Nasty Boy Lovely Girl Part 6
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Nasty Boy / Lovely Girl Part 2 free porn video
Nasty Boy/Lovely Girl
Part 2
By Wendy
Wendy's punishment for the next two weeks was very intense. I could
not begin to write a detailed synopsis of each and every event and
humiliation which Wendy had to endure. But I will try to give the
reader some of the high lights, or low lights from Wendy's
perspective, which might be of most interest to the discerning and
interested reader.
The first events which I will recount to those who love to read
about true life sissification, will be what happened to Wendy when he
returned home to Dad and sister Marie. If you are squeamish about
enemas and douches and Super Absorbent Tampax, please stop reading
now...
1. Wendy's first female cleansing enema, douche, and assisted tampon
insertion
I tried to digest what Mom had told me sitting on that bench outside
Miss Vicky's Salon.
I was in for a rough two weeks. Mom was pretty sure about that.
Today, so far, had been very humiliating. But Mom was right about me
being more comfortable now as I looked more like a real girl and less
like a pansified sissy after Miss Vicky's treatments.
The walk to the Pharmacy and the purchase of the tampons was not too
difficult. I found the proper aisle in the store and waited for a
couple of minutes while a mother and her daughter were looking at
various brands of female products at the far end of the aisle. After
they left, giving me an embarrassed smile as a woman to another
woman, I started my search for Marie's request.
Luckily the Tampax brand was easy to find and the Super Absorbent
type were right at my eye level. I grabbed a box and walked to the
checkout lane.
The young man at the checkout sort of looked me over as I slid the
Tampax to him. And he smiled. When he saw what I had to purchase he
got a little bashful and didn't meet my eye the rest of the
transaction. But I could feel his eyes on my hairdo as I went thru
the doors and back to Mother by the car.
"Good Job, Wendy! You may be the first 16 year old boy in this city
to buy a box of Tampax, while wearing lipstick and a swell new
hairdo. Now hop into the car and watch that you don't mess your hair.
Marie will want to see the finished product, even if she may have
plans for your hair yet tonight. I know she has a lot of plans for
you, my little sissy boy."
As soon as we arrived home, Marie and Dad oohed and aahed over my
make up and hair. Once again Dad repeated that he had to endure wigs,
while I only had to endure the pleasantness of someone working on my
locks. He seemed a little jealous or maybe that was just my
imagination. As you can guess by this time my imagination was working
full time.
They sat me at the table in the kitchen and Marie peppered me with
questions about my afternoon, and my make up and my hairstyling
experiences. She loved the story of how Miss Vickie just had to
change the color and the intensity of my lipstick. She asked me how I
felt wearing lipstick and if I enjoyed doing the actual application.
I could only blush and stammer out answers which I didn't really know
what I was saying. I couldn't tell her that after the first couple of
times doing my own application, I felt that I was becoming quite
proficient and even liked that I was doing something so girlish in a
competent manner.
Mom fixed Marie and I small salads, with little dressing, and weak
tea in china cups with little roses around the lip. (I quickly
noticed that the china bore a lovely lip print from my own lips) Mom
said that we "girls" had to watch our figure. And that tomorrow I
would know just what kind of figure I had to watch. Mom and Marie had
to show me how to eat with my mouth open to receive the salad without
undue damage to my carefully made up lips. I basically realized that
women eat with their teeth catching the food off their forks rather
than the lips. It was quite an experience to see my scarlet enameled
nails clutch my fork and raise it to my carmine lips. Marie made
certain that there was a mirror sitting on the table so I could see
myself.
Dad said that he would take care of the dishes "for tonight" because
Mom and Marie had a lot of work to do to break in their new daughter
and sister. Dad playfully poked me with his index finger in my right
B-cup. "Nice", he said, and left to do the dishes.
"Wendy, come with us to the bathroom. Today you were humiliated in
public but the things which were done to you could even be said to be
pleasant experiences for you. I bet you really enjoyed the attention
at the Salon. But now, dear, you are not going to enjoy the next few
hours as Marie and I prepare you for your first night as a woman."
She guided me into the bathroom. Draped over the edge of the tub was
a pillow with a latex cover. In the corner of the bathroom was a tall
stand, such as you would see in a hospital holding a rubber bag with
long tubes hanging down from it. The bag seemed to be filled with a
sloshing liquid. At the end of the tubing was a long plastic nozzle
and a valve mechanism not far from the back of the nozzle.
"Now, my sissy son, strip down to your bra and panties. Well,
really, MY Bra and Panties because you haven't gotten any of your own
yet. I bet you will be very happy to get out of your mother's
underwear and into your own lingerie. Tomorrow, sweetie, tomorrow."
I did as I was told and stood before my sister and mother in bra and
panties, exquisitely made up and hair styled to perfection. My hands
with their painted nails didn't know whether to cross at my crotch or
over my breasts. My sister laughed out loud and was given a stern
look by my mother.
"Now, Wendy, kneel on the floor by the tub, facing the tub, and lean
over the pillow as far as you can into the tub. Place your hands flat
on the bottom of the tub as far on the other side of the tub as you
can."
"Now spread your legs as far as you can."
My pantied ass was spread high and wide in front of my sister and
mother.
"Wendy, now we have to be sure you are as clean as a woman should
be. Inside and out. Do not say a word unless we ask you to and do not
move any part of your body unless you are told to. Do you understand?"
"Yes, Mother."
"Marie, lower Wendy's panties to his thighs."
I felt my sister's hands reach around my waist and gently tug the
tight panties into the position Mother required. She gave me a little
pinch on the ass as she did so.
"Now, Wendy, do not move or say anything or cry out, unless you feel
like saying Thank You."
As she said those words I felt a tip, possibly plastic, seemingly
smeared with some kind of lubricant, touch my asshole. The pressure
was increased and the appliance went deeper into my rectum. I held my
cry, knowing Mother would be severe if I disobeyed her. I did shiver,
just a little.
"Ah, that went very easily. Maybe we won't have any trouble with
other things later."
"Now, don't move. You will feel the warm enema liquid being fed into
your new little pussy. It is nice and warm and soapy. Just what is
needed to clean all that nasty boy stuff out of your pretty vagina. I
will only give you about two quarts and then we will see how long you
can hold the soapy fluid before you have to shoot it back out. Please
be ladylike."
I could feel the fluid flowing into me and finding whatever region
it could to contain itself. My stomach seemed to be bloating and I
tried to adjust my stomach on the pillow so I could stand the new
pressure. Mother whacked the back of my head with her hand.
"I said: 'Don't Move'. And I mean 'Don't move'!"
"It's not as easy for a boy to become a girl as you may think. I
intend to show you just how hard it can be. You are not to enjoy this
process, you are to hate it and be sickened by it. But you will
endure it. All of it. And this is the first part which may give you
discomfort. Tough! Too Bad! You are only a SISSY and no one cares how
you feel or what you feel! I hope you understand now!"
The enema fluid continued to fill me. I didn't think it would ever
stop. Then it did.
"Now, dear, that wasn't so bad, was it? Don't answer, I don't care.
Now we wait a while while the cleaning fluid does it's work. In a few
minutes you may start to experience cramps. just remember that women
have cramps all the time. Since you are going to be a semi-woman, you
have to bear it."
She put her hand on my back and increased the pressure on my stomach
and intestines.
I could feel the liquid sloshing around inside of me, searching for
a way to come out. My muscles in that area tightened and, indeed, my
womanly cramps did come with a vengeance.
My eyes started to water in tears.
"Don't you dare cry! You will ruin your make up!"
I didn't.
After about ten minutes since the fluid was shut off, Mother allowed
me to get up from the kneeling position. She told me to beg her to be
allowed to expel the nasty syrup from my pussy.
My God, I did beg!
"OK, Wendy, expel now."
I got to the toilet is microseconds and the relief was
instantaneous. Copious amounts gushed into the bowl and I thought I
would never be empty. I slumped on the toilet but Mother had other
ideas for her sissy son.
"Wendy, assume the same position as before. Now we woman have to
smell so good and be so clean, so we have to do what is called a
'douche'. Marie would you do the honors to your new sister?"
I was laying again across the pillow, with my butt in the air. Marie
smiled at me and showed me a box which said "Massengale Lavender
Douche, for proper young ladies".
She opened the box and took out a strangely shaped bottle. The top
of the bottle was curved and came to a small throat of about two
inches in length, with a tapered tubular spout.
Marie said "You're going to enjoy this, Wendy".
She then pushed the spout of the bottle into my new vagina. At the
same time squeezing the plastic bottle, squirting the lavender
scented "douche" into me. She held the bottle in place for several
minutes so the douche could do whatever a douche does inside a 16
year old boy. Finally I was allowed to expel this liquid also. The
room was very fragrant. I was wiped out.
"Well, Wendy, since you are in this position, we might as well do
the next thing that a woman has to endure in this area. I think it
was very nice of Marie to buy a whole box of Tampax Super Absorbent
Tampons for her new sister. They work so very well. I couldn't live
without them. And neither can you. I think your period is just about
to start. All 16 year old girls have periods. So do you. Even if you
are not quite a girl. Close enough for humiliation."
"Marie, do you have the tomato soup ready?"
"Yes, mother, just about a half cup of warm tomato soup in this
turkey baster, as you instructed."
"Good girl. Please insert the turkey baster in his pussy and I will
have the first tampon ready to be inserted."
Mother showed me the tampon. She opened the paper sheaf and showed
me the plastic rounded tipped applicator. As she was showing me this
new instrument of torture, I felt a warm fluid being squirted deep
into me. Then Mother took the tampon out of my line of sight and I
felt the turkey baster being removed and at once the applicator of
the Tampon was shoved into my ass. There was a pushing sensation and
I felt the smooth plastic applicator being removed and in it's place
I felt a sponginess deep within me. Mother took a piece of toilet
paper and wiped me gently around that area and gave a little tug on a
long string which I now had hanging from my ass. She showed me the
red smears on the toilet paper.
"Wendy, welcome to womanhood. You are having your first of many
periods. You will have to learn to apply your own tampons over the
next few days. Because you will have to change them at least four
times a day. And dear, please keep all your used tampons. You will
put them in a little mesh bag and I think that will be a very nice
sachet for you to keep on your pillow by your rollered head as you
have sweet girly dreams."
"You can get up now. Isn't that sensation in your pussy quite
different and fulfilling? You will learn to love it. All the boys do.
Your dad did."
"Marie, dear, Wendy is yours for the next couple of hours. Do
whatever to him you desire as long as it is very feminine and girly.
You know he has to learn to set his own hair every night, starting
tomorrow, so maybe that would be a good starting point for you. At 11
PM I want him in curlers and a bra and panties. I have a special
little punishment for him at that time. Please have his negligee
ready for him to don as soon as his punishment period is over."
"Wendy, don't you dare give Marie any trouble. Everything at the
salon and here in the bathroom has been videotaped and I am sure You
Tube would have a new record holder if these pics would be posted. Do
you understand, Wendy Sissy?"
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2. Wendy's punishment lesson to show him
what could happen if he balks at femininity.
I spent the next two hours uncomfortable with my tampon inserted in
my male vagina, soaking up the tomato soup relentlessly. Marie was in
continuous glee at my predicament and discomfort. Even though Miss
Vickie had spent a lot of time styling and setting my hair and doing
my make up, Marie washed my face and gave me another shampoo and
towel dried my hair. I was made to sit at her vanity table, in front
of her make up lighted mirror, in bra and panties, with a fluffy
towel wound around my chest, in girlish fashion, as she started my
instruction in roller hair setting and basic bedtime make up.
After nine or ten false starts, I was able to roll a section of my
own hair unto the prickly rollers and anchor it firmly at my scalp.
Marie ended up doing most of the thirty rollers which covered my
head. I would have to learn a lot more by tomorrow evening if I was
to do all the rolling by myself. Marie told me that I wouldn't be
doing my lipstick right then so Marie only had to help me with my
night eye makeup.
When Marie and I had finished the setting and make up, Mom came into
the room and told Marie to cover my rollers in a strong net and tie
the net tightly at the base of the back of my neck. This being
accomplished, Mom took a lipstick from the vanity and opened it fully.
"Son, apply your lipstick for sleeping."
I did the best I could. The lipstick was brand new and a vivid blood
red. To do my lips precisely would take a calm and firm hand with
such a dramatic color being applied. As I did the right side of my
upper lip my hand slipped and a smudge of red stained the skin just
at the corner of my mouth. I froze with lipstick in mid stroke.
"NOT GOOD ENOUGH! You must be punished for not being able to do the
simplest of girlish actions. Go stand in the doorway, NOW!"
I ran to the door to the bedroom and stood there. At the level of my
ears on each side was a leather wrist restraint and at my feet were
leather ankle restraints. They had not been there earlier in the day.
"Sissy, you have to know what can happen to you if you do not do
what you are told, immediately and completely and correctly. You did
not to a good enough girlish job of applying your bedtime lipstick.
You must be punished. Take you hand and bring your girlish tit out of
your left bra cup. Place the bra under the flesh so that the nipple
is exposed and raised. Good Girl! Now do the same with your right
tit. Now raise your left hand up to the restraint by your ear."
Quickly Mom strapped my wrist into the leather device. She then did
the same for the other hand and then moved on to the feet restraints.
I was locked in place in the doorway. Breasts exposed while held in
view by the stretched bra underneath.
"Son, some things about being a woman may be quite pleasurable for
you, others may be humiliating and degrading. Great!. But you have to
know that being a bad boy/girl will lead to you being in a lot of
physical pain. Your infraction with the lipstick was not that great,
but we want you to experience a little of the pain which could be
yours."
"Close your eyes."
I did so immediately.
All of a sudden there was a terrible pain at my right nipple. Then
at my left nipple. I kept my eyes closed and bit my cheek to refrain
from crying out. I was in tears.
"Open your eyes, sissy boy."
I opened my eyes and as my head was down in pain, I immediately saw
that each of my new girly nipples had a spring loaded clothespin
attached to it. Mom flicked her index finger and struck the right
clothespin. At the same time Marie did the same on the left.
I whimpered.
"Oh, come on, big boy. That doesn't hurt that much. You know what
will hurt? In about 15 minutes, I will take off each clothespin and
put them back on at a shift of 90 degrees from where I placed them
before on your nipples. OH, now that change will REALLY hurt. The
sore nipples will be compressed in a totally different direction and
THAT is really painful."
"Then you will stand here for another 15 minutes in even more pain,
contemplating your disrespect of your new femininity."
"Let me explain. For a real punishment, if you ever do something
wrong, you will suffer the same nipple punishment for an hour, not a
half hour, and also with 8 ounce weights attached to each clothespin."
"I will tell you something else, little Miss, 28 minutes from now
you will just love the gentle support your bra cups could give you.
The silk would caress your sore nipples and you will never want to be
without those friendly "B" cups again."
Marie watched me suffer for the next 27 minutes, holding the pink
bra top babydoll nightie which I was to wear to bed this night, right
in front of my watering eyes.
"Wendy, repeat after me: I need to wear this lovely nightie. I want
to wear this lovely nightie. I will wear this lovely nightie. I want
my sissy boy breasts to be supported, not sore."
I repeated those lines 137 times in the next 25 minutes. At the end
of those terrible minutes, I meant every word I had said.
-----------------------------------------------------------
3. Wendy sleeps as a girl. Or at least tries to.
As the timer went off after 30 minutes, Marie, bless her feminine
heart, released me from the clothespins and the restraints. My hands
flew to my tits.
"NO, NO, Wendy. Don't touch. Just put your breasts back into your
bra cups, make sure you fill as much of the cup as you can and come
over to the side of the bed."
My nipples were still sticking straight out from the pressure of the
clothespins. As I put the bra cups back up, my nipples made a very
nice presentation through the filmy fabric. But the material felt Oh
So Good on my sore little ladies.
I walked to the bed with my bra thrust out, luxuriating in the
comfort of my bra's support of my sore nipples. Marie met me there
and to my dismay, took by bra off me with a big smile. She told me to
drop down my panties and kick them to the side. Then she had me step
into a very voluminous pair of white rayon panties which had rows and
rows of ruffles all around. Then she had me step into a pink babydoll
nightie with a structured bra bust and offset straps for my shoulders
and layers of filmy sheer pink fabric falling from the empire bosom.
Marie checked that my hair net was very secure around my curlers and
that my tampon was snuggly in place, keeping my female flow in check.
She handed me a tissue and told me to wipe off my lipstick. I
immediately did so, using several tissues to clean the cream from my
lips. Marie then gave me a compact mirror and a new lipstick and
stood inches away from me as I did my lips one last time on this
first day of my girlhood. Marie arranged herself so that her head was
in the mirror with mine and she followed every stroke of the lipstick
wand as I did a womanly precise application. Marie beamed and told me
to lay down and tucked me in the baby pink satin sheets. She gave me
a light peck on the cheek and said: "Good night, Sweetie. If you
thought today was bad, just wait until tomorrow. I think Victoria's
Secrets is stocking the shelves tonight just for you."
Marie left the room, leaving only a pink night light to light my
sissiness. Dad appeared at the door.
"Good night, son. I brought you a beautiful dolly, looks a lot like
Shirley Temple, for you to cuddle with tonight. When I was punished,
as you are now, I wore a Shirley Temple wig a great deal of the time.
I might have to task to Miss Vicky about that look for you. I know
the dolly will help you through the night.
"I am so proud of you, my son, just think you have had your first
period. I hope you are getting used to the tampon. It will be more
comfortable when you are wearing your panty girdles. And, son, I
think that tomorrow, you should go with an additional coat of
mascara. I wonder if mother will style your hair for tomorrow or
leave it in rollers all day. Decisions, decisions. For her, not for
you. Good night. Don't get lipstick on your pillow. That could cause
a punishment session."
Then he was gone. And so was the old me.
To Be Continued
Mei
- 27.08.2021
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