Anal Deflowering Pt 5

This giant slab of meat in front of Charles’ face was genuinely the largest he had ever seen, and he doubted he could do much with it, either with his mouth or his anus, but he was determined to try.

Part 1 | Part 2 | Part 3 | Part 4


There was always a nagging doubt in Charles’ mind about his true sexuality. The recent experiences with men from various life and backgrounds should have convincing evidence that he was gay. However, two ‘things’ prevented Charles from openly admitting his gayness.

One of the ‘things’ holding him back was known, defined, real, and that was his family’s attitude to countervailing sexuality. Admitting gayness meant disappointing kith and kin. Charles had not yet found an acceptable solution to that problem. However, this issue was not uppermost in his mind. Rather, he sought to determine what the second ‘thing’ was.

The moment of reveal and understanding came obliquely by way of Charles’ childhood idol and occasional lover, Michael. Concerned that Charles sexual experimentation might leak and lead back to him, Michael suggested to Charles that he grow a beard to as to “allay” any suspicions of his sexuality. The beard was considered a sign of peak manliness, exemplifying such virtues as wisdom, strength, sexual prowess and high social status. Charles was dubious but gave it a shot.

One night, after Charles swallowed Michael’s second load — the first was deep in his arse — the latter offered the former an unusual proposal.

“The beard is a great improvement,” Said Michael, “But there is a way to guarantee no-one will ever discover your true sexuality.”

“Oh, and what would that be?” Asked Charles, taking a swig of water to offset the saltiness of Michael’s seed.

“A marriage of convenience,” Replied Michael confidently.

“A what?”

“It’s simple,” Began Michael, rattling off the particulars like it was a sales pitch, “People that come here on holiday visas, working visas etc., love this land so much that they want to stay permanently. The problem is that the immigration law doesn’t permit it unless that person is married to citizens. These people are willing to pay large sums of money to someone that will ‘act’ as a husband or wife for a time. A legal marriage comes with a marriage visa permitting the holder to live and work here until they are eligible to become citizens in their own right.”

“Is this legal?” Interjected a skeptical Charles.

“It’s a grey area of law,” Replied Michael airily, “The married couple are subject to periodic checks by Immigration, so they have to ensure they project all the trappings of a bona fide marriage.”

“Including having sex?”

“That part’s optional,” Chuckled Michael, “To the world at large, if you enter one of these sham marriages, everyone will assume you are straight, and you’ll have a tax-free money thrown your way.”

“How much money are we talking about?” Asked Charles.

“The desperate will pay anything, but the going rate is five to ten.”



“Fuck!” Exclaimed Charles.

Not that he needed the money as he had a successful career, but that’s a sizeable chunk of coin that would feather the nest. However, the burden of keeping house with a woman for three years would curtail Charles’ sexual endeavors.

“As long as you keep the act up,” Said Michael, anticipating Charles, “You can chase as much cock as you like, discreetly.”

Michael, whose public profile had exploded recently, became a ‘captain of industry’ with a glamorous wife and all the trapping of wealth and celebrity status. He was keen to protect his reputation and could not afford a scandal. Muckrakers and paparazzi might stumble across Michael in a car receiving a blowjob from his friend, and all hell would break loose.

Charles thought his bum chum was paranoid, rightly pointed out that the risk would be eliminated if Michael stopped asking for his sexual services

“I am gay, though,” Explained Michael, “My celebrity life is all for a show, a sham, but I enjoy it and do not want or intend to give it up.”

Given Michael’s meteoric rise to fame, the two saw less of each other, which freed up Charles to experiment with other men in different scenarios. However, the circle open to gay men was small, and word got around and had gotten back to Michael. In any case, Charles was a comparative nobody and given Michael’s profile, he felt sure there were closet gay men all over the place, so why bother with him? It was a question that Michael refused to answer. He simply called Charles when there was an itch to scratch, and Charles dutifully performed.

“Have you fucked your sham wife?” Charles asked.

“On occasion, why?”

“What was it like?”

“I wore an eye mask so I couldn’t see what she was doing. She made me cum, I guess, so there’s that.”

Michael seemed entirely unimpressed with the encounter, and Charles did not press for more detail. The thought of sex with a woman had never entered Charles’ head, let alone envision such an encounter.

“So, back to the topic at hand,” Said Charles, “If I was to agree to such a proposal, do you have someone in mind?”

“Not yet; I wanted to know if you’re interested.”

“Let’s say I am, depending upon my future sham wife.”

“A friend of mine who works for my company, we went to school together, although I doubt you knew him, runs this operation,” Whispered Michael conspiratorially, “I’ll reach out to him.”

“How big is this sham marriage market?” Asked Charles.

“We have more visa holders than we have willing spouses.”

“When will I get the money?”

“As soon as the marriage certificate has been registered,” Replied Michael, “You show my mate the registration, and he hands over the cash, less a modest finder’s fee.”

“Off course,” Laughed Charles, “Okay, tell your man I’m willing to meet.”

Charles was keen to be off as hard cock in his pants needed attention. The two bum chums kissed each other goodbye, and Charles scurried off home for some self-love.

A few weeks passed before Charles received a message from Michael to meet his friend Rudy at the Irish Pub in town at 8 PM and be punctual.

He arrived at the appointed time, grabbed a drink and a table. A certain level of anticipation flowed through Charles as he scanned the pub, looking for Rudy with whom Michael did not describe.

Suddenly, a heavyset, swarthy man slammed a drink onto the table, startling Charles. The man before him looked so powerful that one punch would smash the flimsy table they sat together.

“I’m Rudy, and you are Charles,” Growled the man.

Charles nodded and noted that Rudy held in his giant paw of a hand a plain brown A4 envelope.

“Take a look!”

Charles nervously took the envelope and took out the contents. What greeted him was a parody of a James Bond file. There was a photo of a woman paperclipped to the upper right-hand corner of what looked to be a dossier.

Tonight’s ‘mark’ was Lynn, 30 years old, an Australian who was so desperate to obtain citizenship that she was willing to trust Michael’s fixer with an enormous sum of money to enter into a marriage of convenience. The dossier even contained a contract of payment, terms of marriage and a guaranteed divorce at the end. With such an extensive and detailed paper train, Charles concerns about legality were partially assuaged.

“What happens if an immigration inspection determines our marriage is a sham?” Asked Charles of his table companion nervously.

Rudy looked askance at Charles and looked put out by spending energy explaining the minutiae of sham marriages.

“You want to make sure it happens in the last six months of the marriage,” He snarled, “Because that’s how long the court process takes, on average, to have the marriage annulled and your wife booted back to Australia. In the last six months, she still has a good chance of obtaining citizenship.”

“How many of these sham marriages have been discovered?”

Again, Rudy shrugged his shoulders at having to answer such questions, but he confirmed that all of the marriages he facilitated were successful.

Thus reassured, Charles went back to examining the dossier. There was something intrinsically alluring about Lynn. She had expressive eyes and an expressive mouth. Charles felt no arousal, but a marriage of convenience could work. Another stipulation of the contract required Lynn to move out of London so that she and Charles could be seen together frequently.

Charles agreed to see no downside to the deal, and the gruff Rudy collected the dossier and stuffed it roughly into the envelope. He leaned in to whisper, and Charles was terrified.

“Michael tells me that you like to suck cock?”

Charles stammered that he did.

“Good,” Whispered Rudy, “I want my cock blown.”

Charles was taken aback and, while repelled by this man physically, felt his cock grow in his pants at the thought of some anonymous alleyway action.

“Let’s go,” The monster growled.

Rudy led Charles to a dark corner of the pub car park.

“On your knees,” Rudy whispered as he undid the zipper of his jeans and revealed a giant penis to Charles.

This giant slab of meat in front of Charles’ face was genuinely the largest he had ever seen, and he doubted he could do much with it, either with his mouth or his anus, but he was determined to try. Failure might result in a broken neck.

Grabbing the monster gently by the base, Charles opened his mouth, closed his eyes and took the plunge.

Fuck, Charles thought, as he grappled with this host, my mouth won’t fit around Rudy’s cock. Time had no meaning as he sought a way to accommodate this slab of meat. At best, about one third was achieved without dislocating Charles’ jaw. This seemed to please Rudy, who purred appreciatively.

Charles cupped and tickled Rudy’s balls and felt the sack tighten considerably. He felt a sense of relief that Rudy was receiving some pleasure from Charles struggle and later relaxed and developed a rhythm of sucking on the head, working the shaft with a hand and tongue and playing with the balls.

Rudy appeared to drop his tough-guy act the more Charles pleasured him. A moment of alarm occurred when he placed a giant hand on Charles’ head, but Rudy gently encouraged Charles in his endeavor.

“What’s your arsehole like?” Asked Rudy softly.

“I don’t think that’s going to fit.”

“Can I try?”

Charles felt powerless to refuse but also intrigued by the thought, so he stood up and unbuckled his jeans by way of surrender.

“Here, let me help you get ready,” Said Rudy by bending Charles over a bin.

Rudy dropped to his knees to Charles’ infinite surprise, parted his cheeks apart, and began gently tonguing Charles’ tight pucker.

As Rudy’s rough tongue danced across his delicate pucker, Charles gasped in surprise and pleasure. Charles cock was aching for attention, and he wanted to touch it but knew that he would probably climax immediately if he did. The joy of being rimmed by this bear of a man was immense and unique.

Next, Rudy switched to fingering Charles’ O-ring, gently loosening up that most intimate holes. Charles hissed initially but quickly relaxed until the second finger went inside, then a third and fourth. Charles controlled his breathing with each additional finger and focused on the pleasure of penetration rather than the momentary discomfort.

“I think you’re ready,” Whispered Rudy.

“Really?” Asked Charles in half disbelief.

“I’ll apply some lubrication to your arse and my cock, and we’ll be ready to try.”

Charles saw Rudy reach into his coat pocket and retrieve a jar of KY Jelly. He applied a liberal amount to his monster cock and them to Charles arsehole. Rudy worked the greasy gel deep inside Charles’ shitter and all around the outside.

“Just relax; this won’t hurt,” Rudy reassured, “But if it does, say so, and I’ll stop.”

This paternalistic demeanor was at sharp odds with that first moment of meeting, and it put Charles in a relaxed frame of mind.

“Then fuck me.”

Charles spread his cheeks apart as far as they would go. Rudy pressed the tip of his cock at the quivering orifice and pressed gently. At first, Charles’ pucker put up too much resistance even to a man as powerful as Rudy. The two both became quickly frustrated by the lack of penetration.

“Push out your anus,” Whispered Rudy, “Like you’re taking a dump.”

Charles did so, and pop, the head of Rudy,s cock breached the resistance. Both men took sharp intakes of breath.

“Shit!” Charles hissed.

“You okay?” Asked a concerned Rudy, whose hands had just gripped Charles’ hip in a vice-like hold.

Escape was impossible, so Charles focused on relaxing his anus. The generous coating of jelly alleviated the worst of the pain, and, slowly, a feeling of euphoria enveloped Charles. I can do this, he told himself.

“Yeah, keep going,” He told Rudy.

Rudy appeared to be scared witless but, nevertheless, applied more pressure, and to his amazement, Charles’ anus willingly accepted more.

“Fuck, you’re tight!” Rudy hissed.

“I’ve never received anything like you before,” Charles grunted in reply.

“I’ll go slowly,” Assured Rudy as he gently impaled Charles.

Charles felt stretched in a way never before experienced, but he was amazed at how much punishment his anus was taking. His cock was about to burst, however, but, tempting though the thought was, he kept his hands firmly gripping the bin.

Suddenly, the inching stopped.

“That’s about as far as I dare go,” Rudy whispered.

“How far are you in?” Asked Charles through gritted teeth.

“Not even half,” Rudy replied, “Let me know when you’re ready.”

The pressure Charles felt by this oversized intruder was almost too much to bear. Quickly the tension subsided, and he felt at ease with the foreign object embedded in his bowels.

“Go ahead.”

Rudy thrust his cock in and out of Charles’ pucker at the slowest rate possible such was his fear about hurting him. Soon though, he noticed Charles relaxing his anus, and Rudy could plunge deeper and deeper.

Charles was breathing deeply now. He enjoyed the build-up and release of pressure with each thrust. He hissed for a moment when another millimeter of meat plunged deeper into his anus. He felt a sense of satisfaction each time Rudy grunted in pleasure.

Rudy was impressed that this young waif of a man could take so much of his mammoth cock, and with each thrust, a little more meat was accepted. Rudy had applied that much jelly, thinking that Charles could maybe take a quarter of the shaft’s length. He reached for the tub and applied more goo, covering all the sides of his entire length.

“You doing alright, Charles?” Grunted Rudy after he placed the tub back on the bin.

“Keep fucking me,” Whispered Charles, “It feels great.”

Amazed, Rudy kept ploughing Charles’ shitter, but the stress was showing, and Rudy felt the first stirrings of an orgasm building. This was usually the point where he built up the momentum, but he had to keep his rage in check not to hurt Charles’ bottom.

“I’m going to come soon,” Rudy hissed.

“Fuck me as hard as you want!”

Charles felt no discomfort now, and he appreciated the additional lubrication. His hole could not be stretched any further. So with girth accommodated, Charles felt confident of taking more length.

“Come on, feed me more meat,” He begged of Rudy.

Rudy felt Charles’ anus suddenly accept more length, and with his orgasm rapidly approaching; he began slamming into Charles with reckless abandon.

Charles was uncertain if Rudy intended to come in his arsehole or down his throat. Both alternatives were welcome, so he waited patiently for Rudy’s signal, all the while impressed with his arsehole’s ability to take such punishment. Another first was becoming an anal size queen.

“Here it comes,” Growled Rudy.

Charles braced for a monster orgasm.

Moments later, Rudy jerked violently as he slammed into Charles’ shitter. He had to suppress what would have been a roar of intense volume so as not to attract attention. As it was, they would have been rumbled if someone had been nosing around.

To Charles, Rudy’s climax seemed to last for an eternity. The cock inside his arse continued violently spasming, releasing rope after rope of hot, sticky sperm that bathed him in a warm glow of contentment.

Rudy came back to earth in a flash and gently eased his cock from Charles’ arse. He could not believe just how much length he got inside. This guy, thought Rudy, had done something few men or women had achieved.

Charles felt the exit of Rudy’s cock suddenly and felt an enormous hole in his bung, which stung as the night air wafted across his hole.

“You’re leaking,” Warned Rudy.

Charles felt a river of hot come dribble down the inside of his thigh, and he immediately tried to close his butthole. Simultaneously, he scooped up the dribbling sperm and instinctively brought it to his lips. He thought the taste salty, although not unpleasant as some he had tasted.

Rudy saw this act and ordered Charles to push his sperm of out his arse and into his waiting hand. The instruction had a filthy and depraved feel that both men understood.

Charles pulled his cheeks apart and relaxed his bruised and battered O-ring. Rudy’s sperm trickled from Charles’ bottom in a steady stream.

“Push,” Exhorted Rudy and saw Charles pucker expand to an insane degree, and the last remaining drops of sperm dribbled into Rudy’s cupped palm.

Charles straightened his back and shuffled around to face the hulking Rudy with his jeans and boxer shorts around his ankles.

“How did I do?” He asked expectantly.

“You’ve done something very few people have ever done,” Answered Rudy softly, “You took so much cock. Not all but at least three quarters.”

“Wow!” Charles shone with pride but knew he would be sore for days.

“Shall we drink?” Asked Rudy, offered his sperm-filled palm to Charles.

Charles greedily took the sticky fluid in his mouth but was stunned when Rudy took the second. Then the two men licked Rudy palm for the last of it, their tongues dancing together.

Rudy wiped his hand against his jeans, pulled Charles to him and kissed him roughly. Chales’ level of excitement had raced over eleven and was rapidly approaching twelve; he needed release and could only think of home and privacy of his bedroom.

“Can I take care of that for you?” Asked Rudy, gently taking hold of Charles raging cock.

“I…I don’t normally take anything in return,” Charles stammered, torn between accepting the offer and the tried and true method at home.

“It’s the least I can do.”

“What do you want to do?” Asked Charles, paralyzed by indecision.

“That’s up to you,” Rudy said, gently stroking Charles shaft, “You can make me blow you, and you can fuck me. Whatever you want.”

In the end, Rudy decided the matter by dropping to his knees and engulfing Charles’ cock. Charles experienced a sudden rush of excitement as this bear of a man expertly throated his cock. When two fingers roughly penetrated his destroyed hole, Charles lost it and emptied load after load deep down Rudy’s throat.

The fixer was truly satisfied with the events of the evening.

“I’ll bring Lynn here next Monday, 8 PM,” Barked Rudy, who disappeared into the night like a phantom.

Charles pulled up his jeans and noticed that Rudy had left the tub of KY behind. Useful stuff to have, he thought, as he grabbed it and walked home.


Rudy delivered Lynn as promised and went over the details of the sham marriage. It was up to the two of them how the wedding would occur, but it had to be before a specific date; otherwise, her visa would expire, and she would be kicked out of the country.

When Rudy left, Lynn and Charles were alone. He felt some instant attraction to her, which he thought was reciprocated. However, they drew up a list of personal boundaries for the sham marriage to work, including an agreement to keep their relationship platonic.

As the weeks ticked by and the more time they spent together visiting family and friends, Charles developed a set of distinctly unfamiliar feelings. He felt a desire and sexual attraction towards Lynn. These feelings intrigued him, but he knew that he had stumbled across the solution to the second ‘thing’.

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