tagAnalHow It All Began Ch. 02

How It All Began Ch. 02



This is the second installment of Jack's voyage of discovery, it involves male anal penetration so again, if this isn't your bag, walk on by.

All feedback is always gratefully received so do feel free, I can take it :)


Jack drank in the sight of Fay's scarlet flushed cunt being lowered towards him as he raised his face to meet it. It glistened with wetness as Fay's legs straddled his torso and he released a short gasp as he felt Fay's fingers stroking on his rigid cock. Pulling her hips to the right position, he pushed his tongue deep into her wet folds, tasting their congress inside her as his fingers pushed on the gold coloured thin dildo penetrating her arse. Fay moaned, buzzing his cock with her approval as his tongue flicked on her sensitive clit to then encapsulate it in his lips sucking on it.

Fay's eagerness on his cock was renewed again as she could feel that familiar tightness and warmth flooding her loins. A deep contented moan left her as she luxuriated in the sensation Jack was giving her. The evening was a revelation, he was a great fuck, sharing, selfless, happy to take charge and yet like the ebb and flow of the tide he was happy to let Fay assert herself too. Despite filling her mouth, splashing his seed over her taut frame and filling her needy cunt, Jack's cock was still responsive to her touch, it was very hard, the heat warmed her mouth as she licked over his fat cockhead before feeding his shaft deep into her mouth. It was getting too much again for Fay as she broke contact with Jack's cock, her head down as she slowly stroked his meat pushing her finger deeping in his ass again.

"You fucking bastard Jack," exclaimed Fay.

Despite the clammy heat of Fay's thighs almost boxing Jack's ears; he could clearly hear Fay's exhortations. He acknowledged her by flicking the tip of her tongue hard under the hood of her swollen clit several times. He had learnt enough of Fay's cunt to know she drove her mad with lust.

"Yes, make your bitch cum, make me," hissed Fay.

That now familiar shudder as the portent of her orgasm had arrived. Fay's hand gripped Jack's cock hard as she stuffed it into her mouth. Jack gripping her hips tightly, holding her down as he forced her to cum onto his face. His lips sucking her clit with a wet slippery violence that he knew would give her what she craved again. It was almost too easy for Jack to make Fay cum now as he'd felt his fingers and cock grasped by her spasming pussy muscles, that relentless undulation that has made Jack yield inside her readily enough.

Those soft feminine moans were louder now, Jack could feel cool air on his cock and the sound of Fay sobbing hard for air, her body shaking on top of his as she tried to free her sensitive clit from Jack's clutches. With another sob, Fay spasmed again, groaning loudly as another hard orgasm shook her forcefully blasting contractions through her lower abdomen.

"Stop, stop, fuck!" gasped Fay.

Fay's body was trembling now, each spasm less and less interspersed with one violent gut-tightening explosion. Fay could feel Jack's grip loosen, his mouth and fingers withdrawing. Lifting her jarred and shaken body from his, she pulled her toy from her arse and rolled off Jack's body.

"You fucking animal," moaned Fay.

Jack was laughing and sliding a finger into her wet sex she winced a little as its sensitivity surprised her. Casting her eyes to look across at Jack's cock it was still swollen and hard. Fay rose onto her knees and looking into Jack's eyes, she leant down to kiss Jack softly on the lips gripping his stiff cock in her slight hand feeling his girth.

Jack moaned a little as Fay straddled him, leaning back to squat over his prone body.

"Jack, there's one place you haven't been yet," whispered Fay coquettishly.

Jack's eyes were closed, Fay grabbed his hard shaft and as she lowered herself onto his cock she pushed his shaft against her tight opening. Jack's eyes opened, Fay could see they were filled with surprise and she countered with a wry smile.

"Want to watch me take your cock?" asked Fay.

Jack smiled.

Biting her lower lip, Fay held the shaft of Jack's cock as it pushed past her sphincter into her, he froze as Fay navigated his cock into her tight passage. As she bore more of her weight onto his cock, it slipped deeper into her. The sticky heat around his cock made Jack gasp loud, it was far more confining than her cunt. The lube and Fay's blatant exhibition of her fucking her own arse for Jack's entertainment had stretched it a little for him. Jack did not break his eye contact with Fay as she started to ride his cock, she looked upon him, feeling his girth as it burned her tight muscles to stretch them a little. She revelled in the pleasure and the pain of it, the juxtaposition of being dominant to ride him yet submissive to be such a brazen whore for Jack's pleasure.

Fay reached over for a toy, a purple one and holding it she slid it down her body towards her red swollen pussy.

With each gyration of her hips, more of Jack's girthy cock had slid into her, she was full and as she bounced with increasing force onto his cock she listened as Jack's moaning becoming ever more breathless. Fay cast her eyes onto his body, his brown hair was spiky and shiny with sweat as his lean athletic torso, arms and stomach was sheened and blotchy with his exertions for her. She leant back, grasping one of his ankles for support she pushed her cunt upwards so Jack could see his cock sliding in and out of her tight hole. Fay fantasised that another hard cock was sliding into her wet pussy and her thoughts were only punctured by Jack's groans as Fay wedged the purple vibe into her cunt applying more pressure on Jack's cock.

"Can you feel that Jack?" asked Fay wickedly.

"God. Yes. You filthy bitch Fay," gasped Jack.

"You love it, Cum in your whore's arse Jack, give me your spunk," demanded Fay.

Pushing herself harder and harder onto Jack's cock, Fay's arse had easily accepted the breadth of his cock. To Jack, it simply felt like the tightest cunt he ever fucked as he watched Fay fucking him, the visual image of her cock sliding in and out of her arse seered into his mind as the visuals, the sounds and the sensations mugged him seizing all of his self-control. Jack's body lurched up, his back arched as Fay felt his thighs tighten and shake, his body started to tremble.

"Yes, Yes. Cum for me, CUM FOR ME!" spat Fay.

Jack's mouth was open but no sound escaped as Fay sat hard on his cock feeling a warmth seep into her, Jack groaned hard, grunting deeply as he stabbed his cock into her, feeling his cock slickened by his own juices.

"Mmmmmmmmm," moaned Fay in approval.

Fay pulled the vibe from her cunt as Jack's post-coital spasms throbbed inside her. She raised the vibe to her mouth to taste as Jack was spent on the bed underneath her. She looked upon Jack's sated body as he feasted on her sucking and licking on the wet slickened vibe, she pulled it from her mouth and offered it to Jack to share. She could feel a small flood of wetness from her pussy again as she guided the tip of the vibe into Jack's accepting mouth, she slowly pushed more and more of the vibe into his mouth.

"Do I taste good Jack?" whispered Fay.

Jack's eyes answered back as she watched him sucking on the vibe, Fay shifted her position to free Jack's semi-flaccid cock of her arse. She could feel the now watery cum leak from her as Jack's cock left her body, it dripped onto Jack's groin as Fay pulled the vibe from Jack's mouth.

"Wow. Fay," Jack paused, "just fucking wow."

"Your first anal babe?" asked Fay.

"God, erm, yes, yes it is," replied Jack softly.

Fay smiled sweetly with a knowing look of a woman twice her age. She lay beside him as she pulled a tissue from the box on the bedside table to dab Jack's cock and groin.

"That cock is perfect Jack, it fits my cunt and arse just right, " said Fay in faux admonishment, "You don't mind being the less experienced one do you?"

"Not when sex is this fucking good, that was pornstar sex," exclaimed Jack.

Fay felt a swell of pride, a comforting affirmation that she had satisfied a man she really considered her sexual equal. Her pussy stung a little, it was certainly a little bruised, she savoured the feeling of being sated as she felt it wash over her body. She enjoyed the clarity of thought it afforded her and the new memories of another lover to recollect in a daydreamy moment and most of all, the consolation of a good deep night's sleep sated from her torment.

"You ok?," asked Jack.

"Me? Yeah, feel fucking great. I think we both needed that," said Fay absently.

Jack smiled, Fay snapped out of her reverie and playfully smacked Jack's chest with the back of her hand.

"You're a dark horse Jack Richardson! I thought you were one of those straight-laced guys not a fucking deviant!," exclaimed Fay

Jack laughed again.

"I never thought I would have you and that magnificent cock cumming in all of my holes," Fay added

They both laughed now, a hearty belly laugh.

"There's not much I don't like. I guess the problem has always been finding the right woman to admit that to. How's those holes of yours?," asked Jack.

"I'll know you fucked me tomorrow," stated Fay adding a small laugh, "Considering each one has been filled with your meaty cock and my toys for the last few hours; they are in good shape."

Jack turned his head to look at the bedside alarm clock; it was just past midnight.

"We should shower Jack," said Fay.

"Yes, we should," Jack affirmed.

They took turns in the pokey small shower as each watched the other lather their bodies, rinse and let the cascade of fine water droplets collect and then torrent down their bodies. Fay took the time to admire Jack's body concluding that with a little fake tan perhaps and trimming some of his more wayward body hair a little that he was definitely her type. That pleased her immensely as too often, the urges from her body forced her to accept perhaps too many compromises.

Jack savoured being watched, Fay's upfront sexuality had cast aside his bravado and he had relented to Fay's obvious experience. Jack was resigned that he'd fucked the office slut, or rather the ex-office slut but this was more than just an easy sexual encounter; she clearly enjoyed sex and he was not going to chide himself for that. Jack was surprised by how malleable she was in terms that there was little that was off limits. With the alcohol, the familiarity of an acquaintance and Fay's forthright attitude, he thought he had pushed her boundaries; he afforded himself a smile that he hadn't.

"Jack, that cock of yours, have you ever measured it?" enquired Fay breaking Jack's train of thought.

"No," stated Jack.

Of course he had, he knew the dimensions versus the average dimensions.

"Liar!" replied Fay.

The sound of Jack's laughter boomed around the small bathroom.

"You want to know? A bit academic now really isn't it?" asked Jack.

"Go on. Tell me," whined Fay lingering on the last 'e'.

"Ok. Almost 8 inches long and 7 inches around," stated Jack.

There was a short pause, Jack thought Fay was buying for time to be diplomatic.

"Holy shit! And big pair of balls too. Jack's got a pornstar cock!" chanted Fay.

"Pornstar cock for a pornstar," laughed Jack.

Stopping the shower and stepping out, Fay handed Jack a towel, he looked into her eyes and smiled. Jack started to dry his short close cropped hair and towel himself.

"You like pornstars Jack?" asked Fay.

" 'course, who doesn't?" replied Jack.

Fay smiled.

"What are your favourite kind?" asked Fay.

Continuing to dry his body, he looked quizzically at Fay and then smiled.

"Young athletic ones, petite, all over tan, shaved tight snatch, nice tight pert tits, tighter arse, filthy dirty mind ............ and a potty mouth!" replied Jack triumphantly.

Fay laughed, playfully slapping Jack's shoulder with the back of her hand.

Wrapping his towel around his waist, they made their way to the bedroom again and the chill on the short landing contrasted with the warmth of the bedroom. They both smiled at each other at the distinct musky smell of sex in the air. Jack dropped his towel first and slid under the down filled duvet. Fay couldn't help but expose herself to Jack as she removed her towel and slowly crouched to the chest of draws opposite the bed, her body obstructed the view but the sound of wood drawn against wood intrigued Jack.

"What are you doing?" asked Jack.

Giving no reply, Fay had a silver disc in her hand which she fed into the small TV opposite the bed. Holding the remote control, the screen was blank, two green bars showed the playback was paused.

"Jack, can you keep secrets?" asked Fay.

Jack's mind raced back to earlier in the evening, his curiosity would only be satisfied by the strength of his character.

"You know I can," replied Jack with a hint of solemnity.

Fay smiled and inside she knew he could.

"Well, seeing as you like pornstars, I thought you might like to see this," said Fay completing the sentence with a wicked smile.

"Porn?" asked Jack excitedly, "Nice!"

She slid under the duvet, wriggling a little to get comfortable as she sat up, leaving her chest exposed and her broad tight breasts, the duvet covered her lap as she plumped the pillows to provide a backrest, Jack did the same as the scene on the TV started.

As Fay turned to look at Jack, she smiled as he watched avidly. To Jack, the camera shake and the relatively poor lighting made him quickly conclude this wasn't a professional porn film or a poor bootleg at most.

The camera came into focus, a woman was sat on the edge of a table and leaning back supported by her arms as what looked like another woman was knelt between her legs. The woman sat on the table was watching her as she was clearly eating her pussy. The camera panned in and moved to provide a view of what the woman was looking at, whilst the colour was rather anaemic, it was clear who was between the woman's legs.

Jack threw a astonished look at Fay, she looked at Jack with a huge smile.

"You look shocked Jack?" quizzed Fay smiling.

"Fucking hell Fay, I mean, erm, fuck!" exclaimed Jack

"You mean? I like women too Jack, you aren't jealous are you?" whispered Fay into Jack's ear, "Besides, you should see what I do to the cameraman."

Jack smiled, squeezing Fay's thigh.

"No, it's just, erm, what can I say? I'm lost for words," replied Jack.

"I can turn it off if it's too much of a headfuck for you," whispered Fay with a hint of faux exasperation.

Jack laughed again, as she looked at Fay's pouting lips which broke into a smile almost immediately. Jack's attention was drawn back to the screen, Fay was clearly good as the woman's moaning was getting louder.

"Erm, no, it's no headfuck, quite the opposite," muttered Jack.

Fay moved into Jack, her thigh pressed against his as the scene unfolded, raising a hand to stroke on one of Jack's nipples.

"So Jack, Voyeur or Exhibitionist?" asked Fay.

The woman looked older than Fay, her late 30s maybe, her hardened facial features and softer curves suggested someone more mature, she was still very attractive. Tall, trim, taut, slightly curvy with heavy full breasts and blonde, there was not much to dislike.

"Sorry?" replied Jack.

"Would you like to watch or do the taking part bit?" asked Fay demurely.

Jack was engrossed as Fay had clearly done this before many, many times judging by the woman's groans and movement.

"I mean, Jack, doesn't the idea of being watched do something for you?" whispered Fay into his ear.

Fay reached under the duvet, the heat from Jack's cock was unmistakable, Fay caressed the shaft with the flat of her hand.

"Mmm, I think being watched turns you on. An exhibitionist too. Good. So am I Jack," murmured Fay,

"Yes, it's a fantasy of mine but this is incredible," replied Jack absently.

"So you wouldn't mind if we had couple join us?" asked Fay, "You clearly approve of my bisexuality Jack?"

A small groan left Jack as Fay pleasured his rigid cock with her soft touch.

The camera was clearly being placed onto a stand and another figure joined the action, naked and male. The woman gestured to Fay to stop as the male figure turned, clearly sporting a fierce looking erection. Fay looked up as she took the cock in her hand and fed it into her mouth. The man kneaded the one of the woman's considerable breasts as Fay began eagerly sucking on his cock.

"Fuck Fay, you dirty bitch!" exclaimed Jack.

"He's got a fine cock hasn't he? A bit thinner than yours but still impressive, are you going to enjoy watching me being fucked?," asked Fay

"Yes, yes he has... this is seriously fucking kinky," stated Jack.

Jack paused for a moment, "He certainly looks ready to give you a good seeing to."

"And that doesn't bother you?" enquired Fay.

"No, it's a turn on to be honest, if that's ok?" Jack laughed nervously.

The soft caress was now replaced by Fay sucking softly on Jack's nipple, gripping his shaft she stroked his cock deliberately, moving to place soft kisses on Jack's neck.

Fay whispered into Jack's ear, "It is ok. I want a partner in crime, so to speak, we could have a lot of fun together with other people."

Returning to Jack's torso and sucking on his nipples Fay squeezed his cock, he was fully hard and as she clasped his balls they were tight.

"Jack, it's good that you like what you see. Do you want to see your whore getting fucked?" asked Fay.

Jack's breathing was becoming more laboured.

"Yes, I want to see you take that cock," gasped Jack.

Engrossed in the action on the TV, Jack watched the woman now standing she leant in to kiss the man. On screen, Fay got up from her knees and standing up, turned to bend over the table parting her legs wide and laying flat with her torso on the table top.

Admiring the woman's form, Jack could see Fay was completely naked as the woman guided the man over to her. She slid a finger into Fay's cunt and Fay was clearly enjoying the vigorous fingering of her cunt. Smearing Fay's pussy juices onto the man's cock, the woman was clearly sliding his cock up and down Fay's slit. Fay visibly winced as he drove his cock into her.

Pulling back the duvet from a distracted Jack, Fay looked up, smiling as Jack was lost on the events unfolded on the screen. Shifting her position, she slid down the bed bringing her mouth close to his cock.

Fay felt a warm affirmation that Jack was not judging her for being such a slut and she was pleased it clearly turned him on to share her body with others. Fay could feel the lust in her body rising on that thought of Jack fucking others using that fine cock of his. It pleased Fay more to watch other moan and writhe to Jack's attention. Her yearning that her own fantasies might be realised with Jack excited Fay immensely.

"Mmm, Jack, so you would be happy to share my wet cunt?" asked Fay, "She could have used a good fuck from you too."

"Fay, I'd fuck you both good and proper," replied Jack.

"Good, good. Keep watching Jack," purred Fay.

With that, Fay's mouth took Jack's cock slowly and deeply, Jack responded with a deep moan as he felt his cock engulfed again by Fay's skillful mouth.

The man was clearly fucking Fay harder now, the table was creaking and shaking with the force of his strokes into her. Fay was more vocal, yelping as the woman demanded he fuck her hard. Judging by the noises he was making he wasn't going to last long. The woman was encouraging him to fuck her harder still, telling him to shoot his load.

Jack writhed a little as Fay steadily wanked his stiff cock into her mouth, sucking on it head, circling it softly with her wet pointed tongue.

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byTheTravellingMan© 3 comments/ 56286 views/ 8 favorites

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