The story about the game of Twenties here on solo touch reminded me about the game of Thirties my friend/roommate/JO-buddy and I used to play.
We would bet something on the game, washing the dishes, taking out the trash, a token amount of money, etc, as well as cleaning up the aftermath.
The game was an endurance game: To take turns trying to last thirty strokes inside my ribbed Fleshlight (an excellent sex toy for masturbation). If you nutted in your thirty strokes, you lost. If you stopped pumping it, you lost. A little pause between strokes, not too excessive, is ok. We would sandwich it between the mattress and box spring of his bed to stabilize it, and you would basically fuck the toy. The only rule was that you don't ejaculate for twelve hours before playing, to level the playing field especially for me, since my roommate masturbated so much more than me. Occasionally just to change it up we'd play with condoms on, but normally without. Cheating in this game is pretty impossible since the ribbed Fleshlight produces such intense orgasms they are very hard to hide.
I'll give you an example of one of my finer moments. I'd had sex for hours with my girlfriend only 15 hours prior and, only cumming once, had blasted a pretty huge load on her breasts, so my balls were spent and I knew this when I bet a trip to the grocery store on the game.
I lost the coin flip and started first. Now if you have ever used a fleshlight, especially a ribbed one, you know how intense it feels. After 3 rounds (90 strokes) my cock was as hard as possible and the head was red and about to burst. As I'd finished the 88th stroke or so I'd felt the load starting to rise in my loins, but stopped just in time. I had a little drip of white cum hanging from my cockhead as I pulled out, but it doesn't count as it's not a full ejaculation. My friend pumped away for the next 15 seconds or so with his eyes screwed shut. He looked to be handling it easily. I was sunk. I knew I would probably cum immediately upon reinserting my impossibly hard, engorged dick into the fake pussy.
He speedily pumped, and neared stroke 30, but then to my surprise, didn't slow down. He didn't stop either. He kept stroking, faster. 35, 40, 45. After about 50 strokes he stopped, pulled his dick out along with a strand of cum hanging from the head, and said, 'I lost.'
As soon as he said this, I forcibly pushed him aside, stuck just my dickhead inside the fleshlight, and let go with an extremely strong orgasm that had me gasping and gripping the bed sheets.
He clapped me on the back, said his orgasm had sneaked up on him and he hadn't realized he was even cumming until it was too late, told me I look like I'd just had one of the hardest cums of my life, and then stood up to get dressed and go to the store.
I pulled my head from the toy and stood up also, but to go to my bed and crash after such an orgasm!