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CHAPTER 3

From Mentee to Mentor

BRADY:

    When I first met David Hillbecker, I was still in the closet. I was in high school, and I met him at the bank where my mom worked, of all places. Hearing him mention his "husband" let me know he was gay, so I made sure to introduce myself to him. We hung out at the mall that day, and we got together on a semi-regular basis after that.

    In the beginning, we didn't have sex. We didn't even necessarily talk about sexuality; a lot of the time it was school, and college opportunities and such. More than anything, I thought of him as a mentor, and maybe a father figure. I didn't know any other openly gay people in our area at the time. David was homeschooling their son Eric, who had been bullied in school for having two dads, and I felt like we shared that connection, living in a place that was not as gay-friendly as we would've liked it to be.

    When I moved to Boston for college, I finally got the taste of big-city life that I'd been craving! Boston ain't even that big, but it felt HUGE to me. All of a sudden, there were thousands upon thousands of gay people around me. By that time, I was already together with both David and his husband, so there was a plethora of dick coming at me 24/7.

    Before I came to Stag Meadow Lane for the summer, I expected it to be a homophobic shithole like the town I'd grown up in. To my surprise… it wasn't. I mean, the most conservative person on the street might've been my uncle, and even he was okay with having a gay son like D.J. I was so used to assuming gays were welcome in cities and shunned in small towns and suburbia, and it felt nice to be proven wrong, at least in this case.

    Still, there was no denying that finding dick here was MUCH more challenging than in the city. Even the local cruising ground had been abandoned after a murder there. So, I stuck to my cousin D.J. as my blowjob buddy for the summer. He and I sucked each off to sleep on a nightly basis now, and I was proud to see him getting better and better at it under my tutelage.

    One evening, after interning all day at my uncle's campaign office, I walked in the bedroom I shared with D.J. only to find him watching a video on his laptop. When I heard my own voice coming from the speakers, yelling out "Oh yes! Daddy, fuck me!" I knew exactly what my cousin was watching.

    "Is that one of the videos I sent ya?" I asked, pulling my shirt off.

    "Aha," D.J. nodded, fully naked and boned up, watching my boyfriends David and Sven spit-roasting me on screen. Even though his dick was hard, D.J. wasn't jacking off, potentially waiting for me to join him. I quickly undressed and took a seat next to my cousin on his bed.

    "Can I ask you something?" he turned to me with sudden earnestness in his voice. "Doesn't that hurt?"

    "What, taking dick?" I smiled.

    "Taking THAT guy's dick," D.J. said, pointing out Sven's huge, pierced member thrusting back-and-forth inside my ass. "He's not even taking it easy on ya. With that piercing and everything… Honestly, it looks painful."

    "Well it's not painful to me," I explained. "Once you get used to it, you'd be surprised what your hole can handle."

    "I just can't even imagine taking that," D.J. said, nonetheless hard as a rock while watching the video.

    "Well, do you think you can take THIS?" I asked, pointing down at my own growing dick. Even though not as large as Sven's, it sure wasn't small either.

    "You mean… You wanna fuck me?" my cousin stuttered nervously, leaking out a huge wad of precum from his piss slit.

    "I mean, if you need a mentor… I'm here," I offered. For me, my mentors were David and Sven; the way I saw it, it was my time to pass the buck. D.J. smiled big and was clearly excited about my suggestion. As he got down on the floor to settle in between my legs for a pre-fuck blowjob, I wondered how much of this might have been planned before I'd even walked on the door. 

    My cousin got to work on my dick with his usual enthusiasm. Each time was better than the last, and I relaxed back into the bed to enjoy his developing skills. After a few minutes he slowed down, and I needed a break if I was going to save my load for D.J.'s ass.

    "Could you tell I was close?" I asked him as I reached over to a bag I kept near the bed.

    "Yeah," he said, standing up but remaining in between my knees. His hand moved to his own dick, which was so hard it looked angry, and he idly spread his oozing precum up and down his shaft. "It's like... you get extra hard at certain points, and I noticed that always happens before you cum."

    "That's good, D.J." I said with more than a little pride. "Part of giving great head is learning to read your partner's responses. Hopefully a guy will be telling you what he likes but... well, sometimes it's hotter if there's no words at all, so you have to go by touch." I thought back to all the blowjobs I'd given at glory holes or at loud dance clubs, where talking wasn't part of the dynamic.

    I handed him one of the small bottles I'd retrieved.

    "Here," I said as he took it from me, "lube up my dick and then put some on your hole." 

    My cousin began to slick me up, and I had to grab his wrist to slow his hand down a little. D.J. just smiled, and it was nice to see that he was getting confident enough not to take my action the wrong way. He knew I only stopped him to keep from blowing my load too soon. He'd gotten extremely good at giving handjobs, though I supposed he'd already logged a few years of practice in that area, pleasing himself.

    My cousin surprised me by taking the initiative and climbing up over me on the bed, knees now on either side of my hips. His hard dick jutted out above my chest and I watched him twist his torso around so he could more easily apply lube to his virgin ass.

    "You wanna try sitting on it, huh?" I said with a grin. "Seems like you might have been giving this some thought." He turned back to face me with a hesitant look, his hands still at work between his cheeks.

    "It's, um..." D.J. began, "it's how I do it when I've... practiced." 

    I nodded slowly, fighting the urge to ask what exactly he'd been practicing with. That could be a conversation for another time, but I felt another surge of pride that he was doing some exploring on his own, as well as with me.

    "Doing it this way lets you control how much is going in," I said as he moved into position, with the wet head of my dick lightly brushing his ass cheeks, "and it's going to feel like a lot, at first."

    "I want it all in me," D.J. said with determination. "I'm pretty sure I can do it."

    "This will help," I said, handing him another tiny bottle. D.J. had seen me use this a few times while he was blowing me, so he knew what to do. My eager cousin took extra care opening the bottle of poppers, which I was glad to see (especially since he was holding it over my chest). He took a timid huff and then replaced the cap. I grabbed the bottle from him since he was already feeling the rush.

    "Oh wow..." D.J. said with a lilt in his voice. He started to relax his legs and lower himself down, enough that the head of my dick poked right onto his pucker. He paused and I saw him brace himself, putting his hands on his knees, his eyes closed and a dreamy look on his face.

    "Okay, just ease yourself down slowly," I said, moving my hands to his waist. I didn't hold him tightly, I really wanted him to set the pace. But feeling his bony hips with my palms made this all even hotter. All of a sudden, my dickhead was slipping into him. It happened fast and I heard him breathe in sharply. He kept himself in the same position, and his sphincter squeezed my dick right under the ridge of the head.

    "Just relax... take a few slow breaths," I instructed, and after a moment I felt the pressure ease. I was impressed again – it had taken me a little time to learn how to control and relax those particular muscles. I'd had plenty of loving guidance from David and Sven at the time, and I tried to be just as supportive of my younger cousin now. 

    Over the next five minutes or so, D.J. worked his way down my dick, about half an inch at a time. A few times when he looked a little overwhelmed, I asked him if he wanted to stop, but he always said he was fine. When I had about three-quarters of my shaft inside him, D.J. reached for the poppers again and took another quick sniff. It was wild (and a bit of a relief) to feel how quickly his insides relaxed around my dick.

    "Mmmmm", he moaned loudly, and then sucked in another breath quickly as the rest of my dick slid into him. I felt the firm skin of his taint up against my trimmed pubes, and the pressure of his ass on my balls.

    "I'm all the way in, D.J.!" I said, squeezing his hips gently. "You're such a fucking stud, bro." He smiled big and kept his eyes closed, savoring the moment and the achievement.

    "See how it feels to move back up a little," I suggested, after we'd stayed in that happy place for a bit. "Just go as slow as you like." 

    D.J. spent the next few minutes experimenting with moving up and down at different speeds. He was definitely enjoying himself, evidenced by the sticky mess his dick was making on my stomach. A steady stream of pre-jizz had been oozing from the tip, and I occasionally reached down to stroke him, which just resulted in more gasps and moans. I fondly remembered the first time I'd ever cum with a dick buried in my ass, and I knew that was going to be happening for my cousin tonight.

    "Let me take over for a minute," I said, tightening my grip on his waist a little. D.J.'s contented sigh told me he was fine with that, and I lifted him up so only about a third of my shaft was in him. "Lean forward, over me more," I instructed, and he moved his hands so they were just below my armpits. For the first time, he opened his eyes and stared down into mine. The moment became pretty intense, and I felt my dick throb as his ass relaxed more. This was the perfect moment to...

    I pushed in about an inch more, but I did it fast, and hit my target on the first try.

    "Holy fuuuuck..." D.J. groaned as his eyes got big. The head of my dick was pressing right into his prostate, and I had to try hard not to laugh out loud with pure joy. His face was so cute, looking amazed and a little loopy.

    "I'm just gonna do that a few more times... if that's okay with you," I said teasingly.

    "Yes! Oh my god, yes!" he blurted out, and I got back to work. I reached down to stroke my cousin's dick as I pulled back and then pressed into his magic spot once again. I only needed to do it twice more before his load started erupting all over my stomach and chest. A few wads even made it to my chin, and from the uncontrolled moans and gasps coming from my teenage cousin, I suspected this was one of the best cums of his life thus far.

    His hole was twitching like crazy around my shaft, and the pressure on my sensitive dick took me over the edge as well.

    "Fuck, D.J., I'm gonna cum in your ass!" I shouted, right as my load started to blow in my cousin's insides. He was moving up and down my dick again, maybe almost instinctively. He was milking both our dicks that way, with his pressing down onto my abs as it let the last of his juices out.

    Finally, D.J. let himself fall forward and pressed his chest into mine. Nuzzling his head under my chin, my adorable cousin moaned softly with satisfaction.

    "Thank you so much, Brady," he whispered. "I... I'm so glad you're my first." I reached my arms around him and held him tightly, and we fell asleep with my dick slowly softening inside him.

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