0 comments/ 160187 views/ 1 favorites Your First By: Riven___Caulfield The following story is true. It contains nothing unusual. Nothing that hasn't happened a million times to a million people. This story's not really mine, and I will give credit where credit is due. It's the story of a teenager jerkin' off. That's about it. My family moved around a lot. Now once upon a time, we lived in Saskatoon, Saskatchewan. Despite popular myth, Saskatoon's not a bad town. Though, not a great town for a teenage kid with nothing but Home Schooling and a mountain bike. Yes, fine, I was home-schooled. And I do regret it's rendered me socially maladjusted, but that comes with a satisfaction that only the socially maladjusted can know. Now, this story begins with my older brother. Upon cleaning his room one day, my mother discovered his stash of porno magazines. She demanded he throw them out, but throw them out he did not. Oh, he threw out ten or so, just so as not to raise suspicion. The rest he tucked neatly under the front steps – a huge hollow box-like stair of concrete. I learned none of this, until I noticed a shiny cover jutting from under the porch one day. I got down on my hands and knees and dug away at the gravel until I could pull it out. Gallery magazine. My gut tightened – I felt sick with nerves. I tucked it under my pants and pulled my shirt over top, and dashed through the front door and up into… Hey, we all know where this story goes. The bathroom had a lock. Now I must admit, I was quite enchanted with the sight of a woman's full-fledged features for the first time. I recall my favorite spread; a redhead who I swear was natural. Looked like a girl-next-door, posing against one of those ancient Chevy trucks. Her pale skin glowing before the chrome and candy-apple shine. Wet marks on the leather seats. But this story's not about her, either. This story is about the first sex story I ever read. I can't take credit for it. It's not even a story – supposedly, it's true. It's one of those letters people send in to stroke mags. I can't remember any names. Or the title. But phrases. Images, are burned in my memory. I'll try to recreate it here for you now, as best I can. The letter was first-person, but I'll give you third; Jimmy. Jimmy's a young lad of eighteen years, living in a small town in the American Midwest in the late fifties. He wears wool pants and swell checkered shirts. He's had a girlfriend or two, but never gotten further than first base. Now that's not to say Jimmy's some loser. He's any guy just like you or me or your brother or your dad. He just hasn't been laid. He's on the football team – though he's just the guy who kicks the ball. And it's such a small town, no one really gives a shit about the sports anyway. So back to Jimmy. Now Jimmy was hoping to cruise off with his friends for the summer between his graduation from high school and induction into college. But Jimmy's mother wasn't havin' it. Before he even got to throw his grad cap, she'd arranged a nice little job with the lady down the street – we'll call her Mrs. Robinson. He'd be mowing her lawn, doing odd jobs for her for the rest of the summer. (cough cough) So off Jimmy goes to Mrs. Robinson's. Here's to you, Mrs. Robinson. Jesus loves you more than you will know / whoah whoah whoah / whoah whoah whoah. When he arrives, she meets him at the door in a t-shirt and sweat pants. He swears that even through that baggy shirt, he can see her nipples. Her breasts are so full, her hips so curvy, he starts a sweat just following her through the house as she pointed to this and that, explaining his duties. Soon he was indeed working his ass off, but staring at her the entire time. He'd be vacuuming, making sure she didn't see the way his less-than-docile hardon was nearly succeeding in busting its way through his jeans. It became apparent that she had no interest in him, and he contents himself with jerking off at night to the etched-and-burned glances of her in her swimsuit, sunbathing. Her in her robe. Her smiling at him, while his dick screamed at him. Throbbing so hard it hurt. One day, Mrs. Robinson is sunbathing in the backyard. As he gathers some tools for the garden in the garage, he suddenly finds that in this dark and secluded place that he has the ideal location to 'peep' on her, as he called it, without her knowledge through a small window. He goes on to explain in great detail that she wasn't what you'd call beautiful, but she was very, very sexy. Her body, apparently, was the sort that Marilyn Monroe might have wished to possess. And as she laid back in that bikini, her breasts overflowing the flimsy top, he shoved his cutoffs down and started stroking his cock. Spitting on the head, he rubbed and stroked and stared at her body. She wasn't what you'd call beautiful, but she had become his version of perfect. Trying to make it last as long as possible, he takes twenty minutes or so. He goes fast sometimes, so his hand becomes a blur. Sometimes he just strokes the shaft with two fingers. He has eight different techniques or so, but he never moves his eyes from her. From her hips. Curvy legs. Thick, dark hair. Full lips. And he wants her so goddamn bad. He's aching for it. Stroking, stroking. Teasing himself. But he takes twenty minutes or so, and before he squirts she leaves the backyard and goes into the house. He waits, patiently. Sweating in the dark, his cutoffs and tightie whities at his ankles, he nervously strokes his cock and waits for her to come back. He won't take any more chances, he decides. When he comes back he'll just get off and be done with it. Click – the garage lights turn on and he spins in time to see her in a terrycloth robe. And he spins fast enough to trip on his cutoffs and tightie whities, and fall flat on his rock-hard cock. "Just what are you doing?" she demands as he manages to get to his feet. He reaches for his cutoffs, but "Never mind those," she tells him. "On second thought, it's obvious that you were peeking at me and playing with yourself, is that right?" "Y-yes'm," is all he can say. He looks at him strangely. "Don't you have a girlfriend to do it to?" she asks. He shakes his head. "You mean you've never had that thing in a girl at all?" He shakes his head. "Oh," she says. "Your prick looks so nice and hard, and it is a little bigger than my husband's. I'd love to let you stick it in me, but I'm married." She lets the robe fall open a bit. Enough to see she's not wearing anything underneath. "Alright," she says. "Touch it." And now, propping herself up on the dryer, she says; "Go ahead – fuck your fist while you look at me." And what can Jimmy do, but keep on jerking his dick in front of curvy Mrs. Robinson? Soon, she's spread her legs, and he can see the pearls of moisture under the thick curls of dark hair. She asks him how she compares to girls his age. He says he hasn't seen many of them naked, but she's the most beautiful woman he's ever seen. She tells him to come closer, and spreads her legs. Gripping his cock, she strokes it. This guy's in Heaven. And now she works it through her pussy hair, making it slick with her juices. And this guy's bouncing between cloud Nine and Thirteen. "Oh," she's mewing. She pushes it against the flat of her pelvic bone. Her skin is so hot. "Oh," she says, rubbing it against her belly. "Look how far in me it would go!" His head is spinning. He barely knows what the fuck is going on, but when she tells him to take his cock and stroke her pussy with it, he does. And soon she's moaning, and squirming against him. "Oh Jimmy," she says, "Your prick feels so good rubbing my pussy, but let me show you where it ought to be." And then she grabs him with her ankles and pulls him in. She's so hot and wet that he begins to come practically on contact, and she's not helping; "Fuck me, Jimmy! Fuck my pussy! Your prick's so hard! Fuck me!" And so within three thrusts or so he's yelling and coming and squirting all over the place. But Mrs. Robinson's not done – she keeps on humping him until she lets out a shriek, and falls back limp. Then she tells him to get dressed and return to his work, and threatens him storely to never tell on her. He promised not to, and swears he never did until he wrote the letter. I didn't write that story, and looking back now it is pretty cliché. But I guess you never forget your first stroke story. Just thought I'd share mine. Your First Flight I've always enjoyed stories in which you get to choose the main character, as I've done here (it's set in 1st person perspective but also in 2nd person perspective). I've purposefully made it vague so you can fill in the details to your own liking. Also, I should have mentioned this before but if anyone wants to offer ideas to stories and wants me to write them, please do. I'll see what I can do with your ideas, just a reminder though, I will not do cross-dressing or transvestite, strictly transsexual (I think this goes without saying but no gay stories either). This is a t-girl top story, but like I said, you can choose who you are. Enjoy! Your First Flight Here we are, you sitting next to me, our hands together over the arm rest. We feel the plane lift off the ground and the sensation of being in the air fills our bodies. I feel you clutch my hand in fear as this is your first flight ever. I reassure you by placing my hand over yours and smile to you, "it's normal, don't worry," I say. You just smile meekly; the rose color in your cheeks brightens slightly. I let go as the plane settles and the turbulence of the climbing ceases. I feel you relax in your seat and pat your hand again to reassure you once more. The ascent takes a little while, I can't keep my eyes off you as you stare out the window watching as the land below drifts further and further away. As we pass through the clouds you turn away from the window and gently rest your head on my shoulder. I sense you close your eyes and let the plane take us away on our first vacation together. I take the time now to read a book as you quietly rest. -------------------------------- A slight bump in the flight causes you to wake. You look around as if you have no idea where you are. You soon realize where you are and blush as the embarrassment settles in. I smile knowing you're struggling to adjust to flying. I check my watch and guess we've been flying for just over half an hour. The stewards haven't come by yet, but that's okay. I hear you rustling in your seat, trying to get comfortable in the cramped space. I stretch my legs under the seat cubby in front of me, which does little to alleviate the slight discomfort. You look to me and me to you. I stare into your green eyes and our lips embrace. Closing my eyes, I feel you want to enter me and I part my lips as our tongues find each others'. Your warm, soft tongue enticingly plays with my own. I hear you moan through our kiss and put my hand on your nearby thigh. Your smooth, bare leg feels warm to my touch as I gently rub it. Spending a heavenly minute in each others' mouths you gently push me away and smile. I smile back and your smile changes to a smirk. You take your hand that's resting on your leg and guide my hand up. I feel your soft smooth skin until I reach the hem of your skirt. You keep guiding my hand up and under your skirt. My heart begins to race as I near your special place but you stop just short. You quietly giggle as my face shows disappointment. I smile back knowing you're just a tease. I feel your hand guiding mine back down your thigh before lifting off and setting it on the arm rest. You lean in again for a kiss and I don't hesitate as our lips embrace once again. I'm surprised by the short length of it as you push me playfully away again. "Meet me in the bathroom," you say with a smile. You nudge me to get up and I do so. Unbuckling my 'complex' seatbelt, the one in which you apparently need a stewardess to explain its contraption... I get up and head down the aisle. As I pass by all the seats I notice most people are asleep or watching a movie on their screens, paying absolutely no attention to me. There isn't a line at the restrooms and I see that neither of them are occupied on either side of the aisle. I look back to see you watching me and I enter the one on the left. I leave it unlocked, having a faint idea as to why I'm here. The area is small and I look around. I feel the urge to pee and decide to do the deed. While doing my business I hear the door being opened and look to see you. You're smiling and quickly get inside with me. I finish up and wash my hands, feeling your body pressed up to mine in the cramped space. Your perfect breasts squish into my back as I dry my hands. I feel you wrap your arms around my waist and I turn my head to you. In your heels you're almost my height, we try to kiss but can't. We both giggle at our predicament but that soon changes as I feel your hands wander down my waist to my butt. Your soft hands glide over my jean covered butt and I feel you slap one cheek as you finish your ministrations. I hear you moan into my ear as I see you in the mirror, your pouty lips deliciously enticing. Your hands soon wander back up my butt and around my torso. They rest at my abs and I feel you caress me there, moaning again into my ear, "I need you!" I smile into the mirror and you just catch it out of the corner of your eye and smile back. Again I feel your hands drift around my torso. I know where they're headed and wait for their arrival as I place my hands on the sink counter just in front of me. "Mmmmm, that's my boy!" you whisper as you watch my actions. I wait patiently and feel your graceful hands unshackle my belt buckle and move to my zipper. I watch as two fingers pull on the zipper releasing me from my trousers. Your body to my back is the only thing holding up my pants now and you pull away slightly to let them fall. I feel the soft fabric of your skirt on my boxer shorts as you press up against me again. Your hands fall back to my butt again and I feel your slender fingers glide over my shorts. Your nails tickle my butt as you gently rake them across the thin material of my underwear. Your fingers swirl over my ass and your touch is slowly getting me aroused. I hear you quietly giggle as a large bulge appears inside my shorts. The damp paint of your lip gloss causes me to shiver when you plant a soft kiss on the nape of my neck. Your pouty lips gently skip on my neck as your hands slide up to the waistband of my shorts. The softness of your fingers sends another shudder down my spine as I feel you curl your fingers around my shorts and slowly pull them down my legs. You follow my shorts all the way down to my ankles and stand back up to see my erection pointing towards the mirror. "There's my big boy!" you whisper with a smile. Your hand glides over my skin, never leaving my body, as it makes its way to my throbbing cock. My impressive member pulses in your enclosed fist and you moan again. "I need you," you trail off. "I know," I say. You slowly start pumping your fist over my member and I close my eyes as your soft touch seduces me. I hear you rustling behind me and know you're preparing yourself. I open my eyes and just barely see in the mirror you pull your skirt up and bunch it up around your waist. I can't see your panties from the mirror but am still aroused just by the feel of your panties on my naked butt. You slowly gyrate your hips in a circular motion, brushing your panties along my butt. The feel of the soft fabric is really nice and you know I like it. "Ready sweetie?" you ask. "Of course my love," I whisper back. You release your pumping fist from my cock and move it back to your panties. I watch your hands maneuver behind me getting yourself ready. "Mmmm, there we go," you whisper. I feel your excitement on my butt, its warm throbbing firmness ready for some attention. What little room we have in the bathroom, I press my hips forward to give you more room. My cock rests just above the cold counter top, pulsing along with my heartbeat. I hear your heels clicking on the hard floor as you rearrange yourself. Your hands grab onto my hips and usher me towards you. I close my eyes, wanting to only feel now. You hug me to your body and the warmth of your body is nice to mine. Your heartbeat increase in tempo as your special gift rests betweens my cheeks. I moan as your warmth spreads my cheeks and hungrily waits at my entrance. I can barely hold myself from grabbing myself as I wait for you. The wait isn't long though and I feel you press into me. We've done this countless times, but I naturally resist your efforts. "Come on baby," I hear you whisper. I relax and finally feel you dive into me. My welcoming hole engulfs your warmth and I moan as I feel you enter my most private place. "Mmmmmm, oh that's it, that's my good boy," you coo. I moan back in response as I feel your hips gently rest against my butt. "I love you baby," I say. "I love you too babe," you kiss the back of my neck again and I feel you pull away. I clench my butt as you leave me and I hear you moan behind me, "god I love it when you do that..." I smile to myself and relax as I feel you push back in. We time our movements together in perfect harmony as you pick up the pace. My cock bobs up and down as you put more power behind your thrusts. I groan as you speed up more and grab hold of my cock. I gently glide my fist over myself as you quicken. "Uuuuhhhh, uuuhhhh, uuuhhhh...." You moan. I know you're getting closer and I pump myself quicker. "Oh shit babe," you groan. I moan as you now slam your hips into me. The sound of flesh slapping flesh fills the tiny compartment as your thrusts become piston-like. I pump my own fist faster now as I get closer. "Oh shit babe, I can't hold out much longer..." you moan. I feel you press your entire body against my back, your breasts smashing into me, as you only use your hips to fling yourself into my hungry hole. You wrap your arms around my waist as you slam and pound into me relentlessly. "Fuck!" you almost scream but you bite into my shoulder to stifle anything else. I know now it's only a matter of seconds before you're about to pop. I hear you groan and moan into my shoulder and then feel you drive as deep into me as you possibly can before I feel your womanhood harden and then release your love inside me. You rest as close to me as your body shudders through your powerful climax. The warmth filling my bowels is too much for me and I barely contain my own voice as my own cock erupts all over the counter top. I gasp as I jerk myself off before feeling spent. My cock slowly deflates and I feel you just finishing your own orgasm. You embrace me again and pull out, I feel empty as you leave my body. The warm goo seeps out of my abused hole as you bend over to put my shorts and pants back on. The cooling juices stick to my boxer shorts as you pull them up with your delicate hands. Just as I pull my zipper up and buckle my belt you give my rear end another swat before saying, "That was great honey! Love you!" "Love you too my dear," I say. I smile to you and wink as you leave the restroom adjusting yourself. You smile back to me knowing I'll get you next time...