My First Time With You Sir

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Someone finally gets my anal cherry.
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I had been disobedient again you walked away after strapping me up and whipping me when I heard you turn the shower on, and my anger grew in my chest like heat in an oven. I was making up my mind to be less cooperative with you when I felt a HUGE something push into me and tensed trying to push out the burning invader, you put your mouth right by my ear and I strained to listen to you say "You better relax and accept this or its really going to hurt next time I fuck you. This is what you get for being a cunt. I heard you bitching and I'll give you something to bitch about. You need to remember that this is my house I know everything that happens in it. I know when you breathe, when you sigh from pleasure and bite your swollen lips to suppress a scream. You keep forgetting that when you are here you are mine." I relaxed the muscles in my pussy and felt you slam the dildo home; it was huge and filled me up completely. I hoped that I could keep it in for you. My anger forgotten I just wanted to apologize for my disobedience and make you satisfied. You patted my bottom letting me now that for the moment you were pleased, you left me there stretched to capacity hanging and waiting.

I imagined you in the shower shampooing your hair soap running down your body to my amazement I felt myself responding to the monster inside me and moaned. After thirty or forty minutes you turned the shower off and I heard the timer on the oven beep letting you know your meal was ready, I was starving but didn't even begin to imagine you would allow me to eat. I felt your hand running up the inside of my leg and stilled every muscle in my body; I wanted you so badly to be happy with me. You a cuff and let one leg down at a time the upper part of my body was still restrained in cuffs and chains. I looked up at you and as always was impressed, you had a towel around your waist and your shoulders were still damp I could feel your skin on mine and I inhaled deeply the smell of your soap. You tapped the head of your cock against my lips and I smiled inwardly knowing you loved the way I sucked your dick.

I let my jaw go slack and you sighed in pleasure as you filled my mouth all the way to my throat I relaxed the muscles there and you pushed even farther inside of my mouth, your balls settled against my chin. I felt you hesitating to stay in my mouth and let me work at getting you excited again or pulling out to leave me panting. You reached down and stroked the top of my head letting my silky hair rain between your fingers cupping the back of my head as I sucked and sucked you. I felt your hand closing on a size able collection of hair at the base of my neck and I knew what was coming, I tried to prepare myself but knew I would gag anyway. You pulled me back by the hair to the head of your dick, my teeth lightly grazing the whole way opening to allow your head to pop out, you reached down with your other hand and aimed right at my open mouth and slammed it into me.

I gagged hard and you laughed and did it again, four times. You dropped the cuffs around my wrists and my arms fell like weights the blood flow returning to normal almost hurting with its path into my shoulders down my arms. You threw a stack of clothes at me and I got excited in a way that surprised me. You had fucked me like a machine just two hours before I thought that there was no way I should be responding to any more stimulation but I was. I stood up and bent over presenting my backside to you, so you could remove the thing inside me you pulled it out and gave my ass a resounding smack and I wiggled it a little tempting you. You told me to get dressed and bring my discipline collar to the dining room.

I shook my head when you left the room, you had gone through my suitcase and found clothes you liked and I laughed a little at them. Fishnet stocking, no panties, a navy blue skirt, white button down shirt, and the most beautiful bra I owned, red lace that held my breasts out and up giving me fantastic cleavage. I dressed quickly and picked the white collar walked into the dining room and felt a bit disappointed there was one place setting and my stomach growled. You ignored it and pushed me to my knees to put the collar on and I noticed the chain attached to the opposite wall of your seat at the end of the table.

Doing rough measurements in my head I knew it wasn't long enough to reach all the way to you and confusion began to mount, you pulled the chain and I felt like a dog crawling to the end of the table you dropped the chain and told me to crawl from one end to the other under the table, I followed your progress and crawled until the chain pulled in resistance, you sat down and you pulled your delicious dick out of your pants. My mouth starting watering I wasn't sure from the food or the sight of you exposed to me. You made a "come here" motion with your hand and I stretched towards you realizing this is what you wanted me extended to my max the collar pulling against my neck.

You sat there waiting for me to figure out how to get my mouth around you all the way. I could get you in a quarter of the way so I made good on it, working that little bit like it was all of it. You slid forward a little and I got a little more. Sighing in pleasure I tried to give you everything I had, if I pulled harder against my restraint I could almost get all of you inside my mouth. But I also saw black spots behind my eyelids and figured it was best if I stayed conscious. You began eating and would every now and then pass me a piece of your food under the table only allowing me a second's break from pleasing you.

Half an hour passed forty five minuets an hour I knew I could be down here all night, and it must have been slightly maddening for you also, knowing how I could please you given the chance but only getting to tease you was making me horny. Then again I didn't know who enjoyed your blowjobs more you or me. Suddenly you pushed your chair back my mouth hanging open your hard cock bouncing with every step I sat back straight as an arrow because of the collar, it wouldn't allow me to slouch in the slightest. Back in the room you tugged the chain and I made my journey back to the other end of the table, my legs were shaking from being on my knees this whole time, you told me to suck you off until you were ready and then to swallow every drop of your come.

I did my best and you filled my mouth a few short minutes later, I savored every drop letting it sit on my tongue. I stood and tensed and relaxed my legs stretching a little we walked to where you were sitting and you had me bend over the table I saw the bondage tape and felt you pull my left leg to the leg of the table as you wound the tape from my ankle up to my thigh tight then you moved to the right leg. Stretching me pulling the muscles I tried to relax them and my body to accept whatever it was I was about to receive. Then it hit me if you get rid of the stockings and tape I was back in my principal's office about to get the spanking of my life. I felt the paddle make its first stroke and I wiggled as much as I was allowed wanting you to stop, but then craving you to go on at the same time.

You pulled up my skirt and I knew in no way would the stockings act as a buffer between your hard strokes with the wooden paddle and my sensitive bottom. You switched from the paddle to a leather whip because you liked to run your fingers over the whelps the whip left on me. I moaned and screamed and orgasmic over and over and over again. I knew you could see it running down my leg, you pushed two fingers inside of me enjoying the warmth and wetness, I felt cold sharp metal push between the cheeks of my butt slicing effortlessly though the strands of the fish net. I knew what you had in mind; you knew I was still technically a virgin in places. You wanted that cherry for your own.

I tensed kind of freaking out thinking about you stretching my asshole with one of the many toys you had, your fingers, your dick. You applied a generous amount of slippery lube there and slowly pushed one finger inside enjoying the tightness. With the other hand you put a clamp on my clit and pulled lightly enjoying the way my asshole clamped down on your digit. I twisted my hips nervous and you barked at me to be still, I was trying my hardest. Pushing two fingers in you stretched me three fingers and I clamped down tenderly you removed the clamp and rubbed my clit. Applying slight pressure gradually getting firmer moving in small circles working me over quickly I came. As I relaxed a little from my orgasm you stood up and put the head of that delicious dick against me.

Pushing against me allowing your body weight to control your advance just the head was in and tears were running down my face, but you knew I wanted this desperately, I bit my lip drawing blood, sucking hard trying to stop the bleeding it distracted me for a second. You used it to your advantage pushing in further meeting more resistance you paused momentarily. Telling me to reach out on either side of me and find the nipple clamps, they were my favorite ones I tried to move as little as possible hating and loving the pain in my asshole at the same time. Your fingers pinched the whelps on my cheeks making me squirm and it moved you deeper inside of me. Noticing that I was putting the clamps on you pulled my hair back elevating my torso and you sank in a little more I cried out in pain tensing and relaxing, every exhale you pushed into me. Talking to me soothing me.

It was a slow advance I was beginning to love the invasion hating that I couldn't just be ready at your command. Trying not to focus on the urge to push my hips against the table and have you out of me. I was trying to be a good girl and you knew it. You played your fingers in my hair as you pushed slowly quarter of and inch by quarter of an inch. You were about half way in when you retreated slowly and pushed in again. Pinching my hips sinking your fingers in deep, grinding your finger tips against my hip bones, making a dull throb there distracting me. You pushed in farther I estimated you had three quarters of yourself pushed into me, I tensed and clamped down so hard if you weren't as far in as you were I would have pushed you out. You had me reach beneath myself and tug on the nipple clamps to distract myself from the pain in my ass, without realizing you were all the way in and satisfied with yourself. Then you asked me if I wanted more. I moaned yes and pushed back against you.

You pulled back and pushed in moving so agonizingly slow. I came. You pulled back my wetness dripping down the front of your thighs, you told me I would be cleaning that up later, and a sinful yearning filled me. You fucked my raised ass for an hour talking to me, telling me we had hours and hours of more fun before you let me go. You told me to squeeze as hard as I could with my muscular ass and milk the come out of your cock. I did as you wished squeezing and releasing working my tight asshole like a pussy loving you moaning and working yourself in and out of me. You collapsed on top of me with your dick still inside and told me to come I was on the verge and did in surprising intensity. One last shot of your sweetness rolled into me.

You pulled out of me and cut the tape from my legs I collapsed onto the floor and looked up at you smiling and waiting. You helped me up and we showered then you brought me back into our room of and rubbed my whole body down with oil massaging my tired muscles, I laid on the floor as you grabbed the tape butt plug nipple clamps and clit clamp. You told me you wanted my asshole ready for whenever you were and slid it home, sucking on my nipples for a little while eliciting moans from me you whipped my pussy for getting you aroused again. In the wake of my rip roaring orgasm you clamped my clit and my nipples bound me and lay back in bed. Spending the rest of the night reading fondling me and sleeping

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