Halloween Story
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A Halloween Story
By Cassandra Morgan
In the tiny pockets of time, eternal truths can be unveiled. You'll be in
the middle of an ordinary conversation, and suddenly, someone will ask a
question about a fundamental truth. Pay attention, and the world will teach
you a lesson.
At least, that's the way it happened with my wife Ginger and I.
We were sitting around, wasting the minutes until dinner. We worked hard.
Ginger was a psyche major at UC. I'm a junior high math teacher. So we
needed a minute or two to unwind. Ginger was watching Jeopardy on TV. I was
trying to solve an online crossword puzzle.
Ginger scowled at the TV. "Hitler," she said, loudly. "Who is Hitler?"
I looked up at her. "What's an five-letter word for 'imbecile?' " I asked.
"Trump," she said, proudly.
I chuckled. "Funny," I said.
"Nick? Did you remember to buy candy?"
"Yeah," I said. "We should be in good shape."
"Did you buy good stuff or that cheap crap?" she said.
"It's candy!" I said. "What does it matter? If it's sweet, kids will eat
it."
"Nick, don't be a cheap ass. Buy Snickers. Buy Butterfingers. Buy Reese's.
Don't buy hard candy."
"I bought Snickers," I said.
"Good." She went back to her TV program.
By now, Halloween was on her mind, however. The questions kept coming.
Suddenly, my wife was Alex Trebek.
"So what did you decide to wear to the party?" she said.
"I haven't," I said. "Maybe the Lone Ranger. What do you think?"
"The Lone Ranger? What? Is this your grandfather's party? No one under the
age of dead has ever heard of the Lone Ranger."
"Well, they had that movie."
"One person in New Mexico saw that movie, and he made a mistake when he
bought his ticket. The Lone Ranger is a lousy choice."
"The Black Panther?"
"Are you black?" Ginger laughed. "If I was a black man, I'd slap the shit
out of a wormy white dude like you when dressed up as the Black Panther.
Besides, we know how you want to dress."
"What do you mean?"
She smiled. "Think about what you've been for the last few years. What do
the outfits have in common?"
"Hey! You thought it was a hoot, too."
"So let's see. Last Halloween, you were a prom queen. The year before, you
were a princess. The year before that, you were a nurse. And the year before
that, you were a cheerleader. I sense a trend here."
I shifted in my chair. "What trend?" I said.
"They're all girls, dummy," she said. "Every Halloween, you go as a girl.
Every. Fucking. Year. You're like Groundhog Day. October comes, and you put
on panties.You don't think anyone notices, but we all know about you."
"Ha, ha," I said. "It hasn't been a big deal. They're just costumes."
"Sweetie, look at you. Your hair is long because you dress on Halloween.
Your ears are pierced. Shit, everyone knows about you and your kink by now.
Mrs. Henderson stopped me on the way to the 7-11 the other day. She asked
what dress you were going to wear this year. And I wondered myself. You're
the neighborhood sissy."
"I don't have to wear a dress," I said. "I'll go as Captain America."
Ginger giggled. "Or maybe you could be Miss America. We could buy you a
sash. You could wear a gown. You could twirl a baton."
"How about Batman?" I said, ignoring her.
"There is a new TV show about Batwoman," Ginger grinned. "More your style."
"Drew Brees?"
"Nancy Drew?"
"Why don't we talk about this some other time?" I said.
"Fine," she said. "But let me ask you a serious question."
"Oh...okay."
She turned off the TV. She turned to me and laid it on me.
"Nick," she said. "How long does a cross-dresser have to cross-dress before
he's a cross-dresser?"
"Excuse me?" I said.
"I'm serious. Do you have to dress once a week too join the club? Once a
month? Once a year? Three times every six months? How often does a trans
woman have to dress to officially be a trans woman? What's the frequency,
Nikki?"
"I...I don't think you measure that in time."
"Ding-ding-ding," she said. "We've got a winner. You cannot measure
compulsion by frequency. The depth of someone's addiction is a moving
target. You don't have to do heroin that often before you're a junkie. You
don't have to lose millions before you have a gambling problem."
"So what's your point?"
"My point is that I think you can be a transvestite even though you just
dress up once a year. I mean, you do it every year. Every year. Like a bad
habit. If you die on Halloween, they'll bury you in a dress like the
transvestite you are."
"I'm not a transvestite," I said.
"It's all labels," she said. "What does it matter what people call it?"
She paused. She looked at me for a long moment.
"But you are," she said, grinning.
I stood and walked into the kitchen. I was not a transvestite, I told
myself. I had dressed up four years ago because we were students with no
money, and she had an old cheerleader outfit in her closet. The next year,
when I was a nurse, we found a cheap set of scrubs that fit me. I'll concede
that going as a princess and as a prom queen were expanding on the theme,
but that didn't make me a cross dresser. Hell, there are more than 1,000
days in a three-year period, and I had dressed up on a couple of them. Big
deal.
I got a bottled water out of the fridge. Ginger walked in behind me.
"I'm not trying to insult you, Nick," she said, her eyes twinkling. She was
enjoying the debate. "I'm talking about the human condition. I think it's a
good question: How many days do you have to wear panties before they're more
natural than boxers?"
"I don't know," I said.
She shrugged. "I don't know either. But there has to be a guideline, right?
I mean, a man has to live as a girl for a year before he can get a sex
change. Do you want a sex change, Nickie?"
"I don't want a sex change," I said. "This is just about ... being
different."
"Nick?" she said "Nick, how does it make you feel when you dress as a girl?
Honestly?"
"Shit, Ginger," I said. "It's been a year. I don't really remember."
"Nick? Talk to me. Do you feel like a woman? A drag queen? Are you a man
wearing a dress? The day after Halloween, how eager are you to put on pants
again?"
"Um...it feels....it feels...nice," I said. "Is that what you want to hear?
It feels like clouds and lace and floating. It feels ... feminine. I mean, I
don't have to do it. But if we're being honest, sure, it feels nice."
Ginger smiled and nodded.
"Then why don't you dress up more often, Nick? Some women might care, but I
don't. You know I don't. Some trans women want to dress as much as they can.
Don't you?"
"You know why I can't."
"The Colonel?" she said, referring to my father. "Yeah, I can see where he
would suck the desire out of you. Your sister? She's a nun, Nick. She's not
the pope."
"My family would hate me," I said.
"Not everyone gets along with their families," Ginger said.
"Once a year will do me," I said. "Once a year is plenty."
And still, I wondered.
* * *
We were still in the kitchen, still talking about desires and addictions,
leanings and compulsions. Ginger sighed. "Nick, come with me. I want to try
something," she said.
She led me into our bedroom. She walked into her closet. She pulled my old
Prom dress off of a hanger. It as as magnetic as ever, yellow and white and
ultra feminine. She fumbled through her bureau and picked through her
underwear. Panties. A bra. A corset. A girdle. Hose.
She turned to me. "Put these on," she said.
"It's ... it's not Halloween," I said.
"Just do it. Let's see how much you like it."
And so, hairy legs and all, I pulled on the underwear. The panties felt snug
and cool, like always. The bra was a gentle hug, as it usually is. The hose
were like angels stroking my legs, as ever. The usual tightness of the
girdle was comforting. As I stood there in my shimmering white underwear, my
penis swelled with excitement.
I stood in our bedroom, dressed only in the lingerie. Part of me felt
silly, but most of me felt as if I was home. There was a soothing nature to
tightness of the clothing, a comfort that spread throughout my nerve
endings. It felt ... right.
Ginger reached up and put my breast forms -- I wore them last. year -- into my
bra cups. I felt their familiar weight. I smiled.
"Do you like boobs?" Ginger asked.
"I.. I think it's the most feminine part of a woman. The boobs feed babies.
They're a miracle."
"And they jiggle nicely," Ginger said, beaming. "But if you get your on,
they'll feel nicer."
I didn't have on any makeup, and my hair wasn't rolled, but as I posed in
front of the mirror, I felt the energy surge though me again. That's the
great thing about dressing so infrequently. It always felt like the first
time. I felt the arousal awaken in my body.
"Let me ask you another question, Nikki," Ginger said. "Do you need the
whole outfit? Or are just the panties enough? The panties and the bra? The
hose? Do you need the dress? The makeup? Do you need someone to see you
until you're officially a sissy?"
I looked at her. I had no answers to her questions. Can an addiction really
come once a year? Was I like one of those flowers that blooms annually? Was
I the fucking Easter Bunny?
I moved around the room, and I could feel the clothes take over my soul.
Teenage boys, wearing their sister's clothes, know how I felt. It wasn't as
much how the clothes made me look; it was how they made me feel.
I don't know if other men who dress as women on Halloween feel this
yearning. To them, perhaps the cloth is just cloth. But Ginger was right.
There was a compulsion that awoke in me when I did my yearly dressing, an
ache that was finely eased.
Hell, I had read the stories of the men who make deals with their wives to
dress once a week, twice a week. My life didn't allow me to do that. I
didn't allow me to do that.
I looked at myself in my mirror again. I loved the image there. I put my
hands on my hips and posed. Ginger giggled.
"It isn't just coincidence, is it Nikki?" she asked. "I mean, four straight
Halloweens -- five if you dress this year --doesn't just happen, does it? You
really are a girlie man, aren't you?"
I hung my head. I felt a tear tumble down my cheek
"I think so," I said.
* *
I moved across the bedroom. This was different for me. It was always hard to
change back into boy clothes the day after Halloween, but I couldn't even
blame this on the holiday. I moved around the room -- the first non-Halloween
dressing I had done since I was 13 -- and felt the femininity in me.
Ginger moved up behind me. She lightly ran her hands over my sides. It was
like sparks. She cupped my breasts and kissed my neck. I rolled my head back
and moaned.
She was rubbing my butt now. It felt delicious. She reached in my panties
and toyed with my anus.
"Are you my girlfriend?" Ginger said. "Are you my woman? Tell me, Nikki.
When I fuck you, am I the husband? Do you feel pretty? Do you wish you could
get pregnant?"
I groaned.
Ginger reached into her bedstand. She pulled out a dildo and a harness.
"From my college days," she said. "With Becky."
I knew she had experimented in college. Frankly, I found it erotic. But now
she was turning me over and rubbing her dildo against my ass.
"Beg me," she said.
"No. Not that," I said.
"Beg me, Nikki. I can make you my woman. Are you ready?
I put my face in the pillow. I felt her ease the head into my ass.Then she
pushed, and it went deep. She pushed again, and I was being fucked. Plain
and simple. My wife was fucking me.
""Please," I whimpered. "Take me hard."
I thought about screaming.
But I could already hear my voice.
* * *
The next day was Friday, one day before the party. I still didn't have a
costume. But Ginger said we were going to fix that. I wore my women's
underwear, including my breast forms. I put on a jacket to help hide it.
Ginger wound through the streets of Cincinnati, and she headed west.
Finally, she pulled into a strip mall in front of a store I didn't know. It
was called "Out of the Closet."
"They have the best costumes in the city," she said. "A lot of drag queens
trade in their old outfits here. Other trans women. I think we'll find
something nice for you."
I didn't say anything. I had surrendered. For all the good it was, and all
the bad, I was going to be a girl again.
We walked into the store, amid the frocks and feathers. There were so many
colors, so many dresses.
"Come here, muffin. Let's shop!" Ginger giggled.
A stock woman with red hair approached us. "Can I help you folks?" she asked
in a dark voice. Obviously, she was a man dressed like a woman.
"Yes," Ginger said brightly. "My husband is looking for a women's costume
for tomorrow night. What do you have left?"
"Oh, we can fix him -- her? -- up just fine," the woman said, looking me up
and down. "Any thoughts?"
"Well,, we're here to get ideas," Ginger said. "Can you show us?"
"Sure," the woman said. "Take this Tinker Belle outfit. It's cute, and the
wings move independently. We have a sexy nurse outfit."
"Oh," Ginger said. "he went as a nurse a few years ago. Not a sexy nurse
though."
"How about this Flapper outfit?" the woman said. "I love the silver dress."
"Can my husband try it on?" Ginger said.
"Sure. She has the hips for it. I'm about two biscuits too big to wear
that."
I took the dress and moved into the dressing room. I slid the dress up my
hips. It was snug, sexy, feminine.
I slipped the rest of it on, and it felt fabulous. I looked, and I could see
myself on John Dillinger's arm. The red-haired woman -- Lois -- helped me put
on makeup to complete the look.
"That's on the short list," Ginger said.
I tried on a Geisha outfit. It was tight and binding, but I loved the look.
I tried on a retro flight attendant's outfit. I didn't care for it. I tried
a western dress -- I could have been a dance hall strumpet -- that had a
flowing skirt I loved.
I tried being Little Red Riding Hood. And Cleopatra. And Glinda the Good
Witch.
I was Marie Antoinette. I was RuPaul. I was a woman cop.
"Look, I have something for you to consider," Lois said. "What do. you think
of this?"
She held out a long purple gown with sequins. It was stunning.
"Wow," I said.
"You don't know the half of it," Lois said. "It comes with a skin dye. You
can be a Supreme, or a Vandella. Nothing gets the white boys going like this
outfit."
"How long does the dye last?" Ginger asked.
"About a week, ten days," Lois said. "But I know a man who never came back.
Once you go black, you never go back. Isn't that what they say?"
Ginger giggled. She held the dress up against my body.
"Ginger," I said. "I don't want to be black. I have friends, and they might
think I was mocking them. I don't want that."
She nodded, sadly. "I'd love to see you as a sister," she said. She turned
to Lois. "What else is there?"
Lois brought out a red leather skirt and a leopard print blouse. "You could
be a hooker," she said. "This outfit pays for itself."
"I have a wedding dress in the back," Lois said. "But I don't think it's
your size."
"Too bad," Ginger said. "Nikki's a virgin. She could wear white."
We looked at a harem girls' outfit. We looked a school girl's uniform. We
looked at a Sandy -- when she was the tough girl-- costume from Grease.
Then, as if a light had come on in her face, Lois smiled. "I have it," she
said. "The Golden Fleece of costumes. The Holy Grail. You're going to love
this."
She went into the back of the store and came out. In her hands she had a
dress that was mesmerizing at first glance. It was black and white, short
and sexy. It had a cute little cap and a feather duster.
You guessed it. It was a Sexy Maid's costume. Commonly known as a French
Maid's uniform.
This one wasn't made for a lot of function. It hinted at pure sex. It was
short and tight with an impossible number. Of petticoats.
"If you want something to work in, you can get those at the uniform store on
seventh," Lois said. "But what's sexier than a sissy maid? What is more
submissive to a man than someone who curtsies and says "oui masseur.'"
"Oh, Jesus," Ginger said. "We'll take it. We'll take two. Three. And a
Brillo pad."
"You can add a leash and a collar if you want," Lois said. "We have plugs
and cages."
"We'll take all of it," Ginger said. "What do you think, Nikki?"
"It doesn't sound like I have a choice," I said.
Ginger shrugged. "Well, you're the fucking maid. Maids don't get their
choice."
"Can I suggest something," Lois said.
"Of course."
"How about something for you?" said Lois.
"For me?"
"Yep. Look here," she pointed to a black leather bustier on a display case.
There was a pair of black, skin-tight pants underneath it. There was a small
whip with it.
"You could be your maid's mistress," Lois said. "You can pick between the
whip and a paddle. You won't believe the power you feel in this outfit."
Ginger touched it gently. She smiled.
"Do you think I can pull it off?" she said.
"Without a doubt. You were born to wear this," Lois said. "Check out your
biceps."
"I want it," Ginger said to herself.
Lois nodded. "She wants it, too," she said, indicating me.
We were checking out when Ginger turned to me.
"Here's a question," she said, again. I was getting irritated by her
questions. "Does the uniform choose the lady, or does the lady choose the
uniform. Lois never recommended the mistress outfit for you. Is that because
you could tell you were a Sissy? Did I get the leather because it's in me?
What do you think?"
I looked at her paddle.
I thought it was going to hurt.
* *
Ginger was right about one thing. My senses were heightened by the
anticipation of being seen. Is it that way for all of us? Do we hunger to be
exposed, to let our friends have their laughs, to suffer the comments?
Ginger drove toward the party. I sat in the back seat, like a good maid. I
watched the people on the sidewalk.
For most of Cincinnati, Saturday was the day before Halloween. So the
sidewalks were empty except for a few blow-up ghosts and that cobweb you can
put onto your trees.
Ginger, in her power uniform, glanced back and me and smiled. "This is going
to be the best Halloween ever," she said. "Hell, we may not let November
ever come."
I was quiet, but Ginger kept prattling on.
"You know, Nikki, the important thing isn't your maid costume," she said.
"It's your attitude. I want you to embrace your role. You're a domestic. If
someone wants an ashtray, I would you to fetch it. If someone needs a drink,
that's your responsibility. You're the maid. Got it?"
"Yes, ma'am," I said.
"Very good. Now, what do you do if Chuck has a boner?"
"Ma'am!"
She snickered. "You service him," she said. "I want you to get the full
sissy experience. Guys are part of that."
"Ma'am, I don't need men. I'm married to you."
"Look, Nikki, when you wear a dress, you accept that we're both going to
expand our lives. That means other partners. That means other experiences."
I inhaled deeply. This was going too fast.The changes were too stark, too
drastic. I wasn't ready for life as a woman, or life as a sissy.
We drove down Cypress, took a right on 42nd, turned again on Elm.
"Let me ask you a question," Ginger said. I groaned. "No, this is a good
one. Nikki, how many dicks do you have to suck before you're bisexual? I
mean, is there one night you're just playing, and the next, you're
committed? How many times do have to suck sperm before you're clinically a
bi? Twelve times? Twenty?"
I flinched. "I'm not bisexual," I said.
"You swapped spit with Chuck last Halloween, remember? If Joyce hadn't
walked in on you, you would have kissed the cobra. Admit it."
"I didn't kiss Chuck," I said. "Chuck kissed me."
"Regardless, my husband played tonsil hockey with another man. Did you think
I would forget?"
"You never forget anything."
"So do you dream about it? When you imagine yourself in a dress, do you
imagine going down on Chuckles? Are you walking up the aisle? Am I even in
the picture?"
"You're my wife. I love you."
"Maybe you're my wife. What about it? Do you want to swap? We could trade
wedding rings if you want. In some places, they're into wife-swapping. This
is just a different kind of wife-swapping."
"I like my wedding ring."
"Awww. That's so sweet. My Sissy likes her ring. When you get your boobs,
maybe we'll get you a nipple ring."
"I should have been the Lone Ranger," I grumbled.
"Maybe Calamity Jane," she said, laughing.
We parked on the street and walked to the front door. I wondered if the
neighbors knew me by sight. Ginger rang the doorbell.
Sue Nellings opened the door and broke into a wide grin. "Look at you two.
Oh, spank me, Mistress. Are you taking numbers? And you! I love a good maid.
Why don't you go to the kitchen and serve the guys some beer? You're
certainly dressed for it."
I made my way through the costumes in the room. There was Iron Man and a
Musketeer and Thor. There was Little Bo Peep and Maid Marion and Maleficent.
There were Romeo and Juliet and Thelma and Louis and Bonnie and Clyde. Elton
John and Superman and Robin Hood. People busted their butts for Halloween
at the Nellings.
But when I walked in, it was as if a light had been turned on.
"My God, she is so perfect!"
"She's a he, you know."
"She's Nick. Nick with a dick. That's our girl."
"Hey, maid. Would you clean my balls?"
"My Sissy. Curtsy for me."
"Fucking fags. I hate it when they're pretty."
And on it went. Most of these people had seen me in a dress for four years.
Still, they laughed and joked and amused each other at my expense.
I went to the kitchen. There was a tray of beers on the counter. I picked it
up, and I began to make my way through the crowd, handing them out. No one
told me it wasn't my job.
"Nice ass."
"I know why those lips are so plump."
"Do you hire out? As a maid, I mean. Or as anything else."
I began to work the room, and soon enough, I faded into the woodwork. Let's
face it. It was really no shock to anyone that I had come as a female. It
began to feel ordinary, serving my friends. I liked the feeling. I liked
having something to do at the party but chit-chat, and I loved the uniform.
The crowd began to pair off to dance. A tall black man named Leon pulled me
into him, and I could feel his gender poking at me. Ted cut in. Then Benny.
Then John.
And then someone familiar cut in.
Chuck.
Chuck was the best man at my wedding, a former college classmate who had
been a golf buddy for years. Now, he stood in front of me with this wicked
grin on his face, his unruly blond hair catching the light.
The year before, late in the party, he had kissed me right on the lips. I
was confused, and I didn't know what to do, and I had kissed him back. We
never went any further, no matter what Ginger would tell you. I never
touched him, and he never touched me.
"Hello Nikki," he said softly.
"Hi Chuck."
"You're a girl again," he smiled.
"Yes."
"Did Ginger make you?"
"No."
"I knew that. I thought you might have the illusion of being forced, though.
A lot of you sissies are."
"Do you think I'm a sissy?"
"I'm glad you're a sissy," he said.
"I think I am, too."
He smiled. "I liked kissing you," he said.
"You shouldn't have. I'm married."o
"As a man, you're married. As a maid? Well, we'll have to ask your Mistress,
won't we? She's dressed provocatively. Last I saw, she was flirting with one
of the six Wonder Women we have at the party."
"Which one?"
"Nancy Olson, I think."
"Nancy's nice."
"Yeah. And you're in the gayest relationship in Ohio."
I turned and started to walk away. Chuck grabbed my wrist. I turned, and I
felt his face close to mine. His lips grazed my mine. His hands were on my
hips.
"Mr. Peanut wants a kiss," he whispered.
"Mr. Peanut?"
"Just a nickname for my dick. Make him feel better, won't you?"
And I did. I slumped to my knees, remembering that Ginger had told me to
service him. I would have thought there would be a big moment before I
became a cocksucker, but there wasn't. He simply slipped his knob between my
lips, and I became to suck gently. And then I was blowing him. And it was
good.
Both times.
* *
I woke up in a heap. I was sprawled out on the spare bedroom, my skirt hiked
up to my stomach. I could taste last night's lipstick. I had on one heel,
but I had no idea where the other was. My butt hurt. My face was sticky. I
wobbled toward the bathroom in the Sissy Walk of Shame.
I started the shower and dug for some headache powders.
Then Ginger came in, smiling as ever. "Oh, baby. You need a morning-after
pill to make sure you're not pregnant?"
"Funny," I said. I stared at the floor. "You know I slept with Chuck last
night."
"I know. You know I slept with Nancy."
"Dyke."
"Fag."
We both started laughing. We had come a long way in a week.
"Look, Nikki," she said. "I want an eggs-white omelette. I want a fruit cup.
I want wheat toast. Can you make it for me?"
"Um...sure," I said. I started to remove the dress.
"Keep in on," she said. "It's still too fancy to wear every day, but I'll
get you some more uniforms."
"More?"
"You're going to be my maid from now on, aren't you? You want it as bad as I
do, don't you?"
"Ma'am?"
"You'll like it. I'm not a heartless bitch like in the stories. So this is
for you more than for me."
"Oh," I said.
"Let me ask you a question, Nikki. How many plates does a Sissy husband have
to clean before it's no longer a game? How many days of wearing a maid's
dress do you have to wear before it's your normal attire? How many dinners
with the Colonel do you have to serve at before he accepts that you're his
daughter, not his son?"
"I...I don't know if I want to be a maid," I said.
"That's your vanilla side talking, Nikki. You love the clothes. You love the
makeup. You love our neighbors looking at you and knowing what's in your
soul. You're a Sissy, Nikki. You're a girl. Admit it. Embrace it."
I took a deep breath. I stood in front of Ginger, my Mistress.
And then I did the damndest thing.
I curtsied.
Copyright (c) 2019 Cassandra Morgan
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- 04.05.2022
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