I was about 5 or 6 I guess. I can remember my dad going ballistic, and right after dinner mom had me change back into my own clothes while she told me it was wrong for boys to dress as girls. After that I was always careful so as not to get caught whenever I dressed up. I always thought I was beautiful, but then, I was always looking at the ideal in the mirror rather than the reality.
My name is Tim Grant, I’m currently 5′ 5″ tall, weigh about 125 pounds, with green eyes with brown hair. My mother was just five foot, Claire my sister 5′ 2″, and dad was 5’6″. I sort of fell in the middle, and didn’t expect to get any taller. I knew I wanted to dress as a girl as often as I could and by the time I was 15 and starting high school, I was well aware of men who dressed as women. In fact I had found a lot of sites on the Internet that catered to them, and had printed out a lot of information, from how to make your own breastforms and padding to how to do makeup and hair. Experimenting, I made some birdseed breastforms and had cut some foam rubber into ovals to pad my hips and let my hair grow out until it was shoulder length, all in preparation for my debut this coming Halloween.
It was the one time of the year I could dress as a girl and `get away’ with it so to speak, and I had planned for that night very carefully. Claire had moved to college, but she had left behind a lot of clothes, and I had carefully tried on every item, and now I had several complete outfits, including shoes. My biggest downfall was hair. No matter how hard I tried I was never able to manage a truly feminine hairstyle. I managed to get close, but I was always unhappy with the results and usually put my hair in a ponytail.
As Halloween drew closer, I knew that I would have to confide in my mother because there wasn’t anyway around it, so one day right after school I told her that I was going to the school Halloween party as a girl. To my surprise, she asked me if I finally figured out how to be a girl! “What do you mean figure it out?” “What I mean is have you figured out how to become a perfect young lady.” I was at a loss for words! “Tim, you cannot possibly believe that I don’t know about you dressing up in private do you?” She knew! I was dead! “If you want to dress as a girl I insist that you let me help you get ready. Do you have everything you need?” “I borrowed some of Claire’s things mom, I have several outfits.” “Show me” Was all she said.
In my room I showed mom what I had selected to wear, all of it, and all she said was “adequate”! “I have to go to the store on Saturday anyway, so why don’t we get you dressed and let me see what you look like, and if you need anything we can get it then. I’ll even do your hair for you.” “Dad.” “Won’t be here all weekend. Now plan on getting dressed right after breakfast On Saturday.”
It was a very long two days as I wondered just what mom had in mind, but I was not about to let this opportunity slip by, and on Friday night I made sure that I didn’t have one stray hair anywhere on my body. Right after breakfast mom and I went to my room where I slipped on a pair of panties, then as she watched I used the foam pads to make my hips rounder. I slipped on the pantybrief and reached for the bra, but mom stopped me.
“Lets do makeup first Tim.” I walked into my sister’s room and sat at her vanity while reaching for the foundation. Mom sat next to, and slightly behind me watching, but not saying anything as I smoothed the liquid foundation evenly on my face. I started to reach for the eyeshadow, but mom stopped me. “Let me show you something Tim.” She dabbed at my face with some loose powder, letting it set for a moment before she brushed away the excess, leaving my skin looking smooth and soft, and all one color.
Mom watched as I added a bit of earth tone eyeshadow, then a soft plum over that, highlighted with black eyeliner on both upper and lower lids. I used a rose silk blusher on each cheek and was reaching for the lipstick when mom told me to wait. She sprayed my hair with hairspray, and began to curl my hair with a curling iron. As she worked I watched her carefully so I could do it myself if I had to, or had the chance. She left my hair all curled up, telling me to finish getting dressed. I slipped the bra on and added my birdseed breastforms to the cups. I now had a full `A’ cup.
Sitting on the bed I slipped on some pantyhose, then went to the closet to get the dress I had planned to wear to the party. “Oh no, not that Tim. For shopping you’ll want a skirt and blouse.” “Shopping?” “Of course! You’ll have to try on anything we buy, and I’m sure that you would rather look like a girl trying on clothes rather than a boy!” “But I thought. I mean. what if someone sees me!” “Then they will see a pretty 15 year old girl! Now find a skirt and blouse and lets finish getting you ready.”
I selected a pleated green skirt and a white blouse with a round neck collar, and as soon as I had them on mom finished brushing out my hair. I stepped into the black flats and mom handed me a soft red lipstick. In the jewelry box I found a pair of gold hoop earrings and slipped them into the holes in my ears after I took out the studs I usually wore.
Mom was grinning at me as she picked up some perfume and gave me a spritz. “I think that will do it for now, except for a name. I can’t call you Tim now can I?” Mom wanted me to tell her my deepest secret, and as much as I wanted to tell her, I was afraid! I was standing in front of the mirror looking at someone else. It was me, but different, like I was my own sister, and I was afraid to tell her the name I had chosen for myself. “Tell me Tim; I’ll bet it’s a pretty name.” “Gail.” I had blurted it out quickly, and mom smiled when she heard it. That’s a very pretty name! Find a purse Gail, and lets go shopping!” I was rooted to the spot until she took my hand and led me out of my room, stopped and picked up her purse, and continued out to the car.
I had never been outside the house dressed as a girl before and I was very nervous as we drove down the street. She reprimanded me twice for slouching down, and when we got to the mall she parked as far away from the doors as she could, even though there were places closer. Before we got out of the car she turned and looked at me. “You are a very pretty girl Gail, and going into the mall is exactly what you need. If you act like a girl, walk like a girl, and watch your mannerisms, nobody will know who you are. Actually I was counting on some of your friends being here, because that way you’ll have to be doing your very best or be discovered.” With that, she got out of the car and waited while I did the same. Standing next to the car I felt a breeze run up my skirt and held it down as mom just giggled. “Come on then Gail, we have a lot to do today.”
We went through the food court, and sure enough, standing right in the middle were some kids I knew at school! I stayed close to mom and we walked right on by, and they never gave me a second look, like they knew who I was! Out of earshot, I mentioned it to mom and all she did was smile. I walked beside her as she veered into a huge department store, and then into the lingerie shop. “We should get you some bras and panties of your own Gail. We’ll start with a half dozen panties and two bras I think.” Please note, she did not ask me, she told me. I selected two bras I liked and some nylon panties, but she said cotton was better, so I got the bras and cotton panties in assorted colors. “This party, is it fancy?” “It’s a Halloween party mom, not the prom.” “A pity.” “Huh?” “Oh, never mind dear, I was just wondering, that’s all. But you should have something to wear that would help foster the illusion; why don’t we go in here?” And in we went, to a store that catered to weddings, proms, and so on. Almost all of the girls in school bought their dresses here, and in fact two of them, Kelly and Jessica were there!
All I could do was act as if I belonged there, and mom and I sorted through the dresses until she found one she said was just perfect for me. Believe me, I was nervous as hell when she took me into the changing area, which was essentially a single huge room. I quickly put the dress on, but it didn’t look very good on me, and I took it off and convinced mom that we had to leave. She didn’t like it, but agreed when about five girls came in just as I was ready to leave.
“Maybe at Sares we can find something for you Gail, but you’re simply have to relax! You look fine!” I tried, and almost did relax once we got into Sares. Once inside mom picked out a pink suit, a sheath style dress and a jumper for me, plus several blouses before we left for the car. “When we get home I want you to try on all of the clothes, especially the suit. Save that to last, and wear the pink heels with it.” I did as she asked, and the new bras made me look a little more pert I guess, and all of the clothes fit me just fine.
The suit was unlike anything I had worn before. It had a short, straight skirt, which hindered the way I walked. The jacket was shaped to accent a feminine waist and only made me look better. I walked out to show mom, and dad was standing there! He looked at me and I waited for him to erupt, like a volcano held in too long, but he didn’t! “Howard, this is Gail, and she will be staying with us for a few days. She has a party to go to next Saturday, so we did a little shopping today.” Then he floored me. “You. look very nice Gail; are you going to dinner with us tonight?” I looked at mom, and before I could answer she said “yes of course she’s going with us!”