Bartended: My Gay First Time

What follows is a true story about my first time at age 18, which due to youth and confusion, was unusually short and largely uneventful. Then the story continues, rewriting the true ending for a fantasy ending that I wish would have happened.

He ran a bar in a dark corner of a dated strip mall on Long Island that was clean enough, but also old in the way that the Chinese takeout place three doors down had become a greasy late night staple for decades, and no one could remember what was in other storefronts before the dry cleaners, pizzeria and hair salon. The main bartender and bar owner's name was Rickie, but I've long since forgotten the name of the bar itself. It was no dive, just a typical small local bar, not a wannabe Irish or English pub, a typical American joint that didn't try too hard, with a dart board, tables, round center bar, bathrooms and just past the jukebox, a storage room where Rickie kept a desk among the boxes stacked on racks to the ceiling. The lights were dim but not overly so, and except on weekend nights, the noise was low enough to carry on a private conversation. My friends and I would frequent the place our senior year in high school, as Rickie was an "easy ID", and this was when the drinking age was still 18 in New York. He didn't card as long as he knew you or someone in your group was of age.

Rickie was about 30, give or take a couple years. 5'10, a slim but fit build, and a neatly trimmed beard of thick stubble. He had olive skin, maybe some Greek in him. He had a fiance that I saw a few times, an attractive blonde his same height with long hair and a tight ass and firm breasts. She never stayed long when she popped in.

I had heard in my group of friends that Rickie had sucked a classmate and another rumor that he had kissed the forehead of one of the guys in my friend group while making a pass. My friend never spoke of it, but others had. I gave it no thought, rumors are rumors and to me, Rickie was a just a nice guy.

One evening, one of his part-time bartenders came in with a box of polo shirts branded with the bar's name. Rickie was going to have all his employees (there were few, mostly part-timers for on weekend crowds) wear them when working. I was sitting at the bar with friends, and his back was toward me. When I saw he was going to try one on by stripping to the waist right there, I found myself feigning interest in the shirts and repositioned myself to get a glance at his chest. As he peeled off the shirt he was wearing, he caught my eye looking at his his defined abs and Apollo belt, and his pecs, all covered by a soft layer of fur more sparse than I had anticipated but still a nice accent to his torso. I was embarrassed to be caught looking, but assumed it would be quickly forgotten. It was a busy night. He got back to slinging drinks and I returned to my friends.

One afternoon a few days later, I got off work as a coach for a local Y and had no where particular to be so I innocently stopped at the bar to grab a beer and shoot the shit with Rickie. Turns out the place was empty at that time except for him and me. I ordered a beer, but he "kindly" upgraded it to a strong whiskey sour (the only hard alcohol my 18 year old taste buds could manage) and I started talking about a recent split with a girlfriend. He walked around the seating area and wiped tables as I explained about how my leaving soon for college was impacting her.

"How's the sex?" he asked.

"It's fine," I lied. She was a good Catholic girl, in the way that Catholic school girls are hot, so a constant if unintentional tease, and I was as horny as, well, an 18 year old.

"So everything works down there," he responded, motioning toward my crotch.

I laughed awkwardly. "Yeah, no issues."

From across the room, he stopped cleaning momentarily and asked, "Can I see it?"

Now two strong sours deep, I answered confidently, "Be careful what you wish for, I like being naked." Which was true, I stripped at nearly every opportunity and was often naked at home. I was a bit of a skinny twink at this time (I later developed into a slim otter) so it wasn't an abundance of body confidence driving me, but again, just that teenage libido. I pulled down my jock and track pants and flashed him.

"Looks good" he said admiringly of my 6" cock, surrounded by a thick patch of teenage pubic hair.

We made more small talk as he made his way around the bar to where I was sitting. "Can I touch it?" he suddenly asked.

I now knew the rumors were true and moreover, I was now out of my depth. Shocked and confused, I just sort of went along. "Yeah, I guess so." He reached into my jock and stroked my shaft, which came to attention quickly. Rickie looked me in the eyes and smiled.

"It gets hard fast, that's good." He released his grip and left my erection peeking up out of my track pants, now caught sticking up between my belly and the jock's wide elastic, with abundant public hair and treasure trail peeking above my waistline. The bar was still empty but anyone near me would have gotten quite an eye full. Did he know I would be a willing mark, based on my glance at his chest days earlier? Did I know it?

Rickie returned to perfunctory wiping of the bar top when he suddenly grabbed me by the wrist and said, "C'mere, I want to show you something." He pulled me into the storage room as I stumbled, partially drunk, with an obvious erection emerging from my pants. He leaned me against the only empty table in the small room stacked with boxes of beer and liquor bottles, and closed the door, leaving the only light a desk lamp in the corner. He dropped to his knees, pulled down my track pants and jock in a single tug, and took my engorged twink cock into his mouth. He bobbed on it recklessly, ravenously, only coming up for air to then lick it slowly, head to base, catch my eye, and swallow it again. It was the eye contact I remember. He stared at me as he sucked my balls and teased the head of my cock with his tongue. In that moment, as a virgin 18 year old on the verge of manhood, I felt so powerful and dominant looking down on this man, with my cock in his mouth, in a such a submissive position of service.

It couldn't have been more than minutes or moments later that I came, although I don't recall the orgasm. I even questioned myself if I came at all until Rickie wiped some of my cum off his stubbled lips, having swallowed my load, moaning to himself, "thats good". Rickie then lifted me, buzzed from whiskey sours and still dazed from what just transpired, to a standing position, pants still around my ankles. We embraced, kissing deeply, and I remember wondering if that salty taste on his tongue was my own cum. In fact, for a straight identifying teen who had just allowed himself to be blown by a man, I had a lot of questions swirling in my head and I wasn't really into the kissing. It was then that Rickie opened his eyes and asked, "do you always kiss with your eyes open?"

Kiss. I was kissing a dude. All that stubble, his tongue, my cum. What was I doing? "Uh, no." The adrenaline subsiding and my buzz lifting, I quickly pulled up my pants and turned toward the door of the storeroom. We passed the bar together when he turned to block my exit. "That has to stay between us. I have a fiance. She knows, but not that I'm still... we're getting married, you know." I nodded I understood, as I certainly wasn't going to say anything.

"Yeah, of course", I mumbled.

"Was that your first blowjob?"

"Yeah."

"They're just as good to give as receive," he hinted, though I wasn't picking up the hint at the time. I nodded.

"Okay, then." I moved toward the door and he put his hand on my shoulder as I went through the door. I'd think of this encounter over the coming years but in the denial and confusion that followed, not for days but for decades, I'd never return to the bar or see Rickie again.

Now, dear reader, that's what actually happened. Today, a grown man looking back, I wish I could replay that afternoon again. Here's a better, hotter alternative ending:

We embraced, kissing deeply, and I remember wondering if that salty taste on his tongue was my own cum. In fact, for a straight identifying teen who had just allowed himself to be blown by a man, I had a lot of questions swirling in my head and I found myself excited by the kissing. The stubble I felt, his tongue in my mouth darting about. It was then that Rickie opened his eyes and asked, "do you always kiss with your eyes open?"

Confused but still excited, I had already allowed the situation to get out of hand so, what the hell, I thought, and I decided to lean into it. I'd soon be a college man and new adventures were around the corner, I reasoned. I spoke slowly and low, but surprisingly confidently. "Teach me," I replied, and fumbled at his belt buckle.

He anxiously helped with his belt and zipper when I surprised myself with my own boldness, "lose the shirt". We removed our shirts and I got to put my flat palm against his warm otter chest. He pulled me closer and Iour chests melded as we kissed again. My pants still around my ankles, my fading erection was again ignited and bobbed as I he released his embrace and I squatted in front of him and pulled down his tight jeans. I brushed my hands approvingly on his hard, firm stomach and pulled down his briefs. His cock sprung forward, grazing my forehead. I backed away, cradling his balls, and looked up at him, awaiting instruction.

"Lick it up and down. Slow."

I noticed he was uncut but somehow instinctively pulled back the foreskin, which was already starting to recede on its own as his cock grew. I obliged with long slow appreciative strokes of my tongue, impressed by his girth and hardness as his cock responded to my beginner's touch. I discovered a strange sense of pride at my ability to get his flaccid cock to full mast - a girthy nine, maybe ten inches. He grunted and murmured his approval.

After a minute or two, "Now lick your lips and take it all." As I moved down his hard shift, he pulled back. "No teeth," he admonished this newbie. "Open wider." He wrapped his lips over his own teeth to demonstrate. "Lig dis" he mouthed. I was a quick study and was soon taking his shaft farther down my throat, circling the head with my tongue, and flicking the tip.

"You're a natural", he repeated more than once.

I loved it. I couldn't get enough of his hard cock, the full, warm sensation in my mouth, and the feel of his chest as I reached up and caressed his hard, lightly hairy torso, using my fingers to brush his nipples, and trace his abs and Apollo belt, all while feeling his pre-cum mix with my saliva as I greedily worked his shaft.

I paused for a moment to take some deep breaths and smile at my mentor, my lips dripping with spit and desire. Rickie brushed the hair off my forehead and whispered, "here, let me do the work for a bit." He grabbed my chin and pinched my cheeks, my mouth forming a perfect O. "I'm gonna face fuck you", his tone turning more dominant, and he thrust his engorged cock far down my throat, well past where I'd taken it before. I choked momentarily until he released. "Don't fight it. I'll let you breathe, but not til you have to." With that he took my head between is hands and used my throat like a sex toy, faster and faster, farther and farther. I thought I'd pass out. I was filled with terror, humiliation, and excitement. I was entirely his.

Suddenly, Rickie pulled out of my mouth and again flipped me around against the table. Breathless and excited, he asked.

"Can I fuck you?"

At this point I was excited and subordinate and willing to do whatever Rickie wanted. He was my mentor in this new experience. The teacher, I was the student. Just minutes earlier I had felt dominant when he first sucked me off. Now I realized that I was enjoying being subordinant even more. I was learning. I was a good cocksucker, Rickie had told me so. Now I wanted to please him more. I wanted to be a good fuck for him. I spread my legs, offering my cherry bussy. He would be my first. I would be his willing faggot.

"I just showered at the gym before coming here," I volunteered.

"I was counting on that" Rickie smiled, teasing my hole with the light brushstrokes of his fingers.

He licked the length of his fingers and inserted them one, then two, into my waiting asshole, slowly in, the out. In again it repeated. He smiled, and leaned down to lick my asshole. I was initially disgusted, but breathless. "So this is gay sex," I thought to myself, as if inspecting a new amusement park ride. He licked three fingers and said, push down this time. You'll think you're taking a crap, but you won't be."

I grabbed the edges of the hard, cold table. "Push," he reminded me as now three fingers went up my virgin hole. I felt full. I felt a chill. But not much of the pain I had expected from prison movies and idle chatter. My saliva, his saliva and pre-cum made a satisfactory lube.

Removing his fingers he then placed the tip of his cock on my hole, swirling it a bit a poking at my entrance. He spit in his hand and worked his shaft. Finally, the press of his cock in my asshole. It filled the space and slowly went farther in to my second button. I gasped. He pulled back, but not out, and entered again slowly. Again and again, with increasing speed, Rickie's piston hips drove his cock farther and farther into my waiting bussy. I held on tighter as the table made a noticeable thumping rhythm. He went all the way past the second button slowly as I took a breath.

"I want to see you when I fuck you."

Rickie pushes me onto my back and then pulls me to the edge of the table and speads my legs, putting my feet on his shoulders. He thrusts repeatedly, faster, aggressively. I squirm and clench, lowering my legs to wrap around his waist, drawing him closer, his cock deeper. My cock is engorged as I focus on the waves of pleasure inside me. His breathing gets heavier, the table still thumping the wall rhythmically. He suddenly, wordlessly pulls out as streams of his cum cover my as yet pale hairless chest and flat stomach. I grab my own cock and stroke quickly with excitement and cum in leg weakening waves, mixing his cum with my own. Rickie then leans in, scoops up the mixed cum with his tongue, and kisses me deeply, painting the inside of my mouth with cum and spit. I'm breathless, exhausted, weak.

We separate, and use dirtied bar rags from a nearby laundry basket to dry off, kissing and quietly chuckling.

"That was good," I say.

"You were good", he says, lightly brushing his thumb across my lips.

Suddenly we hear the door to the bar opening and Rickie speeds up getting dressed. "Shit," he mutters, quickly turning to me for a fit check. I nod and he brushes his hair back as he exits the room. He turns and says, "think of something, quick."

I finish pulling up my track pants and check my walk. It doesn't feel too obvious that I just got my virgin hole plowed. I grab a case of beer off the shelf and walk out of the storeroom. "Here's the last one," I improvise, hoping to convince the visitor that I was helping Rickie stock. I look at Rickie, and he's looking sheepish. I look at the customer at the bar. It's his fit blonde fiance, she in lycra yoga pants and a loose t-shirt. I put the box on the bar, turn to Rickie, and say, "Happy to help, but I have to go." I turn at the door and see them both watching me leave. Rickie's fiance shouts after me. "Whats the hurry, young fella?"