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The Beginning

It was normal day on the road. I was working out of the Los Angles office for couple weeks and I decided I needed to get away from the local staff. There was a local Mexican restaurant in the neighborhood which was nothing fancy but the food was good, it was one of those places you order at the counter and wait for your food. I headed there for lunch planning on getting a couple of enchiladas with all of the fixings and then taking it back to the office and eating at my desk.

I was standing in line behind a very attractive woman. She looked to be in her 40's with a body that was very pleasing to look at. The line was moving slowly. She turned to me and commented about how difficult was it to make a taco. I smiled and agreed that it seemed to be taking a long time. Taking the lead, I told her a few of silly jokes about waiting in line and other slow situations. She smiled and laughed at them all.

Changing my mind about going back to the office, I took one the seats at the counter along the wall. I took the middle seat of 3 empty seats hoping she would take the unspoken invitation to take one of the seats next to me. I smiled when she did and we settled into a casual conversation. As we finished, I offered to take her for real Mexican food for dinner at one of my favorite restaurants in Orange County. She placed her hand on my left hand touching my wedding ring. I looked down and then back up to her eyes. She smiled coyly and asked if there was any reason at home with this would be an issue. I replied with no and I live 1500 miles a way I was in town for a couple weeks on business and that I normally came to LA one week a month. Not quite answering her question but looking at her in a way that said there wouldn't be an issue.

She smiled and said she would love to have dinner. She told me her name was Cindy and told she would meet me at 7:00pm.We parted and I went back to the office. I was a little unfocused for the rest of the afternoon thinking of Cindy and the things I would like to do to her.

I was a little surprised that Cindy accepted my offer. Cindy is an attractive woman about 5'10" with 3" heels on makes her well over 6 feet tall. She has a nice figure with curves in the right places. She has medium length light brown hair which is worn straight with bangs. Her green eye set off her classic "U" shaped face. All though I'm in good shape physically, I'm a man in my early 50's with a little gray hair and a few too many miles on my face. I'm sure that the fact that I'm 6'3" did help some.

We met that evening for a lovely meal at the Mexican Restaurant near my hotel. She had dressed in a red sun dress and heels. She looked so damn good that I wasn't sure we would make it through dinner. During dinner, we became very chummy. It was surprising how easy she was to talk to. As I think back on it, she took the lead in much of the conversation.

During the meal our hands lingered as they touched on several occasions I felt that if I asked I had a chance for things to go further. On several occasions during dinner the conversation had drifted towards sexual subjects and she did seem to be flirting back to me. I was surprised when she asked where I was staying while I was here. I told her the name of the hotel and the location. She laughed and said that was pretty confident. I said yes and told her that I had walked to the restaurant in case we did too much drinking. She asked how many drinks it was going to take before I invited her back to my hotel. I said we were there and I asked her over for another drink at the hotel.

We walked to Cindy's car and got in. We drove to the hotel, parked and exited. In my mind, I was already planning ways to please her and imagining how she would please me.

Cindy was quite a surprise once we got to my room. She started kissing within seconds of entering the room. I started to reach for her breast but she deflected my hand and instead she started unbuttoning my shirt. We kissed and she rubbed my chest and nipples. I tried to reach for her breasts again and she slapped my hands away. We continued to hug and kiss, exploring each other's mouths. Suddenly, I felt her hand at my belt and zipper. Within minutes she had my pants, shorts, socks and shoes off. Her hands and mouth were covering every part of my body. It did feel strange naked in a room with a woman who was fully clothed.

We moved to the bed. I lay back on the pillows as she shifted so she was straddling me. I could feel the silkiness of the thighs on mine as she rubbed her panties on me.

After about 20 minute of very hard necking Cindy unbuttoned a few buttons on her blouse and exposed a near perfect left breast. She positioned the breast in front of my eager mouth. I started to lick and suck her nipple causing it to harden. I heard her gasp.. She pulled her breast away and told me how she liked she breast sucked. I was only too happy to indulge her. I sucked and licked for the longest time. Much too soon, she put her breast away and took out the other. I worked on it for several more minutes. The whole time she was sitting on my erection. Every time I make a move to remove her clothing or get inside her panties she stopped me.

She put her breasts away again and I began to wonder if the evening was over. But just as I started to say something, I felt her hand on my erection. She turned around and put her crouch over my face. I could smell her sex and feel the wetness in her crotch through here panties. She lowered her dripping pussy to my mouth and I felt her fingers move her panties to one side. As with her breast she took some time to explain in detail how she like to be licked. She would alternate between me sucking her pussy and her playing with my cock and balls.

Then she raised her pussy up form my face and took her fingers and buried them in dripping pussy for me to watch. I though I was going to cum on the spot. She looked back at me over her shoulder. She told me she was going to milk my cock. She then took her wet finger and traced my cock and balls. I could feel her warm breath on my cock. Just as her mouth touched my cock I felt her warm slippery finger entering my ass angling straight for my prostate gland. I could feel her finger pushing the cum out of my prostate gland. Every few second she would suck the cum out of my cock. She said don't cum that she would tell you when. For the next 20 or 30 minutes she kept me hard without letting me cum. The whole time she was pushing cum out of my prostate. Every few minutes she would lower her pussy on to my waiting lips.

She turned around and sat back down on my erection. She moved her panties to one side and swallowed my cock on one push. It was heavenly. She slowly pumped my cock for the longest time I was amazed I wasn't shooting cum everywhere. I would see and feel the orgasms rolling thru her body. The more she pumped the harder and longer she came. After 30 minutes she was done.

My first thought was I didn't cum but then I did feel satisfied. My cock was getting soft and I didn't feel like I still needed to cum.

Cindy rose up and was standing at the end of the bed looking wonderful and still fully dressed. She asked if I felt good and I responded with yes. She smiled. I said I didn't think I needed to ask her. She said "no I didn't". She asked if I would like to come over to her house Friday night for dinner and other things. I immediately agreed. She wrote her number on the pad of paper on the desk. Gave a quick finger wave and left, I was so sated that I fell asleep within minutes.

Cindy was all I thought about for the next 2 days.

I got to her house at 7 pm. The house was a nice Spanish style house with a private front courtyard with lots of arches and tile roof. It was typical for the LA area I rang the bell and the door opened as I stepped through the front door I noticed there were shoes by it so I removed mine. Cindy was wearing a very sexy, low cut black dress with fishnet hose. We went straight the dinning room. She told me she just needed a couple minutes to finish up dinner.

It was a wonderful meal. We flirted all during dinner. After dinner I got up to help with the dishes. As we were finishing up Cindy came over and started kissing me in the kitchen.

She asked if I would like to watch a couple adult videos, I easily agreed. Much to my surprise Cindy's video taste were Femdom movies. In the first movie, a busty woman had a houseboy who she always kept nude. The houseboy serviced all her sexual needs. I wondered where I had seen that before. In the second movie, the woman wearing very sexy black leather had a slave with a collar who took care of her and her friends. The slave wore leather and assortment of cock and ball leather straps.

At the end of the movies Cindy asked very nicely if I wanted to stay for the weekend. I responded that I assumed we watched the movies for a reason before she asked the question. She said yes and so did I. I thought I should try everything at least once and I in fact I had a wonderful time Wednesday night.

Cindy said I could store my clothes in the closet by the front door. I felt very naked when I returned to the room with a fully clothed woman waiting for my return. We had a surprising very quiet evening. I'm not sure what I had expected to happen, I spent evening kissing, rubbing, licking and sucking all of Cindy's body. It was wonderful. I never once had to decide what do next as Cindy told me what she wanted and how she wanted me to do it. I brought her to several orgasms during the evening.

She set a couple of basic ground rules for the rest of the weekend. First one was that she would make all of the sexual decisions. Who touched what and when. I wasn't to touch myself without her instructions. I wasn't to cum without her permission. I wasn't to wear clothes inside her home.

It was kind of liberating not wearing clothing all day.

As bedtime approached I wondered when it would be my turn. I didn't have long to wait. Cindy had me get on the coffee table on my knees and elbows. I felt her warm wet finger enter my ass and within seconds I could feel the cum dripping out of penis as she rubbed in tight little circle. The cum continued to flow for 10 minutes into the bottom of the small bowl she had placed under my dick. Just as I had felt the first time, I had the warm after glow of an orgasm but no orgasm. I wasn't sure how this milking worked but it worked.

Then my surprise for the day came. Cindy told me to wait on the table she returned a few minutes later in a bra and panties with large strap-on penis. The strap-on protruded from her crotch like it was real. I knew what she had planned of the rest of the evening, she walked to the front of the table and had me lick and suck her crotch and strap-on. I gave it a blowjob and she fucked my face with it. After she grew tired of the games she moved behind me. I could feel the head run up and down my butt crack then it circle my virgin anus. She slowly worked the head into me. She then started pumping me with little short strokes. She took her hands and started pulling my body in time with her strokes. I knew she wanted me to meet her thrust with a push of my own. With in minutes I could feel her hips as they met my butt. The dildo was fully in my anus. I would no longer be able to think of it as a virgin. I could feel her body beginning to orgasm. She had a long powerful orgasm. Then she went limp behind me. After a short rest I could feel the dildo sliding out of my ass. She petted my head and said I could go to bed now.

I wasn't sure where I was sleeping that night. She had made up the guest room for me and showed me the basics of the house. As I turned to enter the room, she rubbed my butt cheek and then gave me a little slap. I heard her laughter drift down the hall. I laid down replaying what had happened early. I felt my cock getting harder and was tempted to stroke myself. I remembered that it was against one of her rules so I restrained the urges and eventually fell asleep. After all if we were playing the game I should play by the rules.

I awoke the next morning to find a note on the bed table with instruction for the morning. Seems Cindy was an early riser and was out of the house. When she returned at 10am I had breakfast ready and all of the chores from the note completed.

After we ate, I was called the bathroom. She pointed at the toilet seat which was in the up position. She explained that it was always to be down. I told her it wouldn't happen again. She told me to put my head on the bathroom counter looking at the seat and rise on to my toes. I watched as she picked up a hairbrush from the counter. I didn't know how much it would hurt and burn when the backside of the brush met my backside. After 5 firm blows to my butt I was reminded that the toilet seat would always be down from now on.

Cindy told me to stand up and face her. She then kissed me and told me she had presents for me in the living room. I was amazed at how fast she could change from punisher to loving friend. I walked my sore butt into the other room where Cindy sat with a brand new leather V shaped cock and ball separator. It had a ½" wide scrotum straps the force my balls way in front of my body. There are 2 leather straps that go between the testicles forcing them apart. I will say when she first put in on me it looked amazing. My testicles were sticking a couple inches in front of my body and a couple inches apart. The scrotum strap made my cock seem shorter but even soft it was sticking straight up. Then came the reality of walking around with your balls leading the way, they would bump into everything. Every action I took during the day I needed to see how it would affect the testicles. I was sure Cindy liked them that way because they were easily reached and viewed.

There were 3 other straps for other occasions. There was a basic strap made from ½ wide leather straps a cock ring with two extra straps which harness and separate the balls. One of the straps goes around the balls in front and the other runs between the two to separate them. There is a leather harness consisting of two leather cock rings, one to be worn behind the balls and the other at the base of the cock with a "D" ring on top for a leash. The 4th cock and ball harness consists of a black leather cock ring with 3 nickel-plated adjustment snaps that is connected to a 1½" steel O-ring by two leather bands. The bottom band serves as a ball divider and has 2 snaps, while the top one connects the two rings and has one snap.

Saturday afternoon was a pretty normal day we watched a baseball game on TV had lunch. I did spend some time between her thighs but not much. She would have me run silly errands around the house I'm sure was so she could watch how I was adjusted to cock and ball separator. If I lay down on my stomach it required two pillows to keep from crushing my balls. Of course my ass must be sticking a foot up in the air.

After the game Cindy decides we are going for a walk. I was little taken back. I hoped she didn't expect to go outside nude. She returned with a pair dark blue gym shorts and light blue t-shirt and my tennis shoes. With the ball separator the front of the shorts are very full. Just as we got to the front door Cindy stopped me and said she may want to use my ass again tonight and it was a little tight last night. She told me to drop the shorts and bend over. I was fitted with shiny new butt plug to loosen me up a little. She reminded me to not let it slip out on our walk. I couldn't imagine the embarrassment if it fell out walking. Well it was interesting experience walking with a butt plug. I felt it move inside with every step. We took a nice 1 ½ mile walk around the small neighborhood lake. We didn't run across to many people and when we did we just kept walking.

When we returned to the house I made a big error. I just walked inside the house in my blues shorts. Cindy snapped around when she heard me walking. She demanded to know where I was going dressed like that. I knew I had made a mistake. I quickly pulled the clothes off. She sternly told me to wait in the hall. She walked in the bedroom between the master bedroom and the guest room and a couple minutes later she opened the door an invited me in. She said she had hoped I could have gotten a couple more days to know her before she needed to bring me here. There was a big wood "X" in one corner, a couple of wooden saw horses in the other and an assortment of whips, paddles and canes on one rack. The other had hand cuffs, leather straps, blindfolds and several thing I couldn't figure out.

I stood at the door for a long time before I entered the room. Did I really want to go down this road? She said I should come in and talk for a few minutes. We sat on two leather pillows in one of the corners. She explained why she liked the Femdom lifestyle as well as all of the reasons she thought I would enjoy it also. We talked about safe words and trust, giving and holding the power. After about 45 minute I told Miss Cindy I was sorry I had broken the rules. I asked for her to help me to remember not to do it again and I was ready to atone for my behavior. I mean it couldn't be much worst then the hair brush could it?

It was about 3 days before the red cane marks disappeared from my butt. Miss Cindy walked me over the padded sawhorses. She bent me over the horse, took my balls and clamped a long wooden tool on both sides. This in effect prevented me from straitening up. When I jumped from the caning it pulled hard on my balls. She told me she was going to administer10 strokes and that if I didn't take them as she desired, she would start over. I so wanted to scrim between each hit but that was worse than just standing still. The next 10 minutes were hell. The bamboo cane bit the skin on my ass with each stroke. The narrow cane wrapped around the curve of the ass as it struck. I felt each welt forming before the cane is removed. The sting lasted for hours. There was no question in my mind I wouldn't make that mistake again.

It was amazing how loving Cindy was Saturday night. She was careful not to touch the fresh red welts on my butt. She didn't make me bend or sit on them. She treated me like a hurt little boy. She did look at them every time I walked across the room. Near bed time Cindy called me to living room she was sitting next to the coffee table with milking bowl setting on the table. I assumed I was about to get milked. Much to my surprise she unsnapped the cock and ball separator and gently kissed my penis until it was nice and hard. She alternated between sucking and stoking my penis by hand. With in a few minutes I was filling the bowl with globs of cum. I still to this day think it hurt her as much as it did me when she chooses to punish me. Saturday night I slept face down on the bed.

Sunday morning was the day my life changed forever. Cindy woke me with a gentle kiss on my tender ass. We talked for hours about her role and my role in our Femdom relationship. Her hands were tender as she tended my bruised red ass. She said that most submissive men are loving and caring, and want to please she felt that I was that way. Deep down they want to know that someone to accept who they are, and their gift of submission. She told me how much she wanted me to fill that role in her life. She asked me if I was willing to be trained as her personal slave. To be that someone who took care of her personal needs. I decided I was willing to be trained as her personal slave; I would give her full control of us. I would devote myself to making her happy. Her joy would be my joy. Her fulfillment would be my fulfillment. She wanted me to know that she enjoyed being my mistress. In simple terms, she would truly enjoy 'owning' me, and truly enjoy the authority she would have over me. The first new rule being nude in her home now started on the other side of the front door.