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One-Handed reading: A Step-mother's Sissy School-boy (TG)

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
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.

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.

I wrote this particular one-handed story five or six years ago just for myself (2005-6). No one has seen this one. It has never been posted before.

This is a one-sided conversation between an (evil?) step-mother and he delinquent step-son.

I love exploring verbal humiliation alongside being dressed. 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!

The only changes from the original are spelling corrections. (Originally many of the words were spelled phonetically so the text-to-speech program I had could read it to me!)

I am currently considering doing a continuation of this story in a similar style, but with other characters doing the talking. What do you think? Do you like this style of story?
Add a Comment:
GirlGirlBoy Featured By Owner Dec 29, 2014
I LOVE it beyond what words can describe! Thank you so much for writing this. Hey, I'd love to chat sometime. Let me know if you might be interested; we have a LOT in common! ;-)
SissyDemi Featured By Owner Dec 30, 2014  Hobbyist Digital Artist
I am glad you enjoyed the story. :D
TheMad-Scribbler Featured By Owner Jun 25, 2014  Hobbyist
Ohh my god i love this sooo much :happybounce: !!!!!!!
Reading this made me so horny it actually hurtLove 
SissyDemi Featured By Owner Jun 25, 2014  Hobbyist Digital Artist
Then the story had its intended effect.
huberthowhow Featured By Owner Jun 4, 2014
I get it.
SissyDemi Featured By Owner Jun 5, 2014  Hobbyist Digital Artist
You get it? I don't understand. >_>
dooty3d Featured By Owner Apr 30, 2014
great i like you history
SissyDemi Featured By Owner May 2, 2014  Hobbyist Digital Artist
sissyboy101 Featured By Owner Feb 19, 2014
Wish that was done to me
SissyDemi Featured By Owner Feb 20, 2014  Hobbyist Digital Artist
Me, too!
suzzen12 Featured By Owner Feb 29, 2012
i like it wish that was me
SissyDemi Featured By Owner Feb 29, 2012  Hobbyist Digital Artist
jungle-king Featured By Owner Jul 11, 2011
anyone wish that they had a mom or step-mom like that
SissyDemi Featured By Owner Jul 11, 2011  Hobbyist Digital Artist
JamesNylon Featured By Owner May 14, 2011
very nice and well written
SissyDemi Featured By Owner May 14, 2011  Hobbyist Digital Artist
Thank you! :3
JakTheRenegade Featured By Owner May 9, 2011  Hobbyist Writer
I would love to see this continued
SissyDemi Featured By Owner May 9, 2011  Hobbyist Digital Artist
I've already been thinking of the next "scene" or two. But an elbow injury makes doing computer related things (typing, mousework) painful. The continuation is in my mental queue, though. hehe
JakTheRenegade Featured By Owner May 9, 2011  Hobbyist Writer
Hope your injury heals soon
blahblah23454 Featured By Owner Apr 26, 2011
I liked it. Please do continue it.
jungle-king Featured By Owner Apr 25, 2011
reminds me of me
SissyDemi Featured By Owner Apr 25, 2011  Hobbyist Digital Artist
As in something similar happened to you? You have done something similar? You want something similar to happen to you?

Also ... >_> ... <_< ... MUDKIPS! ;p
jungle-king Featured By Owner Apr 26, 2011
i want something similar to happen to me
SissyDemi Featured By Owner Apr 26, 2011  Hobbyist Digital Artist
Yeah, I would love it, too.

I would never actually condone this for a real kid, but it is fun to fantasize ourselves in those circumstances.
FFecchifan Featured By Owner Apr 23, 2011
BTW, I found that this theme (boy turned into female by mother/stepmother) is rather popular. I wonder if it's based at any real story...
SissyDemi Featured By Owner Apr 23, 2011  Hobbyist Digital Artist
In my case? No.

:icondaphnesecretgarden: has based many of her images and stories on real life experiences. Check her out if you haven't!
FFecchifan Featured By Owner Apr 23, 2011
Cool one.
SissyDemi Featured By Owner Apr 23, 2011  Hobbyist Digital Artist
Thanks. I might continue this one with a one-sided conversation from one of the mentioned girls' viewpoint.
PrincessJessica Featured By Owner Apr 22, 2011
cute :)
Add a Comment:

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Submitted on
April 22, 2011
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