A few years ago I was living in Brooklyn and while I was mostly dating women, occasionally I met up with guys on dating apps. The first few times didn’t really go very far – at most a bj, but I never let anyone cum in my mouth. That all changed one weekend afternoon in early summer. I met a guy online in Brooklyn Heights. He was an older guy – maybe about 60 – and I was about 35. (Older guys are my fav when it comes to getting with other men).
I got to his place which was in a nice doorman building and he let me up to his apartment which was on a high floor. The place was really big – probably 3 bedrooms. I got up there and we had a seat on the couch. I was super nervous but he opened a bottle of wine and we got to chatting. Before long we kissed and I reached between his legs and felt his big bulge.
Even though he was older, he was fit (he actually made one of his bedrooms into a gym) and he was hung, I’d guess about 8 inches and thick. He was really the ideal guy for me – hung and older!
Anyway, I pull down his pants and underwear and his big cock pops out in my face. I like the tip and do my best to take it deep in my mouth. I’m not super experienced with cock, but I do my best to lick his balls and his whole shaft and he seems to enjoy it.
So we are fooling around and get totally naked. He leads me back to one of the bedrooms – his big hard cock hanging out – and I tell him I want him to fuck me in the ass, even though I’d never been fucked before. We make out some more on the bed and then he gets out his lube and condoms. He gets himself and my ass all lubed up, and he tries to loosen me with a couple of fingers, but I’m super tight. He tries to penetrate me, as I lie on my back, my legs up on his shoulders. He tells me to breathe and relax, but still too tight.
In the midst of this, his phone rings several times. It’s an elderly neighbor that he helps, and she keeps calling him. Each time he goes partially limp and he needs a new condom and more lube.
Unfortunately he’s not able to get more than his head in my tight asshole. After a while I suggest that I suck him off. So he pulls off the condom and I get down on my knees in front of him, getting a good rhythm going. He keeps telling me to look up at him, which I do. Finally his knees bend and he moans, cumming in my mouth.
I must say there wasn’t much cum at all – I really wanted a big load. In any case, I still haven’t been fucked almost 5 years later, and I still haven’t swallowed a big load. I’m engaged to a woman, but I would love to have both experiences at some stage, maybe as a bi MMF threesome.
Source: reddit.com/r/gonewildstories/comments/hveozk/first_time_anal_mm
Does she know this about you?