The Tallest Sub Ch. 04

Phil had been part of my larger friend group going back to our college days, and I had always suspected he was gay, but never knew for sure. Since my divorce, he had taken a stronger interest in me, and I was more than open to the attention. We had been good friends back in the day, lotta fun drunken nights out, but eventually, we drifted apart.

After discovering my 'other' side, I started realizing his friendliness might have been more than just about being buds, and I made an effort to start reciprocating. Knowing he was coming out tonight, I had put on one of my best shirts, got a haircut, and tried to look as presentable as possible. Half the night passed before I was able to inconspicuously sidle up to him. I had bought a round of beers for everyone, and a Patrón and soda with lime for him, which I remembered was his favorite drink from ages ago.

"It's nice to know I made a lasting impression on you," Phil said.

"I've always been a people pleaser, and I think it's cool you have a signature drink. It sets you apart from the Bud Light crowd," I said.

"Among other things," he replied. "You know we should hang out more. We used to hang out a lot back in the day, and it was a ton of fun. Whatever happened?"

"I got married, settled down to a boring life of network procedurals and house repairs," I said.

"I'm sorry, I fell asleep, what were you saying?" He had a grin on his face, pleased with his own joke.

He wasn't wrong, my married life had been slow. It wasn't just getting older, it was like someone had turned the vibrancy down on life.

"Exactly. Life got boring, I got boring. But that's in the past. I'm free now and trying to make up for lost time. I've been hitting the gym, getting out more, trying new things. It's super cliché, I know, but I'm trying to say yes more," I said, with genuine excitement.

It was true, though I left a lot of details unsaid. I'd been experimenting sexually and finding my place as a submissive. Trying new things helped me find my boundaries, and even the things I didn't like taught me more about myself.

"So, if I asked if you wanted to hang out tomorrow, you'd say...?" he asked.

"I'd say yes, let's do it," I said, trying to keep my smile from giving too much away. I didn't know if this was a date. We had hung out alone many times and while I was straight then, he had never made a move. I decided to proceed with caution.

We continued chatting for a bit, until our friend group started breaking up for the night. Phil told me to come over at seven-thirty, and texted me his address.

I spent the next day, overanalyzing everything. What I should wear, how should I present myself, should I bring a gift, and so on. I settled on a shirt that looked nice enough to show I was putting in an effort, but not so much that it screamed 'date night'. I went out and bought a bottle of Patrón, thinking that it would be a nice-but-neutral gesture. Lastly, I had learned enough about bottoming to prepare myself in advance.

I had started to take pride (and pleasure) in getting myself ready. I lathered up in the shower and shaved my balls and ass, then trimmed the hair above my dick to a neat half-inch with my body groomer. I made sure to clean my ass thoroughly with the shower sprayer, in hopes Phil would appreciate it later. When I got out of the shower, I checked myself out in the mirror, and felt like I was doing pretty well. By the time I left my apartment, I felt like I was nailing this-- my confidence was high that I was going to get laid.

When I arrived at Phil's apartment, I knocked and someone I didn't recognize answered the door. "Uh, is Phil here?" I asked, with a very puzzled look on my face.

"Oh yeah, he just went to the bathroom, you're Derek? C'mon in, the game just started."

The blackhawks were on TV, and while I did like hockey, I had been hoping to do a different kind of stick handling this night. My gut sank, I had completely misread the situation. Here I was with my shaved junk and squeaky clean asshole holding a bottle of Patrón, trying to hide my disappointment.

"Cool. I brought tequila," I said, trying to hide my disappointment. Phil came out and offered me a beer, which I took readily and handed him the bottle of Patrón.

"Thanks bud! I hope you don't think we're finishing this tonight, it's only the three of us. I do want to be able to walk tomorrow," he said. He took a seat on one end of the couch, while Joe was sitting on the other. I wanted to be closer to Phil, even if it wasn't a date, I could at least, maybe, get some accidental touching in. So I took a seat in the middle.

"Sitting in the bitch seat, I see?" Joe said.

"Better viewing angle for the game," I said, trying to cover my tracks.

The game was ho-hum and I was leaning into the tequila. Joe and Phil clearly had a rapport, and they were cracking jokes I didn't always understand. As the tequila bottle got lighter and lighter, I noticed the jokes getting dirtier and dirtier. I didn't think much of it, typical guy stuff. I tried to play along, and by third period, I had a decent buzz going. I looked over and saw Joe and Phil finishing their drinks.

"Let me take care of that for you guys," I said, and got up to make more drinks.

"The game is shit, but the service here is excellent," Joe said.

I felt my face blush, as I picked up their glasses and headed off to the kitchen. I could hear them talking in low voices in the other room, but couldn't hear what they were saying. I came back with fresh drinks, and when I leaned over to put them on the table, Joe had a big smile on his face, and was holding a one-dollar bill. He reached out and tucked it into my belt, as I put his drink on the coffee table.

"I know you're joking, but I'm pretty broke right now, so I'm keeping it," I said.

"You earned it, hon," he said, and I could feel my face flush again.

I sat sipping my drink and trying to focus on the game. Both guys were lying back in their seats, man-spreading across the couch. My left knee was touching Phil, my right knee touching Joe. I didn't know what to do with my hands, I laid them on my thighs, just barely touching both guys' legs. Even that little bit of contact was getting me excited. The mix of booze and the hints of flirting were taking their toll, and I was getting aroused. I didn't really know if I was trying to flirt with Phil or Joe, I was just getting horny, and wanted more attention from these guys.

I waited until the tallest player, Crevier, got checked, and I said, "See? Even the big guys get pushed around sometimes."

The two of them looked at each other with devilish grins, and then just started pushing me back and forth on the couch between them, like a ping pong ball. I turned beat red, I could feel my dick getting hard.

"The key to taking down the big guys is to gang up on them," Phil said.

I was rock hard by then.

Phil told me to freshen up their drinks, and I stood up; without thinking, I was tending the front of my pants. I tried to shift and hide it as I grabbed their glasses and shuffled out of the room. My face was bright red and my breath quickened. I felt a mix of embarrassment and excitement that I knew was only going to make my erection worse. I could hear them laughing in the other room, and it only fueled the fire inside me. When I came back in, holding their drinks, they were both grinning ear to ear.

"So, we were chatting and wanted to know if you're enjoying yourself tonight? We wanted to make sure you didn't feel like a third wheel," Phil said, standing up.

"Oh, uh, no, I mean, maybe a little, but not in a bad way. You guys are fun," I stuttered out, not entirely sure what to say.

"We're a lot of fun," Joe chimed in. "But you seemed pretty disappointed when you saw me at the door. I guess you were hoping for something else tonight?"

"Well, yes, I kinda thought, it would just be Phil and I." I was looking straight down at the drinks in my hands. I could see my own erection tenting out between my legs. I could feel the blood rushing to my face.

"Well, Joe and I have been together for a while now, and while we do experiment with other people from time to time, we always come back to each other. When I told him I had a really tall friend who liked to make me drinks and please people, he was interested, too." Phil stood up and took the drinks from me, putting them on the table, and then he guided me to sit down facing him on the couch.

I felt Joe wrap his arms around my shoulders and pull me back, so I was leaning back with my back against his chest. Phil started to work on my belt and I started to squirm a little.

"Now, you've been walking around our apartment all night with a hard-on, making drinks, dropping hints, and generally being a tease to both of us. Haven't you?"

"Yes," I said, between deep, panting breaths.

My belt was off; Phil proceeded to unbutton my pants and slide them down, showing my cock straining against the thin fabric of my boxers. He took two fingers and gently pulled the band of my boxers down until my dick sprang up.

I turned to ask Joe if he was okay with this, but before I could say something, he pressed his lips against mine and I felt his tongue begin exploring mine.

That answers that question, I thought, as I began to make out with him.

I felt Phil sliding my pants and boxers down. I felt his tongue start at my balls and make its way all the way up to my tip. A deep moan rose inside me, and only Joe could feel it as his tongue explored my mouth. I could feel Phil's hand holding my balls, giving them a tight squeeze, while he swirled the tip of my cock, teasing me.

I was just not going to last. I thought he realized that because he pulled his mouth off my eager dick. Phil stood up and started removing his own clothes. Joe broke our kiss and turned my head toward Phil.

"Isn't that the most gorgeous cock you've ever seen?"

And it absolutely was. Phil was eight-and-a-half inches, cut, perfect purple head with a slight upward curve. It was like an artist's rendering of a dick, not huge, just flawless. To this day, I've never seen a better cock.

Joe's hand slid to the back of my head and he pushed me gently forward, until I took the entire thing in my mouth. I didn't need any convincing, my mouth had been watering since the moment I saw it. I took him into my mouth as deeply as I could and began sliding up and down, trying to give special attention to that beautiful purple head with my tongue. After a couple thrusts, Joe pulled my hair back and that beautiful cock slipped from my mouth. Phil moved to sit and I dove back onto him, putting him into my mouth 'til his neatly trimmed bush was tickling my nose. I heard Joe shuffling around behind me, getting naked.

"God, he's everything you said he'd be," Joe said. He started to massage my ass cheeks with his hands.

"He used to parade this ass around in college in tight shorts, pretending to be straight," Phil said, as he leaned forward and slapped my ass. "Now he's sucking my cock like he was born to do it." He grabbed my hair and pulled me off, then slid his hand under my chin lifting it up 'til our eyes met.

"You need to slow down, I have you for the night and I want to take my time."

"Yes, sir," I said.

When he let go, I switched to taking one of his balls into my mouth, sucking and licking them in turn. I kept a firm grip on his shaft, as if to prevent anyone from taking it from me. I felt Joe spreading my ass and lightly kissing my cheeks. I said a silent prayer of thanks that I had shaved and prepped for this night. I felt him get closer and closer to my puckered asshole, until I felt his tongue begin swirling around it. I let Phil's ball slip from my mouth and moaned loudly, as he pressed his tongue into my ass. I began to lose track of time and felt another stinging slap against my ass. I looked up at Phil staring down at me, his beautiful cock between us.

"Don't forget why you're here," he said, as he pressed his cock against my lips.

I slid him back into my mouth and struggled to concentrate, as Joe rimmed me.

I felt Joe remove his tongue, then felt something cold dribble down my ass. Joe's fingers began rubbing and pressing against my ass, and I realized he was lubing me up. I squirmed and pushed back against his fingers, trying to get him further inside me.

"Damn, he's an eager little slut. He's trying to fuck himself on my fingers."

"You mind if I go first? I've been thinking about taking this ass for a while," Phil said to Joe, grabbing a handful of my left cheek and sliding his dick out of my mouth.

"Of course, I'm going to give that throat a test drive," Joe replied, as if I were just an object in the room.

They knew I'd do anything at that moment. My cock was dribbling pre-cum on the couch, my ass was slick with lube and saliva, and my breath was ragged. I was damn near feral. I needed to get fucked.

"Flip around and get on your knees, slut."

I did as I was told, and found myself staring at Joe's manhood. A bit smaller, maybe seven inches, veiny, and straight as an arrow. He was uncut, and holding the base of his own cock with his hand. I leaned forward with my mouth open and he began slapping his meat against my face teasing me.

"Now, now, we're in no rush. Why don't you return the favor and lick my ass?"

He leaned back and lifted off the couch a little, spreading just enough for me to bury my face between his cheeks. I went right to work, exploring with my tongue, swirling and licking the entrance. At the same time, I felt Phil's head exploring my own hole. He was rubbing up and down my asscrack, teasing my ass. Every time his bulbous head made contact with my hole, I tried to push backwards, and felt him pull back. He did this three or four times, driving me absolutely wild.

I couldn't take it anymore. I lifted my head out of Joe's ass and looked backwards. "I need you to fuck me, I can't take it anymore, please fuck my ass. It was made for that cock. I'll do whatever you want, all night, I'll be your slut, just PLEASE fuck me!"

They both laughed and I felt that familiar mix of humiliation and excitement tighten my balls.

"You really are the perfect little bitch. Okay, slut, you've earned it," Phil said, and pressed directly on my asshole.

I felt a familiar pressure and then a slight pop, as his head pushed past my sphincter. He slid slowly, but surely, into my ass until he was buried to the hilt. I moaned loudly as my eyes rolled into the back of my head. His dick really is perfect, I thought.

Joe, clearly feeling a little left out, grabbed my head and guided my attention back to his cock. I took him into my mouth and tried to focus on his pleasure, but I was so distracted by the long, slow strokes Phil was fucking my ass with. I began bobbing my head furiously on the cock in front of me, trying to will the cock in my ass to go faster. I felt Phil reach down and he squeezed my balls hard.

"Don't try to rush me. I waited a decade to fuck this ass, I'm going to make it last."

I brought my hands up and started to work Joe's shaft with my left hand, while playing with his balls with my right. I let my world narrow to just his pleasure, and tried to ignore the consistent slow fucking of my ass. Joe lifted his ass a little bit more, and I took the invitation to slide my finger under him and start swirling it around his rosebud. I heard him moan a bit and felt a swell of pride.

I briefly removed his cock so I could lick and wet my finger again, making sure to look up directly into his eyes, while I sucked on my own digit. With a little bit of spit, I began to rub his asshole, going a little bit further each time around, pressing my finger inside him. I watched his face as I slid fully inside him, and watched the pleasure as I began to curl my finger forward in a come-hither motion. I took him back into my mouth and began to really work his cock head, while my finger played with his prostate.

"God damn, he's really good at this. I was planning to fuck him too, but I might need to cum down this pretty little throat first," he said, as his breathing began to pick up.

"Go ahead, we have him all night. This ass isn't going anywhere," Phil said, slapping my left cheek.

The stinging brought me back to the sensation in my ass-- the slow, rhythmic fucking I was enduring, the fact that my cock was made of stone and dripping pre-cum on their couch. I pressed my ass backwards almost instinctively and felt my balls tighten in Phil's hand, a mix of pain and pleasure radiating from my groin.

Joe was getting really close; I could feel his dick starting to stiffen, and his ass was lifting further off the couch, letting me get a little bit deeper and really rub his prostate. I started jerking and sucking as hard as I could, while my finger tickled his ass, and soon I felt his legs tense up and his hold began to spasm tightly on my finger. I could feel the cum shooting up his shaft and into my mouth, painting the back of my throat. I didn't let up, milking him with my hands and mouth-- two, three, four, five, six shots of cum into my mouth. I reached up on my finger and hand, but kept my mouth on him as I swallowed all of his cum.

"Good boy, lick him clean," I heard from behind me.

I removed my finger, but kept licking his shaft as he started to go soft.   

Joe put his hand under my chin and made me look up at him, as he bent over to whisper, "You're really a good boy," then he kissed me, and my lips parted as his tongues explored my mouth.

It was too much, I could feel myself about to cum, but a deep squeeze of my balls brought me back.

"Not yet," said Phil, as he slid out of my ass. "Roll over onto your back."

I did as I was commanded, and leaned back against Joe, who was in the process of pulling my legs up toward my head and lifting my ass up off the couch.

"I want you to watch me take your ass and beg for my cum," Phil said, as he repositioned himself and pushed in with one smooth motion to the hilt.

I could feel his balls come to rest on my ass. My dick was pressed against my stomach, a wet spot of pre-cum appearing, my breathing was ragged.

I heard Joe's voice in my ear, "Tell us what you want."

"I want you to fuck the cum out of me. I want you to ram my asshole until I pass out," I said.

His pace started to pick up a little, each time I spoke. I took the hint and just started telling him everything that popped into my sex-addled brain.

"I need you to shoot your load deep inside me. I want you to breed my ass."

A little faster, I could feel his balls slapping my ass in rhythm.

"I'm your dumb cumslut. Fuck me harder."

He was going full speed right then, pistoning that beautiful dick into me.

"He's almost there, push him over the edge," Joe whispered in my ear.

I saw sweat dripping off Phil's brow and landing on my stomach, he was really slamming into me.

"I want you to claim my ass. You own me now."

With that, Joe grabbed my cock and gave it a hard squeeze and three quick strokes. That's all it took, I felt my ass clench and my dick started to erupt. The first shot had so much force, it landed on Joe's shoulder before he adjusted my aim and made me cum on my own chest. I watched Phil's head tilt back and a loud grunt escape his lips, as he shot his load deeply into my ass, slamming home twice more, to drive it further into me; before slowly removing his already softening cock. He fell back into a seated position, and Joe let go of my legs. I could feel some cum starting to trickle out of my ass, as I struggled to sit up.

"I knew you'd be good at that, but fuck, I didn't know how good," Phil said, between deep breaths.

I could feel my face getting red. Somehow sitting here, cum in my ass and covering my chest, I could still blush at the praise.

"I'm going to take a shower and clean up; you're welcome to, as well. And you can't drive after that tequila, so you're sleeping here," Joe said, as he headed to the bathroom.

There was a long, awkward silence, as Phil and I sat there, just catching our breath and recovering.

"So, you should know this is a one-night thing. Joe knew I needed to get this out of my system with you, pent-up energy from all those nights in college, when you didn't realize you were flirting with me. But he and I are pretty good together, and neither of us wants to be in a throuple. Too complicated."

I thought I'd feel crushed, but I wasn't. Disappointed, maybe, but mostly just felt spent. "I'm happy for you guys. I'm still figuring my own shit out, so probably not ready for an actual relationship."

"Let's grab a shower and clean up. No sense in sleeping on the couch, we have a king, you can take the middle, that seems to be your favorite position," he said, with a smile growing across his face.

I woke up in the middle of the night to the feeling of a lubed up cock rubbing my ass cheeks. I didn't know who it was, until I started moaning and a hand covered my mouth.

Joe whispered, "He's a light sleeper."

He very deftly managed to enter me without waking Phil. I moaned into his hand as he took my ass, cumming after only a few minutes fucking me. He whispered something I couldn't quite hear before rolling over going back to sleep.

The next time I woke up, the only pounding was in my head. I tried to stealthily slide out the bottom of the bed. I put on my clothes from the previous night and went to the kitchen. I got myself a bottle of water and two aspirin from the cabinet, and was about to sneak out.

I paused, then went back, spent a few minutes picking up the clothes they had torn off, folding them, and placing them nearly at the end of their bed. I got all the tequila glasses and emptied them and put them in the dishwasher. I got two more water bottles and some more aspirin and left it on the nightstand next to their bed. I left their apartment, noticing I was half hard, and deeply satisfied.