Selling My Anal Virginity To My Neighbour

Jack was followed into Mr Bigg-Cocks house and was pleasantly surprised to find it decorated in an up to date modern style. He did not have long to stand and admire it though, as his Shorts and T shirt were ripped off him, and in seconds he was being picked up and carried up the stairs to the bedroom. “Sorry Young Un but I can be bother with any small talk” the Big Man said, looking the Teen in his eyes.

He stated, “I want you so lets not waste any time.” “Fuck” Jack said to himself. “It’s a good thing that Toby and Mr Long have shown Me a bit of what to I have to do, as I would be completely out of my depth here.” “Can I have drink first please Mr Bigg-Cock Sir.” “Sure in a minute” he said mauling, kissing, and sucking on Jacks sexy body covered with hair in all of the right places.

“Sorry Son I am hungry for some Fresh Teen Pussy, and you will do just nicely.” “Thanks Dag Long you’re a Star,” he leered. After a few minutes, he open a small fridge in the bedroom and asked, “Do you want a beer?” “No can I have some water Sir” he replied. “Hey call me Kenny.” “Thanks Kenny or can I call You Mr Bigg-Cock, as I feel a bit rude calling you by your first name?”

“Well you a well brought up Lad aren’t you.” “I suppose so” he said thinking about his Father Leonardo Gamberini, who impress the use of good manners upon him and his 3 Brothers. He hated his Father, well not as strong as that, but they just did not get on being so a like that they clashed. As he was thinking this he spotted the Older Man’s Erection which was huge which he reckoned was at least an inch bigger than Mr Longs.

The Man was looking at him lustfully, as his Fat Long Cock Bounced about. Jack panicked a bit and said to himself “I can do this” and repeated it to himself several times gulping. “I need to see you properly stand up Jack,” Mr Bigg-Cock said being direct. Jack did as asked and automatically turn round to show off his Assets.

“Jesus Nice” and not wasting anytime the Man pulled him towards him and bite into his Bubble Butt, nipping him, making him jump. His beard tickled him, as he was slurping away at his clenching Teen Asshole and he blew into it. Sticking his thick tongue in the Teen Tight Ass Twat, he was soon munching away, holding Jack in place so that he could not  move. He knew that this was the start and it was not going to be easy and he was right about that.

Kenny Bigg-Cock was a Devil in bed and had worn out many of his Ex-Partners, as he could Rough Fuck Them for Hours on end. At first his Partners were thrilled with his ability to Screw them for the longest time. But soon enough after they were worked over for, hours, days, then weeks at a time with no let up. The result was that they could not stand it and soon broke things off with him. The last Guy left him for his Best Friend which was not nice.

Now Jack came along and he was going to take his frustration out on the ‘Boys Virgin Teen Ass Pussy Cunt’ and was just getting him warm up for long drawn out Fuck. He was going to triple his offer if he could persuade him to stay overnight . He crossed his fingers that he would.  The minute he set eyes on Jacks picture, he was smitten with the Good Looking Teen who at 19 was perfect for him.

Now he had him in front of him and took in the vision of his slim long lean arms and legs. He admired Jack firm fit shape, built from his love of sports activities, and his tight Stomach coupled with hairy  body was cover with dark fur in all the right places just took his breath away. Oh he was adorable and his fatter kissable lips, green eyes, square face, and his jet Black Hair with his dark olive skin.

“Oh God” Kenny Bigg-Cock moaned instantly smitten with the Hot Fresh Straight Sporty Teen. Added to all that Jack was of Italian descent, and this was just perfect, as it remined him of a Italian Guy that he had met years ago, whilst they worked in Hotel as Waiters.  They had the best laughs and as they lived in and shared a room they grew close.

They had slept together after drunken night out and, and it was their first time with Guy. The sex was clumsy as they were both inexperienced, but he was happy as he had thought about it for ages. The Guy was also seeing some Girl at the time and was too afraid to admit his feelings for another Guy, so they split. Sadly, they lost tough ages ago and Kenny never got over him, often thinking about him as you do.  

Kenny was also envious of Mr Long and Toby’s relationship, which he had watched from afar for the last six months or so. Yeah he knew it was for the Money, as Toby made a wad of cash for providing his special brand of services. But who cares, as they both got what they needed. Toby plenty of Cash and Mr Long Well You Do The Maths. He was thinking about this as he ate the Teen Ass out and touched Jack all over stroking him and spreading his wiry legs wide.

He was being a bit rough, but hey this was not a romance. He wanted Jack to have some fun though, as he might just come back he kinda hoped. The Teen on the other hand was thinking to himself, “No chance this is one off Mate, as I need the money and as soon as I am out of here, I will have the longest shower. Then I am off to bed, have to see the Bank Manager to pay the cash I earned in.

Pushing him away, Kenny said, “Show me the rest of you and pose a bit and flex like you are about to play some sports” and he did. Toby ran his hands self-consciously over his treasure trail and his hairy chest was displayed, and his Dick was still soft.  Kenny had been advised by Mr Long to throw some compliments at him, as it worked for Toby and he did. As a result, Jack was pleased and preened displaying his assets off fully.

“This will be a piece of Cake as this old Bloke will Cum like Mr Long did earlier and I can be off.” This wish soon would disappeared,  when the Man stood up and his Dick was pointing at him and it was actually 12 inches. A that point Jack went in to full panic mode going pale. “Calm down Son, Touch it and get yourself familiar with it as soon enough it will be inside this” and Mr Bigg-Cock Finger penetrated the Boys Clenching Asshole.

His long manly fingers, burrow its way in like an electric drill and he started to see stars. With his other hand Kenny pulled him into his thicker muscled body, and he started to mauled him. He gripped Jack thick black hair and pulled it tight. He devoured his mouth hungrily and smothering him with his long beard.

He start to hold him more firmly and started to touch him everywhere and the Jack felt this was too much too soon and pulled away. “I AINT SOME BIRD FOR FCUK SAKE” he said to himself. He was told “Jack Son, stop Fucking about I don’t have time for this.” Mr Long had advised him to be prepared for this and offer him a minimal amount and look sad and he will stay. 

So he did and Jack looked at the cash and instead grabbed it and went to walk out. He said to himself “Sod this I’ll go to  the Bank and see that nice Black Bloke Hugh Cocks-Ville, to see if I can extend my overdraft.” “I know that he fancies Me, as our Valentino his Step Brother told me so.”  So Mr Bigg-Cock went to plan B.

He pretended to talk to Mr Long on the phone and said. “Yeah like you said Jacks not up for it.” “Can you call Paul Russell tell him that he can stay over, tonight, and I will give him the amount that we agreed. He stated the amount, which was far more than he had offered Jack, who was listening indignant as he hovered on the stairs. His famous temper got the better of him.

He rushed up the stairs  and ran into the Main Bed room. He saw Mr Bigg-Cock on the bed stroking his cock pretending to talk on the phone. Jack grabbed it in temper and locked it off and he was angry and complained, “So you want to give that to whoever that Bastard that was, and it far more cash than you offered Me WHY?” He was shouting looking vexed.

Kenny replied, “Because Son, Paul Russel, won’t be a Pussy Bitch and whine and leave like you just did,“ “SHIT JACK, ITS SUCH A PITY, AS HE IS NO WAY AS GOOD LOOKING OR AS CLEVER AS YOU!” He stated this looking sad and pissed off. Jack was secretly pleased hearing this stated about him. “Look Son, I need a Hot Guy Like You To Service Me Properly OK. “

“I will dominate you, take you in the Ass and Mouth and make Cunt Out of You, but I will pay you well so what do you say Boy?” As he said this, he was looking sad, but crossed his fingers. At the same time, he was stroking his 12 inch monster and looking at Jack, who could see that he was lying, but said nothing as he needed the cash badly.

He did not point this out but stated “Thanks for being honest with Me.” “Yeah I need the Cash but please remember, I aint had anything inside me before, and that Thing Is Fucking Enormous,” he exclaimed. His Eyes were fixated on the Man’s Stiff Monster Dick, which he was stroking wildly and it was spewing loads of clear liquid which dribbled down the long Cock Length.

So Jack shred his clothes and lay on the bed next to Kenny, who was trying to control his passion and not flinging his over, and penetrating him to the hilt, which was his usual style. Instead, he started to lick him all over tickling him with his beard saying, “Your One Clean Sexy Lad And Bloody Fit As Fuck” as he reached his crotch and found it was  still soft.

So he concentrated on kissing the inside of his legs and started to suckle his hairy fur covered nuts instead. “Oh, Oh, that’s nice” and he giggles as the Man’s long bushy beard tickled him, and soon pulled him up, so that he was facing him. His plump lips found the Older Man’s Lips and started to kiss him. Jack was a good Kisser and all of his Girlfriends said so, and he concentrated on trying to touch and turn Mr Bigg-Cock on.

He was praised for his efforts, which were endearing, but limited. Kenny said to himself “I am not being patronising but look forward to teaching him what to do, in order to bring him off and entice him back to Me.” This was followed by “Don’t be Dumb, Jack aint coming back just enjoy this for what it is a Sexually Business Transaction Yeah.”  

He was somewhat surprised when without asking Jack kissed his way down his body and started to play with his Cock and started to suck his Balls. “Hey, I thought you were new to this” he said in surprise. “I am” he said but whilst waiting for you Me and My Pal Toby, sucked Mr Long Off earlier” he confessed shyly.

“He Hasn’t Fucked You Has He” he asked sharply?” “No I Am An A Proper Anal Virgin” and your tongue is the first thing which had been Inside Me” Jack replied blushing furiously.

“Good as I want a Virgin to Fuck and you are just what I need” and he stop himself calling him ‘A Hot Fresh Gay/Straight Teen Boy Whore’ as he knew Jack would leave angry at being called/labelled this, and not come back. So instead, he stop speaking and concentrated on how he was going to fit his Massive Cock into this Boys Tight Virgin Butt Hole.

So he let Jack wank and grip his Dick and manoeuvred his way round, and was soon sucking the Lads hairy nuts, which were covered with dense fur.  “Thank God you don’t shave down here” he moaned, in between sucking Toby’s medium sized Nuts into his mouth one at a time. Then taking them both into his big mouth sucking hard on them. The Boy was moaning, and his Dick was hardening.

After giving the Man Fat Cock Head a brief suck, he tried to take Mr Bigg-Cock humongous Prick into his Gullet. The Man watch him struggle try to take as much of him inside him and was pleased to see him taking at least 7 of his 12 inches into him. At the same time, he was sucking Jack so well that that he was crying and thrashing about. He came off the Man’s prick and gurgled, “I am going to Cum Mr Bigg-Cock Sir” and he was panicking.

Good was the response, and in a few minutes of being sucked and tongued expertly, he felt his Orgasm start to rise. With his mouth full of the Man’s Dick, he cried out and inadvertently took another 2 inches inside his inexperience Gullet, as he blast his Cum Load out. “Your Cum is Sweet what you been eating Pineapple” Kenny joked, and he was pleased that he had managed to bring Jack off so easily.

He pulled out of his mouth and Jack said “Aint You Going To Cum.” “Nah not yet lets Kiss some more” and soon enough he found himself lying on top of and flat against the Man Bigger body. Although he was 6ft, Jack felt small in Kenny’s strong arms with his long beard tickling his smooth face. “My God. you are gorgeous so God Damn Fit and Tasty.”

“Two fingers were inserted inside Jack Bubble hole and they were snapping at the man’s fingers as he winched and rubbed himself against him. His 7 Inches was stiff as hell again and he was surprised on how turned on he was. His mouth was devoured and he shivered and he return the kisses with hidden hunger. Mr Bigg-Cock’s Dick was pressing against Jack’s stomach pressing against him.

For a long while they swapped strong urgent man kisses and the Boys long fit legs were spread wide and soon he was rolled over and had them wrapped around his neck. They were almost flat against his head as he was fairly supple as all gymnastic lessons had paid off. “Thanks Dad” he said to himself.

Then said “Blimey if Dad, Uncle Vincent,  Joey 18 his younger Brother, Valentino 22, and Loren 25 his older Step Brothers could see him, they would be shocked to the soul.  

As Mr Bigg-Cock was much bigger, than the Teenage Boys, he looked as if he was crushing him, as he held him close, still devouring his mouth. Whilst doing so, he had lubed his fingers and penetrated Jacks Tight Teen Bum Hole. He was fingering him for a while and removed his finger and placed plenty more lube inside Jack now opened Teen Hole.

He made the Boy spread his legs and lined his dick inside the Teens Ass lips ,which were shivering and pushed forwards. Jack cried in pain at the intrusion and said, “No I Can’t Sorry I Can’t it Hurts” and the Man stopped and said, “Come On Let Go And Sort You Out Ok And Open You Up!” Jack looked at him  gratefully and he pulled out of him and they went to the bathroom.

“Have You Douched Out Before” he asked? “What’s That” he asked puzzled and Mr Bigg-Cock clarified what he meant and said, “Shall We?” “Yes” he replied and he was douched out a few times so that he was fully clean inside and out, and he felt safe although slightly embarrassed especially when he had to expelled the water four times to show how clean he was.

He was told that “I need you clean when We Fuck, as I don’t want any accidents.” “Jack I am going to be honest with you, as I am going to be rough, and it going to hurt and it be too much for you I think” he warned.  If you remember back in Chapter 2, this was just like what happened with Toby., before he was Cored Out.

However unlike Toby,  Jack knew what he meant, as he had looked up some Gay Websites and check out some Gay Porn and view a few Rough Fuck Videos. He thought it best to be educated about any situation he put himself in and nodded as he as escorted into the main bedroom. He was prepped for the next hour, with some more, Fingers, and Dildo and then several larger ones which vibrated inside him.

The preparation too place on an sturdy plastic chair set at the side of the room, and his legs were spread wide over each arm, leaving his Teen Ass Pussy, fully exposed, whilst the man work him over. He could see himself in a big mirror opposite and Jack did not recognise himself. His hair plastered to his head, due to his perspiring so much and his Ass was worked over so he was shivering in anticipation.

“Shit I look like an Ass Whore” he groaned, as he was made hooked his arms under his legs, and his face was red as beetroot. His Man Hole was being opened wider with Bigger Sized Dildos, which vibrated inside him. His Cock was Rock Hard, Spewing Man Cum. He looked at himself in the mirrors all around the room and notice with start, that his Bum hole was Dilated as it Gaped Open.

His Eyes opened in shock. “I have get inside you now is that ok?” “Yeah I Guess” he stammered and Mr Bigg -Cock popped his large Cock Head inside him. This time it went in more easily and 4 inches slid into him. “That’s Not Too Bad” he said breathing as advised and soon enough another 3 inches went inside him. Then another inch was inserted inside him.

Jack winched as he had 8 Inches planted inside him, than another inch went in and seeing his face the Man withdrew his dick and pulled him up kissing him some more and said, “Come Lets Got To Bed.” Jack could not describe his current state, but his legs were shaking as he started to walk the short distance to the bed.

“Nice One Jack” he said as he stuffed four finger inside the Boys Bum Hole. “Open Your Teen Twat For Me” and his succulent lips were clamped to his, and Kenny’s Thick, Rough Man Fingers were twisting a button inside him, causing him to pant and squealed.  He positioned him on the Bed on all fours and placed him just as he wanted.

The he entered him in a one long movement and found not resistance. “Jack You Opened For Me SO Easily, Are You Ok?” “Yes Sir” he groaned and prayed this would not go on to long ,which was wishful thinking as he had long night ahead of him. Kenny ordered him to “Push Out Your Teen Asshole” and this opened him right up and in minutes, he was soon rubbing his pubes against the Teenager Pert Bubble Bum.

“Good Boy” he cried erotically and started Fucking Jacks Tight Boy Pussy, gripping is hair and shoulders, and it felt like was pure heaven. The slow grinding and thrusting was a complete turn on, and the look on Jacks face was a completed Turn On. “Jack in turn, could not quite believed this was happening to him, as he could feel the Man full length inside him, and he was muttering pure gibberish.

After a while of being taken like this, he felt that he needed to change position and asked politely if he could. As result, he pulled over onto his side as they spooned cuddling closely. This was a little easier and at first Mr Bigg-Cock was gentle with him, so that he felt relaxed. Jack  came without touching himself. “Fuck That’s weird he muttered to himself.

“I must be a bit Gay ,seeing as I have Cum twice with this Big Bloke, whose Fucking Dicks Massive.” “Jesus I hope he will Cum soon, so that I can go home.” He was suddenly pummelled out more vigorously and squealed loudly.  His black  hair was plastered to his head  and his neck was marked and sucked on leaving huge love bites.

“It a good thing I aint got a girlfriend as she will be go crazy, thinking that I have got some other Bird having Sex With Me.”  Thinking about it he suddenly remembered, Toby having number of Large Love Bites on his Neck, as did Eric and several of the others. He counted 8 of them in total. He said to himself “I bet they doing the same as Me, renting their Teen Ass Holes Out” and he ran through them all.

“Yeah they were , as they appear to be loaded over the last few months, when he noticed Toby with the latest gear. He looked enviously at him thinking “where does he get the money from to buy all that gear and the others as well.” He was day dreaming and was shafted even more roughly and founds himself overcome as he came again and screamed.

“ Oh God what are you doing to Me Ass, My Bigg-Cock Sir” and he was dominated for a long while. Jack knew for certain at that moment, that he was not going anywhere any time soon. And you know what, he guessed right, as this was the start of long night for our Teen Jack.

To be Continued