Mixing pleasure and business [m/m]

This is the sequel to http://www.reddit.com/r/gonewildstories/comments/1zclih/mixing_business_and_pleasure_mm/

tl;dr – I met someone at a business conference in another state and we found out that we were both curious about other guys, so we blew each other in my hotel room (as one does, I suppose).

After we both came into each other's mouths that night, we didn't end up doing anything else (yes I know I hinted at it at the end of the first story), as we were both quite spent and I had to leave the next morning on an early flight. We parted with a nice long kiss and made a promise to catch up again when I was back in town. This was six months ago.

As it so happened, work sent me back for another conference, but this time my one night stand (let's call him Jacob) wasn't required to attend this time. We exchanged numbers after our encounter last time, and so the week before I sent him a text to let him know I would be back. The reply was quick from Jacob – he still thought about that night, thanks to my 'amazing cock-sucking skills' (yay!), and that he would meet me after the conference to have 'dinner and more ;)'

The conference was a blur as all I could think about was enveloping my lips around Jacob's luscious cock once more. During the conference, I even stealthily re-read my previous story as a reminder of how hot that night was. His slim fit body that I worshipped. His gorgeous blue eyes looking down as I fellated him. And of course, Jacob's eight inch member releasing into my mouth and how I struggled to swallow his love for me. I still found it hard to believe a guy like him was keen for seconds after all this time, but of course I won't complain about a nice dinner and hot sex.

After the conference, I followed his instructions and waited outside a Japanese restaurant on this busy inner-city street. As it was a Friday night there were men in suits everywhere, but Jacob was instantly recognisable even in his suit as he walked around the corner, and his eyes lit up when he saw me there. He gave me a quick handshake turning into a hug and I swore I could feel a tentative poke from the tip of Jacob's erection down there when our bodies closed in for the hug – not that I minded!

We went in and had dinner, exchanging small talk over sushi and wine in an area tucked away from the main part of the restaurant. The alcohol was definitely having it's effect as we once again renewed our dirty talk from that night a few months ago:

"Are you still with your fuckbuddy?" "We sometimes still meet up, but not often, we're always busy" "Have you done anything else with a guy since we hooked up?" "I tried Craigslist once but it was just mutual wanking even though I wanted to try sucking him off" "How does my cock compare to others?" "You know it's enormous, stop fishing for compliments!" "Did you shave for tonight?" "You bet ;)"

I know it was the filthy stuff you'd hear in the typical bad porn videos, but fuck, the naughty conversations did the trick and I imagined both of us were struggling with our erections (I certainly was). What can I say, I'm a sucker for dirty talk. Jacob then explained that his apartment was close by and his roommate just moved out. That was all the prompting we needed as we settled the bill and made our way to his place, which as it turned out was only about a block away.

The mutual horniness was quickly confirmed because as we entered the lobby, Jacob started playfully groping and fondling my erection and I felt my pre-cum leaking onto my underwear. Good thing I planned to ditch it as soon as I got to his place! He brought his lips to mine and I let a small moan escape as we locked lips, his tongue dancing with mine as he continued to massage me over my pants. Like before, he was a great kisser who knew how to use his tongue, and I enjoyed how he was taking the lead tonight. At this stage, even though the lobby was empty I really didn't care if people stumbled upon us locked together in such a passionate embrace in public.

The elevator couldn't come soon enough as I desperatedly wanted my clothes to join Jacob's on the floor for part two of our lovemaking. We continued to swap saliva and molest each other in the elevator all the way to the ninth floor (a bit of deja vu as it was like the first time we had sex), pausing only when the elevator doors opened (just in case), and soon I found myself in Jacob's place for the first time.

Jacob said he needed to take a shower first (it was a long work day, how considerate of him), and with that he started shedding his clothes right then and there on the spot. I casually asked him if I could join him and his cute smile told me what the answer was to that stupid question. He took off his shirt and pants to reveal his smooth body, and black briefs barely covering what I knew was an eight inch monster just wanting to be released from its prison. Fucking hell, I thought, as we took off our clothes without much fanfare. I paused to admire his amazing cock being set free before me as Jacob stepped out of his undies, and it seemed like his erection was pointing towards me, asking for my undivided attention. From the look in Jacob's eyes as I stripped off in front of him, I could tell that Jacob wanted to attend to my cock too, as the pre-cum kept leaking out of my cock even after it already made a mess of my undies.

And so not one minute later, I was on my knees in the shower, sucking his beautiful penis like it was my last meal. I had waited so long for this and I didn't need the shower, I just wanted to milk his cock for the reward it deserved. He completely shaved it for me (how sweet) and I employed my patented cock-sucking techniques to bring him close to the edge. I worshipped him down there as the water spilt over me, my lover moaning as I kissed up and down that eight inch long shaft and showing my love for his organ by licking the base of the head and gently sucking on his delicate balls (which I knew would drive him crazy). I tried a couple of times to take all of him in my mouth, but I only made it about halfway down his enormous penis. Jacob then turned off the shower and I could finally clearly see the pre-cum oozing out, indicating his cock's satisfaction with the oral pleasure. He started moaning more frequently as I spent another minute or so working on generating more pre-cum to lick up, and to my (slight) disappointment said that I had to stop and that he wanted to return the favour.

He motioned for me to step out of the shower and I followed him, as he produced a towel to dry us off. Jacob's idea of returning the favour was using the towel to make sure my penis was really really REALLY dry. I wish I had taken a picture of the moment – two naked men standing together, just out of the shower, with the shorter one embracing the taller one around his neck, looking pleadingly up at him as his poor cock was being jerked off with nothing more than the friction of a towel. Then, the shorter one starts moaning in pleasure and the taller one leans in to silence him with his tongue as he continues the downstairs hand service. Fuck, thinking about it even now makes me horny.

After a while of this obscene action, Jacob again stopped (I'm really liking him taking the lead) and quickly used the towel to dry us off completely this time. I was surprised the towel worked since I assumed it would be soaked with my pre-cum, god knows there was lots of it. Anyway, we moved to the bedroom and Jacob turned off every light but the ones at the top of his bed. Maybe it was just me but the soft yellow lighting and double bed made it so inviting.

I flopped down on his bed and Jacob responded by kneeling at the side of the bed and fellating me. I moaned straight away as he used the techniques he learnt last time (licking the base of my head, pumping about half way up the shaft) to give immense pleasure to a cock that just wanted to cum but wasn't being allowed to. Fuck, he's good, this gorgeous guy really is so enthusiastic about my penis. I didn't even have to tell him what to do this time. I told him that he was great and Jacob just responded by pumping my shaft harder and licking up all the pre-cum. I warned him that I was going to cum and that I wanted to cum with him at the same time. Jacob was a bit puzzled and looked up at me with those blue eyes (how cute), and I said that he should get lube for the next bit.

Jacob might've anticipated this as he quickly got up off the floor, went to his bedside drawer and pulled out a condom as well as some lube. I remember thinking it was going to hurt, having all of him inside me, but I was super horny given his cockteases and I was a complete cum slut at that point. I then said what is possibly one of the dirtiest things I have ever said – "I need you to fill me with your hot cum. Please fuck me, and you don't need a condom". Jacob asked whether I was sure but he predicted my answer as he put back the condom and started preparing to enter me for the first time.

Now, I have had anal sex regularly with my fuck buddy's six inches and I had gotten used to the slight pain from penetration, but I knew eight inches of Jacob was going to be a different thing altogether. The apprehension soon disappeared though as I eyed his enormous cock being covered with lube and I lusted for it to make its home inside me. Jacob once again asked whether I was sure and I nodded as I shifted to the middle of the bed and raised my knees in the air to present my hole for him, ready for the most intense sexual experience of my life.

I grabbed some of the lube for my own hole as Jacob finished off his preparations. I was feeling nervous as he moved on top, his arms either side of me, and then looked down to guide his erection into my opening. I guess he could tell I was anxious as he nibbled my neck while his penis prepared for insertion. Suddenly, the tip penetrated me and I gasped loudly as I felt Jacob in me for the first time. He asked if I was okay and I said that he could go on. How considerate.

So there I was, legs up on Jacob's bed, as his eight inches slowly wound its way inside me while my lover was on top trying to make me feel at ease by kissing my neck. Quite scandalous. We both gasped as his well lubricated penis gradually became one with my tight hole. There was no way he was going in me dry – even with lube and me being extremely turned on, Jacob's cock was filling me up completely as he eased into me for the first time. It seemed like forever and it hurt a little, but finally the entire length of my lover's cock was in and we responded by sharing a sloppy kiss.

Then the real fun began. We both moaned as he thrusted in and out, slowly at first as I adjusted to his enormous cock stretching me out down there. He kept asking if I was okay (I really was but I guess there's a fine line between pleasure and pain, as the song goes), and I kept reassuring him that I was fine. We were fucking like animals in heat, with Jacob moaning with each thrust and me whimpering and clutching tightly onto his back as he began to destroy my hole. Fuck it was hot, pre-cum from my penis just kept coming out as evidence of the level of pleasure, and Jacob did not let up in fucking my poor hole. After a while he sat up a bit to change the angle of his insertion, lifting up my bottom slightly from the bed, and the tip of his lovely cock was exploring my anus in a different way. That was nice of him!

After perhaps less than five minutes of thrusting, Jacob told me he was close to cumming and asked what to do. I told him we were going to cum together and (with great difficulty I might add, given my legs being up in the air), I reached down with my left hand and started jerking myself off. The sight of me masturbating at the same time must've provided extra motivation to Jacob, as he told me it was so hot and that we were definitely going to cum together.

I swear his penis grew an extra inch in me watching my own penis getting worked on, as Jacob began to thrust even harder, wanting to impregnate me with his seed. It was ridiculous, looking down and watching this gigantic cock fill me up completely with each thrust while I was simultaneously playing with myself in an effort to orgasm at the same time. It was hurting, but in a really good way, and as I felt the familiar sensation of climax approaching I told Jacob that he was such a fucking stud and that I needed his hot cum inside me. Jacob was now focused entirely on his pleasure and soon his rhythymic thrusting became erratic, indicating he had reached the point of no return and that I was about to receive his love. And to my delight, I was joining him too in a shared orgasm as my masturbation approached its conclusion.

It was utterly glorious, as Jacob began to unload wave after wave of his seed inside me and my own penis demonstrated its approval by cumming at the same time. Fuck what a sight it must've been. I closed my eyes and moaned loudly due to the overwhelming pleasure, as I ejaculated a massive load while my lover kept pumping cum deep into my hole. My lover must have also ejaculated a lot as he himself continued moaning for quite some time, his penis pulsating several times inside me as my tight hole was rewarded for the pleasure it gave to my lover's cock. It might've been the hardest I've ever cum too as thick globs covered my belly, with some running onto my chest and the rest ruining his bedsheets. After the last few drops of his cum made its way inside me, his spent cock slipped out of its temporary home and we moved to embrace each other side by side, our chests connecting us up there, and our semen lubricating us down there. I could feel Jacob's reward already dripping out of me, but we didn't care as we gently kissed, our softening penises covered with cum and totally spent from the lovemaking.So hot!

We told each other how great it was (although it might hurt in the morning for my poor butt, which Jacob laughed at) and we got up to return to the shower. I apologised for the bedsheets and he said that was fine and that we could stain it again in a few minutes if I wanted because it needs to be washed anyway. Fuck he's such an awesome lover. As he slowly stepped into the shower, deliberately giving me an eyeful of a penis slowly regaining its erection, I grinned and said that although I loved him cumming inside me for the first time, I hadn't actually tasted his cum tonight. My lover responded by grabbing me by the ass and pulling me into the shower with him, stroking my semi-erection, and said that he hadn't either ;)

Source: reddit.com/r/gonewildstories/comments/3beqqu/mixing_pleasure_and_business_mm