Traffic Girl - Highway to Hell? Ch. 04

Author's Note: You'll get an idea of our path forward here. I hope you enjoy. I keep saying it, but this book will take some dark, filthy turns before we reach the end. Thank you for reading!

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"Babe, we're coming in hot," Jess said. "But I need you to do something for us, okay?"

"Okay," I said.

"You can't see us right away," she said. "We have to go change, and then we can show you the makeover. Got it?"

"Got it," I said. "What do you want me to do?"

"I don't care," she said. "Just make sure you can't see us walk from the front door to the bedroom. Once we're clear, wait for us to come out."

"I'll be out by the pool," I said.

"With your back to the windows," Jess admonished me.

"With my back to the windows," I repeated.

It was nearly eight o'clock on Saturday night. Kat and Jess had left the house at ten o'clock that morning for makeover day. I was desperately curious to find out what it all entailed, and here I was, tantalizingly close to finding out.

I took my glass of white Burgundy outside, immune to the suffocating humidity and heavy, windless air. It felt like a beautiful evening to me. I relished the sound of the waterfall trickling into the pool. The soft orange of sunset lingered. I closed my eyes and smiled. There were no requirements in this life other than to live it to its fullest. We were the embodiment of an Italian sports car. What else could you do but max out the throttle and take it out on a curvy road? Just don't crash it, I said to myself.

I finished my wine and wasn't quite sure how much time had passed, when Jess texted me.

"Come to the bedroom, baby," she wrote.

Like a greyhound let out of the chute at the racetrack, I bolted inside. When I reached our bedroom, I thought I had walked into the dressing room at Bimbos 'R Us. The brightness of the colors caught my attention first. It was like a neon explosion. Kat wore a bright green mini dress that had cutouts around the midriff and sides. It was backless and tied around her neck. The exposed flesh indicated she had gotten a fresh spray tan. Her eyes popped with matching, bright green eyeshadow, which created a contrast to the bubblegum pink lipstick adorning her lips. Her hair was teased up, and she wore six-inch stilettos. She posed with a hand on her hip, one leg jutting out and showing a lot of thigh, emphasizing how the dress was shockingly short.

Jess beamed. She looked like a Barbie doll in a bright pink vinyl dress that could have been ironed directly onto her skin. Her hair was pulled back into a sharp ponytail, which framed the matching pink eyeshadow and shining bubblegum lip gloss. Her heels were clear. The spray tan stood out because normally her skin retained a slightly porcelain hue. And I realized that both girls' lips looked plumper. She stood confidently, legs shoulder width apart and hands on her hips.

"How do we look, daddy?" Kat said.

They beamed at me, awaiting my response.

"Like the most perfect, delicious whores the world has ever seen," I said. My cock stirred.

The girls approached me, exuding confidence and sexuality. Each dropped a hand near my crotch, teasing me over my jeans.

"So we look the part?" Jess asked, speaking slowly and drawing attention to her lips.

"It's a total transformation," I said.

"Do you like it, daddy?" Kat asked.

"I love it," I said. It was impossible to keep my hands from just trying to paw at and maul the girls. The bimbo look they cultivated with their presentation was like a magnet for sexual harassment.

"Does it turn you on to see us like this?" Jess asked. She was relishing this.

"Immeasurably," I said. "This is who you both really want to be, isn't it?"

"I feel free," Kat said. "There are so many dirty things I need to do."

"It is a need," Jess agreed.

My hands never stopped moving over their bodies. I was curious if they wore underwear. My sneaking suspicion is that they weren't. I wanted to play, and they could sense it.

"Should we show him the last surprise?" Kat said to Jess, glancing at her.

"Does he deserve it?" Jess said.

"I think he does," Kat said. "He's a good boy."

"Okay," Jess said.

The girls paused and then, in a coordinated maneuver, lifted their dresses above their hips. This confirmed my no-panties suspicion, but, more importantly, it revealed something totally unexpected.

"What do you think?" Jess asked.

My eyes were drawn to it immediately. In a moderate shade of blue, just below each of their bikini lines and to the left of their pussies, was tattooed an infinity symbol. The same symbol of Jess's escort agency. The same symbol I had engraved inside their engagement rings.

"Are these real?" I said, surprised.

"They're real," Kat said. She grinned.

"They're perfect," I said.

"We want you to know that the three of us are forever," Jess said. "But also that our pussies are full of infinite possibilities."

"And unlimited fun," Kat added.

I slowly ran a hand over each of their perfectly smooth mounds. Their arousal was palpable, and their skin was feverishly hot.

"So how are we going to celebrate my two perfect whores tonight?" I asked. "I kind of want to show you off looking like this. I bet I could get us into Steak 48."

"Hold on, cowboy," Jess said.

"Yes, daddy, slow down," Kat added.

"The key word you used is 'whores," Jess said. "We're working tonight."

"You are?" I said, slightly incredulous.

"Of course we are," Kat said. I sensed something new in her tone. It wasn't exactly empowerment. It was more like an odd style of liberation.

"Jonathan Summers just secured another round of funding for his latest venture," Jess said. "He's having a small party, and Kat and I are the entertainment.

I winced when I heard the name. Since I had witnessed what Summers did to Jess the night of Kat's divorce party, I couldn't get the images -- and Jess's emotional reaction -- out of my head.

"Don't worry, baby," Jess said, sensing my unease. "It's Jonathan and three new clients. It's not going to be like that with this group."

"Like what?" Kat asked. We hadn't ever talked about it.

"Oh, nothing," I said but then retreated a bit. I didn't want to keep secrets. "Sometimes I don't like how Summers treats Jess. It's a little... degrading." I chose my words carefully.

"Isn't being degraded part of what makes being a whore so fun?" Kat said. "I mean, besides the money." She smiled. She didn't get it, so I just let it lie. I laughed and brushed it off.

"Well, so it looks like I'm on my own tonight," I said.

"We may not be home until tomorrow," Jess said. "It's a possible overnight."

"But we're making $10,000," Kat added.

"That's major money," I said.

Kat beamed. "Am I a good whore, daddy?" she asked.

"Tied for the best," I said, glancing at Jess. They were in slut mode. It felt a little lonely to be left out.

"There are going to be times like this," Jess said. "Especially in the beginning. I just put Kat's first pictures on our web site. She's going to be very, very popular."

"Don't worry, daddy," Kat said. "We have a special plan just for the three of us tomorrow."

"And we aren't ever going to leave you high and dry," Jess said. "I'll always account for you." She gave me an adoring look before saying, "Oh! Jonathan's driver is going to be here any minute!"

The girls rushed to gather themselves and head to the door. They gave me air kisses, not wanting to ruin their makeup.

"Do you need anything?" I offered. "Condoms? Coke?"

Jess laughed. "I've got plenty of coke," she said. "And no condoms. Their tastes came back clean this morning."

"Clean tests mean extra dirty whores," Kat said.

And, just like that, they were out the door.

A couple minutes later, however, my phone buzzed. It was Jess.

"Hey, babe," she said. "Sorry, we had to run and didn't want to be late." There was some rustling in the background, and the phone was muffled. I heard Jess say, "No, no, Kat, here, take the bullet. Hold on." I heard a brief series of sniffs in rapid succession.

"Babe, are you there?" Jess came back on.

"I'm here, doll," I said.

"Sorry, we didn't mean to tease and run," she said. "But there's a lot of money coming our way tonight. I need you to do something for me, though."

"Anything, of course," I replied.

"I need to get Shelly ready for football season," she said. "Think of this as her training camp, if you catch what I mean. She'll be over in about an hour, okay?"

"Well, geez, I was looking forward to a quiet night with a book," I said and laughed.

"Johnny Burris really likes her and wants her at all the after parties," Jess said, ignoring my comment. "But you know what he demands."

"All too well," I said. "Go have fun. I've got you covered here."

"Thanks, babe," Jess said. "Don't forget how much we love you." Kat shouted, "I love you!" in the background.

"Be good for Summers," I said.

"You know me," Jess said cockily. "I'll be great."

We hung up, and I sat back on the couch. Shelly. That was an unexpected surprise. The younger sister of Jess's best friend, Melanie, I had become increasingly enamored with her since I fucked her. But, so far, it had been a one-time deal. The prospect of seeing her again, especially one-on-one, was tantalizing.

In the hour before Shelly arrived, I got a good amount of weed and various smoking implements ready. I remembered her preference for marijuana over cocaine. I also prepared an anal training station in the bedroom. I laid out three butt plugs, in order from small to large, along with Lelo lube, which I had found was ideal in keeping maximum lubrication without getting too messy. I also took out some cocaine and a medicine plunger, in case Shelly wanted to numb herself for the main event. I didn't know if Shelly had ever tried anal sex before, so I wanted to be prepared for the full range of possibilities.

I popped a bottle of Pinot Noir and sat down on the couch to await Shelly's arrival. My thoughts drifted to how things with Kat and Jess had evolved so quickly in the past couple weeks. They weren't kidding when they had made the decision to maximize hedonism. The tattoos, maybe more than anything else, indicated how serious they were about this. But also about us. A permanent mark, a constant and enduring reminder of our infinite commitment to each other. And their lives as escorts.

Escorts. I swirled and sipped the wine and considered this. These were two women I loved deeply. We had cultivated something honest and enduring, I firmly believed that. It was unique. It was debauched. It was ours. And it worked. Would it continue to work? Kat and Jess showed an undeniable zeal for this new, amped up lifestyle. I was fully on-board with it, but there were doubts that lurked in my mind. Doubts about safety, mostly. I knew Jess had cultivated a high-end clientele for her agency and a level of information-sharing that created a kind of mutual destruction scenario for the clients and escorts if they went beyond the rules. Still, prostitution came with inherent risks. Physical ones. Health ones. Legal ones. Nevertheless, those potentialities lurked in my mind shrouded in fog. The thrill of it, in part driven by those risks, made it even more delicious.

But one thing didn't sit right with me. The girls dictated the fun. Everything happening so far was on their terms. It wasn't their fault. I had been passive so far. I started wondering how I'd fill the time while they were out whoring around town. It wasn't something I had considered. The rapid change that came to our lives hadn't afforded me the time to prepare for it fully. As I did, however, it dawned on me how much freedom their work would give me. If they were out fucking for money? I could be left to my own devices. For the better part of five years, I had been singularly devoted to -- and fulfilled by -- my dual relationships with Kat and Jess.

Now, though, if I wanted to remain true to the "maximum hedonism" mantra we had instituted? Then I would need to find something for myself. I wasn't quite sure how to initiate it. Being the screener for Jess's whores was a good start, of course. Shelly would be a lot of fun to sample again. Part of me wanted something of my own. Maybe we would need more games, to raise the stakes by playing off one another. But maybe I'd also need to channel my old playboy bachelor self. With more money than I had ever dreamed of having, it could be delicious to see how much power it afforded me when it came to attracting the fairer sex. I immediately found myself drawn to the idea of discovering what women would do for a taste of this level of wealth. It settled in on me, and while I may have believed I didn't know how I would fill my alone time, subconsciously I knew it would be in pursuit of leveraging my money and lifestyle to get as much pussy as possible.

I was pouring a third glass of wine for myself, my thoughts already drifting into what avenues would be the best for finding new women to fuck, when the doorbell rang. It was Shelly, and she was right on time.

She stood nervously at the front door as I approached, tugging down the short, tight tube top dress she wore. The royal blue color flattered her gray eyes, which sparkled as I let her inside.

"Hey, stranger," I said and gave her a hug. "It's so great to see you."

"Hi, John," Shelly said. "You're right. It's been too long."

I guided her inside and to the great room sofas, noticing she walked a bit unsteadily in her tall heels. Her perfume was thick and cloying. Her luxurious brown hair teased like she was a pageant contestant. I detected a faint whiff of spearmint and wondered if she was chewing gum to hide her pre-game drinking.

"I have to say, this is a really pleasant surprise," I said.

She took out her gum and folded it into a tissue. "Jess said it was time my menu expanded," she said. Her voice was definitely unsteady.

"Don't worry about business," I said. "You're here as a friend."

Shelly laughed. "A friend with very specific tasks to accomplish," she said. I saw her eyes glance over the weed on the coffee table.

"Why don't we smoke, and you can tell me about it," I suggested.

"I would love that," she said.

I let Shelly take the lead. We went outside, and she packed a bong with bud. A few rips in, and she opened up.

"Football season is coming up," she said. "Johnny Burris made it clear to Jess that he wants me at all the post-game parties."

I nodded. This wasn't new information to me.

"And?" I said.

"He made it clear that anal needs to be on the menu," she said. "And Jess said so, too."

"So you're going to be my new trainee?" I said.

"All the girls say you're the best," Shelly said with a smile.

"You seem nervous," I said. "If you don't want to do it, it makes me less comfortable with it."

She smiled and took another bong rip. "You're too nice," she said as she exhaled a cloud of smoke. "A real gentleman."

I wasn't sure how to respond to that.

"Don't get me wrong," she continued. "I want to. I want the money that comes with it. I love the money. Jesus. But, like, does this make sense? I want to enjoy the things I have to do to get the money. I get it. It's a requirement. But I'm not the kind of person who can just put on a fake smile and say, okay, fuck my ass."

I laughed. "I get it," I said. "I totally get it. Have you tried it before?"

"Once," she said. "It hurt so bad I made him pull out as soon as he put it in."

"And when was that?" I asked.

"Years ago," she said. "In college with my boyfriend."

"Let me guess," I said. "No lube, and he didn't prepare you. Anal sex is not like regular sex."

Her bloodshot eyes lit up. "No! No lube!" she said. "Do you need it?"

"Oh, sweetie," I said, finally putting a hand on her thigh. "Let's start with a blank slate and pretend you never even tried that. Unless you've got an anatomy that simply won't accommodate anal? There's no reason it should hurt. It might be uncomfortable at times, but it shouldn't hurt if it's done right."

"For real?" she said.

The weed had kicked in, triggering my aggression when I was stoned. "For real," I repeated. "Do you want to find out?"

"Honestly, I do," she said. "I really think I want to find out."

Shelly was different from the other girls in Jess's agency. She gave off a more wholesome, innocent vibe. She wasn't as brazen and overt in her pursuit of lust. I think she liked being arm candy more than anything else, and she excelled at that. Her body was flawless, like a fitness model who retained all the curves of the sexiest cheerleader.

As it turned out, she also was an excellent student. It served as a timely reminder about what a powerful motivator money was when it came to some women, their bodies, and the access to those bodies certain financial incentives might give me.

We started with a lengthy oral session. I ate her out and mixed in an increasing amount of rimming her sweet ass. I was mesmerized by her supple skin and complete lack of tan lines. Shelly loved when I licked her asshole, and she pushed my head roughly between her cheeks as I tongued on it. When my face was dripping with her juices, and she seemed at ease with two fingers probing her ass, I decided it was time for toys.

I prepared her with some of the Lelo anal lubricant and took a slight risk. I skipped the smallest plug, which was smaller than the two fingers I had used on her already, and went straight for the medium. I instructed Shelly to do the same breathing regimen I had taught Rita in her first anal session. I ate her pussy some more while I worked the medium plug in and out of her ass. She was tight but showed no signs of discomfort. When she had her third orgasm of the night, I decided it was time for her to graduate to the largest and, finally, her ultimate test.

There was always something magnetically attractive to me about the mystery, trepidation, and anxiety in girls experiencing good anal sex for the first time. Accessing that forbidden hole never got old. Training a girl like Shelly to be paid to have her ass fucked? There was something primal inside of me that craved it and sought it out.

When it was time to use to the largest butt plug, I moved from between her legs to making out. I sucked Shelly's improbably pert, perfect natural tits on the way. Her lips were like pillows, since she had recently gotten fresh filler injections. It was the only enhancement she allowed herself. Her long eyelashes brushed against my eyelids while we made out. I maneuvered the plug into position by feel, spreading her phenomenally firm ass cheeks with one hand while gliding it past her sphincter until it nestled all the way inside. The whole time, I never took my lips off hers, our tongues dancing urgently.

Shelly pulled back and said, "Is it supposed to feel this good?" A wicked smile cracked across her face.

"If it's done right, it can," I said, returning the smile.

"Jess says guys pay a lot more for anal," Shelly said.

"At least a few hundred bucks," I said. "It's definitely worth a premium."

"Then I need to get good at it," she said.

"Are you ready to try it?" I asked.

"There's no reason to wait, is there?" she responded.

"Do you want some coke to help numb you up?" I asked.

"Like a booty bump?" she said. I nodded, and she said, "Yeah. I think that's a good idea."

I patted myself on the back for having the plunger prepared already and directed Shelly to get on her hands and knees. I injected the cocaine-and-water solution up her butt and, while we waited for it to fully take effect, had her suck my cock to get me ready.

It took almost no time for me to become fully erect. Shelly pulled her mouth off and said, "You know, when I first started sucking a lot of dick in college, I thought it was gross and weird. But guys liked it so much, I kept doing it and got good at it. And now it makes me so wet. I figure butt stuff is no different."