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Once my fingers are coated with lube, I make sure to spread it around his hole, getting him ready for me. As I run my finger over his puckered hole, he gasps, arching his back as he pushes against my touch.

I press little soft kisses down his spine, sucking and nibbling as I slowly press the tip of my finger into him. Jake sucks in a shuddered breath, and his body tenses beneath me.

Before I can say anything, Indie says what was on the tip of my tongue. “Breathe, Baby. Don’t tense, just relax. It’ll feel so much better if you are relaxed.”

Jake lets out a harsh laugh that turns into a scoff. “Easier said than done. How do I relax?”

Indie gives him a mischievous smirk before leaning down and kissing him passionately. As soon as he melts into her, I feel Jake relax beneath me, and the rest of my finger slips in with ease.

Jake groans as he feels me press all the way in, but his noise is swallowed by Indie. Her gaze is fixed on me, letting me know I should carry on, though she never breaks their kiss.

I move slowly at first, helping him to get used to the feel of having something in his arse, but when I’m sure he can handle it, I quickly add another finger beside the first.

It slips in easier, and the guttural sound coming from Jake’s lips lets me know it’s tipping closer to pleasure than pain. I make sure to stretch him out as best I can with my agonisingly slow strokes, preparing him to take all of me.

It’s not long before Jake is enjoying the sensation of having my fingers in his arse, and I reward him by speeding up. I press into him deeper, making sure the tips of my fingers sweep over his prostate, and the little whimpers that escape him are like music to my fucking ears.

“Does that feel good, Pretty Boy? Do you like having my fingers in your arse?” I growl, squeezing his arsecheek with my free hand.

He grunts, but doesn’t break away from kissing Indie to respond. I know he’s enjoying himself as he’s rocking back against me, fucking himself on my fingers when I don’t thrust into him fast or deep enough. But that’s not good enough for me.

Using the hand that’s caressing him, I quickly bring my palm down hard against his arse cheek, while thrusting my fingers hard and deep inside him. “Use your words, Jacob,” I snap.

Jake cries out when my hand makes contact, but it quickly turns into a cry of pleasure when my fingers hit that sweet spot. He pulls away from Indie, who is smirking like she knows exactly what he’s feeling right now.

Jake’s eyes are wide as he turns his head over his shoulder to look at me. His lips are swollen from kissing, and there’s a flush to his cheeks that makes him look even more pretty than usual. But it’s the desperate longing in his eyes that makes my cock twitch.

“I’m sorry, Sir. It feels amazing. Please, can I have more?” he whimpers, trying not to rock against my hand as I continue to thrust my fingers into him.

I love seeing this dangerous mafia leader, who doesn’t answer to anyone, submit to me and only me. I want to use him, mark him, and make him mine.

“What more do you want?” I ask slyly.I want to hear him fucking beg me.

“You. Your cock,” he mutters, his gaze dropping, so he doesn’t meet my eyes as he says it.

I slap his arse hard again, opting for the opposite cheek this time, and as he yelps loudly, I take a moment to admire the matching red handprints on each side.

“Keep your eyes on me when you beg for my cock,” I tell him sternly, and he quickly nods his head.

“Sorry, Sir,” he replies, his dark gaze now fixed on mine, letting me see how much he wants this. “Please, can I have your cock?”

The corner of my lip lifts into a smirk as I slow my fingers down, scissoring them as much as I can as I pull back, getting him ready for me.

When I pull my fingers out, he lets out a hiss that turns into a moan, as I gently rub my finger around his red rim. If my fingers stretched him this much, he’s going to be pushed to his limit by my cock, and I can’t fucking wait.

He looks at me with desperation in his eyes, whimpering at the loss of my fingers. Before he can say anything, I grab hold of his hips and flip him over, sitting him on the sofa with his arse at the edge. I push his body backwards, before lifting and parting his legs.

“Hold them open wide for me,” I tell him, motioning for him to wrap his hands around his knees to pull them back. As he does, it spreads his arse wide, presenting himself to me.

His dick is already hard again, resting against his lower stomach, with beads of pre-cum leaking from his swollen, angry-looking tip. The vein running along the underside of his shaft is prominent, and I can almost see it throbbing with desire.

Jake rests his chin on his chest, giving him a better view of where I’m standing between his legs. The sofa isn’t the ideal height for this position, but there’s no fucking way I’m moving us now, and I meant what I said before, I want to see the look on his face when I take his anal virginity.

He looks nervous, apprehensive, but very turned on as he draws in short, panting breaths. He’s watching my every movement, as I reach over and grab the lube again, gasping when I pour a generous amount over his puckered hole.

His chocolate eyes turn almost black as he watches me fist my cock, spreading the lube all over my length, getting it ready for him. I then gently massage the lube into his rim, sliding the tip of my finger in a few times, pushing as much as I can inside him.

When I pull back and shuffle into place, crouching down until my dick lines up with his hole, I pause for a moment to make sure this is still what he wants. I meant what I said before, nothing happens unless he’s sure.