So far, life as a college student was proving to be even better than I'd expected. Living on my own was liberating – not to mention so much sexier! My parents were only an hour or two away, so I knew I could count on them in case of emergency. And then there was my Uncle Austin, who lived in the same city. It really was the best of both worlds: I had my family nearby, but no one was breathing down my neck.
As for the sex… phew, there was so much of it now! My boyfriend Juan and I shared a dorm room, so it was pretty much nonstop fucking when we had the time. We'd always been a couple of hornballs ever since we met in our sophomore year of high school. Back then, I had to resort to sneaking Juan into my parents' house, or fucking him in my truck. Now, we could literally do it until our nuts were completely drained of cum.
There was only one problem with our current arrangement. Now that we had more privacy, Juan wanted to try fucking me for a change. He knew it wasn't easy for me, so we tried taking it slow on a few occasions. But what ended up happening every single time was that I would get uncomfortable and frustrated and tell him to stop. It made both of us insecure and it completely killed the vibe, so rather than dwell on it we decided to stick to what was tried and true and I continued to be the one on top.
After my first week of classes, Uncle Austin invited me out to eat. Our lunch led to a shopping trip, which in turn led to something incredible: me sucking Uncle Austin's dick! The entire time while I was doing it, I couldn't ignore the fact that even though this was my "Uncle" Austin I was blowing, it was actually the very dick that had made me! In my mouth, I had my biological father's penis. When I swallowed his sperm, it was like tasting a part of me.
Moments after Austin's cumshot, Juan burst into the room, amused to see me kissing my uncle's cockhead. "Well, well, well... what do we have here?" Juan asked with a smirk.
"I took your boyfriend shopping, and he decided to replay me with a blowjob," Uncle Austin announced proudly as I put his whole dick back in my mouth. He was still hard as a rock, even though he had just cum. Undoubtedly, Juan's arrival made Austin even hornier.
"You guys look so fucking hot," my boyfriend's voice said behind me. I was on my knees, with my shorts off, so Juan got a perfect view of my exposed ass, my asscheeks spreading open as I leaned in to deepthroat my biological dad.
"You should join us," Austin said. "After all, Brett's got two holes."
Uh-oh. Was Austin insinuating that Juan should fuck my ass? Yeah, this wasn't the time for that. Thankfully, Juan had something else in mind.
"How about I get in the middle?" he suggested. "So Brett can fuck me while I suck you off?"
That was exactly what happened. Uncle Austin helped me get to my feet, holding my hand like a gentleman before planting a big kiss on my lips, tasting the residue of his own jizz in my mouth. Juan approached us, and all of us took off the rest of our clothes. Three naked men now stood in the stuffy dorm room, making out at the same time, three tongues sparring for dominance.
Juan and Austin continued to kiss as I squatted behind my boyfriend and began eating his ass. I knew he didn't need any lube except for my spit. Within minutes, Juan's hole was ready for my throbbing dick. I impaled him, making him moan loud enough for half the dorm to hear. Luckily, Uncle Austin solved the problem by shoving his dick in Juan's mouth.
"That's better," said Austin as he and I made eye contact while spit-roasting my boyfriend. Back and forth, Austin and I thrusted, our hands sliding down Juan's back until they met in the middle. Even the facial expressions we made were kinda similar. It was like looking in a mirror at myself, 22 years older. Would I turn out like Austin at that age – would I turn out like my own father? God, I should be so lucky.
I was so horny that it took me less than five minutes to cum. Austin joined me shortly, blowing a second load. During his orgasm, I observed his face carefully, wondering if that's what I looked like when I was cumming.
After blowing two loads in less than ten minutes, Austin was ready to leave the dorm.
"I'll walk you out," I offered, putting my clothes back on. Juan headed to the shower, and my uncle and I left the room.
"Well, I'm glad to see you boys are making the most out of living together," Austin said with a satisfied smile as we walked down the long hallway. "Sure seems to be working out for ya."
"Yeah. Actually, I wanted to ask you something," I said. "Now that we've had more time to have sex, Juan wants to… he's tried fucking me a few times. But… it never works out."
"Oh," said Austin. "How come?"
"I dunno, I'm just too tight or something. I remember when I started fucking him, there was a bit of resistance at first but then it just slipped right in. And we didn't even really know what we were doing at the time. I should be able to do this, right?" I asked for reassurance. I wasn't used to failing, especially when it came to physical or sexual activities.
"It's different for different people," Austin replied calmly. "Some people just need a bit of practice."
"What kinda practice?" I asked.
"Why don't you come on over to my place on Sunday and I'll show you?" he suggested.
That Sunday, Juan was catching up on sleep after another late night at the library. I left him a note I was going to my uncle's and I headed out. I took the train and it wasn't long before Uncle Austin was buzzing me up to his apartment. I was happy to find it was just the two of us, since Rodney was out at work training clients. I didn't quite know how this morning was going to go, but I was glad Austin and I had the place to ourselves. After a brief chitchat in the kitchen, he led me to his bedroom where he opened a couple of drawers and started taking out an array of poppers, lube, and a sizable collection of dildos and butt plugs all in various lengths and girths.
"Obviously, you want to start with the smallest and work your way up," he explained as he arranged the toys on the bed by size, the smallest being something like a sharpie and the largest was a big black monstrosity that looked like it would rip me in half. I expected him to give me a bag so I could take the toys with me, but then I noticed he'd laid out a towel on top of the duvet.
"Do you... want me to try doing this here, now? Will you help train me?" I asked tentatively.
"If you'd like me to," he replied coolly.
I kicked off my shoes and lowered my shorts. I stood in front of Austin in a T-shirt, jockstrap, and white athletic socks that went up to my calf. I was wearing the same red jock he'd presented to me years ago in this very room. When he saw the familiar jockstrap, he smirked. It was too small on me now, but that kinda made it sexier.
I laid on the bed on top of the towel, parallel with the headboard. Uncle Austin arranged a few pillows under my head and then got on his knees next to the bed. I held onto the back of my knees, exposing my asshole to him.
"I'll start with the smallest," he suggested, taking the thin sharpie-sized toy first. "I'm also going to use this CBD-infused lube, it'll help you relax."
I heard the squirt from the bottle and then his index finger probing my pucker. I twitched, not ready for the touch, but the lube had a warming effect that really did help calm my nerves. Next thing I knew, I felt the tip of the toy lined up with my sphincter. Was I really ready for this? Ready or not, there was no better person to help me find out than Uncle Austin.
"Okay, here we go. You need to RELAX and not clench when I push in," Austin instructed. "And remember, just breathe"
I took a deep breath and as I exhaled, Austin pushed the toy in. Instinct took over and I immediately clenched, but then I remembered his words and I relaxed again, letting the toy into me. To be honest, it really wasn't that bad at all.
"How does that feel?" he asked, the concern in his voice obvious.
"It's not bad, I can probably try something a little bigger," I responded. I was nothing if not competitive, and I didn't want to stop at the smallest toy. However, I did have my doubts if I could handle anything bigger.
Austin continued to use the smallest dildo for a few more minutes before grabbing the next size up. Again, I felt some minimal discomfort, but it was nothing I couldn't push through. These small successes definitely boosted my confidence in this endeavor. Eventually we got to longer and girthier toys, ones that resembled actual dicks. He was attempting to use one that was nearly the size of Juan's cock. This time I began to truly struggle.
"Try some of the poppers. You'll feel a little bit of a high but it'll make your entire body relax," Uncle Austin suggested. I've had a lot of coaches in my life, and that's exactly what this felt like. He was coaching me, mentoring, and training me. He knew when I was struggling and offered advice on how to push forward. Back when I started playing sports as a little kid, it was my dad Charles who mentored me. Now, it was my biological dad Austin's turn to do this.
I took the small vial of poppers and inhaled. It burned my nose a little, but he was right. My head was in the clouds and it felt like all of my muscles were melting. Austin re-inserted the dildo and this time, my body accepted it more easily. This was also the first time one of the toys pushed against my prostate, sending blood to my cock. I let out a quiet moan as I became fully erect, my cock breaking free from the jockstrap pouch.
Austin sensed the shift. He could tell I had gone from struggling to enjoying the sensation of the toy up my ass. He started to pull out, just a few inches, before pushing back in. The action sent a spurt of precum that left a dark stain on the pouch of my jock. He did it again, only this time he pulled out until just the rubbery tip was left before ramming it back in with more force. Each time he shoved the dildo back in, I leaked out more precum.
"Oh, fuck," I gasped, unable to back any longer. "That feels good, Uncle Austin."
I was moaning louder and louder as he continued fucking me with the toy. Being a top for so long, I couldn't believe that I was enjoying this as much as I was. He kept hitting my prostate with the dildo in just the right way until suddenly, my cock erupted, handsfree, shooting a huge load of cum and making a complete mess of my jockstrap.
"Shit! Holy fuck Uncle Austin, I just came," I said in between quick breaths. I just lay there, still with my legs in the air, as he slowly removed the toy from my hole and helped me stand up. My cum started to trickle down my inner thigh as I got up.
"I won't be able to wear these under my shorts on the subway," I noted, pulling off my jizz-soaked underwear.
"Here, I'll wash it for you," Austin offered, taking the red jock from my hand and immediately putting it to his face, inhaling the smell of my fresh load… and possibly even tasting it.