My Story, Making a MaidbyKary_M©
Disclaimer; fiction, x-rated-language -sex; gender issues; all names are fictitious and relate to no one living or dead. Feed back welcome and appreciated.
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When I was young, I knew I was different then the other boys in my neighborhood. Though I participated in their activities, I felt out of place, kind of like I didn't really belong. Often, I would make up excuses to get away and be on my own.
At the onset of puberty, I became really confused. While the boys seemed to be only interested in the girls, I found an equal attraction to both sexes. This fact really put me on the outside, since at that time there was nowhere to turn for help or advice.
My self-being really changed when I took a sitting job after school and on weekends at sixteen. It all started quite innocently when on one occasion, Sandra, my employer left me a note to take the laundry from her washer and with a list of settings for the drier, what to fold and what to hang because she was running late and didn't want all her expensive things damage. I didn't think it would be a problem, her kids never got off their bus until at least an hour after I got there, so at least I had something to do.
It was when I opened the washer and found a couple of netted bags filled with lacy, skimpy things and pulled a few out to inspect them that something seemed to turn inside of me. I suddenly felt like a curtain had opened in my head. A tingling sensation over came me as I felt a pair of Sandra's skimpy little under things and suddenly I had an overwhelming desire to slip them on, soaking wet or not.
For the rest of the day, I couldn't think of anything but wearing sexy, frilly underwear. I thought to myself, that maybe my attraction to both sexes had something to do with my sudden desire to wear female cloths. Realizing that I was sure, that I was neither male, nor female, but a combination of both and I'm not sure why, but suddenly started to feel better about myself.
That night, at bedtime, I undressed in my room and looked at my nakedness with a different prospective. I tried to imagine myself dressed in a girl's skirt. Posing, as I thought a young teen girl would. There was something I saw in the mirror that reinforced my unisex thoughts. Maybe if my hair was a little longer, styled and curled. I knew I would make a pretty girl.
Over the next few days, I thought of almost nothing else. My desire to try on Sandra's things grew to an ache .I never even dreamed my mother might wear anything as nice as Sandra. Besides, it was a longstanding rule in our house, that you didn't go into other people's belongings and you respected the privacy of others if you wanted the same in return. It was different with Sandra she had asked me to help her out with her laundry. I knew were everything went and all the treasures within her scented dresser. Panties, garter belts, bras, hose and other nice looking stuff I couldn't even name. There were different styles of everything and a multitude of colors and fabrics. I didn't know what to do. I didn't want to breech my trust with Sandra by stealing her things and I didn't think the hour or so I had alone in her house after school would be long enough.
So by Friday, I was starting to feel a little depressed. Sandra asked me something that not only cheered me but would forever change my life. Her and her husband wanted to go away for their anniversary. Just one night, they wanted me to stay with the kids from about 4 pm on Saturday to Sunday afternoon. All I could think about was a whole night to satisfy my curiosity. I even said I'd do it for free, as a gift for them. Little did she know the gift she just gave to me.
From 4 to 9, was the longest 5 hours of my life, waiting for bedtime then until the kids were asleep, seemed an eternity. Then it was time. I had no qualms about entering the master bedroom, Sandra insisted I sleep there anyway, just in case one of the children woke up in the night, they always came to her room. I just hoped it wouldn't happen that night.
I totally stripped on the inside of threshold after closing the door. I thought that I should shower first so that I wouldn't get any strange odors on her lingerie. Besides, I wanted this first experience to be total and that meant to me I should use her soaps and sprays. I was amazed at all the different things she had to make a girl feel feminine. I didn't have to worry about any body hair, what I did have, was almost invisible any way. So ten minutes later I was wrapped in a towel standing in front of her dresser searching through her treasures for my first try at finding myself.
My first choice of color was red. Satin and lace matching bra and panties, a wide garter belt that was tight enough to make my hips appear larger. I couldn't believe how I felt after I put on a skirt and a top from the closet. I felt like this was who I was meant to be. I cried that first time, tears of joy. I couldn't stop myself. It just felt so good. I spent a couple of hours walking around the house in heels, tripping constantly at first, and lounging around where I could see my reflection. For the first time in my life I had begun to like myself. I felt terrific.
Later, when I began to fall asleep, I found the most feminine pj's I could and after putting everything away I went to sleep as satisfied as I can ever remember. The morning was a shock as Sandra's kids came running into the room. Jumped on the bed yelling for their mom. It really made me feel weird, but nice.
Over the next year and half, I relished every opportunity I got to dress up while sitting for Sandra. She kept a box by the washer for old cast-offs. I began to collect what ever I could and even wear panties in public under my clothes. I noticed things about myself during that period. When I wore something feminine, my posture improved, my state of mind was more at ease and I even found myself moving different. I started experimenting with make-up. I even bought my own, under the guise of filling a list for Sandra, something I did quite often.
I thought I was smart at covering my tracks. I found out later that Sandra had suspected that I had been tampering with her things from that very first time. Her suspicions where vilified when unsuspectingly I removed a matching set of panties, bra, hose and garter belt that she had bought and planted in the cast-off box. Then she began her own plans to catch me in the act.
It was just after my 18 birthday, Sandra's husband Ken was away for two weeks on a business trip. On his second day away I was asked to sit while she went out with friends and not to expect her home early. The children were already asleep so I wasted no time at all. As soon as the car was out of sight, off came my tracksuit. I had the set of lingerie Sandra had planted already on. So I just wandered up to her room to see if I could find something nice to wear over top of them.
My first mistake was I should of known something was up Sandra never left anything laying around. But there on the bed was a new dress. It was made of pleated satin, black with a very delicate white lace trim on hem and on the top of the bodice. I just had to try it on and that was my second mistake. As I looked at my reflection, I couldn't believe how sexy I looked. The top fit my chest perfectly. The hem stopped about two inches below my bum making it impossible for me to bend over without showing off my bright red satin panties. I thought that she must of bought it by accident, because she would never get her breast to fit into this outfit.
As much as how great I felt wearing it I thought I'd better take it off before something happened to it, just in case Sandra wanted to take it back to the store. As I reached to undo the zipper, Sandra stepped into the room.
Well, I was caught, I swear my heart stopped, I could feel the blood drain from my face. The room started to spin, I was overcome with dizziness and the last thing I remember seeing was the grin on Sandra's face before went I down into darkness and fainted.
As I felt myself float back to realality, I found that I had been placed in a chair with my head between my legs. I felt something cold on the back of my neck. There were other differences also, I could feel a light tugging on my ears and I heard a tinkling sound when I tried to move my head. I opened my eyes and slowly focused my vision on my feet. I thought I was seeing things, on my feet where a pair of black patent leather shoes with ankle straps and at least a four-inch spiked heels.
As I tried to sit up I felt a hand on my shoulder restraining me. I heard Sandra say," Now, now Kary, not to fast, you've had a nasty fall, just relax a few moments until you get your wits back. Besides I wouldn't want you to fall off your new shoes until I get a chance to see you in them."
She went down on one knee in front of me and cupping my chin in her hand raised my face so I was looking up into her face.
" I just knew that you'd like that outfit," she said with a sly grin," especially after you took the surprise I left for you in the cast-off box."
I felt my cheeks getting hot and I tried to stammer out an apologies.
"No, no dear Kary, no need to talk like that, I don't mind at all." She said as she stood up to tower over me." Actually, I've known your little secret all along. Didn't you ever wonder why those things you found in the cast-offs were still in perfect shape?"
I started to cry and Sandra pulled me to her and said," It's really okay, dear I was so glad when you discovered how much you enjoyed my clothes. Ken and I have been searching quite awhile for a girl like you. I'm sure you will enjoy it as much as we have anticipated the day we would find the perfect girl to include in our lives."
She pulled me up from the chair and helped me get my balance before she walked to the door. Turning with a smile she said." I also found the paper you used to practice writing your new name, so from now on I will call you by that name, or girl. Now, go to the basement, the room beside the spare bath will yours when you are here. I'm sure you'll find everything you need."
Dumb founded, I started to walk with out even thinking
Oh, and Kary, do be careful on the stairs, I wouldn't want you to twist your ankle and fall again. Meet me in the dining room after you have put on some make-up and freshen up some, okay dear?"
"Yes ma'am." I replied meekly.
"I like that answer, you'll do nicely I'm sure dear."
I can't even recall what I was thinking as I made my way down stairs. A mixture of fear, dread and embarrassment at being caught. First I went to the bathroom and washed my face, as I looked in the mirror I saw what was tugging on my ears. It seems that Sandra had pierced my ears before I woke up. All I could think of is why? What did she have in mind? Why had she trapped me? As I turned my head and felt my new ear rings brush against my neck and heard the tinkling sound they made I became excited. Then I thought about what she said about her and Ken looking for a girl "like" me. My emotions started to come alive. She called me a girl, I started to become light headed again. I knew she must have planned this day for a while and I started to feel like maybe things will be okay. After all, she could of gotten into quite a fix along time ago if she wanted too.
It was then that I noticed the box beside the sink. It was a plan wooden box with the name Kary written on it. More surprises I thought. My hand was shaking when I reached to open it. It was full of cosmetics and a note;
Now that you are reading this, you have taken the first step
in your new position in our household. Here you will find some
Instructions on how I expect your make-up to be applied and the
Colors I expect you to use. Everything is numbered so that you
Shouldn't take too much time. I don't want to wait too long for your
appearance in the dining room. I would like you to take a moment to
check out the surprises in you're room. But be quick, I will be waiting
Love Mistress Sandra
I couldn't believe what the implications of what that mistress meant. I felt a shiver of fear run through me along with a tinge of excitement. I thought if I ran, where would I go dressed like this? As I looked at the make-up Sandra had given me to use and then at my reflection. I felt like I had no choice and after a few minutes of thinking about it, the excitement took over. I really felt like I wanted this.
I hurriedly followed Sandra's instructions after all I had some practice. I don't think I did to bad of a job at it even with my hands shaking with nervousness. I did a quick check of the room that was to be mine. There on the bed were a few more outfits like the one I had on, in different colors, red, white, and pink. There were also several other things, but I just wanted to get upstairs. My curiosity about her plans was making me very excited and I just couldn't wait any longer to find out.
I found Sandra sitting on the edge of the table. She wore a full-length satin robe I had never seen before. Incredibly long heeled black shoes and black gloves that disappeared into her white sleeves.
"Not to bad," she said as she looked at my face," I'm sure you'll get better at applying it, but I think I'll have to show you a few tricks to bring out your best features."
"I would like that a lot ma'am." I said, as I looked down, still slightly embarrassed at being caught. I could feel myself blushing under her scrutiny.
"Well," She started," If you want to agree to my terms, you will present yourself as you are when possible.'
Sandra threw me an icy glance," Do not speak until asked, you will listen to what I have to say before you speak again. I am about to give you the terms of your service. What will be expected of you and what will happen if you do not."
I became a little worried, it was a little scary to think that I was about to be black mailed into subservience. While, a part of was thrilled that this beautiful woman wanted to enslave me.
" I'm sure you know what would happen to you if you secret was found out, but I don't think that either of us would want that to happen and I'd like to think that you would join us because you wanted to. Are you still a virgin Kary?"
"Are you attracted to girls?"
"What about boys?"
I hesitated, I wasn't sure where this was going," I'm not sure ma'am."
"Well," she smiled," I think that perhaps you are, I did see the way you looked at Ken in his Speedo's at the pool. You see Kary the reason I'm asking these questions is to make sure you understand completely what your new responsibilities will be."
I could feel her eyes burning into the top of my head when she paused.
" Of course you will still do the things for us you have always done, but if you choose to stay on in my employ you will have to see the sexual needs of Ken and myself."
I couldn't believe what I had just heard, all my fantasies were about to come true in one swift moment. I wanted to jump for joy.
" As a matter of fact, dear your first duty will be to prove your loyalty. I want you on your knees directly in front of me."
I was shaking with excitement as I dropped to my knees without even thinking about it.
Sandra released a wicked little laugh before speaking again," So Kary, are you ready to submit to the whims of myself and Ken, be they what they may?"
Looking up at her, I'm sure she could see my excitement know as tripped over my tongue just to say," Yes ma'am."
"Good," Sandra coed," In the next two weeks, I will train you. If at that time I deem you satisfactory, Ken will be home, the children will be away for a while. At the end of that time we will decide if you will carry on in our employ or you will never come back. Think carefully before you answer dear."
I was so worked up that I would have screamed to the world that I wore women's clothes, if she had asked me. As meekly as I could I stated," Yes Ma'am, I would do anything for you to please you."
"That was just what I wanted to hear girl," Sandra said with an evil smile," this will be your first task in you new position."
Sandra opened her robe, it was the first time I had seen a women naked in real life. She was shaved bald. I didn't really know what she wanted. I just stared at her openness, pink and wet.
"The first thing that I'd like you to do Kary is to put on one of these, It will keep you from soiling your new panties and help with your new training. Have you ever tried to put one on before?"
I looked at the condom in her hand and A chill went down my spine when I heard the word training," No ma'am."
"Well then, I will show you how I want you to wear them this time. You will use one whenever you wear your panties, understand. Stand up."
"Yes ma'am." I said as I stood. She instructed me raise my skirt. Sandra pulled my panties down with a sly grin as I blushed with embarrassment.
"Well now," she said in a taunting voice as she held my penis," not much of a cock. But then, it will make a lovely clit. I knew a girl in college that had a bigger one than this."
I felt crushed as Sandra degraded my manhood, my embarrassment increased so much that I felt like fainting again. I could feel my penis soften as she giggled at me. But then she rolled the condom onto me and stretched it out so she could fit my testicals inside of it also.
" Take a good look at this Kary, This is how you will be required to wear them from now on. I think we will have to come up with some form of punishment for when you do not follow all of your instructions perfectly."
"Punishments, ma'am?" I asked with a trembling voice.
"Yes of course punishments dear, how else would you be able to become properly servile if there isn't some form of rewards or punishment. Besides, I'm sure a girl like you would learn to enjoy it. Now fix your clothing and get back on your knees."
I did as told and with in a few heartbeats I was once again less than a foot away from Sandra's pussy. I watched as she reached down to stroke herself and spread her lips. I could smell her aroma and I felt my excitement begin to grow again.
"Now Kary, your first new duty, you will be required to service my little pussy here. Especially after Ken and I have sex. That is why I want the condom in place, so you will learn to enjoy eating cum. So lets start right in by kissing it lightly here."
I was shaking with desire as I moved closer to the spot she spread open between her fingers.
"This is my clit dear," she moaned as it began to swell against my lips," yes, very nice, Use your tongue now.
Sandra began to moan and sigh, her breathing began to increase as I licked her. My own heart began to race and my quickening breath caused me to snort into her pussy.
" Suck on it," she panted hoarsely.
Her moaning grew to shrieks as I sucked and licked on the clit in my mouth. After a few minutes she emitted a long deep groan and her hips shook so violently I almost lost contact with her clit. She stood and stepped away from me, she was flushed and trembling.
Looking down at me she sighed," Yes Kary, I think you will do very well. Now go touch yourself up and meet me in my room for your next lesson."
She turned and swept away. Leaving me on my knees to try and stand. As I made my way to my rooms I realized that I had ejaculated while I serviced Sandra's pussy. I wonder what she meant by," it would help with your training" I figured that I had better wait and ask before I took off the condom though. I was A little frightened of what she might have meant by punishment. But, the thought did kind of give me the shivers.
I quickly washed off my smeared lipstick and applied a fresh coat. I ran as fast as I could in my heels to see what the next exciting part of my training Sandra had in store for me.