`Crossing The Line' is a fictional work of adult erotic fantasy, involving consensual sexual relations between both men and women as it explores the theme of one man's journey into the world of bisexual relations with other men and as such is intended for adults only.
This story is in no way an endorsement of such relationships in real life, and this author adamantly rejects any justifications for such relationships or activities in the same. It is purely a work of fantasy and as such this author maintains an awareness of where real life ends and fantasy begins.
Copyright, Tom Pearce, 2024.
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Crossing The Line
It's Just Sex...Isn't it?
Chapter 1
Michelle was just the sort of girl I was looking for. Big tits and long legs that went all the way up to her pussy...an awesome wet one if I remembered rightly...luscious lips a guy could eat his way through and make a meal of that hot juicy flesh inside...ok so we weren't exactly old friends but we'd fucked a couple of times and it was always good.
And right now, she was just what I needed. Thirty years younger and hot to trot.
Like me she had a son -- I guess that made us both single parents although...well there was no denying there the similarities ended -- Danny was 14, a good 10 years younger than my son, and as wild as I knew Michelle could be in the sack if Danny was home I'd have to settle for a quick fuck in the back of the car...but I figured 20 mins in a pussy like hers would be worth it...there was no way I could take Michelle back to our place.
So that evening I wound up at the Flamingo Club...big mistake...a much younger crowd...at best I must have looked like a father waiting to take his daughter home from a party...at worst an old jerk trying to hold his belly in whilst all around him much younger six packs stretched through tight T shirts and vests...whilst raised smooth arms showed off fine sweat soaked pit hairs and perfectly sculpted biceps...bodies like my sons... young, alive with their own vitality...totally assured in their own skins...knowing their worth...the power of their attraction...the confidence of youth...
Sure, a couple of girls accepted my offer of a drink...stayed around long enough to flirt but I could see they kept one eye over my shoulder looking and holding out for something better...did some young girls look for a father figure...or was I in danger of becoming some sort of pity fuck they could laugh about in the morning...?
`He was HOW old?'
`OMG I KNOWWWWWWWWW...I guess I must have been really out of it lolololol'
No I was no pity fuck...no father figure looking for small girlish tits and a shaved pussy...I had a big dick, full balls and the power to use both...what I needed was a WOMAN...
And there was Michelle...both of us in the wrong place at the right time.
I recognised her immediately...already remembering as she walked towards the bar how those amazing breasts had bounced out when I'd undone her bra...the feel of that dense bush...shit I swear if I'd put my finger in my mouth and licked it I could have actually tasted her cunt on it...the memory was that strong.
Some of the younger guys looked and nudged one another, laughed and licked their lips as they whispered together...
I thought `dream on lil boy! This is one hot arsed gal who needs a real man'...and that man was gonna be me...
The good news was she remembered me, maybe not as well as I remembered her but the more we chatted the more recognition I saw in her eyes...recognition or need? Did that matter? The place was loud...and if she was too old to be there I certainly was...
We chatted about life...not the real details...she was on her own these days...so was I...she wasn't looking to share her life with a man ever again...she had her life, her job and her own home...and I wasn't looking to share my life with another woman...but I realised we both knew more about each other's bodies than our minds...but we knew the game, and we knew the rules...
`A perfect match then Michelle 😊'
`Well Tom I could invite you back for coffee...or.... 😊'
`Or lol?'
Or you could just fuck me with that massive dick of yours lololol 😊
`You still remember it then?'
`Maybe I need reminding just what a stud you are Tom...'
I whispered that maybe I needed reminding what a glorious pussy was hiding in her panties..
`Then let's leave these kids to play in the sand-pit 😊' she grinned.
`And what about that kid of yours?'
`Danny?, Oh we don't need to worry about him he's staying over at his buddies...'
So we left...and headed back to her place...my eager cock already unfurling in my jeans...
Well fuck the coffee!
The door was hardly closed behind us before I grabbed her, driving my tongue deep into her willing mouth...our lips hungrily working over and over each other as if we'd never kissed anybody for an age...as our bodies ground together...my fully aroused bulge pressing against her stomach...my hands cupping her tits through her blouse...that familiar warm wet feeling soaking into my underwear and I swear....the faint scent of a pussy starting to simmer...
Who dragged who into the bedroom? I don't know but we headed straight there...straight on to the bed...my hand reaching behind her and unzipping her skirt exposing her lace covered arse to my touch...her hand massaging my dick...fumbling with my zipper...slipping inside and wrapping itself around my cock through my briefs...
I pulled her skirt off...fuck what a sight...those long legs encased in the sheerest of stockings...the black lace triangle of her panties framed by her suspender belt...the unmistakable scent of cunt...
Raising my arms I let her tug my shirt over my head...exposing my hairy pecs...releasing the scent of my pits...her lips already nibbling across my chest...finding my nipples in a series of sharp bites that triggered such a pulsing in my cock I thought I was gonna cum right then and there...
I'd always been a nip-man. Even masturbating as a kid I'd soon discovered the extra pleasure tweaking my own nips could add to the sensations building in my young teen dick...it was just a shame in never occurred to most women that a guys nips were just as sensitive as theirs...but Michelle wasn't `most' women. She was one crazy lady who knew her way around a guy's body and expected, nope DEMANDED he showed the same expertise with hers...and I knew from experience that under that blouse was a pair of tits any guy, of any age would die for.
It was me that broke the moment. As much as I enjoyed the way she licked, nibbled and bit on those rock hard nubs of mine I pushed her back on to the bed and damned near ripped off her blouse...spreading it wide to reveal her magnificent tits in the smallest of lace bras...breasts I immediately squeezed and sucked through the fabric...working my hand behind her and in one expert movement releasing the catch...the full weight of her breasts causing them to drop out right in front of me...the same big creamy tits I remembered from our last fuck....the same erect nipples in my mouth as I squeezed them roughly into mounds...my hungry bites and sucks matching her moans and yells as we writhed together...my cock aching for release...
I moved a little off the bed -- struggling to remove my jeans and underpants...my swollen cock caught in the fabric....rearing up as it was freed...already dripping precum...my frill half back exposing my knob and then......
`OHHHHHHH FUCKKKKKKKKKKKKKKKKKK'
Michelle went down on me, one hand around my root, her warm tongue flicking every contour of my helmet...her squeezing fingers making the ridge of my knob swell and becoming even more defined....my fingers in her hair...pumping her head on my dick...deeper and deeper each time as she gagged and slurped...those stupendous tits bouncing and swaying all the while.
Eventually she pushed me away...gasping for breath...her mouth wet with precum...the scent of her pussy stronger...intoxicating...
I took one look at her as she sprawled out on the bed and had only one thought on my mind...she was gonna get fucked...good and hard...
...as I kissed down her body...lower and lower until my face was pressed against the wet mound of her pussy...tasting the juices as they seeped through the lace...the slight contour of her slit already outlined through the sheer fabric...my teeth pulling them lower...exposing a fine crop of dark pubes that I licked and tugged with my teeth...pubes that already tasted of her intimate place...
This was a pussy that knew cock...this was no virgin school girl...and there was only one dick it was gonna know tonight -- MINE!
One more tug and there it was...a shining slit with two smooth lips...a red gash between her thighs...the sight as fascinating and arousing as it had been the day a fourteen year old paper boy had gazed upon his first pussy...Marge Henson's pussy...the one that was soon to engulf my half grown teenage dick for the first time....the pussy that took a boy's ejaculation and churned it into a real man's seed...
Only this wasn't a half grown boys cock...this wasn't a young boy looking with a mix of fear and fascination at a mysterious opening...I was man...a big hairy fucker with a throbbing seven inch dick spewing pre-cum all over the bed....a dick that was gonna fuck this pussy into a molten mass of burning quivering flesh...
But first things first. One good tongue deserves another.....
`ARGHHH TOMMMMMMMMMMM!'
I ran my tongue along her slit...long slow licks each one a little deeper than before...losing my senses in the steaming heat ...eventually finding the frilly inner lips...working them apart with my tongue and into the soft flesh of the tight hole they guarded...
Another scream...her legs kicking as I buried my face in her juicy cunt...my fingers spreading it as I worked deeper and deeper....finding that little hard pleasure button with my tongue and teeth...her scent all over my face....my mouth sticky as I satisfied my thirst on the sweetness of her most intimate juices...that mix of honey and musk...jabbing my tongue like a small wet dick in and out of her pussy as I steadily tongue fucked that slimy hole into a state of quivering ecstasy...
Her screams grew louder...her kicks and writhing less and less controlled...her hand pushing my head deeper as she squirmed her pussy against my face, my lips, my tongue in a mounting frenzy until her whole pussy spasmed -- a hot steaming living thing as her climax shuddered through her body....loud...wild...abandoned...
`TOMMMMRRGHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH!'
I knelt back...her open pussy still quivering with the aftershock of its own release...dribbling a trail of my spit mixed with her own sticky sweet juice...a pussy that was now ripe for the taking.
So I moved over her...nudging my wet knob against those spread lips...a pussy that though wet and aroused still resisted my first attempts to enter her....so I pushed harder....she groaned and raised her hips under me...the soft lips of her entrance slipping back my frill...
`TOMMMMMMMMMM....TOMMMMMMMMMMMMMMMMMMMM!'
And I rammed again -- clench my arse tight...forcing the power of every muscle into the veins of my cock...so hard...so deadly and poised for the kill...
OHHHH FUCKKKKKKKKKK...how those wet lips welcomed me into her heat! Engulfing three inches of my cock...then four....then five as I ploughed deeper and deeper each time....six inches and I could almost feel her ready to give way and surrender her body to the thickness of my root as it wedged inside her...stretching that hidden hole tighter and tighter...the heat and slime of her cunt seeping into my bush as she reared up under me...legs locked around my waist...her pussy at the perfect angle to be punched and fucked over and over...my cock at the perfect angle to slam against her clit...over and over...the sound of each thrust as my cock squelched deep into the red twitching flesh....flesh I could no longer see...only feel as her insides parted and closed around my thrusting knob...
Our mouths locked together...muffling our moans and cries...our breaths filling each other's lungs as our bodies slapped against each other...faster and louder...my balls slapping against her entrance...my dick burrowing as it speared those velvet walls....my hands mauling her breasts...savagely squeezing...teasing...torturing as I began to lose control...Her's clawing my back...her nails digging in the firm muscles of my arse as it rose and fell...
This was fucking...pure and simple...everything a man's dick was made for...to thrust and plunder ....everything a pussy was designed to do... to slide and squeeze and writhe...Man sex -- sex as it should be...as it had always been and would be again...
I felt a huge jolt at the base of my dick followed by an orgasm so powerful I threw my head back and yelled...roaring like a lion making it's kill...stabbing my sperm over and over into the rippling depths of her body in a huge explosion that filled her with so much spunk I could feel and hear it squelching around my dying thrusts... .
For a while we lay...sweating...panting...tasting of each other ...the functional afterglow of two people who had satisfied their mutual needs...nothing more...nothing less...I could feel her spasms fading around my cock...each one squeezing a little more life out it...as it softened and shrank...and eventually slithered out of her in a trail of foaming cum and pussy juice....which I ate...
My GOD! Did I eat....our mixed slime coating my tongue ....the soft bruised flesh yielding up its heat to my lips...her body jolting as I licked and sucked her clean...tasting my own cum....
I thought back to that long ago afternoon, my bike lying on the grass of Marge Henson's front yard...the room in half-light...enough light to reveal the naked body of a woman thirty years my senior...enough light to reveal the almost smooth butt of a 14 yo lad suddenly still, his teenage dick spent...his young cock shrinking as his mind whirled in the twin storms of guilt and exaltation...a dick small enough to be expelled as her knowledgeable pussy squeezed me out of her...
There had been no after glow then. And there was none now...
Should I go? She said `stay'...so I stayed...triumphant...powerful...a woman's soft body wrapped in my arms...my hands cupping those breasts...no longer pawing and pulling but caressing...softly teasing her nipples as I kissed the back of her neck...desperately remembering the scents and tastes as other memories crept in...
The hurried dressing, the embarrassed tugging on of underwear. The smile on Marge Henson's face that I took as barely disguised laughter because I knew I'd cum so quick...too quick...memories that were easily banished in my victory...or vanquished in Michelle's.
But it didn't matter who had won or lost as I moved my hands from her breasts...my fingers trailing down her stomach...tickling....making her giggle...giggles that turned to soft moans as they touched her wet pussy...before slowly pushing in...in through the lips...into the slippery heat of her just fucked slit with slow sensuous movements that mirrored the way she writhed slowly back against me...the soft mounds of her smooth ass cheeks squishing against my slumbering cock....
...my awakening cock...
...still wet with her honey...growing and growing... growing between them ...unfurling in the moist heat of her crack...the smooth skin already slippery with my pre-cum...smooth and in total contrast to the hairy pussy my two fingers were now scissoring inside...working the flesh either side of her clit...touches that made her tremble...tremors that vibrated through her body...my solid erection slipping under her arse...it's swollen tip searching out the edge of her vagina...a blind creature searching by scent and touch alone...desperate to burrow its way back into the warm channel of her oozing pussy...
I pulled her leg over me...keeping my fingers rubbing her clit as my helmet slid and nudged those slimy lips...lips that suddenly parted...
`Ohhhhh goddddddddddddd Tommmm....'
My helmet pressed...the pressure of those swollen lips sliding back my frill until my bare head made contact with those velvet walls until I felt the rhythmic squeeze of soft muscle around my shaft...and still my fingers played...
The angle meant my cock was sliding right out of her pussy...only to press in again to spear those wet walls...moulding them to the shape of my cock and then withdrawing...only to press in again...only this time...there was a new tightness against the tip of my dick...a slightly ridged ring of muscle...hardly yielding but giving just enough for me to know it could....and I knew I'd found her arse hole...
`Tommmm lololol nooooooo lolol'
`No? lol'
`Nooooooo' lololol
I moved my fingers a little faster gently pinching her clit between them...rubbing...squeezing...as she whimpered and moaned....
`N.....noooooooooooooooooooo lol'
`Why xxxxxx not ? 😊
`Because....lol'
I laughed and said that's not an answer....and all the time I continued to rub my helmet against this new and strangely enticing place...each slow thrust smearing and leaving a trail of precum.... Each nudge so close and yet....I swear I could feel it twitch...that forbidden hole...as my fingers worked deeper and faster into Michelle's pussy...turning her soft moans into frenzied gasps... and all the time that new heat....that new tightness...warmer...wetter...unyielding yet...slowly giving way millimetre by millimetre...her writhing body responding to my fingers...pushing back... in spite of herself....millimetre by millimetre...tight like a virgin cunt...and yet...tighter... tempting...so tempting...
I pulled back...smearing my sticky fingers in her crack...spreading her own juices over her arsehole...feeing the tight ring on my finger tip...one hand working her pussy one hand working slowly over her other hole....her forbidden hole...
`Tommmmmmmmmmmmmmmm!'
And there it was an almost unnatural heat...as my fingers burrowed deeper back and front...the easy wetness of her pussy folds so different from the grip of her ring...a grip I imagined engulfing around my dick...a grip that suddenly...suddenly.... yielded...yielded...
`TOMMMMMMMMMMMMMMMMMMM!'
...and yielded....
`FUCKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKKK'
She screamed as my helmet began to push through her ring...pushing steadily into the mysterious burning heat inside...that scream a mixture of pleasure and pain...pleasure as the sensations in her clit started to spread through her pussy...
...pain as my fat dick slowly invaded her arse....
Fucking hell! Was her arse EVA tight....like the tightest pussy you could possibly imagine... clamped just over the ridge of my helmet...
`Nooooooooooooooooo pleaseeeeeeeeeee......!'
I could feel her desperately trying to move away... to ease the pain the pressure of my cock was causing...so I eased back, feeling that tight slimy ring closing as my knob withdrew...knowing it was just a little looser ...knowing that despite her screams another thrust and I'd enter her again...and all the time my fingers teased her clit...working deep between those warm lips...deeper and deeper until they were surrounded by her pulsating pussy muscles...my two fingers working like a cock .... In and out....scissoring....stretching...sliding through the hot moist flesh...
....and all the time knowing that if I lifted her slightly...pushed her leg higher I could slip easily into her pussy....or....or back into that awesome tightness newly revealed to me...a tightness that still resisted my cock...
`OH GODDDDDDDDDD TOMMMMMMMMMMMMMMMM!'
I pushed again....just enough to wedge my helmet right through her ring....I could feel it like a tight band somewhere around the first two inches of my cock...already feeling the soft spongy walls buried deep inside parting around the curve of my knob as I sank deeper...her cries turning to moans ... as I got another inch inside her...then another...and another and started to work little thrusts...each one taking me deeper....each time feeling her arse heat blossoming around my cock....opening...closing...opening again as my dick burrowed deeper and deeper...until with one last thrust....
`TOMMMMMMMMMMMMMMMMMMMrrghhhhhhhhhhh'
My thick root was wedged in her arsehole....my entire seven inches buried....sliding...thrusting... ...was I imagining it or could I feel her ring pulling out along my shaft before it caved in again....
I worked her clit again....faster this time...my other hand full of one of her magnificent breasts....sliding my fingers to her proudly erect nipple....mauling the soft flesh... making her....
FUCKKKKKKKKKKKKKKK !!
Making her ride my dick....moving her hips to meet my thrusts .... Sliding that tight hole up and down my shaft...those yielding walls churning around my swelling knob....her cunt so wet I could feel her juices running up my hand...the air filled with the scent of pussy...a pussy seconds away from cumming... a pussy who's pulses spread to her ass as it started to spasm around my length....
Now we were both lost....Michelle lost in the pleasure trapped between my thrusting fingers and my thrusting dick...me lost in the most amazing fuck I'd ever known...her cries no longer pain or pleasure but wild gyrating ecstasy...my own breath ragged...rasping...closer....closer...
I could feel a new strength in my dick...that moment when every guy swears he gains an extra inch...that moment when your balls go tight....when every muscle in your body seems to be joined to the swelling tip of your cock...the explosion building in the pit of your stomach...rumbling along the length of your cock...
`THOMASSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSSS!'
It seemed as if every one of her senses exploded...an earthquake of spasms and aftershocks... ...slamming my engorged cock as far into her heat as I could...her tits shook -- wobbling....trembling...my fingers rubbing the top of her slit...my dick burrowing deep from behind...the rhythmic slurp and squelch...the rising screams and grunts...the slap of my belly against her arse as I thrust over and over...that alien heat burning around my helmet causing a huge wad of spunk to throb up my shaft...before detonating an explosion in my slit as I fired blindly into that churning hot infinity...wave after wave...pulsating...filling...flooding...
...until the power of my rising orgasm obliterating everything except my need to fill that quivering cunt with another load...
Was it luck or judgement...were we so lost in the fuck that our minds joined blindly...with one single thought...as our orgasms tore through our bodies...as my sperm pumped deep into the churning heat....wave after wave...until we collapsed...spent...exhausted...my balls aching and empty once more...
I slid out...wet...spent...wrinkled...my dense pubes matted against my skin....the dying convulsions of her arsehole oozing a thick stream of my seed...
Suddenly I regained my senses...was my cock clean? What would I do if it was coated in shit after all...a sigh of relief...it was clean...kind of...but nothing as messy as I'd feared...
I didn't stay...I got the feeling that whatever had compelled us was now gone...always a sign to leave....but like the adults we were -- we kissed good bye and made vague plans to meet again...plans I would have stuck to ...but plans I could tell she had no intention of keeping...maybe she didn't need a man in her life...or maybe she needed one to love her...well that wasn't going to be me...
But fuck was I a happy man! Once a pussy hound ALWAYS a pussy hound eh?
Except THAT hadn't been a pussy....that was an arsefuck...the one and only time I'd ever...but somehow I knew it wouldn't be the last....if only I'd known how different things were going to get....