I've Met Someone

About six weeks ago I was on a Femdom dating site and out of the blue I received a message from a woman claiming to be a Domme in my area. I was skeptical, but after about a week of daily chatting and picture exchanging I realized that she was indeed what she said she was. Eventually I turned on my webcam and she turned on hers, and we found we had mutual attraction for each other. We exchanged cell numbers and began texting, as well as exchanging email addresses for longer messages. She kept me at arm's length for a while, but eventually let her guard down.

We hadn't physically met, but shared a great deal of information about our lives. She is divorced, in her mid 40's, she has a daughter who just graduated college, a home owner, and she's a successful attorney. She was introduced to the lifestyle by a friend of hers that lives in a female led relationship with her husband. She aspires to have a slave, but also wants a poly lifestyle. She said she's not looking for marriage per se, but at the same time wants a commitment that goes beyond BDSM play. Her aphrodisiac is power and control, and all of her fetishes flow from being an empowered woman. The interesting thing is that in all of our conversations we never really got deep into sex talk, and when we spoke of Femdom or BDSM is was more of a clinical conversation than an erotic one.

...and she's close. She lives in North Austin which is about 25 minutes away from where I live.

So we decided to meet for lunch at a restaurant not far from her office. I felt a little underdressed as she was in a suit and I was in jeans and a button down shirt. The webcam didn't do her justice. In person she lights up the room. She's a redhead and tall, and she has a presence that exudes confidence.

We didn't have much time as she had to get back for a meeting with a client. She had already checked me out pretty thoroughly on-line, and as we progressed through conversation I felt as though I was being interviewed for a job. Perhaps I was. Several times she would start a question with, "If I accepted you as my slave..." When lunch concluded she wrote her address and security gate code on a napkin and gave it to me.

"I'll see you at 8:00 tonight. Don't be early, and don't be late."

And before I could say anything else, she was running out the door on her way back to work. I realized that this is a woman who is used to coming and going as she pleased, and it was up to others to follow her schedule. She didn't have to ask for my input, or to see if I had other plans. Truth is even I did have plans I would have immediately cancelled them to be with her. I know a good thing when I see it.

So I got there about 15 minutes early and just waited outside the gate before entering the code at the appointed time. I had purchased flowers as gift for her, and hoped they would win her favor. The neighborhood was filled with high end multi-million dollar homes, and her house was no exception. I was kind of amazed that she would choose to live alone in a five-bedroom house, but I digress. Point is that she has a lot of space to play.

When she opened the door she had a scowl on her face. "I told you not to be early. Put the flowers on the table and follow me."

It dawned on me that there were security cameras outside the gate, and she must have been watching. Even though I had the best of intention, I had made a mistake following her command and she was about to hold me accountable.

She told me to come inside and directed me into her large living room area. She told me to get undressed and wait for her, but NOT to sit on the furniture. I did as instructed folding my clothes and laying them in a pile on the floor. I stood there naked wondering what was in store for me. I had really gotten off to a bad start.

She returned wearing a strap-on harness outside of her jeans and the dildo attached looked formidable. In her right hand she held a rattan cane. I stood there naked gawking at her, and could not help myself. My penis became erect at seeing her this way.

She looked at me shaking her head. I started to try to explain, but she shut me up in a hurry. "No excuses, no whining, no noise, no talking unless I tell you to."

She took me over to a heavy marble table and had me bend over. I bit my lower lip as she quickly laid the first ten strokes on my ass. The cane was biting hard from the force of her blows, and the pain had made my erect penis run for cover. I was trying my best to remain silent as ten more times the cane fell on my bottom. On the twentieth stroke, I let out a barely audible gasp. She was like a shark with blood in the water.

"I was going to stop at 20, but I told you not to make a sound. Therefore, the punishment is doubled."

The brutal cane rained down on my tender bruised butt, and by the time she got to 35 I thought I was going to pass out. Then the last five came hard and fast, and the pain had me in a full sweat quivering below her. Tears were filling my eyes, but I was determined to remain in place in silence.

She put the cane down on the table and as I glanced at it I saw it was stained with my blood. She grabbed my beaten ass cheeks and exposed my hole. She spit on it several times, then worked her fingers in and out furiously preparing it for a larger violation. There was nothing sensual about her technique. She didn't care if it felt good or not. We had not conversed about her sadistic desires, but as I lay there I understood that is a big part of her makeup.

She removed her fingers and spit on the dildo. I was hoping she would just ease it in slowly a half inch at a time. No such luck. She thrust so hard I though she was splitting me in half. She started with long deep thrusts trying to stuff as much of the toy as possible inside me. I really could have used some lube, or least more spit to get the full dildo in me. Nevertheless, she was determined to do just that.

Five minutes of pegging, then ten, then fifteen...it was actually starting to feel good but enjoyment was short lived. Those last two inches would come at a price.

She moved me off the table and took me to her bedroom. She had me lay on my back on the bed and hold my legs as far back as I could so that she could mount me with her full body weight aimed at my hole. It didn't take long until the defenses in my rectum gave way to the phallas and all eleven fat inches were deep inside me. The pain returned with vengeance, as a part of my body that had never been violated was being forced to accept an oversized object. She kept pounding deep with her full body weight on top of me until I was stretched to point of gaping.

She was watching my face carefully for clues whether I was experiencing pain or pleasure. If it was pain she would continue, if it was pleasure she would pull out. I am not a good poker player. When it started to feel good, she knew it and she stopped.

She told me to get dressed and go home. But there is more to the story to bring you up to date.

I had no idea of her voracious appetite for pegging. That is the focus of my training right now. She takes her strap-on with her everywhere. These last two weeks I've been pegged about a dozen times. She's pegged me in her office twice, once there was another male in the room watching us. She's pegged me and videoed it to her friends. She pegged me behind her car in a bar parking lot late at night. She pegs me in the kitchen, bathroom, and even in her backyard where neighbors could see. Morning, noon, or night my ass is at her beck and call. I'm making her dinner tonight. Wanna bet what the outcome will be?

Our relationship has progressed to the point that after she pegs me, she'll often have me perform cunnilingus or analingus to finish her. She's made it clear that she'll never fuck me or suck my cock. I am there for her pleasure only, and if she wants sex she'll get it from someone who is more worthy. But I also have to say this, even if only to be her chastity peg boi, I'm enjoying the regular domination even if I'm walking a little funny these days.

But at the same time I'm wondering how long I can keep this up? We've watched strap-on porn together and her favorite videos are these Euro dudes who take incredibly large things in their asses. She says she wants to train me that way which makes me more than a little nervous. She's already ordered some dildos even bigger than the one I've been taking. Monster plugs, too, and a pink chastity device (She told me to enjoy jacking off now, because that wasn't going to be in my future).
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slave4owner
ke JUSTLOOKING_305 : She's amazing...like you.
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JUSTLOOKING_305
I love this girl!!!!
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