New Submissive 1

if anyone out there in literotica land would be interested in providing photos to go along with this series, please get in touch. Your photos would add so much to this story.

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I had a totally unexpected and unplanned "happening" recently. We have an acquaintance who is in her early 50's, and who has been a widow for about 15 years. Recently, we were at a social gathering, and she had told one of her friends that she needed help with some paperwork that she did not understand. So they called me over and asked if I could help, since I had taken early retirement and had the time. My wife encouraged me to help her, so I said no problem, and we arranged that I would come by her place a few days later.

Let me say that this woman is an extremely pleasant lady, and has a great smile. She is also very docile and non-controversial. She is not particularly attractive, but that is her own fault. She has never dressed in any way other than what I would call dowdy. Always wears really long dresses, flat shoes, little if any makeup, and wears her hair in a bun! If she got a makeover, I think she could be a very attractive lady. She is about 5' 6" tall, slightly overweight with brown hair, a really nice bust (perhaps 44C?), and the few times I had gotten a glimpse of her legs, they looked pretty good. Her one asset that is very obvious to all is a really nice butt. She had also given me the impression over the years that she kind of liked me.

Anyway, when I got to her house she greeted me with a big smile and of course wearing one of her dowdy outfits, with her hair in a bun as usual. Offering me a drink, and some cookies, which I accepted. It took about an hour to go over everything, and explain things to her. She went out of her way to thank me for coming over to help her out.

At this point, while still sitting at her dining room table, I decided to ask her a few questions that had always bothered me about her. I figured I had nothing to lose, and since she was so grateful and there was no one else around to overhear, I thought she might be willing to talk openly. So I asked her if she would mind if I asked her a few questions, and that I hoped that they would not offend her. I also told her that if my questions made her uncomfortable to just say so and I would be on my way. She said for me to go ahead. So after taking a deep breath, and looking her straight in the eyes, I asked her why she never dressed up more than she did.

She started blushing and cast her eyes down, and said that she didn't know. I told her that I thought that if she were to make a few changes, she could be a much more attractive woman. Of course this made her blush even more, and at first she didn't say anything. Then, she looked up at me and asked me if I really thought so. I assured her that I did. She then asked me what kind of changes she should make. I think it was around this time that I had an idea. Taking into account how subservient she had always been, and the fact that I thought she kind of liked me, I thought I would try to take this to a whole new level.

I told her that in the first place, she should start wearing nice dresses or skirts that were at the most knee length, but shorter would be better. Also, she should never again wear flats anywhere. Only heels, with either pantyhose or nylon stockings. Her eyes were wide open and staring at me. Then I told her to get never again wear her hair in a bun! At this point I stood up and walked behind her and started to undue the bun, but she immediately reached up and said that she would do it. When she was done I took her hair, (which was a little longer than shoulder length), and pulled it over her left shoulder towards the front, and told her that that alone was already a big improvement. She kind of giggled at that, but didn't say anything. So now I really took charge.

I told her to show me her wardrobe. Without saying a word, she stood up and started towards her bedroom, with me close behind. I think she hadn't expected me to follow her, but she didn't say anything. When she opened her closet and turned on the light, I kind of stepped in front of her and started to riffle through everything while she stood meekly by and watched. There was not much there to work with except a green skirt that was never the less still on the long side. I told her to go and put it on so I could see how it looked, and that she should also put on a blouse of some sort. So she went and pulled a blouse out of her dresser and was heading for the bathroom to change, when I told her to hang on a minute. I stooped down to look at the shoes in her closet. Only one pair of heels, which were black, and they only had about a 2" heel. So I handed them to her and told her to put these on too.

While she was changing, I went to the living room and sat down in the recliner, which kind of faced the bedroom, and waited for her to come out. When she did, she again acted very shy and unsure of herself. I have to admit that she really did look a lot better. I told her to walk towards me, and when she got to my chair, I told her to turn around and walk away again and turn around to face me. Then I told her to pull up the skirt and kind of roll it over at the waist to make it shorter, which she did. Then I told her to come back to me again. She was standing to the right of the chair, so I reached out and with my right hand patter her upper thigh, and told her that she looked very nice. However, I told her there was still a lot of room for more improvement, and were she to continue to do as I said, she would be pleasantly surprised with what might come of it.

She asked me what I meant and I told her she would see. At this point I stood up and got behind her and took hold of her skirt and pulled it up a little higher, so that now it was about 4" above her knees. As I came back around, I then kind of briefly ran one hand over her ass, but there was no reaction. She did indeed have nice legs, but she was not wearing any hose. When I asked her why not, she said that she had gotten a bad run in her last pair, and had not yet bought a new one. She also had on no makeup, and I told her it would have been nice if she had thought to at least put on some lipstick, but all she said was that she was sorry, and looked down at the floor.

Now I tried to be a little more demanding and see how she would react. I told her that I wanted her to go shopping, and buy herself a new skirt, short and in black. Also a tighter blouse, that would show off her tits better, (which again made her blush) either in white or red; a new pair of 4" or 5" heels, black nylons or thigh highs, her choice. She was also told to get a new bra that had little openings at the points. She looked at me wide eyed and said that there was no way she could afford all that, since she really didn't have a lot of money. I knew this to be true since I had just helped her with some of her financial paperwork. So I took out my wallet, pulled out three $100 bills and told her to do what I said. She of course tried to refuse, but I was very forceful in telling her that either she could pay for it, or she could allow me to do it since it was my idea. She then acquiesced and accepted it. I told her I would give her exactly one week to get it all done, and that I would then be back.

Standing in front of her, I reached out and put my hands on her upper arms, looked into her eyes, and leaned forward to give her a kiss on the cheek. She did try to turn her mouth towards me, but I pretended not to notice. Then I told her that if she looked as sexy next week as I thought she could, I would have a surprise for her that I felt sure she would like. With that, we made our way to the front door, said our goodbyes, and I left.

Never before had I had the opportunity to dominate a woman like I had done, but had a hunch that I would be able to take this a lot further. I was going to try to become her Master!

The following week, with my briefcase in hand I rang her doorbell and she let me in. I could not believe it was the same woman. She had a big smile, but was still very reserved and I could tell she was a little nervous. I thought to myself Wow! To her I just said that she looked much better, and gave her a big smile in return. She had bought everything I had told her to, and she looked great in it, but I didn't want things to end just yet.

I again sat in the recliner, and we repeated the walking back and forth. Then I asked her to step directly in front of me, with her legs up against the chair. I told her I needed to verify that she had really bought the right kind of hose, and reached out and pulled her skirt upwards. That took her by surprise because she tried to pull away but I had a good hold of her skirt. I looked underneath, and saw that she had on pantyhose, which is not what I had told her to get. When I asked her why she didn't do as I had said, she said that she didn't think it made any difference. I looked at her and let her know that I was not pleased. Then I gently pushed her back and stood up stepping behind her again. Now I told her I wanted to check to see if she had bought the right kind of bra, (although I had already seen that she had not) and slid my arms underneath hers and placed my hands on her breasts. She took a deep intake of breath and started begging me not to do that. After gently squeezing her boobs, and running my hands over her nipples, I dropped my hands, shook my head and told her that I was very disappointed in her. She started telling me how sorry she was, and said that she would go shopping again and buy the correct items.

Shaking my head again, I told her that it was too late. She had disobeyed, and I need to come up with a way to punish her, so that in the future she wouldn't make mistakes like that again. She was very apprehensive and asked me what I meant. After considering for a minute or so, I took her by the arm and led her to the couch and sat down, pulling her into my lap face down. Over her complaints I told her to relax, and it would be over quickly and then I would forgive her. She calmed down a little, and I started spanking her butt. Not hard, but strong enough for her to feel spanked.

Then I let her up and I stood up too. She was kind of bewildered, so I stood directly in front of her, again put my hands on her upper arms as I had done the previous week, and leaned forward to give her a kiss. This time on her lips, which looked really sexy with the red lipstick she had on. She did not pull away, and it was a simple kiss. I did not use my tongue. Then I took her by the hand and walked to her bedroom door and stopped there.

She looked at me apprehensively, not knowing what I was going to do next. I told her I wanted to see her dildo. She looked shocked. I explained that knowing she has been alone for so long, I knew she must have some fort of dildo, and I wanted to see what she had. She insisted that she didn't have one. When I asked her how she got herself off, she at first didn't answer. I told her that we were both adults, and that I expected an answer. If not, I would again punish her as I did before. She still did not answer, so I led her to the bed, sat down and told her to take off her skirt. She just stood there looking at me. I told her that if she didn't take it off, I would have to punish her twice, and if she didn't like it I would leave and not come back.

At that she unzipped and dropped her skirt. Then I told her to turn around and pull down her pantyhose, which she slowly and reluctantly did. Then I gave her a few swats on her bare bottom, and told her she could pull her pantyhose back up. Now I knew she would be my obedient servant. Again I repeated my initial question and she admitted that she sometimes used a vibrator, but no dildo because she didn't have one. When I asked her if she ever got off by playing with her clit, she nodded her head yes.

When asked to see her vibrator, she went to her nightstand and pulled out a small massage type vibrator. I told her to lie on the bed, and when she did I handed her the vibrator and told her to show me how she does it. She just looked at me while holding the machine and didn't move. I went and sat next to her, leaned close to her ear and told her that I really want to see her using it, and I did not want to do any more punishing. She still did not move, so I turned it on and started running it up and down her legs, but never touching her pussy. I could tell she was getting really worked up by how wet she looked between her legs.

At this point I told her that I had almost forgotten the surprise I had brought for her. I handed her the machine, and got up to go back into the living room. On my way out I turned on the lamp on her nightstand, and turned off the main light of the room. I went back in to see her with the vibrator on her pussy, but she pulled it away as soon as she saw me. I told her not to be so shy. Then I told her to pull her pantyhose down a little, which she did. I used this as an opportunity to go down on her, and started licking her clit and sliding my tongue into her pussy. The way she responded, I doubt if anyone had ever given her this pleasure before. After a while, I pulled away and slid the rotating rabbit dildo, which I had brought for her into her pussy, and since she was already sopping wet, it started to slide in very easily.

She suddenly gasped and asked what it was, and I told her that I would show her in a minute. In the mean time I gently slid it in all the way. Then I turned it on. She threw her arms out to the sides and started moaning like I'm sure she hadn't done for a long time. I pulled her pantyhose up, and this kept the dildo inside her pussy. Then I undid the buttons on the front of her blouse, pushed her bra up and out of the way, and started to lick and gently bite her nipples. She threw her arms around me and squeezed me really hard, and then had a massive orgasm.

I untangled myself, and yanked down her pantyhose and pulled the dildo out of her pussy and told her to roll over and get up on all fours, which she did immediately. Then I started kissing and nibbling at her beautiful ass and after a few minutes, once again brought the dildo up to her clit, which got her going again.

I had also brought along an anal probe, which was about one and a half inches in diameter, and about six inches long and had a series of bumps along it's length. I flipped open a bottle of lube with one had and squirted some on her butt hole and on the probe. She was starting to move her ass around trying to get more of that dildo on her clit, so I slid it back into her pussy, and told her to reach back and hold it in place, which she did immediately. I told her to lay her head down on the bed so that her ass would come up a little higher. Then, I slowly started working on her butt. At first she jerked away, but I told her to just relax and keep that dildo in the right place.

Eventually I got the probe all the way in, and she was whimpering and moaning and moving her ass all around. I asked her if I should stop and she of course said no. When I told her that I was going to pull both the probe and the dildo out unless she told me in no uncertain terms what she wanted. She said she wanted to cum. I asked her how. She said with the dildo. I asked what about the probe. She said yes. Yes what, I asked. Keep doing it she said. Doing what? I asked, and told her she better be specific or I would stop. That's when she finally said to keep fucking her ass, which I was happy to oblige. I kept up a steady motion, pulling it almost all the way out, and then quickly shoving it all the way in. Every time I did she gave out a loud grunt and moaned almost continually now. Finally she was bucking her ass like crazy, screamed and collapsed on the bed, allowing the dildo to slip out. I then pulled the probe out, and rolled her over onto her back.

She reached out to me and placed her hand on my cock, but I pulled away grabbing both her hands in mine and pinning them to either side of her head, and gave her a deep kiss and ran my tongue into her mouth. I asked her if she had enjoyed our session, to which she answered yes. I told her that I was not going to fuck her nor let her give me a blow job, until she had bought and worn exactly what I had told her to. She just looked at me and didn't know what to say. I told her that she could keep the rabbit and the anal probe since they were the gift I had promised her. I also told her that she was not allowed to use it until I came back again. She said OK and with that I got up to leave, and she too got up and came to see me off. She threw her arms around me and I kissed her hard, while running my hands over her ass. I told her she had a great body, and that if she promised to be obedient when I came over again, I would consider fucking her in her ass while the rabbit was in her pussy. She promised to be good.

I know it might seem crazy not to have fucked her that night, but I was already laying the groundwork for the future. Besides, when I got home I gave my wife a fucking like she hasn't had in a while.