The Billionaire and the Escort

by Evelyn Mahony

  “Probably just keeping it professional,” Josh suggested lamely because he had no idea why she’d still call James that after years of service. James shrugged as he set the bottle down and picked up the glasses, handing Josh his.

  “Probably. I just feel like I should know her better, y’know? She’s been in my life longer than…anyone personally. She’s seen me on some bad days. She has four daughters and never had a son. Sometimes I think that’s why she mothers me the way she does from time to time.”

  “She only works for you?” Josh inquired.

  “Oh yeah. I make sure she’s well taken care of,” James explained without hesitation. “I take care of the people closest to me.” They maintained eye contact for an extended period of time, Josh trying to come to grips with what exactly that meant before a timer from the kitchen interrupted them. Josh jumped slightly, unprepared for the noise. “Oh! Let me get our food. Have a seat. I’ll be right back.” James started for the kitchen.

  “Can I help? I can—”

  “No, I’ve got it! You sit. You’re my guest.”

  Josh wasn’t sure if he should overstep and insist or listen, so he sipped his wine and settled down at the table in front of the fire. It was a table big enough for four but with a setting only for two. A black linen cloth with red napkins covered the table. He unfolded one and set it on his lap as he leaned back in the comfortable chair. He considered his evening, because this was unusual for him. His clients occasionally offered a drink or took him out to dinner as a showpiece, but they didn’t wine and dine him before sex. He was still trying to decipher what was happening when James returned with a basket of warm bread and a plate of crispy calamari and sweet pepper rings. Josh’s mouth watered. This was definitely welcome, he decided, regardless of what was the norm.

  “So, whenever I’m in town, I have to eat at DeGrazia’s,” James began as he set down the food and settled himself in the chair across from Josh. “But since it’s cold tonight, I figured we would eat here.” He raised his glass, grinning so brightly that it made Josh’s stomach flip.

  He smiled too, just as wide, since James’ smile was completely contagious. He raised his glass as well.

  “To your schedule being clear tonight. And to a successful trip to Jamaica. I honestly couldn’t have done it without you.”

  Josh let their glasses come together as he pondered that statement. He let it float between them as he sipped his wine. “It was honestly the best vacation I’ve ever had. I can’t thank you enough.” Josh’s cheeks heated as he ducked his head slightly. “I’m glad I could be there for you,” he added as he glanced up shyly.

  James was gazing at him intently and with such utter kindness that Josh floundered inwardly. “I’m so glad I could give you such a good vacation. I hope you were able to relax as much as you wanted to.”

  “God, I was,” Josh answered quickly, before shutting his mouth abruptly. He cleared his throat and ran his hand over his lips as James looked on with sweet amusement. “I mean, it was hardly work. Honestly. I felt relaxed and enjoyed every minute.”

  “Maybe you’d be interested in joining me in Italy for two weeks then?” James asked the question like he was asking Josh to pass the bread, and Josh gaped a little. James was busy serving himself calamari, but when he looked up, he immediately jumped to amend his invitation. “I mean, my staff thinks I have this boyfriend now, and it’s a really important trip for me. You helped me so much in Jamaica, keeping me sane, and you know I’d pay for every expense. There’d even be time to sightsee if that’s what you’re worried about…”

  Josh watched James ramble, the confident man of moments ago suddenly nervous and making Josh feel a little less so. Italy? For two weeks? It was the chance of a lifetime. He couldn’t say no. Not to mention that he didn’t want to say no.

  “Absolutely,” he replied after a brief moment of silence as he processed the invitation “I’d love to go to Italy with you. Are you sure, though? I don’t want to be a burden. I—”

  “You’re so far from a burden, Josh. Please. I really want you to come…if you want to.”

  Something about all this suddenly seemed so intimate to Josh. “I really want you to come” had made Josh’s heart leap in a way it wasn’t supposed to over a client. That was all James was, a client. He had to remember that.

  It became increasingly difficult, however, as dinner went on. James talked about the trip to Italy and what it would entail. They’d fly over together this time—same fake relationship, same sexual arrangement. The money he offered Josh was obscene. Josh would have to cancel more than half a dozen clients, but it wouldn’t matter financially. And when James was in meetings, he’d be able to explore and draw. It sounded like a dream, especially because the sex was so easy. Nothing about being with James was hard.

  They shared chicken marsala and chicken piccata for dinner, with salads and vegetable sides. The food was decadent and to die for. The conversation centered around James, his recent visit to Miami and a silly scandal the local South Florida tabloids had posted about him. It wasn’t true, and James took it all in stride, but Josh was entertained.

  Josh ate more than he should have, he decided. James was right there with him, though, and they were both full as they settled down on the couch in the same room, having moved the table that apparently actually belonged elsewhere. Josh realized somewhere in the back of his brain that James had done that for him. What world am I in?

  The couch was comfortable as they sipped their wine. The conversation had dwindled, but it was easy silence until James cleared his throat, seeming to be searching for words. “So…what’s in your bag?”

  Josh had forgotten all about his bag until that moment, slight heat blooming over his cheeks. “I’ll tell you,” he began, twirling the very nice wineglass in his hands, “but first let me say thank you for dinner. You didn’t have to do all that.”

  “I wanted to. Trust me,” James assured him quickly. “You deserve to be treated like that. But I’m dying to know what’s in the bag.”

  Josh really enjoyed this about James—his curiosity and openness in bed. “Well”—Josh tried to focus on work—“I had a few ideas when you said adventurous.” He licked his lips, nibbling on his bottom one. “I brought silk ties for your wrists and a pair of black panties I picked out just for you, because I know you’d look so fuckin’ pretty in them.”

  Josh had expected that James would blush at the words but seeing it was so much more satisfying. James lit up, his cheeks bright, even in the dim light, and he chewed his own bottom lip, a tell he had for nerves.

  “Panties, huh?”

  “Mmm-hmm. If you don’t want to wear them, I’ll wear them instead. There’s one other thing, too, but I’ll need your explicit consent—and none of them will leave with me,” Josh urged, turning to face James a little more on the leather sofa.

  “Okay…” James motioned for Josh to keep talking as he sipped his wine.

  “I brought a Polaroid and figured I’d take a few photos of you all tied up and looking pretty.”

  James blushed crimson, and Josh grinned. Yes. He was in. “I mean, I’ve never done that before, but…”

  “You’ve never done any of this before,” Josh reminded him gently. Suddenly the fullness from dinner was gone and replaced by a new hunger for James.

  James chuckled a little as he shifted. The man was aroused. It seemed that not only did praise arouse the man, but so did the unknown. James was too much fun. “I-I guess you’re right. I mean…if you want to. If you think I look good enough for that…”

  “You definitely look good enough for that,” Josh assured him with a low voice and a pointed look. James didn’t need to know the copious number of drawings Josh now had of him.

  “I probably shouldn’t have eaten so much.” James laughed, and Josh couldn’t help but join in.

  “I’m sure those abs will only benefit from the food.” James kept a clean diet most of the time and worked out hard. His body wou
ld look just fine.

  “Well, where are these panties? I should put them on, right?” James asked shyly and Josh saw James slip into his sweet, submissive role, right before his very eyes. Their dynamic turned him on just as much as James himself did.

  “Follow me,” Josh urged, setting his wine down and reaching for James’ hand. James put his own wine aside, took his hand and followed. Josh absorbed James’ warmth as they walked to the stairs and the waiting duffle bag. He only released it to open the bag and pull out the small, lacy scrap of material. It was a boy-short cut but made to fit a man of their size. James eyed it and Josh could tell he was shy and unsure. “No pressure, Jamie. We don’t have to do anything you don’t want to…ever. Okay?”

  The gentle reminder seemed to soothe the older man. He chewed his lip and took a deep breath, taking the garment from Josh. “I’ll go put it on. Give me a few minutes?” He looked so shy, which didn’t suit the beard he wore at all. It made Josh’s cock throb suddenly—and hard.

  “Of course, sweetheart. Take your time. I’ll finish my wine and be up shortly.”

  Josh leaned in to kiss him and James met him halfway. It was sweet and tender, but the wanting was just below the surface. He hoped it reassured him that this was okay, that this would be fun. He had James’ best interests at heart. He’d take great care of him. He always would. It was his job

  But it was also so much more than that now.

  * * * *

  James stared at himself in a full-length mirror in his closet. He was naked save for the lacy black boy-shorts that hardly covered his ass, let alone his full length. He was half hard simply from anticipation. He’d turned up the heat just slightly for comfort before he’d gotten undressed, and he was glad for it now. It helped…a little.

  Josh Roberts sure knew how to put a confident man on the edge of uncertain territory.

  The thing about it was that James trusted him. He trusted him to make sure this didn’t go downhill. He trusted Josh to know what he was capable of. He was indeed ready for more. He wasn’t sure this was what he’d meant when he’d thought about more, but he was willing to try this—all of what Josh had planned.

  He had to give himself credit. He didn’t look that bad. His Adonis belt abs slipped into the panties, his chiseled chest on display. If he was gonna wear them, at least he didn’t look horrific.

  He padded quietly out of the bathroom, running a hand through his wild hair. He’d mussed it as he’d paced prior to actually putting the little things on. He didn’t really care. It was hardly something to be worried about when someone was about to tie him down and photograph him.

  He knew he could say no—but he didn’t want to. He’d charge through the nerves and let Josh show him a good time. He always did.

  That was the real issue about all this that James was having a hard time confronting directly. Josh was becoming a problem. The man had become someone James needed. It wasn’t hard to invite him in, to laugh with him. He was charming, sweet and when he blushed…it made James want to do it more, more than he was ready to even comprehend.

  He would also continue to ignore the fact that by taking Josh to Italy, he was compromising his time. He would also continue to ignore the fact that if this man left him to sleep with other people, it was his job. It didn’t matter if it didn’t sit well with him when he considered it—so he ignored it and paid him a lot of money, a lot more money than he asked to be paid, to take him away from that for a while and have him all to himself. Thank goodness he didn’t have anyone to tell him how wrong that was.

  A soft knock came on the doorframe of the bedroom as James was just reaching the side of his bed. He stopped and took in Josh’s eyes, which were wide as he seemed to be taking in James’ new attire. James rubbed the back of his neck, feeling those eyes on him heavily and everywhere. “It fits.”

  “It sure as fuck does,” Josh replied in a raspy tone that sent a chill up James’ spine.

  James flushed hard. “How… Where do you want me?” he asked as he ducked his head and looked up shyly through his lashes. Josh set his bag down as he rounded the bed toward him. Sometimes he was shocked by how easy this all came.

  Josh stopped before him and James was surprised to feel his fingers along the lace trim at the top of the panties. They toyed with the material, not pulling or adjusting, just touching and caressing. James had been half hard in anticipation, but the small touches made his erection grow fully. He groaned quietly, letting his eyes fall shut as Josh gripped his balls through the fabric, caressing them.

  “Lie on the bed, head on the pillows, arms above your head. I’m going to tie you down by the wrists,” he explained quietly against James’ ear. “The ties are silk. They’re not easy to break but they won’t hurt you either. Traffic lights tonight, okay? Once you’re tied, I’m going to take some Polaroids and play with you. You’re too fucking gorgeous not to play with.”

  James shivered and found himself thrusting into Josh’s hand fully, groaning when he pulled away. He opened his eyes slowly and was surprised to find Josh staring at him with an utterly gentle gaze.

  “Tell me that’s everything you want, Jamie. Tell me so I can get my hands on you properly. I’m dyin’ to.” Josh’s pinched eyebrows and needy expression told James that he’d meant his words. It filled him with a confidence that he didn’t know he had to do this and made him desperate to see that expression more.

  “Yes,” he breathed. “God, yes. Please. It all sounds like just what I wanted, Josh.”

  “You’re so good to me, Jamie,” Josh replied quickly, leaning in to steal a kiss James was beyond ready to give him. It only lasted a few seconds before Josh pulled away, his expression dark with arousal. James shivered again. “On the bed, baby—on your back.”

  James didn’t hesitate, pulling the comforter off and climbing onto the heather gray sheets. He hadn’t planned it, but he knew now that the panties would stand out. Josh seemed very pleased with that as he grinned and approached with black silk in his hands.

  “Arms up.” James complied immediately, placing his arms where he knew Josh could tie them to his wooden headboard. Josh leaned over him, explaining how much he’d thought about doing this to James, and James wanted to squirm. He has been thinking about this… It made James’ cock throb.

  Being tied tightly to the headboard was a new experience but not one that James disliked. He felt vulnerable and exposed but also warm and comfortable in his own bed with someone he trusted. Josh stripped slowly, down to his own black Calvin Kleins, before grabbing the Polaroid camera. He loaded the small deck of film in, the camera the only noise in the quiet room.

  As Josh approached, James’ heart stuttered. Josh was all lean lines and chiseled muscles. He’d committed most of them to memory, but it was still something he couldn’t get over. Josh’s shoulder-to-waist ratio alone still floored him. He chewed his bottom lip as Josh hovered around him, seeming to prepare for the pictures and deciding which angles he wanted. “Close your eyes.” Josh murmured it in that voice that James was starting to hear in his dreams. James closed them quickly, being very good at listening these days. “Good boy.” He also heard the snap of the camera. The whirring followed and James knew the picture was printing. It was surreal—terrifying and yet exciting. “So fuckin’ beautiful,” Josh whispered moments later, discarding the picture on the table beside the bed. James cracked his eyes and Josh shook his head with a grin. “Roll your head to the left. Bury your face in your arm—yeah, just like that. God, you’re so pretty, Jamie. Shit…” The last word was more of breath as Josh began snapping pictures.

  He’d instruct James occasionally—sometimes his eyes open, sometimes shut. When James would squirm, he’d get a tap to his cock. He’d groan and try to hold still. It was exhilarating.

  What felt like an eternity later but was probably a mere twenty minutes, Josh was crawling onto the bed, the camera and photos forgotten. “I’ve got to get my mouth on you, Jamie. I can’t wait any longer.”


  James was a whimpering mess, a strangled ‘please’ leaving his lips. Anticipation had worn his resolve thin. He needed to be touched. Josh didn’t disappoint as he nuzzled his face into the black panties and cupped his balls through the fabric. He shivered and James moved his hips, a groan escaping. James caught Josh’s pleading grin and his face flushed. Yes. He loved this. There was no question. He was so glad he’d flown home.

  Josh mouthed at his straining cock through the fabric. It was hot, wet and simply not enough. James hissed and tried to move so he could encourage something more. A strong arm settled across his hips and he sucked in a breath. “Hold still,” Josh admonished with a dark look. James stilled, his heart pounding.

  “Please,” he whispered. He needed something, anything.

  “You want me to suck you, fuck you with my fingers?” Josh asked as he lazily pulled James’ length from the panties. He cried out at the first graze of his tongue.

  “Fuck…yes…” He was in so much need that it seemed impossible to wait. Josh seemed to understand as he opened his mouth and engulfed James’ length in the warm, soaked heat.

  James felt the tear of the fabric more than he heard it, along with the rush of air on his skin as his balls and ass were now exposed. It was so many sensations all at once, but Josh kept a slow rhythm on his cock, simply massaging with his tongue and sucking. James didn’t even hear the cap of the lube before there were slick fingers between his cheeks, rubbing his hole experimentally. He jerked, despite his best efforts, widening his thighs and biting his bottom lip with a vengeance. Yes, right there, right there…

  Josh teased him with one, pressing forward to breach slowly as he sucked his cock harder. James would have been lying to say he hadn’t used his toys lately, thinking of Josh the entire time. There was a quick pinch, but he relaxed into it, moaning loudly into the dark room.