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Naughty Kelly

I was 59 years old at the time but most took me for 10 years younger or so. I am 6' tall with an athletic build. I hit the gym almost daily. I am not a hardcore muscle head by no means, but I do take pride in keeping tone and fit. In the looks department I have never had a problem with the ladies. I am a Master and have trained many slave/subs over the years. In fact it was this type of relationship that brought us together.

Kelly is 11 years younger than me 5'8 or so with 36 DDD boobs. Long blondish hair with even longer legs. She is an executive with a national company and owns her own home in the suburbs. She shares time with her 8 year old daughter, otherwise she lives alone. She has always been an independent woman and has never had an issue getting men to sexually satisfy her. She confided in me that she has had many lovers over the years. Threesomes, foursomes and moresomes, she has found herself on occasion being passed around after a night of partying by as many as 6 guys. Taking care of them in anyway they desired. These stories that she shares with me always makes my cock rock hard. When she tells me of all her escapades it only makes me love her more.

On our first date I met her at an upscale restaurant in the city she lived in. When I pulled up in my SL 500 and got out she just happened to be getting out of her car at the same time. She asked if I was her date, when I remarked yes, she responded with I am glad you are tall and good looking. During dinner I set the rules on what I was to expect from her if indeed she wanted to be my submissive. She claimed she had a so called Master before but he was nothing like me in the intelligence department. I Dom more with my mind than with ones fist. I am never physically nor mentally abusive, rather I build one up and look at their submissiveness more as a gift and strength rather than weakness.

During dinner we had some great food, wine and conversation. Because of her independent nature and her VP status in the corporate world she has no problem talking over others to get her point across. When this happened during dinner I shushed her to be quiet and listen. She did and confided in me later that was the first time a man ever shushed her. I wondered was she truly a submissive or was it a game she played in the bedroom. I looked for signs as this was not new to me. I did not want to get involved with a controlling sub as the outcome would probably not be good.

After dinner I asked her if she wanted to invite me back to her place. She said yes, but she didn't think we would be a good match as I am a Leo and she is an Aries. I found out later it was her way of playing hard to get. I followed her back to her place and fucked her brains out all night. The only thing she asked is that I cum on her face when I was ready. I eagerly obliged and shot my load across her face and in her mouth. I wondered aloud if I had finally met my match. The next morning we said our good byes and both went to work.

The next day we texted back and forth reliving the evening’s events. She invited me for dinner that evening. Typically I would have declined as I was having way to much fun living the bachelor life and didn’t want to jump into something so quickly. Yet the thoughts of her naked with her big boobs and my cum on her face had me saying WHAT TIME. I brought the wine as well as my bag of bondage gear. When I arrived I had her kneel down on the kitchen floor as I put on one of the larger collars in my bag. I told her in no uncertain terms that she was now mine and had to do as I asked with no hesitation. I then ordered her to stand and remove all her clothing less the collar. Being a nudist she had no problem obliging. I then ordered her to get back on her knees and suck my cock. My cock is on the larger size and thicker than most. I have and many women compliment me on it. Kelly took my cock in her mouth and moaned with pleasure as she slurped on it and rubbed it all over her face. I then ordered her to bend over the kitchen island as I then proceeded to fuck her from behind all along pulling her hair and calling her dirty names. We were both ready to cum and I had her swing around and get back on her knees. I ordered her to open her mouth and stick her tongue out and beg for my cum. I told her to look at me slut as I cum all over your face. I couldn't hold back as she looked so beautiful and sexy as I released and covered her entire face with my entire load. I made her wear it thru the entire evening. I allowed her to wear an apron after that as she was preparing dinner, but nothing else. She even had to remain naked during dinner.

After dinner and a few more glasses of wine, I took her upstairs where I fucked her again this time I dumped my load in her pussy. We then fell asleep and said our good byes the next morning.

We continued to talk and text the next few days. She wanted me to come over every night, yet I was still hesitant to jump in to quickly. Besides I was having too much fun putting myself out there. In the 7 months after my not so amicable break up with my ex and before meeting Kelly I went out with over 50 different women, ages ranging from 26 to 65. Of those I bedded over 35. Some where strictly for sex others I have made life friends with. One thing I can say is I never led them on and told them the truth never wanting to say one thing and do another. I even met 2 nice couples where the husband’s enjoy watching me have my way with their wives. That was always a super turn on and I guess led me down this path.

On one particular day I drove down to Providence to meet a young lady I met on alt.com. She claimed to be submissive as well. I met her at Federal Hill and had a very nice dinner. She asked me if I wanted to go to a party later, never one to say no I agreed. I followed her to her house where we dropped her car off. She gave me directions to the house all the while rubbing my cock. Once there I realized this was a swingers party. We got the tour and after a drink she brought me upstairs to a semi private room. Once inside we got down and dirty. I fucked her for about an hour all the time being watched by a few guys enjoying the show. I wanted them to join but she insisted I was enough for her that evening. We were being very naughty and loved for me to talk dirty to her. I only saw her once after that. After driving home at 2 o'clock in the morning and taking a nap I got a text from a young lady I had seen in the past. She was married and we use to hook up a few times a week for sex in her back seat before she would go home to see her husband. She was 20 years younger than me and she also wore my collar and loved dirty talk. I had not seen her in almost 4 months and was surprised to hear from her. She was going to be in my town and wanted to meet in the parking lot behind the local supermarket. As tired as I was I could not say no. There we were an hr later fucking in her backseat in broad daylight. After 15 minutes or so of crazy sex I shot off all over her delicious D boobs. I thanked her and we kissed good bye. We talked a few times since but that was the last time I saw her. Later that evening after dinner at the local pub I got a call from my couple friends inviting me over. Their kids were with the grand parents and they were feeling frisky. I declined politely but they kept pressing. They were all worked up with the thoughts of it. I finally agreed and met them at their home. Thank god they lived in the same town. He answered the door and invited me in. We went into the kitchen where his wife was waiting with a glass of wine. Being the take charge guy I am, I thanked her then kissed her on the lips. I turned her around and pulled her pants down to her ankles. I then bent her over their hand carved wood island bar and fucked her from behind. After spit roasting her and having her suck both of our cocks and fucking her in 3 different positions I was ready to leave. She was not done and thought we should go up to the bedroom. Again I was exhausted but obliged and the 3 of us proceeded to fuck in different positions and scenarios for the next hour. I had cum over 5 times that day. I had fucked 3 different girls at 3 different times. I was spent. I slept till 11 am the next morning. Can you see why I was reluctant to give this all up even though it was wearing me out. My house was a revolving door for ladies coming and going. My room mate was getting jealous even though I offered him to have his way with a few of them. One of the girls I was seeing lived a 1/2 mile up the road. She was 26 years old and was living with her parents. She would sneak over for a night of sex. She wanted to be the house slut and take care of us both. I offered this to him but he refused. He was telling me about all the woman he was seeing, yet I never met or saw any of them. He was always sitting in his chair in the living room watching TV every night. When he lost his job it was morning noon and night. Even though he was10 years younger than me, I felt like I was living with my Grandfather. He became weird and judgmental even though we were both renting the home and I was paying all the bills. It was time to find another place till my home that the Ex lived in sold.

I continued to see more of Kelly. The next date she invited me over for dinner. I showed up with wine and flowers for her. I went thru the ritual of collaring her and stripping her naked. While she was preparing dinner I told her that she was going to get a spanking that night just to show her who was in charge. After dinner I took her upstairs and had her lie over my knee. I then gave her a 15 minute spanking using different techniques and strokes until she came all over my lap. By that time my hand was as red as her butt. After that she got on her knees and sucked her Masters cock till I exploded all over her face. She was the dirty slut I always wanted.

We eventually moved in together. We were having sex as many as 4 to 5 times a day. She was wearing my collar and doing as she was told. One night I put an ad on Craigslist looking for a younger guy. This 20 something kid answered our ad , we agreed to meet in the parking lot of a local supermarket. It backed up to the Mystic river bicycle path. We parked in a very remote area in the dark and told him we would be in a white SUV. As we waited I was getting Kelly warmed up by rubbing her boobs and kissing her all over. I then saw a guy walking toward us, at first he seemed lost, but he walked directly toward us. I assumed at that point he was the guy we were supposed to meet. I told Kelly to pull her skirt and shirt up when he came over to the car. It was dark and he went around to the passenger side window and looked in. There she was boobs and pussy exposed to this stranger. He started playing with her boobs thru the window. Once we opened the door to give him better access the interior light went on. Because we were in a public area I suggested we move to the woods behind us. Kelly got out and he followed her into the woods. I locked the car and followed behind a minute or so. It was dark but I found my way to the clearing and in the moonlight I could see Kelly on her knees giving our new friend a blow job. That made my cock stiffen. Not to be one to be left out, I unzipped my pants and put my cock in her mouth. She now had 2 cocks in her mouth and she was loving it. I then noticed there were people walking the path. It was dark and we were right off the path. Most didn’t notice us but one guy stopped to watch the action. We didn’t stop, in fact we put a show on for him. I then turned her around and as she was bent over sucking his cock I fucked her from behind. After about 5 minutes of this I told them I was going to cum. I pulled out and moved around front to unload all over her willing mouth and face. The kid was so turned on he followed 30 seconds later. We put our cocks away and I told Kelly to thank him and we went back to our vehicle. We said our good byes and by the time we got home I was so horny. I jumped her when we walked in the door and fucked her again on the floor with our cum still on her face. She loves telling me what a slut she is as much as I love telling her what a good slut she is for me.

The next time we met a single guy at his apartment which was literally 5 minutes up the road. He was about 30 years or so younger than me but he loved older women. When we arrived I had Kelly strip naked. She crawled over on her hands and knees to where he was sitting on the couch. She pulled his pants down and proceeded to suck his cock to life. After about 5 minutes of this I ordered her to kneel on the couch. I went over to the back of the couch and stuck my cock in her mouth. He took her from behind and we double teamed her taking turns switching back and forth. We then laid her on the floor and I fucked her while she sucked his cock. I pulled out and exploded on her face and he soon followed. She thanked him and we got dressed and left never wiping the 2 loads of cum from her face. When we got back to the house I had her get 2 dildo’s and I watched her fuck herself with one while sucking the other. After watching her lost in her orgasm I got up and jerked off on her face. Load number 3. Yikes she was one naughty girl. ( to be continued )