It Was My First Time                       by: Janet L. Stickney                   JanetLynn17@Hotmail.com

 

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 the midst of 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 some 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 just a boy in a dress, but I had boobs and a trim waist! My hair was still in a ponytail, so I let it out, which improved my looks, but only marginally. That's when I jumped off the deep end. I took the dress off, sat at her vanity, and tried my hand at makeup, doing the best I could, which I knew wasn't that good, then brushed my hair out until it resembled a girls style, and put the dress on again. This time, while not exactly pretty, I decided it wasn't as bad as I thought it might be, 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 my sister Cheryl walked in on me.

We looked at each other, shock on her face, a frog in my throat and shame coloring my face.

"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 ugly, or 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, became over awed at what I saw there, and stupidly let a slow nod happen. Why? To this day I don't know, but something caused me to let her do a makeover.

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. My hair, once stringy and without shape was now done in a swept back style, accented with pink and gold earrings and a delicate pendant that lay between my 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, and while not forgetting about that incident, I did not try it again. 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 or find a job?"

"Well…yes and no. I was going to lounge for 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 with her, in her office! The implication was that I would be doing it as a girl! My first thought was to deny everything, but with a second thought and a look at my mother, I knew that was hopeless to deny that I had tried on Cheryl's clothes. I didn't admit it of course, I just didn't deny it. It was a one time thing that turned out okay, but…

"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.

"As a young girl 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. Then 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. I told them you are my daughter.

"Dad…"

"Agrees that you cannot sit around all summer, and he 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. There is no way I could earn enough to put myself through school, so I was stuck between becoming a girl like mom wants me to, or risk not going to school in the fall. 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 because he thinks I'll become a better man for it, whatever that means. 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 an answer by the way. "Please undress. 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 same girl had reappeared! This time my 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!

"Mom, I hate the name Tammy! Don't call me that. It sounds like I'm three."

"What name do you like dear?"

I didn't have any girl name that I liked for myself, and since I never gave it any thought at all, I was momentarily stuck. Then the radio announcer introduced a song by Janet Jackson, and I quickly told mom I would use the name Janet. She smiled and told me she liked the name, and motioned for me to follow her. Being dressed as a girl at home? Okay. Out there in the mall was something entirely different! I certainly did not want to go into the mall like this, but I really had no choice. Like I said, I was stuck. Mom walked out of the room, leaving me to stare into the mirror and wonder why my parents thought it was necessary for me to become a girl for the summer. No answer came, and I slowly walked out of the room and joined mom. The ride to the mall was about twenty minutes, every one of them torture for me as I just knew that someone would recognize me as a boy in a dress. My first step inside the mall was not met with laughter, yet I did not relax a bit. I stayed close to mom as she led the way inside, up the escalator, and into the lingerie section. I wasn't exactly lost, I knew what most of the stuff was, but mom began to hand things to me, starting with panties.

Embarrassed by it all I said nothing as she quietly added things she said I would need. Like the padded pantybrief. It would give my hips some roundness she said. It grew worse in the dress department when she insisted that I try on a skirt and a dress, but, I managed to get through it without being discovered as a boy. On the way home she stopped at a small shop where, to my great dismay, I was actually fitted for breastforms! Standing there naked to the waist while the woman glued them to my chest was almost more than I could handle. We came home with new shoes, a dozen panties, two bras, a skirt and dress plus the breastforms! When the woman put them on my chest, she mentioned that the glue would hold for at least 3 months, which is when I knew that any chance I might have had to escape this lunacy was gone. I was beaten, and started to cry a little, but mom held me and told me that I would enjoy this if I simply accepted it. I had no choice did I? We went to the salon for my appointment, and by the time we left my hair was 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 Janet, 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 had been attached to my chest, I had to learn to get used to them, sleeping on my side or back, how to put on a bra and so on. Having the twin mounds pushing at my shirt was odd enough, but the weight of them and the way they moved every time I took a step also took a bit to get used to. Twice I went braless, and quickly understood why women wear a bra. Each day I learned how to do something else while getting better at everything from makeup to hair. Cheryl stopped by a few times and we talked, but not once did she laugh at me.

On Monday morning, dressed in that same blue dress mom started me out in, I went to work with her. I went through personnel, filling out the forms like mom told me to, then I was assigned to another department. Being extra careful, I did not encourage friendships, but it was unavoidable, and was quickly drawn into a group of girls about my age. They talked about all sorts of things, like periods and how yucky they are, babies, which I know nothing about, and boyfriends. Twice they tried to set me up on a date, and each time I refused. I had to dress this way, not become a girl, and could not see me kissing another guy. It wasn't hard to figure out how to act, or bend, or things like that, and I 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 almost natural for me to get up, then get dressed as a girl. I got used to the restrictive was the clothes fit, doing my hair, makeup and so on. I had all of the mannerisms down pat, and since everyone seemed to accept me for the girl that I seemed to be, I no longer thought that I was about to become a laughing stock.

An opening came up in medical, which paid more, and since the only reason I was there was to make money, I applied for the job and got it. They required that I wear a white nurses uniform, so mom and I went shopping for uniforms that night. We bought three, plus a white pantsuit. Mom also included white panties and two slips, since color would bleed right through the 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 as a nurse, then, when it came time to enroll in college, I told mom I was going to State, but not as a business major. As the time grew closer for me to return to my old self, I knew that I couldn't do it. Somehow, I had grown to love being a girl, and did not want to give her up. Especially now. You see, I met this guy at work. Gus. Tall and handsome, he asked me out, and for the first time I broke my own rule and went out with him. That's all I'll say about that, except to say that he is a really great kisser.

"I've decided to go to the Nursing school at State 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 Janet, 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!

 

 

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