This happened a few weeks ago, but I (19F) lost a bet to a coworker (26M) and had to pay up.

We had a flirty relationship but he always had a girlfriend so it was more roasting each other and teasing than anything else.

He would always tell me how sexy his gf was but that she was awful in bed. (she really is pretty AF.) even telling me at one point that he couldn't cum when they did stuff unless he was fucking her.

Me being how I am gave him a hard time and called bullshit. and I told him he probably didn't even make it to the point of having sex before he came. he of course disagreed.

I teased him over being a "minute man" for at least a month before he got mad at me one day and said that he would prove it and went to show me a video. which, while tempting, I wasn't about to sit there and watch some out of focus video of him and his gf.

So I shot him down saying it wasn't my fault that his girl couldn't work a dick. I made the mistake of saying that all dicks are the same and that I could make any man cum in under five minutes with just my hands.

(to be fair, I was messing with several men, outside of my relationship at this point and I had yet to encounter anyone who could prove that wrong.)

But he called me out on it and said to prove it. I said I'd bring a video in. He told me no and pulled his dick out right there in the car and told me to get started and that I was done calling him a minute man.

The terms were that if I couldn't make him cum I had to do whatever he wanted for a week, and if I could, he had the same deal. (I know I was about to give a hand job but I honestly didn't think it would be a sexual punishment at that point. )

Well I failed to make him cum in my 5 minute limit. as soon as the 5 minutes were up he said he wanted his payment to start right then. and he grabbed me by my hair bun and pushed my head down to his dick and fed me his throbbing cock… he came in my mouth no more than a minute after that.

I gave him a blow job everyday that week during lunch, which usually got him off in 5 to 10 minutes. I also had to fill out all his counselings and inventories which was a huge pain. by Friday I was ready to be done.

Friday was an early day and we were getting off work around noon so I thought I was getting out of my last day of "punishment," until he asked me to stay late and help him clean up. I did, and I also figured at this point he wanted his Friday to end on a high note so I expected that I'd be paying up after all.

Once everyone was gone and we had cleaned up he sat down at my desk with his legs opened up to me and said, "last time." I grinned and got down on my knees, pulled his dick out and got to work.

We were a couple minutes into it when he stood up and grabbed me by my hair and shoved his cock down my throat. it caught me by surprise and gagged me, which made it really wet as he fucked my face harder and harder for what felt like several minutes. as I pushed him off me to catch my breath he pulled me up by my hair and turned me so I was facing away from him.

He pulled my pants down and pushed me forward to bend me over my desk. I can't lie, I didn't even try to resist. I was pretty turned on myself and he hadn't tried to fuck me at all before now so I was excited. I was excited up until He shoved all 7 inches of his dick straight into my ass. I like anal so my asshole is used to it, he was not gentle at all and I liked it.

He bent me over my desk, with my pants around my ankles, pulled my hair and fucked my ass relentlessly. every thrust felt better than the last and felt deeper than the last… it felt so good as I was rubbing myself. and just as I was going to cum, he stopped and pulled himself out of me.

Snatching me by my hair he pushed me back down to my knees and moved his cock to my face and shoved it straight down my throat. it happened so fast I didn't even really process what bad happened until I was already gagging on his dick.. he grabbed my hair with both hands and fucked my mouth like he had just fucked my ass. after one especially deep thrust he pulled out of my mouth and came all over my face and shirt I was still wearing.

He laughed at me as I was still gagging and asked me if he was still a minute man.