Jeremy - Sexual Awakening: Will

I couldn’t stop thinking about that night with Will. Since I took the walk of shame from his dorm to mine, I haven’t seen him around campus. I wouldn’t say I was obsessing; that’s not the kind of person I am. I was starting to wonder if I had ever seen him around before that night. There are thousands of students on campus, and I’m sure a majority of them have not crossed my path, but in my experience, once you’ve met someone, you suddenly see them everywhere. It counts double for people you’ve had sex with. I would’ve thought it would be four times as much if you were the first guy to penetrate my very tight hole.

I decided to have a reset. I made a point only to watch straight porn and willed myself to think about the women I’ve fucked and how good that felt, just to cleanse my mental palate. It was sort of working, but the images of Will between my legs, thrusting into me, and how good it felt would creep into my mind when I was nearing orgasm. In the heat of the moment, even when just masturbating, I often lose self-control, resulting in an incredible orgasm, but the catalyst of that orgasm was beyond my control.

When Wednesday rolled around, my roommate asked me again to join him, Misha, and Will at the courts for pickleball.

“I don’t know, man,” I said, setting down my backpack and flopping down on my bed.

“Come on. I haven’t been able to get a moment with Misha since she snuck out of my bed last week. I really need an excuse, and I can’t go without you; I’m not good enough to hold my own on the court,” he said.

I grinned, “You’re right about that, you suck.”

“Hey, I tried my best; I was on the soccer team in high school. I’m fast on my feet, but my hand-eye coordination isn’t tennis quality,” he shrugged, pulling his shirt off to put on a workout shirt.

“I’m not sure I’m up for it,” I said, watching as he dropped his jeans, then his boxers, and slipped on a pair of white Jockey sport briefs.

He turned to me, I couldn’t help but checkout his package in the skimpy underwear. Having seen him nude in full view, I was impressed by how the underwear enhanced his package, his legs, and his ass because none of those were all too impressive in the moonlight. “Come on, dude, I’m activating bro-code,” he smiled and then pulled up some running shorts over his briefs.

“Ugh, that’s not fair,” I groaned.

He shrugged, “Bro code mi amigo,” then grabbed a hoodie and zipped it up over his shirt.

Seeing my roommate stripped down, his manhood on display like that, immediately undid the work I put in with all the straight porn this week. My body suddenly needed to see Will again and…see what would happen. “Alright, but only because you activated bro-code. You owe me.”

I pulled off my shirt, swapping it for a sleeveless athletic shirt. Then my jeans and boxers went to the floor. With my ass on full display to my roommate, I felt a sudden rush, knowing he could be checking me out right now. I couldn’t help but spread my legs a little, just to help him get a good look…should he be looking. I was also digging through my underwear drawer, realizing I mostly had trunks and loose-fitting boxers. I don’t own any briefs or anything that will enhance my look should someone see me with my pants off. Whatever, I grabbed a pair of red Tommy trunks and slipped them on. Then I put on some running shorts and sweatpants over them.

When we got to the courts, Will and Misha were already there waiting on us.

“We’re on number 4,” Misha said before we exchanged any kind of greeting.

Will gave me a knowing look. He didn’t have to say anything. We both know he popped my cherry a few days ago, and I liked it. I felt a rush, a feeling I hadn’t experienced before, like excitement combined with a hint of embarrassment and a dash of…something else I can’t quite put my finger on yet. Whatever it was, it was intense. In the same way the Sea calls to Moana, Will was calling to me, or at least one particular part of Will was calling to me.

Lucky for me, or maybe unlucky, one of the emotions I’ve never been able to control is my competitiveness. I couldn’t help but crush Will and Misha, but it was mostly aimed at Will. I had this visceral need to show him through pickleball my masculinity and how I dominate.

In the lockerroom, my roommate quickly stripped off, standing in just his Jockey’s, “bro, you were a beast tonight, where did that come from?”

I pulled off my shirt, glancing over at Will, whose back was to me, “I don’t know what came over me, but it wouldn’t kill you to score one for the team,” I joked.

“Yeah,” he lowered his voice. "Well, if all goes well, I’ll score one for the team tonight.” He grinned, grabbed a towel, dropped his briefs and tossed them into his locker, and walked to the communal showers.

I glanced back toward Will, who was already gone and in the shower. I quickly stripped, tossed my clothes in the locker, and almost sprinted to the showers.

The communal showers have ten shower heads. Everyone knows the first one on the left barely works; you get more water out of a dollar store squirt gun, and the shower head in the back on the right barely gets any hot water. In hindsight, I should have taken the cold shower. Instead, on the left, there was one open shower head next to my roommate, the other two used by guys I don’t know, and to my right, the options were the cold shower to the left of Will or a hot shower to his right, so I went to his right and turned on the hot water.

I did my best to ignore Will, though, from the corner of my eye, I swear he was deliberately flexing under the water and trying to get my attention. I turned away from him, washing my hair and then soaping up my body. I couldn’t help but over-soap my cock, balls, and ass, and as I slowly spun in the water to rinse off, I noticed Will was staring at me. The attention instantly sent my blood rushing to my cock, I had to spin towards the wall so the other guys in the shower wouldn’t see me chubbing up, but I was still visible to Will, and that just took me from 6 to midnight. I quickly spun the dial on the water to cold to get my dick to go back down. As soon as it was soft enough, I darted for my towel.

My roommate was already dressed and closing his locker. As I toweled off, he came over to me and said, “Hey, I’m going to try to take Misha out after this; if she asks you and Will to join us, can you make up an excuse?”

I gave him a look, “That’s no problem. I have to study for my mid-term anyway.”

“Yeah…about that,” his eyes dropped down to my dick as I pulled my towel off, but then quickly made their way back up to meet my eyes.

I said nothing, but I pulled up a pair of clean trunks—the same white ones I was wearing last week with Will, I realized—and then quickly redirected my thoughts back to my roommate's problem.

“If all goes well, I’m hoping to…need the room to myself for a little while,” he finished.

“Bro,” I grumbled.

He smiled, “I know, I know, but…you know, my options are limited. Can you make yourself scarce for a while?”

“How late are we talking?” I pulled up my sweats, tossing my other clothes into my backpack.

He looked at his phone, “It’s seven now, dinner – sex, cuddling, just until, like, ten o’clock?”

I huffed, closing my locker, “Fine, you owe me big, though.”

“So big,” he got all excited.

As expected, Misha invited Will and me to join them for dinner and drinks. I made the excuse that I had to go to the library for some studying. Will didn’t seem to get what was happening. He said he didn’t have anything to do and was up for dinner.

My roommate shot me a look.

“Actually, Will,” I started, not knowing where to take that. “You mentioned that you are taking one of the classes I’m studying for, and I had hoped to pick your brain about something.” I stared at him right in the eyes and saw a look of confusion and the wheels turning.

“Uh…yeah, okay, I guess,” he took a pause. " To the library then?”

“Yeah, Misha, it's always a pleasure.” I gave her a hug, then looked at my roommate and mouthed the words, “You owe me big.” I gave him a fist bump and walked back toward the campus library.

As soon as we were out of earshot, Will said, “I don’t recall having any overlapping classes.”

I chuckled, “No, I was just giving my boy some space so he and Misha can have a proper date.”

“Oh,” he grinned, “Here I thought you were just trying to get me alone again.”

His words bounced around in my head, hitting sensors like a pinball machine, lighting up those parts of my brain that need and want sex and pleasure. “I um…”

“It’s ok, you don’t have to say anything; I wasn’t looking for anything other than more sex anyway,” he laughed.

“Oh, ok,” I said, unsure how to respond.

We walked a couple of blocks before he felt the need to fill the silence between us. “So, you’re locked out of your room again?”

I shook my head, “The things I do for other people’s pleasure.”

He laughed, “I don’t suppose you want to do something for my pleasure?”

I looked over at him to see how serious he was, and his face was not joking, “I…I don’t know,” I said nervously. “What did you have in mind?”

“Well, I wouldn’t mind a repeat of last time,” he tossed it out there.

I chuckled, “Maybe if the roles are reversed,” I glanced over to gauge his reaction.

He grinned, shaking his head. “Ahh, I mean, we’ll have to see about that. It’s not usually the game I like to play,” he rubbed his chin stubble as he spoke.

His words rang true for me, too, and I couldn’t help but laugh. “I hear that; that’s why I ask,” I looked around quickly for other people. “I never bottomed before last week,” I whispered.

“You are a natural,” he quickly added. “I jerked it every night this week thinking about getting a repeat tonight,” he chuckled.

Fuck, I do get turned on by the idea of being someone else's sexual muse. My brain was starting to lose focus on my reasons for not going back to his place.

“Why don’t we go smoke a bowl, hang out, see what happens? Unless you actually wanted to go to the library?” He asked.

I laughed, “No. I do need to study, but all of my notes and stuff are in the dorm, and…” I gestured towards the other side of campus, “My dorm is experiencing some kind of sex right now, or at least it will be.”

He laughed, “Perfect, my dorm is free, we can do…whatever we want there.”

My heart started racing, but I followed him anyway. I know what he wants from me, but I don’t think I want to try that again. That was kind of a heat of the moment thing, and right now, yes…I admit I’m horny, but not ‘get fucked in the ass’ horny.

When we got back to his dorm, he immediately pulled out his bong and packed it with his stash. He handed it to me. “You take the first rip,” he said. Then he put a towel under the door and opened the window as far as it would open. I took a big rip and let the weed do its thing.

We talked for a while and went through a decent amount of his weed before I was rolling pretty hard.

“So, what’s the deal with your roommate? Have you guys ever…” he started making gestures with his hands, miming jerking off and then blow jobs, then he grabbed invisible hips and started thrusting his pelvis up into them. That move made my dick twitch.

I laughed, “No, he’s…well, I’m pretty sure he’s straight.”

“That never stopped me,” he joked. "I’ve had a lot of fun with straight boys.”

“That’s fair. My best friend back home is gay, and I thought I was straight, and we jerked off together several times,” I told him.

He cracked open a beer, “want one?”

“Yes, please,” I took the extra can from him.

“Your best friend is gay, and you guys never fucked?” He looked at me in disbelief.

“Well, I mean, we’ve fooled around, mostly just jerking off and the occasional drunk makeout, but nothing more than that. Not even blow jobs,” I chuckled.

“Damn, why not?” He kept drinking.

“For one, his dick is huge,” I chuckled, “I figured if I let him blow me, I would have to return the favor.”

“Nah, as a gay guy, I can say I’ve had a lot of no reciprocation blow jobs with straight guys, and it was still hot for me. I’m sure he would’ve loved to suck you off.” He was looking at my crotch as he said it.

“I don’t know. Jackson isn’t like that, I don’t think,” I said as I sipped my beer.

“Well, I’d love to blow you,” he said, licking his lips subtly.

I chuckled nervously, feeling relaxed from the weed, horny from the conversation, “I mean…I won’t stop you,” I leaned back on my elbows.

He didn’t hesitate to see if I was serious. He quickly dropped to his knees in front of the bed, between my legs, and started reaching for the waistband of my sweatpants. My heart started racing; my blood was flowing towards my dick. I was hard the instant he grabbed my waistband, pulling my trunks and sweats down with one good yank.

He dove onto my dick, licking and sucking me, reminding me how good a guy can suck a dick, and I was here for it.

I dropped down from my elbows as he pulled my sweats and underwear off the rest of the way, tossing it across the room with a clank. He started jerking my cock as he sucked my balls and that space under my balls. I was moaning and spreading my legs, letting him do his thing, fuck, it felt good. Girls don’t normally suck my balls, and his mouth was able to take most of my sack with little effort. I don’t usually cum from blow jobs, but I was getting close after only five or so minutes of his torturous pleasure.

“Fuck, I’m getting close,” I warned him.

I heard him open his desk drawer and pull out his lube. With a squirting sound, I almost instantly felt him pushing lubed-up fingers into me as he continued to suck me off. The penetration stung a little, backing off my orgasm, but his blowjob kept me in the moment, and fuck did this feel good.

Will picked my legs up, putting the heels of my feet on the edge of the bed, giving him easier access to my hole as he fingered me. Then he stood and dropped his pants and underwear; his hard 5” cock sprung free, and he quickly started adding lube. I was nervous, I knew what he wanted and I kind of wanted it too. He stood at the edge of the bed and started rubbing his cock head on my lubed hole.

“Mmm,” I moaned. Something about that just feels so good, like the calm before the storm. Then I felt the head pop in, and it hurt like hell. “Oh shit, no, wait,” I scooted up the bed and off his cock. “Fuck, that hurt,” I closed my legs and looked at him standing there in just a shirt, naked from the waist down, his glistening cock sticking straight out like it was staring at me. “Dude, you’re not wearing a condom?”

“Oh, sorry, did you want me to wear one?” Will asked, slowly stroking his cock.

“Yeah, man,” I chuckled, “I didn’t start barebacking since last week.”

“Yeah, that makes sense, I guess I thought that was like a ‘first time’ thing, I don’t know, stupid,” he chuckled, then reached for his three pack of condoms, pulling out the last two and tearing one off. He quickly rolled it down his cock and lubed up. “Do you want to ride me so you have more control?”

“I don’t know, I guess,” I said, feeling oddly effeminate as Will lay flat on his back and I straddled his waist. I reached back and grabbed his cock, aimed it straight at my hole, and let my body weight push me down on it until it popped in. The pain shot into me just as before, but I was able to stop it from going deeper like this, so it was easier for me to relax. As I relaxed, I slowly slid down his cock, feeling all of his inches push up into me, pulsing and flexing with excitement as my ass met his lap. “Mmm,” I groaned, letting my head fall back as I took in the feeling of a cock inside me.

His hands went to my hips, stroking my thighs and holding me as he gently rocked his hips up to me. The feeling was getting better the more he did it.

“Stroke your dick,” he suggested.

My cock had gone soft, but the second I started playing with myself, it sprang back to life. I adjusted my legs around his hips so I could raise and lower my ass on his cock. He helped by thrusting up into me, and I leaned forward, placing my left hand on his chest as my right hand continued stroking my cock. I quickly started to enjoy his cock pushing into me. I was able to adjust myself to be at the perfect angle to get pegged in the prostate. My hips were stretching out so I could get maximum pleasure, “Ummm, fuck,” I groaned.

I looked down into his eyes, he was getting so much pleasure out of fucking me, and that really flipped a switch inside me, turning my inner slut into an outer slut as I was riding his cock the way only another guy could. “Fuck, that feels so good,” I whispered to him.

“Jeremy, I’m gonna cum soon,” he moaned.

I didn’t want it to end, I was just getting used to his size, but at the same time, his cock was already swelling inside me and my ass instinctively clamped down to push him harder into my prostate.

“Fuck, I’m gonna cum,” he grabbed my hips and started slamming up into me. “Oh fuck,” he whispered, and his torso crunched up as his hands gripped my ass tightly, and I felt a new warmth inside me. He let out a few more choked grunts; then his shoulders fell back onto the mattress.

I knew he blew his load, and I wanted to blow mine. I picked up the pace on my cock as I let my ass go all the way down his softening dick. I rocked back and forth to wiggle his dick inside me. That was all it took; my balls tightened, and my abs crunched as my first rope shot out of me and landed on his chest. He put his hand out to stop it from hitting him in the face, and my next couple of shots pooled in his hand. “OH fuck...Jesus,” I groaned as my orgasm subsided, and I relaxed, still impaled by his dick.

I took a few breaths, then slowly raised my ass off his cock, feeling him slip out of me and the cum filled condom as well. Fuck, even that felt good. I lay on my back on his bed, catching my breath. He hopped up and got a paper towel to clean the cum off his chest and hands, then gave me one to clean myself up.

“Oh shit,” he picked something up on the floor. “I think I accidentally threw your clothes at the bong, and it looks like your boxers are soaked in bong water,” his face scrunched up as he held them up.

“Oh shit, that sucks,” I chuckled.

“Sorry, man,” he said, grabbing a plastic bag from his trunk and tossing the underwear in there. “You’re going to want to wash them as soon as you get back,” he handed me the bag.

“Thanks,” I handed him the cum covered paper towel.

“Why don’t you grab something from my top drawer to wear home?” He suggested, pulling the drawer open and grabbing some shorts to sleep in.

“Thanks, you don’t have to…”

“I insist,” he cut me off, snapping the waistband of his shorts on his waist. “It’s the least I can do since you gave up that ass twice now,” he chuckled.

I couldn’t help but grin, getting up and going to his dresser. I took a look at the underwear drawer, but most of the stuff looked too big, “do you have anything that will fit me? I’m like a 29 waist.”

“Oh, umm, most of that is 32, some 34, but in the back, under my ties, you might find something in the 30 range from when I was in high school,” he smirked.

I dug in the back and found a pair of white CK briefs that looked a little older, the tag said ‘30’ so I slipped them on. I got a rush out of how the briefs cupped my balls and looked on my ass, but when I noticed him watching me check myself out, I got a little self-conscious and quickly grabbed my sweat pants, pulling them on over my new briefs. “I’ll return them when I get…”

“Don’t worry about it; they don’t fit me anymore,” he cut me off.

I looked at my phone, and I had a text from my roommate: Misha didn’t want to come back tonight, so feel free to come back any time.

I rolled my eyes.

“Everything ok?” Will asked.

I shook my head and smiled, “All good. I guess I can head back now; I got the ‘all clear’ text.”

“Oh, nice. Well, thanks for the sex,” he joked.

I laughed, “Yeah, thanks for the invite.” I am not sure of the protocol here, so I just gave him a fist bump and grabbed my stuff. “I’ll see you when…ugh when I see you.” I unlocked the door and performed the walk of shame for the second time in about eight days.

Back at the dorm, my roommate was already asleep, this time in some boxer shorts and a ribbed tank top. I stripped down to my underwear and got into bed as quiet as possible. Something about wearing Will’s underwear got me turned on again, and there was no way I was going to fall asleep with a hard-on. I quickly and as quietly as possible to not wake my roommate, rubbed one out, thinking about how good it felt to get fucked by Will. It didn’t take long for me to nut all over myself, so I grabbed the t-shirt I was wearing to wipe up the cum and tossed it on the floor to deal with in the morning. I tucked my cock and balls back into the briefs and fell asleep moments later.