Teaching An Old Dog A New Trick

This story is dedicated to the author called Madison018. Her stories are so fine that I decided to write this because I learned something about myself while reading her stories. I hope that she likes this one. I wrote it because I’ve been reading about Dom/sub relationships and am VERY curious to find out whether I’m a Dom or not. This is kind of a fantasy and kind of a reality story. Some parts are real but I’ll leave it to the reader to decide where the line is.

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I’m just your average guy. Or I thought so… up until the events that I’d like to tell you about. Up to this point in my life I never thought of myself as unusual. My tastes in women were just “normal”. What turns me on is slightly built women with small breasts. I like olive skinned women with all but red hair. Now, don’t get me wrong…I have lusted after, dated and even married a red headed women. It’s just that blondes, brunettes and raven-haired women are more to my liking.

I’m recently divorced and live fairly close to an Ivy League University In New Haven. The neighborhood is pretty well dominated by apartments that cater to the University’s students. My own apartment is modest but comfortable. It’s in a rather large house that’s been converted to apartments by the landlord and as I said there are students living in the other apartments. I know all of the kids in the building because for some reason, I’ve been unofficially designated as kind of the house protector and father figure. There’s a really nice assortment of men and women of various classes. We have three seniors, four juniors and one sophomore. Everyone has their own kitchen/dining room, bathroom and two rooms that can be used as a bedroom and living room. As I said, cozy. Up until about a week before the fall semester began, there was one empty apartment. That’s when a nice looking woman moved in. I didn’t meet her until about a week after she moved in. I literally bumped into her one day in the hallway. I apologized and introduced myself.

“Hi. My name’s Tom and I live in the apartment at the front on the second floor”, I told her.

“Oh, hi. I’m Madison and Sherry told me about you. She said that you’re nice and that you’re friendly. She told me that if I have any problems that you’re very helpful.”

“Well, Madison, I keep to myself when it’s warranted but I like the people that live here. If you have any parties, let us know and we’ll keep an eye out for you. If you need anything else, look me up and I’ll do what I can.”

“Thanks, Tom, but parties aren’t my style. I’m a freshman and I’d like to make good grades while in school so there won’t be much of that in my place.”

“No problem even if you do, kiddo. We like to have what we call “community dinner” about once a month or so and this month is my turn. It’s pot luck and everybody contributes, so stop up on Friday night at about seven and we can all get acquainted, ok?”

“Thanks, I’d like that, Tom.” With that she flipped a wave at me and disappeared on her way to classes, I guess.

I remember thinking that she was a pleasant woman in every way. She’s pleasant to chat with and very pleasant to look at, I said to myself. She has brown hair that reaches a little below her shoulders and a very nice shade of green in her eyes. She’s thin, about 5’ 5” tall and nice curves. What struck me, though, was the fact that she has smallish breasts. Her breasts are not very small but on the small side. However, they had a nice fullness and shape. She has the body type that has always turned my head.

Friday night arrived and the other kids (as I called them) started to drift in with their cheery banter and a small dish to share. Everyone had arrived except Madison but nobody gave it another thought. As we heated up the dishes and started in on the feast, I finally recognized that Madison hadn’t arrived. I mentioned it to Dina who was in the kitchen with me. She also seemed a bit surprised that Madison hadn’t yet arrived. I told Dina that I would go down and see if she was home and extend another invitation in case she felt out of place.

I knocked on the door and I was pleasantly surprised when she answered. “Hey, are you attending our little house dinner?” I asked as nicely as I could.

“Well, I thought that I’d skip this one because I really don’t want to impose,” she replied.

“Impose? What impose? We do this all the time. How else are you going to meet your neighbors?” I bantered. “Come on, everybody’s up there already and you are definitely not imposing,” I tried to reassure her.

“Well, I don’t have anything to bring,” was her reply.

“Never mind that. It’s your first time and I really don’t think that anybody would mind all that much. You can get to meet your neighbors and they will be more than happy to help you get oriented to your surroundings and the fact that you’re a freshman would be to your advantage, you know.”

I think that was what convinced her to join us. The rest of the evening went pleasantly and I think that everyone enjoyed the company. I know that I did. Madison fit in pretty well and the talk seemed to flow easily enough. We all chipped in with our advice on the area and the kids seemed happy to help Madison get oriented to the university buildings and the culture of the place. Madison was the last one in the apartment and she and I just chatted away the night. I learned about her, told her about me and we just filled the night with idle chat about everything and nothing. When she said her good night, I was struck at the fact that she was, indeed, a pleasant young lady and told her so. She smiled and said that she, too, had enjoyed the evening. I told her that if she needed anything that she shouldn’t feel that she was imposing. She immediately got the joke, giggled and graciously accepted the offer. She surprised me when she moved close as if she were going to whisper something but gave me a peck on the cheek and closed the door behind her.

Nothing much happened for the next few days and weeks. You know how it is…life just seems to roll on. I saw all of the folks in the house and we chatted and went our way. Then one evening after I had come home from work, there was a knock on my door. I answered the door as I was changing my shirt. I quickly pulled the shirt over my head and opened the door to find Madison in an agitated state. She seemed upset at something, so I invited her in. I expected her to cry at almost any moment. I asked her what seemed to be the problem. She told me that her computer had crashed and she was in the middle of writing an important paper for a class and that she could not get the computer back up. I offered to look at it for her to see if there was anything that I could do. She knew that I was into computers and that I had one of my own so she gladly accepted the offer.

We sat down at her computer. The power lights were on but the screen was blank. I asked her to describe what had happened. When she told me what had happened and after some cursory diagnosis, I figured that her hard disc had crashed and was unsalvageable. Then she did start to cry. I quickly told her that she could use my computer to finish her paper. I asked if she had her notes and whether she could rewrite her paper from scratch. She sniffled, and nodded her head in the affirmative.

“Well, then, I think we should make tracks up to my apartment and get you going if you’re going to get it finished in time,” I said.

“Ok, but it’s going to take me all night. Can stay there until I finish?” she asked.

“Of course you can. I don’t have any plans to use it tonight, anyway. You can stay until you’re finished, ok?”

That seemed to do the trick. She settled down and followed me out of her apartment. We ambled up the stairs to my place while did my best to cheer her up. I think most people would call it flirting with her. The funny thing is that most people would be right! I was flirting with her. The realization almost floored me. I hadn’t flirted with a woman in a long time…certainly not with a woman almost twenty years my junior and DEFINITELY not one of the girls in my complex! I went to the dining room, armed with my checkbook and the stack of monthly bills that had to be paid. I figured that this was as good a time as any to do the monthly chore.

When I looked up, Madison was standing in the doorway to the room and was leaning on the frame watching me work.

“What’s up?” I asked.

“Nothing, just taking a break,” she said.

“Well, come on in and I’ll get a soda for us and we can take a break together or a beer if you’d rather that,” I said.

“No, soda would be fine,” she said as she sat down.

I retrieved the glasses, poured the soda and sat down to chat. After a few minutes, I again realized that this was more flirting than idle chat. Then IT happened. The it was something that, at the moment, seemed innocent. Madison knocked her glass of Pepsi over and it spilled onto the pile of “paid” bills. She jumped up and seemed to run in three different directions at once. I calmly rose to get a towel to wipe up the spilled soda. But Madison was anything but calm. She kept muttering to herself about being so clumsy. I tried to brush off her comments but she wouldn’t hear of it. What she said next still reverberates in my brain. It seemed like a strange thing at the time and after we’d cleaned up it still hung in the air. What she said was and I quote “I deserve to be punished for ruining your paperwork.”

“There’s no problem, Madison. Why don’t you go and continue working on the paper for class,” I suggested.

“Ok, but I’d like to talk about this later. Ok?” she asked.

“Ok, but there really isn’t anything that needs talking about.” I thought that I was reassuring her about the accident.

After a long while, the checks were written, the envelopes stamped and I was in the mood to watch some television. It was getting late and I decided that I would just go to bed instead of disturbing Madison. The television and the boob tube were in the same room so it just seemed natural to hit the sack. I told Madison of my decision and that she was welcome to stay as late as she needed to finish her paper. I would turn in and she should turn out the lights on her way out of the apartment when she was finished and that I’d see her tomorrow and look at her computer to see what she needed to fix the problem. She agreed and went back to her task.

The next day, after I arrived home from work and had changed into more comfortable clothes, I went to Madison’s apartment to look at her computer. As it turned out, she wasn’t home yet from classes, so I went back to my digs and set about preparing dinner. After I had eaten dinner and cleaned up the kitchen, I was just going to watch some television and laze about for the rest of the evening. Then I realized that I’d promised Madison that I’d look at her computer. I headed out the door and when I reached her door, I gently knocked. Apparently she had just arrived home because she was dressed in her usual class attire. She had on a pleated skirt that came to about mid thigh, knee length socks and a pretty blouse that accentuated her feminine curves.

“Hi, Tom. I just got home and was about to come up to your place.” She delivered this almost in a whisper.

“Hi Madison, I came down to look at the computer to see if there’s anything that can be done to salvage the hard drive,” I said.

“Oh. Ok, come on in, then.” I couldn’t understand her hushed tones and reminded myself to ask her about it when we were through with the pc.

The examination of her computer was done pretty quickly. I turned to her and gave her the bad news. “You’ll need a new hard drive and I can do that for you and have you back up in about three days, depending on our schedules meshing. As long as I can get to the store and into your apartment tomorrow night and the following night, you’ll have a working pc by Friday. Are you free tomorrow night as well as Thursday night?”

“No problem, Tom. I’ll make sure that I’m free. I depend on the pc to study and to research class assignments. I’ll do whatever I have to do so that I can have it back as soon as possible.” She was still conversing in those hushed tones and it was starting to bother me. It felt like she was not fully responding to me.

“Madison, what’s wrong? There’s something happening and the way that you’re responding to me isn’t like you at all. I feel like you’re treating me like you expect me to hurt you somehow.”

“Well, last night is still bothering me.”

“ What do you mean? You used my pc to do a paper and left when you were finished. It doesn’t bother me, so what’s bothering you?”

Her voice got quieter still as she responded, “ Well, I DID spill my soda all over your paperwork and I need to be punished.” We were still seated at her desk and her eyes never left her feet.

I almost fell off of my chair. “Punished?! Punished for that? It was an accident and we both cleaned up the spill quickly.”

“I know it was an accident but I wasn’t paying attention and made a big mess. For being so careless I deserve to be punished.” She was still looking like a little girl and speaking in those hushed tones.

I was, to say the least, curious about what she meant by punished. I decided to dig deeper into what she thought should be an appropriate punishment. “OK, let’s say that you should be punished. What do you think we should do about it?”

“Well, usually I’d get a spanking.” That line was delivered so quietly that I thought that I hadn’t heard her correctly.

“Oh. Just who usually did the spanking?” I asked.

“Well, my father usually punished me but I’ve been punished by a couple of teachers and once by my neighbor. He was my father’s close friend.”

Sweet Christ, I thought. This isn’t an act, and furthermore, there’s more going on here than just corporal punishment. “Is that what’s warranted here, too?” I asked.

“Well that’s what usually happened when I was careless or misbehaved. Is that what YOU think should happen?”

I continued along this tract. “Well I’ve never administered a spanking to a young lady. What usually happened when you were spanked?”

“My teachers and my fathers friend put me over their knees and spanked me.” She was blushing at this admission; but I knew that there was more, much more, to this story and I wanted to find out the entire tale.

“Madison, look at me when I talk to you. Tell me exactly what happened when they spanked you.” I felt that I needed to assume a stern tone to get to the bottom of this spanking business, so I put on my best game face.

In barely a whisper, Madison told me, “ After I lay across their knees, they lifted my skirt and pulled my panties down and as they talked to me about my behavior, they began to slap my behind. I was so ashamed but at the same time I was extremely excited.”

BINGO! I thought. That’s what’s going on here. I immediately knew what was expected of me so I then calmly but sternly told her that she must indeed be punished and that I would begin to administer her spanking right now. “Lay across my lap,” I told her.

She looked a bit apprehensive but quickly complied. As she lay across my legs, her skirt had ridden up her thighs a bit. I began to caress her bared legs and slowly slid my hand up her legs, slipping her skirt up in the process. As her panties came into view I noticed that she was wearing black, sheer panties. They allowed just a hint at her fine, fine ass cheeks and I was truly mesmerized by the sight. When her skirt was out of the way, I began to caress her cheeks while I spoke to her sternly. “This spanking will make you aware that you will be more careful and more attentive when you are in my apartment. Do you understand, Madison?”

When she whimpered in the affirmative, I slid her panties to about mid thigh. I then asked her again whether she understood what I had said. There was another whispered, “ Yes.” I brought my hand down hard against her pretty left ass cheek. A loud crack startled her. I told her that she must answer me and to let me hear the answer. More convincingly, She said, “I’m sorry, yes.” I administered another hard slap to her right cheek and I was sure that the contact is what made her jump. I also heard a slight moan from her. I began to administer a first class spanking to her tight ass. All through her punishment, I spoke to her and began to tell her that this is what she could expect whenever she misbehaved or became careless. To her credit, she received her spanking without the tears and crying that I had expected. As I approached slap number 12, I realized that she was becoming excited. Rather than moaning from pain or humiliation, she was writhing on my crotch in a very suggestive manner! Then it dawned on me that I was rock hard! Her movements were right on my cock and only increased my own excitement.

At this moment, I knew that she was getting some stimulation from my spanking and at that moment, I began to caress her cheeks. I started to caress the reddening skin of her ass and as I did so, I deliberately began to inch my way to the slightly parted juncture of her legs. When I reached that juncture, I felt the unmistakable wetness of sexual arousal. Her secretions had soaked the hair that surrounded her treasure.

I knew that I was in VERY unfamiliar territory. I ran my fingers through the leakage of her pussy. I felt astounded that a woman could get this aroused from a spanking but like a magnet I was drawn to continue running my fingers through the fine hairs of her most private parts. When I heard Madison’s breathing become more labored and slight sighs, I asked her “Does that feel good, Madison?” Her only reply was to moan louder. I slapped her ass again, harder than I had previously. “You didn’t answer me Madison.”

This time I got the required answer. “Yes, it feels really good, Tom.” I slapped her ass again and said, “You will address me as Sir when you get a spanking. Do you understand that, Madison?” Her reply was immediate and in the manner that we had agreed upon. “Yes, Sir,” was all that she said. “Good. Now let’s see if we can take some of the sting out of the spanking, shall we?” When she replied in the proscribed manner, “Yes, Sir.” I began to caress her cheeks again. I also began to make my way down to her cunt. When I reached the wetness in her crotch, she spread her thighs slightly. However, her panties, being at her thighs, prevented her from going too far. I then pulled them down to her ankles before removing them completely. I then put her panties on the desk. I was again reminded of my own arousal because she began sliding her crotch over the shaft of my cock. I hadn’t been this hard in a long time and decided to prolong the sensations that she was re-awakening.

At this point I remembered that her punishment had aroused Madison but I wasn’t sure what more she needed. So I asked her to tell me what else her teachers and neighbor had done to punish her.

She got really quiet again as she answered me. “Do I have to tell you?” she softly asked. “Yes, you do and because you didn’t call me Sir, I want all of the details. Remember that if you don’t tell me everything you will be punished again and that will be more severe, so I suggest that you give me all of the particulars.”

Madison began to softly sob as she told me her tale. “ I was punished by my teacher first because I was late for class. He made me come to see him after school was out for the day. I met him in his office. He made me lay across his lap as he spanked me on my bare bottom. He then rubbed my cheeks, like you did. It started to feel good and I noticed that he was getting hard, like you are now. I started to rub his hardness with my pussy and he got harder. I noticed that his rubbing got closer to my pussy, like you were doing. He then told me to get on my knees and take his cock out of his pants. I never heard a penis called a cock and it sounded so dirty that it made me hotter. I got on my knees between his legs and opened his pants and took hold of his penis. I had never seen one in the light and so closely before and I was so hot. I then took his pants down while he lifted himself up. His penis was so big and hard. I took hold of it and he showed me how to rub it so that it felt good for him. He was moaning that it felt good. Then I noticed a drop of liquid was at the tip and he saw me looking at it and he told me that it was called pre-cum. He told me to lick it off of his cock and I did. It was strange because it tasted a little salty but the consistency was like nothing I’d ever tasted before. Doing that only made me hotter, if that was possible. Then he told me that he was going to teach me how to blow him. I’d heard of blowjobs before from my girlfriends but never imagined that I would do something so gross. I was so hot for his penis that I let him pull my head towards it. I kissed it when he said to do that and I licked his pre-cum when he told me to do that. I couldn’t believe how excited I was. My pussy was so wet that it was practically dripping. Then he told me to take the head into my mouth and lick it while it was in my mouth. After a little while, he started to slide it in a little bit further and then back out. He kept doing that but he went a little deeper into my mouth each time he slid back into my mouth. It wasn’t long before he was touching the back of my mouth near my throat and I gagged. He told me that later he would teach me to do it without gagging but that for now I shouldn’t let it go that deeply into my mouth. He also told me to move my head up and down and to keep my lips tight around his cock. I began doing that instead of him sliding it in and out of my mouth. I was able to do it without gagging. Before long he said that I was doing it just right and he was almost ready to cum. I got scared and started to pull him out because I had never even seen a penis, let alone make him cum into my mouth. He grabbed my hair and pulled me back so that he was almost at my throat and I felt his penis throb and then he began to spurt into my mouth. He told me to keep his cum in my mouth and not let any dribble back out. So I did. He tasted salty and it was a lot of stuff coming out of his penis. I was scared but at the same time I was really excited. I had never been so hot, not even when I made myself have an orgasm with my hand. When his penis stopped throbbing, he told me to swallow all of his cum. I felt so dirty but I did as he said, I swallowed it all. His penis was still in my mouth and he started to get small and soft. He pulled my head back away from his penis and told me that that was the best blowjob that he had in a long time. Then he told me to stand up, turn around and lay across his desk. I did it and he pulled my skirt back up around my hips. When he did that, I realized that my bare pussy was exposed to him. He began to play with me and slid his finger up me. I felt like I was on fire there as he began to play with my pussy. He played with my pussy and then with my clitoris. I had never felt this hot. He made me orgasm and I just lay on his desk, afterwards. As I got my breath back, he told me to stand up and face him. When I did, he told me that I should never tell anyone about what we just did. I told him that I wouldn’t. I knew that we would get into trouble if I told anybody. He told me that I should go home now and to think of the consequences if I misbehaved again. He punished me a couple of times after that but then school ended and I graduated.”