The Apprentice Pt. 01

This evening, I was hanging out in the chat room of the matchmaking site, where I had a full-paid membership. This was when non-paying members could chat for free for two hours. It was the best time of the day when there was a higher chance of attracting someone.

However, I was not having a good run lately. I had no trouble initiating conversations with prospects, but they never followed through with meetings. Regardless, there was always a flutter of hope when someone clicked on my profile.

On this evening, I was pinged by a member that went by the handle "Blow&Go69". With some resignation, I decided to check his profile out. Despite my misgivings, I was surprised at what I read:

"I am a bisexual guy who, after fantasising for many years about having sex with a hot man, has now had a handful of nice Bi experiences.

I'm particularly turned on by licking, kissing & sucking a hot cock, and I also like to lick & suck your balls. I love the feeling as you fill my mouth with hot spurts [of] cum. Big cummers ( like myself) as especially welcome!"

Blow&Go69 went on to describe his other - non-sexual - interests in an erudite, intelligent, and engaging manner. This man came across as educated and exciting to me, and when I checked his location, my cock jumped at the fact that he lived in Chadstone, a mere two KMs from my home.

I winked "Blow&Go69" back and waited.

The wait was quick, and I received a "whisper" through the chat functionality. This allowed us to send and receive messages between each party, but the chemistry was evident, and we quickly gravitated to WhatsApp.

"What are you looking for?" I asked cock hard.

"Ideally, I'm looking for a straight-acting guy that I can hang out with, go for drinks, be friends and have some intimate fun once in a while."

"Nice, I replied, "You're straight acting; I take it?"

"Yes," this enigmatic stranger replied, "I date women in real life, but I have dark desires for M2M action."

"You mentioned in your profile that you have had some M2M experiences."

"There were great, seedy, but great!"

"Why were they seedy?" I tapped, fully interested.

"Public places, in the outdoors, that kind of stuff."

"Nothing wrong with that," I replied, noting my interest in outdoor sexual activity.

"Wow," My enigmatic chatmate said, "I have not done anything like that."

"Well, there's a whole world of possibility out there for you," I said, "If you have the imagination."

"I want to be led...'

There was more back-and-forth dialogue that helped establish interest and trust, much of it non-sexual, but it helped pin us together, which gave me optimism.

"I fancy a beer," I said one night during a chat, "You feel like meeting?"

"Sure," he said, "When and where?"

"How about this Thursday at the Rosstown Hotel," I suggested, "It's halfway between where we live."

"Perfect," He said, "I'll be there."

To be fair, I had heard such agreements many times, and there was no reason for me to put any stock in this latest meeting, but, in the back of my mind, this man's intelligence and flair with wording gave me cautious optimism.

On the appointed day, I arrived home and took a shower. After much personal sculpting and the application of aftershave left behind by a previous girlfriend, I was ready for our first meetup, or date, for those that call it as they see it.

From exchanging photos, we knew how to recognise each other, and Nathan had a firm handshake when he approached me at the bar.

"What are you drinking?" I asked with a fifty at the ready.

"Is that a whiskey?" He asked.

"Bourbon and coke."

"Make that two."

We grabbed our drinks and sat at a table that had a window that looked onto the highway. Nathan was a good-looking bloke, every bit the straight man with chiselled features, cropped sandy hair, a taut body and tall, like me. In most respects, we were the analogue of each other. As a result, we hit it off in person, as we had online over the last few weeks.

"I am glad you turned up," I said, as an ice breaker, "Most don't."

"That profile of yours," Nathan replied, "Had me hooked."

"In what way?"

"You've listed so much experience," Said Nathan confidently, "But not everything was to my taste."

"Fair enough," I conceded, "What did you like?"

"Well, you're a good-looking guy," Nathan stammered nervously, "You're close by, and you can teach me some tricks."

"Tricks?"

"Anal," Nathan whispered, not that anyone would have overheard, "I'm very inexperienced with receiving anal, but I have done it when I have been very turned on."

"What turns you on?" I asked.

"Personality, intellect, physicality," Nathan stumbled, "Experience."

"Does it get you off?"

"With the right guy," Nathan became suddenly animated, "Every single time."

"In what way?" I asked and mentioned my indifference to anal sex.

"I come multiple times from anal sex," Nathan confessed, "Why don't you?"

"I don't know," I confessed, "I can take cock in my arse easily, but aside from the giver's pleasure, I don't derive any personal sexual satisfaction."

"The giver's pleasure?" Asked Nathan.

"Yes, someone pumping my hole for their gratification," I said before adding, "I enjoy when they cum inside me."

"And that gives you no pleasure?"

"That does," I confirmed, "But, in and of itself, that act does not get me off. I do not orgasm at any time."

"They must not be doing it right," Quipped Nathan nervously.

"Perhaps," I smiled, "It's been sometime between innings."

"What do you mean?"

I went into some detail about my uni days in the UK when four of us would turn gay when one or all of us failed at scoring with the fairer sex. This was the period of my most gayness. Between 2005-2007, I was involved in gay and bisexual shenanigans with some exciting playmates.

"My last encounter was six months ago," I told Nathan.

"How come?"

"Quality over quantity," I repeated, "I only play with attractive ones, that pique my various interests."

At my compliment, Nathan straightened his back and seemed pleased. For my part, I was mesmerised by his good looks and his physicality.

"So, you like me?" Asked Nathan, his glass shaking.

"Of course," I said, "And you?"

"Very attracted."

"What now?" I asked, cock hardening in my jeans.

"Car park or somewhere else?"

"For what?" I asked, knowing the answer.

"Well, I would really like to give you head."

Hmm, I thought, Nathan was direct and to the point, which I liked.

The car park of the Rosstown Hotel was not particularly accommodating, so we had to find a dark, secure place on either side of the highway. To his credit, Nathan did act as a straight guy in public, as I did, but where we found a dark place, he would attempt to hold my hand or assume other amorous poses.

When we found a quiet park where no one was around, Nathan turned around and kissed me furiously. At first, I was maddened at his presumptuous act, but his lips were so soft that I quickly forgave his "transgression" and quickly submitted to the moment.

Shortly after, Nathan dropped to his knees and struggled with my belt buckle. After a short struggle, my jeans were by my ankles, and Nathan took my hardened shaft down his throat.

I gave an audible sound of appreciation as Nathan expertly blew me to his boasts in this online profile. No woman has ever made me cum so quickly and so powerfully as filing up Nathan did that night.

When I came, I came hard, loud and large. Nathan swallowed my overdue load with ease and enthusiasm. The smack of the lips at the end was amazing.

"What about you?" I asked when Nathan stood up.

"I'll sort myself out when I get home," He replied.

"I can sort you out now," I offered, horny as hell.

"Next time," Nathan said apologetically.

"I look forward to next time," I answered as I pulled up my pants, realising there was no more action to be had.

"Cannot wait." I said as we departed.

Over the course of several weeks, we chatted online frequently, sometimes calling each other which ended with me getting Nathan off, or so he said.

The lack of follow-up meetings was somewhat frustrating, and I wondered if he was seeing other guys. I quickly reined in my green goblin, and told myself, when my sexual frustration was at its highest, to practice patience.

All good things come to those that wait, according to the English proverb.

Out of the blue, one weekday, Nathan called me up and invited me for a drink after work.

"Where?" I asked.

"The Racecourse?" This was a pub was 100 metres from my front door, and a place where I was widely recognised.

"I'd prefer the Glasshouse," I offered as an alternative.

"Perfect," Nathan replied, "Right next to the station."

We met at the appointed time, and this time, Nathan chose the drink, from which I am very grateful for because it has become a staple.

"Two Lagavulins please."

"Fuck, this stuff is strong!" I spluttered after swallowing a sip of Scotland's finest.

"I love this stuff," Nathan smiled, "Gets me in the mood."

"The mood for what?"

"Some nasty action!"

"What does that mean?" I asked, as my cock twitched in my jeans.

"I have wanked off a lot over you doing me anally," He said, with a twinkle in his eyes, "I want you to give it to me."

"I'd love to arse fuck you, my man," I whispered, "You want to come back to mine?"

"Not tonight," Answered Nathan, with a cheeky grin, "I want this to be seedy."

"How so?"

"I want to be holed outdoors, and to be treated as the lowest slut cunt you ever railed!"

"Wow," I answered, taken aback, "Someone's hot to trot."

Nathan, who sat opposite me initially, shifted to next to me.

"Feel my cock," He whispered and took my hand and placed it on his crotch.

His hardness led me to take a sharp intake of breath in surprise.

"Not too much of that here," I hissed while making a little space between us, "There are so many cameras."

The Glasshouse venue was basically a mini casino located across the road from the Caulfield Racecourse. The audio senses were bombarded by the constant cacophony of poker machines, and there was no escaping the inveterate gambling that went on 24-hours a day. As a result of the high degree of constant gambling, the venue was blanketed by CCTV, forever recorded, and constantly reviewed. In hindsight, my choice of venue was poor, given Nathan's horniness.

To be honest, I was at a loss to decide where to go that would satisfy Nathan's seedy urges, but I knew we had to exit the Glasshouse as quickly as possible.

"Drink up," I ordered, as calmly as possibly.

"Where do you want to do me?" Asked Nathan, and I suspected that he had imbibed a few additional shots before we met.

"Not sure," I stammered as we walked past security, "I'm thinking."

Thinking fast, I came upon the idea of the telephone exchange building that bordered the back of my townhouse. The property was uninhabited at night and faced an access road that nobody ever used. The place was dark, unpopulated and, for our purposes, off the beaten track.

It was a place to start anyway.

"Follow me," I said, as I walked toward the traffic lights.

To his credit, Nathan continued to act the straight man, but there was a volcano bubbling inside him, and mantle was stirring in anticipation.

"What do you think?" I asked when we arrived at the exchange.

"Works for me."

"Cool," I said, pleased, "What now?"

Nathan pressed his body hard against mine and pinned to the wall, his breath in my ear. My cock instantly hardened.

With his face millimetres away from mine, his foetid breath flaring my nostrils, I thought he was going to kiss me, which, as my heartbeat rapidly, I was prepared to accept, Nathan instead dropped to his knees and tugged at my jeans.

"I need to get you so hard that you can't resist my arsehole!"

"There is no need to worry about that," I sighed, as my jeans were tugged down to my ankles.

Nathan did not have the best oral technique, and on the last few encounters, I ended up wanking into his mouth, to his delight. However, this night I was so turned on that he drained me only after a few minutes, expressing gratitude for the milky gift flowing into his gut.

As I deflated, I suddenly panicked about not recharging in time to satisfy Nathan's craving for anal satisfaction.

Thankfully, my self-doubt only lasted for a second, for when Nathan stood up, he pinned me by the throat to the wall and kissed me, his tongue reminding me of the taste of my seed.

My semi-deflation instantly turned into another diamond cutter, and my level of arousal burst through the roof.

Fuck me! I thought, this guy is going for it.

In a somewhat unusual role reversal for me, I deflected Nathan's hand against my throat, grabbed his scruff and swung him against the wall. His physique impacted with dull thud.

We kissed some more, but I began roughly fondling his bulge much to his satisfaction.

Seconds later I began fumbling with his belt and jeans. Nathan's briefs were coasted with pre-cum, and my knees gave me. Dropping to my knees this time, I yanked the fabric covering down and grabbed the base of his cock.

"No," Nathan pathetically protested, "I want you to fuck me!"

"In good time, slut," I breathed before devouring his gorgeous cock.

"Oh, fuck," Hissed Nathan, completely taken aback by my aggressiveness.

I throated his salty cock with much enthusiasm, remembering how much I missed such mutual intimacy between two blokes of similar mindset.

However, within a minute of my bold oral move, Nathan pulled his cock from my mouth, with the repeated groan of "No, no, no."

"What do you want?" I asked, wiping the slime from my face, and standing erect in front of him, as his head lolled from left to right in complete ecstasy.

"I want to come with your cock in my arse," He answered in an almost dreamlike state, and slowly turned to face the wall.

Indeed, Nathan's arse was beautifully round and when he reached around and spread a cheek for me, I almost nutted for the second time.

I could not resist. Dropping to my knees, as if ordered, I spread the second cheek and aggressively tongued Nathan's soapy flavoured arsehole.

"What...What are you doing?" Stammered my surprised host.

"Preparing you," I said, spitting onto his arsehole.

"Feels good," Nathan replied, nervously, "Nobody's ever done that to me!"

"Well, I hope you like it," I breathed before burying my tongue back where it belongs.

After a minute or so, Nathan could not take it anymore.

"Babe," He sighed, "I need you to fuck me!"

I must confess that no male lover, ever, has called me 'babe', but the innocence and urgency in his voice ramped up the blood flow in my cock.

I was ready, and Nathan was ready.

Time to go.

Standing up, I spat on the head of my cock and rubbed Nathan's saliva-drenched pucker.

"You ready," I asked, placing my purple-raging head against his chocolate starfish.

"Fuck me," He pleaded, "Fuck me hard."

Easing into to Nathan's backdoor was easier than I expected, and judging by his relaxation, the same applied to him.

"Give me a second," He hissed as I buried my length into his athletic behind.

"Sure," I reassured him, as I placed both arms around his torso and waist.

"Okay," Whimpered Nathan, as his right hand went to his cock, "Fuck me!"

I began slowly, but his anus quickly adjusted to my foreign object and soon relaxed. The spongier Nathan's O-ring became, the more he enjoyed the buggering I was administering.

"Fuck that hole," Nathan kept repeating between sharp intakes of breath, "Give it to me."

Over and over again.

As soon as Nathan began pushing his anus against the base of my cock, I knew my days were numbered.

"Fuck, I'm going to come!" I hissed, griping Nathan's body tight.

"Oh, yeah," He squealed, "Inside me!"

There was nowhere else I was going to come.

"Here it comes!" I grimaced as my orgasmed travelled up my legs, centred in my balls before shooting up my shaft and exploding in Nathan's tender rectum.

As I came, Nathan came.

His body jerked in my tight grip, and I heard spurt after spurt of fresh semen wash against the wall that he was pinned against.

"Let me clean you up," Breathed Nathan after our sweaty bodies relaxed.

My flaccid pipe exited Nathan's creamy arse with a pop before he involuntarily dropped to his haunches and took my funky member in his mouth.

What a clean-up job!

"Let's see about you," I said, raising Nathan to his feet.

His DNA graffiti on the wall of the exchange was impressive, but watching my sperm bubble and dribble down each leg from a gaping hole was sublime.

"That was so good," Nathan sighed, trying in vain to pull up his briefs and jeans, as his limp body rocked against the spunky wall of the exchange.

"Glad you enjoyed it," I said with better composure, "As I had a great experience."

"Can we do this again?"

"Call me, and let's do it."

Nathan and I walked towards the end of the access lane, but in the shadows, we exchanged a tender kiss before departing for our respective homes.

Lying in bed that night, following a shower, I reflected on what an intense and satisfying sexual encounter that was. Falling asleep, I eagerly awaiting Nathan's next move.