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.
