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Shopping with the Boss's Daughter

I came home from work after a successful morning meeting where we finalized a big project. I decided to celebrate by going out to buy a new dress. I changed out of my business suit and grabbed a quick shower to shave smooth. I put on my make-up, choosing to go with a conservative look for the day with a pink lipstick.

I got dressed with black panties and bra, and pulled on the silky nylons and attached them to my black lacy garter belt. I then slipped into a long navy skirt with matching blazer and slid into a pair of black flats. Since I am tall, I usually wear flats going out, unless I am going out nightclubbing. I put on my short brown wig and fixed my hair, before I grabbed a purse and headed out the door.

I love the feeling of walking out side and enjoyed the short walk to my car. I drove to the King of Prussia Mall and parked near the Nordstrom’s store (which is one of my favorites). I walked into the store and headed over to the dress section.

A saleswoman came over to see if I needed help and she was showing me some of the newer collections when another younger saleswoman came over to assist. She was a medium height girl wearing a yellow cashmere sweater with a black pencil skirt, and I immediately recognized her as Amanda, the college-aged daughter of my boss. We had had several conversations at different company functions over the last couple years, and she was really cute, but she was still the boss’s daughter, so I kept my distance.

She looked at me like she knew me, but wasn’t sure. I didn’t want to get “made” there so I causally, but quickly, became disinterested in the dresses, and started to leave that department. As I was walking away, Amanda asked if she knew me because I looked very familiar to her. I replied that she looked familiar, but that I didn’t remember meeting her, and thanked her for her time.

I continued out into the mall and started strolling around looking at other stores. After looking at a few stores, I walked into a shoe store and was looking at some stiletto heels. I heard a familiar voice behind me say, “I think you would look good in them.”

I slowly turned around and there was Amanda, looking at me and smiling. She said, “You must have a brother, because I realized where I had seen you, you look just like a guy who works for my father’s company that I have a crush on.”

I smiled at her, but was shaking on the inside, not sure what to do. Do I say something or blow her off? I gambled and said what the hell; the large project that we had won that morning required my skills, so I took a chance. I told her that she was mistaken and that I was an only child. Her eyes sparkled and she said, “I know.”

I said, “Please don’t make a scene here, we can walk somewhere else and talk about this.”

She smiled again and said, "Okay." 

We walked out of the store, walked over to the food court and got a drink and sat at a table. She was asking questions as fast as she could get them out of her mouth. She wanted to know how I got into this, why I did it and finally, was I gay?

I explained myself as best I could, but first I had her promise that my secret would stay private between us, and she quickly promised to do so. She seemed interested as I gave her a brief rundown of my past and then admitted that I wasn’t gay, but that I enjoyed being with women, I just liked dressing like a women better than a man.

She complimented me on my make-up and wardrobe choices and asked if I was really looking to buy a dress that day. I said I was, but that she had spooked me off from my original plan. She said that she wanted to help me pick out a dress and promised to be helpful. She called back to her store from her cell phone and made an excuse to get out of the rest of her shift.

We had to leave the mall so that she wouldn’t be seen by other co-workers, but I met her in the parking lot and we drove to a nearby outdoor shopping plaza that had several stores that she liked. We parked beside each other and went into the first store. This was a store that catered to evening and formal wear, but they also had a smaller section of nightclub wear outfits.

She told me that she was treating me to today’s dress since she had interrupted my original plans. We looked at some long dresses that were beautiful, but I didn’t have much call to wear them out. She finally led me to the nightclub section and we both liked a short red and black dress that had cut outs on the hips. She asked me to try it on, so I grabbed my size and went into the dressing room.

I couldn’t believe this was happening and wondered where this was going to lead to. I decided to just enjoy this and let play out whatever would happen. I slipped out of my conservative skirt and blazer and wiggled into the dress. I was so tight on me, it showed my underwear and bra lines. She called out how did it fit, and I opened the door so that she could see. I said that it was too tight, but she shook her head and said it was supposed to fit that way and she loved me in it.

She walked into the booth and ran her hands up and down my body and said that I looked great in it and she wanted me to wear it out of there. She ripped the tag off and took it to the register to pay for it. I slipped my shoes back on and straightened myself up as best I could and stepped out of the changing booth.

Amanda met me in the clothes aisle and walked me to the door, as if she was showing me off. She led me to other store two stores down the strip that was a shoe store and we went straight to the boots section. She asked for a pair of knee-high black leather boots in my size and had me sit on a chair.

When the clerk returned, she had him slide my shoe off and slide the boot up my leg and zip it up. I took a tentative step in the boots, but fell in love with the way they looked on my legs. She apparently did too, because she said we’ll take them and that I would be wearing them home. She paid for my boots and we walked back to our cars.

She asked me to follow her to her apartment so she could talk to me some more. I agreed, since she had made my day, and I followed her to a suburban mainline complex. We parked and she showed me into her condo. It was tastefully decorated and once we were inside, she gave me a hug and thanked me for coming over.

She said she wanted to get more comfortable and asked if she could change clothes. I agreed and sat in her living room waiting for her to get changed. She kept yelling out questions to me while she was changing, and it was easier to answer them when I wasn’t looking her face to face. I felt more comfortable as we talked and was enjoying myself when she came back out of her bedroom.

She had changed into the same dress that I was wearing, with almost identical boots to match. She asked, ”Do you like what you see?” and I quickly answered yes.

She came over and sat down next to me on the couch. She leaned in and gave me a quick kiss. I started kissing her back and soon our hands were roaming over each other. I couldn’t believe that this was happening, but I was enjoying every second of this and didn’t want it to stop.

She broke for air, and asked if I would join her in the bedroom. I jumped up and followed her to her bedroom and she pushed me onto the bed. She took my boots off and then took hers off also. She climbed between my legs and pushed them open, which hiked my dress up near my hips.

She said, “What kind of surprise do we have down here?” and started rubbing my crotch.

My cock was already bursting to break free from my panties, and I ached for her to free it. She rubbed up and down my thighs, which was driving me crazy. She finally began kissing my thighs while she worked on freeing my cock out of the panties. I was ready to burst when she began to lick my cock and I almost passed out when she swallowed me in her mouth. She worked me over and within minutes, I was cumming a huge load down her throat.

I pulled her up and gave her a big kiss, and then told her it was my turn. I pushed her back on the bed and began to kiss my way down her body. She helped me slide her dress off and she was naked underneath, which didn’t surprise me. She had a neatly shaved pussy and I started kissing all around it. She started writhing around and was asking for me to please lick her.

I did as she asked and began giving slow licks of her pussy and she began moaning wildly. I dove in deeper with my tongue, and her moans turned into shrieks and within a few minutes, my face was covered in her juices. She slowed her writhing down and caught her breath and just laid there. She said, “That was the most intense orgasm that I have ever had, I hope you will stay and try for more.” 

Needless to say, we spent the rest of the day together enjoying ourselves and making love multiple times. I still work for her dad, and a couple times a month, Amanda and I get together, get dressed up and go out shopping or clubbing. Each time we end up back at her place for some of the greatest sex either of us has ever experienced.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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