From Glory Hole to Hotel Room

After breakfast on the third and penultimate day of the conference in Melbourne, I decided to skip the sessions. I could not concentrate anyway after a chance meeting with an athletic young man in an adult movie theatre. We had two intense sessions of firsts for both of us that had me questioning my sexuality.

Over the course of two evenings, I had sucked my first cock, swallowed come, enjoyed giving a rim job and taken a facial. He had received his first blowjob by venturing to boldly stick his cock through a round hole that separated our respective movie viewing booths on the first encounter. Quite the leap of faith for someone so young and inexperienced. Going into the movie theatre a straight man, I did not hesitate to suck the cock presented to me, and I left with a stomach full of sperm.

That question was partially resolved the next night when I actively engaged in some nasty acts that I had only previously done with women, very few women. The pleasure my impromptu and imaginative behaviour brought to my mysterious stranger was incalculable.

Gary was young but of age with strikingly good looks, wiry framed with long hair wrapped in a ponytail. His eyes burned brightly in his youthful face, and he was as keen as I was to explore this mysterious yet pleasurable world of man-on-man action.

Admittedly gay but having sampled the fairer sex on occasion, Gary enjoyed the company of older men, especially straight dudes, but had been a giver up to the point he ran into me. Now, he understood the pleasures of receiving and what I offered. Gary relished it in spades.

With only one evening remaining in Melbourne before flying back to Sydney, we both wanted to make our final encounter memorable. Gary wanted to do to me what I did to him the night before, which was lick my hole while he jerked my cock and ventured to some fingering. I was up for that, given Gary's explosive orgasm when I treated him to such pleasure.

"What about anal sex proper?" He asked via a text message on Thursday morning.

"I don't know," I replied, sceptical that our arses would accept the other's cock, "We could try, I guess."

"I'd like to try it," Gary said, "Because your fingers felt great."

Working two fingers inside Gary's bung launched him off a cliff and resulted in an almighty release of sperm that soaked my chin, cheeks, and hair.

"Like I said yesterday, we need to prepare properly so that penetration doesn't hurt."

"Okay, what shall we do?"

The thought of penetrating and being penetrated with a thick cock had me instantly hard. The idea of taking each other's anal virginities had me leaking pre-cum.

I tapped out a series of messages about what needed to be done based on my experience with women, and I told Gary that I would buy some lubricant from the adult movie theatre.

"Do you want me to meet you there after work?" He asked.

"That's probably not the best place to engage in that type of activity," I replied, not wanting to be anally deflowered in a small, both in seedy adult movie theatre.

"Then where?"

"How about my hotel room?"

"Really? That'd be great."

"Yeah, we can shower and make the proper preparations."

"What time?" Gary asked.

"Whenever you can make it," I replied, "I can't be arsed with the conference today."

"Okay, well, I'll try and get off work early so that I can join you," Gary said, "Exford for a drink first?"

"Sure, let me know when you can make it."

That was it for several hours. After showering, I grabbed my backpack and headed to the city. For lunch, I grabbed a meal and a beer at the Duke of Wellington down the road from my hotel. Curiosity got the better of me, and I began researching gay sex and how best to approach anal penetration. Initially, I began discretely watching gay porn. I do not know if it was the platform or the random selection, but what I saw was repellent.

Next, I consulted some online written resources and felt more comfortable. Regardless of gender, the approach to anal sex was similar. Various lubricants were suggested that helped to loosen the O-ring, as were enema mixes. Butt plugs were suggested but not strictly necessary because fingers were a viable substitute. Now, I was intrigued and feeling very horny.

As soon as I finished my meal, I hastened to the closest sex store to purchase the items I needed to make the evening as pleasurable as possible. In front of me was a cornucopia of products, including toys, lubricants, lingerie, magazines, and DVDs. There were a handful of other shoppers browsing the aisles, and some elevator music played in the background.

"Can I help you?" Asked a male with a pitched voice and slight lisp.

"Oh, hi," I replied, "I'm looking for these items."

"First time," He asked with a knowing smile after quickly glancing at my phone screen, "Him too?"

I nodded to both questions, and the male attendant led me to an aisle that was stocked with a variety of lubricants. He grabbed two alternatives and presented them to me.

"These are the ones I recommend to newbies," He said seriously, "They help to lessen the irritation at the initial penetration."

"Okay," I said nervously, "Does anal sex hurt?"

"I heard that there is a momentary pinch," He smiled, "But it quickly passes."

"And these lubes reduce that pain?"

"That's the feedback I have received."

"So, it doesn't hurt you, I take it?" I asked with a cheeky smile.

"Nope, never did," The attendant chuckled, "We hardly use lube these days."

"Why is that?"

"For me, I enjoy the friction."

"Nice," I said before settling on a choice of bottom grease.

"When is the big event?" He asked after I selected an enema kit.

"This evening, hopefully."

"Can I give you another recommendation?"

"Sure," I replied, and I was led to another aisle containing a vast array of sex toys.

Murmuring to himself while searching, the attendant grabbed what he was looking for. He showed me a small black butt plug no wider than 2 CM and no longer than 15 cm.

"If you wear this for a few hours before the main event, then the lucky man's entry won't hurt at all," He smiled with a twinkle in his eyes, "Assuming he's gentle with you."

I took the package from his outstretched hand and examined the toy upfront. Scepticism took hold, and I doubted my tight bung could take it.

"Use plenty of this, and you'll be able to take it," The attendant chimed in after reading the doubts on my face.

Intrigued, I agreed to add the plug to my shopping cart. Adrenaline coursed through my veins and my hands trembled with anticipation as I followed the attendant to the cash register.

Ten minutes later, I slammed the door to my hotel room and retrieved my purchase from the backpack. After stripping naked and going to the bathroom, I mixed an enema and proceeded to douche my back door for the first time. Applying grease to the nozzle and to my twitching shitter, I gently eased the bottle inside.

The intrusion felt alien at first but not unpleasant. I got down on all fours with my arse high in the air so that gravity forced the warm, soapy mixture deep into my dirt tunnel.

"Fuck!" I exclaimed at the unusual sensation of feeling full of liquid.

The sensation felt so pleasurable that my cock started growing rapidly. With the bottle empty, I gingerly withdrew the nozzle. The next challenge was to stand up without losing the contents of my bowels while I duck-walked to the toilet. I read earlier that control of my sphincter was key to enjoying anal sex. It took some serious control to keep the muscle tightly closed, but I managed it.

Sitting on the toilet, I will my back door shut for as long as humanly possible as my cock twitched violently. Waiting until the last possible moment, my nerves were on tenterhooks. When I let go, the sensation of expelling the liquid was sublime and almost climatic!

A strange, calming sensation washed over me after my bowels were completely evacuated. I did not notice how much I sweated during this experiment and wiped my brow on a nearby towel. My cock head oozed pre-cum with a long tendril of fluid dripping toward the floor.

Buoyed from the positive experience with the enema douche, I ripped the packaging from the butt plug and examined it up close. Dubious that my virgin bottom could take such an intrusion, I remained keen to try. Flicking the lid off the bottle of lubricant, I squeezed a generous amount on the tip of the toy and proceeded to coat every aspect of the surface area. Next, I squeezed another dollop onto my hand, smeared my index and middle fingers before pulling an arse cheek apart, and massaged my twitching starfish. The cool grease felt smooth.

I tensed momentarily when I inserted my index finger inside, and after the douching, there was no irritation or negative feeling. With two fingers working my hole, I felt a flash of pain, but that quickly passed. I circled the digits across the surface of the O-ring. As I did this, my dick was raging for attention, but I resisted the shortcut to orgasmic pleasure. The temptation to come would rob Gary later in the evening.

After withdrawing my fingers, I tentatively grabbed the toy, pressed its tip to my greasy pucker and gently pressed. Initially, the muscle accepted the first couple of centimeters, but I quickly encountered resistance. Forcing myself to relax, a little bit more of the toy disappeared. Helping to get used to the foreign intrusion, I slowly eased the silicone in and out, forcing a little bit more each time.

My pucker groaned in protest as the widest part of the toy came closer. As the muscle reluctantly opened, the stretching sensation was alien and not entirely pleasurable. For a millisecond, I was about to give up, but the strength of my hardon overcame such doubts.

"Oh, fuck!" I moaned as I continued forcing the toy inside.

Through gritted teeth, I reached the widest point before my sphincter snapped around the toy's base.

"Shit!" I exclaimed after realising the plug had been completely swallowed.

For the second time that day, a warm and calming sensation washed over me. My cock certainly approved, and I felt a sense of pride in being able to accept the toy in my bottom. I took a few tentative steps around the hotel room and felt no discomfort at all. I sat on a chair, no drama at all. I now had the confidence that I could wear the plug for a couple of hours as the sex shop attendant recommended.

I glanced at my watch and realized that I had better get to the Exford Hotel in readiness for Gary's arrival. There were no messages from Gary, but I was sure he would arrive as he was as excited about the evening's planned activities as I was.

One thing I quickly noticed was my cock did not deflate. Rather, it remained in a semi-hard state of tumescence. As self-conscious as I usually am in public, I did not care if anyone saw the bulge in my jeans as I made my way to the pub.

With a drink on the table, I forced myself to read a book I brought. However, I could hardly focus as the words darted across the page, and I could not stop massaging my crotch. Sitting on a chair seemed to force the butt plug deeper inside was an intoxicating thrill.

As my head swirled, the phone screen lit up with a message from Gary.

"Be there in an hour. Can't wait."

"Fantastic. Me too." I replied.

Relieved that the 'main event' was going ahead, I began thinking of what acts might be performed. With a newly liberated mind, I envisaged a plethora of activities, some more extreme than others. I was thrilled with the idea of douching Gary's intimate hole, imagining his expression and the warm mixture filling him up. I figured I would need another one, too. Everything was so new but so very exciting.

As promised, Gary walked into the pub at the appointed time. After shaking hands like the straight-acting guys we were, he gestured toward my empty glass and brought two new beers.

"Cheers," I said, "How was your day?"

"Fucking dragged," He snorted, "What about yours?"

"It was an eye-opener," I replied, updating Gary on the day's activities.

"You're wearing it now?" Gary asked with wonderment.

"I am," I confirmed, "And it feels amazing!"

"I'll have to get one."

"My cock hasn't gone down since I put it in," I whispered, "Look."

Gary leaned over and tried, as discretely as possible, to gaze at my pulsing bulge.

"Shit!" He stuttered, "I want to touch it."

So did I, but there was zero chance of it, given the post-lunchtime patronage of drinkers coming and going past us. The constant twitching was driving me wild with lust. If I were not careful, there was a real risk of blowing my top prematurely, which would rob us both of a good time.

Matters were not helped by Gary's boyish good looks and wiry physique. I look at guys all the time but never felt any attraction to any of them, regardless of how good-looking they were. Gary sparked something deep inside me, a primal urge to surrender to urges previously unknown.

Gary, on the other hand, was a straight-acting gay youth with limited experience and body count. A chance meeting in an adult theatre had placed us on a journey of sexual experience together. So far, I have been enjoying the discoveries made along the way.

As the afternoon wore on, we were both on tenterhooks, and neither of us could wait any longer. Before leaving, I grabbed a six-pack, and we made our way to the hotel. The lobby was crowded, so no one noticed us as we entered the elevator.

"Wow!" Gary exclaimed, amazed at the room's opulence and the view across Port Phillip Bay, "This place is amazing."

"Yeah, it's pretty good," I said after strong-arming the six-pack into the fridge.

I stood up, and Gary turned away from the window. We stared at each other, seemingly frozen with fear, stunned at the realization that the moment had arrived and unsure what to do next.

Arresting the initiative, I walked to Gary and embraced him without saying a word. His bulge pressed against me as we started kissing softly and slowly. As our tongues and lips danced the tango, I was almost at breaking point. My cock was ultra hard and begged for release, but I desperately needed to restrain my passions.

"You want to get started?" I whispered while softly nuzzling his ear.

"Yeah!" Gary replied as his head tilted in reaction to my tongue.

"Undress me!"

Gary removed my shirt before dropping to his knees and removed my shoes. He was in no hurry and took the time to help build the passion. After unbuckling my belt and jeans, Gary told me to bend over the desk. I knew exactly what he had in mind. I did as requested and thrust my butt towards Gary and he hooked his fingers into my jeans and boxer shorts and gently pulled them down.

"Wow!" Gary took a sharp intake of breath as the plug was slowly revealed, "That's the hottest thing I have ever seen."

"You like that?" I asked rhetorically and did a quick booty shake.

"Can I touch it?" Gary asked excitedly.

"Of course," I replied, "Why don't you slowly withdraw it."

"Oh, man! I'd love to."

I felt Gary's delicate finger take hold of the plug's base. Simultaneously, I grabbed both arse cheeks and pulled them apart. On feeling the tug, I flexed my O-ring muscle to help ease the toy from my back door.

Gary was as delicate as his youthful frame. He gasped as my starfish slowly expanded to an insanely wide degree. The withdrawal was an intense feeling, and I came close to exploding ropes of steaming come onto the hotel carpet. Once I got over the widest part of the plug, the rest of the length slipped out easily.

Then I was empty, hollow, devoid.

My first anal experience was supremely intense and successful. I hungered for more and felt confident that I could take Gary's length and drooled at the thought.

"Fuck, man!" I sighed after standing up and kicking my jeans and boxer shorts away from my ankles, "That was great."

"You liked that I see," Gestured Gary as my cock spasmed repeatedly with pre-come oozing from my cock head.

Gary extended a finger and raked the nail across my crimson helmet, scooping up the translucent fluid, before licking it clean. He complimented me on the taste.

"Give me a minute to recover from that experience," I said before breaking open a beer and slumping in the chair by the desk.

Gary, remaining on his knees, examined the plug minutely, not having held one before. I watched him intently, his youthful curiosity a delight to behold. Without warning, he plunged the toy into his mouth and sucked on the smooth rubber enthusiastically.

"Mm, it tastes so musky," He observed, "I like your butt flavour already."

Gary idled up to me and we kissed furiously. Grabbing the beer from me, he took a long deep chug.

"I seem to be overdressed," Gary said, before standing up and discarding his clothes.

His cock was hard and raging. I beckoned Gary forward, opened my mouth and invited him inside. With both hands on his arse, I throated his length with a longing hunger, enjoying the feeling of his head hitting the back of my mouth.

"Let's get on the bed," I suggested.

Gary lay down on his back with his head on the pillow. I grabbed his legs and pulled him down and told him to roll on his side. I climbed on the bed but in the opposite end, my head pointing towards the bed's base. Initially confused, Gary quickly understood. We engaged in an unconventional 69'er that had the advantage of allowing access to each other's shitter.

With our mouths clamped over cock meat, I wasted no time in fingering Gary dirt tunnel. Shit, he was tight! Little by little, I worked two fingers inside, his body shuddering repeatedly. I encouraged him to do the same to me, but Gary had an easier time because my bung was super relaxed from the plug.

"You keep that up, you'll make me come!" Panted Gary after maybe five minutes of mutual oral.

"We can stop if you like," I replied, "Or, if you can perform again later then I'll let you come in my mouth."

"Yeah, I'll be able to recharge," He replied, "I really need some relief."

I knew what he meant but I wanted to hold back a bit.

"Then, come in my mouth."

Quickly rolling off the bed, I sat on my haunches and waited for Gary to stand in front of me. I told him to clasp his hands behind his back and allow me to jack his cock to a heavenly climax. Taking hold of the shaft, I started wanking it while tilting my head back, opening my mouth and sticking my tongue out.

Gary's eyes bulged and one leg began shaking. I knew he was close, and I dribbled in anticipation. As soon as he crunched his eyes closed and thrust his head back, Gary gave up his prize. Rope after sticky rope erupted from his cock head. Most landed on my tongue but several overly excited spurts shot across my upper lip and cheek. Gary held his breath and was silent despite the violence his body experienced.

As his orgasm subsided, Gary fell on the bed. He opened his eyes and looked straight at me; my tongue out coated in steaming jizz and smile on my face.

"What a load," He exclaimed in wonder.

"Uh, huh," I gargled in reply before pulling my tongue into my mouth.

I swirled Gary's seed several times savouring the taste before swallowing. I then scooped up the stray shots and gulped them down too.

"Yummy," I smiled.

"Man, that was one strong orgasm," Gary breathed with delight, "Thank you."

"My pleasure," I smiled, delighted at the compliment, "Next load I want in my arse."

"I can do that," Gary chuckled, "But only if I get yours after."

I cracked another beer, and we sat in a comfortable silence drinking and recovering our strength. Afterward, we decamped to the bathroom where I prepared an enema mix while Gary cleaned the butt plug.

"You ready?" I asked.

"For sure."

Gary got down on all fours, his beautiful hole exposed. I could not help myself and I dove face down and began furiously rimming Gary's intimate bung. We moaned with mutual pleasure, and, when I grabbed his floppy cock detected the faintest signs of life returning.