Jeremy - Sexual Awakening: Chuck

As it would turn out, Misha wasn’t interested in my roommate after they had sex that first night. She gave him the “let’s just be friends” speech and then proceeded to backslide into her ex-boyfriend. My roommate was upset about it for about a day and then found someone else he was into.

“So, no more pickleball?” I asked him.

He chuckled, “No, hard pass, stupid fucking sport anyway. Thanks for playing, though, and keeping Will distracted.”

“You still owe me for that,” I told him.

He laughed, “I know. Next time you need me to dive on the ugly fat friend grenade, you let me know,” he joked.

I focused the best I could on finals and swung my masturbation back to straight porn as much as possible. I didn’t see Will around campus. None of our classes overlapped or seemed to be in the same buildings. Which I was ok with. I can look at what happened with Will as an experiment that I tried…and enjoyed but don’t really need to do again. As sexually fluid as I am, I much prefer to top if I’m with a guy or fuck women if the opportunity presents itself.

With all my time focused on studying, I still struggled with midterm exams. When the grades came back, I was pretty frustrated with myself. So, I decided to buckle down. I started a routine of classes, then the gym, then the library until all of my homework and reading was done, then home, repeat.

My acting classes would occupy most of my spare time outside of my regimented routine. Keeping up with those classes was relaxing for me, so I considered it my “play time” with my friends. I was able to get into character and be someone other than myself for 90 minutes; it really helped me take my mind off of life while also getting my fix of being social without drinking or any other partying that kept throwing off my routine in the recent past. One notable exception was Jayce, who dropped the class but would still show up for rehearsals sometimes. He was good friends with some of the other students and would read lines with them in his free time.

“Hey, Jeremy,” I heard Jayce’s distinct lispy voice.

“Oh, hey. It’s been a while. How are you?” I asked, awkwardly hugging him.

“Ugh,” he let out a dramatic sigh, “busy as always. My pre-law classes are a lot; you know how it is.”

“I don’t, but I can imagine,” I smiled.

He not so subtly looked me up and down, “I don’t suppose you want to grab a bite…or something, later?”

I was flattered, “I don’t know, last time…”

“Last time was…last time. This is different,” he cocked his hip out and put a hand on it, showing me he was confident we could be friends.

Two hours later we were back in his dorm, he was riding my dick like a cowbow. His eyes rolled back into his head, and it made me almost jealous; I know the pleasure he’s feeling right now, and even though his ass feels…so good, and I’m getting close to blowing my load, no, nope, I’m not going down that road. I grabbed his hips and thrust hard up into him, eliciting a whimper.

Then I rolled him onto his back, crossing and folding his legs to give me a human handlebar to hold onto as I pummeled my dick into him.

“Ung, fuck Jeremy, that feels so good,” he started jerking his dick faster. That look on his face, I know that look, I started fucking him and watching his face, waiting for it to light up when I pegged his prostate and it did. I kept aiming for that same angle. “Oh shit, oh shit,” he was panting and stroking his cock. I felt his ass tighten around my cock, and I just thrust harder, not letting his ass slow me down. “I’m gonna cum,” he squealed in a high-pitched moan. Then his ass started to tremble, then his cock erupted, shooting his cum onto his stomach. When the third rope of cum shot out and landed on his chest, he moaned and breathlessly held up a hand to my abs, “wait, ungh, wait, ahh…it’s too much, you gotta pull out,” he groaned as another rope of cum shot out of him and his body convulsed under me.

I quickly pulled out, ripped the condom off, and frustratingly jacked my dick; having to jerk myself off instead of being able to cum in him almost gave me blue balls, but I forced myself over the line and shot a wad of cum all over his balls, then another onto his cock, then let the rest dribble out on his grundle and his mattress.

“Oh my God, Jeremy…that was so good,” he huffed out of breath.

I just smiled, knowing it was good for him, which was good enough for me. I take pride in making other people cum.

I dressed shortly after, heading back to my dorm. I didn’t get any whining from him, no emotional baggage, he got what he needed out of this fuck and from the look on his face, he was very satisfied.

Again, my roommate was already asleep, this time in only a pair of grey Abercrombie briefs, his dick was hard, he must be having a hot dream. I’ve woken up in the middle of the night to him moaning and humping his mattress, but as far as I can tell, he’s never had a wet dream since we’ve been sharing a room.

I passed out around 3:00 am and my roommate managed to wake me up at 10:00 am, coming back from the gym. After he was dressed and out the door, I couldn’t fall back asleep, so I decided to get up and get myself some breakfast, then the library, then the gym. I wasn't going to break my routine because of mediocre sex with Jayce, but even mediocre sex is still sex, so I can start my routine a little late today.

I had a text from my roommate telling me to join him and some other friends at a local pub for a monthly trivia night against his ex-girlfriend's sorority. I texted him back, letting him know I’d be there, but I had to do some studying and then go to the gym. I quickly grabbed my books and started heading out, then remembered to grab a change of clothes for after the gym, just shoving a t-shirt and clean underwear into my backpack and running to catch breakfast before they stopped serving.

I was most of the way through my set at the gym, still sweating from the treadmill warmup, when a jock I had worked out with a couple of times, who I knew was gay and into me, walked in and started working out. I had never given him the time of day because, well, his physique is amazing, and he has model good looks, but intellectually…I tried to connect with him when I bumped into him in the library one day but the guy is about as mentally stimulating as watching paint dry.

Now, here I am, after mid-terms came back shitty, I am sexually frustrated after last night's unimpressive experience with Jayce, and Chuck was over there curling 50lb dumbells like it was no big deal while checking me out from across the room. So, to make myself feel better, I went over and started working out next to him. He flirted with me, which is all I needed to feel better about myself and instinctivly started shutting it down like usual, but when he kept on…I let him continue.

After I showered, I realized I hadn’t grabbed my white CK trunks, I grabbed Will’s white CK briefs, and it made my dick twitch. I had only worn them for my walk of shame back to my dorm and then mostly forgot about them. I pulled them on; something about this item of clothing, maybe because Will had worn them and his dick had been inside them many times, maybe because they accented my body in all the right ways, I don't really know, but wearing them instantly turned me on.

The second I stopped checking myself out in the mirror across the locker room, Chuck walked in with a towel wrapped around his beefy waist. He is not a subtle man; when he saw me standing there in tighty whities, he grinned and wagged his eyebrows.

“You have plans for tonight?” he asked in his deep, manly voice.

I looked up and down his defined, hairless body, he really is the definition of a gym rat. “I’m doing trivia night with some friends down at Ambrose,” I told him.

He looked disappointed. “Oh yeah, I hear that’s fun. It’s not my thing, though.” He opened his locker and started getting dressed. I can't say I'm all too surprised this guy doesn't do trivia. He's a pretty face, but...a bit of a blank space between the ears.

As soon as I zipped my bag and threw it over my shoulder, he spoke again, “You still have my number, right?”

“I…um, yeah, I’m sure I have it,” I pulled my phone from my pocket.

“Good, use it sometime,” he smiled, then pulled his pants up over his boxers. Turning back to his locker, he pulled out some deodorant and started spraying it under his arms. I couldn't help but watch.

I glanced at my phone as I walked out. Three texts from my roommate were wondering where I was, and I realized I was going to be late. I ran across campus and made it just in time to sign up for our team before the game started.

My roommate is good with sports trivia and science, I’m good at literature and pop culture, our friend Matt is good at history and current events, and Sharon, Matt’s girlfriend, basically filled in the pop culture gaps of the things I didn’t know, like reality TV.

I had a couple of drinks throughout the game and maintained a steady buzz. I was planning to head home with my roommate after the game was over, but something happened while I was in the bathroom because I came back to find him tucked into a corner booth sucking face with his ex.

“What the fuck did I miss?” I asked Matt, nodding my head towards the booth.

“Oh, I don’t know, he went over there to rub it in her face that they did worse than us; the next thing I know, she’s groping him in that booth,” Matt laughed, sipping his beer.

“Damn, ok,” I pulled out my phone. It was almost midnight. Fuck, if he was going to try to bone her tonight…that means our room will be occupied.

I quickly text my roommate, “Are you taking her back to our place tonight or what?” I didn’t want to pressure him, but I didn't want to hang out all night either. I sipped my beer and glanced over at his booth; I knew he felt my text vibrate in his pocket, but he didn’t check it, which really was all the answer I needed. He was trying to get some tonight.

“We’re heading out,” Matt said, signing the receipt for his and Sharon’s drinks.

“Nooo,” I said dramatically, knowing this left me alone until my roommate got done fucking and waved the all-clear flag.

"Sorry bro got things to do," Matt winked and tilted his head towards Sharon.

I rolled my eyes, giving him a fist bump of approval.

Wondering what my next move was, I looked around the bar to see if maybe I could find someone that interested me. Perhaps I can wipe away last night's disappointing sex with Jayce from my sexual history and start with a clean slate.

Everyone seemed to be in groups or not giving off the right vibes, so I did the next best thing: I texted Chuck, you know, to see what’s up.

Me: Did you end up doing…anything fun tonight?

Before I could put my phone away, he texted back.

Chuck: I went out with the guys, was hoping to get laid, but no luck lol.

Me: I know the feeling.

Chuck: I can change that 👿🍆💦

Me: Lol, now?

I hit send before realizing that could be interpreted as me asking him if he was down to fuck right now instead of questioning if he was suggesting we fuck this late instead of waiting another night.

Chuck: I’ll be at my dorm in about ten minutes. Meet me outside the Schneider building?

I guess he took it as me suggesting we fuck right now. I’m sure I’ll regret this, but I text back: I’ll be there in ten.

I grabbed the check and paid in cash so I didn’t have to wait. Then, I walked as quickly as possible toward the Schneider dorms.

The entire walk over, I was picturing the tight round glutes that I've seen in the shower at the gym, my dick chubbing up at the thought of how tight he's going to feel around my dick. A drop of my precum no doubt staining Will's white briefs that were doing their best to hide my hardening cock.

I had seen Chuck in the showers at the gym and knew his dick was smaller than mine, so I wasn’t surprised when we got back to his dorm room, and clothes started getting pulled off that he was about 4” cut, a little thicker than Will, but not by much.

I don’t know why; I just assumed he wanted to bottom for me. Stereotypes maybe, I’m taller, I have a bigger dick, I’m more straight identifying, but when he tossed me face down on his bed and started groping my ass the way I grab breasts, humping his cock across my hole, I got the idea that he was actually planning to top me.

“Fuck, I’ve been waiting to get into this ass for months,” he slowly slid his dick across my hole again; this time, it got a low sensual moan from me. Feeling the wet rubbery tip of his bare cock glide against the crevice of my pucker was so erotic for something so innocent in its own right.

I realized how hard I was just from knowing he was going to fuck me, and I didn’t want to fight it, not right now, not in this moment. I arched my hips slightly on his next run across my hole, this time, the head lingered on my slightly relaxing pucker, feeling a little more wet this time from his precum.

I heard the snap of the cap of his lube and then the cool liquid dripping onto my crack, being smeared in by his now lube-covered cock. When his dick slid across my hole, this time, it had almost no friction, and “Mmm, fuck,” I groaned, spreading my legs wider on the floor as my torso wriggled on the bed, giving us both a better angle for pleasure.

On his next slide across my hole, he pushed the head of his cock down with his thumb, not yet breaching my entrance, but that added pressure sent all kinds of horny signals through my body to my brain, the lust taking over both our bodies as we repeated that movement a few more times.

On one of his strokes, I felt the head break through, parting my tight outer ring in the gentlest way possible, “Mmm, ungh, shit,” I groaned at the pleasure, not the discomfort I felt with Will, but not quite an easy entrance either. His head slipped out, and he continued his sliding up and down my crack, teasing my hole a few more times before trying again to push in, this time the head caught at the right angle with the perfect amount of pressure, and the entire bell end went right into my sphincter. “Ahh, fuck,” I hissed and groaned feeling my ring stretching to accommodate his girth.

“Mmm, yeah, that's it Jeremey. Let me in, open that ass up for me,” Chuck’s voice had dropped a few actives and became much more aggressive. He gripped my hips tight and continued to push his cock in another inch.

“Ahhh,” I sucked in air, “do you have a condom on?” I groaned, feeling the strain of my hole opening and the slight panic that he was pushing in bare.

“Not yet,” he said, “I wanted to get you open first. Tight holes respond better when you open them up bare,” he chuckled, pushing a little deeper, more than half of his raw cock inside me now.

“Mmm, no, no, we need to be safe,” I said, popping my head up and craning my neck to see his face, his eyes locked on his cock penetrating my ass.

“No problem, let me get a few strokes in bare?” He tried to negotiate.

I chuckled, shaking my head, “Nah, man, wrap it up.”

He smiled and slowly pulled out, my ass holding onto his cock, feeling every vein and ridge of his bare cock as both of his girthy inches slid out. I swear my ass lips licked the precum off the tip of his cock since he pulled out so slowly, and I’m that tight. We both let out a groan as the tip completely separated from my ass. Mine a sigh of relief, his a clear disappointment as he reached for a basket under his bed that had condoms and other sex goodies in it.

He wrapped up quickly and then was less interested in fucking for my pleasure and focused on his pleasure. He pushed in quickly to the hilt. Then gave me no time to adjust to the full length of his cock before he started pulling out and building up a rhythm. I groaned and tried my best to relax, knowing he was getting off on my hole, knowing he had lusted after me for months and was claiming his reward turned me on enough to find pleasure in his cock, jackhammering my hole.

He fucked me hard and fast, but thanks to his size, I was able to quickly get passed the penetration sting and get right to the pleasurable parts of getting fucked.

He was only fucking me for about 5 minutes before I noticed the telltale signs of a man that’s about to nut. “Are you close?” I groaned, my cock had not had any attention since I was pushed onto the mattress.

“Yeah, getting close,” He groaned, holding my hips as he slammed into me.

I quickly adjusted myself, pulling my legs onto the mattress, spreading my knees wide so I could get my hand around my cock and start stroking. I was not going to leave here without getting off. He adjusted his stance behind me to meet the new height of my ass and gripped tighter to my waist.

“Fuck you feel so good,” he grunted, each thrust punctuating a word.

The pounding of his hips hitting my ass was a new feeling, not quite as good as Will’s cock hitting my prostate, but it resonated in a way that was helping me get off. I gripped my cock as tight as I could and really went to town. Rocking my hips to meet Chuck’s thrusting, getting maximum pounding on my ass. I was getting close.

With my free hand I reached between my legs and past my balls, I wanted to feel his balls and cock sliding into me. His balls were pulled tight to his body, and my hand tickling them sent him over the edge, “I’m cumming,” he grunted, and I felt his balls twitch in my hand as he slammed hard one last thrust and held himself against my ass.

The twitching of his balls sent me into overdrive. Knowing I just let this stud have my ass for his pleasure and feeling his orgasm happening in my hole, the extra heat radiating off his cock inside me had to be his load shooting off; it was too much. I felt my hips spread wider, relaxing to get a little more of an angle on his cock, which was just holding in place inside me. I rocked on his dick a little more as he panted behind me, catching his breath. The slow gyration of my hips combined with the jerking of my cock, that was it; I felt the cum gates inside me release, and a wave of pleasure rushed through my body, “Oh…fuck,” I groaned and popped off my first rope of cum onto the sheets below me, “shit…ungh,’ I groaned as my ass clenched so tight on his softening cock that it forced him out of me, adding more pleasure to my orgasm. I twitched and shot a few more ropes of cum onto his bed before my balls relented, and I could breathe again. “Fuck,” I huffed, the last of my orgasm reverberating through my body.

He chuckled, “That was worth the wait,” he said, holding the ring of the condom around his softening cock as he pulled the cum filled reservoir tip from my tightly clenched hole. A feeling I'm beginning to love.

I looked back and saw a decent-sized load in his condom as he pulled it off and tied a knot around the end before tossing it in the trash.

When I returned to my dorm, walking a little funny but feeling sexually satisfied, I quietly opened the door to not wake my roommate. Once again, he was asleep, nude, only one of his legs covered by the blanket, his uncut, shriveled dick on full display. He was in a deep sleep, not even flinching when the door latch clanked shut. The room smelled like his weird condoms and sex.

As I undressed quietly, stripping down to the white briefs gifted to me by the guy who popped my cherry. I couldn’t help but keep glancing over at my roommates dick. I’m not into him, but there’s something intriguing to me about his uncut cock. Now that I’ve played with a few cut cocks, in a few different ways, I’m curious.

I folded my pants and put them on my dresser, pulling my money and phone from the pockets. I tossed the receipt from the bar into the trash, which landed right next to a used condom; a much smaller load of cum pooled in the tip than what both Will and Chuck had released when fucking me, which filled me with an odd sense of pride. Still…the sight of it did make me glance over at my roommate's cock and balls one last time before hopping into bed and passing out.