Maiden Voyage

by Janet L. Stickney

Comments and Disclaimers.

This story was inspired by the fine graphic artistry of Jenny North. Her grasp of the conflicts and impossible situations we sometimes find ourselves in, are without a doubt some of the best I have seen, as she brings a refreshing and sometimes funny peek into our secret lives. Jenny North's site is worth a serious look. Laugh, cry, or snicker all you want, but please, hope you don't end up on one of her magazine covers. This story was inspired by her cover entitled "Maiden Voyages."

Jenny's site is tgfa.org, which is a link on Crystal Sprite's site: Storysite.org

Thanks, Janet

Maiden Voyage

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. Wearing these "hand-me-downs," I began to get dressed up and go out alone more often. On that fateful 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. Styling my hair into a flip, I then applied makeup and donned my pantyhose, a waist nipper, a bra that I had filled with birdseed filled nylons, and a white blouse over a short red skirt. I finished my outfit with low black heels and gold jewelry.

My parents were going to the club, so I merely waited until I heard their car pull out. Then, I did my lips in a soft red, dashed on some perfume, and opened the door to my room. I took a few steps into the hallway, listening to make sure they were gone. Once I was certain that I was alone, I then turned to walk down the stairs and stepped right in front of my mother. We both stared shocked for a moment. Then, without a word, she grabbed my hand and took me into my sister�s room. She looked me over from head to toe, and proceeded to tell me that since I obviously planned on leaving the house, there was no reason I could not go with them to the club. Without a word, she selected a very nice dress for me to wear and handed it to me, asking me to put it on. Still in shock, I looked dumbly at the dress and then back at her. She repeated her request in a more commanding tone and waited until I changed into the dress.

"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�

"Rita," I squeaked out.

My sixteen-year-old mind was still spinning from the events of the last few minutes. I certainly knew that boys generally did not dress as girls, but I simply could not stop doing it. I guess on some level I always knew I might get caught, but I never really thought it would happen. I got careless and this was the result.

I looked down sheepishly at the dress my mother had made me wear. It was black, fitted on top and 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 several times 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!"

I was stunned. "H-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 even left your makeup out. All we had to do was plan just a bit better than you, then wait."

I was terrified, but Mom took my hand and we walked into the family room to wait for my father to return. I heard his footsteps approaching, then he appeared in the doorway. He looked at me and 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 stated simply.

He held the door for Mom and me, as I nervously made my way out to the car. 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. I was trembling like a leaf during the entire ride to the club, and to say I was nervous when we walked in would be a tremendous understatement. However, Mom took one of Dad's arms, I took the other, and Dad led us to the table--our usual table. I kept waiting to be exposed, but nobody gave me any funny looks, dinner was pleasant, and the music quite soothing. By the time we returned home, I had relaxed to the point where I simply started to feel like 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. 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. After nervously turning that over in my mind for a while, I finally fell into a peaceful sleep.

In the morning when I showed up for breakfast, all that remained of the night before was my messed-up hair. It was Saturday, but I knew that Dad sometimes worked on the weekends. That was apparently the case this morning, so it was just Mom and me.

"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, I went to my room and quickly changed into a pair of shorts with a white pullover top, put on just foundation and powder, added some pink lipstick, then rejoined my mother. Once again I got that very calm look from her as she assessed my appearance.

"We have decided that since you like to dress as a girl--and are obviously quite good at it--as soon as school lets out for the summer you will become Rita full time and work in your father�s 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, however, 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 breast forms that were my size. That's when I asked her why she and Dad were doing this. I mean, I was 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 rather than be a scared little boy in a dress later on."

I nodded thoughtfully, then excused myself to go get ready for our little excursion. Returning to my room, I slipped my shorts down, then rearranged things and pulled on a pantybrief. Pulling the shorts back on, I then added earrings, a watch, and finally a pair of rings and some perfume. I wore my gym shoes because I didn't have any flats.

Mom seemed satisfied with my appearance, so she handed me a small purse and we left for the mall. Mom let me drive for the short trip to the mall, which helped me to keep my mind occupied, as I was still quite nervous. Arriving at the mall, I followed her inside and stayed as close to her as I could. I knew that I had entered dangerous territory, since so many of my classmates went to the mall to hang out.

As I watched apprehensively for anyone I knew, I noticed that Mom had made a beeline for one of those stores that cater to women who needed 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 the breast forms into my bra. She also suggested a padded pantybrief, so Mom bought two of them, as well. I slipped one on then discarded my birdseed falsies on the way out of the shop. Adjourning to the In the lingerie department of the biggest store in the mall, Mom then let me pick out three new bras while she chose the panties. She also added a waist nipper to the selections.

Now I at least was starting to feel 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. At one store I had my colors done and we purchased some better foundation and colors of makeup, then we returned home.

I went to my room to put my new things away. I wanted to remain dressed as a Rita, but I still had 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 dinner. Nobody said a word about our day, or the fact that I looked like myself again.

The week passed slowly as I began to anticipate my summer. I was elated and scared to death at the same time. I was anxious and concerned about becoming Rita, since I knew that so many of my friends might see me. Then what would happen? 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 about my concerns, 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 very busy."

I shook my head in disbelief. "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?" I asked.

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

"No."

"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.

In the past, every time the hair on my body would start to grow back (usually after a week or so), I would either use the cream hair remover, or take a bubble bath and shave it off. Today, I opted for the bubble bath. 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 a package of new panties, and selected the flowered ones. Then, after making careful marks on my chest, I attached the breast forms using the glue that came with them. The concealer hid the seams, and when I saw myself in the mirror, it looked as if I had grown a pair of boobs overnight. I did not put a bra on, but instead went back into the bathroom 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 smiled as I felt the forms bouncing gently on my chest as I moved�without a bra to constrain their movement, they seemed to take on a life of their own.

I used my new foundation, just the barest minimum I could get away with, then used 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 pantybriefs. 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 then pulled on the pantybrief without the pads, and had a nicely rounded shape. The pantyhose always felt good when I pulled them on, and today 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 snuggled 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 family room. Mom smiled when she saw me, and indicated for me to sit down so that she and I could talk a bit.

"It would kill your sister to hear me say this, but I think that 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 my matching navy jacket, touch up my lipstick, and grab a purse. As soon as I was ready, Mom, who was also wearing a nice suit, drove us over to Dad's office. I was taken to the personnel office, and filled out the form correctly--except for my name, of course. I was momentarily stumped when I realized that I had not selected a middle name, so I wrote in Elizabeth, and turned in the form. Since the lady knew my father, 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," he said, smiling

I gave as good as I got.

"Hi, Daddy."

He introduced me to the woman, and I learned that she was to be the person I would be working for. After we exchanged pleasantries, Dad then Mom and me 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 whom I knew from before as Ronald, but none of them ever gave any sign that they knew who I was. Being slender like Mom and standing a mere 5'7" in my bare feet, I fit right in, and as long as I didn't do something stupid, I figured I should be fine. The next few weeks flew by like a dream. I had become used to doing my hair and makeup, and found that I was able to get dressed quickly in the mornings. I was just generally getting used to being a girl. My mannerisms improved, I had my hair styled and my nails done, and I no longer carried fear in my side pocket.

I had been working there about a month and was sitting at my desk when the news came. Dad had been killed in an accident on the freeway. Both Mom and I were devastated, but everyone was really supportive. I knew that 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. I struggled with it for a while, but I did as she asked, and returned to work. I was just getting settled in when my new boss stopped by to offer his condolences. He also told me that they had decided to promote 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, but truth be told, I didn't want to. However, 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 suspected as much, and we agreed to change my name legally. We took care of that the very next week, and I became Rita Elizabeth. Now, it was just a matter of getting the rest of the package together.

I had to remove the breast forms 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 the prolonged usage. I called the company that supplied the glue, and they sent me a different version, along with a lotion to use on my skin before I reattached the forms again. According to the instructions, the new glue would allow me to wear the breast forms 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 was so rushed with all of the new students that she 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 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 either of us? 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 breast forms, 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! After I took it I 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 bikinis 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. It read:

"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 and asked me if I got his note.

"Yes, but you're married!" I exclaimed.

"Not really. We're separated."

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

"I've always thought 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. Ken 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?" she asked.

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

She looked at me thoughtfully for a moment and asked, "Kenny hit on you, didn't he?"

I was still in shock, but her bluntness still managed to take me by surprise. "He said you two were separated, and I let him take me to dinner, and that's all!" I explained quickly.

"I know," she answered. "I was watching him."

"I take it you're not separated?"

She shook her head. "He uses that line whenever he thinks he can get away with it. When Kelly told him where you were going on vacation, I overheard the 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."

She laughed at that. "True! Still, I wish there was a way to get his attention and make him stop running 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," I explained. "However, he would end up losing his job in the process."

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

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!" Then, reading the obvious concern on my face, she amended, "And don�t worry, Rita, your secret is safe with me."

It was easy to set it up, and Ken willingly followed me to my room. I had worn my red bikini, and 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! Then, remembering why I was here, I slowly undressed him and 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?" I asked.

"Of course," she said enthusiastically. "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, explaining that she had another copy of the tape.

Propping myself up on my elbow, I draped the covers over my body and watched in amusement at the little scene playing out before me. Kenny was almost shaking in impotent anger, but I couldn�t resist one last parting shot. "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. After 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, but at least it had 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. Even better, he would no longer be around to bother the women in the office, and Carolyn now had a hammer over him to keep him in line. I even managed to wrangle a little promotion for myself out of the deal. I guess sometimes it does pay to sleep with the boss, I thought smilingto myself.

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, and 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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