Selling My Anal Virginity To My Neighbour

Toby was in desperate need for Cash and he was flat broke. He was 19 and had just finished college for the summer and was bored and desperate. He was moaning away to his Best Pal Eric, as they had planned to go on 2 week Lads Holiday to Malaga and the deposit was needed next Friday and he was only one in their group that had not come up with the money. Eric had no problem with cash, as he had manage to gain a part time job that paid fairly well at a local gym. “What am I going to do” sighed Toby running his hand through his thick wavy dark brown hair which badly needed a cut. He was 6ft, slim with long lean arms and legs and had peaches and cream skin. His skin glowed and he had full kissable lips and deep blue eyes and a square face. He was good shape as he played lot of sports and  his stomach was tight and his body was cover with fur in all the right places.

For the last couple of years, his chest and stomach hair had grown so that he covered with tantalising trail of hair which lead down to his crotch area and way down to his hairy long legs and size 13 feet. His 9 inch cock which was always semi hard, bobbing about as he played sports. He hit the gym a lot recently as he was trying to build himself up and Eric got him in for free which was bonus. He was also a runner and always jogged past his neighbour who lived down the road Mr Long 45 who always waved at him, but he never waved back ignoring him as his long legs and broad sports Bubble Ass, which thundered past him bouncing with attitude and covered in a pair of luminous running shorts.

Mr Long notice him all right and could not take his eyes off him. He had just moved into the area about a year ago and thought it was fairly ok. He was one of those big built Scandinavian types with flaming red hair and a full beard and he always looked serious, until he smiled which lit up his face. He had high sex drive and was completed in lust with young Toby, who he looked out for everyday and as soon as he saw him, waved, and was ignored as usual. After each encounter he would walked back into his house and crack one out, thinking about how he could get inside the fit College student Bubble Ass as he spurted a decent load on the floor, table, tissues etc. Each time he came, he told himself off saying “He is young enough to be your Son You Fool , Come To Daddy” he laughed.

Eric said to his best friend, “if you are that desperate for cash, why don’t you let Mr Long down the road take your ‘Anal Virginity’?” “WHAT DID YOU SAY?” Toby spluttered. “I said if you are that desperate for cash, why don’t you let Mr Long down the road take your Anal Virginity” he repeated looking dead serious. “Are you crazy?” Toby said not quite believing that his best mate that he knew since knee high, had suggested such a nasty thing to him. “No Pal I’m Straight, so that is never going to happen” he spluttered. “Fair enough it was only a suggestion, but I heard that Mr Long is very generous, and he is loaded, and he is always looking at ‘YOUR ASS’, which you have said to me loads of times remember?”

Toby ignored the last bit and asked, “How do you know that he is loaded” and at that moment his phone rang, and it was his Dad reminding him that they had to go to his Aunts for the evening. “Sorry Mate I gotta go family stuff catch up soon.” “Yeah sure, just remember what I said ok”, and Eric got up fist bumped him and left. The rest of the evening and week went by and Toby could not get Eric’s suggestion out of his head. “No way can I let that Big Burly Beefy Bearded Bloke, Take Me In My Tight Asshole” he said to himself massaging his buttocks and touching his sweaty asshole which snapped shit and he fell asleep.

That evening Toby had a dream about Mr Long and his dick just about to enter his greased asshole. The man was on top of him, with his cock having just popped his Virgin Cherry, and Toby was crying with lust and locking lips with him, yelling “Fuck Me In My Virgin Ass Hole Mr Long.” He woke up with his sheets all wet with sweat and he was perspiring, and he was lying in pool of spunk and his dick was still erect and in seconds his hand was massaging his 9 rock hard pole. He was so turned on that he soon increases the speed and just could not stop and was so confused.

One hand was soon flying going up and down his rock hard erection and he was sucking three fingers of his other hand.  He imaged being on his back and his big burly red head serious looking neighbour down the road, plowing into him with his big prick, which was far larger and wider than Toby’s. He was imaging the lips of his asshole being stretched obscenely as they were being pulled right out and then pushed back in, then out and in and then Mr Long withdrawing his prick, leaving the Boy with an ‘O’ opening gape, which was flapping like an open mouth hungry for his next mouthful.

Toby was muttering to himself, “Cum Inside Me Mr Long” and in his fantasy, he was re-entered and flipped on his side and their bodies moved as one and Mr Long cried, “ I’m Cumming Young Toby You Fucking Ass Sluttttttt” and he shot off inside him, so much so that his excessive jizz spilled out of his hairy muff  and ran down his back and dripped on the bed. At the same time Toby shot off 10 spurts of spunk all over his stomach, the pillow and wall being him and was still hard.  “Fuckkkkkk What The Hell Is Wrong With Me” he cried “this can’t be right can it as he came down off his sexual high feeling guilty as hell and disgusted with himself. “It’s only a Fantasy, Thank God” he laughed nervously “”as if I would let any bloke let alone that Geezer Fuck My Ass” and he fell back asleep.

In the morning, his Dad Melvin came in and found his son on  his back sleeping and sniffed the air and recognised the sweet sour smell of Cum. He looked closer at his son’s stomach, then the pillow and the wall behind the bed, which had dry spunk on it, and said out loud “Son that must have been some wanking off Session you had last night.” He cleared his throat and his prick was hard and said “Son you need to get up now it 11am, let’s not sleep the day away ok” and as he said this, still half asleep Toby’s prick was tenting the sheets and he threw the covers off and was absently stroking his semi not caring if his old man saw him. “Sure Dad” he said and as his Dad left tearing his eyes reluctantly away from his sons semi hard on, which he noted was bigger than his and ran to his study and wanked off and cracked one out all over the wall, stifling his moans.

Toby meanwhile  got up and remembering his fantasy grew hard again. “Right no time to waste I’ve got to meet Eric later as we are off to the gym” and he left and met Eric and the others were there. The deposit was required on Friday and it was Monday now. Toby looked a bit down and once again Eric stated what he had the week before into his ear, and this time he did not say anything remembering his fantasy last night and he blushed and started to perspire which his pal noted but did not comment on. “How can I make an excuse to go and see Mr Long” he thought to himself and carried on working out but was clearly distracted thinking about what he should do?

As luck had it, he set up for an early afternoon jog and as he passed the man’s house, he was there waiting waving as usual.  Toby stopped and pretended to do up his laces showing off his Bubble Butt and then did some warm up stretches. He noted the man watching him like hawk which was quite uncomfortable as he usually did that to women, but though this is going to be easy. “Hey Mr Long, I’m Toby” he stated as he was doing his stretches, showing all of his wares. As usual his prick was semi erect, and his chest hair was peeking out of his running top.

“Hello, its Toby isn’t it, how are you this fine day great weather lately isn’t it?” the man clearly enthralled with the Hot Teen being so near within touching distanced stated. They made some small talk as Toby did some pretend lunges on the spot and turn his Money Maker to the man who was salivating over his good fortune today and pretended to do his other shoe lace up showing off his long legs and Bubble perfectly. “Ok then see you around, I gotta go” he said and just as he was about to take off, he said, “Mr Long I don’t suppose you got any odd jobs to do around your house or garden, do you?” “It’s just that I’m flat broke and need the cash urgently?” “Yeah, I got a few things that you could take care of, young man, drop in on your way back and I will show you what needs doing.”

An hour later after a long run, Toby turned up wet and sweaty and said “sorry about this, I stink.” “No problem have some water” and he did, and Mr Long eyes were glued to him. “So what do you need the money for?” “A Lads Holiday and I need it by Friday.” He thought here goes, “I’m desperate and will do anything that you need to Sir.” “Like What?” and Toby babble on not quite sure how to say what he was prepared to give up.” After stammering and stuttering for a short while not making any sense, so Mr Long cut in. “Son, what can you give me that going to cover that sort of cash as its lot of money.” He stated this looking at him directly and the boy sat with his mouth open, his heart was racing, and he was silent and gulping trying to work up the nerve to ask him.

“Son stop pissing about and tell me what you can give me, that would warrant that amount of cash” he snapped. “Here Goes “Toby said to himself. “Mmm I can let you ere” he stammered nervous as hell, “Let Me What?” “Oh Fuck” Toby said, “I Could Let You Fuck Me In My Ass!” “What, I don’t do Teenage Boys, are you taking the Piss Son?” Mr Longs face was like thunder. “Ere Yeah, Sorry I was Joking” Toby said embarrassed and flushing crimson thinking that he had made a stupid mistake he was going to kill Eric the Bastard for setting him up.

“Sorry I’m So Sorry I gotta go” and he got up and went to rush out of the house as he was perspiring like crazy and water ran down his face. “Here use this towel and sit down” Mr Long said and guided him back to the chair. “Toby, I know you need money but offering yourself like this to a stranger is dangerous, What Were You Thinking?” “I wasn’t me it was my so called mate, he told me to ask you as you loaded” and the Boy was scarlet with embarrassment and put his head in his hands and groaned with shame. “Who’s that then?” “Eric.” “Oh that little Asehoe he said to himself “Yes, my Pal Mr Cock-Hound down the road told me about him, how he seduced him, and he had been visiting him and many other guys in the neighbourhood servicing them regularly for Cash spinning the line that he’s a Virgin, no wonder he was loaded.”

“Look Boy your Anal Virginity is Precious, don’t waste it on this!” “But I need to go in this Lads Holiday “Toby cried “and I am desperate.” “Really why?” “Cause I just am, and all of my mates will be going and scoring all of those hot girls out there.” “Anthony my other mates brother, went last year and shagged loads of women” and as he said this his dick rose in his wet shorts which clung to his long slim frame. Mr Long was salivating and said “look come over later and we can work something out as despite his reservations this was too good an opportunity to miss, he reckon as the Boy was ripe for the taking.

4 Hours later Toby had showered had a light dinner and said to his parents “I am out tonight and will be back late, so see you in the morning.” He was wearing a white t-shirt and a pair of fitted shorts which showed off his long legs, big feet and accentuated his perfect ass. His hair hung like a crown and he had shaved. “Phew” his Dad said, “Son are you off for a date tonight?” “No Dad I’m just meeting the lads “and he left and walked round the block and back to Mr Longs House the long way, as he did not want any of his neighbours seeing him going into the man’s home, especially as  he was about to lose his anal virginity and the thought of having this man’s dick in his Butt was not something that he wanted to think about too much.

At 8pm Mr Long open the door and held his breathe as Toby was looking totally fuckable and he wanted to rip his clothes off and take him right there on the front door, not caring who saw them. But he pulled himself together and said, “come in, do you want a drink” “Yes please” and he got him a beer and they sat looking at each other. “Toby, I thought about what you said, and I’ll agree to give you the money, but I do want to take you up on your offer.” “Really what do you want me to do?” he asked super excited forgetting that he had to have sex with this older guy whose 10 inch cock was hardening already.

“Let’s go through a few things first. I don’t want any trouble later on, so let’s go through a few details first.” “I’ll give you cash, and I want you to stay all night so let’s take thing slow.”” I want to make love to you, but I do like rough sex and want to fuck you all night long.” “I want us to kiss, suck each other cocks and I want to eat your Boy Cunt out.” “I need to douche you out, before being inside you, so that you are clean, as I fuck deep and want to finger you and open you up properly.” “Then I want to enter you taking your anal virginity and fuck you in a number of different positions, it will hurt at first but will give you so much pleasure.” “What do you say?”

Toby clearly was not listening like a lot of Teenage Boys his age, he was just so happy he was going to get the money and going on holiday with the lads. He was given a list prices that he could ask Mr Long for and the more that he would do,  the more money he would get which was quick simple really. But it all went over his head as figures was so not his bag. “So if I let you do that, I will get my money to go on my Lads Holiday right?” Toby had no idea what he was letting himself in for, but he just kept on thinking “I need the cash it can’t be that bad can it. Mr Longs an old man like my Dad”  and like most young naïve guys he thought the older man won’t last that long so this will be easy.

However 12 hours later Toby was waking up his hair stuck to his sweating face and with a tender ass hole full of cum and a sore throat and could taste the slimy cum in his mouth. He face was covered with dry jizz all and his hair was mattered when he touched it with stick semen. He was being screwed on his side feeling every inch of the man’s thick 10 inched prick as it thrusted and throbbed inside him and he groaned, “When is this going to be over, as ‘I Just Want My Bloody Money For My Holiday?” “Surely this Old Cunt Can’t Last Much Longer CAN HE Oh Fuck I am Cumming again?”

Unluckily for him, Mr Long had an insatiable appetite for Fucking Teen Boy Ass and had been fucking Toby all night long and was still plowing away inside of the Sweet Tender Boys Pussy, which despite  being plunder all night, was almost as tight as when he first entered him many hours ago. Mr Long had made him cum multiple times Toby was embarrassed to say, and that after he got over the initial pain, his body had just about coped with all of the pleasure that he was receiving as his ass was full of the man cum loads which were sloshing about inside of him and leaking onto the bed below.

To Be Continued