My Boyfriend and My Best Friend

The cabin trip reaches a wild and chaotic climax as a high-stakes game of truth or dare pushes everyone's boundaries to the absolute limit. Conflicting desires and intense new encounters force Alex and Jeff to confront the future of their relationship, changing their dynamic forever in this final chapter.

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  • 15 Min Read

Weekend at the cabin Part 2 

Final Chapter

Alex Pov

My breath caught in my throat. The dare had escalated dramatically. My eyes darted to Jeff, who looked both surprised and excited by the prospect.

Max didn’t hesitate. He positioned himself between Jeff’s legs, pulling down Jeff’s shorts with ease. Jeff’s cock sprang free, already hardening in anticipation. Max turned his head to look at me, a smirk playing on his lips. He lowered his shorts in preparation.

I was happy to accommodate. Max had a great body, and his ass looked hot. It didn’t take long for Max to start sucking on Jeff’s cock, his experienced mouth working Jeff into a frenzy. I grabbed the lube from the side table where someone had conveniently left it earlier, coating my fingers generously.

Max’s muscular ass was on display as he bent over between Jeff’s legs. I circled his hole with slick fingers, surprised at how easily one finger slipped inside. Max moaned around Jeff’s cock as I added a second finger, stretching him open.

“He likes it rough,” Ben commented from the couch, lazily stroking himself as he watched. Hmmm, I wondered how Ben knew that his dad liked it rough.

I lined up my cock with Max’s hole and pushed in to the hilt. Max moaned; fuck yeah, Alex, let me feel that cock. The feeling of his tight ass enveloped me. The sensation was incredible, different from Jeff, tighter and hotter. Max pushed back against me; he clearly wanted me to fuck him hard. I gripped Max’s hips and drove into him harder, watching as his mouth worked Jeff’s cock.

The sight of my boyfriend’s face smiling with pleasure as Max’s lips slid up and down his shaft sent a confusing mix of jealousy and arousal through me. Jeff’s eyes locked with mine over Max’s bobbing head, his mouth slightly open, breath coming in quick pants.

“Fuck, your ass feels good,” I groaned, surprised by how much I was enjoying this. Max pushed back against me again, taking me deeper, his muscles clenching around my cock.

“Time!” Ben called out, sounding almost disappointed. “Two minutes are up.”

I reluctantly pulled out, my cock slick and throbbing. Max straightened up, wiping his mouth with the back of his hand, a self-satisfied smirk on his face.

“Your turn,” Max said, looking at Ben, Truth or dare.

“Dare,” Ben replied, ok, I dare you to fuck your best friend for 2 minutes. Oh shit, this was really pushing things now. Until now, Ben and I had never fucked, only because we had agreed years ago that we just worked as friends. Recently, we’d fooled around a little, we’d kiss when we were drunk, he’d jacked me off on occasion, and I’d sucked him off, but we’d never crossed that line.

Ben moved over to me and whispered in my ear not to worry, that he would be gentle. He started lubing my ass, sticking his middle finger in, stretching me. He added another finger, and I moaned. I was loving the feeling.

I know Ben’s cock was at least 8 inches, and I was a bit worried. I felt his head nudge my hole, then he slowly started slipping his cock through my sphincter. It was a lot of cock. He moved forward and I felt his cock rub against my prostate and I moaned, mmm Ben said, your ass is so fucking tight, his stomach was now on my back and he wrapped his arms around me and started kissing my neck, fuck my body was vibrating, it felt so good, Ben was giving me the fuck of my life and I was all there for it.

The pressure against my prostate sent waves and waves of pleasure coursing through my body. I’d never experienced anything like this before, not with Jeff, not with anyone. Ben’s thick cock stretched me in ways I hadn’t imagined possible, hitting spots inside me that made my vision blur at the edges. I guess I now understand why Jeff loved Ben’s cock so much and kept going back for more.

“Time’s up,” Liam called out

But Ben didn’t stop. He kept thrusting, his pace increasing as he stared directly at Jeff over my shoulder.

“Sorry,” Ben said, not sounding sorry at all, “but Alex’s ass is just too good. I couldn’t stop if I wanted to.”

His rhythm intensified, each thrust pushing deeper. I felt myself surrendering completely to the sensation, my body opening up to take more of Ben’s impressive length. My cock throbbed painfully, neglected and dripping precum onto the floor below.

“Fuck, Ben,” I moaned, unable to form more coherent thoughts as pleasure overwhelmed me.

Ben’s hand snaked around to grasp my cock, stroking in time with his thrusts. The dual stimulation was too much. My entire body tingled, my toes curling against the wooden floor as he continued to pound into me relentlessly.

“Fuck,” Ben grunted, his pace becoming more frantic. “I’m gonna cum.”

His fingers dug into my hips as he slammed forward one final time. I felt Ben’s cock throb inside me, filling me with warmth. The sensation triggered my own orgasm, my cock pulsing in Ben’s hand, unloading thick ropes of cum onto the floor.

We stayed like that for a moment, catching our breath. When Ben finally pulled out, I felt strangely empty, my hole twitching from the sensation.

“Holy shit,” Liam whispered from across the room.

I looked over at Jeff, nervous about his reaction. But he just looked back with that dopey smile of his, pupils dilated from the weed. Something had shifted between us all, and I knew this weekend was only going to get more intense.

Liam got some more beers, and Max suggested another game, higher/lower. “We all pick a card from the deck,” he explained, holding up a worn pack of playing cards. “The person with the lowest card will be everyone’s slave for the rest of the night.” He must be naked, must kneel, and must submit to all requests,” Max continued, his voice dropping to a husky growl. “No matter how perverted.”

I raised an eyebrow, my heart rate quickening. I had a sickening feeling I knew how this was going to end.

I needed some fresh air; I was overheated from the fuck I just had. I went outside on the back deck for a bit, unsure if I wanted to continue with these games. Things were starting to get out of control, and I could only imagine what would be coming next for the person who pulled out the lowest card.

Jeff followed me out to see if I was okay. I told him I was worried this was going to end up like the party had and the slave is going to get his ass railed. Jeff told me it was just fun, that if you got picked and didn’t want to do something, then he would back me up.

We both went back inside. The air in the cabin seemed to thicken. I glanced at Jeff, who gave me a wink, his eyes glassy from the weed and alcohol. The memory of Ben’s cock still burned inside me, my hole tender from the unexpected intensity.

“Ok, let’s start,” Liam said eagerly, reaching for the deck.

We gathered in a loose circle, the tension palpable as Max shuffled the cards. One by one, we each took a card. Fuck me, I pulled a two of clubs from the deck and immediately felt my stomach drop. I looked around as everyone revealed their cards; of course, all were higher than mine.

“Looks like we have our slave for the night,” Max announced with a smirk. “On your knees, boy.”

I hesitated, my heart racing. The others were waiting to see what I would do. I could have piked out and told them I wasn’t feeling well and gone to lie down, but I didn’t want to allow Max to have another opportunity to fuck Jeff without me around.

I knelt on the timber floor, cold against my knees. Max disappeared into the kitchen and returned with several items. “You’ll have to wear these for the rest of the night,” he said, holding up what looked like a plastic cage. “Since you’re here for our pleasure, not yours.”

Max grabbed my cock and slipped the cock cage over it, and clicked it shut around my softening cock. The small lock snapped into place with finality. Max then pocketed the key with a smirk. He then produced a leather collar, which he fastened around my neck. The leather felt cool and strange against my skin.

“I’ve also got a leash and a doggy tail for later,” Max added, dangling them before me. Now you have to do as you are told and submit to everyone’s requests for the night.

The first request was from Ben; he told me to crawl over to him and give him a foot bath with my tongue. He was just lying back on the couch, and I had to lick Ben’s feet. I had never really done anything sexual with feet before. Bens didn’t smell too bad, and they were pretty soft.

Taking Ben’s lead, I began by licking the sole of his left foot, then all around his foot, the ankle, the heel. He then told me to suck his toes and lick between them. Ben started to moan, Mmm, yes, suck on those toes…. I started to really get into it, slobbering all over Ben’s foot. I guess we all have our little kinks, and I was learning what Ben’s were.

He started to rub his other foot over my cock cage. My cock was trying to get hard, straining against the cage. The pressure against my caged cock sent conflicting signals through my body. My mind wanted to respond, to feel the fullness of an erection, but the plastic cage kept me painfully restricted. Ben seemed to notice my discomfort and smiled, pressing his foot against the cage more firmly.

“I think that’s enough,” Ben said, pulling his foot away. “You did well.”

Liam’s request came next. “I want you to tongue my ass, slave,” he announced, his cock already hardening at the thought. “Lie down on your back.”

I lay down on the rug on the floor as Liam straddled my face; he faced toward my feet to give the others a clear view. The musky scent of Liam’s ass filled my nostrils as he lowered himself. I began licking and kissing around his ass tentatively at first, then flicked my tongue over his tight hole, mmm, yes, he moaned.

I increased the pressure and started to ease my tongue into Liam’s hole. This was one of my favourite things to do with Jeff, so I began to really get into fucking Liam’s hole with my tongue.

As my tongue probed deeper into Liam’s hole, the man above me started to moan loudly. The saltiness of sweat mixed with the musky scent of Liam’s body filled my senses. I knew I was good at rimming. Jeff always loved it when I rimmed him. I put everything I had into pleasuring Liam, circling my tongue around the puckered entrance before plunging back in.

Liam rocked against my face, grinding down to get more of my tongue. “Fuck, that feels amazing,” Liam groaned, stroking his cock frantically.

I glanced up past Liam’s body to see the others watching intently. Jeff and Ben were now stroking each other’s cock; their eyes were dark with lust. The sight of my boyfriend and best friend getting aroused by watching me service another man sent a confusing jolt through my body.

“I’m cumming,” Liam moaned, rocking back and forward over my tongue. I increased the pressure as shot after shot of cum landed on my body. Fuck that was intense.

I was dreading what was coming next. I wasn’t sure what Max was going to do, but I knew he was going to push my boundaries. I’m not sure where he got all these props from, but he pulled out a leash, he then pulled out the dildo in the shape of a doggy tail.

For the next half an hour, I was his pet. He walked me around the lounge room and told me to sniff and give a quick lick to everyone’s cock. I was playing the inquisitive puppy, walking up to everyone, getting them to pat me, and I would lick their dicks. If this was all that Max had in mind, then I was happy.

Max looked at me with a smirk and said, “ok, puppy, time for a piss.” I knew something was up when everyone was agreeing it was a good idea, and they needed to piss too.

I assumed Max just wanted to walk me outside so I could take a piss, but fuck, I was so wrong. He walked me outside, and I sniffed the ground a little, looking for a good spot to pee. As I looked up, I was shocked when a stream of golden piss was coming down on my face, first from Max and then from everyone else; they were all laughing and aiming their cocks at me. Fuck, Max had set me up big time, and they were pissing all over me, even my boyfriend.

I had never been into any type of kink, so of course, trying watersports had never been on my radar. I thought I would be more humiliated, but I think because we were all drunk and high and having fun, it felt good. Everyone was now pissing on me from head to toe.

I started to get some in my mouth, and then everyone got the idea that aiming their piss in my mouth should be the main goal. I would let the piss pool in my mouth, and I would then spit it back at everyone. Apparently, spitting the piss back at Max and the others wasn’t in their rules, and Max told me I would have to be punished for that.

Max got the hose and washed me and the others off before going back inside. I was told to get over Max’s knee, as I was now going to be spanked for spitting the piss back at everyone. He started pretty mild, but my ass was stinging badly after the 10th spank. For some reason, my cock was trying to get hard in my cockcage; surely, I wasn’t getting turned on by being spanked.

Jeff’s request was next, and I thought surely, I could relax a bit as my boyfriend would take it easy on me.

Fuck was I mistaken. “Lie on top of Max,” Jeff instructed with a gleam in his eye. “We’re going to recreate what happened at the party, but this time you’ll be taking two cocks in your ass, and Liam will be fucking your mouth.”

My stomach dropped. Was he fucking kidding? The memory of watching Jeff sandwiched between Ben and Max flashed through my mind. I know it had looked incredibly hot when Jeff was doing it and I was the spectator, but I wasn’t even sure if my ass could handle two large cocks at once. I shot Jeff a pleading look, but Jeff just smiled back wickedly. Don’t worry, babe, he said, you’re going to love this. I know I did, his voice husky with desire.

Max was already positioning himself on the couch, his thick cock standing at attention. He looked at me and said you’ll get to find out first-hand why Jeff loves my cock. Jeff got some lube and started to finger my ass. It started to feel good. He added another finger and was now sawing his fingers in and out, stretching my ass. Alex, relax, Jeff told me, you are going to love this, he added a third finger, and I could now feel the stretch.

Ben’s dad reached around and aimed his cock at my hole and started to push in, fuck, it was so thick. Jeff was sitting back smiling, watching as Max started to slowly fuck my ass. I was uncomfortable for a bit, then he started to hit the right spot inside me, oh fuck, yes, there I moaned, he was getting a good rhythm now, and it was starting to feel good.

Liam moved closer. He slapped his cock on my face, I put my tongue out, and he pushed his cock inside my mouth, fuck, this was hot. I was moaning and really getting into being fucked now, I had to admit, my previous worries were unwarranted, and this was probably the highlight of the night.

When I felt another cock try to push up inside me next to Max’s cock, I got worried again. I let out a yelp as this was too much to handle. Max reached up with a little brown bottle and told me to close my other nostril and sniff, and then sniff again on the other side.

Fuck, it was like pure bliss had just exploded in my head. I was lost in the pleasure of it all. The other cock pushed further into me and was now starting to get a good rhythm against Ben’s dad’s cock.

Jeff started to kiss my neck, you love it, don’t you, he said. You love how my cock is in your hole with Max’s. I looked up in surprise, for some reason I assumed it was Ben’s cock fucking my ass, but it was actually Jeff who was now starting to fuck me hard with Ben’s dad… oh, fuck this was so good.

Jeff pushed my face forward to Ben’s dad. I started making out with him. He was sucking on my tongue, fuck, this was unreal. I could feel my cock trying to get hard, but the fucking cock cage was destroying my erection, fuck, I desperately wanted to cum.

Ben was standing next to Liam, leaning into him, and they both had their hard dicks pointed at my mouth. They pushed in at the same time with limited success. I decided to alternate between the brothers. I looked up at one stage, and they were lost in a messy, sloppy kiss, while I was sucking on their cocks.

Everyone was caught up in this hot, messy moment. One after another, everyone got close to cumming, Max moaned loudly as he unloaded inside me first. The vibrations of Max’s throbbing cock set Jeff off, who was now shooting his load in my ass. Liam shot his load down my throat, then Ben let his cock shoot all over my face. Fuck, I was a mess, and my cock was still straining against the cockcage.

After a couple of minutes, we all caught our breath. Jeff pulled his cock out of my ass, followed by Max, and we started to clean up. I had cum oozing out of my stretched-out hole and all over my face. Ben’s dad told everyone it was time for bed, and he was bunking in with Jeff and me this time. Ben said that was fine and grabbed Liam’s hand and pulled him into their bedroom.

I jumped in the shower quickly to clean off the sweat and cum of the evening. I was so tired, I dried myself, got into bed and fell asleep.

Sometime in the middle of the night, I woke up to the bed rocking, and Jeff moaning, Oh fuck, Max, yes, harder, harder. Max was looking right at me, kissing my boyfriend, you love my cock don’t you, he was saying. I was still locked in the cockcage and hadn’t cum since last night. I was getting frustrated when Max moaned and dumped another load in Jeff’s ass.

I got out of bed and left Jeff and Max kissing. I was feeling quite left out. Jeff came into the kitchen as well and asked if I was ok. I just looked at him and walked out.

I sat down in the living room, worried about our relationship going forward. I knew that this weekend had triggered something, and I was afraid our relationship wasn’t going to be the same. Jeff followed me and sat down next to me, and hugged me. He asks what’s wrong. I tell him I am feeling alone, and I think he has feelings for Ben’s dad.

He looks at me and says he likes Ben’s dad a lot, but I’m in love with you, you are my boyfriend, and just because we may have sex with others, that doesn’t change our relationship; it makes it stronger. I tell him how I don’t like how it makes me feel when he’s fucking you and getting you to say how much you love his cock.

I know he likes to push boundaries, he tells me, but I love how Max makes me feel. He has got such a large, thick cock, and it feels so good when he’s fucking me. You experienced his cock, you know, and I know you love watching him fuck me and using me. After this weekend, I’ve also got the feeling you like getting fucked by other people as well, especially Ben. I couldn’t disagree.

How about we open our relationship up for 6 months? If it doesn’t work out, then we’ll go back to how we were.

We went back to bed. I was on one side, Jeff in the middle and Ben’s dad on the other side. We both put our heads on Jeff’s chest and looked at each other, and smiled. I knew from this moment our relationship had changed, and Jeff’s attraction to Ben’s dad was obvious. I suspected that Max was going to be a larger part of our lives going forward.

The End.


Stay tuned for My Boyfriend and My Best Friend's Dad coming soon......


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