Becoming An Anal Slave

I have always had a penchant for almost anything anal. I had met a man who claimed to have the same enjoyment in that regard. He told me he was a dominant, and me, being the naïve young girl that I am really had no idea what that meant. We began dating, and I had told him that I wanted to take things slowly, not rush into anything. So we began to see each other, and he was so sweet and kind, and never made me feel like he was pushing me into anything. We were dating for about a month, and things were going extremely well. He was always such a perfect gentleman.

I didn't notice the little things that he was doing that were slowly taking control of my life. I thought he was just a very kind man who enjoyed my company and didn't want to rush me into anything before I was ready. It didn't strike me as odd at all when we would go out to dinner, he would always order my drinks for me, and even order my dinner. He almost always chose things that he thought I would like or thought I should try and I was enjoying all the attention he was lavishing on me.

Pretty soon, he started buying me outfits that he said he would like for me to wear when we went out. He told me that I was so beautiful and he wanted me to dress in a way that showed off all of the assets that he found so attractive. He was treating me so well, I didn't give it a second thought. The blouses he purchased for me were all very low cut, but they really did show off my ample breast to their full potential. I asked him if it bothered him that men kept looking at my cleavage that was so much in the open, but he just replied that he liked while they looked at it, they couldn't have it. The skirts he always wanted me to wear became shorter and shorter as well. The shoes he liked me to wear were always at least 3 ½ to 4 inches high. He made him so happy to see me dressed that way that I never questioned what he asked.

One day, a package arrived at my door, as I was getting ready for another date with this man that I was coming to believe was my perfect match. We had been seeing each other for a month now, and all he had ever done was lavish me with beautiful clothes and shoes and kiss me goodnight. He never pressured me for anything else. There was a note inside the box that told me he had a special surprise for me that night. The outfit inside the box was unlike others he had asked me to wear. It was not terribly revealing at all, although it was a very nice dress.

Having gotten used to the ritual of wearing what he told me, I showered and got ready and dressed and then had a glass of wine while I waited for him to pick me up. He arrived with yet another package in his hands, making me very curious, but telling me I will find out what is in the bag when he felt the time is right. He then told me to pour him a glass of wine.

As we sit drinking our wine, he tells me how much he has been enjoying getting to know me. He remind me that he told me when we first met that he was a dominant, and explains that he has been seeking a submissive that would suit his needs. Over time, he says, he has learned that getting to know someone in the "vanilla" sense has given him a much better perspective on whether or not the woman he is seeing will meet his needs. Now that he has gotten to know me, he tells me that he thinks I might make a very good submissive for him.

Still not really understanding what he means by that, but by now being totally enamored with him, I tell him that I am certainly willing to try it. "Good," he replies, "because I have decided that tonight we will begin to take on those roles more completely." He then hands me the other package and I open it to find a butt plug laid out in a velvet box as though it were a piece of jewelry. Looking at him quizzically, he explains to me that as one of the first attractions we had to each other was my love of anal play, he decided that he would like me to wear a plug when we are together because he wants a submissive that he will train as an anal slut.

"But I already explained to you that I very much enjoy anal sex, so I still don't understand why you would need this."

"Whenever we are out publicly, I will continue to treat you the way I have treated you all along, with respect and consideration. However, if you are to be my submissive, you are going to have to learn that in our private life, you belong to me, and I will use you for my pleasure. Having a plug in your ass will serve as a constant reminder of that fact."

I'm stunned by what he just told me, but I had already agreed that I would "try" being his submissive, so I am not sure how to respond to what he has said. Looking at the plug, it seems to be somewhat small and as I have already become so accustomed to doing what makes him happy, I just nod my head and say "ok".

He instructs me to lie across his lap, and he lifts up the hem of my dress. He takes a moment to caress my buttocks and slide his hand between my legs to gently stroke my pussy. This is the first time he has touched me this way, although I have been longing for him to do so for some time. He slides his finger in my pussy and finds that it is very wet. Using the wetness of my pussy, he begins to slowly finger my asshole. He isn't the least bit surprised when I raise my hips up to meet his probing finger. "See? I knew this was going to turn into something that you would enjoy." He slowly slides the plug into my ass and pull the hem of my dress back down. "Let's see how this suits you for the evening while we are out tonight."

The plug wasn't very big, just big enough to know that something was in my ass. We went out to dinner and the evening progressed like every other dinner date that we had. Except of course for the fact that I was sitting in a very elegant restaurant with a plug up my ass that was there for the sole purpose of letting me know that I now belonged to him and had agreed to let me use me in this way as he saw fit.

After a very enjoyable evening, we get into the car and he reaches up under my dress to feel my pussy. "You are quite wet down there. Are you enjoying having the plug in your ass?"

"Yes, I am" I answer, blushing.

"You seem to be handling that size quite easily. I wasn't sure what size to start you with, but apparently, this one is too small to train you properly." He starts the car and we leave the restaurant. As a passenger, I never really pay much attention to where the driver is going, and was quite surprised when he pulled into a local adult store. "We must go and find something that will be more adequate in your training." He gets out of the car, and in true gentlemanly fashion, he comes around to my side of the car, open the door and help me out.

When we enter the store, he leads me right to the section where all the butt plugs are on display. I can't believe how many different sizes and shapes there are. He reaches out and takes one off the display and hands it to me. "This is what is currently inserted in your ass. I'm going to pick out several plugs tonight of varying sizes. None of them will be as small as what is in your ass right now." I watch as he take three plugs off the display. The first is a size larger than the one still in my hand, and the other two graduate in size from that one. He takes the plug from my hand, puts it back on the display and hands me the three he has chosen. "Part of your learning to be my submissive will be to perform certain tasks that I demand of you." He takes out his wallet and hands me enough cash to pay for the three plugs in my hand and then some. "I am going to go and wait in the car. You are going to purchase these butt plugs and I also want you to go over the BDSM section and pick out an implement that you will be disciplined with. There are paddles, straps and all sorts of other things. I am leaving you to choose whichever one you would like, but I warn you, if you do not come out of this store with all of the items I have instructed you to purchase, I will come in and choose for you, and you more than likely will not be pleased with what I choose."

Having given his instructions, he quickly turns and leave the store with me standing there holding three large butt plugs in my hand. I doubt that I was redder than with the worst sunburn I had ever suffered. Not even sure why I am doing it, I walk over to the BDSM section and begin looking at all the paddles and straps and such. I know that I must pick one, but all of them look like they will be horribly painful if used. I finally settle on a deerskin flogger. The deerskin is soft to the touch and I foolishly think that it might be the mildest implement I can get. Now more anxious than ever to leave the store, I quickly proceed to the cashier and pay for all the items.

When I get outside, he is standing by the passenger door, waiting to open the door for me. He takes the bag from my hand and inspects the contents, smiling to see that I have done what I was told. He kisses me passionately and opens the door for me to get in.

He drives to his house and leads me inside. I have been here many times in the past month where we have cooked many meals together and just sat watching movies and talking. Suddenly, his house appears so different to me because I sense how our positions have now changed.

He places the bag on the counter, and reaching inside removes the plug the next size up from what is currently in my ass. As much as I enjoy anal play, I look at that plug with trepidation. It seems huge to me in that package. He takes me to a room in his house that I have never seen before. I had read about, but never seen a home dungeon in my life. He takes me in his arms and again kisses me passionately. "Don't be frightened. I waited as long as I did because I wanted to be sure that you would really want this. This is who you truly are and I am so glad to have found you and that you are allowing me to bring you to your full potential." He unzips my dress and lets it fall to the floor, leaving me standing naked before him in nothing but my shoes.

He walks over to a bench and motions for me to follow. I follow him over and he assists me into position on the bench. I am stunned as I feel him lock my ankles in place and then come to the front to secure my wrists. I am completely immobilized now and helpless. He walks back behind me and removes the butt plug. Walking over and dropping it in the trash, he smiles as he tell me that we won't be needing that one anymore.

"One thing we never did talk about when we talked about our mutual enjoyment of anal play is that I have a very, very thick cock. I am putting you through this training now, because you need to learn to take my thick cock in your ass whenever I feel like putting it there. While this may be difficult for you to endure now, in time, you will be grateful that I have taken the time to train your ass to take my cock."

I feel the lubricant squirt on my ass hole, as he makes sure to slide his fingers in and out of my ass to lubricate inside as well. I gasp when I feel the tip of the larger plug begin pressing against my asshole. "Shhh," he says gently, "I know this might be a bit uncomfortable at first, but trust me, it is a very important part of us moving forward." Continuing to move slowly, he slides the plug in and out a little at a time. As the fattest part begins to stretch open my asshole, I whimper quietly and try to squirm away. When I squirm, I feel a sharp, stinging smack on my ass. "Now I told you this is necessary. If you can not sit still, I will take that flogger you bought and whip your ass until you learn to sit still, is that clear?"

I am completely shocked at this totally different side of him that I have never seen. When I don't answer quickly enough for him, he smacks my ass again, even harder this time. "You will answer me when I ask you a question. Now are you going to stay still or not?"

"Yes, I will stay still." I answer as quickly as I can. Immediately, he goes back to being as gentle and kind as he usually is, slowly and gently sliding the large plug in and out, a little further each time, but this time he strokes my pussy while he is sliding the plug in and out. When I begin to moan, he slides the plug in further, continuing to stroke my pussy as the fat part opens my ass. Finally, he has the plug all the way in my ass. It feels enormous, but now that it is all the way in, it is far less uncomfortable.

Leaving me strapped to the table, he walks back around to the front. "Now I am going to show you why this is necessary." He undoes his pants and take out his hard cock. He laughs as my eyes widen looking at the enormity of his member. "Based on the difficulty I had inserting this most recent plug, you certainly are not ready to take my cock in your ass, are you?"

"I don't know that I will ever be able to take that monster in my ass!" I cry.

"Don't worry, it will fit in your ass. That is what all this training will be for, because when I am done, you will be taking my cock in your ass several times a day." He then proceeds to undo the restraints and helps me to stand up, warning me that I had best not let that plug fall out before he has had the opportunity to harness it in.

After he has harnessed the plug in, I ask him how long I will have to keep this plug in. "Well, I'm not sure yet. Are you telling me that it is unbearably uncomfortable already?"

I shake my head and say, "No, it is just that I am so new to all of this, and I don't know what it is you expect of me."

"I expect you to learn how to please me. Sometimes, like now, your lessons might cause you some discomfort. I expect you to accept that it is all so you can learn to please me. You will be required to take my cock in your ass very frequently; therefore it is necessary that your ass be trained to accept such a large object for extended periods of time. I thought that you enjoyed making me happy? You certainly enjoyed dressing in all the clothes I asked you to wear. You have enjoyed my taking you to nice places, have you not?"

"Yes, I have enjoyed all of that. I enjoyed it very much and it has made me very happy when you look at me and seem so pleased with what you see."

"Earlier tonight, you told me that you wanted to be my submissive. Have you changed your mind? I certainly don't want to train you to be my submissive if that is not what you desire. However, I believe that you are just frightened by these things that are so new to you. I see in you someone that I could keep with me forever, giving you your every whim. Is what I am asking of you now not worth that?"

I stand there naked before him, a large plug stuffed in my ass listening to every word he says. The last month with him has been nothing short of a dream. Each night when he kissed me goodnight, I went to bed dreaming of the day that he would stay and we would enjoy each other's bodies. During the last month, I have never felt so cared for. I can't remember ever having someone who was so attentive to my every want and need as he has been. We met because I needed someone who would enjoy anal sex with me, and that is exactly what he wants. I can't deny that the thought of that monster cock of his in my ass right now is downright frightening. Surely, he is doing this so that someday I will be able to take that cock in my ass and enjoy it, which is what I was seeking to begin with. As frightening as his cock looks to me right now, in the back of my mind, I can't help but think how much I do want to have it in my ass filling me.

"I'm sorry. You are completely right. I have never been happier in my life than I have this past month. I want to be able to take your cock in my ass, and I believe that you are doing this so that eventually, we will be able to experience the pleasure of you in my ass. Again, I'm so sorry. I never should have questioned you."

"I accept your apology. So now I am going to ask you one more time....I want to train you to be my submissive, train you to be able to take my cock in your ass whenever I want. In exchange, you will never want for anything. I will take care of you, but I will have expectations of you and you will have to learn to accept and meet those expectations. Do you want that? Are you willing to accept I want you as mine and sometimes will need to do some things that you may not like in order for you to learn this new way of life?"

"Yes. I want the happiness I have felt to continue and I want to make you as happy as I possibly can."

"Good. Now that we have settled that issue, let's go back to how long you will have to wear that plug in your tight ass. I have found through experience that with a cock as large as mine, it is best that a plug be kept in my partner's ass whenever I am not using it to keep the muscles from tightening up too much. So while that particular plug may not always be in your ass, something will be in your ass at all times from now on."

I am dumbfounded as I realize that I have just agreed to have something large in my ass at all times, but realize quickly that I would rather that than lose him. He takes me in his arms and whispers into my ear that he is so happy that I have agreed to this, and he promises that in the long run I won't regret it. He then tells me to kneel on the floor in front of him, because while he knows my ass is not ready to take his cock, he wants me to start learning how to take as much of it in my mouth as possible.

I kneel down and begin to lick the head of his huge dick. I feel him begin to run his fingers through my hair and offer encouragement. Knowing that I am making him happy, I begin to take him in my mouth, and surprise myself when I begin to suck him more eagerly when he tells me what a wonderful slut I am going to become.