Isaac - My Best Friend's Brother

***All Characters are 18+***

In the spring of 2013, I was well into my freshman year of college. My roommate, Christopher, and I got along great. We had a lot in common, and he quickly became my best friend. No, I didn’t have a crush on my roommate. He’s cool, but as a Christian from the deep south, I know being gay is a sin and have every intention of living my life in celibacy. I steer clear of porn, and the gym, don’t go to bars or places where I can lose control and put myself in a situation I don’t want to be in, I also keep my self gratification to a minimum, but I am still human.

This was working well for me until the temptation came to me the week after spring break. Staying in my dorm room, in the form of a 6’2”, 200lb Adonis named Asher. Sigh, Christopher’s older brother. He’s here for a week while his college is on spring break. Christopher thought it would be fun to have his brother around for the week, show him around, let him get to know all our friends, and me, mainly because we’ve become so close. To say Asher is a wet dream in human form would be an understatement.

I’ve never been so sexually frustrated in my life. Asher is always finding excuses to take his shirt off and show off his rippling muscles. I’m shocked at how comfortable he is hanging out in his sport briefs, which leave very little to the imagination. Not that I need to use my imagination, I’ve seen it anyway. He’s made me go to the gym with him every day this week because I have access, and he wants to work out while Christopher is in class. I made the mistake of telling him I wanted to get some muscle on my skinny frame, and he lobbed a compliment my way that made my brain flatline. I agreed to go with him so he could teach me a few things. This required me to get up every morning, work out with him, then to add fuel to the flame, we shower together, and I basically have to think of the most awful things so I don’t get an erection. It doesn’t end there, though, because we get dressed in the dorm, and he doesn’t put on more than his skimpy underwear until we are ready to head out, and it’s driving me insane.

Thankfully, he’s leaving on Sunday, so I just have to get through tonight and Saturday night, and I can go back to my everyday life with very few temptations.

“Isaac,” Asher burst through the door with Christopher in tow.

I nearly jumped out of my skin. “What?”

“Chris told me about this party tonight, and you’re coming with us,” he said.

“Oh, I don’t think so,” I pushed my glasses up on my nose and picked my book back up.

“See, I told you. It’s not his thing,” Christopher added, pulling some clothes out of his closet.

Isaac sat on the bed, grabbing my leg at the shin, “Bro, you’re coming. I’m going to be Chris’s wingman, and I’ll wing for you too. Get you both laid tonight and I’ll have a story to tell when I get back to my school,” he grinned.

I laughed at the thought. “I’m really ok, but you guys have fun.”

“Chris, what’s wrong with him? Is he depressed? Does he always stay in on a Friday night?” He asked as if I weren’t right in the room with his big hand wrapped around my leg.

I smiled. His personality is intoxicating. While I do see the similarities between him and Christopher, Asher is just sexier in every single way. “Where are you guys going?”

“It’s a house party, right, Chris?” His New York Accent was much thicker than Christopher's, and it only added to how sexy he is.

“Yeah. You know Franklin?” Christopher asked, looking at me from his closet.

“Yeah, of course,” I shrugged.

“It’s at the house he shares with the rest of the guys from his ultimate frisbee team. One of the roommates has a birthday,” he shrugged. “It should be fun,” he started to unbutton his shirt.

“See, it’s going to be fun,” Asher said, looking at me, his silver-blue eyes melting my defenses.

“Franklin’s girlfriend is inviting her sorority, or…maybe they have a rule about partying together, but either way, there’s going to be plenty of single women there,” Christopher said, tossing his button-up shirt and pulling on a different button-up that was a little more form-fitting.

“See, plenty of women. Or dudes, if you’re into that, right Chris?” Asher added, getting a chuckle from Christopher. I know he meant it as a joke, but he has no idea how right he is.

“Okay, I’ll come,” I said, against my better judgment.

“Yeah, all right, man, now it’s a party!” Asher hopped up off my bed, all excited. “Let’s find you something to wear. Chris, did you bring any of your clothes from your freshman year of high school? Isaac might fit into those,” he grinned, then turned back to me. “I’m just playin', I actually have a shirt I think you’d look great in, if you want.”

The shirt Asher had me wear was big on me. I’m 5’9”, 140lbs, but mostly skinny, so it kind of hung on me like a mannequin from the children's section, but he rolled up the sleeves and had me leave more buttons undone than I would’ve liked to show off my chest a little. I had no intention of actually getting laid, or even talking to women at this party, but being wrapped in a shirt that smelled like Asher, and having the entire night to hang out with him, had me throwing caution to the wind.

When we got to the party, Christopher introduced us to a bunch of people, and then we all ended up in the kitchen, where the snacks and drinks were.

“Oh, perfect, I’ll get us some drinks,” Asher said, heading to the crowd by the keg.

“Ok, see that girl over there in the purple dress?” Christopher leaned into my ear and nodded at a pack of women.

I scrunched my face, “That’s magenta.”

“Huh?”

“The dress, that’s not purple, it’s magenta,” I corrected.

He chuckled, “Whatever, that’s Violet.”

“It’s definitely magenta, Violet is more of a dark purple leaning towards blue,” I told him.

“Bro, her name is Violet,” he shook his head, smiling. “Anyway, I’m hoping Asher can wing her right into my pants tonight.” He grabbed his crotch instinctively, and I tried not to look at the size of the bulge.

“Mmm, ok, got it. You’re not at all worried he’s going to hook her for himself?” I asked honestly.

“Pff, no,” he scrunched up his face as if that was an impossible thought.

“What, Asher is good-looking,” I shrugged.

Christopher did a thing with his face that let me know he was trying to be nice. “Look, I love my brother, but I am not worried about him trying to steal women away from me. Besides, I’m the charming brother,” he winked at me.

I chuckled, “Oh, yeah, you’re suave. Go…”

“Here we are, gentlemen,” Asher said, coming over, holding three red Solo cups. Christopher took one, and Asher handed me the other one.

“Oh, no, that’s not…I don’t really drink,” I told him.

“Just take it. You don’t have to drink it, but you can’t be at a party looking like you’re not having fun, and this will be a good prop,” he said.

That made sense, so I took the cup.

“Alright, cheers queers,” he said, clinking his cup against ours then gulped the beer inside.

Christopher shook his head, chuckling, “Cheers,” and then took a sip.

They both looked at me. I rolled my eyes and took the tiniest sip of my drink.

“Yeah, that’s it, Isaac,” Asher said, putting his massive arm over my shoulder, pulling me into his torso.

The beer tasted like, well, what I imagine urinal water tastes like, but I continued to sip it anyway. 

Asher dragged us over to where Violet was with her friends, introducing himself as Christopher’s less attractive but more charming older brother, which got a giggle out of me. Then he spent the next twenty minutes building Christopher up in very clever, but subtle ways. I didn’t think that would work, but Violet seemed to be going for it. Then the conversation bounced between Asher, the other three women, and me, but I mostly just responded to direct questions and sipped my beer.

When my cup was empty, Asher noticed right away. “Isaac, I need a refill. Come with me?” He winked.

“I…uh, sure,” I said.

“Great, we’ll be right back,” he said to the group, putting his arm over my shoulder and walking me to the kitchen.

He dodged a bunch of people and came back with Jell-O shots, two for each of us.

“Oh, definitely not,” I smiled at him.

“Isaac, don’t be a pussy, take the shots and I’ll do them with you,” he handed me a red one and a green one. “Just do like I do,” he said, then stuck out his long tongue and used it to scoop the jello from the cup, sucking it into his mouth before it could fall out. “Ahh…yeah, wow, that’s good.”

I smiled, wishing his tongue were in my mouth. Then I felt that rush of blood heading towards my crotch and had to distract myself, quickly tonging the plastic cup and sucking the worst jello I’ve ever tasted into my mouth. “Ugh, gross,” I coughed. “That tastes like rubbing alcohol.”

Asher laughed, “Yeah, it’s not good vodka, but it’s like 100 proof.” He held up his other cup, “Cheers,” and knocked it against mine.

“Ugh, cheers,” I groaned and sucked the jellow into my mouth, trying to swallow without tasting it. “Ugh, nasty,” I groaned again.

“Here,” he said, handing me a cup, “Wash it down with this.”

I chugged the beer in the cup. The taste of the nasty beer was a thousand times better than the jello.

Asher pumped more beer into our cups from the keg. “Ok, now, we float.”

“What do you mean?” I asked, already feeling a little buzzed. A feeling I thought I would hate, but…I kind of liked it. I felt cool, invincible, and kind of sexy.

“We can’t go back over there. If Chris wants to get laid, he needs those girls to leave him with the purple dress girl, and they aren’t going to leave her alone if two studs like us show up to talk to them all night. They will leave if they realize purple dress girl is already into Chris and they only have each other to talk to,” Asher explained.

“It’s magenta,” I said with a smile, feeling woozy and giggly.

“As long as it’s on the floor next to Chris’s undies tonight, I don’t care what color it is,” Asher laughed.

The image of Asher in his underwear flashed in my head. He put his arm around my shoulder again, his manly scent wafting into my nose as he dragged me around the house, saying…Well, I don’t remember because I spent the entire time fighting an erection.

After circling the house a few times, Asher noticed the two drinks and two Jell-O shots were hitting me pretty hard. “Isaac, you’re drunk,” he chuckled.

“What, no, I’m not drunk. I’m just–very relaxed, and…” I did a move with my arms akin to doing the wave at a football game.

He smiled so big I could see most of his teeth, “Isaac…you’re drunk.”

I held my thumb and forefinger slightly apart, “Maybe just a little, shhhh, don’t tell Christopher,” I giggled.

He looked over at his brother; they seemed to have an unspoken language with each other. Even from across the room, Asher was able to tell him that he was taking me back to the dorm, and we left in an Uber.

When we got into the dorm, Asher pulled off his shirt and tossed it on Christopher’s bed. “Man, it’s so warm in here. Is it always so warm?”

I struggled to get my sneaker off, and it flew out of my hand, landing on the floor with a loud thud. “So…so hot,” I shook my head, trying not to stare at his chest, but also hoping it stops the room from spinning.

He laughed at me, “You’re so drunk, I love it. You’re adorable when you’re sober, but drunk is even funnier.”

I flung my next shoe off. “You’re adorable,” I said accusingly.

He grinned as my shoe landed next to him on the floor. “Hey, that was a compliment.”

I started unbuttoning the few remaining buttons on the shirt he loaned me. “I love this shirt.”

“Oh yeah?” He stood off the bed and unzipped his jeans, exposing his underwear, which had no waistband and looked like a Speedo with a million thin black and grey stripes.

I couldn’t help but look at his unzipped jeans, wanting to see more. “Yeah, it smells like you,” I grinned, thinking it was a clever, highbrow comment that would go over his head. It didn’t, though.

“You like that it smells like me?” He grinned, eyes focused on me.

I leaned back on my hands, shirt unbuttoned, with most of my torso exposed, “Mmm, you smell so good.”

“Isaac?” He pushed his jeans to the ground.

I drank in the sight, “Yeah?”

“Are you…gay?” He asked.

I grinned, “Shhhh, that’s our little secret.”

He chuckled, stepping out of his jeans. He crossed the room to me, planted his hands on the bed next to my hips, his sexy face an inch from mine. “Prove it.”

I didn’t know what he meant, but my heart was pounding out of my chest and my dick was already so hard in my pants it hurt. I kissed him quickly, then pulled back to see the look on his face.

“You can do better than that,” he said, slowly leaning in and pressing his sexy lips to mine. I wrapped my arms around his neck. He pulled his shirt off my shoulders, exposing my skinny body, and quickly worked my pants open. In no time, he had me naked and was between my legs, pushing me further up the bed. I ran my hands all over his body, tracing every single muscle, memorizing the touch. Even in my horny fog I knew this was a one time experience and I’d have to lock this side of myself away in the morning. I wanted to savor it.

He kissed down my chest and engulfed my rock hard 5” cut dick.

“Ungh,” I cried out, the feeling of being touched by him was incredible, but his mouth on my virgin cock was too much to handle. He worked me over like he was an expert. He spread my legs wider as he bobbed up and down on my dick, his big hands on my thighs, pressing my legs into the mattress as he spread them as wide as they would naturally go. I ran my hands through his short brown hair. “That feels so good,” I said, feeling my hips rock up into his mouth.

He sucked me for only a few minutes before pulling off, sitting up on his knees and pushing his briefs down, his dick wasn’t quite hard, but it was growing. He shimmied around as he kicked his underwear off his legs, then quickly straddled my chest to tap his dick on my lips. I was so nervous, but I wanted this so badly. I opened my mouth and tried to steady my swirling head to let him enter my mouth.

Naturally, I gagged right away, and he chuckled. “Just relax and take what you can, don’t force it.” His voice was quiet but clear. His dick in my mouth was more than I could’ve ever expected. He tasted so good, smelled so manly. I tried my best to give him an amazing blow job, but I’m sure I fell short. I reached up to stroke his abs and chest, down to his furry legs as I bobbed on the last four inches of his six and a half inch circumcised dick. Tasting every bit of his sweat and precum, I was in heaven.

He pulled his dick out of my mouth and spun around so he could push into my mouth and suck my dick at the same time. I wasn’t able to suck him very well like this, with his body weight on me, but he started humping his dick into my throat. It made me gag a bit, but I tried my best to breathe when he pulled it out. He was bending me and sucking my dick, sucking my balls, then he spread my ass cheeks and licked my hole. I moaned around his cock and he pushed it into my throat, almost making my eyes pop out of my head. All I could do was let him use my mouth as I held onto his waist and tried not to blow my load as his tongue got really deep in my hole, lighting up pleasure sensors I didn’t get when I tried to finger myself during a few masturbation sessions.

He kept doing this thing where he’d push his dick deep into my throat at the same time he’d force his tongue deep into my ass and I didn’t know if I should moan or scream but I squirmed in pleasure until he’d let me relax and breathe. He fed me his dick for a few more minutes and without warning I felt it swell and twitch before he pushed deep and fired off a massive load of cum. All I could do was swallow or choke, but more and more cum kept pumping out and filled my throat. I tried to pull off, but he just pushed deeper, grunting and burying every inch into my mouth as the last of his orgasm oozed into my throat. 

He finally gave me relief, pulling out of my mouth and letting his sloppy wet dick slide over my face. “Fuck, Isaac, that’s the best head I’ve had in a while. There’s no way you’re a virgin,” he chuckled. Then he spun himself around so his face was next to mine, his legs found their way under mine, and he wrapped mine around his waist as he leaned in to kiss me. “Mmm, I can taste myself on you,” he moaned into my mouth. I could still taste his cum, and my horny fog just had me wanting more.

He got off the bed and went over to Christopher’s dresser, digging around in his underwear drawer. He pulled something out and quickly jumped back into the bed between my legs. He popped the cap on a little plastic bottle and squirt some of it onto his fingers, then I felt his thick fingers probing my hole. He smeared the lube onto my brown pucker, but then he started sliding not one, but two fingers in, breaching my hole and pushing straight into the knuckles.

“Ahh…shit, that hurts,” I clenched my teeth and my ass, pushing on his forearm, trying to get him out of my hole. It was like having sticks shoved up my ass and I tightened up around the two fingers.

He groaned, “You’re so tight, maybe you are a virgin,” he grinned down at me. He continued to finger me while his other hand stroked my dick. When his two fingers started to push on my prostate gently, I squirmed and involuntarily moaned. We both felt my ass start to relax around his fingers. “That’s it, how’s that feel?”

I clenched the bed sheets in my fists and whispered, “So good,” as he pushed on my prostate again.

His hand left my cock and I opened my eyes to see him smearing lube on his cock. My heart started racing faster than the room was spinning. “Are you going to…” I tried to think of a less crass word.

“Say it,” he insisted.

“Are you going to fuck me?”

“Do you want me to fuck you?” He pushed on my prostate again.

“Ungh,” I groaned and nodded quickly. "Do you have a condom?"

"No" he replied, pulling his fingers from my hole and lining up his slick dick.

"Mmmm," I felt his head make contact with my tight hole. He didn’t push in, but he was teasing it, smearing more lube between us. “Does Christopher have any?” I asked, a desperation in my voice.

“I didn’t see any when I got the lube. Do you have any?” He asked.

“I…mmmm…no, I wasn’t planning to have sex,” I felt his head poking at my hole. “We can’t have sex without a condom,” I said.

"That’s ok," he said gently. "Just let me poke the head in for a second." 

“Ah,” he poked it in with minimal effort. There was a quick, sharp sting that dissipated quickly. The spongy head was so much better than his rigid fingers, I couldn’t help but let out a low hum of pleasure.

"See, not so bad," he said. I reached up and touched his well defined chest and traced down his abs to feel him flex under my hand as his dick kept poking ever so slightly deeper and deeper with every flex of his abs. 

I realized he had a couple of inches in me when he hit resistance from my tight anus. I groaned as the stretching became really painful. “Ahhh, shit, wait,” I pushed on his abs. He leaned in and made out with me frantically. I could feel my heart beating like crazy. His raw dick pushed deeper and deeper into my ass and I closed my eyes trying to steady the spinning of the room and trying not to focus on the pain of being stretched open for the first time. I broke our kiss when it started to really hurt, and that pang crawled deep inside my guts. I struggled and groaned through clenched teeth, "Oh fuck, take it out man. It hurts too much. Pleeeassse take it out." 

“Mmm, you’re ok, Isaac. I’m almost all the way in; if I take it out now, it’s going to hurt even more. I’ll take it out in a minute when I feel your hole relax, ok?”

I hissed and groaned, nodding as I pushed on his tight abs to try and keep him from going deeper into me. He stayed still with what felt like a huge cock lodged a couple inches inside me. I closed my eyes and tried to breathe, tried to will my ass to loosen up. Then he rocked his hips and I groaned, “Oh fuck, Asher, please, it really hurts, just pull it out,” I almost begged.

“I’ll pull out when you relax, I promise,” he insisted, holding himself inside me. “Just take a deep breath and relax.” He reached for my dick and started stroking me.

I took several deep breaths and felt the pain start to subside slowly. Not gone, just ever so slightly less. I could feel my ass begin to loosen up around his dick. He must have felt it too because his hips began to gently rock, not really thrusting, but his cock was moving inside me, but not going deeper either. It was starting to feel better; it still felt painful, but nothing like when he first pushed in.

He rocked his hips inside me like that for a minute while stroking my dick, then he reached for the lube and added more, gently rocking it into my ass as his rocking turned into small thrusts.

"Mmm…ok, we should stop," I said, feeling my ass start to give over to his cock. 

“I just want to work this lube into you first,” he said, squirting more onto his exposed dick and gently pushing it into me. His next thrust went even deeper and I felt his cock head stretching new depths in my ass.

"Ow, ahhh, ow, shit, Asher, ungh…this hurts so bad, ungh, you're going deeper." I groaned as the sting plunged deeper into my guts. He lay on top of me with his face buried in my neck and rocked his hips deeper into me. He started to kiss my neck, and I groaned under his weight. My legs spread wider as his cock sank deeper inside me.

“Your ass feels so good, I haven’t fucked a tight hole in so long,” he kissed me again.

“Ungh, I can’t handle anymore, it’s too much,” I groaned as he hunched up into me.

“It feels so good, Isaac, I need this,” he hunched up deeper into me.

“Ungh, shit,” I groaned, feeling his pipe sliding in and out of my chute.

He was breathing heavily in my ear, and I started to get worried about him being in me bareback. "Wait, stop," I groaned.

"Shhhhhh," he said gently as he continued to thrust. "You feel so good. Let me fuck you a little longer,” he said as he pumped into me and I felt his cock hit my prostate.

“Mmmm…ungh,” I groaned. The head of his bare dick pegged my prostate again, flipping the switch from painful to pleasurable instantly. “Wait, Asher, we should really have a condom," I muttered. 

"Don’t worry, I don’t have anything,” he huffed into my ear before kissing me and thrusting deeper into me.

I realized my hips were rocking to meet his thrusts, trying to get his cock to hit my prostate again. “Ok, ungh" I groaned, holding him tight as his weight held us both in place and fucked me deeper into the mattress.

He groaned and started to piston his dick in and out of my hole. “You feel so good,” he moaned in my ear, holding me tighter. He was hitting my prostate at a much faster speed now, and my eyes rolled back into my head as the intensity built up. I wrapped my legs around him and felt my dick leaking precum between us.

I moaned in his ear, “That feels so good.”

He sat up quickly, his hips not skipping a beat as he pushed my legs up and out to the side, making it even easier for him to hit my prostate. Holding my legs under my knees he looked down and thrust harder into my ass. I grabbed my dick and started jerking off. My right hand pounding my dick as my left hand drifted below my balls to feel his hard dick sliding in and out of my hole. I watched his face, euphoric in pleasure as his mouth hung open, the lust in his eyes, and the sounds he was making as he relished my hole. I felt my balls tighten up and I tried to warn him, but the thrusting into my prostate forced my orgasm out so quickly and with so much intensity I was only able to mumble, “ungh, cumming,” as the first shot fired out. He increased his thrusting as the next few shots of cum spurt out onto my chest. “Ahh…mmmm…ungh,” I groaned and moaned as my body trembled under the pleasure of him pounding into me.

“Oh yeah, that’s it Isaac,” he moaned, as his thrusting increased in intensity and my ass clamped down on his cock.

“Ahhh, shit,” I groaned, releasing my dick from my death grip.

He put my legs on his shoulders, leaning into me and slamming his hips into my ass. “I’m so close,” he moaned.

“Ungh, ahhh,” I hissed, the incredible pleasure from ten seconds ago was quickly turning into a similar pain from when he first thrust into me. “Asher, ungh…it hurts, you gotta stop,” I groaned.

He huffed and took one last thrust, burying his dick deep inside me, holding himself balls deep. "Isaac, I'm so close to cumming, just give me a few more minutes?” He huffed, sweaty, all of his muscles straining, “You're so hot, and your hole is the tightest I've ever had, just a couple minutes?" The pleading in his voice made me feel bad.

“Just a few more minutes, then you gotta pull out if you can’t cum,” I told him.

He nodded, pulled most of the way out, added more lube, and slowly re-entered my hole. The lube cooled the burning sensation and I felt his cock pushing on my prostate again. We both moaned. He quickly ramped back up to a deep fucking, pushing my legs up towards my head, putting all his weight on me, I could barely breathe as he worked himself into a frenzy. He kissed me between my legs, muttering about how good my hole felt wrapped around his dick and his forehead dropped onto mine. I rubbed his back, sliding my hands down to his ass to feel him thrusting into me. “I’m so close, Isaac, ungh, I’m cumming,” he hunched up into me hard, then one more hard thrust, “ungh…mmmm,” he groaned and I felt his dick spasm inside me, a wetness and heat spilling around his shaft as he groaned on top of me.

“Shit, did you cum in me?” I was barely able to squeak out with his weight on me.

He nodded his head, biting his lip as he continued to twitch inside me and hum.

I lay under him, the room spinning, the gravity of what just happened quickly settled in as I caught my breath.

He slowly pushed himself up and pulled his softening dick out of my hole. “Mmm,” he moaned as the head popped out, and my hole closed shut like a blast door. “That was…amazing,” he smiled at me. “That’s the best ass I’ve had in months,” he insisted.

I didn’t know how to take that, but I forced a smile.

He got up off the bed, grabbed my underwear to wipe off his dick, then wiped my cum off my stomach and dick and tossed them toward my clothes basket. He pulled on his underwear and got into Christopher's bed. “I’m so tired,” he said.

I got up to pull on some clean underwear. “Are you going to sleep in Christopher's bed?”

“Mmmhmmm,” he mumbled, pulling the covers over his body.

“What about your brother?” I asked, snapping the waistband of my BVDs.

“He’s probably fucking that girl in the purple dress, he’s not coming back tonight,” he groaned. “Can you kill the light?”

I flicked off the light, then put the bottle of lube back into Christopher's top drawer. I lay in bed for a few minutes, trying to ignore the sweaty warmth of my sheets as the room spun faster and faster until I fell asleep.