The Shot Glass Bet

We didn’t stop until he filled the shot glass.
NonFiction
A guy i knew in college messaged me recently and it reminded me of a story im sure some of you will appreciate.

So in college it was the first time i was on my own and i really took advantage of it to explore my sexuality. I hooked up with a lot of guys and experimented with a lot of kinks/fetishes i had seen or heard about but never tried. One guy specifically was super into handjobs and what i know now to be milking. So we chatted for a bit and he explained how he wanted me to jerk him off and tease and edge him until he couldn’t handle it anymore. Being the people pleaser i am, i made sure to do my very best to make his dream come true.

I had devised a plan that i would see how far i can push his fetish. So i had told him to make sure not to cum for a few days before we met at least. The day we met it wasn’t much of a meet and greet and more of a lets get down to business. I told him about my idea. I took a shot glass and told him i would keep jerking him off until he filled it fully. He was very confident of his ability. So much so he agreed to a bet. If he won, he got to be the first guy id have anal sex with. If not, he had to drink the contents of the shot glass.

We began like always, kissing and touching and groping until we were both fully naked. Then i started. Slowly at first, teasing his dick up and down. Watching him fight the urges to cum already. Using lube i made sure it was always wet and would rub around his head while he squirmed. This wasn’t the first handjob ive ever given but it was the longest and most attention ive spent on one till this point. After a bit he said he couldn’t hold it and to get the glass. He held his dick and pointed at the glass. To be fair he did get a good amount to start, but he messed up. He shot a bit outside the glass onto my chest. He said to scrape it off and put it in the glass. I did the first half but oops my finger got lost on the way and ended up in my mouth.

Now to round two. I continued right where i left off. No breaks. He was buckling in front of me. He was trying to muffle his moans and i was doing everything in my power to make him give up. But sure enough after a while he grabbed the glass and shot his second load. Not even close to the first amount but it was ok. He had filled about 1/2 of it at this point but i could tell he was losing momentum.

Round 3 and he had to stop. He was so sensitive he couldn’t handle it. So we took a break. hung out and made out for a while and when he was ready we went for round 3. This took a while but he managed to cum leaving us 2/3 of the shot glass full but we were running out of time and he was running out of cum.

Round 4 took the longest and he only managed a few drops. The reality started to sink in and he begged to go again. His dick was barely hard at this point. He started jerking himself but couldnt manage any more.

And there we were. The end of the day and we had a decision to make. Would he fulfill his end of the deal or back out? He sure tried to back track but i ensured him that would be the last time we met up. After i had gotten dressed and was ready to leave he finally agreed. In one big moment he shot the glass back and he swallowed what was almost a full shot glass of cum. I was shocked. Impressed he did it but shocked. He asked if we could meet again and i said wed see. Spoiler alert, we did meet up again but he didnt get to have anal sex with me. Sucks for him.

Anyways. Thats the story. A fun trip down memory lane. Hope you enjoyed.