My first time

The night i made the best mistake of my life

  • Score 9.5 (51 votes)
  • 2457 Readers
  • 2373 Words
  • 10 Min Read

It was a cool night in Perth, around 18C and i was laying in bed feeling way to horny for just beating off so i decided to bite the bullett and try out craigslist for some fun. I posted that i was looking for some fun in what i thought was the M4W section, however i had inadvertantly put it in the M4M bit. I am quite an attractive guy with a nice build to me, about 6'2" with a nice firm body, not cut but toned enough. Within about 10 minutes my email was flooded with horny guys looking for a guy to fuck. I was a little confused until i saw my mistake in posting my ad, but looking at all those cocks in their different shapes and sizes got me feeling really horny. As i looked at all these e-mails i came across one from a guy who had included a face pic. Even though i didn't consider myself gay at the time i found him really attractive. He had nice dark features and looked to be about 6ft tall. As i had been drinking a little i for some reason shot back a reply to him asking to see his cock and within five minutes he replied with a pic of a nice 7 1/2 inch cock that had a nice fat shaft and a tapered head. On my next email to him i said that i wasn't sure what i wanted to do with him and that i couldn't host but i knew of a nice quiet park nearby that had a disused jetty that we could get to. He responded instantly to this saying that he would be 15 minutes. "Fifteen minutes" i thought, "shit what am i doing?"

Fifteen minutes later though i was waiting down at the park on my street hiding behind a tree watching all the cars go by. Then i saw a hotted up ute slowly cruising up the street and pull into the carpark opposite the park. I gulped in some deep breaths and watched as the guy that i had emailed hopped out of the car. He wandered over to the park looking around for where i was, checking his I-phone and looking some more. It was now or never so i decided to call out to him. "Hey man, you looking for the jetty?"......."Yeah man, where the fuck are ya?".....This was it, so i walked out of the shadows and greeted this anonymous guy. "Follow me man i'll show you the way down."

We made some bullshit small talk whilst we walked down and he kept grabbing at my arse (i do have a real cute butt) and asking what types of things i wanted to do. I really didn't know but said that i just wanted to see where it all went and that anything was possible. When we got down to the jetty we stopped and looked around to see if anyone else was nearby. With the coast clear i turned around to find him standing right there in front of me with a devilish grin on his face.

He leant forward and put his hand in the small of my back pulling me in closer to kiss me. I didn't stop him and his kiss started to get me stirring in my pants. Soon i was kissing him back just as hard as he was kissing me. He started to move his hands down to my arse and grind his hardening dick into mine as we stood there entwined in each others arms. I started to get into it more and more and i got brave enough to move my hands from his shoulders down to his waist, i wasn't game to touch his dick so i just held him there on the hips and continued kissing. In the meanwhile i could feel his cock pressing harder and harder into my groin and i started to want to touch it more and more.

After what seemed like hours of doing this (probably 5 minutes) i became a little more brave and put my hand over his bulge and felt the amazing hardness of another guy for the first time. He started to moan and grind hard into my hand whilst he stuck his hands down my pants and started to play with my arse some more. This was getting too much for me and i broke away from him and stepped back. "What's wrong?" he said. I regained my composure and replied "Nothing man, just wanted to take off my top and i'd love to see you take off yours too"

So there we stood, both with our tops off looking at each other with lust filled eyes. I could see the head of his dick poking out of the top of his pants and decided that now was as gooda time as any. I moved towards him and fumbled with his fly, slowly pulling it down and pulling his dick out to play with. Feeling him in my hand, skin to skin had me thinking so many different thoughts i could barely concentrate. I tried to use the same techniques i use on myself and low and behold he started to get real hard. We kissed again as i continued to play with his cock slowly stroking him, feeling precum all over my hand. He whispered in my ear "Do you want to suck it?"....."Yes" was all i managed to squeeze out of my mouth before i found myself kneeling down infront of him.

I didn't really know what to do but i knew what i liked when chicks had sucked me off and i had watched enough porn to know that going deep is the ultimate thing to make the guy feel in command. So i started off by running my tongue up and down his shaft while he stood there. Slowly tracing around the head then back up and down the shaft. After a little of this i put my lips around the head and slowly took him into my mouth. I was really starting to enjoy his taste and it prompted me to take him deeper in getting almost to his balls before i gagged and had to take him out. But this was only for a second as i wanted him in my mouth so bad by this point it wasn't fair. I grabbed him by the shaft with my hand and started to bob up and down on his dick, sucking gently and running my tongue up and down the vein whilst jacking him off. He was starting to get a really deep breathing thing going on and was holding my head when he suddenly pulled away. Now it was my turn to be worried, "Sorry i said, did i get you with my teeth?"......"No it wasn't that" he replied, "I just don't want to cum yet." This made me feel pretty good that i had got him so hot and wild so quick.

He pulled off his pants and asked me to do the same and to turn around on all fours so he could eat my butt, at this point he could've asked me to climb Everest without a complaint from me so i did what he asked. I had never had anyone licking my butt before and boy was i pissed about that once he started. The sensations ran the whole length of my body and i felt my balls tingling in ways they never had before. I could also feel my hole starting to open up just a little when he pushed a finger straight up inside me. At first it felt a little uncomfortable but as more and more of his saliva made its way into me it felt better and better. Soon i was pushing back at his finger moaning and trying to say things that were sexy, which in reality were probably just more moans. Soon he had worked another finger in and was fingering me quite fast. I couldn't believe how great it was feeling when i finally managed to blurt out three desernable words, "Fuck me please!"........."You sure? he replied............Almost with anger in my voice i demanded that he fuck me now.........."I'm sorry, i don't have any condoms" he said right back. At this point i was beyond caring and i told him that he could just pull out when he was going to cum..... "Well if you're sure you want that i will be real gentle on ya"

I turned around and sucked him till he was really covered in my saliva then turned back around looking out over the river with him behind me. He took some lube out of his pocket and rubbed it into my arse (why he had lube with no condoms i will never know) getting two fingers back in me. I knew that his dick was way bigger than two fingers and was happy when he managed to get three in. He kept adding more and more lube into my arse until i could feel myself absolutely gaping around his fingers. But then he pulled them out and i got a bit more nervous. Then there it was, the feeling of the head of his dick at my hole. Slowly he swirled it around the edges of my hole picking up the excess lube then slowly pushing in the head......"Shit!" i yelled as he pushed in. But there was no stopping him now and he pushed it halfway in before stopping to let me adjust to this new feeling. After about a minute he pushed in a little further and the pain started to subside. Slowly he moved just a little in then a little out getting me a looser and looser until i wasn't all tense any more and he could push it all home. This was the moment that it all clicked for me and started to feel so good i could barely breathe. He rested there for a few seconds and leaned down and kissed my neck. I turned around ans kissed him as he slowly pulled back out halfway before he thrust back in again.

Now i knew that i was going to be OK with this guy fucking me i started to get hard again and pushed back into him to let him know that i wanted him to fuck me properly now. He certainly didn't have a problem with that and was soon pumping away at my tight little chute moaning and groaning telling me how tight i was and how hot i looked with his cock in me. It felt so good feeling that bare dick rubbing my insides that i almost came there and then but i wanted to hold out as long as i could. After a while he started to really slam my hole and pushed me to the ground so i was laying on my stomach with my legs spread as wide as i could and i instinctively raised my arse as high in the air as i could to get him in nice and deep. He started to breathe deeply again and i told him that i didn't want him to come yet and he stopped and pulled out.

This time it was me that was in charge and i told him to lay down on his back so i could ride him. As i sat down on his hot cock i leant forward and kissed him whispering in his ear "You have made me realize that all i need sexually from now is a dick like yours"......he laughed at me then kissed me deeper than he had earlier before saying "If i can stick my dick in an arse like yours i don't need anything more" At this i started to bounce up and down on his cock, squeezing my arse tight around his shaft moaning all the time. Pure lust was now coursing through my veins and my common sense had long since left me. He started to get that deep breathing thing happening again and said i better get off or he would come. I'm not sure what had come over me but i quickly told him that i wanted him to fill me with his cum. He smiled up at me and said "Well at least let me do that doggy style.".......I hopped off and turned around as he got behind me and just slammed his dick right into me and went straight up to full speed. I was right on the edge of cumming at this point and started to moan so loud i thought that everyone in the neighbourhood must have heard me. I had just noticed that one of the feelings i felt earlier had been his balls slapping into mine when he grabbed my hips really hard and started to drive real deep in me. I realized that he was about to cum and made my little chute as tight as i could for him. Then he started to cum in me, jet after jet of hot sticky cum shooting up my arse. I was surprised that i could feel it but i was loving it so much that it sent me over the edge and i came all over the jetty whilst he kept slamming into me still cumming. He mustn't have blown for weeks as it started to leak out my arse while he kept on cumming in me. I felt totally dirty and was loving it. He leant down and kissed me before slowly pulling out of my hole and it was the best post sex kiss i've ever had. Having an arse full of cum and cock whilst being kissed by the guy who put it there is the best.

After he pulled out we just lay there on the jetty for a while talking about everything that happened and how i had enjoyed my first time. He suggested that we might do it again sometime and this ongoing relationship lead to me living with him. I've had sex with other guys since, sometimes with my man involved but none have taken my heart like he did.

Report
What did you think of this story?
Share Story

In This Story