The Billionaire and the Escort

by Evelyn Mahony

  “Please,” Josh begged one more time, grasping the sheets below him as he watched James’ every move. His own cock jumped at the first touch of James’ slick, rounded tip. It drooled all over his belly as James teased him, making Josh moan incessantly. It was pressure everywhere but where he needed it, until finally, finally James pushed against the loosened ring of muscle, gaining entrance after slow and steady pressure.

  As soon as the crown of his thick cock pressed through, Josh was gasping. The stretch was more than James’ fingers, the shape less forgiving but in the best way. He forced his eyes open to watch as James took his time, pressing into him gently. James’ hands were on his hips now, and he held Josh still as he slipped his cock inside him, making Josh’s mind go completely blank of anything but obscene pleasure.

  “Holy fuck,” James groaned, and Josh forced his eyes open to glance down at him. James was focused on their joining, his eyes wide and dark, his face red with tension and pleasure. “You should see yourself…f-fuck.” His words stuttered as he pressed forth, Josh’s body slowly accommodating him. It was erotic, sensual and somehow something Josh hadn’t experienced in the times he’d done this before. He felt open and vulnerable, but also like James would take the best care. It was a heavy feeling that weighed over him until James bottomed out and began to pull back, making Josh moan wantonly because… No, not yet, I need…

  James pulled his cock out and Josh gasped at the loss. He traced his finger around Josh’s hole, humming to himself in a way that made Josh shiver. Then he plunged back in slowly, that initial notch of his cut head inside making Josh see stars. The drag, the twinge of stretch mixing with the insane pleasure of being penetrated was going to make Josh go mad. “Fucking hell, Jamie.” He stretched his head up and back, pleasure ricocheting off every nerve, “S-so…oh,” he huffed in surprise as James began to move, a slow rock of his hips that was sinful. Josh gripped the sheets tightly, his biceps and abs flexing as pleasure drowned him.

  He caught James, hands on the bed on either side of his hips, rolling his into Josh with purpose, roaming his gaze over Josh’s body. Josh felt like a prize under his scrutiny. He let the sounds fall freely, let his body move as it wanted to, meeting thrust for thrust until James was repositioning them, bringing Josh’s legs up and over his shoulders. This gave him more leverage and the curve of James’ dick allowed his head to scrape Josh’s prostate every time he pulled back, until he was almost completely out, driving Josh mad. Then he’d thrust back in, pushing a whoosh and a groan from Josh’s lips. The man knew how to fuck—it was evident—even if he’d never fucked a man before. Josh was so close to losing his mind, so full and stretched, his toes curling, every muscle tightening…

  “Jamie… Jamie… Daddy… Please,” he chanted, letting himself fall into the well of pleasure. James nodded, on the edge himself.

  “Touch yourself. Come all over yourself while I come inside you. God…fuck…” It was punishing now, and between that and James’ words, Josh was in a mad dash to come.

  “Come inside me, please,” he said as he jerked his cock frantically. Their moans mingled in the hot air between them, their bodies slick and sliding together with practiced ease. Josh didn’t want this to end, but God, he had to come so badly or he’d die. He was sure of it. “I’m…oh, God… Jamie, come inside me, please…”

  “Good boy. Come on, beautiful boy. Come on. Come on yourself and I’ll come inside you, just like you want.” James knew just what to say, it seemed, and Josh didn’t question it. He did as he was told, basking in the praise as he came hard. He clenched down on James hard cock as cum covered his chest, his chin and his abs, his moans broken as he rode the waves.

  James followed him right after, but Josh was barely aware. With three more punishing thrusts, he stilled with a shuddering groan that Josh felt more than heard, then pumped his hips a few more times, slow and shallow.

  Shockwaves traveled through Josh for several moments before he opened his eyes again. James had his forehead pressed to Josh’s right calf, his own labored breathing evident. Letting go of the rumpled sheets, he slid his hands down to rub at James’ thighs. That grabbed his attention, and he raised his head to grin down at him.

  “Hi.” James blushed hard, and Josh couldn’t help but flush in return with his own small hello. They chuckled a little, the passion of the moment fading and leaving aftereffects in its wake. “That was…”

  “My best bottom experience ever,” was out of Josh’s mouth before he could stop it. He slapped a hand over his mouth and actually laughed, his cheeks flushing. James snorted.

  “I’m going to think you’re actually serious since you reacted that way.” He chuckled, rubbing his beard against Josh’s calf. “Honestly… That was fucking amazing.”

  Josh nodded, letting his hand fall away as he ruffled his sweaty hair with his other hand. “I’m serious, though. I shouldn’t have said that, but fuck. I felt that in my toes. I might be dead.”

  James flushed a beautiful crimson as he pulled out of Josh slowly, both men groaning at the separation. James shuffled unevenly off the bed to dispose of the condom and Josh contemplated a second shower. There was no way he could go again, not for at least an hour. Maybe James would join him…

  James returned with a warm towel and a cup of water and Josh had to blink. People did not take care of him. Aftercare was never in the agreement. But James swiped the warm towel over Josh thoroughly, disposing of it and climbing back into the bed. Josh reached for James and they locked their hands together as they slid their bodies close.

  “You’re sure you’re okay?” James asked quietly, nuzzling against Josh’s ear. Josh’s cheeks went hot and a smile formed as he nodded.

  “Far beyond okay. You’re…that…wow, Jamie.” He turned his face toward James, their eyes locking as their faces were level on the pillows. James roamed a hand over Josh’s chest absently, and it was warm and calming.

  “You are, Josh,” James replied softly before closing the distance and kissing him slow. Josh’s heart fluttered and his body gravitated toward James without a second thought.

  It was apparent that somewhere in his post-sex rush, somewhere in his addled mind that he was falling for his client. And there was seemingly no stopping it.

  * * * *

  The sun made the day outside look deceiving as it came through the lace curtains. James knew it was no warmer than New York outside, but the sun made it seem like spring. And the shape it illuminated on the bed made it seem all the warmer.

  Josh was curled up on his side, one arm curled under the other, his face tucked against them. The sheets and comforter had fallen to his waist as he slept, leaving his bare upper body on complete display. His blond hair tousled, a barely there shadow of scruff on his jaw, his pink lips parted just slightly, eyes still very shut with sleep, he was the picture of handsome peace. James didn’t want to wake him, but the fresh pastries and coffee would get cold if he didn’t.

  He’d woken before the sun, wanting to get emails out of the way so he and Josh could spend time together with Maria, working through this new job opportunity and Josh’s future. He wouldn’t normally be involved in such matters, but this was Josh—not only his faux boyfriend but also someone he cared about. He wanted to make sure his company did right by Josh—and that Josh was prepared.

  That in itself was enough to wake him before dawn—the worry about the why he cared for Josh so much. He had boiled it down to their arrangement, their friendship and close proximity. He was determined to only see it as that. He was paying the man, for goodness’ sake. There was no way to back out of this arrangement without someone getting hurt or something being ruined. They were in this now, and James was determined to keep things the way they were.

  Even if last night was more than incredible.

  Setting the tray down on the side table, he sat on the bed beside Josh, folding one leg under himself as he contemplated how to wake the sleeping beauty. He couldn’t stop himself from brushing th
e soft hair off his forehead, trailing his fingers down the light strands. Josh’s long eyelashes fluttered, and he let out the softest sigh James had ever heard. His heart clenched. And that was why he had to stay focused off his heart.

  “Good morning, sleepyhead,” he murmured, letting his fingers run down Josh’s arm. Josh opened his eyes, blinking a few times in the bright morning light. James couldn’t help finding him utterly adorable, all youth and clean, hard lines blinking like a sleepy puppy. The yawn he tried to cover solidified that comparison.

  “Hey, Jamie,” he rasped, shifting under the covers to stretch. James couldn’t tear his eyes away as the sculpted arms rose over his head, his long legs stretching under the covers. His abdominal muscles shifted, his pectorals hardened and James’ cock was growing more interested with every second he stared. He was literally insatiable for this younger man. It was still shocking sometimes.

  “Brought you some coffee and pastries, baked fresh this morning,” James offered, unable to pull his hand away when Josh slid his fingers into it. It was a tender gesture that warmed him more than the sun could.

  “Yeah?” Josh shifted again to lie back on his side, assessing James’ own morning hair and sweatpants. “I think that’s my shirt.” Josh sounded amused and didn’t hide his smile. James glanced down at the soft gray T-shirt and chuckled, his cheeks heating.

  “Huh. You know, I didn’t remember buying it, but it was too soft to take off.” James ran his free hand through his hair, surprised at not feeling awkward in the slightest as Josh smiled up at him like a ray of sunshine.

  “You can keep it. I don’t mind. I have like ten of them,” Josh offered without hesitation. “Looks better on you anyway.” His free hand fell to James’ thigh as he spoke and James knew then that they were on the same page. “Like the way it fits your arms, across your chest.” Josh dug his fingers into the muscle there, caressing as the words grew quieter but heavy with intent. “You should come closer. I’m hungry…”

  James scoffed in mock surprise but moved closer without waiting more than a beat. “Your coffee’s gonna get cold,” he teased, though he suspected the man didn’t care. And as he rose and flipped James to his back, pinning him to the mussed sheets, his suspicions were confirmed.

  “Ain’t coffee I want.” Josh’s Brooklyn slipped out and James shivered, gritting his teeth with anticipation. With the top sheets shifted, it was obvious that Josh was very aroused. It was a pleasant surprise and something he never grew tired of seeing.

  “Well, far be it from me to stop you from having what you’re in the mood for,” James replied, trailing his hands across Josh’s round shoulders as Josh worked on getting his sweatpants off without much fuss. He licked his lips as James’ cock sprang free, also very interested in the morning’s turn of events. James’ heart rate jumped.

  “Don’t mind if I do,” the younger man all but growled as he wasted no time wrapping those beautiful pink lips around James’ cock. Yes, this was the way every morning should start. James had zero questions about that.

  Josh couldn’t believe their trip was almost over. Ten days ago, he’d arrived in Italy as just an escort away on a job with one of the most eligible bachelors in the world. Now he was an artist contracted with a billion-dollar company, about to embark on a whole new journey. He hadn’t quite figured out what he’d do with the rest of his life when he got back to New York, but he wasn’t worrying about it. He was soaking up the Italian sun, wine and all the sex he and James had been having since they’d arrived. This was the best trip of his life.

  He looked at James over his tiny espresso cup as they sat at a small coffee shop in Otranto. They’d taken a day to go exploring, driving a little over two hours south. While Josh was at a loss with the language, James was completely content, touring them around, speaking to the locals like he belonged. It was a little more than Josh could handle after spending so many nights in bed with the man.

  James finished ordering another espresso from the young waitress and turned back to Josh, raising his eyebrows as Josh knew he’d been caught marveling. “Need something?”

  “No, no.” Josh shook his head, setting the tiny cup down to choose his words wisely lest he say more than he wanted to. “You’re just so…comfortable here. It’s nice to watch. And you didn’t tell me your Italian was that good.” He added the last part because he couldn’t help it, their banter still holding up outside the bedroom.

  James laughed a little and Josh enjoyed the way his cheeks turned pink. “Well, when we built the resort, I spent a lot of time here—got to know my favorite spots, learned to speak the language. I enjoy being here a lot.” He sipped the rest of his current espresso before a small grin took over. “I’ve enjoyed being here with you. Thank you again for coming.”

  “Stop thanking me.” Josh laughed off the part of James’ enjoyment, because if only… “I should be thanking you. This has all…changed my life. I can’t even begin to—”

  “Don’t. You don’t need to thank me for anything. Having you here has been more than a joy. I’m still sorry Maria accosted you the way she did, but honestly, getting to know you has made this even more fun—and not just sexually, the real Josh.”

  The way James said the last part made Josh’s body flood with goosebumps. It was such an intimate thing to say, and of everything Josh was sure of, he knew James was a genuine person. He wouldn’t say it if he didn’t mean it that way in his heart.

  “Well…feel special, because everything I told you, I hardly tell anyone. I mean, I have my roommates, but…” He drifted off with a shy shrug, smiling a little as he thought of his friends.

  “Tell me about them,” James pressed with interest. Josh chuckled a little.

  “They’re not that exciting or anything—Nadia and Andrew, my two best friends and roommates. Nadia I met through…work.” He cleared his throat a little then laughed. “And Andrew is normal.” The word made him laugh again and they settled into easy conversation as Josh let James in on more of his personal life. It was far too easy, but Josh never questioned it because this was James.

  Once they finished their coffee, they continued exploring. Hand in hand, they walked the streets, James’ security not far behind but giving them distance. It was still sometimes strange to Josh that no one in James’ camp knew they weren’t together, but it didn’t bother him, because deep down inside he knew that being real was becoming the one thing he really wanted. He couldn’t have that, so pretending was the next best thing. And pretending without anyone else knowing they were pretending…? Well, that was the best it was going to get, Josh knew.

  * * * *

  The next morning brought more of the life Josh had grown accustomed to in Italy, mixed with meeting Maria and ordering supplies, setting up trips and planning his work through March of the following year. Josh had texted his friends the news, and much to his appreciation, they seemed genuinely excited. He had yet to tell his mother about any of it—Italy, Jamaica, the job—because how was he supposed to explain all this to her? He kept up with her via text, the occasional casual exchanges to keep her from worrying about him and to keep him aware of what went on in her life. She could handle her own affairs. She was as strong as Josh himself, stronger really, but he looked out for her as her only child. He’d sent her flowers two days prior as a gesture and because he was feeling guilty about the lies and omissions, so when his phone rang midafternoon, he smiled and figured she’d finally received them.

  “Hey, Ma,” he answered as he shifted on the couch in the lavish living room of their villa where he was sketching. He continued mindlessly shading in one of the people in the picture as he held the phone to his cheek.

  “Joshua Grant, explain to me why you’re in Italy.”

  His hand stilled, charcoal against the textured paper as her tone and words hung over the line. “Umm-m…I can explain.”

  “I’m sure you can, sweetheart.” Sarah Roberts wasn’t beating around the bush, and Josh honestly didn’t expect
anything less. “I can’t wait to hear about why I’m staring at a picture of you and a handsome, older man strolling hand-in-hand down an adorable cobblestone street overseas and why you didn’t bother to tell your mother you were leaving the country?”

  Picture…? He didn’t remember anyone taking pictures of them, and he was momentarily distracted as he set the pad down and grabbed his laptop roughly off the coffee table that his feet had been resting on moments ago. “Pictures? Where?”

  “I went to get my hair done an hour ago and Shelly had that Daily Mail website up on her phone and she said ‘Sarah, is this Josh? Who’s he with?’ and sure enough, it was you and this resort designer I had no idea you were seeing. Care to enlighten me on when you got a very wealthy, much older boyfriend?”

  Josh put her on speaker as he typed rapidly, googling James’ name and Daily Mail. Sure enough, there they were, a feature article for that day. A dozen pictures had been taken of them, and he was silent as he scrolled, his heart racing in his chest.

  “Joshua? Are you there?”

  “Yeah, yeah, Ma, I’m here! I’m just… Hang on. I can explain,” he said, scrubbing a hand over his face. He held the phone closer to his mouth, not afraid to keep her on speaker as James had gone up to the main building for a meeting two hours before. He scrambled to concoct a story, though he knew his mother would see through any lie he spewed unless he was utterly convincing in a way he’d never managed to be before. “I…met James—James Barnwell—a couple of months ago back in New York. We started seeing each other a little after that. I didn’t tell you because”—he closed his eyes and leaned his head back on the couch, hoping the heavens would forgive him for the lies he was telling her—“he’s much older than me and I didn’t want you to know until we were serious, in case it didn’t work out. If I’d known someone would publish pictures of us, I would have told you. He’s wonderful, Ma. I promise.” Well, at least most of that was actually true, he realized as he held his breath and waited for her reaction.