Lovely Leon

I am sexually versatile and the top and bottom role-play always bored me because I prefer a more holistic approach to sex. Sixty-nine and flip-flopping is my passion and turns me on more than the one-sided methodology, into which some partners often pigeonhole themselves. Being broadminded, I am not a size queen. Early on, I discovered that even below-average guys were often better lovers than many horse-hung dudes.

Truthfully, I generally gravitated toward men of my age or older and mostly avoided twinks. That all changed in my mid-thirties when I met ‘Lovely’ Leon. He and his mother rented a small apartment that an entrepreneurial neighbour a few houses away from me had built for additional income. His mom was a waiter, and Leon was in high school.

I had a home in a modest suburb and got surrounded by earthy neighbours. That was all my low-paying job could afford. I was a security guard and worked the night shifts. The women in the neighbourhood were all frumpy-looking, but the blue-collar men were a treat for my eyes. They were all ultra-straight-looking rough men and nourished all my fantasies. I often found myself drooling when I engaged them in the odd bit of conversation from time to time.

I was not naïve enough to believe that I would get lucky with any of these neighbourhood hunks. I, however, enjoyed an active sex even though I was not in a relationship and had no interest in one. Being off duty during the day, I frequented adult bookstores and a bathhouse where there was always plenty of action. On my evenings off, I also frequented an action gay bar. I always hoped to bump into a stray hunk from my environment on one of these visits. Regrettably, that never happened.

On the day I officially met Leon, I was in the front yard. It was on a day when I was not visiting a bookstore or bathhouse. Previously, I had seen Leon on his skateboard performing his tricks up and down the road. Leon had a lithe body and was no more than five-foot-eight-inches tall. He was wearing a wife-beater t-shirt and a pair of ridiculous shorts that looked too large for him and low on his hips. In keeping with the silly garb of most youngsters, his cap was on backward.

As observed him, one of his tricks ended in disaster. After sprawling on the asphalt, I immediately ran toward him to see if he was injured. Apart from lightly scuffed hands, he had a bloody knee.

“Are you okay?” I blurted.

“Yeah… It is nothing he countered, almost dismissively.

“Your knee is bleeding,” I contradicted with concern.

“Pfft, it happens all the time,” he matter-of-factly replied.

“Well… Let me at least disinfect it and put on a plaster,” I offered.

After a few seconds of deliberation, he said “Sure,” before picking up his skateboard and following me into my house.

Inside, I placed one of my dining chairs in the kitchen and asked to sit down while I retrieved a tray of medical supplies. While cleaning the wound I got my first good look at Leon. He was a handsome little fucker. Although only sixteen, he already exuded a masculine roughness. The blond shoulder-length locks exuding from the bottom of his cap appeared to be slightly damp, presumably from his physical exertions. His hands, although somewhat icky, had no damage from his fall. I was also happy that he clipped his fingernails very short. What intrigued me most, were the size of his skanky trainers. For a shortish man, they were at least a size eleven.

Once I cleaned the wound, I placed a suitably sized plaster over his knee.

“Listen, Leon, there is blood on the bottom of your shorts. Blood can stain very badly if you do not take immediate care of it. I have an excellent detergent spray that will prevent that and after a quick rinse you’ll only have a small damp patch,” I suggested.

“Should I take my pants off?” he asked.

“That would be advisable… We don’t want to get detergent on your plaster,” I recommended.

Unfazed, he stood before saying, “I don’t wear underpants, so if you don’t mind looking at my cock, I’ll hand you my pants.”

As cardiac arrest almost set in, I tried not to act flustered.

In as measured a tone as possible and practically pissing myself with excitement, I replied, “Don’t worry, I have seen many cocks.”

“Mmm, but I’ll bet not one like mine,” he uttered with bravado.

There was a mischievous look in his eyes as if he was toying with me.

As I watched in anticipation, he undid his belt and let his trousers drop to the floor. The initial sight of his cock was incredible. Leon then bent over and disentangled his pants from his trainers before handing them to me. Next, he sat down wide-legged and let me fully absorb the full splendour of his knob. It was breathtaking!

His cock looked like a torpedo. The remarkable length parenthesized a fat mid-section that was as thick as my wrist, and which tapered a smaller head smothered in a thick foreskin. The wrinkled foreskin overhang was deliciously enticing and my tongue began twitching in anticipation. After lifting his t-shirt above his nipples, he sat there brazenly looking at me as the index finger and thumb of his right hand fondled and tugged on the foreskin overhang.  

I was trembling as I walked to the basin with his shorts and commenced my cleaning process. Once I had completed my task, I handed his shorts back to him. As I did so, the arrogant little shit tossed the pants next to him, before asking, “So… Faggot, are you going to suck my dick or not?”

“Why do you assume I am gay?” I challengingly inquired.

“Oh, come on… Much as you try to act cool when I play in the road, your homo eyes always give you away,” he facetiously blurted.

“Does that mean you are also gay?” I rhetorically inquired.

“Pfft… Maybe, maybe not. I have not yet decided. The thing is, this cock has supplied me with a lot of pocket money in the past,” he glibly informed me.

‘Oh, shit, I am being hustled,’ I thought.  

Trying to act as calm as possible, I asked, “So, how did that work.”

“Well, before my mom and I moved here, I had a chubby sissy boy who got lots of pocket money and was happy to generously share it with me,” he facetiously informed me, before adding, “He couldn’t keep his chubby lips off my dick.”

“Did you also fuck his arse?” I boldly inquired.

“Yeah… But that came at a substantial premium,” he confided, in a business-like manner.

“Did he pay you by the hour?” I queried.

“Nah, once he sucked me off or I fucked him and unloaded, I fucked off with money in my pocket,” Leon matter-of-factly informed me.

I was now beginning to enjoy the interplay and challenge. I was also becoming determined to teach this little arrogant shit a lesson.

“So… What kind of money are we looking at?” I asked.

“Twenty-five bucks if you suck me off and fifty bucks if you want me to fuck you,” Leon boldly stated.

“Sounds reasonable,” I uttered.

With an impish demeanour, he wriggled his hips invitingly. As I got to my knees, the torpedo had substantially inflated. As I lifted the bulky baton, the silkiness of his knob was mesmerizing. I felt like a snake charmer in the throes of a Middle Eastern ritual. After lowering my head, my lips commenced gnawing on the pouty tube dangling off the front of his hidden glans, overwhelmed by the smell of his heady crotch as I did so. The odour was potently pungent and the masculine fumes made me wince with lust. Hygiene was, definitely not at the forefront of his daily regimen. Although I was too far gone to care, I did wonder what the inside of the hood would reveal.  

Deciding to take things slowly, I first let my lips and mouth caress the tightly hooded torpedo, as my right hand fondled his ball sack. Leon was in ecstasy, and as his left hand shrouded the back of my head, his right commenced slapping the top of his left hand, to demand a fuller entry.

“Open up, you bitch, you can do better than that,” he commanded as my mouth expanded to his expansive onslaught. My lips were at full stretch and his hand hammered the back of my head. My mouth now endured the upward slamming of his urgent hips. With my head being used like a fleshlight, it did not take too long before the lava began erupting from the elephantine snout of Leon’s dick. I was gobsmacked by the discharge and swallowed as never before.

“Well… That is twenty-five bucks. Now let’s go for the fifty,” he arrogantly asserted as my oral attack ended.

“Shouldn’t I first pull the skin back and clean you cockhead?” I inquired.  

“Nah, not possible. I have phimosis,” Leon informed me. Although I had heard of this condition, I had never encountered it before. As if to prove his point, Leon pulled his foreskin back as far as it would go. All I could see was a red piss slit surrounded by thick folds of puffy skin.

“Can you push your finger in there?” I asked, intrigued.

“I can only get my little finger in. But as your hands are slimmer than mine, maybe your index finger might fit in,” he proffered.

With difficulty, I managed to insert my finger into the extremely tight aperture. It would only go as far as my first knuckle. After I extracted my finger, I lifted it to my nostrils. The odour was unearthly, and it smelled like an alley where men frequently urinated. Inexplicably, I found the stale fragrance arousing.

“Do you like it?” Leon inquired.

“Yeah,” I honestly replied.

“Me too,” he countered, before pushing his little finger into the constricted opening. After twirling his digit around, Leon then removed his finger and smeared his little finger in both of his nostrils. With a smile, he then inhaled the aroma approvingly.

“How do you clean it?” I asked, mesmerized.

“With piss. I simply clamp the snout and let the piss fill build up before releasing it when I shower. Urine is a great disinfectant and I have never had a problem,” Leon concluded, before asking, “Do you like the taste of piss?”

“Yeah… I guess,” I dishonestly answered. I had never indulged in piss-play, not because of abhorrence, but simply because the opportunity had never arisen. Yet, here I was in my mid-thirties, getting instructions from a sixteen-year-old boy.

“Cool,” he said as he stood. “Open your mouth.”

I watched as he clamped his snout before placing his cock at my mouth. As I observed the ballooning foreskin, he pushed his dick into my mouth.

“When I tell you, you must swallow like crazy… Swallow!” he yelled as a torrent of piss splashed on my face and into my mouth, also spilling down my shirt. His hands then gripped hold of my head, plugging my mouth with his fat knob, as a waterfall of nectar erupted into my throat. I have no idea how I did not choke.

Scary at it was I also found it wildly exhilarating. Once he was done, he lifted my body and after pushing me toward the dining table, he pulled down my shorts.

“I want the extra fifty bucks,” he said as he lodged his dick at my hole. Without pause, he swiftly entered my backside. As I yelped, Leon commenced hammering my backside, spread-eagled over the table. The domination from this little fucker was mind-blowing, and in keeping with his ‘aggression,’ I bleated like a virgin on her wedding night as the torpedo thumped me. It was glorious!

After an age in heaven, Leon roared as he unloaded.

As we stood looking at one another afterward and sweating like racehorses, he extended his hand with his palm facing upward.  

“Do you have any change, because I only have a one hundred, dollar bill?” I queried.

“Nah… But I can bring you your change tomorrow…” Leon stammered.

“Mmm, but I hardly know you, and therefore don’t know if I can trust you,” I reasoned.

I had enjoyed our encounter very much thus far, and was also, determined to fuck him.

“Tell you what… I will just give you a hundred bucks… After I fuck you,” I deviously suggested.

“Whew, that’s not my thing,” Leon apprehensively refuted.

“You’ve got a lot to learn, boy. Right now, I am the one with the full nuts. To succeed in life, you have to learn that customer satisfaction is very important. But, if you are too much of a pussy to take it, then I’ll give you fifty and you can collect the balance tomorrow,” I assertively challenged him.

“I’m not a pussy!” Leon shot back.

“Then prove it!” I countered.

After turning slowly and hugging the dining table, he said, “Just take it easy.”

“Aah… So you are not a pussy, but a sissy,” I scoffed.

“Just do it,” Leon defiantly responded.

No second invitation was required. After applying a minimum of spit to my knob, I performed a slam-dunk. Watching the arrogant little cunt squirm and squeal, was heavenly as I nailed his tight arse.

“Please just get it over with,” he began imploring.

“No. I’m going to take my time,” I barked as began a slow rhythmic anal penetration. Tough as Leon was, I knew that my larger frame could control him. I could also sense that his moans of distress were morphing into groans of pleasure. After flicking off his cap, I grabbed a handful of his golden locks. After pulling his torso up, my left arm encircled his body tightly.

With my lips at his ear, I gruffly exclaimed, “You fuckin’ little hustler, now we’re going to the bedroom, where you’ll earn your fuckin’ money.”

After shuffling through to the bedroom with Leon impaled on my knob, I pulled my cock out of his backside and spun his body around to face me. Next, I shoved him on the bed and jumped on top of him. As I commenced kissing him, he tried to avoid my mouth but I was having none of it. After I slapped Leon a few times, my hands closed on his head like a vice and soon my tongue was boldly sloshing around in his mouth.

Shortly, Leon’s reluctance turned into acceptance as we fervently commenced snogging. For me, this was turning into the most unbelievable experience of my life.

As our bodies melded together in a blissful union, my cock grew impatient to traverse the gate of heaven once more.

Lifting my head I curiously asked, “Have you ever been fucked before today?”

“No,” Leon blushingly admitted.

“Well, buddy, you’ve got the hottest arse I have ever fucked,” I informed him.

“So… What are you waiting for?” he mischievously uttered.

What impressed me most as I lifted his legs over my shoulders and re-entered him, was that his dick was rock-hard. 

“I hope you are not in a hurry to leave?” I questioned.

“Take your time, give me all you’ve got, papa,” Leon impishly chuckled.

From here on… We made love, frequently interchanging positions as we flip-flopped and sixty-nined. The day was turning out to be a tour de force. Our interplay had a wonderful element of fun as we constantly swapped the domination role, drenched in a heady haze of masculinity.

“Fuck… This room is beginning to hum,” I eventually said.

“Yeah, you’re beginning to smell as bad as me,” Leon chuckled.

“Well, man stink rules” I replied with a laugh.

When I eventually unloaded, I did so in his mouth as he plugged my arse with three fingers. It took Leon a few more minutes before he came a third time.

We cuddled and kissed a long while before he was ready to leave.

As I handed over a hundred bucks, I ruefully admitted, “Listen, buddy, I can’t afford this daily, much as would like to.”

“Yeah, I realize that,” Leon replied with a smile, before holding up the cash and saying, “This is more than enough for a week.”

As a joke, I asked, “Do you have any other special needs in the future?”

“Yeah, don’t ever use soap when you shower,” Leon hornily replied.