He was standing at the end of the room with his hands in his pockets; presumably taking in the gorgeous view of the city. Or he might have been staring off thoughtlessly. I couldn’t tell.
I knew he’d heard the door open and shut when the assistant let me in but he didn’t turn around just yet. I wondered if I ought to announce my arrival but I just stood there like the nervous dope I was.
When he finally turned, he revealed himself to be quite the handsome man. He was tall with broad shoulders; a lean and toned frame even with the fitted suit on. His face had the sort of perfect symmetry that made you intuitively envy him for being so goddamn gorgeous but there was brutishness to it too. Perhaps it was the thin jagged scar across his cheek or the fact that he seemed to be biting down on his molars.
He kind of looked at me with an odd surprised expression and I wasn’t sure if I was in the right room. (Later — much later — he’d claim that his expression was because he was stunned by me but I hardly believe that he, with all his masculine and heart-stopping sexiness, could have been stupefied to see a thing like me.)
“I-I’m Jordan Baker,” I stammered as I walked forward. “I’m not sure if this is the right—“
“It is,” he said cooly as he walked towards me.
He held out his hand and I took it. His grip was firm and confident. “I’m Oliver Simmons.” He gestured to one of the two leather chairs facing each other in the middle of the room. “Take a seat.”
God, I was nervous! I’d been told that it was already a sure thing and that this meeting with Oliver was one of the last steps — to finalise the “gig”, as it were.
I watched him undo the button of his jacket as he crossed his legs. “Tell me about yourself,” he said.
“Oh god, I don’t know,” I said with what I’m sure was a dumb-looking expression. I was nervous though like I said. And the way he was sitting in front of me, looking so composed and unnerving, made me feel like I was being set up to fail some kind of impression test. I was already getting off to a bad start. “I thought I already covered that in the first interview.“
He tilted his head and I looked down, embarrassed by my lack of preparation. They just hadn’t given me any clues as to what this was all about.
An empty, practised smile crept on his face and he shifted in his seat so he was leaning forward.
“Jordan, isn’t it?” I nodded apprehensively and breathed out. “What I want from you at this stage is to get an idea of who you are and what your interests are. And based on what you tell me, we’ll be able to pair you with appropriate clients — men with whom you’re most compatible.” So that was what I signed up for — a gay hooker matchmaking service? That seemed a little OTT for a business that sold sex.
“We find it best to make matches that are… symbiotic,” he said. “Do you understand?”
“I think so.”
“Good,” he said as he leaned back into his chair. “So, what sort of things do you like to do?”
“Like, hobbies?”
“Sure, and activities and so on,” he said, not looking up from the notepad he was scribbling on. “What do you do in your leisure time?“ Eat left-over take out and binge watch TV, I thought.
“I write,” I said.
“Books?”
“Sure,” I lied.
“What kind of books?”
“Memoirs,” I said. His eyes shot up and he crossed his legs again. I gulped.
Why the fuck did I tell him that?
“Jordan, I’m sure Annette and — who did your interview?”
“Garth—“
“Right,” he continued. “I’m sure they explained to you how important discretion is in this line of work.”
I’d read the contract several times over. I could have recited it in my sleep at that point.
“They did. I didn’t mean anything by that,” I laughed anxiously. “To be honest, I mostly write about my deadbeat dad and growing up in friggin’ Idaho.“ He pursed his lips at me and my smile receded. Clearly, my answer hadn’t quashed his worry, so I tried a different approach. “I’m not interested in people knowing I’m doing this,” I said.
Another lie.
“Is there anything else you like to do?”
“I’m not all that interesting.”
“I disagree,” he said but failed to elaborate. “What do you like — sexually?”
“Uh…”
“You can be specific.”
I licked my lips and considered my answer. “I guess I like not being in control. Um, I kind of like, you know, um, being ‘taken.’”
“Do you like rough sex?”
“Uh, yeah?”
“What type of men would you like to be paired with, ideally?”
“What type?”
“Physically.”
“I don’t know,” I said. “I guess I like older guys.” He looked at me then, for a moment, and I realised that I was sort of describing him.
“How many lovers have you had?”
He’d asked me so many personal questions already and yet I was taken aback by this one. I’d slept with only three people in my life and at twenty-six, that number was starting to get a little embarrassing.
But I answered.
“And were any of them older?” he asked.
“No,” I said. “But you said ‘ideal.’”
He paused a bit and just looked at me. “Okay,” he said after a moment. “I think I have enough information to determine a profile for you.”
“That’s it?”
“For now,” he said. “You still have to be, uh, vetted.”
What he meant was that I still had to be evaluated. I’d been told by Annette and Garth that I’d have to be appraised; to see what “skills” I had and what I could improve on.
“We’ll contact you soon,” he said as he stood. I took this to mean the meeting was over. When I stood up, I found him staring at me.
Something about his gaze made me feel like jelly. I got up and started to leave before turning back around and looking at him.
“I like being held,” I said. It was such an odd and silly thing to say but I felt compelled to tell him.
He tilted his head at me and I bowed mine in embarrassment. “I’ll make a note of that,” he said.
I sighed and looked up again. “Bye,” I said.
“Goodbye Jordan,” he said. He said it so gravely and it occurred to me that I probably wouldn’t see him again. That filled me with a weird sense of unresolvedness. But that wasn’t the last time Oliver Simmons and I would be in a room alone together.
~
The address I’d been given was for a very fancy apartment building uptown. I didn’t know what to expect. Charlie told me that it would be like an audition.
“Like a casting couch thing?” I asked with a laugh.
He shook his head bemusedly. “You'd better take this seriously,” he said. “This is probably where you’re going to fail.”
“I’ve had sex before Charlie, I think I’ll do fine.”
“Being an escort isn’t the same as being a hooker. This is about showing up as a person, not just a body.”
“Do you always pontificate about sex work?”
“Do you want my fucking advice or not?”
He told me to be as accommodating as possible. “They like yes men,” he said. “So just do whatever. You’re probably going to get Anthony. He’s their go-to dom. He’s hot as hell and he fucks like a god. But he’ll demand a lot from you. You probably won’t walk right for a week.”I laughed. “And what’s the purpose of all this anyway.”
“To see how good you are,” he said. “And to see if you were bullshitting about the kind of stuff you’re into.”
“Oh?”
“Some guys lie because they think that’ll better their chances. They won’t kick you out or anything, they’ll just adjust your profile to something you’re more comfortable with.”
“Sound like they’re the accommodating ones.”
I remembered the line that man, Oliver, had given me; about wanting to create symbiotic pairs. From what Charlie was telling me, it sounded like he meant that.
“But you want your article to be on the freaky side, right?” he asked and I nodded. “Then you’ll want to be paired with doms. They tend to be more interesting than your mild-mannered client.“
I was starting to get nervous as I passed the doorman and walked into the building. I could have backed out right then if I wanted to. Annette — the CEO of Luxe Escorts — had made it abundantly clear that my contract could and would be terminated at any moment of my choosing. But the curiosity and the thrill of what I was getting myself into was too overpowering to give into my reservations.
I rode the elevator up to the penthouse apartment. I had no way of knowing what kind of profits Luxe made but it must have been a lot if this was where they held their appraisals.
The doors of the elevator opened to reveal a small space in front of french doors. I stepped out and breathed before knocking on the door.
“Come in,” a voice said. I twisted the handle and walked into the suite. The room was both opulent and minimal as it seemed to be the case with all Luxe spaces. Their offices were also like that. I set my messenger bag on one of the sleek grey couches and then walked to the window.
The view of the city was spectacular! Everything but the skyscrapers seemed so little; the people below me appeared to be tiny ants.
I was so absorbed in what I was looking at that I didn’t hear him behind me.
“This is one of my favourite views of the city,” he said.
I spun around to find Oliver behind me. He was wearing a light blue suit. I furrowed my brow as he stepped closer.
What was he doing here?
Oh God, is he here to watch?
The idea sort of embarrassed me. The meeting I’d had with him had left me so flustered. There was something about this man that stirred a nervousness within me.
“Hello?” I stood straight as he walked past me to the table in the corner.
“Would you like a drink before we start?”
Before we start?
“You’re gonna be—“
“Yes,” he said as he sipped scotch. “Is that a problem?”
“I—“
“You do prefer older men, don’t you?”
“I do,” I said. “Yeah, sorry, I just wasn’t expecting that it’d be you here.”
“Are you sure you wouldn’t like a drink?”
“I don’t like scotch.”
“Why not?”
“Because it tastes like poison.”
He didn’t even crack a smile. I stood there, feeling like an idiot, as he put his drink down.
“For this session,” he said. “We’ll run a scenario.”
“Like role-play?”
He huffed a little laugh. “No, something tells me you’re a terrible actor.”
I wouldn’t be so sure,
I thought.
“I’ve just had a long day at work. I’m feeling stressed and so I call you,” he said.
My fuckboy.
“I’d like you to show me what you would do in that situation.”
Tentatively, I stepped forward. I figured I’d just do to him what I did whenever I felt stressed. I stood in front of him, my face only coming up to the collar on his shirt. I reached for his belt and started to unclasp it when he put one hand on me.
“There’s no need to rush,” he said.
I looked up. His grey eyes were fixed on me in a cool expression. My hands left his belt and I moved behind him. I tucked my fingers into the collar of his jacket and peeled it off of him. My hands trailed his shoulders and his back. He was fit, that was for sure. I didn’t have to feel his actual body to see that.
“Maybe you should sit,” I said. He was tall.
He turned around and a sly smile shaped the corner of his face. He held my hand and led me to the bedroom. Still holding my hand, he sat down on his bed and pulled me so I was standing between his legs. My heart pounded as he took off the blue hoodie I was wearing and tossed it to the floor. Then his hands were trailing my abdomen as he lifted the shirt I was wearing, I pulled it over my head as he unbuttoned my jeans and pulled the zipper down. I stepped out of them so I was just standing in my briefs.
I was so nervous. How could I not be when the hottest man I’d ever seen was looking at my lesser body?
Then his hands were on my upper arms and he tugged at them, bringing me lower. He kissed me then, lightly and slowly, as I straddled his lap.
I moaned as he deepened the kiss and ran his hand up along my back before his fingers were running through my hair and pulling.
I could feel my cock getting harder as his other hand played with my nipple, flicking it several times before giving it a little pinch.
I gasped as I pulled away from our kiss. Then I bowed my head and met his lips with mine once again. I tugged at his tie, pulling it off, before undoing the buttons of his shirt. He was wearing a white t-shirt underneath which I also took off.
I ran my hand on his hairy chest and breathed as his smouldering eyes looked at me.
I wanted him. Almost desperately. But something told me he wasn’t there yet. So I leaned over to the side and crawled on the bed so I could be behind him.
I placed my hands on his shoulders and began rubbing him there. He threw his head back and breathed deeply as I hugged him from behind. I pressed into him and held him tighter as one hand caressed him.
I trailed kisses all over the curve of his neck as I finished unclasping his belt and pulled it off.
“You’re so hot,” I whispered as I unzipped him and pulled out his cock.
He was big and he felt wide in my hands. I held the base of his semi-erect cock and then slid my hand up and down along its length. He shifted and I could tell he was getting more turned on which, in turn, fuelled my lust.
I stroked him further, feeling him harden completely in my hand. He lifted his hand and tightly gripped mine.
He turned his face to the side and tilted his head so I would kiss him. As our tongues wrestled, he shifted to the side so that he was facing me.
Then he lowered himself, pushing me down so I was lying on my back with him on top of me.
As he kissed me, I lowered his pants over his ass and he pushed them off completely. Then his fingers held the waistband of my briefs and he took them off with ease.
He got on top of me and captured my mouth with his, kissing me passionately as we ground our cocks against each other.
“You’re beautiful, Jordan,” he said when he broke the kiss. “So beautiful.” He certainly made me feel like I was. The fact that he seemed so turned on by me delighted me in the vainest way possible.
“Turn around,” he commanded. And then I was lying on my chest. He pulled on my waist so that my ass was in the air. And then he lowered himself.
I felt his tongue on my hole, teasing me. I moaned as I felt his thumb along my ass. And then it too was tracing my hole.
He pressed deeper and pulled out several times, making me tremble with need. He was an awful tease.
“Oliver…” I pleaded.
He inserted his thumb briskly into my hole, making me yelp. Then his hand was on the small of my back. I craned my head and watched as he fingered me. I began moaning as the massage felt more sensual than uncomfortable.
“Oliver…” I pleaded again. There was no doubt about what I was asking for now. “Please,” I said.
He didn’t let me beg anymore, thankfully. He got on his knees and I felt his rigid cock behind me, tantalisingly stroking my hole. I worried that he’d be much too big for me. And that it would hurt. But did that lessen my desire in any way? Fuck no!
I found myself shamelessly wiggling my bottom at him. Then the head of his cock was pushing into me and I braced myself for the intrusion. He gasped and let out a strangled moan as I buried my head into a pillow. I bit down on the fabric as stray tears fell from my eyes.
Both his hands caressed the skin on my back. “Relax for me, Jordan.”
I did my best to stop my body from tensing up. I wanted him to take me. I just needed a little time to adjust.
He made a trail of kisses on my back as he massaged my chest. “It’s okay baby,” he said soothingly, as I loosened up.
I started backing up on him and more of his cock entered me. Only there was no sharp pain this time.
He held my hips and slowly thrust into me. The sensation seemed to light my nerves on fire.
I moaned as he pumped into me, loving the way his cock was making me feel. I backed up a little more, to let him know it was okay to go all the way. He fucked me hard but slow; and oh so exquisitely. I was delirious with lust and ecstasy.
I moaned as he got lower, making me lie flat on the bed. I was hardly aware of the words coming out of my mouth — just a lot of incomprehensible expressions of elation.
“Mmm yeah, daddy,” I said absentmindedly. Oh hell! He stopped thrusting on top of me and I buried my head in shame at having uttered that slip.
He pulled out of me completely. His hands were on my thigh and my knee, twisting to make me turn over and face him.
I lay on my back but averted my eyes.
“Look at me,” he said. My heart was in my throat when I looked up at his face. It was softer somehow as he lowered himself between my legs.
He pushed his cock into my ass before kissing me deeply.
“You like that?” he asked as he thrust his cock deep inside me.
I nodded my reply before he kissed me again.
“You like that, baby?” he asked as he pressed himself down, closing the space between us. “You like it when daddy fucks your pussy?” My eyes widened at his vulgarity.
“Yes,” I whispered against his lips. “I love it. I love it, sir.”
“You want it deeper, don’t you Jordan?”
I was moving my hips to meet his thrusts by then and he took my hands in his and held them tightly at either side of my head.
“Yes, sir, fuck me deep.”
He pushed further into me and I gasped with raw delight. My strangled moans never left my throat, his mouth was on mine the whole time he pumped into me.
He pulled away from me and his breaths became shallow and jagged. “I want to cum inside you Jordan,” he said.
“Yes, daddy, whatever you want,” I gasped. “Use my body sir.”
That sent him over the edge, it seemed. Because then his movement above me became jerky as he filled me with his seed.
He pumped into me a little longer even after he came.
Then he raised himself and knelt in between my legs. He held out his hand and lifted me as well. He wrapped one arm around me while the other held my hard cock.
He began stroking me, gently at first and then furiously as he held me against him.
My hands were around his shoulders as he jerked me off. Soon, I could feel myself at the edge of climax.
“Oliver,” I whispered.
“Cum for me, baby,” he said as he continued jerking my cock.
He pulled me tightly against him as I experienced my release. He squeezed my cock until I shot every bit of my load.
“Come here,” he said before kissing me again. His hand trailed my body as I came down from my orgasm.
Then he lowered us so that he was on top of me again. He kissed me for a long time and let me rest my head against his chest. He held me until I dozed off.
“Is this your apartment?”
Upon perusing, the room wasn’t as clinically minimal as I had first assumed. Then again I was the sort of person who lived by the phrase “homely means messy”.
“Yes,” he said. He was dressed now as was I, only, of course, he looked a lot finer than I did.
Why would he bring me to his apartment? And why did I assume this was a Luxe apartment. It was way too stylish and spacious to be a fuck house, wasn’t it?
“I’m going to dinner,” he said. Meaning I had to leave.
“Oh, let me just grab my bag, I’ll be out of your hair.”
“That’s not what I meant,” he said as he crossed from the kitchen where he was standing to the living room.
“What?” I asked as I slung the bag over me.
“That was an invitation.”
He looked at me with such an absurd expression. Like he just couldn’t believe I’d missed his meaning.
I gestured toward my body. “Like this?” I looked… frumpy is a nice way of putting it.
“I’m sure no one will be paying attention to you, Jordan.” There was amusement in his voice but his face was straight.
“Yes, they will,” I retorted. “They’ll be looking at you — obviously — and then they’ll be like ‘What’s that thing next to that gorgeous man?’”It was the first time I saw a genuine smile from him. That he was laughing at me didn’t matter. I just liked it.
“Wait here,” he left the room and then came back with a business card in his hand.
“What’s that?”
“The stylist,” he said. “You should call her.”
“Luxe has a stylist?”
“Yes, we do.”
“Does the stylist dress you?”
“No,” he said, taking a step closer. “I dress me.”
I was looking at him, not saying anything. He kissed me goodbye and I smiled under his lips.
“I guess, I’ll see you later?” I asked, praying that the answer would be yes.
“All right,” he said. Then I left.