NOT Your Grandma's Book of Progressive Erotica: Vol 5

All In

Gambling was something that I found myself doing a lot. Work had cut my hours for the winter and so I was struggling to make ends meet. I was good at gambling; I would win more often than not. The problem I had though, was that I never knew when to walk away.

I went alone, which was ultimately my downfall. With no voice of reason, or someone to tell me I should walk away and buy a tea for the drive home, I was sucked back in every time. It didn't matter whether I was up a thousand or three thousand, I never could say no to that one final bet that would suck me in for another two hours or more. Glancing at my phone one minute, it would be just after midnight, the next it's four in the morning and I lost over half of my winnings.

Self control is something that I certainly lack, but I don't blame anyone else for my mistakes. I own up to the fact that I could have gone on vacation ten times over if I had been able to walk away. Just when I thought I could never leave without being up, I was given a dose of reality and put more than just money up for grabs.

The game was war, a straight up game where highest card wins. I was getting lucky all night long, winning hands while everyone else at the table was losing. When everyone else was cleaned out, I was the only person left, so I continued to play on by myself.

I checked my phone for the time and saw that it was almost three in the morning. I decided double or nothing was the best option to end the night and pushed a little over a thousand dollars worth of chips into play. If I was able to win this hand I'd have my rent paid for and some extra money to go towards school. It was actually the first time I saw the potential with the money and wanted so badly to be ahead for once.

As the cards were laid out, I saw a king followed by another king. Is was a tie which meant I could get half my bet back, or front the same amount and have a chance at winning my original bet and possibly more if I tied again. The temptation was too great, but I didn't have the money.

Sitting there as I tried to remember how much money I had in my bank account in case I wanted to withdraw the money, an older gentleman walked up next to me and realized I didn't have the money to continue. He placed an equal stack of chips down in front of me.

"Oh no, I can't," I told him.

"Go ahead," he insisted. "I just won it at Blackjack. I could easily win it all back again in ten minutes."

I was hesitant to use his chips, but if I won I could just go home with what I originally won and split the rest with him, or just give him all of it as a thank you. On the downside, we could both lose and I'd have to beg for an extra shift from a co-worker since I was gambling with my paycheque.

"I won't be able to pay you back if I lose," I warned him.

"Like I said, I could easily win it all back in ten minutes."

Pushing the chips forward, I felt a huge weight on my shoulders. The dealer burned three cards and drew me a deuce. Fuck. Their card comes a ten and I hang my head. I not only lost my winnings and my paycheque, but I just lost some stranger's money.

Standing up, I look at him and he's smiling.

"Why are you so happy?" I asked him.

"Because now you can watch me win it back at a game that doesn't have your odds so stacked against you."

Ten minutes later, sure enough he had won all the money back. He had not only his money, but my money as well. Playing with a large stack of chips made it easy for him to succeed in doing so, but I was speechless when he did it.

"I would give you all your money back, but I think I should get something in return. Don't you?"

The idea of having to earn my money back felt a bit like blackmail, but that extra shift at work wouldn't quite cut it.

"What did you have in mind?" I asked.

"Well I have a hotel room, so I'll leave it up to you."

Without thinking twice I lied straight to his face. "I'm on my period and I'm allergic to latex."

"Then I guess you know what you have to do," he said as he slid the handful of chips into his pants pocket.

I thought the elevator ride was long enough, but then as I waited on my knees for him to take off his pants, I felt as if time was slowing down. He was going to be enjoying himself while I on the other hand, was not. The amount of money I was getting back was too much to pass up and it was only a simple blowjob. He was an older guy, so I was expecting something quick since it probably didn't even work that well anymore.

When his pants finally came undone and his dick was staring me in the face, I realized what I had gotten myself into. It wasn't a large dick, but it was still an old man's dick. I looked up at him and then back down as I began to jerk him off.

Once I worked up enough courage to stick it in my mouth, I closed my eyes and imagined it was someone else. I did what I had to do with my tongue to make it enjoyable for him, causing him to moan and groan. The last thing I wanted to do was disappoint him and then get no money at all.

It seemed like a long time had passed and I began to wonder if he was ever going to tell me to stop. As the thought finished crossing my mind, he then grabbed my head and fucked my mouth as hard as he could. I started to gag, but before I puked all over him, he came into my mouth.