The Apprentice Pt. 04

The Apprentice Pt. 04

Admittedly, I was sceptical about Nathan's offer to share women and never followed up on his enigmatic offer. I was happy he felt more comfortable coming to my house and playing indoors. We continued to find thrilling outdoor settings where we engaged in mutual cocksucking. Still, by coming to my house, Nathan signalled his willingness to engage in anal sex - he was a taker, not a giver, and I was comfortable with that.

Our sexual relationship was based firmly on friendship first. Not every catch-up led to a happy ending, but we were comfortable around each other and shared similar interests. We even leered at women. I did not need to know if Nathan was seeing other people, nor did I care if he was. There were additional sexual partners in my life, but they did not interfere with my time with Nathan.

One evening, following several quality whiskeys at a local bar, Nathan asked me if I had ever experienced a threesome. I hesitated before answering in the affirmative, wondering why he was asking me such an obscure question when the conversation was centred on the merits of Xbox versus the PlayStation.

"What type?" Nathan asked.

"With two men and one woman," I replied.

"How was it?"

"Really good," I said, casting my mind back to that Saturday afternoon years earlier in Perth, "Pretty much did it all."

"Such as?"

"Oral, anal, DP and creampies."

"Nice."

I gleefully recounted the details in vivid detail as Nathan kept probing for more. He agreed that such an experience would have been memorable.

"What about group sex?"

"Not with women," I replied after thinking for a time.

"Oh, do tell!

"Years ago, during my university days, me and a couple of mates went hiking in the countryside and discovered a hidden stash of scud magazines," I recounted, "And partook of an orgy of sorts."

"Wow!" Was Nathan's wide-eyed response after I detailed the shenanigans we got up to, "Did you have a follow-up with those guys?"

"Once," I confirmed, "It went all night and took it to extreme levels."

"Extreme, how?"

"Double anal, bukkake, water sports."

I needed to explain some of those acts to Nathan in minute detail.

"Wait, so you took two cocks up your arse?" He asked incredulously.

"I didn't personally, but I certainly double fucked a friend."

"How was it?"

"Clumsy," I laughed, "We didn't know what we were doing, and we used too much lube."

"But your friend took two cocks up his arse?"

"Eventually."

I don't think there's enough alcohol in the world to convince me to try that," Winced Nathan.

"Same here," I agreed, "The two guys that attempted it had sore arses the next day."

"When the booze wore off?"

"We all had varying degrees of soreness, to be fair," I said, "I don't think I touched my cock for a week!"

"What about your arse?"

"Not nearly as raw as my cock," I replied, "I came so many times that night that I was spoofing air by the time the sun came up."

"What was the best part?"

"The bit where one guy was laying on the coffee table with his legs spread, I was fucking his arse, another guy was taking cock up his hole while the fourth guy got his cock sucked."

"Airtight?" Nathan smiled, "Seen it on a porno."

"It was such an erotic experience that the four of us came almost simultaneously."

"Mm, so much cum," Drooled Nathan, who was visibly massaging his bulge under the table, "I would have loved to be that guy on the coffee table."

"He got a thorough working," I laughed, "He took a load in his arse and mouth and creampied another guy."

"Amazing," Said Nathan, "Sounds like a fun night."

"Why did you start this conversation?" I asked, still baffled by the complete left turn in our discourse.

"I have this woman friend, and we've been talking about threesomes," He replied.

"You fucking her?"

"I have on occasion," He smiled, "She's good too."

Nathan unlocked his phone and showed me some nudes. This woman was indeed sexy but had far too many tattoos for my taste.

"So, yeah," He continued, "She's keen to take on two guys."

"Oh," I said, allowing Nathan to direct the conversation.

"So, I mentioned that I have a 'friend' that could oblige," Nathan continued, "We've been talking about making this a reality for a while."

"Is she ready to take the plunge?" I asked with rising anticipation.

"I think so," Nathan replied, "She's already checked out your online profile and likes what she saw."

I did not recall a woman checking out my profile recently. However, it was heartening to hear that the tattoo girl was considering me to partake in a threesome.

"If you want, I can add you to our WhatsApp group," Nathan said, fiddling with his phone.

"You have a WhatsApp group?"

"Yes," Smiled Nathan, "There's a second girl in there, too, her friend."

"Threesome or more some?"

"Ultimately a foursome," He said, "However, both want to see us play together."

"I don't have an issue with that," I said, "I'd like to them play together."

"That won't be a problem," Nathan grinned knowingly.

We chatted more about threesomes and how they might pan out. Later, we disappeared to a favourite, discreet public spot for some oral fun.

It took several weeks of conversation and getting to know each other on WhatsApp before the threesome occurred. While we got on well, there appeared to be some hesitation on the tattoo girl, whose name was Riley (her friend, waiting in the background, was Leslie). Meanwhile, Nathan and I continued playing together.

As the chat continued, Leslie, the more confident of the two, wanted the four of us to meet socially. After a bit of to-ing and fro-ing, we locked in a weekend date beginning at Young & Jacksons, across the road from Flinders Street Station at 3 PM.

Separately, Nathan and I arrived an hour earlier for several pre-date drinks. He seemed a tad nervous, and the reason for that was a performance fear.

"What do you mean?"

"It's been a while since I've had sex with a woman," He replied, "Been too much into the male side of the business."

"It's just like riding..." I began.

"A bike," He chimed in, "Yes, I know."

"You don't think anything will happen tonight, do you?"

"Depends on the ladies, I guess." Nathan shrugged, "Depends how it goes today."

The iconic pub, on the corner of Flinders and Swanston Streets, was packed with a mix of tourists and Melbournites. We secured a table for four and did battle with patrons wanting to steal our spare seats.

"Where are you?" Leslie asked on WhatsApp shortly after the agreed meeting time.

Nathan replied, and we stood to greet the girls, who looked amazing, although Riley was overdone with trashy makeup which spoiled her natural beauty. I went to the bar and ordered a round of drinks. For the next couple of hours, we drank, ate, conversed and laughed. The chemistry between us translated well from WhatsApp to real life.

Leslie was a finely constructed strawberry blonde, busty and slim, with a fine derriere, a pretty face and a sonorous voice. Riley, by contrast, was a stocky, short-haired ginger with substantially larger chest than her friend. She seemed dour most of the time until something made her laugh; then her face lit up brightly. Most of her flesh was covered up, but I knew from WhatsApp photos that her body was covered in piercings and tattoos.

As we crawled from pub to pub, we frequently shared the girls, walking arm-in-arm, comfortable in each other's company. The girls frequently went to the bathroom together, no doubt to gossip about us, then returned and exchanged knowing glances.

Inevitably, the conversation turned to sex. The girls asked me about my bisexual and gay experiences. When I completed my 30,000 ft overview, both agreed that the experiences were hot.

"So, do you have a favourite between cock, arse and pussy," Leslie asked, captivated.

"I like it all in equal measure," I grinned, "I also like titties."

Both girls laughed and shook their breasts provocatively. Then they squeezed each other's chests abd pecked their lips. I looked around nervously, but the bar was too packed, and no one noticed.

"Your turn," Riley teased.

"What do you want us to do?" Nathan asked, nervous and confused.

"Kiss, of course."

This time, Nathan looked around before looking at me, terrified. Placing a hand on his thigh, I leaned in and kissed his lips for the briefest moment. The ladies were momentarily stunned before turning to each other and grinning.

"So hot!" They said, "We'd like to see more of that."

In the instant our lips touched, I moved my hand further up Nathan's leg to his crotch. His bulge was unmistakable, as was mine. The dim illumination of the bar kept my cheeky move hidden from view.

"Let's swap seats," Leslie suggested as she got up to take my position while I sat next to Riley, "Give me a kiss."

Nathan and Leslie engaged in an erotic and extended passionate kiss right in front of us. Riley and I did not know where to look but could not turn away.

"Your turn," Leslie grinned at us.

I placed my hands on Riley's chunky waist while she gripped my shoulders. Our lips locked, and it took a moment to synchronise, but once that happened, we engaged in a passionate kiss that brought my cock to diamond strength.

"Mm, nice," I said as we disengaged.

Riley looked deeply into my eyes and smiled. We turned and faced Leslie and Nathan, who were both smiling.

We made our way to Chinatown for a light dinner, then decamped to the Exford Hotel. Leslie and I had exchanged a lip lock, while Nathan and Riley experienced the same.

"So, ladies," I smiled above the din, "Cock, pussy, arse, titties?"

"We like them all," The girls laughed out loud, placing their heads together and clinking vodka glasses.

Unbeknownst to us, the weather had deteriorated to the point of torrential rain. None of us had properly prepared for the change. Upon exiting the Exford, we ran awkwardly into Little Bourke Street, and I grabbed a couple of boxes. Under an awning, Nathan and I ripped apart the cardboard to make crude umbrellas. Lightning ripped across the sky and the clouds boomed with thunder.

"This way," Nathan shouted.

We ducked into an alley and into a double-doored fire escape that provided temporary shelter. Across the road, Leslie spied an independent bottle shop across the alley.

"While we are here, we should drink."

"Sounds good," I said, "Shall we go?"

Leslie grabbed my hand while I placed the damp cardboard over our heads as we made the short dash. Inside, we bought two bottles of wine and ran back to our colleagues who were cuddling and kissing.

Leslie handed a bottle to Riley, and I gave the second one to Nathan. Like common bogans, the four of us drank wine directly from the closure. Such disgraceful behaviour did loosen any inhibitions we had.

"Kiss me," Leslie demanded.

For several minutes, Leslie kissed me, Nathan kissed me, and Riley kissed me. My three colleagues enjoyed the same rotation of partners.

"I want to see some cock sucking," Leslie panted, as she slimped against the concrete wall, hitched up her dress and began rubbing her hairless clit.

"Okay," I grinned, looking at a nervous Nathan, "Cool with you?"

"Sure," He said, voice wavering.

I pulled him close to me, we kissed slowly, and, when we disengaged, I whispered into his ear to relax.

At that moment, the two girls were not even in my orbit. All I wanted to do was please my apprentice. Dropping to my knees, I watched as Nathan undid his belt, unbuckled his jeans and freed his magnificent cock.

As I took his impressive meat in my drooling mouth, I immediately tasted an odd mixture of soap and piss. My tongue also detected the unmistakable flavour of precum. I cupped Nathan's heavy ball sack as I used my lips, tongue and hand to massage his shaft.

"Oh fuck!" Nathan repeated as his head rested against the wall.

As I throated Nathan to an inevitable climax, I was aware of the ladies masturbating next to us, talking in foreign tongues followed by a rhythmic squeak and the smacking of lips.

"Shit, I'm coming!" Nathan hissed, seemingly surprised by the speediness of his approaching orgasm.

I pulled my head back, kept my mouth open and stuck my tongue out. Using my hand, I jerked his shaft until Nathan exploded over my face and filled my mouth with hot ropes of thick sperm. This was an unusually strong orgasm, even by Nathan's enthusiastic standards. Without hesitation, I swallowed his tasty gift and gently sucked on Nathan's deflating shaft until he withdrew his meat from my mouth.

Rising, the girls pounced on me and licked Nathan's errant shots that smeared my face while aggressively stroking my groaning bulge. The apprentice seemed spent as he pulled up his jeans and grabbed the wine bottle.

"Holy fuck, that was good!" He panted, barely able to function.

Once the girls pulled back, I saw that Leslie's dress was hitched up and she wore no panties while sporting a hairless snatch, while Riley's jeans were drawn down to her hips, exhibiting a neatly trimmed pubic area.

"How was that?" I grinned, wiping the saliva and whatever else on the sleeve of my shirt.

"I came so many times," Riley grinned in a rare first move.

"So did I," Leslie agreed, "Watching you suck cock was so hot!"

"How about you two put on a show for us?"

"More than happy to do so," Leslie chuckled.

Leaning against the wall and sucking from the bottle, Leslie spread her hairless snatch. Riley took a courageous swig before dropping to her knees and lapped at Leslie's clit and pussy.

Watching this action, I undid my belt and unzipped my zipper, releasing my groaning cock. Nathan handed me a bottle and took a bolt that erased the aftertaste of his sperm, but gave me a much-needed hit to the brain.

As Riley munched the pink taco, Leslie had freed her breasts and massaged them, aggressively pinching her stiff nipples.

"Keep going, baby," Leslie begged, "Almost there."

"Uh, huh," Riley grunted, "You got something for me?"

"Yes, baby!"

"Here it comes!" Leslie growled.

Riley moved her head back from Leslie's cunt but opened her mouth. Her paramour violently smashed her clit while grunting furiously. Suddenly there was a hiss, followed by a muted scream, Leslie climaxed into Riley's mouth. In the dim light, I clearly saw Riley's gullet jerk as she swallowed Leslie's girl squirt.

After a well-deserved break, Nathan had recovered his senses, and we shared the wine as the storm continued its violence.

"Riley's turn," Nathan said.

"Oh, goody!" She said, while turning around, leaning against the wall and sticking her ample butt out for Leslie's consumption.

Nathan and I were impressed with Leslie's technique. We could clearly see her tongue switch between pussy and arsehole, while Riley was rubbing her clit. It seemed to me that Riley enjoyed being rimmed, which is a sex act that I get off on.

"Tongue my arse!" Riley begged at the tipping point.

Riley held her breath and said nothing for a few moments before releasing a low, guttural noise that seemed to shake the foundations of the building. No girl squirt, but Riley's orgasm seemed stronger than Leslie's.

For maybe half an hour, we sat in the alcove and swapped bottles as the storm raged. Three of the four had enjoyed thundering orgasms, and I waited patiently for my turn. For fun, both girls took turns pissing into the alley, then they laughed without restraint while they held Nathan's cock as his pissed arced high into the air before being lost in the driving rain.

It was Riley, the less confident of the two, who, surprisingly, took the lead. She approached me and leaned in for a passionate kiss. This time there was better synchronicity with our lips and tongue; she also firmly rubbed my bulge. As she did so, I placed my hands on her boobs and squeezed them hard. I pulled up her top and reached around and unclasped her bra. Both nipples were stapled and, I imagined, heavily tattooed.

Picking up on the building action, Nathan and Leslie wanted in on the action. As Riley kissed me, Leslie and Nathan pulled down my trousers and freed my long-suffering cock. They both took turns licking and sucking my shaft and cock head.

"Bend over," Riley ordered.

Placing my hands against the wall, I bent over and thrust my butt out. Riley and Leslie worked my cock while Nathan used some impressive imagination and scooted behind me and rimmed my twitching arsehole. The sensations from this triple act were unparalleled.

"Fuck, guys," I panted, "That feels so good."

In return, all I could hear were moans of pleasure from the three people who were going the extra mile to make this experience so very memorable. I edged until they could take it no longer.

"Come, you fucker!" Riley slapped my arse hard.

"Okay," I sighed.

Standing and turning, my three companions repositioned themselves on their knees in front of my cock, with Nathan sandwiched between Riley and Leslie. As I wanked my cock, they licked my piss hole and rapidly shrinking ball bag.

"Give us your seed," Leslie urged.

"In our mouths," Nathan agreed.

"Please, I really want to taste your come!" Riley begged.

With such enthusiasm, it did not take me long to top Mount Pleasure. I made sure everyone knew. Leslie and Riley gripped my shaking legs as I ejaculated a massive load over the faces of Riley, Nathan and Leslie, respectively. They tried to capture as much of my seed in their gaping maws as possible, but my aim was off.

Coming down, three mouths and tongues on my deflating cock was a sublime experience. Looking at them, I saw them sharing my cock, lips and tongues.

"That was fucking amazing," I puffed while wiping my brow.

"Superb load," Leslie smiled, leaning in for a spermy kiss.

The three of them directed all the errant shots of jizz into their respective mouths, all washed down with cheap wine.

I doubted there was any further possibility of action, particularly so given the weather. All four of us were spent after such thundering oral orgasms. We sat and chatted innocuously while draining the wine. Once done, the rain had slackened sufficiently to let us to get to a public transport hub.

After saying our goodbyes and departing in different directions, we waited with bated breath for whatever future adventures awaited us.