The Billionaire and the Escort

by Evelyn Mahony

  “Yeah, sweet boy. I’ll be the only name in that pretty head of yours after tonight…”

  James undid Josh’s belt at that, unzipped the slacks and pulled them down around Josh’s thighs. Josh’s erection bobbed out, showing just how much he needed James. James was eye-level with his length for the first time and seemed to take a minute for him to appreciate the view.

  Josh swallowed hard and found himself unable to stop begging. “Please, Daddy, suck me… Dying to feel your mouth… I need…”

  “Shh-h, sweetheart. I’ve got you.” It felt a little like they were playing a game, some kind of role change as James wrapped a tentative hand around Josh’s length. Josh nodded and swallowed hard, needing more but taking what he was given with grace. James stroked him a few times, leaving Josh feeling exposed and a little nervous as he let his free fingers graze Josh’s inner thighs and over his balls. Josh keened, needing more, very sensitive to the touch. James grinned, cupping his sac and squeezing as he started to stroke with more purpose. Josh didn’t hold back on his noises. He let James know just how good it felt, just how well he was doing.

  “So good,” he groaned, swallowing hard. “So, so good, just—”

  Josh’s brain short-circuited as he watched James flicker out his pink tongue and curiously lick over his swollen red tip, and in that moment, it was the most erotic thing Josh had ever seen or felt.

  “Mmm-m,” James moaned, seemingly delighted with his first taste. He parted his lips and wrapped them around the tip of Josh’s length, and Josh about lost it to the sight alone. Knowing this was James’ first time was beyond exhilarating. Somehow, he’d gotten to be the first person James had experimented on. His heart raced as James played, getting a feel for the shape and curve of his length. He was slow—and Josh didn’t mind one bit. The man could explore all night if he wanted to. The problem was that once James really got going, it wouldn’t be long before he exploded. He could only hold on for so long. He was just human, and the closer that bearded face got to his hips, the harder it became to hold it together.

  James was working his way down, taking Josh deeper with every bob of his head. He sucked and pressed his tongue to the underside, and Josh knew he was trying to recreate all the things Josh had done for him. He ran his hand through James’ thick hair, the tendrils soft under his fingers. “That’s it, Jamie.” Josh kept his voice low and sweet, maintaining the dynamic they’d created. He let out moans as James took him deeper, swallowing around him before he coughed and pulled off for a moment. His cheeks were red, but Josh didn’t focus on the floundering. He desperately wanted to come down that throat. He knew it wouldn’t take much more. He was on the edge, just almost there… “Suck the tip, Daddy. Squeeze my balls. I promise I’m right there,” Josh begged. “Please, please…”

  James went back in for more and didn’t disappoint. He did just as Josh told him to, wrapping his lips around his length about halfway down and sucking with intent. He squeezed and rolled the ball sac in his hand, no doubt having done it to himself, and Josh basked in the impending orgasm. He whimpered and moaned and gripped James’ hair without forcing him. For a novice, the man was ambitious and determined. “I’m gonna… Jamie, I’m right there— I’m—” He tried to warn him, but James didn’t move. Instead, he sucked with more vigor and had Josh’s toes curling as he stared down at the glorious man on his knees in front of him, pleasuring him because he wanted to. Josh lost it. He bellowed and shook as he came hard enough to see stars.

  James did his best to swallow it all, backing off to let a little more room in his mouth as Josh emptied himself. He was panting as he finished, a complete wreck against the villa wall as he forced his eyes open to find James licking him clean, still on his knees. Josh wished momentarily that his cock could respond already, because that was a sight he wouldn’t soon forget.

  James looked very pleased as he stood, brushing hair from Josh’s sweaty forehead. “That’s my boy,” he praised, and Josh beamed tiredly. James kissed him deeply, letting Josh taste the saltiness left behind, and he pulled James in, wrapping his arms around him and holding him close. It was a dangerous kiss, the kind one could lose themselves in and that made one want to die happily having had the best kiss of their lives. Then Josh realized James was hard and heavy in his own slacks and, well, he couldn’t let that continue.

  Reluctantly pulling away from James’ delicious lips, Josh turned them around and dropped to his knees in front of James, all innocence and want. James looked pleased and hungry, but Josh had other ideas. “Mark me,” he requested in that destroyed voice. “Mark me and my suit and all that’s yours. Prove that I’m yours…”

  It was vulnerable and they hadn’t experimented with this yet. James stared in something that was a mix of awe and desire, rubbing that thumb over Josh’s swollen bottom lip once more. “Want me to come all over your face, handsome boy? Is that what you want?”

  “Yes, Sir. Please. Tell me I’m yours. Show me.”

  James didn’t need to be asked twice, it seemed. He dropped his hands to his slacks and pushed them down to his ankles, pulling his sweater over his head and tossing it aside. Josh swallowed thickly in anticipation, that hard cock he’d grown to have a deep need for standing just inches from his face. He placed his hands in his lap in the ultimate submissive pose, tilting his chin up so James didn’t have to aim much. God, he wanted this so badly that it scared him.

  James wrapped his hand around himself and let out sweet noises as he began to work himself over. He wasn’t slow. He didn’t tease. He was running toward his release, seeming to want to mark Josh up as much as Josh wanted it. He was always generous in his sounds and he kept his eyes on Josh’s the whole time, the heat between them inexplicable.

  Josh memorized the way James touched himself, the stroke he used, the grip of three fingers and his thumb. He stared at the way his skin moved, the glistening tip. Josh was so hungry for what came next that he found himself silently begging, Please, Jamie. God, yes…look at you. Please, Sir. I need it, Daddy.

  James didn’t disappoint. He let go with a low, long groan, his mouth falling open as streams of white covered Josh’s face. Josh closed his eyes out of instinct but basked in the warmth as it landed on him, covering his cheeks, his lashes, his skin all over. It was personal, it was filthy and it was somehow the sexiest scenario with James that Josh had found them in yet. The afterglow resonated around them as both James and he were gasping, one from exertion and one from the thrill, and Josh knew that if he could rebound quickly, they’d be in trouble. He had every intention of rolling over and taking James in the night. He just needed to rest and soak up this moment between them.

  “My God,” James murmured as managed to crack his eyes carefully. His cheeks went red as James stared, but Josh could tell it was awe in his eyes. He swiped some off Josh’s cheek and put his thumb to those lips once again. Josh hungrily licked it off. James moaned a low, “such a good boy.”

  It was different for James to be the one doling out all the praise, but Josh knew it was to ensure that Josh didn’t forget who he was with—as if he ever could. He was sure nothing would ever compare to this.

  Cleaning up was slow, methodical and sweet. James cleaned Josh’s face with a warm cloth then they kissed until they both needed water and aspirin. They undressed and slipped into more comfortable clothes before raiding the kitchen for peanut butter and biscotti. James brewed them decaf espressos and they collapsed into bed not long after, both getting rid of their clothing to sleep skin to skin.

  Josh couldn’t then be held responsible when his cock woke him, hard and hot and pressed against James’ round ass. Josh didn’t tease him and simply slipped on a condom, coated his cock and pressed himself against that tender, hungry hole. James, barely awake, consented with moans and cries for Josh, the stretch apparently a little more than normal but nothing unbearable.

  Lying on their sides together, Josh peppered James’ back with kisses and nips until he was fully seated. They
moved together, slow and rhythmic. James held on to Josh’s hand, gripping tightly as he whimpered. Josh angled his hips, knowing just where and how to make James lose his mind, even slowly like this. In and out, deep drags, an extra thrust just before I pull out. Wrapping a towel from the bedside table around James’ length to avoid mess, Josh fucked slowly and deeply into him until they both released. Curled against one another, hot and sweaty, Josh almost forgot to rid himself of the condom.

  For a brief moment, he wished there would be a time they didn’t have to use the protection anymore. His hazy brain reminded him that would probably be never, but he pushed the thought away as he cleaned them up thoroughly and slid back into bed, wrapping himself around an already-asleep James. He didn’t blame him and didn’t even wake him, pressing a kiss to his cheek before letting himself fall back asleep as well.

  * * * *

  Sitting in the sunlight on the resort terrace, sunglasses on and a third cup of coffee at hand, Josh remembered why he preferred not to get drunk. His head was finally no longer pounding, now just a dull ache behind the eyes, and he was feeling less sluggish than when he’d first woken up to an empty bed and a sweet note left by James.

  Josh,

  I have a nine a.m. meeting. I wish I could have woken up with you, enjoyed breakfast then some time in the shower. I’ll make it up to you later. More aspirin and water on the table. Take it. It’s not a suggestion.

  See you later this afternoon.

  James

  Josh had lain in the bed with a dopey smile and reread the note at least five times like a lovesick fool. Somehow, he was able to not focus on that, to ignore the lovesick part and simply call himself a fool as he dragged himself to the bathroom. He looked like death and felt very close to it.

  Now he was getting some sunshine outside a cafe, sucking down hot coffee and eating fruit in hopes he’d be alive by the time James found him. Still in a black tank top and cotton sweatpants, he wasn’t exactly a fashion statement. Luckily, no one bothered him, though—or seemed to care.

  He sketched the cliffs from where he sat, able to catch a lot of the town below, the sunrise and the ocean. It was therapeutic to sketch, his portfolio full of different projects from Jamaica, New York, Italy and now James. He’d begun a new one upon meeting James, leaving his other sketches at home and using a new leather-bound portfolio with a new class of nice paper and pencils. He’d used some money from what James had paid him to indulge. While he didn’t use that money for much, traveling with someone like James made him feel the need to portray the lifestyle. At least when he carried this beautiful folder around, he felt the part he was playing.

  Emptying his cup, he decided he needed more. He slipped the latest sketch back into the folder, not bothering to zip it as the loose-leaf papers lay inside. He was just going to grab another cup and head back outside, get a little more sun and maybe take a nap. By then he’d feel better about seeing James, and maybe his cheeks would be pink enough to let James think he wasn’t as hungover as he still felt.

  Shit, he cursed himself as he rushed through the open-air doorway into the cafe. The change in light messed with his eyes and he blinked rapidly. Unaware of his proximity to the woman passing him, he bumped her roughly with the arm carrying the folder. Not only did he drop the coffee cup while trying to catch the woman from falling on her tall heels, but he dropped the folder too, sketches fluttering all over the marble floor. He successfully grabbed the woman’s arms, holding her up, despite the mess he’d made otherwise.

  “I am so sorry!” Josh exclaimed, helping to steady her on her feet. A stream of expressions crossed her face, surprise to horror to…is she blushing?

  “Goodness! Has anyone ever told you that you’re built like a brick wall? I think you broke my—” She stopped and was gazing down, and Josh’s eyes followed then widened in his own horror. “Is that…? Are you…?” The woman looked between the several sketches of naked James Barnwell and Josh, recognition dawning now on her face. Josh wanted to melt into the floor and disappear from his life at that very moment.

  “Umm…” was all he could muster as he dropped to his knees, frantically—but gently—gathering up his artwork. The woman seemed frozen for a good thirty seconds before she dropped down to help, picking up three pictures in particular.

  This is terrible. Awful. Like someone seeing into his soul. He shouldn’t have been sketching pictures of James, but it wasn’t against the law. And the man was beautiful. He shouldn’t feel bad about it, but a pit sat heavy in his stomach. If she knew James…

  Josh was sliding the rest back in, hiding the pictures of James under several landscape pieces. When he finally looked up to see the woman holding a few, he tentatively reached out. “May I—”

  “These are incredible.” She spoke with a fierceness he hadn’t expected. “You drew these?”

  She turned the pieces so Josh could see them. One was of the Jamaican resort, the new area James had just opened. Another was James, naked and face down on the bed, his visage hidden by his blankets. It was a personal favorite of Josh’s, drawn in Jamaica as well. It was an explicit piece of James’ backside, as Josh had sat in the chair at the foot of the bed and drawn from that direction, every detail memorized and saved to paper. Josh’s flush intensified dramatically. The last piece was the one from this morning, of the Italian landscape. He swallowed hard and nodded.

  “Yes, ma’am. Every piece is mine,” he answered meekly, that hangover no match for her gaze of steel.

  “Are you a commissioned artist? Do you have a gallery? What’s your full name?” She peppered him with questions like fast balls and Josh hardly noticed the barista cleaning up the broken porcelain behind him.

  “Josh Roberts, ma’am. And no, I don’t. I’m not. I sketch for fun. I mean, someday I hope to open my own gallery, but I don’t think that will happen anytime—”

  “Do you sell your work?” She was back to staring at the sketches. Josh’s forehead was furrowed so hard it hurt. Why is she asking so many questions? And why is she still staring at James’ ass?

  “I-I haven’t, no. I don’t really show it to—”

  “Come with me. Now.” She stood swiftly, spinning on her heels and heading for the elevator.

  “Ma’am? I’m—”

  “Come, Mr. Roberts! We have a lot to discuss.”

  Josh made sure to zip up the folder as he stumbled to his feet, grace to be desired in his flip flops. He scurried after her, feeling the adolescent, small and sickly version of himself, being dragged to the principal’s office for punching a bully in the eighth grade. A terrible thought overtook his brain as he watched her turn the corner toward the board room that he knew James and his team were occupying that morning. She was going to tell. She was going to expose Josh for drawing James and accuse him of selling the works. There was no way he could let her tell James—

  But she was flinging the door open before her could reach her, but he stumbled in soon enough to see her set the three images down before James himself. Josh stood in the doorway, his shoulders hunched and panicking. “Ma’am! James! I can explain—”

  “I just ran into your freight train of a boyfriend, James. Quite literally. It seems he’s an artist. How come you didn’t tell us about his talent?” The brunette woman leaned on her palms against the table, looking at James with what Josh decided was a cross expression. James looked utterly confused and flushed as he stared at the middle picture, which most certainly was his ass.

  “Hello, Maria, Josh.” James’ gaze flickered to Josh’s for a split second—and not nearly enough to settle Josh’s anxiety.

  “Did you know? Were you hiding this from me?” Maria demanded, switching the order of the sketches so the Jamaican resort was in the middle. The dozen people around the table were all peering at the art, and Josh was sure this was the end. He’d be shipped back to America on the next jet out of— “You knew what I was looking for and it was right under your nose. This”—she tapped the picture—“needs
to be hanging up front and center in the lobby in Jamaica! It’s perfect!”

  Wait…! She said what? Josh’s mind tripped over her words.

  “Maria, I had no idea he was an artist. I can assure you.” James looked up to Josh and their eyes locked. Josh shrugged helplessly.

  “It’s a private hobby, honestly,” Josh finally interjected, his voice sounding small to his own ears. “I don’t really tell people about it.”

  “A hobby? Mr. Roberts, what you have here… You should be selling this. In fact, James, we need to get him under contract. I need these. I can see it now…” She stood up, looking around the room. “If he can do pieces for each resort, for the suites even, the lobbies, it would give such an authentic, personal, family feel to each location. A theme.” She was enthusiastic as she spoke, and Josh’s jaw was dropping with every word she said. “Barnwell, I’m having it drawn up. Mr. Roberts, can you do this? Can you see my vision? I want this, and this, and maybe even a little of this.” She tapped her finger over each picture, James’ being the last. “With less nudity, of course, for each resort. Several. Can you draw people? Faces? Do you use color? Paint?”

  Josh was gripping his portfolio so hard that his knuckles were white. Everyone was staring at him, including James. He was not dressed for a business meeting, not even showered, and somehow something huge was happening to him right before his eyes.

  “I um… Yes ma’am. I do all those things,” he managed to squeak out. A grin was pulling at James’ lips.

  “Perfect. Bruce”—she pointed at another man Josh had yet to meet, but who looked strangely uncomfortable and was staring at the naked sketch of James—“draw it up. Mr. Roberts, we’ll meet at two o’clock. James”—Maria patted the man’s shoulder and Josh could tell it was affectionate, like they knew each other well—“you should check out all the sketches your boyfriend has drawn of you. He leaves out no details.”