Chapter 6

Author’s Note: Thanks for your patience as we’ve laid some key groundwork on the plot of this book. This chapter should take care of that, and we’ll have a longer stretch of sheer debauchery ahead. I hope you don’t get tired of it!

With nothing better to do and work gone as an anchor, it was too easy to throw myself head-first down the slide of scanning the app and sugarbaby site for hookups. Plus, it was fun. It was exciting. I threw myself into it with zeal, perhaps too much zeal, and I was only too willing to overshoot with girls I found attractive. In my target age group, which realism had caused to shrink to 21-25, flashing a couple hundred bucks for an initial meeting over coffee for the sugarbabies showed them I was serious. It also gave me some easy and rapid distractions while I was working on the harder nuts to crack -- or panties to drop -- on the app.

I never fully understood how girls on hookup apps thought they had higher moral ground on the sugarbabies. At least the sugarbabies got some financial benefit out of being sluts. Both of them got my respect, but why condescend to someone willing to take a little cash for the sex they would be having anyway?

At the moment, however, I wasn’t focused on the nuances of civilian hook-ups versus paying a sugarbaby. Instead, I marveled that Rachel, a cute blonde, had said yes when I suggested we duck into a downtown parking garage for a quickie. Like a couple high school kids, we laughed while scrambling up the stairs to the second level. It was largely deserted. At noon on a Saturday there was almost nothing happening in downtown Houston.

“Is this good?” Rachel said as she walked behind a concrete pillar that was in the corner of the empty floor. She was already unbuttoning her jeans with a sly smile on her face.

“Perfect,” I said, pulling my balls above the edge of my athletic shorts. I hadn’t even bothered to dress up.

“I can’t believe I’m doing this,” she said. “It’s so bad.” She put her hands against the pillar and bent over, the jeans now below her knees.

“It’s not bad,” I said, putting a good amount of spit on my hand and stroking my cock a couple times to wet it and get it harder. “Being naughty is always good.”

“It’s crazy,” she said, as she licked one hand of her own and made sure her pussy was ready for me. The hand stayed between her legs, working her clit as I entered her for the first time.

“Fuck, that’s so tight,” I said. A grin stretched across my face. Thirty minutes ago, we exchanged nervous hellos at a Starbucks across the street. We talked about how she loved going to the lake and traveling. I nodded along, being a good guy and attentive listener. Now I had just put my cock into her pussy without a condom. The dumb bitch hadn’t even asked to use one.

“Damn, you’re thick,” Rachel said. “That’s so good.”

“Your pussy is fantastic,” I said. “Goddamn, Rachel. You’re so wet.”

“Funny guys make me cream,” she said, throwing her cascade of blonde hair to the side and looking back at me with a grin. Her brown eyes showed the fires of desire. She was enjoying this.

“You sure it isn’t the big cock?” I teased her.

“That’s not bad either,” she said. “I really needed a good fuck. Shit. Don’t stop because you’re going to make me cum.”

I focused on stroking in and out of her. Her pussy frothed with thick cream. I watched her asshole, which winked as my thrusts went back and forth, and gave the distinct impression she was no stranger to ass play. I took the risk and licked my thumb before plunging it in her butt.

“You like it dirty, huh?” was all she said.

“You’re going to find out I’m such a dirty boy,” I said.

Her breathing changed. It got shorter and almost frantic. Her head dropped forward, and she bashed her hips back into my cock. We were sweating copiously. The humidity was already wrecking the day. My cock squelched now on each stroke inside her. She was close, so I decided to urge her on with some more dirty talk.

“You’re a dirty girl,” I said. “Letting a stranger fuck your pussy raw.”

Rachel seemed like she had something to say in response, but her orgasm took her over before she could. She simply screamed out, “Yes!” repeatedly, echoing loudly through the harsh concrete structure. When her pussy stopped spasming, I focused on myself. On filling up this stranger with a hot load of sperm. She was such a slut, I felt a mixture of derision for how easy she was and admiration ... for how easy she was. Ultimately, I adored women like this, the ones who would let me do what I wanted, when I wanted. It was a great first meeting that, as I got close to unleashing, was just about to get better.

“Oh, shit, here it comes,” I told her. After all the wine and cocaine the night before, my cum was especially thick and viscous. But it was a big load, and I enjoyed that Rachel seemed to relish feeling it spread inside her.

“Oh, yeah,” she said. “That’s my favorite. That’s so hot.”

I pulled out and quickly pulled up my shorts, instinctively glancing around to see if we had been observed. The parking garage was lifeless. Rachel bent over to pull up her jeans, pussy glistening from her arousal and my fresh creampie. She turned around and pecked me on the lips. It was our first kiss.

“That was fun,” I said.

“Let’s totally do that again,” she said, bouncing up and down from her tiptoes to her ankles. She was maybe five-foot-four and a bundle of energy. She paused for a moment. “So, um, were you serious about that gift for the coffee?”

I had promised her $200.

“Of course I was,” I said. “I’m not one of those flakey guys, okay?” I pulled out $500 from my wallet and handed it to her. “But just remember that I’m one of the nice ones.” Hook, line, and sinker.

“Oh my god!” she said, her eyes getting wide when she saw the five, crisp hundred-dollar bills. “You’re so nice. You can seriously text me whenever. What time is it?”

“A little before one o’clock,” I said.

“Shit, I’ve got to go,” she said. “My boyfriend is probably going to wake up soon.”

I chuckled. “Don’t get busted on my account,” I said. We walked down the stairs and out the front entrance of the parking garage, looking none the worse for wear if you ignored our sweat-covered faces.

“I’ll see you around,” she said. She glanced around furtively.

I simply gave her a brief hug, and we walked in separate directions. Ramping up the hedonism had been the best idea, I concluded. I headed home, pleased with my conquest, but totally unprepared for the surprise that awaited me.

“I didn’t realize that Tommy was a client,” I told Jess. I’d been home long enough to shower and see Kat off to her next escort date.

“I’ve got three dozen clients, John,” Jess said, a little defensively. “I didn’t realize I needed permission from you on their identities.”

“Come on, Jess,” I said. “Don’t be pissy. This is Tommy we’re talking about. You didn’t mention it. That makes me think you’re hiding something.”

“I’m not hiding anything,” she said. “It was a simple oversight.”

“Don’t lie to me,” I said. “You made Kat an appointment with him, and you told her it was a special one. You made sure she teased me about who it was with. You knew. You knew!”

“Okay, I knew you wouldn’t like it,” Jess said. “But he is a perfect client. I know he and I have a history, but this is about making money.”

“Have a history, Jess?” I said, scowling at her.

Tommy Boatman had been a central figure in the near-total breakdown of my relationship with Jess the first time around. Back then, he was in his late 20s. He was handsome, charming, and packed a really big cock. He was a classic underachiever who was really only interested in partying and pussy. Jess had been introduced to him by accident. One of Jess’s sorority sisters from college was doing engagement ring shopping and had asked Jess to join her. As it turned out, they shopped at a jewelry store where Tommy served as the manager. He was less the manager, really, than simply using it as a vehicle to pick up women. He had a particular penchant for attached women, and the store gave him a perfect avenue to meet them, as well as satisfying his family’s requirement that he do something productive with his time.

As soon as Jess had seen him that spring day, she lost all interest in helping her girlfriend ring shop. She saw Tommy’s football physique -- he had played in college -- and chiseled good looks, her panties were soaked, and she was a goner. He took her to lunch that afternoon, got her drunk on margaritas, and played to Jess’s love of animals by asking to have her meet his dog at his apartment. It was pretext, of course, and they both knew it. Within ten minutes, she was on her knees sucking his cock. A cock that, until Marco Vivianno, had been the largest and most addictive Jess had ever experienced.

Jess had been up front that she hooked up with Tommy. She played it off as a one-time thing, a novelty hook-up that had passed as quickly as it had surfaced. And then, six months later, I found out they had been dating since they met. She saw him four or five days a week, and she put forward a litany of increasingly flimsy excuses to me to cover her real whereabouts.

In short, Tommy Boatman had almost broken us. He was only too happy to feed Jess’s increasing coke habit back then, and learning he was back in the fold at a time when I saw Jess as vulnerable to those same dark forces now made me hesitate. About everything.

“He’s just a client,” Jess said.

“Has he,” I said, but Jess cut me off.

“No,” she said. “I made it clear that I won’t see him. He and I are done.”

“You realize that’s tough for me to believe,” I said.

“I know,” she said. “I’ve thought about that.”

“How did he find you?” I asked.

“One of my lawyer clients is his cousin,” she said. “He said he had a wealthy friend who liked women who were a sure thing. It turned out to be him. I didn’t even know it was Tommy until after he had already had appointments with Alix and Brittany.”

Hearing her say his name was like nails on a chalkboard.

“You can understand my skepticism,” I said.