4 comments/ 108977 views/ 4 favorites First Explorations By: MrShyTown The boy was newly 18, and had the run of his father's house for almost a full week. His newly acquired, and for that matter his "girlfriend" Melissa, his first ever, was prone to showing up at his door late at night unannounced, essentially looking to make out. The boy didn't mind this at all, of course, but as the living room was bounded by windowed French doors, she was likely to catch him watching a porn video or pleasuring himself to a Playboy magazine, so he had to be cautious. Their make-out sessions had progressed slowly since the first night in the movie theater parking lot, where she had surprised him by forcing her tongue into his mouth, pressing her warm, 18 year old body against him. The sensation had awakened an extremely quick and thrilling response, as his cock grew quickly against his leg, spreading downward along his thigh. He knew she felt this as well, and while they didn't talk much, the unspoken lust between them had kept them both coming back. On this particular early summer night, the boy was watching a Playboy video at around 11:30pm, stroking his crotch through his jeans as a sultry centerfold stripped out of her lingerie on the screen. He heard a slight tapping at one of the French doors, and turned to see the pale, creamy skin of Melissa's face and her dirty blonde hair peering in the window. He opened the front door and she walked past him into the living room. She was wearing a white, buttoned blouse, brown Khaki shorts and pale white pantyhose leading down her shapely legs to black slip-on shoes. The night was hot and silent, and they exchanged few words before they found themselves on the couch, French kissing feverishly and allowing their hands to roam freely over each other's bodies. Melissa's breasts were small but perky, yet she disliked his hands on them, most likely out of shame at their small size, and would not allow him to caress them for any length of time. He would reach under her blouse, up toward the smooth silk of her bra, intending to slide his hand beneath it to her nipple, but his hand would be brushed away at the last second. This did not overly concern the boy, as he was too much in thrall with the rest of her body, particularly her soft round behind, and his hands constantly slipped up inside her shorts from below, trying to grasp the firm cheeks. Her shorts were too tight, however, for him to move them as far as he wished. On this night, keenly aware that he was alone with a real girl in the house, and they would not be disturbed, he decided to attempt to extend their make-out session to realms heretofore untapped. Somehow he knew that they would not reach intercourse tonight, as he never had, and she claimed to be a virgin as well, but this only enhanced the thrill of seeing just how far she would let him go. With this in mind, he laid her back onto the couch and climbed atop her as she willingly opened her legs enough for him to bring his crotch into direct contact with hers. The soft smoothness of her pantyhose was exhilarating to the touch of his slightly shaking hands, and their private parts strained and rubbed into each other through the fabric of their clothes. Even through the rough denim of his jeans, he thought he could feel the subtle slit in her womanhood as he guided his rigid bulge up and down between her legs. After a few minutes of this, he pulled her up and turned her around until her back was to him, with her elbows resting on the back of the couch. This was what he had been imagining in his dreams. He placed his covered member into the enticing valley between her ass cheeks and began to rub in earnest, his hands on her hips. Melissa was breathing heavily with the shared pleasure of this experience. The boy looked over and realized that the video was still playing, and this excited him even more, for at the same time the centerfolds were baring their bodies to the camera, he had his own real live female to explore. In this way, over the next half-hour, the boy tried every position he had seen in the movies, and Melissa willingly let him, as long as no articles of clothing were taken off. At one point, she was straddling him, grinding her firm pussy lips against his rock hard package. He was fairly sure that she had an orgasm during this, as her breathing quickened, her legs tensed around his, and her grinding slowed. He was thinking that this is almost the same as having actual sex, since he was using his cock to pleasure her pussy, and he felt as intimate with her as he imagined sex partners would feel. At last he found himself on top of her again, their tongues exploring each other's mouths, and slowly he slid off to one side and began to move his hand down her body. He wasn't sure about her willingness to let him do this, but he had to try. Through all of this, neither had placed a hand on the other's nether regions. It seemed a frontier that could not yet be crossed. His hand reached the top button of her shorts, but he decided any attempt to undo it would be thwarted. Instead he moved further, down the front of her shorts to the warm, steaming, and, he thought, almost moist "v" of her crotch. Here he used what little he knew about the female anatomy to begin to rub up and down the length of what he imagined was the slit of her young snatch. Her breathing increased, and she even moaned a few times in what he thought could be either pleasure or pain. More importantly, as he rubbed her pussy he found that his cock was flush up against her leg, and was becoming harder and more urgent in it's motions. He also felt the familiar tingling sensation in his loins that meant the onset of intense pleasure was imminent. After a few more seconds, he buried his head in the shoulder of her blouse, and with his hand still rapidly fondling her now wet crotch, he felt a burst of fluid from his straining cock, flooding the inside of his underwear with sticky cum. He felt almost ashamed that he had come in his own pants, and without acknowledging that this had occurred, he stopped his rubbing and kissed her long and hard. Soon they got up, and he carried her to her car, where he placed her in the driver's seat. As he stood in the open car door talking with her, she reached up and placed her hand on his inner thigh, slowly moving it up until it was touching his cock, which was once again growing rapidly. She gave it a squeeze, and him a look that seemed to portend more exciting adventures to come... First Explorations I was still in college, senior year. I was 5'9" tall, a bit soft from spending six months typing up papers instead of hiking, without a girlfriend for about a year. Now, at that point I had been curious about guys for a while. I had joined a couple of BB systems and chat rooms since I had no clue how else to go about it. Since I ended up chickening out more often than not, the added anonymity helped by giving me the handy "oh, sorry, I lost connection" excuse. Eventually, though, I did end up meeting up with a couple of guys at last. My first time was not quite what I expected: After chatting to this guy for a while, we agreed to meet at his place. It was nearby, in a good neighborhood and seemed safe enough to meet up and see what happened. I drove up in the late afternoon. It was fall- just cool enough for me to be in jeans, T-shirt and a loose sweater. I walked to his front door- it was a modern home, square and white with what looked like a loft and big windows overlooking the beach. It was very nice, and I had a minute to admire the location while I listened to someone coming down the stairs. He opened the door wearing a bathrobe and sandals. He was about my height, with round features and a jovial expression with short cropped brown hair and blue eyes. I believe he was in his mid 30's, about ten or twelve years older than me and single. When I got over the surprise at the robe, we said our hellos and I stepped inside. His house was warm and filled with the scent of plants- it's hard to describe, but distinctive. He had plants filling every corner of the house, it seemed; I was looking around during that first lull in the conversation where you have no idea what to say when he reached over and squeezed my ass. That broke the ice a bit. I laughed nervously and he stepped around to wrap his arms around my waist. Instinctively, I put my arms around him as he leaned in to nuzzle my neck. I was a bit scared but could feel myself getting hard. He must have felt it, too... he stepped back just enough to tug at my sweater. I helped him slip it off, then my t-shirt. He ran his warm, soft hands over my chest as my breathing quickened a bit. Looking into my eyes the whole time, he unfastened my pants, then. As I stood there shivering with adrenaline, he pulled them and my briefs down to my ankles, then held my hand again as I pushed my shoes off and stepped clear of the last of my clothes. With another smile he reached down and wrapped his hand around my cock. I gasped or moaned as he turned and led me up the stairs to the loft, tugging on me gently but insistently. The loft was filled with a tall, king size mattress. There were white sheets and pillows; the setting sun hued everything red. A big screen TV and entertainment center dominated a wall next to the big windows. He lay down and pulled me down next to him. The terrycloth of his robe felt soft against me as he cradled me in one arm. It had opened enough as we lay down for me to know he was wearing nothing underneath- he had very hairy legs and chest, his skin was paler than mine. We had been talking all this while- about how nervous I was, how it was my first time doing anything at all with a guy. When we lay down I shut up without him having to do more than smile. He asked if he should put on a movie to help me get in the mood and I agreed. He switched on the TV to a movie already running. It was gay porn, of course... two lean and muscular guys in some indistinct bedroom. The first thing that struck me was that they were wearing socks; the second was that they had huge tools. He had been stroking my shoulder and I could see his robe stir as he watched the screen. Taking my cue, I gathered up the courage to reach down and untie his robe, then parted it slowly open. He must have been ten inches long and very, very thick. Not quite as thick as a forearm- though it seemed that way to my very inexperienced self- but big enough that his shaft looked like a bat: a good sized head tipping a shaft that expanded and then tapered a bit again where it met his curling blonde-brown pubic hair. He was not fully erect, stirring as he watched me looking at his length where it rested against his stomach and up to his navel. Even with my head on his chest it was impressive. I laid my hand on his shaft and he murmured his approval as he moved under my fingers. It felt smooth, almost slick as he grew harder... hot, velvety and heavy. I just lay there for a while, ignoring the movie and just watching his cock as I stroked him slowly, running my palm over his length and around the head, then trailing my fingertips down to run over his growing balls. They were fair sized, smooth... but looked small next to his thick meat. When I felt his hand on the back of my head, pushing me down toward him, I did not resist. He smelled clean, like soap. My hand stroked and cupped his sack as I opened my mouth to get my first taste. I could hear him encouraging me as I kissed the ridge of his tip. I kissed his entire length, my dry lips slowly moistening as I went down his shaft from tip to root and back. Then I grew a bit bolder, my tongue darting out to taste his skin; he was so hot, jumping a little and growing even larger. I could taste the faintest trace of soap, but mostly tasted him... not quite sweet, not unpleasant. As I licked him with longer strokes of my tongue, bathing him in my saliva, he tasted... muskier, more salty. I lapped and licked him more hungrily, my hand wrapping around the base of his shaft. He was so thick my fingers did not quite meet; I jerked him off slowly as best I could, moving my hand up and down to stroke his wet flesh with the ridges of my fingers as I concentrated on the bright red head. When he shifted his hips a little and guided me with his hand, I opened my mouth and took in his head and as much of the shaft as I could manage... which was not much. He stretched the sides of my mouth painfully, and I knew right off that I would not be able to take more of him in. So I kept stroking him, jacking him off as I sucked lightly on his head, licked and lapped around the ridge and down his shaft to keep him well lubed for my hand. My mouth and hand were full of his meat, I was breathing quick and shallow as I tried to please him. I was hard, pressed against his warm sheets and thrusting my hips in unison to the movement of my mouth, horny and starting to sweat from the effort of making him happy. He stroked the back of my head and arched his hips to meet my mouth, urging me to go faster, to lick him more, and to take more of him in. I licked and sucked him for maybe ten, twenty minutes- I lost track of time. My mouth was beginning to ache and my arm was getting tired when I heard him groan. I pulled him out of my mouth and jacked him off faster, opening my mouth wide and swirling my tongue against the bottom of his shaft just under the head. He pressed down hard on my head and arched up as he moaned and shot his load. A pearly white, thick stream sprayed his stomach and chest; it spattered the sheet and pillow by his head. His cock pulsed and jumped in and against my mouth, bucking wildly in my hand as I kept on pulling and stroking, emptying him out until he moved his hand to rest on mine, signaling me to stop. He was panting as he pulled me back up and into his arm; he was sticky and warm where he was covered in cum. I could smell it on his chest and against my cheek where he held me, strong and almost sweet. When he went to take another shower I got dressed and left, his drying residue warm and slightly tacky on my cheek, chest and arm. The second time was more... rushed, than anything. A few days after that first time, I was back on the boards. I had enjoyed things as far as they'd gone, but I wanted more. My curiosity had been, piqued further. So when I got a private text message from someone saying that they wanted to get together right then and there, I only hesitated briefly. He was nearby, maybe ten minutes away, and was on his way as soon as I responded with my standard disclaimer that warned I was no hunk and made no attempt to hide the fact. He was thirty-something, married and looking mostly for a quick fix before work, so looks did not matter much to him. He was knocking at my apartment door before I had even managed to fully close down the chat program and turn off the computer. My apartment at the time had a half loft, just a low bed and some furniture for whenever someone would want to crash with us for the night. My roommate for the semester was away for the semester, and so I had the place to myself. Up we went. He was taller than me; easily 6'2" or so, and with that long and lean runners build. Graying hair... and he did not smile much. He was there for one thing and we both knew it, so we did not pretend otherwise. Once we got upstairs he sat on the bed. Reclined back, leaning on his elbows and thrusting his hips up as he opened his legs slightly- clearly showing the bulge in his pants. As I stood in front of him hesitating a moment, he said "get undressed. I want you naked when you go down on me." I could feel myself hardening a bit at that. I kicked off my shoes, pulled my shirt over my head. He watched me as I unbuttoned my jeans and pulled them out, leaving me in a pair of dark briefs... he grunted or said something unintelligible, and I hooked my thumbs on the waistband and pulled them down. It almost hurt as the elastic slipped past my hard cock. I straightened again- pale skinned, not much hair except for the thick dark nest at the base of my shaft. I was hard already, my blood-dark 7" angling up and slightly to the left. He did not stir except to thrust his hips up at me... it took me a moment before I stepped forward and knelt between his legs. I had been curious, and I had my chance... my hands trembled a little as I unbuttoned his 501s and pulled them open. I could clearly see his erection through the straining, tented white briefs he had on. He arched his back and lifted his hips off the bed for me to pull his pants down over his legs. My mouth felt dry as I folded his pants and laid them to the side before running my hand up his hairy thighs. I heard him hiss as I ran my palm over the bulge of his cock, felt him grow a little harder. I pulled down the briefs, my eyes not straying from him as he sprang free- literally, his hard shaft jumping to stand almost straight up before me. Moderately thick and veined, he was circumcised and must have been around 7" long, cradled in a mat of black and gray hair. I could smell him, too: sweat and a musky aroma that I've come to associate with sex. His legs were warm from the jeans and the California sun, but his groin felt much warmer: I could feel the waves of warmth against my cheeks as I rested my arms on his thighs and looked at his cock for what seemed like minutes... but must have been seconds, just long enough for him to get impatient. I felt his hand on the side of my head, then, slipping into my hair and behind my head to pull me down and closer. The smell got stronger that much closer. I felt the warm, soft tip of his cock touch my lips and I instinctively tried to pull back a bit- but he would not let me, his hand firm as he muttered some protest I could not make out. I parted my lips and slowly enveloped the head. He groaned and shifted. My fingers were curling and straightening against his thighs as I took more of him into my mouth... I could taste his sweat and his flesh, slightly bitter and hard to describe. I took as much of him as I could into my mouth, maybe half his length- then pulled back again, keeping just the head of his shaft inside before sliding forward again. I licked the underside- felt the ridges and felt him shiver a bit at the sensation, so I kept my tongue moving from side to side as best I could as I tried to swallow him. I had to stop when he hit the back of my throat and I felt the gag reflex threaten; I pulled back again, and I took as much of him as I could yet again. His fingers were wrapped in my hair and I was breathing heavily through my nose, each hurried breath full of the strong musk and taste of him in my mouth. He was growing stiffer, harder: I could feel the hard center of his cock through the silken, pliable layer of damp, skin. I settled into a steady rhythm, engulfing as much of him as I could take and then pulling back until only his head rested in my mouth. I'd swirl my tongue around, suck a little... and slide my head forward again, cheeks puffing as I took a little bit more of him into my mouth until I could take no more; he was bumping the back of my throat at the end of each stroke, I had more than half of his length inside my mouth. I cupped his balls, fingertips caressing and gently kneading them as my other hand kept stroking his leg. He started rocking on the bed, pushing his ass against the mattress and then rising to thrust into my mouth. I was moaning around him as he filled my mouth, sending vibrations along his nerves that made him shiver and moan. I had pushed closer as I started sucking on him, my own hard cock rubbing against the mattress as I rocked on my heels, between his knees. I quickened my pace a bit, panting around his shaft and sucking harder at the end of each movement of my head as I squeezed his balls a bit tighter. I could hear him groaning and taking labored breaths... and I tasted his pre-cum, saltier and slightly bitterer than his sweat and flesh as he started leaking into my mouth. I was so engrossed in the new taste that I did not feel him shift and move until he was literally pushing me off him. Surprised and confused I looked up at him as he stood up- rumpled polo shirt, pants and briefs around his ankles. He was breathing heavily and looked as flushed as I was. His dripping, red cock brushed against me as he pulled at me to get up. As soon as I did so, he turned me around and pushed me down and against the half wall that separated the half loft from the living room below. It was only then that I figured out what he wanted. I moaned as he put one hand on the center of my back to keep me down while he guided his shaft with the other. He pressed me down harder, the hard edge of the railing pressing against my hips as he pushed his tip between my cheeks and along my crack. I felt him slide against me, slick with my spit as he finally found my virgin, puckered entrance. As soon as he did so he grunted and pushed, hard. I hissed and gasped, tensing and arching as he pressed on, pushing me against the railing until I had to hold on with both hands. He shifted his grip to my shoulder to give himself some leverage, rocking and grunting hard as he tried to push harder against my tense, resisting muscles. I was breathing raggedly in pain, now, whimpering a bit as he thrust again and again... finally managing to barely push the tip of his cock in me. Another thrust and he got the head almost inside before pulling out- leaving me feeling battered, my ass burning from the rough attempt and him frustrated and still hard. I pushed from the railing and went down to my knees before him, knowing I had to finish him... he grabbed my head with both hands, pushing his cock- sharp with the smell of pre-cum, sweat and my own bitter scent- toward my face. I half closed my eyes and opened my mouth, and he thrust in hard and fast. He fucked my mouth, roughly, grunting as he hit the back of my throat. I licked and sucked at him, swirled my tongue around his head and shaft. I placed my hands on his hips to keep him from trying to push all the way down my throat and let him take me... thrust after thrust, he pulled and pushed my head around as he took his pleasure. Until at last I felt him tense and jump in my mouth as he hissed and pulled out to finish: one hand held onto my head as he jacked himself off with the other, flesh glistening brightly with saliva and the sound of his pants mixing with the slap of his hand as he stroked his length... and shot his load on my face. I closed my eyes and mouth as he came, feeling the hot, viscous fluid hit my eye and lips and run down my cheek in thick drops. He released my head and pulled up his pants without a word, his breathing still rapid and deep while I wiped at my face with the back of one hand. He was gone a minute later, as I picked up my scattered clothing, limping slightly from the pain in my abused, still mostly virgin, ass.