The Darker Side of Trey Grey

by Tara Spears

  “I didn’t mean to scare you. I took a chance you would be here tonight.” He looked towards the Bentley. “I’ve been waiting.”

  He seemed a little breathless, and his hands were pulling nervously at his jeans. I wondered what was running through his head that had him so riled. Scotty was a sweet, if slightly shy kid that was incredibly fun to tease, and I loved him— in a strictly business sense of course.

  He’d originally come to the Ave a year ago when he was sixteen, unsure of his sexual orientation and wanting to find out once and for all. He had found me. In the interim, the silver Bentley had slowed as it passed my corner before driving off again. After playing this game for two weekends, he finally gathered the nerve and had his driver stop.

  His first time with me had been just that. He had been so cute. Blushing outrageously as I led him through his first gay fuck. He always topped, and he’d lasted about three stiff and wary strokes that first time. The second wasn’t any better. He had asked, with a face the color of beets, if he could touch my “penis”, and when he did, he just about had a meltdown. He was definitely a dick man.

  I was pretty sure he was smitten, but he kept things on a strictly professional relationship, which I appreciated. His dad was some richer-than-god bastard, stretched tighter than spandex on a fat chick, and I could tell Scotty was afraid of him. Thanks to his father, however, Scotty was loaded and very generous with his money. Well, at least with me anyway.

  I gave him a sensual smile and he flushed deeper. “I’m all yours. What’s your pleasure tonight?” I stepped into him and his breath caught.

  Yeah, he definitely had the hots for me, despite seeing me a few times a month for a year now. He was being shyer than usual though, so I bent down and kissed him. He was the only trick I kissed as I knew exactly where he dipped his wick. I had been his first, and I was sure, his only so far. He was too shy to be able to trump me on that one.

  When I pulled away, he was still acting timid and nervous.

  “Scotty, what do you want? Something new I can tell,” I crooned teasingly.

  “I met someone— I think I really like him.”

  I laid my arm across his shoulders and steered him away from the Avenue.

  “Mm, and you want to expand your knowledge.”

  He smiled, twisting his hands in front of himself.

  “Bentley or the alley?” I asked, sliding my hand up and down his tense back.

  His driver was remarkably discreet, considering he was flagrantly disregarding his boss by taking his only son out to screw a prostitute several times a month. A gay fuck at that, and I was confident his father didn’t know about Scotty’s sexuality.

  “Alley. I don’t think the Bentley will be comfortable.” He gazed at the silver car as if contemplating the spacious interior before nodding decisively. “Yeah, definitely the alley.”

  “This is your first time isn’t it?” I knew he had never bottomed, but I asked hoping to quiet the tremors I could feel under my hand. I wasn’t sure if they were from trepidation or excitement, either way he calmed at my soft inquiry.

  “Yeah.”

  “You’ve never asked for this before, so why now?”

  “He, um, like’s to drive.” He let out a woeful sigh and I understood. Scotty wasn’t sure about this, but he liked the guy enough, so he was willing to give it a try.

  “I got it.”

  We turned the corner into the narrow alley I used for tricks. It was set behind a few scraggy businesses that closed conveniently at six. There were no lights here, and the green dumpsters provided enough cover from peeping eyes, not to mention the occasional cop.

  “Face the wall, Scotty, and put your hands shoulder width apart. Trust me on this. I’ll go slow.”

  He did as I asked, and I huddled up to his backside, reaching around to undo his artfully torn jeans. Jeans, I was sure cost more than what he paid me.

  I shook my head, amused, when I felt him hard as concrete. “Do you think of me when you pound one out, Scotty?” I whispered into his ear, making him shudder. “You are always so impressively hard when you come to see me.”

  Tugging his jeans over his hips, I let his dick out to play. He wasn’t long, but the kid was as thick as a tree trunk, and would make a boy that liked to fondle his partner very happy. I kicked his feet out as I unbuttoned my own jeans, and pushed them down just far enough to free my flaccid tool.

  I slid one hand over his dick, as my other tugged mine, and soon he was trembling and “IT” was ready. I pulled out a condom from my inside pocket, rolling it on. I found my lube in the opposite pocket, and set to readying him.

  “This is your first time so no rough stuff, Scotty. Don’t push back, understand?” I lubed his hole then slipped my slimy finger through the tight entrance. He moaned, clenching hard enough to cut off the circulation in my finger, leaving it tingling when he released it.

  “I know I like it,” Scotty said, breathless.

  “Relax. How do you know if this is your first time?”

  “I’ve been playing with toys. I should be— ahhh...” I slid my finger in farther upon hearing that. “Some of them have been pretty big.”

  As he relaxed, I slid another finger in. “So you think you’re ready.” It wasn’t a question, yet his response was to sit down on my fingers, sending them almost all the way in. As he rolled his hips he began to loosen up, bringing a smile to my lips. Man, he was going to make some boy VERY happy. I slid my fingers in and out until he was fully relaxed, then removed them and tore open a sani-wipe, scrubbing the digits clean.

  This was the weirdest thing about me. This, having my fingers up a guy’s ass, didn’t gross me out half as bad as seeing his jizz squirt out.

  Leaning against Scotty’s back, I spread his ass cheeks and settled my tip against him.

  “You really like this guy, Scotty?”

  “Yeah, but he has a lot more experience than me.” He pushed his hips back.

  “You’re pushing. Stop. Maybe he would have liked to fuck a virgin. You ever think about that?” I spread him wider, and gently but firmly pushed against him until my head cleared the tight skin. Scotty rocked back with a deep groan. I grabbed hold of his hips to stop him.

  “He... ahh... likes it rough. He told me.”

  Oh. One of those. I personally liked boys like that. No bullshit, right to the action, and they usually didn’t want much foreplay. Of course I was all about the quick fuck, however I felt Scotty wanted the intimacy.

  I rotated my hips, sliding in a little farther, and Scotty moaned again. I could feel “IT” beginning to throb over his obvious and delicious pleasure. I wriggled my hips and gained another inch. So. Fucking. Tight. My head lolled back. Jesus, I was going to come over this. The thought should freak me out, and I was sure, later, I would probably be hanging over my toilet or playing with my scrub brush. But right now I actually wanted to pound Scotty’s ass, which had me amusedly baffled and I couldn’t really stop what I said next.

  “Did you cream your pants when you heard he plays hard, Scotty?” I flicked my hips as he rolled his like a hula dancer. “Do you want it rough? To be someone’s bitch?”

  He groaned at my words, and I dragged his hips back sliding in the rest of the way.

  “More, fuck— more, harder,” Scotty pleaded and demanded all at once. I don’t usually pick up a rhythm with a first timer, but shit. Scotty was a born bottom and he kept sitting on my dick, and clenching, and he had “IT” throbbing so hard it fuckin’ hurt. I started to move, slowly at first, and every time I pulled back he tightened his ass. Soon I found myself biting off my own moans.

  He shuddered, clenched, and rolled his hips around my cock causing me to drive in hard before I remembered who was wrapped around me.

  “I need a condom... Ahhh... shit... I need a condom,” Scotty stuttered while squirming against me, making my stomach clench in a good way. A way I hadn’t felt in awhile.

  “Fuck, Scotty, you’re gonna come on your first t
ime?” For some reason that had “IT” jumping for joy.

  “Sorry, I know— Ohh God— it kinda freaks you out.” His hips rocked again, and I couldn’t help picking up my tempo. He began to shiver as if cold. “Condom, condom, condom,” he breathed over and over.

  “Shoot your wad, Scotty— fuck...” I fisted a hand in his dark hair and tugged much harder than I intended.

  He cried out, his hands never leaving the wall as he came. His whole body clenched and I lost it, pounding through the tightness of him, and finding release myself on a loud growl.

  It wasn’t spectacular, or gut wrenching, or anything of the sort. It didn’t leave me shaking or sweating. It was just a means to an end. A release of sexual tension.

  As the last surges wracked my balls, I fell against his back and let loose of his hair. I took his hands from the wall, and folded them against his body so he could lean against me. He collapsed into my chest, panting and shaking. I held him up, enclosed in my arms. I’d never let a trick do this, but then I’ve never gotten off on a trick before either. And, well, damn it, I liked Scotty for some reason.

  After only a minute, however, my mind began revolting and I pushed Scotty off me. I fished a sani-wipe out of my jacket pocket as I walked the few steps to a dumpster. With my eyes closed, unable to look at what lay in the condom, I whisked it off and tossed it in. My demented nature reared up, and soon I was scrubbing myself with one, then another sani-wipe. Tearing open yet another, I scoured my hands clean, and then chucked it in with the others.

  Scotty knew my aversion to semen. All my regulars did, and they understood for the wrong reason; disease. None of them knew I had an aversion to even my own though. Scotty might have an idea now.

  Without turning around, I tugged my jeans up, and buttoned them. “Maybe this should be the last time, Scotty.”

  “What? No... why?” he said, confused.

  I turned towards him, lips thin, and blew a sigh through my nose. “Because I never get off on my tricks and I got off on you.” I hitched my thumbs into my front pockets.

  He tilted his head, looking even more confused at my admission. “Huh?”

  I had to admit it sounded ridiculous, even to my ears. “I know you don’t understand. Why shouldn’t I get off on tricks, right?” I asked.

  He nodded, watching me as he pulled his jeans up.

  “Well I don’t, and never have,” I explained, closing the gap between us.

  “But you did with me-ee.” A cocky grin crossed his flushed face, making me laugh.

  At least I was good for his ego. I threw an arm around his neck, and tugged him next to me as we strolled to the Bentley. I kissed his cheek as he slid some bills into my breast pocket then grabbed a handful of my denim jacket.

  “I’m not ready for you to be rid of me you know,” he said earnestly as I opened the door for him. I looked at him for a moment, and realized for the first time how handsome he was becoming. His boyishness was fading and being replaced with a refined, strong, and affluent man. He gazed back at me in a soft and sturdy way.

  “I won’t kick you to the curb yet. But I won’t be here next weekend, just so you know.”

  His hazel eyes crinkled in the corners. “You do need the time off.” His tone was all knowing as he dipped his chin resolutely. With that he slid into the Bentley and pulled the door closed, leaving me to shake my head.

  The night took my mind off Scotty quickly. A few simple cheaters and a few blow jobs, one right after the other. I was having a nerve numbing smoke before heading back to the club to deal with Georgie.

  “Hey, baby, you do good tonight?”

  Without even turning I knew that high toned, floaty voice.

  “Marie, dahling... How are you hot stuff?” I turned to her with a wicked grin. “Yeah, I did alright. You?”

  She smiled as she shimmied her wide, feather clad shoulders back and forth. Marie was actually Mark and had fake tits and a real dick, but if you valued your life you didn’t ever say her tits were fake. In her opinion, she should have been born as she was now. A true perversion of nature. Yet she could turn em’, and did.

  “I did good. I think we were the only two out here tonight, sugar.”

  I took a draw on my smoke then offered it to Marie. She sucked on it still in my hand, leaving her purple pearl lipstick smudged on the end. She rolled her big brown eyes appreciatively when the poison hit her lungs.

  “I saw Cherry earlier in a compromising position under some fat, grunting, sweaty dick,” I said.

  Marie blew the smoke out and waved her hand in front of her mouth, making her bracelets jingle. “Eww... Better her than me.”

  “Yeah, I agree.” I chuckled, glad I hadn’t had one like that tonight. “Can I ask you a question?” I said, straightening up.

  She hunted my face before nodding.

  “Do you get off on your johns?” I took another drag as I glanced down the Avenue.

  “Oh, Trey honey, you just made me so sad. You don’t get off on your tricks?” she said. I shook my head once. “Oh, baby, I couldn’t imagine doing this without the reward, no matter what the money.” She gave me a concerned pout then wrapped her arms around me in a bear hug. She was almost twice my size, even without her five-inch heels, and my face got wedged between her large tits. When she finally let me go, I took a hasty breath then another toke on my cig.

  She took it from me and drew deeply before handing it back. “You and I have been hitting this section of road since you were a kid, and I know nothing about why you still do this— and don’t say for the money. That’s not a reason.” She paused and I stayed quiet. Her perfectly plucked and waxed face turned sad for a moment. “Maybe someday you’ll want to talk. I have broad shoulders and big ears,” she offered, and I knew it was true just by looking at her.

  “Thanks, doll. That means a lot.” I took her hand and slopped a silly kiss on top. “I’ve got one more trick, then I’m gone.”

  She swooned over the kiss dandily. “Honey, you take care of yourself. I worry about you. You’re too fine to be out here. You should be modeling, or at the very least someone’s gig you know?”

  Just then a private red limo sidled up in front of us. The window whirred down, and a fiery haired, rich sophisticate came into view.

  “She ain’t looking for me, honey. Have fun,” Marie said against the side of my head before she sauntered away, swinging her ample hips.

  I was ready to be done and gone, yet this was money, and more than likely an easy three. I snapped my smoke off my fingers as I walked to the car. I hipped the red machine and gave the woman a disarming smile. She smirked back, her emerald eyes twinkling.

  “Can I tie you up?” she asked, laying her hands over each other on the door ledge.

  “No.”

  “Spank you?” She rested her cheek on her hands, and looked up at me. Her sleek copper hair tumbled down the outside of the door in a wild clash of color.

  “No.”

  “How about butt toys?”

  I nodded.

  “Whips?”

  I shook my head.

  “So, no dominance games?” She raised her head.

  “No.”

  “Why not?” she asked curiously.

  I gazed at her contemplating my answer and for some reason the truth, or a version of it, tumbled from my lips.

  “I have an aversion to being subjugated.”

  She smiled as if she understood, then she settled back into the dark interior of the car. Her hand shot out holding a piece of flat plastic between two fingers. It was about the size of a credit card. I took it, rolled it over, and saw Temptations scrawled in flourishing red across the black card.

  Everyone in and out of the industry knew of the scandal over the opening of the BDSM fantasy club a year ago, located smack dab in the middle of Seattle. The club was owned by porn industry mogul Lila Luscious, and it was rumored the lower level of the club held Lila’s studios. It wasn’t to say Seattle didn’t have a thriving ero
tic industry, but it stayed in the shadows, quiet and unassuming. Temptations had entered the scene screaming; I am here.

  The club was a high rollers type situation, and I didn’t know anyone rich enough to get through the door. Well, probably Scotty when he was old enough.

  She leaned on the door ledge again, and boldly ran a bright red nail along my belly just under the waistband of my jeans. I didn’t move, keeping my eyes locked with hers. I wondered if this was Lila, herself, gazing at me with the side of her crimson-painted mouth quirked up. Everything matched, I realized wryly. The car, lips, nails, and name on the card.

  “You are too sweet a package to be out here on the Avenue. Are you clean?”

  I nodded, thinking ironically; if only she knew.

  She ticked her nail against the card in my hand. “Come to the club and check it out. Play a little. That card will give you full access on the house. If you like what you see, we can talk later.” She grinned like a cat, showing scads of pearly teeth. “If you don’t like the club, we should talk anyway.” She winked. “I have other ventures.”

  She was offering me a job?

  I shook my head at her. “I’m not looking for work. I do damn fine out here.”

  She shot me a sly smile. “I’m offering you security and safety. How much do you pull a night out here?”

  I shrugged, “Fifteen to twenty-five on a decent night.” More like a really good night when I hustled my ass off.

  An eyebrow lifted in surprise. “That’s high end for out here. I’m more than intrigued now,” she purred. “I can guarantee you five Gs a month, plus tips, if you’re willing to work.”

  Now my eyebrow rose. That was some decent change for a regular gig, and red lights were flashing erratically in my head.

  “You just happen to be strolling along the Ave, spotted me, and liked what you saw? I find that hard to swallow, lady,” I said, my eyes narrowing down suspiciously.

  She laughed. “Not exactly. We share some clients and you came up. At least I assume it’s you. Built lithe and pretty like a model, longish brunette hair, big package, and the most beautiful blue fuck-me eyes you’ve ever seen? If there are two of you, well... no reason to be perverse,” she said with a little sigh, her hand fluttering at her throat.