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Pleasure Ride

"On the ride home, Sterling takes a ride on his friend's dad."

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The silence between me and Phil stretched on until I began to squirm in the passenger seat of his car. At the beginning of the drive, I'd tried to strike up a conversation, but Phil just kept his eyes fixed ahead, offering only an occasional grunt of acknowledgment. I'd never had trouble talking to him before. His distance made me anxious, and I had to remind myself that he was the one who offered to give me a lift.

I'd spent the evening at Phil's, since his son Daniel and I were close friends. But Daniel wasn't the only reason I hung out at that house so much. Home from college for the summer, I wanted to do more than play video games and show up for my shifts at the hardware store.

During my first year away at school, I'd grown far more comfortable in my own skin. Now, being back in this town felt constraining, almost suffocating. I longed to throw off the weight of my parents' expectations. And oh, how I wished my mom would stop asking me why I didn't have a girlfriend. Every time she brought up the topic, my father gave me a sidelong look, full of suspicion.

Glancing over at Phil, I searched his face for a sign of irritation. His window was down, and the night breeze ruffled his wavy brown hair. He'd recently shaved his beard; it was still a bit strange seeing him without it. Yet I was quick to compliment him on the new look. He appeared years younger. 

His strong hands rested on the steering wheel. Beneath his T-shirt, his shoulders seemed relaxed. Maybe he was just deep in thought, I told myself. 

It was then that I realized Phil was taking the back roads in order to get to my house. Though it was only half past ten, there was hardly any traffic out this way. Furrowing my brow, I wondered why he hadn't chosen the faster route. This would add a good ten minutes to the trip. 

"Tell me something, Sterling." Phil's voice wasn't loud, but I still started at the sound of it. Turning a little in the seat, I waited for him to go on. 

Finally, he looked over at me. A faint smile twitched on his lips, threatening to grow wider. "Is there actually anything wrong with your car?" 

I froze while trying to hide my alarm. Had I been that fucking obvious? 

For days now, I'd been planning the deception. I would spend this Friday evening hanging out with Daniel for a few hours. Then I'd head out around ten since he had to be up early for work the following morning. Once outside, I'd conveniently "discover" my car wouldn't start. I'd have no choice but to stay overnight.

Instead, Phil offered to drive me home. "You have to be at the coffee shop before six tomorrow," he reminded Daniel, "whereas I can sleep in. Go on and get ready for bed. If your mom happens to wake up, tell her I'll be back soon."

And that was how I found myself sitting in Phil's car, pretending to be shocked at his suggestion that I hadn't been truthful. 

"Of course, there's something wrong with my car," I said. "I told you it wouldn't start. Why would you ask me that, Phil?" I offered him my most innocent look. I'd been told my large blue eyes could get me whatever I wanted, and I prayed that was true tonight. 

Imagine my disappointment when Phil shook his head and snickered.

"Oh, the reason I ask is because you've been coming on to me ever since you got back home for the summer."

I stammered out a response as my face burned with embarrassment and sweat beaded on my upper lip. "I didn't mean—I wasn't trying to..."

"Relax." Phil reached over and rested a hand on my leg. I stared down at it in astonishment. Even through my jeans, I could feel the warmth of his heavy palm.

"I'm sorry," was all I managed.

"It's fine." Phil kept his hand right where it was. "Daniel told me you're out at college, but you aren't ready to tell your parents. I understand that. And I understand how you might have a crush on someone older, someone you feel you can trust."

It was more than a crush. During freshman year, I'd given and received numerous blowjobs, and I'd offered up my anal cherry to a junior who happened to be a skilled top. Throughout all those experiences, my mind kept returning to Phil. Sometimes, I imagined it was him I was going down on. It was his hand on my dick, his cock claiming my ass.

Daniel was cool with me being gay, but I knew I could never tell him about my feelings for his dad. I couldn't even joke about it. I could only hang around and hope for an opportunity with Phil. 

An opportunity like tonight.

Running a hand through my short dark hair, I tried to regain my composure. "I hope I haven't made you uncomfortable," I said. "I mean, I wasn't trying to be blatant or anything."

That made Phil laugh. "You backed your ass right up against me when we were in the kitchen, Sterling."

"It was an accident!" I protested.

"Uh-huh. And tomorrow, I bet your car is going to start up with no problem at all, isn't it?"

I knew it was time to stop bullshitting and be honest. "You're not upset?" I dared to ask.

He flashed me a smile. "Nah, I'm not upset. I might even be a little flattered. After all..." His gaze swept over my body, which was covered in shadow. "You're, uh, quite sculpted now. I bet you don't want for attention."

So he had noticed! For the better part of a year, I'd spent most of my free time at the gym, working on my body in the hopes that it would turn a certain straight man's head. More than once, I'd nonchalantly lifted up my shirt while in Phil's presence. It was just for a second or two, but long enough to show him how much I'd changed.

He was now looking back at the road, his expression almost somber. I feared he already regretted what he'd just said. When he started to withdraw his hand, I covered it with my own.

"But it's your attention that I want, Phil." I slid his hand upward, along my thigh and toward my groin. I was growing hard under my jeans. 

He didn't pull away, didn't do anything but let me guide him. The moment I had his palm firmly against my crotch, I released a moan. 

Beside me, Phil was rigid, as if fighting a war within himself. But then he started rubbing me, strengthening my erection by the second. I ached to touch him as well; I was desperate to know if he was becoming aroused. 

He placed his hand back on the steering wheel. I sat at his side, breathing fast, my dick pulsing for more of his attention. 

Phil slowed the car, and I looked around in confusion. We were nowhere near my house. We were nowhere near any house. He pulled onto a narrow gravel road, then cut the lights and engine. Immediately, we were immersed in darkness. I scrambled to turn on my phone's flashlight so I could see Phil's face. When he unbuckled his seatbelt, I did the same. My hands were shaking so hard that the flashlight's beam skittered all over the car's interior. 

Phil took the phone from me and placed it on the dash. Through the open window, I heard crickets and myriad other insects trilling away. I was glad for the noise, which covered the sound of my heavy breathing.

Leaning toward me, Phil again placed his hand between my legs. "Is this what you've been wanting?"

Through another moan, I told him yes. In the semidarkness, his grin looked wicked. When he unbuttoned my jeans and then lowered the zipper, I couldn't resist the urge to try to kiss him. I was dying to feel his lips on mine.

Though his fingers worked into my briefs, seeking out my erection, he easily dodged my mouth. 

"I'm sorry!" I said again, fearful of being too pushy.

"It's okay." His voice had deepened until he sounded almost hoarse. "It's just that I only do that with my wife."

I started to nod, but the feel of his fingers encircling my dick emptied my mind of all thought. My eyelids fluttered from the pleasure that first touch gave me. 

"Doesn't take much to get you excited, does it?" Phil teased. "You're rock-hard already."

"You can't imagine how much I've wanted this!" Looking down, I watched as he freed my cock from my underwear. With the pad of his thumb, he stroked the tip. "Can I..." I had to take a deep breath before finding the courage to continue. "Can I touch you, too?"

"Well, now, if we're gonna take it that far, we should move into the backseat where there's more room." 

My eyes widened. Here I was, all alone with the man who'd inspired countless jerk-off fantasies of mine, and he was willing to let me play with his cock! The thought of taking him in my mouth caused my own dick to pulse.

My obvious excitement made Phil laugh. As soon as he opened the door to get out of the car, I did the same. Neither of us hesitated to climb into the backseat, and I saw Phil eyeing my erection before we shut the doors and enveloped the vehicle's interior in darkness once more.

While he leaned back and unfastened his jeans, I yanked my shirt over my head, mussing my hair in the process. 

"Go on and take everything off," Phil said.

My phone's flashlight provided enough illumination for me to see the flash of his teeth. Another sly smile. And he must have noticed my dumbfounded expression.

"You want me to strip naked?" My voice held a slight tremor.

"Sure. I know you're proud of that body. May as well show it off." The sound of his zipper being lowered seemed amplified now. "Of course, if you're too shy, we probably shouldn't do anything else..."

"I'm not!" As I took off my shoes and socks, and then my jeans, I prayed no one would drive by and spot us in Phil's car. 

Beside me, Phil fisted his cock. I could discern the rhythm of his stroking. 

"Come on, lose the underwear, too."

The way he ordered me around had my dick twitching. In no time at all, I'd stripped myself free of all clothing, but Phil merely lowered his jeans and underwear down his legs. 

"Now you can touch me, Sterling."

I slid my bare ass across the seat, even closer. He let me nuzzle up against him, and when my lips brushed against his neck, I heard no protest. Meanwhile, my hand sought out his cock.

Since his lap was mostly concealed by shadow, I grew familiar with him through touch more than sight. He felt similar to me in length, maybe a little longer. A little thicker, too. His tip was more prominent than mine. He let out a soft sigh as I traced the underside of his cock with my fingertips. 

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"That feels really good," he said. "You have a nice touch."

"My mouth would feel even better," I whispered before suckling his earlobe.

Phil's erection pulsed in my grasp, as if to summon my lips. Still, I waited until he lifted a hand and pressed it against the back of my head. I happily let him guide me downward, and when his cockhead brushed my cheek, I set to work licking and kissing his entire length.

"Ooh, fuck yeah," he breathed.

Closing my eyes, I inhaled his scent. I couldn't help but bury my face in his crotch; his trimmed pubes rasped against my skin. Again, my tongue traveled along his shaft, toward that bulbous tip.

He released a loud groan when I wrapped my lips around him. The taste and scent made my mouth water for more, and I was soon leaking saliva. I was reminded of a past partner who'd told me he loved my messy blowjobs. I could only hope Phil felt the same way.

The ample spit provided lubrication while I stroked him. Though I had some experience with this act, I was far from an expert, and my jaw quickly began aching. Yet that didn't stop me from sliding my lips lower, and lower still, until they met my hand at the base of Phil's dick.

I sensed him shudder when his tip invaded my throat. "My God!" he cried out. "You're trying to take it all!" 

His shock led me to believe Daniel's mom never attempted such a feat. Even as my eyes watered and my gag reflex threatened to kick in, I refused to pull off until my lungs screamed for air.

Finally, I sat up and worked to catch my breath. Phil's hand was still on my head, his fingers weaving through my hair. I sensed his need like a physical force.

The aching in my throat couldn't stop me from taking him deep yet again. While sucking his dick with wild enthusiasm, I made sure to fondle his balls. His moans were continuous, filling my ears and causing my cock to leak precum. I loved hearing how excited he was, and knowing I was the reason for it.

He struggled to keep still as my head bobbed up and down. Tightening his grip on my hair, he said, "You've got me close!"

That was exactly where I wanted him, with his erection swelling to stretch my lips even more. Maybe it was selfish to think of my own needs, but I knew I had to take my chance while the opportunity presented itself.

I sat up and wiped my mouth with the back of my hand. Phil was breathing hard, clearly desperate to come.

"What's wrong? Why did you stop?" He sounded strangely vulnerable, near pleading.

"Because I want you to fuck me." I waited for his refusal, and when it didn't issue forth, I hurried on. "Let me ride your dick, Phil. Please."

"But don't you need to... uh... prepare?" 

Of course, I hadn't prepared for this. Ideally, my hole would be stretched and lubed up. And at this point in my life, I'd been penetrated only a few times, by the same top. He'd taken care not to rush me, and as a result, I was able to relax and fuck him with little pain.

Tonight would be entirely different. Yet I refused to deny myself this experience. 

"I'll be okay," I promised while moving to straddle Phil. "But you should take off your shirt."

"Why's that?"

"Because I might come while your dick is in my ass."

As he followed my suggestion, I couldn't resist sliding my cock against his. That illicit sensation made us both moan.

Once I was presented with his bare torso, I caressed his skin. He had a lot of chest hair, more than anyone else I'd been with. Being this close, this intimate, had me trembling with excitement. If Phil noticed, he was kind enough not to comment. Still, I figured he realized how helpless I was to my desire for him.

His breathing again quickened when I reached for his cock. I had a knee planted on either side of him, with my neck craned to avoid the car's ceiling. He sank a little lower in the seat to give me more room. 

The feel of Phil's tip at my hole, and his hands on my hips, spurred me on. His erection, hard as ever, was ready to push past my tight flesh.

I tried not to wince as he started opening me up. Of course, I was controlling the speed at which I took him inside me, so that initial ache, which I both dreaded and craved, remained bearable. The lack of lube made the process more painstaking, but Phil was patient. His touch, warm and tender, soothed me through the burning stretch. 

"Easy," he whispered. "Take it slow." 

That perfect mushroom tip of his soon pressed against my prostate, and my own dick, which had stayed hard, now jumped in response. My whimper did little to convey how incredible the sensation was.

"You're in the perfect spot!" I told Phil through heavy breaths. "It's like your dick was made for my ass!"

His pleased laughter coaxed forth mine. Taking hold of my cock, he started stroking me again, and though my pain hadn't fully subsided, I took him deeper. My body trembled as I rested my palms on his shoulders. He felt so large and thick buried inside me! I could have sworn his dick had swelled even more.

His hand moved faster, encouraging me to do the same. It wasn't long before I worked up to a rhythm I trusted, one that ensured continual prostate stimulation without inflicting too much discomfort.

"That's it, ride me, baby!" Phil pumped away at my cock, banishing every last remnant of pain and replacing it with a fierce need to come. 

As I bounced on his dick, feeling stripped and raw inside, yet hungry for more, distant headlights appeared up the road. "Fuck!" I shouted. "Someone's headed this way!"

"Don't stop." Phil issued the order through clenched teeth. "Not till you come for me."

Sweat coated my skin, its odor mingling with the smell of sex in the car. I closed my eyes against the onslaught of high beams, but I couldn't help wondering how visible I was to that late-night driver passing by.

Fear of being caught didn't slow me down. My cries were constant now, and my dick remained in Phil's expert grip. I had time only to warn, "I'm gonna come!"

An instant later, the orgasm rolled through every inch of my body. Its heat seemed to expand and constrict as I shot my load all over Phil's chest. 

He kept jerking me off, determined to milk me dry. All the while, my ass muscles clenched around his dick. The climax left me shaking. I was panting by this point, close to hyperventilating. 

Still, I kept rocking my hips. I fucked Phil faster and faster, ignoring a fresh twinge of pain. "Come. Please, come!"

He grunted and groaned, straining beneath me. "I'm close, Sterling. Gonna fill you up!"

He gave a powerful thrust upward, deeper into my ass, then abruptly stilled. I heard his sharp intake of breath. Impaled on his dick, I was aching for my reward.

Phil gave it to me while shouting from the force of his orgasm. My palms still rested on his shoulders, and I felt the tremor accompanying his release.  

Even after he was finished, I stayed upright. It didn't matter that I'd made a mess all over his chest; I still wanted to rest against him. I wanted to feel the warmth of his skin and listen to his breathing slow. But uncertainty froze me in place.

It was Phil who drew me close. As I leaned toward him, his cock slipped free of my ass. That sudden emptiness had an ache all its own.

In the darkness, he pressed a hand against my cheek. "You are an amazing fuck, Sterling." 

I grinned, overwhelmed by his nearness and the lingering scent of our fucking. I longed to lick every inch of this man's skin. 

"And I hope I was everything you imagined me to be," he went on.

"Beyond my wildest dreams! But we've made a mess." Already, I was worried about the cum I'd leave behind. 

"These seats wipe clean real easy," Phil assured me, then gave my ass an affectionate pat.

I took that as my signal to ease off his lap, but before I could, he gently grasped my hair and guided my mouth to his.

That first kiss, filled with heat and hunger, made me swoon against him. As his tongue met mine, a satisfied moan emerged from his throat, and my dick tried to return to its fully hard state.

Our second kiss was tender, softer, but no less arousing. It was only the approach of another car that made us separate.

Once the vehicle's taillights had been swallowed by the darkness, Phil and I cleaned up with a pack of tissues he retrieved from the glovebox. 

"I'll go over the backseat tomorrow," he said while wiping my semen from his chest. "It'll be good as new."

Minutes later, we were dressed and back on the road. The silence between us was now comfortable, for we were both relaxed and content. I couldn't help but think ahead to when we might do this again. I knew I should be grateful for what Phil had given me. And I was. But my infatuation hadn't dimmed in the least.

Glancing my way, he gave me an easy smile. I was relieved that he didn't appear troubled about what had just taken place. When he again rested a hand on my leg, I dared to graze his knuckles with my fingertips.

We reached my house all too soon. Mom had left the porch light on for me, but the windows were dark. Tonight, I considered it a blessing that my parents went to bed around ten, even on the weekends. 

Slowing to a stop in my driveway, Phil looked over at me. I held my breath, letting my eyes do the pleading. 

"Tomorrow, I'll swing by and pick you up," he said. "Around noon?"

I nodded, excitement making my heart race. I could feel my pulse in my chest and between my thighs.

"We'll head back to my place," Phil added, "so you can get your car." He offered me a knowing wink. 

Somehow, I refrained from touching him before getting out. Standing in the driveway, I met his stare and said, "I'm looking forward to the ride."

Phil laughed and shook his head, as if not quite sure what to do with me. But I must have given him a few ideas, for he replied, "I'll make sure you enjoy it, Sterling."

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Written by Obsolete_Fox
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