Jeremy - Sexual Awakening: Jackson

When summer break started, I flew home and once again found myself sitting by the fire, catching up with Jackson. Though we were much better about staying in touch this year than we were freshman year, in-person hangouts are always better.

Somewhere around beer number three, the conversation finally got off of his recent breakup, which was more than three months ago, and the conversation turned to my sex life.

“You still aren’t dating anyone?” He asked.

I did a slow head shake, pictured all the people I had sex with this year and how most of them were guys, “nope.”

“Lots of masturbation, or were you playing the field?” He grinned.

“A little of Column - A, a little of Column - B,” I said.

He took a sip of his beer, studying me with his eyes, “You had sex with another guy, didn’t you?”

I blushed instantly, “what?”

“You little slut, you’re just putting your dick in every hole that comes your way, breaking hearts at every turn,” he joked.

I shrugged, “What can I say? My dick is in demand.”

He took another sip of his beer, continuing to study me. “No, something’s up. What are you not telling me?” He grinned.

I can never lie to Jackson; he can read me like a book, “I might have had sex with… more than one guy.”

“Oh man, I knew it! Brooooo, are you on Grindr now? Are you gay now? I won’t judge your journey, but you gotta tell me what’s going on?” He insisted.

I chuckled and sipped my beer, “Well, no, I’m not on Grindr, and no, I’m still…just…fluid, I guess. I’ve just had more opportunities to explore that part of me, and, well, you know me, I don’t like to limit myself.”

He shook his head, “you little slut,” he chuckled. “Wait,” his eyes got huge, “Noooo, did you get your cherry popped?” His eyes locked on mine; even in the glow of the fire, I could tell he was wirelessly hacking my brain without me saying anything. “Oh my Gawd, you did!”

I blushed and shook my head, the grin on my face giving him all the information he needed to know.

He sipped his drink, “fuck, I can’t believe it; after all these years, Jeremy, my Jeremy is a bottoming for hordes of college guys,” he feigned disappointment.

I just held my hands out, palms up, and shrugged as innocently as possible.

He pulled a preroll out of his shirt pocket, lit it up, took a hit, and passed it to me. He blew out the smoke towards the fire, “Did you like it? Bottoming, I mean?”

I took a long hit, tossed my head from side to side, shrugged, and then blew the smoke out towards the fire. “I mean…I guess. Not at first…”

“But once your tight ass got used to it, you loved it?” He grinned.

I took another hit and passed it back to him, then started laughing, which made me go into a coughing fit. " Yeah, I guess,” I choked out.

He laughed at me and then took a hit. “So are you, like, dating this guy?” He blew out his smoke and passed it back to me.

I giggled, “Fuck no,” I took a hit and passed it back.

He smiled, “So, just fuck buddies?” He took a hit.

I blew out my smoke, “I guess,” I had to think about that for a second.

He blew out his smoke, taking one more hit and passing it back to me to finish off. I took a long hit and flicked it into the fire.

“So, you going to let me tap dat ass or what?” He asked, grinning at me and taking a sip of his beer.

I blew my smoke out, “Fuck no,” I chuckled.

“Oh damn, that’s fucked up,” he chuckled.

I laughed, “It’s not you, it’s me,” I laughed.

“Oh, I know it’s you,” he laughed, “I’m in demand back at UNC,” he groped his cock in his sweats to accentuate his point.

“I don’t doubt that. You’re a very sexy guy, Jackson,” I said in a moment of honesty and took a sip of my drink.

“You know, you did promise me, if you craved dick, you’d call me…so, you kinda owe me,” He grinned at me.

I couldn’t help but laugh, “you’re not wrong.”

“So what’s up then? You gonna let me get some or what?” He adjusted his dick in his sweatpants again.

I thought about it for a minute, then shook my head slowly, “I don’t think so, man.”

His head tilted back and to the left, as he huffed dramatically, “Oh come on, Jer, I need some ass; you’re my best friend…you said you’d give it up to me before giving it up to some random dude…”

I chuckled, “I know, I know, but…well, one, your dick is huge, I can’t handle that thing, and two…wouldn’t it be weird? I mean, you and me, we’ve been friends forever. Wouldn’t it be weird if I let you fuck me?”

He was already shaking his head ‘no’ before I finished. “Look, I know I have a big dick, but I know how to use it,” he gripped it through his sweats; the outline was like a Maglite flashlight. “Second, what do you mean, weird?

“I mean…I don’t know, it would change our friendship, wouldn’t it?” I shrugged, not 100% certain what I meant at this point, feeling the effects of his preroll.

“Nah,” he took a sip of his beer. “The way I look at it, it’s just like when we jerk off together,” he shrugged, “just two good friends helping each other out.” Then he burst out laughing, “It ain’t like you’re suddenly gonna fall in love with me,” he continued laughing.

I chuckled, “Yeah, I guess you’re right. Still…you’re too fucking big, dude,” I laughed.

He cocked his head to the other side, and he looked at me disbelievingly, “Are you for real?”

My eyebrows shot up, “100%, man. Look, the biggest dick I’ve taken was like…5 inches, and it hurt like hell. The only other dick I’ve taken was like 4 inches. Ok, that one felt good, but that’s like half of your dick,” I shrugged.

He nodded, “Less than half, but I feel you.”

We sipped our beer in silence for a minute. I was feeling really horny, and the talk about his big dick was getting to me, “I don’t suppose you’d want to jerk off together?” I instinctively groped my hard dick through my running shorts.

He grinned at me, then groaned in disappointment, leaning back in his folding chair, “To be honest, I would, but I kinda set up a hookup with a guy on Grindr for tonight.” He shrugged, “It’s been a few weeks…and I really need some ass,” he chuckled.

I smiled, feeling a bit disappointed, “I get that.”

He looked at his phone, then let the front legs of his chair rest back on the ground, “speaking of, I gotta get back to my place and shower before I head out to his.”

“Oh, ok,” I stood up; my dick was chubbed, so I quickly slid my hand into my underwear and adjusted it, “ignore him; he has a mind of his own,” I grinned.

He stood up, did the same adjustment, “Mine thought you were gonna let me finally fuck you,” he laughed.

I laughed with him, and he walked into the dark trail of trees that goes between all the properties in the neighborhood. His parents' house is on the other side.

I went into my house. It was quiet and empty. My parents were in Philadelphia visiting my dad's youngest sister, who is going through a divorce. My older brother moved to Michigan last fall, where he got a job, so I had the house to myself.

I took a quick shower, the water cascading down my skin; the weed and beer had me thinking about the first night Will fucked me. While soping up my ass, I let a finger slide in, and it reminded me of how good it felt when Chuck fucked me. My dick was rock hard, and I started stroking myself. I continued to finger my hole, adding a second finger as deep as I could while fisting my cock a flexing my leg muscles, getting myself closer and closer to cumming. My foggy mind couldn’t help but drift to think about Jackson and the guy he was about to fuck. How he was going to use some guy's ass the way Will and Chuck used mine to get off, the same way I used Jayce’s hole to get myself off.

The hot water started to turn cold, so I quickly rinsed off and decided to finish myself off in bed.

I toweled off, walked across the hall to my room, and flopped down on the bed. I pulled out my phone to look for porn, and while I was browsing, I saw in a thumbnail a guy that looked like Jackson. I watched the video and slowly stroked my dick back to full hardness; my balls were aching at this point. I clicked over to message Jackson.

Me: Hey man, we’re cool, right?

Jackson: All good, man, just got out the shower, about to head out.

I pictured Jackson naked. Remembering how good it felt when he was between my legs, jerking us both off the last time we fooled around. Thinking about how sexy his body looked, how good he felt touching me, how easily we got off together.

Me: So, you’re going to go fuck that guy?

Jackson: I’ll come fuck you if you changed your mind lol 😉

Me: Man, I’m horny AF, but I don’t think I could take your dick lol

There was no response for a bit, so I clicked back over to the porn. My dick was still rock hard, and I gave myself a few good tugs, edging myself a bit before my phone vibrated.

Jackson: Well, look, I’ve fucked a lot of tight asses, most guys can’t handle my dick. I’ve gotten good at fucking guys and getting off with only about 4 or 5 inches in them. It’s fucking great, I could do that for you if you want.

This made my insides ache for sexual relief, stroking my dick to the idea of letting Jackson push in a few of his massive inches, a drop of precum pooling on the tip of my dick. My dick is 6” cut, so I’ve never thought about only pushing halfway in.

Me: Really?

My heart started racing as soon as I hit send.

Jackson: Fuck yeah man. U down?

I was thinking this is a bad idea, but at the same time, fuck…I’m horny. My balls answered for me.

Me: Only like 4 or 5 inches max?

Jackson: I do it all the time, well…often lol

That made me feel less nervous.

Me: Ok, come over before I change my mind lol.

Jackson: On my way.

Me: Just come upstairs. I just got out of the shower so I’m naked. 😉

Jackson: mmm, I’m already in the back yard, I’ll be up in a minute lol

Almost a minute later, there was a gentle knock on my bedroom door, and it slowly pushed open. The only light on in the room was a 40-watt lamp, so my pale white skin didn’t glow like it did when my dorm room light was on. Jackson walked in slowly. He was only wearing a loose-fitting tank top and some basketball shorts. I could tell he was freeballing since his dick was swinging back and forth as he walked and getting harder with each step closer to me.

For the first time in our friendship, I wasn’t sure how to act, but I’m horny, and I’ve never felt sexier. The way Jackson looks at me like I’m the sexiest guy he’s ever seen does something to me. He slowly pulled off his tank, dropped it on the ground, and slipped off his sneakers before dramatically dropping his shorts. His dick was rock-hard and incredibly intimidating. The head was already leaking precum, and I realized I hadn’t unpacked my lube since I got home.

“Shit,” I hopped out of bed.

“What?” He looked worried.

I chuckled and shook my head. “My lube is in my backpack still.” I grabbed my bag out of my closet, unzipped it, and dug through the front pocket. Then, I felt the tube and pulled it out. I dropped the bag and rushed back to the bed, handing it to him. I was about to say something, but he cut me off.

“Only four or five inches,” he grinned, then pushed me playfully onto the bed.

I lay on my back in the center of the bed, my head on the pillows. Half-jokingly, I spread my legs as wide as I could and lifted them up. "Do me like one of your French boys, Jack-son,” I grinned.

He shook his head and smiled at me, “Nah, you're my boy; I’m gonna treat you right,” he grabbed my legs aggressively and dropped his head right down to my hole. His large tongue flicked at my hole, sending little shocks of pleasure into my body like he was whispering the secret password to my hole to get it to open up for him, and I felt it working instantly. I had never been rimmed before, and Jackson seemed to be an expert.

“That feels good,” I whispered, spreading my legs wider for real this time, letting him get better access. It was pure ecstasy. He continued to push his face into my cheeks, and I felt the tip of his tongue starting to separate my ring; l moaned again at the intensity, which only encouraged him to dig in deeper. I was so turned on I let my hands fall on top of his head, intending to massage his head as he rimmed me, but I was enjoying the sensation so much that I accidentally pulled his head deeper into my ass instead. “Fuck that feels good,” I moaned, my legs floating in the air and my toes curling.

He took his time and made love to my hole with his tongue. I was writhing and squirming and letting out small moans every time he dug into me deeper, all for my pleasure. He ate my hole for at least 20 minutes, getting me nice and relaxed with his tongue, occasionally adding his fingers and spit; I was in heaven. I didn’t know Jackson was so talented. Every time I tried to jerk myself off, he would reach up and stop me.

When I couldn’t stand it anymore, he pulled his head out of my ass, letting my legs drop back down as he scooted up between and started stroking us together. I was so horny and so ready for this. He reached over for the lube, looking at the bottle like he had never seen it before, then squirt a good-sized glob onto our dicks, stroking them together.

“Mmm, fuck,” I groaned; the pleasure of his big strong hand and the lube all sliding on his warm big dick sent chills through my body directly into my balls.

I felt him adding more lube and then spreading it on my hole, using his finger to gently push some into my hole. He pushed his cock down my crack; the girth alone was spreading my cheeks more than the other two dicks that had been down there, but it was also somehow softer and felt better as he teased my hole with the head of his cock for a minute.

“Are you ready?” He asked, in a tone I don’t think I ever heard from him.

“Shouldn’t you put on a condom?” I asked, lifting my head to look at him. The familiar scene of a sexy guy between my legs, but this time, it was Jackson, and it felt right, so right.

“I didn’t bring one, I’m on PrEP,” he said, with a grin, still teasing my hole with his cock head.

“I’m not,” I said.

“Well, fuck, Jer, I didn’t bring a condom,” He smiled and shrugged, adding a little pressure to my hole. I felt my ring start to give way to the fat head of his cock.

“Mmm, umm, fuck, wait, I think there should be one in that drawer,” I pointed frantically at the nightstand.

He smiled and dashed for the drawer, digging inside, “I don’t, umm,” he kept digging, “ah, got it,” he chuckled. “Jesus, have you had this since junior high?” He held up a Trojan condom in a faded white wrapper that had been through the washer and dryer at least once over the years it hung out in my pocket in the hopes I’d get laid. He smiled, using his teeth to tear it open. “I don’t think this is gonna fit, man,” he chuckled again and tried to roll it down his cock, but it kept rolling up. He rolled it out completely, and it looked tight on him. He quickly added lube; then the head was right back in the cleft of my excited hole. He lined himself right up and gently wiggled all nine inches with his hand while adding gentle pressure until the head popped in.

“Ah - ah,” that familiar sting shot into my body, and I sucked in some air with a groan.

Jackson held his cock head in my ring, leaned over, and started kissing me. We had never kissed like this before. This wasn’t just playing or practicing; this was passionate, this was intense, and with his kissing, he slowly curled his hips under me and pushed a few inches into me with only a slight resistance from my hole. I couldn’t help but moan into his mouth and wrap my arms around his neck, pulling him tight to me, feeling his broad shoulders and strong back. He moaned into my mouth, and God, it felt good. I wrapped my legs around his tight waist and held on to him as two and then three of his thick inches sank into me.

“Mmm, fuck,” I groaned, feeling my ass stretched further than it’s ever been stretched.

“Oh my gawd, Jeremy, you’re so fucking tight,” he whispered, his lips touching mine as he said the words and then continued to kiss me.

He pulled out slowly and then pushed into that same spot as promised, “Ungh, fuck you’re so big,” I groaned as his cock stretched my anal walls to new limits, but there was a pleasure in it that was making my toes curl.

He started kissing my neck and nibbled my ear, “I’ve wanted to fuck you for so long,” he said and rocked his hips again, out then in, out then in again. “I didn’t know how good this would feel,” he instinctively pushed a little deeper.

“Ungh, fuck, too deep,” I groaned.

He groaned at the idea of not pushing any deeper but continuing to try and build a rhythm, but I was already feeling that burn I felt when Will fucked me.

“Mmm, need more lube,” I whispered.

He sat up quickly, pulling his cock out; he quickly squirt more lube on the head and used his cock to push it into me, lubing my chute as his cock stretched me back open. That’s when I felt it, and I saw the look on his face as it snapped while he pushed in two inches of well-lubed bare cock.

He hung his head, “fuck, condom broke,” he said. “It’s too tight,” he smiled.

“And it’s like ten years old,” I chuckled.

“Do you have another one?” He asked, not so subtly pushing another inch of his bare cock into me.

“Mmm, no,” I moaned; the feeling of his raw dick pushing into my tight hole felt so good, so smooth as his cock head seemed to swell as it slid over my prostate.

He leaned back over me, holding himself up, his muscles flexing as another inch sank into me. Lowering himself onto his elbows, his beautiful chocolate face hovering right over mine, he kissed me gently. “Do you want me to stop?”

I licked my lips, looked into the eyes of my childhood best friend, felt his massive raw cock flexing inside me, and slowly shook my head left and right.

He grinned, then kissed me with the tongue he used on my hole a few minutes ago, moaning into my mouth as he sank another inch into me. Then he started sucking my neck and building up a rhythm. His raw cock felt unbelievable; it slid so easily inside my tight chute I couldn’t help but moan. He was putting constant pressure on my prostate, and his flexing abs were stroking my cock every time he rocked his hips into me.

My hands were exploring his back muscles and the back of his head as his mouth hit all kinds of erogenous zones I didn’t realize I had.

“Fuck me…feels so good,” I moaned.

“Your ass feels so good,” he moaned right back. “Fuck, I need more,” he groaned, curled his hips into me a little harder, and sank another inch into me, going deeper than I’ve ever been penetrated before, stretching my hole beyond its limits; it was nothing but pleasure for me.

“Fuck, your cock feels so good,” and it really did.

“Want some more?” He whispered in my ear.

“Mmm, yeah,” I moaned.

“Yeah, you want my full dick?” He asked again, laying on top of me and fucking me so gently and so passionately.

“Yes, fuck - fuck me, man,” I groaned, wrapping my legs tighter around his waist.

“Ok, take a deep breath,” he said.

I didn’t know what he meant, but I did, and no sooner were my lungs filled, he thrust hard up into me, hitting what felt like a wall and pushing painfully through until his entire cock was inside me. The pain shot up into my guts, and a new, fiery sting rushed through me.

“Ahhh, fu…ck,” I tensed and bucked under him, but his weight held me in place while his cock skewered me.

“Relax, relax baby, that’s your inner ring,” I felt his dick twitch inside me, massaging my prostate, “It will feel better in a minute, just like the outer ring. It just needs to stretch around my cock,” he said into my ear in a low, sex voice, then kissed the crook of my neck. Holding his cock all the way inside me, my legs spread so wide I thought my hips might pop out of their sockets.

“Shit, ungh,” I felt tears welling up in my eyes, but at the same time, I felt so full, and the heat from his cock was radiating through my entire body, and that…that felt amazing. I hissed and tried to breathe.

He gave me a few more seconds before he slowly pulled a few inches out, leaving my inner ring, and then pushed right back into it, this time with a dull sting but also with a bit of pleasure. I groaned, trying to focus on the pleasure.

“That’s it, baby,” he slowly rocked his hips up into me, “Yeah, Jer, my whole cock is in you right now. You’re taking all nine inches,” he kissed me, and we moaned together.

My head was spinning; I couldn’t believe it. Jackson was fucking me; his entire massive cock was deep inside me bare, and the way he kept calling me ‘Baby’ was really triggering something slutty inside me. “Oh fuck, Jackson,” I cupped my hand on the back of his head, holding him tight to me, trying to spread my legs and open my hole for him.

“Yeah, Jer, that’s it, take my dick,” he started to pull out more inches and push in deeper with every thrust.

My prostate was so stimulated my cock was leaking precum between my and his abs, dripping more every time he thrust into me. The sting of my inner ring had turned into a new pleasure sensor, and every time he thrust into it, my brain lit up like a pinball machine. “Oh my god, that feels so good,” I moaned.

“So good,” he moaned, thrusting faster into me. Making sure to get every inch in before pulling back out and doing it again, and again. I felt every ridge of his cock every time he pulled out slowly, and then he hit all of the pleasure buttons with his fat cock head as he quickly thrust balls deep again. I reached between us and started squeezing my cock. I didn’t need to stroke it; the pleasure of Jackson fucking me was so unbelievable, I only needed to give it a few hard squeezes, and I felt my balls tighten. His prickly, trimmed pubes tickled my balls with every thrust, and I felt my hole clamping down on his dick, and on his next thrust into me, he hit my prostate just right, which was all I needed to be sent over the edge.

“Fuck, I’m cumming,” I said as he shoved into me again. Pegging my prostate even harder. I stretched my legs out wide, getting as much dick as I could, my toes curling as my fist tightened around my cock, and my entire body started to shake with pleasure as my orgasm boiled over. A massive wad of cum shot out of my cock, creaming between our abs. The second shot added to the puddle, “Oh fuck,” I groaned as my body twitched under him, his next thrust into me adding to the pleasure; I almost blacked out, “fuck,” I groaned, squeezing out another rope of cum as my orgasm continued.

“Fuck,” Jackson grunted, thrusting hard into my tightening hole, “Can I bust in you?” He thrust harder and deeper, then once again.

The images of the massive loads I’ve seen him shoot in our past jerk-off sessions flew through my orgasmic brain, and I shook my head ‘no’ but mumbled, “Yeah, cum for me.”

“Oh fuck,” he grunted, thrusting hard into my second ring, “Oh fuck yeah,” he thrust again and again, harder each time, until his body finally tensed. I felt the base of his cock twitch inside my outer ring, “Oh…fuck,” Then I felt the first shot of boiling hot cum blast off deep inside me, “I’m cumming,” he thrust hard into me again as his arms wrapped tight under me, my legs around his tight waist. “Fu-ck,” he twitched, abs tightening and flexing on my spent cock; holding his hips tight to my ass, I felt his big dick jerking and twitching inside as he continued to shoot his massive load into my guts, warming me up and moaning in my ear as he drained his balls. “Oh my…fuck, Jer…ungh…so good,” he mumbled incoherently before finally, he stopped twitching inside me, and eventually, his body stopped flexing as he relaxed on me.

We lay there breathing heavily, holding each other, as he gently kissed my neck. My legs were still wrapped around his waist, his arms still under my back, holding me tight, just enjoying the after-orgasm bliss.

He slowly pushed himself up, pulling our sweaty bodies apart, my cum smeared on both our torsos. I unhooked my legs carefully and released his waist as he straightened up and very slowly started pulling his cock out of my hole until the head popped free. I saw the broken concom pushed around the base of his cock like a collar, his soft long inches shiny and slick with lube, and some of his massive load. I felt my hips relax back into their normal position as the rest of my body relaxed into the bed.

I watched as he pulled the spent condom off his cock with the familiar sound of the latex snapping. He tossed it in the trash under the nightstand. I don’t know why, but I expected him to get dressed and leave. Instead, he used the tissues to wipe off his cock, and then he wiped off my cum from his abs. He grabbed a clean tissue and cleaned up my abs. Then he lay back down on the bed beside me, taking a deep breath of pride and satisfaction.

I curled up with him, putting my head on his chest, listening to his breath and heart beating. Then, I drifted off to sleep.