Max - A Long Time Cumming

***All Characters are 18+***

Gabe and I met in 5th grade when his family moved into the neighborhood. The teacher sat him next to me in class, and we quickly became best friends. Our parents signed us up for Little League together, so we were always together. Between school, sports, and regular sleepovers, we basically had no choice but to be best friends or enemies, so I’m glad it worked out the way it did.

Puberty struck in sixth grade for both of us. Gabe shot up about a foot; I did not. He got shy, and I became the “funny one.” Sleepovers were more fun because we were able to laugh all night, eat nothing but Doritos, drink Mountain Dew, and talk about the changes our bodies were going through and how sexually frustrated we were. At that age, though, it was mostly sharing stories about the girls who might have flirted with us and how often we jerked off and supposedly had wet dreams. I might have embellished a bit because he said he had one every other night.

By 7th grade, we had gone to our first makeout party, where we both had our first boy/girl kiss. Then back at my place, we talked about it for hours and shared how horny we were. That was the night we jerked off together for the first time. It was under the covers in the same bed, and we couldn’t see anything except the covers popping up and down as we stroked ourselves. Looking back, I realize it is silly because we had a few “I’ll show you mine if you show me yours” moments over the last few years, so there wasn’t anything to be shy about, but Gabe was very shy. I guess we hadn’t seen each other orgasm, so that was a reason to be timid. That became a regular thing at sleepovers throughout the rest of the year.

The summer going into 8th grade, it was super hot, and we decided to ditch the covers; that was when I saw his dick throw up for the first time, and it made me cum pretty quickly. By the end of that summer, we had progressed to jerking each other off; that was awesome and became the new thing we did at every sleepover.

In 9th grade, we went to our first high school party thrown by the seniors on the baseball team, so even though we were freshmen, we were still on the team and, by default, invited to the party. There was a keg, and we drank our first beers that night, followed by a few more, and managed to get pretty shitfaced. He only lived a few streets away so we crashed at his place that night. We stripped down to our tighty whities and climbed into bed, trying not to wake anyone else in his house. Of course, we started talking about girls and what we had hoped would happen that night.

“I was with Christina all night, and you know her reputation,” he laughed.

“Yeah, I heard Steven in the locker room saying she gave him blow jobs all the time,” I had a twinge of jealousy in my voice. “I saw you making out with her at one point; I figured you’d make it to a bedroom before the night was out,” I admitted.

“Nope, no such luck, she just gave me blue-balls,” He laughed.

“Aww, poor baby,” I joked, casually cupping his balls from outside his underwear like it was a bump on the head.

“Fuck you, dude,” he quipped, shoving my hand away.

“You’d like that, wouldn’t you,” I joked.

“Well…if you’re offering,” he laughed, jumping on me and pretending to hump me basket to basket, pinning my arms down as he dramatically rubbed our hardening packages together.

I struggled, trying to push him off and laughing, “I’ll jerk you off, but I’m not having sex with you!”

He pulled down his briefs, his hard dick flew out, “you know, a good friend would give me a blow job for my pain,” He tried to hide his smile as he said it.

I laughed, grabbed his dick, and started jerking him, I was pretty drunk, and in my head, I thought it would be funny, so I popped his dick in my mouth like a popsicle and gave him one suck, and popped it back out, “There, I sucked it,” I laughed hysterically.

He laughed, “Oh man, I can’t believe you did that,” he laughed, slowly stroking his dick and hopping off of my lap.

I lay next to him, pulled my briefs off, and tossed them at him, “what can I say? I’m a good friend,” I mocked.

“Fuck you, Max, I’m an awesome friend,” he got defensive.

I lay on my back, my hard dick in my hand, “Prove it,” I smiled and cocked an eyebrow up.

“Are you serious?” He squinted.

“Why not?” I shrugged.

He smiled, shaking his head, “fuck it,” and put my dick in his mouth.

Oh wow, a warm, wet mouth is the most amazing feeling in the world! He didn’t stop with one bob of his head, though; he went for it. Making all kinds of noises as he did; it was so hot I didn’t last long at all.

“Gabe…I’m gonna cum,” I whispered; he popped his head off my dick and gave it a couple strokes, making me shoot my load on his hand and my abs. My body quivered under his touch until he finally released me and flung the cum off his hand onto my stomach.

I did my best to return the favor, though I can’t imagine it was any good because I kept panicking that he was going to cum in my mouth, and when he would let out a soft moan or breathe heavily, I would pop my head off his dick to make sure he wasn’t cumming. It still didn’t take him long to cum, and he shot pretty hard, most of it landing on his chest and some getting on my hand.

That experience was often joked about, but we only repeated it when we returned from parties where we had drinks. The status quo was just to jerk each other off quickly and go to sleep.

I got a girlfriend in 10th grade that lasted through senior year, so our jerk-off sessions were much more rare.

She broke up with me just before graduation because we were going to different colleges, and she didn’t think we should be “tied down.” Whatever that means. I’ll admit I was pretty broken up about it, but I did the manly thing and buried my feelings into working out and playing video games.

Gabe and I didn’t get to really talk much over the next few weeks. His mom took him on a trip to visit family in Miami for the first three weeks of the summer. He ended up staying for an extra two weeks to help his uncle with his day cruise business because it was the busy season, and Gabe was having fun helping. I didn’t get many details, but it was basically tourists getting on a sailboat and drinking for a couple of hours while Gabe, his uncle, and a few others sailed them out into the ocean, turned around, and dropped them back off where they started by the end of the day.

It wasn’t until the middle of July that I saw Gabe in person again. We were at a mutual friend’s going away party. He was leaving for college early. It took most of the night before I was able to get Gabe alone to catch up.

We had both had a few cans of beer by that point. I couldn’t help but notice how working on a boat did him well. He lost the last of his baby fat and got pretty lean and tan; his hair grew out and was just a couple of inches above his shoulders, and he had blonde highlights in his curls from the sun.

He told me he made a boatload of money in tips and how he even had a summer fling with one of the customers twice his age.

“No shit, did you lose your virginity?” I asked.

“No, we fooled around a little, nothing wild, but I was too nervous and didn’t let it happen,” he took a swig of his beer. “What about you? Did you and Courtney finally seal the deal?”

I laughed, “Wait, didn’t I tell you we broke up?”

“Oh, you know what, you did,” he laughed, “Sorry, the sun kinda melted my brain out there. So, still a virgin?” he smiled.

“Yup, you?” I smiled.

“Yup,” he laughed, looking more shy than ever.

I couldn’t explain it at the moment, but I felt nervous around him, almost like we had just met for the first time. His body language didn’t help. He kept crossing his arms and breaking eye contact the way he would when girls at school flirted with him. It was part of his charm, but he never did that with me.

We continued drinking for a while, but he got pulled away by one of the freshmen who needed a beer-pong partner. I got sucked into a debate about who was the hotter cartoon character, Jessica Rabbit or Babs Bunny, in the Space Jam movie we all went to see as a team over the Christmas Break.

Somewhere around 1:00 am, a slightly drunk Gabe came and put his arm over my shoulder. He had more than six inches of height on me since I never got taller than 5’6”. I looked up to meet his eyes and scooped my arm around his waist to hold him up, making my best Pauly Shore impression, “What’s up buuuuddy, you ok?”

“Yeah, just ready to go home; you coming?” he slurred a little.

I laughed, “I guess I am.” I looked at the two girls I was talking to. “Ladies, good luck at NYU. Hopefully, I'll see you before the summer is out.” I lifted my beer, clinked theirs, and chugged quickly.

We walked back to his place, sprinting at one point, but we were a little too drunk to run and stumbled a few times. We cut through a series of trails connecting our cookie-cutter neighborhood development and then did a terrible job climbing the privacy fence in his parent's backyard, nearly breaking it…again.

He was laughing at me because I fell in some mud.

“Shh, dude, you’re going to wake your parents.”

“You shh,” he bopped me on the nose with his finger and put his arm around my shoulder again as we staggered to the back door.

I grabbed the knob, “It’s locked, where’s your keys?”

“In my pocket,” he smirked.

I rolled my eyes, and I stuck my hand into his pocket, feeling the heat coming off his groin as I did; no keys, though. The other pocket is next.

“Oh yeah, get a little deeper,” he joked, rolling his hips to get my hand to push into his package through the pocket as I clutched his keys and pulled them out, trying not to laugh at him as I unlocked the door, and we stumbled into his family's kitchen. I slipped off my sneakers and told him to do the same. Then I took off my muddy jeans, stripping to my briefs.

“What are you doing?” he asked.

“I have mud on my pants,” I stage whispered and laughed at him.

“Oh,” he smirked, then ran up the stairs to his room.

I took off my shirt with mud on it, leaving my muddy clothes by the door, locked it, and ran up the stairs to Gabe’s room in just my tighty whities.

He was on the bed and had already stripped down to his underwear, laying in the middle of the bed and groping himself from the outside of his briefs.

I puffed out air and closed the door, “what are you doing?”

“I’m horny,” he smiled with half-lidded eyes.

My eyebrows raised, “And?” I walked over to the bed, feeling myself getting hard, knowing we were going to jerk each other off.

“Come on, man, we haven’t jerked off in such a long time,” he stuck his hand inside his briefs, groping his dick.

“Speak for yourself; I jerked off last night,” I smirked.

He tossed his head to the side, “You know what I mean.”

I chuckled, climbed on the bed beside him, and lay down, my hip inches from his. Our legs touched, the warmth of his body radiating on me, his familiar scent filling my lungs and getting my heart racing like a drug I’d kicked in a 12-step program. The beer was really hitting me. I skipped our usual non-foreplay foreplay of getting ourselves hard in our underwear, then taking it out and stroking ourselves until we eventually stroke each other. I lifted my ass and whipped my briefs down and off onto the floor. He followed suit and started rubbing his dick.

We lay there stroking in silence for a few minutes, his legs stretching and flexing into mine as he edged himself closer to orgasm.

“You want to try something I learned on the boat?” He whispered.

“Uh, sure,” I said hesitantly, unsure what he might have learned.

“Here, come sit on my legs,” he said, tapping his naked thighs like he was calling a puppy.

I chuckled, “You want me to sit on your lap?”

“Yeah, I’m too big to sit on yours,” he laughed.

I shook my head, sat up, threw a leg over his, and sat on his upper thighs.

He grabbed my waist, pulling me forward, “scoot closer,” he said.

I lifted my ass and scooted closer until his hands stopped pulling and sat back down. Our balls were touching, our cocks perfectly lined up with each other. “Like this?”

“Yeah,” he breathed heavily, still holding my hips.

“Now what?” I asked.

He grabbed both our dicks and started jerking them together; a rush went through my body as he did. He looked up at me as I squirmed under his grip.

“Oh shit, that does feel good,” I admitted as I rocked my hips on his legs, thrusting up into his hand as he jerked us.

“Yeah, it does,” he whispered in a husky voice I had never heard from him before. He reached up with his free hand and stroked my abs like he was counting each one individually, slowly bringing his hand down to my pubes. I let out a soft moan and leaned back on my hands. His fingers rested on my bush, but his thumb circled under my balls and put pressure on my taint, and it sent me over the edge.

“Oh fuck,” I felt my sphincter tighten and an amazing tingle inside me that triggered my balls to tighten. “I’m gonna cum,” I whispered.

“Do it,” I felt his hips gently thrusting up as he jerked us tighter.

His dick pulsed against mine, and I blew my load with a moan that I couldn’t hold back, shooting cum all over his chest, pooling in the valleys of his abs and his new cum gutters, just completely coating him. The last drizzle pooled on his pumping fist, lubing our cocks as he continued to push himself to orgasm. After a few more pumps, I nearly screamed from the overstimulation of his hand on my cock, wreathing on top of him since he didn’t let go, using my cum for lube, until I felt his balls pull up tight under mine as his ass pushed up, lifting me off the bed, his cock twitched, his abs flexed, his face scrunched, and he shot his load all over his chest and abs, mixing his cum with mine.

I fell back between his legs once he released my dick. Panting, I rubbed my face, “holy shit, that was intense,” I muttered.

He was breathing heavily, “oh man, that’s a lot of cum,” he chuckled, swirling his finger through the puddle.

I sat up on my elbows, looking down my torso over my limp dick to see he was coated and looking at me. He scooped some up on a finger.

“You want to taste it?” he smiled, wagging his eyebrows at me.

I grinned, “fuck no, all yours,” I joked but watched just in case he did.

To my surprise, he took his cum coated finger and put it in his mouth without hesitation and swallowed, licking it clean. It blew my mind. I didn’t know if I should razz him or what, but I just fell back on his hairy legs and rubbed my face. It hit me that we were both drunk, and this just got out of hand, so I chuckled and took a minute to enjoy being close to him again before I got off him clumsily, almost kicking him in the head as I rolled off him and stood up.

My legs were oddly wobbly; I guess I’d never stretched like that before. I grabbed my underwear and pulled them back on with a snap of the elastic waistband. I grabbed his briefs and tossed them to him; he immediately used them to wipe up the cum off his body and then, with impressive accuracy, threw them into the hamper in the far corner of the room. We went to sleep almost minutes later. He slept nude, me in my underwear.

I woke up to him cuddling me, which wasn’t uncommon for our sleepovers, but this time he was nude, so I felt his morning wood pushing against my ass. I pushed him off me and got up to shower; nursing my hangover, I took a long, hot shower.

We didn’t get a chance to jerk off together again that summer. We went to different colleges in the fall.

****************

The first semester of college was rough for me; my course load was much heavier than I expected, and I wasn't enjoying college like the movies suggested I would. I thought it would be all parties and sex and occasionally doing classes and homework. Nope, it was not fun. I was invited to parties but could only go to the first mixer, and then I was one of those guys in the library studying until finals.

I didn’t get laid at all. I was barely able to jerk off because my roommate always seemed to be there, and the shower situation was awful. Because I had early morning classes, I always hit the morning shower rush, and you had to be military quick before one of the other guys was rushing you. So I found time about once a week if I was lucky, and only because my roommate was out with his study group, and I’d rub one out in about 90 seconds just to relieve the stress. It kinda made me chuckle because Gabe used to say, “A forced jerk is no jerk at all,”

Winter break was better; I was back home and able to jerk off every night, but it felt more like I was trying to catch up on lost orgasms than it felt like fun.

Gabe had gone with the family to Miami for most of the winter break, so we only got to catch up for a couple of hours with some of the other guys from our former baseball team when we went out for pizza. We did promise to catch up online, though. A new chat platform called AOL Instant Messenger had just come out. I talked him into signing on when he was in the library at college so we could chat since he didn’t have his own computer. My parents had surprised me with a PC as a gift when they dropped me off at Cornell, so I had told him I would be online most nights and we could chat.

Alas, it almost never worked out that we were online at the same time, but once in a while, I would sign on just as he was going offline, or he would sign on just as I was heading out. But we were able to maintain the occasional conversation to make sure the other was doing well.

Summer break of ‘98 was the first time we were able to really reconnect. He spent the first 5 weeks of summer on his uncle's yacht again, showing back up in town near the end of July. I didn’t even know he was back in town but was at a bonfire party at a friend's place on the far end of the neighborhood. I hadn’t been able to party in a long time; most of the summer was spent with my parents parading me around to their friends BBQ’s where they introduced me as their college son, and I would tell them my classes and “what I intend to major in,” and wasn’t allowed to drink or enjoy myself. So I hit this party hard.

I had already drank a six-pack on my own and was playing truth or dare with a couple of townies.

“Max, truth or dare,” my ex-girlfriend asked.

“Dare,” I grinned at her.

“I dare you to strip down to your underwear and run around the block,” she giggled and took a sip of the beer she had been nursing all night.

I jumped up, “Time me,” I said to the nerd to my right, who I hadn’t met before tonight, stripping off my clothes and putting them in my chair. I slipped my sneakers back on and took off through the gate and down the driveway wearing just a pair of white briefs. I ran fast down the block and turned left, faster down this block. I hadn’t run this much since I stopped playing baseball, but it felt good. I eventually made it back to the driveway and jumped the gate, clearing it with an impressive height and back to the circle where someone sat in my seat.

It was Gabe; he stood up, looked at me, and smiled, “oh shit, Max,” he opened his arms for a hug.

“Gabe, when did you get back,” I hugged him, lingering in my best friend's familiar and comfortable arms.

“Just yesterday,” he looked me up and down, pausing to find the right words before just laughing and blurting out, “Where are your clothes, man?”

“You were sitting on them,” I laughed, pointing at the Adirondack chair. He laughed, and I pulled my shorts back on, leaving my shirt off because it was hot and I had just run a quarter mile.

He was wearing a tank top cut low on the sides, offering a flash of his abs and tight pecs. I couldn’t help but stare. I stayed in shape, but it was more skinny than shredded like him. We shared the wooden chair. He sat on the seat, and I sat between his legs. His legs rubbing against mine gave me flashbacks to when we would jerk off together, and it took a lot for me to focus on the game. I don’t know why; maybe it was the lack of sexual experience in college, indeed the lack of personal masturbation time, but I couldn’t help but think about the last time we jerked off together the previous summer and how good it felt when I had that intense orgasm. An orgasm I’ve been chasing ever since.

“Tanya, truth or dare,” I asked.

“Truth…no dare,” she took a swig of her drink.

“I dare you…” I looked around the circle, “to kiss Gabe,” I grinned and elbowed him.

Everyone cheered. She took another swig of beer, then stood dramatically and did the most exaggerated sexy walk over to Gabe, leaned over at the waist so her ass popped out, and she gave him a long hard kiss with her tongue. Everyone hotted and hollered as she curtsied, walked back to her seat, and sipped her drink.

“Ok, Gabe,” Tonya cocked her head, licking his taste off her lips, “Truth or dare?”

He took a sip of beer, “ah, um, truth,” he got shy.

“Tell us about your most recent sexual conquest,” she grinned, staring him down as everyone cheered her on.

Gabe got shy, took a sip of his drink, went to speak, and then took another sip, “changed my mind, dare,” he grinned.

“No, he has to do a double dare,” Tim, the former pitcher for our baseball team, chimed in, and everyone grumbled in agreement.

“He should have to get naked,” Frankie, the current catcher for our former team, shouted out.

“I dare you,” she started, looking around the circle, “To kiss…” her finger pointed from one person to the next, “Max,” everyone oohed; she cocked her head to the other side, “with tongue,” then she took a swig of her beer.

“Yes!” Tim fists the air and then high-fives Frankie.

I shook my head no and took a sip of my beer. “Why am I being dragged into this?” I shrugged and felt Gabe's legs tighten around my waist. He chugged his beer, set it down, and put his right arm over my shoulder, pulling me back toward him as his left hand came around my waist rubbing my abs, and he pulled me until I lost my balance and couldn’t resist falling onto him.

I raised my eyebrows, unsure what he was doing. I felt his right hand come up and fist the hair on the top of my head, and to my shock, he pulled my head back, and his lips came down hard on mine. His tongue parted my lips and started to explore my mouth. Time seemed to freeze, and I instinctively kissed him back and let out a soft moan. The kiss blew my mind for the next five seconds, and then he let me go, and the sound of people cheering filled my ears.

He leaned down, grabbed my beer, and chugged it until it was empty. I sat there in shock until he handed me the empty cup.

“Ok,” Gabe started to say, looking around for his next victim.

The game went on for a few more rounds; Gabe got up to get another drink and then disappeared for a while.

About an hour later, I found him cornered in the house by a girl we went to high school with. She was definitely trying to get some from him. I waved at him and mouthed that I was heading out.

I was halfway down the driveway when I heard heavy footsteps running up behind me, and then a big arm came around my shoulders; the familiar scent of Gabe surrounded me, “you were just going to leave me there with Regina?”

“Well, it looked like you were about to get a room, and I’m no cock block,” I joked.

“She wishes,” He laughed, which made me laugh.

We walked for a while toward both our homes. For the first few streets, we talked about nothing, but then things took a turn.

“So, do you have a girlfriend at Cornell?” He asked.

I scoffed, “I don’t even have time to masturbate,” I joked.

He laughed, “Oh shit, that bad?”

“You have no idea, and my roommate suuuucks,” I laughed.

“Sucks like…when you sucked me off back in school?” He bumped into me.

“God,” I laughed. “I wish, no, he’s no fun…at all,” I laughed again. It got me thinking about the last time we got off together. “Have you been dating anyone at UNC?”

“No, well, there was someone for a little while, but that’s long over,” he shrugged.

“Oh, sorry,” I nudged him. “What about the boat? Did you get your dick wet” I joked, referencing a conversation we had last summer about how life on a boat had him wet all the time and how he was worried his dick would shrivel up and fall off.

“I mean… I’ve had my fair share of fun on and off the boat,” he laughed. “Miami is filled with people looking for summer fun.” He put his arm back around my shoulders, pulling me in tighter to him.

“Dang, your ugly ass got someone to punch your V-card, huh?” I looked up at him as we walked.

He laughed, “Wait, are you still a virgin?”

I shrugged, “Man, not for a lack of trying.”

He laughed, and we came up on his street where his house was three down on the left. “Do you want to stay at my place...like old times?”

It was definitely the alcohol in my system, but what I heard was, “Do you want to come jerk off like old times?”

“Yeah, ok,” I shrugged.

We stumbled into his bedroom, hopefully not waking up anyone living there.

Stripping down to my underwear for the second time tonight, I watched as he stripped. I noticed how his muscles had developed and how even his underwear hugged his body more. I caught myself biting my lower lip and forced myself to stop.

I jumped into his bed dramatically, belly-flopping onto the mattress and spreading like a starfish to take up all the space. I inhaled, and my lungs were filled with his scent and other familiar smells from all the nights we slept in that bed; it was calming and somewhat of an aphrodisiac. He climbed on the bed and lay on top of me; I felt his bulge on my ass and started to get turned on, which made me laugh, but it came out as a long, drawn-out hum.

“Well, if you’re going to take up the whole bed, I’m sleeping on top of you,” he stretched out on me, his body completely covering mine. It felt good until I felt his semi between my ass cheeks, and I instinctively pushed my ass up hard to push him off me. Making us both laugh.

We adjust ourselves, getting into the same positions we would sleep in back in school. His leg brushed against mine, and my dick got instantly hard.

“You’re hard,” he said, pointing at my crotch, my dick snaking up the leg of my briefs.

“Ha, yeah, like Pavlov's dog, I guess. When I lay in this bed like this…I guess my dick just assumes we’re going to jerk off,” I smiled and rubbed the front of my underwear.

“Yeah, I know what you mean,” he slid his hand down his abs into his underwear and groped himself. “There’s no reason we can’t… I mean, the last time we jerked off together was a lot of fun,” he whispered as his hand worked on his dick in his briefs.

My heart started beating fast; I had been chasing that orgasm for a year; it was like a drug I only got once for free as a tease. I tried to play it cool, “if you want, yeah.”

He quickly stripped his underwear off, and I watched his dick flop out in all its glory. It was a solid 7” cut, twice as thick as my 5.5” cut dick. I followed suit, stripping off quickly, my dick so hard you could cut diamonds with it. I lay back and started to stroke my dick slowly.

“Do you want to do it… like last time?” he asked shyly.

My heart started beating faster, still trying to play it cool, but I think the alcohol was really driving me, “yeah, that was fun,” I said and quickly straddled his thighs again.

He grabbed me by the hips again; this time, his muscles flexed, and he was able to slide me forward without my help. The feeling of his strong hands gripping me made me even more horny. I hadn’t been touched by anyone sexually since the last time we did this, and I needed it. He gripped both our dicks and slowly started stroking us.

“Wait,” he whispered, reaching over to the old wooden file cabinet he used as a nightstand, pulling out a tube of lube and squirting it on our dicks, and then set the lube next to us and started stroking our dicks together. The feeling was incredible; I couldn’t help but moan. “Feels good, right?”

“Oh yeah,” I rocked my hips into his fist, leaning back on my hands, gripping his hairy thighs.

I felt his hand rub my abs, sliding down to my now trimmed pubes, and his thumb circled my cock to massage my grundle again, and I moaned a little louder from the pleasure.

“Shhh,” he hissed.

“Sorry, it feels so good,” I groaned.

“Yeah?” he circled his thumb a little deeper, and it rubbed on my asshole, “right there?”

“Mmm yeah,” I groaned, taking a deep breath, and rocked my hips up to meet his hand on my dick but also instinctively let him play with my hole. I had never even played with it myself but fuck did it feel good. That gentle pressure on my hole somehow shot like lightning up into my body, tingling my insides in a way that already had my balls pulling up tight to my body. I wasn’t going to last long, and I think he knew it because he slowed his hand that was pumping our dicks but added more pressure with his thumb down between my ass cheeks.

He quickly withdrew his hand and spit on it and then reached behind me and under my ass. His wet middle finger slid across my hole, circling it and then gently pushing in.

“Oh shit,” I groaned; this felt good…but weird. I was so horny, though; I just wanted him to get me off and let him continue without question and just trusted that he would take care of me.

He didn’t say anything; he just pushed his middle finger deeper into my hole until it was completely inside me, and he started to wiggle it.

I couldn’t help but moan. “Mmm, fuck Gabe, what are you doing to me?” I arched my back even more, rocking my hips more dramatically so they came up so he had even better access. I didn’t know I was this flexible, my knees completely bent under me, my elbows holding up my torso, my body stretched over his.

“Something I learned at UNC,” he whispered, “do you like it?”

“Ungh, yeah, man,” I admit.

“Let’s try something else I learned,” he said, pulling his finger from my ass. He grabbed more lube and stroked his dick, leaving mine alone.

I dropped my hips back to his thighs and sat back up on my haunches. He dropped his dick and grabbed me by my ass and hips, lifting me up and over his dick. I wasn’t sure what we were doing, but I was going along. I was sitting on his lower abs now, his pubes tickled my balls, and he thumped his dick on the top of the crack of my ass.

I looked down at him; he was smiling, staring up at me. He grabbed my ass with his left hand and gently pulled to lift me. I helped by getting up on my knees, my balls dangling on the muscular adonis belt he developed on the boat, his happy trial tickling my nuts.

“Spread your legs a little,” he said, and I did. “A little more,” I was almost doing a split, straddling him, stretching muscles I didn’t know were tight. His hand let go of my ass cheek, and he spit on it, then reached around and rubbed the spit on my hole. “Jerk off,” he said, “Slowly,” and he rubbed two spit-covered fingers on my hole and gently pushed in.

“OH fuck,” I groaned as his fingers played with my sphincter, then pushed a little deeper. Thanks to the alcohol speeding through my bloodstream, I was able to relax into it and felt him pushing on my prostate. “Oh…fuuuck,” I groaned in a lower register.

He smiled and kept playing with my hole, going deeper and deeper, wiggling his fingers aggressively. I started to stroke myself faster as I rocked my ass on his digits.

“Slower, don’t cum yet,” he whispered, and I did as I was told. “You like my fingers in your ass?” He asked in a hushed tone.

I didn’t know the right answer, but yeah, I did. “Uh-huh,” I breathed heavily, rocking my hips to get his fingers deeper inside me.

“Good,” he continued for another minute. Then he slowly pulled them out, added lube, and gently reinserted them.

“Oh fuck, that…that…fuck, that feels good,” I rocked my hips on his fingers, ignoring my dick.

He slowly pulled his fingers out and started stroking his dick under me. He put a hand on my hip and pushed me back gently until I felt it; the head of his lubed cock slid up my crack and stopped right at my hole. The slick dick felt both soft and hard in my crack, even better than his rigid fingers. I heard myself let out a soft moan, and it shocked me back to reality. What the fuck was I doing? He rocked his hips up, and his dick pressed up into my hole; the head popped in effortlessly, and I moaned from the feeling of my outer ring being penetrated, but then it sank too far in, and I sat up quickly on my knees.

“Ah, fuck,” I hissed.

“Shhh, Max, just relax,” his hands on both my hips, pulling me back down onto his dick.

I don’t know what came over me, but I just went with it, slowly lowering myself back down until the tip of his cock hit my hole. He gently rocked his hips up, and the head popped into my hole, and he moaned; it was the sexiest sound he had made in our entire friendship. This low rumble of pleasure. He pushed my hips gently, and I sank slowly on his dick as much as I could before it became too much about halfway down but fuck…the inches that were inside me felt amazing. I leaned forward, laying my head on his chest, the trimmed hair on his pecs tickling my cheek, and I could hear his heart beating faster than my own. He wrapped his arms around my back, hugging me, then slowly slid his hands back down to my hips, hooking his thumbs around me and pushing me further down as he gently rocked his hips up, pushing his dick deeper into my hole.

“Ah…shit, Gabe,” I gasped for air.

“Just relax; this is happening,” he whispered, still pushing my hips down, and I kept slowly sinking on his dick until I felt my cheeks resting on his lap. “That’s it, fuck Max,” he panted. “I need this ass so bad,” he whispered to me, rocking his hips so his dick pulled out just a fraction of an inch and then pushed back in deeper than before.

I slowly sat up, taking a deep breath and impaling myself with the remaining inch of his massive cock as I set all my weight on his dick. He flexed his dick and rocked his hips up into me, and hit a little deeper.

“Mmm…fuuuuck,” I groaned, putting my hands on his lower abs and feeling his muscles on my fingers. “Fuck…Gabe,” I let my head fall back, trying to catch my breath.

“Mmm…Max,” he moaned, holding my hips tightly and rocking up into me, hitting my prostate, and a dollop of precum leaked out of my dick that was back to full strength. “Ride my dick, Max,” he held on tight and rocked his hips even more.

The initial shock of having anything in my ass had worn off quickly; having my best friend's dick in me was so weird, but fuck…it felt good, I did my best to rock my hips to meet his thrusting, and each time his dick hit my prostate, it nearly blew my mind and my load.

“Oh fuck…Gabe,” I moaned.

“Yeah, that’s it, ride my dick Max,” he shifted his legs and pushed his ass up off the bed so he could get me up enough to pull his dick at least halfway out and thrust up into me hard enough to make the clapping sound I’ve only heard in porn.

“Mmm, shit, that feels so good,” I moaned, forgetting about my dick entirely as I focused on this new amazing feeling of having a dick inside me. My head spun from the alcohol as Gabe rearranged my insides with all of his inches. I was in heaven.

“Fuck Max, you feel so good; I’m not going to last long,” he warned me, trying to slow down his rhythm so he could hold out longer.

The words rang in my head, like when he gave me a blow job when we were younger. I knew it meant he was about to cum.

“You better not cum in me,” I almost chuckled, rocking my hips on his cock, inching him closer to orgasm.

He let go of my hips, reached between my legs, and started stroking my cock. I threw my head back; the amount of pleasure I got from him stroking my dick while he stretched my asshole is indescribable; I moaned again, forcing him to reach up and put a hand over my mouth so I didn’t get too loud.

“Shhh,” he hissed, rocking his hips again up into me even harder.

“Sorry, it feels,” he rocked his hips up hard, sending shivers into me, “fuck, it feels so good,” I admitted.

“For me too, Max; ride my dick, man,” he told me, and I did the best I could, but we got out of sync as I found myself getting closer to orgasm.

As I rocked on his dick, I found that clenching my ass in time with the rock up gave me even more pleasure, and I moaned again. He kept stroking my cock with one hand and my abs with his other hand; I was getting close.

“Fuck that feels good,” I whispered.

“Yeah, it does; I’m getting close,” he warned.

He rocked up into me, walloping my prostate, and I felt my balls tighten and my ass clench, “Oh fuck, I’m about to cum,” I warned and rocked harder on his dick as he rocked harder up into me.

“Cum for me, Max,” he whispered and rocked harder up into me.

I pushed his hand off my dick, shifting my weight and stroking myself off. He grabbed my hips and started pounding my ass hard and fast as I just held myself over him. “That’s it, don’t stop,” I told him, clenching my ass and getting my prostate beat up. I couldn’t hold back any longer, “oh fu-ck,” I inhaled and felt the first volley of my load shoot onto his chest. He thrust harder into me, forcing out my second volley, hitting his chin and neck. I rocked my ass harder on his cock and felt him twitch inside me as he moaned.

“Fuuuuck, ungh,” he groaned and thrust up hard.

I twitched and shot rope after rope of cum onto him until I had completely emptied my balls, even the backup reserve from not being able to jerk off in the dorms, just buckets of cum dribbling onto Gabe's abs as his thrusting came to a brutal halt, his dick still twitching inside me as he relaxed under me and I just sat on him. Both of us are trying to catch our breath. I noticed he was losing his erection inside me, and he was just as out of breath as me, and all his muscles had relaxed.

“Did you cum?” I asked quietly and out of breath.

His hands loosened their grip on my hips, “uhh…” he chuckled, lifting his head off the bed to look at me, “Yeah.”

I scrunched my face, “Oh gross, man,” I tried to lift my hips off his dick, but his hands grabbed me at the waist and pulled me back down.

“Just…wait, let me enjoy it,” he whispered.

I chuckled, “You’re so gross,” I huffed and shook my head with a smile that was stained on my face.

“I know, but fuck Max…” he huffed with all his teeth grinning at me.

I let him enjoy his post-orgasmic bliss for another minute before I slowly raised off his dick, and it fell out of my hole, wet with his cum, and flopped down on the bed on my back. My legs were weak in a way they had never been before. I can’t believe Gabe just blew his load inside me. Was this going to change our friendship? What does this mean?

I lay there for a few minutes, my head swirling from the sex and the alcohol, until I passed out.

When I woke up, Gabe was not in the bed with me. I was completely naked, sore, and hungover. I could hear his family downstairs having breakfast as they always had on a Sunday morning together. I slowly sat up and looked for my underwear. They were nowhere to be found. I went into his dresser drawer to grab some of his; in the drawer were some condoms and Polaroid photos. I slipped on a pair of his Hanes briefs and looked at the photos. It was Gabe and a guy who looked a little older than him on a boat in Speedos. The next one, the guy was kissing Gabe. It made me angry and jealous at the same time. Was Gabe…gay?