SUMMARY: I finally got together last week with another man after 4 years, immensely enjoyed lots of foreplay (too much foreplay?), that I describe below, but lost my erection before penetration. I so wanted to fuck him that night, only the second man I would have done that with, and we're getting together again tonight!
After all my chatter on here about how I haven't been with another man in 4 years because I fell in love with a woman and was together with her on again off again for 3 years in a relationship that ended last December; and how my gay feelings and fantasies have been roaring ever since; and how I was arranging to get together with a guy in March when the lockdown happened; and how things changed for me in 2013 when I finally had anal desires with a real guy that I was naked with (after 21 years of only anonymous oral and tons of anal fantasies), rimmed him for over an hour before finally giving in to his begging pleas to fuck him (my only time so far); and how after that up until I started seeing my ex-girlfriend I finally for the first time started making it more personal and hooking up with local guys in each other's homes for oral play and rimming: I FINALLY GOT TOGETHER LAST WEEK WITH A GUY IN HIS BEAUTIFUL HOME!!!
He was my age (57), bisexual, and divorced. We met online on Squirt and enjoyed sexy chat together there for a while. We both eventually felt comfortable enough in the pandemic to get together in person. I shaved my pubes--cock and balls, but, even though he was mostly a bottom he said, I also shaved my ass and cleaned out my hole with an enema bulb I just purchased, just in case we both felt like me bottoming for my first time as well (such a huge fantasy for me too).
We first chatted on the sofa for a while, with a television on mute, and with candlelight around us, but I could tell that he was nervous (it had been well over a year since he was last with a guy), as he was talking a lot, and kept reiterating the same non-sexual story. Because I knew what he liked from our sex talk online, I kept trying to start a sex story that happened to me at a gym many years ago, and finally managed to relay it. That finally turned things around, and I could see he was relaxing and getting horny again and in the mood.
We started playing there on the sofa, started taking each other's clothes off, when we decided to take it to the bedroom. We were both very hard and very hot for each other in the candlelit room, started grabbing each other's bodies with lust, started kissing, grinding our cocks together, frotting, and he finally started sucking my cock. With my overwhelming desire for cock, I took my turn, and finally had another man's cock before me, and I couldn't believe it! I began kissing it all over, licking it all over, and finally sucking his beautiful manmeat. I asked him whether he liked 69, and he did very much, so I flipped around on top of him, and we sucked each other's beautiful cocks. It was so wonderful! I love 69ing with a man in particular, and so rarely have had the opportunity in the 21 years of anonymous oral and 3 years with more personal hookups. I finally got his entire cock down my throat, with my lips pressed to his pelvis. I started massaging his cockhead with my throat, and he went crazy with that feeling. I went to town deepthroating his cock, while enjoying his mouth on mine so much.
We enjoyed a lot more rubbing and hugging of each other's bodies, deep kissing, cocksucking, but finally my desire for his ass became too much, and I dove in with my lips, and then my tongue, to make oral love to his hole. His beautiful puckered asshole! My wild desire was all there, as it was with those other guys between 4-7 years ago. I licked and licked, and finally tonguefucked his ass like crazy, to both our hearts' content. We switched it up with more cocksucking, deep hugging, and kissing. But I always ended up back inside his asshole with my tongue. I then began to use my fingers to loosen him up, first an index finger slowly for a while, with tons and tons of saliva, going in for more deep tonguefucking at times, and then eventually two fingers, really fingerfucking his beautiful manhole good. With his permission I also started rubbing my bare hard cock up and down in his ass crack and my cockhead against the opening of his asshole. We both loved that so much. I'm back-and-forth between that and more rimming.
I then asked him whether he had some lube, because even though I brought condoms I forgot my lube. He wasn't sure and went to go look for it in another room, and I went to get a condom. I don't know whether it was that break that messed my head up. But even though I was hard as rock since we first got naked, I started losing a bit of my erection. Back in bed we started playing a little bit again, and I got it back. But then, because my fingers were all drenched in my saliva, I had trouble opening the condom wrapper (it's not a regular condom wrapper, because it's these high end condoms I ordered from the United States because my girlfriend liked them). I was working on that thing for like 30 seconds, and finally with a combination of my slippery fingers and teeth, got it opened and had the condom in my hands. But my cock by then had begun to lose its hardness again. Dammit!
We both tried getting me hard again, but it wasn't working, and I was just getting softer. And of course my brain was getting in the way too. From time to time this happened with my ex-girlfriend as well. If we would spend way too much time in foreplay, sometimes a couple hours, and then I would go for the condom and open it, I don't know, but the combination of the long foreplay and the condom caused me to lose my erection sometimes. Then my being anxious about that prevented it from coming back again. And now this happened again with this man. So I was anxious again I guess, and just went softer and softer.
I so very much wanted to fuck him, and he definitely wanted it. But he was totally cool about it. Inside I wasn't so much. I tried a lot more with my bare limp cock against his asshole, to get it harder, and even trying to push the tip of my cockhead into his hole with my fingers because that was such an arousing experience for me with the first man I fucked in 2013, and simulating fucking with my slightly less soft cock against his hole, with me getting all sweaty with the vigourous simulated fucking, slapping against his ass like crazy, but it all didn't help.
He was then begging me to just cum all over his ass. He wanted to feel my hot cum on his ass. So even though I was soft, I was somehow able to stroke one out, jerking that cock like crazy, and cum on his ass crack and hole (but nothing like the powerful orgasm and cum shot I know I would've had if this had not happened). I then dove in and licked every drop of my cum off of his ass and hole. We then deep kissed while he masturbated. I was hoping that he would be making some sounds just before orgasm, so that I could go down and lock my lips around his cock, because I at least wanted to give him that much, to cum in my mouth and down my throat. But he's a silent cummer as he later told me, and I missed my chance, and he came all over the bedsheets. We both took showers after that, but separately as he disappointingly didn't join me in my first shower.
So overall it was a great experience, though disappointing. I was again so disappointed in myself especially. But I'm sure he also really wanted a good pounding deep inside his asshole, so I must've disappointed him, but he never said so. But I had finally been naked with another man, which I have been so desiring since the break up with my ex-girlfriend, and to tell you the truth, throughout that relationship. And I loved having sex with a man again; I felt desire for him, something that I wasn't sure that I would, given how my gay fantasies these last 28 years have not always matched real life, in terms of the desire and chemistry I feel with the man I'm naked with. And I've always fantasized about having a FWB, or even a boyfriend, a man who I can regularly make love with, and bareback. I don't think this will be the guy though, since he is out of the country 6 months out of every year.
But we're getting together again tonight! And I haven't masturbated in the 7 days since we hooked up, except for the little bit of stroking of my hard cock that I'm doing while writing this, lol. I'm definitely going to get to the main attraction quicker this time, and if my head (the one on top of my shoulders) doesn't get in the way, especially now with this precedence with him, I'm hoping that I will give him the fuck of his life! I just want to focus on loving this man and giving him as much pleasure as possible. Pray for me!
I'll let you know how it goes.
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Originally Posted by emerging
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