My First Anal

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I wanted to share my first time having Anal Sex and the first time writing so be kind! It is also a true story so if anyone has any feedback or wants to hear more, please let me know.


I’m not sure where my obsessions with anal sex came from but it had increasingly begun to monopolise my fantasies. At 21 I was mocha skinned, 5ft 9″ I was pretty lean but relatively muscular, cocky and easy going. But after my first serious relationship I had rebounded into what seemed like a shallow but frisky relationship with Nicole. She was pale skinned, thin but a well stacked fiery redhead. In retrospect she reminded me of a cross between Faye Reagan and Nicole Scott.

Most nights out ended in drunken, blazing rows or dirty sex but in the light of day we never seemed to get on. However repeated attempts to end it never seemed to work. My latest attempt to politely end it in a bar initially seemed to go well until the end of the night when she successfully goaded me into a bar fight by making out with the nearest available man. I had stormed out furious but hopeful that the embarrassment of the evening’s public rawkus might lend some finality to my decision.

Nicole had other ideas. She arrived at my tiny flat that very evening. She was adept at causing a scene and I thought I owed her closure so I let her in to talk. As my flat was tiny we had to talk on the bed and I tried to explain how ill-suited we were and why a break was for the best.

Despite all my best intentions Nicole stilled seemed adamant that she wouldn’t take no as an answer. What she did next was pretty surprising, even for her. As I protested the finality of it all, and after her desperate apologies and pleas for forgiveness she started to undo my jeans and pull out my cock. I almost laughed at the ludicrousness of the situation but she started to stroke my turgid penis slowly with some aggression. As I pleaded to her, “no,” to stop, she took my cock in her mouth, and swirled it around her tongue. As it grew firmer, it buzzed with anticipation overriding most of the good intentions in my head. I managed to push her head away slightly but she forced back enveloping my lengthening cock entirely in her mouth.

I paused for a moment taking in the sensation of her deep throating my entire penis. This was a battle I was rapidly losing.

Nicole took my momentary weakness and stood up on the bed. Her light green, summery dress clinged to her pert breasts with her pink nipples just lightly protruding from beneath it. The soft, thin straps holding the small dress up, revealed a pale slim chest of porcelain white which she suddenly revealed in full as she dropped them either side of her shoulders. The dress gracefully slid over her nipples across her flat stomach and over her slight hips to reveal a wild strip of ginger red pubes brightly sat above her pink pussy lips.

She kicked the dress aside with her glossy black high heels and dipped her fingers into her mouth coating them quickly and thoroughly with as much saliva as she could and spread them over her clitoris and down her parted lips. She then turned round and crouched back down almost as quickly as she had gotten up.

Taking my twitching cock from behind her crouching legs she rubbed it along her moist pussy lips and before I could protest further she placed the weight of her pert, white arse down on my cock, sliding it into her pussy with some resistance. Nicole could become very wet but usually required a fair amount of foreplay so the eagerness to take me inside her so quickly seemed an indication of her desperate determination.

Whilst my body was enjoying the guilty sensations of it all, my mind was still objecting to her sexual manipulation. I cupped my hands around the underside of her pale arse and tried lifting her off exclaiming a conflicted, but firm “no!” But she refused to listen, raping me rhythmically, with her arse riding my cock up and down like a pneumatic pornstar.

She grabbed one of her 34C tits seductively then used my hand to squeeze it firmly until she squealed. Her hand slid down between her bouncing breasts and to her engorged clit, rubbing it furiously before spreading her fingers around the cock she was fucking and then bringing them back up to her mouth to taste her own cunt pendik escort juices.

Sensing my waning resistance Nicole groaned, “Ughnn… finger me!”

I really wasn’t sure what she meant seeing as her pussy seemed pretty full up with my engorged knob so I asked where and she replied, “Finger my arse!”

As instantly as the penny dropped, so did my resolve. Because of my previously resisted attempts to circle her arsehole with my finger, Nicole knew full well my fetishized weakness. And had seemingly planned her backwards facing rape to expose her twitching arse to my filthy mind.

Unsure of when I would have this chance at depravity again I relented.

Sitting slightly more upright I began stroking the curves of her round arse, a movement that usually turned her on. Signalling this, she began to rock back and forth grinding her clit into the base of my groin and exposing her arsehole further. Grabbing her butt firmly I helped her rock furiously and then stretched her cheeks apart so I could see right into her crevice. My fingers crept gradually inward until they circled the edges of her anus. Pulling the cheeks even further at this point exposed more of her wrinkled sphincter, a tantalising glimpse into her forbidden fruit. I nudged a finger over the surface and we both twitched in pleasure. I began massaging in gentle motions over her tight anus but it was still shyly closed tight.

Changing tact I moved my finger to the meeting point of my cock and the base of her pussy lips. Running my finger over the hot, mess of juices lubricating us, I returned it to hover over her arsehole before plunging it in. She gave me little entrance but contracted in surprise. I returned to circling my finger over her anus, gathering a few millimetres of lubricated progress at a time. With just over half of the tip of my finger tightly gripped by her hungry arsehole, she silently squirmed.

She could sense that she was reeling me back in, but her arse wasn’t quite ready to be entered yet so she made moves to assume my favourite position; 69 with her on top.

Nicole’s virtues were questionable however one thing she seemed proud of was her ability to give incredible head. So sliding her arse off my cock, she shuffled her body backwards and she took my throbbing penis that was fully drenched in her own pussy juice… and licked it clean. Her filthiness never failed to turn me on. She then went about her business deep throating my cock as expertly as ever whilst presenting her moistening crotch to my face.

Her pussy and ass were now very much in close-up above my head. My tongue went to work on her pussy.

One of the delights of fucking a redhead is their unique fiery crotch. I equated the colour to a raw, animalised passion, so the fact that she had let the wiry mound on her pussy grow somewhat unkempt was a disgusting turn on.

The fact that her pussy was engorged by alcohol fuelled sex and a sordid tinge of sweat and wee was a disgusting turn on.

And the fact that her now close-up puckered arsehole was lightly surrounded by a few small, wiry, ginger pubes was also a disgusting turn on.

Nicole couldn’t usually climax through penetration alone so long bouts of oral sex was usually a necessity but not in the way it was about to go down.

Working her pussy with my tongue was already having an effect on her as I could hear the moans escape from her cock filled mouth. Grabbing her pale arse cheeks I gently rocked her pussy up and down on my tongue, dipping both index fingers into her sloppy pussy as she ground her juice into my face. However this close I could see more of her arsehole than ever. I spread her ass cheeks widely inching each fingertip closer and closer inwards. Eventually my middle finger tips bristled past the few pubes around her arsehole and her body began to flinch.

Getting braver and more adventurous I moved my tongue further south from her hungry clitoris, along her pink lips and then deep into her pussy, fingering her with my tongue whilst savouring her salty, musky juices and eventually further back around to her untouched perineum. Nicole could sense what might be coming but didn’t flinch until my tongue reached her puckered arsehole. It danced around the ridges on her surface before quickly pushing inside her constricted muscles a few millimetres, tuzla escort but her reaction was instant and uncomfortable, “Not with your tongue.”

So I relented and using my hands I kept her bottom close to my face and inched my fingers inwards to the edges of her wrinkled anus. To see every inch of hidden detail so close-up was scintillating! My fingertips once again tugged gently at the edges of her sphincter, spreading her asshole slightly more open. I returned my fingertips to the horizon of her arsehole gently massaging the surface again.

When her body resisted, my hands pinned her closer to my body whilst my tongue distracted her back into sexual oblivion.

Dipping my finger through the tight opening proved difficult, I only managed to depress it inwards slightly so I awkwardly removed my wet fingers from her pussy and brought them back up to her opening. With the slightest of dirty lubrication the tips of my fingers were already making progress, pushing their way into her tight arse.

The sensation was alien and familiar at the same time, reminding me of the newness of feeling your dick in a warm pussy for the first time.

Nicole’s body rocked at the foreign intrusion into her butthole, but my grip held fast and my tongue worked harder on her clit to continue to distract her.

Not only did the anal grip on my moist fingertip tighten, but her mouth’s grip on the length of my penis also tightened. The feeling of my fingertip in her ass for the first time was both driving us to the edge of climax. I worked the digital rhythmic movements in her ass harder in time with the licks to her pussy and felt the wave of orgasm start to rock her body.

It was then a magical thing occurred. As her body arched, her asshole momentarily opened up, fully relaxed and dilated I slid my finger quickly in, past the first knuckle, and then her anal muscles tightened again. As the second wave of orgasm broke against her body, she arched her body again, and her asshole flowered open and sucked my finger into the second knuckle. I gently pulsed my finger in and out, eager to soak up the sensation of movement and suction. As the third and final wave of her orgasm washed over her I made one last push, inching my finger almost midway past the second knuckle, once again pulsing and arching my finger to feel the darkest parts of her body that I had never touched before.

With my finger nearly entirely swallowed up by her asshole, my face covered in the juice from her pussy overflowing in pleasure and my cock buried deep in her throat, I finally exploded a powerful stream of cum into her throat. Shooting multiple spurts until my cock was left twitching in her paralysed mouth.

Was that possibly the best 69 ever?

But the deviancy hadn’t ended there. As we lay in a post coital embrace, our bodies entwined more deeply than ever, Nicole asked, “How many fingers do you have up there?”

I replied with, “Just the one,” and she seemed surprised. The sensation was so unfamiliar to her she couldn’t tell what was in her ass or how far it had gone.

This may be the reason for her braveness, however it would turn out there had been ulterior motives.

With my finger still static in her ass, she turned round to me and said something I thought only porn stars say in my dreams, “Fuck me in my ass.”

My brain couldn’t’ quite believe the fantasy that seemed to be coming true so I stumbled and she once again begged, “Please fuck my ass?”

Did Cosmo teach her this pornified theatrical dialogue? I didn’t stop to contemplate it any further. Sliding my body and still erect penis out from under her, I kept my finger inside her arse, gently massaging it and feeling the inside walls of her.

She reached down the side of the bed for her small tub of Vaseline. I wasn’t sure if it was still the recommended lube for anal sex but I wasn’t going to quibble. Taking a lump of the lumpy moist Vaseline she reached behind her to spread it generously on my still hard cock. It throbbed at her oily grip. Her hand glided over my balls, which seemed a strange thing to lube until I realised where she was going. She stretched back to try and slide a finger up my crevice and into my arse. She partly nudged her oil finger easily in which sent a shuddering sensation of anticipation through my kartal escort body but the position was too awkward for her to maintain.

So I took the tub of Vaseline, smoothing out parts on my penis with my left hand. I then returned my left hand to her arse cheek, spreading it widely and inching a glistening finger back to where the other was still comfortably embedded. I spread the Vaseline around parts of her bum and coated my right finger as much as I could before trying to prize a second finger in. Her arsehole was still tightly gripping one so as I pushed the second finger in I slid the second out. She quickly opened and closed back on the single digit. I applied Vaseline to the other finger, still warm from its cosy time in her arse, before struggling to squeeze it back in. Eventually I had to stretch her arse cheeks with both hands whilst trying to fit both in at the same time.

Nicole seemed impatient or eager to have me inside her so she turned back and said, “Just put it in. Fuck my arse now, please!”

So whilst keeping both fingers partially inside, and stretching her arsehole as wide as possible, I pushed my rock hard cock into her opening. The fingers were still getting in the way so I had to quickly let go and push the head of my cock in with some force and speed.

Nicole’s face seemed to wince but not complain. My head was still only partially in so I tried gripping the base of my cock and pushing it through the opening but with little give. So I then tried spreading her cheeks apart, sitting a little higher and pushing downward. I was slowly gaining a few millimetres in traction.

Eventually I moved to the best combination. I pushed her back down and grabbed both of her hands commanding her to spread her arse cheeks wide, whilst I grabbed the base of my cock to keep it firm and steady. With one hand on the base of her back, I slowly but forcefully pushed downward.

Gradually my penis inched closer inwards, pushing globs of vaseline out of her opening. Unrelenting, I pushed harder and deeper until finally with a satisfying grip, her anal muscles swallowed the head of my cock and gripped it like a vice. She gave a groan of pain, satisfaction and pleasure. I pulled my foreskin a little further back to full appreciate how much she was enveloping my head.

From here each movement was slow, deliberate and precise, all with the intention of inching my penis further and further insider her anal canal. Watching my long brown cock disappear into her pale round ass was enough to make me want to blow my load right then but I was starting to gain traction.

With each slow rhythmic motion inside her, Nicole was wincing, whilst I was barely trying to hide my ecstasy. As finally half of my penis had disappeared inside her tight arse, I started pounding her heavier and more deeply. I could see the pain on her face as she was also getting lost in the pleasure. The temptation to fuck her arse as aggressively as I might her pussy was too much so I started pounding it with light aggression slowly gaining further depths inside her.

Each time I did this Nicole would plead, “Not too hard.”

And I would momentarily ease up before pounding her a little harder, a little faster and and a little angrier. Soon her groans of pleasure and pain were growing louder and more guttural whilst her hands soon dropped from spreading her cheeks. Each time I punctuated a rhythmic fuck with a deeper entrance she would grip the sheets and wince a little harder. Sensing that she was either losing herself to the moment or reaching a limit of pleasure and pain, I grabbed her arms back by both wrists in one hand and her long ginger hair in the other hand, pounding her arse as deeply and aggressively as I could, watching her tear up whilst a secret part of me became even more aroused at what sexual pain she was enduring for my pleasure.

As my long, hard, brown cock disappeared in and out of her pale round arse I finally released her arms and hair, angrily grabbing both cheeks before digging my cock right up to the hilt whilst ejaculating gloriously into her deepest, darkest recesses coating her dark walls with my white warm cum.

As my cock twitched inside her dribbling the last spurts of sperm into her arse, I basked in the glow of what may have been the greatest fuck of my life before looking down at Nicole, who despite looking bedraggled with tear stained mascara running down her face, returned a look of pleased satisfaction at what she had achieved.

At that point, I realised who had really been fucked.

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