Rob rode on the back of my bike back to his place, with his hands around my waist and trying to work his hands into my crotch all the way. We grabbed a couple beers out of his kitchen fridge on the way up to his room. As soon as we shut the door we put down the beers and our tongues went into each other's mouths. Rob's hands were all over me. As he was biting my ear lobe he said, "I want to watch you strip for me stud", he said. I took a swig of my beer and pushed him onto the loveseat and took off my shirt. "Fuck man, you just look hotter every time!" he said. I stood up on the couch with my hips even with his head and pushed my growing bulge into his face. "Undo my pants Rob." He did and I slowly pulled them down and stepped out of them. "These are hot," he said, talking about the underwear. "When did you get these?" Shit, after the whole nude stripping issue, telling him Tim gave them to me just tonight might be a bit awkward. Rob knew Tim through me, and could probably make some guesses about Tim, but we never spoke about my history with Tim.
Being the clever guy that I am, instead of trying to explain about that now, I just said "they're new" and shoved my crotch into his face. With my hard cock pushing through the underwear and somewhat into his mouth I'm pretty sure he stopped thinking where they came from and only how he preferred they not be in the way for very long. I turned around and started pushing my ass into his face next. He reached up and started pulling of my underwear. I stopped him. "You first, I'm not on the clock", I said with a wink. I climbed off the loveseat and back onto the floor. "Stand up", I told him.
Rob stood up. I grabbed his hard cock through his jeans and squeezed it as I we kissed again. I wanted to say "I love you" but didn't. I stepped back and looked at him. His was wearing a pretty tight shirt and showed off his biceps and a good hint of his awesome chest. His cock was straining against his jeans. "You're so damn hot", I told him as I pulled his shirt up and over his head. I squatted down and started kissing his stomach, then gradually worked my way back up to his lips, making sure to feel his pecs and arms on the way. Then I reached down and undid his pants. I slid them off and kissed his cock - the cock which would be the very first to enter my ass. Rob's cock was thicker than Tim's. I'd seen pics of guys' cocks, but you don't know what's really average from pics. I would learn in the years to come that Rob was thicker than most. Not that I've bottomed for a lot of guys since then, but Rob would rank second in girth to those I've taken. I licked his cock all over, took his balls in my mouth and then took his cock in my mouth for a few minutes. Rob pushed me off and said something like "Someone's over dressed". He pulled me up and took off my underwear, did the same thing to me and we made our way over to his bed.
Rob lay down on his bed and put his arms over his head. I have to say I still have that image in my head to this very day. Rob was just plain awesome to look at. His face, his pits, hit chest, his abs and that cock of his which pointed straight toward the ceiling. Any guy would want to just jump on top and start riding this dude, but he was mine now. I climbed on top of him, our cocks pinned between and us we made out for the longest time. Rob started leaking precum as our cocks ground against each other.
"Looks like the lube machine is getting ready for my ass", I said. Rob turned me over on my stomach and started massaging my shoulders, then made his way lower. "You're going to need to get good and relaxed for this. I'm gunna lube you up good, but it's going to hurt like hell for a little bit stud." I remember fucking Tim that first time. Tim just had to know what it was like and suffered through the pain. Rob is definitely bigger than me and I know Tim had been playing with his ass before I fucked him. I was a total virgin in that regard, not having even fingered myself.
Rob finished the massage with my butt and legs. Then he put a pillow under my waist and spread my legs apart. He spread apart my butt cheeks and started rimming my hole. That felt sooooo good. He told me to relax and started to press his tongue into my hole. "Going to push in a finger, try to relax", he said. He slid in a finger, then a couple. Although I felt a little stretch, it felt good after I relaxed. "That's good", he said, "way to relax. Feels good, doesn't it?" "Uh huh", I moaned as he slid his fingers in and out.
He pulled out his fingers and went to get some lube. "I'm gunna loosen you up more with another finger or two." With the lube Rob slid his fingers in and out several times. I don't know if he was using three or four, but I could tell I was resisting. My mind told my ass to relax and it did, but when I felt him on the outside and pushing it, I just tensed up. After a little while Rob asked if I was ready to try him. I didn't know if I was, but wasn't going to turn back, so told him to go for it. He crawled over next to me, put his arm around me and gave me a kiss. Since I was already on my stomach we decided to try doggie style. I wanted to watch him, but just left him in control, figuring he knew what was best.
Rob put more in me lubed up his cock then placed it against my hole. I knew to try to help him by pushing out like I was taking a dump. As he started to push in though I tensed up. We tried a few more times and on one of them I felt some intense pain. He was in!
Me: "Damn that fucking hurts. How far are you in?"
Rob: "Hardly at all man."
Me: "What? You've got to be shitting me. Hardly at all?"
Rob: "You've got to relax more Brant."
Me: "Maybe if your cock weren't so big I wouldn't have to."
We started laughing and what little bit he was into my popped out.
Rob: "Let's try another position."
Rob flipped be over on my back, pulled me to the edge of the bed and put my legs on his shoulders. Again I could feel the tip of his cock against my ass, but the view was awesome.
Me: "I like the view better this way."
Rob: "Me too stud. Now close your eyes, relax and take a deep breath and blow it out."
I was determined to make this happen. I took a deep breath, closed my eyes, exhaled and pushed out. Rob gave a push in against me, sending my eyelids wide open.
Me: "FUCKIN A!"
Rob: "Stay still. I'm in. Just let the pain die".
I didn't think it ever would, but after what seemed forever of breathing heavy I actually felt myself relax. Really relax though, not trying to, but actually doing it.
Rob: "Good man. The hard part is over."
Me: "Good. I still like the view."
Rob: "It's awesome from here too stud."
I just loved it when Rob called me stud.
Little by little Rob rocked back and forth, working his way deeper. At times it still hurt, but not as bad. I sort of drifted off a little into fantasy land, looking at this fantastic looking guy I was really into, showing such signs of enjoyment on his face and at the same time, concern for me and not taking it too deep too fast. I watched him look at and admire my body and could see the expressions of enjoyment on his face, both of me and by the feelings from his cock getting deeper inside me.
Rob: "I'm in all the way. How's it feel?"
Me: "Okay. I'm not feeling the pain that I was before. Not exactly feeling the joy though either."
Rob: "That will come."
Rob leaned forward and kissed me, his cock fully embedded in my ass. Then he got back up and started rocking back and forth a little.
Rob: "You need to keep trying to relax. Try to just feel the warmth and the motion. I'll do the work, you just try to feel the experience."
Rob then started with short strokes, then longer ones, nice and slow. Like a switch was thrown I started to enjoy it. Rob could tell immediately, he was watching my face which was a total turn-on. Our eyes were just locked onto each other, like we were talking but without words. Such a connection we had. He was totally in control of me, I was totally submissive but at the same time he showed his caring and love.
Before long he picked up the pace and the length of his strokes. I knew I was moaning and I could feel my cock hardening. For a couple moments I thought I was going to cum. But I didn't. To my shock a little precum oozed out. I NEVER precum. I'm totally jealous of the guys who precum like crazy. But this time I did. Rob reached down with a finger and tasted it.
Rob: "Mmmmmm, nice and sweet."
I precame a little more and tasted it myself.
Me: "Shit, I've never done that before."
Rob: "We'll have to do this more often."
Me: "Yea...."
Rob started taking full thrust. I remember myself moaning and was beginning to stroke my cock a little too. It came upon me pretty suddenly.
Me: "Fuck man, I'm about to cum."
I shot a huge load over my stomach and onto my chest. If his cock hadn't been in me I would have easily shot over my head. And I came and came and came. So much cum.
Rob: "That was amazing."
Me: "How close are you?"
Rob: "Close, but I'm not gunna cum in your ass. Cum on your face turns me on too much - gunna own you."
Me: "Hell yea".
Rob pulled out, put my legs down and climbed on top. He took maybe two or three strokes on his cock and started blowing several loads onto my face and neck as I watched the volleys shoot out.
Rob: "Totally fucking hot!"
He leaned down to kiss me.
Rob: "Next time it's in your ass stud".
Me: "Hmm. Felt like it was my ass. Must have been someone else."
Rob: "You know what I mean. Your ass is mine."
Rob lay on top of me, our cum squishing between us and we made out for a bit. As the cum started cooling down we got off his bed and took a long hot shower together.
The next morning Rob fucked me again, this time cumming in my ass. It was easier. The pain wasn't as much, but I didn't enjoy it any less. I watched Rob the whole time. Submitting to someone so hot is such a turn on.
As we left to grab a bite to eat, Rob claimed the underwear Tim had bought me for his own. I sure didn't mind seeing his cock and ass in them, so I went commando with a hard on.