A few weeks ago I met a woman online. We started chatting and found we were attracted to each other. She then told me she was married and was looking for fun on the side. I was ok with it and told her I would be discreet. All of our communicating took place over email. We asked each other our turn on's and turn offs. She told me she had never tried a D/s type relationship. I hadn't tried it either. I didn't even know what those letters stood for, but I found her very sexy, so I was game to try.
Her name is Stacy. She is in her late 30's. She has blonde hair and a great body. She sent me some sexy pictures of her that got me very excited.
Stacy explained to me that what she wanted was a man who would be very dominant to her. Someone who would tell her what to do and how to do it. She said she would do whatever was asked, no questions. Neither of us were sure if this was a D/s type thing, but we both loved the idea where it was going.
"So, are you ready to start this?" I emailed her.
"Yes sir." She replied back.
"Look at your schedule and tell me when you are free." I told her.
"My husband works late on Thursday nights, maybe I can be free from five until about eight on Thursday. I would have to meet you right after work though." Stacy answered.
"Thursday works." I told her. "We can still work out the details on the evening over the next few days."
The next day I emailed Stacy at eight that morning. "I want you to go into your closet at home, try on your sexiest dress and heels, take a picture of it and send it to me."
"What do you think of this?" Stacy replied in an email back about noon that same day.
I opened the picture and Stacy was wearing a tight little black dress and some 5 inch black heels. "I like it. The dress is very tight, but it's not short enough. I want you to find a shorter one."
"Hey, I'm at the store now and can buy this one, what do you think?" Stacy emailed to me about thirty minutes later.
I opened the picture and it was another tight black dress. This one came down to about mid thigh.
"Stacy, what store are you at? Are you on a lunch break from work?" I asked.
"Yes, I ran to the store real quick to find one. I'm at some store in the mall. I don't remember the name but I saw this dress walking by and decided to try it on. Do you like it? Will it work?" Stacy asked.
"No, I want it shorter!" I told her.
"How about this?" Stacy asked as she sent another picture of her in a dress. "It's one of those tight lycra type skirts that cling to you. I can always make it shorter."
I opened the picture and saw Stacy in a black skirt and a tight top. The picture was a selfie of Stacy facing the mirror. The skirt was up just high enough I could see the pink of Stacy's panties underneath.
"That one is perfect!" I replied.
"You really are going to have fun with this aren't you?" Stacy asked. "I've never worn anything this revealing before. I can't imagine where you would even wear anything like this other than the bedroom. I'm wet just thinking about wearing it for you."
"Meet me tomorrow night at that new Italian restaurant that just opened. Let's say 5:30, and wear that skirt and your heels." I told her.
"You want me to actually wear this out in public somewhere? I can't do 5:30 either. I get off work at 5. I won't have time to drive across town to my house to change." Stacy replied.
"Stacy, we are failing at this D/s thing. For this to work, you are going to have to be more submissive." I replied to her.
"I want this to work. I want to do this. I promise to be more submissive." Stacy told me.
"Ok, from now on, I only want you to answer me with 'yes sir'" I told her.
"Good, I can do this and I can be submissive." Stacy replied.
"Stacy, I only want to hear you say 'yes sir' starting right now." I told her.
"Yes sir." Stacy replied.
"Meet me at the restaurant at 5:30. You will be wearing that skirt and those heels. Your office has a bathroom where you can change. Take them with you to work, change into them at the end of the day and meet me at the restaurant. One last thing, I want you to wear those hot pink panties as well." I told her.
"Yes sir." Stacy replied.
I arrived at the restaurant a little early and waited for Stacy. I saw her car pull up a few minutes before 5:30. She waited a little while in her car. It looked like she was still putting on makeup and fixing her hair. I watched for the car door to open.
When the car door opened I saw Stacy hesitate before getting out. She looked around to make sure nobody was watching and quickly brought one leg out and then another as she got up out of the car seat. She moved so quickly trying to make sure she didn't flash anyone in the parking lot that when she finally was standing her skirt was right at her ass cheeks.
Stacy closed the car door and tried to pull her skirt down some for the walk to the restaurant. Her skirt was so short that after three steps she had to tug it backdown. After multiple pulls to keep it down she kept her hand on her side permanently, holding it down the best she could.
I had only seen pictures of Stacy and never seen her in person before now. Her legs were much longer than I expected. With that skirt, she was all legs and high heels. She had a tone, fit build, so the skirt fit her body very well. She was much more attractive than I originally though. One of the waiters came running to the front to watch her walk in and get a better look.
"Stacy, good to see you." I told her as I gave her a quick hug.
Stacy smiled and said hi back and we then followed the hostess to our seats. The hostess brought us to a booth. It was a larger booth, one that could fit three people on each side.
Stacy sat down on one side and I sat on the other. We both took a moment to relax and look at one another. I was very pleased by her appearance. He body was amazing and her eyes were erotic.
"So, I know I told you I want you to answer a certain way to my every statement or question, but we are going to need to talk here at dinner. I want you to answer every question I ask with an answer and I want you to reply to every command I give with the 'yes sir'. Do you understand?" I asked.
"Yes sir!" Stacy answered with a smile.
"So you were able to somehow figure out how to change into your clothes at work for tonight I see." I said.
"Yes, it was a challenge and I'm fairly certain I will be receiving flowers now from a junior accountant at my office." Stacy told me.
"Oh yeah? Flowers?" I asked.
"Yes, I think I made an impression on him walking out of our office." Stacy said.
"So that little skirt has already been good for you then?" I asked.
"I don't know if I would say good for me. But exciting, yes." Stacy said smiling as she was starting to tell me about her adventure getting out of her building in the skirt. "I changed in the first floor bathroom. I thought I had a clear path to my car. I walked out of the bathroom and saw our CEO heading right at me. I turned and went to opposite direction and out the back door. As you can tell from this skirt, it was up on my ass by the time I got out the back door. My heart was beating so hard I didn't even feel it rise up. I had to walk all the way around the building. On the side of the building was a junior accountant I work with. He watched me walk the entire way. I didn't notice him there until I heard him calling out my name. At that point it occurred to me that my skirt is up on my ass. He got a great show. Of course when he walked up to me he forgot what he was going to ask me. His eyes wouldn't make eye contact with me and all he could do was look at my legs in this skirt. I'm sure his view of me leaving the building to walk to my car was exciting for him. So I'm fairly certain I'm either getting flowers tomorrow or I will now have a stalker."
"Well, at the very least you have had an amazing experience. So how did it make you feel in that skirt and knowing how turned on you made your coworker?" I asked.
"I liked it. It turned me on." Stacy replied.
"I think you look very good in it. You have an great body. Seeing you in it has gotten me hard." I told her.
"Really?" She asked.
"Yes, really." I told her.
