Naughty Skylar

Skylar was a naughty girl. She did something she knew she wasn’t supposed to do.

She broke a rule.

I smile as I gaze on her bare ass in front of me. She wears a special collar. It has two chains that stretch to the leather bands on her wrists. They are just long enough to allow her to lift her head just slightly over a foot above the floor. The leather cuffs are chained to a wood post in front of her. She has just enough freedom to move her hands, or to spread them enough to keep her balance as she is doing now.

Her knees rest on a small padding. If she moves at all, she will be scraping her knees on the rough floor and she knows this. She has to choose to either let me administer her punishment, or to move and endure the pain and punishment she would inflict on herself.

I swing the small paddle through the air. Listening to it whistle is I do. Her body tenses with anticipation, but the paddle does not connect. She knows I play mind games. This is not new to her. She still can’t stop her body from tensing, though she expected me to just tease her with the anticipation.

I know her too. I know I have not given her what she wants me to give her. I have failed so many times to give into her desires and let her have what she has asked me for. She wants pain. She has said it to me so many times. I did not believe she wanted true pain. I believed she wanted the hints of pain, the stings of my bare hand and the scratches of my nails. I believed she would enjoy me squeezing her tits until they bruised, or bit her enough to leave a mark, but not to break her skin. I gave her all of that. I was never Sadistic enough to give her more.

I am still not Sadistic. I will never be Sadistic. But I truly want her pleasure. I know her pleasure now. This will not feel natural to me.

“Tell me to stop.” I order her.

“Stop what? You haven’t even done anything but swing that stupid paddle.” I can hear the insolence in her voice.

I grab her hair with my left hand and jerk head back forcefully. As she gasps with shock at my reaction, the paddle whistles through the air and strikes her bare ass with a smack that echoes in the room. “Do not make me repeat myself.” I growl into her ear.

A look of fear strikes her face for just a moment. She swallows and regains her composure. “Please stop daddy. Don’t spank me.”

She will be angry that I made her feel fear. I had to. She wanted this. I could not give her less. This time she hears the paddle’s whistle before it strikes her other cheek. Both of her ass cheeks are turning bright red from the force of the paddle.

“Now tell me the one word that will make me stop. Tell me the safe word I told you to remember.” She looks confused. “I will not stop now. You are going to tell me so I know you know what to say. If I hear it again tonight, then I stop.” She understands.


“Good.” I release her hair and stand up again. Skylar’s head drops for a moment and I hear her take in a shuddering breath. I do not have to ask if she really is ready. She barely fought me as I stripped her and put the cuffs on. She has waited far too patiently for me to just let go and do this to her.

The paddle whistles. The smack echoes loudly.

As I grip the paddle, I realize I am amazed at how smart she really is. How she did such a masterful job of leading me to the point where I could give her what she wants, what she believes she needs.

The paddle whistles. The smack echoes loudly.

Skylar gasps. Shock, pain, and pleasure resonate in her gasp. I drink it in.

The paddle whistles. The smack echoes loudly.

Her ass remains up in the air for me. Her knees stay on the padding. I see her pussy glistening from this angle. The soft hair that she keeps neatly trimmed for me looks so inviting.

The paddle whistles. The smack echoes loudly.

I let my mind remember what it felt like for her to tie me up and have her way with me. I saw the look in her eyes. She truly wanted to draw my blood. She wanted to be my master and make me submit to her.

The paddle whistles. The smack echoes loudly.

Skylar’s gasp has a tone of a painful cry to it. Her head is hanging down now. I can barely tell she is biting her lip. She has not said what is needed to make me stop. She still needs more.

The paddle whistles. The smack echoes loudly.

I see lines on her ass now. The edge of the paddle is creating welts on her ass. Those welts will become bruises. This is where it gets hard. This is not normal for me. I am not Sadistic.

The paddle whistles. The smack echoes loudly.

Skylar cries out louder. She gasps chokingly. Her cries are like sobs, but she has not spoken that word. I can’t continue to use the paddle. There are too many welts. She is too red. I step back and set the paddle on a nearby table.

I pick up a small whip. Several leather straps extending from a small rod covered in leather. I will have to swing hard to make her feel this, but it won’t cause as much damage. I hope it will not cause as much damage.

The whip whistles loudly as I swing it down across her back. I aim carefully so only the leather straps strike her back. I flick my wrist at the last moment, whipping the leather across her pale skin.

The skin starts turning red immediately. Skylar lets out a moan of pleasure. I think she has entered the zone where the pain is her pleasure now. She has crossed the threshold she has waited so patiently for me to take her across.

Faster I pull the whip back and bring it down on her back.

The leather straps whistle loudly. The whip cracks across her skin.

Red marks line her back from the bottom of her hair to the top of her glowing red ass.

The leather straps whistle loudly. The whip cracks across her skin.

I move to the back of her legs. The whip cracks across her legs just below her ass and pussy.

Whistle! Crack! Whistle! Crack! Whistle! Crack!

I move lower and strike the whip across the bottom of her bare feet. She flinches. She curls her toes and tenses her muscles forcing her feet to stay where they are.

Whistle! Crack! Whistle! Crack! Whistle! Crack!

Skylar’s cries grow louder. More desperate. She is fighting now not to sob, but I can hear it in her breathing still. I am at the end of my limit. I am not Sadistic. I also admit to myself that my arm is growing tired. I have no idea how many times I have struck her beautiful skin with the paddle and whip.

I throw the whip aside and strip out of my pants. My cock is hard and ready. I don’t have to touch Skylar. She is so wet I can see it perfectly clearly. I can see some of her pubic hair is dark and matted because of juice from her pussy.

I push her legs open a little more with my knees as I get behind her. I rub my cock on her slit, getting the head wet. I begin sliding it in. Skylar lets out a squealing sound of pleasure as I penetrate her. I push all the way in until my body presses against her ass.

I look down amazed at the heat radiating from the skin of her ass. She isn’t just red, she is red hot right now. I grab her hips. Carefully avoiding the welts and I begin to fuck her. Every time I move. Every time I thrust she lets out that squeal. I can tell clearly she is experiencing pleasure I have never given her before now.

I speed up my thrusting. I let my body smack against her ass. She cries out each time. I feel her body growing tense. She is going to cum. I can see her fighting it. I can see that she is losing. She is going to cum. I don’t change. I just keep fucking her. I just keep my cock thrusting into her cunt and my body smacking against her red hot ass.

Skylar grabs the chains leading from the cuffs on her wrists. I can see her fists balled up tightly around those links. The wood creaks as she involuntarily pulls tightly on the chains. Her head drops down to the floor as her hair cascades around her face. Her body is so tense and her muscles are pulled tight against her skin.

Skylar fought with everything she had, but the orgasm takes her. She cries out with rasping breathless gasps as the orgasm shudders violently through her body. I grab her hips tighter and hold her body up so my cock can stay buried inside of her. I smile a wicked smile as I think about how angry she will be at me for making her lose control like this.

I watch her body shuddering and twitching. I know her eyes are fluttering in time with the quivering of her body.

She may be angry with her for making her lose control like this, but it has driven me past control. My fingers are digging tightly into the soft skin of her hips. My breathing is shallow as I fight against the orgasm building in me. The muscles of her pussy rippling up and down the shaft of my cock are just too much for me.

I know I can’t hold it back. When it hits that point that I know nothing will stop it. When my body is trembling in anticipation of that glorious release, I look up toward the ceiling and close my eyes.

I feel the first spurt of my cum shoot out of my cock forcefully. My muscles spasm uncontrollably, forcing my cum to shoot out of my cock again and again. I can see in my mind, that if I had pulled out, my cum would have shot out of my cock so hard it probably would have gone past Skylar’s head, or maybe gotten caught in her hair. But I didn’t, I can feel it traveling thickly through my cock and shooting forcefully into her.

I don’t know how long I hold her there pouring my cum into her pussy. I don’t even know what I said when I came. It was just so freaking intense, that it was like I blacked out for several minutes.

When I become aware again, I am still holding Skylar tightly against me. I can feel my cum and her juice dripping down both our legs. I let my cock slip out of her very slippery pussy. My cum follows, dripping out. I had no idea I had cum so much until I see it so clearly.

With sheer will power, I grab the keys and unlock the chain from her neck, and the chains from the post in front of her. Skylar sits heavily on her ass. She feels the sting of pain, but the muscles in her body or so tired now, she can’t hold her weight off her bottom. She presents her wrists to me to unlock and remove the cuffs. She holds still while I unlock and remove the collar.

With the collar out of the way, Skylar stretches her arms toward me, child like, asking me wordlessly to hold her. I lean forward so her arms go around my neck. I wrap my arms around her waist and gently pull her forward so that she is sitting on my lap. The tenderest parts of her bottom comfortably between my legs, held just above the floor.

I feel the moisture from her face as she nuzzles against my neck. I can’t tell if it is from sweat or from tears.

“Thank you daddy.” She whispers almost breathlessly, yet emotionally as she holds herself against me.

I hold her close, hoping the pain I gave her will subside soon. I am not a Sadist.

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