The Comebac Tour: Promises to Eep

I've had a rough life in high school. Well, rough isn't exactly the word, uneventful seems more fitting. No one actively disliked me, nor did anyone actively had any interest in me, apart from a handful just as uneventful and awkward friends. I graduated as a kissless virgin, even though the female sex had more than piqued my interested, although this interest was never reciprocated. I moved to a university city after a few years of work, got a studio there, built up confidence, grew a beard, got into poetry and I soon found myself in the middle of a sexual renaissance, or naissance, since for a re- to be in effect, it must've happened before. Every other week I had another choker-wearing hipster girl tied to my bed, her soft voice begging for my cock to fill her little holes, to fuck her obvious daddy issues away. I happily indulged in their little fantasies, being the brooding poet until they shoved me aside for a guy who's more into vegan non-gluten fat-free soy foodtruck festivals. It was a mediocre life in all respects, my philosophy major went decent, the poetry-performances brought in a little cash and the girls were always willing to go home with me after a little bit of effort and scotch. I always joked to myself that my 17-year old me would never believe the life the 24-year old me is living, yet I still owed my younger me a promise: to fuck my high school crush.

It's not like my socially awkward high school-version ever admitted to crushing on her, my behaviour at that point in my life was so antisocial she never even bothered to put me in the (in retrospect non-existent) social prison that is called the friendzone. She sort of acknowledged my existence and I jerked my cock raw thinking about blasting my hot seed all over her firm E-cups. But luckily, times changed and so did I. A few weeks into my second semester I went to a local pub after a reasonably well-received performance. After I took a sip from my slightly overpriced scotch a voice with a hoarseness usually reserved for sorority girls called out my name. Actually, not called, sung almost, there was a melody to it, a melody that crushed my ego back to the insecure seventeen year old me. "Robbie?" the voice repeated, her fingers ever so lightly touching my shoulder. I turned around and the sight I took in was even more breath-taking than the last lingering look I gave her on graduation day. The locks of her dark brown, curly hair cascades over her ample breast, the tight black and white dress accentuating her nothing short of magnificent assests. Her cheeks had light dimples as she smiled at me, the freckles on her face framing her pale blue eyes as my gaze inadvertently went over her body, from her tight belly down to her toned legs and her pretty feet in black, open-toed heels. As my mind and gaze unfroze I tried managing a coherent sentence:

"Jessie! Long time no see!" I exclaim far too enthused as I extend my arms for a hug, she hugs bag, the scent of her perfume intoxicating me slightly as my fingers touch her bare shoulders. "what brings you here?" I ask, her hand still lightly resting on my shoulder.

"I lost my friends." she answers, her hand still lightly lingering on my shoulder. "Well, lost, the two of them went home together and I didn't want to go home yet, so I went here for a nightcap. What brings you here tonight?" she asks in reply as I stand up, loosening my tie as I motion towards the smoking-room in the pub as I pull out my cigarettes, she nods knowingly and starts walking towards it as well.

"A nightcap as well, just finished performing." I say as I hold the glass door open, leading her inside and stealing a glance at her perfectly trained ass, she glances over her shoulder and smiles mischievously.

"Still like staring at me huh?" she says bluntly as she sits down on one of the worn down leather couches, crossing her legs as I stand there slightly frozen, shocked by her bluntness, I gather my bearings and take a quick sip of my liquid courage.

"Of course I do, you're gorgeous." I blurt out. She bursts out laughing as I sit down next to her, lighting my cigarette and offering one to her as soon as her fit of laughter dies down.

"What did you do to the timid kid in high school?" she jokes, chuckling after her full lips take a drag from the cigarette.

"I guess he died about the time I got the beard." I joke back, my eyes looking into hers a bit too long as she shifts her gaze to my beard.

"It suits you." she says, her fingers teasingly brushing the beard before she grabs my scotch and takes a sip. "I guess we're both hot now." she adds as she puts the glass back, flashing me a brief, playful gaze before she leans back on the couch, thrusting her breasts forward. "So poetry and philosophy huh?" she says as she shifts on the couch, getting more comfortable as she focusses on me. "I don't like any of those things." she adds.

"Well, we can't all have good taste." I retort, actively using the confidence I gained in the last five years.

"Yeah, which is probably why I'm flirting with you right now." she replies before bursting out laughing again. I shake my head and chuckle softly in defeat.

"You got me there gorgeous." I manage to say between her laughs, the fact of her flirting with me not even dawning on me. The laughing slowly dies down as we both lean back on the couch, gazes crossing. "Let's go." she suddenly says after a moment of silence. "You're poet, I'm pretty sure having a stash of booze in your apartment is mandatory, and possibly drugs as well." She grabs my hand after she finishes her cigarette and soon we're walking out on the street, my hands deep in my pockets as she walks next to me with an elegant grace uncommon to this hour of the day.

After a bit of small talk, underhanded flirting and discussing what we've been up to the last five years of our lives we turn the corner to a long street, on the end of which I live.

"I know you had a crush on me." she says, smiling almost sweetly as her tough, no nonsens girl-façade slightly cracks. Before I can reply she continues. "I never liked you in that way though, you were a sweet kid. But hot damn you've changed." she bites her lip playfully. "For the better that is." she adds almost sheepishly. "To be honest I figured you'd still be living in your moms basement, doing some community college thing after which you stay wilfully unemployed until your lonely death in the same basement at approximately 43 years old." she says, rebuilding her façade in a single sentence. I chuckle in response.

"Yeah, now I'm majoring in a subject that'll leave me unemployed as well, but at a university. A step up from your expectations I guess." I start getting more brash, wanting to see how far I can go. "You haven't changed though. You're still a bitch. A drop dead gorgeous bitch. I admire that, it's attractive." Admittedly the alcohol may have fed the overtones in that comment, as she stands in front of me, blocking my way, her five foot nine with four inch heels still way too short to look even the slightest bit of intimidating to my towering six foot six.

"A bitch huh?" she says, a mischievous smile on her face. "How about this bitch decides to go home on her own right now?" she looks me dead in the eye. I chuckle. "A pretty girl like you alone in the street? That's asking for trouble." I take a step closer to her, our gazes not breaking, my heart beating in my throat.

"I can hold my own." she retorts, stepping closer herself as well. "I could break you if you want, boy." her chests heaves as her breathing becomes heavier. I know she could, her toned body could sling my frail pencil-like physique around if it were nothing, yet I step even closer to her, towering over her as I pin her against a wall, my hand next to hear head as I think I hear a sliver of a moan escape her lips, our bodies almost touching as the tension could be cut with a knife.

It's palpable, one could smell the sexual energy in the air around us as our heavy breaths are the only noise in this dark night on the outskirts of town.

"Prove it." I almost hiss, my lips almost brushing against her ear. "Go ahead. Try it, bitch." emphasis heavy on the word 'bitch' as she casts her head down briefly before looking me in the eyes again.

"Fuck you Robbie." she groans before grabbing my hair and slamming her lips into mine. Without giving my brain a modicum of time to process what's happening, she slips her tongue between my lips, I feel the coldness of the scotch and the bitterness of the cigarettes on her tongue as I kiss her back just as feverishly. My hands slide down the curves of her body, grabbing her toned ass as I pull her closer, one finger hooking under the hem of her dress, teasing the bare skin of her cheeks as I make my kissing more aggressive, lightly sinking my teeth into her lower lip and pulling it towards me, eliciting a soft moan and a lust-filled look from her icy eyes as one of my hands travels up her spine, her skin feeling electric up until I grab her hair and suddenly pull it hard, drawing a loud groan and a "Fuck" from her as I let my lips explore her neck, the smell of her perfume now lingering on my lips as her hand travels down my body, pulling my shirt from my slacks before her cold fingertips travel over my belly, her hand snaking inside my slacks without warning. I let her hair go as she leans in close to my ear.

"Someone's exited" she whispers playfully before she nibbles my earlobe, her thumb rubbing precum all over the head of my cock. "I need that thing between my lips." she adds, almost making me cum on the spot. To turn the tables on her I suddenly turn her around, making her face the wall as I grind against her, her hips grinding back passionately.

"I definitely am excited to turn you into my little fucktoy." I hiss in her ear, the words alone causing her nails to dig into the brick wall. I grab her arms and bend them behind her back, she letting me use her as I use my tie to tie them behind her back. "Walk." I say, slapping her ass, making her let out a little scream as she walks in front of me, her hips moving just that bit more as we finish the final yards towards my apartment, Jessie occasionally casting a wanting look over her bare shoulders, a streak of lipstick smeared over her chin.

As we enter my apartment I waste no time before bending her over my desk, Jessie wilfully obliging as I push her dress over her hips, her heavy breaths interspersed with small, hoarse moans. I rip off her panties, smelling her scent on the black, lacy thong as her two holes are now exposed to me: one shaven and dripping and the other part of the most magnificent ass of human history. I start kissing the unblemished skin of her perfect cheeks.

"Robbie, fuck. You fucking tease." she groans, her hips grinding in anticipation. "Lick my fucking pussy I know you want to." she lifts her hips, almost pushing her dripping sex in my face. I stand up and spank her hard, drawing screams, shouts and moans from her as I continue to do so. I pull her hair. "Don't tell me what to do, you bitch." I growl in her ear as I pull her dress and bra down, exposing her large tits, her left nipple adorned with a piercing. I pull the pierced nipple. "Someone's a kinky little girl." I hiss, making her moan and shriek as I toy with her body. "Now, if you want me to lick your greedy little pussy, then beg like the slut you are." I let her hair go, her body slouching over the desk as I stand behind her, my fingers teasing her soft skin as she weighs her options.

"P-please." I hear faintly after a while. I lean close to her, my bulge pressing against her.

"Please what?" I ask, knowing she's mine now.

"Please lick me..." she swallows hard, almost sighing. "...sir." I can feel the redness of her cheeks as she utters the final word, knowing she's beaten by her awkward high school classmate, knowing that she desires nothing more than my tongue sliding over her wet slit and my cock ramming in and out of her perfect little pussy.

Having teased her long enough, I push her shaking legs apart, slowly dragging my tongue over her wet slit, gathering her juices on my tongue, savouring the taste before I swallow them and start to go down on my high school crush, my tongue frantically dancing over her wet lips as my thumb rubs her clit, my nose almost buried in her puckered, untouched asshole. My ministrations draw moans and bucking hips from her, her arms straining against the tie around her wrists to no avail. I decide to up my game and spread her cheeks. "What are you doing?" she asks, out of breath, but instead of replying I slowly let my tongue inch closer to her little ass. "Robbie no." she says, now straining harder as I push her ass down on the desk. "Robbie no-oh my god." she says as my tongue now reaches her asshole, her reservations turning into moans as she grinds her ass against my face. "Jesus fucking christ Robbie." she moans deeply, my thumb once again finding her clit as she starts to buck more feverishly.

"Please don't stop Robbie, please don't stop sir!" she corrects herself, loudly I might add, as my tongue and finger continue to play with her body. Her moans turn more frequent, after a while being replaced by a collection of profanities, figures of religious authority practicing odd hobbies (Jesus tapdancing Christ) with her rise to climax culminating in a seemingly endless string of "yesyesyesyesyes" as she cums, loudly screaming my name as her juices drip down her legs, her entire body trembling as the grinding slows down, her moans now soft and gentle. I untie her, slowly kissing my way up her back until I find her lips, we kiss deeply as she turns herself around, her hand immediately reaching for my bulge as she passionately kisses me back, even biting back sometimes. "Lie down on the bed, I want to fuck you until you pass out." she manages to say between kisses before she guides me to my bed and pushes me down on it, immediately climbing on top of me and teasing my cock with her wet, tight lips. She moans lightly as she looks deep into my eyes, not breaking her gaze as she pushes down on my cock, her mouth taking on an o-shape as her incredible tightness envelops my cock.

"Fuck, you're so tight." I manage to groan before she starts to slowly bounce up and down, her tits swaying with the rhythm of her motions, her hands wrapped around my neck as she starts to properly fuck me, gaining pace, throwing her hair back, allowing me to sink my teeth into her neck, making her moan once more. I grab onto her ass as I start to meet her thrusts, a playful noise coming from her lips as we continue to fuck like animals.

"You really like my ass, don't you?" she says mischievously, in response I spread her cheeks and slowly push a digit of my index finger inside her tight little hole. The o-shape of her mouth returns as I do this, drawing more religious figures and profanities from her mouth as I find her lips to kiss her and shut her up, not wanting to wake my neighbours with our romping. She bites down on my lower lip and smiles at me.

After a while of fucking in this way she slowly gets off of me, crawling further onto my bed as she casts a glance over her shoulders, a teasing smile as she moves her ass upwards and her face towards the bed. Not denying this hint, I get behind her and ram my cock back into her, leading to a scream from her side as my thumb finds its way inside her ass once more. Her moans get muffled by the pillow as I see her hands claw and grab onto the sheets. Not being able to take the sight any longer without doing anything, I start to spank her ass hard and repeatedly, with her screaming louder at every spank as I continue to give her the fuck of a lifetime. Knowing I can't last much longer I pull her hair back. "You're going to suck me and I'm going to cum in your mouth. Understood?" she smiles and moans in reply.

"Yes sir." she adds as I stand next to the bed, her lips wrapped around my cock before I even had time to notice. Her eyes look into mine as she manages to slowly fit the eight inches inside her throat, my hand buried in her hair. Her tits are glistening with sweat as I slowly start to fuck her mouth, her own hand disappearing between her legs as she expertly sucks my cock, sometimes stopping to take a long lick from the base to the tip or to take one of my balls into her hungry mouth. "Cum for me daddy." she suddenly says, imitating the hipster-girls I may have told her about during our small talk. Yet the sight of her pumping hand wrapped around my cock, her big, innocent eyes looking at me and the sight of her tits make me quickly shoot a hot load of cum, with a few strands landing in her hungry little mouth, but the most of it landing on her firm, big tits. She moans and giggles with glee as I do so, cleaning her tits with her fingers as I lie down on the bed, exhausted. She curls up next to me as she takes her dress and heels off, her pretty toes teasing my lower leg as she looks at me. "We should do this again sometime, say tomorrow morning." she states matter-of-factly. I pull up the sheets, giving her a small peck on her lips as I wrap my arm around her.

"We definitely should, I'm not yet done with you." she moans in anticipation before we fall silent.

"Good night." she whispers sweetly as she snuggles up closer.

"Sleep tight." I reply, not yet knowing, but looking forward to the days to come.