The compulsory punishment

Printer-friendly version

Sam was just a normal boy. So what made him do something so different is a mystery.

His sister, Jane, was going to be a bridesmaid at her friend's wedding in a few months. She was very excited about it, and especially loved the dress she'd be wearing for the day.

She still lived at home with Sam and mother , Angela. She worked as a receptionist at a solicitor firm in town.

Angela also worked in town at a busy store and they both used to catch the bus to and from work Monday to Friday and sometimes Saturday for Angela.

Sam, on the other hand, was unemployed, as he had only left school a few months ago and as yet, was still to find a job.

He was quite happy with the situation but sometimes would be bored watching television if his friends were not around.

So, what ran through his mind on this particular day was quite out of the ordinary for him.

Being bored he would go searching for something to do in the house. Often he'd sneek into his sister's room to play her records on her stereo record player she had.

Presumably it was initially his intention on this fateful day. The day that his life changed and became a living hell.

As he entered her room, he couldn't help but notice her bridesmaid dress hanging on the wardrobe door. It was a calf length pink dress with puff sleeves and a full skirt.

Feeling very mischievous, he wondered what it was like to wear such a garment. Without hesitation he laughed to himself as he took it off the hanger, unzipped the dress and stepped into it. Carefully he pulled his arms into the sleeves but his shirt made it very difficult. He removed his shirt making it easier for his arms to go through the sleeves. Then he reached round and zipped up the dress as far as he could. It was about 3 inches away from fully zipped and he noticed the pull that the dress had around his waist and chest.

He laughed as he stood in front of the mirror and then preceeded to select and play his sister's records.

After an hour or so, he decided he'd had enough. He turned off the record player, put the records away and reached round to unzip the dress.

Eventually, he managed to hold the zip and tugged it downward. It moved about half an in and stuck. In a panic he tugged harder but the zip was stuck fast. He started to sweat with panic and shake which only made the dress stick to his body.

He tried to calm down by sitting on the bed and as soon as he was calm again, he tried the zip. But it was not budging at all.

He tried to lift the dress over his head but the zip was in such a place that he couldn't even lift even the lower part of the dress.

What on earth was he going to say. What excuse is there. He just panicked more thinking of excuses and looking at the time, he knew that his mother and sister would be home very soon.

He sat in silence waiting for the front door key to sound and sure enough, the front door opened and he heard the sound of their voices as they chatted about work etc.

Sam quietly went into the bathroom and after a few minutes he heard his sister coming up the stairs.

He heard her shout down to mother "mum? Where's my bridesmaid dress? "

Angela started coming up the stairs "what do you mean? "

She joined his sister in her room and looking bewildered she went back to the landing and saw the bathroom door shut.

"Sam are you in the bathroom? " Angela called.

"Yes mum "

"What are you doing in there? "

"I'm having tummy trouble "

"Have you seen the bridesmaids dress? "

With that, it went very quiet for a while. Then, after his mother asked the question again, the door unlocked and a very sheepish looking Sam came out wearing the dress.

Both his sister and his mum were speechless for a moment. His sister didn't know whether to laugh or cry. But his mother was visibly annoyed. She took his arm and propelled him into his sister's room.

"What the hell do you think you are doing? " she barked.

Sam tried to mutter something but his sister noticed that the zip was stuck

"Brilliant! " she said. "He's ruined my dress"

Angela tried tugging at the zip and eventually it freed.

"Well I am not wearing that dress now, not after my pervy brother has worn it " his sister said.

Sam began to remove the dress but was quickly stopped by his mother.

"Oh no you don't " she shouted, and quickly zipped it up again, this time all the way to the top and fastened the hook and eyes at the top.

"You stay there while your sister and I call her friend and tell her that she can't now be her bridesmaid " his mother said.

About an hour later they both came back up to the bedroom, still looking angry.

"It's been decided that you will pay for a new dress " his mother announced. "And that's going to be difficult as you don't earn any money isn't it? "

His mother started to undo the dress but had hold of same while she slid the top of the dress down but only to his waist. His sister then came to fasten a white bra around his chest, filling the cups with tissue.

Angela then zipped the dress back up and fastened the hook and eyes again.

"That looks better doesn't it " she said.

Sam tried to say something but Angela was not listening. Instead, she cut him off and ordered him to take his socks and trousers off which he eventually did after much reminding.

They then slid on a pair of white tights and the full underskirt of the dress which made it stand out. They fussed around for a while tugging at the sleeves and the hem of the dress until they were satisfied .

Sam was mortified and again tried to say something only to be cut off again by his mother.

"We haven't finished yet " she said, looking over at his sister.

Angela instructed him to sit at her vanity table and started applying make up. The full works including foundation, powder, eyeshadow, blusher, mascara and lipstick.

Finally his sister fitted him with false nails and painted them pink to match the dress.

Then after brushing his long shabby hair, made it look extremely feminine and placed clips and a huge pink bow at the base of a ponytail.

Angela then took numerous photos of this newly feminized boy.

"We'll need to get a few more things yet, like shoes etc" his sister said as they took him by the arm to the full size mirror.

"What do you think? " his mother asked

"I..I. .." he spluttered.

"Well it doesn't matter what you think anyway " his mother said as she stood behind him.

"You are obviously jealous of your sister being a bridesmaid. So we called her friend and guess what? She said she would like to have an extra bridesmaid, providing we can make you look the part. So that's exactly what we intend to do. You are going to pay for a new dress for your sister too and you will pay by earning for it. The brides mother and the bride will be here shortly to see what a great job we've done. If she agrees to you being a bridesmaid, you will obviously thank her then you will dress and act as a girl right up until after the wedding. That means full make up every day, and only skirts and dresses to wear. Do you understand? "

Sam again spluttered

"Furthermore, if nobody guesses that you are a boy at the wedding, we intend to keep you as a girl until you can convince us that you had a valid excuse for ruining your sister's dress in the first place. We will now update your social media profile with your new picture of you as a bridesmaid and your name is now Samantha "

The two women left the room to Sam's room to empty his wardrobe of all male clothes and replace them with a few skirts and dresses.

up
229 users have voted.
If you liked this post, you can leave a comment and/or a kudos! Click the "Thumbs Up!" button above to leave a Kudos

Comments

Stuck on dress literally...

fits for the crime. This was a fear for those who have snuck to crossdress. How many close encounters and instead of scaring us out of doing it. The attraction of visibly seeing drives us to do more. I suspect the outcome of this punishment will be different from what the three think.
Since he kept on the dress as long as he did, he must have enjoyed the experience. The nice snug fit was part of why the zipper caught.
Good story.

Hugs, Jessie C

Jessica E. Connors

Jessica Connors

Good first story

laika's picture

It flowed well, with solid writing and Sam's predicament in the first half was funny. The ending was pretty standard forced fem, a genre beloved by many but this kind of cruelty-for-cruelty's-sake so far in excess of what her child actually did always infuriates me and makes me hope Mom dies alone, unloved and in great pain in a nursing home... but that's my hang-up. Welcome new author!
~veronica

.
We now return to our regular programming:
https://www.youtube.com/watch?v=qTl00248Z48
.

putting it on social media is

putting it on social media is a bit overkill are they trying to get him hurt or killed or just ruin his life.

Drive-by feminization

licorice's picture

uhh... what just happened? I mean this is pretty part-and-parcel for a feminization story, but the whole thing just is so... weird? I'm sorry, I can suspend my disbelief but this goes way beyond my ability to do so. Boy tries on a dress, gets stuck in it, accidentally ruins it, and suddenly is going to be a bridesmaid and be forced to be feminized? More than that, the whole 'if nobody suspects' thing is blown out of the water by their immediate decision to upload it to the social media account, which WILL spill the proverbial beans.

This would definitely result in the kid getting severely bullied by anyone and everyone, not to mention raise a lot of questions with the school administration and... I'm sorry, I'm really sorry but I can't suspend my disbelief for this. It's like a drive-by feminization, it just happens so fast and so randomly I can't make sense of it. My apologies.

A bit harsh you think ?

That's pretty arch punishment for a bit of curiosity don't you think.

ShadowCat

Exceptionally good prose

Your writing is great. The story flows well, the boy caught in the dress is something that could easily happen. Making him stay in the dress is a believable punishment, although as the punishment is extended to participating in the wedding it falls into the abyss of unbelievable with the posting to social media and possibility of forcing him to remain that way.

I think if you were to rewrite the last part, removing him being forced into the wedding, posting to social media and forced to remain that way and have him "having learned his lesson" at the end or he finding he likes being dressed up in that way and continues with mom and sisters help, it would become much more believable.

We the willing, led by the unsure. Have been doing so much with so little for so long,
We are now qualified to do anything with nothing.

your first?

That was fun, maybe untrue and beyond what could happen, but it's your story, ignore those who want you to write the story for them.

Compulsory punishment

I love this story and can't wait to see what happens next
And what they have in-store for him next

The compulsory punishment

This was an excellent story
Is there going to be a part 2