It was my first time, really, it was. But my mother acted as if I had gone crazy, and all at once my life changed. My name is Tim, I’m 17, and almost out of school. Just a few more weeks to go and I had the entire summer before I start college. My sister had gotten married almost a month ago and moved, with her husband to an apartment. But she left behind all sorts of things, including a lot of her clothes. Cheryl is a real beauty, dark hair, green eyes, and a trim, shapely figure, with a smile that charmed almost anyone she decided to use it on. Mom and Dad had gone away for the weekend, and I found myself in Cheryl’s room, why, I didn’t know. But when I saw her clothes in the closet I decided, as a lark, to try them on. In my dementia, I decided on one of her prom dresses. The pink one with the huge skirt. I quickly stripped and put the dress on and found out that it would not zip up. Close, but my waist was too big. I took it off and looked in her dresser and found panties, decided what the hell, and put them on. Then, in another drawer, a padded pantybrief! I guess it was from when she didn’t have any shape to speak of. I put it on, then some pantyhose, and finally, a corselet. I struggled with that hooks in the front until I had them secured, and drew the laces tight. Looking down, I saw that all at once I had boobs, so I pulled the skin up and put that dress on again, and this time it fit.
Looking in the mirror it was obvious that I was a boy in a dress, but with boobs and a trim waist! My hair was still in a ponytail, so I let it out and improved my looks, but only marginally. That’s when I jumped off the deep end. I took the dress off again and sat at her vanity, and tried my hand at makeup, and brushed my hair out until it resembled a girls style, and put the dress on again. This time, while not I wasn’t pretty, I’m not bad I thought, and found the shoes to match the dress and stepped into them. That’s how I was dressed, standing in front of the mirror when Cheryl walked in on me.
We looked at each other, shock on her face, a frog in my throat.
"Not bad Tim, but I think we can to better. Let me help you."
As if I had a choice. I was so scared that I let her do what she wanted. My makeup was washed off and she redid it, then my hair was curled with an iron and spritzed, and finally, she gave me some lipstick to wear. Then I looked in the mirror. A girl was standing there! Again, not pretty, but not exactly me either.
"With a little more effort we could turn you into a ravaging beauty Tim. Want to try?"
I looked at the girl in the mirror and let a slow nod happen.
It took us another two hours before the girl reappeared, this time in a short, tan skirt, pink blouse with puffy short sleeves, and short pink heels. Her hair was done in a swept back style with pink and gold earrings, a delicate pendant between her breasts.
"That’s much better! You look really nice Tim!"
"Thanks."
"Want to go to the grocery with me?"
"No thanks Cheryl. I was just playing around I guess. I wanted to see how I would look, that’s all."
"Okay then, have a nice time."
Then she left! Without a word about how I was dressed, or to stay out of her clothes, nothing! I stayed dressed for the rest of the day, and that night put her things back and washed off all of the makeup.
I never gave it another thought, my parents came home, and life went on. I graduated right on schedule, and looked forward to having the summer free.
"You’ll need money for school Tim! Are you going to lounge around all summer?"
"Well…some of it anyway mom, why?"
"Because we have an opening in our office, and Cheryl tells me that you would fit right in."
Now, mom worked in an office that was mostly women, so the only conclusion I could manage was that Cheryl had told mom about my foray into her closet, and how I looked. Now mom was telling me she not only knew, but wanted me to work as a girl… with her! My first thought was to deny everything, but with a second thought and a look at my mother, I knew that was hopeless.
"It pays $12 an hour, and we could ride together to save costs Tim. Think of the adventure!" ‘
Think of the problems’ I thought to myself! Then she dropped the hammer.
"I told them you would start on Monday, so we have from now until then to get you prepared. That’s five whole days, plenty of time."
I was sunk!
"Just exactly do you mean by ‘get me prepared’ mom?"
I thought I would toss it back in her lap and see what would happen, but that backfired when she told me.
"You’ll need your hair styled, and your nails done of course, then we have to make sure you have a proper wardrobe. Of course we’ll get your other ear pierced, and maybe your eyebrows trimmed with a better arch. Of course you’ll need panties of your own, and maybe a few new bras, but I’m sure we can manage."
"Mom! That was a one time thing and you know it! I don’t want to work as a girl!"
"I’m sure that’s all true, but I gave my word and we are committed now. Starting on Monday you will be working in our office…as a girl named Tammy."
"Dad…"
"Agrees that you cannot sit around all summer, and thinks that doing this will make you a better man. Now, shall we begin?"
I wanted to jump up and yell hell no, but my mother was a forceful woman, and I had to rely on her and dad to help me get through college. If I said absolutely no way would I do this, I might just find myself on the short end all around. But if I did dress and work as a girl, I would have lots of money in the fall, my mother would forever be indebted to me, and dad would feel better. I knew what the answer would be just as she did. After all, she had planned it this way.
"Okay mom." She never forced me into dresses, she merely gave me several very bad choices. This was only the least bad!
She pointed, and I started towards my room, but she steered me into Cheryl’s old room.
"I think this room is better for a girl, don’t you?" She did not expect and answer by the way. "Please undress Tammy, I have something to make your skin smooth."
She smeared it all over me and then, after a short wait I went in the shower and rinsed it off, shaved, and washed my hair. When I felt, my skin was silky smooth and hairless! After that, it was pretty much like when I was with Cheryl. Except the hair. Mom put in a lot of rollers, and let them set while I got dressed, in the clothes she had picked out for me. An hour later I looked in the mirror and the girl had reappeared! This time her hair was fluffy with curls down the back and had bangs. I was wearing a dress, a sheath mom called it. It hit me just above the knees, was sleeveless, with a round neck and was all blue.
"You had better wear the black flats Tammy, we have a lot of walking to do today."
"Why? Where are we going?"
"Shopping of course, and you have a three o’clock appointment at the salon. Take this dear, you don’t have pockets any more."
She handed me a purse!
At home? Okay. Out there in the mall was something entirely different! But, I managed to get through it without being discovered as
a boy in a dress. We came home with new shoes, a dozen panties, two bras, and a pair of breastforms! Mom even told the woman they were for me! My hair was now set in a soft perm and tinted a lighter shade, my nails were made longer, filed into a nice oval shape and painted a soft red. Dad saw me for the first time, and all he said was, "Hi Tammy, you look very nice." Great! Now that dad had seen me, he was telling me I looked nice! The next day it was more shopping. Another padded pantybrief, pantyhose, rings, earrings, necklaces, socks, shorts, slacks, a coat, two nightgowns, and makeup of my own. For the rest of the week mom insisted that I learn how to do my own makeup and hair, so I would spend several hours each day on it. After the breastforms were attached to my chest I learned to get used to them, sleeping on my side or back, how to put on a bra and so on.
On Monday morning, dressed in that same blue dress mom started me out in, I went to work with her. I was assigned in another department and quickly got used to working in a dress, bending at the knees for example. I was accepted for what I appeared to be, and the time went by quickly. At the end of two weeks it was natural for me to get dressed as a girl, and I got used to the restrictive way the clothes fit, doing my hair and so on. I had all of the mannerisms down pat and no longer thought that I was about to become a laughing stock when they found out who I was. An opening came up in medical, which paid more, so I applied for it and got the job. Mom and I went shopping for uniforms that night, and after that, I always wore white. Dad said I looked like a young Connie Stevens in the uniforms, which was a great compliment because she is so pretty.
I worked there all summer, and when it came time to enroll in college, I told mom I wasn’t going to State.
"I’ve decided to go to Nursing school mom. That way I can keep working."
"But you’ll be a… working as a girl!"
"Right! And I intend to graduate as a girl mom. I’m your daughter now. I’m Tammy, remember?"
And so it was. I went on to nursing school, discovered the benefits of hormones, and by the time I graduated I was a woman. All because I was curious about a pink formal!
© 2000
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