Introduction: Banging the older woman next door is every teenage boy's fantasy, but actually doing the did turned out to be better than I ever dreamed.
My name is Nicholas, but everyone calls me Nick, or Nicky. My parents were barely teenagers when I was born, so most of my parents’ friends are still pretty young. In fact, my parents’ best friends are barely in their thirties. My dad’s best friend, Steven, had known my dad since before I was born. Steven married his wife, Megan, when I was still in diapers. Needless to say, I grew up around them, thinking of their two kids as my own sisters.
As I hit puberty, I began to take notice of the female species. I had girlfriends; I even lost my virginity at the age of thirteen with my girlfriend at the time. It wasn’t that I didn’t enjoy sex, it was just that the girls my age were so “proper’ about the whole thing. In fact, most of them did it just to say that they had, not taking any real pleasure in the act. It was always the same with each of the three girls I had slept with: missionary position, no oral sex, condom on, hurry up. Not that at sixteen I lasted longer than a few minutes, it was the principle of the whole thing.
About the time I hit fifteen I started hanging out with this guy who had a brother about ten years older than us. This brother loved dating older woman, and often shared his little sexual adventures with us. He would always say, “Sure, the young ones are hot on the outside, but if you want one who knows what the hell she’s doing, go for the older models!’ I began looking at my friends’ sisters and even their moms, but the sisters were all too snotty to be bothered with the likes of me and their moms…well, their moms were much too old to catch my attention.
It was the beginning of the summer right before my sixteenth birthday that I developed my first real crush on an older woman. Best of all, it was someone that I saw on a regular basis. And it just so happened to be the wife of my dad’s best friend, Megan. Megan was my mom’s age, but she didn’t look it. One of my friend’s even mistook her for a senior in high school.
One weekend last summer all of us went to the beach, and it was seeing Megan in her bikini that really woke me up. Megan has long brown hair, pretty blue eyes, and tanned skin. She was much shorter than me, barely five feet tall. She had full round hips and perk little 34C tits that still held up despite the two kids she had already given birth to. She had been around my whole life, but it wasn’t until I saw her splashing around in the surf with her youngest girl that I realized just how hot she really was. And unlike my own parents, she would openly flirt with her husband, rubbing her cute ass against his crotch when she thought no one was looking, or giving his crotch a quick grab from time to time. None of my girlfriends had even touched my cock, and seeing her little hand grab hold and release his with that wicked little smile on her face gave me an instant boner.
I spent the better part of a year masturbating to the memory of her wiggling ass and roaming hands, pretending that it was my cock that she was groping and fondling. As the months wore on, I began to daydream about what it would be like to sink my dick into her pussy, to see that sweet mouth of hers suck me until I came. Oh yeah, I wanted to pound her pussy alright, but I also wondered just how much she could teach me about sex. I knew I had had more sexual partners than her or even my mom, but I just bet Megan could teach me a whole world of perversion that no one my own age could even dream of.
So my days went, walking around school with a semi-hard on, and my nights spent jacking off to countless fantasies. I was so obsessed that I didn’t even bother my girlfriend for sex, and she damn sure didn’t bring the subject up.
Towards the end of that next summer, my parents planned one of their frequent bar-b-ques. I knew that Megan would be there, but when my friend Jeff asked if I wanted to stay at his house, I decided to not torture myself by being around a woman I could not have, and relented. Megan and her husband never stayed at the parties for more than a few hours. Their kids were still young, the oldest not even out of elementary school and the youngest not out of diapers. So they often disappeared around eight or so. I decided to go to Jeff’s house before they even got there. I knew if I saw her in a tank top and shorts then I wouldn’t be able to bring myself to leave the house, and would no doubt spend the evening trying to cover up a raging hard-on.
I arrived at Jeff’s house about four that evening, but after spending the entire night watching his sister and her boyfriend make out, I decided that I was better off at my own home where I could at least jack off in privacy. With that, I told Jeff I was going home and walked the mile and a half back to my own house. It was nearing midnight and I figured the party might still be going. When I got home, I immediately went around to the back yard, seeing a variety of my parents’ friends sitting around the fire chatting and drinking. Megan’s husband was there, sitting propped up on a lounge chair and apparently mostly passed out. I figured Megan had taken the kids home, so I headed to my room without even letting my parents know I had come home.
I share a bedroom with my fourteen year old brother, Eddie, but he had also spent the night at a friend’s house, so I had the whole room to myself, which was good because at this point I was so damn horny from seeing Jeff’s sister sucking on her boyfriend’s tongue that I was about ready to explode. I stopped in the kitchen and grabbed one of the many beers that were stashed in the fridge, knowing that my mom nor dad would notice one missing with so many people going in and out of the house. I popped the top as I let myself into my room, locking the door behind me so that I wouldn’t be disturbed. I sucked half the beer down and set it to the side as I stripped off my jeans and t-shirt. Sighing a bit, I plopped down on the bottom bunk of the bunk beds that Eddie and I shared. I yanked my briefs off and swung my legs into bed.
Something beside me moved, scaring the shit out of me. I jumped up out of the bed, reaching to turn on the little desk lamp sitting beside the bed. As my eyes adjusted to the dim light, my heart nearly leaped out of my chest as my eyes fell upon the beautiful face of Megan, her brown hair fanned out across my pillow and her lovely face looking even younger in the pale light.
I stood there with my dick sticking out and my mouth gaping open as Megan murmured in her sleep, kicking the covers off her body. My eyes raked up and down her body, taking in the tiny little boy short panties that she wore and the tank top that had ridden up to reveal the lower half of her tits.
“What the hell?” My mind fumbled around for a reason on why Megan would be in my bed before I realized that she, like her husband and half the guests at the party, was passed out. I figured my mom had told her she could crash in my bed since me and Eddie were suppose to be out of the house until the next day.
I quickly pondered my situation. Her husband was passed out outside in the yard, my mom and dad were passed out in their own beds, so there was practically zero chance that anyone would be checking in on her until the morning. My mind reeled with the possibilities, and my dick grew hard as steel as I thought about what I could do to her in this state. I was counting that if she did wake up, she would be so embarrassed that she would just turn me down flat and wouldn’t utter a word to anyone. On the other hand…..well, I wasn’t gonna think about that just yet.
I walked over to the bed and slid in beside her, pushing her top up and staring down at her perk little boobs. I leaned down to lick each nipple in turn, loving the fact that they grew hard under my touch. In true teenage fashion, I wrapped each one of my hands around a boob, squeezing and massaging them. Not satisfied with just this bit of groping, I decided I might better take full advantage of this situation. I slid further down in the bed, carefully removing her panties. She showed no hints of waking up, so I spread her legs and helped myself to her cunt. I lowered myself between her legs, breathing deeply the faint scent of her pussy. My hands shaking, I used two fingers to gently open her cunnie lips, taking in every fold and curve with my eyes as I had not ever been this close to any of my girlfriends’ pussies. Sure, I had fucked them, but none of them would let me see them or touch them for that matter. Other than magazines, I really didn’t know what one looked like, which is weird considering I had fucked a few in my life.
I ran my middle finger up and down her slit, amazed at how wet she was. None of my girlfriend’s had ever been wet. If it hadn’t been for the lubed condom then I might never have been able to get my dick in them. But not Megan. Even the insides of her thighs were moist, and I eagerly lowered my face to lap up all the juice that I could find. She tasted heavenly, just as I knew she would.
At that moment Megan moaned, shifting her weight slightly. I held my breath, watching her with fear in my eyes and silently praying that she wouldn’t wake up. Thankfully she settled back down, and I returned to licking her slit. I flicked my tongue across her clit, taking it into my mouth and sucking on it gently as I inserted two of my fingers into her dripping pussy. To my amazement, she was surprisingly tight despite having had two kids. I began to finger fuck her slowly as I continued to suck on her clit, feeling the tiny bud grow larger under my administrations. I had dreamed of doing this for so long, I could hardly believe my fingers were knuckle deep inside her warm cunt.
“Nicholas,” her voice whispered my name softly, and I froze in place. I had been so engrossed in what I was doing that I had noticed Megan’s breathing becoming heavier and heavier. With dread I lifted my face slowly to look at hers, and was shocked to see her face full of rare lust, her eyes almost glazed over with passion. “Come here,” she whispered to me, taking my free hand and pulling me towards her. I just knew she was about to tell me to get dressed and leave the room. Instead, she wrapped her arms around my neck, one hand tangled in the back of my hair as she pulled my head to hers, her warm lips pressing against mine in a delicate kiss. For a moment I kept still, my brain still shocked that she had caught me between her legs eating out her pussy. But it only took a split second of her lips being on mine before my brain checked out and my dick took over.
I kissed her back, my tongue parting her lips to delve into the depths of her mouth. She groaned, pressing her naked skin against mine. I lost it then, pulling her legs up around my hips as I ground my loins into hers. My dick felt like it would blow up at any given moment, so turned on was I. Megan broke the kiss, scooting herself up a little as she managed to switch our positions on the bed. “Not so fast, sweetie,” she whispered as she slid down my body, dragging her tongue along my flat stomach. “I want to take full advantage of this situation.”
I watched in lust filled anticipation as she wrapped her hands around my dick, starring at it for a moment before slowly lowering her head. Her tongue flicked out and caressed the tip teasingly before her hot mouth engulfed the entire head. I moaned, thinking I had no doubt just died and gone to heaven. My eyes fluttered shut as her head began bobbing up and down in earnest on my dick. I was surprised that she managed to get all eight and half inches down without gagging, but then again, I should have known she could since she had had years of practice at it.
Soon I was thrusting my hips up to meet her, effectively face fucking her as she continued to devour my dick every time she went down. I knew I wasn’t going to last very long, and I guessed she sensed it to since she slowed her pace and then removed her mouth completely. I did not even have time to miss her wet lips before they were licking and sucking at my balls. I thought for sure I was gonna blow my load right then, but somehow I managed to hold back as she slid up my body, pulling her tank top off as she went. Within moments she had lowered her hips until just the head of my dick was at the entrance to her pussy. I held my breath as she moved further and further down, the head slipping into her. Without any warning she thrust herself down, impaling herself on my dick. She moaned loudly, her head thrown back as she began to ride my cock with complete abandon. Not satisfied to let her have all the fun, I flipped her off of me after a few minutes, turning her around until she was on all fours.
“I’ve been dreaming about fucking you like a dog for the last year,” I whispered in her ear as I rammed all eight inches of my cock into her pussy, marveling at how tight and wet she was. She buried her head in my pillow to stifle the steady moans that were coming from her mouth as she thrust herself back, meeting each thrust of my hips with an equally powerful thrust of her own. I had never been able to let loose with any other girl and really fuck them like I wanted to, but Megan obviously liked it rough as she tried to cram more of me into her dripping cunt. I felt her tighten around my dick suddenly, and I slowed down, thinking something was wrong.
“Harder,” she hissed at me, thrusting backwards with such force that I thought for sure she would rip herself in two. Loving the sensation of her pussy gripping my dick, I fucked her for all I was worth, pounding her with more and more force. Suddenly her body tightened and began to jerk, and I could feel the muscles of her cunt pulsing around my cock. I groaned and buried myself balls deep in her, feeling my balls tense up and then explode inside of her as her pussy milked every drop of cum from my body.
We both collapsed on the bed, our breathing slowly returning to normal. “Jeeze, Nicky, you fuck like an animal,” she said between breaths. I wasn’t sure if that was a compliment or not until she turned and kissed me deeply. Despite feeling like I had just squirted a gallon of cum into her pussy, my dick jerked of its own accord, the semi-hard organ springing back to life. She moaned softly into my mouth as her hand began to slide up and down my shaft, the juices from both our bodies making it slick.
Megan pulled back, giving me a wicked little look that I had caught a few times in the past before, but never directed at me. She slid back down my body to capture my dick in her mouth, her tongue and lips licking every bit of our combined cum from my body. “Nicholas,” she whispered, giving me that devilishly naughty look again, “have you ever fucked someone in the ass?”
Her question caught me completely off guard. Slowly I shook my head, the thought of ramming my cock into her little ass making me pulse with need all over again. She moved to the side, laying on her back and pulling her knees to her chest, her ass up off the bed as she spread her cheeks to show her little button of an ass hole to me. “Fuck my ass, Nicky.”
I needed no further invitation as I hopped right on top of her, positioning my ram rod hard prick at her ass and guiding the tip of it the tiny opening. Her pussy was dripping with her juices and my cum, effectively lubing her little asshole as I popped the head of my dick into her ass. She moaned, whispering, “Don’t hold back, Nicky, fuck me hard.” I did as she commanded, shoving my entire length into her ass in one swift movement. We both groaned as my balls hit her ass cheeks, the skin barely touching before I had pulled out and shoved myself in again, over and over, as hard and as fast as my seventeen year old body could. I lasted longer this time, fucking her ass like a jackhammer. She jerked and spasmed around my dick nearly continuously, one hand shoved in her mouth to muffle the sound and the other one working furiously at her little clit. “Oh, Nicky, fill my ass with your cum!” Her words coupled with the constant grip and release of her ass pushed me over the edge. I shoved into her hard, feeling that tightening in my balls as I began to shoot rope after rope of cum into her ass for what seemed like an entire minute before the stream finally subsided. I fell on top of her, not bothering to remove my dick but letting it slowly deflat on its own. We lay that way for several minutes before I finally rolled off the bed, grabbing up a towel from my hamper and wiping off the leftover cum from my dick, offering her a second towel so that she could clean up as well.
“Um, I guess I might better sneak back out of the house and back to Jeff’s,” I said sheepishly, giving her a smile. She returned the smile as she wiggled into her panties and tank top again.
I moved to open the door when her voice came softly to me, “If you or your friends need a tutor, Nicky, you know I’m always available.”
I smiled and nodded, slipping out the door and out of the house. I replayed every single minute of our interlude during the mile and half walk back to Jeff’s house. Yes, I could think of a few friends who might need a few good lessons, and my dick twitched at the thought of using her over and over again, my cock crammed in her dripping pussy as she sucked off another one of my seventeen year old friends.
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