My Stepmothers Sissy Daughter
- 3 years ago
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Step-mother's Sissy School-boy free porn video
One-Handed Reading: A Step-mother's Sissy School-boy
This is a one-sided conversation between an (evil?) step-mother and her
delinquent step-son.
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Author's Note: This is not some attempt at a Pulitzer, or to make some
earth shattering literary statement. Nope. If you are looking for deep
characterization or nuanced subplots, move on. This tale is not for you.
I love exploring verbal humiliation alongside being dressed.
This is what I call One-Handed Reading. It is an exploration of my
fantasies involving crossdressing. Sometimes it is sweet, sometimes it is
sexual. And while many of them involve teen-aged characters, they are
merely manifestations of my own psyche, glimpses of my deepest fantasies.
I would never condone anything like this happening in real life. And I
love stories where the clothing is described in decent detail. Just
giving a color and article of clothing doesn't do it for me. Bleh!
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Time to get up sleepy head. You need to get ready for school.
I've laid your outfit for today out for you honey. Oh, don't look at me
like that! You know exactly what I'm talking about.
I've laid out a very cute outfit for your first day going to school as a
sissy boy, and you, my dear sweet sissy, will wear it!
I don't care if you are scared, and those tears won't help either. You
didn't seem to care when you threw all those poor girls clothes into the
dumpster. You ruined a lot of moneys worth of clothes for those girls
Chris. And for that, you are being punished. You were a bad boy, a
naughty boy.
You could have been expelled, but you agreed to abide by whatever
punishment the girls came up with for you. It's your own fault you will
be wearing pretty girly clothes to school. You could have had it easier
you know? The girls were only going to dress you up in their clothes,
like a normal girl, like them. They would have done a nice job, a
convincing job, of making you look like a girl.
But, no! You had to stomp and scream that you did not want to look like a
girl. They couldn't make you look like a girl. You wouldn't let them, you
would do any thing else they came up with, just so they wouldn't make you
look like a girl. The principal and school board agreed to let the girls
come up with something else for your punishment, but you had to agree
that no matter what it was, you would do it. You agreed, like the naughty
boy you are, thinking you got out of big humiliation.
Can I help it if the girls agreed they would not make you look like a
girl? They gave you a much worse punishment, a very fitting punishment I
think.
Oh, don't cry Chris. I told you that would not work. You out smarted
yourself.
I couldn't help but laugh when I heard the girls new plan for you. They
thought that with me being your step-mother I would be against it, but I
am all for it. You have always been a bad little boy, now you will be a
good little sissy.
Oh yes. I love their compromise. They agreed to not make you look like a
girl, they would just make you look like a sissy. A pretty sissy boy in
girls clothes, nice trendy girly clothes. No pads or shapers to give you
a girlish figure.
Nope. Just your boyish shape in sweet feminine clothes.
They sent over a bunch of cute outfits for you to wear. You'll be so
adorable in them I bet! Don't you think? An adorable sissy boy wearing
cute girls clothes to school. Everyone who sees you will know you are
just a boy underneath all those girls clothes. How embarrassing that will
be for you. Won't that just make you blush?
They even have a name for you Chris. They will call you Chrissie. Do you
like that name Chrissie? I think it a very pretty name for a sweet sissy
like you, very appropriate. Say it with me. Chris See. No Chris. Say it
now. Chris See.
That's a good girl. I mean, a good girly boy.
Now, to get you dressed Chris. I mean Chrissie.
They girls decided, for now at least, that only real girls wear skirts
and dresses. Though Sarah told me she was dying to see you in a nice
dress or a short skirt. The others agreed, but decided to wait.
Don't look so relieved boy. No skirts does not mean you won't look
girlish. They have so many adorable outfits for you to wear, I can't
wait. All of them are pants or shorts too. Girls pants. Girls shorts. All
very cute and girly for our trembling little sissy school boy.
We have capris, scooters, skorts, shortalls, overalls, palazzo pants,
split skirts, jumpsuits, cropped pants of all kinds, and some dressy
trousers. And the jeans. Oh Chrissie, the jeans are so wonderfully cute,
they just scream girl. Flared legs, whiskered details, embroidered,
laced, you name it! All for you to wear to school, all screaming you are
a wanna-be girl, a cute sissy boy in who likes to wear girls clothing.
At first, I couldn't decide what to put you in, what to make you wear for
your first day to school as Chrissie the sissy boy. I am so enjoying
having you to dress up in pretty things. My little Ken to dress as
Barbie. My little teen-aged dress-up dollie. You will be so adorable
Chris. Ooo, I meant Chrissie.
My first choice was this scrumptious pair of dress pants. I like the way
they would be snug on your thighs but come down to that adorable flare
just above the ankle. And black is so in for young girls these days. For
girly boys too I guess. The side zip would have made you think about them
girls' trousers all day long, every time you had to go wee-wee. And the
flat front and back of it would have shown off that boyish, ahem, charm
you have. Oh! And the little chain belt is just so cute too.
The top was just wonderful too. Here it is. Do you like twin sets
Chrissie? I find them to be very fashionable for girls. I figured you
being a boy would look adorable in it too. Especially this lilac color.
Very girlish. I like the soft cotton knit of it. It'll be very
comfortable, and snug without being tight or constricting.
See how the cardigan covers up the pretty spaghetti strap tank
underneath? You aren't allowed bare shoulders in school, you know. Not
even for sissies like you Chrissie. That's why twin sets are so great.
You slip on the tank, then shrug yourself into the soft cardigan. for
warm days, like today, you can either let it stay unbuttoned, or do up
the top button for a fly-away look. A lot of girls do that, so you'd fit
right in, eh? Or, a trendy option is to do up one or two in the middle,
just under your breasts, so your cleavage up top can be seen and you
still have the fly-away feel. But. You have no cleavage, do you? Since
you are only a boy wearing girls clothes that is.
Anyhow, I also thought maybe a more casual look for you. See these jeans?
I think the laced up front is so cute.
And there are laces on the sides too, see? You'd look fantastic in this
Chris, don't you think? We could add this top. No, this one. The one with
the smocked waist and the short puffy sleeves. You could wear it either
up or down on your shoulders, or both, whatever your sweet new
girlfriends at school decided.
Oh, yes. I forgot to tell you. They are in charge of you at school dear.
They may make you change, or add things.
Who knows. But you will do just what they say, won't you my pretty sissy
pet?
Anyhow, what I finally decided for you was to go with a sporty look.
You'll be a sporty sissy Chrissie. I guess you would be a reverse tom-
boy, a Tommy Girl! Oh, by the way, the girls actually left several Tommy
Girls things here for you too. Hee Hee!
First my little sissy, you need to take off your boys' briefs and put on
your new girls' panties. I had to buy these ... the girls didn't want a
sissy wearing their panties. At least not yet, if I know Sarah.
I of course had to tell the sales-girl at Wal-Mart they were for my step-
son. You know the girl I mean? Gwendolyn, the one you flirt with all the
time when we shop there? She was so surprised, but when I told her you
just loved to wear cute girls clothes she begged me to bring you by next
Saturday when she'll be working the changing stalls. She said she wanted
to see how adorable my sissy step-son is and to help you pick out some
cute girls clothes for your own.
She's actually the one who gave me the idea for your sporty type outfit
today Chrissie. Gwen said she thought you would be too cute in it. So, I
went ahead and bought what she suggested. Oh! Look at the time.
We have to hurry. Can't have our sweet sissy be late for her debut as the
Belle of the Ball at school, can we Chrissie? Oopsie. I mean his debut as
the Sissy of the School! giggle giggle
How do those panties fit? Do you like the color? I thought the pink and
lavender stripes were the cats meow, and I was right. They look simply
wonderful on you! Those are called boy cut briefs. A little pun to poke
fun at your sissified state. Funny, no?
Oh, stop pouting like that before I add matching lipstick for your
outfit. Yes. I bought you some makeup at Wal-Mart too, honey. A sweet
shade of pink called Coral Crush. Do you want some lipstick, dear sweet
Chrissie? I will put some on you if you like? No? Okay, then. Maybe
later, eh? giggle
Now put the matching bra on. Yes. A bra. It's a sports bra, but we will
not pad it. Sissy boys like you don't have cleavage Chrissie. Just your
boyish flat chest under the girls clothing you will wear so no one
mistakes that you might be a girl. Your hair is short, so that will
always help, but some tom boys have short hair. Maybe you'd like a girly
hair-do sometime sweetie? Your hair looks long enough for a couple of
cute pigtails. Right there on the sides of your head, near the top. Ooo
that would look so adorable. Yeah, later though.
Now for your outfit!
Here you go. Put this tee shirt on. Do you like the soft pink color
Chris? Just right for a cute sporty sissy like you.
No, the sleeves are supposed to be that short. They are cap sleeves,
silly. You'll learn all about girls clothes honey,I promise. You'll learn
as you wear each piece, right? Good girly-boy.
Stop tugging it down. It's supposed to be that length. It's called a crop
tee. So when you move certain ways your cute little belly button will
show. Yes, I know you cannot wear a top that exposes your midriff to
school. We aren't done yet either, my impatient sissy. Oh you must be
positively dying to get into your other clothes.
You certainly are what your cute pink tee shirt says aren't you? Spoiled
Brat Princess! Are you a bratty girl Chris?
Is that what you are? You want to be a spoiled little brat sissy who who
gets upset if he can't wear his girly clothes to school? Aw, poor
Princess Chrissie the Spoiled Brat Sissy.
Now, here are your bottoms you will wear today. Ooo, your eyes lit up. Do
you like them? Such soft and pink jogging pants. Or was it because you
think they are like boys wear? No no no! These are very girlish, through
and through. Put them on, honey. That's right. Good sissy boy. Good
Chrissie.
See? They only go to your lower waist, and the ties are on the outside of
the wide ribbed band. And see how they cling to your upper legs then
flare out by your ankles? A very girlish style. The material is velour.
It is very soft isn't it?
Oh! Looks like you enjoyed it when I ran my hand on your leg to show you.
Don't get too excited little sissy. I can see your sissy thing start to
get happy. Maybe, if you are a good sissy boy, and make sure you enjoy
your girly clothes, one of your new girlfriends will help you with that?
Maybe Gwendolyn down at Wal-Mart? Or maybe Sarah at school? They both
seemed very excited about my sweet sissy Chrissie wearing his girls
clothes all around. To school, out shopping, to the movies, everywhere!
Uh oh! Look at the time! We'd better hurry, sweetie. Let's finish
dressing you up, okay?
Here's a matching zip up hoodie for you. It's velour as well. Slip your
arms into it Chrissie. I'll hold it open foryou, my pet. There you go.
Now turn around. That's a good girl Chrissie. Oopsie, I did it again. I
know you are a sissy and not a girl Chris, but you look so sweet and
adorable in your girly clothes I just want to eat you up!
Now, the way to wear this is you zip it up just a little bit, like this.
That way, the ribbed band on the bottom keeps your midriff covered while
in school, but lets everyone see the cute tee shirt you have on. So they
can read it you know. giggle giggle
The hood stays down, too. You can slip your sleeves up a little if you
want. Many girls wear their hoodies like that. It's like the three
quarter sleeves. Something that would look great on a sissy girl-boy like
you Chris. Oops, Chrissie.
Now, for your feet. Here. Put these little ankle socks on. They are just
plain white, but you fold them over. No, like this. Here, let me show
you, dear. There we go. Like that, just like the girls wear. I have some
cute trainers for you too. The girls donated them. Do you like the way
the pink accents shimmer against the white of the shoe? I like the
glittery pink laces too.
There. My little sissy is ready for her ... his first big day at school
in his new clothes! You look just like a teenaged sissy. A perfect little
boy wearing sporty girls clothes ... a soft pink confection that says,
"Hey! I am a sassy girly boy, so watch out!" But the pink says you are
soft and sweet and a demure little sissy princess. Sissy Princess
Chrissie the Bratty Girl-boy Sissy. That's you my pet.
Are you certain you do not want to try the lipstick? No? Oh well, later
then I'm sure.
Off to school with you. Have a nice walk, dear. And you'd better do
something about your little friend poking out in front, Chrissie! giggle
giggle
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