Lessons on Making OutbyVV_Valiant©
My older sister Nadia and I had always been close, but it wasn't until she graduated high school that we really bonded. She decided, with my parents' blessing, to take a year off to just relax before heading off to college, and so she was around with nothing to do for pretty much my entire school year.
Not that I minded, really, because, like I said, we bonded. Every day, after I came home from school, she would ask me about my day. I'd tell her about whatever was troubling me, like grades or teachers or just people I plain didn't like, and she would listen to it all and give me advice that could only come from someone who had to deal with it all before. I really liked that she listened, and started to depend on her to help me get through my final year of school.
Of course, it certainly helped that she was easy on the eyes, something I didn't notice until we started hanging out a lot more. At first it was little, harmless things, like noticing how her long dark hair hung over her eyes when she tilted her head a certain way, or the graceful way she moved, but as I grew more and more into my role as a sexually frustrated teenager, I noticed more. I would find myself glancing at her big tits as she talked, or watching the way her nice ass moved when he would walk by me. I'll admit it; it's hard being a sexually-frustrated eighteen year old boy when you have a hot sister living with you. Whenever I would jerk off, I would find Nadia intruding upon my fantasies. Again and again I would imagine her stripping in front of me, or what those gorgeous tits looked like when they were freed from her bra. It got to the point where I wouldn't even fight it anymore and masturbate to the thought of fucking my older sister. I would feel guilty, yeah, but it wouldn't stop me from doing it again.
Of course, a lot of it came from the fact that, as I said, I was getting cockblocked on a regular basis. Whenever I could actually get a girl I was interested in alone with me, we would fool around for a while until she'd stop me, panting and nervous, and tell me we were moving too fast. That was kind of the problem as I saw it; time was moving too fast. In a year I would be off to college, and the thought that I would graduate a virgin was preying on my mind.
All of this I kept as best I could from anyone, but I think my sister intuited my problem, at least a little, considering what happened. Either that or she'd been checking me out as much as I'd been dreaming about her.
The day it happened, I was late coming home. I'd stayed a couple hours trying to work through the pile of homework that would carry over into my weekend, and failed miserably. Added to that the fact that, the night before, I'd gone out with Stacy, who'd let me go so far as to finger her before telling me that she wanted to save herself for marriage. It had gotten to the point where I wondered what I was doing wrong.
Such was my mindset when I crossed my front lawn, backpack over one shoulder, to see my parents' car missing from the driveway. Dimly I remembered them saying they would be out of town for the week and warning me against any parties, but I hadn't really been paying much attention. It didn't really matter, however; I had enough of a work ethic to know when to party during the weekend and when to buckle down, and this was definitely time for the latter.
I walked into my house, throwing my backpack in a corner where I promised I wouldn't look at it for a whole hour, then started up the stairs to the bedrooms.
"Nadia?" I called out. "You home?"
"Up here!" She answered back, and I followed her voice into her own bedroom, where I found her sprawled on her bed, flipping through a magazine.
I tried not to stare at her too much, but it was hard. Her blouse was tight, her tits straining against the fabric, and I could make out the outlines of her bra. In my mind's eye I mentally placed where her nipples would be, and felt my cock stir at the image. He jeans were tight, too, accenting her wide hips, and I followed her legs with my eyes to her feet, which were crossed carelessly at the end of the bed.
I tried to contain the fantasies, like I always did around her. Sometimes I even succeeded.
"Hey, Jake!" She said, sitting up and throwing the magazine on the floor. "What's up?"
"Nothing much." I admitted. "Shitty day."
"Well, sit down here and tell me about it." She patted a place beside her, and I fell onto the mattress gratefully, trying to keep the bulge in my pants showing to much.
I told her what was bothering me, about my grades being behind and the homework I would have to do. She told me to relax.
"You got all weekend." She said, smiling. "Why not wait until Sunday? You could spend Saturday just hanging out, maybe take a girl to dinner or something..."
"Oh, God, that's another thing." I said, not really thinking about it but needing to vent. "I keep striking out with girls. I don't know what's wrong with me, but..."
"Wait, wait..." She stopped me. "Hold on a second. What do you mean you keep striking out? Didn't you just take that one girl, Stacy, out last night?"
"Um...yeah." I admitted lamely. "Yeah, I did, but..."
"But what?" Nadia asked. "That doesn't seem like striking out to me."
I shrugged, not having any idea about what to say. I couldn't see myself admitting to my older sister that I was annoyed my date didn't put out. Not only because it sounded shallow, but because she was my sister, and I was still a little weirded out that I couldn't be in the same room with her without thinking about what it would feel like fucking her.
"So, what's the problem?" She pressed. "Was it just a crappy date?"
"No, no, it was fine." I admitted. "Just fine. I, um...just after..."
"What do you mean, just after?" She asked. "What'd you guys do, anyway?"
"Well...we went out, watched a movie..." I cleared my throat. "Made out a little bit..."
"Oh yeah?" Nadia raised an eyebrow and I felt myself flush.
"Well, it's not what we did, it's what we didn't do." I said, finally getting it out. I got the reaction I'd expected. Nadia broke into a huge grin and started giggling.
"Oh, my God!" She exclaimed. "You mean..."
"You didn't...you didn't go all the way?"
"Yeah, yeah." I rolled my eyes. "Yeah, that's it."
"Oh, wow, Jake." Nadia stifled another giggle. "I mean, I'm sorry and all."
"Look, it's not a big deal." I flustered. "Let's just..."
"No, no, it is a big deal, really." Nadia breathed deep, and I was uncomfortably aware of the way her chest came out when she did it. She was obviously trying to get her laughter under control, and as I waited through it I found my eye wandering down to her breasts. I snapped them up guiltily, forcing myself to stop it.
It was going to be hard if I didn't get laid soon, I remember thinking. My sister was just too hot not to fantasize about.
"Okay, okay, I'm better now." She said. "So...when was the last time you did it, then?"
I shrugged. I really did not want to have this conversation with Nadia, especially not since I was a virgin, and ESPECIALLY not that I kept thinking about her nude.
"Well..." I stalled.
"Oh my God, you haven't, have you?"
I shrugged again, and finally nodded. There didn't seem to be anything to say.
"Oh my God, WHY?" She asked. "I mean, you're pretty decent looking..."
"Yeah, thanks." I said, rolling my eyes.
"No, I mean it. You're pretty hot. I don't know why the girls aren't throwing themselves at you."
My eyes widened. Did she just say I was hot? Did that imply that she thought of me as a potential sexual partner?
I squashed the thought as soon as it came up. It was pointless thinking about that. Christ, I was in enough trouble as it was, not being able to keep from lusting after her.
"Thanks." I said. "Really, thanks. And I don't know what I'm doing wrong. I mean, it must be something..."
"Maybe, or maybe you're just going out with the wrong girls." Nadia shrugged. "I can help, if you want."
"What do you mean?" I asked, raising my eyebrow. I thought she was thinking of asking one of her friends to take me out, and I was more than a little interested. Although not as eye-popping as Nadia herself, she hung out with a pretty sexy crowd.
"Well..." Nadia stalled, and I could see a flush creeping up her cheeks. "I could help you with your technique."
"My technique?" I asked.
"Yeah, like, you know...kissing and stuff." She shrugged, and then giggled a little, self-consciously. "I could help you with that."
"Oh." I didn't know what to think, but a little help could never hurt. "All right, that sounds fine."
We stared at each other. She was obviously flustered, and I was still trying to work out where this was going.
"So, should I tell you how I do it, or...?"
"No, no!" She shook her head. "That isn't going to work. I have to...you know, experience it."
My mouth suddenly went dry, and my heart started hammering in my chest. Did Nadia, my hot-ass older sister, just ask me to make out with her?
"What...like kiss you?" I asked, not believing it.
"Well, not if you don't want to." She hurried.
"No, it's fine." I reassured her, perhaps a bit too eagerly. "It's fine, really. Let's do that."
She turned to face me, seating herself cross-legged, and I did the same, trying to keep my raging hormones under control. Short-sightedly, I thought about how much masturbation material I'd get out of this. If I was really lucky, I thought, I could grab a quick feel of her ass, maybe brush up against her fantastic tits.
I didn't know how to proceed, though. I sat there, looking at her face framed by her long strands of dark hair, her eyes flashing in a way that excited me, and had no idea how to proceed. Although she'd given me the go-ahead, and I couldn't make myself take the first step.
"Oh, no wonder you didn't get any!" She exclaimed, frustrated. "Here, like this."
She took my hand, and I felt myself jump a little at her touch. I don't think she noticed, however, because she took it and placed it on her shoulder.
"Here, just grab me like this." She took my other hand and placed it on her hip. "And just kind of fall into it."
I watched as she closed her eyes, coming toward me with her mouth slightly open, and then I closed my own eyes and leaned toward her.
I felt my nerves tingle as our lips met, and as I kissed her, I was uncomfortably aware of my hand on her hip, on the waistband of her jeans. I was even more aware of her breasts pressing against me. I could feel their softness and started thinking again about what the would look like, unbound and dangling in front of me. I felt my cock grow hard in my jeans and knew if I stood up she'd probably see.
Palms sweaty, feeling the bra strap on her shoulder and the swell of her hips, I kept pressing my lips against her, making out with her for all I was worth. I decided I'd at least show her how good of a kisser I was, and danced my tongue with hers, darting it into and out of her mouth as sensually as I could.
After a few moments, I felt her tits brushing against my chest more and more, and realized that she was breathing as hard as I was. Occasionally she would moan and sigh against my lips, and I got even more aroused realizing my sister was getting as turned on as I was.
After minutes I was in no frame of mind to count, she broke the kiss, slowly. Eyes still closed, she leaned away, and I was already thankful for what I got out of it. Then she smiled, her tongue darting out to lick her own lips, and she opened her eyes again and stared at me.
"God, that was amazing." She admitted. "But I think I know what your problem is."
"What's that?" I asked.
"You didn't move your hands at all!" She said. "You have to move around a little bit, you know?"
I laughed nervously, aware that my hands were still where she had placed them.
"I know, I know." I said. "It's just weird, you know? I mean..."
"I know, I'm your sister." she said, grinning now. "But I can't help you unless I really know how you move. So just pretend I'm somebody else for now, all right? Like, just pretend I'm what's her name, Stacy."
I laughed again, still buzzing from nervous energy. I couldn't believe what I was hearing, and didn't know what I would do next. What happened was another in a long string of surprises that evening.
"That'd be pretty hard." I found myself saying. "You're WAY hotter than Stacy."
Nadia bowed her head to hide her sudden smile, and when she looked up again she was blushing fiercely. During that time I noticed her nipples were standing out against her shirt, and for the first time wondered if this wouldn't turn out exactly as I wanted it to.
"Oh, thank you, Jake." She said, then leaned forward again and placed her lips near my ear.
"Then just think about making out with your big sister." She whispered, and I was suddenly as turned on as I've ever been. I moaned softly as she kissed my neck, and then licked my lips briefly before kissing me again.
I didn't know what to think. I really didn't. But I kept kissing her as hard and passionately as I could, and, remembering what she said, started massaging her side and shoulder with my palms.
As I rubbed my hand over her side, I felt her shirt slide up, and a rush of excitement filled me as my hand came in contact with her bare skin. I faltered, but when she didn't stop me I started kneading her soft, supple skin, my cock straining against my jeans as I did it. All I could think of was her big tits pressing against my chest, and how close my hand was to them, and the feel of her tongue dancing with mine. She continued moaning and breathing heavily, as into it as I was. My hand on her shoulder crept around her bra strap and down her arm.
Her own hands, meanwhile, were wrapped around my back, and she was rubbing me much more vigorously than I was her. Already this session was better than all the times I'd felt up protesting girls in the backseat of my car, and we hadn't even taking our clothes off.
I continued rubbing the the same spots on Nadia's body, and finally she broke the kiss with a small giggle. She didn't lean away, however, but stared into my eyes, still breathing heavily.
"First lesson." She whispered. "Rub more than my side. Stroke my back, too, and right beneath my armpits."
I was shocked, having pretty much been given permission to feel up the side of her tits, but I wasn't one to shirk duty. I slid one hand over to her back, stroking along the curve of her spine, while the other hand came down and around. I rubbed against her hips before becoming bold and coming up to the side of her breast.
It was soft and full, with only the think fabric of the blouse and bra to keep me from it, and the effect on Nadia was immediate. She gasped, suddenly, and with no warning, leaned forward and kissed me.
This time I wasn't leading. She made out with my heavily, her hands wandering over my back to my chest. I felt her fingers play along my nipples before coming down to stroke my belly, and for a moment her wrist brushed the tip of my cock, which made me jump as sudden pleasure coursed through me.
Meanwhile, I was rubbing the side of her tit heavily, almost forgetting about my other hand in all my excitement.
Briefly, Nadia broke away again and whispered "Grab my ass. Girls love it when you do."
Not one to disobey orders, I slid my other hand down and cupped her beautiful, tight ass, squeezing the cheek through her tight jeans. Nadia moaned loudly and pressed her tits against my chest, and I responded by sliding my hand across her blouse and running my thumb over her erect, tight nipple.
Things were progressing way too fast, but I was in no shape to care. My cock strained against my jeans every time I rubbed Nadia's luscious ass, and my other hand was busy squeezing her large tits. She was grinding her hips, moving back and forth to the rhythym of our kiss.
"Kiss my neck." She whispered, and I obliged, running my lips down her jawline and along her neck to her shoulder. She arched her back in pleasure.
"Yeah, that feels good." She said, finally breaking off the kiss for good. "Keep kissing me. Oh my God, girls will love that."
I did as she said, all the time running my hand over her beautiful tits. Occassionally she would reach over and press my hand to her breast, but most of the time she continued to rub my belly, brushing up against my cock enough times for me to know it was no accident. Every time her slender fingers came near my manhood, I moaned, and when I did a flash of knowledge came into her eyes. She knew what she was doing to me and, what was more, it was getting her even hotter.
"Keep kissing me, Jake." She said hoarsely. "That feels so good."
Abruptly, she grabbed my hand off her ass and brought it to her stomach, where she slid it under her shirt. I didn't need any more encouragement. I lifted her blouse up over her head, and marvelled at her perfect, large tits.
The bra she picked showed her cleavage off well, letting the sides spill over and pressing them together. Her nipples were clearly visible against the white fabric, sticking out blatantly. For a moment I couldn't do anything, dumbfounded by what I was seeing.
Nadia took the initiative to grab my head and bring it back to her neck. Letting myself go fully, I began kissing her up near her ear, nibbling on the lobe while below my hands ran themselves over her breasts. I would pinch her nipples softly, eliciting a small cry the first time I did it, and then grab them and squeeze. She pressed herself forward, fully enjoying herself.
When she reached back I knew what she was doing, and sure enough, her bra fell away, letting her tits swing free. Not willing to contain myself, I bent forward and popped a nipple into my mouth, sucking on it hard, while my other hand continued it's stroking.
"Yeah, Jake, just like that." She said, biting her lip. "Just like that. Suck on your big sister's titties."
Her words turned me on even more, and I crossed to the other breast, licking the mound before centering in on her erect, sensitive nipples. I flicked my tongue over her aureola, and then nibbled on her nipple.
"God, yeah." Nadia told me. "You're so hot. God, you're doing well."
While she spoke, I handled one tit while my other hand slid down to her jeans. I pressed my palm against her pussy and was rewarded with warmth. She ground her hips against me, sighing.
"Oh, unbutton my jeans." She said. "I need to feel your hand over me."
I snapped the catch and pulled down the zipper, revealing a swath of pink cotton material. Not wanting to waste any time, I slid my hand beneath her panties and reached until I could feel the moistness of her pussy.
"Oh yes!" My sister cried. "Right there. Right on your sister's clit."
I dug my finger in, pressing her clit and then rubbing it. She responded by grinding up against me even harder and more frantically, her ass coming off the bed and she bucked against my hand as it ran over the folds of her pussy. The movement loosened her jeans, and I was able to reach further, finally sliding my finger inside her.
"Ooh, Jake!" She cooed. "Oh my God, right there! Yeah! Right in my pussy!"
I started sliding my finger in and out, while at the same time nibbling on her erect nipples, delighting in the way her tits bounced as she fucked my hand.
"Yeah, Jake, it feels so good!"
Suddenly her hand was over my cock, reaching in to my jeans and grabbing the shaft. It happened so quick that I was stunned.
"You're such a good student, Jake." Nadia purred. "I thought you could use a reward."
And then she was stroking me. My beautiful sister was pulling my cock, wrapping her slender hand over it and jacking me off.
I responded by fingering her more furiously. Nadia ground up against my hand, sliding my finger deeper inside her. She started moaning as the sounds of me finger fucking my wet sister filled the room. I wrapped my arm around her and held her as I sucked her tits, moaning against her nipples as she stroked my cock.