The Beginning of Sissyjackie
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The Continuation Of Sissyjackie free porn video
This is a continuation of my story into becoming a sissy boy. I am
adding chapters 2 & 3 in this section. Please read The Beginning of
SissyJackie for the start of my journey.
2. The Beginning-Addendum
In addition to "Some Like it Hot," there were also other crossdressing
themes I saw on TV; namely Bugs Bunny cartoon. They had a profound
effect on me when I was just starting to dress and reinforced my desire
for women's clothes. How I loved seeing him as a mermaid and as
Brunhilda wearing those lovely cute bras in each. How I wanted to have
boobs like Bugs. I also liked when he dressed s Carmen Miranda. I loved
the tight dress, his full red lips and his high heel sandals. In fact
when I saw that I begged my mom to let me dress as her for Halloween.
She agreed and was able to get a fruit basket headdress. She asked a
neighbor who had a teenage daughter if she could borrow a form fitting
gown and some HH sandals and she agreed. If fact, both she and her
daughter came over to help dress me. It was both embarrassing and
thrilling. I remember these CD cartoons would make me feel anxious and
warm all over. As I did not know much about sex, I was not sure why it
had that effect on me.
The biggest effect a CD cartoon had on me was "The Big Snooze." I
remember vividly the first day I saw it. I was about 2 months after I
received the box of Mary's clothes with the high heels. It was a sunny
morning and I was going to play baseball that afternoon with my friends.
I was still in my PJ's when it came on. My Mom was straightening out the
living room and would glance up whenever I laughed at something. All of
a sudden I said oh, as I saw Elmer was naked except for a row of green
flowers. I said, "Mom, Elmer is wearing panties!" My mom stopped what
she was doing and sat down next to me to watch the cartoon. Next thing,
Bugs wraps him in a green strapless gown with matching HH sandals, puts
a long red wig on him, painted his lips a deep red. While doing that,
Elmer's lashes become very long and he started to bat them. I was
mesmerized and even gasped as I watched. A hot feeling took over my
whole body. In fact, my mom asked if I was okay. All I could do was nod
and stare at the screen. The next thing that happened was that Bugs
lifted a curtain and 3 or 4 wolves in suits and hats howled and started
chasing Elmer. He had to lift up his dress to run away. God was that
powerful.
When it was over, I just stared for a while. "Honey are you okay?" she
asked. "You are all flushed in the face." I finally just turned to her
an asked, "Can you please dress me like Elmer? I want to do it right
now!" "But, you said you wanted to play ball this afternoon. It is such
nice day," my mom replied. She later told me she was startled when I
begged, pleaded and even whimpered that I want so badly to have her
dress me as Bugs did Elmer. She agreed as long as I stopped being such a
Drama Queen. (Funny, it was the first time I was called a Queen, but
obviously not the last!)
We went into her bedroom and she sat me at her makeup table. I asked for
the beautiful red nail polish for both my fingers and toes. "Elmer did
not have nail polish on," my mom said, but I insisted. I wanted my nails
to sparkle. She laughed and started painting them. She said, "You know,
girls your age start to paint their own nails. I want you to study how I
do it so you can do your own. Maybe you can even do mine sometime." I
agreed and just looked in wonder at each digit as I blew them dry. While
my nails dried, she painted my lips a deep red. "Don't forget my lashes
I said, and she laughed as she took mascara and brushed them.
We then went into my room and opened the bottom drawer, where she kept
my girl clothes. I reached in and picked out a flowery pair of panties.
I told her I wanted to match Elmer's panties. When I looked for a bra, I
realized that all my cousin's bras that she gave me had straps. "Mommy,
Elmer had on a strapless gown, I cannot wear these bras. Also, none of
my dresses are strapless." "Wow, are we the clothes horse!" my mom
giggled as she thought of what she could use. "Let's go back to my room,
I have an idea." When we got there she pulled out a strapless bra of
hers. I was obviously too large, but she used safety pins to make it
small enough to stay around my chest. I pushed the cups and said that I
did not have any boobs. My mom got a couple of stockings and put them in
the cups. "There," she laughed, "Instant boobs." I do remember walking
up to her mirror and putting my hands under my boobs and admiring them.
"Stop playing with your boobs!" she demanded. We have to finish dressing
you. "I do not have a strapless gown that wil fit you, but I think I
have an idea. Wait here, and sit like a proper little girl." "Yes,
Mommy," I said.
In a little while she came back with a pale green bed sheet. "This is
all I have but I think I can make it work." She pinned the top of the
sheet to my bra and had me rotate slowly as she wrapped it around me. I
laughed and said, "You are making me spin just like Bugs made Elmer
spin." Soon the sheet reached the floor and she pinned it like a hem. I
remember looking down and seeing my sparkly red toe nails peeking out at
the bottom of my "dress." I told my mom I needed to put my heels on and
she said to go get them. They were hidden in the back of my closet. I
came prancing back swishing like I had seen women do in the movies.
"Okay glamour girl, we need a few last touches. She produced some dangly
earrings and a necklace. Finally, she brought out a long red wig of
hers. It was too big for my head, but she was able to pin it to my head.
The hair came down below my waist but I loved it. "Wow, I look just like
Rita Hayworth," I exclaimed and my mom agreed. My mom told me to slowly
walk around and she warned me to take small steps as my "gown" was very
tight around my legs. "What we girls have to do for fashion," she said
offhand, but I remember thinking that she called me a girl for the first
time. I left a profound mark on me after that.
She told me to continue practicing my walk. She even said to put one
foot in front of the other just like models due. She also had me out one
hand on my hip and put out the other with my wrist down. I felt very
sophisticated as she watched and directed my every move. She also had me
sit telling me to keep my legs together and even to cross my legs. I
asked why but she said I would learn when I got older. This made me even
more curious but I did not press the issue.
After about an hour of that we had lunch. I sat at the table with my
hands folded. I was admiring my nails heels and dress so much, my mom
went into a drawer and pulled out a small table mirror. "Here, you are
such a girly girl. Now you can check out your hair and makeup while I
make lunch. As she was making it the doorbell rang. "Those are the guys
wanting to play baseball," I said in a shaky voice. "Why don't you
answer the door and tell them were are having our girl time," my mom
said matter of factly. "I can't mommy, they do not know about girl time.
They only know I dress as a girl for Halloween," I cried out. "Well,
maybe it is time they see you like this," and she grabbed my hand and
started dragging me to the front door. I really started to panic and
begged her not to let them see me like this. Finally, she relented and
as I hid in the corner, she opened the door and told them I was sick and
could not come out to play.
We she came back, she told me to go back to the kitchen so we could
finish lunch. She then told me that in exchange for answering the door
for her, I would have to helping with chores around the house. She put
an apron on me and had me do the dishes. They we both sat down and look
at pictures of movie stars in a big Hollywood book she had. From that
point on my dressing took on a different meaning between me and my mom.
3. My First Orgasm
As I said earlier, the Elmer dress episode changed things about my
dressing. After supper, my mom asked me about the "strange feeling" I
had when I saw Elmer in the dress. "I don't know," I said, "I just felt
a warm tingling all over, but it was especially intense below my
stomach." "You mean in the area of your penis," she said as she smiled.
Then she added, "My little boy is starting to grow up...or should I say
my little girl?" I blushed and look down at my nails and my dress and
again felt the same strange feeling.
"Well," she said, "do you still want to dress up or do you want to
stop?" "I still enjoy dressing up. Please don't make me stop. I
especially liked wearing your bra and wearing Mary's heels." "In that
case, we are going to have to go shopping. You and Mary are different
sizes. Also, girls your age do not have big boobs yet so you need a
training bra. Since tomorrow is Saturday, we are going shopping for some
clothes and shoes," she stated.
I stated to protest, but she refused to listen. "You make a very pretty
girl, and no one will know since we are not going to any stores around
here. We are going to ones near Aunt Joan and Mary's house. "Why there?"
I asked. "They are coming too. Aunt Joan wants to see how pretty her
niece is." I must have looked frightened because my mom said. "Sweetie,
they have known all along. They both guessed when I asked for Mary old
clothes to give to a neighborhood girl who just happened to be the same
age as you, they guessed right away. I tried to deny it but I guess I am
not a very good liar. I also must confess, I secretly took pictures of
you to show them. They thought you were very pretty," she giggled at the
last sentence. I was horrified and stared to tear up. "Don't be upset,
sweetie, they both love you very much and so want to meet you. Mary
especially says she want to meet her new cousin "Jackie," so she can
help you try on more clothes she has to give you. BTW, we settled on
Jackie because we all adore Jackie Kennedy and how she dresses."
The next day she dressed me in a little girl slip and pink dress, white
ankle socks and my pink Maryjane shoes. She combed my hair in a girl's
style a put a couple of red barrettes in it. I still had on my red nail
polish, but she only put clear gloss on my lips. "Little girls your age
do not wear bright red lipstick," she told me. For the final touch, she
added clip on earring, a small necklace and a pink bracelet with the
name Jackie on it. She said it was a gift from Aunt Joan and Mary for my
"Coming Out Day." (I did not realized how significant that phrase was to
become later in my life)"You look beautiful. Perhaps your should have
been born a girl," she laughed. "No, I like being a boy," I protested,
but I must admit I loved what I saw in the hall mirror as we walked out
the door.
Soon we stopped to pick up Aunt Joan and Mary, who both kissed and
hugged me and told me how pretty I was and happy they were that I was
coming out with them. Aunt Joan said, "Girl just love to shop and I am
sure you will like it too." Mary took my hand and sat in the back seat
with me. She was now 15, and she kept talking very low about all the
boys she liked, the latest clothing trends, new makeup items, etc. She
did not talk to me about sexy things, but she made it clear she was gaga
over one boy in particular. She loved watching him when he was swimming
and she could see his bare chest and muscular arms. "He also has very
beautiful eyes." She looked into my eyes, and said, "Yours are beautiful
too...for a girl." She then hugged me again and said she was so glad
that I agreed to go shopping.
For me the best part of shopping was the shoe store. A HS senior about
17 was helping us out and he could not take his eyes off of Mary. She
wanted to try on several pairs of high heels and I felt jealous as my
mom and Aunt Joan told her how lovely her legs looked in each pair. For
me it was flats only. She did allow me to try on patent leather ones as
she knows how much I like them. There were even a few with peep toes. My
Aunt Joan gushed about how pretty my painted toes looked in them.
However, I did not get those since I prefer my toes showing in heels. I
settled on three pairs, one of PL black, PL red and PL pink. My mom
said, "Jackie, you're too young for heels." When the salesman went back
for more heels for Mary, my Aunt Joan said, "Soon you will be old enough
for heels then you can show off your lovely legs and toes and get all
the boys excited." I gritted my teeth and said, "I am a boy." All three
of them laughed and Aunt Joan, added," You could have fooled me." They
then each hugged me as my tears started to well up and told me they
loved me, They said I was so brave to be out with them. I did hear my
Aunt Joan whisper to my mom that the salesperson may prefer pretty boys
like me to girls, since he knew so much about women's shoes. "I bet he
prances about in them at home and would love to be alone with our sweet
Jackie," she said in a low voice. They both looked at me and giggled not
knowing I heard them. I blushed picturing us both in heels and dresses.
I got that funny feeling again.
I continued to dress but less often, only once or twice a month. With
school, ball playing afterwards, and doing guy things, I did not have as
much "girl time" with mom. So all my friends thought I only dressed for
Halloween and I did nothing to discourage their thinking. My mom and I
did reserve girl time for when the Sears and the JC Penney Catalogues
came out. I would dress up and after doing the chores that she demanded
I do, we sat down to look at the latest fashions. I just loved looking
at the dresses, bras, panties, girdles, but especially the high heel
shoes. My mom would ask me to pick my favorites and they were invariably
the highest heeled shoes. I also was partial to d?colletage bras and low
cut dresses, with long slits. "You will have to grow your boobs bigger
to wear them," she laughed as I stared at the dresses and bras. She then
hugged me and said if I was born a girl, my boobs would be the
prettiest. Again that warm feeling came over me and I think my mom
noticed but did not say anything.
I did notice that warm feeling coming over me more and more whenever we
saw the catalogues, whenever I was dressed, painting my nails, prancing
about in my shiny PL flats and especially my cousin's old heels. I was
not sure about the feeling but I did love it. As my mom said earlier, I
was growing up, but did I want to grow up as a normal boy or as a pretty
girl. That question hung out in the back of my mind.
I also found that I wanted to dress in a more sexy way. I kept thinking
about how many sexy women in the movies like to flirt and excite men.
More and more as I dressed, I would pose in a provocative way like I saw
them do on the screen, bat my eyes, hold my hands in such a way to show
my painted nails, look over my shoulder and lower my eyelids, purse my
lips, sway my hips, etc. All the time I would imagine boys getting
excited at the sight of sexy Jackie. I even imagined running away from
them in heels and a tight skirt like Elmer did when the wolves chased
him. I would wonder what the boys would do if they caught me and kissed
me on my bright red lips. Would I fight it? Would I like it? It made me
nervous and excited at the same time. Since I did not know much about
sex yet, the daydreaming stopped there. However, it was about that time
that Halloween costumes turned more daring, like a Vegas showgirl, or a
Dancer in Top hat, Tails, black tights, heels, etc. All with stilettos,
long painted nails and ruby red lips.
I finally found out about that feeling on a momentous occasion. I still
remember it was early in the sixth grade and as if it was just
yesterday. It was late on a Friday afternoon in early November. I was
sitting at my desk taking a history test that was much harder than
normal. I do remember sitting with my legs crossed under my desk. As a
test wore on and the time getting short, I was getting nervous. I
started to squeeze my legs together and noticed that I was getting that
same warm feeling I got when I was dressed. The more nervous I got, the
harder squeezed my legs together. My penis was trapped between my legs
but it was it was so close to the end of the test that could not adjust
it. I just kept squeezing more and more as my nervousness increased and
the time to finish was getting shorter. As I was answering the final
questions, I squeezed and squeezed and stared to perspire, hoping to
finish but also enjoying the warm feeling between my legs. As I put down
the last answer, the teacher said, "Times up." At that moment, I felt a
tremendous shutter in my body and stood still as I felt something warm
and wet in my pants. I was so nervous that I wet my pants but when I
looked down there was no wet spot. It was also helpful that I was
wearing dark slacks. Nervously I went up to the front desk and handed in
my paper. I must have been flushed, because the teacher asked if I was
OK. I said I was fine just nervous about doing well on the test. I
quickly got my coat and raced home. I remember walking past my mom and
into the bathroom. I took my pants down and looked into my briefs. They
were wet but there was a white substance I had never seen before. I
touch the stuff and it felt slippery in my fingers. I then put them to
my nose to smell. It smelled different to urine. It was not anything I
smelled before. Just then my mom walked in and saw my fingers covered
with my cum and holding it to my nose.
"Oh my," she said "when did that happen." "When I was taking my test," I
cried. She held me and told me that it was all right. She explain I was
just had an orgasm and that I was becoming a man. She told me that it
was there was normal for a boy my age and asked if it felt good when it
happened. I admitted that it did. She told me we would talked to me
about it at dinner. She then kiss me on the cheek.
At dinner, she asked what I knew about sex. I told her the little I
knew. She then went into a very detailed explanation of what happens
when a man and woman have sex. "A man puts his penis in a woman's
vagina," she said. She then took out a medical book and showed me a
detailed drawing of a penis inserted in a vagina. To get the penis to go
inside, it must be hard, or it will not go in. Obviously, anxiety of
that tests did that for me. "Most times a man gets excited by how a
woman looks. That is why a woman dresses up emphasize her boobs, puts on
makeup and lipstick, paints her nails, and wears high heels. It all
serves to entice the man to get his penis hard," she explained to me. I
was fascinated by the explanation, but I asked her if it hurt the woman,
when a man stuck in penis into her vagina. She smiled and said "Oh no,
honey. If the woman likes the man, she gets much pleasure from it. In
fact, a man usually gets to have only an orgasm a time. A woman can have
more than one orgasm. It feels very good to have multiple orgasm. It is
also why I think woman have it better than men when it comes to sex.
Perhaps, subconsciously that is why you want to be a girl at times," she
laughed. I denied it, but I was amazed by her descriptions of sex and it
was the first time I realize I would love to feel what a woman feels
during sex. I also start to wonder if she was right and if my dressing
up was part of me wanting to be a girl.
She also told me in no uncertain terms that a woman makes the decision
on who has sex with her. She made me promise to always politely ask and
never to force myself on a woman. I swore I would not do that and it is
this promise, along with many other things, that laid the groundwork for
my meekness and submissiveness toward women.
Oprah
- 17.06.2021
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