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The Natural Progression

Nate and Emily move from best friends to lovers.

“Nathaniel James Hollander.”

That certainly caught his attention.

My best friend stopped in his tracks and spun around cautiously. The caution was exaggerated, as were the furrowed brows. It would have been a truly comical sight if he wasn’t so good-looking.

“Okay, I need you to review this for me. It’s a competition entry,” I said briskly, thrusting a sheaf of papers into his open palm.

The piece was flash erotica and the competition, a Lush Stories one. But Nate didn’t know the fine details just yet. The both of us write for leisure (and occasionally, the college Drama Club) and we recently started going to each other for feedback on our work.

I trusted Nate to read my writing because I knew he would give me an honest opinion. Too honest, sometimes. I was still reeling from his remark last week: “Em, it’s a great script -- if the aim’s to get a snoozing audience by the end of the play.“ He only got away with that because we’ve been best friends since the fourth grade. And as much as I hated to admit it, his comments were usually spot on.

“So what’s this one about?” Nate asked casually. He flipped the cover page open and my mind conjured up an image of his deft fingers flicking at something. Of mine.

I panicked when I caught his intense green eyes scanning the top line of the story. “Nate!” I snapped, causing his gaze to shift quickly from the paper to me. Heat rose up my cheeks. I was mortified that my best friend was standing in front of me, reading erotica that I had written. Or perhaps the embarrassment really stemmed from the lusty thought of having his fingers on and in forbidden places; secret places that were off limits to best friends who were ‘just friends’ anyway.

“Sorry, I was thinking, maybe you should look at this after academic hours,” I suggested, eliciting a raised eyebrow from him. “The story’s pretty…complex. So you might want to read it in one sitting,” I explained, surprised by how calm I sounded when I told this little white lie.

I saw a sceptical look cross his face, but it was one that faded as quickly as it appeared.

Nate placed a comforting hand on my shoulder and peered at me, asking, “Are you alright, Em?” I just smiled back lamely. “You seem a bit jumpy about this one. It must be a pretty big competition. Which I’m not aware of. Strange, ” he mused.

I simply shrugged and breathed an internal sigh of relief when he proceeded to stuff the story into his bag.

Around us, students and teaching staff were walking hurriedly to get to their classes; which meant that we should already be on our way to ours. “I’ll see you at lunch?” he asked, waiting for my response, a nod, before walking down the hallway to the Maths Department while I started in the opposite direction towards the Language faculty.


I’ve never seen Em so antsy about her writing before. In fact, in the ten years I’ve known her, she hardly ever got flustered over anything.

But I might have a good clue why she was so nervous about me reviewing this piece. The opening of her story had been permanently seared into my mind. How could it not? Especially when it read: James Deen’s grunts from the idle laptop were drowned out by her lover’s own articulations of pleasure. They were not very articulate at all. And that’s how she liked it.

It was a bold opening, unsuited for a college-organised writing contest. My first thought was smut. But a girl like Em doesn’t do smut. Or does she? That opening had my curiosity piqued. The hardcopy of her story felt like it weighed a ton on my shoulders. And when I settled down in class, it still made its presence known by searing a figurative hole in my bag. (Melodramatic, I know. But I don’t apologise for sounding like an amateur writer.)

I rushed through the day’s calculus assignment so that I could set it aside and start going through Em’s piece. I re-read the opening line just to make sure I wasn’t imagining things.

I sure as hell wasn’t.

Her lips framed his girth nicely as she bobbed her head, deliberately letting him feel her tongue stroke the underside of his hardening shaft.

That line came after a few redundant sentences and I felt a sudden head-rush reading it; the kind you get when your head registers say, a naked girl on her knees for you, and relays the message to your other head, sending a rush of blood there.

Don’t ask me why, but the mental image that came up was one of Emily pulling my cock out of her mouth with a muted ‘pop’. That, along with the tantalising sight of her smiling in spite (or maybe because) of the sloppy mess we’ve made: my pre-cum blending with her saliva, stringing from her tongue and chin to my cock. Which she would, by now, be stroking rhythmically.

I resisted the urge to let out a guttural groan at that thought. But only because I was sitting in a classroom, flanked by my lacrosse team mates.

Admittedly, this wasn’t the first time I envisioned my best friend like that. I have lusted after her lithe body for about five years now. Even when I got my first proper girlfriend at sixteen, I still fantasised about what it would feel like to slide myself all the way into Em’s heat. And have her scream my name in wild abandon as I slam my cock into her tight-fitting snatch over and over again.

There went my head again.

“Man, I know you love maths. But not this much,” Terry on my left whispered, his eyes alternating between my blank face and the slight tent I’ve pitched in my jeans.

“Yes, the Fundamental Theorem of Calculus turns me on big time,” I deadpanned. He wore a look of disbelief but didn’t question further; one of the perks of co-captaining your college lacrosse team is not getting stick from the guys over a faux pas like that.

The next four hours of getting from one class to another were a blur. All I could think about was how badly I wanted in on Em’s sexy persona. It was one thing to read about it on paper, and I bet, quite another to actually be getting some with her.

Lunchtime rolled around quickly enough. I had promised to meet Em at our usual spot on the quad but first, I had something to take care of. In private.


I couldn’t believe what I'd just heard!

Nate bailed on me during lunch so that he could – get this -- wank to my Lush Stories competition entry in the last cubicle of the second floor toilet. Either this was the most ridiculous excuse I’ve ever heard or he’s patronising me. Just look at the straight face he kept when he told me that!

But then again, that may very well have happened; I noticed a few dodgy-looking spots on the top right-hand corner of page three, where the fictitious couple were finally on the edge of their release. Either those were bona fide cum stains or my imagination was running in overdrive.

It was nine at night and we were at his place now, discussing my first attempt at erotica. As usual, Nate got right down to business, telling me point blank which bits didn’t work while I defended them to the death. I’d admit, most died. Despite the nature of my piece, we somehow managed to keep the discussion light.

I was surprised that Nate didn’t have very much to say about my writing this time; he’s normally more critical, picking on the most minute of details.

“You sure you’ve got nothing more to add?” I prodded.

“To be honest, Em, it’s pretty much perfect,” he said.

“Wow, I never thought the day would come when I would hear Nate Hollander say my work was “pretty much perfect”,” I responded with a smile when I heard the sincerity in his voice.

“Well, don’t get used to it,” he teased, a smirk tugging on the edge of his lips. That earned him a playful smack on his bicep. The smug look gave way to a full-blown grin and we just stared at each other for a few quiet moments.

I could sense the playful mood shift to something else entirely. Something hung heavy in the air; I couldn’t decide if it was awkwardness or sexual tension.

Thankfully, I didn’t have to as Nate leaned in to me, the tips of our noses nearly touching. His warm breaths caressed the sensitive skin just above my upper lip. And then he spoke.

“Actually I just thought of an amendment we could make to your piece.” His voice was lowered to a whisper. “Tell me,” I whispered back.

The silence between us felt almost sacred. We both knew this was a crucial tipping point in our relationship. That neither of us dared to desecrate the moment with idle chatter or brash humour was a sign of our mutual acquiescence to embark on this.

“I was thinking, the introduction could start with Based on a true story.” He said after a pause. His voice was thick with conspiracy.

“It could,” I replied coyly. “But let’s do without the James Deen flick. I have all the inspiration I need right here.”

The hint of a smile played on my lips as I slid a hand down his torso, towards his fly.

My heart thumped against my chest as I got down on my knees before him and felt his fingers tuck a stray lock of hair behind my ear.

As tender as that gesture was, it did nothing to alleviate the deliciously dirty feeling that our first sexual encounter would be with our clothes still on. What a thrill. And the evidence of it would remain on my lace knickers after.

“So you’re going to be my little cock slut tonight, Em?” His tone was light, but his green eyes flashed with an intensity I’d never seen before. He meant business.

And so did I.

I tugged his boxers down and wrapped my lips around his flaccid member, confident that once I was halfway through, it wouldn’t be so soft anymore.


She kept her warm, hazel eyes locked with mine the whole time. The glint in them invited me to press forward, fitting more of myself into her warm mouth. I was about to withdraw but she kept me there and shook her head rapidly from side to side, letting my tip rub against the back of her throat.

Oh god, that felt so good.


At this point, most guys would callously thrust their hips forward to try and get right into my throat. I was pleasantly surprised that Nate didn’t. I made a mental note to reward him for that later.

I kept him deep until I was out of breath. Withdrawal was done skilfully with my tongue deliberately stroking his underside as I pulled him out.

The clear fluid seeping out of his slit excited me. Unable to resist, I flicked my tongue at his pee-hole and looked up at him as I clamped my protruding tongue between my lips and drew it back in, leaving the luscious frame of my mouth wet with a mixture of his pre-cum and my saliva.

That move produced the desired effect; Nate tilted my chin up and bent down to kiss me, forgetting about his cock for a while.


She wanted a kiss and I was more than willing to oblige, although my unattended cock was throbbing like crazy. Her tongue tangled with mine in a frenzied dance as my hands framed her gorgeous face.

Whoa, what was that taste?

Fuck, that was me. Never before have I kissed a girl who’s got a mouthful of my arousal. This felt so strange and so right, in the filthiest way ever. I just couldn’t get enough of it. Of her, of us. Good Lord, Em was turning me into a kinky bastard.

We were definitely champions for the dirtiest first kiss ever.


After what felt like a dizzying eternity, Nate finally pulled away.

“Em, get back to work,” he said in a terse voice. It was an order I was only more than willing to comply with.

I spit on the head of his cock, wrapped my fingers around his shaft and started to stroke him furiously.

“Mouth, Em. I want in on that sweet little hole of yours,” Nate said kindly. Well, as kindly as he could in that painfully aroused state.

Obligingly, I popped him back into my mouth and was pleased to notice that he had hardened considerably in a span of just about five minutes. I let my teeth graze the length of his rigid shaft before tugging gently at the mushroom tip.


The kiss was amazing but my cock needed to be inside her mouth again. I could barely watch as she sucked me with an enthusiasm that would put a cheerleader to shame. It was such a turn-on, watching her revel in this as much as I was. And I was more than happy to let her know how much.

“Jesus, Em,” I groaned, robbed of the ability to speak in proper sentences as she gently grazed my cap with her teeth. The sensation of hard enamel on raw skin was electrifying. I shuddered slightly as she continued doing that.


Nate had elicited quite a few guttural groans by now. Don’t get me wrong, I was turned on by each raw, masculine cry of pleasure. (Especially when they’re coming from my best friend who just turned into my – um -- we’ll just figure that out later.)

But I wanted more than just aural enjoyment from giving him head. I wanted something tangible. Something I could taste, touch, smell. Share.

This time, I swore I wasn’t going to pause for a break. I’d give his his reward now.

Hungrily, I took in as much of him as I could and felt a sense of Déjà vu as his head pressed against the opening of my throat. I took a deep breath and widened my mouth, simultaneously relaxing my throat muscles.


Holy shit. Was she planning to deep throat me?


I felt fingers bunching in my hair.

No! No! Don’t force me down!

I panicked and my throat muscles clenched. I wasn’t ready for this yet. Deep-throating needed to be put on the backburner for now.

“Em, just do your thing,” came Nate’s voice. The strong pair of hands at the back of my head was not pushing me forward as I feared. They were just holding up my long hair, keeping them out of my face as I continued to bob my head around his length, alternating between sucking and licking.


She wasn’t ready for this yet and that’s fine. Actually that was more than fine. Every nerve in my body was responding to her expert tongue as it alternated between swirling around my tip and stroking up and down my length. Watching each cheek puff outwards as she filled them with my cock only heightened every jolt of electricity that was coursing through my veins now.

“That’s my girl,“ I whispered coarsely, sweeping her bangs away from her eyes.


I felt slightly ashamed for doubting him and falsely leading him into thinking that he’d get to fuck my throat tonight. But more than that, I felt empowered by his reassuring voice and touch.

The stubborn girl within decided to get the better of me by emerging right this moment. I parted my lips wide and relaxed my throat muscles again. This time my head followed with a quick nod downwards, taking his cock right into my deepest oral cavity.

“Ohh fuck!” Nate exclaimed in surprise. I didn’t care that I felt like gagging -- I was just basking in the excitement of catching him off-guard with that.


Ohh fuck! My body convulsed slightly at the snug fit of her throat around me. I exhaled slowly, afraid to hurt her with any sudden movement. Maybe I was even more afraid that I might cum right there and then in her orifice. My mind was paralysed by the excruciating tightness around my cock.


I placed my hands on his firm ass cheeks and urged him forward. I think he was still adjusting to the grip of my throat muscles because it took a few gentle smacks on his ass to finally get him to start lightly thrusting his hips.


God, I couldn’t think straight anymore.


The feeling of getting stretched like that was overwhelming. My eyes could no longer contain the salty tears that were welling up. I felt them spill over and roll down the sides of my cheeks as Nate continued to rip at my throat.

He was fucking me at a new intensity now; the sound of his ball sacks slapping my chin rang in my ears. All manner of expletives were flung with abandon as he used my tight little cavity to find his release.

Just when I thought I couldn’t take more, Nate pulled his entire cock out of my throat. I doubled forward, choking, and felt his hand at my shoulders, steadying me.

“Open wide, Em,” he commanded, his voice firm but strained.

My mouth was already agape as I was gasping for air. Nevertheless, I stretched my lips even further apart and looked directly into his eyes as he clenched his fist around his cock and stroked his pulsing shaft.

My vision was still blurred by the tears from earlier but I definitely felt the first spurt of his cream hit my tongue. I started to close my mouth to savour the taste of it when Nate snapped, “No, I’m not done.”

Each rope of cum that hit me was punctuated by a fragment of my name. Emily. Olivia. Sharp.

The hot, sticky fluid that had not made my tongue streaked my cheeks, chin and neck. The stuff on my neck was dangerously close to soaking my favourite blouse but right now, I didn’t care. I just felt a swell of pride in my chest, knowing that I had somehow managed to extract such a huge load from him.

My tongue was still sticking out slightly and Nate, wearing a look of pure satisfaction on his face, seemed enthralled by the sight of it coated in cum.


I swear I lost my mind back there.

“I can’t remember the last time I came this hard,” I told her. I didn’t bother to disguise the wonder in my voice and was rewarded with the most beautiful smile I’ve seen on her. It didn’t matter one bit that I had made a Pollock out of her face with my cum.

I chuckled. Only Emily Sharp could have put the thought of Jackson Pollock in my head after giving me mind-blowing head.


Wait. Did he just laugh? I hoped he deduced correctly that I was frowning because I didn’t like being an outsider on an insider joke. Especially after what I’d just done with him!

“You look beautiful, Em,” he said, cupping my face gently in his hands. That didn’t explain anything, I thought.

“You probably weren’t expecting this, were you? Otherwise you would have opted for waterproof mascara.”


“Did you just diss my ruined mascara?” I rasped at him with mock fury. Nate laughed again and dismissed my question with a wet, sloppy kiss. This time, the tongue-dance transferred not just the taste of himself but also the mess he made on my face.

“After all these years, I still don’t know how you can stand my brutal honesty,” he said quietly when we broke for air.

“Must be “all these years”,” I theorized, earning a wink from him. 

“Shall we celebrate “all these years” by getting naked then?"

The orange lava lamp casting a faint, sensual glow on their now-naked bodies was a gift from her for his sixteenth birthday. No last-minute ‘Are you sure’s were uttered as his pulsing dick teased her wet opening, coating her lips with his arousal.

Tonight would change nothing and everything between them.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © © 2014-2015 X Sharp.

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