Timmy's Tribulations

by Caliban

31 Jan 2020 3115 readers Score 9.5 (130 votes) PDF Mobi ePub Txt


Timmy came from a family where brain cells were in short supply, and to put it mildly, they were a bunch of dumb-fucks. Timmy had three siblings, two older brothers and one a year younger than him. The two older brothers were both plumbers, and his younger brother was so stupid that Timmy’s parents even believed that he wouldn’t even be able to get a job sweeping streets.

Unlike his brothers, who all looked like their dad, Timmy was the best looking of the bunch and took after his mother. Unfortunately, being of smaller of stature he was like a magnet to the rough bi-curious guys in the neighbourhood and by the time he turned sixteen; he was regularly sexually preyed upon and used by them. Timmy accepted his lot, because being a snitch in the tough neighbourhood he grew up in was considered the lowest form of life for a man. Resultantly, giving a blowjob certainly beat the hell out of having a thick ear or fat lip.

After failing his penultimate year at school, Timmy got a job as a cashier in a neighbouring town. Timmy was very happy to get away from his family and start his own life. He did not miss the pawing of these guys who only ever used him for their own selfish gratification. He was simply used as a fuck-toy by them, and found the quickie sexual interactions with them rather unfulfilling.

Timmy was rather attractive. He had an excellent body with a lovely bubble butt. His petite frame was very fair, and his skin, flawless. Timmy’s crowning glory, however, was a mop of golden blond hair.

The apartment he rented was skanky, but it was all he could afford. His landlord was a bulky alpha, named Godfrey. Given the fact that Timmy was under twenty-one, Godfrey had insisted on retaining Timmy’s identity document and driver’s licence as collateral. Uncomfortable as this made Timmy, he simply had no choice in the matter.

Sadly, some people are just born shit magnets, and Timmy was at the head of that class. After two months and three written warnings at his new job, Timmy was fired for having a bad attitude.

Upon explaining this dilemma to Godfrey, Timmy was surprised by how relaxed Godfrey was when Timmy was unable to pay his weekly rent. Timmy even felt that he may have misjudged Godfrey and that he wasn’t such a bad guy after all. Not only did Timmy have a roof over his head, but bags of groceries and pocket money was now also regularly being left in his apartment. Naturally, Timmy was trying his best to find a new job, but given his brief and unsuccessful employment history, this was proving to be impossible.

What was also perplexing to Timmy was that Godfrey appeared to be revelling in Timmy’s misfortune, and it was almost as if Godfrey wanted him to fail. In addition, Godfrey’s behaviour toward Timmy now seemed to be increasingly salacious. Every time Timmy would bemoan the fact that he had once more been unsuccessful in finding a job during the day, Godfrey would sympathetically hug him. As these hugs became more and more intimate, Timmy began to realise that Godfrey would soon start taking things further.

In what psychoanalysts would most probably refer to as a form of Stockholm syndrome, Timmy found himself becoming ensnared by this new comfortable existence. In all honesty, Godfrey was certainly not the Prince Charming of Timmy’s dreams, and also reminded Timmy far too much of the boorish guys from his past.

With every passing day, however, Timmy knew that his financial position was drawing him further back into the abyss, which he thought he had escaped from. Interestingly enough, however, the prospect of what was unfolding began to frighten Timmy less and less.

Godfrey had a very open-minded approach to sex. Although he predominantly fucked women, Godfrey never suffered from gender paralysis when it came to sex. He was equally comfortable fucking both men and women.

Godfrey owned several apartments blocks and in the preceding years, he had often got lucky with gay tenants. Three years before, he had rented an apartment to two guys. The one worked night shifts and the other had a daytime job. Before long, he was fucking both of them. What amused him most about them was that they were unaware of one another’s duplicity. Sadly, they moved on after several months.

Subsequently, Godfrey had not been too lucky until Timmy’s arrival, whom he was totally sure was gay. Best of all, being the control freak that Godfrey was, Timmy was heaven sent.

Three weeks after Timmy had still not been able to find another job, Godfrey’s true motives were revealed, as Timmy had anticipated.

“Listen, buddy,” Godfrey said, as he once more hugged Timmy after a fruitless day of job searching, “You’re building up quite a tab. I think it’s time for me to take control of your situation.”

“What do you mean?” Timmy asked, innocently.

Godfrey’s reply, however, was about to floor Timmy completely.

“Well, I know a couple of guys that would happily pay to have sex with you,” Godfrey casually stated.

As a flood of former memories now rushed through Timmy’s mind, in a last-ditch attempt, he rhetorically asked, “Why would straight men want to have sex with me?”

“Well, for them, action in the bedroom is not exactly flourishing, and the temperamental bitches they live with mostly wear their pyjamas back to front, if you get my drift.”

“Huh?” Timmy asked with a frown, not fully comprehending the metaphor.

“Jesus, boy, you’re really not the brightest pebble on the beach..., these guys aren’t getting laid at home any longer,” Godfrey concluded, with an air of exasperation.

“So, why would they want a guy to relieve their needs?” Timmy persevered, grasping at straws.

“Because these guys need sexual release, Timmy.” Godfrey answered in a fatherly manner, before continuing, “You’re young and pretty, and your two holes will offer them the unfettered access to the gratification they require.”

“But what if they misuse me?” Timmy asked, in an attempt to postpone the inevitable.

“I won’t let them… Boy, why would I allow them to damage the merchandise?” Godfrey said with total reassurance.

As his words sunk in, Godfrey quickly added, “All the money they pay will belong to you. I will keep it secure for you in my safe and who knows, in a few months you may have paid off your debt. After that, you are free to leave whenever you like,” Godfrey concluded, magnanimously.

In a rare moment of lucidity, Timmy asked, “But what’s in it for you?”

Godfrey was initially stunned by Timmy’s clarity, but soon became equal to the task, before gripping hold of his crotch and answering, “Well, buddy, naturally I’ll have free access to the merchandise at all times. Think of me as a ‘quality controller.’ It goes without saying that I must make sure that my customers are getting produce of the highest quality.”

A myriad of thoughts now raced through Timmy’s mind. He had begun to find Godfrey more appealing and maybe the Stockholm thing was finally taking its full effect. Timmy was enjoying the freedom and security that he had never before experienced. With the sanctuary of his apartment and the sustenance of his living conditions, ironically, his captivity felt like the weirdest kind of liberation in his brief existence. Timmy had also instinctively begun to trust Godfrey and knew that his sexual acquiescence was a small price to pay for his current state of comfort.

“Tell me what you want me to do?” Timmy asked, having now fully given into the machinations of his new ‘master.’

Godfrey was beside himself with excitement as he mentally saw the white flag waving. All his plans had now fallen into place. After pushing Timmy onto his knees in a show of dominance, Godfrey lost no time in unbuckling his belt and pushing his trousers and underpants downward.

Oh, yeah, payback time has just commenced. I love it when a plan comes together,’ Godfrey lustfully ruminated.

Timmy was stunned by the thickness of the uncut cock before him, but shortly began to put his mouth to work.

Godfrey had every intention of putting Timmy through his paces. Of course, he wouldn’t be too rough initially, because he had to break the little foal in without scaring him. Godfrey did, however, need to make sure that the two customers he had in mind, Dennis and Alvin, would be satisfied with the service he was about to offer them. Dennis, in particular, had told him that he liked rough sex and that his wife had frequently complained about his coarse approach.

Naturally, with both men, there was an obstacle to overcome, because Godfrey believed that Dennis and Alvin were essentially straight. With his powers of persuasion, nonetheless, Godfrey knew that this would be a minor hiccup. In addition, Godfrey was a master manipulator, a skill he absolutely thrived on.

In addition, the thought of coercing these guys into sating his voyeuristic pleasure as he watched Timmy getting solidly fucked by them, was simply the cherry on the cake for him. Once Godfrey had ripped their blinkers off, he was sure that they would be begging to come back for more pleasure.

As Godfrey reverie ended and he focussed on the blond head lapping on his genitals, he immersed himself into the pleasure of the moment.

Fuck, yeah,’ he figured, ‘the little bitch is now totally under my spell.

Soon, Godfrey commenced administering light slaps to Timmy’s face. As they intensified, he was overawed that the boy didn’t start protesting.

This little whore likes the rough approach,’ he intoned in his mind, before reasoning, ‘why don’t I escalate the process and see how he responds to a bit of spanking?

Once Timmy had been turned and placed on his stomach on the bed, Godfrey was further delighted when Timmy started whimpering as Godfrey’s rhythmic arm swayed to and fro administering slaps.

Jesus, this little bitch is in seventh heaven,’ Godfrey thought, as Timmy’s hips swayed on the bedcover like a sidewinder on hot desert sand.

The hypnotic undulation of Timmy’s hips was totally mesmerizing, and all Godfrey wanted to do was confine the creature like a seasoned snake catcher. Finally pouncing, Godfrey impaled the creature like Saint George in a mythological contest of life or death. This, however, was not a battle of good over evil, but instead, one of carnal supremacy.

As Timmy gasped and groaned in total subjugation, Godfrey’s ecstasy knew no bounds.

For Timmy, all the discomfort he felt was assuaged by the adrenalin pumping through his system, as pain became like an elixir to him. Shortly, when Godfrey lowered his torso and his ravenous lips and febrile tongue commenced daubing Timmy’s neck and ears, Timmy was completely overcome with lust.

Godfrey now began to pound Timmy’s backside with gusto. This first outing was turning into a tour de force and it was as if all the pieces of Godfrey’s plans had fallen perfectly into place. Later, when Godfrey’s balls began to twitch with insistence, he simply gave in to their craving for release.

Roaring, Godfrey erupted into Timmy’s portal.

Once Godfrey had returned to his apartment, he was overjoyed by the events of the evening. Godfrey really didn’t need the money from Timmy’s ‘enslavement’ and having Timmy as a fuck-bunny, more than served his needs. There was, however, another dimension to Godfrey’s machinations.

Godfrey was a voyeur of note and watching Timmy getting fucked excited him incredibly. For Godfrey, mental stimulation was the greatest precursor to physical stimulation. Godfrey loved the build-up that watching fornication engendered in him. He would often watch porn for prolonged periods and then relieve himself manually once he had gorged on the visual stimulation. What now excited him most was the potential of watching live porn in the build-up to his gratification.

Naturally, henceforth an added bonus would now be, using Timmy once his visual stimulation had been sated. All in all, it was like a new sexual dawn had miraculously materialized in his life.

Over the following few days, Godfrey’s ‘quality control’ with Timmy ensued prior to his meeting with Dennis.

In the past, Dennis’ financial fortunes had ebbed and flowed and Godfrey had often come to his rescue. Having the upper hand, therefore, Godfrey was not concerned about Dennis’ reaction to his bizarre proposal. Dennis would obviously never provoke Godfrey’s displeasure given their history, and Godfrey derived a perverse pleasure at the thought of goading Dennis into his web of visual debauchery.

With meticulous strategy, Godfrey now went about orchestrating his plan. He told Timmy that his first customer would be stopping by for a few drinks later that day, and after receiving a text from Godfrey, Timmy should pop into his place and bemoan the fact that he once again had not been able to find employment.

To Godfrey’s total pleasure, things that evening with Dennis progressed even better than Godfrey could’ve imagined. Dennis was really throwing back the beers as he grumbled about his unhappy life with his wife, and once Dennis had unburdened all his woes, Godfrey took up the reigns.

Slowly, and measuredly, Godfrey then began to boast about his newfound sexual exploits. Initially, Godfrey was met by disbelieving glares as he explained his relationship with Timmy. Nevertheless, unperturbed Godfrey expounded his philosophy on the matter. Although primarily uncomfortable, Godfrey could soon see that Dennis was guardedly intrigued by what he was hearing.

“I didn’t know that you swing both ways, buddy,” Dennis finally uttered.

“Well… you live and learn in this life,” Godfrey stated matter-of-factly, before continuing, “Women are complicated and need all kinds of boring shit to open their fuckin’ legs, unlike the cock-hound that I’m currently fucking. Timmy gives me what I want and when I want it, without any lip. Whether I’m fucking his face or very tight little arse, I’m in charge. Best of all, once I’m done, I don’t have to hug him and say all the bullshit women require and I simply tell him to fuck off. It’s fuckin’ awesome.”

After a brief silence, Godfrey then laughed before concluding, “There’s no greater pleasure than falling asleep with empty nuts.”

Following a momentary reflection, Dennis answered, “Yeah, but he’s still a guy, bro.”

“Fuck, buddy, when you look down at a head pleasuring your dick, of a tight pink pucker about to milk your deprived dick, what does it matter?” Godfrey replied.

After a sustained silence, Godfrey then asked, “When last did you have a good fuck?”

“Don’t even ask,” Dennis replied, forlornly.

“So… what have you got to lose?” Godfrey countered, “Besides... who’s going to find out about this?”

Godfrey could see Dennis’ mind working overtime at this point.

After another prolonged silence, Godfrey then dealt the finishing blow; “Listen, buddy, why don’t I summon the boy so that you can have a good look at him? He’s as pretty as a girl. I’ll tell you what… although the boy needs the money, as you will hear. If you want to give it a try…, I’ll give you a freebie.” After a pause, Godfrey then dealt the final blow. “Best of all, Timmy takes it as rough as you like.”

Godfrey could now see Dennis’ mind working overtime. Dennis had a blend of intrigue, lust, and apprehension on his face.

“Just meet the boy and then decide,” Godfrey finally suggested.

After Dennis nodded uncomfortably, Godfrey dialled Timmy’s number.

When Timmy arrived, Godfrey could clearly see a look of approval on Dennis’ face. Godfrey now asked how Timmy’s job search had gone, to which Timmy replied with a forlorn shake of his head.

Perfect,’ Godfrey thought to himself.

“The boy needs your help,” Godfrey next responded, feigning a look of compassion.

Dennis was very impressed by how pretty the boy was, but nervously became somewhat fidgety.

“Buddy,” Godfrey said, “Why don’t you just lie on the bed and let Timmy show you how skilful he is?”

After a minute or two, Dennis then began to remove his clothing very gingerly.

As Dennis lay back on the bed he asked Godfrey, “Are you going to leave us now?”

“No, I am going to sit and watch,” Godfrey answered as he pointed to the easy chair in the room. “I have to make sure that you get the attention you deserve, so that you become a satisfied customer.”

“Oh,” Dennis said with a puzzled frown.

By now Timmy had removed his shorts and t-shirt, before kneeling next to the bed to commence his duties. Timmy left his jockstrap on, just as Godfrey had advised.

As Timmy began his oral responsibilities Dennis began to relax. To the drone of Godfrey’s voice issuing instructions, Dennis couldn’t remember the last time that his knob had been sucked and instantly began to enjoy this forgotten pleasure. Timmy went all out to please his customer and soon his mouth was in full cry. Fortunately, Dennis had a very comfortable cock, far less taxing than Godfrey’s much larger dick.

For the following twenty minutes, Dennis’ genitals were given the most gratifying service imaginable, as Timmy’s head animatedly bobbed around.

Their ecstasy was then interrupted when Godfrey suggested, “Why don’t you fuck the boy’s pink pussy, Dennis? Remember, the boy likes it hard.”

Delighted by this idea, Dennis began to arise. As he did so, Timmy moved to the bottom corner of the bed and lay on his stomach.

Next, reaching behind him he used his hands to open his cheeks for Dennis. As Dennis glared at the pink portal, Godfrey could see an expression of overwhelming horniness on Dennis’ face.

Leaning over Timmy on outstretched arms, Dennis now rubbed his dick in the boy’s crevice. After a short while, Dennis then used his right hand to place his dick-head on Timmy’s manhole. In an instant, Dennis entered Timmy’s backside with force.

As Dennis commenced stabbing the boy’s butt and pausing between thrusts, Dennis was totally elated by Timmy’s grunts and groans. If Dennis had ever done this to any of the women that he had previously had sex with, they would have told him off. Yet here he was, rough-fucking Timmy with no repercussions. Dennis couldn’t remember when he had last been this turned on.

Dennis now also began to join in with Godfrey’s lustful banter as he hammered Timmy’s arse ever harder. It was as if a primitive force was completely overwhelming his senses.

Godfrey loved the visual stimulation as he sat toying with his dick. In addition, watching Dennis’ ample butt cheeks flexing as he manically pounded Timmy, was breath-taking.

In an attempt to further enhance his visual pleasure, Godfrey suggested, “Pull your cock out and give the boy a good spanking. You won’t believe how much that tightens his hole.”

Dennis did as instructed and really began to whack Timmy’s arse. When Dennis returned his knob to Timmy’s butt-hole, he grunted in satisfied agreement with Godfrey.

This procedure now became the routine over the next fifteen minutes, before Dennis, thankfully, became so overexcited that he unloaded into Timmy’s backside with a roar.

Afterward, once Dennis and Godfrey returned to the living area for a drink, Timmy simply remained lying on the bed, knowing full well what would follow later.

After Dennis had departed Godfrey returned to the bedroom. With a smile, he announced, “Well done, boy, you have your first happy customer.

As Timmy had expected, Godfrey was as horny as hell by now, and Timmy found himself in the same position as before with Dennis. This time, however, given Godfrey’s superior endowment, the fucking he received was far more intense.

With a very sore backside, Timmy fell asleep happily that night, knowing that he was finally employed again.

Godfrey’s was far more confident about Timmy’s next customer, Alvin. The reason for this was that a year before, he and Alvin had once a threesome with a woman.

On that occasion, as he and Alvin spit-roasted the female, at one point during their session when Godfrey stood to the side to allow Alvin access to her pussy, Godfrey tweaked one of Alvin’s nipples. When Alvin showed his approval, Godfrey instinctively moved behind Alvin with the female in the doggy position at the edge of the bed.

Godfrey now encased Alvin’s torso before both Godfrey’s hands went to work tweaking Alvin’s nipples. Upon this happening, Godfrey’s dick lightly touched Alvin’s backside. With no protest from Alvin, Godfrey’s cock soon slid into Alvin’s crack. To Godfrey’s amazement, Alvin next altered his to and fro hip action, and commenced swaying his hips in an inviting manner.

Unfortunately, nothing further happened because Godfrey didn’t wish to freak-out the female they were with. Instead, Godfrey then simply moved onto the bed before her, and let her suck him off.

***

When Alvin arrived at Godfrey’s home as arranged, they had a few drinks before Godfrey again started his pitch. Unlike with Dennis, Alvin, nevertheless, needed no convincing before agreeing to meet Timmy, and in no time at all the action got going in Godfrey’s bedroom.

Unlike with Dennis, Alvin preferred to remain standing for his blowjob, with Timmy kneeling before him. As Godfrey watched from his seat, he was interested to see the differing technique from Timmy’s oral encounter with Dennis. Unlike with Dennis, Alvin lovingly caressed Timmy’s head as he went about his work.

Finally, when the time for Timmy’s anal penetration arrived, Alvin first removed Timmy jockstrap before asking him to lie at the edge of the bed on his back. After Timmy held his legs back for Alvin, Alvin very slowly entered Timmy’s backside. Once in, Alvin’s hips commenced a leisurely grinding motion.

Much as Timmy had enjoyed Dennis’ harder approach, this change of pace was simply fantastic.

Godfrey was also enjoying the show and found the sensuality of what he was witnessing, very pleasing. Although he had seen Alvin’s backside before, Godfrey had never realised just how sexy it actually was. What further stunned Godfrey; was when Alvin lowered his torso and began kissing Timmy.

Much as Godfrey was enjoying his voyeurism, Godfrey now began to feel an inexplicable force to join in the action start overcoming him. Although this was certainly not part of his original plan, a horny compulsion began impelling Godfrey to partake in the scene he was watching.

After moving toward the bed, Godfrey placed his hands on Alvin’s lower back and stroked him. Then, as Alvin lifted his torso onto outstretched arms, Godfrey began rubbing his dick in Alvin’s crack.

Looking up at the two guys, Timmy was totally awestruck by what he was witnessing. ‘Christ,’ he thought, ‘can this really be happening? It’s so fuckin’ hot.

Instinctively, Timmy’s hands slipped down Alvin’s body and after lifting his shoulders slightly upward, he placed his hands on Alvin’s butt before pulling Alvin’s cheeks apart. With Alvin’s hips now stationary, Godfrey commenced nudging his cock ever forward.

Looking up at Alvin’s face in anticipation, Timmy was overjoyed when he saw Alvin’s face contort in sexual submission. Not long after and spurred on by Godfrey’s momentum, their train got underway. As Timmy kept looking up at Alvin’s mouth that was twitching with stressful delight, the scene he was a part of just became more magical.

For Alvin, this was a dream come true. He had often wondered, how it would feel to have a dick up your arse whilst fucking someone else, and it was even better than he had imagined.

The next event that now followed made Timmy’s bliss escalate even further. After pulling Alvin torso upward, Godfrey now commenced tweaking Alvin’s nipples while simultaneously nibbling on Alvin’s ears. Still totally intrigued by Alvin’s lips, Timmy observed Alvin’s open mouth now begin to gasp with gratification.

Much as Timmy was enjoying the physical stimulation, he had now also assumed the role of the voyeur.

As Godfrey’s oral action intensified on Alvin’s neck, ears, and shoulders, it soon became clear that Alvin’ overstimulation was reaching fever pitch. Shortly, Alvin’s body began to shudder when he creamed Timmy’s backside.

After Alvin moved aside, Godfrey immediately plugged straight into Timmy’s arse.

With Timmy now also frantically tugging on his knob it didn’t too long before both he and Godfrey reached the point of no return. After Timmy began spewing his cum all over his stomach, Godfrey pulled his dick out of Timmy’s arse before adding to the spunk deposit.

Both Timmy and Godfrey were now amazed when Alvin bent over and began to suck and lick all the jizz off Timmy’s torso.

When the trio moved through to the lounge for a drink, Alvin went in raptures about the double delight that he had experienced in the bedroom.

Shyly, Timmy then said that he hoped he too would one day experience that pleasure.

Then, after glancing at his watch Alvin said, “Well, I’m in no hurry.”

Next, after looking at Godfrey, Alvin added, “If you’re not sick of me and prepared to make Timmy’s dream come true, I can stay a while longer.”

Godfrey was very happy to make Timmy’s dream come true.

***

As Timmy lay on his bed that night he smiled, thinking about what had recently happened in his life. Timmy then reflected upon the fact that being a shit magnet, as he had always thought of himself, wasn’t that bad after all.

by Caliban

Email: [email protected]

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