One thousand dollars cash at the end of the party for any boy that dressed "convincingly" as a girl his age. Another five hundred dollars, as a bonus, if the boy dressed as a pretty little girl no older looking than seven. Five hundred more if that boy came dressed wearing a cloth diaper and baby pants. That was for any boy and didn't include the winner in those three categories with each getting an additional one thousand dollars.
one knew who was organizing the party but the local bank confirmed that the money for those attending and the winners had been deposited. Someone also rented the grange meeting hall and a specialty company that did props and decorations for proms, pageants and wedding was already doing the decorating. Only boys dressed as girls could attend and only those boys who looked like girls would be paid. Girls were allowed but couldn't participate.
spread all over town as to why and who it was doing this but no one really knew. There were a half dozen layers of companies behind the name used to set this up. Even the local newspaper couldn't unravel the complexities of this event or the events sponsor. All everyone knew was that a boy, dressed as a little girl in a diaper could take home three thousand dollars if he won and even if he didn't it was at least two.
of the boys refused to participate at first. Most joked over the party as they watched the hall come together in it's pinks and lavenders and lace. No one would admit they were willing to do such a thing for any amount of money but that didn't last. There were a lot of hard working people just making ends meet and a few with ends that didn't. Some desperate enough to start begging their boys to take this on. A few, or at least so they swore that their parents were making them go.
all of the boys going would be little girls and wearing diapers. "Too much money to ignore that part of it!" One mother said as she bought a bolt of Birdseye cotton for her son's "costume". Hundreds of yards of satin, lace and ribbon went out of Patricia's Sewing and crafts store and all three of the local seamstresses were booked solid.
was really odd was that no wigs were allowed. The boys had to be wearing their own hair but could wear it any way they or their mother's might chose. Ribbons and Alice bands were allowed and if the boy's hair was long enough any style suitable was also OK, but no wigs or hair pieces.
were other odd things added like an additional one hundred dollars for the boy who brought a girl's baby bottle in and nursed it. Fifty dollars if he had just a pacifier, fifty additional for a cute dolly and so on. If the boy wore a diaper and if it was pinned with pink diaper pins that was also another fifty dollars. Ruffled panties or rhumba panties another hundred. Some of the mothers had to go out of town to buy they son's those accessories.
the time registration came there wasn't a boy left not going to the oddest Halloween party of all. There wasn't a scrap of pink ribbon, nor lace left in town. Most of all of the dolls and baby bottles and even pacifiers had been sold out by Saturday and that was the oddest day of all. The boys had to come dressed with at least one parent to register.
parent had to sign a registration form, agree to three photos covering the front, side and back and the release of those photos. There was a five hundred dollar signing fee that the parents took home with them. Sam's mother was beyond words when the flyers started circulating. If Sam didn't win they would still have almost five thousand dollars by the end of October.
tried to keep a stiff upper lip through the process but it was difficult as his mother began making his dress. He was going as a toddler girl obviously and just as obvious he'd be wearing a diaper and those adorable ruffled baby pants on the pattern his mother laid out of the dining room table.
watched his outfit come together including his new baby bottle, those diaper pins with the pink bunnies and just to be safe a pacifier he'd have clipped to his dress. Sam's slips numbered six layers of tulle, organdy and that softer, silkier layer of taffeta that would rustle next to his legs. His dress was pink, satin, laced and then covered in organdy before being trimmed out in ribbons.
was wearing his diaper and those ruffled baby pants three weeks before the party and his slips a week later. Each day his mother did something to his outfit she had him dress up again. He was getting diapered at least once a day and sometimes two. If there was any good to come out of that at all it was that by the time registration came around Sam was use to his new outfit.
Sam wasn't alone and nearly sixty boys were lined up for the forms and pictures that Saturday. The local newspaper was doing the registration with the president of the bank doing the verification before the boys got their signing bonus. That envelope came after the pictures and Sam had to admit that seeing his mother happy like that was worth his outfit. Of course he wouldn't admit that to anyone including the boys he hung with but they had their own outfits and problems.
two boys didn't participate and one of those was in the hospital and the other moved with his dad a few days before registration. The rest of the boys in town were, to put it the same way as the newspapers did, dressed as little sissy babies. Of course the girls already slightly miffed not to be participating didn't make it any easier. Most were there on Saturday teasing the boys and taking their own pictures.
wasn't until a week after Halloween that the story came out. An exclusive for the local newspaper after all of the boys received an album with their pictures in it. On the front was a neatly lettered title that read: "Our Little Sissies". Each boy had all three pictures of the pictures taken on a single page with his name and address and what he wore. The rest of the album was pictures of the party.
years ago there was a boy teased for his effeminate behavior. He was girlish in the way he acted and obviously branded a sissy. His mother vowed one day to see justice served and that justice came on the day the story broke. That day came beginning with the boys all dolled up and standing in a line for registration.
was a personalized note in each album, on the day it was delievered, that read: "My son was born feminine but, as you've discovered, some boys can just as easily be taught to be little sissies!