Making The Sale

I suppose I should have listened to my inner voice warning me not to go in but I didn't. I stepped into the upscale women's clothing store just to look around. The store had just opened and I saw that Liz was working today. She had been very helpful a couple of weeks ago when I walked in and responded honestly to her inquiry as to what I was looking for. I told her I was attending a Halloween party and I needed an outfit. I then cringed as I expected as repulsive look or some snobby reply that would indicate she could not be of assistance. Instead, she smiled brightly and started asking all kinds of questions.

Would you like a dress or a more casual outfit? Etc...

Before I realized what was happening she had started a dressing room for me. I noticed there was no one else in the store and I decided I could not pass up this opportunity so I took her up on her offer and tried on several outfits. I couldn't decide which one would be best but I felt obligated to purchase at least one item as she had gone to so much trouble to ensure my privacy and was quite helpful. In fact I guess she me treated just like she would have treated any other female customer.

So that was my first experience with Liz. She made me promise to show her pictures of the party but I did one better and showed up in my outfit right at closing time on Halloween. I figured who would care on Halloween and also, from a distance at least, no one could tell I was a guy anyway. My make up was professionally done and I had on skinny jeans, pumps and a nice low cut sweater. Liz was happy to see me and told me I looked great. All that happened a couple of months ago and the other day I had the opportunity to visit Liz's store again. As fate would have it Liz was preparing to open the store and as I entered I noticed she was putting up a color advertisement of some sort on the door. As I walked in Liz greeted me warmly and welcomed me back and then as I looked into her eyes I could see the light bulb go off in her head.

She smiled at me and said, "Perfect timing. You will be great for this". I looked at the ad and realized for some reason she was promoting a "salespeople in drag day".

I replied that I didn't understand and then Liz told me how the girl sales staff had decided to have a "dress as guys" day for fun. I said that she was too pretty too really pass as a guy and she laughed and said the girls just thought it would be different and fun.

So I took the bait and asked, "How was this event perfect for me?

She said I should join them as a guest salesperson for the day.

I said okay before fully realizing what she wanted me to do. Since it was a dress in drag day she wanted me to be a "saleswoman". Deep down I thought about how exciting this could be to walk around dressed and acting as a woman all day in a store. I played it down though and did not immediately agree. After some cajoling I said I would do it. Liz was perhaps more excited than me with her response and quickly said they she would arrange everything. Everything meant an appointment at the salon next door for a full makeover and that she would select my outfit to wear to "work". It was a good thing that this was happening in just two days because had there been more time for me to think about this I might have changed my mind. As it was I showed up for my appointment at 9:30AM, greatly relieved that no one else was in the salon at that time.

As I entered Andrea greeted me with a warm smile and announced she was ready to get started on me. She asked me to go in the back room and remove my clothes and put on the robe she had hanging on the door for me. I took and a deep breath and told myself this was an experience I had secretly wished for quite some time so I went in and stripped, put on the robe and walked out to begin my transformation process. Andrea was happy to see I had already completely removed my body hair so waxing would not be necessary. She sat me down in a chair and went to work on my nails. After a relaxing pedicure I was becoming very comfortable and compliant. She then went to work on my hands. She gave me a full set of medium length nails that made my hands look decidedly feminine. I didn't stop to think how I was going to get them off. She then waxed my brows and I got a little nervous when I felt the wax being placed under the bottom of my brows as I knew she was created a feminine arch that would be with me for a while. Andrea must have sensed my apprehension and quietly reassured me that everything would be fine. I could not see the results as I was turned away from any mirrors but I accepted her reassurance. I was totally shocked when she began placing some hair extensions next to my head. I assumed she would have a wig for me but Andrea insisted extensions and a great hairstyle would make all the difference. I thought to myself what she meant by that and I realized she was doing everything she could to make me look as passable as possible. So I guess I should not have been shocked when she had me lie down so she could glue two very realistic looking breasts to my chest. After some drying time and some makeup to hide any lines I looked down at my chest to amazement at two perky perfectly formed breasts. There was no turning back now.

Andrea then said I should get dressed before she finished my hair and makeup. The clothes that Liz had picked out were great. I simple black a line skirt, a pretty low cut top and a very feminine jacket. I wondered how I was going to manage in four inch platform pumps but I found myself excited to try. Liz knew I was around a size four skirt but she had had left a couple of different sizes just in case. She had also given me a VS push up bra and matching panties as well as a body shaper to round out my rear and hide any bulge. As I got dressed my adrenaline was surging through my body. Judging by Andrea's response when she saw me dressed I could tell she was impressed. She quickly went to work on my make up and hair as she noted it was almost time for work. Through all this excitement I had somehow forgot that I wasn't just getting dressed up in private... I had agreed to go to Liz's store and be her salesgirl for the day! When Andrea spun me around in the chair to face the mirror I was in complete shock. I was staring back at a woman! I am sure up close and with my masculine voice some people would figure out I was a guy but from a distance, no way.

So I thanked Andrea immensely and I got the nerve to walk out the salon to Liz's store. The store opened at 11 and as I walked up to the door I noticed it was 10:50. Liz had told me to just come in the front door as she would have it open so I did. A few steps into the store I saw Liz, who is close to six feet tall, walk out from a storage area. She was dressed in a men's suit. It looked like she had cut her hair into a short men's style. From a distance she looked like a guy but as I said before her feminine beauty showed through her disguise. Liz stopped in her tracks when she noticed me. She ran over to me and could not stop telling me how great I looked. Another employee who I had not met emerged from the back dressed in men's pants and a shirt and sweater. Her petite body left no doubt she was a woman dressed in men's clothing. I was introduced to her as Amy and she simply said I looked great. She did notice my legs and said she was jealous. I told her it must be the heels.

The next few minutes were a whirlwind as Liz began telling me all the things we needed to do to open the store. I quickly fell into my role and followed her instructions. As the first two female customers walked in I held my breath and stayed near the back of the store. Liz greeted them and they commented on her nice suit. She informed them she was going by the name of Lou today and they smiled and replied, "Of course". Liz then asked me to bring out some items to hang up which meant I would have to walk right by the customers! I was reluctant but I figured I needed to dive in some time. What happened next completely shocked me. As I walked by the customers, one of them greeted me and asked why I was not dressed as a guy too.

Liz heard this and let out a chuckle. Then she said, "I knew that would happen". The customers were a little dismayed and then Liz explained I was in drag. Their eyes widened as they looked me up and down. They both announced they were very impressed how pretty I looked. As the day went on this happened a few times and Liz finally offered a little wager.

She said if 10 out of the next 15 customers don't realize you are a guy then you will agree to work with me as a woman tomorrow too. I thought this was quite impossible o I agreed... but it happened! I wondered if Liz had set me up for this but a bet was a bet. Now I knew I would be wearing a dress and heels tomorrow too! As the day progressed I found myself becoming quite comfortable and realized I was acting quite feminine in a very natural way. I closed the store with Liz and as we were tidying up the back dressing room which is quite large.

I jokingly asked her how it felt to have one "strapped on". She responded that she knew I wanted to feel it all day and then took my hand and placed it between her legs. To my surprise I felt a fairly large dildo. I took a deep breath and without hesitation Liz pulled me close to her and kissed me. Even in my heels she was slightly taller than me and she was now assuming her male role as she held me tight against her body. She pressed her cock into me and I wondered what she had in mind. Her hands found my breast and she expertly manipulated them. I could feel my nipples growing and my breathing increased. She knew she had me. She gently laid me on the floor. She pulled down her pants to reveal her cock. She deftly removed my panties and began massaging my groin. I guess my female persona took over as my mind told me I wanted her in me. She must have had this all arranged as she quickly lubed up her cock and pressed it against my opening. She slowly entered me and told me how beautiful I looked today. My body was on fire as she plunged her cock deep into me. I exploded in orgasm. Liz was now frantic and in wildly enjoying herself.

After a few minutes she collapsed and said she was excited to have me working for her. As I stood up and looked at myself. I appeared quite feminine with long shapely legs and heels. I decided working one more day for Liz would be an experiment worth trying.