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The Best friend and the Boyfriend

The best friend and the boyfriend

We met on the first day of seventh grade in the girl’s washroom. She told me she liked my headband and asked me where it was from. I gave her the name of the store, a snobbish little girl look through the bathroom mirror, and walked out through the swinging door. Lauren Styles and I had been best friends even since. It was a friendship based on similar tastes, similar backgrounds, and rivalry.

Both natural blonds, when we turned 16 Lauren convinced me to dye my long, golden locks a dark brunette shade. People who had watched me grow up, my Daddy especially, were shocked. But my fair skin was not pale, I had colour in my cheeks and lips, and the dark hair did not look unnatural. My once blue irises now had gray in them and it added a depth to my eyes that had not been there before. I looked much older than I was, my body having developed at an accelerated rate compared to my mind.

In short, I looked like I had some dirty secrets and the problem was, I did not. I knew about the secret crushes of my best friend but other than that I was pure as snow. I was fresh 16 and looked as though I had already done deeds that had not even occurred to me and wouldn’t for years to come… or at least they shouldn’t have.

Miles lived in a nearby city where Lauren’s family had a retreat home that we would often take weekend getaways to, with Lauren’s parents of course. They met in the summer after tenth grade, while I was traveling overseas with my parents. Miles was a local and Lauren was a city girl spending the summer. He was older, she was innocent, it was in the heat of summer... I think it’s pretty obvious how these things happen.

When Miles and Lauren started dating I was jealous, for a lot of reasons. I was jealous that the girl I had grown up with was suddenly more sophisticated and experienced than I now that she had a boyfriend. I was jealous that she’d gotten there first. I was also jealous of Miles for taking my best friend, whom I used to spend all my time with, from me. No more weekends filled with shopping, sun tanning and sleepovers – Lauren would be with him.

But there was another type of jealousy, a jealousy I didn’t recognize. Not the territorial, “she’s my best friend not yours” I’d felt when we were preteens but instead an intense and overwhelming feeling of not wanting Miles to touch my sweet, beautiful blond best friend - or her body.

And Lauren was beautiful. Standing at 5’8" she was three inches taller than I, but weighed the same 120 pounds. Her breasts were only A cups, but they were proportionate with her slender frame and her full, round bum made up for any curves she was lacking. Her brown eyes were soft and although she had no especially alluring quality other than her flaxen hair, her delicate features were those of a classic beauty.

Unfortunately Lauren had convinced herself her infatuation was love and she was determined to give her virginity to this “Miles” character, despite my best efforts to dissuade her. None-the-less I was an important person in Lauren’s life, if not still the most important, and my best friend wanted me to meet the infamous Miles before they went through with the act. I was more than happy to oblige.

It was a weekend in September just after Lauren had gotten her drivers license. Her parents, assuming with the rest of the world that we were the nice and responsible young girls we appeared to be, let us drive alone to the cabin in Lauren’s new SUV, for a “girls weekend.”

He was already waiting on the porch when we pulled up. I kept my legs closed as I exited the passenger seat in my swirling olive-green miniskirt. I wouldn’t want to flash my best friend’s new boyfriend my panties, at least not yet.

“Baby,” Lauren squealed, her blond head bouncing over to the muscular, dark haired figure. After greeting him with a kiss she spun around, “This is Sybil.”

I watched Miles’ face tense as his eyes made their way past my exposed, golden legs and small waist, landing on my 34D breasts, barely confined in my flimsy, toffee coloured camisole. He wasn’t as handsome as Lauren seemed to think he was. But he had a casual air about him and a probing stare and sometimes that was enough, I thought, as I watched the boy take in the shorter and curvier dark haired figure of his girlfriend’s best friend.

“So nice to meet you,” I smiled sincerely, swaying my hips as I walked up the porch steps and extending a hand to Miles.

Feeling my soft, manicured hand in his, Miles swallowed, “You as well.”

“So, what do you think?” Lauren demanded as soon as Miles had left us alone to unpack, “Like, so sexy hey?” I smiled inwardly, it wasn’t just men who loved hearing how beautiful their prey was before devouring it. Even though Miles’ look was not’t my personal taste, I enjoyed the fact that other girls my age found him desirable, and in turn it fueled my desire for him.

“He’s cute,” I shrugged, “mind if I join you guys later?”

Lauren let out an adorable little giggle, “Sybil, you are so bad! I wouldn’t mind though actually…”

My ears perked up and I spun around from the vanity I had been applying lip gloss at, “Seriously?” I asked my best friend.

“No not seriously!” Lauren exclaimed, “You know how I feel about stuff like that. Anyways I’m gonna go see if Miles still wants to go to that bonfire later, you got everything you need babe?”

I nodded, watching Lauren’s flawless ass in her tight fitting yoga pants as she walked out of the room. Damn, I thought, for a second there I had let myself believe she might actually want me to join her and Miles. The forbidden idea excited me like nothing else.

I turned again to the vanity, taking in my sultry reflection. I reached for the strap of my camisole, pulling it down. That looked sexy, I thought, as I undid the zipper of my skirt.

I let the garment fall to the floor, never taking my eyes off my own reflection. So maybe Lauren wasn’t into the idea of me joining them, running my hands over my milky thighs, staring at how my pussy looked through my see-through lace underwear.

I bet Miles wouldn’t mind too much, I pulled the panties down, taking in the sight of my smooth, hairless pussy.

Mmm, why would he mind? I smiled at myself through the mirror while peeling off my camisole. I wasn’t wearing a bra – I didn’t need to.

My full tits bounced as I released them, their prominent nipples already hard from the thought of my best friend’s blond head next to my brunette one… kneeling at the feet of one lucky guy.

I did a little twirl in front of the mirror, loving the way I looked naked, taking a minute to appreciate the changes that were happening underneath my clothing.

I let my small hands take hold of my heavy breasts, tweaking the nipples between my fingertips. Gosh that felt good. I massaged my breasts with one hand, tracing tiny circles on my flat stomach with the other.

The circles lead my dainty fingertips to my now moistening slit. I watched in the mirror as my fingers parted my pussy crack, already slick with juices. One hand on my tits, the other headed for my clit, imagining Lauren, Miles and I…

“So babe Miles wants to leave in an hour," my best friend’s voice coming from the doorway of my room stopped my hand dead in its tracks. I watched through the mirror as Lauren registered what she saw.

Me standing in front of the three way mirror, naked, clearly groping my own tits and exploring my little cunt.

I could have sworn that her gaze lingered for just a few seconds longer than appropriate on my bald pussy… and then

“Oh my gosh Sybil! I am so sorry!” Lauren screamed, nearly hitting her head on the door frame in an attempt to escape the room faster.

“No, no I’m sorry Lauren!” I yelled back like an idiot, frantically reaching for the near by bed sheet and using it to shield my naked body, “It’s okay you can look, I’m covered.” Lauren’s embarrassed face turned around to look at me, her cheeks hot. “I’m sorry I was just putting on lotion,” I lied.

“Oh, uh, that’s okay,” Lauren avoided my gaze, “I just wanted to let you know we’re pre-drinking upstairs if you wanna join us.”

I did, want to join them.

To numb the awkwardness of our earlier encounter, Lauren and I quickly downed a bottle between us of wine from her parent’s cellar. Miles looked on delightedly at the underage rebellion that was rather uncharacteristic from both of us.

“So, Sybil,” he asked, “Why don’t you have a boyfriend?”

“Because Sybil’s too picky,” my drunk, white clad best friend answered for me, “Sybil gets hit on by everyone but no one is good enough for Sybil.”

As Lauren blabbered I watched Miles’ head turn to me and his gaze again fall on my cleavage.

“That’s not true,” I half heartedly protested, giving a little wink to Miles.

Miles put his hand on Lauren’s thigh, never taking his eyes off me. I felt jealousy run through me like a thunderbolt.

Later at the party, Lauren was drunk and unlike Lauren, I was not perpetually fascinated by the lame stories of every half-decent looking snowboarder we met, so I decided to part ways with my best friend for a while. Miles had deserted us long ago to do keg stands with his friends.

I decided to go and sit by the bonfire alone and drunkenly ponder, as I like to. Maybe it was because, selfishly, I somehow wanted to be apart of Lauren losing her virginity. Maybe it was because I was drunk, or maybe it was just because I really am a jealous bitch. Whatever the reason, when I saw Miles’ dark eyes staring at me from across the flickering fire, I decided to take advantage of it.

Slinking my way over to him, I really did not know how I was planning to act. This was nothing but a fraction of womanly confidence shining through the body of a girl.

“Wanna take a walk,” I gestured towards the dwindling fire, “Get some more wood?”

Miles was standing before I had finished my sentence and, not bothering to ask where Lauren was, began leading me into the dark forest. We made it about 50 feet away from the group before it became clear that we were not looking for firewood.

I felt Miles’ hands on me suddenly as he pushed me up against an especially large tree trunk.

“You’re gorgeous, you know that?” Miles breathed in my ear, his hand pulling one of my legs up around his waist.

“What about Lauren?” I purred, “Isn’t she gorgeous?” I felt his hand move farther up my skirt, having no apparent reservations at the mention of her name.

“Yeah, she is too,” he admitted “don’t get me wrong both of you are fucking hot but you’re just so…” I felt his hand move to my bare ass under my miniskirt, my tiny, pink thong doing nothing to cover its ripeness.

“So…?” I prompted, genuinely curious to have an older boy tell me exactly what he thought of me.

“So much of a tease,” Miles said sternly as his hand firmly squeezed my ass cheek and I felt his warm, hard mouth on my surprised lips. My intent had been to make Miles desire me, in an attempt to be included in the night’s fun, it had not been to steal him from Lauren.

Yet now that the muscular arms were around me, making me feel tiny in comparison, and my body was being roughly pressed against the solid wood of the tree, I was starting to see what Lauren saw in this guy. None of the awkward teenage boys I’d kissed before had attempted to push me up against anything, nor had I wanted their bony hands anywhere near my full ass. But this, this was different. This was new.

I felt my body immediately respond to Miles’ firm grasp, I kissed him back, not aggressively, but I did not push him away.

Clearly taking my kiss as an invitation to go further, I felt his rough hands slip under the thin strip of fabric between my ass cheeks, traveling under my thong to my moistening slit.

Whimpering helplessly as his tongue explored my mouth, I let Miles’ rigid fingers pry apart my pussy lips. My virgin cunt had never had a finger inside of it, not even my own.

It may as well have been a dick slamming into me as Miles thrust two of his fingers up my truly never been touched hole. I cried out in shock and pain, breaking away from the kiss.

Without his tongue probing my lips I realized more fully just what was happening. This was my best friend’s boyfriend, the boy that she was planning to give her virginity to tonight, and yet I had his hand under my skirt and his fingers up my too virgin pussy.

I started to freak out, feeling Mile’s hot breath on my neck as his fingers explored under my skirt.

“No, no Miles, I’m sorry no, I don’t know what I was thinking, please stop,” I pleaded frantically, trying to push his hand out of my now throbbing crotch.

“No what baby?” Miles crooned into my ear and kissed my neck as he started to finger fuck my poor little pussy, I was not used to this. For someone who had acted so bold – asked for this, brought it upon herself – I was suddenly in over my head.

“It’s wrong,” I tried to reason with myself as much as him, “Lauren is my best friend” I said firmly.

“I know she is baby but you were the one who wanted me to come on this little firewood cun… hunt,” Miles sneered as he pulled his two fingers out from my pussy, smearing the juice on my pussy lips and making his way to my puffy clit.

“She’s going to sleep with you!” I cried, desperate to think of something that would make him stop, “Tonight, she’s going to give you her virginity tonight!”

Miles stopped kissing my neck, but his hand did not stop rubbing my hardening clit. He kept one hand on the back of the tree, leaning back to look at my face as his other hand continued to assault my pussy.

“She is huh?” His cocky, delighted face smirked at me, “And how does that make you feel? Does it make you jealous baby?” Feel? How did I feel? Right now all I could feel was the slipping and sliding of Miles’ hand between my legs.

“What are you talking about?” I croaked, “Jealous of Lauren you mean?”

Faster Miles worked his hand, alternating between furiously rubbing my clit and pushing his fingers deep into my pussy. The sensations were intense and overwhelming and unlike anything I had ever felt before.

“No baby, jealous of me. Jealous that I get to fuck your best friend’s sweet little cunt”

My body froze, which only drew more attention to the action happening at my crotch and despite my best efforts my moans had been consistently getting louder the more Miles mentioned Lauren’s name.

“It’s okay if you are baby, she does have a nice pussy,” Miles drawled on, “and she thinks you have a nice one too.” I thought back to earlier in the evening, Lauren’s reflection staring at the dimple between my legs.

“Did, did she say something about my pu-pussy?” I gasped in Miles ear, no longer pushing him away but instead bracing myself against his broad shoulders.

“Yeah baby, she told me all about walking in on you earlier, how bare your cunt was and what nice tits you had.”

So I hadn’t been imagining the staring, I thought. I felt the bark of the tree scratching my back, the thought of Lauren’s eyes taking in my body and then her recollecting the memory to Miles was turning me on.

“So don’t worry baby just say it, you think she’s pretty don’t you?” Miles urged.

“Yes,” I felt my vagina muscles constricting.

“You’d like to touch your best friend’s sweet little pussy wouldn’t you?”

“Yes,” I admitted shamefully.

“Say it.”

“Yes I think she’s pretty, yes I’d like to touch her sweet little pussy” Oh gosh, I knew my orgasm was building, had I really just said that?

“I know you do baby, now say her name,” Miles demanded.


“Say it again!”

“Laurennn” I moaned

Lauren whom I’d shared beds with at sleepovers and changed in front of, Lauren who I’d practiced kissing pillows with and told all my secrets to. Lauren with her blond hair and her graceful form and her sweet little pussy. Lauren who was a mere 50 feet away, possibly getting closer should she be looking for her missing best friend and boyfriend.

The thought of her catching us combined with saying her name aloud put me over the edge, my walls spasmed against Miles’ hand, forcing his fingers out of my tight pussy as I bathed his palm in my sweet juices. I felt my entire body shudder and bit Miles’ shoulder hard to keep myself from literally screaming out my best friend’s name as I came.

“Fuck that was hot,” Miles complimented me, “mm Sybil you really are just as sexy as I thought you’d be.”

As though cumming was something I had practiced in front of a mirror – another one of my choreographed moves to seduce men – as if that hadn’t just been the first orgasm of my life.

“And I wasn’t lying baby girl, Lauren really did talk about your tits, and now it’s time for me to see them.”

“What?” I asked naively, only now noticing the bulging hardness pressed against my bare leg. Had I really been foolish enough to think that, having his fingers thrust deep inside this young and curvaceous body that melted under ever movement of his whimsical hand, Miles wouldn’t get hard? That he had made me cum with his hand while talking about his girlfriend, yet had somehow not become aroused?

“What do you mean it’s time to see them?” I asked timidly, already knowing the answer.

He moved my own hand down to the bulge in his pants, “Well we’re gonna have to do something about this now aren’t we? Wouldn’t want me going back to Lauren all hard and having to tell her who made me this way would you?” Miles threatened.

I knew he was right. Miles could tell Lauren that I’d brought him here and he wouldn’t be lying. Some innocent flirting would have been fine, she may have even forgiven a harmless kiss, but not this. Not knowing that I had for months denied the wandering hands of every boy I had met, only to drench her boyfriend’s knuckles in my sticky juices the night she planned to give him her virginity. No, she couldn’t find out.

Miles pushed me down, pulling off my shirt as he did so. I felt my bare knees scrape against the gravel and dirt as Miles hastily unfastened my bra.

“Oh yeah,“ Miles admired my full breasts as I knelt before him in the moonlight. He grabbed both my hands in one of his and placed them on his belt buckle, instructing me to unfasten it.

A large, very hard and dripping with precum cock was waiting for me at full mask beneath Miles' trousers. Pulling off his boxers, Miles asked? “You ever sucked on a cock before sweetie?”

He didn’t wait for the answer, which would have been no, before cupping my chin and sliding his length into my unsuspecting mouth.

“That’s it, suck on the head,” Miles said as he bent his knees, wrapping my tits around his thick shaft.

I did as I was told and worked my tongue around the salty but smooth tip as Miles began to thrust his cock between my tits and into my mouth. With both hands he held my tits around his girth as I bent my neck back to take his cock farther down my throat, each time him pulling back and slamming forwards just a little harder.

I stared up at Miles, my eyes filling with tears as I choked on his cock. How had this happened, how had I gotten myself into this? I wondered. Yet part of me loved serving Miles. He knew what he wanted and he was not holding back. After all he had given me an orgasm so I should be a good girl and help him cum too, I reasoned with myself.

I could feel him getting close now, his hands clutched to my breasts while he fucked my mouth. “That’s it baby, just a little more, you’re doing great,” his words encouraged me as I felt his hand take hold of my long, glossy hair.

I didn’t really feel I was doing anything at all as he savagely used my upper body for his own enjoyment.

“Mmm baby I don’t know whose mouth I like more, yours or Lauren’s,” the prick said as his thrusts became more rapid. I just kept my mouth wide open, taking his cock. I felt his cock hit the back of my throat a few more times before I heard him moan

“Fuck, I’m cumming.”

Miles yanked his throbbing purple cock out of mouth, my saliva coating the shaft and the mushroom shaped head swinging before my eyes as he stroked his load onto my face and tits. The consistantsy of the white substance was unlike anything I had ever felt before.

Lauren’s POV

It hadn’t surprised me when Sybil flirted with Miles, that was just what Sybil did. Sybil did things for two reasons, because she was bored and because she knew she was charming enough to get away with them. Smart as a whip, she was the girl who infuriated teachers by not giving a fuck in class, despite being so evidently capable. And yet Sybil, steadily, managed to match my grades, either skillfully bullshitting her way through or flashing some leg so she could cheat off the guy beside her. And so what if she got caught? What were our male teachers going to do, fulfill their fantasies of “punishing” her for being a bad girl? That was just the type of thing that would keep the beautiful, wealthy and spoiled Sybil from being bored.

So no, it did not surprise me when Sybil, with her serpent like movements, had hit on my boyfriend. What did surprise me was watching through the trees as Sybil got titty fucked by Miles.

Her big breasts bouncing, looking every bit as luscious as they had earlier when I’d “accidentally” on purpose caught my best friend naked in her room. The way she’d looked standing in front of the mirror touching herself, innocent and wicked at the same time, like her face in the moonlight now as Miles thrust his cock into her face. 

Her perfect body, why had I mentioned it to Miles when I had caught Sybil touching herself? It’s not like Sybil needed any drawing attention to. No, I’d wanted to make Miles think about being physical with Sybil. I’d wanted to make him think about her so I would feel less guilty about thinking about her.

And evidently he had thought about her, and now there he was, taking her. And it was making me so. fucking. hot.

My hand was in my white silk panties as I watched my boyfriend with my best friend. I felt the light blond peach fuzz around my slit dampen as my fingertips searched for my swollen nub.

Miles had hold of Sybil’s hair now and was fucking her pretty face. Ha, if the girls at school could see the queen bee now, I thought, dipping a finger into my cunt. I used both hands, one to rub my clit and the other to finger fuck myself, feeling no reservations despite being a virgin. After all, it was nothing compared to the dual action of Sybil’s tits and mouth my boyfriend was currently experiencing.

“That’s it baby,” I said to myself, “fuck her mouth good, you enjoy that.” I knew the soil would stain my white dress as I knelt on the forest floor, grinding my hand into my pussy, but I didn’t care. I was getting off on Miles using my best friend’s mouth unabashedly for his own pleasure.

“She deserves it baby, she’s been bad” I moaned, seeing Sybil trying to turn away as Miles picked up speed. Oh yes, I thought, this is it. I was so wet I managed to slide another finger into my soaking virgin cunt, in and out, in and out. In and out of Sybil’s mouth, that’s it baby, treat her like your WHORE.

I said the last word aloud, overwhelmed with feelings of anger and lust as I drenched my own fingers in cum. Frantically slapping my clit as I came, I watched Miles empty his load onto my best friend’s beautiful face.

More to come with Lauren involved, feedback is greatly appreciated

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