F****d to Cross Dress on Halloween

I could tell he was anxious. Informing him about the
Halloween party raised a lot of questions on his end
which I skillfully either ignored or diverted.

I had not been mean right from the start, but I clearly
told him he had 3 chances to come up with a suitable
Halloween outfit idea. If he failed, I would choose for
him. That was our deal. My partner, thinking he could
get away easily, did not listen.

The ideas he came up with were very boring, the typical
football player, Clark Kent lookalike, or superhero
costumes that are so overdone. Worst of all, he chose 3
costumes in which he was a male character, thinking that
I would be lenient this time and that I wouldn’t force
him to cross dress on Halloween.

I had tied a frilly apron on him in front of visitors
before, or made him wear a pink rain poncho to the store
during a not-so heavy downpour. But fully dressing him
as a female in front of my friends, or anyone
actually… well, in that aspect he was still a virgin.


“Alright, it’s already 2pm. It’s time to get you ready
for tonight.” I said to my partner, Mark, who was
lounging on the couch.

“Tonight? Are we still going… I thought you changed
your mind.” He replied without much interest.

Typical Mark. He can be quite the handful when he is not
properly motivated. I would make him pay for this. I had
not told him about the fact that we would actually be
hosting this year’s Halloween party, which was probably
for the better as I did not want to scare him so early

“From now on you will address me as Mistress and I won’t
tolerate any more back talking. Get in the shower and
make sure to be hairless from the neck down.” I said in
my stern voice, a tone very familiar to him since this
is the way I talk to him whenever I’m wearing the pants
and he is wearing the panties.

“Of course, I’m sorry mistress.” My now more timid
partner replied as he turned the TV off and hurried
towards the bathroom.

“Just report back to me whenever you are ready.” I

With my ‘soon-to-be-maid’ in the shower, I had time to
pour myself a glass of wine and get some things ready in
the bedroom.

I spent quite some time shopping for a new outfit for
him this year. It wasn’t cheap, but at least it would
come in handy even after Halloween was over. The whole
charade about him picking his own outfit was just a
trick. Only if he would have said “I want to be a French
maid for Halloween” would I have agreed, since that’s
exactly what I wanted him to be this year.


“I’m ready mistress.” Mark’s words echoed through our

With a blind fold in hand I stepped into the bathroom to
find my partner standing there anxiously with a towel
wrapped around him.

“You smell nice. Now, let me put this on you so it won’t
spoil the surprise.” I said while tying the black satin
blindfold firmly around his head.

“Yes, mistress.”

He was in a meek and obedient state, just the way I like
him to be.
With the thick satin blindfold tied tightly around his
head, Mark could not see how much trouble he was in.

With the thick satin blindfold tied tightly around his
head, Mark could not see how much trouble he was in.

“Follow me.” I instructed my pet as I grasped his hand
and led him into the bedroom.

With a quick tug I removed the towel that was wrapped
around his body. Quite literally his safety blanket fell
to the ground.

He let out a moan and cringed a little.

“Oohh, I like how smooth you are.” I stated while
inspecting his handiwork.

In front of me stood a male in his early thirties who
was completely hairless from the neck down.

“Now, be a good boy and spread your legs for me. Right,
that’s it.” I encouraged him.

The amount of accessories, toys and pieces of clothing
that I had prepared while he was in the shower was
impressive. To start things off, I grabbed a big steel
butt plug and applied some lube.

With my left hand I put pressure on his shoulders,
forcing him to bend over while whispering “Now, be a
good boy and grab your ankles for me.”

Eagerly, my little pet obliged and he was now showing
off his naked butt. He probably had some idea of what
was to happen next, he was no virgin when it came to his
little naughty hole.

The cold tip of the lubed butt plug touched his ass and
I could sense the shivers going through his body. I
applied some pressure with my right hand while I grabbed
his balls with my left hand and squeezed a bit.

“Accept your new cold friend, sweetheart.” I said with a
smirk on my face. I was enjoying this.

“Aahh!” he called out as the plug was slowly sucked all
the way into his ass.


With a lot of force, I slapped his ass with my right
hand as I still held on to his precious balls.

“Be quiet.” I hissed.

“Sorry mistress.” He replied, almost whispering.

This cold toy had already gotten the attention of his
manhood. It was growing, which was something I did not
want just yet.

While I expertly grabbed the first piece of the next
t*****e instrument with my right hand, I squeezed a
little harder around his balls. I could feel his pulse
through my tight grip. His erection responded by slowly
becoming smaller and retreating.

I fit the outer plastic ring around his balls and base
of his cock while grabbing the cage, a new chastity toy
I’d purchased recently which we’d had the not so nice
pleasure of experiencing a few times before. With a
little lube on the inside, it quickly slid over his hard

Mark was aware of what was happening and wanted to
protest, but before I let him say a thing I squeezed
just a little harder while whispering “Don’t even think
about complaining. We have a long day ahead of us.”

I let go of his balls, hearing the relief wash over him,
but it was short-lived.


The padlock that firmly kept the cage attached to the
ring around his cock and balls was now locked in place.
This would make sure he stayed motivated and wouldn’t be
too much trouble to deal with.


Still blindfolded, Mark had trouble putting his feet
into the satin panties I kept open for him to step into.
Once he did manage to put both feet in, while keeping
his balance by holding on to me, I slid the satin
panties up his stocking-covered smooth legs until they
were high enough to keep his new cage concealed.

In front of me stood a very anxious man in stockings,
panties and a garter belt. The plug and cage were
already having an effect on his behaviour. He was no
longer unruly, but instead simply scared. He was at the
point where he would do just about anything I would tell
him to.
The satin suspender belt firmly kept the stockings up
Mark’s freshly shaved legs.

The satin suspender belt firmly kept the stockings up
Mark’s freshly shaved legs.

“Hold onto the door for me.” I told him after leading
him towards the bedroom door. I placed his hands up near
the top of the door while I grabbed the next installment
of his outfit for tonight.

With the laces loosened and the front unhooked I easily
wrapped the underbust corset around my soon-to-be-maid.

“Keep your stomach in.” I ordered as I started
tightening the laces at the back, hooks all clasped in
the front. This would prove to be quite the job.

Quite a few minutes later, the result was definitely
worth my effort. I was sweating a little, but Mark’s
figure had changed drastically. He now stood in front of
me, still blindfolded, wearing his corset. The hourglass
figure he now boasted was one that many women would be
jealous of.

“Stand straight.” I said as I pressed the medium sized
fake breasts to his chest. Mark shivered because of the
cold adhesive that I applied to them. “Now hold on to
your new boobs while I get a few more things.”

It was quite the sight, my partner standing there,
wearing just a pair of soft satin underwear and a corset
while holding on to his fake breasts so the adhesive
could dry and make them more permanent additions to his
new figure. I just had to add the bra before the real
fun could begin, putting on the outer layers of his

One thing was for sure, this would be a Halloween to


Still blindfolded, but this time a little taller due to
the 3 inch heels I had strapped onto his feet, Mark
stood in front of me wondering what would be next.

If he knew, if he could have seen, he probably would
have refused, or at least tried to. I wouldn’t expect
anything else from him, that’s why I wanted to have him
blindfolded for this stage of the process.

I picked up the mass of black satin from the bed and
prepared it so I could drape it over my prisoner.

“Raise your arms… yes, forward… put them in.” I
guided my helpless partner into the satin trap.

Once his hands made it through the long sleeves, I
guided the silky sea down the rest of his body. With the
help of gravity, the long dress fit like a glove around
my corseted victim.

“Let me zip you up.” I said as I grabbed the zipper
which started at his lower back.

Slowly, suspenseful, I zipped him up while whispering
into his ear, “Once you are zipped, there is no way

He almost lost his balance right there, standing in his
high heels. He was so scared and horny at the same time.
It was making me wet seeing him like this.

Once the zipper was all the way up, I used a padlock to
clasp the two metal rings at the back of the neck


Another padlock to make sure he would behave.

I folded the collar of the dress over the padlock so it
would be our little secret. The thought of having him
locked in this sea of satin made me even hornier.

The white satin garment on the bed was next. I grabbed
it and tied it tightly onto my new maid. It was a long
white pinafore apron which matched the dress.

“Turn around for me.”
Mark’s new uniform transformed him into a Victorian

Mark’s new uniform transformed him into a Victorian

Slowly, my new perfectly-shaped maid turned towards me,
his head bowed downwards in shame. He must have realized
he was in some sort of uniform, though he probably did
not want to believe it.

“Very good, just a few minor details.” I said while
grabbing my lipstick.

Getting the lipstick on neatly was no work at all, but
the blonde wig was a whole different matter. Since my
maid was still blindfolded, I had to work a bit to keep
him from seeing while I put the wig on his head. He must
have felt the hair tickle his face because I could sense
he was getting more and more anxious. I was soon ready
to unveil his new identity for the day.


I stood behind him as I asked, “Are you ready to see
your Halloween costume?”

“I… I… don’t know.” He meekly answered, clearly
confused by the complicated mix of arousal and fear.
Honestly, him being so scared only made it more fun for
me. It got me really excited to see what the night would

“Well, here goes!” I said joyfully as I undid his

“Oh my…” his mouth fell open.

He was almost in shock, looking at himself in the full
length mirror on the back of our bedroom door. Well, not
really himself since it was a Victorian maid who was
staring back at him in the mirror. I went all out,
making sure his costume included heels, bright red
lipstick and a blonde wig.

“Why?” he managed to squeak out the question.

“Well, you weren’t very helpful with selecting a
Halloween costume this year, so I figured I would help
you a little.”

“But, I can’t…” He tried.

I did not let him finish. With my right hand I pushed
him forward abruptly, him swaying on his heels, and
lifted the long skirt of his uniform from behind. I
found his panties and through the soft satin material I
immediately grabbed his balls and squeezed them. He
stopped talking right away and just made pleading sounds

“You were saying something?”

“No… ahh… I…”

“What is it?”

“No… Nothing mistress.”

I kept my grip on his balls as I continued.

“Why don’t you thank me.”

“T…Thank you.”

“You can do better than that.”

“Thank you mistress.”

“For what?”

“F-For helping me get dressed.”


“Selecting my outfit.”

“Good girl. Now, we don’t have much time. I want you to
start vacuuming the house, then clean the bathroom and
lastly the kitchen.”


Who did he think he was? For one last time, I squeezed
even harder while I almost yelled. “Okay what?!”

“Yes mistress.” He responded in a high pitched tone.

Finally, I released him.

As he walked past me, taking baby steps in his high
heels, I slapped his ass. It sure was lovely having a
maid do your housework.


I could hear the water running in the kitchen. I was
getting ready in the bedroom, stepping into the harness
straps. After pulling the whole installment up, I
tightened the straps so the big dildo was firmly pressed
against my mons.

My maid was too busy with his chores to hear me approach
him from behind. He almost jumped as I told him to turn
the water off.

Still standing behind him, I guided him towards the
kitchen table. I f****d his legs apart while I pushed
him forward so he was bending over onto the table, his
elbows propping him up.

I undid the straps of the pinafore apron on the back and
grabbed his left wrist. I guided it behind his back and
wrapped the soft material around it a few times. His
right wrist followed.

“Now, you have been a bad girl today. I have to make
sure you will behave tonight when the guests are here.”
I said while tying his wrists together with the apron

I lifted up the skirts of his maid’s uniform.

“Guests?!” He anxiously asked.

“Of course dear. Some of my friends are coming over.” My
hands found his panties.

“I… I don’t know Deborah.” I could feel him pulling
slightly on his bound arms to check if he could move. I
knew he couldn’t get out of it and so did he. I had
enough experience with bondage to know how to
effectively tie someone’s hands together.

My hand moved to the front side of the panties where I
could feel a big wet spot. He was dripping through his
cage, soaking his panties.

“What don’t you know?” I asked him while slowly lowering
his panties just enough to expose his bare ass.

“This is fun and all, but I can’t be seen like this.” He

“Oh, but how can I keep you to myself? I put so much
effort into your costume.” I said mockingly as I slowly
started pulling out the butt plug.

“Ughh… no, but seriously Deb.” He tried again.

I had heard enough. The lubed up butt plug was now
completely out and I dropped it onto the floor of the
kitchen. I lifted the skirt of the dress up so that he
was fully exposed.

“I think you need to learn a lesson.” I stated as I
guided the tip of the big dildo towards his ass.

“But, Deb…” He tried once more.

With my left hand I parted his butt cheeks a little bit
so I could see the stretched hole which was going to be
punished for his remarks.

Slowly, I moved my hips forward until the lubed tip was
now perfectly positioned against his naughty hole.

“But Deb what?” I said with a clear hint of annoyance in
my voice. How could he disrespect me like this,
especially after all the effort I went through?

I swiftly thrust forward and shoved my big cock into his

He almost screamed.

I kept on forcing the dick forward so it slid all the
way in.

“Don’t ever call me Deb again. I’m your mistress…” I
said while grabbing his hips and slowly sliding back out
of his ass until only the first two inches of the dildo
were still stuck inside of him.

“and you are my maid!” I said while slamming the full
dildo back into his ass again.

“Aahhhh…” was all the helpless maid could respond.

I kept this slow out, fast in rhythm going while
listening to his whimpering. It was turning me on.

“Who is my maid?” I asked while still fucking his ass.

“Me.” he said quietly.

“What did you say? LOUDER!”

“ME.” He almost yelled.

This was getting me really wet. I used my right hand to
squeeze into the harness and find my wet pussy while I
kept the slow out � fast in rhythm going. I started
rubbing myself down there and it just felt heavenly.

“Tell me you are my maid.” I continued.

“I am your maid.” He said while breathing heavily.

“Ask me to wear this uniform all night so everybody can
see it.” I pressed on.

The fucking continued, but apart from heavy breathing
and moaning, my new maid wasn’t following my

“Ask me!” I repeated myself while pounding him as hard
as I could.

“AHH… Please mistress, please let me wear my uniform
all night.” He begged.


“So everybody can see it.”

He was beaten. I had clearly won.

This feeling of victory rushed through my body, from the
power I felt through the large strap on, to the rubbing
of my wet lips. I burst into a giant orgasm which made
me fall forward, half on top of my maid who landed on
top of the table.

Breathing heavily, we both laid there for a few minutes
catching our breath.


After slowly pulling out my huge strap on dildo, I
replaced the emptiness with the steel butt plug once
more. My maid was moaning, clearly struggling with the
a***e of his ass.

“Now clean up this mess. We only have about half an hour
before the first guests arrive.” I commanded while
untying the apron strings that had kept his arms in

He slowly rose from his compromising position and pulled
his panties up while I retied the knot that kept his
pinafore apron in place.
The straps of the white pinafore apron were tied firmly
once more.

The straps of the white pinafore apron were tied firmly
once more.

“You will clean the rest of the kitchen, including the
floor, counter tops and the oven. Understood?” I said
while enjoying the mix of humiliation and fear in his

“Yes mistress.” he replied while blushing.

“Good. Now I will be cleaning myself up and getting
ready for the party. When the intercom rings, be a good
girl and buzz up our guests and open the door. Make sure
to offer them something to drink as well.”

“Yes mistress.” my maid repeated.


I was just out of the shower, putting my make up on,
when I heard the phone intercom system ring. Somebody
had arrived downstairs.

I could hear the sound of heels taking small steps on
the hardwood, followed by a quiet ‘hello’.

He’s actually buzzing them in. I thought to myself.

Even though I just had an amazingly intense orgasm, I
was getting wet once more. The thought of my helpless
maid having to open the door and welcome my first guests
in was just too much. The anxiety on his part and the
sheer power on mine was thrilling me.

I thought of the cage keeping him trapped, the butt plug
reminding him of his new position and the lockable
French maid uniform covering it all up. This was too
good to be true.

Suddenly, I heard two knocks on the front door. I
couldn’t help myself… I guided my hands down to my wet
pussy and started rubbing in between my lips again. God,
this felt so good.

The familiar creak of the front door opening didn’t
follow the knocks though. Instead, I heard the sound of
heels coming towards the bathroom door.

“Mistress?” my scared maid’s voice came quietly through
the bathroom door.

“Are you going to open the door or what?” I responded.

“But, mistress…” He tried again.

“Don’t make me come out there and spank you in front of
my friends.” While I said this I got to a new high. I
was so ready to come now… but I wanted to wait. Not

“Yes, mistress.” he said with a clear sound of defeat in
his voice.

Again, two knocks on the front door.

“Hurry!” I screamed, nearing my climax.

The front door finally creaked open and I could hear two
high pitched voices filling up our front hall with a
mixture of laughter and pleasant greetings. I recognized
the voices of my two co-workers from the office.

“Oh my, look at you.” One of my co-workers said.

“Hah, that’s quite the outfit you’ve got there! How long
did it take to put that together?” My other co-worker

“I… I… just…” My little slave tried.

“Oh, wow, and look at those high heels!” They continued.

I couldn’t help myself, I was about to burst. The power
I felt, the anxiety emanating from my naughty little
slave, the teasing from my co-workers, it was just too

I exploded into an even bigger orgasm than I’d had just
an hour ago. It was so intense that I almost fell to the
floor right after.

One thing was certain. Our Halloweens would never be the
same after this.

Would you like to be f****d to cross dress on Halloween?
Perhaps next year it’s your turn to be a French maid…
Let Mistress Deborah know in the comments!