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First Time Disaster and Second Chances
By
flytoomuch

First Time Disaster and Second Chances

Not all first times are this memorable.
I’m a really terrific liar. It’s a talent. I know it sounds awful. My mom totally grounded me like a billion times when I was in high school, for being a liar that is. My lying is problematic and I worry about it. Sometimes I can’t decide if I’m a “good girl” wrapped up in a “bad girl”, or if I’m a “bad girl” wrapped up in a “good girl”? You decide. But actually I’ve found my lying to be a very useful talent. But that’s another story.

I don’t really know why I lie so much. Maybe it’s because I’m fragile. Inside I’m fragile. I act tough and people think I’m tough, but I’m not. No fucking way. I’m fragile so I hide. I don’t exactly feel like handing people a blueprint of who I am. Who knows what the fuck they’ll do with it.

You can’t really trust most people. I learned that early. Plus it’s fucking true. My dad died of a heart attack when I was three. I learned: don’t trust the fucking world, even your dad. People are unreliable—they die. So many people tried to fuck my mom over after that. Pretty much everyone tries to fuck you over.

I don’t really know what kind of crap you want to know about me, but it’s probably stuff like my email, or my last name, or my Skype ID and shit like that, but actually that shit bores me and there’s no fucking way I’m giving you that kind of stuff. Okay? So jump in a cold shower and disabuse your fantasizing brain about that little horny gem. It’s not exactly like I’m short of male admirers if you know what I mean.

I can tell you tons of random shit about my self. Like how super clumsy I am. My own view of this is that the floor hates me and tables and chairs are secret bullies. What else? Aside from lust, my other favorite sin is gluttony. If we go for dinner and get to the desert menu you’ll know what I mean. I always gorge myself, especially if I’m nervous. I have a sweet tooth. Sweets and sex seem to be my downfall.

What other random shit can I tell you? Growing up I was skinny as a weed. People thought I was a boy. Now they sure know I have a pussy. Okay what else? Oh, I’m stubborn. I love to surprise the shit out of people. Frozen yogurt with sprinkles of red gummy bears makes me happy. Oh and don’t forget, I’m a sleepyhead who has frequent mood swings. Bipolar? Nah more like multipolar.

Anything else? Let me think. Well I’m a really good actress. My mom can attest to that. I can play two people simultaneously (yes your best lover ever AND your worst nightmare). I’m such a good actress half the time I don’t even know I’m acting. And in spite of all of the above—no-- I’m not perfect.

I could tell you all kinds of additional personal crap from my past. Like about how I almost got kicked out of my highfalutin prep school. Or maybe the time my mom wanted to lock me in the house when I was sixteen, but I’m still feeling kind of touchy about those two sore points. I’m pretty touchy about some things. Well a lot of things actually. I guess I’m a touchy person.

Did I tell you how I’m not really very tall, but people always remark on “how tall” I am? I guess the impression I make is taller than me. Anyways I’m rambling again. I’m trying to think how to make this interesting? Okay let me think?

I could tell you about my mom and how she’s still single and all the guys she fucks. But hey she’s totally touchy as hell about that. I mean colossally touchy. On this single subject she’s even touchier than me, so I’m not going there even if you begged me. Everyone has his or her own little sore point, right? So basically my crumby life is awfully boring. You might compare it to watching a single goldfish meander in a bare glass bowl. Got it?

So anyways as subjects for discussion go, how about my virginity? Or I mean my lack of virginity. Or how I got rid of it. Oh shit you get my point, right? Shall I continue? Okay so my name is Kelly, but my mom always calls me Pebbles. She says I had reddish hair when I was a baby. She thought I looked like this cartoon character in the Flintstones. Anyways by the time I got older my hair had changed to mostly blond and the red had become more of a bronze. But still all my friends call me Pebbles. Whatever.

Okay so because of my dad’s life insurance policy my mom could send me to this fancy prep school. You know tartan mini skirt, white blouse, up tight rich kids. The guys wore bleached-teeth smiles and too-blue blazers with faux gold buttons. Half the girls were gifted fake boobs for their sixteenth. Got the picture? Do you know what I learned? I learned a singular lesson: the more rich kids you have in a school the more thieves you have. Fuck I can’t tell you how I hated that place. Bunch of phonies. One thing I can’t abide is phoniness.

Anyways when you were in high school did you learn any talent? My greatest talent was just to be myself. My trademark back then was just “me”: the “me” without make-up, the “me” without being showy and especially the “me” without pretending to be someone or something I’m not. Not a phony, got it? Anyways I’m rambling again. I’m pretty sure you don’t really care about all this random shit. Anyways it was a long time ago.

Want me to get on to the really, really personal stuff then? Well like all girls I was once a virgin and then I wasn’t anymore. Interested now? I’m pretty sure you’re interested. I haven’t run into many people, who aren’t interested in sex, especially stories about how girls lost their virginity. Those seem to be crowd pleasers.

Okay so I think you get my point about what kind of girl I am? Or should I clarify to say the kind of girl I was back then in high school when I was sixteen. Too many girls in high school spend all their time trying to be something else, or “someone” else. It’s not like they are all morons or anything. It’s just they act so phony it stinks. When I was in high school I didn’t fucking waste my time like that, so yeah? What the fuck? I’m just me like I said, so if you aren’t interested then fuck off and stop reading.

Anyways it was 2004 and a few days after my sixteenth birthday. I was supposed to be “grounded” by my mom. It was because of some truculent fucking lie that exploded in my face. I was in my room reading “Out of Africa” when I heard about a house party a few blocks away for seniors. I mean “Out of Africa” is actually a pretty good book and all, but then Cristina called.

“Pebbles…hey can you sneak out?”

She knew I was grounded so I presumed something pretty important was happening. I looked outside my door to check if my mom was listening. No one was there so I asked Cristina what was up. She told me about this house party. The guy she had a crush on was going to be there so she was hankering to go. It was Friday night and I was desperate to go too so I snuck out of my mom’s house.

I walked since it was summer and the house for the party was pretty close to mine. It was at this guy David’s house. He was a senior. Cristina agreed to meet me at the corner two blocks away. It was a warm night and I could feel the cool breeze off the ocean blowing my hair. Yep, I live in Orange County (the OC baby!) so I hope you’re not too jealous.

I don’t really have any sense of “style” actually, even today. Back then I was trying to pull off “edgy” you might say? I guess I thought that “edgy” was stylish. I thought I was a rebel or something romantic like that. I was wearing this see-thru coral colored short sleeve top with a black bra underneath. You could really see the black bra through the thin fabric of the top. I guess I thought that was pretty sexy and would catch the boy’s eyes? At sixteen I wasn’t very subtle and figured if a guy could see my bra he’d get the message.

I had tied the thin flimsy fabric of the top in a loose knot under my firm young boobs. I wanted to bare my flat tummy. I had paired the top with an 80’s style tiered mini skirt with three sets of ruffles. My long hair was all streaked and blond with bronze highlights from the sun and pulled into a loose ponytail. Quite a few strands were flying loose in the summer breeze.

I’m usually pretty casual about my hair and can’t be bothered to do much. Except back then I really liked to color it. I was sixteen what do you expect? So yeah I mean it was like seriously “California blond” compliments of a few tubes of cheap “Sun In” hair bleach from CVS. Only a few hints of my natural golden bronze hues had survived the cheap bleach job.

My skin was smooth and golden, pretty youthful and perfect actually. Fuck I was only sixteen. I had always been skinny as shit, but finally that year I had filled out and now I even had real hips and some noticeable tits; only thirty-two almost-B’s, but hey better than before.

If I don’t say so myself I was looking pretty fucking cute. I was also pretty good at playing “brave” since at school I took a lot of abuse for hanging out with punks, losers, dorks, nerds and retards. So yeah I was pretty much a really sexy and cute bookish nerd. Yes hot and smart does exist in the same girl so stop being so skeptical.

Anyways there I was, a cute and sexy but nerdy freshman, walking to this house party. I was a freshman about to crash a party for seniors. I was all pumped up and feeling pretty stinking brave. My stomach was full of butterflies, but I wasn’t going to let that stop me. Cristina held my hand and we couldn’t help giggling the closer we got.

I had decided (compliments of long and heated discussions with Cristina over the previous week) that I really wanted to lose my virginity to a boy based solely on his looks. Since at my lame prep school I couldn’t really find a boy worth my time (I’m smarter than pretty much any boy my age I’ve ever met) so I decided to turn to more basic and primal criteria—looks!

Hey cut me some slack. I was a healthy sixteen-year-old girl with a body pumped up with raging hormones. After all in caveman times I would have probably popped out two or three kids by the age of sixteen. To have never even experienced penis-tration at sixteen was a tragedy in my mind. I intended to rid myself of the big “V” that very night.

Since I hadn’t as yet been able to locate a boy worth my time I decided other Darwinian choices needed to be made. Mate selection based on a cute smile and hot body seemed the right way to go. I was fucking horny and decided to jump one of those pliable sun-bleached-brained boys I lived amongst who’s biggest interest in life was his surfboard and getting a feel of a girl’s tits while slow dancing in the gym or sitting on a log at the beach in the dark.

Cristina smiled as I approached the corner where she was standing under a street lamp. She looked super hot in her jean mini skirt and sparkly flats. Her long black hair was really shiny. I had noticed that Cristina’s long hair would just mesmerize some guys. Oh yeah and she had really nice firm “C” tits: those firm cones sort of also mesmerized boys. Even though we were freshmen girls I didn’t think the boys were going to throw us out of the party. Cute girls just get away with all kinds of shit, right?

After we arrived at the party I sauntered around and said hi to a few people I knew. Cristina was looking for this guy she had a crush on named Rob. When she saw him I knew I was on my own. Some of the older girls looked at me in a pretty paranoid manner. Older high school girls hate younger girls invading their territory. I could sense their claws coming out. I pushed out my tits and kept up my brave face.

I had my own plan so I scanned the crowd. From the look of the scene I was in the right place. This was a summer surfer boy party and I was looking for a perfect plastic surfer boy to fuck. I’d been masturbating like crazy the past few days. I had been reading porn and dreaming of a guy licking me to orgasm. I wanted sex unbelievably badly. My body was like some kind of volatile powder and I knew I might possibly explode upon contact if a guy actually touched me. It was fucking embarrassing how horny I was. I wondered if the guys could tell when they looked at me? Still I kept my nerve.

Other girls can tell when you’re on your own and on the prowl. Later when women are married they use this animal instinct to protect their cock-property. I got more than a few seriously dirty looks. The ones holding hands with their boyfriend would hang on even tighter as I cruised past. The fear in their eyes indicated they regarded me on the same level as a Great White Shark. I knew they all wanted to tell me to leave their boyfriends alone. As if?

Guys at seventeen or eighteen will fuck anything that walks. Now that I’m older I can laugh about it, but at the time it was serious girl shit; survival of the fittest shit. Basically if I had wanted any of those boys it would have been easy. When you get older you soon realize it’s not brain surgery to cut a male loose from the herd, even if he’s married or “going steady”. In my experience hunting men is pretty much like shooting ducks in a barrel.

Whatever! I didn’t like any of these senior girls. I didn’t even like the fucking party. It wasn't my scene; they knew it and I knew it too. I was invading their boy cliques and they could sense the threat. I was a hot, sexy, fertile interloper and I sent a chill up their spine. Well I kept weaving in and out of the crowd looking for my chance. Someone handed me a plastic keg cup. Holding the cup made me fit into the scene better so I held onto it even though I hate beer. When hunting for prey it’s good to blend into the background. The beer was a prop that formed part of my camouflage.

I looked over the crowd of plastic too-tanned people. I eyed up every last one of them fearlessly. I respected none of them. I walked through them as if in a force field with my polarity repulsing theirs. My eyes were roving over the unsuspecting grinning young males like the Terminator's heat sensors. My computer-like teenage brain was seeking the correct pussy prey. My skin was tingling in anticipation as my eyes took in their glittering sea of phoniness. I was certain they were all secret slobs with this civilized veneer of phoniness.

There were exactly two special boys at our school that all the girls wanted. They were the two shining stars of OC surfing. Young tanned specimens of summer who played in the ocean all day and fucked anything that moved on the beach at night. How can I describe them except to use the term “golden boys”. Everything about them was golden. Their tanned smooth blemish free skin, their sun-kissed bleached eyebrows, the way their eyes danced and flickered with teenage confidence. They knew pretty much any girl at the party would spread her legs for them. All they had to do was ask. Maybe not even ask.

Out of the two golden boys I decided I wanted Gordon. More than anything I decided I wanted him to fuck me and take my virginity. It stuns me now thinking back, but I can’t even remember his last name. I must have forgotten it? Whatever. Maybe I’ll remember it later. It started with an “L” I think.

I began to stare at him and move closer. I wanted him so badly and yet I bet he didn’t even know I existed. Don’t get me wrong. I didn’t want to know him, to date him, or whatever. I didn’t want to go steady or anything. Yuck no. I just wanted to fuck him. He was gorgeous and all the girls knew it. He was standing with his friends, holding court, constantly pretending to be someone I was certain he wasn’t, but still he was pretty enough to eat.

I had never even talked to Gordon at school or even approached him. It was more than obvious he didn’t have too many brain cells so I hadn’t felt the need. The other golden boy next to him was Craig. The two of them were best friends. They were huddled together with a few other guys near a keg drinking beer. I sidled up to their group to listen and then casually slipped in to pump some more beer into my half-empty plastic cup. I caught two or three of the guys checking out my tits. Looking back on it I almost giggle. I was actually pretty smooth about the whole thing.

I pumped more beer in my cup. Gordon was explaining to the group of surfers circled around him that his goal for the evening was “Really Big Tits”. My heart sank. What the fuck? Is that all he wanted. I looked down at my recently expanded chest and knew I would definitely NOT qualify. Even the see-thru black bra would not be enough. Big tits? Is that all guys cared about. He was a senior and had been fucking girls for what I imagined was ages. I looked down at my pathetic budding almost B-cups and frowned in disappointment. My plan was in disarray.

I imagined that this golden boy senior surf god knew everything about sex. I imagined he would be the perfect instructor to take my young body where it wanted to go. As I had been staring at his chiseled physique my brain had gone places I don’t even want to discuss. It’s too embarrassing.

Gordon’s perfect bleached white teeth sparkled as he talked about the huge mammary glands he was searching for. Cristina was more his cup of tea? Maybe I should go get her and make a holy sacrifice of my best friend’s pussy to the god of virgins? Okay that was a stupid idea.

Anyways knowing I didn’t have even a sliver of a chance with my surfer golden boy reduced my inhibitions of approaching them. After all I had no chance. With nothing to lose I blundered ahead without a clue as to what my end game would be. So somehow I joined the conversation and introduced myself. I glanced around at the faces of these young surf kings with ripped bodies. Taking a measure of their interest in my body I picked out Paul. We chatted and while he might be one of the least cute of the group, he was still quite fuckable and he seemed rather interested in me.

I wanted to get Paul’s attention so I told him I was supposed to be grounded. I giggled and mentioned in a voice loud enough for the others to over-hear that I’d been in such a hurry sneaking out of my house unnoticed that I had forgotten to put on underwear. My palms were sweating and Paul’s eyes went wide. I knew I’d made an impression. With young guys you can’t be subtle. I was preparing my brain to settle for a guy I never even would have considered fifteen minutes ago. Was Paul really going to be the guy who took my virginity?

Just then a sort of miracle occurred. Not the fake sort of OC Disneyland miracle, not a balloon trick, but a real honest to god life changing moment. The guy next to Paul was David who was a senior and he was the guy hosting the party. David looked up and I turned to see what he was looking at. At that moment John the uber-king of Laguna Beach surfers pushed in beside me. John was David’s older brother and all twenty-six hunky years of him was right next to me, his bare muscular arm brushing mine.

John tousled David’s hair and grinned the most electric genuine smile I had ever seen in my life. I was ready to melt into a puddle. How good looking was he? He was yearbook good looking. He’s the kind of guy that you’re mom would look through your yearbook and ask “Whose that?”

John was not only good looking he was also charming. He was armed with witty banter and was confident and funny. John complained that his little brother’s party was all he had for entertainment that night. I remember gazing at his golden tanned skin and being entranced by the light freckles sprinkled along his cheekbones and nose. He towered above me in his six-foot-one glory. I couldn’t help gazing at his strong broad shoulders and strong biceps.

I still remember the first time our eyes locked. Bright golden flecks danced in pools of green emerald and his eyes twinkled with a mischievous playfulness as if to say we were all just a bunch of silly underage kids drinking Kool-Aid and pretending to be grown ups. I didn’t say anything at first. I just stared at him. Every other guy around faded into insignificance. John’s body attracted mine like a magnet. My pussy began to get wet as it readied itself for the mating ritual.

This was John’s house and being so close to him made me nervous. For someone so talented with her tongue I was suddenly tongue-tied. He played the part of a wise old man to the hilt and played with me in ways no boy at school ever had. He had me blushing, stammering and giggling until I was twisted in ways I had never been twisted before. I was struggling to keep up with him. Not only did he look like a god, but he was smart and funny too. This was a fucking miracle. I wanted to drop to my knees and thank whatever fucking god had intervened to save me from all these phonies.

I needed to get him away from this group of posers. I had not come here to talk about surfing or to gush over his tales of the huge curls off the coast of Portugal. I had other plans. Important girl plans. I wanted him to ride me. I wanted him to make me into a woman. The wheels in my brain spun frantically. On the outside I flicked my hair, batted my eyes and did my best to flirt. I sent so many signals I almost confused myself. I turned to David to make my final move.

“Hey so you guys have an amazing house. Which room is your brother’s?”

I said it loud enough for John to overhear me. John grinned a huge cute grin. I just stared back playing the precocious ingénue to the hilt. My stomach had a million butterflies. His eyes twinkled playfully as he looked my hot young body up and down. The lust playing in his eyes was pretty obvious. My nubile young body and my flirting had hooked him I was certain.

“Well I’m on the road a lot surfing, but you wanna see?”

John took my hand and led me upstairs. My heart was pounding and ripping at my chest. I had fantasized about this moment for so long. I knew exactly how I wanted it to be. I was going to be a tigress. I would amaze him. I would dazzle him like no other girl. My mouth was going dry and my throat was tight. I was searching for all the brilliant and witty quips I knew I had somewhere in my brain. Where had they gone?

I wanted so much to be confident and perfect. Instead I was incredibly shy and just gazed at this god-like man in adoration that could not be spoken. I had terrible cottonmouth. In his bedroom he had thin shitty worn carpeting. I kept moving my feet nervously and almost tripped. I wanted so badly to be confidant and perfect, but I ended up being shy, nervous, fidgety and clumsy. Overall I guess I acted just like a sweet and innocent virgin. In hindsight perhaps I wasn’t as brave or as good an actress as I thought.

I was trying so hard to act like some other girl that I must have looked really foolish. I wanted to kick myself. I was so mad. I was ruining it, ruining the moment I had waited for. John stared at me grinning for a moment. I didn’t know how to fathom his look. Was it a leer? Was he just an older guy after quick sex? Was this a huge mistake? Was he phony too? My nerves were exploding and I was about to blow the whole fucking thing.

In a flicker his eyes softened and he touched my cheek gently with his finger. He brushed my face as if I wasn’t real. He knew somehow that inside I was fragile. At that moment I felt like an angel. I knew everything was perfect. He slipped his arms around my tiny waist and our lips touched. It was bliss. It was like nothing I had ever experienced. Silently I again expressed my gratitude to some unknown god of first-time sex.

John’s strong arms lifted me over to the large bed and lowered me like I had no earthly weight. We were kissing and I was rubbing against his body like a cat in heat. It was the first time I had ever French kissed. Sorry, I was a nerd. I was so entranced by the whole experience I forgot to breath. It was like we were underwater and I would break the kiss desperately to gasp for oxygen. John laughed lightly in the most amazing and charming way.

I had been masturbating and reading porn so much before this night that all I had imagined was that I wanted “sex”. I had no real idea what that meant, but I knew other girls had “sex” and I wanted to have “sex”. Then John started kissing me and the bliss and the tingles started and I forgot all about sex. I had my tongue in his mouth and I never wanted it to come out. I didn’t want “sex”. I wanted this; this perfect moment.

While we kissed and I rubbed my hips grinding them against his thigh my eyes were glued tightly shut. I would crack them open a tiny slit to glimpse my god, checking to make sure he was real, and then glue them shut again to enjoy his kiss, to enjoy the hardness and warmth of his body. I was afraid if I opened my eyes and he noticed he might stop. I was afraid this might all end. I was terrified he might just get up and call me a “kid” and say he was bored and it would be all over.

Each time I cracked open my eyes John’s remained closed. I got braver and stole more and longer glances, my heart pounding furiously. I was astounded that I was kissing such a handsome and smart man. My nerves abated and my hands began to tentatively explore his upper body. God he had strong shoulders and biceps. My pussy was getting more and more wet. His eyelashes were so long. I had this terrible urge to get my curler and see if I could curl them.

Then I could hear a boy talking loudly in the room next to us. I was pretty certain from the voice it was Gordon, the poser surfer god who wanted only “huge tits”. He was with a girl. They were laughing. I checked but John still didn’t open his eyes. I knew Gordon had found a girl with big tits. John said nothing and we just kept kissing. I sure as hell wasn’t going to stop him.

We both began to move and probe with our tongues. I was exploring his body with my hands, getting braver. We were rubbing against each other and felt each other’s bodies, as we got more and more excited. Next door the girl started making more and more noise as Gordon did something seemingly amazing to her no doubt huge tits. I couldn’t help listening they were so loud.

At some point Gordon was about to fuck her. She was resisting and playing hard to get. I wanted to go next door and inform her that she was at a keg party and in bed with a guy who just wanted to fuck a girl with big tits. But that would have meant leaving John. Finally the girl relented and we could hear the noises of hot sweaty sex. The action and noises from next door only made me more and more horny.

We kept kissing and touching. I could smell John’s hard male body and taste him. Having this real body to explore intoxicated me and I wanted more. He opened his eyes at the same time as me and we both smiled. The connection was something we both felt. We were riding a wave as big as any he had ever surfed off the coast of Portugal. I knew he wanted me. I certainly wanted him. Out kissing, our touching had made John huge. Somehow everything was a blur and he had removed all my clothes and then we were naked together.

I was fumbling nervously with his buttons and John helped me without comment or laughter. Our tongues tangled and probed and the way he touched me was so intimate. I was so fucking wet I blushed. He sucked on my lower lip and I groaned rubbing against him. John was driving me insane with desire. As John’s hand neared my hips my body tensed. I clenched my legs together. I was so fucking scared. I don’t remember what he whispered, but whatever it was it calmed me and I relaxed. He began to stroke the light tufts of hair on the outside of my pussy while he whispered and we kissed.

Eventually with coaxing and whispers my legs were pried open. All sense of time and space were gone. All I knew was John and his body and what he was doing to mine. My chest was heaving and my body was flushed and hot. At some point my small hand was holding his cock. It shocked me how big it was and I wondered if something so huge could actually fit inside me. But no thought could stay lodged in my brain for long. Everything was a blur of desire.

John pushed me back on the bed. In the dim light of the room he got on his knees and went between my spread legs. He was a dark shape above me, about to take me, to take my virginity. The fragile girl inside me, the first time girl, was so scared. Then his lips were on mine and he was using a hand to position his cock. John fumbled with his cock trying to find my pussy lips in the dark. My fingernails nervously dug into his shoulders as my body tensed.

John kept moving his cock, fumbling and shifting. I moved my hips up a bit to help him find my pussy entrance. Finally I felt his huge thick cockhead at my wet lips, my tight virgin entrance. I guess my pussy clenched up? I was nervous, what can I say? He tried to push in gently, but couldn’t get in. My pussy was not having it. I was terrified he’d give up. Instinctively I spread my legs further, coaxing him to try again. I guess I was in the middle of breathing when my pussy relaxed and John pushed. The grunting sound he made as he pushed into me was like music to my virgin teenage ears.

The next sensation was searing pain. As John pushed in it was the most painful thing I’d ever felt. It was like a hot knife driving into my pelvis. I guess I wasn’t as ready as I thought. I tried to not make a sound. I tried not to cry out. I bit my lip to stifle the pain. I put my lips to John’s ears and whispered. I whimpered for him to please take it out. It just hurts too much I implored. Take it out I begged.

In the room next-door Gordon was slamming into his big tit slut and she was screaming at the top of her lungs. She kept screaming how she was going to come and how big it was going to be. The walls were so thin she might as well have been in the room with us. Needless to say I felt shame and humiliation. I felt like I was a failure as a woman.

John slowed and eased up, but he was not easily stopped. We had done so much petting he wanted me pretty badly. He tried to calm and soothe me. He brushed loose strands of hair off my forehead tenderly. He whispered that he just needed to be gentle and slow and then it would get better. John tried to pull his cock back slowly and even that felt like fishhooks ripping at my insides. I let him push in a few more times with tentative thrusts, but I felt like I was being torn apart. Even John being careful seemed like it was too much.

I let John push at me gently a few more times and I tried to grind my hips back. I prayed he would come soon. The pain seemed like eternity. This seemed like the cruelest joke the god of first-time sex could play on me. I let John push a few more times, but my despair was building. I decided I needed a new strategy. I slowly eased off his big thick cock with as few whimpers as I could. Even in the room’s dim light I could see the disappointment written on his face.

John lay back on the bed and sighed. He extended a sympathetic hand and I knew he was doing his best to act the gentleman. No matter his disappointment he was still being sweet. I was about to try something else I’d never done before. I hoped the results would not be as pathetic and hysterical as my attempts at intercourse.

I crawled towards John’s huge erect cock. All I’d ever heard from my girl friends were things like “suck it”, “pretend it’s a lollipop” and “every guy loves a blow job”. Beyond this I had no idea how to really give one. I had no idea how fast I should go up and down? Nor any idea how hard I should suck? And how would I breath while doing all this sucking I wondered?

I began to suck and lick and blow hot air on the head of his big cock. I squeezed my hand around his cock and stroked up and down. It was so thick my fingers barely made it around. I licked the pre-cum off his tip when it oozed out. I figured that was a good sign and meant I was doing something right. John let me do whatever I wanted with his cock and didn’t say a thing. I’m sure he was baffled by my teenage ineptitude, but was too gallant to damage my self-esteem by commenting.

Finally I squeezed his cock and wrapped my lips around his head, sucking like a vacuum. He groaned more loudly than ever before. John’s groan inspired me to greater efforts. I sucked and licked and bobbed up and down like a demon. I was determined to salvage something from this night. My “first time” would not be a total failure if my mouth had anything to do with it.

Eventually John’s body went rigid, he gasped sharply and then he spurted huge gobs of salty cream into my mouth. I gagged and almost choked his load was so sudden and so huge. I would have grinned except my mouth was full of cock. My heart was filled with relief. With that accomplishment I crawled up into John’s strong arms and he stroked my hair gently. We both fell off into a slumber. I wanted to cry, but I fell asleep instead.

In the morning the dawn light pulled my brain from a deep sleep. I could still feel his strong arms wrapped around me. I felt him slip away trying his best not to wake me. I feigned sleep and he sat up on the side of the bed. I had no idea what a girl should say after having sex with a guy? I was too scared to open my eyes. I heard a bit of commotion in the bathroom and then I heard his voice. He was speaking softly, like in a half-whisper.

“Kelly are you awake?”

Then I heard the door softly close and his Mustang started up and peeled away from the house. I felt so hurt and disappointed about all the events of the previous evening. I just lay there in a state of indecision and pretended to be asleep until he was gone. I was too nervous to face him.

With his car gone I realized I needed to get out of this house and back to my own before my mom took a shit. I sat up in bed and literally I was sitting in the middle of a total mess. There was blood everywhere. It was between my legs, all over the blankets, it was everywhere. My face turned beet-red and I felt flushed and nervous all over. How could that much blood have come out of me?

It was then I realized that it wasn’t just John who had made me so “wet”. I had started my period just as we had started to make-out. I got up and groped my way over to the bathroom realizing I was still dripping blood. I was stunned and embarrassed. I looked for a towel and stuck it between my legs to stop the blood dripping. I tried to wipe and clean myself, but now I was so upset my hands were shaking. I just wanted to get the hell out of that house as fast as I could.

When I got home I snuck into my house through the back door turning the key as quietly as I could. I walked on my tippy toes into my room and into the bathroom making as little noise as possible. I sighed in relief. I thought I had made it. I used a warm wet cloth to start wiping the blood away from my thighs. Then I saw my mom in the mirror. She was in the doorway with a worried expression on her face.

“And where exactly were you young lady?”

I thought of all the lies I could tell. Several options whirled through my head. But in the end she was my mom and I started to cry. The whole thing poured out like Niagara Falls. A river of tears was unleashed and I sobbed uncontrollably. At some point in the telling of my pathetic tale of woe my mom started to laugh. Her laughter caught me by surprise. Then I started to laugh too. My mom looked at me with new eyes.

“So my little girl is a woman now?”

She said it with a sense of wonder knowing that the miracle she had started years before had now transformed into a full-grown woman. She almost had an expression of disbelief. She repeated the words slowly like a mantra.

"My little girl has become a woman!"

Mom cried, a small tear forming in the corner of her eye. Then she pushed me into the shower with tears and giggles mixed equally.

“Clean your self up Kelly.”

She went to her room to find me a box of Tampax.

So my “first time” was pretty much a disaster. The story does not end there however. John got my number from someone and called. He wondered why I had run off? He laughed about the blood and said he’d had to throw the sheets away. He convinced me to go on another date. He was so cool about the whole thing.

The second date was adorable and sweet and awesome and he became my first real lover. We fucked like rabbits for about a year until we drifted apart. I had to go to university and he had to surf even bigger waves. It’s been a few years now. He taught me so much. I have always treasured my memories of that first love with John. My girlfriends all say that my “first time” story is the funniest they’ve ever heard.

Weird thing is John recently found me on Facebook. He’s coming to where I live and he asked me if I was single. He’s stopped chasing waves and is a lawyer now. Who would have thought? It just so happens I am single. Who knows, life is strange right?

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Continue reading My Best Friend's Daughter: Part I-Temptation

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