Crystal's StorySite

I started by going out when he was 14. Things progressed until my parents set a trap and caught me fully dressed. I was 16 at the time. Insisting that I take the opportunity to dress full time, I took a job in my Father's office. After a few months, I joined Co-op and continued to work as a girl. I took several promotions, then my first real vacation. The French Riviera called to me, and I went, only to be hit on by my boss. I found out he was lying, and a trap was set. One that curtailed his amorous ways, got me promoted, and gave his wife a chance to rein in his leering eyes.

This story inspired by the cover "Maiden Voyage" designed By Jenny North, and can be found on her website.


Maiden Voyage                  by: Janet L. Stickney      


Starting at a young age I had always liked to dress up as a girl, then, as time went on, and I could no longer stand the pain, I began to go out. My first foray out of the house as a girl came when I was 14. Nervous and edgy, I managed to walk around the block and make it home without any complications. When my sister went to college she left behind a lot of her older clothes, most of which fit me, and I began to get dressed up, and go out alone, more often. On that Saturday, I had carefully taken the time to rid my body of any hairs I could find, then, with the door securely locked, I started to get dressed. My hair in a flip, my makeup okay, pantyhose, the waist nipper, then the bra I filled with birdseed filled nylons, and the white blouse over the short red skirt. I wore low black heels with gold jewelry.

My parents were going to the club, so I merely waited until I heard their car pull out, then did my lips in a soft red, dashed on some perfume, and opened the door to my room. I took a few steps out of my room, listening to make sure they were gone, then turned to walk down the stairs, and stepped right in front of my Mother. We both stared, both shocked for a moment, then, without a word, she grabbed my hand and took me into my sisters room. She looked me over from head to toe, then told me that since I obviously planned on leaving the house, there was no reason I could not go with them to the club, then, without a word to me, selected a very nice dress for me to wear, handed it to me, insisted, then waited until I changed into it.

"It would helpful if we knew what to call you. Have you a name dear?"

I did, and I had kept it to myself up to now, but…


I was 16 when this happened, so I certainly knew that boys generally do not dress as a girl, but I simply could not stop doing it, and this was the result. The dress I had on was a black, one that was fitted on top then flared at the hip. The hem was just above my knees, and I knew I looked good in it. I had worn it in private before.

"You look quite pretty Rita. You have a much better face than your sister, and your hair is very well done."

All I could think of was what my Father would say when he saw me. "Dad?"

"Oh, he went to get gas for the car. He and I were simply waiting for you to appear. We were expecting you to get dressed up. I was only shocked at how nice you look!"

"He knows? You know? But how?"

"We've always known! Once in a while, usually when we were going to be out for the evening, your room would smell like makeup and perfume the next morning, and twice I have found panties or a bra under your bed, and once you left your makeup out. All we had to do was plan just a bit better than you, then wait."

I was so scared at that moment, yet mom took my hand and we walked into the familyroom to wait for my Father to return. I heard his foot steps, then he appeared in the doorway. He looked at me, then motioned for me to stand up, which I did. He didn't smile, but he didn't frown either.

"Dinner is at six, we should be going."

He held the door for Mom and I, then, on the way to the club Mom told him my name. From that moment on he never once slipped. He always called me Rita. To say I was nervous when we walked in would be an understatement, yet Mom took one of Dad's arms, I took the other, and Dad led us to the table, our usual table. Nobody gave me any funny looks, dinner was pleasant, and the music wonderful. By the time I got home I had relaxed to the point of simply being a girl, which was an entirely new feeling for me. As I slipped into my room to get ready for bed, Mom said she and I would talk in the morning. As I slipped into bed I wondered what she was going to say. I mean, she said they both knew, they had arranged that bit at the club, and both of them had treated me as a girl all evening. I had no idea what she had in mind.

In the morning, when I showed up for breakfast, all that remained of the night before was my messed up hair. Dad had already left for work, so it was just she and I.

"You looked very nice last night. I'm a bit surprised that you're not dressed this morning."

Not being quite that stupid, I said nothing.

"Why don't you go up and get changed, then we can have a nice Mother daughter talk?"

Since it only sounded like a request, so I went to my room and quickly changed into a pair of shorts with a white pullover top, did just foundation and powder, added some pink lipstick, then rejoined my mother. Once again I got that very calm look from her.

"We have decided that since you like to dress as a girl, and are quite good at it, as soon as school lets out for the summer you will become Rita full time and work in your Fathers office. If, at the end of the summer you decide to stay as Rita we will talk about it, but from the moment school is out, you will become Rita. Right now, obviously, we have to let you finish school as Ronald. Any questions?"

Hell yes I had questions! But right then wasn't exactly the best time to ask them. Besides, I had always wanted to be a girl for more than a day, and now I had my chance. Then Mom asked me if I had ever been shopping. Of course I said no, then she told me that I should not be wearing another persons panties, and since I would become Rita for the summer, it made sense to her that she and I remedy that. She also told me that we would look for some affordable breastforms that were my size. That's when I asked her why she and dad were doing this. I mean, I am their son, yet they were both acting as if they wanted me to become their daughter, at least for the summer.

"We would rather you do this in the open, with our help, than sneak around and always be afraid. This way, I'll be here to help you when you need to know things about being a girl, and your Father will protect you, just like he does your sister. By letting you do this for the entire summer you'll get to know what it means to be a girl, then you can decide for yourself if this is for you or not. In other words, we would rather have you become a lady, if this is for you, rather than be a scared little boy in a dress later on."

I went to my room and slipped the shorts down, then rearranged things and pulled on a pantybrief. Once I had the shorts back on, I added earrings, a watch, then a pair of rings and some perfume. I wore my gym shoes because I didn't have any flats. Mom let me drive, then, at the mall, I followed her inside, staying as close to her as I could. I was in dangerous territory, since so many of my class mates went to the mall to just hang out. Mom went straight to one of those stores that cater to women that need help because Mother Nature had been unkind to them. The minute the woman saw me I think she knew, but with just a wink, she measured me, then returned with a pair of boxes. She explained the size, which was a B, and let me slip them into my bra. The woman also suggested a padded pantybrief, so Mom bought two of them. I slipped one on, then I discarded the birdseed on the way out of the shop. In the lingerie department of the biggest store in the mall, she let me pick out three new bras while she picked out the panties. She also added a waist nipper to the selections.

Now I at least felt like a girl, and I noticed that my shorts fit a lot better. Having breasts that bounced in my bra was a new feeling, but I liked it and did not mention it to Mom. I had my colors done and picked up some better foundation and colors of makeup, then we went home. I went to my room to put things away, and wanted to remain dressed as a Rita, but I have another week of school to go, so I undressed, took a shower, and slipped on some jeans and a tee before I went to watch a little television before bed. Nobody said a word about our day, or the fact that I looked like myself again.

It became a very long week as I began to anticipate my summer. I was elated and scared to death at the same time, anxious, yet concerned about becoming Rita, since so many of my friends might see me. Then what? What if they recognized me? By the time I got home on Friday afternoon I was an emotional wreck, but Mom was waiting for me. When I told her what I was worried about, she told me that our neighbors, with their daughter, had been sitting across the room from us at the club!

"Neither Kitty or Mike knew it was you, and they had a clear view of us all evening. Kitty told me that Rachel wanted to get together with you, but I had to tell her you were where very busy."

"I don't know what Dad was thinking when he said he wants me to work in his office. I mean, how can I? I'm not really a girl."

"What does that have to do with anything? You'll be answering phones and some minor filing. Think of it this way. You'll get a chance to see how girls manage while having to work every day."

"No, I mean, what about the other people that work there?"

"Do you plan on telling them you're a boy in a dress?"


"If you look, smell, and act like a girl, it shouldn't be a problem should it?"

My Mom is an expert at winning circular arguments, and it was foolish for me to even bring it up. I knew, and she knew, that I was going to become Rita for three months, and work in Dad's office, and that's all there was to it. She told me to go change, so I went to my room. Every time, in the past, my hair would start to grow back out after a week or so, and I could either use the cream hair remover, or take a bubblebath and shave it off. I opted for the bubblebath. I luxuriated in the hot water, and carefully shaved every inch of skin I could reach. By the time I stepped out of the tub that familiar feeling of femininity was washing over me. I opened the package of new panties, selected the flowered ones, then, after making careful marks on my chest, I attached the breastforms using the glue that came with them. The concealer hid the seams, and it looked as if I had grown a pair of boobs over night. I did not put a bra on, but went back in the bath and used a blow dryer on my hair to add fullness and make it easier to style. With a few rollers and a curling iron, I created a very nice modified flip that was curly in the back with longer bangs that I brushed to one side.

I used the new foundation, just the barest minimum I could get away with, then powder to set it. On my eyes I used light gray with copper, black eyeliner and pencil, then a peach blusher on my cheeks. That done, I slipped on one of the new bras, adjusted the straps, then pulled the foam pads out of one of the padded pantybrief's. I had read more than a few stories on the Internet about doing this, and wanted to see for myself if it would work. By removing the pads from the pantybrief and slipping the pads under my panties, and moving them around a little, I got a smoother line without any lumps. I pulled on the pantybrief without the pads, and had a nicely rounded shape. The pantyhose always feel good when I pulled them on, and this was no exception. The skirt I wanted was a short navy one with pleats, and after I had it on I pulled a pink shell over my head and snugged it down over my breasts, showing off my new charms quite well. I slipped on the low heeled navy shoes, then added gold earrings and a bracelet, pink lipstick and perfume. Without a worry, I walked out of my room, down the stairs, and into the familyroom. Mom smiled when she saw me, then, when I sat down, she and I talked a bit.

"Your sister would be unhappy to hear me say this, but you're prettier than she is. Now, if we can get rid of some of those male mannerisms of yours, you'll be just fine."

Carol had left home the minute she graduated, and we have not heard from her since. Last we heard she was in Europe someplace, but I knew Mom was right. Carol would choke if she ever saw me like this. Mom had me sit in a chair a number of times, then simply stand still after walking around a little. Each time I was shown how to hold my arms, place my feet and so on. After a few hours of that, she told me to get the matching navy jacket, touch up my lipstick, and grab a purse. As soon as I was ready, Mom, also wearing a nice suit, and I drove over to Dad's office. I was taken to the personnel office, and filled out the form correctly, all that information was correct except for my name. I had not selected a middle name, and was momentarily stumped. Then I wrote in Elizabeth, and turned in the form. Since the lady knew Dad, I was hired on the spot, and told to report on Monday morning. Then we went to see Dad.

There was someone in his office, but he didn't miss a lick when he saw me.

"Hi Kitten".

I gave as good as I got.

"Hi Daddy."

He introduced me to the woman, and found out that she is the person I would be working for, then he took Mom and I to lunch. I was having a hard time understanding why he was going along with this, but decided not to ask him. I was dressed as a girl, which is what I wanted, so I didn't want to upset things. After lunch, Mom and I went home and I changed into a pair of jeans and flats.

I started work on Monday, wearing that same suit with a white shell and low heels. It was easy work, and I actually liked it. There were four other girls working in the office, two of them I knew, but none of them ever gave any sign they knew who I was. Being slender like Mom, and standing a mere 5'7" in my bare feet, if fit right in, and as long as I didn't do something stupid, I thought I would be fine. I worked there for a month, and became used to doing my hair and makeup, dressing quickly and generally got used to being a girl. My mannerisms got better, I had my hair styled and my nails done, and I no longer carried fear in my side pocket. I was at my desk when the news came. Dad had been killed in an accident on the freeway. There was no way I could appear as a male for the funeral, so I wore a black sheath dress and stood next to Mom as his casket was lowered into the ground. A week later, when I returned to work, I had a new boss. Mom had urged me to continue at work, even though Dad was gone now, and while I struggled with it, I did was she asked me, and returned to work. My new boss stopped by, offered his condolences, then promoted me to office manager, provided I agreed to work in Co-op. I must have had a moment when my brain cells went dead, because I agreed.

When I realized what I had done, I didn't know how to back out, and truth be told, I didn't want to. But being in Co-op would mean that I would have to attend my last year in high school as a girl. Mom and I discussed it, and when I told her I didn't want to revert to my male self, she told me she already knew that, and we agreed to change my name legally. Mom took care of that the next week, and I became Rita Elizabeth. Now, if I only had the rest. I had to remove the breastforms once a week to let my skin breathe, but I noticed that my skin was getting severely red, and I was afraid that the glue was damaging my skin because of prolonged usage. I called the company that supplied the glue, and they sent me a different kind, plus a lotion to use on my skin before I reattached the forms again. The new glue would allow me to wear the breastforms for a month at a time.

On the day school started Mom and I went to the office armed with my legal name change and the application for Co-op. I expected at least some questions, but the secretary, rushed with all of the new students, merely stamped the form and entered me in the rolls. Since the girls I worked with were also there, I had a few friends that only knew me as a girl, and I was introduced around to kids I had known for a long time. The boys now looked different to me, and the way they looked at me felt very strange. I continued to work at the office, gaining responsibility as time went on. At school, an old friend of mine began to talk to me, walking me to class and so on, then he asked me out. I had not been on a date in months, with anyone, so I said yes. Tim was thoughtful and very nice with me, and I found myself easily letting him kiss me. Tingles and shivers took over that first time his lips touched mine, and I loved it. He and I became an item of sorts, and while I never let him touch me, I wanted to let him. But what good would a handful of silicone do him or I? Once again, I talked to Mom about it, and she told me to be patient.

By the time Christmas came I knew why she told me to be patient. All the hair on my body fell off, and I had small but very real breasts of my own! By Easter I no longer used any padding or the breastforms, and I finally let Tim slip his hand under my sweater and bra. His hand felt wonderful, but not as good as when he kissed me there. He took me to the Prom, which is when I took care of him. I didn't mind at all, and I know he loved it. At work they threw a huge party for the four of us girls when we graduated, then I was offered another promotion, as the head of billing! I took it and settled into a routine. Mom and I still shared the house, but she had met someone, and I knew that my time staying there was coming to an end. With the raise, I was able to get an apartment, and began life on my own. I planned my vacation in August. I was planning on going to the Riviera. I bought new bikini's and some lightweight traveling clothes, then, when the time came, I flew to France.

I was just in my hotel, ready to change, when a note was slipped under the door.

Met me at the pool. I think you're the most beautiful girl I have ever seen."

It was unsigned, but since I was going to the pool anyway, I stuck the note in my purse, changed into the red bikini, grabbed a towel, and walked out of my room. By this time I had been a girl for five years, and no longer doubted my own femininity, even though I am still, technically a male. I found a lounger, then spread out to enjoy the warm sun and fantastic sights. I saw him as he walked over to me. It was my boss! He sat down next to me, then he asked me if I got his note.

"Yes, but you're married!"

"Not really. We're separated."

"I see. How did you know where I was?"

"I've always though you were beautiful Rita, but until now I haven't said anything because I was married. Kelly told me, and I arranged to be here. How about the two of us getting together tonight? Over dinner perhaps?"

Mom had told me about being careful, and I had a rule not to date men I worked with, but…

"Just dinner Ken, nothing else."

"That's fine. Seven?"

I nodded my head yes and he walked away. Later I went to my room and changed into a slinky black dress with spaghetti straps, black heels, and not much else. Just panties, makeup and a smile. He was pleasant and attentive, and clearly wanted to get into my panties, with me still in them. But something nagged at me, and I wasn't about to let him come near me, just yet anyway. I let him kiss my cheek when he walked me to my room, then went in alone. The next morning I was out for a walk, stopped at a local café, and had just sat down when a woman's shadow loomed across me. When I looked up, I saw that it was Ken's wife!

"Can I sit down?"

I waved my hand and she sat, then smiled at me.

"Kenny hit on you didn't he?"

"He said you two were separated, and I let him take me to dinner, and that's all!"

"I know. I was watching him."

"I take it you're not separated?"

"He uses that line whenever he thinks he can get away with it. When Kelly told him where you were going on vacation, I heard that conversation on our extension phone. I'd really like to shut him down. But I love him, and don't want to lose him."

"Men are men Carolyn. All they think about is sex."

"True! I wish there was a way to get his attention and make him stop chasing around."

I knew that Ken was on thin ice in the office, our general manager had warned him several times about bothering the women that work for him, and a nasty thought entered my mind. I could make him faithful, and get his job at the same time.

"If I tell you something, it could hurt me, but if you want Ken to be true to you, I think I can arrange it, but he will lose his job in the process."

"I'm not worried about his job Rita. I just want him to have only eyes for me!"

So, for the first time ever, I trusted someone with my secret. Carolyn listened, her eyes growing wider and wider, until, when I was done, she started to laugh. I thought I had made a mistake trusting her.

"That is so delicious! He'll be nothing but eager if you let him into your room, and if I tape it, leaving your head out of the tape, I will have plenty of incentive to keep him in line! I love it! By the way, your secret is safe with me Rita."

It was easy to set it up, and Ken willingly followed me to my room. Since I had on the red bikini, I swayed back and forth sexily all the way to my room. Once inside he grabbed me and began to fondle me, taking my top off and kissing my nipples. Boy did that feel good! Anyway, I slowly undressed him, then lay back on the bed, my hand over my groin.

"I want you to kiss me there Kenny. As soon as I take my panties down, I want you to open wide and kiss me. Okay?"

His head was bobbing up and down in eager anticipation as he moved to get closer to his prize. With a flick I yanked them down, grabbed his head, and pulled myself into him. He recoiled, anger filling his face as he looked at me. He was about to slap me when Carolyn walked into view.

"Did you get it all?"

"Of course. He looked so cute going down on a little boy that I can hardly wait to run the tape!"

He made a grab for the tape and got it, but Carolyn merely smiled at him. Then she told him to get dressed, and reminded him that she had another copy of the tape.

"By the way Kenny, since it was so good for me too, I'll let you resign your position. I do most of the work anyway, so I might as well get the money too."

He was beaten and knew it. He and Carolyn left, and I got dressed in a flippy little skirt and top, then went to eat. I did not like what I had done, yet it served a purpose. Teenage boys are all horny, and getting one into a high state of readiness isn't hard to do. But as an adult woman, I had yet to prove to myself that I was desirable. Ken did that for me. He also made it possible for me to move up at our office, the women would no longer be bothered by him, and Carolyn now had a hammer over him to keep him in line. On the way out I bumped into a tall handsome man, and after some words, let him guide me to a small pastry. Later that night I served his needs as well as I could. It was my Maiden Voyage into womanhood, and I'm glad I did it.

Ken did quit, I was promoted, Mom got remarried, and I finally had my surgery. I met Tim at our five year reunion, and our romance started up again. He's an attorney now. He has asked me to marry him, and I will, next June. Then I'll complete my voyage from little boy to girl to woman, then wife.




© 2000

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