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CHAPTER 3

Not Too Late to Try

BRAD:

    For the past ten years, I had primary custody of Avery, who saw his mother a couple of times a month. This was one of those weekends, which would normally mean I had the house to myself, free to walk around naked to my heart's content. However, we now had a new housemate – Avery's buddy Chase – so I put on some sweatpants and a T-shirt before going down to the kitchen to make my typical Saturday breakfast: waffles.

    "Morning, Chase," I said fifteen minutes later as the shirtless teen strolled into the kitchen, wearing pajama pants and nothing else – as far as I could tell, not even underwear.

    "Morning, Brad," he greeted me back, stretching his arms up and thrusting his crotch in my direction. "Waffles for breakfast?"

    "Yup. I made some for you as well, so grab a plate."

    "Mmm, tastes delicious," Chase said after we sat down and started eating. "Even better than my mom's."

    "How is your mother? Is she liking the new house?" I asked.

    "Yeah. She and her new husband seem happy there," Chase nodded.

    "What about your dad, if you don't mind me asking?"

    "Oh, he's married too. But they live in a small apartment in Hollywood, so there wasn't enough room for me to move there," Chase explained.

    "I see. Do he and his wife have any other kids?" I asked, trying to be conversational.

    "He's actually married to a guy," Chase smirked.

    "Ah. That's nice," I said, blushing slightly.

    "It's the reason why my parents divorced a few years ago. Now Dad lives in West Hollywood with a gogo boy named Mateo," Chase added, seemingly amused by the information he was sharing.

    "Well, you never know where life might lead you," I said vaguely, since I wasn't sure how else to react. 

    "What about you, Brad? You ever fooled around with a guy?" Chase asked casually. I stared at him for a few moments without answering, but he didn't back off. "Like in high school or college or something?"

    "Uh, well, people do all sorts of things in college," I chuckled, continuing my vagueness. By this point, my cheeks were definitely starting to burn.

    "Haha, I knew it!" the teen laughed triumphantly. "What did you do? C'mon, you can be honest with me. I won't even tell Avery."

    Although he was prying into my private life, I decided not to shut down the conversation. After all, I was the one who spied on Chase masturbating with my son a few days ago. The boys were clearly at that age where they were exploring their sexuality, so maybe I should be honest with them. I'd never told my son about my (brief) history with men, but talking with Chase right now felt less awkward than talking to Avery about my sex life.

    "When I was in college I… let a guy go down on me a few times," I said, trying to strike a balance. I didn't want to get too explicit, but I didn't want to sound too conservative either.

    "Cool. And what did you think?" Chase asked, leaning back in his chair, flexing his abs in the process.

    "It was nice," I mumbled, not fully wanting to admit they were among the best blowjobs I'd ever had.

    "Yeah, blowjobs are usually nice," the teen chuckled. Clearly, he wasn't a shy one. "So, did you return the favor?"

    "You mean…?"

    "When the guy sucked you off, did you blow him as well?"

    "No. No, I didn't," I admitted.

    Now that Chase was leaning back in his chair, it was painfully obvious the teen was sporting a hard-on. The flimsy material of his pajama pants was turning into a tent, growing taller by the second. His dick bounced, flexed even, almost like he was doing it on purpose to wave at me. I looked up and made eye contact with the teen, who smirked. I was embarrassed that'd been caught staring at his crotch, but Chase didn't seem uncomfortable at all. Quite the contrary.

    "It's not too late to try," he said, motioning with his head down to his crotch.

    I watched dry-mouthed as Chase slid his hand in his pants and started to slowly stroke himself. There was no mistaking what he was suggesting. I gulped, once again staring at his obscene bulge. Could I really do this?

    My hands were shaking, but another part of my body reacted differently. My dick was twitching in my sweats, fully hard by now. To make matters worse, Chase noticed my erection too. He gave me a sly grin, like he knew how close he was to getting what he wanted. He used his feet to push his chair away from the table, angling himself toward me. He was giving me space... space to kneel down in front of him.

    I took a deep breath and then quickly moved from the chair down to my knees. This was it: I was finally taking the plunge. I looked up at my son's friend, waiting for him to pull down his pants and release his boner.

    "Give me your hand," Chase said in a surprisingly stern tone.

    I reached up toward him. The hand that had been down his pants grabbed mine. He set my palm onto his cock firmly, encouraging me to rub his dick through his pajama pants. After a few seconds he let go, but my hand remained on his firm tool, milking out drops of precum that were already leaking through the fabric.

    "You know what to do next," Chase continued in that dominant voice. "Take it out."

    My heart started racing, but there was no turning back now. I held my breath as I reached for the waistband of his pajamas with both hands. I tugged at the elastic and Chase briefly lifted his hips from the chair, allowing me to tug his pants down. As his dick broke free, it slapped me on my cheek, leaving a wet spot of teenage precum.

    "Now lick it, just like a popsicle," Chase said, coaching me along my first-ever blowjob.

    I did as he instructed, leaning forward and dragging my tongue along his shaft. I started at the base, working my upward until I could taste his salty-sweet precum. My body tingled at the first taste of manly juice. I found it oddly arousing. I repeated the action, going faster and trying to coat more of his pole with my saliva.

    "Mmm, that's good," Chase commended me. Something inside me fluttered at hearing those words. "Now, look me in the eyes and put it in your mouth."

    The teen's voice was as soft as a whisper, but I felt like he was shouting from a megaphone. Again, without much hesitation, I did as he asked. I looked up at him and we held eye contact as I leaned in. He reached down and pointed his cock toward my mouth while I inched closer. Finally, his cockhead brushed past my lips and across my tongue. I kept going until his prick hit the back of my throat. Fuck!

    I was doing it – I was actually blowing another guy. I smiled (as much as I could with a mouthful of dick) and I started sucking on him just like a lollipop, trying to emulate the people who had blown me before. Chase responded with appreciative groans that made me want nothing more than to please him.

    Even when I gagged, I kept at it, bobbing my head back and forth but never going down more than halfway. My own cock continued twitching but rather than jerk off, I let my hands rest on Chase's muscular thighs. I wanted to give him all of my attention for now.

    Although young, Chase was so sure of himself, and sure of what we were doing. His confidence was incredibly attractive. This couldn't have been his first time getting a blowjob. Hell, even I'd had plenty of them by the time I was his age. It made me wonder: had my son ever been in this position? Had Avery had his dick sucked yet? Or maybe… maybe he was the one sucking other guys' dicks? Maybe even Chase's?

    "Try to take me deeper. I know you can," Chase told me, bringing me back to reality.

    The teen reached down and took my glasses off, setting them on the table. Then, to emphasize his words, his hands came to the back of my head. He started pushing down assertively, yet not forcing me too much. We made it past the halfway point of his shaft, and I did indeed gag, but he let off. We did this again and again, and each time I gagged less and swallowed more of his cock.

    At one point, while he lodged most of his dick down my throat, Chase bent over me and pushed down my sweatpants. With my cock and balls free, I couldn't ignore it any longer. My right hand shot down and I started stroking. I had to be careful, as it felt like I could cum at any moment.

    I couldn't quite deepthroat Chase, but I was sure having a good time trying. I was at least getting more used to controlling my gag reflex, something Chase picked up on. His hands came back to my head and he was more forcefully guiding my mouth up and down his cock. Sounds of his moaning and choking filled the room.

    "You ready? You ready to taste your first load?" Chase panted.

    Seconds later, I felt his hot jizz splattering the back of my throat. His cumshot was so big, it was quickly filling my mouth before I even had a chance to swallow. The salty bitterness was unusual, but I knew I wanted more. I gulped it down like ice water on a hot day, all while my son's friend gripped my hair with his fists.

    Finally, I started to pull back, smiling up at Chase as I finished swallowing. He still had a few pearls of cum dribbling from his piss slit. I happily licked it up, adding that to the load already in my belly. I sat back on my heels, admiring this teen hunk sitting in front of me. It didn't take long before I was cumming all over the kitchen floor, some of it even landing on Chase's toes. Chase laughed, using his big toe to wipe up some of my jizz off the floor, before holding his foot up to my face.

    "Clean it off."

    I quickly grabbed his foot, greedily lapping and sucking on his toes. My jizz tasted similar to his, maybe a little sweeter. When I was done, my son's friend shook his head and said, "We're gonna have a lot of fun together," flashing me a mischievous smile. 

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