Chapter 4

I got Jess the eight ball. She went to work preparing it as she told me about her third sugar daddy.

"With the oil and gas guy being so vanilla," she began, "I needed something more exciting. I went back to the site. I wanted to find someone who seemed, I don't know, almost dangerous. That's when I found Peter."

She stopped her narrative for a moment to snort two healthy lines of cocaine. I followed suit.

"That is not bad for being captive on an island," I said. "So often they cut it to shit."

Jess kissed me, and there was emotion behind it. "I want you inside me when I tell you the rest of this," she said. In a flash, her dress was on the floor. She led me to the bedroom and started telling me about Peter as I undressed.

"He was a lawyer," she said, slowly playing with her pussy as she told me. "He had an interest in bondage, but like in a Fifty Shades sort of way. He was tall and handsome, and honestly he reminded me of you, which is why I agreed to meet him.

"We met for a drink first, and he was a perfect gentleman. I almost didn't believe there was a darker side to him. Then we met for dinner, and I was convinced he was full of shit because he was just so sweet and proper, and I was getting bored with him already."

I climbed on top of her and slid inside. We took a moment to savor the glove-like fit of her pussy around my cock. I noted how wet she was as she recounted her exploits.

"I think he sensed I was getting frustrated," she said and paused to gasp as I savored giving her long strokes with my cock. Our hips moved in unison, like a wave. "When all of the sudden, just as our cocktails arrived, his face turned cold and hard. And in front of the waitress, he said loud enough for her to hear, 'Go take off your panties in the bathroom, and bring them back to me so I can see how wet you are, slut.' I think my jaw actually dropped to the floor."

I pulled my cock out of her, and her hand instinctively reached for it to put it back in. I wouldn't let her.

"And what did you do?" I asked, hovering the tip of my cock just out of her reach.

"Of course I did it," she said, happily. "He took me to his place that night and gave me $2,000 in cash. He showed me the permanently installed restraints on his bed. He had one wall of his walk-in closet that had all kinds of BDSM toys hung from it. There were only two problems with him."

I plunged back in, touching her cervix.

"First, his cock was short. It was super thick, but it was short. Not even six inches," she said. "It was hard to cum with him as a result. And, second, he would get so rough it would put me out of commission for two or three days so the marks could heal."

I was dumbfounded at how Jess could surprise me so greatly. She kept me off balance, and I loved it.

"But oh my god the money!" she continued. "The rougher he was with me, the more money he gave me. Like one time he had this contraption where I was on my knees, with my arms spread to the side and above my head and bound that way to this metal bar. And he used a riding crop and flogger all over my body. It made me so wet, being deprived and teased for like three hours. He gave me $5,000 for that one evening. And that's when it occurred to me that no matter how rough he was, I had all the power. I loved it."

I took the pause in her story to slip out of her pussy and line my cock up against her asshole. I was eager. This was a new Jess. Her love of power in this context showed she was still a people-pleaser, but she also prioritized what it gave her strategically. She really had undergone a tremendous amount of personal growth. I glazed my cock head in her pussy juice before pushing the tip into her ass.

"I never pegged you for the hardcore bondage type," I said casually.

"It's not that," she said. Her face registered mild discomfort as my cock worked its way in her ass, then bloomed in satisfaction. "I learned that I was collecting secrets. Being a slut? You're just out there collecting pleasure and making memories. I realized I had achieved a more powerful position by sugaring."

"My little Jess is all grown up," I said, savoring the view of my cock sliding in and out of her ass so effortlessly. "But still an anal slut."

"I think I might want you in my ass more than I want you in my pussy," she said.

I hooked Jess's knees around my elbows and drove her legs above her heads as I thrust in her ass. I was penetrating her as deeply as I could. She howled in pleasure and urged me as her panting increased. Her ability to take rough ass fucking was a marvel. I didn't stop for a moment when she screamed out, announcing her orgasm. I kept going, pushing myself to the brink. I admired Jess's golden hair, spread out on the pillow below her, and the sparkling blue eyes. Everything about her urged me on, and I pushed her feet above her head as I drained my balls into her ass.

She held me close, arms wrapped around my back, as my cock twitched.

"That is my favorite feeling," she said and kissed me. "Think you've got another couple rounds in you? Let's get some coke and keep going."

She bounced out of bed, her body lithe and graceful. She returned with the cocaine, cutting it into lines as she sat on the bed.

"I think I just ruined these sheets," she said with a laugh. "You cum so fucking much."

I cleaned up in the bathroom and returned to see Jess forming two more lines. She had done all four herself.

"Being a greedy little coke whore?" I said.

"Shut up and do yours," she said. "Then you can face fuck me on the edge of the bed." She was already lying down with her hair nearly touching the floor.

I happily obliged. Jess had such a strong sense of how to keep me going nonstop. The coke and her mouth brought my cock roaring back to life in no time. She was very high, which stripped her of any limits. I didn't hold back in fucking her mouth. I buried it down her throat over and over and rained down a torrent of dirty talk with it.

"You want to be a full-time whore, don't you?" I said. "You can talk about power all you want, but you were the one getting your holes filled and getting abused. Selling your body for money. You just stopped giving it away for free."

It wasn't until I felt my orgasm rising again so quickly that I realized how turned on Jess's confession had made me. I saw her in a different light, not just the fun, in-the-moment hedonist she had been before. She was more strategic. I pulled out and came on her face, dotting it with a small load. I was panting hard, sweat making my body feel suddenly cold.

Jess rose up and grinned at me.

"You are an animal," she said. "That was so fucking hot." She was wired.

"You'll have to give me a little bit before I can go again," I said.

We went out on the balcony and smoked another joint. She hadn't even wiped the cum off her face.

"So what secrets are you collecting from me?" I asked her.

She laughed. "You don't have secrets from me," she said. "But I have learned that you love me differently now."

I nodded, feeling stoned and contemplative.

"I do," I said. "It's less superficial."

She climbed on top of me as I lay on our double lounge chair and blew a hit in my face.

"We're only going to go deeper," she said confidently and gave me a kiss.