Molly's anal punishment and humiliation

 

"You know, I had such great plans for this weekend." you say as you slowly pull my pale bottom cheeks apart. I’d kneel at the bottom edge of the bed, face down in a pillow, ass up in the air, legs spread wide. 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 private areas, taking in every exposed inch of flushed skin. You don't mind tears, or crying, or begging as long as I understand that they have no effect on the severity or duration of my ordeal.

"I was so looking forward to start training your ass. 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 slowly, stretch you out, getting you ready for your first plug as you requested." My knees start to shake as I listen to your description. I had never allowed any of my boyfriends to get close to my asshole. The idea seems 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 our conversation 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, what did you do to get you here this morning." I couldn't help but let out a tiny little sob as I thought back to this morning. "I... I got another speeding ticket," my voice is just above a whisper. Body still bent, eyes staring at the floor.

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 on time. I didn't know it would look like…" my voice is cut off by your hand coming down on my right butt cheek. A gasp passes through my lips as my body surges forward slightly in surprise.

"I don't want excuses. Eyes back on the ground. I don't care what you think. All I care about is that you once again put yourself and others in danger, and because of that I have to take time out of my busy morning to make sure you remember to obey the law for the rest of your life." I hear you shuffle behind me, searching through the small bag. What sounds like a bottle being opened reaches my ears.

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

"But after that ticket, I need it to be a real punishment, not pleasure, to remind you to obey the law." 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 stick out and up relaxing my anus, hoping those fingers will find their way to my core. That they will give me the release 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 wide open for me" 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.

"I was going to use my finger to start you off, but there's no way I'm entering your little hole without a proper inspection to ensure cleanliness. I feel both my holes clench at your humiliating words, the tears start to fall, at the same time I feel the juices from my pussy start dripping down my legs. If my head was clearer, I would probably be embarrassed by how easily just your words make me wet.

So, take a position. My stomach was in knots as I placed both hands on the footboard of the bed, planting my feet firmly on the ground, spreading my legs as far as I could without losing my balance. Bending forward at the waist I positioned my upper body to be parallel to the floor. With my head up I fixed my gaze to the middle of the headboard, waiting and ready for my inspection.

Gently your fingers trailed up and down my spine, causing bumps to rise all over my body. Your hand stopped at the round of my ass, cupping one cheek and then the other. Your fingers began to trail down the crack of my ass, letting one finger trace my anus, probing and tickling but not entering. I shuddered but did not dare make a move.

"Have you gone to the bathroom yet?" It occurred to me that I hadn't, but it would have to wait until after the inspection. Your finger slipped into my pussy quickly, not wiggling, using my juices for lube. Your pointer returned to my anus, pushing into me. I arched my back, fighting the urge to grind my hips.

"No, Sir." I felt your fingers moving in my rectum drawing little circles, opening me, seeing how far I could stretch. This was the hardest part of my inspection. Up until today I had never failed an inspection, but due to my growing need and the wetness now dripping down my thigh, I wasn't sure if I would pass today. I began cursing myself for not using the bathroom before our meeting.

"I trust you know the rule, but I want to hear it." You pulled a chair up behind me, rolling your sleeves up for the last inspection. "Yes, Sir. I must not cum. This inspection is not for my pleasure." I tensed as you reached your hand out, sliding your finger up and down my silky pink folds. Your finger circled my swollen clit sending electric shocks deep into my pussy. I accidentally moaned softly but you did not get upset with me. Up until now I had managed to keep my composure and control my body. I could hear my juices each time your fingers ran over the entrance to my pussy. You slipped your pointer finger easily inside of me and I felt it press firmly against my g-spot and then rubbing it. I couldn't hold back a deep groan as my bladder threatened to release. You paused.

"Stay still. I don't want you to release your bladder. Remember, not even a leak." My stomach flopped and I clenched as hard as I could. A few more moments and we would be finished, and I would run to the bathroom and release. But you continued your assault on my g-spot, adding a second finger in my pussy and one in my rectum as well. You stopped and removed your fingers.

I could hear the mischievous tone to your voice, seeing the grin in my mind without looking at you. "This inspection is going to be a little bit longer than usual. I'm going to grant you a pardon and allow you to use that bucket to release. "Until I am satisfied that you have learned to keep yourself clean, you will be squatting over one of these buckets when you need to pee, and you will squat facing me and do your business. When you are finished, I will tell you to wipe yourself clean." You have two minutes to do so and then you will return to your position. Understood?"

"Yes, Sir! Thank you, Sir." I quickly squat over the bucket under his full supervision. I know that you are desperate to go, but if you wish to pee, you do it on my terms, not yours, with no privacy." An evil smile on his face as he knows I struggle with this, that I can be desperate to pee and yet not be able to if someone is watching me in this exposed and humiliating position. You lean back fully relaxed and in control, enjoying my embarrassment. I cannot bear knowing you are watching this mess of my need and urge to relieve myself. It humiliates me in a way I have never felt before. I am ashamed of my lack of control. That I have allowed you to reduce me to such a base level, and yet here we are, in your living room with you sitting comfortably. Almost as if you are watching a movie. So incongruous. So humiliating. So humbling and yet arousing on a different level.

I cry out at the invasion of my most basic right, at the humiliation. I can't stop the pee coming, there is too much, and I need to be empty, and I feel a surge of intense arousal that I'm squatting here, peeing in front of you, and you are watching me intimately.

My stream kept flowing for a good thirty seconds before I finished. I used a baby wipe to freshen up before being allowed to stand. "I'm ready to continue, Sir." As I stand up. "You're such a good girl. You did well, stand up straight with your hands behind your head. Push your chest out. Good." Your hands cupped both of my breasts, giving them a firm squeeze. Your fingers gave attention to my nipples. At first you were gently twiddling them causing them to stiffen, then you pinched them firmly, pulling them as far as you could before my face scrunched in discomfort.

"Very nice. Resume the position." Nervously I got back into position. My hands grabbed the blanket on the bed tightly, scream and moan and incoherent mumbles escaped my mouth as I fought to slay still with my ass and pussy up in the air.  However, the sudden feeling of the blunt tip of a cold plug at my entrance causes me to startle from my thoughts and almost lose my balance. You chuckle behind me.

The most painful insertion would be a dry plug, but experience had taught you that a dry plug was almost impossible to insert, at least in my inexperienced hole. And while the aggressive pushing elicited more than the requisite cries of pain, you really don’t have any intention to “actually” hurt me. So, before the plug went in, you would take a small amount of cinnamon or pepper oil on a gloved finger. I would cry out as the finger worked lightly over my delicate anus, then again as your finger pushed open my sphincter to coat the area just inside my hole. The pepper oil is a satisfying compromise, the small amount of oil easing the plug past the sphincter while creating a burn on the asshole. And if the plug carries with it the residue of the oil down the deep, dark path of my rectum.

The burn is sudden and intense but despite the pain, or because of it, my little pink pussy would spread open, lips engorge, and a creamy white substance cover my crotch and run down my thighs. My immediate reaction is to tense up my whole body 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 girl. We both know that this is what you need. This is the control you need to give up staying in line."

You push the plug into my ass at steady speed, not letting any resistance from my tiny hole stops you as I scream my distress into the pillow, never think of moving away but remain, ass offered upward, to allow for my punishment. I hear the undignified moans leaving my mouth unrestrained. I feel the widest part of the plug pushing past my anus, the burn and stretch are almost unbearable. I try to pull my body away but have nowhere to go. 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 enjoy the pain and embarrassment. This is my punishment, one that I have brought on myself. And if my pain brings your forgiveness and pleasure... I can endure. Please, I'll be good. Please. Oh god it hurts...hurts so much. Please. Please. I'm sorry. I'll be good, I promise. I'll be good.

As the widest part of the plug reaches my sphincter, you stop to allow me to feel the full impact of the stretching of my hole. You wait until my begging stops then wait another minute for me to quietly accept this modification of my body. Then, recognizing the slight body shift that signals her acquiescence, you push the plug all the way.

The room is quiet, except for the sounds of my heavy breathing as I try to mentally process the new feelings. 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.

And there it is. That's why I'm here. Your praise washed over me like a feeling of euphoria. I want nothing but to please you, even with my most private area.

I feel you pulling up my panties and pants. 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 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, unless you need to go to the bathroom with my permission, understand?"

I nod, "Yes, Sir."

"Good." 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.