Traffic Girl - Jess Ch. 02

Author's Note: Thanks for reading, votes, and support. Framing up where Book Two is going, and then we'll roll headlong into the adventure that awaits. Enjoy!

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Jess put a death grip on my hand as the single-engine Pilatus PC-12 banked to make its final approach into Gustaf III Airport on the island of Saint Barthélemy.

"I hate small planes," she said as she buried her head in my shoulder.

I squeezed her hand back and kissed the top of her head. We landed without incident and rapidly passed through customs to meet our driver for the short trip to the Eden Rock St. Barths. The resort sat in the center on the island's north side. A butler escorted us to the Waterlily suite, laying out our suitcase in the bedroom, while we immediately opened the expansive French doors to the main balcony. Underneath the alcove sat two deck chairs with matching tables and a double-wide beach lounger. The far end of the balcony comprised an infinity pool, raised about eighteen inches above floor level. The pool looked out over the greenish-blue purity of the Caribbean Sea, with the resort's pristine white sand beach directly below.

"John, oh my god," Jess said. "I love you."

I walked up behind her, slipping my arms around her waist and pulling her close to me. Her oversized beach hat and airy coverup afforded glimpses of her white bodysuit and linen shorts. I tipped our butler handsomely and checked on the bar. It was stocked as requested, overflowing with Champagne and cold white wine. I chose the Dom Perignon and two elegant coupés to pour it into and rejoined Jess on the balcony. She drank in the splendor of the scene with unadulterated joy.

"Just being here makes me so happy," she said. "Like there are zero cares in the whole world."

"It suits you," I said. "I want you to be this happy."

I passed her a glass of bubbly. We clinked glasses, kissed, and drank.

"Do we have to do anything but sit here all weekend?" she asked and laughed.

"Nope," I said. "We can get all our meals brought in, too. Even the Jean-Georges restaurant will send up anything we want."

Jess shed her coverup but kept on her hat and oversized Chanel sunglasses. "No, I want you to show me off," she said. In a fluid motion, she unbuttoned and slipped off her shorts, folding them and setting them down on one of the side tables. Her white bodysuit was a thong, which snapped between her legs.

"This is your weekend," I said. "We do what you say."

"I wish we had some party favors," she lamented.

I laughed. "I guess you weren't paying attention in the car," I said. The driver was arranged through a friend, who had been to St. Barths regularly. He was a good connection, and I had scored some cocaine and weed for us. The price was outrageous, but we were held captive on the island.

"What?" Jess said, her eyes as big as saucers.

"An eight ball and a quarter of weed," I said.

"Fuck, that is so perfect," she said. "I would love to just sit out here and smoke and listen to the waves."

"We'll do that tonight," I promised. "Right now? Let's ditch these clothes and get in the pool."

The infinity pool was a long rectangle, giving us an expansive view of the beach and sea. The water was warm, making it feel natural to enjoy it nude. Jess loved the water. Being here rekindled memories of the Hill Country house we had rented for her birthday several years prior, where we played endlessly in the pool. Jess made the connection, too.

"The water makes me so horny," Jess said, swimming up to me as I took a break on the edge of the pool, admiring the view.

"Is there anything that doesn't make you horny, sweetheart?" I asked.

"You're right," she said. "Now let me show you some appreciation."

Her mouth enveloped my cock, soft, warm, and wet. My erection distended as she moved back and forth, increasing the pace quickly. She gulped at my cock greedily, hungry for the creamy reward she craved so badly. Jess gave sloppy head, but like a pornstar she always remained in control. She swirled her tongue around my head and flicked the opening at the tip. I put my arms behind me and leaned back, pushing my legs closer to her. She rested her forearms on my thighs and easily took my shaft fully down her throat.

"See anyone cute on the beach?" Jess asked as she briefly pulled off me.

"I don't see anyone, but you're feeling frisky," I said. "So I'll keep an eye out. There ought to be interesting people here this weekend."

Jess had a legitimate cuckquean tendency. She loved scouting a crowd for women to potentially join us. She especially loved trying to guess who might be what she called a "secret slut" -- someone who looked prim and proper but hid a wild side. Someone like Kat. She also truly enjoyed watching me fuck someone else. For her, it boosted her ego to have a man who was with her but also coveted by others. She had a very free sexual mindset, and it was something I cherished because it was the same mentality as mine. There was a secondary aspect to it for her, which was that she sometimes had a dominant streak with other women. She was demure almost to the point of submissive with me, but she adored adding a woman to the mix we could control.

"We really should find a little fuck toy," I told her as she pushed me closer to orgasm with her exquisite mouth. "I want to get you a strap-on and let you dominate her. Let me fuck her ass while you take her pussy."

"Oh god," she groaned as she briefly pulled her head off to spit on my cock.

I lost my train of thought as Jess doubled down on my cock. She had decided it was time I came. Her tongue moved back and forth on the underside of my shaft, while her cheeks created suction around the sides. I was putty in her hands once she started this. She squeezed my balls. This was a very practiced routine that never got old. I smiled as I felt the cum rise and shoot into her mouth. Jess was an unabashed cum lover, clamping her mouth down and swallowing each rope as it came. I bucked my hips a couple times and then eased her off me.

"Fuck, I am never going to let you stop sucking me," I said.

"Don't," she said. "I'm such a junkie for your cum. I literally could drink all of it. I wish you could bottle it and just let me have it anytime I want." She laughed.

We kissed, and I let my hands wander her wet, naked body now that she had slipped out of the pool and next to me. The view was superb, and we would have a great view of the sunset.

"I really want some of that coke," Jess said. "But it's probably smarter to smoke before dinner."

"Do you want to eat before or after sunset?" I asked. "I think we're going to have a great view from here."

"Before," she said. "I want to get coked up and fuck all night."

"I am so up for that," I said.

We went inside and dressed for an earlier dinner. Jess skillfully rolled a joint. She had become a substantial marijuana enthusiast since our previous stint together. She favored edibles, but smoked frequently, too. I thought it was sexy to see her puff on a joint or a bowl. When she was stoned, it made her more submissive than usual. Perhaps paradoxically, she liked it extremely rough while high.

Sitting on our deck, we passed the joint back and forth until it was finished. Jess had a dreamy, relaxed look on her face. She had changed into a white halter dress that was long but had dramatic slits up both thighs. Her nipples poked through the tight top, and the billowy fabric frequently bunched between her ass cheeks.

"Let's go eat and capitalize on these munchies," she said slowly. "And then you're going to come back here, take out my butt plug, and absolutely punish my asshole."

I raised my eyebrows. The high from the weed was pleasant and mellow. "Oh really?" I said.

"I need a really hard anal fuck," she said. "I've been a bad girl, and I need you to punish me accordingly."

"Have you been a bad girl?" I said with a hint of surprise.

"I'll tell you at dinner," she said. "I've been waiting until our getaway to talk about it."

The meal was superb. There always was something magical about eating seafood that had been caught yards from where you sat. The wine was expensive but good, and it was worth the island markup.

"So I set up a sugarbaby profile," Jess blurted out after we had finished a bottle of wine.

I looked at her with a surprised smile. "You are feeling frisky," I said.

"I haven't done anything yet," she said quickly. "I mean, I haven't messaged anyone. Just set it up. And my face isn't in the pictures or anything. I just." She stopped short.

"Is there something more I can do for you?" I asked.

"No! Not at all!" she said. "You're perfect. You know me." She had a sheepish look on her face.

"You know, now that I think about it," I said, "you haven't had any fun in almost two years. And you've let me have a good bit of fun. Kat, Rita, Gloria..."

"So, technically, I may have not been totally forthcoming about my year of celibacy," she said.

I raised my eyebrows. She knew I liked hearing everything she did.

"When I was getting back on my feet and didn't have a full-time job, I had to get out of my parents' house," she explained. "My ex and I had talked about moving in together, but we broke up shortly after. I needed a little financial boost.

"Long story short, I was talking to Melanie about it," she said, referring to her best friend, "and her younger sister Alison. Have you met Alison? I don't think you have. She is so gorgeous. Anyway, Alison suggested I find a sugar daddy. She had done it during college and said it was the best experience of her life. Money, travel, shopping. And all you had to do was go with older guys. I mean, obviously you know I have no problem with older men, so."

She stopped, wanting to give me a chance to catch up and ask questions. I just gazed at her. It was a non-judgmental, warm look with a slight smile.

"What I didn't realize was that Alison wasn't using some regular sugar baby website," Jess continued. "Initially she had just met a guy who got her into it, and she dated him and a few of his friends. But there was a kind of underground, Houston sugar website. Alison said otherwise you'd have to wade through a bunch of fakes.

"Alison referred me, and I signed up, and within a couple days I had meetings with a half-dozen potentials. And two weeks later? I had two arrangements and had moved out of my parents' house. I didn't realize until later that it's more common to have one arrangement at a time, but you know me. I'm anything but traditional." The words poured from her rapidly.

She looked at me, this time expecting a response. I honestly didn't know what to say. It didn't bother me. It didn't surprise me too much. That she wanted to do it more? It was a turn-on.

"Wow," I said. "That's a lot to take in. But obviously it worked out really well for you, it sounds like." I was searching for words to reassure her, as well as tease out the dirty details, which is what I really wanted.

"I don't think I knew what to expect," she said. "At first, meeting for coffee or a drink, it was just like real dating. But once I found a guy I was really attracted to, that's when I understood how much of an expectation the sex part was."

I smiled at her. "You were a whore," I said. My tone was one of appreciation.

Jess took the hint. She licked her lips. "I was," she said. "I had my job three days a week, and the other days I fucked my sugar daddies. I was such a whore for them."

"You know I want to hear all about them," I said. "I want every little detail. There is so much racing through my mind, I don't know where to ask you to begin. But maybe with this: how come you signed up again? And was it the same site?"

She nodded. "It was," she said. "I didn't want to waste my time."

"So you're serious about it," I observed.

"I think I am," she said. "Moving in with you is a big step. You know I don't like to be dependent on someone. This is a way to express a little independence." She looked intently at me. "Plus, I want the money. The money makes me so fucking wet."

"I have to admit, this is a bit of a surprise," I said. "But I am really hard right now. Why don't you tell me about one of them while we close out and head back to the room."

"Here's an easy one," she said. "The first arrangement was with an old oil and gas executive. I'll jump ahead a little bit, but this is a quick story. He had a friend who became my third sugar daddy. But all he ever wanted to do was take pictures of my feet. And jerk off on them. I learned really quickly that guys with fetishes like that are really common."

"I can't imagine paying a woman just to jerk off on her feet," I said. We started the walk back to our suite.

"He gave me a thousand dollars every time I saw him, too," she said.

"Jesus," I whistled.

"The oil and gas executive was my main daddy," she said matter-of-factly, revealing that she had gotten familiar with the lifestyle. I marveled that she could have kept it from me. "After our first couple meetings? He would just give me $3,000 on the first of every month, wired straight into my bank account. I think he had a self-confidence problem. He was polite and perfectly good looking, but he really couldn't believe I'd have sex with him. Or maybe he just didn't want to put in the effort it would take to get younger women to sleep with him. Whatever. The sex was vanilla. He was very into romance. I put on a show for the money. I realized I was good at it! I was very convincing. It became such a power trip."

We arrived back in the room, and I pushed Jess against the front door after it closed and kissed her urgently.

"I can't believe you could keep this from me for so long," I said, breathing rapidly. "It's so fucking hot."

She looked at me seriously. "Does it really turn you on?"

I took her hand and put it against my linen shorts, so she could feel my erection. "That answer the question?" I said.

"And if I do it again?" she asked.

"Just like in the past," I said. "You tell me every detail? I have no problem with it."

She smiled like she had just won something. "You're really going to love hearing about my third daddy. He was my favorite. I called him Dirty Daddy. Where's the blow?"

I got Jess the eight ball. She went to work preparing it as she told me about her third sugar daddy.

"With the oil and gas guy being so vanilla," she began, "I needed something more exciting. I went back to the site. I wanted to find someone who seemed, I don't know, almost dangerous. That's when I found Peter."

She stopped her narrative for a moment to snort two healthy lines of cocaine. I followed suit.

"That is not bad for being captive on an island," I said. "So often they cut it to shit."

Jess kissed me, and there was emotion behind it. "I want you inside me when I tell you the rest of this," she said. In a flash, her dress was on the floor. She led me to the bedroom and started telling me about Peter as I undressed.

"He was a lawyer," she said, slowly playing with her pussy as she told me. "He had an interest in bondage, but like in a Fifty Shades sort of way. He was tall and handsome, and honestly he reminded me of you, which is why I agreed to meet him.

"We met for a drink first, and he was a perfect gentleman. I almost didn't believe there was a darker side to him. Then we met for dinner, and I was convinced he was full of shit because he was just so sweet and proper, and I was getting bored with him already."

I climbed on top of her and slid inside. We took a moment to savor the glove-like fit of her pussy around my cock. I noted how wet she was as she recounted her exploits.

"I think he sensed I was getting frustrated," she said and paused to gasp as I savored giving her long strokes with my cock. Our hips moved in unison, like a wave. "When all of the sudden, just as our cocktails arrived, his face turned cold and hard. And in front of the waitress, he said loud enough for her to hear, 'Go take off your panties in the bathroom, and bring them back to me so I can see how wet you are, slut.' I think my jaw actually dropped to the floor."

I pulled my cock out of her, and her hand instinctively reached for it to put it back in. I wouldn't let her.

"And what did you do?" I asked, hovering the tip of my cock just out of her reach.

"Of course I did it," she said, happily. "He took me to his place that night and gave me $2,000 in cash. He showed me the permanently installed restraints on his bed. He had one wall of his walk-in closet that had all kinds of BDSM toys hung from it. There were only two problems with him."

I plunged back in, touching her cervix.

"First, his cock was short. It was super thick, but it was short. Not even six inches," she said. "It was hard to cum with him as a result. And, second, he would get so rough it would put me out of commission for two or three days so the marks could heal."

I was dumbfounded at how Jess could surprise me so greatly. She kept me off balance, and I loved it.

"But oh my god the money!" she continued. "The rougher he was with me, the more money he gave me. Like one time he had this contraption where I was on my knees, with my arms spread to the side and above my head and bound that way to this metal bar. And he used a riding crop and flogger all over my body. It made me so wet, being deprived and teased for like three hours. He gave me $5,000 for that one evening. And that's when it occurred to me that no matter how rough he was, I had all the power. I loved it."

I took the pause in her story to slip out of her pussy and line my cock up against her asshole. I was eager. This was a new Jess. Her love of power in this context showed she was still a people-pleaser, but she also prioritized what it gave her strategically. She really had undergone a tremendous amount of personal growth. I glazed my cock head in her pussy juice before pushing the tip into her ass.

"I never pegged you for the hardcore bondage type," I said casually.

"It's not that," she said. Her face registered mild discomfort as my cock worked its way in her ass, then bloomed in satisfaction. "I learned that I was collecting secrets. Being a slut? You're just out there collecting pleasure and making memories. I realized I had achieved a more powerful position by sugaring."

"My little Jess is all grown up," I said, savoring the view of my cock sliding in and out of her ass so effortlessly. "But still an anal slut."

"I think I might want you in my ass more than I want you in my pussy," she said.

I hooked Jess's knees around my elbows and drove her legs above her heads as I thrust in her ass. I was penetrating her as deeply as I could. She howled in pleasure and urged me as her panting increased. Her ability to take rough ass fucking was a marvel. I didn't stop for a moment when she screamed out, announcing her orgasm. I kept going, pushing myself to the brink. I admired Jess's golden hair, spread out on the pillow below her, and the sparkling blue eyes. Everything about her urged me on, and I pushed her feet above her head as I drained my balls into her ass.

She held me close, arms wrapped around my back, as my cock twitched.

"That is my favorite feeling," she said and kissed me. "Think you've got another couple rounds in you? Let's get some coke and keep going."

She bounced out of bed, her body lithe and graceful. She returned with the cocaine, cutting it into lines as she sat on the bed.

"I think I just ruined these sheets," she said with a laugh. "You cum so fucking much."

I cleaned up in the bathroom and returned to see Jess forming two more lines. She had done all four herself.

"Being a greedy little coke whore?" I said.

"Shut up and do yours," she said. "Then you can face fuck me on the edge of the bed." She was already lying down with her hair nearly touching the floor.