Chapter 5

Author’s Note: Thanks for your time and votes, readers. This chapter sees John make a key decision about how he’s going to handle this new lifestyle. This is kind of “soft rock” debauchery here, but it’s key to what’s happening moving forward. Enjoy the ride because it’s going to be a ridiculous tour through debauchery!

Shelly and I had another round of anal sex that night before she went home. I dared to think she was bordering on becoming a legitimate anal enthusiast after I was done with her. Two more rounds of booty bumps probably hadn’t hurt the cause. Regardless, it was a genuine pleasure defiling such a beautiful girl’s ass. The natural high of playing anal teacher coupled with the fair amount of cocaine I had ingested myself put me in a wired, frisky mood. I wanted to play predator. I wanted more pussy. I was going to find it, and I was going to get it. This was a feeling that had laid dormant for several years now, and they rushed back with force.

After Shelly left around 1 a.m., with no word having come in from Kat or Jess, I decided to start my hunt. If there was going to be more alone time, I needed multiple options to fill it with fun. Jess’s agency girls were a great resource, of course, and I enjoyed them. A lot. I could stand to play with some of them more often. But now that a sleeping giant had been awakened inside me, I wanted to play the field again.

I settled into the couch with my laptop and a fresh bottle of wine. I was tipsy, high, and wanting to scratch an itch that had gone ignored for too long. I wanted college pussy. Coeds who swooned over unimpressive amounts of money and a little bit of coke had always been a weakness of mine. So I followed an old pattern on where to find the low-hanging fruit when it came to that demographic. I hit a sugar baby website, signed up for the highest level of premium membership, and threw myself down the rabbit hole of searching for 18-23 year-olds in the Houston area.

There was no shortage of candidates. I had become pretty good at weeding out the fakes, like the girls who obviously weren’t in college. With the abundance of colleges and universities in the area, I had sent messages or winks to about a hundred girls in a couple hours. If I found a half-dozen to fuck out of that, I’d be in great shape. I was plowing through the wine and had bumped on coke a couple more times. And, before I knew it, it was past 3 a.m.

I wasn’t tired, though, so I decided to press on. I got on a dating app that focused on casual hook-ups, but it let women make the first move. I hadn’t realized that it was not long after bar closing time on a Saturday night, and almost immediately my phone notifications lit up with matches. My profile, probably due to my inebriated state, was extremely blunt. I made clear I wanted no-strings-attached fun, was wealthy and not afraid to leverage that to get what I wanted, and wanted girls who were open-minded in their desire to party.

Within a half hour, I was texting with a 24-year-old hair stylist who, if her pictures were accurate, was built like a brick house. Aside from a garish tattoo of a feather on her left forearm, she was gorgeous. Once I got her real name -- Riri -- I was quickly able to find her Instagram and confirm she was being honest about who she was and, more importantly, see she really was a knockout. She was half Latina and half white, giving her an exotic appearance. Her tits were large DDs, and I got a kick out of it when she told me they had been enhanced by the late Marco Vivianno. Her butt was juicy, and it appeared she liked dressing to show off. This was the kind of bimbo I could get in trouble with.

I talked a big game, wanting to take my new wealth and its power out for a spin. Riri was gentle about wanting to make sure I was real. She had a healthy skepticism forged by past scam artists. That was a double-edged sword. It probably meant she was serious. On the other hand, it might indicate she was jaded, which would just put me in a sea of negative boredom. But I was fucked up, and she was the first real fish to tug on the hook, so I decided I needed to fuck her. I was honest, and I assuaged her fears. I sent her a picture of me holding up three fingers, like she requested. That broke the dam.

Riri upped her game. She sent some lingerie pics. I pushed her hard for more. I told her we should go to Vegas. She was skeptical that I was serious -- or had any Vegas connections.

“I’ll fly you out on a private jet,” I said.

“Bullshit,” Riri said.

“Let’s go tomorrow,” I said arrogantly. “Name the time.”

“Can I bring a friend?” she offered.

“Is she hot?” I asked.

“And easy,” she said.

“Send me a picture,” I said.

Riri did. Her friend was hot. Taller and skinnier than she was. A fit blonde with bolt-ons. An interchangeable hot chick. I would fuck her in a heartbeat and enjoy it.

“So?” Riri asked.

“I’m dead serious,” I said. “Let’s go to Vegas.”

“I can’t tomorrow,” she said. “I have to work this weekend.”

“You’re a flake,” I teased.

“Could we go Thursday?” she said.

“Are you serious?” I asked.

“Yes,” she said.

“You and your friend?” I said.

“Yes,” she replied.

“Send me a nude,” I said crassly.

Without complaining, a picture quickly showed up in my texts. She showed her face and everything. It was a bathroom mirror shot, with her leaning forward, letting her impressive breasts hang, showing off pale pink nipples. Her pussy was completely bare. She looked like a delicious slut.

“You like?” she asked.

“Vegas Thursday,” I said. “Tell your girl.”

“I’m not going to believe you until we talk on the phone about it,” she said.

“I don’t flake,” I said. “But let’s talk tomorrow.”

“I have to go to bed,” she said. “Work starts early.”

“Shame you’re not here,” I replied. “You could just do another line with me.”

“Liar,” she said. “You’re too old to really party.”

It was stupid, but I sent her a picture of the pile of cocaine on the coffee table in front of me.

“Holy shit,” she wrote.

“I’ve got nothing to bluff about,” I said, “so there’s nothing to call me out on.”

“Thursday,” she said. “It would be nice to meet for a drink beforehand. I don’t know if you’re a serial killer or something.”

“Wednesday night happy hour,” I said. “Bring your friend. I’ll give you each $500 for the trouble.”

I put down my phone and realized the sun was coming up. I didn’t know what time it was, and I didn’t care. I poured myself another glass of wine and sniffed a short line of cocaine. Fuck yeah, I thought, Vegas with a couple twenty-something sluts. That’s exactly the kind of boondoggle I needed.

The front door opening shook me out of my intoxicated daydream. If I had a silly grin on my face at the thought of cavorting with silicone sluts in Sin City, it must have gotten even sillier when I saw Kat and Jess walk through the front door.

“Oh my god, babe!” Jess said. “You’re up early!”

“Hi daddy!” Kat added.

It was obvious they were as fucked up as I was.

“Girls! Holy shit!” I said. “You look like two well-fucked whores!”

“Daddy, you’re high!” Kat said. She ran up and kissed me. Her mouth tasted like peppermint. It was the only clean thing about her. Her dress was wrinkled and akimbo. Her hair was a tousled mess, looking as wild as her massively dilated eyes. Her makeup was disheveled. She reeked of sex.

“Have you been up all night, sweetie?” Jess asked. She walked to me and also gave me a peppermint-heavy kiss. “Is Shelly still here?”

“Shelly took off a while back,” I said. “I was just missing you two, so I decided to stay up.” I don’t know why I lied about what I was doing. I didn’t need to.

“Aw, look at you,” Jess said. “That’s so adorable. You wanted to make sure we were okay.” Jess looked as used as Kat. The pink, vinyl dress remained painted on her, but her hair was now down and wild. Her eye makeup streaked her cheeks. Most prominently, it was clear there was cum all over her body.

“It looks like you could both use a shower,” I said.

“At least a real shower and not a cum shower,” Jess said.

“I know,” I said. “That’s why I suggested it. They really made you earn your money tonight, huh?”

Kat shrieked and pulled a banded stack of $100 bills out of her purse.

“Ten grand plus another two thousand for a tip!” Kat said excitedly.