This is a work of fiction. More importantly, this is a work of erotic fiction. Even better, this is a work of erotic transvestite fiction. If you are under the legal age in your state, country or planet to obatain adult literature, STOP READING NOW!
The Sitter
It was Friday afternoon and I was on my way home. It was only a half day of school that day. Parent/Teacher conferences or some bullshit. Who cared I had another half day that I didn't have to be in that crummy new school? The school itself was OK, I guess. But the other kids there didn't seem to want to make an "outsider" feel welcome. No really overt hostility, mind you, just an indifferent and biased attitude. Almost all the kids were from wealthy families, and they knew I was just an "upper middle class" slob. They looked down on me for that and tended to dissociate themselves from me. Just as well, being a bespectacled (almost) 16 years old non-athletic bookworm suited me fine.
Ninety-nine percent of the other students were either 90210 model dorks (guys and girls), brawny beefcake sports guys or lithe, sinewy cheerleader types. You could count the overweight or nerdy people on one hand (well, maybe two or three hands). But all of them were even more obscenely wealthy than the others, which ostracized me even greater than the less well-to-doers.
It also didn't help being brought into the freshman class near the end of the school year. Not only did I not know anybody, as a freshman, I was bottom feeder on the school foodchain. Several people had gone out of their way to make me feel . . . inadequate to their standards. A few had even physically accosted me. Nothing major, just your usual rude bumps or accidental trips.
Even a few of the teachers seemed to despise my very presence on their little world. Especially the two physical education instructors, Travis and Edna Whit. Brother and Sister twins who make Arnold Swarczenegger look like the pillsbury doughboy. You rarely see them not together, outside of their classes, of course. That prompted me to name them Half-Whits when they were by themselves. And, of course, it got back to them what phrase I had coined so they made my life a reasonable facsimile of Hell whenever they could.
And all this social comfort was brought about by my parents. Two intellectuals who had a brainstorm of an idea concerning computers that made them independently wealthy (except next to the bozos we ended moving into). They spent alot of their time at their company testing this and debugging that, I hardly ever saw them. But that was going to change that day!
That Friday after school, me my Mom and my Dad were going to spend time together. They had promised dinner out, a few movies, even a trip to the amusement park for the whole weekend. Just us. I wouldn't have to worry about the kids at school.
So I was in a decent mood when I got off the bus and meandered toward my new house. As I got closer, I noticed both their cars in the driveways. Strange, I thought, I guess they wanted to get on early start on the family thing. They were probably just as excited as I was about it.
I rushed in the front door expecting them to be in their "civvies," not their usual suit and tie with labcoats they were prone to wear. I spied a suitcase on the couch of the front room and figured they had decided to make it a weekend away for us. Cooooool!!!!
About that time my mother walked into the room with another suitcase, dressed in her "work" clothes. She smiled sadly at me and did one of those sappy head tilts moms get when they are about to break bad news to you. Like: the subscription on your Money magazine ran out yesterday, or your grandmother contracted herpes, or your dog died, or . . .
"Your Father and I have to go away for the weekend, honey." My jaw dropped almost as far as my heart did. "Now don't look at me like that. I know we promised you some time together, but there has been a major breakthrough in the program and we have to fly to the labs on the West Coast to help with the problems."
"But Mom," I whined, "You guys prooooomiiiiised!"
"I know, sweetheart," she cooed, running the back of her hand along my cheek in that annoying patronizing mother way. "But there is no help for it. Your Dad and I took on this responsibility with the increased pay and promotion when we moved out here. You understand, don't you?" She looked pleadingly at me.
I sulked and pouted, scuffing my feet on the carpet.
"No, I don't!" I petulantly said, "It's not FAIR!"
Her hand grabbed my chin in a vice grip and forced me look at her.
"LIFE," she intoned harshly, "is seldom fair. You'd do well to learn that Chris. We put clothes on your back, roofs over your head, food in you gullet and numerous gadgets for you to play with. And do you know where all that comes from? Huh?" She was getting into her usual bitch mode, only dad was worse.
It comes from the sweat of your Fathers labor," she finalized, "And of mine! I'm sorry you cannot make friends here. But, frankly, that's your problem not ours. I'm sorry our to-do this weekend was cancelled but work is work. Understood?"
I had seen my dad come up from the hallway and watch this exchange, his eyes cold and almost emotionless. I looked pleadingly at him, knowing what he would say.
"Your Mother is absolutely right, Chris," he said severely. "You'll have to make do. Besides, it's only for a few days and there will be other weekends."
"Yeah, Right!" I muttered.
"And that attitude is exactly why we got you a babe. . .uhhh. . ." he stammered over the word, "Housemate while we are gone. To keep you company and out of trouble."
"Whatever," I said, subdued. "I can't friggin' believe this crap. . .A babysitter?!"
My dads face smoldered and my moms eyes got that dangerous look in them. I looked down at the floor again so they wouldn't see the defiant anger burning in my eyes.
Suddenly the doorbell rang.
"That's probably her now," my mom said as she headed towards the door.
"HER?!?!?!?!?" I almost screamed. I turned to look as my mother opened the door.
The girl in the doorway was really very pretty. Almost my height, a bit thinner, but built up in ways best left to the imagination of romance novelists. Her hair was a flaxen blond, shoulder length. Her eyes a penetrating blue in blue with green flecks. . .and a slightly cunning look to them. Almost catlike the way her gaze fell directly on me first and foremost, a slight mischievous grin on her face.
My mom ushered her in and introduced her to me.
"Chris," she said, all trace of her former hard tones banished. "This is Crissy. She will be your. . .companion for the next few days. I thought it was cute that her name so closely matched yours. I'"m sure you'll get along great."
"You are to obey her as you would us, son," Dad spoke up sternly again. "If she tells you to do something, you are to do it. No fuss, no arguments. Do you understand? I don't want to get a phonecall or you'll be in big trouble." I nodded meekly, secretly wishing they would all drop into some burning pit of silicon chips.
"Crissy here is twenty-two," my mother began, "Legal age for watching you. We have written a note to those in charge, like the police and your school, letting them know we'll be gone a few days and she has charge over you. So don't try any stunts, OK? Just behave and all will go well." My moms face softened a bit.
They speak highly of her at the club. She is well known and respected for one her age, so we feel comfortable in leaving you to her capable care." They pulled Crissy aside for a minute or two while I sulked on the couch. Probably giving her last minute instructions and warning her of my temper.
"I can handle a bad temper and bad attitudes," she spoke loud enough for me to hear. Twisting her head sideways enough so I could see her sardonic smile and wicked glance. "There will be no problem of that, I assure you."
With that my parents kissed me goodbye, grabbed their suitcases and were out the door. I just mumbled goodbyes and sat dejectedly on the couch, picking at imagined loose threads. I sat there for a few minutes lost in thought until I noticed a shadow across me.
I looked up and saw Crissy standing in front of me, arms crossed and feet spread. The look she gave me was one of little tolerance for poor behavior. she studied like this for a moment or two. I stared back at her in open defiance of her perceived authority. Her smile widened a bit and her face relaxed.
"Chris," she said my name softly, almost as if tasting it. "Would you be a dear and get my bags from my car for me, please?"
"Get 'em yourself!" I snarled and nearly leapt to my feet brushing past her forcefully. "I am not your slave."
She turned and glared at me for a second. Nodded her head as if to say, OK the game is on, and went out to her car. I went upstairs to my room and changed out of my school clothes and into a pair of shorts and ragged T-shirt and tennies. I went back downstairs just in time to see her struggle in the door with several smaller suitcases, a large garment bag and two small travel cases. She stood in the doorway a second, probably to give me chance to help her. Yeah, like that would happen, then dropped everything by the endtable.
I blew past her towards the door. Her arm shot out and grabbed my upper arm. Damn she was a strong little wench!
"Where do you think you're going?" Crissy asked archly.
"Out," was my curt reply.
"Just make sure you are in here before dark. Your parents said that was your curfew. They asked I run a few thing to the cleaners so I'll pick up dinner on the way back. You had better be in if I'm not back before it starts to get dark." The short tirade only infuriated me more.
"Whatever!" I spat and then was past her racing towards the woods bordering the property. I planned on staying out until I felt like coming in and not when some girl sent to BABYSIT me says so. Who did she think she was, anyway?
I went to my favorite tree and climbed up into it's leafy embrace. I came here on occasion when I wanted to vent anger without being too destructive. I just sat in the wooden arms of a silent comforter, verbalizing what was on my mind while absently plucking leaves and shredding them.
"Who does that bitch think she is," I complained to my unanswering companion. "Giving me orders like she was my mother or something. I don't take that crap from anyone, let alone a girl who is barely my size!"
'Be in before dark!' " I mimicked. And that half veiled, albeit nonspoken threat of what will come if I wasn't. I'd show her, I wasn't going to go in until waaaaay after the sun set. Humph!
I just sat in that tree for several hours, watching the clouds go by, tossing twigs at the dragonflies and any other thing to occupy my attention until nightfall. My stomach began to growl. I had not eaten lunch because I disliked sitting by myself in the cafeteria and figured I would be going out to dinner with my folks when I got home. That's what I get for thinking.
Eventually the sky darkened and the land took on the blue-black shades of night. I waited until the last vestiges of any sunlight were quite thoroughly gone before dropping out of the tree to the ground below.
Pain lanced through my feet as they struck the hard woods ground. Damn! I couldn't wait for my doctors appointment to see what was wrong. I hope my double-faced parents had at least remembered to reschedule the visit. I looked towards the house and noticed the lights burning through the windows. Good, that means Crissy the Queen Wench was back from her errands and probably (hopefully) fuming that I wasn't in the house yet. I started back home.
The front door ripped open just as I was reaching for the knob, startling me. Crissy stood framed in a halo of yellow light, imperiously glaring down at me from the steps above. The smell of food drifted out as well, tantalizing my nostrils. I ignored her and moved past her into the foyer.
"I thought I made it very clear that you were to be INside BEFORE dark," Crissy began. "As per your parents instructions." I still didn't look at her. I just kept moving towards the kitchen, hunting the elusive aroma down. She grabbed my shoulder and spun me to face her. "I'm talking to you, young man. Look at me!"
I slapped her hand from my shoulder and glared at her, my distaste for her very presence burning in my eyes. She placed her hands on her hips and spread her feet. Great. I thought, a lecture.
"Your parents have entrusted me with your care while they are gone," she said through clenched teeth. "I take that responsibility very strongly. They have left written instructions for me on a few things, including your curfew." She put up her hand to stall me from interrupting. "They themselves told you to obey me as you would them. I expect no less. They also told me to discipline you as needed and as I see fit if you misbehave or don't obey me."
She waved a sheet of paper in front of my face which I snatched from her to look at. It was in my fathers handwriting and basically said she had the authority to punish me for disobedience. It also mentioned that he had contacted the constable, school and a couple other authorities naming her as my legal guardian while he and my mother were gone.
"Now march into the dining room and eat your dinner I brought for you." she snapped, grabbing the note from my sweaty grip. "It's getting cold."
I stared at her in defiance a second or two longer before turning and walking to the dining room. I could feel her following closely behind me. I entertained the idea of suddenly stopping in my tracks to throw her off balance, but discarded it. I didn't want to have her touching me even if she fell.
I did slam on my brakes when I got to the dining room though. Not in spite, but in angering disgust. The mouth watering aroma I had scented was coming from several containers of Chinese food cartons on the table. I despised most Oriental foods. I turned to her and made a face of disgust.
"I'm not eating that!"
She looked at me and her face hardened.
"That is all your getting, Chris," she growled, " Your mother had not gone food shopping yet this week. That's why I brought this back. You will eat." She forced me into a chair. I resisted by squirming and whining, but she won out. Damn was she stronger than she looked.
"Now eat!" She ordered. I grabbed the least distasteful item, which was rice, and looked around for utensils. Crissy handed me a pair of chop sticks. I argued and complained that I didn't know how to use these and I wanted a fork right now, but she refused and insisted I use the little wooden instruments. I decided to make as big a mess as possible.
I tried eating using the chopsticks, but dropped most of the food on the table, floor and myself. And not all of it was unintentional. I also tried to gross her out by not chewing with my mouth closed and letting pieces of the food fall out occasionally. Bodily functions also played into my repotoire of annoying manners. All the whole while I whined about the food and treatment.
She just sat across from me, quietly eating her food with an almost mechanical manner. Not one piece of food was dropped from her chop sticks. This continued for about ten minutes when I decided I was done and shoved my plate across the table and started to get up.
"Were you given permission to leave the table?" She asked suddenly.
I stammered a reply but sat back down, a little daunted by the sudden harsh look in her eyes. She spent another few minutes eating then got up and came to stand by my chair. she informed me that I was to finish all the food on my plate before I could leave. My arms crossed in front of me and I settled in for a wait, a petulant look on my face. I was not going to eat any more of this crap.
"Fine," she said, "You can stay there until I say you can move." With that she grabbed all the dishes and washed them, then cleared the rest of the table. I sat in the same position if I were like a statue. Crissy didn't say a word to me or even look at me she just went about her business as if I didn't exist. I wished the opposite were true and she didn't exist. My tormentor eventually finished and left the room, heading upstairs. Subdued noise drifted back down to me, knocks, bangs, rattles and even running water. I assumed she was finishing putting her things away and cleaning up or something.
An hour passed before Crissy made another appearance downstairs. She sauntered over to me and stood in her commanding pose she used so often. her eyes were glinting with wicked glee.
"Since I have been here today," she spoke softly, "You have acted in a very babyish manner. And since you want to act like a baby, I will treat you like a baby. Come along, little one."
She reached out and grabbed my ear. I stood up quickly and followed behind her, head bent as she towed me along by my ear. What was she doing? I wasn't going to treated like a baby! I succeeded in getting out of her grasp, at the expense of almost losing my ear. I confronted her at the foot of the stairs.
"What the Hell do you think you are doing!" I screamed. "I am NOT a baby, so you can just stop this stupid little game of yours and leave me the Hell alone!"
"Such language from a baby!" the wench said in mock shock. "What would your parents think? I think I'll just call them up and tell them all about your bad behavior today. They would really appreciate a call like that just when they get there, don't you think?"
Her hand reached out and picked up the phone from the table. She punched in a few numbers from a list by the cradle. She stopped and looked at me.
"Well?" she asked, her eyebrows arched. I was getting a bit nervous. I'd be in BIG trouble if they had to come back because I was acting up. I swallowed hard.
"I'm sorry," I murmured.
"What?' she inquired sweetly. "I didn't hear you."
"I said I'm sorry," I said a bit louder.
" 'I'm sorry'. . .what?"
"I'm sorry, Crissy," I said subdued. She shook her head and hit another number on the phone. "I'm sorry, Ma'am?" I squealed. She smiled a little and shook her head again.
"I'm sorry . . . Nanny," she stated. My jaw dropped. "Isn't that what all little babies call their caregivers?" I was speechless. She raised the receiver up a smidgeon.
"I'm sorry . . . " I gulped, and paused. Crissy hit two more numbers into the phone. "Nanny!" I almost yelled.
"Veeeeerrrrry gooood!" she cooed, reaching out to tickle me under my chin. I blushed in humiliation. "Now you're going to be a good baby for Nanny Crissy, so she won't have to call up bad babys Mama and Dada on the telephone, won't you?" It was more a demand or threat than a question. I lowered my head and nodded. She looked expectantly at me and jiggled the phone menacingly.
"Yes, Nanny Crissy, " I said swallowing the remnants of my pride, "I'll be a good . . . baby."
She smiled broadly as I said that, a clear look of triumph on her face. She hung up the phone and gently took my hand. I meekly followed her up the stairs and towards the end of the hall. I thought we were going into my bedroom when she veered into the bathroom. I halted a bit and was tugged into the most sacred of domains.
She told me to put my arms above my head and peeled my sticky T-shirt off of me. I risked a glance into the tub and saw it frothing with pink tinged bubbles and a few rubber duckies floating in it. My mind snapped back to the here and now as I felt her hands working to undo my shorts.
Instinctively I swatted at her hands. She grabbed them and pinned them to my sides.
"Uh, uh ,uh," my "nanny" admonished me, "Baby needs to let Nanny help get baby undressed for bathtime. Unless baby wants a spanking." I decided a little embarrassment was betting than fighting her off trying to spank me, so I let her pull my shorts down. My underwear quickly followed. I was beet red all over, but Crissy just ignored it and gently pushed me to sit on the toilet. She lifted on leg and started to untie my shoe. I was told to go bathroom now because I would be punished if I went in the tub.
Crissy continued to work on pulling my shoes and socks off, first one foot, then the other. The whole time cooing to me like I was two or three years old, cajoling me to tinkle like a good baby. Between the embarassment, encouragement and watery Chinese food, I let loose a trickle of urine into the bowl. It stopped after a second and before I could do anything Crissy reached up and lightly tapped the tip of my penis, shaking the last drops off. I was shocked. I also started to get a mild hard-on. She noticed and murmered something about wiping properly and reached into the tub pulling out a wet washcloth.
My eyes widened. She slowly and gently rubbed the warm washcloth over my penis and scrotum, taking a minute to wash it further when it got harder and harder. My eyes closed half way and my slipped into a sort of pleasure trance. I thought I heard her say something like "Goo Ghurl" right before she stopped her ministrations and tossed the towel back into the bubbles.
The nest thing I realized she was pulling me up and guiding me into the bathtub. The bubbles tickled as they crawled across my skin, a slight floral odor wafted up from them as they burst. She told me to sit quietly with my eyes closed so I wouldn't splash or get soap in my eyes. The warm towels resumed its caressing travels, but this time all over my body. It felt sensual having the terrycloth glide over my skin.
Next came a sweetly scented lotion that was rubbed on my chest, stomach, arms legs and back. I opened my eyes when she first started to apply the stuff, to voice my objection, but her finger quickly pushed against my lips and I closed my eyes again. Crissy stopped applying the lotion and busied herself in my bedroom, telling me not to move and not to open my peepers. The lotion began to burn a bit, but it felt like a cold sensation more than heat.
I spoke up and said this to her. She came in the bathroom again and said she had told me to keep quiet. Then again washed my body down with the terrycloth towel. The sensation was much more intense this time, as if it were touching my skin more than it had been before. Again I started to speak but a mild slap on the cheek quieted me right back again.
A few minutes later Crissy had me get up onto all fours in the tub. I was nervous and began to shake, expecting the worst. But she softly chided me for trembling and said all she was going to do was wash my hair. A second later I heard a lid snap open and the old familiar smell of baby shampoo assailed my nose. Crissy turned the water back on as she let the old water drain out of the tub and poured some on my head, thouroughly wetting it. My hair was longish, about shoulder blade length, maybe a little longer and it hung past my face obscuring my vision when I tried to peek. Suddenly I felt her hands begin to work on my scalp, lathering up the shampoo. She worked on my hair for a few minutes then rinsed it out with the water again.
"OK," she said," keep your eyes closed and stand up. I'll help you." I did as she asked and wobbled a bit, but her firm grip held me still. She maneuvered me out of the tub and began to dry me off with a big fluffy white towel. I could still smell the scent of the water on me as she did so. The air felt different on my skin, and so did the towel. I figured it was due to the stuff in the water and the fact that she patted me dry instead of rubbing like I did.
Eventually she finished and walked me into the bedroom with the towel over my head to keep the water from dripping. She sat me on a chair and began to dry my head with the towel. Again she told me to keep my eyes closed. I acknowledged with "Yes, Nanny"'s when applicable. This was almost enjoyable and I didn't want her to contact my parents.
Soon she was brushing my hair out and it felt like she massaged my scalp or something. The towel was draped across my naked lap, masking the stirring of another erection. all this attention was turning me on. Maybe Crissy wasn't such a bitch after all. Maybe I'd try to be nicer to her, maybe. . .
Just then she interrupted my thoughts to tell me to open my eyes.
I did and saw I was facing the mirror in my room. The first thing that hit me was a white satin ribbon tied in my hair like a headband, the bow at an angle on the side of my head. The second thing that hit me was the total absence of hair on my chest. I quickly glanced down and saw that everything was gone where she had rubbed that lotion on me. I stood up and spun around.
Crissy stopped me with a hand to my chest and looked me in the eyes, daring me to speak. She reached behind me and turned the chair around, pushing me into it as she did.
"What are you doing?" I asked in stunned horror and humiliation.
"Well, babies don't have coarse hair all over them like you did," she explained. "So I just made it so you'd have smooth skin like they do. And as for the ribbon . . . I didn't have any baby boy clothes with me so I decided you'd just have to be a baby girl!"
With that she stepped to the side and motioned at the bed with her hand. My gaze followed and widened in even more shock at what they saw. Some sort of long, shiny white material lay on the bed with some other things. she stepped back in front of me before I could make out what it all was. Crissy reached out with her hand to take mine but I snatched it from her. She tried again, but without success.
A warm hand enveloped my cock and squeezed just a little.
"Stand up, baby girl," she hissed in my ear. My penis hardened yet again, and I stood up at her insistent tugging lest I lose it. "Now put your arms over your head."
I did as she said and she released my genitals, reaching over for the white material. She fiddled with it a second then placed it over my arms and head, pushing my arms down as she did.
It was an ankle length satin sleep robe, the thick kind with the soft insides. It had long sleeves that ended in lace edged ruffles as did the bottom. Lace covered the neckline and chest area and had pink ribbons interlaced in it. One thick pink ribbon was quickly tied into a bow, tightening the neckhole and completing the girlish look.
Next Crissy reached over and held up a satin pair of panties overflowing with lace ruffles. she ordered me to lift up my nightie and slid them up my legs, carefully placing my half hard cock inside them. The ruffles were on the front back and sides of the panties and felt like a diaper probably would have under the soft nightie. She motioned for me to drop the skirt and proceeded to smooth out the satin material, especially around my crotch area, patting and caressing. My dick got rock hard.
"Awwwww, my widdle baby girl wikes this, doesn't she?" Crissy cooed as she noticed the obvious bulge. "Now isn't this much nicer than some coarse pajamas or sheets against your skin?"
I gulped and nodded, hoping that was what she wanted me to. Maybe it would spare me further indignities. Not to be, though.
She sat me on the bed and kneeled in front of me holding up frilly booties, saying don't want baby getting cold feet. They were quilted thick cotton and had little pink flowers on a white background. There was some lace and pink ribbons to tie them closed.
Crissy then stood me up and ushered me downstairs to the living room and sat me on the floor. I noticed a few dolls and a coloring book. She told me to start playing with them like a good baby girl. I did as she asked. About fifteen minutes later the doorbell sounded. I almost had a heart attack.
I started to crawl away but Crissy stepped on the hem of my nightie and told me to sit and behave like a good girl. She said this loud enough, i know whoever was at the door heard it. I kneeled on the floor with my hands in my lap and dolls scattered around me as she went to the door.
Crissy opened the door and spoke to someone standing there a few seconds and then turned to me, motioning to move back out of the way. She then widened the door and allowed two guys carrying a couple of baskets in the room. They were from the cleaners my mom used. They picked up and delivered for a small fee. They saw me once or twice a week as I took and picked up laundry for my mom.
I almost passed out as the entered the room and looked right at me. Recognition flickered in both their eyes as they did so. Ones mouth opened in shock and the other began to snicker.
"Problem?" Crissy said harshly, stepping between them and me.
"No, Ma'am," The two replied in unison, but still failing to hide their laughter.
Crissy turned to me.
"Move your playthings out of the way, sweetie, so the two nice men can put the baskets down," she said like you would to a two year old. Her eyes told me to obey and answer.
"Yes, Nanny," I meekly replied and moved the dolls out of the way. Both guys broke out into another peal of laughter which was quickly silenced by a smoldering Crissy.
"Where is the rest of it?" Crissy asked. She was told that there had been a problem and alot of people clothes had been stolen by someone and the company wanted an estimate on the cost as they would replace it. Crissy told them she'd get it to them the next day and ushered them out the door, still giggling.
"Well," she said to me after they were gone, "I guess it's time for bed." She had me gather up the dolls and crayons and put them on the couch then led me up to my room. She tucked me into bed and turned out the light.
"Sleep well, little one," she whispered. "I hope tomorrow will be a better day for both of us!"
tbc????
If you wish to reply or comment on the story, please direct them to ATTN: Sissy Demi on the alt.sex.stories.tg newsgroup. I do not have direct net access... :(