Sissy Mission 6

Poodle Skirt
By Cheryl Alison

I sat on the bench assessing my surroundings. It was

a well-kept small town, with a cobblestone main

street and nicely maintained historic buildings.

Banners and awnings in the front of shops fluttered

in the breeze, advertising everything from antiques

to hardware. Since it was a town located on a large

lake with lots of recreation opportunities, it was

busy on this early June day. People strolled up and

down the sidewalks, ice cream cones in hand, most of

them escaping from stressful jobs in the city or

feeling the freedom of being out of school for the

summer.



The breeze tugged at my skirt, and instinctively I

moved my left hand to the hem. I looked down at the

skirt, reminded of how out of place I was here.

Rather than a light cotton or rayon summer skirt, I

was wearing a heavy pink poodle skirt right out of

the 1950s. I was also wearing black and white saddle

shoes with white bobby socks, and a pink sweater. My

hair was done in what my beautician had called a

"pixie cut" and my nails were painted pink to match

the outfit. Pink blush, lipstick, and eye shadow also

complimented my ensemble, while a pair of vintage

cat-eye sunglasses provided the finishing touch.



In short, I was an anachronism. Most of the people

around me were dressed in L.L. Bean casual, while I

was a pink 1950s girl surrounded by the millennium.

Only the town, perfectly restored in its brick

facades, was a fitting surrounding for me. People

were beginning to take notice the moment I sat on the

bench, and passers-by were very interested in what I

was doing. The first group of strollers was three

older women, who had probably grown up in the 1950s.

They stopped, lining up to scrutinize my outfit.



"Well, honey, that is a cute outfit!" bubbled the

more outgoing of the three. "Why, I haven’t seen a

poodle skirt since high school. Where did you get

it?"



I gathered up some courage and spoke. "My mistress

gave it to me. I am being punished for being a bad

little girl."



My voice spilled the beans. In makeup and shades, it

was not obvious to the general public that I was a

man. However, when I spoke in my usual deep voice,

the ladies could hardly avoid the truth.



"Oh!" yelped the woman. One of her friends covered

her mouth and then sort of giggled nervously. "Well,

we have to be going, girls," she finally said and led

her friends down the street, bewildered.



In the meantime, more and more people seemed to be

taking notice of me in my unique situation. Many

probably thought I was part of some sort of store

promotion, so it seemed that folks on the other side

of the street were gravitating toward my side of the

street.



A couple of girls in their teens stopped by in shorts

and crop tops, complete with lip-gloss and sun-

bleached hair. "Are you giving away coupons?" one of

them asked.



"No, I’m here to be punished."



Once again my voice gave me away. The girls began

giggling uncontrollably, but instead of moving on as

the older women had, they stayed.



"Punished for what? You’re a man." The two statements

didn’t really seem to fit together, but marked their

confusion pretty well.



"I’ve been a bad girl."



"Oh, I see," smiled the taller of the two. "Well,

you’re very pretty. Do you have a boyfriend?" she

said, smirking.



"Err, no." I said, turning beet red and hoping they

would leave.



"Do you have panties on under that skirt?" piped up

the other of the two.



"Yes, they are pink," I answered, with the statement

that Mistress had told me to use if anyone asked.



"Do you like to wear dresses and stuff? Are your

boobs real?"



I squirmed on the bench, wishing they would leave.

"Yes, I like to wear girlie clothes. My breasts are

forms that I stuff into my bra."



"Are you a crossdresser?"



"Yes, my mistress doesn’t allow me to wear any men’s

clothes anymore outside of work."



"Well, we think you’re cute. Bye."



Finally! It was about time to end that humiliation. I

looked at my watch. I had only been on the bench for

fifteen minutes! It had felt like the proverbial

eternity. I had three hours to go.



"Mommy, look at that lady!"



"Nice skirt!"



And it went on and on. Every time I interacted with

someone, his or her eyes got big in shock as I

revealed my maleness with my voice. Then it would

turn into a long explanation about how I was being

punished.



It wasn’t until someone offered me an ice cream cone,

though, that anyone noticed another aspect of my

predicament.



"I’ve seen you over here for about an hour, and I was

wondering if you would like an ice cream cone," said

the woman in her thirties.



"Yes, I’d like that," I said, reaching out with my

left hand. I didn’t catch her reaction at my voice,

but as I was taking the ice cream cone from her hand,

I dropped it on my skirt. My urge was to bring my

right hand forward to grab it, but I lurched against

the bench. You see, my right hand was handcuffed to

the bench.



"Oh, dear. Let me help you," she said graciously,

pulling out some napkins and helping to wipe off the

mess."



"Thank you," I said.



"Poor dear, why are you handcuffed to the bench?"



"I’ve been a bad girl and I’m being punished."



She erupted into laughter. "What are you being

punished for? It’s kind of unusual to be punished by

dressing in a poodle skirt and being handcuffed to a

bench."



"My wife caught me with her pantyhose."



"Oh, you’re a crossdresser! How interesting!" she

said, just a little too loudly, drawing the attention

of the seven or eight people adjacent to our area. A

few threw disgusted looks our way, and others sort of

milled around, mumbling to each other. I could hear

the occasional "weirdo" and "freak" come out of those

conversations.



"How long do you have to sit here?" she asked.



"Until 6 o’clock," I answered.



Her eyes actually flashed something like sympathy.

She sat down on the bench next to me, putting her

hand on my knee. "Well, I’ll sit here for a minute

with you."



I was glad to have found someone to talk to, hoping

it would pass the time. She seemed very sympathetic,

and it was almost a turn-on to have a woman

interested in my state, rather than repulsed by it.



"You don’t recognize me, do you?" she said.



"No," I said, expecting her to relate to me that she

was some kind of local celebrity.



"I’m Nancy’s friend Julie from work. She asked me to

come by and see you."



My wife’s friend! I had met her and her husband at a

holiday party we had held at our house. Now I

recognized her. The sense of humiliation took another

turn, deepening and forcing me to realize that

Mistress never leaves anything uncomplicated.



"You look really good. I’m surprised. I thought you

would look like a guy in drag, but you look like a

fifties girl, just maybe a little bit on the tall

side," she complimented.



Well, maybe it wouldn’t be so bad after all. Perhaps

Mistress had just sent Julie to check on me. She was

certainly being sympathetic.



"Nancy did ask me a favor, though. You see that

female police officer down the street? I’m supposed

to ask her for a handcuff key. Then you’re to come

with me."



Crap--here come the complications, I thought.

Mistress is never happy just humiliating me in a

simple fashion.



Julie motioned the police officer over. "Ma’am, I

think this poor girl here has been the victim of a

trick. Can you unlock her?" I kept my face down,

hoping that she wouldn’t notice that I was a man.



"Sure," said the lady cop. "How did you get in this

situation?" She had done what I dreaded most—asked me

a direct question.



"I was a bad girl and I’m being punished."



"Oooh!" she said, taking some delight in my

predicament. "Perhaps this is a punishment I can

suggest to our local judge!" she joked. "You’re

cute."



I didn’t feel so cute; as a matter of fact, I was

beginning to feel a little sick, knowing that Julie

had been sent by Mistress to take me to entirely

another level of humiliation.



After the cop left, Julie said, "Come on, I’m

supposed to take you for a drink."



That didn’t sound too bad—Mistress had taken me to

the House of Pancakes in drag before. I figured I

could handle a half hour in a bar.



Julie took my hand and led me down the street to

where a sign said "Big John’s Pub— Happy Hour 5:00."

It was noisy inside and filled with patrons. As we

entered the doors, though, my heart just about

stopped. On a stage across the bar was Mistress,

dressed in her favorite black leather mini and a

sleeveless shirt, perfectly made up and wicked.



"Happy hour has begun," she yelled into the mike,

amid cheers from the patrons. "Today’s happy hour is

special. We have a drink promotion for the ladies.

Its called Spank the Transvestite! If you swat this

little girly man’s bottom, you get a free drink!"



The crowd loved it, anything for a free drink, and to

watch the humiliation of another human being to boot.

What a deal! Many of the women in the bar rushed

forward to participate.



Mistress came down from the stage and took my hand,

leading me up to a chair. I expected her to tell me

to lean over it, but instead, in the final crowning

humiliation, she sat down, and pulled me over her

knee. She whispered in my ear, "I want to hold you

and watch your bottom get red."



In a flourish for the crowd, she raised my pink

skirt, revealing my skimpy pink ruffled panties for

all the bar patrons. A cheer rose up, and someone

started chanting, "Spank! Spank! Spank! . . ."



As each woman came up, they had a tray of beers ready

to hand out. The first woman raised her hand and

joked "This is going to hurt me more than it will

you!" and laid into me with a good SMACK! Although

most showed some restraint in their spanking, the

fire in my bottom grew as the night went along.

Periodically, Mistress Nancy would make me stand up

and twirl me around, showing off my red bottom.



As a finale to the evening, Mistress got very

creative. "Our little sissy has been so good tonight,

let’s cool down her bottom!" The crowd cheered as she

made me bend down, placing my hands on the floor with

my bottom high in the air. "Bottoms up!" she yelled

as she splashed her drink across my pink panties. It

ran down, soaking parts of my skirt and sweater.

Patron after patron ran up to the stage, splashing

their drinks on my ass until I collapsed on the

stage, soaked in everything from beer to rum.



Mistress grabbed my hair and pulled me up. With a

glint in her eyes and a sly smile, she leaned toward

me, placing her hands on my face tenderly. "My little

sissy. Mission accomplished?"



"Yes, Mistress," I managed to squeak out.



And with that, she gave me the unusual reward of

placing her wine-red lips on my pink lips, and

kissing me long and hard, her tongue darting around

mine. "Let’s go home and get a shower, Sissy."