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We'll See (Part 1 of 2)

"Vaughn finds himself in an intimate situation with his friend's son."

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When I arrived at the house that Friday afternoon, I noticed Dex's car parked in the drive. I was staying with my friend, Wayne, while my own house underwent renovation, and so far, the arrangement was working out well. Dex, Wayne's son, was home following his first year of college, but I hadn't seen him all that much in the several weeks I'd been under Wayne's roof. At nineteen, Dex kept busy working or hanging out with his buddies. 

Stepping inside the living room, I basked in the cool air, which provided a delicious contrast to summer's heat. I took off my work boots and left them by the door. The main level was quiet, with few traces of Dex's presence. I spotted a soda can on the kitchen table; picking it up, I discovered it was lukewarm, still half-full. I returned it to the fridge and then headed toward the guest room. 

I gave the stairs a cursory glance while passing by. I figured Dex was up in his room, maybe sleeping. He tended to stay out late. 

A strange, unexpected sound drew me to a halt. Placing a hand on the banister, I held my breath and waited to see if the noise reoccurred. 

It was faint but unmistakable: a muffled cry that must have come from Dex. It sounded as if he was in pain.

I bolted up the steps, all the while wondering if I should have grabbed some kind of weapon from downstairs. Had someone gotten into the house? Were they hurting Dex? I'd lose the element of surprise if I happened to stumble upon them. 

In the upstairs hallway, I saw that Dex's bedroom door was closed. As I rushed toward it, his anguished cries grew louder. I didn't hear anyone else, only my friend's son. Frantic, I reached the door and threw it open.

Dex was on his bed, with his head lowered and his ass lifted in the air. He was also stark naked. The sight of him, alone and in such a vulnerable position, should have prompted me to turn around and immediately leave, but I was too shocked to react. 

Realization slowly permeated my astonishment: the cries I'd heard were due to the fact that Dex had worked part of what appeared to be a sizable dildo into his ass. In the moments before he spotted me, I noticed his face drawn taut with a combination of pain and pleasure. He was trying to fuck himself with a toy. And it wasn't a starter toy.

Though I felt a surge of mortification for both him and myself, I couldn't stop staring at the flesh-colored silicone. In observing Dex's profile, I was treated to the shapely curve of his ass, and the dildo protruding from it. He'd worked it far enough into his hole that it stayed put without him needing to hold onto it. Involuntarily, I glanced at his groin area, but his position prevented me from seeing much. 

Dex kept moaning, his eyes closed as he reached behind him. At his side was his phone, and though the sound was muted, I caught a glimpse of the screen, which displayed a man's lips wrapped around a huge dick. 

Still oblivious to me watching, Dex tried to take more of the dildo. A whimper escaped him, making me fear he might hurt himself. 

Before I could decide whether to caution him about anal tears or simply retreat back into the hall, he opened his eyes. 

"Shit!" he cried, lifting his upper body so that he was balanced on his hands and knees.

I held up my palms. "I'm so sorry! I heard sounds coming from up here, and I thought you were hurt."

I feared his embarrassment would make him lash out in anger. His face held a deep blush, but I couldn't tell if it was from humiliation or arousal. 

"I'm gonna go," I said, reaching for the knob so I could close the door as I departed.

"Vaughn, wait!" Dex's voice was edged with desperation.

I froze. My muscles were painfully tense, and, to my horror, my dick had hardened beneath my jeans. Was I imagining Dex's gaze dropping to my crotch? Fuck, could he see my erection?

His eyes locked with mine. "Um, could you help me?" 

"Sure, okay," I quickly replied, unable to conceal my relief that he wasn't furious. 

Dex remained on his hands and knees, appearing almost submissive. His hair was short and dark like mine, but while my eyes were blue, his were a deep, expressive brown. I felt ashamed for noticing that he had a fantastic body, one his snug T-shirts and jeans only hinted at. He spent a lot of time at the gym, whereas my strength came from the physical labor of my job. 

"You've been with guys before, right?" Dex asked me. 

Though his tone was nonchalant, I bristled at the question. "Did Wayne tell you that? I'm gonna beat the shit out of him." I'd trusted my friend with that information about my past, never dreaming he'd run his mouth.

"Don't be mad!" Dex's eyes took on a pleading look that made my dick pulse. "He only told me because I came out to him earlier this summer. I think he was trying to let me know he's fine with me being gay. I mean, his best friend is bi, and he doesn't have a problem with that, so..."

"I wouldn't say I'm bi," I protested. "I experimented a little in my twenties, before I got married. My wife and I were together for almost fifteen years." I didn't need to add that our divorce hadn't been a pleasant one. When we split up, she got the house, and I bought a fixer-upper on the other side of town. The renovations were obliterating my savings.

"I know it's not my business," Dex went on. "I only brought it up because I was wondering if you could, um..." He glanced over his shoulder. "Could you see if my ass looks okay?"

My mouth dropped open. "What?" I finally managed to blurt out.

"I've been working up to this toy, and I know it's big, but I think I can take it. Even though I used lube, the dildo won't move another inch." Dex related all this to me as casually as he would a film summary, or the highlights of a football game.

I wiped my hand over my face. Despite the room's air-conditioned coolness, I'd begun sweating. "Um, I'm not sure..."

"Please," he begged. "Can you just pull the dildo out and make sure my hole isn't too stretched?"

The insistent throbbing in my groin was a warning sign, a signal I should stop this in its tracks. But it was tempting, so tempting, to get a better view of that perfect ass. Wordlessly, I took a step toward the bed, and then another. 

Dex smiled before lowering his head again. The phone kept playing a gay porn clip: some guy was getting absolutely railed by a thick, meaty cock. My erection grew almost painful, wanting free of its confinement.

I drew in a deep breath and let it out slowly while sitting on the bed. Before me, as if in offering, was Dex. And more specifically, his spread buttocks. The base of the dildo shifted slightly, and I could imagine Dex's tight hole clenching all around that toy. 

Tentatively, I lifted a hand and grasped the base. "Bear down for me," I told him in a soothing tone. My gaze darted to the clock on the nightstand; I'd managed to cut out of work early, which was why Dex hadn't expected me home so soon. We still had another hour before Wayne would arrive.

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As I gently withdrew the toy, I said, "I didn't know... about you being gay."

He moaned faintly, his sphincter relinquishing its grip on the dildo. "Mmm... I didn't feel comfortable coming out until I was at college. People are a lot more accepting there."

"I hear ya." My stare was fixed on the dildo as it slid from Dex's tender hole. The toy was realistic, veiny and thick. When the tip popped free, I discovered it sported a nice mushroom head. My own cock wasn't as long, but it had almost the same girth. 

And at that moment, pre-cum was dampening my underwear. Fuck, I'd gotten laid just once since my recent divorce, and I was horny as hell.

"How do I look back there?" Dex asked.

For several moments, I didn't respond. Instead, I stared at his entrance, so open and inviting. He didn't have a single hair surrounding that gaping circle of flesh.

"Vaughn?" 

His voice drew me from my filthy reverie. "Uh, you look stretched," I said in a casual voice, "but I think everything's okay. Are you in pain?"

"Nah, I'm good." He turned his face to the side, giving me a view of his gorgeous profile. "I'm not sure why I had trouble. I didn't rush or anything."

I looked from the dildo to his ass. "Maybe you need more lube," I suggested. By this point, I was uncomfortably hard. The minute I got out of this room, I was heading to my own so I could jerk off.

"Or maybe I just need the real thing." Dex moved to lie on his back. With his head resting on the pillow, he flashed a seductive smile while taking his semi-erect cock in hand. 

My eyes widened at Dex's blatant advance. Even as I was forced to adjust my dick in my jeans, I pretended my friend's son was joking. "Well, you'll be back at school in just a few weeks. I'm sure you'll have plenty of chances to get the real thing then."

"Why wait that long?" His smile widened while he stroked himself from base to tip. His fingers lingered at his cockhead, teasing forth some pre-cum. Swallowing hard, I allowed myself to ogle his erection. He was average in length and girth, his balls on the smaller side. His entire pubic area was shaved smooth. The thought of taking him in my mouth sent a tremor of arousal through me.

Dex must have sensed my need, for he lifted his legs and drew his knees up toward his chest. "You know, I am a little sore," he revealed. "Maybe you could lube up your fingers and give me a massage?"

"We can't." The pleading in my tone was obvious. "Your dad trusts me, and..."

Dex kept himself spread. Despite my protests, my stare returned to his entrance. So vividly, I could imagine how tight he'd feel around me.

"Dad just wants me to be safe," Dex said. "And I know I'm safe with you, Vaughn."

A trickle of sweat worked its way down my back. "Were you with anyone at college?"

"Just one guy," Dex said. "It was the first time for both of us, and we only did it once."

I moved closer, my hand inching closer to his ass. "And why's that?"

"We both realized we're bottoms," he said with a low laugh. I watched, transfixed, at the way that chuckle caused his hole to flex. "After that, we stuck to blowjobs."

"Christ," I sighed. Everything about him—his cock, with its tip flushed red; his smooth sac; his sweet little ass—made me ache to fuck.

"Touch me," Dex urged. "Play with my hole."

I groaned, my will promptly losing its battle with lust. Gritting my teeth, I reached for the lube. Within seconds, I'd climbed onto the bed and gotten my fingers good and slick. Dex gazed up at me, his grin triumphant. 

My breathing had grown shallow, and as I extended my hand, I noticed I was trembling. My fingers were calloused from work, but I'd just trimmed and filed my nails, so I didn't have to worry about causing Dex discomfort while I digitally penetrated him. 

Fuck, this was my best friend's son, offering me his ass for play! Though I felt a surge of preemptive remorse, it didn't dissuade me from easing my index and middle fingers into Dex's opening. Since he was already stretched from the toy, I slid effortlessly inside him. 

"Mmm, that feels so good!" he moaned. Keeping his legs elevated and parted, he resumed jerking his cock. When our eyes met, he slowly licked his lips. The sight of his tongue gliding over his skin made me fight back a needy whimper. 

Gently, I continued my exploration, my fingers massaging Dex's inner walls. We were both breathing faster, and I glimpsed his balls draw up tight. While studying his expression, I began finger-fucking his hole. 

The way his jaw slackened and his eyes rolled let me know how much he enjoyed this. With a grip that bordered on punishing, he furiously masturbated. 

"Yes, oh, fuck yes!" he said in a guttural voice. "Don't stop!"

"You like that?" I was no longer being gentle. "You like being a little slut for me?"

Dex's eyes widened as astonishment mingled with his lust. He looked at me as if I were a stranger, and for a moment, I felt ashamed. 

But then he smiled again. "I love being your little slut!" His words were almost a growl. "You're gonna make me come!"

I curled my fingers upward, homing in on his prostate. The second I found it, he began quaking. His face twisted into a mask of abject pleasure, so intense it appeared to border on pain. 

"Come for me," I demanded, applying varying degrees of pressure against that exquisite spot inside him. 

Dex's shout reverberated throughout the room. Just before he climaxed, a tremor shook his entire frame, and his ass tightened around my fingers. 

Semen spurted forth to coat his stomach and chest; a few splotches reached his neck. My fingers continued working their magic until I was certain I'd drained him dry. 

Dex whimpered and groaned, still quivering. Slowly, carefully, I withdrew from him. When our eyes locked, I felt a fresh wave of guilt, well-earned this time. I told myself this meant nothing; we'd simply fooled around a little. It wasn't as if I'd whipped out my dick and— 

Dex sat up in a single, fluid motion. Covered in his own cum, he slid toward me. I gasped as he placed a hand between my thighs, yet I didn't pull away.

"Wow, you're so fucking hard!" he murmured. His lips were just inches from mine. "Let me see it."

"We can't." It was the same pathetic argument, which neither of us had heeded before. 

In response, Dex worked at the buckle of my belt. As I sat there, practically panting with lust, I let him unbutton and unzip my jeans. I let him reach inside. 

The moan had barely escaped my throat when Dex kissed me. His mouth was hungry and demanding, his tongue wild for mine. My moans grew louder, and all the while, his hands stayed busy. 

In a final attempt at restraint, I broke the kiss and grabbed his shoulders. "If we don't stop now, this will go too far."

Dex grinned. "We're not gonna stop, Vaughn." His fingertips grazed my briefs, teasing my cock through the fabric. "Not until you've given me the real thing."

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Written by Obsolete_Fox
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