An Anal Punishment

I squeeze my eyes shut. That small voice in the back of my head asking myself why I'm here.

Why am I here, bent at the waist with hands braced against the wall of the janitors closet. The smell of cleaning chemical tickling my nose. My professional black skirt hiked up over my hips. Eyes almost wet with tears because of my mistake. One stupid, stupid mistake, that to the outside world would seem like nothing. But I know I've disappointed you, perhaps even made you angry? And the feeling is almost more than I can take.

I feel your shoe kick the inside of my heel, my cue to spread my legs wider- or at least as wide as my underwear and pantyhose, that were currently held up at my knees, will let me. I bite my lip as I feel the light touch of your hands on my ass.

"You know, I had such great plans for this weekend." you say as you slowly pull my cheeks apart. My face burns hot with the embarrassment that I still can't shake when I'm on display in front of you. I can feel your eyes sweeping across my body, taking in every exposed inch of flushed skin.

"I was so looking forward to starting to train this ass to take me. Was going to give you a nice warm enema to clean you out, that way I could start off with my finger. Take it nice and slow stretching you out, getting you ready for your first plug." My knees start to shake as I listen to your description. I had never allowed any of my boyfriends to so much as touch my asshole. The idea seeming unnatural and unpleasant to me. You had been patient in waiting to start my training, but had been quick to assure me from the beginning of... whatever this was... that you would take every part of my body, I could not deny you.

I hear your disappointed sigh as you remove your hands from my backside and take one step away. "It was going to be so sweet and enjoyable for both of us. But no, you couldn't let me give that to you. Tell me again, pet, what you did to get you here this morning."

I couldn't help but let out a tiny little sob as I think back to this morning. "I... I was flirting," my voice is just above a whisper. Body still bent, eyes staring at the floor.

"Louder, slut. I want you to explain with details," I can hear the annoyance in your voice.

"I was flirting with Phil, at my desk." I feel the knot forming in my throat and I can't help but lift my head to look at you over my shoulder, tears brimming in my eyes. My words start to come out in a rush. "I don't mean to, Sir. Honestly. I... I was just trying to be polite when he brought me the coffee. I didn't know it would look like-" my voice is cut off by your hand coming down on my right buttcheek. A gasp passes through my lips as my body surges forward slightly in surprise.

"I don't want excuses, you bellow from behind me. Eyes back on the ground. I don't care what you thought. All I care about is that the whole office, including myself, saw the continuation of your little office romance with Phil from accounting. And because of that I have to take time out of my busy morning to make sure you remember for the rest of the day who you belong to." I hear you shuffle behind me, searching through the small bag you had brought into the closet with you. What sounds like a bottle being opened reaches my ears.

I wanted this to feel so good for you, baby. "That beautiful ass of yours was meant for this, I could have made it such a wonderful first time." I feel you behind my again, one hand squeezes my right cheek, the tingle from the slap still lingering.

"But after that little display this morning I need it to hurt, to remind you of whos slut you are." Your fingers lightly play across the skin of my ass, caressing touches sweeping down my thighs and back up again. My legs quiver at just this simple touch. I can already feel my mind and body craving more. Without even thinking my hips jut back and up, in hopes that those fingers will find their way to my core. That they will give me the realise that I'm now in almost a constant state of longing for. My heart drops as I feel your hand leave my skin before providing any sense of satisfaction.

"Pull your ass open for me, little girl," your tone is sharp and clipped, I know not to keep you waiting. I awkwardly try to keep my balance as I reach back to open myself to you. My breathing quickens as I feel a cold wetness hit my asshole. I know I should thank you for using lube, it's a bit of mercy even after my failure.

"I was going to use my finger to start you off, but there's no way I'm touching that dirty shit hole without proper cleaning. Such a shame really. I bet your ass would take a finger so well, I bet I could have made you cum with just a finger in your ass and a thumb on your clit."

I feel both my holes clench at your humiliating words, the tears start to fall while at the same time I feel the juices from my cunt start drip down my legs. If my head was clearer I would probably be embarrassed by how easily just your words make me wet. However, the sudden feeling of the blunt tip of a plug at my entrance causes me to startel from my thoughts and almost lose my balance. You chuckle behind me.

"You need to relax, pet. Or else this will go a lot worse for you than I've already planned. I'm not going slow and gentle, that's for pets who can stay loyal. But for sluts like you who go whoring around the office..."

The burn is sudden and intense. My immediate reaction is to tense up my whole body in an effort to keep the intruder out. Your words of advice ring in my ears though, so I try to control my breathing and relax my hole. "Don't try to get away from me, little whore. We both know that this is what you need. This is the control you need to give up to stay in line."

You don't slam the object into me. Instead you push the plug into my ass at steady speed, not letting any resistance from my virgin hole stop you. I let go of my ass with one hand to brace against the wall to keep from toppling over. I hear the undignified moans leaving my mouth unrestrained. I feel the widest part of the bulb pushing past my anus, the burn and stretch are almost unbearable. I try to pull my body away but have nowhere to go with the wall in front of me. I can feel the tears flowing freely down my face now. It hurts. But in some dark and dirty part of my mind I begin to revel in the pain. This is my punishment, one that I have brought on myself. And if my pain brings your forgiveness and pleasure... I can endure.

The tip scrapes against my walls adding to the new sensations of pain as it continues its push in. As the last of the plug is sucked into my ass I feel myself involuntarily clench around it. The lung full of air that I hadn't realized I'd been holding is let out with a gasp. The feelings of stretch and pain and invasion shudder unchecked through my whole body. But even amongst the pain I can already feel my pussy quiver ever so slightly. I know that my nipples are growing hard behind the confines of a modest office blouse.

The room is quiet, except for the sounds of my labored breathing as I try to mentally process the new feelings. Both my hands are propping me up against the wall now. After a few moments I feel you behind me, pulling my cheeks apart to check your work. I shudder as you use a finger to press against the end of the plug, pushing it that much deeper. "There's my good girl. Taking a plug in her ass for the first time, just like the good girl I knew she could be when her focus is in the right place... my dirty little slut."

And there it is. That's why I'm here. Your praise washed over me like a feeling of euphoria. I want for nothing but to please you.

I feel you pulling up my underwear and pantyhose. Still in a slight daze, I don't register your moves to pull me up to standing until the change in position causes the plug to scrape and stretch in a new way. I can't help but grab onto your arm to keep my balance as I grimace and another shudder courses through me.

You laugh out right now, "Looks like you are going to have quite an interesting day navigating the office, Little One."

As you adjust my skirt back down you look me in the eyes, face serious and eyes once again dark. "You are not to touch that plug or take it out. It stays right where it is, reminding you of what you are and who you belong to. Understand?"

I nod, "Yes, Sir."

"Good. Oh," you look back over your shoulder at me before you open the door to leave. "Make sure you keep your phone close today. I may have some special instructions for you as the day goes on."

And with that, you are gone.