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.
