NOT Your Grandma's Book of Progressive Erotica: Vol 4

High Roller

"Does your husband know you're spending all his retirement money?"

The older lady I directed the question at was gambling away at two slot machines, pressing buttons on both at a leisurely pace. Her graying blonde hair was curly, her eyes a faded green and the lines on her face indicated lots of laughter in her past.

"Actually," she said, turning towards me as I stood next to her, "he doesn't. He never will. He's dead."

"Oh, I'm–"

"No need to apologize my dear, have a seat."

I felt bad making such a joke, but she insisted that I take a seat at the second machine she was playing.

"I could use the company," she continued. "You can play this machine for me if you'd like?"

After making such a horrible joke, I felt a bit obligated to help her out at that moment. It wasn't very often that I was so stupid and bold, but at that moment I wished to bite my own tongue. She spoke willingly about her husband for a bit, talking highly of him and saying he left far too soon. It was just after his retirement that he passed away. She said it was a cruel punishment for him to have dedicated so much of his life to work to then get cheated of his retirement when it finally came.

"I'm sorry to hear that," I said as she finished her stories of him.

She smiled and then pushed the machine's button again. "I'm managing without him though. Tonight I found a young stud." She laughed.

I couldn't help but laugh and compliment her on the joke after mine had so horribly backfired in my face. We played for a while, her handing me more twenty dollar bills, one after the other as the machine ate them up with a never ending hunger. That was until the machine I was playing for her hit the jackpot.

"You won!" I said excitedly to her as she stopped playing her machine.

"Oh good," she replied. "Now I'll have all my money back and we can go for a tea."

When the Casino worker counted out the money into my hands, I handed her the money immediately and she tipped him a five. He thanked her and then carried on as I played the remaining few dollars left in the machine. Before she put the money in her purse, she handed me a hundred dollar bill and closed my hand around it.

"Please, I insist," she said sweetly.

I nodded. "Thank you, it's very kind of you."

Walking out of the Casino gaming floor, we headed to the nearby coffee shop where she bought teas for both of us. I would have used the bill she gave me, but they had a sign that read 'No hundreds accepted here'.

Riding in the elevator up to her room, I sipped on my tea. I followed her to the room and once inside, she turned on the television and insisted I watch as she freshened up in the bathroom. After about ten minutes, I heard the door finally open.

"Do you mind helping me with the toilet?" she called out. "I think someone forgot to unplug it when they cleaned it."

Standing up, I set the remote down on the television stand and walked to the bathroom. When I rounded the corner, I found her standing there butt naked with a smile on her face.

"Oh my God," I said, turning away in embarrassment.

"Please, don't be shy. You're such a nice young man. I feel as if I owe you a little something for spending some quality time with me."

I slowly turned back to find her walking toward me, sagging breasts, blonde bush, rather flat stomach and an erection creeping up on me in my pants. As she stepped within a foot of me, she kissed my cheek and then groped my crotch. She was shocked to find me getting hard already and knew that I wasn't going to back out of having sex with her.

As I walked over to the bed, she lifted my shirt up and I finished taking it off. Getting down on her knees, she undid my pants and then started sucking my cock. For an older lady, she definitely knew what she was doing. Her body aged considerably well and I found myself enjoying the moment more and more as it carried on.

When she stopped sucking my cock, I took my pants off completely and then joined her on the bed. I straddled her chest and began to titty fuck her saggy breasts; it might have been a sign of old age, but it was a blessing since it made the act much easier to partake in.

Minutes later I was now rubbing my cock up and down on her slightly hairy pussy. Despite the lack of trimming, her pussy didn't look bad, nor feel bad. As I slid my cock into her pussy it felt wet and warm just like any other.

"Ou," she said excitedly. "Big boy."

I smiled as I fucked her slow and then began to pick up the pace as she began to talk dirty to me. Moaning was something I was used to from younger woman and occasionally dirty talk, but this older woman was surprising the hell out of me.

She went one step further when she asked me to fuck her from behind and pull on her hair as I periodically slapped her ass. It jiggled like crazy as I fucked her from behind, but I rather enjoyed it. I had never considered having sex with an older woman before, but after this, I was ready to try it a second time.

"Oh my," she whispered.

Rubbing her pussy as I fucked her from behind, she squirted all over the bed and I could feel my balls getting a bit wet as well. I pulled out and then jerked myself against her wet pussy until I came into her hand. Surprising me the most was the fact that she ate my cum after it landed in her palm. I expected her to walk to the bathroom to wash her hands, but instead she ate my cum willingly, or out of sheer curiosity.

As I finished cleaning up in the bathroom, I walked out to find her already dressed and ready to go back to the gaming floor for some more fun.

"Going back already?" I asked.

"Yes," she replied. "I feel as though I have a second wind, so I'm going to use it."

"Well, good luck then," I said, putting my pants and shirt back on.

"Thank you. If you're ever looking for me, I should be in the high roller section."

"Why do you want me to find you?" I asked.

"Because I'm a sucker for punishment."