Beginnings – Day 7 –Donna's Story

by Carolyn

  

As we settled in for lunch, Felicia and I sat on one side of the booth facing Don. She made sure our legs were touching – oh how I loved the feel of my pantyhose rubbing her's!

"Ok Don, let me tell you about CC's. I work for a wonderful man named Harry who owns a number of clubs. His vision for CC's is to have it be the place for cross-dressers to party here in town. As you know, there used to be such a club but it closed a few years ago."

"Harry has hired me to manage the club. One of my initial projects is hire a solid staff to help me make this a delightful, safe place for the girls to enjoy. I'm looking specifically for guys that would be interested in working for me in the persona of women. Of course, I'm not going to refuse employment to any qualified person that isn't comfortable with that idea, but I certainly hope to find a number of good candidates that would enjoy dressing up for work."

"Wow, Carolyn," Don responded, "you sure don't mince words! What an interesting concept. I am a bartender and, as I'm sure you guessed by my presence at Felicia's store, have occasionally dressed as a woman. I've never considered a job where I would be able to do that all the time!"

"Well, Don, if you don't mind, why don't you tell me about yourself, especially how you came to cross-dress. I promise that I won't think any less of you but I do request that you be entirely candid with me. If I am to consider hiring you, I don't want any surprises. Is that fair?"

"Well…..Ok Carolyn. Please understand I've never shared this with a woman before. There are a few people like Felicia and some close friends that know about me. As you can imagine, I'm pretty nervous about opening up. You seem like a great lady and since you are a friend of Felicia, I guess I'll trust you."

"As with most cross-dressers, I became interested in women's clothes as a young boy. My parents worked and I often found myself home alone for a few hours after school. One day I was in the basement and pulled out a slip from the clothes hamper. I stripped and put it on. From there I was hooked. I used to dress all the way from panties, a bra and panty hose. My mother's shoes fit me back then, although it wasn't long before I outgrew them. That was a sad thing at the time!"

"I never ventured out, of course, and tried to be very careful to replace everything where I found it. In my heart, I felt what I was doing was very wrong. However, when the opportunity arose, I stifled those feelings and put on her clothes. You probably won't understand this but it was quite stimulating. I would look in the mirror and become very excited. Since I'm being so open with you, I'll tell you that I would always relieve myself. The orgasms I achieved standing in front of the mirror looking just like my mom from the neck down were pretty spectacular."

"Don," I interjected, "I am so glad you're being so open with me." I took his hand and gave it a gentle squeeze as I smiled at him.

"Wow, Carolyn, I would never expect a woman to be so understanding. Felicia, you are right, she is a great gal."

"For years," he went on, "I stopped dressing. I was too big for my mother's clothes and frankly didn't have the time. I rarely was home alone and had a pretty good social life in high school. I dated some girls but never really was into heavy petting or sex with them."

"Cross-dressing was slowly put aside for me. I went to college but didn't graduate. I took a job as a customer service representative for a tire company and moved into an apartment. I had a room mate named Mike who was a bartender."

"Mike and I became friends and he offered me a job checking IDs at the bar. It was an easy job: I sat at the door and checked everyone I didn't know. I got to meet a few people there and soon it became my favorite place to be."

"One year for Halloween the waitresses decided to dress as nurses. Mike thought it would be fun for him to put on a nurse's uniform too. He told me about that and suggested I do so as well."

"I'll admit I was pretty scared to do that. I knew that I really wanted to dress up again but I was afraid everyone would realize that I enjoyed it and would think less of me. I told him I would think about it."

"The next day I told one of the girls I worked with about the idea. Instead of laughing it off she told me it sounded like a great idea. She offered to help me, if I decided to go through with it."

"After starts and stops I finally decided to do it. What the heck, it was just a Halloween night at the bar. Since Mike was going to do it I wouldn't stand out. In my heart, I was thrilled to have this chance to dress in public!"

"My friend at work, Nancy, had always been just a good friend. We had never dated so it wasn't awkward to let her help me with my costume. We went together to a surplus store and picked out a nurses uniform. It was simply a white dress with an open collar."

"She advised me to wear woman's underwear or I would simply be a guy in a dress. I thought this was a bit much but she sat me down and explained that doing this fully was clearly the best option."

"By now, I was fully on board with the idea. Of course, I protested a bit so she wouldn't realize how much I was looking forward to the project. She invited me to her apartment for measurements. She determined my bra size and told me that she had a friend who had large feet, for a woman, who would be happy to loan me a pair of white shoes."

"We agreed that I would come to her place again on the weekend for a fitting. I gave her the cash to buy whatever she thought I'd need. When I left I was shaking with anticipation in the car."

"That Saturday was a day I'll never forget. Nancy told me to shave my legs before coming over. I was glad she suggested it because I wanted to do so but figured it would be pretty obvious. When I arrived she took me into her bedroom. There on the bed was everything I would wear. It was more than I had expected. There was a bra, a slip, a girdle, panty hose, my uniform and a pair of heels!"

"Nancy told me to just try everything on and come into the living room so she could see that everything fit. She closed the door and I sat on the bed. I wondered if I could really do this and decided to give it a shot. I'll admit, I was getting pretty aroused!"

"I stripped and started with the panties, followed by the bra. I put on my slip and then sat to pull on my white panty hose. Memories flooded back and I was beside myself. I stood and put on the uniform dress. Finally I slipped on the heels. They were open toed and three inches high. I teetered a bit before I remembered how to walk in them."

"Taking a deep breath I went into the living room for Nancy's inspection. She was grinning from ear to ear. She told me I looked fantastic but would need to stuff my bra, figure out what to do with my hair and makeup."

"Since my hair was pretty long, she told me she would be able to fix it for me on Halloween's afternoon. She also promised to do my makeup and nails. I was into this and I realized she knew it."

"Am I going into too much detail for you, Carolyn? I don't want to bore you."

I realized how fascinated I was with Don's story. I smiled at him and said, "Not at all, my dear. This is a delightful story and I can't wait to hear about your night as a nurse!"

"Ok," he replied and went on with his tale.

"Nancy recommended I take the costume with me and practice walking in the heels. I was more than happy to do that; in fact, I knew that I would put everything on the minute I was home alone!"

"For the next week I dressed each chance I had. Halloween morning I was a nervous wreck. Nancy and I planned for me to meet at her house at 3:00 to get ready. We both had taken the afternoon off."

"I wasn't brave enough to get dressed to drive over there so I brought my costume with me. She let me change in the bedroom and then began my transformation. She started by putting extensions on my nails and painting them bright red. While they dried, she worked on my hair and clipped a cute nurse's hat to it. She was able to give me a nice flip style. When she did the makeup, I was getting pretty worked up inside. I couldn't believe the sensations I was feeling!"

"When I finally stood to look in the mirror I was astounded. I really looked like a cute nurse! I knew then and there that I was going to keep doing this. I simply loved the look!"

"The night was great. Nancy had given me a purse to carry with everything I needed. When I arrived at the bar, most patrons thought I was just another of the girls. Most of the cocktail waitresses were dressed in sexy nurse outfits but one or two were in traditional dresses like mine. Mike's outfit wasn't bad but he didn't have his nails done and just wore a splash of lipstick."

"I enjoyed the night immensely. Everyone was complimentary about my costume although a couple of the girls told me I looked too good for this to be my first time dressed as a woman. I let that pass."

"It was great fun walking through the bar in my heels and feeling the swish of my dress. I liked looking at my nails and couldn't resist staring at myself in the bar mirror. It seemed as though the night ended in a flash, although I know it lasted for hours."

"Since then, I've dressed up a few times for Halloween. It is the only time of year I have the nerve to go out in public. I think I would be a great candidate for your job, Carolyn.

I've learned to tend bar and would be a great bartendress for you!"

"Well, Don, I think you have marvelous potential. Of course I'll want references to ensure you can tend bar for me. Also, what about a name? Do you have a feminine name you use?"

"I know it isn't creative but I like Donna. Sometimes I actually feel like a Donna when I'm dressed. I've always thought it was a nice girly name. Is that ok?"

"Of course and Donna it will be from now on, my dear. Do you have references that you can email to me?"

He said he did and I gave him my email address. We had finished eating our lunch during his story and it was time for Felicia to get back to work. Don, that is Donna, had to leave as well so we parted ways. I walked Felicia back to her store.

"What an interesting story Donna had for us. Is that a common background for most of your customers?"

"Actually, it really has some common ground to many of the people to whom I sell. I would be interested in seeing how Donna presents herself. I sense she is a rather pretty woman."

"Oh I agree, Felicia. It will be great to see how she looks. Hopefully the references check out. I'd love to be able to report to Harry that I've hired a bartender!"

When we got to Felicia's store she asked me to come into the back room with her for just a moment. When we got there she closed the door and pulled me to her. As we kissed I felt a surge of energy coming from both of us.

"I just couldn't bear your leaving without kissing you, Carolyn. Sitting there during lunch, feeling your leg on mine and occasionally rubbing my arm against you was almost too much for me!"

I immediately returned her kiss. Breast to breast we languished against each other. My tight skirt couldn't hide my excitement. As I pressed my groin into her we both began to purr. It was delightful!

We finally stepped back, smiling fondly at each other.

"I must confess I'm counting the hours until we meet tomorrow night, Felicia. I can only imagine what lies ahead for us."

"My darling Carolyn, I agree. I wish it were tonight except I have to close the store at 9:00 and won't get out of here until nearly 10:00."

"Would you like to stop over on your way home? I'd love to see you again, if only for a few minutes. I'll have a bottle of wine ready for you!"

Our plans made, we stood together facing the mirror while we each fixed our makeup. It was fun primping next to her. Had anyone seen us they would have thought we were two professional women chatting merrily as we applied our lipstick.

I left soon after that with my thoughts already focused on the night ahead. I was already thinking about what I would wear. I was becoming such a girl!

  

  

  

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