Successful Fundraiser (Halloween)

 

Every year the staff at Emory High School would host a Halloween fundraiser, where

the students who raised the most money

would get to choose the Halloween

costume of a specific teacher. In years

past it would be used to make one of the

older, cooler teachers come in dressed

like a clown or something silly. Other

years they'd pick a female teacher to

dress in something skimpy or suggestive,

but still obeying the school's dress code.

It's all in good fun, or so they told Mr.

Stamp, or rather Ms. Stamp, as he would

be known for the day.

Emory High was in a rural county and was

the definition of a sports school, all of

their teams ranked high in their respective

divisions, so a lot of the student body was

made up of athletes or farm boys like the

ones who bullied Steven Stamp in high

school, but he was confident' now that he

was the creative writing teacher he'd earn

their respect, but he was wrong. They

took the time to show him up physically,

attempt to scare him in the hallway, and

this new form of humiliation, pulling their

resources to win the fundraising contest

and nominating him to dress as a

schoolgirl for Halloween.

Steven was hurt by this, he was always

scrawny and non-confrontational, bullied

and singled out for being sensitive and

more interested in writing. So, he turned

to his Mother, which wasn't too difficult

since he didn't make enough to move out,

she reassured him and told him he

wouldn't earn any respect by stubbornly

refusing, and maybe he should roll with it.

Her being a beautician, she invited a few

girls from her work to turn Mr. Steven

Stamp into Ms. Sydney Stamp.

All of the women he called Auntie for all

his life turned up early in the morning

before heading to work to work on their

project, Steven apologized, but they

agreed they'd been dying to doll Steven up

since they saw puberty didn't do much for

him.

After a long time in the chair, having his

hair styled, his face made up, his body

waxed by the member of the group that

was closest to his age, and was

embarrassingly his current crush who

complimented his already womanly legs,

soft skin, and how easy it was to hide his

bulge, telling him that after the glue dried

he filled out the bra better than the

panties.

They decided that his voice was high

enough that she didn't have any work to

do their and she'd be wearing Mary Janes

so she didn't need to practice in the heels.

So after a few lessons in walking, the girls

were on their way, leaving Sydney a few

hours to mentally prepare herself, look

into the mirror and realize... She was the

hottest girl that had ever been in Steven's

room. So she turned on the flirtation and

took a few videos to save for later... Even

if it did make her tuck job a little

uncomfortable.

Driving to school, Sydney fought off the

nerves, the cool air blowing across the

freshly-smooth skin between her knee

socks and skirt, and even under her skirt.

Her biggest concern was getting pulled

over and needing to fish her wallet out of

her borrowed purse. If only that were the

worst outcome. Upon getting to the

school she was confronted by the

principal, mistaken for a student in a

skimpy costume and constantly

interrupted when trying to explain herself.

The gym teacher/Football coach decided

to assist in the altercation and scoop

Sydney up as if she weighed nothing and

carried her to the office, desperately trying

to hold her skirt down. They wouldn't let

her spit out more than a single word until

she gave them her Mother's number to

bring a change of clothes, but she

explained that Ms. Stamp was a teacher,

leading to her exiting the office to a

chorus of hysterical laughter.

Upon getting to class, Ms. Stamp sat with

her legs crossed greeting the students,

playing it cool. Everyone was impressed,

a few of the girls who were actually

excited about the class complimented

Ms. Stamp. The jocks who picked on

Steve and just needed the English credit,

were all silent, even asking for her help

with their stories. Sydney felt she'd

earned their respect for taking it in stride,

she proudly continued her classes for the

day, even playing up the girly character in

the teacher's lounge, to the discomfort of

the gym teacher. After school she was

floating so highly that she agreed to wear

a dress her Mother picked out to wear to

a Mother-Daughter Dinner date after

handing out candy. Then Ms. Stamp

checked her phone, forgotten in the purse

to find dozens of notifications notifying

her that the students who asked for her

help had been sneaking upskirt photos of

her and filming her lesson to upload to

voyeur sites under the title "Sissy Bitch

Teacher Sluts it Up for Halloween"