Intimidating New Guy I'm Sharing a Room With 05 (Patreon)

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Chapter 5: Trying New Things

I was sitting there with my ass out, legs in the air, my lithe little body ready for anything that the big jock who lived in my room wanted to do to me. 

He leaned over and lined up his big rod between my small, perky buns. 

“You’ve actually got some juicy butt down there,” he said, poking my ass with his dick. “Enough meat to clap.”  

He started spitting on his dick, rubbing up and down against me. Every time he ran over my hole it felt like heaven. In my head, there would be no pain involved, but I knew it was going to be a mountain to climb. It was worth it. I had seen it enough in porn, and I wanted to be fucked.

He prodded my hole gently, like he didn’t know what to do, and didn’t want to push too hard. Eventually he surprised me by leaning forward and kissing me, then gently inserting himself, just barely, into my opening.

The ring of my hole stretched and burned, even though his head wasn’t even fully inside yet. I groaned into his mouth and reached for my dick, trying to make it easier. It worked a little, but I was still tense. He pulled out slowly, letting my hole relax back down. I felt it return to its normal size, the tension leaving, but I already felt empty. I wanted him back in me. 

His tongue returned to my mouth as he pressed forward again, just slightly stretching another centimeter wider than the last time. He was calming my body by kissing me, making it easier to take his dick, and it was actually working. My first kiss, and it’s Ben, while he’s trying to stuff his dick into me. I hadn’t cum in a full twenty four hours, and it had been the horniest day of my life, and It felt like Ben was using some trick on me that he had learned from fucking girls. I thought about all the girls he had probably fucked over the years, and it was so hot thinking that I was one of them now. His first boy, probably. 

I was never truly warmed up, but I could take the whole head after another minute of making up and gentle probing. He shoved his thumb in my mouth and started to drill me hard with just the head of his dick. My ring stretched and closed back and forth, and it felt like heaven after another minute. I could tell he was struggling to hold back, but still enjoying the sensation of putting himself into my warm hole. He put his second thumb in my mouth and played with me a little, stretching my lips like I was an amusing toy for him, while my body satisfied his dick.

Right when he started to actually pick up the pace, inserting a couple inches of his dick into me at a time, his mom knocked on the door.

“Not now!” he yelled quickly, not even pausing his humping.

“Jeez, fine,” she muttered on the other side of the door as she walked away, “Teenagers…”

I had been so horny all day, I knew I was going to cum just from the repeated contact with my body, even if I didn’t touch my dick.

“I think I’m gonna cum,” I whimpered, surprised at the submissiveness of my own voice. 

He didn’t respond, silently inserting himself another inch, making my body tense up.

I came without touching it, feeling him inside me, blocking my hole from contracting as I pulsed with the most intense orgasm of my life. I squirted up to my neck and chest before I grabbed my shaft, trying to aim it at my belly button. I milked out another few ropes while he continued his gentle thrusting into my body. The pressure continued to build as he grabbed my body by both sides, holding me tightly, trying to push in further. 

The mix of pain and pleasure was almost too much to handle, but I still wanted it, even after I had finished.

“Cum inside me,” I said quietly. 

“Ok,” he said without changing his rhythm at all.

He looked down and spit onto his shaft again, pressing into me repeatedly and giving me the strangest and best sensations of my life. In seconds, I felt like i could cum again, and started stroking myself. 

He held my hips and easily lifted my body off the bed, slamming into me roughly. It hurt, but in a good way. 

“I’m gonna cum in you, bro,” he said.

“Cum in me,” I whispered, as his body clapped against mine rapidly, my body shaking. 

I barely knew which way was up as I held onto my dick like I was riding a bull. I spanked my pork until I blew another load onto myself, and he started pulsing inside me shortly after I started pulsing.

The feeling of his giant cock pulsing inside me while I rode out another orgasm was a wild treat. I felt my brain spinning on overdrive. I didn’t think I would ever come down from that high.

He finally slowed, and froze, before slowly starting to pull himself out of me. 

“Damn,” he said as he set me down, letting his dick fall out of me. “I’ve never done anal before, or fucked a guy.”

“That was awesome,” I said, “It hurt, but it was good.”

“That hurt?” he said, “I thought for gay guys your ass was like a vagina.”

“We have the same ass as you,” I said, “Plus your giant hog isn’t going to be easy on a vagina either.”

“That’s true,” he said, “I just thought guys could take it easier. Pain in general.”

“Have you stuck anything in your own ass?”

“No!” he said, laughing. 

“Just my fingers,” I said, smirking.

He looked a little embarrassed for a second. “That felt good though.”

“Maybe I’ll try something a little… bigger than my finger on you next time.”

For the first time since we’d moved in here, I saw the slightest hint of fear on his face.

I went to bed that night feeling like a new guy. My hole was sore, almost too sore, but it was a pleasant reminder of what I had done. I felt like I had accomplished something important, gotten over the hump of something. Just as I fell asleep, I started to think about what the next thing would be for me to accomplish. 

—[]—

The next day at school, I felt a surreal sense of joy all day. There was something thrilling about having “lost my virginity”. I had proven that I could take a huge cock, and the soreness in my ass was only a positive reminder of how good life could be. I felt like everything was different. I wasn’t afraid of the future. I was a man now, even if I didn’t look like it yet. I could take a big dick, and it would only get easier with time, if what I read on the internet was true. 

I noticed I was also less afraid of growing older. I looked at my third period teacher, Mr. Rockins, in a different way. He was the fit, older guy that all the moms chatted about. He was attractive, but obviously he had never been my type before. I didn’t look at teacher-age guys as sexual objects like I did with guys closer to my own age. But now, I felt like I had conquered the teen male concept, getting the best there was to offer. I had fucked Ben, or rather been fucked by him, and it left me wondering what a hunky, mid 40s dude, slightly older than my parents had to offer. 

One thing about Mr. Rockins, that maybe no one else had noticed but me, was that one time, a few months prior, he had used the term “partner” to describe a relationship of his. It didn’t necessarily mean anything, but I clocked it, as a closeted boy often does, as a “potentially gay” flag. 

I stayed after class and chatted with him. 

“Hey, Mr. Rockins,” I said as I approached his desk, the other students shuffling out of the room in the periphery. 

“What’s up, kiddo?” he said, his typical, cheery voice perking up.

“I, uh, wanted some help with something,” I said, trying to make up a reason to talk to him on the spot.

“And what’s that?” he said. 

I paused for a moment, before admitting I just didn’t feel like going to my next class yet. Being the warm teacher that he was, he told me to sit down.

“You know, when I’m feeling overwhelmed by things, I take it out at the gym,” he said, giving a subtle flex of his big arm through his shirt. 

“I’m not great at sports,” I said, looking down at my hands. 

“You don’t have to do sports to work out,” he said, “You just go move some metal around and feel a burn. You should try it sometime. The one right across the street is good. I go there before class sometimes.”

I took careful note of what he was saying, even if he didn’t know the real reason I was doing it. A plan was forming in my head before I even realized it.

After school, I walked straight over there and talked to the guy at the front desk. He was hesitant at first, since apparently a lot of the high school guys come and fuck around at the gym, but he eventually approved me for a day pass. I walked out of there with a giant smile on my face, with my plan set in motion. To be honest there was no plan, all I knew was that where there was a gym, there were showers.

—[]—

That night, I told Ben about what I was doing. 

“Mr. Rockins??” he hissed, incredulous, as we sat naked on his bed.

“Yeah,” I said, “I have a feeling about him. I’m gonna see what happens.”

“Bruhhh,” he said, sinking back into his pillow.

“What?” I said, “He’s hot.”

“That’s so… kinky. He’s your teacher. You’ll both get in trouble.”

“Not if no one finds out.”

We both paused for a moment, chuckling.

“I actually heard a rumor about him,” Ben said, sighing as he leaned up on his elbow. 

“What kind of rumor?” I asked, curious.

“Someone saw him at the gym once.”

“And?”

“He has a big dick, I guess.”

I felt the feelings stir inside me.

“Are you ok with my trying to suck him off?”

He thought for a moment, shaking his head. “Better than the assholes on the football team, I guess,” he said. “He is hashtag goals to be honest. I hope I look like him when I’m older.”

I smiled a bit, watching him think, before he went on.

“Whatever you wanna do. Just… be careful.”

“Ok,” I said.

“And tell me the details when you get home.”

“I will,” I said, as I crawled over his body on all fours, ready for my daily dose of Ben.

—[]—

I was so nervous as I got up early the next morning, throwing some shorts and a tank top on and putting my school clothes in my bag. Before I left, I woke up Ben, telling him to wish me luck.

“Good luck, buddy,” he said with sleepy eyes, holding up his fist.

As I turned around, he gave me a smack on the ass. “Go get ‘em tiger.”

I chuckled, but my heart was racing as I left the house.

When I got to the gym, I froze as I looked at all the dad-types doing their pre-work routines, mixed in with a few guys my age in pajama pants that I recognized from school, spotting each other on the bench. A couple things hit me as I stood there, trying to take in the intimidating scene. First, straight guys get very close to each other and even touch each other while they’re working out, their bulges on display right in the other’s face. And second, I had no idea what I was doing. 

It was more crowded than I had ever seen it, and I didn’t realize til I got there that I had no idea how to “do” the gym. I quickly grabbed some dumbbells so I wasn’t just standing around doing nothing, and tried to copy what others were doing. I picked up the small five-pounders, while a fit, mom-type lady next to me picked up the fifteens. I lifted the weights in little curls and wondered if I was doing anything right or wrong. I felt kind of helpless, but determined to do something, hoping that Mr. Rockins would walk in eventually. 

Then I saw him.

Mr. Rockins strolled in, and he gave me a wink when he saw me. I felt a tingle in my stomach. 

It was strange. Two days prior, I had never thought about him sexually, but after my mind was opened to the joys of sex, I wanted more, and I wanted to try everything. He was a natural next step in my mind. He’s the only guy I knew that was older that was fit and possibly into dudes. Maybe my perky little ass would get him to try things with me. 

I tensed up as he walked toward me. I even felt my sore hole in the moment, like it was preparing for something.

He came over and offered some help. 

“Keep your elbows in place,” he said, touching my wrist and gently indicating how to do a simple curl.

“Thanks,” I said, looking down at his hand as it touched me. 

“Good job,” he said, abruptly walking away to the locker room.

He came out a minute later, and I was still doing my mild version of curls. 

“You want to spot me on bench?” he asked.

“I have no idea what that means,” I admitted, half a nervous smile on my face.

“I’ll show you,” he said, and I followed him over.

“Step closer to me,” he said once I got in position. 

As weird as it seemed, I looked around, and that was indeed how everyone else was doing it. It was clear that he could see up my shorts, even if he wasn’t looking. 

No one looked at us, but I was glad I wore my tight briefs under my gym shorts, because I was starting to get seriously hard. 

He spotted me next, and his bulge was right in my face, making it hard to focus on any direction he was giving me. He even had to repeat himself a few times, and I could tell he was getting a little annoyed about it. I could barely lift the bar, but I got through a couple sets.

We split up and he finished his workout solo, while I went back to trying some curls. I used the ten pound dumbbell this time, and actually felt some resistance. Oh, I thought to myself, that’s kind of nice. Maybe I’ll look like Ben in a couple years. 

I saw Mr. Rockins get really sweaty doing his pump, until he disappeared into the locker room. I followed him in, naturally.

Inside, it was surprisingly empty. I guess all the professional people got out of there by 7:30, and it was just us school people left behind.

I took the locker across from his, and when I turned to say something to him, I was surprised to see he was already butt naked. His body was bangin, and he had legit chest hair. He looked like Ben in 30 years. He even had some salt and pepper grey hair on his chest, and his dick hung down like a tree trunk. I looked down at his cock out of instinct, scanning upward across his muscles and gentle body hair. When I reached his face, he was looking at me. He gave me a wink as he threw on a towel and headed to the showers. 

Fuck. 

He went into the farthest shower in the back, and the two of us were the only ones in this area.

Now is my chance.

I took the shower stall across from him. I was pissed off to learn that there were glass doors on these stalls, but I noticed that he didn’t close his all the way. I left mine open a bit as well, watching his naked form as he started rubbing his body under the hot water. I watched him for a minute before he looked back at me. He looked me up and down, scanning my features, like he was torn about something. I knew he was gay, and we were doing this. It was just a matter of time. I watched as his dick got hard, a big, thick, piece of meat gaining mass before my eyes.

This was better than Johnny or any other random jock from school. This was the perfect next step after Ben. 

I peeked out of the shower to make sure no one was around, then crossed over the tile to his stall trying to step into it, but he put his hand up. “The fuck are you doing?”

Fuck.

“I just…,” I said, my face red, scared, “I thought…”

I started to turn away when he grabbed my shoulder.

“I’m just fucking with you. Get in here, twink.”

I felt the smile stretch my lips from ear to ear. I stepped in carefully, trying not to slip as I joined him. The hot water burned my back as my body pressed against him, my hard dick pressing against his much larger boner, still gaining size. His light layer of chest hair felt like heaven against my hairless body, and his hands grabbed my hips, pulling my into him.

“I’ve seen the way you look at me in class,” he grunted as he pushed his body into mine.

“I’m a horny little pervert,” I said, looking up at him, our faces inches apart.

“I bet you’ve dreamt about my big cock.”

I didn’t say anything. I just reached forward and grabbed it, giving it a tight squeeze. 

“You’re such a real man,” I said.

“And you’re a good boy,” he grunted quietly, raising his hand up my body to my shoulder.

He pressed down gently, and I sank to my knees. 

Apparently, he had no time to spare. He pressed his thick hog past my lips immediately, giving me no time to even soak in the idea that I was actually about to suck my teacher’s cock. He fucked my face quickly and relentlessly, and it was perfect. My brain turned off and I held his body, encouraging him to be as rough with me as possible. I wanted to show him that I knew what I was doing. I had been trained on large cocks. My red eyes teared up while the hot water drowned my face, his thick rod plugging my throat. I was nothing but a wet cock receptacle. 

It was different than Ben’s, the curves hitting me differently as I tried to maintain composure and take the pummeling. The noises in my throat were drowned out by the shower water, and my groans were barely audible since my lips were fully plugged by the hunk of meat he was shoving into me. His hands held my head tightly, and he alternated between pushing me down onto him and fucking me like a sex toy.

His grip on my head was different than Ben too. He was less of a desperate, horny jock and more of a controlled, dominant daddy. 

After a minute, I barely touched my boy cock and quickly squirted onto his feet.

“Fuck,” he whispered, going even harder against my poor throat, shoving in deep and bringing himself to orgasm using the soft, internal walls of my orifice. He came suddenly, making me gag as he held himself deep in my throat. I let him do it, even though my body fought against it.

“No one finds out about this,” he said, reason returning to his brain after cumming inside his student’s throat as he pulled out of me.

“Sure,” I said while coughing out the juices from our session. I stepped out, my head still fuzzy from the lack of oxygen, forgetting which shower I was in for a second, and looking for my towel.

I looked up and froze when I saw two guys from school. One of them, this blonde guy named Jared narrowed his eyes at me. He looked down at my boner just as I wrapped my towel around me to cover it up. I nodded and walked past him, but he looked next at Mr. Rockins behind me, who was exiting the same shower in his towel. My face turned red, and I grabbed my shit, got dressed, and booked it out of there as quickly as possible.

—[]—

In class, it was strange, but awesome. I was horny and tingling. Mr. Rockins was good at pretending that nothing had happened, but my sore throat reminded me of everything the whole time. Maybe he had done this before. Maybe with lots of guys. The idea turned me on so much, I couldn’t wait to explore more. 

I saw Jared at lunch sitting at a different table. He was talking to his friends, when suddenly they all looked at me at the same time, giggling. I just shook my head. 

Later on at home, Ben was still at practice as I lay back on my bed, scrolling through things, when I got hit up on snapchat. It was Jared.

“Hey,” the message read.

“Hi there,” I said back, bracing for some homophobia or worse.

“Do you wanna hang out right now?” his next message read.

I laughed out loud to myself.

—[]—

The next few years of my life were mind-opening. I ended up getting fucked by Ben a lot, almost every day once I learned about douching. I even fucked him a couple times when he was curious what he was missing. It felt like we were secret boyfriends until he got a serious girlfriend that lasted until college. He let me fuck around as much as I wanted, but he was always somewhat protective over me. 

Rumors got around school and I ended up getting with many closeted and curious guys, even servicing a group of “straight” friends one Friday night after a lacrosse game.

By the time I got to college, I was prepared for wild sex, and I introduced a few fellow freshman into the joys of man-on-man bonding.

And it all happened the way it did because my Dad and Ben’s Mom decided to get married. The rest is history.