Forced to Cross Dress on Halloween
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Forced To Cross Dress On Halloween free porn video
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.
***
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 accesoiries, 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 instalment 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 d**** 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, suspensefully, 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?”
“Fo… 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 instalment 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 its your turn to be a French maid… Let Mistress Deborah know in the comments!
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.
***
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 accesoiries, 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 instalment 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 d**** 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, suspensefully, 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?”
“Fo… 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 instalment 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 its your turn to be a French maid… Let Mistress Deborah know in the comments!
Nova
- 17.08.2021
- 8
- 0
