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On a Sunny Day in A Small Town

By Heidi Lower


Do YOU have a First Time Story? We think you do. Email it to Cindy and we'll publish it!



My older sister, a (GG), has known and shared in my passion to be a woman for many years. I visit her often and when I do, I always dress. She has provided me with a sanctuary and closet to transform myself into her sister whenever I visit. We do makeovers, facials and fix each others hair. I count myself very fortunate to have this type of relationship with her. I'm her best girlfriend.

Okay, here goes, it was several years ago. I arrived at my sisters home, and it was my birthday, the next day. So, she wanted to do something special, and I had to say I would do it before she told me what it was going to be. I did, and committed myself to an adventure that has continued ever since.

The next morning I awoke and took my shower, shaved myself clean, and got dressed. She had picked out a short denim skirt, a red and blue striped top. I put these on over my bra, panties and pantyhose. Slipped on a pair of low heels and went to the kitchen for breakfast. She then gave me a hint what she had planned, so I wouldn't be too worried, she said I should trust her. I always did, so I went along without reservation. She fixed my makeup and did my hair, and out the door we went.

We drove to the next town about a half hour away, and this gave me the opportunity to relax a bit. I was in broad daylight, on a beautiful sunny day in California, driving my sister's little red Mazda, which made me feel great! I could see myself in the vanity mirror and I looked fabulous, I was gaining confidence. Our first stop was the K-mart store.

Needless to say, getting out of the sanctuary of the car was scary. I adjusted my purse over my shoulder and the two of us headed for the entrance. A guy was coming out and held the door for me, with a big smile. I tipped my head as I entered, not sure what he was thinking. We were inside, looking around, I couldn't see anyone paying any particular attention. My sister said, "relax, and act natural" easy for her to say. She grabbed a cart and put her purse into it. I did the same and she allowed me to push it seeing I needed a little security to hold on to. We proceeded into the store passing through the women's section and back to the rear of the store.

The photo shop had a sale, 100 copies of your portrait for only $4.99. My first photo session. The girl running it asked if she could help "you ladies" then handed me the paperwork with a nice smile as my sister asked about the pictures. The girl talked to me and seemed to be making no indication of my real gender. It was as if it either didn't matter, or she believed me to be the woman I appeared to be. She led me to the photo room and worked me through several poses. After about 20 minutes, we were done, she thanked us and gave us the receipt and told us when they'd be ready.

We stopped in the lingerie section, where my sister took several snapshots of me holding up bras and teddies. I was getting more comfortable and confident. We then headed for the door and I was greeted with normal reactions, as I passed others and made momentary eye contact. It was great, I was passing!

Our next stop was a Chinese Restaurant, we were treated very nicely and I visited my first ladies room. It was thrilling walking into the room and seeing myself in the large mirror. I checked my lipstick and my shape, thinking to myself, not bad, I'd date me. Back to the table, my sister had the waiter take a picture of us. He asked us if we were sisters. Wow, I was flying, what a statement. My sister and I looked at each other and she said "why yes, how did you know". He politely said he just thought we looked a lot alike. He then left us. My sister giggled and said "see, you are doing fine," what a vote of confidence.

Things went on and on like that through-out the rest of the day. That night we went to the Harbor Cocktail lounge to party right. I was now feeling still a bit uneasy, but after a couple of drinks I was moving in my seat as the band played on. I made half a dozen trips to the ladies room, and was having so much fun passing the other girls on my way to the stalls and back out into the club. I never stayed around to get into their conversations, nor made much contact with them at all. I wasn't that bold or sure of myself. I'd pause at the mirror and check my hair or lipstick, but as soon as another girl came to the mirror, I was out the door.

Back at our booth, the biggest surprise awaited me. I had just returned from my seventh trip to the ladies room, which was really amusing my sister, when this really handsome guy came up to our booth and looked straight at me and asked if I cared to dance. My mind went blank, I looked over at my sister, and she was smiling really big, time stopped, I was swimming in confusion, when he asked again. I said okay, and slid out very lady like, got up as he held out his hand. I placed mine in his and off he led me to the floor.

Fortunately the music was up tempo, and we danced apart, but he smiled and watched me so close. I was losing my confidence, and was thinking too much. Then my sister appeared with another guy and danced right next to us. She looked over at me and said "go girl go". and I was transported into the role I was trying to become.

The song ended and a slow one started and he pulled me close, and we were dancing slow. Oh my, I was swimming in thoughts, he said he liked my perfume. I blushed and had to remember to keep my mouth closed, I was awe struck. Finally the song ended and I said I needed to sit down, so he led me back to the booth. My sister got up, grabbed my hand and said we were headed for the ladies room. I followed, and once inside she gave me a big hug and asked me how I felt. I tried to tell her I was both thrilled and confused. She said that this was enough for one night, and talked me easily, into leaving.

We left and went to an all night restaurant, Ordered some coffee and a breakfast, which we split, and talked for hours, before heading home.

I am so thankful that I can recall this event with the help of my sister and all the snapshots she took while we were out on this most memorable occasions to me, my birthday. When I think back of that day, I realize that it was indeed a birth day, I am woman, and I am having the time of my life living it. I hope all of you are having as much fun as I am, because no one person should have to share this feeling alone. Get out there girls, it's worth it.

Hugs and Kisses,

Heidi ;-)

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