My grandfather was still young when he passed away. He was a cruel joker, and had the sense of humor of laughing gas is what his friends always said. He took care of me when I was young, my mother passed in c***d birth, and no knowledge of who my father was. So my grandfather took care of me, with the help of the maid. Until I was in college he lived in the city, so I could take the bus and go to school, but once I left for college I became busy, and he moved out of town, up on a hill with the lake on the back side, very private, very beautiful, but yet old and creepy.
When he passed away I was a few weeks from finishing school, then I would learn to run his company. I let my teachers know, and all of them gave me the assignments and an extra week to finish them. After the funeral the lawyer read the wills, he had a few to be read privately, and for many reasons as an emergency plan. The one read to me had the old line “I leave you my lake mansion under the condition that you stay in there for a whole week” I laughed and the lawyer was curious, and I explained his humor. Then at the end of the reading “the house is yours my boy, I love you, and I hope you live a long happy life.”
After college was over, passed my finals, and received my degree, I packed up and drove to my new home. I walked up to the master bedroom and there was a note on the door, “The master bedroom was saved for you, if you want to come and remember me, I was down the hall second door on the right.” His careful planning and ensuring I was happy even after he passed was awkward and made me feel so warm inside.
Now that I am unpacked, time to do what I love to do most, kinky cross-dressing. I walked into my closet one side was my normal clothing, the other side a lot of sexy women’s clothing I had collected over the years. I spent plenty of time getting myself ready and planned a whole weekend long cross-dressing bondage experience. During college I had my entire body hair laser removed, from neck down and my facial hair, so I now could never grow a beard of mustache but saved a lot of time not having to shave. I let my hair grow longer, so I could style it like a girl with shorter hair. I grabbed my panties, a nice pair of black latex, with white latex frills and a bow in the front, it was a thong, and glided between my cheeks. I pulled the back off to the side, and sat a butt plug down on my stool, covered it in lube, and took my seat on it. After it was nice and deep, I pulled the layered latex throng over the plug and set it into the grove of the plug like it was meant to be worn with a thong.
Next was the makeup and hair, I took plenty of time making sure my hair was perfect. Then I pulled out my makeup kit and started with the eye shadow, a little blush, then a dark red lip stick, and finished off with some glittered gloss. Of course it’s not as simple as applying it, but to go into detail would take me too long, so let’s leave it at, I looked gorgeous. Next was my nails, I painted them all black with a shining glitter paint, I then laid back in bed for a little bit to let them dry, but not all the way down so my hair could not be ruined.
Next was the fun part, a black latex corset, I pulled it on and slowly started the lacing process. I learned a few things over my years about lacing up a corset. One was having a hook set up on the wall, the next was from a few years of me playing hockey. When lacing up skates, you would use a lace hook to pull the loose lace, and tighten them up, one by one. I was flexible enough with my arms that I could get the hook onto the lacing, and pull the loose ones tight, and lean away from the wall where the ends were tied off to the hook. It took me a good amount of thirty minutes to get it all the way laced up. Then I gave the laces one last hard pull before swiftly tying the ends in a tight knot.
Next was my final bathroom break for the next 6-8 hours. And I pulled the ice block out of the freezer I had placed in there a few nights ago. It was a mild summer day, so next to an open window over the sink in the kitchen I expected it to be done in the 6-8 hours.
Back up to my room I walked into the closet and pulled out the garter clips and latex leggings. The clips could hook onto the corset, and I fed them below my panties, in case I had to use the restroom. I gave my cock one last check that it was in position, I always pointed my cock down over my balls, so when wearing tight panties, even if I tried to get erect, it stayed in place, and didn’t poke out. I pulled up my leggings, and took all the time I needed to get them tight and all the air out, except between my toes, then clipped them off and went back to the closet.
Finally it was time to put on my dress, a black, white lace trimmed, maids uniform with a skirt that barely went half way down my thighs. I tightened the belt, and fed a cord through it, and into the top. Once the cord was right, I pulled up the zipper in the back and I gave myself a look in the mirror, and felt so sexy and girly. I then pulled out six small pad locks, and locked on my belt, four up the back of my top, and the last one locking the zipper so I can’t pull it down. And I could not remove it for hours now.
Next was my heels, which were six inches tall (15cm) stilettos and had a thick latex strap to be locked onto each ankle. I pulled out a twelve inch long chain and locked each ankle to the chain, effectively making a hobble chain that was now impossible to remove for hours. After that was my gag, a black ball gag with chin strap, which I took great care in ensuring it’s the tightest possible. After that had its lock on it, I made sure my hair was still looking very neat and then put on my hair band to finish off the maid look. I looked deeply at the mirror, the gagged maid, with her lush lips, and sexy look all over, and could feel my cock trying to escape, but the latex held it in its place.
Finally I put on my gloves, and got out all of the air, and over them placed my cuffs, with a small chain under four inches long, I locked each wrist to each hip, and I was now in my total bondage. And now the real fun can begin, I grabbed my accessory feather duster, and slowly hobbled my way down stairs to begin cleaning.
The cord I placed under my maid uniform earlier was my headphones cord for my mp3 player, which was hooked to my belt next to my left hand, I started playing my music, and dusting off the furniture. I was enjoying myself, cleaning and walking around the home when I walked back by the front door. On the table next to the door was a hand written note.
“Hello I am Amanda the maid,
Your grandfather hired me to clean the house and had a payment plan for me to clean for the next year. It seems I came when you were out, so I started my work, and left you this note so you did not think I broke in or you were not robbed.
Today I will be cleaning the bedrooms, kitchen, and library, as well as sweeping the whole house.”
I looked up the stairs, and saw my bedroom door was opened. I made my way up the stairs, and noticed the carpeting and that was why she didn’t hear my heels clicking on the floor. I had turned off my mp3 player, and snuck up to my doorway, and saw her with one of my latex dresses in hand, looking in my mirror.
She was talking to herself, “Oh my, he must have some very attractive women in his life, into some very sexy things. I wonder if this would fit me?” she slowly pulled down the zipper, and I saw her check out the window to make sure no cars were pulling up the drive, but had not yet noticed me peeking in.
She removed her clothing and pulled on the dress and zipped it up, looking in the mirror. I stepped back a bit knowing she would turn to look at the back in the mirror, and I wanted to not be caught by her in my current state. “I wish I had a boyfriend like him, rich heir to a lot of money, cute by what the pictures show, I would love to tie him up and make him all mine, and pleasure him for hours to make him love me.”
At those words my cock tried to escape its latex prison, and my heart was pounding. I looked in seeing her sexy figure. She was very cute, and had a very stern but so gentle look on her face. I thought of what I should do, and my arousal took over my choice. I stepped into the room, and made my first heel click on the bare wooden floor of my room, she turned about to freak out. We starred at each other, “um, hello”
I muffled a hello to her.
“I am Amanda the house cleaner, you must be his girlfriend? I can explain all this” as she noticed me looking her over.
I shook my head no, to answer her question.
“You are not his girlfriend.”
I shook my head again, then tried to tell her my name, just enough for her to understand.
“You are Tyler?”
I tried to muffle again.
“Taylor? Your name is Taylor?”
“You are the owner now, and all this stuff is yours?”
I nodded again.
“I guess you want me out of your clothing, don’t you?”
I shook my head no.
I signaled her to follow me, and I made my way down stairs, to the kitchen. She looked at the keys, hanging from a hook, all trapped in ice.
“Okay, I am taking this outside, and I am getting these keys, so I can ask you a few things, and if you want me to set the keys back so you are stuck, I will do that after we talk and I clean the house.”
I nodded, and she went outside, and I heard a large cracking sound of the ice breaking on a stone. She walked back inside and started at keys on my gag. She took out my head phones and pulled out a chair for me at the table.
“I am sorry I tried on your clothing without asking.”
“It’s okay, the dress suits you well. I am sorry I scared you. I saw your note, as I was dusting, and saw my door open, so I came up to see what you were doing, I was planning on hiding from you the whole time you were here.”
“Why did you step in?”
“I heard what you said, about tying me up,”
“I meant metaphorically, not really.”
“If you are not busy tonight, I would love to go on a date, and we can see where things lead.”
“That sounds lovely Taylor. How about I get back to cleaning, and I will take off your dress.”
“No please, it looks beautiful on you, you can wear anything you want of mine.”
“Thank you” I noticed her blushing. “You look very beautiful too. Oh my I just had an idea, come back up to the bedroom with me.”
I slowly made my way up to the bedroom, she was in just her underwear leaning against a pole at the foot of the bed, with a tight black latex corset in her hands. “Do you think this will look sexy on me, as your dominating girlfriend?”
“Yes Mistress.” I walked over to her slowly, and before I got to her, she pulled out a leash and collar from behind her, getting it around my neck, knowing I could not run away from her. She then walked to the closet, and I was tied to the footboard of the bed, unable to get away while she changed.
“Sorry to rush this relation, but you got me excited, and rather than a gag you will have something else in your mouth.” I was pressed back against the bed, and she straddled my head.
Hours later I awoke still tied to the bed, curled up at the foot of the bed, as she lay normally with the pillows. She had one of her feet on my waist, the other in front of my face. I kissed is softly and she woke up. “Guess I didn’t get any cleaning done today, looks like I am going to have to stay a little longer” she said with a smile.
“I hope you stay a lot longer, and we still have a date tonight.”
“Well there is one thing I can clean, since he didn’t get to come out and play yet!” she hooked her finger on my panties, and pulled them down, revealing my cock, covered in pre-cum, and a little bit of cum from the hour of her riding my face, and me getting way too excited.
She then noticed the plug in my ass and toyed with it a bit, “Looks like we are going shopping after dinner, cause I need to get something if my new boyfriend likes anal, and I as his lover wish to give him pleasure.”
I smiled knowing what she meant, and as she stroked my cock, we kissed.
That was over a year ago now, we are engaged to be married, and at home I am not allowed to wear normal clothing, either I am naked or in one of my dresses that she lays out for me. The company my grandfather owned was mine and I expanded it, and left control of it to a lot of well qualified people, and I would only have to go in once a month to ensure the company is going well. The cleaning company that Amanda was hired from was paid the amount that my grandfather set forth to pay her to clean my house for a year, since she didn’t need the money, and I supplied her with a happy life, and she never took advantage of me, and always seemed to worry that she was taking too much, even though I barely got her anything, since I already had a lot of sexy clothing that fit her.