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Porter's Proposal


    I've never admitted it to Owen, but I admired him. I don't think I would've been brave enough to come out in high school if he hadn't done it first. All of a sudden, he did it and it was like it was no big deal anymore. 

    He seemed to be doing okay for himself in New York as well, at least judging by the way he looked. He was always a jock, but damn, he was fucking ripped now! Made perfect sense that he'd start working as a personal trainer.

    As summer went on, we got close in a way you only do with someone you share a room (and a bed!) with. Unfortunately, we didn't get too many chances to hang out; he often worked evenings and weekends, and I worked office hours. Still, we tried to find at least one day a week when we could spend a few hours together, so he could show me around the city and we'd catch up.

    "How's work going?" I asked over lunch one Saturday afternoon in August.

    "Pretty good, man," Owen answered with his mouth full. "Got a few more clients, been pretty busy lately."

    "I've noticed. Good for you. You working tonight?"

    "Yeah, I'm meeting that guy Porter. My first client."

    "Don't you usually see him Wednesdays?"

    "I do. I see him twice a week now."

    "Wow, he must be really determined to get in shape."

    "Not really. Listen," he leaned in and started talking more quietly, "I think he has a thing for me."

    "You think everyone has a thing for you," I laughed, then I looked him up and down. The weather was swelteringly hot and he was wearing a flimsy tank top that showed off his upper body almost completely. Some sweat dripped down his pecs and biceps. "Then again, you might be right," I added.

    "I'm serious," he said. "You know how he gave me an iPhone the second time he saw me?"

    "Ah yeah, that's the same guy."

    "And after that, he just kept buying me gifts. Or like, he'd give me cash at the end of a session, 'as a tip.' I told him there's no need, but I think he knows that. The tips are bigger than the cost of the sessions by now. I never said anything, I wasn't gonna complain, but it's weird."

    "For real dude, really fucking weird. What's the catch?"

    "At first I thought there is no catch. He never asked for anything extra. Some clients will ask for a massage or something after working out, but he was never like that. I just thought he's a crazy rich guy who has nothing better to do with his money. Then, he asked me out for dinner last night."

    "Is that where you were?!"

    "Yes. He suggested this fancy steakhouse downtown and I figured, what the hell, I'll go. Then during dinner, he had a… proposal for me."

    "Ah, here we go. What's the offer, Pretty Woman?"

    "Well, he's into some kinky stuff. Likes being dominated and shit. Took him forever to get the words out."

    "Aha. And he wants you to spank him around?"

    "Occasionally, but it's not just that. He wants to be my cash slave."

    "Your what now?" 

    "He wants to keep giving me money. Apparently it turns him on."

    I stared at my friend with my mouth agape.

    "You're serious?" I asked.

    "I can't make this shit up."

    "God, please make me rich enough to do stupid shit like this some day," I said, taking a bite of my food. "You're paying for lunch, by the way."

    "That's not all," Owen said. "He asked about you?"

    "Me?! How does he even know me?"

    "He's seen us in the locker room together, apparently. Noticed you have a huge schlong."

    Owen eyed me mischievously. 

    "Oh Jesus, what's next?"

    "He wondered if… you and I would fuck him together," he grinned.

    Even though I could use some more money, that's not the reason why I said yes. Sharing a bed with Owen all summer, I was horny like a motherfucker. I hadn't gotten laid all summer; I didn't really know the city and I didn't wanna bring guys back to Owen's. As for him, he and I were both mostly tops, plus we were friends so I didn't wanna fuck that up. However, I figured there was nothing wrong with admiring him silently.

    If anything, the fact that I couldn't touch just made it hotter in a way. Every night, Owen would get down to his underwear (always very revealing) and strut around the apartment cockily in front of me and his roommates. He stayed like that while having dinner and brushing his teeth. Then, in his room, he'd take his undies off and get in bed next to me.

    The whole night, I'd be tempted to reach for that ass of his. It was so perfect, I couldn't not look when it was in front of me. Add to that the fact the rest of his body was just as gorgeous, and it's no surprise I started to jerk myself off to sleep while he was lying right next to me in bed. 

    A couple of times I wondered if Owen knew what I was doing. If he did, he never said anything. Somehow I had the feeling Owen enjoyed having that effect on people; turning them on and teasing them, pushing them over the edge. Cocky motherfucker.

    My last weekend in New York, we headed to his client's apartment. He'd sent his driver to pick us up, and I tried to act like being picked up by someone's personal chauffeur was something I did all the time. In the back of the car, there was a chilled bottle of champagne waiting for us to enjoy while in traffic heading downtown.

    "Hi. Welcome," Porter greeted us nervously at the door, dressed in a nice designer suit. His fancy apartment looked exactly how I'd imagined it. "Would you like something to drink?"

    All of a sudden, a loud bark I wasn't ready for echoed from Owen.

    "Get on your knees, faggot!!"

    As I turned to look at my friend, Porter bowed his head and kneeled in front of Owen.

    "Take those fucking clothes off," Owen barked again.

    Porter started to undress, keeping his head bowed down at all times. Meanwhile, Owen shot me a discreet smile, as if to reassure me everything was okay.

    When Porter was completely naked, Owen reached in his pocket for something.

    "Put this on your pathetic little dick!" he bellowed.

    He handed Porter a small metal cock cage, as I stood there watching, still feeling dumbstruck. I'd seen stuff like this on video, but it's a whole nother thing to see it in person; especially when it's someone you know. Owen was my high school friend, for fuck's sake! A few years ago we were both pretending to be straight, and now we were here doing this.

    I observed Porter as he put the cock cage on. His dick wasn't particularly small, it was what I would call average; but looking at him right now, it did seem shriveled and pathetic. The salt-and-pepper pubic hair growing unruly on top didn't make it look any nicer either.

    "Where's the money?" Owen said loudly. He always sounded confident, but this was… different. It was like Owen's confidence on steroids. 

    "H— Here, Sir," Porter crawled on his knees to a nearby table and picked up an envelope. He crawled back to Owen and offered it to him, head bowed down.

    "It's not enough!" Owen said without even opening the envelope. "Empty out your wallet."

    "Y— Yes, Sir," Parker agreed and without missing a beat he started rummaging through the pile of clothes on the floor, retrieving his wallet. He took out several hundreds' worth of dollars in various notes, and handed them to Owen obediently.

    "You pathetic faggot," Owen laughed while pocketing the cash. "You barely even know us, and look at what you're doing. You know," he reached down and picked up Porter's chin so the two made eye contact, "some people would wonder why you're doing this."

    "Because I'm a pathetic piece of shit and you're a superior man, Sir! You deserve my respect," Porter recited with a solder's discipline in his voice.

    Owen's hand moved slowly from Porter's chin to his neck, chocking him lightly. Then, Owen loudly coughed up snot and saliva and spit it right in Porter's face.

    "At least you know your place," he said and walked casually to the beautiful sofa in the living room.

    Porter crawled to the kitchen. Unsure what to do, I went and sat next to Owen.

    "You okay?" he whispered, while Porter struggled to get us drinks while crawling like a dog.

    "I'm fine. Just threw me off a bit."

    "I know it's a lot, but it's alright, we have a safeword and a sign and everything. He gets off on it."

    "Do you?" I asked.

    Owen thought about it for a second and smirked.


    Porter crawled back to the living room carrying a tray with more champagne and two glasses on it. Owen opened the bottle and poured some for himself and me, and we toasted. Then Owen, whose feet were on the table, kicked the bottle so it fell and spilled on the floor.

    "Oops. Guess we'll need more."

    "Yes, Sir," Porter crawled back to the kitchen. 

    "And clean this shit up!" Owen barked after him.

    When he was back by our side, Owen told Porter to bend down and show us his ass.

    "Not bad for a faggot his age, huh?" Owen said, and I wasn't sure whether I was supposed to answer. I didn't know anything about Porter; I didn't know if he was openly gay and having sex with men, or if he'd maybe never been fucked before. Either way, his hole was smooth and didn't look bad.

    "It needs a dick up in it, doesn't it?" Owen smacked Porter's ass cheeks a few times.

    "Yes, Sir, please!"

    Owen got up and stood behind Porter and started playing with his ass. Porter started moaning in pleasure.

    "Aaah, thank you, Sir."

    "Shut the fuck up!" Owen barked at him. Porter didn't say anything else, but continued to moan out occasionally as Owen's fingers played with his hole.

    Owen slowly started to take his clothes off, as I sat next to them on the sofa, watching them. A few seconds later, Owen was standing right in front of me, bare ass naked, his beautiful ass right in my face.

    "Fuck," I said out loud and licked my lips, savoring the view.

    Soon enough, I was hard. I thought to look at Porter's cock, and noticed it was straining to rise but, confined by the small cock cage, it couldn't get very far. Swiftly, I took out my hard-on and started stroking, enjoying watching my friend play with this man. There was something about Owen… This role made him even more attractive.

    "Fuck!" Porter said quietly as another one of Owen's fingers went inside his hole.

    "I thought I told you to keep quiet!" Owen yelled out, reminding me of my father's voice when he was really upset. "Guess I'll need to stuff that mouth for you to shut the fuck up."

    He walked in front of Porter, and as he turned around, I noticed Owen was hard by now as well. He grabbed Porter by the throat carelessly, and shoved his dick in his mouth.

    "You like that, buddy?" Owen asked me, fucking the man's face and pulling his hair, as I sat on the couch and watched them.

    "Fuck yeah, man," I said.

    "Help yourself if you need a hole," he said. "That's all this faggot's good for," he slapped Porter's face loudly as he chocked on his dick, "a hole to be filled."

    "Don't mind if I do," I said, getting off the couch and kicking my clothes off. Porter's hole had been opened up by Owen and ready for fucking. I got in position, and slowly started to go inside him.

    "Fuck," I exhaled. I hadn't fucked anyone all summer and hadn't realized how much I needed this.

    "You don't need to go slow," Owen reassured me, standing right in front of me, stuffing Porter from the other end. "He can take it."

    "Oh yeah?" I said and, to impress Owen more than anything, I slammed my cock all the way inside Porter without warning.

    "Gufff!!" Porter struggled to yell out but he couldn't, his mouth full of Owen's thick cock. 

    Having a huge cock has downsides people don't often talk about. More often than not when I fucked somebody, they either needed me to go extra slow or they flat-out gave up. I never got a chance to fuck someone fast and carelessly. Well, this was it.


    I went balls-deep into Porter's hole, thrusting all at once; then pulling back and doing it again. His whole body spasmed, barely able to take it, as he gagged on Owen's dick as well. I looked down and noticed sweat, snot, and saliva all dribble down Porter's face.

    "Yeah, man, give it to him. Show him what a fucker you are," Owen encouraged me.

    "Oh, I'm showing off for you," I thought, as I started to thrust faster and faster. Owen smirked at me and I grinned back, both of us looking each other dead in the eyes. Who'd have thought, when we both came out in our junior year of high school, that this is where we'd be a few years later? "Man, I love being gay," I thought and laughed to myself, tipsy off that expensive champagne, fucking our bottom faster and faster.

    "Just don't cum without me, buddy," Owen said. By this point we were fully focused on each other, completely ignoring the man we were both fucking. Like Owen said, he was nothing but a hole to be filled.

    "Fuck yeah, man," I grunted. "You wanna go at the same time?"

    "Fuck yeah."

    We fucked faster and harder, Porter gagging and struggling for air. As I was holding Porter's waist, Owen leaned forward and put his hands on mine. For some reason, this felt both horny and intimate. It was exactly what I needed to send me over the edge.

    "Fuck yeah, man, I'm cumming," I said, thrusting harder than ever, holding my buddy's hands.

    "I'm almost there," Owen said, pulling one hand back to grip Porter by the hair. He started fucking his face so mercilessly that normally I would be concerned. Right now, I was too close to cumming to really pay attention. I started shooting my seed inside his asshole.

    "Fuck yeah, buddy!" Owen screamed and I could tell he was cumming too. Porter moaned noisily as he struggled to take Owen's cum down his throat.

    A minute later, our thrusts were getting slower and slower, until we finally both pulled out. Porter took a deep breath, as if his head had been underwater this whole time and just resurfaced. 

    "Thank you, Sir," he mumbled, still drooling all over the floor.

    "It was our pleasure," Owen smacked his cheeks lightly and came to sit next to me, so we could cuddle up and finish the rest of the champagne.

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