This story is about a friend I had for about 6 or 7 years until he found that special piece of man candy and stopped doing the ‘hook-up’ thing (much to my dismay). He was older, much older late 50’s I believe, but he had a fantastic cock and knew how to suck me better than ever I had ever had. He was also the first man to subject me to anal pleasures, he loved my ass.
It all started about my third or fourth time seeing him, up until this point it had always been blow and go’s, but this time when I lowered my pants and sat on his couch he sat next to me reaching over and playing with my already rock hard cock. I’ve always been the more repressed bi guy, sadly. I like to be played with but not really return the favor unless I’m really horned up and in the mood and I trust you. At this point in me and my friend’s relationship I didn’t do much.
So, when he leaned over and started kissing my earlobe and breathing into my ear, I just… kind of let it happen. God knows I didn’t want to stop. It felt fucking amazing having him do that while he played with my dick. He then kind of leaned over and stuck his head behind me and licked at my ass crack. This really drove me wild, and I didn’t let him do it too long because I needed him to start sucking me. He got the hint and climbed down to his knees in front of me taking me in his mouth.
I’d close my eyes and move my hips meeting his downward bobs sucking me. His hands still hadn’t finished playing though, I could feel a finger rubbing that little spot just below my balls and eventually rubbing my asshole. He then gave his finger a long slow lick and slowly stuffed his finger knuckle deep into my ass. My god, I couldn’t believe how good it felt. I didn’t last much longer after that until I blew and he gobbled down every drop.
… this man has probably swallowed gallons worth of my cum in the almost decade we’ve been hooking up…..
This was all it took for me to be in love with ass play. I soon incorporated at home with my wife with dildo’s and butt-plugs and pegging, that’s how much I grew to loving my ass being played with.
Eventually, my friend would all out rim me and he would tell me how bad he wanted my ass, but he would never force the issue or make me feel bad about not finally bottoming for him. He was content fingering and licking my ass. He let me top him once, but I didn’t really like it, it was much nicer getting sucked off. Man ass isn’t really for me.
Years would go by, and we had done just about everything. One of my favorites was when we would lay with our legs overlapping and I would jerk us off together, the only thing I didn’t like about this was that I loved being swallowed so much. Still, he had a glorious cock and I loved playing with it and sucking on it, I always blew buckets whenever he and I played.
As the years progressed and I went away to school or moved to then next city over we didn’t see each other as regularly but whenever I came home I’d make sure to see him at least once to play with him.
One of my last visits with him (might have been a year ago now or so) we were doing our usual routine. I was on all fours in his bed with my ass sticking straight up for him while he ate and fingered me. With all my dildo at play, I felt like it was finally time to let him fuck me. I knew he had toys on the side of his bed and I looked over and happened to find a condom and some lube. I kind of sheepishly handed both to him with a smile and mumbled that I wanted him to stick it inside me.
It only took him moments to lube himself up and wrap up before I felt that cockhead knocking on my backdoor. He went slowly pushing himself in my ass. It was amazing. It felt better than any dildo or strap-on I had ever played with. He pushed hard into me making me lay on my stomach as he fucked me. I couldn’t believe how good it felt, and I still can’t believe this is the only time I’ve ever bottomed for someone, because fuck I want to do it again.
Pre cum was oozing from my little uncut cock all over his sheets as he eventually laid back and had me reverse cowboy him. Holding myself up against a wall that was close by I took to riding that cock like I had owned it. I can’t remember exactly what had happened, but for some reason we had to take the condom off. I didn’t mind, I trusted that he was clean after all, we had played so often if he was dirty I would have caught something by now. I just didn’t want him to cum inside me.
Sadly, I didn’t cum from him fucking me, but he did all over his stomach. I couldn’t believe how bad I needed to cum, I laid ontop of his chest and forcefed him my dick. Grabbing his head I mouth fucked him until I writhed and blew in his mouth. Having him greedily gobble down every drop I gave him was amazing and after it was all said and done I couldn’t do anything but fall onto his bed and lay there a few minutes to regain composure.
To this day, I wish he would fuck me again. I send him a msg on Facebook every so often and wish that he’d agree to meet me one more time so he could fill me up. I don’t generally trust a one time blow and go guy to fuck me, but god. I so want to.
Source: reddit.com/r/gonewildstories/comments/gj05av/first_time_i_took_it_mm