The Sadist Has Feelings Too

Mason's pov

Saturday 3rd July 2021

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This painting will be the death of me. I just can't seem to get the colours right of the dog's fur. I've done paintings for this client before because I do commissions so I know I have to get it right to keep her business. The painting I'm doing now is of her Great Dane that I've actually met when I dropped off the last painting. It's a tan colour but I can't get the right shade and I have to leave soon to go to the club.

"I can do this tomorrow," I say to myself as I stand up from my little stool and put away the supplies. I change into some clothes that aren't covered in paint and get my bag with everything I need.

I'm meeting Will and Cole in the subs room tonight so we can chat before we go and find a Dom for the night. Well Cole has his husbands Nathan and Marcus, so he's already got some people for the night.

The club we go to is called Club Sin, it's a gay bdsm club where kinky guys can indulge in their dirtiest fantasies without judgement. Some people have contracts where they are in a Dom/sub relationship whereas others like me stay single and have one night stands.

It's a little more difficult for me to find doms because I'm female to male transgender. I've had top surgery but not bottom so I still have a front hole. The testosterone I take has made my former clit grow to be an inch long so the doms I get with just refer to it as my dick. Majority are very accepting, although there are some assholes but Marcus deals with them. He's the Master Dom of the club, he's in charge and looks out for everyone.

I'm hoping to find a tough sadist, I really need a good fucking tonight. I haven't been with anyone rough in at least two weeks and I'm craving a whip on my skin or a dick ramming into either of my holes.

I go out to my car and drive to the club as my favourite music plays. I park in the usual place then I put the code to open the door and go straight to the subs room. I see Will is already here so I go over to our lockers and he gives me a hug.

"Marcus came in looking for you," Will tells me. "When you've changed you need to go to his office."

"Am I in trouble?" I ask cautiously.

"I don't think so, I think he's found a Dom for you," Will says with a wink.

"Really? I didn't even know he was looking," I say with a blush.

"Don't be nervous! I'm sure he'll be perfect for you if Marcus is suggesting it. Look at Issac and Dylan, Marcus got them together and they're an amazing couple," Will tells me as Cole arrives.

"Good evening my cherubs! How are you doing?" He asks with a cheery smile. How is he always so energetic?

"Marcus might have found Mason a Dom," Will says excitedly.

"You have to let us know how it goes!" Cole says as he looks at me. "Although I'm mad Marcus didn't tell me, I could've tested the guy first."

"Don't be angry with him," I say to Cole and he sighs.

"Fine, but only because you're so cute!" Cole says and plants a kiss on my lips before he starts stripping off to get showered together.

"You're always so hyper," I say with a small laugh.

"Not always, I'm not on a morning or after sex," he says as I take my clothes off.

"That's a lie," Will laughs. "I've seen you bouncing off the walls even after sex on the couches."

"Well sometimes, but majority of the time I'm tired after it. Having two men fuck you really tires you out," Cole says.

"That's true," I say with a blush as we go to the shower stall.

We all share the stall and help each other shave when we've done our enemas. I only trim my pubes because shaving completely gives me dysphoria. That's why I keep the rest of my body hairy, but I do trim so it's not too long.

"I'll see you guys later, I've got to see Marcus," I say when we leave the subs room.

"Tell Marcus he better hurry up because my ass is ready for his dick," Cole shouts as him and Will walk down the corridor. I blush deeply and go to Marcus' office quickly. I knock on the door and he tells me to come in.

"Will said you were looking for me?" I say as I step inside, my eyes going straight to a man sat on the couch. He's in only leather pants and has his sculpted chest out on display as he looks at me coldly.

"Come sit down Mason, I'd like you to meet Damon, he's a new Dom and I think you would both be very good for each other," Marcus says as he gestures to the other couch. I keep my eyes lowered because Damon is radiating dominance that is making me want to drop to my knees already.

"Hello Mason," he says in a deep voice.

"Hello Master Damon," I reply quietly as I sit down.

"I've looked at both of your interests and I think you'd both be good to have scenes together. Although Damon doesn't want a contract," Marcus says with a pointed look at the sexy man.

"I just want you in my playroom some nights. No strings attached," he says and I nod, keeping my eyes on his legs so I don't come across as rude if I catch his eyes. And maybe because his intense gaze is making me feel tingly.

"That sounds good Master Damon. Would you want me tonight?" I ask nervously.

"I would, I'd like to go straight to my playroom if you accept," he says and I nod quickly.

"I'd like that Master Damon," I reply.

"You two can go to Damon's playroom now," Marcus says and Damon stands up.

"You can crawl behind me slave," Damon says firmly and I get down on my hands and knees without hesitation.

"Yes Master," I say and he starts walking. I follow on my hands and knees and thankfully he walks slowly so I can keep up. I feel myself getting wet in my shorts already just from his firm commands. We get to his playroom and I crawl inside as he locks the door.

"Inspection," he orders and I stand up and put my hands on the back of my head. I keep my eyes looking down as he walks around my body. I jump slightly when I feel his hands on my ass over the shorts.

"You have a very nice ass," he says and I bite my lip so I don't moan out loud from his hands massaging me. They slip around to the front and unzip my shorts, pushing them down to my ankles and then his fingers feeling close to my little dick.

"Step our of your shorts," he says in his baritone voice. I do as he said and wait for the next command. His hands rub across my body and goes to my nipples where he pinches them harshly, making me gasp in pain. One of his hands goes up to settle around my neck as the other goes down and rests against my dick.

When I get aroused it gets hard like a dick does so Master Damon doesn't hesitate to rub it and make me moan. I try so hard to keep my hands on the back of my head as he jerks off my long clit with his fingers.

"Please Master Damon," I beg and he pulls his hand away.

"Just call me Master," he says in his emotionless voice.

"Yes Master," I reply as he stands back from me. He goes to the grid and beckons me over with his finger. I walk over and let him attach cuffs to my wrists then clip them to a chain hanging from the grid. He then pulls it to stretch my arms up.

"Remind me of your safewords," Master Damon says.

"Red to stop, yellow to slow down, Master," I say and he nods. I watch as he gets a paddle and a whip then puts the whip down in front of him, keeping the paddle in his hand to use.

I inhale a sharp breath when he rubs the paddle across my stomach to tease me.

"Look at me slave," he orders and I lift my eyes to look at his sculpted face. His cheekbones are so mesmerising. "I'm going to give you some warm up hits with a paddle then we'll get to some real fun with the whip. I expect you to thank me after every hit."

"Yes Master," I say as I make sure I keep eye contact. His eyes are such a dark brown it's almost black to match his hair which just adds to his overall appearance. My body gets anxious as he walks to the back of me slowly. I suddenly feel the thud of the paddle on my ass which makes me gasp.

"Thank you Master," I say just as another hits my other asscheek. I thank him again and he slaps my ass several times in a row with the leather covered wooden paddle, making a stinging pain build up.

"Thank you Master, please whip me Master," I beg after the burst of the paddle.

"I decide when I whip you slave," he says firmly and hits the back of my thighs with the paddle.

"Thank you Master!" I say as my hands hold onto the chains above me tightly.

He hits me several more times until my chest, back, ass, and thighs are a light shade of pink and ready for the whip. He puts away the paddle and picks up the whip, his arm muscles tensing beautifully when he cracks it in the air. He tests his strength for a moment by cracking the whip again which sends shivers down my spine.

"How many do you think I should give you slave?" He asks as he stands behind me again.

"It is up to you to decide Master," I answer respectfully.

"Correct answer," he says before I feel the sharp pain of the whip across my shoulder blades. I scream in pain but I can only feel myself getting wetter.

"Thank you Master," I breathe out as my body writhes as the burning pain from the whip lingers on my skin. I hear it crack again as pain explodes across my ass cheeks and makes my body tense up. I thank him again and watch as he walks around into he's stood in front of me with his dick now out of his leather pants. It's the perfect length for me, probably 6 inches but it's also quite thick. He's circumcised which is interesting. I can't help but stare at it which makes him smirk.

"Do you like what you see slave? Do you want me to fuck you with it?" He asks and I blush as I nod my head. "In words slave."

"I want you to fuck me Master," I say quietly as my cheeks burn bright red.

"I'll give you one more whip then I'll fuck whichever hole I feel like," he says as he raises his arm to send the whip across my chest. I let out another scream as it hits my left nipple. He drops the whip and steps in front of me as I recover my breathing. His hand goes between my legs and rubs my front hole as he smirks again.

"You're so wet for me slave," he says and lifts his soaked hand and makes me lick it clean. "Clean up your mess, whore."

I suck on his fingers and lick his hand to get all my juices off him as he slips his other hand down and pushes a finger inside my front hole. I moan when he brushes my sweet spot and forces another finger inside me roughly. I love how he's taking control as he uses his thumb to rub my dick and his fingers to fill my hole.

"Maybe I'll fuck this hole," he says as he pulls his fingers out and makes me clean those ones too. I look down at his dick as he pulls his pants down more to expose his muscular thighs. He gets a condom from his pocket and puts it on as I get ready to be fucked by his beautiful dick.

"Lift your leg around me," he orders. He puts his hand on my right thigh so I lift that leg and wrap it around his waist as he lines his dick up with my hole. He rubs the head on it a few times before he pushes forward and easily slips inside my very aroused hole. The thickness is a little much and makes me wince as the entrance to my hole stings as it gets stretched.

"Do you need me to wait?" He asks cautiously but I shake my head.

"You can move Master," I answer and he nods. He puts his hand on my waist and the other on my thigh to keep it up as he pulls out and pushes back in. I moan as he starts thrusting roughly straight away, giving me a mix of pain and pleasure that's driving me insane.

"Master it feels so good," I say as I tip my head back. His dick rams into me quickly and deeply as he lets out strained groans. His dick feels so good in my hole as he holds onto me in a bruising grip.

"Keep moaning for me slut," he says in a husky voice as he pistons into me and drives me closer to cumming.

"I'm going to cum Master, please let me cum," I beg but he slows down his thrusting.

"Can you cum more than once?" He asks bluntly and I nod.

"I can Master," I answer and he nods as he starts roughly fucking me again.

"You can come whenever you want," he says as he uses his hand to rub my dick again. I let out loud moans as my abs contract and my body jerks forward. Pleasure fills me as I moan uncontrollably and let my body tremble at the intense feelings going through me. Master Damon doesn't stop rubbing me and fucking me as pain starts to take over as I get too sensitive.

My body jerks to get away from the overstimulation but Master Damon keeps a tight hold on my thigh.

"Please Master, it's too much," I beg but he ignores me because I haven't said my safeword. His face is full of lust and something else that makes my body shiver as his dick fills me up and rams into my sweetspot. The oversensitivity slowly turns into painful pleasure as Master Damon grunts with his powerful thrusts up into me.

"Cum for me again slave," he orders as his hand keeps working my dick. I let out a few breathy moans as I start to get near the edge again, my dick much more sensitive and ready to cum already.

I drop my head back and pull on the chains as my body is overwhelmed with another orgasm, Master Damon's dick feeling amazing inside me. I moan loudly as my body trembles again and makes Master Damon groan. I feel his dick pulse inside me as his hand on my thigh tightens and his thrusts get sloppy.

He slows down until he stops and pulls his dick out of me. I take deep breaths as I regain control over my shivering body. He puts my leg down on the floor and uncuffs my hands as I still try to catch my breath.

"Lay down on the bed, I'll massage your shoulders," Master Damon says and I nod as I lay on my front on the bed. The bed dips beside me then I feel his hands gently massaging my muscles. His massage isn't the best but I'm still grateful that he's trying to do it. His hands seem scared of my body as he carefully rubs my muscles.

"Thank you Master," I say quietly. "I really enjoyed tonight."

"You're welcome, would you be willing to have more nights together?" He asks me.

"Yes please Master," I say and smile to myself.

"Good, I look forward to our time together."

"Me too Master."