As a starter I will say could be fantasy or reality.

The whole idea of the community center in our little town was just to get a nice
indoor pool and meeting room for the few families to use and to have as an addition
for the summer rentals who came to our small bayside village. With each
householder owning two to three cottages we could all benefit if the outdoor pool
could enhanced so our renters would not have to brave the midsummer jellyfish
bloom and off season the locals could have a swim and a place for parties and
meetings. For several summers we had bake sales, boat rentals, and all of the beach
concessions made large contributions. Finally we had the center built and the pool
open but needed to make the last big payoff. My wife being on the finance committee
informed me of the last idea the group came up with.
"We are having a 'Womanless Beauty Pageant' this summer and all the money raised
for the voting will go to the final payment."
"This impacts me how?"
"You have to wear women's clothing for the pageant.'
"Like hell I do."
"Well if you don't take part you have to pay a weekly fee to wear men's clothes and
you can't stay in the house you'll have to live in the back lot cabin."
"Why do I have to do that?"
"It's part of the pageant rules all men take part so no man gets singled out. All of the
guys collect money donations in their vote cans and at the end of the pageant we
declare the winner and pay out half of any money over and above the needed
amount. We need only $10,000.00 bucks there are 30 guys in town so each guy
raising $333.33 bucks pays off the last bit and we will ask for a minimum amount per
vote of one dollar. It will be fun and all you do is wear women's clothes."
"I wear skirts."
"And blouses, oh and panties and a bra, and high heels"
"What?"
"Marie Logan has a connection to a clothing distributor so she is providing all the
clothes and lingerie so you do have to pay her a startup fee and go get measured
tomorrow."
"Tomorrow?"
"At 10:00"
"10:00 PM?"
"NOOO, doofus 10 AM just before her store opens at 11. Now come with me she
needs you ready to dress."
"Huh"
"I have all the depilatory we'll need strip off and let's get the party started."
I sputtered on for some time and complained all the while but that night I went to bed
hairless and clad in my wife's sheer pink nighty. Adding to the frustration my wife
informed me she had her monthly visit from 'Flo' so she was wearing pajamas and off
limits for playtime. She did spend a lot of time rubbing me through the nighty and
keeping me aroused. The next morning she oversaw my dressing and sent me off to
work in a pair of lavender panties a pair of white slacks that zipped in the back and a
pink shirt. With no pockets in my pants I had to place my money in a small bag that
hung from my shoulder on a strap.
"When I am done at Marie's I am coming home to change this is ridiculous."
"Okay if that's what you want."

With that she sent me off to Marie Logan’s shop in the small shopping area of our
little bayside village. Marie’s dress shop was at the far end of the pedestrian
boardwalk that served our village shopping area. I would have to walk the entire
length of the boardwalk to get back to my own shop. I had a half-mile to cover just to
get to the square two-story boardwalk complex. As I walked long the lavender
panties slid beneath the snug fitting white slacks and the soft friction of the cloth
tickled my tucked but stiffened maleness. When I got to the boardwalk I tried to enter
the employees door and found my keys were missing so I walked to the main gate
where several women were loitering.
“What’s going on here Kelly?” I asked my neighbor.
“We’re checking in the contestants in the pageant. Julie your appointment is for 10 so
you better put a wiggle in your butt so you’re not late. Now sign in on the logbook on
the table there.” She indicated a book on a low table. I started to stoop to reach the
table and felt my shoulder bag slip and as I caught it I slipped on the sandy floor and
flopped belly down onto the rail in front of the table hanging with my pants pulled
snug over my rear. Kelly my neighbor pushed her hands firmly on my rear and
stepped between my legs so I was prevented from getting back on my feet. She held
me and worked her leg against my crotch so I was embarrassed by her feeling my
erection. One of the women handed me an ID card and a nametag. Kelly helped me
upright still keeping her thigh pressed into my crotch.
As I rose I felt my slacks and shirt catch on a snag and started to protest but Kelly
pulled on the back of my slacks’ waist band and the two ladies at the table pulled my
shirt’s shoulders back so I slid around the railing and fell. As I fell I felt my slacks rip
and my shirt pull up over my head. The zipper in the back opened and the thin fabric
slipped off my hips and as I struggled to rise the slacks fell to my ankles and the shirt
slipped off my torso leaving me standing in lavender panties and heels. As I stumbled
I sat down in the loose sand beside the boardwalk and Kelly slipped the torn slacks
off my feet and all the women roared in laughter. Blushing I struggled to my feet as
Kelly laughed and told me to get the logbook signed. I stumbled again to the table
leaned over to sign but did not see my name listed.
“Where’s my name on this thing?” I asked.
“Look at your nametag and ID.” Kelly replied
I looked and saw ‘Juliette Markham’ on the ID and ‘Silly Sissy Julie’ on the nametag. I
found Juliette Markham on the list and wrote in the time then saw a question on the
line ‘Did anyone see your panties?’ Kelly leaned over me and check yes and be sure
you write in the correct number of people who have seen your panties.”
“What for?”
“The rules of the pageant require men who show off their panties to spend 15
minutes in the pillory for everyone who sees his panties, if the man puts down the
wrong number his number is multiplied by the right one. Don’t worry we cap the
day’s time at an hour, but you have to finish up the time accumulated by the end of
the pageant so be careful.”
I wrote 4 down as the three tormentors had to know Marlee my wife had seen my
panties. I straightened up and retrieving my purse went around the boardwalk to
Marie’s shop. At her door was a sign “Sissies report to upper level” this made me
retrace my steps to the opposite side of the u shaped complex to mount the stairs
then walk back to Marie’s shop. At the door was another sign “Sissies ring bell and
wait” I pressed the button and all through the complex rang out a loud recording
“There is a man wearing panties on the boardwalk”. All around I heard doors open in
the shops and heard women laugh. Marie came to the door and led me to the back of
the shop. “Sign the log book and put in the number of women who saw your panties.”
“I don’t know how many just saw my panties!”
“Take a guess all of them will check your count. Remember your number will be
multiplied by the correct count.”
“That’s not fair. There could have been twenty see me and even if I am off by one I’ll
be pilloried for more than five hours.” I whined.
“We want you sissies to make a real effort to be ladylike and demure so the penalty
for sluttiness is severe so you won’t repeat it. Besides that old pillory will look cute
with a man in a dress standing in it.”
I wrote in the time and guessed from the sounds about 15 had seen me. For the next
quarter hour Marie measures and fitted clothes and then said “Okay I’ll send it all to
your house tonight.”
“Wait don’t I get something to wear now? All I have on are panties, please Marie I
need to cover up. Let me wear something. Please Marie please?”
“You are so whiny Julie. Okay let’s get you looking girly.”
Fifteen minutes later I walked back to my shop wearing a floral print dress over a
white slip padded bra, garter belt and stockings. Pinned to my bodice was the
nametag declaring me “Silly Sissy Julie”. I let myself in and began to open the store.

The sound of my high heels clacking on the floor seems to taunt me as I opened my
front door to start my business day. I ran a book store which catered to the summer
trade I kept a large area of used books that could be had for a low price with a
guarantee of return for half the purchase price. Some of my books had been cycling
in and out of the shop for years. In the extreme back and up the stairs was an adults
only book and video room. My summer trade seemed to like kinky stuff so a lot of
the adult books were well used. Upon requests I kept a supply of some toys. Mostly
plugs and padded restraints but a couple of paddles and crops hung on the wall as
well as a few adjustable penis chastities that had been brought in when I found one
customer’s order had been over filled. (She only wanted one but made her ones in
the European style so they sent seven). I was uneasy as I turned on the lights in the
room, as the most obvious thing was the huge strap on dildo on of my clerks had put
on the mannequin wearing a corset. Marlee had joked about buying it last year as a
gift for her aunt. I sat at my desk in the store and read the rulebook Marie had given
me as I left her shop. The rules were few but I now knew the women had all of us
under their collective and individual thumb.
THE RULES OF THE ANNUAL WOMANLESS PAGEANT
1. All men must participate no exceptions
2. The winner of the pageant shall be the man who has the most votes at the end.
3. The pageant ends when all men have amassed votes enough to fill the
containers.
4. No man may amass votes on a day he shows his panties or thighs above his
stockings.
5. All contestants must sign each logbook at his assigned time there are seven
logbooks.
1. At the main gate sign at reporting time 30 minutes before your shop’s
opening
 2. At Marie Logan’s shop 5 minutes after first sign in
3. At Sally Kirkland’s hair salon 5 minutes after signing at Marie Logan’s
4. At your shop at your arrival (be sure to look for your shop log)
5. At Brenda Mason’s Diner at your lunch reporting time
6. At the Town Square at the Olde Pillory (10 minutes before your start)
7. At the end of the pier 10 minutes after your shop closes.
6. All contestants must log the number of women he notes seeing his panties or
thighs.
7. For each woman reported the contestant shall spend 15 minutes in the pillory
daily but none shall exceed 1 hour on any given day. If the women checking his
log note more women seeing his “dainties” than he reports the duration shall be
the product of the two numbers. No man may resume men’s clothing until all
pillory time is served.
8. The final tally of votes will occur when all pillory time is served and each man has
performed a perfectly ladylike duty for every wife of every contestant.
9. No man may attempt his ladylike service until demoted to the rank of
“Pussywhipped Pantywaist”. There are six levels above “Pussywhipped
Pantywaist” to be demoted the contestant shall:
1. “Silly Sissy” be male and live in the village of Lacy Shore
2. “Henpecked Sissy” have been a “Silly Sissy” for two weeks and not to have
shown dainties for at least three days.
3. “Horny Sissy” have been a “Henpecked Sissy” two weeks and to have proof of
complete celibacy and abstinence from all sexual release for two weeks.
4. “Bathing Beauty Sissy” have been a “Henpecked Sissy” and have a visible
maillot bathing suit tan (requires application and six countersigners)
5. “Dance Hall Sissy” have been a “Bathing Beauty Sissy” for two weeks and
completed the dance classes needed.
6. “Atoning Sissy” has performed three dance hall shows and has permission
from the committee to make atonement.
7. “Pussywhipped Pantywaist” have made all atonements for offenses and have
served all pillory time.
In the event that no male has been demoted fully the contest will continue until all
are fully demoted and have served.
As I finished reading the rules Marlee my wife walked in. She spoke quietly “Aren’t
you going to stand up when your Mistress enters?”
I looked up and asked, “Are you speaking to me?”
“Yes I am Juliette and it will not go well for you to b heard being so rude. Now have
you signed in at Sally’s?”
“No I just read about it, what’s all this crap about logging in and being demoted to
Pussywhipped Pantywaist?”
“You did not want to bother with the fund raising so all the wives planned a solution,
drew up a system, and executed the plan. Now I checked the two logs you claimed 4
at post 1 but there were 10 so you have 40 quarter hours from that log. At Marie's
you claimed 19 but there were 22 so you have 418 quarter-hours, which added to the
40 gives you 458 quarters or 114 and a half hours. You will be standing in the stocks
for 115 days if and that’s a big if you don’t show the dainties another time. And there
are at least a dozen ways you are set up for a fall there. By the way you will be girly
for 16 weeks or more if the dainties stay hidden. There is no way out except straight
through. Now are you ready to go sign in at Sally’s?”
“I guess, this is so unfair, why are you doing this to me?”
“Julie you are such a whiny little twat. Come with me I’ll show you your log here and
then walk with you over to Sally’s the big bad dommes will eat you alive if I don’t
protect you.”
We walked back to the adult book section where I unlatched the door and followed
Marlee into the room. The log was attached to the floor under the table where the
dildo-wearing mannequin stood. Marlee stood at the edge of the table and pointed to
the floor. I crawled under the table and marked the time by the date and wrote in a
zero for women who had seen my dainties. I backed out and as I did I felt my dress
sliding up and heard Marlee say “Cute panties.” I jerked upright and banged my head
on the table and squealed in pain. I stood rubbing my head as Marlee went under the
table to sign it.
“Smart move Julie, you wrote in zero, so no matter how many say they saw your
panties the product is still zero. Be sure to let the other sissies in on the deal.”
“So now you’re being nice to me?”
“Sweetie I’ll always be nice but this summer you are going to be squirming in
women’s clothes all the time. Now go in the toilet and take off your panties, I’m
putting a chastity on the little dangly thingy.”
“What?”
“You read the rules ‘Horny Sissy’ rank requires celibacy and total abstinence. The
sooner you start the sooner you finish. Of course the hardheads will prevent any of
you from getting done too quickly. Now double quick panties off and tucked in your
bra then out here with skirt up in front.”
“I don’t want to. I don’t like this.”
“You don’t have to like or want it you just have to do it.”
“But I didn’t get to have sex last night or for the three nights before because you
were having your monthly. I’m already horny, promise me you’ll let me out for some
relief.”
“I promise I’ll have sex with you like I never did before.”
“Okay” I whimpered knowing when I was whipped.
“You know I love you don’t you?” Marlee asked when I returned.
“Yes, but why are you going along with this?”
“It’s fun and kinky and you look so embarrassed and flustered. I was laughing my ass
off watching you click those heels on the boardwalk. This is just a perfect little event
for our little town. All we have is the summer season to make a year’s income. We
have every cabin rented through the early fall. These gadgets are going to sell like
hotcakes.” She said clicking the chastity on my manhood. “Even with the renter
discount we make fifty bucks on each one. Turn around and bend over sweetie.”
“What now?”
“Skirts up let me see your sissy pussy.”
“What?”
“Your sissy pussy, bend way over and spread out.”
“What are you doing?”
“Just making the play things secure. Can’t have some other woman playing with my
cutie. Now this is cold.”
“OOH. That IS cold, what is that?” I asked as the shocking cold substance anointed
my opening.
“Lubricant for your pretty purple plug sweetie, now smile here it comes.” She said.
“OH NO”
The cold lube was followed by a probing object that soon plunged in and stretched
me painfully then eased as it seated its shoulders inside my rear. She murmured,
“such a tough guy to take such a huge plug with out crying. Now go get your panties
on while I wash my hands.”
I slid my lavender panties up my legs and made sure they were not holding my skirts
up. I went up the stairs to my main room wincing as the plug tormented my stretched
bottom. My assistant Ashley was getting her purse and walking shoes stowed in our
break room and chatting with her sister Arlene who ran the jewelry store next to
ours. Arlene giggled as she said,
“Look Ash Marlee made Jerry into a perfect little miss sissy. Ooh let’s see your
nametag. Julie, just darling. Gotta go Ash, Bye Julie hope to see you soon I have some
nice earrings for all the sissies.”
I walked by the breakroom after acknowledging Ashley and Arlene’s greeting and as I
did Ashley called out to her sister, “Arlene look how Sissy wiggles her butt.” I cringed
as Marlee spoke up and said, “Julie has her plug in so none of you wicked girls can
take advantage of her. I don’t share my sissy with anyone.’