There’s a divide here for me, it’s between volition and non-volition. Is it longest it took to cum because you just couldn’t get your orgasm, or longest it took to cum cause you were holding off orgasming? The distinction is important to me cause I don’t like to cum until my partner has first, because I like knowing they’ve been thoroughly satisfied, and also seeing them cum makes me cum even harder.
Non-volitionally
So longest it took non-volitionally would be 6 hours.
First time I ever had penetrative sex with a guy, and it was terrible. He wanted me to top him, but he was worried about my dick being too big (valid concern) so he huffed poppers nonstop during the sex. The smell of the poppers was distracting and it made his hole loose even for my cock which is a feat because almost every hole is a super tight fit for me. Because his ass was so loose it didn’t feel pleasurable and the guy was a complete dead fish/pillow princess (i.e. he was so unresponsive and unpassionate) that I pretty much lost my wood and was fucking him with my flaccid cock. Which to my credit is still quite sizeable since it’s as big as many average sized guy’s erect cocks.
I don’t know why I kept at it though, I guess because it was my first time at anal that I was just committed to finishing. He rode my flaccid dick and because it’s sizeable even flaccid, I didn’t pop out much, but eventually a few hours in and trying hard to get the sex to be pleasurable for us both and successfully reach orgasm, I started getting sore. I already had trouble getting hard with this guy, and now that I was sore, it was hopeless to try to get hard because if his popper-huffing and loose hole weren’t distracting enough, now o had pain to contend with. His weight on top of me riding me just wore on my hips after a while and it began to hurt. So he finally jerked himself off while riding my flaccid dick and came, then I pulled out and half-heartedly jerked myself to semi and managed to bust a load on him. I am known for cumming fountains worth of jizz, but this was a pathetic load even for me.
Volitionally
Probably 2 hours.
I know I’ve held off for a long time to cum just waiting for my partner to cum first. In the instance of 2 hours though, it wasn’t because they couldn’t reach orgasm, but because they were holding their orgasm off as long as they could cause they wanted the fullest load I could give them. It worked too, talk about one hell of a creampie.
My ex-gf and I would last a really long time. I just really enjoyed making her squirm and cum as much as I could, so I would prod her pussy for as long as it took for her to cum as many times as I could get her to before I couldn’t hold my own floodgates back any longer. Best of all, she was a squirter so it was even more fun to just overstimulate her with my large member - I’m so thick that my dick hugged her walls tight, and her clit was constantly stimulated by my thrusts, and as a bonus my dick is so long that it stimulated deep inside at her fornix, which prior to me, no guy had touched inside her before. Girl wanted seconds, thirds, and more. Most number of times we did it in a day was six and I was spent, something that’s very hard to accomplish with me haha.
It wasn’t 2 hours long, maybe an hour, but first time my bf and I did it, that hour was enough to build up one hell of a load release from me. When I finally came, I shunted my cock as deep as possible and just let it explode. My whole body was shaking, eyes rolling back, could feel the spurts just launching out of my dick forcefully deep into his insides. He said he felt so full from all I unloaded. A couple of days later, he said my load was still coming out of him - so not only do I cum deep, I cum tons haha.