Not So Anonymous Hook-Up

by Late Night Charlie

5 Jan 2023 3333 readers Score 9.0 (63 votes) PDF Mobi ePub Txt


I was at home enjoying the first day off for Christmas Holidays from work for a couple weeks. I was taking it easy and relaxing from working like a dog for a couple months. While tinkering in the garage drinking a beer, I had a sudden urge to have a hook up with another guy. I'm 29, 5'11, stalky but firm build, pretty relaxed and outgoing. Having sex with both girls and guys is fun, I just enjoy sex. I'm a masculine closet bi guy however that enjoys bottoming, we'll call me Bob. Anyways, I hit up the Ol' Grindr and started browsing. Took a while and a couple flakes of course, about 6 hours later I found someone that was going to come over. He was 35, white, 5'7" stalky build, masculine guy also. He lived in a town I used to live and grew up in. We didn't share names, face pics, or any backgrounds. Time was set, a top was on the way and I had 25 minutes to prep. While I was in the shower I started wondering who this person was. Lived in my old town, about the same size and description of someone I knew, and double checking his age, he was also 35. I started thinking, damn I might know this guy. This hasn't happened before, and I was actually kind of looking forward to it unfolding if it was who I thought it was. Worst case he leaves in a panic, but the cats outta the bag already, I wouldn't say anything anyways. Or he'd be just as surprised as I am and we roll with it. It would be simply a true FWB's.

30 minutes went by, I was ready to fuck and excited to see who was going to roll up any minute now. I was on edge, and getting antsy. I had a quick little bump of the Columbian Bam Bam and slammed a beer. Nerves got settled just in time as a familiar vehicle came around the corner into my driveway. I laughed in disbelief but still not convinced it was him yet.. Well I believed it 15 seconds later when buddy who we will call, Rick for anonymity to everyone else that may be reading, stepped out of the SUV. I was nervous about this and looking forward to it, I've never fooled around with anyone I knew and grew up with. He didn't know who I was since he didn't know where I moved to, it's been a few years since we seen each other. Rick walked up to the door, as I opened it Rick looked up and said "Holy shit, Bob. I wasn't expecting to know you and I'm not sure what to do right now. I hoped this would never happen!"

I was quick to respond and calm the situation as I was feeling pretty good eh, and already solved the puzzle. As I laughed and said, "I knew it was you! I had a feeling after we talked and you were headed over."

Rick replied with a bamboozled look, "Why didn't you call it off then?"

Bob, "I figured screw it, see what happens and maybe have a real discrete FWB with an actual old friend?"

Rick, "This is fucked, what now?"

I gave him a big spiel to not sweat it, we're both discrete and in secret. We know each others secret now. Might as well go for it. Rick thought about it and wound up coming in. Rick was on edge and this wasn't going to go well at all if he didn't wind down a bit. So naturally a Degen like myself grabbed two beers from the fridge and a little plate from the cupboard and set it on the counter. Figured take a gamble, why not. He either does the recreationals or doesn't, I was going to anyways ;). He looked at the plate then cracked a beer and looked relieved. We drank a couple beers, did a couple drag strips and caught up. I'll skip over all that yada yada yada.

We wound up in the living room downstairs watching tv and still having beers. Rick was just getting into this game he mentioned this was his 4th time topping, and did some sucking stuff a couple times. I, on the other hand was a healthy and careful (It's True) bottom that lost my butt cherry when I was 22 and I've been doing this off and on since. Trying to stay with the same cocks eh. We are both clean bills of health and know where each other lives now, so RawDog she is. 

We finished our beers and got up off the couches. I went up to Rick as he set his hat and sunglasses on the end table. I pulled his shirt up over his head and tossed it. I went down on my knees and unbuckled his belt and button and slid his jeans down as he kicked them off. I was already hard as a rock in my jeans with a jock on. Jocks are great. I seen Rick was excited and ready to go, he was raging in his grey boxers with a spot of wetness at the tip. I pulled his boxers down slowly over his cock until.. Spring, Yahtzee! Rick was packin heat with probably an 8" GIRTHY, smooth, straight with a slight up curve Uncut microphone. I love uncut dicks, something different than mine.

I looked up at Rick's eyes as he said, "I was blessed, is that going to be alright?"

Moving my sights back on his hog pointing in my face, excited that he was a possible well-endowed FWB. I uttered lowdly, "It's not that big." Pfft, it was actually a sledge hammer. 

I took his huge cock in my hand and wrapped my lips around that fatty's head and started slurpin'. Sucking on the head for a bit, pulling his hood back and fourth with each motion. I started going down on that lockness monster as my hands went down to undo my jeans and pull my luxurious sport utility 6" cut dick out. It wasn't massive but I had a nice dick, just looked clean I tell ya. Nothing in size compared to this air craft carrier I was pathetically sucking. I was trying to get it all but no chance. I can't deep throat fuck all, especially something like that. Truth be told I could do without sucking dick, but it's the best way to get the ball rollin' towards the dick in butt part! So, I will always do it. I gagged a few times and Rick, that prick figured I could take more!! He grabbed my head and rammed that thing as far as my skull would allow repeatedly, until I gagged and pulled away dry heaving. Rick was laughing his ass off. "No More", I said. It's go time. I stood up and pulled my shirt off and removed my pants and wound up pulling the jock off. Rick went down on me for a couple minutes slobbering on my dick as he mentioned how nice of a dick it is (Told You). Rick stood back up and it was almost go time!

I walked over to the end table where I placed the lube and the plate of goodies. Firstly, laid out two treasure trails for the boys, then I grabbed the lube and told Rick to rip his first. As he went to do his bump, I was lubing up his cock and handsomely applying lube to my hole and pushing it in each time until I felt as moist as the amazon rainforest back there. Rick grabbed another beer and backed away from the table. I moved in to rip mine. Before that, I bent over with my fore arms on the table, straw in one hand, spread my legs, arched my back and pushed my ass out to Rick's Directional Drilling Ditch Witch. Rick pressed his fat head against my hole and rubbed up and down slowly slightly pressing hard every time he glided over my hole. Rick asked if I was ready, in turn I replied, "Oh Fuck Yeah Bud, might as well slip it in there!". Rick started pressing his monster head into my ass, very slowly. I'm fairly experienced as a bottom but that thing was thick! I told him to keep slowly pressing on, there was some pain for sure but momma never raised a pussy. Right when he head was about to bust through the seal, I ripped a massive line and he was through the blast door. The pain was subsiding as he slowly kept creeping in. I could feel every single bit of that dick reorganizing my guts. As the base of his cock approached my ass, I pushed back against him slowly, until I could feel his pelvis pressed against my ass. It felt so hot in the room, Rick's massive balls were sagged down so far when he pushed me forward on the table to rest himself on my back, his balls cradled around my own balls. At this point, my dick was soft as baby shit, perfect. That means the top is doing great in my eyes.

I did one more rip and pushed my self up. Rick started sliding his cock back out slowly halfway, back in halfway, out and in, out and in halfway. My ass was adjusting to his dick nicely. I was feeling great. After a couple minutes, he was able to pull all the way out and go back in. Rick's fat cock stayed in my ass and started slowly thrust, he was horned up and said he won't be able to last long.

Rick, "Man, I love your ass. It grips and handles my cock like a champ!"

Me, "Fuck man, I haven't been fucked by a cock this long and girthy, it fuckin hurt but I can't get of your colossal cock man!" Few pumps later with Rick's balls clapping my cheeks, my balls and cock went full retreat up inside me like I jumped in ice water, but pre cum was drooling down my soft cock.

Me, speaking with heavy overwhelmed breathing and my voice was bouncing up and with each thrust, "Man, I've seen your cock in the showers when we played hockey, but I never realized how much you were packing. I just knew it trumped my prick and fantasized about it not going to lie. I discretely checked everyone's cocks out when I could. I can't believe your cock is inside me right now, your cock feels AMAZING!!" 

"Man, I've fantasized about fucking your ass after showers. You were the only guy that would drop your towel and bend over to put on underwear with your ass and balls full view. I couldn't be the only guy in there that had thoughts of fucking this ass!" Ricks word were course and winded and cutting short. "Fuck, your ass is so fucking good! You love my cock wrecking your cock loving ass!?"

Me, "Fuck yes, fuck my ass, this is your ass! I want you to breed me! Fuck my ass Rick!"

Rick was full length jack rabbit fucking my horny gay asshole like no tomorrow. My hands were pushing my shoulders up as Rick was pushing with everything he had on my back. I felt arched like the cables on golden gate bridge! I've never been fucked my a cock this big, and couldn't get enough. Couldn't believe a friend I grew up had secrets like I do and is re-arranging my guts right now! The moment was unbelievable. I wasn't even hard but I was on the edge of cumming. Every thrust from Rick's Reamer pushed me closer and closer. Rick was getting close, he was starting to stammer and slow down.

"I'm so close man. I'm going to unload every drop deep in your pussy!" As Rick was leaned over me talking in my ear.

"Fuck YES, put a baby in me Rick, I fucking want you to fill my ass right up!" Speaking as I was all twisted looking back and arched.

"I want to look into your eye's as dump my load in your hole!" As Rick pulled my upper body up off the end table and slid his fat soaking, throbbing cock out. I leaned down and ripped one more dump. Rick told me to lay back on my pool table, put my legs up and spread wide and wait for his cock. I did what he said, I was all in for being a submissive bottom slut at this point. Rick, hammered one more rail and shot gunned a beer all in a matter a minute and walked towards me with his ragger bouncing up and down. My ass was spread wide and begging for Rick's cock. I was so close to cumming.

Rick grabbed my thighs and pulled in to his cock. His fat leaking cock rubbed my hole teasing me. 

"Fuck my hole man!" As I waited laying on the pool table.

Rick's cock slid into my ass with haste, steady hard thrusting followed.

"I'm gonna fucking cum dude! Your ass is so fuckin hot!" Rick said with a coarse winded voice after giving a viscous pounding for 5 minutes.

"Fill my hole man, I fucking want it so bad!" Looking up at Rick with my hands behind my head.

Rick pushed my knees up to my head and let out a ferocious groan. He was blowing his hot heavy load into my ass. With every quick thrust I could feel his warm cum filling me more and more. We were both in another world. I felt Rick's cum dripping out of my ass and he kept his still hard cock balls deep in my hole. I could tell he could barely stand his legs were so tired. He unleashed a can Campbell's Cum into my hole and I couldn't keep it in. There was so much it started dripping on the floor. I was shaking and my mind was rushing. Rick leaned down and laid his head on my chest, still inside me and starting to get softer. He pushed himself up and started rubbing my soft dripping cock. He insisted after I told him he doesn't have to. My cock instantly got a rise and got hard, I was pretty much at the point of coming already. My purple head swelled up and my load blew out of my cock like a hydrant. One initial heavy stream that got my nose all the down to my pelvis. With countless spurts to follow. My whole body was shaking. 

We were in the position for a while, breathing heavy and not saying a word looking at each other. Rick's cum soaked cock slid out of my hole dripping wet. My ass felt empty, stretched, wet, and satisfied! That was the best fuck I've had, by the looks of Rick, him also. We got cleaned up and chilled for a bit having a beer, then Rick left. 

We are going to meet again... Hopefully sooner than later.  

by Late Night Charlie

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