First Time

By Paula

Just write your true story about the first time you knew you were transgender or some other important "first" in your life as a transgender person. Email it to Cindy. Cynthia Smith edits the stories and will be in contact with you. Drop us a line!

The first night there I could not sleep. I looked on her book shelf and found nothing but romantic novels. Curious I started reading one, then another. As I continued, I was getting strange chills while reading words describing the female characters in the book. The words were effecting me, particularly those that that detailed the way the girl in the novel was dressed. One thing led to another and I made the choice of a life time.

I started by getting a set of her panties and her bra. To my surprise they fit like they were mine. A pair of pantyhose came next and those chills became even more aggressive and a funny feeling of euphoria arose and I knew I should do it all. Seeing a copy of a glamour magazine I took everything off and started painting my nails, fingers and toes. Then I combed out my shoulder length hair and placed it in a bow. I put the panties back on along with the bra and pantyhose and stuffed the bra with two pair of pantyhose.

I searched the closet and found a denim mini skirt and a sheer white blouse. In the drawers of her dresser I found a half slip and camisole and put them all on. After putting on all these lovely things the bedroom door opened and my cousin Janet walked in.

Giggling she closed and locked the door behind her. She smiled and said she had thought her cousin Paul was down for a visit but it seemed her cousin Paula was here instead. I asked her what she meant, she said "look at yourself." I turned toward the mirror for the first time, and wow didn't I ever look great. She said that for the rest of the month I would have to do what she said or she would rat me out. Well what was I to do? I did not want anyone else to find out, and I liked being dressed very much. She told me to stay dressed and to get into bed.

After my aunt and uncle went to work Janet came in and woke me up. She said now how do you feel my little miss? I said OK and she got me up and fixed my makeup and curled my hair and gave me a nice red dress to put on. She then announced lets go, and I asked her where? She said we "girls" had a lot of shopping to do, so we went out to ladies clothing stores looking for bargains. With a little help from Janet I began to feel convertible walking in heels. Walking from their house Janet told me to walk like I was sliding along, not to be so choppy with my steps and to put the heel down before the toe of the shoe, but most of all relax and feel the silk.

After a few boys gave us "the" look, I began to feel so elegant. With the sway of my steps and the breeze on my satin smooth stocking clad legs brushing against my skirt and slip. The further we walked the better I got. Well finally we got to Leachmeir Sales and we spent the morning trying on dresses, skirts, blouses, coats and other things. This being my first time I felt such a rush of excitement. Janet stayed with me in the fitting room for safety sake.

We then went to the makeup counter and a woman demonstrated base make-up and eye liner on me as well as lipstick. The best of it all was that Janet made me try all the perfume until I settled on Charley and so we bought some.

On the way home we took a bus with all the packages we got from our shopping trip. As we rode Janet would whisper in my ear to pull my skirt down as I sat, and to cross my legs so my panties would not show . After a few stops a couple of girls got on and came over to us. They were Janet's friends from school, Cathy and Cindy. They said that they were going to the drug store for a soda and that we should come. So we did, after a while I started to become more comfortable with talking to them. They would talk about themselves , clothing, makeup and such and I started to interact with them quite well. It seemed they had no idea who I was and just took me as Paula.

Well that is how it all started, every day we would get dressed and got out for the day and at the end of the evening we would return home, sit around and giggle like girls and she would teach me how to dress, do my hair, walk, talk, and all the things ladies do in life. She even taught me how a desirable woman wanted to be kissed, and showed be what it was like to have a hand up my skirt and how it felt to have my buns squeezed while dressed. I began to feel more natural, and sassy in woman's clothing, men's clothing was just like putting a bag on. After living like that for a month it was difficult to go home. When I went home all this had to stop, it would not be acceptable behavior with my parents or my sister.

So for about 10 years this was put on the back shelf until I got married. One winter afternoon, it was snowing so we didn't go to work. Donahue was on television and the topic was crossdressers. I love my wife Jill very much but those old feelings began to fester in me. I walked down stairs to work on my computers to get away from it, I could feel the rapid beat of my heart and the emotional pulse on just the thought and memory of that month up in Boston.

After dinner we were watching a movie and I said to my wife what does it feel like to wear a dress? To which she replied, it's like a man wearing a suit. Thinking to myself she has never seen that from my side of the gender. I asked her if it would upset her if I tried it. She said OK. So I went into our room and did myself up. Panties, bra, slip and the rest. After coming into the bedroom she saw me and chuckled a bit and replied is that "my crazy husband or is it a wife or girl friend?" That evening while I stayed dressed working on my computer installing software and I just felt so fine. When I went upstairs my wife was drawing a bath, for me. She said she thought I liked being dressed, so she said I should take a bath, use a hair remover and remove all the hair from my body, and so I did.

After soaking in the tub I got out all clean, smelling of the bath oil she had put in the water. I called out for her and asked her where she was and she replied she was in the other bathroom. She said there were clothes on the bed for me and to get changed for bed. Walking into the bedroom I found a full length nightgown and matching robe. She said after I put that on to go into the living room and do my nails, hair and makeup. She said she would be back in about two hours.

I filed, trimmed and put red nail polish on my toes and fingers, dried my hair, and even curled it. Then I sat back and watched some television. Later I heard the garage door open and she came up stairs. She was carrying packages filled with shoes, makeup, bras, slips, and every thing I needed for dressing up including makeup.

She said I could be dressed up in the house only, and when I was dressed as a woman I was to wear only dresses and skirts and at night I was to wear a nightgown or a teddy. When dressed I was to do the cooking, cleaning, laundry and all of those things ladies do. She asked if I agreed. I agreed right away.

She continued to ask if I had ever done this before because I did very well getting dressed in the first place especially the make up. With that I told her about my Boston vacation 10 summers ago. She had always wondered how I could go to store and buy her clothing for her birthday and Christmas, with out any help and it was always a good choice and the correct size.

Here it is some three happy years later and I am out here in California due to a job transfer and am staying with friends that do not know about this and would not understand, so dressing is out. In a few weeks my wife will join me after the house is sold. I just looked for a house today, at lunch time I stopped by the mall and went shopping and bought a pair of panties, slip, garter belt, bra , blouse, mini skirt and some stockings. Now all I need is a nice set of white pumps and some makeup for when my wife comes out here. Sales clerks don't give me any looks dressed as a man in the store due to the fact I am calm and know what I am after.

I love the clothing, and the makeup and all that goes with it, but I would never go anywhere near a man, I am faithful to my wife but love being her girlfriend too.