Traffic Girl - Highway to Hell? Ch. 16

Story Info
A successful playboy raises the stakes. Can he handle it?
4.3k words
4.73
5.7k
8

Part 80 of the 207 part series

Updated 03/30/2023
Created 07/22/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Author's Note: Are we getting deeper in the darkness, or is there a hint of light? Let's find out. But not before I thank you, readers, for your spirited discussion and feedback on the recent chapters has been phenomenal! It's really flattering to see that kind of engagement. I know these recent chapters create a lot of emotions and tension about where things might be going. I hope, in the long run, you see that it is faithful to these three characters.

* * *

I left Kat tied and gagged for about three hours. I ran some errands, picking up new supplies of wine and liquor for the home and Hooker House bars, along with setting some plans in motion. I showered off at the Hooker House. The only question I was torn about was whether I should release her alone or ask Jess to come with me.

Jess was unequivocal and convincing in her answer when I asked her what she thought I should do.

"The three of us are together," she said. "We all make mistakes. It's important for each of us to know that we're loved and supported inside our relationship. I want to be there. I want her to know I understand your feelings and hers, and that we all need to be on board with the decision regarding how to move forward."

Jess and I met at home that Wednesday evening and welcomed Kat back to the land of the living. Red marks remained on her breasts, thighs, and around her pussy. The cum mostly had dried on her face. When I saw how desperately she conveyed her regret, I felt satisfied that we were back on track together. Almost. There was a detail that didn't sit right with me, but fortunately one of my stops that afternoon would help put my mind at ease.

And that's how we ended up here. In the great room. The girls sat next to each other on the couch, their backs straight in perfect posture. Around each of their waists was a black leather belted harness. They sported black leather collars, wrist cuffs, and thigh cuffs. Their arms were fastened behind their backs by leather harnesses that clipped their wrist and thigh cuffs together. They made an absolutely tempting and delicious sight.

The clerk at the store had called this package an "ObsessHarness." She said it was a personal favorite and noted that it was the perfect vehicle to assert control over someone. Who was I to doubt an amazonian blonde working at a sex store?

"John, these cuffs are kind of at an awkward angle," Jess said in mild protest.

I gave an amused chuckle. "That's weak, Jess," I said. "Take that shit someplace else."

"I'm so tired, daddy," Kat said. "Could we at least have a couple bumps?"

I shook my head. "If you're good girls while I conduct this exercise tonight," I said, "you'll receive rewards. If you're not? We'll have to measure what the appropriate consequences are, got it?"

They both nodded.

"Jess," I began, "both of you are here right now because you aided and abetted Kat's secret relationship with Tommy. You lied, too, and I'm not going to stand for that. But that doesn't mean a punishment has to be bad, right?"

They nodded again.

"You both like to be punished, I've learned all too well," I observed. "So I'm going to start by letting you know the answers you give here have to be completely honest. You both already should know I find out everything. So if you lie? Well, let's just not do that, okay?"

"Yes, sir," they said in unison.

"You start, Jess," I said. "There's something you want to tell me, isn't there?"

"I guess so," she said.

"Go on," I invited her.

"I saw Tommy this morning, before my appointment, while you were with Rita," she admitted.

Kat shot her a poison look.

"And?" I said.

"He fucked me," she said. "He fucked me so hard in all three holes."

"How much did you love it?" I asked.

"I came too many times to count," she said.

"I thought you said," Kat started, but I cut her off.

"Speak when spoken to, Kitty Kat," I said.

She looked dour and turned her eyes down.

"I swallowed both his loads," Jess continued. "Even after he was in my ass. I didn't care. I needed his cum."

"How's that make you feel, Kitty Kat?" I asked.

"Pretty stupid," she said. "I thought I was his whore."

It was Jess's turn to laugh.

"No one is special to Tommy, honey," she said.

"We don't have a ton of time here, girls," I said. "I've got plans for you this evening. So, Kat, why don't you tell us a couple highlights of what a dirty whore you were in Miami?"

"Um, he took me out on this yacht," Kat began. She fidgeted to the extent possible. "And for the first half a day, he made me crawl on my hands and knees attached to a collar and leash."

"How did that make you feel?" I asked.

"Humiliated," she said. "Turned on. I didn't have a choice. He was my only way home."

"What else?" I prodded her.

"If I did something he liked," she said, "my reward was being flogged."

It was Jess's turn to let her eyes bulge widely. "Are you serious?" she said.

"Jess, shut up," I said casually.

"And?" I said. "There's a big one. That's right, girls, I had a little chat with Tommy today. We came to an understanding."

"You did?" the girls said simultaneously, in shrill, high-pitched tones.

"Answer me, Kitty Kat," I said firmly.

"He gave me a Polaroid camera," she said, "and a list of ten things I had to do for him. It was a sex scavenger hunt. I had to have photographic evidence that I had accomplished each task."

"There was one thing in particular on that list, wasn't there?" I said.

"Yes, I think I know which one you mean," she said nervously. "He made me dress like a streetwalker and made me turn a trick. I sucked a guy's dick in his car in an alley for $20."

"Did you get the picture?" I asked.

"Yes," she said.

"Here it is, isn't it?" I held up my phone and flashed a picture of the Polaroid. "Tommy sent it to me. Look at you. Vacant eyes and lipstick smeared everywhere. Cum leaking down your chin. What does that look like to you, Jess?"

"A cheap fucking whore," she said.

"How did it make you feel?" I asked Kat.

"Turned on," she said. "It was the last of the ten tasks. Tommy called me a good girl and didn't stop fucking me the rest of the time we were in Miami."

"All it took was to be a $20 streetwalking hoe to turn you on that much," I said with amusement. "This is who you are, girls. And where am I?"

"You're right here, daddy," Kat said.

"That's right," I said. "Now if I haven't left you yet, what does that mean?"

"You love us," Jess said. "The real us."

"That's also right," I said. "But I realize now that what was missing was ensuring you knew that. So from now on? If you keep a secret from me, if you deprive me of the knowledge of just how depraved and slutty you are, you are going to face my wrath. Kat, this afternoon? That was just a trial run. It will be so much worse if you cross me again."

"Yes, daddy," she said.

"You need to take me seriously," I said. "Because it will be a lot less fun for all of us if you're both actually out turning tricks on the street because you have to survive."

"Yes, sir," Jess said.

"And I'm not so arrogant to say I don't make mistakes, too. Allowing Nicole into the house was a mistake. I realize that. That's why I want us to work through this together, and I think I have just the way to do that. So, okay, let me get those wrist cuffs detached from your legs for right now," I said. "Keep the outfits on. Do some lines, and then we're headed out."

The girls were relieved to have the use of their hands back, and with desperation they dropped to their knees in front of the coffee table and greedily filled their noses with cocaine. The leather looked sexy on them. The thigh cuffs pushed up against their asses, making them look even firmer and more inviting.

For weeks, we had been on cruise control. We were indulging our hedonistic sides in ways we never had before, but we did it without second thoughts or strategy. In other words, we were careless. We were three individuals operating on our own, not a unified threesome. That needed to change, or the fun would all come crashing down.

I had considered long and hard whether it was worth keeping this thing going. I knew what to expect from Jess. She didn't surprise me, and it didn't bother me. Given the length of time we had been together, I didn't hold it against her too much. Even in her dishonesty, it had become clear to me who she was. There was part of her that needed that secret fun. Kat, on the other hand, had always been open. Her honesty was a defining characteristic, I felt. The Tommy thing shook me. At the same time, I tried to contextualize this, without the past history between Jess and Tommy. Kat saw a client off the clock. Was that bound to happen at some point? And what about me? Nicole was a known flash point for Kat, in particular. Yet I had paraded her through the house like it was no big deal.

So, upon lengthy reflection, I had decided that what we needed was to pull back a little and sprinkle in a little discipline. The girls needed to know I was serious. I wanted to satisfy this darker side they had kept buried, but we couldn't simply continue down the highway of hedonism without thinking about where it might take us.

And that's why, quickly but with care, I had set up an evening that I thought would serve as a course-correction. Four of my former coworkers at the bank had been promoted to managing director. When I had received that title, my mentor and I had banged a couple hookers. So it occurred to me that their promotions could serve my purposes at home well, too.

"Here you go girls," I said as we moved toward the door. I handed them masquerade masks, which would cover their faces and provide a degree of anonymity. "Let's get in the car."

"Um, daddy, we're just wearing this harness," Kat said. "Don't we get a cover-up?"

"No, Kitty Kat," I said. "This is what you're wearing, along with the mask."

"It's kind of sexy," Jess said.

We drove in silence initially, until Kat spoke up.

"I'm nervous," she said, "in a kind of excited way."

"Good," I said flatly.

"It's more fun to do something like this together," Jess added. "It's been a long time, I'm starting to realize."

"It has been a long time," I said. "It's fun to see you girls whore around, and it's fun for me to play around, but that's all a sideshow to the three of us and what we have. Nothing is more fun than when we're together."

"What are we going to do, daddy?" Kat asked.

"You're the entertainment tonight," I said. "But that's all I'll say for now."

My former coworker's house was only ten minutes away. I hadn't seen these guys much since I retired a year earlier, so it would be fun to catch up and exert my control over the girls at the same time.

"Mysterious," Jess said.

We pulled into the driveway of a sleek-lined, modern house near the Galleria.

"Masks on," I instructed the girls. As they stepped out, I refastened their wrist cuffs to their thigh cuffs, pinning their hands behind their backs. "Let's go."

I rang the doorbell. Kat and Jess stood proudly, if nervously. Jess's nipples were especially erect. Kat bit her bottom lip, which was obvious through the generous mouth opening of the mask. They liked it better when they were whoring for me, too.

"John! What's up buddy?" my friend Jason said as he opened the door. "Whoa, and what is this?"

"I told you I wouldn't show up empty-handed," I said.

"Come in! Come in!" he said.

"Girls!" I said and snapped my fingers. They followed me into the house.

Inside, three other men mingled. Kevin, Brett, and Mike stood around a bar holding glasses of wine. With Jason and me, the five of us were cookie-cutter white banker types.

"Holy fuck," Brett said, seeing the girls enter.

"Meet your entertainment for the evening, boys," I said proudly.

The rules and plan had been set ahead of time. Each girl would be set up in one bedroom. I wanted them alone. My girlfriends were free use for my former colleagues for three hours. They could take breaks for drinks, water, and cocaine, but that was it. While they were occupied, I could catch up with my friends, whom candidly I had neglected during my slide into nonstop debauchery. I took Jess by the hand first, leading her up the stairs to a guest bedroom. I passed her a cocaine bullet and guided her to the bed. She didn't say anything.

"Are you nervous?" I asked.

"Why would I be?" she said. "This is exciting as fuck. I'm almost trembling I'm so excited. These guys are your friends?"

"They are," I said.

"Have I met them before?" she asked.

"A couple of them," I said. "It's been a while. I've neglected my friends."

"I'm sorry about Tommy, John," she said.

"I know," I said. "I also know you just can't help yourself."

"That sounds so weak," she admitted, "but it's true."

"But now I think I've figured out you're not going to change," I said. "So I'm going to take back control. You'll know what lies ahead of you if you act like this. And you'll get to decide if that dishonesty is worth the risk."

She started to speak, but I was done with the conversation. I cut her off and said, "Save it for later. You've got cock to suck."

I heard her sniff from the bullet as I walked down the stairs. When I returned near the bar, I found Kat chatting with the guys and drinking a glass of Champagne. Jason rested a hand comfortably on her ass.

"Let's go slut," I said, which elicited laughter and a couple whoops from the boys.

"Yes, sir," Kat said.

She walked up the stairs in front of me. The thigh cuffs really made her ass stand out. It was the perfect bubble of a shelf. I let my hand fondle it, admiring the firmness. While Jess was in the guest room to the right at the top of the stairs, I turned Kat left to the other. Inside, I gave her the same rundown I had to Jess and passed her a coke bullet.

"Thank you, daddy," she said, immediately holding it under her nose. "I'm so sorry. I really betrayed you."

"You did," I said. "All I ask is honesty. Without honesty? We can't protect the love we have."

"Daddy, can I tell you one thing?" Kat asked with genuine hesitancy.

"Of course, Kitty Kat," I said.

"At first I thought Tommy was giving me coke," she said. "But I think it might have been oxy or heroin or something. I didn't feel like I was in control of myself. Like legitimately not in control. Does that make sense?"

"Are you serious?" I asked.

"Yes," she said. "It felt amazing at first, but I didn't feel like I had the capacity to make any decisions or do anything. I literally felt like a prisoner."

"Did he really make you turn a trick like a streetwalker?" I asked.

She nodded her head.

"Thank you for telling me," I said. "I'll deal with it. Don't worry."

"I don't want Tommy around, even if I'm fucking him for money," she said.

"Neither do I," I said. "I'm glad we're on the same page finally."

I gave her a quick kiss on the lips. "You've got cock waiting," I told her.

"I love you, daddy," she said. "I'll show you I'm worthy of it."

"I know, Kitty Kat," I said.

Her contrition was genuine, and it made me feel the best I had since she had disappeared. Before I walked out the door, I spun around to add one final thing.

"Oh," I said, "so these are some of my old work friends. They won't know who you are. But be a good slut for them, baby."

"I will, daddy," she said.

As soon as I got downstairs and poured a drink, the five of us toasted. As much as I loved pussy, I didn't realize how much I had missed hanging out with the guys. No sooner had we clinked glasses then did Jason and Brett head upstairs. Jason went into Kat's room and Brett into Jess's. They had no idea what they were in for.

"So what have you been up to, man?" Kevin asked. "It's hard to catch up when you're not around the office!"

"Have things been crazy?" I asked.

"Crazier than ever, man," Mike said. "We've done a ton more Jonathan Summers business."

"Good to hear," I said.

"But, yeah, what are you doing in your old age?" Mike asked with a laugh.

"Partying and pussy, basically," I said. I pulled out a vial of coke and tossed it on the table.

"Shit, let's bust into this," Kevin said.

"How'd you find these chicks?" Mike asked.

"They're part of a very small, very under-the-radar escort service," I said. "Just a handful of girls and a private house to party at. So basically? I've made them a harem."

"Fuck, if you're getting blow like this, they must be all over your cock," Kevin said after taking a bump of coke.

"You better believe it," I said.

"Not seeing anyone?" Kevin asked.

"A couple here and there," I said. "You know me. I like to keep my options open."

We shot the shit for a few more minutes until Brett returned.

"That was quick," Mike said.

"That girl has a mouth like you wouldn't believe," Brett said. "I haven't cum that fast since high school."

"Hit this powder, man," Kevin said. "Unbelievable quality."

Brett didn't need to be told twice. He sent a line rocketing up his nose as if he were going to the moon. As he did, Mike headed upstairs to Jess. Another fifteen or twenty minutes later, Jason came downstairs with a shit-eating grin on his face.

"Now that's a piece of ass!" Jason exclaimed. "Where did you find this slut? I haven't had a bitch crave cum in her mouth like that in years."

I relayed my cover story of the harem.

"Jesus, how do I get in on this?" Jason asked.

"I'll talk to the owner," I said with a wry smile.

And so the party carried on like this for another two-and-a-half hours in a blur of booze and coke. My four friends took a turn with each of the girls and had nothing but the highest praise for their performances. When I walked out with them, harnesses still intact but hands free at their sides, I was proud. This was the kind of good fun I loved my girlfriends for, and we needed more of it.

We got home, and my body felt like it was about to give out. All of us had hit an emotional wall. I took the girls out of their harnesses, and we showered together. It was slow, rejuvenating, and sensual. There was a lot of kissing. Their mouths were salty with cum. They had swallowed every load that evening, so as I soaped up their pussies, it made it extremely tempting to play.

But exhaustion set in on me. I was spent and, shortly after drying off, collapsed into bed. It was relatively early, and for a while I enjoyed a perfect night's sleep. But around 2 a.m. I woke up and realized the girls weren't in bed with me. That made it impossible for me to get back to sleep, so I got up and went searching for them. As I reached the bedroom door, I heard them talking in the great room.

"Do you want it to work?" I heard Kat say.

"Oh my god, how can you even ask that?" Jess said. "It's the only thing I know for sure in the whole world."

"Then you've got to get over the idea of having a dirty secret," Kat said.

My interest was piqued. My ears perked up and nerves tightened up my stomach. What was I about to find out?

"I'm just so used to having something that's my own, you know?" Jess said. "Tommy was that. It's weird not to have anything. But, I have to admit, being with Tommy again was super scary because that pull was still there."

"Tommy is bad news," Kat said. "I'm so embarrassed. I put you in such a bad position with John. That wasn't fair."

"I did like how jealous and rough it made John, though," Jess said with a giggle. "If he gives me that once in a while, I don't need a Tommy in my life."

"That's so true!" Kat agreed. "I didn't see that dark side of John coming. It was such a fucking turn on. I literally thought I was going to squirt when he had me tied and gagged."

"But Tommy is cut off," Jess said. "I don't want him around any of my girls. I forgot such an important rule. No drama."

12