one of these long nights of drinking, I awoke with the strangest feeling...I tried to think back to the details of the night before for something that could explain it. My memories of the last few hours of those types of nights was non-existent; I would have what Jill called 'black outs' where I just couldn't remember the last hour or so before passing out the night before. She told me it was a symptom of over-doing it and that I should watch it. At least I wasn't driving, I'd say, and we'd leave it at that. Anyway, this was a little strange. I couldn't quite put my finger on it. It seemed that my cock was a little sore; did I get laid last night? I'd have to wait until I saw Jill later on; If anything like that happened she'd be sure to tell me. And I'd be pissed that I couldn't remember it!! More likely, I'd jerked off before passing out.

I saw Jill just after lunch that day. I asked her if she had a good time the night before; fishing for information. She looked at me as if puzzled; then said 'Oh, blackout again, eh? Well don't worry, you didn't embarass yourself or me or anything. Your big sister took good care of you and when we got home you were out like a light. You really ought to slow down, though, Andy. You worry me with these blackouts. Sometimes I think an atom bomb couldn't wake you when you're sleeping like that.' I guess I didn't get laid, I thought. Must have just beat my meat. Oh well.

The next big night out was a house party a few streets down. Jenna was there and yes, she was causing trouble; the kind of trouble that a really hot young girl can cause at a party full of horny guys. Girfriends were pissed at her, pissed at their boyfriends; guys were fighting over who might take her home. Nobody did. Jenna got a charge out of this kind of scene, but she wasn't easy. Jill was getting hit on as well, as was I, but we weren't there to hook up, just for the social thing, catching up with friends and such. That night, during my deep sleep, I dreamed of sex. A blow job, to be specific. When I woke up sure enough, I had that strange feeling again; and the pee-hole at the front of my boxers was sticky with drying jizz... I strained to remember and yes, I remembered having a sex dream, but...well, I had never had a wet dream before...Maybe I jacked off in my sleep. This was starting to severely bug me.

That weekend, I didn't go out with Jill or Jenna; instead I went out with the guys. We went to a local strip club where the beers cost 2x as much as anywhere else, so I hardly drank at all. I got home super late, though, and went straight to bed. I had just drifted off to sleep when something woke me. I opened my eyes to my darkened room and saw what I thought was one of my sisters standing in the doorway, silhouetted by the light in the hall. Just before I opened my mouth to ask what was up, she took a step forward. Then she stopped again. She seemed to be trying hard not to wake me. This was just weird enough for me to let it go and see what she was up to. She reached the edge of my bed and ever so slowly sat down on it. At this point I could see that it was my big sister Jill. She was watching my face intently but she obviously couldn't tell in the dark that I had one eye open just a tiny bit. I could barely make out that she was wearing nothing but a nightshirt and panties. What the heck was she up to? She reached up to the top of my blanket and slowly, noiselessly, pulled it down at the corner to expose most of my body, clad only in boxers. I was being careful not to change my breathing one bit; I had to let her think I was sleeping so I could see where this was going. My sister then reached straight for my crotch with both hands and delicately unsnapped the button in front. Then, my entire world was rocked: Jill reached inside my boxers and gently pulled out my flaccid penis.

Not reacting to this was perhaps the hardest thing I've ever done in my life. At first I was embarassed that my sister might see my cock; then she was holding my cock in her hand! Suddenly I knew: this was the source of my morning mystery. Jill was coming into my room at night and playing with my prick while I slept! She must have thought I was blacked out tonight as well! Before I could think any further, she lowered her head to my groin and popped my soft dick into her warm, moist mouth. Dear God in Heaven!! I thought about putting a stop to this, but just as quickly, that wonderful 'blowjob' feeling overwhelmed me. To my partial embarasssment, my cock started stiffening in her mouth, but I could see that this is exactly what she wanted. As her head gently bobbed up and down, swallowing a good portion of my 8 inch dick, she kept looking up at me for any signs of my waking. Jill gave me head gently, quietly, lovingly; my head spun as I tried to understand just what all of this meant. She slathered her hot saliva all over my big dick and pulled her head off for a moment while softly stroking it with her hand. She looked up at me to be extra sure and then leaned back over to continue her slow-motion sucking. To my amazement, I saw Jill reach under her nightshirt with one hand and begin to fondle her boobs as she moved her lips over my now fully-erect cock. She pulled and pinched on the puffy nipples that had begun to poke against the inside of her nightshirt. Her sucking became a little more urgent then. Watching my sister play with her tits was too much; soon I felt the cum rising to my cock. But she didn't stop. Quickly I thought, well, I never woke up before, so I better not 'wake up' now! My hips were moving involuntarily; Jill didn't stop so this must have been normal. When I saw Jill's hand quickly move to the front of her panties and rub her crotch I couldn't stand it anymore. I came into my sister's mouth, trying not to thrust too hard. I made a little noise, hoping it was ok, and just kept cumming. I watched Jill swallow almost every drop of cum in 2 or 3 quick gulps without releasing my cock from her mouth; I marvelled as she sucked (and I mean Sucked) the remaining cum from my dick. Cleaning off my cock with her tongue, she took another quick look to see if I was waking and, satisfied that she had gotten away with this again, slowly got up and whispered across the floor and out of my room. My door shut with a click. There I lay for what must have been an hour trying to come to terms with what had just happened. God it was good! But was it OK? Should I have stopped her? I didn't know what to think. All I knew was that the next day whe I awoke, I would know exactly what had caused that 'strange feeling'...

The next few days at home were strange, to say the least. I acted as if I had no idea what went on during that night and so did Jill, but I found that I was looking at my sister in a whole new way. She had blown me, for god's sake! I was fully realizing, when our paths would cross around the house, just what a gorgeous babe she really was. I found myself craving another night like the one where perhaps more than just head might take place...but I was confused. If it was OK with her to suck my cock as I slept, would other stuff be okay too? How about while we were both awake? I decided to play it by ear. And to make it happen again, of course.... So the following Thursday evening we went out barhopping. I tried to make it look like I was drinking hard; I wasted alot of beer and money that night, but I hoped it would be worth it. After calling it a night (though it was really early morning), we headed home, Jill at the wheel. Hey, what the hell, I thought, and pretended to pass out in the car. Sure enough, after calling my name 5 or 6 times and after giving me a few not so gentle pokes in the ribs, her hand was at my crotch. She massaged my dick through my jeans with one hand as she steered with the other. I kept my eyes closed for the entire ride, not risking a look. When my dick was completely erect, I felt her fumble with my zipper for a bit but she must have decided we were too close to home and let it alone. I wanted more, however. She had gotten me hard again and I prayed for my sister to blow me again once we got home.

She helped me in the house; I put on quite a show by being 'too drunk' to get out of the car on my own and 'too drunk' to climb the stairs. When we got to the front porch, Jenna met us at the door and helped Jill get me inside. Jill whispered 'I told you--look at him! He's trashed! He won't remember a thing!'

Really pouring it on, I said 'Hi, Jen!' far too loudly and headed for the couch.

'Oh, no, big guy, you're going to your room. Straight to bed! You had a bit too much tonight; I told you you better watch it!' She swung her arms around me and led me down the hall and into my room. Jen just stood and stared. I mumbled goodnight to both, pretending a drunken stupor and hoping for Jill to make a move on my prick once we were in my room.

But she didn't. She lay me down onto my bed and I immediately pretended to be out cold. Then Jill clicked off the light and left. That was it. Hmm...Maybe she was waiting for Jenna to go to sleep? Maybe she wasn't falling for my act. To tell you the truth, I was a little drunk (I had to drink some that night; Jill's no dope) and after listening for her return I fell asleep. And was re-awakened soon after...

My room was dark. My jeans were being removed; then my boxers. I lay there, completely exposed, before…who? Was that 3 hands I felt? Clad in only my shirt, I waited for my sister's mouth on my cock. But instead, I heard her speak: 'Just sit down! Don't worry; he's out, trust me.' Another person was in the room, too; I heard Jenna's voice but I couldn't hear what she said as she whipered. Jill continued. 'Be quiet and watch, I'll show you.' Then, finally, I felt Jill's hand on my dick. She stroked my balls with the other hand and soon she massaged me into a full 10 inch erection. I heard Jenna say 'Move over a little, I can't see it!' I felt Jill move on the bed as she continued stroking my shaft. My eyes were adjusting to the light from the hallway and I could see Jenna sitting in the chair near my bedroom window, wearing a grey cotton pajama set consisting of shorts and a top. She wasn't wearing that when she met us at the door...Jill wore a white nightshirt that ended just above the knees. Jenna was staring at my cock.

'Wow...I've seen a few, but not like that...'

'Like what?' Jill whispered.

'So...big...You really put your mouth on it and he doesn't wake up?'

'Yeah! Watch this...' And with that, my sister proceeded to give me the second greatest blow job of my life. She took care not to block Jenna's view of the action; pulling her hair out of the way if it fell into her line of sight. Jenna watched, amazed, as her big sister slurped and sucked their brother's cock.

'Do you think he can feel it?' She asked.

Jill slid her head up and off my dick. 'Oh, yeah--he moves around and moans a lot, especially before he comes. Sometimes he even opens his eyes. But he never wakes up. And he never remembers anything about it 'cause he 'blacks out' when he's this drunk!'

'What do you do with his...cum?'

Jill just looked over at her with a look like 'what do you think?' and continued to suck.

"Have you ever fucked him?' Jenna abruptly asked.

Jill shot her a look as my dick popped out of her mouth. 'No way! That would be cheating on Mark!'

'And this isn't?'

'SHSHSH!! No! It's just oral sex! And besides, it's not like this is another guy; he's my brother! And he doesn't even know. C'mon! Be quiet and let me finish. I told you you could watch only if you were quiet.'

Jenna's questions stopped. Jill concentrated on my member, blowing me just like the night before. My sister's warm mouth felt phenominal. I started moaning and writhing; Jill didn't stop and Jenna leaned in for a closer look. She leaned forward in the chair with one hand pushed into her crotch. 'Ohhh, yeah, he likes it,' Jenna whispered. "Suck it, Jill. Yeah, suck Andy's cock.' The hand in Jenna's lap started to move. She began masturbating her 18 year old pussy through her pjs. 'Suck that big dick.'

Jenna's hot talk seemed to heat things up for both of us. Jill sucked me harder and deeper and I felt the jizz rising. Peeking out from under one eyelid, I watched as Jenna pulled the crotch of her pajama shorts over to one side, exposing her cunt. The hall light shone through my open door and spilled over the chair she sat squirming in, illuminating her pretty pink pussy. I didn't get much of a look, though, as her other hand started quickly rubbing the exposed mound of her cunt. 'Suck his big hard dick Jill. Suck it for me.' An animal look crossed her face as she played with herself and watched Jill inhale my long, fat prick...I caught sight of Jenna sliding a finger into her pussy and finger fucking herrself...This was just too much for me. The cum was ready to blow and Jill knew it would gush any second. She let out a series of moans as my hips fucked her face, 'mmm, Mmm, MMM!' and I let flow another throatful of thick, hot cum. Jenna watched, writhing in the chair, her hand slapping at her wet mound as Jill swallowed all of my load hungrily. I spied Jen biting her lip and shaking to orgasm, grinding her finger into her puss. I let out a loud "Ohhh!" and they both froze momentarily; but I just smiled and rolled over.

I couldn't see either one any more, but I heard Jill say 'See? That's the fourth time I've sucked him off and he has no idea! It's great! I can get off while I'm here and it's harm done!' Jen lay back in the chair, panting. Jill looked down at her baby sister's still-exposed cunt. 'Wow. You really get off on that...' Jill said, as Jen slowly straightened her pj's.

I'm assuming Jenna nodded her head in the affirmative. 'But how do you get off? Just by sucking his dick?' she asked.

'No, I sometimes play with myself while I do it; sometimes after when I'm in my room.' Jill replied as she slowly got up off the bed.

'Well, I'm wondering...If it's okay to do with your brother then it would be OK with your sister, too, right?' Jenna said as she took a step toward Jill. She was unbuttoning her top as she spoke.

'What would be OK?' Jillian asked, truly surprised. She watched mesmerized as her little sister opened her top and exposed her pretty pert boobies. 'I’m so fucking hirny, Jilly. I bet you are, too. Let me get you off. It'll be OK. You won't be cheating, right?' Standing directly in front of Jill now, Jenna took her big sister's hands and brought them up to her tits. Jill offered no resistance. Jenna moved even closer and whispered in Jill's ear. I could hear every word of their exchange. My dick was already hard again. Had I died and gone to heaven? 'Let me eat your pussy', she breathed into Jill's ear.

Jill let out a breathy sigh as she felt Jenna's breasts. Jen put her hands on Jill's ass and started kneading her cheeks, reaching around and under and feeling through her panties for her now-wet vagina. Jill never answered, never gave permission, but it was clear she wanted Jen to lick her. Jen led her big sis the few steps over to the chair and slowly slipped her panties down from under her night shirt, feeling Jill's long slender legs all the way down. Jill started a sentence; 'Jen...', but she never finished. They were totally oblivious to me at this point; I watched their every move. Jenna sat Jill down at the edge of the chair and spread her ankles, one over each arm of the plush chair. Jill's beautiful pussy was fully exposed to me. It was the most perfect pussy I'd ever seen: Neat and closely trimmed patch of soft brown hair, mostly-exposed fleshy pink lips, pouting partly open, slightly glistening with her moist lube. Then Jenna's head obscured my view as she began licking Jill's gash up and down in long strokes. Jill threw her head back in ecstacy as her little sister licked, sucked and kissed her vagina. Soon she was panting; I think Jen inserted a finger; maybe two, but I couldn't tell. Jill removed her nightshirt in one amazing move, it was over head and on the floor in a split second.

And there they were, Jill's beautiful tits. Not 'big', but long...they stood straight out from her body for what seemed like a foot and their ends were capped with big puffy pink nippples. She was squeezing and pinching them as Jenna ate her pussy; she tried to speak again and failed. 'Jen...Ohhhhh, ohhhhh, Jen....' I was wishing I could see some of the detail work that was going on over in my chair, but counted myself lucky and reminded myself that the view from over here was just fine. Jenna and her perfect ass with her short-short pajama bottoms riding up her crack; on her knees in front of Jill's long lovely legs spread wide; Jill pulling on those fantastic naked tits I'd marvelled at since I was a kid. My two gorgeous siblings were getting it on and I had a front row seat. God I wished I could fuck them. Jill shook in the chair as she came, pushing Jenna's head into her groin with a grunt. Her nipples looked brown and hard; Jenna reached up to play with them as she brought her sister off. As she orgasmed, her face contorted into what looked like agony. But I knew better. For a second I thought she might scream, but she held her breath instead. Red-faced, she fell completely limp in the chair. Jenna leaned up to kiss her and said something I couldn't make out. Jill reached down and took Jen's face in her hands and kissed her.

The sun was coming up soon. Jen left first; Jill followed moments after. I fell asleep wondering if this entire week had been a dream.

The next two days were even more difficult; we had a pretty tangled web of secrets going on and it wasn't easy to interact naturally. While Jill and I could deal with each other pretty well, never letting the other know something was up; Jenna wasn't very good at it. I caught her looking at my crotch regularly; she stammered when speaking to me, avoiding eye contact; and she asked what Jill's plans were for the night about 5 times a day. Jill gave her 'cool it!'-looks every so often, but poor Jen couldn't help herself. She was obsessed with what had taken place the other night. Jill didn't want Jenna to ruin a good thing, sure, but she also knew our parents would have strokes if they ever knew what was going on between us. So saturday night, Jill wanted to cool it for a bit and went out with some old friends from the neighborhood. Instead of making plans myself, I decided to stay in and watch a movie. My parents always retired at around 10, and Jenna was sure to be out 'causing trouble'; I would have the entire downstairs to myself. But my assumption about Jen proved incorrect; when she found out I'd planned on staying in, she was thrilled.