Student Jess accidentally loses virginity to insomniac friend.
Hey, this is a story from my college days about my old friend James, hope you enjoy. Any feedback in comments appreciated. X
He had insomnia. That meant we spent a lot of time together because I'm a night owl. During the first few weeks of college it seemed like it was getting worse, he was normally so sweet and kind but he had gotten erratic and snappy. So they upped his medication, and it worked! He returned to his old self, but I'd lost a friend to hang with during the nights.
He lived just down the hall from me in our college accommodation so one night when I was bored I went down to his door, knocked and creeped in, like I'd been doing for weeks. His dim lamp in the corner was on but he was fast asleep, his sleeping medication next to him on his bed side table. Fuck!
I sat down in my usual chair and faked a conversation between us but he didn't stir, he was out cold. And then I spied under the single sheet he had half draped over him, a small mound over his groin in a peculiar shape. I had never looked at James in a sexual way before so I was surprised to feel the heat rise down between my legs. I was a virgin and had never seen a penis before, but my instinct told me that the strange shape clearly outlined on the thin sheet in front of me was a cock. I stared hard, watching it rise and fall with his breathing, my own breathing growing faster and more desperate, the heat between my legs turning to wet, I rubbed my thighs together and felt my juices fall from my panting pussy and lubricate my thighs. Fuck, so this is what it feels like to be horny. Exciting and frightening, I felt like I was losing control.
I stood slowly, a single tear of pussy juice rolling down from my lips to my ankle, and approached the small mound, my breathing turned to panting as I looked over him. I called his name several times to make sure he was asleep. I placed my hand on his bare chest, the first sprouting of chest hair appearing on his well defined body. My hand ran down over his hot soft skin, over the crevices of his six pack until my finger reached the edge of the sheet. I hesitated, looked hard at the mound rising and falling. Leaving the sheet, I slowly lowered my hand onto the mound where I met a soft and squidgy bulge. Now able to manipulate the sheet I pulled it tight around the bulge and I could now clearly see the outline of a penis and balls. My hands were shaking, my pussy was sweating. I stroked the penis through the sheet but I could wait no longer. I'm sorry James, but I have to see!
I delicately took hold of the edge of the sheet and slowly pulled it up to reveal his sleeping cock and balls. Wow! It looked smaller than I had imagined, I guess I'd seen too many pictures in magazines, his penis lay entangled in a thick forest of pubes and was dwarfed by his enormous balls which sat on his thighs. The penis must have been smaller than my little finger although fatter than my thumb and try as I might I couldn't see his head. The end of his penis seemed to be hidden in a strange sort of cork screw of skin. I was surprised, shocked and a little disgusted by what I was seeing, but damn I was horny. James' was the first penis I was seeing and while it was small it was still thrilling.
My pussy continued to burn, the temperature rising, the juices rolling down my thighs, faster and thicker and hotter. I couldn't help myself. I tentatively put out my hand and watched in shock as my shaking hand slowly lowered itself over James groin, my outstretched finger eventually touching his penis. Ah! I immediately withdrew it. It was soft and squidgy, not what I was expecting at all. How could that ever go inside my vagina? Once again I slowly lowered my hand and placed the back of my finger on his small penis, closing my eyes I slowly stroked his penis with the back of my finger, revelling in the soft touch of his small penis, the occasional itch of his long hairy pubes. While my right hand continued to slowly stroke his little penis my left moved down between my legs to find that magic button I had only just discovered a few months ago. A single touch was enough to almost buckle my knees and send me to the floor in a shuddering heap. I started to stroke my magic button very slowly, my pussy now gushing juices, I could feel them tickle their way down my legs past my ankles and in between my toes. I tore my nighty over my head and shivered as the air bit at my erect nipples, I ran my hands over them quickly before returning to my magic button and his beautiful tiny penis. My legs were shaking as my orgasm built and soon I was screaming as waves of pleasure burst through me, I was forced to stagger backwards and collapse onto my chair, fighting for breath as I was watched in ecstasy the uncontrollable shudders of my thighs.
As the orgasm subsided I heaved myself out of the chair and onto my feet. I staggered over to the bed and stood mesmerised by James' little cork screw penis. My sexual thirst had abated a little now and I was able to look at him more objectively. His balls were huge! I slowly edged my fingers in between his balls and thighs and lifted up his balls. Wow, they filled my small hand and felt extraordinarily heavy. I loved the feel of his soft warm ball sack in my hand and let it rest there. I noticed then that I had knocked his penis backwards. Where it before had been resting on his balls I had forced it to flip over so it was now facing his bellybutton. Transfixed by this new angle I took my other hand and slowly started to run my finger up and down the soft skin of his little penis, though it looked slightly bigger from this angle. My finger stopped when it reached the strange cork screw of skin where - according to my research - the tip of his penis should have been. I fingered it slowly and looked down in awe as my finger slowly retreated from his penis with my fingertip wet and a long string of clear liquid attaching it to his cork screw. What was this?! I continued to pull away until the string of liquid snapped, half of it falling down onto his penis and pubes where it sat glistening, the other half wrapping itself round my finger. I don't know why, it was instinct, but I had to taste it. I tentatively licked my finger tip and swilled my tongue around my mouth to search for the taste. Oh my god! From the first taste I was an addict. Salty yet sweet, just how I like my popcorn. I soon licked my finger clean and went back for more.
With one hand still cupping his delightful and ginormous balls, the other set about collecting all of the juices it could from the tip of his penis, every ounce of which I devoured with a hunger. My pussy started heating again, I could smell my juices flowing from my lips as I licked up the strange liquid leaking from James' tiny soft penis. After a while I grew tired of fingering the juice out and then licking it. Slowly, my heart beat screaming from my chest, I lowered my mouth towards his small penis, and took him in my mouth. What a sensation! The ultra soft skin of his small squidgy penis sat in my mouth as I licked and sucked with all my might, the tastes of his penis and juices exploding into my mouth.
But then my left hand felt something. My left hand, which was cupping his balls, felt movement, as if his balls had a life of their own and were dancing around. Then too I felt movement inside of the small squidgy penis in my mouth. I immediately leant back, his small penis falling out of my mouth now glistening with his juices and my spit, I was delighted to see a string of his juices run from my lips to his cork screw. My left hand stayed in place and continued to feel the movements. And then, something incredible happened. My jaw swung open as I was witness to a magical scene. While his balls continued to move around in my hand, I watched totally enchanted as his tiny beautiful soft penis started to grow. The penis was lying backwards, covered in my spit, lying on his tummy facing his bellybutton, and started little by little to expand. What had been a tiny soft penis no bigger than my little finger was now longer than my middle finger and wider than three of my fingers put together. But that was not all. As it continued to expand the corkscrew of skin at the tip seemed to get stuck in his snail trail of pubes which led towards his bellybutton, for several seconds the penis stopped growing as I watched the tension grow, then with one final jerk his penis slipped free of the entanglement and burst upwards, now pointing at a 45 degree angle, but far more incredibly the cork screw of skin started to open, like a hidden cave of treasure the skin started to slowly part and reveal underneath a large bulbous purple head glistening with his juices. His balls which before had been so large and floppy were now shrunken into my palm, whereas his tiny soft penis was now transformed into a mammoth six inch cock as wide as my wrist, his large engorged penis head glistening and shaking.
I was mesmerised. It was all too much to handle. My pussy was shuddering with lust, my eyes glued to this giant penis which stood shaking with a life of its own. Before his tiny soft penis had seemed far too small for sex, but now this giant glistening shuddering snake which stood hard erect at attention seemed far too big, how would that ever fit in a pussy, let alone a virgins? Without even knowing what I was doing, red lust descending upon me, my hand reached out and took hold of his cock, my hand not even able to reach fully around his fat girth. Without thinking my mouth was soon sucking and slurping at his engorged purple penis head which continued to leak sweet salty juices down my throat. The temperature was rising. I took my hand away from under his balls and again started to play gently with my magic button.
It was a feast of sensations the like of which I had never experienced before. The taste of his juices, his rock hard yet immaculately smooth penis head, his balls twisting and turning, the scent of his sex juices, my juices racing down my shuddering legs in great streams, and finally my finger working away at my magic button. I was on edge, the pleasure at breaking point, but I didn't want this moment to end, I wanted this feeling to last for as long as possible, to treasure it. I swirled and sucked and gurgled his penis in mouth, taking more and more of his penis in my mouth, sucking out ferociously any of his juices and drinking them down greedily as I managed to keep my pleasure right on tipping point, my legs and arms shaking with the pressure. But then I felt his penis buck hard in my mouth, it seemed to grow even bigger, filling my mouth right to the brim, before I felt a strange sensation rise from the base of his swollen cock right to the tip, which rested at the back of my throat. His hips bucked too and out of nowhere his penis was rammed down my throat, choking me and sending jet after jet of his juices straight down my throat, some trickling down into my mouth. All these strange sensations immediately sent me into orgasm, my legs giving way I fell onto my knees kneeling now next to his bed, my head thrust upon James' pulsating cock which continued to fill my throat with wave after wave of his juices, filling my tummy with his delicious cream. My legs were spasming beneath me, I held myself upright only by my mouth's steel hold onto James' steel cock.
Finally his rock hard beating cock stopped sending his semen down my throat, I sucked greedily for more as my legs ceased to shake uncontrollably. His fat cock started to go softer in my mouth. I let his fat cock fall from my mouth onto his snail trail, his fat 5 inch penis now covered in my saliva and his semen. I licked my lips and smiled down at the scene.
Part II
Transfixed by his cock, shrinking before my eyes, his purple head slowly being covered by his foreskin. His penis was now only two inches but still retained some of its girth. I could not believe the transformation from his tiny cork screw hidden in the dense bush of his massive balls to the giant fat cock I had held in my mouth and sucked the sweet juices from. Now as his penis lay there before me, glistening with juices, a terrible thought struck me. My pussy juices were still dribbling down my thighs as I recovered from my orgasm and the thought occurred to me, looking down at the two inch penis, now soft and meagre, that it would be a perfect fit for my virgin pussy.
I had fingered myself a few times before with my middle finger, but only after playing with my magic button for a long time and soaking my pussy and thighs in sweet slippery juices, and never pressing my finger in too deep, normally it took only the tip to send me into orgasm. If I ever tried to press in any deeper I would meet fierce resistance, I think it is what my auntie called my 'flower', which blooms the first time I am with a man. But this little two inch penis wouldn't be too much bigger than my finger, and I could easily fit it in without going too far, sending my flower into bloom.
My legs started to shake with anticipation, the red mist of lust was descending once again. I looked at James' pretty face, still totally lost in dreamland. Then I looked down at his little two inch penis, and I gently climbed onto the bed, placing my knee in between his legs I slowly knelt forward and lifted his penis off his tummy and pointing it towards the sky. I could see a large drip of juice had formed at the tip of his shrivelled cork screw and instantly bent forward and licked his sweet juices into my mouth, savouring the taste before swallowing. My hot burning pussy had settled onto his thigh, drenching him with my juices, I slowly gyrated against him, revelling in the tickle of his leg hair rubbing against my magic button. I leant forward and took his little penis in my mouth and sucked hard at the soft penis, swilling it around in my mouth. I was an addict, I could suck this dick all night!
I could feel my pleasure building in my pussy as I rubbed against his knee, but now I was ready for the real thing, I looked down at his cock. Yes, I could do it, I could take this little penis now into my pussy and not break my flower. I was ready. Breathing heavily, my heart thumping in my ears, I was now kneeling over him, straddling his groin. I took his soft two inch penis into my hand and played with him, I managed to grab the penis in a certain way and pull back on the skin so I could reveal his purple head, although smaller now than before it was still shining. I lowered myself very slowly onto his penis and gasped with pleasure as I felt the first caress of his tiny penis on my magic button. At this point I lost all control, my instinct took over. My eyes closed I started moving faster and faster against his penis, which I still held in my hand, my pussy leaking juices onto him as his purple head rubbed up against my magic button and along my pussy lips over and over again, my pleasure was approaching peak. With one final thrust I moved his head down towards my burning pussy opening and let it slip inside, promptly dropping my weight onto his groin, forcing the tiny soft penis into my hole, totally filling it. I sat there stunned for several seconds, struggling to catch my breath as I concentrated on the beautiful feeling of his cock stuffed in my virgin pussy. It was a perfect fit, I blessed nature for making it so, this tiny cock sending pleasure rippling through me as I kept my flower safely intact.
I slowly started to grind against his groin, my magic button rubbing against his pubes, his tiny penis head massaging my insides. My eyes firmly closed my pace increased. It felt incredible, I couldn't believe I had waited so long to taste sex for the first time, it felt so right. I was covering his tummy in my juices, streams of my liquid rolling down towards his belly button where they were forming a small puddle. As the pleasure grew so much within in that I could feeling it pressing on my heart, it felt as though his penis was expanding my pussy, sometimes even tantalisingly brushing up against my flower. His soft two inch cock was hitting spots I had never even felt inside of my pussy. My wild grinding increased in pace, the sounds of the juices leaking from my pussy squelching in my ears, when a terrorfying thought hit me, what if his penis was growing now like it had done before? I had felt sure that now I had milked it that it would stay small and shrivelled. My pace increased frantically as I realised that the tiny soft two inch penis inside of my virgin pussy was expanding, growing, enlarging, engorging, hardening. My eyes opened wide with terror and delight as I felt his small cock grow wider and wider and stretch my tiny tight pussy more than I had ever felt before, that purple head which I had sucked on so greedily was now hard as a rock and pressing against my flower. The fear and the pleasure combined in an orgasmic crescendo until my heart burst within me and tsunamis of pleasure burst through me from my tiny tight stretched pussy, I lost all control. I threw my head back, my hands shot to my tits where they gripped my nipples sending shockwaves through me, and finally my legs started to spasm, my knees now shaking, a terrible thing happened.
As the biggest orgasm of my life raced through me my spasming legs gave out beneath me and I fell forward, impaled on his hard cock. I felt the hot penis press hard against my flower, and in a split second there was a searing pain as I felt my flower blossom. The rock hard cock burst through my hymen as I collapsed onto him, the seething pain matched only by the ecstatic pleasure racing through me. My hips bucked wildly as my orgasm continued, ignited by pain and fear, his cock now stuck into my tiny tight pussy.
As my orgasm subsided the image of his huge six inch cock which I had sucked clean burst before me, the thought of that beast inside of me sent shivers down my spine. It will never fit, I'll burst, split in two, it will get stuck inside me and I will never escape, he will find me in the morning when his sleep medication wares off impaled upon his cock. The penis was still growing inside of me, fear took a grip of me as I tried to lift myself off him, but searing pain burst through my pussy. In desperation I put my hand down to his cock and felt the rock hard base of his penis, he must nearly be fully erect, the walls of my virgin pussy were being stretched to oblivion, I was going to tear. With one final heave I tried to lift myself off him but again the pain raced through me, and I noticed, down on my hand, blood. I was bleeding! From my pussy! My flower had blossomed?
It was too late. Unable to escape from his cock I sat writhing in terrible pain as his cock grew, deeper and wider inside of me. Tears streaming down my face, my bloody hand before me, I was impaled and desperate, stuck here on top of James, until he found me and humiliated me in the morning, his huge cock wedged inside of me.
His penis had stopped growing, but still I cried in pain and humiliation. And just when I thought nothing could get any worse, James suddenly jerked and thrust his rock hard cock deep inside of me sending pain down to my toes. I looked terrified down to his face but he remained asleep. I tried to relax myself, to stop whimpering like a little girl. I could feel his heart beating through his cock in my pussy. His fully erect 6 inch cock, as thick as my wrist, was stuffed deep into my virgin pussy, I tried to move as little as possible to avoid any extra pain, but again his body jerked wildly thrusting his cock into my tiny pussy again. I cried out in pain. I looked down to James' face, he was muttering unintelligible words. I pulled back his eyelids and saw that his eyes were still lost to dreamland. I tried to relax myself and prayed that his penis would shrink before morning came. But again his body spasmed and thrust his fat swollen cock into my tiny bleeding pussy, tears once again welling in my eyes. He continued to mutter gibberish, but he was now breathing deeper, heavier, and I started to feel an all but unsusceptible movement in his hips which was thrusting his fat cock gently into my virgin hole.
His muttering grew louder and Griffey and I was just able to make out, "Oh yeah, you like that don't you Leah? You like that don't you, you dirty bitch, fuck..." He again trailed off into gibberish. But his hips were now definitely bucking, finding a rhythm as his fat cock sent tremors of pain searing through my body. I was stuck, with this giant cock inside me, all I wanted to do was escape, and so one last time I tried to lift myself off his cock, but I was stuck fast. My pussy was too tight and his cock was too fat, I would never escape. Tears streamed down my face as his hips started to move faster and faster, sending his cock deeper and deeper into my tiny virgin pussy. Sometimes he would stop. But then would mumble to himself again and start to slowly hump his giant cock into me.
He stopped, and slurred, "Oh yeah bitch, you want it hard, you want daddy to fuck you dirty you bitch, you want me to fuck you hard and deep like the little slut you are? OK baby, I'm a fuck you good and hard just like you want it."
My eyes opened wide infear. "No James!" I shouted, "Please don't do it, just let me go. James don't do it, I'm not ready, you're too big! James!"
But then I felt his hands rest on my hips and he started to thrust again, slowly now but with a steady rhythm that sent pain shooting through my pussy.
"You love my fat dick don't you baby? You want it deep inside you? You want me to fill you with my cum til you burst, baby?"
"Please, James, stop!" I hissed but it was too late. He stopped mumbling, his hands gripped hard onto my waist, and his cock thrust deep into me, harder and faster. The tears now rolling freely down my face, falling from my chin onto my tits where they tickled their way down my body. I tried to stroke the tears off my chest but as my hand brushed my nipple a ripple of pleasure burst through me straight from my perky tits down to my pussy. Again I stroked my nipple and waves of hot pleasure raced through me. I started to pinch my nipples, biting my lips and tasting my salty tears as James continued his slow assault on my virgin pussy, his tight grip on my waist hurting a little.
Pinching my nipples harder and harder I could feel my pussy start to ignite, the flame of lust rekindling, the hot juices started flowing once again, I abandoned myself to James' ravishing of my tiny virgin pussy. His thrust not only became faster but stronger, deeper. He was now thrusting up into me with all his might, his cock reaching deep inside me, I didn't know if it was my vagina or my stomach, but the feeling was incredible. As my juices really started to leak the pleasure only increased, his cock now thrusting deep into me more easily, I was no longer glued to his fat cock but he moved in and out of me with more ease, still hurting and stretching me, but this only added to the blinding pleasure which was engulfing me.
His cock now ramming into my pussy, sliding in and out with ease, lubricated with our juices and my blood, I could have escaped him if I wanted. I knew there was enough lubrication for me to slip off his cock and be free, but the delightful melange of pleasure and pain was like nothing I had ever experienced, nothing I had ever experienced, and when I thought about that fat six inch penis actually being inside me, my tiny tight virgin pussy, I grunted and started to follow his rhythm, smacking down into him as he thrust up, his fat cock crashing into me, my magic button drowning in a puddle of our mixed juices.
"Oh fuck Leah, you like that, bitch?"
"Oh yeah James" I blurt out, "Fuck me James, fuck me hard."
"Do you like my dick inside you?"
"I love it! Oh, it's so big, so fat in my tiny pussy. Don't stop James, it feels so good!"
"Oh yeah, fuck your tight little pussy with my fat cock and you love it, don't you? Everyone loves me and my cock!"
"Oh yes, oh fuck, don't stop."
James was now grunting with each thrust as his hips bucked wildly, smashing his fat cock deeper and deeper into my pussy. I was smashing down into him, waves of pain and pleasure coursing through my veins.
"I'm gonna cum! I'm gonna cum in you!"
"Do it James!" I screamed hysterically, "Cum in my little virgin pussy with your big fat cock!"
His face contorted as he made one final devastating thrust so deep into me that I swear I could feel his cock in my belly. The sensation was too much and tipped me over the edge into orgasm, as I felt his semen burst into my vagina, imagining his beautiful engorged purple head firing wave after wave of his sweet salty semen right into my virgin vagina. My legs were shaking uncontrollably as I bucked and shuddered on his pulsating cock, the sensations of his cock so deep inside me filling me with pain and pleasure, my magic button shuddering against his body in puddles of our juices and blood, the orgasm would not stop. I could barely breathe as stars flickered in my visions, my body contorted in pleasure, his fat cock still pumping deep inside of me.
Slowly I came to my senses. I tentatively lifted myself off his now softening cock and watched as it flopped out of my penis, the fat five inch penis fell with a smack into the puddle of juices on his tummy, covered with our cum and my blood. As his penis slipped free of me another small orgasm took hold of me, my pussy now feeling empty, I could feel the cold air tickling the insides of my tight pussy and his white semen trickle out of my hole, tickling my pussy lips.
I climbed off the bed and I looked down in awe at his beautiful cock, now four inches but still as wide as my wrist, his purple head slowly disappearing into his sheath. I stroked my still trembling pussy, so sensitive now I thought I would collapse in a never ending orgasm. I lifted my fingers to my lips and sucked the sweet taste of his semen, my juices, and my flower. I was exhausted. I hurriedly grabbed my nighty of the floor and tried to wipe his cock and stomach clean of my juices and blood. I gave a goodnight kiss to his now two inch cork screw penis and staggered back to my room, still in a total daze, and looking forward to tomorrow night. Where again I would suck his fat cock clean and stuff my pussy full to bursting, reaching climaxes of pleasure I thought not possible.