Sissyjackie Continues His Journey Part 3
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Sissyjackie Develops Further Part 4 free porn video
Chapters 5 & 6 Here continue Sissyjackie's exploration of femininity,
bisexuality and submissiveness with the help of his understanding mother.
5. Caught with the magazines
After these series of masturbation sessions with those erotic and deviant
magazines, I started to worry about where it was heading. I was now almost
13 and in the summer before the 8th grade. I was playing baseball with my
friends and of course continuing to look at Playboy and Penthouse with
them. Again, as boys that age will do, they bragged about wanting to have
sex with those lovely women in the pictures. They also started to use gay,
faggot, cocksucker, etc. as derogatory terms. I did not use them but
laughed along with them for fear they would turn on me. Even so, one or
two of the guys would ask if I was gay since I dressed for Halloween. But
several defended me saying it was only during Halloween. Besides, I was a
good ballplayer and was usually picked second or third for the team. In
addition, my biggest defended was Robert, and he was the best player at
all sports.
When I was home, I thought about the excitement I felt looking at these
magazines. I felt ashamed and tried to stop looking at them. I kept
thinking about what my Dad was doing with them but was afraid to ask my
mom. As it turned out, I would find out, sooner than I thought.
It was a rainy Friday when my Dad was on another business trip. My mom
said, "Jackie, sweetheart, I think it is a good time for a girly weekend.
This time just put on your pink lace panties and meet me in my bedroom."
It had been a while since I dressed, and I was nervous about starting
again. However, it was about a week since my last orgasm, so my resistance
to her pleading for me to dress up for her weakened my resistance. Soon I
was sitting at her vanity along with her, dressed only in pink panties.
"Put your makeup on like I taught you sweetie," she said with a soft but
firm voice. She coached me, while I did my foundation, eye liner, eye
shadow, mascara, etc. When I was ready for lipstick she firmly stated, "I
want to see a bright violet lipstick on you." She handed me a new lipstick
and said it was a present for a very naughty sissy boy." I wondered why
she said naughty but stayed silent as I applied the luscious color to my
lips. When I finished and was looking at myself, I could see a sly grin as
she watched me. She then told me to brush out my long hair and comb out
the bangs. (I started to wear my hair longish and with small bangs.) She
then but red barrettes on either side to keep it out of my eyes. The final
touch were long dangly earrings which she clipped to my lobes.
"Get the Revlon Red Nail polish and paint my nails, starting with my
toes," She asked with a definite command in her voice. I went to her
dresser, to retrieve the bottle and was soon on my knees painting each toe
as carefully as possible. Being in such a subservient position reminded me
of the men in my Dad's Femdom magazines. When I was done, she wiggled
them and asked me to blow them dry. After 5 minutes, she them asked me to
sit on the chair and do her fingers. Again, when I was done she had me
blow them dry.
"Wow, what a great job. You learn fast. I should let you give Aunt Joan
and Mary a manicure and Pedicure. They would love to have you serve them."
I blushed at the complement and found the idea of serving them very
exciting but said nothing.
"I have another present for my naughty sissy boy. I am going to use it to
paint your nails," she said as she produced a bottle of deep purple nail
polish. She proceeded to repeat the process that I performed on her,
except I had to blow my own fingernails dry. When my finger and toe nails
were dry, she produced a package of tan stockings and black PL sandals
with 3" stiletto heels. "Put these on," she commanded. I did as she said
and was soon looking at myself in her full-length mirror. I looked
straight ahead and then turned my head right and left enjoying my
reflection. I was careful in my heels as mom said, "You are doing so well
in those heels. They make your legs look so sexy. Soon you will be able to
handle 4" or even 5" ones. So we will have to go shoe shopping again soon.
A girl can never have too many sexy heels."
"Do you like the color of your lips and nails? I picked it out for a
special reason. I will tell you but first I want to ask you a question,
and I want an honest answer. Did you take anything out of your father's
tool box?"
"No, honest," I almost shouted, but she just asked again. Again, I denied
it, not wanting her to know what had excited me so.
She came up to me with fire in her eyes, grabbed my wrist and bent me over
her lap. "I do not like liars."
She exposed my bottom and started to spank me. I was shocked as I had not
been spanked since I was about 4. I started kicking my legs more from
embarrassment as she told me what a big sissy baby I was. Finally, she
stopped pulled my panties back over my bottom and had me stand in front of
her. She then went to her dresser and pulled out the exact magazines I had
taken from the toolbox and laid them out on the bed.
"Now, no more lying. I have proof you took the magazines, now tell me what
you did with them."
"I looked at them while masturbating," I sobbed.
"Thank you for telling me the truth. Normally I would not intrude on what
you do with your personal time, but since you took something that was not
yours to take and more importantly you lied to me, you do not have privacy
privileges. Tell me exactly which ones you looked at?" she said in a very
sarcastic tone.
"All of them" I meekly said. "Even the gay ones?" she asked in a surprised
voice. "Yes," I whispered.
Instead of being mad, she giggled and said, "Then I picked the right color
for you. Purple is usually the color associated with gay boys. The way
you're dressed now with your little boy boobs showing you're your long
legs and high heels, you would have those gay boys drooling over you. And
by the looks of that bulge in your panties, you would like to get those
gay boys excited."
I sobbed loudly, "I like girls. I don't want to be gay. Please stop me."
She put her arms around me and comforted me. "It is okay, honey. Just a
few instances of infatuation with boys does not make you gay. Although as
I said before there is nothing wrong with boys loving boys." She hugged me
even tighter as I cried.
Soon I calmed down and she asked me about the crossdressers and the femdom
magazines. I admitted they all excited me. I then asked why Dad had them.
She paused and seemed like she was going to ignore the question, but she
sighed and said, "I told him not to keep them here. I knew someday you
would find them. So it is his fault that I am going to reveal something to
you. Your father is very interested in that lifestyle. Some day when you
are older, I will tell you more about it, but let's finish dressing you
like a proper young lady instead of a sissy boy."
And we spent the rest of the evening having my try on the latest dresses
Mary and Aunt Joan sent over and had a lovely mother daughter weekend. I
went to bed in a lovely pink sleeping gown will puffy sleeves. It felt
lovely as my mom tucked me in and said, "Good night, my little princess."
The next day, my mom woke and said, "Time to get up and start your chores.
Remember, that was the deal we made. When you dress, you must do chores,
and you must remain in femme the whole weekend, no matter who shows up." I
got up but was very panicky. I did not mind doing the chores, in fact I
felt very submissive working under the command of my mother, like the men
in the Femdom magazines. However, I worried that one of my friends might
come over and I would be exposed as the faggot some thought I was.
After I took of my nightgown, my mom gave me a short silk robe to wear and
some black pl ballet flats from my cousin. She was already dressed in a
tight low-cut top, capri pants and peep toed pumps. I must have been
staring at her lovely painted toe nails, because she said, "Honey, if you
like my peep toed pumps so much, we will have to get you a pair. Would you
like that?"
"Oh yes please, mom. I just love seeing my painted toes." She promised on
our next shopping trip we could do that, but also teased that the shoe
salesman might get excited seeing me prance about in them. I blushed and
protested but she just giggled and told me to eat my breakfast.
After my bath, she had me dress in a jumper and with the same flats gave
me a list of chores. It took me all day to complete them, and the other
chores she added as they came to mind. I noticed she did little but read,
exercise and otherwise had me wait on her. At the end of the day, she
asked if I liked serving her. When I said I did, she reminded me that this
was the lifestyle that those men in my Dad's magazines enjoyed. She asked
if I wanted to think about that in my room and have girly time alone. She
asked if I wanted to take along any of those magazines, and I said yes. I
took the femdom magazines, and went to my room to enjoy an evening of
masturbatory bliss.
It was then that I decided that I would very often take up my mom's offer
to help me dress up for my masturbating sessions.
6. Psychoanalysis of a budding sissy faggot by his mother
As promised, my mom helped me dress for my "sessions" when I wanted to be
en femme for them. In return for this help, she wanted to know all about
them. While helping me dress, she would tell me how pretty I was; how
wonderful it would be if society would allow me to dress full time; asked
me if there were any girls I liked in school, or perhaps a boy or too.
That last question, I always denied, but she just shrugged and said if I
changed my mind, she would support me.
My mom was a psych major in college and she wanted to analyze my awakening
sexuality. She dove into this work with determination. The notebook that
my mom used to keep on my masturbating was turning into a lengthy diary.
She took copious notes to statistically determine my preferences. She
recorded what I thought about as I masturbated, both en femme and in drab.
She left me alone in my room, but quizzed me about after each session. It
was like going to a Shrink.
She always asked if it was a boy or girl it was thinking of, if I was
dominant or submissive, if it was a boy, was he in drab or femme, etc.
When I was en femme, she asked if I pranced about in my heels, held my
wrists limp, refreshed my lipstick, etc. She also asked if I used any toys
while masturbating and how I used them. It was very embarrassing, but also
exciting to talk about it.
One recurring conversation was about the harem dream I talked about
earlier. She wanted to know if I thought about that as I masturbated. I
admitted I did think about it a lot.
"What do you imagine?" she asked.
"I and 4 other harem boys are dancing for the sultan," I said.
"Oooh, that sounds sexy"
"I felt very embarrassed, but he insisted I dance, and the women who
dressed us giggled and told me to obey. I jiggled my shoulders and butt as
i was taught and so did the other boys, as we teetered on our stilettos. I
remember seeing my red nails as I tapped the little cymbals on my fingers.
Then the sultan commanded me to sit next to him on the floor. He then
told 2 of the other boys to start kissing each other. The women insisted
they do it when they hesitated, and soon they were kissing each other
passionately.
I was mesmerized as I watched their painted lips touch. All this time, as
the sultan watched, he stroked my hair. Soon he snapped his fingers and a
woman came over to him and opened his robe at the waist. She gently pulled
out his large penis and started to stroke it. She told me to look at it
and I saw him smile as I did. I was hypnotized by its length and large
mushroom head. He then took the hand that was on my head and gently but
firmly pushed it toward his penis. She told me to open wide and as if in
a trance, I did. She called me a sissy faggot as I closed my mouth over
it. She touched my penis which then squirted and wet my panties, both in
the daydream and in real life."
"Wow," my mom said. "That really excited you didn't it."
"Yes," I admitted as I blushed red.
"You enjoyed watching the boys kiss, didn't you? Did you wish you were
kissing one of those cute girly boys? Did you have favorite boy?
Again I blushed as I admitted I did.
Sweetie, it is okay if you like boys. You are not the only one that does.
How about sucking the sultan? You really enjoyed that because you wet your
panties.
But the woman played with me. She made me cum.
My mom laughed, "Oh sure, it had nothing to do with the cock in your
mouth. "
I started to tear up. "Being gay is nothing to be ashamed of sweetie."
"But I like Girls, I protested.
Okay sweetie, you like girls. By the way, did the sultan come in your
mouth? I could only sheepishly nod, and she smiled and said, "And I bet
you swallowed his cum."
As I sat there humiliated and embarrassed, my mom made notes in her book.
Although I asked many times, she never let me see her notes. She locked
them away in a desk in her bedroom, where she sat as I sat on the edge of
her bed relating each episode to her.
One day after about of year of this, over the summer between grade school
and high school, when I was alone, I snuck into her room and found the
desk unlocked. I could not help myself and opened to see what she had
recorded.
I found that it was an accounting book with many columns, much like todays
spreadsheets. She had recorded my masturbation sessions with excruciating
details about my habits filled in each column. The information included:
date, length of session, tie between ejaculation in days, whether I was
naked, in drab or dressed. If dressed, what I was wearing, color of my
lipstick and nail polish. She recorded if I put anything up my ass, such
as my finger, enema plug, etc. She also recorded whether I was thinking
about boys or girls as I masturbated.
The most informative and erotic items where in her remarks column. There
she would use a point system on how the session rated in various
categories, such as dominant/submissive; straight/bi/gay,
crossdresser/transvestite/drag queen, etc. She would also opine about
which way I was tending to go. Needless to say I was definitely trending
in her mind toward submissive, gay/bi, CD.
I found this very disturbing as I wanted to be a normal straight boy.
However, I could not stop from touching myself as I read all the entries,
especially the last one: "The way things are going I feel that John is
truly a sissy, but has a hard time admitting it. He seems to fight it
because he is afraid of being called faggot, fairy and other bad name at
school. However, I feel he will never be happy unless he comes to term
with his effeminate nature. I will try my hardest to get him to realize
this and be comfortable with it." I put the book away and wondered what
she would do to have me "come to terms." It did not take too long to find
out.
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