Vincent's pov
Sunday 15th august 2021
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"Have you heard from Stefano?" I ask Emilio when he walks into my office.
"He called to say he is going to Italy with Martina for a few months," Emilio says.
"Good. Hopefully when he comes back he'll accept Enzo is gay and will stop giving me problems," I grumble as I look back to my laptop on my desk. I'm trying to solve an issue with a shipment that the buyer wants today but bad weather means the cargo ship is coming in tomorrow.
"Need any help?" Emilio asks as I furiously type.
"Call the number I will send you and explain his shipment will be late by no fault of my own," I say and text him the number. He picks up his phone and dials the number as he leaves the room. I sit back in my chair and sigh loudly, picking up the box of cigarettes I've been working my way though today. Damian would be pissed but I'm too stressed to care about a punishment right now.
I light a cigarette and take a deep breath of the burning smoke as I let my head fall back onto the chair. I didn't expect taking over as Cappo to be so stressful, Antonio made it look easy.
My phone rings and I see Damian's name on the screen so I answer and put the device to my ear.
"Good afternoon my love, how are you?" He asks.
"Stressed," I mumble.
"I've got an idea for a scene if you can ditch work for a couple of hours?" He says excitedly.
"I could, what kind of scene?" I ask as I sit up and put out the cigarette.
"Well you'd have to go to my house while I finish what I'm doing now and strip naked in the living room. Then you'd have to hump a pillow until I get home and I'd take it from there," he says and I can hear the smirk in his voice.
"Sounds good mi amore, should I go now?" I ask.
"Yes, I'll see you soon," he says and hangs up. I get my keys and send a quick text to Emilio to say I'm going for a few hours before I drive to Damian's house.
I unlock the door with the key he gave me and go to the bathroom to prep. I strip naked and do an enema then trim my pubes with the electric razor. I know Damian likes me smoothly shaven but I don't think I have enough time right now.
I go to the living room and see he's left a pillow on the floor for me. I stroke my dick and think of naked Damian until it gets hard and then I awkwardly straddle the pillow. I start moving my hips forwards and backwards as I lean forward enough to grind my erection against the fabric. I moan and lean on my hands in front of me as I thrust my hips onto the pillow. This is good, why haven't I done this before?
I close my eyes and bite my lip as I keep humping the pillow like a horny dog. My dick leaks some precum onto the fabric as I hear the front door open. I look up as Damian walks in with a small bag.
"What a beautiful sight," he says as he looks across my body. My hips stop moving as I smile at him. "Did I say you could stop?"
I continue thrusting my hips as he approaches me and runs his hand down my back and to my ass crack. He pauses for a second and moves back to look at me.
"Did you smoke again?" He asks and my eyes widen when I realise he can smell it on me.
"I am sorry Master I was very stressed," I say but he cuts me off.
"You agreed in the contract to stop stress smoking," he says darkly.
"Mi dispiace," I apologise as I look down and stop humping the pillow.
"I was going to show you the gift I got you and then take you to the playroom but now I have to punish you. I'm going to tease you relentlessly and if you're good you can ride me. Although I don't promise I'll let you finish," he warns.
"I accept any punishment from you Master," I say respectfully. He sits down on the couch and stretches his legs out as he looks at my naked body.
"Tell me your safewords," he orders.
"Giallo to slow down, rosso to stop," I say and he nods.
"Crawl here and kneel on at my feet," he orders. It's a little humiliating but it's only us in the room and I'm being punished so I swallow my pride and crawl to his feet. I kneel in display and wait for my next instruction.
"Hump my shin," he says as he watches me. I shuffle forward so my chest is against his knee and I'm straddling his foot as I rub my dick on his leg. I rest my head down on his knee so I don't have to look at him as I grind onto his jeans desperately. "If it gets too humiliating you can safeword," Damian says and I shake my head. I can do this. It's not too bad.
"I am okay Master," I say between quick breaths as my dick is stimulated.
"Good. Keep going and you can stop when I tell you to," he says and turns the tv on.
I don't know how long I'm humping his leg for but soon my muscles are aching and I'm so close to exploding all over him. I can hear him watching some kind of tv show and it must have been a whole one by now.
"Please Master," I whimper when I feel like I can't hold back my orgasm anymore.
"You can stop," he says and I sigh in frustration. He makes me kneel at his feet for a while longer as I try to focus on anything but my throbbing erection. His punishment is working, I've had plenty of time to think about what I've done and now I feel terrible. I shouldn't smoke when he's told me not to. I agreed to the rule.
"Straddle my leg and keep your hands behind you back," he orders. I slowly stand up and he widens his legs so I can sit across his thigh, my knees on the couch either side of it. I watch as he strokes me slowly and spreads the precum across my length. I choke on a moan as he tightens his fist around me.
"Fuck my hand and stop when you're about to cum," he orders. He looks past me to watch the tv which makes me feel left out. I lower my head as I thrust my dick into his hand as I moan quietly and whine as I try to get his attention. I hate it when he ignores me like this.
"Be quiet," he says and I stop making pathetic noises and keep fucking his hand. I slow down when I feel close to cumming and eventually stop when I'm almost on the edge. I stay as still as I can while he keeps his fist closed around the middle of my dick. My chest rises and falls quickly as I try not to push myself over the edge. He waits until I'm not about to cum and starts moving his hand slowly as his other hand wraps around my throat.
"I'm going to choke you gently, when I let go of your throat I expect you to beg for my dick. Tap my arm if you need to safeword," he says and squeezes his hand on the sides of my throat as he strokes my dick. I struggle to breathe for a moment but he releases his hand and I take a breath.
"Please fuck me Master, I want your dick," I beg and he tightens his grip again. The mix of pleasure from his handjob and his hand blocking my airway makes me feel to hot and bothered. I never thought I'd like this but my god I could cum right now. He lets go of my throat again and I take a deep breath before I beg.
"Please mi amore I need your cock," I beg him and he narrows his eyes.
"Don't try and win me over with mi amore," he says and wraps his hand around my neck again. He's barely applying pressure but it feels so good as he pleasures my dick in time with it.
He lets go to hear me beg a few more times before he stops stroking my dick and looks up at me.
"Do you think I should let you ride me?" He asks as he makes me look at him.
"I really am sorry for smoking Master, I will not do it again," I say truthfully.
"If I ever catch you smoking again you're getting a much worse punishment than this. I'll let you ride me but you're not cumming today," he says and I nod. I just want to make him feel good at this point because I feel so bad that I ruined his plants for our time together. He unbuckles his belt and pulls out his very hard dick. He puts two fingers in my mouth and I suck on them to get them wet enough. He doesn't give me very long before he reaches back and pushes them both into my asshole. I let out a pathetic whimper as he stretches my ass and leaves a sting.
"Relax," he says calmly and I focus on relaxing my hole. I close my eyes and take a deep breath so my body relaxes more so he can comfortably finger me for his dick. He curls his fingers into my prostate and I rotate my hips to get more stimulation.
"Please," I whine and he pulls his fingers out. He guides my hips onto his dick where he's leaking precum and I slide down until he's filling me up completely.
"Good boy," he praises. "Now make me feel good."
I keep my hands behind my back and raise my hips and lower them back down. I grind my hips on him and he groans as he puts his hands on my hips. I watch his face as he closes his eyes and tips his head back to enjoy me gyrating on his dick. I clench my hole a few times and he grunts.
"Can I hold onto you so I do not fall?" I ask as I find it difficult to stay balanced.
"Of course," he says and I put my hands on his shoulders so I can lift up and down properly. His dick goes into my prostate over and over which is making it very difficult not to cum. My dick slaps against my stomach as I move faster to fuck myself on his large member.
"I'm going to cum," I warn but he puts his finger and thumb behind my balls and holds it tightly to act as a cock ring.
"You aren't cumming today. I don't back down on punishments," he says sternly. I nod and keep going up and down until he starts to groan louder.
After a few more minutes of my best riding skills he tells me he's going to cum and I feel his dick pulsing inside me. He moans so sexily as he cums in me. When he's done he helps me get off him and takes me straight to the shower so I don't leak cum from my ass onto his couch.
"You did so well, you're forgiven now," he says when I'm stood in the shower with his cum dripping down my leg.
"Thank you mi amore," I say and hug him. He takes off his clothes and gets in the shower with me and helps clean my body. I smile when he washes my hair and massages my scalp as he does. My eyes roll back and I let out a moan which makes him laugh.
"You're still hard?" He asks when we're about to get out of the shower. My dick is still painfully pointing up at my stomach so Damian turns the shower water cold to deflate my horny member.
I get out of the shower and dry off with a towel as he tells me he's going to get something for me. I sit on his bed in the bedroom as I wait for him to come back. He brings the small bag and hands it to me with a nervous smile.
"Open it," he says and I take out a small box from the bag. I open it and see a gold ring that matches my collar.
"It's a promise ring, it means I promise that one day we'll get married. Right now isn't a good time because you're still taking over from your dad and I'm still in therapy so it's just a symbol to show that it will happen when the time is right," he explains and I smile widely.
"Ti amo mi amore," I say and hug him tightly. He hugs me back and then slips the ring onto my right ring finger. I smile at the simple band as I hold my hand out to look.
"I love you Vinny, and I want to spend my life with you," he says and I kiss him passionately.
"You are my love," I say and hug him with my head on his chest.
Vinny got in trouble but it ended with some big promises for the future so you can't be mad at me 😉