Better Late Than Never Ch. 04

Sorry it took so long to complete this chapter. Of course, you won't fully understand what's going on if you haven't read the previous parts.

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Marley checked in with me just as I was finishing up my breakfast. I grabbed my coffee and settled into the recliner in the den. I knew it was a little weird, but I admit it excited me to have someone for whom I could recount my last night's experience in lurid detail.

Of course, Marley being Marley, she was especially interested in each course of the dinner and demanded a full review. It didn't surprise me that she frequently asked about the size of the portions. I'm no gourmet, and I was getting frustrated because I wanted to get to describing sex with Doug.

I rushed through a description of his ridiculous suit and vest and my frustrating attempts to get a conversation going.

I slowed down when I got to the moment I slipped into the passenger seat of his car and my eyes were drawn to his beautiful long, thick cock with that pronounced helmet head. I was so eager to lick it, suck it, and feel it filling my mouth that it's beauty didn't register at the moment. It did as I described it, and I couldn't resist bringing my hand to my hardening cock.

As I recalled the details of how I had pleasured him, I realized that beneath my lust, I had felt a sense of pride and power as my mouth and tongue made him even longer, harder, and thicker. I remembered the anxiety in his voice--"Are you going to fuck me?"when I slipped my fingers into his ass. I remembered how that had pumped my arousal to another level.

Marley only responded with a few "uh-huhs" or "Mmm" or "okays." I couldn't gauge her response.

When I described fucking his ass while he was sprawled across the leather seat of his Mercedes, I realized that while I'd been gentle and attentive to his experience at first, I'd really gotten off on pounding him like crazy. It went beyond anything I'd done with Tom.

If Marley had been in the same room, I probably would have been blushing when I relived the scene where I'd given him a lingering, teasing show in the shower. It was probably illusion, but as I remembered stroking my cock before him, my balls fully retracted, I had never felt my rod so hard and perhaps stretching to a record length.

When I described how I held his cock and spurted my cum up and down its length and frantically sucked it clean, she responded, "Um, you are so creative in the heat of passion. If it wouldn't compromise my research objectivity, I just might ... well, you know. You do have an aggressive streak. Doug liked being dominated. You really got off on giving him a show. That's an interesting development."

Her analysis didn't surprise me. The retelling had led me to a similar reflection. I filed away her "just might" in the back of brain. I was a little surprised that it went in the "If Only" folder.

"Anything regrets?"

I didn't have to think long about that. "Yeah, I would have loved to take those gorgeous seven and half inches up my ass. I would have loved to lower myself on to it, control the sensations."

"I'm sure you'll get to that," she said with a chuckle.

Damn, straight, I thought.

For some reason, I didn't mention that I'd reached out to Matt and Jerry about a possible threesome. Maybe it was because I didn't want her to argue against it, claiming I needed more experience before taking that step.

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I wasn't surprised that I hadn't heard back yet from the two guys since I'd set the message pretty late. Besides I was fixated on how Doug's big cock would feel in my ass. And, I must admit, I was imagining what sort of show I might give him this time.

Text Messages:

Me: How you feeling today, Buddy?

D: My butt's a little sore, but pleasantly so. Also, I little empty.

Me: I have a remedy for that. Are you game for another session?

D: Oh, yeah.

Me: No dinner this time. And no suit. I'll be over at 7:00 sharp. Be naked on the couch with your rod nice and hard to greet me. Don't jerk off today. Save me all your cum.

D: Sorry, the horse is already out the barn on that one. Couldn't resist jacking my meat this morning in the shower remembering watching you.

Me: LOL. I know it's a lot to ask, granted your impressive member, but try not to let the carpool see a tent in your pants as you drive them home.

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Doug had left the door open for me. I made sure to lock it before leaving the foyer.

Anticipation had me semi-hard, but the sight of him on the couch lightly stroking his beautiful cock had the tent pole in my pants rising. I don't think I mentioned that he was rather slender and he'd followed my example and shaved his pubes, cock and balls. The effect was stunning, making his length and girth even more impressive.

While I wanted nothing more than to rush forward and get my hands and mouth on that amazing cock, I walked slowly toward him, kicking off my shoes, and unclasping my belt. I let my pants drop to the floor, giving him a view of the cock stuffed pouch of my teal thong.

I slowly turned as I lifted up my shirt to give him a view of my ass cheeks split by the narrow thong strap, and before I turned back I adjusted the thong to expose the head of my cock.

I reached down to slide three fingers and my thumb over the head of his cock and lightly stroked his ridge. I reached behind his head and pulled him forward for a kiss, thrusting my tongue into his open mouth. For several moments we were heatedly sucking tongues and lips.

I stood up straight and pressed his mouth to the exposed head of my cock.

"That's it. Kiss it. Lick it. Suck it. Pull down my thong with your teeth and let it loose."

When Tom and I had fucked, neither of us had been very vocal. This was something new for me, and I found it was really turning me on.

With my cock filling his cheeks, I managed to reach behind me and grab the tube of lube. I flicked open the top and squeezed a generous supply into his hand.

"Coat your fingers and finger fuck my ass. Get me ready to ride your beautiful cock. You're going to watch every inch disappear into my ass and you're going to feel my tight warmth and the grip of my sphincter muscles. It will be so amazing, you'll hunger to blow your load deep inside me."

His tongue was lashing the head of my cock and he swirled the lube around my rim and I gripped his probing finger to resist a bit before I let him slide in.

"Two fingers," I commanded. "Press as deep as you can. Curl them up. Find my prostate with those long fingers. That's it."

His head was bobbing up and down on my cock as he sucked me hard. Man, he was really getting into cocksucking. He'd definitely picked up some of my techniques.

I pushed him away and got him to lie back on the couch with his head propped under a pillow. I tossed the back cushions to the floor to give me enough room to straddle him. Before I did so, I couldn't resist kneeling and stroking his cock, lowering my mouth to lick and suck his well-defined helmet.

It was hard to stop, but I so hungered for his length and girth filling me.

"Lube your cock for me," I said as I handed him the tube. "You're proud of that cock, aren't you? You love stroking it. After I ride you, you're going to hunger for fucking ass."

I climbed up onto the couch straddling him. I grasped his lube slick shaft and brought it to my opening. I lowered myself, loving the feeling of resistance as he took the head and first inch in.

I felt my cock lose some of its hardness as my pleasure center shifted to my ass. I lowered myself slowly, savoring every sensation, feeling his rock hard shaft scrape against my prostate.

When I had lowered myself all the way, taking him all in, I never felt so completely filled. In truth, he wasn't all that much longer than Tom. Maybe it was my imagination.

I raised up slowly. His eyes were riveted on each inch slowly appearing until I tightened my sphincter muscles to hold in his head and the last inch while I slowly twisted my hips.

"You want me to go deep again, don't you?" I teased.

"Yes, oh, yes," he replied shaking his head up and down.

"I want to be filled again, too," I moaned. "Tweak your nipples with one hand and stroke my cock with the other."

He followed my instructions as I lowered myself again, taking each delicious inch deeper into my bowels. Three or four times more I repeated the process.

Stopping again at the top, I said, "You want to thrust your hips and fuck me hard. Do it! Fill me with your cum."

What a frenzy of fucking it was. Doug thrusting up while his hand jerked my cock, and me slamming down against his thrusts. His spasms as he blasted his load deep in my rectum sent waves of pleasure through me.

When I sensed his discharge was complete, I pulled off his cock and surged forward. Taking my cock in my hand, I jerked myself hard, pointing the tip at his open mouth. I came hard, multiple spasms ripping through my cock, most of my cum spurting into his mouth but also coating his lips and chin.

I collapsed on top of him, hungrily licked the cum from his lips and face and darting my tongue into his mouth to scoop up more.

When our panting subsided, we sat back up.

"That was awesome," Doug said. "You're right. Now I'm going to hunger to fuck ass even though you did most of the fucking."

"Guess you bring out the control freak in me," I said. "Hope that's not a problem."

"No, it was beyond fantastic. But I might change over time."

"That could be interesting," I laughed. "Variety is the spice of sex."

We headed to the shower to clean up.

"Damn," Doug said, "I can't believe how much I cummed." He was running a washcloth up and down my legs.

"Resist the urge to lick it off," I warned. "The ass has its own special bacteria." The thought of a threesome again crossed my mind. What would it feel like to fuck an ass already filled with cum?

Being younger, Doug had another full erection by the time we had finished washing each other. Being older, I'd only managed a rather inconsequential semi-hardness. There was nothing I could do about it now, so I resolved not to give in to regretting I hadn't gone down this road sooner.

Doug did discover how much I loved to have my nipples tugged, licked, and sucked. The more aggressive the better. I stood behind him, pressing my cock between his ass checks and gave him a long, and, I hope, skillful hand job.

Yes, I'd loved sucking him and had stroked him a bit, but it was a new experience using my hands to pleasure that seven and a half inches of hardness. He supported himself by pressing his hands against the wall. I was plastered against him, and I almost felt as if his gorgeous meat was my own cock. He went up on tiptoes and I could feel his muscles tense as he approached orgasm. I cupped one hand to catch his load as my other hand flayed his shaft. Experiencing his excitement had brought my cock back to rock hardness and I ground it hard back and forth between his ass cheeks.

I couldn't believe how much cum he jetted into my waiting hand as he shook three, four times.

I turned him around and moved us out of the direct stream of the water. Scooping up his cum from the left hand, I brought the coated two fingers of my right to his mouth and was thrilled by how hungrily he sucked them clean. I fed him two more loads, saving a bit to coat his lips.

I pulled him into a tight embrace. I took care to suck those cum-coated lips before plunging my tongue into his mouth as I ground my hard cock against his softening shaft and drained balls.

Finally we pulled apart and gave ourselves a final wash. We were all smiles as we dried each other off and shared a few kisses.

We headed back to the living room. He had the heat set to a warmth that made clothes unnecessary.

"Right on!" I exclaimed when he brought out a pitcher of martinis that he had prepared and a couple of chilled glasses. He even had the twists of lemon that I preferred.

We clinked glasses multiple times to toast blowjobs, anal sex, tasty cum, and Mercedes' front seats. During the first two glasses and into the third, we shared a few more personal details. After all, we were basically strangers up to that point.

Of course, there had been enough spicy talk to keep up both about three-quarters hard, aided by a few casual strokes of our cocks now and then.

He put his glass down on the coffee table. He seemed a little nervous.

"I want to watch you get off," he said softly.

"Really?", I said. "Is that the best you can come with?" I chuckled, not believing he was serious. It seemed a little weird after all we had done. I wouldn't have been at all surprised if he had asked me to fuck his ass. Still, I had enjoyed giving him a show last time.

"Yeah, that's what I want. Let me make it more interesting." With that, he got up off the couch, stirred what martinis, and filled the glasses almost full. He dropped a slice of lemon peel in each. I wasn't quite sure what he was up to, but I enjoyed watching his half-erect cock sway back and forth as he moved.

"When you cum, cum in my glass. I'll cum in yours. Then will drink two very dirty martinis and drink to the art of masturbation."

Maybe he was a little drunk already, but he seemed serious. I had enough of a buzz to find the idea intriguing.

"Yeah, sort of martinis with a twist and a twisted twist. A bit perverted, but I can't wait to drink to the joys of perversion." Not the easiest thing to say after three martinis. "One more thing would make this perfect. Do you have any butt plugs?"

"Sure do," Doug replied and headed, rather unsteadily, off to get them.

I gave his ass a slap as he stumbled past me. He leaned over and spread his cheeks. I got the idea and gave his asshole a quick lick and a kiss before sending him off with another smack.

The butt plugs he brought back were on the wimpy side, but I didn't complain. We took turns lubing them and inserting them into each other. We sat back facing each other on opposite ends of couch.

Show time.

Well, I suppose the activity that had been the most consistent part of my life was masturbation. Though I would have liked a bigger one, I loved my cock and the intense pleasure it had always given me. Nothing like a long slow tease building to the moment when it demanded a hand flashing up and down the shaft until the spasming release.

Of course, I'd tried a variety of techniques over the years, but I seldom used all of them. This, however, seemed like the time to put all of them, or at least most, on display.

I made a point of keeping my eyes focused on what I was doing. When I rolled my head from side to side, I closed my eyes because I didn't want to see what he was doing.

I didn't always fondle my balls, but I started with slow easy strokes from my perineum, tracing my balls, and up the underside of my shaft. On a few strokes I let a finger on each side glide over the edges. With three fingers and a thumb, I swirled my precum over the soft pink head and brought my fingers to my mouth.

I gripped my shaft and tugged my foreskin down to fully expose the head. With my saliva-wetted index finger, I flicked my frenulum and caressed my ridge.

I stroked my shaft with the palms of both hands before I began slow stroking while making sure to continue massaging the head with the palm of my other hand.

"You're mesmerized, aren't you?" I said with a smile. "I bet you're drooling, you're so hungry for my cum."

As my stroking became more firm, I felt him move toward me on the couch. When I opened my eyes, I saw that he was holding the martini glass in anticipation of my load.

I got up on my knees and started stroking faster with a firm grip, the smooth skin of my cock sliding up and down against the firm shaft beneath. I kept my cock aimed at the glass he held. I supported myself with one hand on his shoulder, my breathing ragged, as the pleasure built and built until my cum erupted into the glass.

"Erupted" may be an overstatement. At my age, I couldn't produce the volume I could in my youth. It was a little more watery, and I had to scoop some off my shaft and flick it into the glass.

"Get me off," he begged. He put his glass on the floor and kneeled in front of it.

I got in a similar position on the other side of the glass. I pulled his face to mine and my tongue darted into his mouth and he sucked it hard. My hands reached for his gorgeous cock and I massaged the head between my palms. I reached down to his ball sack, massaging his big globes between my thumb, index and middle fingers. I slowly dragged my fingers up the silky smooth taut skin of the sides of his full erection.

Fuck, there was no denying that I was totally mesmerized by his beautiful, hard cock. So as to not risk tipping over the glass, I moved to his side and lowered my mouth to swirl my tongue over his precum slick head. I wrapped my hand around his shaft and began to stroke him.

I firmly gripped his ridge with my lips and lashed his slit with the stiffened tip of my tongue as I tightened my grip on his shaft and stroked him fast and hard. I slid the fingers of my other hand over his retracted balls and I knew he was close.

I aimed his head at the martini glass. My right hand was a blur, flashing up and down his shaft. With my left hand and reached around and rammed the butt plug in and out of his ass.

"Fuck, yes, yes," he moaned as his spasming cock shot his load into the glass. I certainly got the best of the bargain; I couldn't wait to taste the thick, creamy whiteness floating on the surface.

Before we picked up our drinks, we licked and sucked each other's cocks clean, smiling and laughing.

"Was it everything you hoped it would be?" I asked as I lifted my glass and prepared to take my first sip.

"Most definitely," he replied. "Extremely hot."

"You do know that I can't drive home after four martinis."

"I was counting on it," he replied.

As we slowly sipped our cum spiced martinis, I wondered if a cumless martini would ever taste as good to me again.

Arm in arm, we stumbled down the hall to the bedroom. I seem to recall that there was some awkward fondling, the exchange of tongues and saliva, before we both fell asleep with butt plugs still in our asses.

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I woke on my side, feeling Doug pressed against my back, his stiff rod lodged in the crack of my ass.

"Mount me again, please," he whispered in my ear. He rolled over on his back.

"Gotta take a piss first," I managed to croak. The shades were drawn, so the room was pitch black, but I managed to stumble to the bathroom and find the light switch. Pissing with an erection slowed the process down, which was frustrating, because I so hungered to be filled with his beautiful cock.

Before removing my butt plug, I stroked it in and out a few times. I grabbed the lube that he'd left next to the sink and prepared my butt hole. I put some lube on the palm of hand to ready his cock.

I shut off the light and carefully made my way to the bed. Somehow the total darkness made it more erotic. I lubed him and straddled him and used a hand to direct his shaft to my cock hungry anus.

I let out a moan as I lowered myself unto his warm, thick hardness. I gripped my thighs to steady my balance as I pressed down and slowly rose up. Being surrounded by darkness made the sensation of the smooth, thick, hard shaft filling me my only reality.

I added some rotation of my hips in addition to the up and down movement. I experimented with different angles of my back, yearning to find every iota of pleasure that gorgeous cock could give me by finding the sweet spot that maximized the pressure on my prostate.

I don't really know if I was close to a prostate orgasm, but the sensations spreading through my body were stunning. I felt dizzy, flushed; my heart was racing.