Most I’ve ever made a guy cum was 27 times in one session and all of those happened in the span of about 5-10 minutes

Got him really warmed up and started fucking him with a dildo while I alternated between whispering in his ear, biting his neck, playing with his chest etc. After only a minute or two he shyly muttered out that he was going to cum. I stopped, stared directly at him and we had this brief, telling moment of eye contact before he got so embarrassed he had to turn away. We both knew he was under the impression he couldn’t cum without touching his dick and the fact he almost just did was so fucking hot to me.

I pinned his leg over my shoulder and continued. Within a minute he was back to how he was before, just on the verge and I kept moving it while he shook beneath me. Finally let up after he came all over my hand and I asked if he’d cum sarcastically to make fun of how obvious and hard it was and he just whimpered out “… I came twice”

He absolutely should not have told me this because as soon as I knew making him cum over and over was on the table I was determined to go as far as I possible could, and hearing him say two like that was addictively cute. I Pinned him even more and continued, told him to count every time he cums before quickly getting back into it.

27 times I made this very masc dude cum. 27!

Didn’t even think that was a possible number. Every 15-30 seconds I’d feel him tense up and clench on the dildo then I’d hear his little chocked voice murmur out a number before I kept going. He made a giant fucking mess, squirting basically each time in the beginning. I kept moving the goal post further and further, “come on let’s just get to 10 puppy!”, “I think we could do 15 don’t you?”, “Whoops that was a 16th one, well we might as well get to twenty, right?”. He was fully trembling, shaking, crying. His eyes were in constant state of being rolled back and the noises he was making were so intense. The best part was hearing him count though, it was the only coherent thing he would say and he struggled to get out each number but if he didn’t count I’d start choking him.

Hearing a grown man moan out “25” or whatever ridiculous number we were on has to be one of the hottest things I’ve experienced. I would have kept going forever but he was begging and pleading for me to stop and for some reason I don’t think he believed that I’d really let him be done at 30

He was a complete fucking mess after as you’d imagine. Basically just sat there in a daze for 10 minutes but I made sure to make fun of him. I mean 27? Really? Just an embarrassingly high number. He also physically couldn’t handle any play for like several days after this so safe to say I throughly worked him out.