Sissyjackie Develops Further Part 4
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Sissyjackie Continues His Journey - Part 3 free porn video
I move further down the hole to sissydom with chapter 4 added here. To
catch up you should read the first two (2) stories of Sissyjackie
4. Masturbation/Anal Play/Humiliation
Even since my first accidental orgasm, I tried many times to recreate
that wonderful feeling. I finally did when I was laying on my bed one
day looking at one of those wonderful catalogues I talked about earlier.
I had pushed my penis down between my legs to be able to lie smoothly as
I looked at the lovely models in the beautiful and sexy dresses,
stockings, and heels. Many had on lovely red lipstick and nail polish. I
dreamed of dressing like them and I especially enjoyed those that wore
peep or open toed pumps with painted toenails.
The more I saw this the more excited I got. I then pushed my pelvis down
which squeezed my penis to the mattress, getting that warm feeling
again. I started pushing harder and harder and was soon fanatically
humping my bed until I moaned and trembled with a shattering orgasm. My
moans must have been a little loud because my mom knocked on my door,
opened I, and asked, "Are you okay?"
Sheepishly I looked back at her from the bed and nervously said, "Yes,
it was just a tickle in my throat." She said okay, but I sensed a slight
grin as she left.
Later, at the dinner table, she told me she knew what I was doing. I
blushed red, but she said, "It is normal for boys reaching puberty to do
it. What I was thinking about that got you so excited?"
"I was looking at the sexy women and the clothes in the catalogue, just
like we use to do together on girly weekends." I explained
She smiled and giggled, "Well, not exactly. I do not remember you
masturbating while we looked at them. I blushed and hung my head in
shame. "Oh darling, I am only teasing. I told you it was normal for boys
to do it." She hugged me and asked, "Was it the women or the clothes
that excited you? Again I blushed and admitted, "It was the clothes, the
heel, the lipstick and nail polish." She just smiled and said that next
time, perhaps I should dress up before masturbating. She said she would
help me dress up and then leave me to do "my thing". I really blushed
then but the idea of doing it en femme intrigued me.
During the summer of my junior high school years, my friends and I would
walk to the town pool. The guys did not know about my dressing other
than for Halloween. They would brag about wanting to have sex with all
the beautiful girls. They would sometimes get copies of Playboy and
Penthouse from older boys or sneak them from their Dads. We would look
at them in a wooded lot near the pool. I smiled and went along with
them, but never admitted I was afraid of girls. I talked to girls but
they seemed to only think of me as a friend, never a love interest. Deep
down, I knew my dressing would make me seem inadequate as a love
interest and doubted they would want me for more than a friend.
Besides, when I looked at the magazines, I would admire their heels,
makeup, and nail polish. When I did look at their chests, I thought what
it would be like to have a nice pair boobs. When I looked at their
waist, I imagined how wonderful it would feel to have a hard penis
inserted into their vagina.
It was about this time that I was looking for a wrench in my dad's
workshop. I did not see one on his bench so I pulled out the tool chest
he had under it. I lifted up the inner tray and to my surprise I found
some porn magazines in the bottom hidden under some clothes. To my
astonishment they were not the typical naked women type. They were
female domination magazines. I guess I should not have been surprised,
because as I said earlier, my mom ruled the house, and from the looks of
the magazines he had, she ruled him personally.
All the women were dressed in sexy tight cloths or cat suits. They had
lovely full pained lips and long enameled nails. The heels and boots all
had high stiletto heels. Most had whips or crops in their hands. The men
were submissive, tied up bent over benches or on their knees. Many of
them had dildoes being pushed up their asses or in their mouths. Some
were even being fucked by a women with devices that I later learned were
called strap-ons. Another magazines had men dressed in women's clothing,
especially as maids serving their wives, Gf's, etc.
There were crossdressing magazines, such as "Female Mimic", among
others. They showed men dressed as showgirls, French maids, school
girls, harem girls, etc. These magazines really intrigued me because up
until that point, I did not know men liked to dress as women. I thought
I was the only one.
There were also two (2) gay magazines. They showed men kissing and
hugging each other. They also showed small skinny men, with no body
hair, either on their knees with their mouth around a larger man's
penis; or on all fours with a larger muscle-bound man shoving his penis
up the smaller guy's ass.
There were even a few with a penis in their mouth and ass, which I later
learned was called spit-roasting.
I was in awe of what I saw, but when my mom called down to ask what I
was doing, I shouted that I could not find the wrench as I scrambled to
put the magazines back. As I left the basement, I kept thinking about
what I saw and what it meant to me. Also, what did my father liked about
them?
I knew my dad would be away for a month so the next day, while my mom
was at the store, I snuck the magazines into my bedroom and hid them in
the back of my closet. When I had the opportunity, I would pick one and
look at it as I humped my bed to orgasm. I would even put a pillow or
rolled towel under me to push my penis even harder. Seeing all those
emasculated men being tortured and humiliated by those lovely women
really turned me on. I especially wanted to feel something up my ass,
but has nothing. That is until I found in the bathroom, an enema bag
with a long thin nozzle at the end of the tube. I took the nozzle off,
dipped it into a jar of Vaseline and brought it back to my room. I laid
on the bed with those sexy magazines opened to the strap-on pages, and
slowly pushed it slowly up my ass. It felt so good but a funny thing
happened. My penis which was very hard, softened, but the feeling at the
base of my penis was incredible. I soon had it all the way in and was
slowly moving it around as I found that very pleasurable. I imagined a
lovely severe women pushing it up and down my ass and I was getting very
hot. Soon I felt down there and looked to see cum dripping slowly from
my flaccid penis. I had a non-orgasm release. I felt humiliated and
emasculated, but it was very erotic. I kept wondering if this was like
the wonderful feeling women have when a penis is inserted in their
vagina.
As I got used to the pleasurable feeling of the thin nozzle in my
rectum, I wondered what a larger item would feel like. As luck would
have it about a week later, I found a larger nozzle with a round
rubberlike bag at one end of it. I did not know what it was for, but it
was much fatter than the thin enema nozzle, and I wanted feel what it
was like. The next time I was alone, I took it to my room and got it
ready with a big dollop of Vaseline. This time I decided to look one of
the gay magazines for a change. As I was looking at the picture of the
two men fucking, I concentrated on the look of fear, wide eyes, and open
mouth of the smaller man. I got very excited imagining me being the one
on the bottom, and took the large nozzle and started to work it up my
ass. I struggled to inert it. Slowly it went in further and further and
my own eyes, and mouth emulated that guy in the picture. It hurt but
felt good also and I humped my bed as I pushed it farther and farther
in. Soon it was all the way in and I was bucking wildly hoping to get an
orgasmic release. Finally, after humping and humping for what seemed
like an eternity, I came violently and was shuttering as I spewed into
my undies.
I was still shaking as I laid there for a few minutes. My rectum was
still filled. I reached back and slowly extracted it, enjoying the fell
as it left my ass. As I took the nozzle to the bathroom to clean it up,
I was thinking about what just happened. I just had what seemed to me
the most powerful orgasm in my short experience, and it was as I was
looking at men with men. There were no women involved in any of the
pictures. Am I gay? Is that okay? Mom said there were boys like that.
Was I one of them? I was conflicted, because I like girls. But do I
really like them, or am I jealous of them because of their makeup,
clothes, heels, etc.? Do I just dress en femme because I just enjoy it,
or because I want to flirt with boys? All these thoughts swirled around
my head as I cleaned up and prepared supper for mom and I.
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