My second encounter with Jim Pt. 02

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Jim and I start getting down to business.
5.5k words
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Part 2 of the 2 part series

Updated 06/09/2023
Created 04/27/2020
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I kept my room cold, so the first thing I did was turn the thermostat from 64 to 70 degrees.

"How do you like your whiskey?"

"Rocks and a splash of water, please."

I made the drinks and handed him his. I told him to give me a second, then walked to the bathroom and grabbed two towels.

"Here you go." I tossed him the towel. He looked a bit surprised as I stripped my wet clothes off and put the towel around me. "I had less on yesterday," I said jokingly.

Mark followed suit and hung his wet shorts and shirt over the back of the couch. He sat back down in his towel. We were sitting across from each other, leaning back, both of us with our legs spread enough so that we could see each other's cocks. He smiled. "Doesn't smell as cummy in here as I thought it would after last night."

"The maids do a good job, but at this point they must think am some kind of pervert, with all the cum soaked washcloths they pick up daily, and now the spots on the floor."

We both were staring at each other's crotches. As soon as my cock started slowly swelling in anticipation, Mark's cock started to grow too, which only hastened the blood flowing to mine. Within a short time, both our cocks were rock hard, jutting out through our towels.

"Well, I really didn't expect to be in this situation today. I planned on jerking off and staying in," Mark said.

I told him I wasn't sure either, but part of me wanted it to happen again.

He said it was a bit weird, since normally it's a dimly lit room, and you hardly see each other. I agreed that was is a bit odd, but grabbed my laptop, sat it on the coffee table, and sat next to him.

"Here's what almost made me blow my load earlier."

I clicked on the tab titled "Bi Married Fuck Buddies." restarted the video from the beginning, then clicked Full Screen. Mark leaned forward a little bit and stared intently. The two guys on the screen were in a sixty-nine position, their wedding rings clearly visible. Shortly after the guy on top moved down and sucked on the cock and balls of the other. Then, in an instant, he pushed his legs up and shoved his face and tongue into the other guy's hole. I heard Mark say "fuck yeah" under his breath and I noticed that he was breathing a little heavier too.

Since I'd seen it, I knew what was going to happen, but I still loved every second of it. I leaned back further and started slowly stroking myself. I noticed Mark fondling his balls a little while also massaging his hole with his finger.

Mark was really getting into the video, quietly coaching the guy like he was in the room with him.

"Yeah man, shove that tongue in there, tongue fuck that ass. Swallow that cock, man up and push your face into his crotch, let him fuck your throat."

There was a slight break in the action as the guy who was sucking cock and eating ass stood up and turned around, positioning himself over the other man's stiff rod. Mark came out of his mesmerized state and looked at me stroking my cock. Before I could say anything he was between my legs licking my shaft and working it with his mouth. I moved forward, pushing my hips out towards the edge of the couch so Mark could get a better angle to on my cock. I took a sip of my drink and leaned back, enjoying a nice buzz and a masterful blow job.

After a couple of minutes he said, "Let's get some more room," stood up, and moved toward the bed. His cock was so hard it seemed glued upright to his stomach. I took the laptop over to the TV in front of the bed and plugged it into the TV. Suddenly the screen was filled with a giant cock wearing out another man's ass, and the room was filled with the sound of panting and moaning emanating from the TV. I grabbed the remote to quickly turn it down so the neighboring rooms wouldn't get an earful of man-on-man sex.

Mark was at the foot of the bed on his knees, so I laid on the bed so his head was between my legs. As soon as I was in position he attacked my cock with his mouth, holding it as deep as he could until he almost gagged, then coming up for air before diving back on it. After a few rounds of what felt like him trying to suck it free of my body, he caught me off guard, throwing my legs back toward my head and diving tongue first into my ass. I wasn't sure what to think at first, but after the initial shock was gone, it felt good, really good. My head was spinning. Was he going to try and fuck me this time? I wasn't sure about that, but right now it felt like heaven. I could tell he was getting a bit tired of holding my legs back, so I moved up the bed and rolled onto my stomach, reaching back and pulling my ass apart. I could feel all of his spit dripping down my crack. I couldn't see anything since I was face down, but I heard Mark get off the floor and felt his presence above my ass. Not knowing what was going to happen, I decided I'd go with it. I was bigger than him, so I figure if he tried to hard fuck me, I could man handle him off of me. But at the same time I decided, since the tongue lashing he gave my hole felt so good, if he went slow, I'd try getting fucked for the first time.

I felt his hands spread my cheeks even further apart, then jumped a little in anticipation of a cock being pressed against my hole, which I supposed showed me that my virgin hole wasn't going to be as willing to surrender as I would hope it would. However, it wasn't his cock, it was his tongue again. This time he gently licked me from my balls up past my tightly puckered hole. It felt euphoric, though admittedly I was a little disappointed that it wasn't the tip of his hard cock pressing into me, since I had mentally prepared for it. I was lost in a world of pure pleasure, only to be brought back by him getting me to roll on my back.

Before I even got fully rolled over his hand was around the base of my shaft, standing it up straight, so he could lick the tip, in an attempt to savor any precum he could get. Then he went back to pushing his face down into my crotch and with his mouth agape, slamming my cock into his throat. It felt weird--different than the blowjob he had been giving before. There wasn't any sucking this time. His mouth wasn't closed around my cock, there was no feeling the warmth from the inside of his cheeks sliding up and down as it went in and out of his mouth. This time I really only felt the head of my dick punching against the back of his throat. It didn't feel great, but it didn't feel bad either; I just remember copious amounts of spit and slobber coating my shaft and running down into my crotch and onto the bed. At the same time, I could see his ass in the air writhing up and down, using his free hand to furiously finger himself. After a short while the purpose of the odd blow job became clear.

I don't think my cock is big. It's average length, I guess, six inches long, but thick. The mushroom tip is the thinnest part, after the head, it starts expanding the further down the shaft you go, until at three quarters of the way down it's at its thickest and stays that thick all way to the bottom. The first time we fucked, we used a couple bottles of the hotel lotion to really lube him up, and it still seemed a bit tough for him to take at the start.

So, after thirty seconds of a rough and sloppy throat fucking, Mark sat up and said, "I need it and I need it bad."

He turned around and faced the foot of the bed, positioned his ass over the top of my hips, grabs my cock, stands it up, lowers his hips just enough so the tip is pressed against his tight little hole, which now has been slightly opened due to his self-fingering. Without warning he slammed himself down, forcing the full girth of my cock deep and stretching his hole open all at once.

Mark had surprised me again. I was in a bit of shock over what he just did to himself. While it seemed all the spit was enough lube to ensure he didn't rip himself in half, I know he had to have felt some pain from the force at which he took my rock-solid cock deep in one quick go. The instant his hips bottomed out against my crotch, he let out a loud low bellow. It sounded like someone had punched him in the gut and knocked the wind out of him. There was silence, and Mark was still for what felt like an eternity, though I'm sure it was only a second or two. Then he said, "FUCKKKK, O MY GOD!"

He panted a little bit and then started sliding back and forth against my hips. My cock was still buried deep inside of him, and very little was sliding out as he gyrated his hips back and forth. I felt it inside of him being pushed forward toward his belly as he shifted forward, and then slapping backwards towards his spine as he slid his hips back towards my chest. The tip of my cock swung back and forth like an upside-down pendulum, slapping hard against his prostate with every rotation. Each time it pressed up against it, he moaned a little louder. Soon he started to pick up speed. I could feel his entire body tighten and his hole grip my cock like a vise. I felt him tighten around my dick internally, his hip much shorter now. I felt his prostate pressed hard against my shaft. Each little hip slide moved it up and down against the bump of my mushroom tip. Then his movements stopped, his body twitched, and everything loosened up.

The first thing I thought was, "Fuck, he just came and now he's going to leave and I'm going to be stuck jerking myself off." But after a few seconds, he slowly stood up. My cock slid out of his ass, sprang back and slapped against my belly.

Looking at the TV he said, "Restart that fucking video, that shit has gotten me so hot, keep it going."

"Didn't you cum?"

"I've never felt that before. You were hitting my prostate just right, it's the hardest I've ever cum, and it happened a couple times, the last one was crazy for me, but I never dumped my load."

I got up to restart the video. He lay on the bed on his belly, head up so he could watch.

"Skip to where they just start fucking, that one scene where you can see them both wearing their rings as the one dude gets his ass pounded."

I got to the spot he was talking about and started the video a little before, so I could get back in time to see the scene start, with the one guy pushing his cock into the other guy for the first time. I looked back at Mark. His legs were together, but he reached back and pulled his ass apart.

"Your turn to do some work. My legs are jelly right now."

I got on the bed and straddled him, his legs between mine, my hips right below his pulled apart ass, in a position that looked like I was about to give him a back massage. I looked down, expecting to see his ass all torn up, but to my surprise, the little gape that was there earlier had closed up. I moved forward a little bit more, pushing the tip of my cock down and against his hole.

"You good to go?"

Without skipping a beat he said, "Fuck me like a man."

As if punctuating his sentence with an exclamation point, I thrust my cock forward with all the weight I could. Since this was my first time in this position, my cock was a little low and I pushed it hard against his ass. It slid up and slammed into him. He let out a little yelp and tried to move forward, but it was too late. There was a little bit of resistance to start, but nothing like the first time, and as soon as I was embedded in his gut, he let his cheeks go and grabbed the bed, pushing himself back, in part to keep himself from falling off the bed, but also to get my cock as deep as he could.

As I mentioned before, I'm thick but average in length. Though Mark didn't have a bubble butt, once we started into a rhythm, my cock would slide all the way out and then only get a few inches deep before sliding back out. Don't get me wrong, it felt fantastic. The tip of my cock was sensitive, and as it popped out of his ass then back in it was pushing me to the edge. I wasn't ready for the sinning and debauchery to end for the night.

On one of my thrusts I paused and said, "Hey, we gotta swap positions."

Mark laughed and said, "My ass getting too loose from you popping it open with each push?"

"No, it feels too good having just the tip pop in and out. I'm gonna cum quick if that keeps up, and I'm not ready to be done."

I told him to get on his back with his head to one side and his legs pulled back as far as they would go. Well, Mark wasn't as flexible as those tiny little things in porn, but he did what I told him to, which pulled his ass up off the bed and his hips a little forward" the perfect position for me to lie on him and use all of my body weight to push the full length of my cock deep into him, without any cushion from his ass in the way.

He lay there, holding his legs back, eyes fixated on the two guys still going at it on the screen, and like a blacksmith slamming his hammer down into a piece of hot steel sitting on an anvil, I dropped down with my full weight, piercing him with the full length of my cock as deep as I could get it. Damn it felt so good, the warmth of his body around my entire shaft again. He let go of his legs and gasped while trying to yell "Fuck," but since he was breathing in it barely came out as a whisper. It was too late for him to save himself. His eyes were wide and his hands clenched the bed so hard they were turning white. Before he could get any other words out, I had already raised my hips up so all but the tip of my cock had slid out of him. At that brief moment his expression changed from panicked to resolved, and I slammed down again.

I don't know what happened to me. Everything felt so good! At that moment I had no concerns for the outside world. We could have had a gallery of friends and family watching in horror, we could have been on top of the pulpit with my entire church congregation watching me sodomize another married man. Nothing would have stopped me. I was a primal beast. Years of pent-up sexual frustration were being released with each thrust. The harder and deeper I went, the faster they disappeared. Mark's gut was my therapist. My body burned with the need to pound Mark's ass. I was insatiable.

Mark's eyes were closed tightly, and either watering or crying a little bit from the punishment he was subjecting himself to, though it seemed he had regained enough composure to grab his legs again and keep them pulled back. He was making certain that his hole was exactly where it needed to be in order for me to bottom him out with my cock each time. I stared at him intently, waiting for any signs of surrender, but by the fifth or sixth thrust, the water from his eyes rolling down his face, jaw clenched, lips pursed, he started making moaning sounds each time my body dropped. My cock invaded his ass over and over, only to retreat and mount a new charge.

He was moaning louder, and I was starting to breathe heavier trying to keep up the pace. My body was on fire. Droplets of sweat began to grow on my brow, and I felt some roll down my back. I didn't want it to stop, but I was betrayed by my arms. I could no longer hold myself up. I came crashing down in one final thrust, causing Mark to lose his grip on his legs. We ended with his ass still in the air, my cock buried inside, his legs wrapped around my back, face to face, panting like dogs after a long run. After catching my breath, I rolled off of Mark and laid on my back. It felt a little uncomfortable laying together, but we were both still trying to regain a bit of energy. As I relaxed I could feel my cock losing a little bit of its rock hardness. I reached down and started slowly stroking my shaft up and down to ensure I didn't go limp. Mark had regained his composure, and I guess he noticed I was playing with myself. He positioned himself between my legs again, his face in my crotch. He pushed my hand away and slowly started stroking me as he took my balls into his mouth, massaging each one in turn with his tongue. It was a welcome reprieve from feeling them slammed hard against his ass.

After a minute, he slowly moved his head back and let them dribble out of his mouth. Then he moved forward far enough to lick the precum off the tip of my cock, before gently sliding it into his mouth. The sensation of his mouth enveloping me made it feel as if it had healing properties. Partly it was due to the change of pace and Mark doing the work so I could recover, but what also made it so good was it being my first ass to mouth ever. I've been with some freaky girls, and not a single one of them would ever do that. But here he was, just going for it. I'd just rammed my cock up this guy's gut for the last forty minutes, and as soon as I took a break he was face down in my crotch without a second thought.

I reached between Mark's legs to start stroking him off too, figuring he still had an aching boner, but he doesn't. He was limp and dribbling long sticky strings of precum. I looked at him, my cock filling his mouth.

"Hey man, did you cum?"

"No, after you started jackhammering my ass like you were working to fix potholes, I went limp."

My first thought is that I somehow fucked him up internally. "Did I break you, can you still get off tonight?"

He pulled his head off my cock again. "No, though this is the first time this has happened to me. Each time your cock rearranged my insides it nailed my prostate. Next thing I know it's like orgasm waves rolling over me, totally different than when I blow a load, but fucking awesome! Then my cock went soft and just started pouring precum. Didn't really care at that point though, I just wanted to keep getting hammered."

I told him to hold on, got up and started the video again, just before the point the two guys start fucking, then pulled a chair from the other room and put it in front of the screen.

"You've gotten yours a bunch, it's my turn. Bend over the chair." Mark got up, repositioned the chair so he could see the TV a bit better, then knelt in the chair, leaning over the back a little, and spread his ass as wide as he could. His hole was red and looked like it had taken a pounding, but as I walked up stroking my cock, I saw it slowly trying to close to its original tightness.

I positioned myself behind Mark and rubbed the tip of my cock up and down his ass, each time circling around his broken hole. I smirked, knowing that I was about to mercilessly ruin its futile attempt to get back to its normal state. I looked up to see the two guys in the video were finishing the blowjob/rimming scene and about to get down to business. I wanted to time this right, so I started at the same time the guys in the video. Mark figured this out pretty quick, he didn't say anything as I teased his ass, he just watched the video as I did my thing. As the first guy stood up and straddled the one sitting down, about to impale himself with the other man's cock, I leaned forward and in a low tone said, "it's time to get what we are both here for."

I slowly slid my cock into Mark at the same time as the men on screen, my thrusts matching their speed and depth, deeper and deeper, until our onscreen friend had his buddy's cock entire buried in him, as mine was completely buried in Mark's ass. The two guys on the video had some experience apparently, because they started going at it pretty hard fairly quickly after that. But Mark's ass was loose now, so it was no issue to keep up with them.

Doggy style is my favorite position and this was pretty much it. My arms were long enough to reach forward and grab Mark by the shoulders while still standing almost upright. This allowed me to swing my hips forward with all my might, while also pulling a him back towards me at the same time, giving me the same deep penetration as earlier in the night, but at a quicker pace and with a harder thrust.

Looking down, I enjoyed the sight of my cock sliding in and out of Mark. I start to get lost in watching it. His ass lips were stretched down around my cock a bit as I pulled it out, then inverted as I thrust forward. For some odd reason I found it enjoyable to watch. It reminded me of a porn where a woman with large labia is getting fucked, her pussy lips wrapped around the guy's cock as he pulls back, then folded in as he pushes in deep. I was mesmerized, enjoying the feeling of Mark's ass and finally being able to watch what my cock was doing to it, when I realized Mark had started rhythmically moaning to my thrusts again. I stopped admiring the handy work of my cock and got back in the moment. Hearing his moans each time I thrust forward brought back that urge—I wanted to fuck him harder.

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