When I wake up the next morning, it’s with a pleasant sort of ache. There’s a song in my heart and a skip in my step as I slip out of my bathroom, freshly showered and ready to face the day. Apparently my good mood is infectious, though my mother can’t know exactly why I feel so peppy. I can’t tell her that a man who hired me for a night of pleasure is tap dancing through my mind, that I can’t wait to hear from him for another night together. He seemed rather excited about the prospect of getting me into his sex dungeon of sorts and though I was slightly agitated, I had little doubt that I’d oblige his request.

It was just a matter of him contacting me, first. It’s not like you can message your client and tell them, hey, pay me another five grand for sex I thoroughly enjoy and would offer for free. At least, that’s the impression I had from this whole… scenario. I had to repeatedly remind myself that this is a strictly professional relationship and I can’t allow the lines to get blurred. The moment I start developing feelings for the man, there’d be no turning back and our working relationship would be ruined. It’s wasn’t like I was in love with him, it’s just… an infatuation! A passing crush on the guy who’s paying to fuck me.

I couldn’t be more screwed if I tried; literally and metaphorically.

It was nearly five in the afternoon when my phone vibrated. I felt my heart immediately leap into my throat. Surely he wouldn’t contact me again so quickly? Though, I couldn’t deny that I’d gotten my hopes up somewhat. When I swiped the screen, I was thrilled to see a text message from the very man I’d been daydreaming of. It’s short and to the point, simply reading ‘My place at 8’. There’s no room for argument, not that I’d dare pretend that I was any less than thrilled by the idea of meeting with him.

The following hours couldn’t seem to pass quickly enough. My mother is conveniently catching a nap when I slip out the door. I’m so used to telling her everything, but this is one thing I have to keep on the down low. I can’t risk getting arrested or something equally terrible, leaving my Mom to fend for herself. The money I’m making from my nights with Caleb is enough to get the debt collectors off of our back, at least for a little while. Five thousand, however, isn’t enough to support my mother for the rest of her life.

The drive to Caleb’s place seemed to drag on for an eternity, though I’m probably going around twenty over the speed limit. Thankfully, there are no cops to throw a wrench in my plans. Rushing inside to the elevator, I enter the code and step inside, bouncing up and down on my heels as I ascend up to the penthouse.

Upon arrival, I’m immediately greeted by the sight of Caleb lying naked on the couch, boredly flipping through the tv channels. His eyes widened in delight upon seeing me and he shifted to his feet. It’s a bit embarrassing that he’s already so comfortable with me; enough to lie around naked when I’m coming over. Considering the nature of our relationship, I can’t say it’s too surprising though.

“Maggie! I’m so thrilled to see you,” he grins, approaching me with a smile. My eyes are immediately drawn to his manhood and it’s all too evident just how thrilled he is. I smile to myself, setting my purse on the coffee table.

“Right to the point, aren’t you? I have some news that should make you all the happier. I think I want to experiment in your sex dungeon a bit…,” I trail off, feeling a bit nervous as his eyes widen further. His cock stiffens and all at once he draws me into his arms.

“That’s perfect. Just perfect, baby. Go ahead and get undressed, I need to do a bit of setup, but I’ll call you in as soon as I’m ready,” he announces, kissing my forehead before rushing off to the room in question. As I undress, I can only wonder what exactly he’s got to ‘set up’. However, I’m left with little time to actually wonder as he calls out for me, peeking his head out the door. He has that increasingly familiar glint is in his eye and I try to take long and confident strides towards him. I find myself faltering a bit, however, when he steps aside to allow me inside. There are shackles suspended from the ceiling, though they seem to be padded and not made of the steel I might have expected. There is a matching set on the floor and I can tell from looking at them that it’ll be a bit of a stretch.

“Uhm… what did you have in mind?” I ask nervously. He guides me to the suspended shackles, gauging the height before lowering them a bit. Still a stretch, but I won’t be ripped in half from the looks of it.

“Just a bit of an introduction. Nothing too intense for your first time,” he says warmly. I part my lips to speak and he very gently presses a finger to my lips. “No speaking unless I address you. If you are to speak to me, in this room I am your master. You will call me ‘sir’. The safe word is ‘red’. Do you understand?” he continues, his tone growing serious. I nod hesitantly, pausing for a moment before shaking my head.

“Safe word?” I implore and he reddens a bit, averting his gaze.

“I forgot you’re not familiar with all of this. The safe word is what you say if you want me to immediately stop what I’m doing. Things can get intense and I want to be sure you know you’re allowed to have your limits,” he assures me. A bit of uncertainty creeps up within me as I wonder what he plans to do to me. However, I simply nod again before allowing him to strap me into the suspended shackles. My arms are pulled up tight, my breasts thrust out for all to see. As if to strip me of my last piece of dignity, he spreads my legs to stretch me even further so I can be strapped into the second half.

After a moment, he steps away as if to admire his handiwork. He reaches down to slowly stroke himself and I’m forced to watch. Not that I’d turn away. After a moment, he ceases his strokes and circles around behind me. I feel him rubbing my rear, but before I can get too swept up in the sensations, he smacks a hand firmly against my asscheek. I gasp, tensing up as I await the next strike. However, it doesn’t come. Instead, he shifts away from me for a moment to grab something else. Panic grips me for a moment as he blindfolds me, but I try to swallow my unease.

“What’s the safe word?” he inquires gently.

“Red,” I reply softly. He hums his acknowledgement, circling around behind me to do… God knows what. I’m surprised when he reaches down to spread my cheeks. He presses a finger to the tight ring of muscle, his finger covered in some slick gel that I can only guess is lube. I stiffen against the intrusion, but he simply continues to work his finger inside me. After a moment, he slips another inside of me. Gasping, I take a moment to adjust to the invading digits. Then, as soon as I’ve gotten used to the sensation, he removes his fingers. For a moment, I can’t feel anything. His touch is absent and I can’t even hear him breathing. “Caleb…” I implore, only to receive a sharp slap on the ass. I cry out in pain, though it’s mixed with a strange sort of pleasure.

“You are to call me Sir,” he says assertively. I nod my head obligingly, the sting in my rear bringing a tear to my eye.

“Y-yes, Sir. What… what are you going to do to me?” I ask nervously, able to sense him looming behind me.

“Have you ever been fucked in the ass?” Caleb asks crudely. A blush covers my face and I manage to stammer out a response to the negative. “That’s about to change. The sensory deprivation from the blindfold will heighten your other senses,” he rumbles. I begin to tremble in the suspended shackles, but don’t move away as he begins to probe my hole again. This time, something larger than his fingers presses against my hole. He slowly enters me and the initial pain is agonizing. I manage a choked cry, unable to squirm as I’m held firmly in place. The thing he’d said about the blindfold is all too true and the sensations wash over me like nothing I’ve ever felt before.

Though his sizeable member is obviously well lubricated, there’s still a sting as he pushes inside of me. I feel stretched to the limit, but I’m surprised as I feel a gentle touch begin to brush against my clit. It’s not enough to take my mind off the strange mix of pain and pleasure from behind, but the combined sensations are enough to work me nearly into a frenzy. I’m gasping, drooling as he pounds into me. All at once, my orgasm washes over me in a rush. A strangled cry spills past my lips and I unwittingly clench my ass around him. That seems to be enough to push him over the edge and he moans loudly as he empties himself inside of me.

“Thank you, sir,” I say shyly, thinking he may enjoy hearing it.

“Good girl. From now on, this is my hole. Only I can touch you here,” he declares, pulling out of my stretched ass. I nod obligingly, feeling exhausted as he circles around to take off the blindfold. There’s an undeniable thrill in his gaze and I can’t deny that I feel much the same. Feeling owned by him is one of the most addictive feelings in the world.

Though I don’t remain in the penthouse for much longer after our little… session, I find myself feeling more fulfilled than… quite possibly, ever.

Can this get any better?