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Long time mates, First time ANAL pt.2

November 24, 2015 - A True Story by | GayMatchMaker Stories
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SO there we were best friends, having just had our first time of sucking each other's dicks. Nick and I talked about what had just happened and how awkward, funny and great the experience was.

With the porn video coming to an end, Nick asked how I was feeling. I grinned at him and told him that I was feeling great and that I was almost ready to go again. He asked me "if i really wanted to go again?" I said "yeah why not? We just had an awesome suck session and I was starting to get hard again". He smiled at me and put on another porno on the dvd player.

Nick asked me if i wanted to push it a bit further and I asked him what he had in mind. He said that i talked about sucking and FUCKING Daina earlier and that I would do anything to get my cock sucked or FUCKED and we had got the sucking part done but we hadn't got any fucking done YET!!

At this point I was a little apprehensive but we talked about it and agreed that we both wanted to fuck (each other's) arse, but we would use dingers/condoms when fucking each other. I told him about my only anal experience which I had fucked a girl in the arse about 3 years before. We both had a quick shower and got a carrot out of the fridge to use to loosen our arses up a bit, as I know that the first time it was going to be really tight.

Nick got his lube out and we gave a couple of fingers and the carrot are coating of lube - we then played with each others arses. Using 1 or 2 fingers or the carrot to loosen our buttholes. We had a bit of fun and a laugh while doing this and it was actually quite enjoyable if not a little awkward.

Once we could both get 2 fingers easily into each others arses, we decided we'd start the action again. I pushed Nick onto the floor and grabbed his cock and started wanking and sucking. It's an amazing feeling to have that cock growing in your mouth while you suck it. Nick laid back and relaxed and enjoyed me polishing his knob with my mouth. Every time I came back up to the top of his knob I could taste and feel the pre-cum leak out of his cock and was really enjoying it, even more so as Nick had started to talk dirty and I found it a real turn on. I was fondling his balls with my left hand and playing with his perineum, and he was really loving it. I then subtely shoved one of my lubed fingers up his arse. He gave a little groan and was surprised as I pushed my finger in but relaxed almost immediately, so I pushed a 2nd finger up his arse and made my way to his prostate gently rubbing and stroking it back and forward, all the while giving his cock are good lathering of spit while sucking it. An ex-girlfriend of mine, used to do this to me and she called it milking the prostate. I found it wouldn't make me cum as much but my orgasms were super intense when this was done. Nick was losing control, so I pulled my fingers out and stopped sucking his now rock hard pulsing cock. I looked at him and he was loving it, his helmet bright purple and massive staring me right in the face. I grabbed a condom and ripped open the packet, I rolled it down over his throbbing cock and gave it a quick coating of lube, as well as giving myself a little squirt around my butthole. I climbed on top of Nick and mounted his cock for the first time, gently lowering myself down slowly taking his cock into my arse. I was still very tight and found a little resistance after only a couple of inches. I tried to force myself lower but felt a little sharp pain as my arse muscle wouldn't give in so easily. I rode the top of Nick's cock for a few minutes just getting comfortable with the 2 or 3 inches I could get in and then I relaxed and my arse muscle gave way to the rest of Nick's swollen shaft. I didn't get all the way down but was taking most of his cock and riding it while watching a woman do the same thing to a guy in the porno we were watching. Nick was loving it, he kept telling me how great my arse felt and how he wanted to pump me so hard. Now that I'd relaxed and my arse had given way to Nick's member, I told him he could fuck me. I rolled off his cock and lay on my back, I lifted my legs up and grabbed hold of them and pulled them back so he had unrestricted access to my now wet and open butt. Nick stood up and pulled on his cock and looked down at me and said " Now I'm going to fuck that arse so hard". I just laughed at him and he leaned down guiding his rubber coated cock into my arse. He slowly pushed all the way in as deep as he could go - it was slightly uncomfortable and it felt like he was in my stomach. I groaned loudly and told him to pull back and go easy first. He pulled back and fucked me slowly with the first 3 inches of his cock, just taking shallow strokes and allowing me to relax his cock into me. As he fucked me it felt great and I could see pre-cum dripping out of my now semi-limp cock.

Nick was starting to get excited and I could sense that he really wanted to pound my arse. He pulled his cock out and I could feel my butthole gaping open. Nick looked at my open arse and smiled, I said to him "Well you wanted to pound me, what are you waiting for?" - He didn't need another invitation and launched his throbbing dick into my welcoming arse. He started with long and thorough strokes, taking his time but making sure I felt every single time his cock got as deep as it could. It felt amazing and I loved the feeling of his cock burying its way balls deep into my anus. Nick started to build up the pace and the force and after a few minutes was furiously pounding my arse with his weapon. I stopped him as I needed a break and my butthole needed it too.

Nick had loved fucking my arse and said that he wanted to fuck me in a few more positions but said that he would give my arse a break and let me fuck him now. My cock was limp but dripping from pre-cum that had been leaking out of it while he pumped my arse. Nick took my cock in his mouth and gave me a quick blowjob getting my cock hard and ready. I rolled a condom over my pulsing red knob and gave it a good coating of lube and lay back on the couch, ready for Nick to climb on my cock. He fingered his arse and gave his butthole a generous coating of lube before climbing up on the couch and looking down at me while he lowered his arse onto my cock. He was so tight, even tighter than the girl i had fucked in the arse, even after we had tried to loosen him up. After a few minutes of slowly and gently working his arse on to the top of my cock, he was able to relax and ride my cock slowly working my knob deeper and deeper into his anus. I was absolutely busting to start thrusting and fucking Nick's tight hole. As Nick came sliding down he squealed(I think it was a mixture of pleasure and pain) and I could feel his arse muscles clenching around my cock. He was still very tight but I was desperate to fuck his arse and give it a pounding like he had fucked my arse. Nick was starting to get used to it and was building up some speed sliding up and down my throbbing cock, but he was still very careful as he said it was too painful for him to take all of me in his arse. I told him to get up and we would try a different position.

I got him to lay on his back and rolled his legs back over his head, so his ankles were around his ears and his arse was pointing straight up in the air. In this position his butthole opened up a bit on its own and with a little more lube around his anus and along the head of my cock, I plunged my dick straight into the open hole. There was only a slight bit of resistance but I managed to push through quite easily and nearly bury my cock all the way into his tight arse, it was an amazing feeling and even Nick let out a groan of relief as he felt me deep in his arse. I gently rode him from a standing position for a short period of time to work open his butthole, just gently and easily sliding in about half of my cock for Nick to get used to me fucking him. His body was trembling as my cock kept up a steady rhythm, in and out of his arse. I then pulled out and let him lay back down and just pull his legs up. I asked him if he was ready and he said"As ready as I'll ever be, so just fuck me already!" I used a little more lube on his arse and then ploughed his now sopping hole. I started on a fairly steady fucking pace and was even stroking in nearly 3/4 of my length, Nick had finally relaxed and was now enjoying me fill his butthole with my cock. His moans and groans were getting me more hot and horny. I started to thrust quicker and harder and finally he was taking my full length, Nick's moans became louder and i asked him if he was in pain, I could barely make out the "no, just keep fucking". So I went full tilt and pumped that arse as hard and as fast as I could. Nick and I were both yelling, as I was screaming at him "Take that COCK you DIRTY SLUT!" and he was smiling at me yelling back " YEAH, fuck my ARSE, fill me with your COCK! FUCK YEAH!" It was incredible and I had to stop as I could feel I was about to cum. I told Nick that I was about to cum and pulled my cock out of his now RED and GAPING arse. We were both laughing and I said to him "ok now its my turn again!", while Nick took stock of his now open butthole prodding it with his fingers, leaking lube and arse juice.

I again sucked his now semi-limp cock to get him hard. There was now no thought of hesitation, I just gobbled down on his now bare skinned cock, his helmet covered and leaking pre-cum at an amazing rate, taking it all the way into my mouth and down my throat. I managed to withhold the gag as his cock stiffened and swelled in my mouth and throat. Nick pulled his now stiff and throbbing cock out of my mouth and I told him to fuck me from behind and I bent over on all fours opening my butt for him. Nick grabbed a little more lube and shoved his cock straight in with no hesitation, letting out a loud moan of "FUCK YEAH!" as his cock buried itself balls deep in my arse with his first stroke. "OH FUCK!" I yelled. Nick's HARD and now BARE cock was inside my arse. His rigid member had a slight bend downward in it and while fucking me from behind his cock rubbed on my prostate. I could feel the pressure with every pump and stroke he took and noticed my now semi- hard on, twitch every time he hit my prostate, pre-cum now flowing from my cock. I asked him what he was doing as we never agreed to go no rubber and he said "that we were best friends who knew what our previous sexual histories were - we both knew we were clean of any STI's" and we were already taking each others cocks in our mouths bare, what's the difference if we had them in our arses and plus he wanted to feel my cock in his arse bare too." So I agreed and let him keep fucking me. He drilled me hard and I could feel his balls slapping against my perineum and my now nearly erect cock swinging back and forward with the momentum of Nick's body as he pumped me full of his cock, We had now forgotten about the porno on the TV, which had nearly finished and I noticed the 2 guys in it emptying their loads on the girl's face and thought about what Nick and I would do when it came time for us to drain our loads. Nick suddenly pulled out and I could feel my arse gaping not wanting to return itself to the tight little hole it originally started out. I looked behind me and Nick was leaning forward to lick and rim my arse, he then spat in the hole and launched his cock back into my butt with a ferocious thrust, my body rocking and I could hear him moaning and screaming, except it took a second for me to realise it wasn't Nick screaming, it was coming from me. Nick's purple headed helmet was pounding my now gaping ARSE as hard as as fast as he could and I could hear the constant slapping of skin as he pumped away - I can't even remember what I felt, it was sensation overload, as my cock was twitching and spasming uncontrollably and my arse taking Nick's cock all the way balls deep.

It wasn't long before I felt Nick's cock twitch and his body tense up and he started screaming " FUCK!!! FUCK YEAH!!!, FUCK!! FUUUCCCKK!!!" HIS cock went rigid in my arse and twitched violently in my arse, he was shooting his cum deep, deep inside me. I don't even remember but Nick told me later I was moaning the whole time as he came inside me and he was still pumping a couple minutes after he'd dumped his load inside me, his cock still rock hard in my arse. I could feel a large wet patch below my cock from all the pre-cum I had leaked while Nick was fucking me and noticed that it was a little looser around Nick's cock in my arse. I asked him"if he had finished?" He said "no that he was still hard and was going to give me another fucking!" He flipped me over on my back, lifted my legs and proceeded to fuck me again, his cock still purple and hard, I was now struggling even though my arse was loosened as he had worked over my prostate and I think I orgasmed while he was fucking my arse. He pounded me hard for another couple of minutes my butthole starting to feel sore, working his way to climax and he pulled his twitching cock out and fed it into my mouth, shooting two small loads into my mouth and fucking the cum into my throat. I was done and needed a rest. Nick was exhausted and lay back on the couch with his now limp cock, wet from my arse and his cum. We both needed a breather. I knew what to do and lay on the couch across from Nick, I showed him my full arse and spread my legs so he could get a good view of his baby batter leaking out of my arse. I felt his cum leak out of my butthole and slowly leak down my arse, Nick loved it and I could see him starting to play with himself again. I tried to tighten my butt and force some more cum out and I cumfarted and it spurted out and more poured out flowing down my crack. Nick got up and wiped his limp dick around my bum trying to get as much cum as possible on his cock, he then leaned over me and told me to "Eat it! Eat the cum off my dick!" I thought what the hell, I'd already gone this far and taken his cock in my arse, and a load in my mouth, a little more cum off his limp dick wouldn't make much difference. So I took his limp cock dripping with his cum from my arse, and put it in my mouth again and sucked and licked it all over. He twitched a few times as I polished his helmet with my tongue and he got back a semi hardon. I released his now clean cock and spat his cum out of my mouth and down my chin. Nick was grinning from ear to ear. He then said "You're a dirty cumslut" and laughed, before leaning over me and starting to suck on my cock. He looked back at me after a few sucks and said " now lets see how much cum we can drain from your cock?" He worked my cock in and out of his mouth focusing mostly on my knob, once it had swollen and hard, he stopped sucking and got down on all 4's and spread his arse cheeks with both hands. His arsehole had nearly returned to normal, so I took a little lube and shoved 2 of my fingers into his butt, his arsehole immediately gave way. I spat on my cock, my saliva mixed with some of NIck's cum still in my mouth. I rubbed my helmet and slowly fed it into his hungry arse. I pushed all the way till I couldn't go any further and I heard Nick groan loudly. I grabbed his hips and started to slowly pump in and out the full length of my 7 inch cock. He was groaning everytime I pumped in to the hilt. After a couple of minutes I pulled out all the way and looked at his now gaping butthole, he turned and said "What's wrong?" I smiled back at him and said "Nothing. Now I'm going to punish your arse!"
I spat in his butt and ploughed my cock into his welcoming hole. He shuddered, I started to ramp up my fucking, harder and faster, full length strokes, almost pulling out entirely before ramming my entire length all the way into his arse. He was no longer groaning but giving out little whimpers everytime I pounded his hole. I was really using his hips to pull his arse back onto my throbbing cock while I was thrusting forward. His face was now buried down into the carpet, his butthole now sticking up in the air and giving me a new angle to fuck him from. I shoved my pulsating knob into his gaping butt and fucked him as hard and as fast as i could. His moans, groans and yelling were muffled by the carpet. I could still hear him "Yeah, fuck my arse" he was yelling back at me repeating over and over . I could feel my orgasm coming on and my cock was ready to burst. I pumped as hard as I could and yelled back at Nick " I'm cumming. FUCK, I'm cumming in your ARSE!" and with that I could feel my cock unleash my hot cum deep inside Nick's butthole. I just kept pumping and I could feel my cock ejaculating more of my man seed inside him - 2, 3, 4, 5, 6, 7, 8 ..... I'd started to lose count of the strokes and each one felt like I was unleashing more cum. I was still fucking his arse furiously a few minutes later, even though I'd stopped cumming by now. Nick's arse was hot, wet and sloppy. We were both groaning now and I slowly pulled my still hard dick out of his jizz filled hole, leaving a thin trail of cum leaking out of his butt and down his crack. I lay back on the couch, sweat pouring off me and I told Nick "I'm done!" He looked at me seriously and said " Not yet. I need to get this cum out of my arse." He climbed on the couch and stood above me, 1 hand holding his butthole. Nick told me to hold my still stiff cock up towards him and then turned around and lowered his sloppy arse down onto my knob. He slowly fucked himself on the top few inches of my knob. I was bucking violently as my cock was extremely sensitive after blowing my load earlier, Nick was riding me reverse cowboy and he was loving every second of it - he stopped and looked over his shoulder at me and then lowered himself all the way down taking the entire length of my cock again and then grinding his arse into my pelvis. If I had any more cum left in me I would have blown it right then and there but I was completely empty, it didn't stop me from having an orgasm though and I felt my prostate going crazy and twitching madly. It was FUCKING awesome!!! After a minute Nick stopped and grabbed each of his butt cheeks and spread his arse while he lifted himself off my rigid, twitching cock. I could see as he lifted off, my cock was coated in my cum and as he completely lifted off, his gaping arse emptied the rest of my cum. It was like a mini flood - my knob was coated from tip to base in my pearly man juice, with cum matting my pubic hair all around my cock, and pooling in my belly button and creases of my stomach. I also felt a lot of cum run down my balls and between my crack. Nick looked at me and laughed "That was a MASSIVE load!". He said through a grin, "Now I just need to clean you up and we're done", and with that he grabbed my sloppy cock and took it in his mouth, licking and sucking his way down my shaft. I smiled back at him and said "go for it" and let him do his thing He even licked up the cum on my stomach and followed the trail of juice down by scrotum and balls and into my crack.

After a few minutes - Nick asked me how I was? I said tired but good. We started talking and discussed in length and detail what just happened. We both agreed that tonight was just about us, 2 horny guys desperate for a root(with a girl) that didn't happen and just helped each other have a fun and enjoyable night of sex. We pushed our boundaries further than either of us thought we'd ever go but neither of us regretted it, actually we both enjoyed it immensely. Neither of us was attracted to the other in any way, we just used each other for sex and to get off. But we said that we probably weren't hetero guys anymore but more likely bisexual, as not only did we have sex with another man and enjoy it but we both said that we would probably do it again(and we did a lot sooner that we thought we would). We agreed that we would be fuck buddies but we would have to keep it discrete and we would still both go out looking for women, but if we were on a rough patch as both of us had been prior to tonight, then we could essentially call on the other for a suck and/or fuck session. We also used this agreement a lot over the following 2 years.

We both crashed out early in the morning, I slept on the cum soaked couch and Nick went back to his bed. Knowing Nick for so long and having been best mates allowed me to trust him enough to not only suck his dick and let him fuck my arse, but to bareback me as well. I suppose the friendship and trust we had for each other allowed us to go where not many best mates would go(into each others bare arses!).

We woke about lunchtime and we both got cleaned up and had showers - Nick's living room smelled like sex from the night before. I told Nick I would catch up with him later that night as we were supposed to go to the footy and catch up with some mates for drinks and left his place satisfied, with a smile on my face, an empty ball sack and a long limp dick!!!!

What happened to Daina? I hear you bi-guys ask.... Well she did contact us later that day, but that's another story.......

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