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Forced to Cross Dress on Halloween
by lokokolo (no address provided)

***

Halloween is a great reason to show your submissive side 
and cross dress for your mistress. Other than writing 
these articles and stories, I also enjoy dominating my 
partner. This Halloween was no exception and I wanted to 
share this exciting day with you. Below you will find a 
story that is heavily based on the events that took 
place in my house this year. (Fdom/M, d/s, 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 
on.

"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 
added.

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 
apartment.

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.

*SLAP*

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 
torture 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 
member.

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.

*Click*

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 
costume.

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

***

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 
out."

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 
together.

*Click*

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 
maid.

Mark's new uniform transformed him into a Victorian 
maid.

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 
bring.

"Well, here goes!" I said joyfully as I undid his 
blindfold.

"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 
instead.

"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."

"And?"

"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."

"Okay."

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 forced 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 
strings.

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 
pleaded.

"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 
ass.

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 
instructions.

"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.

"And?"

"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 
abuse 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 
place.

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 
posture.

"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 
yet.

"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 
added.

"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 
much.

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 forced to cross dress on Halloween? 
Perhaps next year it's your turn to be a French maid... 
Let Mistress Deborah know in the comments! 

END

* * * * * * * * * * * * * * * * * * * * * * * * * * * *
It's okay to *READ* stories about unprotected sex with 
others outside a monogamous relationship. But it isn't 
okay to *HAVE* unprotected sex with people other than a 
trusted partner. 4-million people around the world 
contract HIV every year. You only have one body per 
lifetime, so take good care of it!
* * * * * * * * * * * * * * * * * * * * * * * * * * * *
Kristen's collection - Directory 85