The Big Goodbye

My best friend messages me. “You got a screwdriver?”

“What kind?” I ask. He sends me a picture of his computer. 

Being in Canada’s a tough sell right now, with so many cities going into lockdown because of Covid. His parents made him an offer he couldn’t refuse, and now he’s heading back to his home country.

This guy is different that my usual anonymous favourites. After five years, I know everything about him, his favourite colour, his hopes and dreams. I’ve heard about every boyfriend he’s had. He only likes hairy bears, though lately his tastes have been broadening. He goes through relationships every few months. He wants what he can’t have, and once he can have it, he loses interest. I’ve heard the same story from him, as he goes through guy after guy. I always tell him so, he always says “Oh yeah!” Like its some huge insight.  

But him and me, we’re just buddies. No complications. Nothing even happens between us. Except that one time. But we never talked about it after.

I hope he’ll update me on his life today. Is he still seeing the Lawyer? Then there’s Spanish Guy. And the new one from London.

I get there with my screwdriver set. He’s out of work now and lives in a basement room. (It seems the parental pressure to leave came when it posted a video of it). 

His life is in boxes. “I can’t take these,” he says. “You want them?” 

Sure. I sigh. I’ll value-village them. Secretly, I plan to take one sweater I’ve seen him wear. Chuck the rest.

“Where’s the computer?” i ask. 

He points to the floor. The thing has no case. I kneel down and look at it. Instead, I see something fuzzy on the floor. I pick them up. A pair of fuzzy handcuffs, lined in neon fur.

He grins. “I just found those. They’re from Aroon.”

“Aroon? I don’t remember you telling me about these,” I smiled. “That was last year, right?”

“Two years ago.”

“Oh, Aroon, Aroon, how much I didn’t know.” I smile. His relationship with Arron soured after they argued over a restaurant bill. 

Something changes. He seems to make up his mind. 

“Hold out your wrists,” he says. 

“What?”

“Hold out your wrists. Behind you.”

I kneel down on the floor and put my wrists behind me. He fumbles around and clasps the handcuffs on me. 

“Tight?” he asks.

I nod.

“Close your eyes.”

“Okay.”

“WHAT DID YOU SAY?”

Oh shit. I remember this.

“Yessir. Thank you sir.” I close my eyes, and immediately he slaps me on the side of my face. My cheek is stinging and my ears are throbbing. “Thank you sir.”

He slaps me again. I flinch, and then he unexpectedly slaps the other side. “Thank you sir.” I peek and see him grinning at me, like I’m his new toy.

“You can open your eyes.” He falls back on the bed, sticks his feet at me. “Smell them. Smell those dirty socks.”

I pretend to sniff them, exhaling instead. The floor is full of covid, for all I know. 

“Take them off for me.”

My hands are still cuffed behind me. I slide over on my knees, and see that thankfully they are ankle socks. I grab them above the heel and deftly slip them over and off his foot. He doesn’t help at all. He just watches me struggle.

“Lick my feet, slave.”

“Yessir. Thank you sir.” I stick out my tongue. The sole of his foot is cold and thick, and I can see dust on them from the floor. I dance my tongue tip across it. When he sticks out his toe, I take it into my mouth and suck on it, and he looks down at me approvingly.

“I heard you like to suck.”

“Yessir.”

“Get up,” he says. He stands up and I’m kneeling in front of him. “Smell it.”

I can see his boner through his track pants. I press my face into it, tracing its length through the thick fabric with my lips.

He grips me by my shoulders and lifts me up, then slips his T-shirt down over my head. I’m in the darkness of his shirt, with my face pressed against his chest. He lowers himself, and mashes his nipple against my nose. I reposition so I can flick it with my tongue. He stands there for a few seconds, enjoying the flicking, before getting up again. He points to the band of his underwear under the track pants.

“Take them off. With your teeth.” he says.

Like I have a choice? I lean over, cuffed hands aching behind me, and deftly grab his waistband with my teeth and pull it down. It takes a couple of tries as it gets caught getting over his bulge. 

I stay there, kneeling on the floor and staring at my best friend’s dick. I’ve often wondered what it was like and I finally get to see it. It’s not huge, but deliciously round and pointing straight out at me.

“Well, what are you waiting for? Suck it.” he demands.

“Yessir.” I breath. I open my mouth and slide in around him. He stands there, hands on his hips, and watches. Bobbing my head back and forth is not easy. If I go too far forward, I’ll fall over, and I won’t have my hands to catch me.

He steps back. “Bend over. Take your underwear off,” he tells me. I lean down, touching the hard wood floor with my forehead, and I here my open a drawer behind me. I manage to slide my underwear down over my thighs, and they stop there, leaving me even more helpless than before. With excitement and rising panic I here crinkling and a plastic tube snap shut, before I feel his body heat behind me.

I’ve been fucked before, but just barely. I am still not sure I like it. I’m leaning towards no. But he’s my friend, and suddenly I feel him slip between my but cheeks, slippery and cold and gooey.

“Relax your hole,” he says.

“I’m trying–” I say.

SLAP. The crack echos in the room, and I yelp as my ass stings. 

“Yessir.”

“Relax it…. Relax,” he orders. I’m trying my best but these muscles are still unfamiliar to me. It doesn’t matter. He shifts slightly and then pushes hard, against something that is not supposed to give but does.  I grit my teeth and softly whimper into the floor, hoping he does not hear me. He;s fucking me now, pushing further into my body with each thrust. My whole body tenses, and it takes everything out of me just to remain on all fours there, and not fall away from him.

After a minute he stops, and sits on the bed. “Get up,” he says. 

As I roll on my side to get up, I pull a little to hard, and the pink handcuffs snap apart, releasing my arms. I keep them together to hide it. If he notices, he doesn’t say. 

“Be honest with me. What do you like better?”

I hesitate, and look down. “I like to suck, sir,” I tell him.

“Really?” he asks incredulously. “OK. Get rid of the shit covered condom and suck me, then,”

“Thank you sir. Thank you!” I say, with perhaps a little too much enthusiasm. He lays back on the bed and grabs his phone, not even giving me his attention. I use my hands to pull off the thing, revealing his stiff, moist dick. Now I am in familiar territory. I settle down and get to work.

It is difficult to tell what, if anything I am doing right, and I worry that I will not succeed. The minutes pass, and my mouth gets tired, but I am determined. I try going fast, and quickly tire. I try going deep, I try sucking, which gets difficult. The only thing that works is the odd time he slaps my cheek. That makes him harder.

It must have been 20 minutes later when he shifts his legs slightly and finally looks up at me. He’s going to stop me now. I’ve failed. I meet his eyes when suddenly I feel the pulsing, and my mouth is filling with his load.

I don’t get up, but I remain there, with his dick draining in my mouth, for several minutes while he reaches down and runs his hands through my hair, massaging my scalp.

“You are good at it,” he tells me.

“Thank you sir.”

He gets up off the bed. “I gotta piss,” he says. “Come over here.” He moves to stand directly over his computer. It’s lying on its side with the open motherboard exposed to the air.

“Should we get a towel?” I offer.

“Do you want another slapping? Just don’t spill.” he orders.

I sidle up to the other side of the computer, and gently wrap my lips around his dick. I can feel the delicate folds of skin stretched on its underside. I open wider to try not to touch it. We stay there for a while.

“Its just a little hard,” he says, under his breath.

Finally, he grunts and I immediately know it because a few drops of pungent urine drip onto my taste buds. He lets out a deep breath, and some more spurts out. 

He stops and says, “Swallow it.”

I’m sweating now. The computer is right under me. I gulp down a mouthful of hot piss, then open my mouth again for more.

He’s relaxed now, and immediately he unleashes a torrent. The stream hits against my tongue, making it tingle. I can hear it splashing around inside of my mouth as it fills up. Then, when I’m almost ready to pull away cause I’m gonna spill, he stops. “Swallow.”

It takes two gulps to get it down this time. Then he puts his soft dick in my mouth, grunts, and bangs it against my lips, shaking out the last few drops for me.

I sit there obediently, not moving, waiting while he zips up.

“Uh, you can get up now,” he says. “It’s over.”

Later, over a Starbucks, we’re talking, and he asks how it was.

“Actually, it was quite a big load,” I tell him.

“Really? Wow, cause I had sex with Spanish Guy last night too.”

I Topped

He was a tall, skinny 18 year old twink last time. Last October, at 9 in the morning, he invited me over. After I got there he casually mentioned that he was taking a lot of drugs the night before. Okayyyy… His cock was soft and reeked of tobacco. I was afraid I’d get high as I sucked him off in his basement, listening to his younger brother stomp around upstairs. Though I couldn’t bring him to cum, I couldn’t get the taste out of my mouth for the whole day. He was hot, though, and had a really casual attitude that made me feel super comfortable with him. Even if nobody climaxed, it was darn fun to be around him.

Now, a year later, his Mom was working again and his brother was in school, and he had the place to himself during the day. He’d mentioned something about milking him while rimming him, wanting to be “sub trained”, so I brought along a flogger. He knew I wouldn’t top, but he was so horny today it didn’t matter.

“I forgot to ask,” he messaged. “Are you OK with watersports? Like with me being peed on, not you.”

Yes and yes!

“I’m gonna take a shower. Definitely just come right in the sliding door and make yourself at home,” he wrote.

Usually I hate walking into stranger’s houses. Luckily when I showed up he let me right in and led me to the living room.

“Hi!” he said brightly, brushing his shoulder-length brown hair out of eyes. “Let’s get some porn going here.”

I looked around nervously, as the front door of the house was right there, and we were visible through the kitchen to the sliding doors in the backyard. A family desktop computer sat on a small table in the living room, and he already had 18 tabs of Pornhub open.

“Don’t worry. My mom’s at work and nobody’s coming back for a while.” He nonchalantly dropped his pants, revealing a soft cut penis. Then he leaned down to the keyboard, butt in the air, and started looking through the videos.

He picked one with a hot teen in it, but it was just him talking so he had to change it. “So what do you want to do?” he asked, turning toward me.

“Let’s start with the rimming,” I told him.

“My favourite!” He got on the floor. His tiny twink butt pointed in the air and spread, showing his hairless hole. I got down and licked it, and he moaned with excitement.

Without warning, I slapped his ass so hard he flinched and yelped. “Say thank-you sir,” I demanded.

“Thank-you sir,” he said, moaning in pleasure. His penis hung down to the floor, growing hard.

“Very good. Now you will be rewarded.” I slid my head under him and twisted around, sucking his long dick into my mouth. He yelped again in surprise, and then moaned as I used my my thumb to massage his slick hole.

We played a while, with me repeatedly slapping him the teen kept getting hornier. He looked back at me, panting. “What else you wanna do?”

I knew he wanted to be fucked, but I had never successfully topped before. Time to move on. “Well I gotta pee,” I told him.

“Fuck yeah, let’s go to the shower?” he leaped off the ground and bounded down the steps to the basement, cock bouncing under him. I followed him and he rounded a corner, into the bathroom with a small corner shower. By the time I got there, he was bent down on the shower floor with his, tight, slick asshole pointed into the air. “Try to hit the hole,” he begged. “I don’t know what it is, but I am just addicted to that feeling of piss hitting it.”

I pulled out my cock, took aim, and instantly a shower of piss spattered out everywhere. The droplets of pure yellow beaded up all over his back and soaked into his long dark hair. “There you go,” I said as I manipulated it into a stream. I let it all out, sighing with relief as I stood above the teen and pissed as hard as I could directly into his puckered asshole. The sound of it spattering against his skin, running down his hairless balls and dripping down into the drain echoed throughout the tiny bathroom.

When I was done, he turned around and sat down in the yellow puddle of piss, sighing contentedly. “That was awesome,” he said.

“Hit the spot eh?”

“Yeah! I’ll just shower it off quickly now,” Then he closed the glass door, and showered off. As he shampood his long hair, I stood right by the door, staring down at his soapy ass, and rubbed my dick.

“You didn’t bring any other toys, did you?” he asked me once we were back in family room. “I’m kind of weird. I take a while to warm up to fingers in my ass, but strangely cock is no problem.”

“Sorry, I just brought the flogger.” Besides, toy sharing is not safe. “Have you tried a cucumber? Banana?”

His eyes lit up, and he rushed to the kitchen, coming back with a thick yellow banana. We quickly covered it with a condom. He got on the couch and I squirted some lube on his crack, and he began to push it in. I put my hand on his and helped him.

His face twisted in determination, and then he pulled it out. The end of the banana was sagging inside the condom. “It squished,” he said.

“Yeah… Unfortunately if a banana squished there’s no way I’d get in there. The two times I’ve tried before, I’m always too soft.” I took a breath and looked around. “Maybe try a carrot?”

“We have literally no carrots in the house.”

“Marker? Hair brush?”

His eyes widened. “Oh my god yes!” He leaped up the flight of stairs and rummage through a drawer. I saw him grab something and he carried it back down, holding it up high.

“Got anymore of that lube? I mean, I think I might have some somewhere…”

“No problem,” I said, and squeezed a dollop onto his fingers. With one hand, he massaged it over his whole, and lay back on the couch, legs in the air. The other hand was on his phone, finding stuff on Pornhub. I looked down at my own phone, but I didn’t need it. I just stared at the teen on the couch beside me.

He gradually slid his mom’s hairbrush inside himself, and moaned. “I think I found a new favorite thing. I gotta hide this when we are done.”

I just stared at him, transfixed. I couldn’t get my eyes off his hole as it seemed to grip the brush handle on its own and draw it into himself, eliciting a wave of pure pleasure throughout his body with every millimeter he managed to push.

I was slowly pulling on my cock beside him. I was getting very hard and moreover I seemed to be staying that way. I slid off the couch and got a new condom and the lube, and ripped it open.

“You gonna try?” he beamed at me.

I didn’t say anything. Usually by the time the condom gets on I’m squishy again. I squeezed a dollop of lube out and rubbed it over my condom covered cock, which was still hard as ever.

He pulled out the comb and maneuvered himself around, putting his butt over the edge of the couch. He wrapped his hands around hie feet and and pulled them back, and his hole gaped before me. I reached down and positioned my cock head in front of it, and PUSHED.

“Uh uh no you gotta go slow!” he shouted.

“Right, sorry.” I stayed where I was, and started to fuck his hole, just the tip. Gradually I could feel the condom sliding against his skin, letter more of me inside.

“That’s good,” he told me. “Yeah you can go in further now… I can feel it open up.”

And then, all at once, I slid past… something… and I was fucking him. He moaned with each thrust, and I could feel his pleasure as well as my own as I went faster and faster.

“This is great,” he said between breaths. “You’re just the right size and everything!” And then his eyes rolled back into his head as he seemed lost in the moment, still moaning. After a while, a bead of sweat dripped from my forehead onto his taut belly.
“Don’t tire yourself out,” he told me. “I am more than happy with this so far. You are really good at this.

I decided that I really like this guy. I didn’t want to stop, so I kept going. I felt so happy. I topped. I have topped. Am I a top? I just love to give pleasure. And it was plain that the kid was high on pleasure right now, because of my fucking cock inside of him.

Eventually, I did stop, pulled out and lay down to rest on the couch beside him.

He was still gushing about how good I was. “You were so good! I mean it! Some guys are so big and they don’t know how hard to push. I’m so glad you came. I was literally trying to get someone to fuck me all of yesterday.”

When I got to my car I just sat there, smiling. I topped! And then he messaged:

“I know you’re kind of new. If you’re into it maybe I can top you sometime and try and point out the things people taught me that helps.”

“Sure, I’d like that,” I wrote back before I could stop myself.

Too Much Top

“I am hot asian. A few my friends told me so”

Right.

He prefers fucking, but he agrees that I can come over and blow him. I can’t find anyone else that hosts, so it’s him or nothing this week. Turns out he lives in my old apartment building. I park at the market and walk right up to the door. My insides are turning as if I’m on a roller coaster. This is bad. Go back. I knock on the door.

He leads me right into his bedroom. Single bed. A pile of math assignments on the desk. Stuff everywhere. This guy’s a TA.

We get naked. He shoves some shit off the bed and lays down. I get between his legs and start to blow him. It’s fun. He’s hot and his smooth cut dick feels great in my mouth. We go for a while, but I’m not making much progress.

But then he stops, grabs my body. He’s trying to move me. I’m not sure what he wants. Finally, he tells me to turn around. Lay on my front.

Um, yeah but I’m not into anal, I remind him. “It OK, I just hump you,” he says.

He reaches under his desk and pulls a bottle of lube out of a ziplock bag. He squirts it on his dick and he’s on top of me.

WTF is he doing? I clench. I feel the warm slippery slidiness of the lube falling further into my crack, as he humps my ass cheeks. OK, I can deal with this. Whatever, I’m squeezed shut. It’s even a little boring. I’m looking around the room, examining the pile of textbooks. Statistics. Fundamentals of financial models. Just keep squeezing. At least he likes it.

I get an idea. Something I’ve been wanting to try. “Wanna fuck my face?” I ask. He stops and looks at me in surprise. Yeah, that’s more like it. He straddle’s me and starts to fuck my face. I learn that it’s trickier than it looks. As he speeds up he starts to miss or hit my teeth. I do my best, and just enjoy the sight of his taut belly thrusting at me. Fuck, I’m so hard now.

I grab his cock and use my hands and mouth some more. All I can taste is rubbery lube. But he’s turned on enough that he takes over.

“Where you want it?” he asks. I open up and he jets some lube flavoured cum onto my tongue.

I don’t need to cum today. I’m holding out for better. It’s time to leave.

I walk back to my car. I feel the slipperiness in my ass with every step. I can’t wait to shower.

Well, they all can’t be fantastic. Now I know.