The first time I bottomed for my best friend

I'd just turned 18 and riding bikes to the store with my best friend J who was 19. We
did everything together and had been friends for a few years now. We were getting some
things at the store, because like every weekend, I was staying overnight and his parents
were away for the weekend. On our way back from the store of course we were riding like
fools and I went right through a puddle which soaked my pants, especially my ass, which
in tight gray sweat pants, was easy to see. We laughed about it and began riding faster
in front of J telling him I was starting to freeze my ass off. I turned over my shoulder
to see J staring at my ass and then look up laughing again. So we got back to the house
and went to his room where we'd be camped out for the night watching our usual stack of
vhs pornos we had collected. I asked J if he had any underwear I could borrow as mine
were soaked. As I peeled my sweat pants off and knelt down to take off my socks, I
noticed J looking at my ass again laughing saying sure you can as I saw his usual bulge
in his own underwear. At this point we'd been jerking off together for a couple of years
now, so we'd seen each others cocks before. He threw the underwear and they landed on the
floor in front of me, and with my underwear off, I bent over to pick them up. J said nice
asshole and we both laughed with our humor.

J used to lay on his bed and I on a mini mattress on the floor, there we would watch our
porn and stroke our cocks into the night, cumming 2 sometimes three times a night! We
were young and very horny guys. I could always see J's big cock from where I was and had
witnessed him cumming like a fountain on several occasions, he caught me watching a
couple times and just laughed say, I know you wish you a big cock like me as I was not as
endowed. This particular night while watching an anal scene, J had very casually while
stroking his cock says, Hey, I thinking, I wonder what anal feels like? I said I don't
know let's get some women to find out, we both laughed. He now said, You know since you
are clean, and I'm clean, we should experiment a little. I was like experiment how? J
said, with anal, we can do it to each other. I was like, I don't know, I'm not sure about
that. Now at this point I honestly never thought about doing anything with another guy,
but a butterfly type feeling overcame me as he kept talking about it, convincing me it
was a good idea. Eventually he got me to agree, but who will go first? And again J being
the older, bigger and more dominant one, he convinced me he would fuck my ass first!

As we were stripped of our clothes, J had a jar of Vaseline of course and immediately got
a handful and began stroking his big hard cock. Me almost trembling, I got some and with
J's instruction he told me to begin fingering my ass to loosen it up a bit to make it
easier. He knew quite a bit about anal as he heard about it from his older brother who
had fucked his girlfriends ass. I fingered my tight virgin ass for a while, until I could
start to get a second in, J watching me stroking his big cock slowly. I had thought I was
ready and had gotten on all fours, J moving my legs apart a bit, getting closer to me, I
felt the heat of his body and could hear his breathing. After adjusting ourselves a bit,
I felt his left hand on my ass cheek, his thumb opening my crack, then the hot head of
his cock began pushing against my tight puckered asshole. He slowly started to penetrate
me and open my asshole with his thick cock, as I gripped the carpet and let out a dull
whimper, I felt the head of his cock enter my ass. Then slowly, in and out he went,
feeling my ass getting stretched and wondering what have I gotten myself into. Slowly in
and out, in and out, deeper and deeper. My cock began dripping precum constantly on the
towel under me. As he began another thrust I felt his other hand let go of his cock and
grab my other hip, his cock was in good now, he was fucking me. J started to speed up a
little probing deeper in my ass as I gripped the carpet so hard, his breathing and
sweating on me, my cock dripping more. J asked me how I was doing not missing a thrust in
my asshole, I told him OK, how long would he be? He just kept telling me almost. When I
felt his balls touch mine, I knew then I had taken all of his thick cock in my now not so
virgin ass!

As he got faster and faster, I told him to not cum inside me. J grunted ok as I felt him
grab my hip harder, pumping faster, balls slapping, feeling my ass cheeks bouncing, it
hurt, but felt good at the same time. He began breathing heavy and right then as his
thrust became more powerful, I felt his cock begin to pulse deep inside my ass, over and
over again! J was grunting as he gave a few last deep thrusts until he came to a slow
halt. I began to breath again I think, while his sweat was dripping on me. Then J slowly
pulled his semi erect cock out of my loose stretched asshole. Cum running out of my ass
running down my balls dripping on a towel. It was then I realized I'd just been fucked
and came in my ass by my best friend.
And that was just the beginning....