Chapter 39

Author’s Note: Here’s another long one, my friends. Jess and John get away to Cabo. Of all our characters, these two maybe have been through the most together. Where does their future lie? I hope this chapter answers that for you.

Hawaii had been a fantasy, but I had three more fantasies to live out. In the meantime, life at home in LA was cruising along smoothly. I took a couple days to attend to business, which had only been getting easier and easier as Jason took on more of the day-to-day operations. He and Crystal were six weeks away from closing on their house in LA, which was going to make life even more fun.

While Rita and I were gone, Kat had gotten her nipples pierced again. Daydream had plugged away, with Kayla filming a teaser scene with the Sausage King, which would have the industry buzzing. But the porn industry was already buzzing because Manny had very publicly gone out and announced he dumped Kayla and was signing with a new company that was known for dark, rough, deeply kinky scenes. It seemed to suit his personality and would help ensure he left us alone.

In the whirlwind of moving from one trip to the next, there was one essential thing we all agreed we needed to do. We took Katie to get her initials tattoo on her pelvis, and each of us added another K to ours. Katie was almost in tears from happiness as the “JKJRK” appeared on the porcelain skin near her pubic mound. It was emotional for all of us to get the additional K, like receiving a sacrament. We celebrated with dinner at Spago, which had become tradition for marking family occasions.

The next afternoon, Thursday, I waved to the girls at the top of the driveway again en route to Burbank airport. This time, Jess sat next to me, her face relaxed and her hand soft and gentle in mine.

“You need this,” I said, grinning at her. “You’ve earned it.”

“It is going to be so good to get away,” Jess said.

She wore a green A-line dress that flowed around her body and revealed a lot of neckline. And she looked relaxed. It had been a long time since I saw that much peace in her face.

“I’ve been craving some time with you,” I said.

“If it’s anything like Rita’s trip, we are in for a fun weekend!” she said enthusiastically.

“I want it to be whatever you want,” I said.

“I don’t even want to leave the room,” she said. “I just want us to lose ourselves in each other.”

“It’s a good thing we have a beachfront suite,” I said. “We won’t be bored for a minute.”

“I couldn’t stop looking at the pictures online,” she said. “That plunge pool? Oh my god.”

“And a butler to cater to our every whim,” I said.

“What I want the most isn’t something a butler can provide,” she said.

“Eh, in Mexico? They can provide a lot,” I said with a chuckle.

“Mine needs to be exceptionally pure,” she said playfully.

“Maybe we brought too much?” I said.

“You know how my appetite for cocaine is,” she said.

There was an erotic tension building between us. Jess had asked that our getaway harken back to the days when we first met. We would take weekend trips, where we basically locked ourselves in a hotel room and passed two or three days in a blur of coke-fueled fucking.

“You want a little pre-flight snack?” I whispered in her ear before nibbling it.

“I had a couple lines with the girls before we left,” she said, “but a bump can’t hurt.”

I fished out a coke bullet from my pocket and passed it to Jess, who discreetly bent down and inhaled a bump in each nostril. She handed it back to me, and I followed suit. An off-the-rails weekend with Jess was always a treat, and I regretted it had been so long since we had one.

“What are you thinking?” she asked me as I stared out the window.

“Oh,” I said, coming back to reality, “I was just realizing it’s been way too long since we’ve had one of our wild little weekend trips. Way, way too long.”

“Let’s turn back the clock this weekend,” Jess said. “I was thinking how fun it would be like on our old weekend getaways when I was still in college. Like when we went to Austin or New Orleans.”

“Those were so fucking wild,” I said.

“Think you can keep up?” she asked.

“I was going to challenge you with the same question,” I said and put my face close to hers.

Jess had a deeply mischievous look on her face. I stared at her expectantly, wanting to know what was on her mind. She held out briefly, then spoke.

“Want to make a bet?” she said.

“Yes,” I said. “What are your terms?”

“I bet you can’t cum more than seventeen times,” she said.

“Six times each day?” I said smugly. “Easy.”

“It only counts at the resort,” she said. “Not before and not after.”

“That’s going to make for a hell of a teasing plane ride,” I said.

“Isn’t that the best kind?” Jess said with a laugh.

In five minutes, we were at the airport. Ten minutes later, we were airborne. And three hours after that? We were led to our palatial beachfront suite at the Waldorf Astoria Los Cabos Pedregal. It was an insane setup. It wasn’t a suite. It was a two-story house, right on the beach, maybe fifty feet from the ocean. The dining room and living room were both covered but open-air. There was an infinity plunge pool at the rear of the back patio, along with a private cabana just at the edge of the beach. The master bedroom on the second floor had a large terrace overlooking the ocean view, complete with lounge chairs and a fire pit. It was an extraordinary, thoughtfully laid out space, and we took advantage of that immediately.

The butler unpacked us, but we didn’t have many clothes. Jess had two sundresses and three barely-there bikinis. I had swim trunks, a couple pairs of shorts, and a couple t-shirts. We weren’t planning on being in public or clothed very often. There was no doubt it would be a coked up fuckfest. And I couldn’t be more excited about it.

Jess was out ahead of me. After I inspected our closet, chuckling to myself at how few articles of clothing we had between us – and impressed that the butler hadn’t batted an eye at it – I found Jess on the cusp of the second-floor bedroom terrace. There was a chair and ottoman parallel to a beautifully smooth wooden ledge that opened to the outside. The weather was glorious, hot but with unseasonably mild humidity. Jess kneeled on the ottoman, which left her at the perfect height to cut lines across the ledge. She had cut off a chunk of perfect flake cocaine and was chopping it up with loving enthusiasm. She was an artist, and coke was her true medium.

“Come hit this, baby,” Jess said.

Her words were almost washed out by the nearby surf lapping at the beach. But, standing above her as I walked over, I could see her rip two modest lines to maintain her buzz. Her sundress rode up her hips, and I felt the double desire for that wicked coke rush and invading Jess’s tight cunt from behind.

“Hit what?” I said, now behind her and letting a hand wander under the hem of her dress.

“Both,” she said. “This weekend is all about excess. I know you’ve got a big fucking load to give me, and I know you love it even more when I’m a coked up slut. You know every inhibition goes out the window.”

“I’ve never known you to have many inhibitions, Jess,” I said, bending down to kiss her.

She kissed me back and handed me the straw. I did two lines and had to admit, doing them with the beach and ocean right there in front of me added to the rush. We kissed again, then I cupped her face in my hands.

“I really want this to be like the old days,” I said. “Really get a lot of time with just us, no noise. You and me, going off the rails.”

“While we do rails,” Jess joked sweetly, then turned sultry. “Why don’t you fuck me right here? So we can both watch the ocean. Then I want to play with your cum in my pussy.”

My reply was to simply gather a handful of her ass cheeks and then spank her. She lifted her dress above her hips, and I let out an impressed whistle.

“Do you like it, baby?” she said, finally turning around to look at me, biting her bottom lip.

“Gorgeous,” I said, letting my finger trace the outline of the clear glass butt plug that was nestled in her ass.

My shorts dropped to the ground, and I barely bothered to step out of them before I slowly, easily worked my cock into Jess’s proffered cunt. She was wet. Very wet. And as soon as I bottomed out, she helped herself to two more lines of cocaine.

“Fuck, I love that feeling,” she said. “My two favorite things at once.”

“You’re so fucking wet,” I said, my hands firmly on her hips and immediately getting into a groove of long, moderately paced strokes.

There was no way this was lasting long. Luckily, Jess was as pent up as I was. Her pussy juice flowed freely down my shaft, collecting on her thighs, and dripping down to the ottoman. We were both quickly short of breath, and it was a race to see who would cum first. I didn’t want to be too selfish, but it took a significant effort not to simply blow my load. As soon as Jess’s body tensed in orgasm, I unloaded. It was a massive explosion of cum deep inside her, and I worried briefly that the occasional passerby on the beach might hear her pleasured moans.

“Fuck, I needed that,” I said.

“Me, too,” Jess said. “Go get one of my bikini bottoms. I want to keep this inside me. It’ll keep me lubed all day, so you can take me whenever you want.”

“You stay wet all day anyway,” I noted but complied.

I retrieved the least revealing of Jess’s bathing suit bottoms, which was still a sexy thong, and watched her slip them over her feet and up her hips. She stood up to finish pulling them up, and kissed me deeply.

“I can feel you running out of me,” she said. “And I love knowing it’s not going anywhere.”

“That’s just the start, sweetheart,” I said and kissed her.

She put her bikini top on, and it barely held even her medium-sized breasts. I loved how much Jess loved showing off. She never turned off the switch that craved attention. It was pre-wired into her.

“What do you want to drink?” I asked. “I was thinking we could take advantage of the pool and just do whatever we feel like.”

“Margaritas,” Jess said. “I’m going to pack the coke bullet.”

“Awesome,” I said. “Maybe some chips and guacamole?”

“And queso,” she added.

We spoke quickly. There was a vitality and momentum to the vibes between us. This was going to be a lazy beach getaway, but we were going to be traveling at ninety-miles-an-hour. And that was something unique about Jess. A lot of people did cocaine as a party drug. It helped them be social. It was in a crowd, at a club, or to ramp up an already wild time. For Jess, though she had an outgoing and vivacious personality, cocaine highlighted and brightened all those parts inherent in her. Perhaps more significantly, Jess was just a party girl at heart. She loved it. It was an instinct embedded in her DNA. So it didn’t surprise me that, after I placed the food and drink order with our butler, Jess had already slid into our private pool and pushed the coke bullet quickly under each nostril before setting it on the ledge. I joined her, and she wrapped her arms around my neck, greeting me with a kiss before pulling back to sniffle.

“A pitcher of margaritas and a slew of junk food headed our way,” I said, seeing my reflection in her sunglasses.

“This is the most relaxed I’ve felt in a long time,” she said.

Our hands played underneath the water. There was an insatiable, magnetic attraction between us, although too often lately it felt as if something had gotten in the way of it. Because of that, this trip with Jess was perhaps the most important of the four. I didn’t like feeling a gap grow between us, although with Jess, it had always been a constant struggle between getting too close and then drifting before the magnetic field brought us back together, closer than ever. The volatility had lessened considerably over the years, but I was interested in smoothing it out – at least as much as possible – for good.

“You don’t need to put so much pressure on yourself,” I said.

“You always say that,” she replied.

“I mean it,” I said. “Now more than ever.”

“We have been through a lot,” Jess said, briefly pensive. “Way more than in ... since ... well, a long time.”

I knew what she was thinking. I was thinking about it, too. If Jess pushed things too far, we could end up in that place. That off-the-rails place. That left us in the wilderness once before. And had been such a barrier to our eventual reconciliation. Looking back on it, we had really endured a rocky end, then a reckless restart. There was still an aspect of recklessness in our relationship – in part because there always had been.

Jess and I both got off on pushing the envelope. Together? We pushed it far. The one thing that tempered the dangers of that shared mentality was our ambition. But we had reached a place where pushing the envelope sexually had dovetailed to a certain extent with that ambition. Her escort and porn businesses put us squarely in the realm of temptation almost constantly.

“I realize not all of it is pressure, either,” I said. “You know how we both always like to push the limit.”

“Do I?” Jess said with a laugh. “I thought that was only you.”

“You know what I mean,” I said, pulling her into me for a kiss on the cheek.

“I shouldn’t joke,” she said. “I’ve been pretty crazy recently. I’m honestly really sorry about it, John. The whole Manny thing was a stupid idea and a debacle. For so many reasons.”

“Don’t think I’m mad about it,” I said. “Water under the bridge. Things happen. I got the spirit of what you wanted.”

“I wasn’t thinking straight,” she said. “It’s like I have tunnel vision. I see all these things in front of me, and it’s all so fun and tempting, and I want all of it. It’s like trying to pick out things at a buffet. Except with all the Infinity and Daydream things, it’s sex and partying. It’s like living a fantasy all day, every day.”

“It is like a fantasy,” I said, my coke-addled mind running wild with visions. I bent down and kissed her neck. “But we also have more power now. More control.”

“I’m not used to that,” she admitted. “I’m used to reaching for something. Or trying to move to the inside from being outside.”

“You know I’ve felt the same way for a long time,” I said. “But we’re the insiders now. We’re what people want to crack into.”

The doorbell rang. Or, to be more precise, we received a notification on a nearby iPad that our butler was at the door. I slid out of the pool, dried my hands, and pressed a button to signal him it was okay to come in. Five minutes later, Jess and I were washing down delightful chips, guac, and queso with kickass margaritas. It was a perfect pool day. We didn’t even mind the sun or the heat. The ocean breeze moderated it.

“I never understood how I can do coke and still eat,” Jess said. “It’s my superpower.”

“You have a lot of superpowers, babe,” I said.

She smiled while she crunched a chip, and looked at me with her sunglasses-covered eyes.

“I’m going to want your dick again,” she said. “Think you could cum as fast if I let you put it up my ass?”

“Maybe a booty bump and let me give it to you really rough?” I suggested.

“I love the sound of that,” she said.

And she did. Her nipples hardened against the fabric of her bikini. She drained her margarita fast and poured us another round. We finished those and took a break from the heat in the pool. Jess wrapped her legs around me and floated in the water, her arms around my neck.

“I really am sorry, John,” she said. “I’ve been reckless.”

I didn’t say anything immediately. I knew she had more to get off her chest.

“I’ve always been a little reckless,” she said. “I have that edge to me. I mean, god, I lost my virginity in a threesome.”

“You know, I don’t think I knew that,” I said.

“Oh, I definitely told you,” she said, teasing. “An Eiffel Tower with two football players on the first night of orientation at UH. And, just like that, the good Christian school girl went up in smoke.”

“You’ve always reached for ambitious goals,” I said. “I do remember that you had told me that.”

“College was such a blur,” she said. “It’s a wonder I ever graduated.”

“You almost didn’t,” I said and immediately regretted it.

“Yeah,” Jess said, and I could feel her thoughts drifting off to darker times.

“We have always had a lot of fun, Jess,” I said. I kissed her neck lightly.

“Do we have too much fun?” she asked.

“This isn’t like you,” I said, although that wasn’t a fair observation because I had opened the door.

“I’m trying to be more self-reflective,” she said. “More strategic. I’ve always just flown by the seat of my pants. I like acting on instinct. But we’ve raised the stakes, sweetheart. There’s a lot more to lose.”

“There is,” I said. “We have an amazing family, don’t we?”

“It’s the family I’ve always wanted,” she said.

“Is it?” I asked. Rita’s words from Hawaii about Jess wanting a baby rang in my ears. “Or almost the family you’ve always wanted?”

Jess laughed and pushed me away half-heartedly. I noticed she wiped an eye beneath her sunglasses.

“Somebody has been talking to Rita, I guess,” she said, a nervous smile crossing her lips.

I walked through the water and pinned her against the wall of the pool. I kissed her deeply, holding her close with one hand and feeling for her ass with the other.

“Of course I have,” I said. “I think you knew that.”

“I had, kind of ... hoped,” she admitted.

Vulnerable Jess was still something new to me. I kissed her again.

“It’s okay to grow up,” I said. “It’s not like we still won’t have fun.”

Jess sniffled, and I couldn’t tell if I had pushed the seriousness too far, or she was just dealing with the coke drip. Our conversation had been animated, intimate, and rapid-fire. I gestured to the margarita pitcher, and Jess nodded. I poured us another round. We ate some more chips and finished off the guacamole.

We pivoted from our veer toward the serious when Jess took my hand and led me inside. The blast of air conditioning felt good against our hot skin. Jess ran her fingers over my cheek and looked at me with longing.

“Give me a booty bump,” she said, “and then fuck me in the ass. Fuck me in the ass hard and punish me for being such a whore for Manny. Fuck me for being a stupid slut. Remind me whose the only man who won’t fuck me over and treat me like a dumb bitch.”

Her nostrils flared to punctuate her seriousness. I took the hint.

“You were a stupid slut,” I said, pushing her down toward the bed.

I raised my hand high and brought it down on her left ass cheek. Then repeated the motion on her right. The firm flesh instantly turned bright pink, my hand print embedded in it.

“Yessss,” Jess hissed. “Punish me.”

I walked over to the closest and opened the safe. I pulled out a vial of cocaine, which had a small spoon attached inside the cap. I walked back to Jess, who was naked and on all fours on the edge of the bed.

“Spread your ass,” I ordered.

“Yes, baby,” Jess replied.

I smiled as she opened herself to me. Her slit was still wet from the mixture of her arousal and my sperm. Her asshole twinkled with a sheen of those same messy leftovers. I looked at the crinkled, light brown skin that spiraled into a beautiful pink abyss. I quickly scooped three spoonfuls of cocaine onto her hole. After I screwed the cap back on the vial and tossed it onto the bed next to her, I pushed two fingers into her cunt. She gasped as they glided over her clit and probed for her g-spot. But pleasure wasn’t what I was going for; it was moisture. I scooped up as much wetness from inside Jess’s pussy as I could, and my fingers were covered in a thick syrup. Before it had a chance to drip off, I simply jammed both of them into her asshole, forcing the pile of cocaine inside her.

“Fucking shit, babe,” Jess groaned. “That’s intense as fuck!”

I pushed my fingers in and out of her, wanting to ensure every crystal was pushed as deeply inside her ass as possible. When I was satisfied they were, I pulled out my fingers and walked to the side of the bed. I took hold of Jess’s chin with one hand, and made her clean my fingers with her mouth.

“That’s a good slut,” I said.

“Oh, shit, sweetheart,” Jess said, her eyes completely glazed over, “this is really hitting me. It’s really hitting me hard. Give me that dick. Please, baby? Put your dick in my ass?”

She was plaintive, and I didn’t even wait for her to finish begging before I stood behind her and slipped the tip of my cock inside her. I paused for the briefest of seconds and then buried my shaft all the way inside her. At the same time, as I stood on the floor thrusting upward into her asshole, I reached forward and grabbed a fistful of her pretty blonde hair. I tugged it hard, pulling her ass back to me. Her knees gave backward involuntarily, impaling her more deeply on my cock. She cried out happily.

“Take me, John!” she screamed.

With my free hand, I spanked her. Hard. Over and over. I pulled her hair harder. My cock got more inflexible with each stroke. It was a vicious fuck, just like she wanted. Pussy juice and even more remnants of my cum streamed from her cunt, making a mess down her thighs and dripping onto the pristine white sheets of the bed.

Being rough had never been at the top of my list of kinks. It didn’t come naturally to me, and I always felt awkward, even when I knew the girls wanted it. Rough sex had to come from a place of genuine emotion with me. I couldn’t simply turn it on with the flip of a switch like someone like Manny could. My mind wandered back to the angry times I had with Kat and Jess, when they had goaded me into hate-fucking them by cheating. It was something they loved from time to time, a total physical domination by a superior physical force. But I didn’t view myself as that kind of person.

That day with Jess, however, was one of those rare exceptions. I didn’t know it until I felt the vise-like grip of Jess’s asshole against my cock as I pulled her hair just how angry I had been at her. She felt it, too. And she loved it.

“You need to fuck the bitchiness right out of me, baby,” she said. “I’ve been such a bad girl.”

“Take that cock, bitch,” I said.

Jess half-moaned and half-laughed. We both knew this was somewhat half-hearted, but the force with which I fucked her was no joke. And her orgasm, which crept up stealthily, exploded like a supernova. Her legs almost buckled, forcing me to pull her thighs back to the edge of the bed, and I cascaded on. She came again, and her tone changed to one of loving desperation.

“Please cum in me, baby,” she whimpered. “Please. I crave it. I love feeling that close to you.”

“Fuck, I love you, Jess!” I cried, the climax building inside me.

“I love being your dirty fuck slut,” she said. “Your dick fills up my ass so much.”

“I’m going to fill it with cum right now,” I moaned.

“Yes! God! Yes! I’m cumming again!” Jess cried.

Our voices rang out in a pornographic operetta. My final thrust threw us off-kilter, and my cock popped out of Jess’s ass as we slumped onto the bed together. My chest slid across her slippery back, and we wound up in an awkward spoon position. My legs were tangled above hers, and we breathed heavily.

“Fuck, Jess,” I said, her face in my hair and my mouth near her ear.

“That, my love,” she said, “was catharsis. Thank you.”

We kissed, and I wasn’t sure if she meant it was catharsis for her or me. But I knew what to say back.

“I love you, too,” I said.

We had done too much cocaine to take a nap, and Jess, like me, always became energized after sex anyway. So we took a shower, and the demeanor between us was almost sickly sweet. Our hands and lips roamed. When we finally tore ourselves away from the glorious, intense rain shower head, Jess set up four more lines on the bathroom counter.

“Why not?” she said with a shrug of her shoulders.

I only grinned in response. But when she addressed the lines, I couldn’t resist spreading her ass cheeks. She half-heartedly tried swatting my hands away, and I admired the swollen, slightly raw look her asshole had taken on from our anal session. She snorted the lines and threw her head back.

“God, that’s such a fucking rush,” she said. “I’m fucking wired. It’s brilliant.”

I spanked her playfully, then she handed me the straw. The coke rush was beautifully intense. It hit the way it did when I was really in the mood to party, which was a feeling Jess might have been the queen of bringing out in me.

She had put back on the same bikini.

“This still smells like your cum,” she said. “It’s so fucking hot having that against my pussy.”

“I love when you get like this,” I said.

“Let’s go check out the beach,” she said.

“And finish the margaritas,” I added.

The beach was incredible. The sand was fine and hot, but the ocean was warm yet wonderfully relaxing. We strolled as we sipped our drinks. Jess expressed surprise that there were so few people, and I told her that this strip of the beach had controlled access.

“Maybe we should fuck out here, too,” she said.

“The sand might chaff your ass more than that last fuck did,” I said with a laugh.

“Yeah, you animal,” Jess joked. “It might not be until tomorrow that I’ve recovered to let you in there again.”

“Well, I still haven’t used your mouth,” I said. “And I’ve got fifteen more orgasms to go.”

We laughed and walked slowly along the water’s edge. We held hands, and enjoyed the fact that the sun had softened some.

“The sunset is going to be stunning,” I said. “The sky is so clear.”

“Maybe we can watch some stars tonight,” Jess suggested.

“Yes,” I agreed.

Then I noticed Jess squeezing my hand, firmly but quickly, three times. I glanced at her, and she raised her eyebrows at me suggestively.

“Look there,” she said, tossing her eyes to our right.

I finally caught up with what she was trying to tell me. There was a second suite identical to ours next door, separated by a tall stone wall. It created enough privacy that we barely even noticed it. At the edge of the plunge pool, which was just visible as we strolled back toward the manicured pathway to our suite, I saw what Jess was flagging for me.

“That’s,” I whispered, but Jess cut me off.

“Yup,” she said just as quietly.

Our neighbors were one of the hottest tabloid couples in pop music. They were both superstars, although her star burned more brightly than his. He had matured from teen hottie to legitimate heartthrob and was breaking into movies. We could see how their hands roamed as they made out.

“Interesting,” I said.

“Let’s get some Champagne and watch the sunset,” Jess said, smiling at me.

We held hands until I was forced to let go to open the Champagne. As I did, Jess ran another chunk of cocaine through the grinder, refilled the coke bullet, and cut four lines for us. She was attentive and skillful in her movements with the white powder. As soon as she finished, she snorted two lines quickly and cleanly, then ran her hand across the countertop and rubbed her gums furiously.

She sighed and said, “Ah, there we go.”

She sniffed a couple more times and passed me the straw. As I accepted it, I handed her a glass of Champagne. She took a long drink as I snorted the other two lines. The coke rush hit me hard and fast, and it felt like the jolt of energy was attached to my cock. Jess pushed her backside into me slightly and brushed across my crotch.

“The fact that coke only makes you harder,” she said, turning around quickly, “makes me so fucking wet.”

“I thought you wanted to watch the sunset,” I said.

“I do,” she said. “Come on.”

I put the Champagne bottle in an ice bucket and followed Jess to the beach. We sat on the lounge chairs in a small area of the beach cordoned off for our suite. The influx of cocaine wasn’t ideal for sitting still, watching the sun descend toward the horizon. We drank the Champagne fast, and I refilled our glasses. Jess sat between my legs, her back against my chest and her free hand occasionally roaming to trace the outline of my cock under my swim trunks.

We heard a loud burst of laughter to our left. The popstar couple next door had the same idea. They were drinking on their lounge chairs twenty feet away.

“Sorry!” the man said.

“We can be quiet!” the starlet added.

“That’s no fun,” Jess shouted over to them and raised her glass.

We all laughed, then turned our attention to the sun, which made its final approach to the horizon.

“This light is trippy,” I said, watching the orange-and-pink beams fly off the swirling, crashing water.

“Should I talk to them?” Jess asked.

“Sure,” I said.

The sun was gone in only a few more moments. Bold, darkening red hues dominated the sky and beach. Jess stood up and refilled her glass again. She was getting tipsy, and the coke always gave her confidence.