An Evening of Firsts by SouthernRoam

After a few minutes of this, you’re satisfied that I can take all of your cock down my throat with no issue, and pull yourself off me. Choking and coughing, trying to catch my breath, I again ask you what you were thinking. Not hesitating, you smack my cheek, and grab the gag from the chair. “That’s the last time you question or argue with me,” you snap. Grabbing my head again, you force the ball gag into my mouth, and secure it tightly around my head. Now tied up, blindfolded, and gagged, I am left completely to your will and cannot do anything about it. Enjoying the silence now, you let out a quiet sigh, with a “Much better,” before moving on to your next task.

Disconnecting one of my leg restraints, you order me to flip over, on my stomach. I comply, and roll over; the restraints around my wrists tightening. Once over, you restrain my free leg again, and kneel down behind me. Holding the bottle of lube, you put the tip between my cheeks, at the entrance to my hole, and squeeze gently. “I promised you a little bit of lube, and even though you have fought back, I’ll keep my promise. Besides…. With as hard as I’m going to fuck you, you’re going to need it,” you tease. You swipe up a little lube on two of your fingers, and push them into my ass, noticing that it’s fairly loosened up now, and add a third finger to make sure the entrance to my ass is lubed up. Withdrawing the fingers, you take your toy in your hand, and squeeze a decent amount of lube down onto it. Catching the excess in your hand, you wrap your fingers around the shaft, and work your hand up and down, lubing it up generously. Satisfied, you set the lube down, and put yourself in position behind me, the tip of your dick hovering just above my ass.

Leaning forward to whisper in my ear, your toy settles in between my cheeks. Biting my ear playfully, you whisper a question to me.

“Are you ready?” you ask.

I nod my head.

“Ready for what?” I manage to utter a muffled “You” from behind the gag. You loosen it a bit, and ask me again, “Ready for me to what?”

Able to answer, I respond, “For you to fuck me Mistress.”

“Good boy,” you answer. “Now beg me.”

I’m quiet for a moment before you hear my response. “Please Mistress, fuck me.”

“Fuck you how?” you taunt, an almost playful teasing quality to your voice.

“Please, fuck me in the ass, Mistress.”

“With….?” you say, leaving the answer open. Silent again, I finally answer, “With your cock.”

Giggling evilly, you kiss my ear again. “Well then, very well. You might want to put your face in the pillow; this isn’t going to be easy,” you tell me. Tightening the gag again as you don’t want to hear me just yet, you push my head back down on the pillow, and sit back behind me.

Holding your toy in your hand, you guide it towards my now lubed up, loose and waiting hole. You trace a circle around the opening with the head to toy with me, but soon after, you pop the head into my ass. The twitch of my legs and clenching of my ass, mixed with a quiet sigh, tell you that it was a mix of pleasure and pain, and you smile, as that’s what you wanted at first. Able to guide it in without your hands now, you pull my ass apart so you can watch your dick slide into my ass. Putting your weight behind it as you did above me before, you apply pressure and the cock starts making its way deeper into my ass, until you reach the bottom; your body pressed firmly up against mine.

You let the toy rest there for a minute, making my ass stretch around it and accommodate it. Very slowly, you start inching yourself back out so I feel every bump and rib of your toy cock, until you’re almost completely out of me, with just the tip of the head still in. Not waiting, or taking it easy this time, you quickly thrust the entire shaft all the way in, slamming into me. I cry out from the gag. Without any mercy, you pull out and thrust fully back in again. Now that you know how loose I am, you take your sweet time, getting the inside of me slick with lube. Pulling in and out slowly, reapplying lube to your toy, before pushing it back in me. Eventually, you’re satisfied that I’m well lubricated inside, and that my tight hole is now plenty loose for your enjoyment, you sink yourself fully into me again, getting a soft moan from me.

“Now, I want you to raise up on your hands and knees, but do not let my cock slip out of your ass,” you tell me, leaning back to rest on your heels, pulling about half of your toy out. Very carefully, I lift myself up on my elbows. I rise up on one knee, and then the other, but as I go to plant my hands down, I accidentally lean too far forward, and your toy slips out of me.

“Tsk, tsk,” is all I hear from you. I can feel you behind me, and you tauntingly slap your cock against my ass a few times. “You didn’t follow instructions. And that means you get it even harder.” With that being said, you guide the head of your dick back into my ass, then grab my hips. Settling in, you pull me back as hard as you can, while thrusting yourself forward, slamming your cock into me full force. You aren’t being gentle with me anymore. Fully aware that I can easily take it, you start fucking me with impunity. Using my hips for added grip, you ram yourself in and out of me, as fast and hard as you can manage. Our bodies slapping together at the force makes an audible noise, but you don’t slow down. You’re enjoying every second of watching my ass bounce from each hard thrust into me, and the sound of my moaning in delight.

You’re also loving how your end of the toy is fucking you just as hard and fast in return, which is aided by a small vibrator you secured to tease your clit. Unrelenting, you fuck me like you’ve been wanting too; hard and long thrusts, making sure your body slams home flat against me every time. You have no intention of letting up any time soon, smiling to yourself at my cries of joy and delight, muffled by the gag and the pillow. “That’s right, you know you love taking it in the ass from me. Keep making those noises. If I can’t hear you, then I won’t think you’re enjoying this,” you say to me, before resuming your ceaseless ramming of me.

Eventually, you slow down for a second, to grab my cock, which was been swinging back and forth from your hard fucking. You push the rings around it back up tightly, as you don’t want me coming just yet, and give it a few slow and firm strokes, just to push me that much closer and tease me that much more. Leaning forward, you place both hands on my shoulders, while pulling your hips back. You lean as close to my ear as you can.

“Now it’s your choice how I give it to you. You have options. Which will it be? ‘Fuck me faster, fuck me deeper, or fuck me harder.’ Those are your options, so choose,” you tell me quietly. I hesitate, not sure what to say. “Choose,” you bark. “Choose or I’ll choose for you, and you’re not going to like it.”

I pause another moment or so, before mumbling a weak, halfhearted, “Faster, Mistress.”

You think for a second. “You know, I don’t like your answer. You took too long, and you didn’t seem like you really wanted it. So now you’re getting all three,” you say, chiding me. Grabbing onto my shoulders tightly, you pull me back quickly onto your toy cock. In this new position, you’re able to go deeper than before, and you take advantage of it. You don’t stop furiously pounding away at me, but now you’re also pushing more when your hips hit my ass to drive your toy in to me as far and as deep as you can. The harder and faster you pound, the more I can feel the rolling waves of an orgasm building, and you’re not even touching my dick.

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