Maiden Voyage
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Maiden Voyage free porn video
Maiden Voyage Jennifer ronald
Janet L. Stickney
[email protected]
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 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, 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, telling 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....
"Jennifer," I squeaked out.
My fifteen-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, Jennifer. 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 Jennifer. 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 Jennifer full time and work in your fathers office. If, at
the end of the summer you decide to keep living as Jennifer, we will talk
about it, but from the moment school is out, you will become Jennifer.
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 Jennifer 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 finally gathered the courage and 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 very nice young lady rather than always 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 my padded 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 A, and
let me slip the breast forms into my bra. She also suggested a really
good padded pantybrief, which was made of gel rather than foam, like the
one I had on. Mom bought two of them, as well. I slipped on one of the
new padded pantybriefs, then discarded my birdseed falsies on the way out
of the shop. Adjourning to the 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, hugging my new shape perfectly. I was round
everywhere I should be round, including just above my happy place! Just
like all girls! 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 Jennifer, 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 Jennifer, 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, walk, talk, and act like a girl, then 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
Jennifer for three months, and work in Dad's office, and that's all there
was to it. No amount of discussion would change that. 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 breast 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
gel 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 a woman, and I learned that she was to be the person
I would be working for. After we exchanged pleasantries, Dad, Mom and I
went 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, when I
was 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. 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
Jennifer 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 with anyone, ever,
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 will admit that 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
I began life on my own. I planned my vacation in August. I was planning
on going to the theme parks in Florida. I bought new bikinis and some
lightweight traveling clothes, then, when the time came, I flew to
Florida.
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, Jennifer, but until now I
haven't said anything because I was married. Kelly told me where you were
going, 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 I...
"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 caf?, 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, Jennifer. 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, Jennifer,
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 automatically
sent a copy of the tape to her cloud account.
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, 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. Guys 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
smiling to 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.
The above work is copyrighted material. Anyone wishing to copy, archive,
or re-post this story must contact the author for permission.
Mikayla
- 18.11.2022
- 22
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