First Time's a Charm

Andi had been invited to Paul's for an evening he was a little unsure of. He had been having wild erotic fantasies about what could happen, what he wanted to happen.

He was young, just twenty one, and full of raging hormones.

Six foot,slim,athletic,sensual and sexual. Quite effeminate looking. Big blue eyes with long dark lashes, cute pixy nose, large mouth with large pouty lips.Framed by shoulder length luscious brown locks.

Small waiste with a flat hard stomach.

But below the waist he was absurdly endowed, having an enormous python of a cock, even when flaccid he was eight and a half inches and thick with enormous tennis ball sized balls hanging low in his sac.

To say he was over endowed was an understatement!!

But when he got an erection his cock ballooned past the twelve and a half inch barrier and thicker than your wrist.

From the rear he had the most shapely gorgeous arse chicks would kill for. Curvey and firm. Basically a red hot sex machine on two legs.

He was wearing a clinging tight pair of pale blue spandex cycling pants. Which clung and extenuated his every curve and bulge. With no underwear underneath.

His enormous cock snaked down the inside of his right thigh looking obscenely huge and prominent.Writhing and wobbling as he walked to Pauls front door, his enormous testicals bouncing from side to side as he walked.

From the rear the shorts were lodged in his gorgeous arse crack so that his firm cheeks bounced up and down.

He had a skimpy loosefitting singlet and a pair of thongs, and that was it.

He was baring all. But he was nervous as to what Pauls reaction would be when he opened the door and was second guessing his dress choice.

Had he misinterpreted Pauls playful advances. As last time they were at his place and were playfully wrestling with each other and giggling like school girls. Hugging each other, putting each other in headlocks,wrapping their legs and arms around each other. Something had changed and had become sexually charged.

Breathing got heavier, they had started to softly grind their genitals against each other with blood flowing to their nether regions. Andi could feel an impossibly huge pole inside Pauls shorts.

But had been cut short as Pauls sister had pulled into the driveway to discuss her up coming wedding arrangements. So I left him to it.

So here Andi was a week later, hoping to pick up where we had left off.

The dress attire leaving absolutely nothing to the imagination," here it all is ".

He was nervous and sweating, hands shaking as he knocked on his door.

He could hear someone coming to the door and took a deep shakey breath.

The door opened, but not to someone he knew. There was a gorgeous woman holding the door open. Tall, roughly the same height. Stunningly beautiful with long dark brown hair, huge dark rich brown eyes with long dark lashes. Big beautiful luscious lips. Tall slender body, the more Andi looked the more familiar she became. It was Paul, but dressed as a woman. But what a woman. Six foot, slim build, toned. He had white stockings, suspenders going up under a short clinging red skirt. A sheer pale red top with a sheer white see through bra. Red lipstick, eyeliner and eyeshadow which accentuated his gorgeous brown eyes. He nervously said"Hi baby, how do I look?"

Andi stammered "Holy fuck, you look amazing. Beautiful and hot as fuck".

Paul blushed "I wanted to dress like this for you", as his eyes travelled down Andi's body, eyes growing wider, cheeks going redder as his eyes feasted on his huge obscene package, his tongue flicked out licking his top lip hungrily. Watching as Andi's penis had notibly swelled with blood and lust, growing ever longer and thicker.

This stirred Pauls loins. His cock started to swell as well, distending the front of his skirt with a very noticeable bulge, which Andi excitedly noticed.

"Come in" Paul huskily said holding the door open invitingly.

Andi deliberately brushed against him as he entered, feeling his pole rub against his hip.

Paul clossed the door, turned taking Andi's hand in his and as he moved past him he deliberately brushed the back of Andi's hand softly along the length of his slightly swollen member, which was already an impossible length and thickness, even though he was no where near hard. He then turned and led Andi into the lounge area. Sexily gliding ahead holding Andi's hand in his.

Andi's eyes were ogling Pauls sexy arse which bounced and wiggled from side to side in his thin tight skirt as he walked sexily ahead hips swinging from side to side. No shoes, just stockinged feet.

Arriving beside the large soft couch which had a coffee table in front, on which was an ice bucket and champagne glasses already full, which he picked up, handing one to Andi. They clinked glasses.

Paul saying" Here's to us and a fucking wild weekend", flicking his eyebrows up and down, staring directly into each others eyes. Both downing the glass in a huge gulp.

"Well, do I get a welcoming kiss baby?" Paul said huskily.

"I'll give you more than a welcoming kiss you hot slut".

He said turning to him and sliding his arm around his waist dropping his hand onto his shapely buttocks, caressing his firm cheeks with his fingers.

His other hand went to Paul's chin. With a finger under his chin lifting his face toward him as he moved in to gently kiss him on the lips. Their soft moist lips coming together in a sensual kiss on the lips.

Pauls hands slid around Andi's hips grasping his buttocks with both hands gently, but urgently pulling him towards him. Their clothed cocks coming into contact with one another as they sensuously ground against each other, feeling the heat from each others mammoth members. The kiss became more urgent and passionate as their mouths opened and they began sucking on each others mouths while sliding their tongues into the others mouth sucking each others tongue and saliva. Swallowing each others nectar greedily.

Andi felt Pauls hand slide up his arse and slither down the back of his pants onto his bare buttocks groping them urgently as they moaned open mouthed into each others mouth. They were now grinding hungrily against each others monstrous erections. Which had by now both grown to enormous proportions.

Both were super aroused, Andi's cock was now aiming above his navel, having risen steadily skyward. He had distended his skin like shorts hugely. It looked like he had stuffed a baseball bat down the front of his shorts, like they were going to rip apart at any second, such was the mass of rock hard meat down there.

Paul rubbed his other hand along its enormous length and gasped into Andi's mouth.

"Oh my fucking god, it is absolutely enormous. Oh you fucking beautiful boy. I actually dreamed you had a massive cock".

He then thrust his tongue down Andi's throat moaning deeply into his open mouth.

Groping the huge member urgently, sliding his hand upwards until he felt the huge bulbous head about the size of a small apple. His hand sticky and wet from the steady stream of precome steadily leaking from his cock slit.

Bringing it to his face he deeply inhaled the musky heady aroma, then licking his fingers, sharing them with Andi sucking and slurping loudly between them.

Meanwhile his other hand was slowly burrowing into Andi's arse crack. His middle finger sliding into his hot sweaty swampy crack working it's way towards his puckered brown anus. He used his fingers either side to slowly spread his cheeks so he could gain better access to his prize.

He felt Andi bare back against his fingers spreading his arse cheeks. His finger coming into contact with his huge anal pucker.

It was hot and greasy to the touch. Andi groaned loudly into Pauls mouth then thrust his tongue deeply into him mashing his mouth frantically moaning loudly. A huge spurt of precome leaking from his cockhead. He writhed frantically back against Pauls long finger which was circling his huge puckered folds. Hot and moist to the touch, he slowly worked his finger to the crinkly centre pushing slowly and rhythmically against his anus. Tapping against him, putting pressure against the hole then releasing it. Pressing with his fingertip, press,release, press, release. He felt it softly release, allowing his fingertip to slip slowly in to the first knuckle. His anus was like a vice, gripping hotly against his fingertip, pulsating against him, trying to expel the intrusion. He held firm so the hole could get used to its guest.

Andi meanwhile was concentrating on the violation to his most private centre.

While it was painful, it was also intensely erotic and stimulating. Knowing that he was giving his most private secret to his lover, because thats what they had instantly become, lovers.

"Finger my hole lover. I want to feel your finger slide into me and make me yours.

God it feels incredible. But please be gentle. I want to feel you as you finger fuck my shit hole, ohhh fuuucck ".

"Your arsehole feels incredible, it's gripping my finger like a red hot vice. I can feel your pucker pulsating against me".

Slowly he inserted his finger further, now to the second knuckle as he felt it gripping him and releasing. He didn't need lube as Andi's hole was already hot and sweaty and creating it's own natural arse lube.

He pushed further until his whole middle finger was buried deeply up his anus.

"Fuck my arsehole with your finger baby.

Oohh yeahh that's it, fuck me ooooohhh fuuuuuuck me.Shit that feels sooo gooood".Paul was now fucking his finger in and out of him firmly.

"Put another one in me, ohh shiiit fuck my hole. Finger fuck the shit out of me, oh yeah that's it, ohhh fuuucck."

As Paul added another finger. Andi's hole was starting to loosen a little which made it easier to add the second finger.

After a while Paul said" I want to lick your arsehole and stick my tongue up you baby, I have to taste that gorgeous arse and hole of yours".

"I haven't showered so it's probably pretty funky"he said nervously.

"Perfect, I want to taste you, not soap or perfume, the funkier, the better, my arse isn't any better either,no shower for me as well. We can arse stink together, I want to smell and taste you, and have you smell and taste me. I want to sit on your face and pull my hairy cheeks apart and grind my hairy puckered brown arsehole all over your face and feel your long thick tongue deep in my shit hole. But first I want that gorgeous arse".

Pulling his fingers from Andi's hole which made a slurping sound as they exited, to which he felt strangely empty.

Paul brought his moist fingers to his and Andi's nose inhaling deeply as Andi's anal aroma wafted strongly up each others nose. Stronge heady mix of arse crack, bitter and slightly metallic,sweaty and sweet and earthy.

Paul thrust them into his mouth, licking and sucking noisily, then thrusting them into Andi's mouth forcing his tongue inside as well as their tongues wildly licked and sucked each other.Paul suddenly broke away, grabbing Andi's hips spinning him around pushing him onto his knees facing away from him on the couch pushing him between his shoulders forcing his shoulders and face into the couch with his arse up in the air.

Paul knelt behind him grasping his shorts either side of his hips. Slowly he eased them down over his hips exposing the top of Andi's arse crack, leaning over and placing soft butterfly kisses along the top of his crack either side.

He wanted to enjoy this moment prolonging it as much as possible, instead of just ripping them down and diving in like his mind screamed.

He had never been so turned on and horny in his entire life. His cock was so hard and huge it hurt. Sticking well above his navel by several inches and thick as your wrist. His huge head leaking copious amounts of precum that the whole top of his skirt and top wer soaked with sticky precome. The smell was overpowering and pure sex.

He lowered them further his crack growing longer, his gorgeous plump cheeks coming into view.

More kisses and licks. His hands were shaking with nervous erotic excitement, his breathing getting heavier. He could now smell his private place the closer it got to being exposed.

He could hear Andi moaning in erotic anticipation.

Still lower, there was soft thick dark brown hair starting down either side of his crack and a brown tinge to the skin, and those beautiful arse cheeks.

The kisses were getting more passionate now and openly licking his cheeks and down his arse crack.

Pulling them lower still his arse was slowly exposed and the heady smell hit his nostrils instantly. His arsehole was enormous. Like a huge puckered brown flower. Dark brown in colour,flairing out in huge crinkly puckers. It was greasy and moist, with the strongest overpowering intoxicating earthy smell imaginable. There was a brown tinge to the skin surrounding his anus, as well as a ring of soft thick brown hair around his hole.

No cute little pink hole. This was huge, dirty,brown and hairy. Fucken hot shit sex hole!!

Andi reached back spreading his cheeks wide open exposing more of his anal centre. It was pulsing in and out opening even deeper to a darker chocolate brown crinkled centre.

Paul had never seen anything as hot, sexual and dirty in his entire life.

"Lick me darling, stick that hot shit tongue up my dirty hole and lick me clean. Suck the shit out of me. Tongue me, tongue my dirty brown shit hole".Andi said gutturally.

Paul leaned in drawing a huge breath of pure sexual arse, then put his nose to his hole inhaling slowly and deeply taking in all the different rich anal aromas.

Then he began slowly, softly running the tip of his tongue around the outer ring of his anus. Over the bumps and ridges of his anal pucker savouring the rich bitter textures.

Andi was moaning loudly, trying to grind his hole against Pauls mouth and tongue, to which he resisted, all in good time lover!!

After some time he started to work his way inward towards the centre. The closer he got, the stronger the taste and smell became. It was fucken divine. It intoxicated him.He started licking harder and sucking on his anus, sucking his nectar into his mouth, becoming ravenous, noisily sucking and slurping on his hole as more arse juice flowed into his mouth and down his throat.

He started thrusting his tongue against his puckered centre. The taste and smell here was by far the strongest. It was driving him to a frenzy.They were both moaning loudly.

Suddenly Paul's tongue punched through his ring into a hot velvety cauldren. Liquid poured through the hole into his mouth. The most forbidden sexual anal taste that surpassed everything he had ever tasted. He went crazy, tongue thrusting in and out sucking as hard as he could.

After a while he pulled out.

"I have to fuck you baby, I'm going to stick my huge cock in you and fuck the arse off you. I hope your ready because my cock is enormous and I've never been so turned on in my life. I'm going to spurt deeply into your bowels and breed you, split you in half." He said huskily.

"Oh fuck Yeah you hot slut. That was incredible. I thought you were going to suck me inside out through my arsehole. I want your pole up me. My arsehole feels amazing, it's ready to be fucked, it is so tender and swollen. Put your beautiful cock in me and brutalise me. Fuck me and seed me". He panted.

Paul's cock was rock hard, aching and huge, over a foot long. It was sticking out obscenely from under his skirt and out the top of his skimpy white thong. Enormous hairy testicals spilling out either side of his thong knickers hanging low and full of sperm, as he hadn't come since before their last playful encounter. He had been hopefully saving himself until now.

He had lain in his bed dreaming and fantasizing but resisted the urge to masterbate.

He was glad he had, because his enormous testicles were full and painful with a case of blue balls they were so full of seed.

He grabbed Andi's shorts either side and pulled them down his thighs, the front caught on the enormous cock protruding over a foot from the front. Andi grasped the distended front pulling them forward releasing his weapon which shot upwards slapping wetly against his stomach with an audible slap. He then pushed his hands into the couch taking the weight on his feet and hands while lifting his knees so Paul could slip his pants off. He held them to his nose inhaling deeply, then threw them onto the floor.

Gazing hungrily at the inviting sight before him. The plump firm cheeks, the hairy ring which fanned outwards and down around his massive low slung come filled balls hanging halfway to his knees. But in the centre the huge inviting puckered brown moist dark pulsating centre.

Grasping his enormous shaft, which was as thick as his wrist with huge thick veins running up its length, and hot to the touch. The massive head was three quarter sheathed in his foreskin with half the tip protruding from the end. It was an angry deep red in colour with a steady stream of precum leaking from his urethra.

Aiming the head at Andi's anus he leaned forward and touched the head to his hot wet anal opening. They both jumped as though they had been shocked, such was their hyper sensitive sexual state. Both of them shaking and sweating profusely. Their breath coming in shuddering gasps as they took in what was about to actually happen. Both moaning and gasping loudly.

There was so much precome that no lube would be needed.

Positioning his cock head against Andi's arsehole he pushed against him, watching as the puckered folds slowly parted, but then stopped as the tip encountered his anal ring. It was super hot and vice like, not allowing entrance into his forbidden hole. Paul could feel his anus contracting against the tip of his cock.

"Push it baby, but slowly, let my hole open for you, god you feel enormous. But fuck I want your cock in me". As he pulled his cheeks wide open to give Paul better access to his hole.

"Push out your arsehole like your going to shit. It will open up for me, fuck you look hot like that".

He felt and saw Andi's anus protrude outwards growing larger like a flower opening, puckering ever larger.

He pushed forward, again encountering his anal ring. Holding his shaft he pushed forcibly forward feeling the vice like ring suddenly yield and the head of his cock passed through his anal ring, then gripping the head of his cock as it lodged in his anus spasming rhythmically as it tried to expel the unwanted intruder.

Andi screamed in agony and ecstasy such was the enormous intrusion and violation into his very being. His anus felt like it had been ripped apart and was spasming frantically trying to push the head out.

But Paul held his hips firmly holding the head of his cock in his lovers arsehole.

Andi was sobbing and moaning in pain and rapture, as the cock head felt super heated, as it leaked precum into his insides.

Slowly he started to push against it, feeling his anus stretch to try and accommodate the thicker shaft, but also feeling the massive head parting his anal walls as it pushed deeper into him.

The pain was intense but incredibly erotic as well.

It felt like he had a baseball bat up his arse.

Meanwhile Paul watched as the head of his cock finally pushed through his anal ring, watching the puckered hole stretch apart then close around the head of his penis gripping it like a vice. Watching as it spasmed against him. It looked so fucken hot he thought he was going to come right then and there. By sheer will power he managed to avoid coming.

His hole was so hot and tight like liquid velvet.

When he felt Andi push back against him he started to push his cock into him feeling his shaft start to push tightly past his anal ring. Inch by inch it disappeared up Andi's bum hole.