Better Late Than Never Ch. 03

I texted Marley "The Game's Afoot," and filled in the details.

Her reply made clear that she understood the Sherlock Holmes' reference, but she couldn't resist poking a little fun at me.

M: Ah, "The Case of the Casino Kiss." You didn't mention anything about a foot fetish, you naughty boy! Chronicle lurid details and maybe win another sketch.

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There were ten days until the weekend, so I made a couple of resolutions. First, if Tom didn't bring it up, I resolved not to let "The Mystery of the Casino Kiss" get in the way. Second, I resolved not to jerk off before our encore, convincing myself that I needed to allow for sperm resupply. Well, you know what often happens to the best laid plans of mice and men. The vivid scenes my memory and imagination conjured up frequently drew my hand to my cock and a finger or two to my anus.

While most of those scenes involved what Tom and I had shared and what I hoped might take our next time together to even greater levels of pleasure, there were some others without Tom.

Marley's comment that there were guys out there who would find me to be the perfect one to introduce them to male-male sex. While I realized that my limited experience made that a massive overstatement, but it got me wondering and fantasizing.

Once Tom and I got into hot and heavy Zoom chats, I hadn't bothered to going back to the hookup app to check for any messages. "Yes," I said out loud, when I logged in and found seven new messages.

Three in particular seemed to be possibilities. One, I have to admit, that had me stroking my cock to full hardness was from a 50-year-old with a lover in his 30s--Matt and Jerry. He gave a compelling description of the threesome he and his lover had fantasized about. I remembered how when Tom's limp cock slipped from my ass, I had longed for another hard cock to fill my cum-coated rectum. I also had fantasized about servicing two cocks until I received a massive facial as first one and then the other blasted cum at my hungry mouth.

I wrote back a simple response--"Very intrigued," though I wasn't 100% sure if I was ready to be cumdump, a plaything for two well-hung horny guys. Imagining it had me stripping off my clothes, slowly stroking my cock and tugging at my nipples. I'd lick my fingers and massage the smooth skin of the head of my uncut cock and flick the sensitive frenulum with the tip of a finger. The images were so vivid of two strong hands lifting my buttocks off the bed, my legs on his shoulders while his hard cock pounded my ass as another cock filled my mouth that my hand would flash up and down my stiff shaft until I'd cum hard.

In the aftermath, my thinking self would step in and question whether or not I wanted to go there, wanted to be so vulnerable. I reminded myself that I had always found 69 to be overrated--too confusing. But I had to admit that I was probably just too chicken.

I suspected I might eventually go there, but not just yet. Wasn't my goal to initiate another new guy?It would be a real turn-on to be another guy's first, to bring him to the new pleasures I had just finally experienced.

The guy who claimed his name was Doug caught my attention because I understood both his desire and his trepidation. He was in 40s and had just gone through a contentious divorce. No kids. Sexless marriage for several years. He'd relocated, had few family ties, and found that memories of his one experience of sucking a cock in college in a Truth or Dare game were reviving desires he had thought he put to rest for good. He worried that he'd be so nervous that he end up with a limp dick and be totally embarrassed.

Doug described how he'd stripped naked multiple times and scrolled through the nudes I'd posted of myself while he stroked himself to orgasm.

That made me smile. The time I'd spent trying multiple poses and exposure experiments had been effective, I guess. Though I'm pretty skilled in Photoshop, I'd resisted the temptation to add an inch or two to my cock.

Doug didn't have photography skills or the equipment to match mine, but he had posted a few close-ups of his dick. Not as sharp or well-lit as I would like, but he was definitely longer that both Tom and I, probably about seven and half inches though not as thick. He was cut with a gorgeous helmet and defined ridge that I would love to tease. I certainly had a thing for cut cocks, and I wondered for the thousandth time what my cock would look like cut. Well, I'd never find out because now that I'd discovered how much I love cock, I couldn't imagine putting myself out of action for the long recovery period getting cut would require. I wanted to make up for lost time.

It turned out that we lived just a few miles apart, so after some wavering on his part, I got him to set up a meeting at a local Italian restaurant. I sensed that his anxiety was partially eased because he knew the lighting was subdued, provided by candles on each table. Turns out, he was a regular there.

I knew it was a casual attire place, so I choose a polo shirt, some dark pants, and went commando. I skipped socks when I slipped into my comfortable boat shoes. I was eager for more action and figured I could get naked in record time.

"What the fuck?" I thought when I watched him enter the restaurant dressed in a suit complete with a vest. All he needed was a Bowler hat and an umbrella, and he would have been a perfect English gentleman. I could imagine him as one of the few persons left who might be wearing those old-fashioned sock garters. To get him naked, I'd probably have to imagine myself to be a valet or Gentleman's servant.

I got up and gave him a brief hug and pat on the back before sitting back down. I could feel his tension. We only exchanged a few words and smoothed over the awkwardness by silently pouring over our menus.

It was obvious the server who approached us knew him.

"How about we start with a bottle of Cabernet Sauvignon, Uncle Ed?" he asked. Well, I did understand discretion, but this seemed going to the extreme.

"Excellent," I replied with a smile and decided to play along. "You certainly know what I like." My expectations for where this meeting might take us were taking a nose dive and my cock remained dormant.

Though all my attempts to steer him into provocative subjects went nowhere, I began to wonder if his overdressing was actually strategically brilliant. He was like that beautifully wrapped present under the Christmas tree that screamed open me first.

I wasn't getting any vibes from him over dinner, so I began to suspect that this wasn't going anywhere. It seemed that someone else would get to open that present.

"How about you follow me home," Doug surprised me as we strolled to the parking lot. He tried to sound casual, but his tension was obvious. Maybe he figured I was disappointed in him.

"Yeah, sure," I replied, trying to sound intrigued by the prospect but not overly anxious.

It was a relief that we were going to his house rather than mine when I saw him climb into a Mercedes. I wondered if he'd have second thoughts when he saw me following in my ten-year-old Honda Civic.

Maybe it was because he wanted to make sure he didn't lose me, but he sure drove like an old lady on the way to his house. Maybe he was working up his nerve. The slow pace gave me time to imagine how this might go, and I found my dick getting semi-hard for the first time of the evening. But what I was conjuring up in my mind was quite different from what transpired.

Finally we reached our destination, a well-kept yard and a neat looking ranch house. The door to the two car garage slide open and he pulled in. I pulled in to the driveway and surprised that he didn't get out of the car.

Doug pushed open the passenger door. When I took the hint and slide in to the passenger seat the garage door began to slide down.

Memories of the awkwardness of making out in parked cars with bucket seats back in high school flashed through my mind, but if it was his thing, I was willing to go for it.

Doug's pants and boxers will pulled down to his ankles, and his fully erect boner was gushing precum. Perhaps he had dropped his pants before leaving the parking lot and his slow driving was the result of stroking himself.

My fingers were drawn like a magnet to the silky taut skin of his shaft. I lightly slid my fingers up and down before using my index finger to whirl around the bulbous head of his cock.

The absurdity of the situation--fondling a man still in a suit jacket, vest, and tie in the front seat of a car--didn't really hit me until later. My hunger for cock consumed me.

I pulled his head toward me, but he didn't respond to my lips tugging at his or my tongue seeking to probe his mouth. I let him lean back and lowered my mouth to those beautiful seven and a half inches.

As my lips slowly slid over his head and my fingers cupped his balls, he lowered his seat to the reclining position. My right hand stroked his shaft as I licked, tongued, and kissed his helmet. My left hand fumbled with the buttons of his vest. I used my thumb to stroke the underside of his shaft, milking more drops to precum to feed my lust.

With the tips of my fingers, I gently pushed his cock back, so I could drag the flat of my tongue over his balls and up the underside of his shaft. My lips planted a sucking kiss on his frenulum. My tongue pressed hard against it and swirled round and round.

I slid forward, locking my lips around his ridge and flicked the stiffened tip of my tongue against his pee hole. At its thickest, his helmet protruded a full quarter inch from his shaft.I twisted my head from side to side, sliding my lips round the ridge.

I felt his hand on the back of my head. I didn't need his help to take more of his beautiful cock into my mouth, feeling its warmth and hardness on my tongue and against my cheeks.

My sucking lips and swirling tongue moved slowly up and down his shaft. I wanted to savor every half inch, in no hurry to reach the limit I could take. I loved the feeling of my mouth stretched and full of cock. It felt so right; why had I denied myself this exquisite pleasure for so long?

When I'd finally got the vest unbuttoned and the tie loosened, I felt him unbuttoning his shirt and I slid my left hand up his abdomen to grasp and tug at a nipple. I hoped that he would get the idea and play with both of them himself.

I let his cock slip from my lips, so that I could coat the fingers of my right hand with saliva. He gave out a low moan of frustration until I slid his cock back into my mouth. My left hand reached under him to lift his buns off the seat a bit, giving my right hand access to his anal bud.

I wasn't sure if his moans were of pleasure or surprise. Maybe both. He was definitely tight, resisting my probing finger.

"Oh, God, are you going to fuck me?" he broke the silence. His tone could have been fear or longing. Maybe both.

I felt him getting close to cumming, so I gripped the base of his cock firmly with the thumb and index finger and reluctantly let his cock slip from my mouth. If he came, I feared it would be over far too soon.

My finger finally slipped past his sphincter muscles and searched for his prostrate. Could I hit it? Yes!

"Oh, oh, oh, Yes!" he uttered.

As I discovered with Tom, when I suck cock, I lose sense of my own cock. Now its full hardness and desire for release called out to me.

"I really want to fuck you," I exclaimed. "Do you want to be fucked?"

"Oh, oh, yes!" he managed to pant between moans. "Lube, glove compartment."

Shit, I thought. He had this planned.

"Get ready, now," I ordered.

Doug scrambled to reposition himself when I stepped out of the car and reached back for the lube. By the time I got around to the other side, he had stretched out with his chest on the front seat. His feet were planted on the garage floor, and his ass was sticking out the car door. He reached back to spread his buttocks. His legs were spread giving me a clear view of his luscious long cock hanging down. He did have this planned.

I wondered if plan had included getting rimmed. I bent over and coated his whole crack with laps of saliva before zeroing in swirling my tongue over the entrance my cock would soon penetrate. My right hand stroked his cock.

The only light was from the car dome light. I dropped my pants and lubed my cock. I squirted a generous amount onto my hand and spread more around his rim. I was able to work two fingers into him. Man, he was tight.

I so wanted to ram my cock up his ass to the hilt, but I knew his virgin ass couldn't take it. I teased him a bit by dragging the head of my cock up and down his crack.

I loved his tightness caressing my head as I pushed through his resistance. When the head was in, I began to push in slowly. His moans at first were clearly pain-filled, but soon they were a mix of pain-pleasure, and then pleasure with a hint of pain.

I lost sense of time, but it had to be at least five minutes of slow in and out before I felt him begin to push back, hungering to be filled. His warm tightness felt incredible, and he discovered how to clench his muscles to add to my pleasure as I came close to pulling out on each stoke back. I knew I would not last too long as I picked up the pace.

Soon I was pounding into him, meeting his hard backward thrusts. I gripped the edge of the roof above the door opening to give me more leverage. I loved his panting groans each time I slammed into him.

"Mmmmmm," I yelled out as my orgasm ripped through my spasming cock. I savored each surge of pleasure as I felt each separate jet of cum filling him.

I pulled out and reached between his legs. I wrapped my fist around his cock and jerked him hard until he splattered cum all over the leather seat and carpet of the car.

I stepped back and watched him gasping for breath. I knew that amid his moans he was stunned by the new pleasure he had experienced but feeling the emptiness in his rectum. I remembered that feeling; with it came the yearning certainty that I'd crossed a boundary and that I now had a hunger that could only be satisfied by being fucked again.

I could tell he was pretty spent when he finally pushed off the seat and stood up. Still half-dressed with his pants and boxers dragging along on top of one of his shoes, he waddled over to the wall and flicked on the light.

We were quite a sight, that's for sure, and we both burst out laughing.

"Can I offer you a drink," he said.

"Of course," I said," we need to toast your loss of virginity."

Doug tossed his suit coat, zest, and pants on the floor. The suit, I'm afraid, definitely needed a trip to the dry cleaners. He headed for the wet bar at the far end of the island in his spacious kitchen.

"I need to clean up a bit," I said. Doug's butt wasn't as clean as Tom's had been, so I really need to give my dick a quick wash.

Doug halted what he was doing and walked me past the half bath. He brought me to the master suite with a nice walk in shower and got me a wash cloth and towel.

The shower had a great hand wand with a long hose, so I wouldn't have to get my hair wet. I soaped up my dick and balls and went slow to make sure I was thorough.

This guy has a great fan, I thought because I noticed the glass doors of the shower weren't getting steamed up. I glanced toward the mirror over the double sink and was surprised to see Doug sitting on the counter in just his boxers. He was stroking his cock through the fabric, which had a large wet spot.

My glance was a quick one, and I don't think he noticed. His eyes were riveted on my cock.

While my body wasn't going to win any beauty contests, I was proud of how I had slimmed down. I figured for my age, I was at least semi-hot or at least substantially lukewarm.

Though I'd never thought of myself as an exhibitionist, washing my cock turned into caressing my cock. I really didn't expect to get more than semi-hard since I hadn't had much time to recover, but perhaps the novelty of the situation made a difference because I was soon fully erect.

I put back the hand wand and let the shower flow on my body. He must have figured out that I knew he was watching because I was gaving him quite a full show of all the stokes, fingering the shaft, and massaging of my head that made up my long intense masturbation rituals. I turned around a few times to tease him and give him a view of my ass.

Of course, Tom and I had played with our erect cocks on Zoom sessions, but during those I had been focused on watching him. This was different and somehow more intense. There was a bench built into one wall of the shower. I sat down on the edge and leaned back against the wall with my eyes closed. I stoked hard while tugging on my nipples before bringing my fingers to my mouth to wet them with saliva. I reached down and slipped two into my ass.

I shamelessly exaggerated my moans. Then abruptly I got up and turned off the water.

Stepping out of the shower, I grabbed the towel to slowly dry myself off. The distraction caused me to lose a bit of hardness, so I brought my hand back to my cock as I dropped the towel. After several firm strokes, we were both staring at the drops of precum sliding down the head of my cock and onto my thick shaft.

His boxers were on the floor, and he his hand was wrapped around those amazing seven and a half inches. I reached up and grabbed his cock and pulled him off the counter.

I was so caught up in the moment, I just acted from some deep instinct. I took his cock in my left hand and my right jerked up and down my shaft until I knew I was about to cum hard. There wouldn't be much so soon, but I spread a line of cum over his shaft.

I scooped up a bit on two fingers and dropped to my knees, I pushed him back against the counter and slipped my cum-coated fingers into his ass. I took his shaft deep into my mouth, savoring the taste of my cum. I'd never sucked so hard and soon he was trusting his hips. I so wanted his cum and pulled back a bit to take it on my tongue, his spasms sending shock waves of pleasure through me.

I coated my lips with some of his cum before swallowing the rest. I stood up to bring my lips to his. He sucked his cum off my lips as we were locked in an embrace, our wet, slippery cocks pressing against each other.

We cleaned up a bit then headed to the kitchen so he could finish making drinks. Sitting on the leather couch in the nude, we did finally have a decent conversation. He admitted that he hadn't been sure about kissing another man, and during the next half hour, I finally got him over that hurdle. After about 10 minutes, he got around to fondling my cock and having a go at cocksucking. His technique needed improvement but that would come with experience.

I slid down a bit on the couch so that my ass was hanging over the edge. I spread my legs, hoping that he'd take the hint and finger fuck my ass, but he didn't. Frustrated that he couldn't get me to cum in his mouth, he gave me a vigorous hand job. I managed to spurt a little cum that he eagerly licked up before giving me a nice clean up with his tongue and mouth.

Just before midnight, I rounded up my clothes and got dressed. He had to work in the morning.

Doug let me out through the garage.

"What an amazing night," he said. "I can't thank you enough." He grabbed some detailing spray and some paper towels. "I need to clean up the car. My turn to drive for the carpool."

"Better spray some air refresher," I laughed. "Otherwise your co-workers might detect the scent of hot male-male sex."

Driving home, I was amazed by how things had turned out. His automotive scenario was nothing I would have ever come up with, but I guess I was more flexible than I thought. And I never knew I had it in me to be such an exhibitionist.