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My first time For me my first time going bareback was also my first time taking anal. Back in 2011 I joined Fabguys.com, after being on there for about 6 months I had met with a few guys and sucked them off but it never lead to anything more, in fact most of them were just one time meets; that was until I met Steve, Steve was in his early 50's, nice face, about 6 foot tall, hairy, and built like a bear with a muscle gut, to top it all off he had a great cock, it was about 7" long, uncut, and had a real nice thick girth, that kind of girth where you can wrap your hand around it and your fingers and thumb don't quite touch. For about 3 months we would meet almost every weekend for a few hours at a time, hang out, watch a film or rugby etc; during which I would blow him 2-3 times, he often offered to suck me but most of the time it was satisfying enough for me to just swallow his loads. On this occasion though we had been sexting each other all morning and were both horny, as soon as Steve turned up I took him straight my bedroom where we stripped down. As we stood there kissing I stroked him to half mast and then slid down on to my knees where I continued to stroke him while sucking on his balls, I could hear his deep grunts of enjoyment when he suddenly spoke "I see you already started without me today" I glanced around and there it was sitting on my bedside table, a small pink vibrator I sometimes used while jerking off, sitting right next to a tube of KY, I could feel my face turn bright red burning with embarrassment, considering I had a mouth full of balls, I didn't know what to say so, I just looked up at him with a guilty stare and began to suck on his cock, to my surprise though he pulled away. "get up on the bed and show me your arse" I was still reeling from the embarrasment but did as he asked, I laid on my front with my legs spread and my ass raised a little at the edge of the bed. His massive hands and thick digits traced down my back to my ass cheeks, slowly spreading them apart to get a better view of my pucker, "Mmm nice, not seen much use" up until that point my ass had never seen any use other than that little vibrator, I felt his finger give a gentle prod to my ring, then a quick spread with 2 fingers and finally he licked his thumb and then began to work it in to my hole, all I could do was lie there while little gasps and moans escaped. "Want me to keep going?" My head was spinning with pleasure, I didn't know what to say or how to answer, that's when I felt it, he dragged his engorged fat cock head over my hole and gave a couple of teasing pushes, I knew right then what I wanted, without saying a word I leaned over and grabbed the KY off the bedside and handed it back to him, Steve took that as my answer, in went the first finger covered in lube, then the second and then both at the same time working it while spreading, I knew what would be coming next so I grabbed a pillow and hugged it, Steve grabbed me by the hips and pulled me back a little towards himself while pushing my ass down to give a better angle, there it was, his burning hot bulb pushing against my hole, this time with a lot harder but it wasn't painful. He worked my ass perfectly easing in back and forth until I felt his cock head push all the way inside, I let out a gasp of surprise, nothing could have prepared me for how thick he felt, there was a bit of pain but it wasn't bad, the most pleasant heat spread though my ring as he pushed more of his cock inside me stretching me as he went deeper, after bottoming out in me he let me rest for a few seconds before pulling almost all the way out and then pushing all the way back in with a single stroke, by this point my own cock was rock hard and drooling, his hands on my hips, he held me in place as he began to fuck me at an increasingly earnest pace, each time dragging his cock tip back to almost pulling out and driving back in, again and again, I could feel it building, I couldn't take it any more "Steve" I panted "I'm gonna cum", he said nothing, he just kept fucking me, then without warning he pulled his cock out of me completely, it caught me by surprise and for the briefest moment all I felt was empty, I felt some lube squirt in to my gaping hole followed by the entirety of his cock being shoved in to the hilt, the whole thing pushed me over the edge both literally and figuratively, as he push me further on to the bed and in to the mattress I came hard blowing my load on to the sheets beneath me, a wave of pleasure washed over me as my orgasm rendered my body to jelly. Steve's cock still hilted in my ass, he was now also kneeling on the bed with his weight on top of me, his hands over mine, fingers interlocking between my own as I gripped the bed, he gave my neck a kiss "I'm almost there, can you take it?" I gave a half conscious nod, "Good boy"; He began to rock his hips back and forth grinding his cock inside me, each time putting pressure on my prostate, postponing my post orgasm bliss, the grinding turned to fucking, he started slow and built up to where he was fucking the life out of me, the house was filled with the sound of sex as he pounded my ass, his breath was deep and heavy on my neck, I could tell he was gonna cum soon, that's when he hilted me one final time, and I felt a wet warmth spread through me, his body relaxed and still on top of me, we laid there for a good 15 minutes.

So I went to the regular Sunday afternoon jacks n jocks session at lateshift, which as the name suggests is a party in which, once you’ve paid your $15, you strip down to your jacks or jocks, check in your clothes and basically fuck anything that moves. I was heading to one of my favourite rooms, dark and often packed with dudes looking for anonymous sex, when I walked past another room off the hallway and noticed a couple of hot, physically well built sexy guys making out with the door open. I stopped and perved for a while before inviting myself to join them. They seemed to enjoy the thought of a little threesome action and we began to molester each other, it wasn’t long before I discovered that they both had incredibly large cocks that we’re standing to attention. I took this as my que to get on my knees and invite them both to take turns mouth fucking me. I’m a versatile guy but all I could think about while sucking this beautiful pair or huge dongs was god I hope they are both tops, I wanted them so badly to take turns ploughing my little hole. I’m not really a big talker during sex and often to shy to ask if a guy will fuck me bare, instead, I left there dicks dripping with spit, stood up and straddled the side of the bed and slapped a big glob of spit around my hole, I thought if they wanted to grab a condom from the container on the wall they would but I just crossed my fingers. It wasn’t long at all before I had a couple of hands squeezing and slapping my arse and fingers exploring my anus, more spit got added which was great as I really don’t like lubes, and, as I was just about to scream “please fuck me!!!” I felt a big bell end positioned against my tight bum hole and with one hard thrust I had been empaled by an 8 inch fat cock all the way to the balls, raw!! Yes!! “Fuck me hard” I instructed and he needed no second invitation, he went to town on my poor hole banging away on my now stretched arsehole, after a good few minutes of this I heard him ask his mate if he wanted a turn, this made me so hot knowing I was being shared around as they pleased, he pulled his massive beast out of me jumped up on the bed to allow me to continue sucking him. My arse was now being filled by the 2nd guy, who felt even bigger as he slowly slid in inch by inch, a different approach to guy number one but both work well, it wasnt long before he built up speed though and was moaning quite hard, it was only a minute but I knew he was close “don’t you fucking pull out” I yelled and with that he gave a almighty grunt and buried his cock deep inside me while he shot his load all the way into my guts, he kept fucking me for a bit before slowly withdrawing from my sopping hole. Guy number one decided he wasn’t done yet either as he repositioned himself behind me and pushed me back down onto the bed and once again drove his giant dick in hard, he had a lot more stamina and proceeded to fuck me for what felt like an eternity, often making mention of how great it felt with his mates load soaking his cock and dripping over his balls, he eventually started making noises that he about to blow and with a couple of deep hard thrusts I knew he was creaming my insides adding to his mates well fucked cum load. No sooner than he had pulled out, I stood up and turned around only to discover they had both split leaving me with a double dose of jizz, I wasn’t done yet though the session had only just began, I managed to score another 6 loads that day and went home with an extremely sloppy well fucked man cunt. Can’t wait till next Sunday.