Chapter 45

Author’s Note: We’re closing in on the end of Highway to Hell? Just a couple or maybe a few chapters to go. There will be some things to tie up here and others that will propel us into book four. Thanks so much for reading and the feedback. It’s a constant marvel. I hope you enjoy the continued ride!

It took me a couple days to process everything that had taken place. Kat was on a kind of spiritual retreat. We spoke frequently, and I became increasingly convinced she was going to come back closer to us and in a much better place. Jess seemed relieved at the realization that she could entrust more of her business to people like Alix. She had built a reliable team and could count on them. Rita and I also started texting constantly, trying to figure out how to increase the amount of time we spent together. Nicole started working as a real whore right away, hitting the ground running. And Crystal, my Baptist housewife, was begging for more attention – probably because the last vial of coke I had left her with was empty within forty-eight hours of our encounter.

Despite all this flying around our lives, I felt like we had come out through this period of unchecked hedonism in a stronger place than when we had entered. That hadn’t always been a foregone conclusion, or even a likelihood. I was excited about our prospects and thought about what next moves we should consider. But I also was easily distracted. I liked having a shiny new toy, which is what my budding relationship with Rita felt like. I liked having an outlet for my devilish, dark side to corrupt Crystal, an endeavor I really enjoyed. And, deep down, there was a thrill to the danger of having Nicole around. It gave life an element of uncertainty that could be fun. If it didn’t go wrong.

I woke up Thursday morning with my arms wrapped around Jess. We had crashed early after another round of sex. She stirred and smiled at me as I got out of bed.

“Guess what?” she said.

“What?” I asked as I walked into the bathroom.

“We have a whole day alone,” she said. “Just the two of us. When was the last time that happened?”

“Honestly, Jess?” I said. “I can’t remember. And that’s a problem. We need to prioritize it.”

“I agree,” she said, stretching her arms and legs and letting out a long, satisfied yawn. “Let’s not go anywhere. Let’s sit by the pool and get high and drink and see how many times we can make each other cum.”

“That sounds fantastic,” I called from the bathroom as I peed.

“Do you want to have breakfast or just smoke some weed?” Jess asked, appearing in the doorway. The morning sunlight captured her nude body perfectly. Shining between the gap in her thighs, it made her vagina look like a prime source of energy. Her hair looked like tousles of corn silk.

“You are so fucking beautiful,” I said. “Let’s smoke some weed. And no clothes today. None. God, I want you so badly right now.”

“I’ve never turned you down, stud,” she said.

“You did one time,” I said. “But I’ve forgiven you.”

“Should we try out that new vape pen?” Jess suggested.

“Sure,” I said, then added, “We are going to get so messed up.”

We sat near the pool and passed the THC cartridge back and forth. My phone pinged, signaling a text from Crystal. She wanted to get together on Saturday. As I started tapping out a message in reply, Jess asked who it was. I told her.

“What’s the real deal between you and her?” Jess asked.

I filled her in, in detail, on how things had transpired.

“She’s dying to get out of her marriage,” Jess said. “She doesn’t have the courage to do it to his face, so she’s going to force him to make the decision for her.”

“You think so?” I asked. “I think she’s just a naive girl who has been repressed and suddenly got infatuated with something naughty for the first time in her life.”

“She’s having you over to her house,” Jess observed. “She wants to get busted. That way he’ll make the decision to get a divorce for her.”

“That’s a good point,” I said. “But, at the same time, she seems to be really genuine in her love for fucking around. And, Jesus, has she taken to the coke fast.”

“You may be onto something there,” Jess said. “I actually think there’s a possibility she’s playing naive and isn’t really. Maybe she’s done this before. Some guys like to think they’re corrupting a woman for the first time.”

“If that’s the case, I wonder just how far I could push her down the hedonistic path,” I said.

“Honestly, John?” Jess said. “In either case, I think it could be fun to see how far she’ll go. Have you thought about how far you want to push her?”

“Do you want to know the truth?” I said.

“Do you want me to answer that like you do every time I’ve asked you the same question?” Jess shot back.

“Touché,” I said. “I’ve thought about this. Crystal is pretty. She’s fun. She’s a really good lay. I’ll be honest. I want to see if I can turn her into a bimbo. A Gloria-style bimbo. And I want to see – if she really is infatuated by escorting the way she’s implied – if I can turn her out. I want her to go to work for you. I want to make her a real, working whore.”

Jess laughed heartily.

“Oh, my god!” she exclaimed. “Could you imagine? What I wouldn’t give to have some super religious Baptist bitch come be a hooker. That would be so delicious. I want you to do it.”

“You think I should?” looking at Jess and smiling.

“I’m going to be disappointed if you don’t,” she said.

“Challenge accepted,” I told her.

The day with Jess was like a dream. It reminded me of when we had dated the first time around. We never put on clothes. Even after we swam, we just let ourselves air-dry in the sun. We fucked nonstop. At the end of the day, I had put seven loads inside her, and I felt like I could have kept going. We ate leftover pizza and watched movies. We never stopped kissing and touching. It was a day of such incredible intimacy, it served as a potent reminder that no amount of philandering and hedonism or anything else could overpower the connection with my girlfriends.

As we drifted off to sleep, early for the second night in a row thanks to the pizza and a sleepy wine buzz, Jess posed one of the most important questions she would ever ask me.

“Don’t you think we should plan a wedding sometime pretty soon?” she asked.

We were too tired to discuss it in more detail just then. But I let my hand run softly down her cheek, down her side, and then gripped her hand.

“Yeah,” I said. “We should.”

As the weekend approached, real life intruded on us again. Not that real life was bad for us. Kat had started to do video calls with us multiple times a day. She and Kelly were doing a lot of yoga and swimming. She seemed brighter and happier now, rejuvenated in a way I hadn’t seen her since before our leap into football season debauchery. She mentioned the possibility of cutting her stay short and coming home in a few days instead of staying another week. I was delighted at the possibility.

Jess had to get back to work, taking appointments on Friday and Saturday before getting ready for another football party on Sunday.

Rita, to my disappointment, had to cancel our standing Sunday date night. Her husband was coming home from his hunting trip that afternoon instead of his usual Monday, so she suggested we switch to Saturday. But Jess and I had planned to go out to dinner Saturday night, after her afternoon appointment.

“Invite her over,” Jess said.

“But we’ve got date night,” I said.

“John,” Jess said, looking at me seriously, “I know how you feel about Rita. You’ve told me how you feel about her. If this goes down the path you want? I need to know her better. I think she’s great. But let’s make it a date night for the three of us.”

“Are you sure?” I asked.

“I would love it,” Jess said. “I’m not making a concession at all. I want to welcome her into this crazy world we’ve created.”

At that moment, it hit me hard for the first time that Rita really could be my girlfriend. I knew Kat was fine with it – more than fine, she was incredibly excited. She loved Rita. This invitation from Jess was a huge step. I was bursting with happiness, and lingering in the back of my head was

So I texted Rita and said, “Why don’t you come over for dinner here Saturday? Jess will be here.”

“Is that okay?” Rita responded immediately.

“It was her idea,” I said.

“I’d love to,” Rita replied.

And that’s how, on Saturday night, I found myself at the dining room table with Rita and Jess eating steamed mussels and homemade french fries. I was anxious about the evening. Jess and Rita were friendly. They had played together before. But we all knew this was different. Rita knew I had told Jess about my feelings. Jess knew Rita was receptive and eager. Yet the conversation flowed naturally. Rita talked about work, and Jess talked about the agency with a particular focus on the football parties. The girls had a natural rapport. Dinner passed by quickly and easily, with three bottles of wine bathing the festivities in good spirits.

After dinner, Jess casually turned the conversation more serious.

“So, Rita, I have to say,” she began, “that I really like you. You are so much fun. You’re so cool. Obviously, you’re so beautiful.”

“Thank you,” Rita said, beaming.

“But I am compelled to ask if you know what you’re getting into,” Jess added.

“What do you mean?” Rita asked.

“John, be a dear and grab the tray from the bar, if you would,” Jess said, directing me to bring the cocaine over. “We adore you, but you two are in a honeymoon phase. I don’t mean to scare you, but I want you to come into this relationship with your eyes open. John has appetites.”

I put the coke in front of Jess and smiled at her. I leaned down and kissed her.

“I do have appetites,” I said with a laugh.

“What kind of appetites,” Rita said, briefly becoming uncomfortable.

“John likes variety,” Jess said. She bent over and snorted two lines. “You have to be okay knowing he might go to the Hooker House and play all day.” She rubbed her nose and smiled contentedly. “He loves my whores.”

“I know John is a ladies man,” Rita said.

“He also likes his little projects,” Jess said. “Like this new girl, Crystal. God, I can just see how we’re going to ruin her. In the best way possible.”

“I’m not sure I know about Crystal,” Rita said.

I sketched out, slightly sheepishly, what I had been doing with my Baptist housewife and the goals Jess and I had discussed for her.

“That’s audacious,” Rita responded. “And sexy. What a power trip that would be.”

“Does it turn you on?” Jess asked.

At this point, I worried a bit that this was too much for Rita. Maybe it was more than she had bargained for. Maybe she would bail. The look on her face betrayed no position, either positive or negative. She merely met Jess’s gaze and sat there for a moment. Jess and I exchanged a brief glance, waiting for Rita’s response.

She finally gave it to us. From under the table, she held up her right hand, which was glistening and coated in her vaginal fluids.

“Does this answer the question?” Rita said and flashed an electric smile. “I want to be part of this. I’ve never felt more satisfied, curious, and fulfilled in my life. I’m in. I’m all in.”

Jess beamed at her. She stood up and slid the cocaine tray over to Rita. As she did so, she bent down and licked her sticky fingers clean.

“You taste so sweet,” Jess said. “You want to do a couple lines, and then we can drain John’s balls of every last little bit of cum that’s in them?”

Rita was already snorting an indulgent line of coke before Jess finished her sentence.