After I had broken up with my girlfriend, I was horny. Very horny. I also was interested in blurring the line between sex and control. I wanted to be dominated by a woman and try dominating her. I made an unusual choice of sex partners.

I was still fairly young - 23. I was living close to where I grew up. About an hour away from my boyhood home in a nearby city. It was a weekday night, and I was shopping in an expensive mall. Out of the blue, a woman stopped me. She gave me a warm smile and big hug. I took me a moment and then I recognized her even though I hadn't seen her in eight years. She was Mrs. Clarkson, the last babysitter I had.

She was chatting me up. Asking how my younger b*****r and f****y were. She kept saying how handsome I had become. She was smiling from ear to ear, occasionally touching my arm or shoulder. It was the way she was...at least to me.

Mrs. Clarkson babysat me from when I was about 12 to 15. She would check in on me and my b*****r when our parents were away. She would stay the night to keep an eye on my much younger b*****r and make sure that I wasn't hosting any parties. I didn't like having someone in that role but Mrs. Clarkson made it bearable.

We knew her because she lived three doors down from us. Mrs Clarkson's only daughter went to college, and she missed k**s. She decided to do a little babysitting. She always was friendly. My b*****r and I liked her. As I was just starting to like girls and ask them out, Mrs. Clarkson gave me some advice. I wasn't going to talk to my parents about girls. She always was interested in who I liked at school and if I had a girlfriend.

Mrs. Clarkson was pretty. When you hit puberty, almost any woman seems fuckable, but she was pretty. I would stare at her breasts. When she would catch me, she would smile and sometimes remind me to look at her eyes. Her breasts were much bigger than any girl I knew. She also seemed to wear outfits that showed them off. I think that she liked the attention.

As a teen, I had dreamed of fucking her so many times. I must have cum over 100 times thinking about her while I was in the shower, in the bathroom or in bed late at night. I wanted to kiss her beautiful face, feel her blonde hair, lick her breasts, suck on her nipples, taste her pussy and fuck her like crazy. There were so many scenarios where she would seduce me or teach me about sex.
Now I was an adult and talking with her like an adult.

She asked me what I was doing in the mall, who I was dating and how I was. I asked her how she was and learned that she lived nearby. I knew that she moved out of our neighborhood three years before. She explained that she was growing apart from Mr. Clarkson. Under the circumstances, they weren't going to live in that house together and decided to sell it. She was working in a doctor's office in the area and had a townhouse.

She also let me know that she wasn't dating anyone. The divorce was made final a year ago. Mrs. Clarkson has gone on a few dates but wasn't seeing anyone. I was surprised. She was older than when I last saw her but still pretty.

Mrs. Clarkson had her daughter when she was 23. Somehow her daughter was never that attractive. She must have talken after Mr. Clarkson. Now Mrs. Clarkson was about to reach 50.

She still was hot though, even to a 23 year old. Her blonde hair was short now. She still showed off her cleavage. Her ass was a little bigger but is was nice. Her face looked a little older. She had a few lines by her eyes and mouth, but I still wanted her.
I thought that I might not see her again, and no one would know if I made an ass out of myself, so I asked her to dinner.

Mrs. Clarkson was a little taken back. Her eyes got wide. She started to say no, then caught herself. "Why not!" she said. I asked her out that for Friday. She was a little slow to agree but I talked her into it. We would meet at the same mall again and meet at one of its restaurants.

When Friday arrived, I got nervous. What was I doing? She may not show. As I thought of her, I got hard. That decided it for me. I had to try. No chickening out.

I went to the restaurant and put in my name. Ten minutes later she arrived. She was looking nice. Very done up, even more than before. She kept it conservative though. Her dress didn't show much skin. There was just a little cleavage. It looked like she was dressed for a business dinner.

We hit it off. Laughed a lot. I tried to keep her drinking. After sharing a bottle of wine, she loosened up more. I learned more about her divorce and how strange it was for her to date again. She made a point not to call our dinner a date. We were just olde friends catching up.

When dinner was over, I asked if we could do it again. I asked her about her townhouse during dinner. She was proud of it. We decided on next Saturday night. After talking about going out or having dinner. She suggested a place that was quiet. I thought that she was feeling a little uncomfortable having a dinner date with a guy half her age. She eventually offered to make dinner, so that I could see her place. I jumped at the opportunity.

A week passed. I was getting ready to drive over. I decided to wear sometime less dressy but have an open shirt. I arrived with flowers and wine. This time she was dressed differently.

Mrs. Clarkson was wearing a short black shirt and a red blouse that showed a lot of cleavage. Those were the tits that I had stared at so many times.
She showed me around and we had dinner. We polished off the bottle of wine. The discussion changed from the preceding week.

She told me more about what she was like when she was young. She insisted that I call her Wendy. We also talked about her babysitting. I apologized for staring at her as a k** and thanked her for her great advice with girls. She asked more about my dating life. I gave her more details. She asked a lot about that.

Wendy also asked what I thought of her. I explained that I worshiped her and thought that she was the most beautiful woman in the world. I even admitted to dreaming about her. She told me that it was sweet that I stared at her so much. We moved to her couch.

We kept talking. I asked to kiss her. She started to say, "I don't think that would be a very good..." when I leaned forward and kissed her. She was shocked but didn't move. I looked in her eyes and kissed her again. She slowly started to kiss back. Soon we were making out. I was all over her, and she was responding.

I took it slow but did not relent. Soon my hand was in her blouse. I was cupping her large, droopy breast in her bra. It felt great. The bra had a clasp in the front, so I took the chance and released her breasts. In that moment, I looked down at these beautiful breasts peeking out from her open red blouse. They were just as I had imagined. Big silver dollar areolas with eraser tip nipples. My face must has looked like a k** opening a big present. She was looking at me, star at her. Our eyes met and she slowly blinked both eyes in approval.
kissed her again, then down her neck and began kissing and licking her breasts. When I would lightly suck her nipple, Wendy let out a low moan. I began to suck harder. She was loving it.

I reached up her skirt. Her thighs were full and shapely. She was wearing garters! When my fingers reached her panties. I felt this wet satin. She helped take off her skirt, blouse and bra. I saw this beautiful cougar half-reclining on her couch. Wearing just black stockings, garters and panties. I kneeled on the floor and looked up. Wendy slowly blinked her eyes again in approval. I started kissing up her legs and was licking her pussy through the black satin. I could taste her. She was wet. I pull her panties off her full hips and took them off entirely.
Wendy had a trimmed pussy. The hair was short, light brown and a little white. I immediate began eating her pussy. I started to lick her gently and politely. In time, I was slobbering all over her pussy.I had three fingers squeezed together and sliding an and out of her as I licked and sucked her clit. Her legs were spread wide open. Her legs soon were on my shoulders and d**** dover my back. Her legs were squeezing me closer to get pussy. Her grip became stronger. I looked up to see her biting down on her fist. She then had a long, shaky orgasm. Her whole body trebled with the waves of her orgasm. It was long. She was grunting and snarling through it all.She was loving it.
I kept sucking her until she brought my head up to her. I sat beside her. She told me that was, "the best one she has had in years."

I was so hard and clothed. I started to strip. after taking off my shirt, socks and shoes. she asked me to stop. I stood in front of Wendy. Her hands started exploring my chest. Red nails touching every inch. She looked up at me, and I slowly blinked both eyes to her. She started to examine my bulge. She unbuckled my pants and let them fall to the floor. I stepped out of them. She looked at my underwear to see the tip of my hard penis sticking out from the top of my boxer briefs. Her fingers traced my cock. She even started to jack it a little. She then pulled my underwear down as her eyes got wide. She wrapped her whole hand around my cock and made a comment about being bigger than her ex.

She looked up at me. I was hoping that she would blow me. She knew that and decided not to.

She sat back on the couch and told me to lay back on her lap. My head was on the couch's arm rest. My torso was on her lap. She told me then to suck them again. I started to lick and suck her large breasts. Wendy then reached over and began jacking me off. She was good! Her warm hand was strong and soft. I could hear her bracelet jingle as me massages my cock and balls then jacked me harder. She held my cock much better than any girl had ever touched me. There was no friction. She knew what she was doing. She had a very firm grip on my shaft, would occasionally flick my head with her forefinger, and then jacked me hard and fast. I came in no time. My cum was shooting all over my chest and stomach. I mad a mess. She was loving the control.
After I came, she brought her hand up to her mouth and licked the cum off her fingers as she stared at me. I was hooked.

That characterized the first two months of own relationship. We would go out, keep a low profile, go back to her townhouse and have sex. Sex was me going down on her and she jacking me off as she took control. We began talking about sex more. She let me know that she never knew her nipples were so responsive. She encouraged me to suck them and hard. I wasn't hurting her. She was loving it. I had the courage to ask if she would suck on my cock. She said that she never really did that before. She would either jack her ex off or have intercourse. She tried oral a few times but didn't like it.

I then asked if we could have intercourse then. She thought about it and eventually agreed. Later that night, we tried it.

We were in her bed. I had just gone down on her to another orgasm. She was getting more verbal now. She started to demand. Instead of just grunt or moan, she would order me to "lick it" or "suck me." It was working for both of us. Instead of moving up next to her for her to jack me off, she then got on top of me. It was a great view.
I saw her sex-crazed look, her big, hanging breasts with nipples brushing against me, a little of her stomach, these wide hips and the full legs on either side of mine. She started to ask, "Is this what you want?" again and again. I breathlessly agreed. She ordered me to beg. I started to beg politely. Soon I was talking nasty. "I want to slide my swollen young cock in your wet pussy." "Sit on my cock, please!" She then rubbed the head of my cock all around her opening and clit. She asked, "Is this what you want?" I responded "yes, please!" She then ordered me to look at her as she slowly sat on my cock. I fit in her perfectly. I went all the way in. She was so warm and wet. She then ordered me to grab her hips. She has full, womanly hips. I grabbed her and started thrusting. I tried to start slow.

I was going faster and faster. She was talking in my ear, "harder" and "is this what you want?" I started to cum in her. It felt so good. When I eventually flopped out of her pussy, my cream dripped out of her and on to my lower stomach.
That was a big step for us. We then would mix up jacking off and intercourse. She was great at intercourse but didn't cum unless I went down on her.

That winter, I convinced her to go on a vacation with me. We went to Florida. That trip changed everything.

Maybe because we were in a unfamiliar place, she stop caring what other people thought. We didn't know anyone there. She wore a bikini to the beach and dressed in sexy clothes the entire trip. We held hands and kissed in public. We acted like lovesick teenagers.

The first night at the resort, I decided not to go down on her until she orgasmed. I had a surprise. She was nice and wet, and I got on top this time. I entered her. While my cock was in her milf pussy, I took out a little vibrator. I told her to trust me.

When I slowly pumped my cock in her pussy, I ran that little vibrator around her pussy. She wanted me to go slow. Eventually I was fucking her hard, and that vibrator was directly on her clit. That was it. She came. It was a surprise for her. She started to yell as she came. This very well-mannered, professional woman was yelling "fuuuuccckk!" Her strong pussy muscles gripped my cock hard. Her pussy was squeezing my cock hard the soft, hard then soft. It was too much for me. I came with her. That was our first simultaneous orgasm.
That next morning, I convinced her to try sucking cock. She started jacking my cock again. I gently guided her head down to my cock. She looked at me. I asked her to try. She started sucking the tip. In time she had most of my cock in her mouth. She became comfortable and started sucking harder. I came in her mouth without warning. She swallowed me down. Every drop. When she moved up next to me again, I kissed her passionately.

While on the beach the next afternoon, we started to make out. No one was around us or could see us. I told her that I wanted to suck her pussy. That was her 50th birthday. This 50 year old lady was laying on a beach with her bikini bottoms off. Her legs were wide open as a 23 year-old, me, was sucking her pussy to orgasm. She loved it.
A day later, I was driving the car. I convinced her to touch my cock while I was driving. She was jacking me. We saw other cars and trucks around us. I asked her if she would blow me. To my surprise, she did! This demure lady, who once was my babysitter, was sucking my cock as we drove around Florida. I couldn't believe it.

She was really getting into to it, so I didn't tell her that a moving truck pulled up next to us at a stop light. There were three buys in the front seat of the truck. Two were watching her blow me. They only saw her head bobbing up and down. They told the driver to beep the horn. He beeped the horn loudly. I was cumming at that point. Wendy was started. She looked up to see two men watching her from the truck above us. She froze. They saw this 50 year old lady look up from my cock with cum dripping from her mouth. They were shocked also. They went crazy, laughing and cheering.

I was concerned about what Wendy was thinking. I gave her a big kiss. She looked at me. She was fine and started to smile. I asked her if she felt like a slut. She said "yes." I asked if that was ok. She said "yes."

That was it. Our sexual relationship changed on the trip. When we returned home, we played power games all the time. She would order me to touch her pussy under the table during dinner. We went for a walk in a park, found a secluded place, and I went down on her while she sat on the bench. We would whisper nasty comments to each other such as, "Are you dressing like a little slut tonight?" and "Are you going to be suck a thick cock in the parking lot?" We even did a little teacher/student role play at home. She also started to like being fucked doggy style as she ran our vibrator on her clit. Just the sight of this mature blonde with a hourglass figure on her hands and knees was exciting. When she would start to yell "fuucckk!" I couldn't help but cum as I held on to her round ass.
It turned into crazy and uninhibited 14 month relationship.