Trick And Treat

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I don't know what it is about rent boys and handcuffs that goes so well together in my head, but they just do. Sometimes, as high-end escort Jonathan discovers, a sly client spots you hiding your emergency key, and then all bets are off.

Oh, and I just released a new book: "Show Me" is all about what happens when you get caught gooning by your twin brother's best friend. It's available on Amazon, Smashwords, and more, and you can find more details at my site, www.alexpendragon.com

I love getting emails from readers (alexp336@gmail.com) and I have a mailing list with a free story for new sign-ups. Happy reading!

-Alex

"Trick And Treat"

It was a soft, pillowy bed, certainly not small, with the sort of high-thread-count sheets you'd expect from a hotel that prided itself on its five stars, and so the only discomfort I could really complain about were the handcuffs around my wrists. Arms held up as a result - hitched not quite so high as to drain the blood and leave them numb, thankfully - since the cuffs' chain had been looped, very effectively, around the sturdy wooden headboard.

I'd had - since waking, stretching, flirting, being enthusiastically fucked, and then abandoned - plenty of time to consider my life choices, curse regular clients with offbeat senses of humor, and scold myself for never saying no.

"You look so hot, all plowed-out and sweaty," he'd said, as he watched me from the foot of the bed. Dressed, by that point, in a somewhat rumpled version of the vampire costume he'd worn for the party the previous night. Minus the top hat, cane, and teeth of course; without them, the tuxedo could be mistaken for regular evening wear.

I'd glanced at the nightstand clock, then flashed him one of my most effective come-hither grins. It looked slightly different, I figured, with the plastic fangs he'd asked me to put in again. "You're welcome to show me exactly how much you enjoy it."

He'd laughed, shaking his head with the sort of expression that suggested further indulgence was being genuinely weighed. "I would," he told me. "But someone's got to earn the money to keep you in the manner you're so clearly accustomed to."

Some of my clients, I've found, preferred to ignore the transactional aspect of our relationship. Usually because they want to pretend that a doting twenty-something guy was hanging on their arm for their personal merits, not their credit score. More rarely, though, I'd find one who seemed to positively relish the fact that my attentions were paid for.

I was happy to play up either angle, just like I was happy to do a lot of things to keep the customer satisfied.

"Next time, then," I'd suggested, and got a wink in reply. Then frowned, at the key he was suddenly brandishing.

"I'll just leave this here, then." The sliver of metal - still with the strip of tape with which I'd surreptitiously stuck it to the back of the headboard - made a soft clink as he set it down on the table. A table that, it was impossible not to notice, was well out of my reach. "I'm sure someone will be along eventually, to let you loose."

I'd tried more flirting, and then scolding, before outright threats and then a little common-or-garden pleading, and by the end had only slightly sore wrists and the unpleasant realization that yes, he'd been serious, and yes, he'd just left me handcuffed to the bed in some fancy boutique hotel room.

The obvious next step would've been to strain against my bounds and yell my head off. I certainly considered it for a brief, frustration-filled moment, but I knew that was a lost cause. The bedroom was at the far end of a suite that had proved throughly soundproofed (at the time, that'd been a plus not a minus), and the handcuffs were the sort of law enforcement quality that professionals preferred. The most I could hope for, from the strain-and-yell strategy, would be bruises and a hoarse throat.

And so I lay there, waiting for who I assumed would be housekeeping to find me at checkout time. Wishing - even though the room was pleasantly warm - that I hadn't kicked the sheets down quite beyond my toes' reach. If only because, carbon steel bracelets and joke store teeth aside, I was entirely naked.

The TV remote was also out of reach, sadly, which was annoying considering a pay-per-view movie was probably the least of the things I was owed right now. Even if it'd only be some dreary blockbuster I'd missed at the theater, since the dates I tended to go on invariably skipped popcorn and went straight to dinner and a ruthless dicking. I'd dozed off when I heard the click of the door.

You have a choice, when you're about to be discovered naked, to either announce yourself or leave it to be a surprise. I figured whoever had just come in would probably prefer at least some advance notice that they had company.

"Uh, hello?"

It was past one, the clock informed me, suggesting I'd napped a little longer than I'd thought. Late enough that whoever was pushing the slightly squeaky cleaning cart would've reasonably assumed that the room was empty.

"Hello?" I called out, a little louder. "There's someone in here."

It was, I decided a moment later, a fairly ridiculous thing to add.

"Sorry, it's housekeeping." A man's voice, from the lounge next door. "I thought... well, the room is checked out."

I sighed, allowing myself a brief moment to curse "playful" clients who were obviously more observant than I gave them credit for. I really had thought my backup key went unnoticed.

"I'm in a bit of a bind," I admitted, voice still raised. "If you could help me, I'll get out of here straight away."

It was possible, of course, that hotel policy insisted housekeeping staff were meant to contact reception, or some sort of manager, in situations like this. Which had the promise of exponentially greater embarrassment. I found myself hoping that - if only in aid of an easier afternoon - whoever was on the other side of the door would ignore the rules and just come through himself.

A head stuck just around the frame, eyes downcast. "Um, checkout is at eleven, sir."

I felt a small, but not-unnoticeable, flush of satisfaction at the thought that my client would probably be charged a late checkout fee. It was a minor triumph - a fraction, undoubtedly, of what the glass of whiskey had cost him after dinner, when my bare toes had been squirming around his crotch under the table - but I'd take my victories where I could get them.

"I know," I agreed, amiably. "But unfortunately..." I shook my hands, making the ASP's chain jingle.

He looked up, frowning. First at my face - the frown deepened slightly, at the sharp incisors - then my raised arms, before his gaze skittered down my naked body.

I saw his eyes go wide, for a split-second, before he hurriedly closed them. A flush rapidly spreading across each cheek.

"I... Uh, I..."

No way not to wince, in sympathy, at his stuttering. The forty-something guy at reception hadn't even blinked when we'd checked in the night before; I figured his career had been long enough that a late middle-aged man dressed as Nosferatu and booked into a superior suite with someone half his age didn't even register on the "weird stuff" scale any more. Clearly, though, the housekeeping team was less familiar with the concept of walking in on five-foot-eight of stark naked rent boy sprawled out on a California king.

"Wh-what happened?"

His turn to wince, then. At, I guessed, the just-too-late realization that even if he was permitted the impertinence of asking guests direct questions, some answers he might not want to hear.

"A practical joke," I explained, trying to keep my tone casual. All I needed was the key from the table, and I could escape to lick my metaphorical wounds and decide just what sort of overtime fee to demand.

"I should go get..." he started.

"No!"

I swallowed, instantly regretting my volume. He seemed skittish, even though he had to be about my age. At least, as far as I could tell from a head still sticking around a doorframe with the eyes shut.

"No, it's fine, just... I need the key, from the table over there."

He opened his eyes, studiously not looking in my direction. "The key?"

"For the handcuffs, yes."

"How did you get handcuffed?"

Rolling my eyes probably wouldn't endear me, even if I was pretty sure he was doing everything in his power to avoid glancing my way. "The guy I was with likes it."

His head flicked around, eyes wide again. "Oh." Then, as if seeing my nakedness properly for the first time, he bit down on a gasp. "Oh!"

I shrugged.

"Your boyfriend just left you like that?"

His indignation on my behalf was actually quite charming, though that didn't stop my snort of laughter. "He's not my boyfriend."

A slow nod, like he was processing. Not that I was entirely convinced of the accuracy of his conclusions.

"Look, just come in, will you? I promise I won't bite."

He chuckled, looking something less than shellshocked for the first time. "I mean, you can't do much, I don't think. Not like that."

I couldn't help it; I flashed him a knowing smirk. "Oh, don't underestimate me."

It was fun how quickly his expression paled, but he still pushed open the door and tentatively took a step in.

I figured twenty-four, or thereabouts. Taller than me, though standing in that way shy people do when they think their presence should be less obvious. Dark hair, with a fringe that fell down almost over his eyes. The braces on his teeth only made him look more innocent, more naive, though it was clear from the stretch of the hotel-branded polo shirt that he wasn't exactly weak.

"Could you pass me the key, from over there?"

He glanced at the table, then back at me. Expression more curious, now.

"How did you know the guy? The one who left you?"

I made a face. "We've hung out a few times before."

"But you're not dating?"

I tried for what I hoped would be a friendly, patient smile. "No, we're not. The key?"

His gaze flit down my body. That was one of the downsides of sex work: after a while, you started to forget that a lot of people still had hang-ups about nudity. Then, eventually, it became second-nature to take advantage of that fact.

"Why are you naked?"

I couldn't help it: the eye-roll was too tempting, and his incredulity too annoying given the circumstances.

"To make it easier for him to fuck me," I snapped, bluntly.

His mouth dropped open. "So you..."

Ripping off the band-aid would be easier, I decided. Otherwise we could tiptoe around the truth of the matter for an hour.

"He likes to handcuff me, so I can't squirm away, and then fuck me raw until he breeds me. Only then he's meant to unlock the cuffs, and today he didn't."

From the way his jaw was working, it looked like he was auditioning a few possible responses.

"And the... the teeth?"

I licked across one pointed tip, as though just remembering it. "Halloween party. He was the scary vampire, and I was the slutty one." It'd been a cute costume; he'd not been able to keep his eyes off my ass in the shorts. "Then dinner, then I spread my legs and earn my keep."

"And you... you're okay with... with that?"

I shrugged again. "It's what he pays me for."

In theory, discretion was also part of what I was being paid for. Which included not blurting out details of the arrangement to random guys from housekeeping, only it didn't seem like we were playing by the pre-agreed rules any more. Not to mention the fact that it was past lunchtime, I was getting pretty hungry, and my shoulders were feeling increasingly stiff.

I sighed. "Look, what's your name?"

For a moment, and the way he frowned, I thought he was going to refuse to tell me. Perhaps his mother had warned him about conniving demons who only needed your real name in order to steal your soul. Frankly, though, I wasn't in need of it.

"Juan," he admitted, finally.

"Nice to meet you, Juan." I gave him a beaming grin, one I'd seen work miracles on grumpy old men who might be on the cusp of questioning the boys they paid to spend their time with. "I'm Jonathan. I realize this is all a bit... unusual, but I'd really appreciate it, if you could help me out."

He took another step into the room. Juan seemed a little less shaken by my presence, now, though his eyes still didn't linger on my body. Gaze scurrying, as though if it paused too long he'd be accused of something.

"Is it not... illegal?"

It was as dour a look as I could risk, given I wanted his cooperation. "Are you a cop?"

He shook his head.

"Then maybe we're getting hung up on details that don't matter, no?"

He blinked a couple of times, then grinned. "Yeah, maybe."

I nodded, then looked pointedly across at the key.

Not that he seemed to notice. My openness had apparently left him with the impression that I was willing to answer more questions.

"So you just... have sex? And get paid for it?"

On the one hand, that was a gross - and almost insulting - simplification of the seduction, flirtation, and occasionally pneumatic gymnastics expected of me from every date. Not to mention the background effort at the gym to keep my sleek-but-not-intimidating muscles, the studying to make sure I could hold my own in dinner conversation, and generally everything I did to leave clients with the sense that I was the perfect no-strings boyfriend.

At the same time, though, there was no denying that a not-insignificant part of my job involved spreading my legs, moaning, and letting men cum in me.

"It's a little more complicated than that," I hedged, "but something along those lines, yes."

Juan nodded, slowly, looking thoughtful. "How much?"

I squinted at him. "Excuse me?"

He gestured, as if to take in the bed, and my presence on it. "How much do you get paid?"

"How much do you get paid?" I fired back, sharply.

A grimace. "Not enough."

"Yeah," I agreed, shaking the handcuffs pointedly, "I feel the same way sometimes."

He chuckled. "And you let them... y'know... inside you? Is that not..."

This swinging between coy and blunt was getting tedious. "Presumptuous? Fun? Dangerous? Messy?"

Juan's shrug seemed to encompass all of the above.

"I'm on PReP. And they get tested, regularly. And, frankly, I'm getting paid for a service, just like you are. For a lot of guys, that service involves not having to worry about a condom."

From the way his bottom lip was caught, absently, between his teeth, I decided Juan's sexual experiences to-date had all been resolutely rubbered-up. Not that playing safe was a bad idea: if I had the time to actually date - as in, with real guys rather than men paying for my company and my flexibility - I'd probably be a lot more skeptical about trusting people who wanted to unload inside me.

"When did he..."

I allowed myself a slow, wide smirk. Gratified by the way his cheeks flushed again in response. "This morning, just before he left." I frowned. "Just before he left me here, like this, in fact."

Juan swallowed, thickly. "So you've still got..."

It was unclear whether he'd ever be able to finish a question, though I could guess the intended direction. "His load in me? Yeah. Why, you wanna see?"

He looked genuinely horrified. Though didn't, I noted, say no.

I let my stare drift down from his expression, across his broad chest - the hotel logo skewed across his left pectoral - and to the scuffed, faded black jeans. Well-washed, and snug around his crotch.

Sometimes, I just can't help myself.

"He's big, really hung. The guy who I let breed me, I mean. Long, and thick." I shifted my hips, legs spreading slightly. Watching as he tried and failed not to look down, to where my cock was thickening at the memory. "Some of the men, the sex is shit. I have to be an actor as much as a whore. But this guy... he knows how to fuck."

It wasn't a lie, either. I was pissed, at how he'd locked me up and walked out on me, but I knew I wasn't going to deny him another date. All those hours in the gym would be a lot easier to stomach, if every man who bought my time could work me over so effectively.

"How big is 'big'?"

It wasn't the question I was expecting, but then again it didn't surprise me much, either. Men were generally competitive, in my experience.

"Has your girlfriend complained?"

Juan screwed up his face. "No girlfriend."

It was less of a shrug, and more just my jingling the handcuffs chain. "Size isn't everything. But I like them thick. Just personal preference, y'know?"

The wide-eyed look he was giving me made me reconsider my previous assessment. I now had a strong suspicion that Juan hadn't in fact been inside anyone, yet, condom or otherwise.

The way the crotch of his jeans looked markedly fuller, now, also made me think that just hearing about other people do it was enough to get him turned on.

Not that I was anything less than three-quarters hard, too. Spreading my legs wider on the smooth sheets, feeling that shiver of pleasure at how the young guy's attention instantly snapped to my cock as it lolled against my thigh. I usually bottomed - the guys who paid for me seemed to invariably prefer that - but the few who had gone down on me never complained about what I was packing.

"His loads are huge, too," I said; my voice low, like I was confessing a secret. "He likes to watch, as I push them out on his chest."

Juan grunted, face twisted. "That's gross."

Not that it stopped him squeezing his junk through the tight denim, though. Absently, like his brain didn't know what his hand was doing. Kneading the heavy bulge that I could now see straining at his palm.

"Sometimes, when that fat dick's done with me, my hole is just gaped wide open." I watched Juan's face, the shock and barely-disguised fascination passing across it. "I can hardly keep his cum inside me."

"B-but it's in you now?" So low, I had to strain to hear him.

I nodded, smirking. Spread my thighs wider still, tilting my hips to push my ass up on the bed toward him. The guys who paid for me all seemed to agree that I had a great butt, perky and round. They certainly had no complaints pounding against it.

"You ever been with a guy?"

Juan looked terrified, as he shook his head jerkily.

"With a girl?"

He swallowed, looking embarrassed. Then shook his head again.

His body language said he was fearful, but the fat ridge of his erection told me not every part of him was so unsure. I beckoned him closer with my chin.

"Look, here's the secret," I murmured, as he got up on his knees at the edge of the mattress. "A hole's a hole, yeah?"

Swollen pupils almost eclipsed the brown of his eyes.

I stared at his crotch, grinning. "You wanna show me, and get a professional's opinion?"

Despite everything, he laughed. "What's that gonna cost me?"

I winked at him. "We'll call it the fee for rescuing me."

He smiled, bashfully, and I expected to hear him decline. Politely, though; in the way the hotel had probably taught him how to speak to guests.

Instead, he tugged at the button of his jeans.

Gray Hanes boxer-briefs underneath, but it was the heft inside them that I was more curious about. Wishing that my hands were free, that I could reach down and pull Juan's cock out and stop this tauntingly slow pace, yet forced to merely watch between the splay of my legs as he eased his underwear down.

I hissed, as the fat length of it sprung out. Already drooling precum, bobbing as arousal fought his cock's heft. Enough to have that itch inside me start up in earnest; a reminder that, though my getting plowed was usually the customer's choice, that didn't mean it wasn't in line with my own general preferences, too.

Some things, I didn't have to fake.

Juan looked apprehensive, when I glanced up at his face. As if braced for bad news.

No way to hold in my snort, or to temper the expression of disbelief. "Are you fucking kidding me? I want that in me. Now."

A grunt of shock, and then he was laughing again. Moving nearer, clumsy on his knees with his jeans and underwear a tangle between his thighs, but it didn't matter. Not when I was mentally doing the math on how close he'd have to be for me to seize him with my legs and pull him in against me.

"D-do I need..." he started.

"Just spit on it," I interrupted. "Cum makes a decent lube."

I wondered, even as I said it, if that would be a step too far for him. The idea of pushing in where another man had already left his mark: the thought of some stranger's load squishing around his dick.

Questions rendered unimportant by the sound of him spitting in his hand, before he stroked it down his fat inches.

I watched his face, as Juan watched the head of his cock push into me.

Thick enough, flared enough, to make me gasp. Shaking my head a moment later, at his look of concern; urging him on with my heels against his ass, my body reshaping around his shaft as he leaned over me.

"Holy fuck, it... it feels so..." He sounded distant, like his brain had ballooned right out of his skull.

"Do you want to talk to me, or do you want to fuck me?"

A snort of laughter, and then he shoved his hips forward.

"Oh, fuck." The curse escaping without thinking, as the ripple of pain-pleasure shook through me. Knowing, too, that what came next, I'd invited upon myself. Juan already dragging back, my sloppy hole trying to grip him as he pulled almost free, and then all the air punched from my lungs as he buried himself again.

His head down, he slammed into me, over and over. Reaching up, long fingers wrapped around my neck and my jaw. Then looking up in shock as I opened my lips and sucked in his thumb, nipping at it with the plastic canines, nursing on it as he plowed me with desperate enthusiasm.

The way he was staring at me, as I ran my tongue around his rough digit, suggested Juan was now wondering just what else my mouth might be good at.

Not that I'd have let him pull out, even if the idea of deep-throating his meaty, inexperienced prick had me groaning in anticipation. Not with the haphazard strum across my prostate as he slammed me, the exquisite stretch as my body was forced to accommodate him.

"Gonna... cum... in you," he panted out.

I hadn't expected stamina, for it to be long-lasting. Didn't care, either: would've gladly traded a hundred leisurely fucks for the sight of this handsome, blushing, near-overloaded virgin realizing he was about to breed his first hole. Drooling, practically, as he stared at me with wide, glassy eyes; hips hammering, as though if he could just pound me hard enough, he might find another half-inch of dick to do it with.

Not that I needed it, not that he did. Nothing for me to do but lay beneath him, urge him on with my legs wrapping his waist, and count down the seconds until the conclusion we both knew was imminent.

His face twisted, the groan rumbling from the depths of his chest.

I could feel him throb inside me, my own cock rigid between our bodies. Rasping against his shirt, the friction a torment not quite sufficient to get me off.

Another few, haphazard strokes, and Juan collapsed on me.

I could smell him, fresh sweat and musk. My brain spooling out in lazy spirals as his chest heaved and I savored his weight; wondering about the life choices which had brought him here, to the corridors of this hotel, and those which had put me on my back under men old enough to be my father. Not that I'd planned for any of this, just like I figured Juan hadn't planned his trajectory. Circumstance and fate bringing us together this one afternoon, and you could ask a million questions, come up with a thousand theories, and never reach a proper answer.

I grit my teeth, as he dragged his cock out of me.

For a moment, I wondered if the mood was about to turn. Felt - perhaps naively - the first ice-cold twist in my stomach. Lulled, through my work, and my confidence, into forgetting that not every man's reaction to hooking up with another guy was safe, or free from violence.

Not like, either, I was in much of a position to defend myself.

Juan rolled onto his back, at the foot of the outsized bed. Panting, face flushed but the angle denying me a true glimpse of his expression. His cock lolling, heavy and slick with mingled juices.

Finally, he let his head drop to the side, to look up at me. "Do I get a refund, after cumming so fast?"

I stared at him, for a moment, brain struggling to process. To match the words to the impish grin on his blushing, exhausted face. Almost didn't realize I'd understood, until I heard the crackle of amusement burst out of me.

"We only give store credit, I'm afraid," I said, dryly. Though I couldn't stop my grin.

He sat up, smirking. "Oh, so there'll be another opportunity to spend it, then?"

I shook my head, slowly. "That's not how this usually works."

He watched me, wordless, for a beat.

"The key?" I prompted.

He fixed his clothes as he walked over to the table, tugging his boxer-briefs and jeans up. Fastened them, then scooped up the means of my liberation and examined it, carefully.

"What's it worth to you?"

I scowled, even though he was studiously avoiding looking my way. "You already got the answer to that, remember?"

Now he did look over. "So that..." Juan seemed, momentarily, lost for words. "What just happened, it was just to get me to unlock you?"

I'd been naive, and inexperienced, once. It felt like a long time ago, another world even; certainly another version of Jonathan. My first time hadn't been in a four-figure-a-night hotel suite, but I could remember some of the feelings afterwards.

I let my head drop back, against the headboard. Squinting at the overhead lights, suddenly too tired for mind games, or manipulation, or even just flirting. Not that the three were necessarily all that different, in practice.

"No, that was because you're hot, and I was horny," I conceded. Speaking that one truth to the ceiling, so that I didn't need to see how it landed.

His silhouette obscured the halogens. Shadows shifting, and then the click of the lock.

I'd underestimated just how numb my arms were getting. Rubbed them, to try to coax the circulation back through.

Juan was watching me from across the room. Warily, as if he'd just freed some sort of monster, only there was more than just fear in his eyes.

"Thanks," I told him. Pushed myself to the edge of the bed, then stood on legs that were shaky from our fuck, not my confinement.

"You have time for a shower, I think. If you..."

I squinted at him, automatically suspicious. Wondering what might be next on his sexual to-do list, what kinks had unlocked as readily as the handcuffs had been. Whether it was my mouth he wanted, or to add a third load to my ass, or some other combination of awakened flesh.

"If I...?"

He was blushing again. Shrugged, the movement self-conscious, making him look younger.

"If you give me your number," Juan blurted out, words a hurried jumble.

I blinked at him, mind thrumming. Of all the things I'd expected, of all the requests I'd had confessed to me, whether shyly or bluntly, this was perhaps the most perverse.

Or, maybe, the one I'd regret most for indulging. But that's always been my problem: I can never say no to treats.

Hope you enjoyed it! I really do love getting emails, and you can find more stories at my site, AlexPendragon.com.