Understanding Aunty
by anonymous Writer
"So that's why the lingerie in my dresser drawers always seem like somebody's
been rummaging through my things!" My aunt said as she undid my pants and
pulled them down to reveal I was wearing a pair of her lace trimmed, pink satin
panties! She then pulled my shirt up to see I was also
wearing her matching lace trimmed, pink satin camisole! She became a little
angry
"And my best lingerie too! You naughty boy!" With that she made me undress right there in the kitchen until I was standing totally naked in front of her. She looked me over then after a moment of thinking of what to do with me she got an idea.
"Come with me!" She said as she took me by the arm and marched me through the house and into the bathroom. She turned on the bath then began rummaging through the cabinet. She took out perfumed bubble bath soap, a large bottle of Nair and her makeup case! She then made me get into the tub! As she left the room and headed for her bedroom I laid there totally embarrassed, wondering what would happen next! I had only been with Aunt Madge for two weeks. I was spending the summer with her like I had for the past three years because my mom would attend summer school at college and didn't want me hanging around our apartment by myself. Madge knew about my secret dressing hobby. Mom had caught me a couple times before and had told Madge but I had never looked through my aunts things on any of my visits here. But I had taken a chance this summer and it was a big mistake because now she had caught me!
Aunt Madge lived alone. She was nearly ten years older than my mom and had been living alone since a divorce years earlier. She got the house and with her settlement she didn't have to work. She was always such a nice and understanding lady. But even after I apologized for what I had done I still felt bad. She was such a feminine lady though. I loved the silky clothes she would always wear and loved the smell of her perfume and the sound of her jewelry as she moved about. She loved wearing feminine dresses and tight wool skirts and bright, shiny satin blouses with sashes that tied into a bow in the front. She always wore lipstick, eye shadow and other makeup too! My favorite thing though was watching her sit in those tight skirts! To cross her shiny, nyloned legs with a zip and then hear the nylons swish against the satin lining of the skirt and see just a bit of the pretty lace of the frilly nylon slips she always wore. I loved the fact that she always wore high heels too, usually black, patent leather pumps that were shiny with four inch heels! I loved watching her tug her skirt down and loved to watch her large bust jiggle under her blouse as she'd get comfortable in the chair.
I guess it was just too much for me. So I thought I would take a chance and start
sneaking into her bedroom to look at her sexy lingerie. She always dressed way
more feminine than my mom and had lots more lingerie, nightgowns and dresses
and skirts too. Everything was feminine! But as I laid in the hot water of the
bubble bath I began to worry that I might be in for a pretty serious punishment
because although aunt Madge was always nice to me she could be strict if you
made her mad! It wasn't long until she came back from the bedroom then closed
the bathroom door and went to work.
The strong floral perfume and hairspray stung my eyes a bit as Madge led me to her bedroom. I was wrapped only in a pink bath towel but now she had done up my hair with a curling iron, and she had completely made my face up like a girl with lots of makeup saying "Isn't this fun" as she worked me over. She had also plucked my eyebrows and completely Naired me! I was now pink skinned and totally hairless! Still holding me by the arm she pulled me into her bedroom and closed the door. I then noticed the pile of lingerie on the bed, the dress and the high heels on the floor! I started to get squeamish and pull away.
"Please aunt Madge, please...le...let me go! I won't touch your things again!" I
gasped as I started to become nervous. She could hear it in my voice and feel me
start shaking. "No, no, no. We're going to have fun sweetie!" She said with a little
giggle as she took my towel away then started looking through the pile of lingerie
on the bed. "Since you like pretty, feminine lingerie next to your skin we should
do it right, don't you think?"
She clasped a white nylon garter belt around my waist and hooked it tight! She made me sit on the edge of the bed. I watched as she took a pair of stockings then rolled one of them up and kneeled in front of me. Without saying anything she worked the nylon stocking over my foot with the red painted toenails then she started pulling and working the stocking up my leg until it was all the way up. She then attached the three garters and smoothed the stocking out before tightening the garters. She put me in the other stocking and did the same thing. She had me stand and brought over a pair of panties and had me step into them! These were white satin, had lots of lace at the leg openings and were almost sickeningly feminine, complete with a blue satin bow in the front of each leg and another one at the center of the waist band. She pulled them up nice and tight and smoothed them out. My bulge was clearly evident. She then added one of her white nylon brassieres then put in two water balloons she had filled with warm water! "I don't have any breast forms sweetie so these will have to do for now." she said with a giggle as she hooked the brassiere, put the water balloons in place in the cups and then adjusted the straps!
She took a pair of old fashioned bloomers and made me step into them next.
They were a heavy, creamy red nylon with lace trim around the legs. I shivered as
she pulled them up to my waist. They swished easily over the nylons she already
had me in and then after she pulled them tight she smoothed them by running her
hands over my shiny, nylon clad bottom and smoothed out the front too! I
accidentally shuddered in excitement at the feel and in being alone in the lingerie
filled bedroom with aunt Madge. I could smell the perfume as I stood in the
middle of the bedroom as she continued dressing me. I could hear the swish of
all the satin and nylon and could hear her clothes too as she moved, her jewelry
tinkling and her breasts jiggling under her deep blue satin blouse!
She took a white nylon slip and, after making me put my arms up, she pulled it down over me and adjusted the straps. I was amazed to realize that all the clothes fit so well. Aunt Madge and I were about the same size, making it easy for her to put me in her things.
"I...I want to quit, aunt Madge" I said as I gasped through my dry throat as she
selected still more lingerie from the bed. She could tell I was starting to shake
with nervous tension now because I had never worn this much before and I think
she knew it! She swished another full slip up and put it over my head. It was all
nylon like the other one but this one was a nude colored, light tan nylon. She put
the straps over my shoulders and let the slip fall. It swished into place over the
white slip as it fell to it's full length showing the frilly lace trim at the hem. As she
adjusted the straps I began to feel faint!
She giggled and then she started running her hands over my sides, my stomach,
my hips and bottom, feeling the slips and making them swish and zip teasing me
mercilessly as she worked the slippery, silken material against me! "Mmmmmm
doesn't that just feel delicious Timmy? Hummm" she giggled as she worked the
fabric.
"Please, please aunt Madge" I begged "I ca...can't ta...take it, I shouldn't be..."
I tried continuing as I stood there, visibly shaken and weak all to Madge's now
satisfied pleasure.
"Yes, boys shouldn't be wearing women's clothes, should they..." She cooed "But
you've been a naughty boy, haven't you?" She said as she stopped momentarily
then went back to the bed and picked up an old fashioned taffeta dress. It was
very feminine and I watched as she started to take it off the hanger. I gasped,
"Plea....please don't, don't make me wear that aunt Madge!" I begged. She stood
there for a few moments then put the dress aside. She then had me sit on the
bed. I was horrified when she went to the closet and brought out a pair of pink,
stiletto high heels! She worked my nyloned feet into them then began buckling
them tightly on me so they wouldn't come off. "Such a stroke of luck isn't it
Timmy? Even these pretty high heels fit you!" She beamed.
She then had me stand once again and as I teetered on the five inch heels she went back to the closet and started rummaging through the clothes hanging there. "Don't you fall and hurt yourself sweetie" she said as she then returned with a long nightgown and a robe! It was a blue, nylon chiffon gown done up in layers and layers of slippery, gleaming chiffon with a silky nylon layer underneath that was a little thicker. She quickly gathered it up and swished it over my head and worked my arms through the short sleeves then let it fall in a loud rustling swish as it fell all the way to the floor. I was noticing the lace trim with red faced embarrassment as she put the long sleeved robe on me and tied the little bow in the front that was just under my new bustline!
She rubbed me again, feeling the perfumed fabric and making me listen to the silken swish as she rubbed the material. Then she brushed against my front and found out that under the nightgown, under the creamy slips and under the bloomers and satin panties I was getting an erection. She seemed a bit excited then seemed a bit satisfied. "Mmmmm my sweet little sissy boy, mmmmmmm he loves the feeling of all this nylon hummm?"
She then got another idea and went back to the closet and after rummaging for a moment longer she returned with an arm load of more of those chiffon nightgowns and robes! She then started swishing them over my head! After she had me in the gown she put me in the matching robe then put me in yet another gown! There was a tan colored one, then another powder blue one then a green one and then she finished with two final sets of full length pink nightgowns! When she was done and tying the front of the last robe closed I looked like a satin doll all done up in the feminine frills!
I started to faint, I tried walking and moving away from Madge as she finished with me but she caught me before I could fall or get away then steadied me and walked me over and sat me on the bed. She took away all the other lingerie and the dress then sat next to me with her arm around me and held me close She pulled me to her, I could feel her breasts pushing against my face as she rubbed my back feeling the slippery nylon. She started rubbing my nyloned legs through all the slippery gowns and the slips as she worked me, teasing me to a fever pitch.
"It's not nice for boys to play dress up in their aunties things now is it Timmy?" She said. I started to gasp and couldn't talk as she continued. "But since you can't seem to stay out of my dresser drawers we might as well do it right, don't you think dear?" She began rubbing me all over then started rubbing between my legs. When she had worked my hard on to a fever pitch and could see it poking up and tenting all the nightgowns and slips up she then got up, took the large pink bath towel and spread it on the floor in front of her full length mirror. She then led me over to the mirror then stood behind me and watched as I finally saw myself. She seemed to like watching as I squirmed and turned even more red faced with embarrassment as I stood there, her nephew all dolled up like a girl!
Madge then fluffed the front of all the slips and nightgowns up then pulled down the bloomers! I tried to pull them back up but she only pulled my arms behind me then held me tight as she continued. She held the gowns and slips up as she pulled the waist of the bloomers down and then pulled the panties down exposing my shaved balls and throbbing hard on! I felt her breasts pushing into my back as she held me. Then she took my penis and began stroking me with her pretty, feminine manicured hands with the long red nails. She began working, up and down, up and down slowly as she cooed in my ear. The excitement was too much! I tried to squirm away but she held me tight!
"Such a pretty boy, all excited in aunties pretty lingerie....yesssssssss, mmmmmmmmm, ooooooohhhh! It just feels delicious doesn't it dearie? Don't fight it now, you just let aunty Madge work all of that excitement out of you boy. Yesssssss, it feelssssssssss so goooood doesn't it? Yesssssssssss!" She giggled as she continued. " But maybe baaaaby want's even more!" She said as she reached over to the bed and grabbed a pink nylon half slip and took it in her hand. She then folded it over to layer the slippery material then she wrapped it around my hard on and started stroking me once again! The room was quiet. The perfume hung in the air as all that lingerie swished and gleamed in the light. Madge's manicured hand, now holding the pink frothy, lace trimmed slip now worked me in a steady rhythm! I felt my hips twitch and then stumbled on the heels and started falling with my hips forward but she held me and wouldn't let me fall as she continued working me even faster until the slip in her hands was zipping and swishing in a frilly, pink whirl!
"Why didn't you tell me you liked such pretty feminine lingerie you poor thing? You need aunt Madge to help you enjoy these little feminine feelings. Look in the mirror, look in the mirror Timmy, aren't you just the most precious little feminine sissy? Aren't you?"
I couldn't talk now, all I could do was grimace and gasp as I tried to fight the feeling and what she was doing to me My nyloned legs gleamed in the light as they trembled and zipped together as I teetered on the pink stiletto heels! The slips and nightgowns rustled and swished as I fell weak. But Madge held me tight and kept working me!
"Yes, maybe for the rest of the summer I will dress you like a pretty girl! Would you like that Timmy? Would you like me to dress you up every day as a pretty feminine girl? Maybe we could go shopping for dresses and lingerie just for you! Would you like that Timmy!? Wouldn't that just feel delicious wearing dresses all day and then pretty nightgowns every night? Yes, I think that's just what we'll do!"
I gasped in horror at being made to go outside dressed like a girl and then being forced to go shopping with aunt Madge in a dress shop where all the ladies there could see me!
"A scolding won't work it seems so maybe aunt Madge will just make you my pretty, , feminine niece for the rest of the summer! Won't that be fun Timmy?"
I gasped and grimaced once again.
"Look into the mirror Timmy, look into the mirror and watch as I work you! You
need to get your fill of these pretty, feminine things so maybe you won't want to
sneak in here, sneak into my lingerie drawers and be a naughty boy! Do you
understand? Look into the mirror Timmy! Yes, look into the mirror at all the pretty
sissy clothes, all dolled up and all pretty and squirming as aunty Madge works
him! I started to sob at the humiliating experience. My mascara started to run but
she didn't stop!
She pushed me forward causing my back to arch and my fake boobs to jiggle as
my hips flung forward, straining my high heeled feet until I was on my toes! She
swished and worked me in the constant rhythm until I couldn't take anymore! I
squealed like a girl and gasped as I felt the first twitch of my penis. I started
spurting drops of come into the air and watched as they landed on the pink bath
towel that was spread out in front of me. Madge exclaimed with excitement as
she continued, milking all the sperm out of me until my penis head was a deep
reddish purple and my balls ached!
"Oooooo! Such a gooooood little boy, come for aunty Madge! Yesssss, yesss
let's work out all of that nervous energy, yessssss! Let aunt Madge make you feel
good Timmy, yessss, make you feel all nice and relaxed!"
She giggled as she finished me off and I became soft once again. I couldn't take
any more and my head was in a whirl. She cleaned me off with the bath towel
then instead of taking me out of all the clothes she tucked me tightly back into
the satin panties then pulled them up tight until I looked like a girl! She then
pulled up the satiny bloomers then dropped the slips and all the nightgowns and
robes back down with a swish. She then wiped off all my makeup! But she wasn't
done with me yet!
Madge took off all the covers off of her bed and soon had me laying in the middle of it propped up by several of her satin pillows. Using several pairs of nylons she had tied my wrists tightly to the ends of the large headboard and as I struggled on the satin sheets still in all that slippery lingerie! She took off my high heels then tied my ankles tightly together then ran the stocking down and looped a knot through the bed frame. She gave a pull that cinched the stocking tight making my legs taut and as immobile as my arms! My penis ached and my balls still throbbed at the working over I had received from Madge. I watched as she continued. She then fluffed out all my slips and gowns then started putting the satin top sheet back on the bed and tucked it in.
She then added a pink blanket and finished with the shiny pink satin comforter that whistled and zipped as she pulled it up and tucked me into the bed. "There! Nice and still now!" She exclaimed as she looked me over now tightly tied and tucked into the feminine four poster bed! She then turned and minced on her heels back toward the dresser. I watched her move in the tight skirt, her hips wiggling, her bust jiggling as I could hear her nyloned thighs zipping as they rubbed together. She grabbed yet more lingerie and more of the sheer nylon stockings then returned and sat on the bed in front of me.
She set the things in her lap then took a sheer beige colored nylon stocking and began rolling it up. She then pulled it wide and reached over and swished it over my head! She pulled until she had much of the material gathered at my forehead! She then took a pair of blue nylon panties and wadded them up. "Such a precious dear" she said as she took my chin and then started pushing the panties into my mouth to my wide eyed surprise! "Open up for auntie sweetie" she said as she pushed the panties in causing my cheek to fill out a bit. She then took a pair of white nylon panties and filled my other cheek then took the last pair of the soft white nylon panties and worked them into the center of my mouth until it was brimming with the lace trimmed nylon. She then quickly pulled the stocking down and over my mouth before I could push out the panties! She continued smoothing and pulling the filmy material until It was gleaming and tight over my head with the stocking welt now coming down the length of my neck! I gasped and struggled in surprise as she giggled then started rolling up another of the sheer nylon stockings.
"It's getting late dear and I am sure you are very tired after your little 'workout.'
You just relax and let aunt Madge do all the work sweetie it won't be long and
we'll be all done. You will be spending the night in my pretty bedroom under
those pretty, shiny satin sheets and all those layers of lovely nylon, isn't that
exciting?" She said as she reached up to put another stocking over my head!
I squirmed as I fought against my bonds and tried to steer my head away but with
one nylon already in place the second one was much easier to get on. I could
hear the zip and feel the pressure on my head as she pulled the stocking quickly
down with a swish and made sure the gleaming fabric was wrinkle free as it
stretched taut across my face. "Now that wasn't nice, trying to get away Timmy.
For that we'll just have to add another couple of stockings then maybe you'll calm
down you naughty little boy!" She giggled as she pulled another stocking over my
head and then another! With each layer it got harder to see! The gleaming, taut
nylon stretched tightly across my face as she swished the stockings down tightly
and made sure they wouldn't come off. I noticed in her vanity mirror as she
worked me over that my head now looked like a round beige knob! She then took
another stocking and put it around my head. I felt her lean in and start tying it in
back and then felt the fabric push into my cheeks and force the panties even
tighter into my mouth as the tight nylon pushed between my lips! She cinched it
down then tied it tightly in back. She took one more stocking and as my nyloned
knob of a head bobbed and I "mmmmphed" into the gag she tied the last stocking
off the same way as well. After getting up she tucked me in once again.
She wasn't going to make me dress like a girl for the rest of the summer. She
wasn't going to make me go outside dressed as a girl or make me go shopping
for dresses either like she had threatened. She just wanted to see me squirm. I
am sure she didn't want anyone to know that her nephew Timmy was really a
sissy. But she had been very convincing and I knew this, what was happening
now, was my punishment and it had been a severe one! For the rest of the
summer now I knew that I wouldn't go anywhere near aunt Madge's things! I
watched her smile at me silently. Then I realized she was now certain I would stay
out of her things for good as well! But either way I wasn't going to test the theory
and wind up shopping for dresses!
"Don't you just look darling!" She said as she smiled, enjoying my punishment
and watching as I struggled and twitched silently. Then she continued. "Now
Timmy, you know now that boys shouldn't wear pretty girls things don't you?" I
wriggled and glubbed through the gag trying to answer as my gleaming, nylon
encased head bobbed helplessly and my gowns swished under the satin sheets.
"Why yes I believe you do understand now don't you!? You do understand! That's
so nice. You shouldn't go through your aunt Madge's lingerie drawers or closet
anymore either! Because if you can't stop your sissy compulsion then I guess
that aunt Madge will have to help you once again just like we did today and work
all of that bad, boy energy out of you and then put you to bed to think everything
over once again! Isn't that right Timmy? Hummm?"
She then put everything away and cleaned up the room then shut the dresser
drawers and the closet. She pulled the satin drapes closed then returned and
kissed me on the cheek as she held my face gently. "Nighty night my precious!
Such a darling boy." She said as she minced in her tight skirt to the bedroom
door then shut off the light. "Sleep 'tight'" she said with a lilting giggle as she
then stepped into the hallway and closed the door behind
her!
I laid back in the darkness. I could smell the perfume and hear the rustle of the
satin sheets against all my nightgowns and the heavy satin comforter as I moved.
My nyloned knob of a head slipped and swished against the satin pillowcases of
the pillows as I grunted, struggling to get loose but it was hopeless. I struggled a
bit more but could only twitch and "mmmmph" and had to finally calm down
because being dressed in the slips and so many gowns and being under all the
heavy satin covers that were tucked tightly around me any further struggle would
only serve to make me unbearably hot! I laid back and tried to relax but it looked
like it was going to be a long night.
I heard the rustle of the satin drapes as they were pulled open and the room filled
with the morning light. I heard Madge's mincing steps, her nylons swishing under
her tight skirt as she
moved around the foot of the bed and went to the other window. I was just
waking up and then realized I was still in her bed, still tied securely as she
opened the other drapes with a swish
to further lighten the room. She seemed matter-of-fact, like nothing was out of the
ordinary as she moved around the bed once again humming a lilting tune in her
feminine tone as she came
over and sat on the edge of the bed in front of me.
I could only "mmffffhh" through my panty gagged mouth as I looked on through
the glossy sheen of the nylon hose pulled tightly over my face and head.
Madge giggled "Oh really? Aren't we just so talkative this morning" as she
leaned across me and untied my left wrist from the bedpost, her large, pendulous
breasts jiggling and rubbing
against me as she leaned over.
"How are we today Tim sweetie?" She questioned with her feminine, lilting voice
and a slightly satisfied giggle at seeing that I was still all trussed up and had
endured my
"punishment" like she had intended.
I glubbed and "mmmffed" a response as I looked at her, my nylon encased head
bobbing in understanding.
"Yesssss, I know!" She smiled, then started untying my right wrist. She undid
the stockings that were gagging me and keeping the panties firmly in my mouth. I
did relax my arms but didn't
move as she began taking the stockings off of my head, then took the panties out
of my mouth.
I was feeling my sore wrists and working my sore jaws as she pulled down the
covers on the bed and untied my ankles, then removed the stocking from the bed
frame. She came around and got
a good look at me squirming on the satin sheets in the cloud of nylon chiffon of
all those nightgowns as I sat up and swished my nyloned legs over the edge of
the bed.
"Let's get you changed out of those things hummm?" She said as she started
helping me undress. Once the lingerie was piled high
on the bed and I was totally naked once again I was given my orders by my
auntie, orders that seemed nothing out of the ordinary, like nothing ever
happened.
"You run along into the shower Timmy dear, and when you get dressed you come
into the kitchen and we'll have breakfast, understand dear?" She said in her
feminine tone.
I could feel my face flush red with embarrassment but I did
exactly as I was told. "Yes auntie Madge," I said as I got my
bearings then hurried out of the room and into the bathroom and
closed the door still embarrassed. I listened for a moment as she
straightened her room and could hear her giggling with
satisfaction!
I took my shower and it felt good as the hot water soaked the
soreness out of my muscles from being tied to the bed all night.
The soap washed away the perfumed fragrance of all of Madge's
lingerie as well. I dried off then returned to my room and got
ready for breakfast. It felt good to be back in my blue jeans,
shirt and tennis shoes.
I was setting the table as Madge returned. I took my seat as she
entered and tied a feminine apron around her waist and began
cooking breakfast. I could smell her perfume and hear her nylons
wisp under her tight satin lined wool skirt as she moved about
mincing and clicking on her high heels! I noticed her breasts
jiggling under her satin blouse and the "tinkly" sound her
jewelry made as she moved. But then I began to remember the night
before and earlier in that evening, my being discovered wearing
her lingerie and then being forced to endure my punishment by
being given a feminine overdose. I turned back to the table and
waited for breakfast.
Madge looked at me like nothing was out of the ordinary, or
nothing had happened. If that had been the case it would have
been like before, but now it wasn't. She had forcibly dressed me
in her lingerie and humiliated me like a little "sissy boy" in
front of her mirror all the while making me watch as she held me,
then jerked my pathetic little hard on and then giggled at the
little twitching "boy" spurts as I came. It was embarrassing and
I could hardly look at her but now, it seemed as if everything
had been forgotten. With my punishment now complete, things would
return to as they had been. However, I now had those memories
seared into my mind! I finished breakfast then decided to take a
walk to the park to get some fresh air. "Have fun Timmy dear and
don't stay out too long," she had said with a smile as she took
away the dishes and I left out the back door.
I thought about a lot of things on the way to the park. I still
had nearly the whole summer to spend with aunt Madge and with
nowhere else to go I decided to get my act together and then try
to forget about everything that had happened. Supper went well
that night with the usual small talk then afterwards we both
watched a few television shows until bed time. The days started
passing by and then a couple weeks. It was nice to see everything
back to the way it was and Madge never mentioned or even hinted
about the little punishment episode with me. That was a relief at
least, and, I was always on my best manners and behavior and did
what I was told. I was the perfect houseguest because knowing my
auntie now, and how severe things could become if she was
displeased, I didn't want to risk further punishment!
I went back to doing a bit of cleaning and yard work for Madge
like I had done all along and the small talk between us
continued. Between the times I wasn't watching a show or a movie
or out riding my bike somewhere or when Madge wasn't baking
something or attending a ladies meeting somewhere we would
usually talk about all sorts of things. She would ask if I was
getting excited about school, about girlfriends and the like. But
I never liked school much and didn't have a girlfriend. She
thought it a bit strange I guess but I told her I didn't have any
guy friends either, not really, a few back home, but we just
hung out. A pretty boring conversation really.
The next Saturday it was business as usual. While Madge went to
the beauty parlor for her weekly hair-set and manicure It was my
job to vacuum and dust the house. After doing the breakfast
dishes I watched Madge gather her purse and coat and as she left
I continued my work. I watched her drive out of the garage, down
the drive and then down the street. I got busy and started,
because I knew I had only a couple hours to get things done and
knew how much Madge appreciated a clean house when she got home.
It usually meant a few dollars extra for me to go downtown and
see a movie or head for the toy store or the magazine rack to
look at the science fiction comics and then she'd even get us a
big pizza or something just as good for supper.
It was a weekly routine I liked. I worked quickly and everything
was going along just fine until I came to Madge's bedroom once
again. I quickly vacuumed the room remembering what had happened
in here just a couple weeks ago as I noticed the large, full
length mirror in it's wooden frame sitting in the corner. I
noticed the large queen-sized bed with the satin comforter too
then quickly finished and after that vacuumed the hallway and
finished with my room.
It had been easy for the most part, but now, as I moved through
the house cleaning and ended up back in Madge's bedroom with the
dust cloth, I began thinking once again. I began dusting the
chairs and the bed posts and headboard then moved to the large
white dresser. I began dusting the top and paused. The room was
silent. I felt my heart start to pound and my throat tighten as I
thought about looking through the dresser drawers again!
I looked at the clock to see that Madge would still be gone for
at least another hour. I started dusting, but within moments
there I was, standing motionless at the dresser once again. I
opened the top drawer and could instantly smell Madge's perfume.
The piles of lacy, frilly lingerie gleamed in the light! A dozen
pairs of her sheer nylon hose were all carefully folded in their
little lingerie compartments, shining, waiting for their next
use.
I noticed the garter belts and the brassieres, I ran my hands
over the cool slipperiness of the panties, the lacy nylon full
slips and camisoles and felt the tight Lycra spandex of the
panty-girdles as I marveled in a trance-like state. Then the
thought of my punishment returned! I could feel Madge's tight
embrace as she held me, fluffing those slips and nightgowns up,
holding my panties and bloomers down as my gartered, nyloned legs
trembled on the stiletto heels as she worked me! I could hear her
giggles, see her determined, smile and remembered her wild-eyed
look as she took an almost sadistic pleasure in my punishment. I
quickly closed the drawer finished dusting and
then just as quickly left the room!
My head was filled with all sorts of thoughts the whole next
week but things went about routinely. But soon it was Saturday
once again! I went through my chores as I always did, but once
again I paused while dusting as I found myself again at the large
white dresser in Madge's room. My breath was short and my hands
trembled as I opened the top dresser drawer once again. It was
intoxicating! I studied the neat rows and folded piles of Madge's
lingerie as I smelled her feminine perfume. My mind seemed to go
into a whirl for a moment. I closed the dresser drawer then
quickly went to my room.
Madge made dinner that night as I set the table and looked
through a couple of magazines. We talked about how the day went
and she mentioned how pleased she was at how nice I was doing my
chores and in keeping the house clean. I thought it was nice of
her, but now, like always, I could only study the sexually
exciting auntie Madge and how she moved around the kitchen. I
noticed she had on a silky dress tonight. It was amazing to watch
it swish and flutter as she moved. And she always wore those
slippery, shiny stockings that teased me so and those ever
present high heels that clicked across the floor as she minced
along, her silken hips wiggling with each step. She joined me on
the couch after supper while I had tuned in a movie. She sat next
to me, I heard the swish of her nylons as she crossed her legs
and then smoothed her dress. She then
hugged me telling me how much she enjoyed my company for the
summer and said she would hate to see it end in the fall! A bit
of polite talk continued during the commercials and for a while
after the movie, but soon it was getting late. I said goodnight
and then with that it was off to my room to get some sleep.
I felt weak as I entered my bedroom. I closed and then locked
the door then started undressing for bed. I took off my shoes and
socks, my shirt, my T-shirt and then undid the belt on my blue
jeans. I took them off and then looked in the mirror. I was very
excited, but felt a bit sickened to see myself wearing the lace
trimmed, black satin camisole, the matching tap pants and
the shiny, slippery taupe colored hose that were tightly gartered
to one of Madge's garter belts! I quickly took the lingerie off
then changed into my pyjamas. I pulled down the covers on the bed
and after carefully folding all the lingerie I put it between the
mattress and box spring! I laid down exhausted and tried to
sleep.
"Stupid idiot!" Was all I could think. How stupid I had been! I
should have just dusted Madge's bedroom quicker I thought or even
avoided that room all together, at least for a while. But I
hadn't! And even with those memories of my punishment still fresh
in my mind I was back at it once again! I could have been caught
just like before. When Madge hugged me I was lucky she didn't
feel the nylon of that camisole sliding under my shirt! I had
tucked my shirt in, but left it lose this time to not show any
straps by accident and had buckled my belt tightly as well to
keep everything in place. I'd been lucky! But I tried to relax my
thoughts by telling myself it could still work. I could have my
fun and if I was careful this time, much more careful, Madge
would never know! I wouldn't be able to try on any of her dresses
or those nice high heels of hers and no makeup either but I could
quietly enjoy her lingerie. And after all, once the summer was
over everything would get back to normal and no one
would be the wiser.
I had gotten a break that helped in my decision. In addition to
my Saturday routine she had me helping with the wash now too.
Madge had taught me how to wash clothes and what went where and
how to wash all the different fabrics with different wash cycles
and how to use different soaps. Blue jeans were separate, just a
scoop of Tide, while whites were separate, washed on hot and
with the same soap. I was a bit nervous in washing her lingerie
though. She showed me how to set the washer to the delicate cycle
then showed me the proper wash temperature and amount of Woolite
to add and how to hand wash her nylon stockings and then hang
them on the drying rod in the basement! It was a bit embarrassing
with her standing over my shoulder as she watched me wash her
lingerie in the wash basin but added that I was getting to be
quite the little helper, secure in the knowledge that this was
most likely as close as I would ever get to her things ever
again!
I often heard her stifle a giggle when ever she would watch me
handle her things, but little did she know. Now I could borrow
her lingerie and then wash it out and mix it in with all her
other things and finally put them in the laundry basket when they
were clean and dry. She then would take the basket up to her room
to fold and then return everything to her dresser drawers. I
remember her giggling when she asked me If I wanted that chore as
well.
"No ma'am, I would rather not do that," I said with a quickly
reddening face.
"Are you sure?" She would tease further. "Such a darling boy,"
she would finish as she would leave and take the basket upstairs.
I couldn't help feeling she was toying with me, but we both
remembered my "punishment" and it was simply left as such, just a
memory and an understanding.
Little did she know that while she watched me wash her nylon
stockings in the sink I was wearing a pair of the same kind under
my blue jeans firmly attached to another of her garter belts
under a pair of her lace trimmed satin panties! It was a bit
embarrassing but I could feel the excitement return. The
excitement of doing what I wasn't supposed to do, that swagger of
arrogance on my part that wanted to tell auntie that my legs were
probably prettier than hers! And I guess in secretly standing up
to her in defiance even after my punishment.
Another week passed and I found I was now wearing nearly
everything that wouldn't show through my street clothes. I tried
her briefers, pantyhose and teddies along with panty girdles too!
It was quite an enjoyable sensation in having my run of that
lingerie drawer and in wearing her clothes. And since I was
more than careful this time I wouldn't be caught again.
I began waiting for the next Saturday when I would have another
chance to get a fresh collection of lingerie for my secret
under-bed hiding place. I was careful not to ever take too much
though and so far everything was working. I found I wasn't scared
at entering Madge's bedroom anymore and it became almost
second nature now to rummage through her dresser drawers making
my selection for the coming week.
I carefully looked through the lingerie making sure to keep
everything just so and wrinkle free so she would never know I had
been in her things. I took out some nylon stockings and two pairs
of her glossy, taupe support hose almost without a thought, but
this time I heard a "click!" I turned quickly then
heard another "click!" My heart started pounding immediately, I
couldn't have been stupid enough to get caught, not again! And
then I noticed something new that had been added. On a little
table in the corner of the room I noticed a little air purifier
machine! I noticed the little red light that showed it was
working as It hummed along and then heard a "pop" and another
"click" as it continued cleaning the air.
It was a bit unnerving but I composed myself, finished making my
selection of panties, camisoles and even borrowed a silky, nylon
pants liner like a slip for your legs! I straightened the dresser
then left the room. I found it felt delicious over the nylons
when I tried it on that afternoon then wore it the rest
of the day. And all the while poor "dizzy" Madge didn't have a
clue! I didn't mean to denigrate her because I liked her so much,
but really, she just didn't understand me, or who I was. I wasn't
hurting anyone and she should have understood that. But that's
the way it was I guess. I looked at the calendar then
realized summer vacation was almost over! It was now only three
weeks before I was scheduled to hop the plane for home and say
goodbye to dear auntie for another year.
And then it was three weeks later, and another Saturday! After
my trip to the dresser in Madge's room I had selected my favorite
outfit of hers. It was that black satin camisole and the matching
lace trimmed black satin tap pants and the garter belt that held
those long taupe nylons so nice and shiny and tight on my legs!
Once I got changed into that outfit I put on my shirt and jeans. I finished my housework as usual then planned on spending my last weekend with dear auntie Madge before flying back home that Sunday night. Things had gone really well and I was even thinking about my visit for next summer when Madge returned with a surprise!
I was in the kitchen straightening up when she got back from the
beauty parlor. She was nearly an hour late this time though and I
soon learned why when I saw my mom come through the front door
with her! Madge put her coat away then excused herself to go to
the basement. I hugged and greeted Ruth! We sat and talked in the
kitchen and were into quite a conversation about her
schooling and in talking about the fall and everything as Madge
came through the kitchen with her basket of lingerie to take to
her bedroom just like usual.
Ruth seemed glad to see me! I guess I should have called her
"Mom" as I usually did but she wasn't really my mom. We weren't
even related! And although "Auntie Madge" wasn't really my aunt I
still called her "Auntie" just the same. I had been living with
Ruth for several years as a foster child and had stayed on even
after she had gotten divorced. We got along great but I always
figured it was a little strange that Social Services didn't place
me with another family. But I had been caught by one other foster
mom. I had gotten into her things when I was only eight or so. It
was embarrassing to me and I don't remember all of the details
but she didn't find it funny that a little
boy would be going through her dresses and lingerie. I guess she
didn't want me around anymore because It wasn't long after that,
that I was placed with Ruth and her husband. Anyway, things were
going alright now so it didn't really matter anymore. I was just
looking forward to getting back to my regular life.
Ruth had me go get packed and soon all my things were boxed and
stacked neatly by the front door. Madge was making coffee in the
kitchen and getting ready to see us on our way. She then went to
a cabinet and took out a large photo album. "Come on you two!
Let's have another look through some pictures for old times sake
shall we? You know how lonely it can be for me living alone here
all winter." She said as she led us out to the living room. I sat
in the middle with Madge and Ruth on each side of me. They sat
close as Madge crossed her nyloned legs with a swish then began
paging through the old photos.
I guess I was part of the family now. There was a picture of all
three of us at our house in early spring and another at Madge's
for the holidays. There were other people as well but more of me
as an even younger kid and me on my bike and hitting baseballs
and at a summer barbeque from a couple years back showing me and
Madge. She seemed to enjoy having the pictures as memories as
she paged through the large album. She then turned another of the
thick pages to reveal more photos. My stomach began to churn at
what I saw as Madge and Ruth sat close looking over the pictures.
Madge turned the page again, then again and again. It was me, and
in these new pictures I was in Madge's bedroom,
dusting, and going through her lingerie drawers!
"Such a clever little sissy sneak isn't he" Ruth said as they
continued looking at the pictures of me. "Maybe 'he' won't be a
'he' for much longer. Maybe our precious sweetie here really
wants to be a girl! Isn't that right
Timmy!?" Madge giggled as she continued paging through the
pictures.
I noticed that every one of them were in order too, every
Saturday from nearly the beginning as I started in rummaging
through Madge's lingerie drawers and wearing her lingerie once
again. Both ladies giggled at seeing me holding the lingerie and
feeling it as the pictures plainly showed. Madge kept turning the
pages showing the Saturdays passing.
I started to squirm but the ladies sat me tight between them as
they continued. They reached the last couple pages which were now
today's pictures!
"Isn't that just darling!" Madge said with a giggle at the
picture showing me holding up the black satin tap pants to myself
in front of her dresser mirror modeling them, and taking out the
garter belt and those sheer garter nylons!
I felt my head spin, my ears ring and my stomach twist into
knots as I started to say I was sorry, just like before but
although both ladies heard me it didn't make a bit of difference
this time. Madge closed the photo album and set it on the end
table.
"And now for the proof!" Ruth said with curiosity as she quickly
started pulling at my shirt and undoing my belt! She worked fast
as Madge held my arms and in my confused state it wasn't long
before my shirt was torn open with buttons flying exposing the
gleaming, lace trimmed, black satin camisole.
"Well, you won't need this boy's shirt anymore anyway Timmy,"
Ruth said as she continued working until my pants were down
around my ankles. There I was now, sitting between Ruth and
Madge in that black satin camisole, the matching tap pants and
those tightly gartered nylons that now swished and gleamed in the
room light as I struggled to get up and get away in
embarrassment. Suddenly
I felt something wet being pushed across my face! Madge had taken
something out of the end table drawer, I noticed the cotton
wadding and the little bottle of liquid sitting there as well as
two little bottles and what looked like syringes!!
As Ruth helped hold me Madge held my upper chest with one arm
pulling me tightly to her while at the same time keeping the damp
cotton pressed against my face. I gasped and coughed at the first
whiff. I could smell the sickly "hospital" odor of the liquid and
tried to struggle to get away not knowing what was going on! I
"mmmuummmfffed" into the mound of cotton wadding wild-eyed and
flailing to escape but Madge held me tight to her chest, my head
firmly between her large swaying breasts as it slipped on the
satin of her blouse as I struggled!
"Don't worry sweetie, you just relax and don't struggle" she
said as she held me tightly!
I could hear my nylons swishing as I squirmed my legs but Ruth
held me tight as they waited in the silence while the chloroform
took effect.
I jerked and twitched struggling further but Madge fixed that by
easily pulling me around on the couch and putting me into a
scissor lock! With my arms stuck behind me and with her legs
tight around my waist and Ruth holding my legs down I quickly
began to feel weaker and weaker! I could feel my strength ebbing
as I twitched, my head tight between Madge's satin bloused
breasts as she held the cloth to my face. I could feel my eyelids
begin to sag as I blinked weakly. Then my gasps and moans began
to quiet as well.
"Just a bit more," I heard Madge say a bit out of breath from
the struggle "he's almost out now."
I flailed weakly once again and issued a muffled babble into the
cotton wadding as my eye's fluttered for the last time. I felt
Madge and then Ruth relax their grip on me.
"There! Nighty night little princess," I heard Madge say with a smile as I finally went limp and the room went black!
I didn't know if I was dreaming or not. I remembered being
caught, again, but this time it was different. I was worried
about Madge carrying out her threats to take me shopping for
dresses dressed like a girl but,this was nothing like before and
it was embarrassing to have Ruth here now but since she already
knew about me it didn't make much difference.
Madge had proven to be smarter than I thought. She must have
known I wouldn't change. Adding that air purifier to her room,
that was clever. The noise it made disguised the camera she had
hidden in the room that took all those pictures of me. She had
rigged the bedroom door to activate the camera to take a picture
every twenty seconds or so until the door closed again. So each
time I entered the room she had several pictures of me dusting
and especially going through her things! The clever part was how
she got the pictures. She had hidden a printer down in the
basement and with a little lap top computer simply printed out
the pictures she wanted to add to the photo album later. It was
all quite a plan and it scared me when I realized that Ruth was
in on it as well!
I felt like I was floating in limbo! I could hear laughter and
giggles and could feel water running against me, feeling someone
working me over! I could feel hands on my face, the pain of my
eyebrows being plucked and someone doing something with my hair
and voices commenting all the while in a faint discombooberated
laughter mixed with purposeful speech but couldn't understand!
I felt a dull click then felt the pain in each earlobe and could hear more giggles, more talking and planning. I felt myself floating once again then felt the swish of satin and nylon and could smell perfume but couldn't associate it with anything and couldn't do anything about it as I floated in the blackness.
Then suddenly I noticed something bright and pink! It started
coming into focus. I awoke to find I was lying on Madge's bed
looking up at the frilly satin canopy of her large four poster
bed! I blinked and turned my head slowly and groggily and could
already smell the perfume. I then saw Madge in her closet moving
and looking through things. Ruth then entered the room and began
searching the dresser drawers and taking out several items of
frilly lingerie.
I moved my leg and felt the nylon swish on the satin comforter
as I tried to lift my head but fell back silently still to weak
to move. Madge noticed then approached with a smile, and she was
holding a large garment bag filled with some frilly concoction.
"Well, well, well! Look who's finally awake!" She said as she
laid the garment bag on the edge of the bed smoothed it out then
undid the long zipper. She then took out the large dress and
fluffed it out.
"That's really a beautiful gown Madge" Ruth said as she took
notice.
"I never thought I would have need of it again but we'll put it
to good use now!" Madge said with a giggle as she set it aside.
I then started drifting in and out as I heard them continue their girl talk and giggle. I heard mention of me as well, how the name "Timmy" wouldn't suit me anymore and that "Tamara" would be much nicer and in talking about measurements and other things, but I still wasn't sure what was going on. I then felt a light slap at my cheek which brought me back to reality. It was Madge.
"Now, try and stay awake Princess, your head will clear much
faster that way. I am so sorry we had to resort to putting you
out sweetie, but you were so much more manageable that way and it
made our work much easier," she said as she smiled sweetly then
moved away once again.
I looked at my hands after instinctively raising them to protect
my cheeks then noticed my arms were once again totally smooth and
hairless and my fingernails had now been worked on! They had
glued salon nails on me and had painted them a bright gloss red!
I tried to sit up. I raised my head to see I was already wearing
a garter belt with long opera length white nylon hose. They
gleamed in the light as I moved my legs, swishing them on the
satin comforter as I rose to my elbows to look further. They had
me back in those creamy, white satin panties with the delicate
lace trim and the pretty blue satin bows on the front of the legs
and at the waist and had also put me into a pair of
white, open toed ankle strap pumps with six-inch heels that were
tightly strapped to my feet. It was then that I noticed my
polished toenails matched my manicure! I got a shock to see I now
had breasts! I squeezed them then noticed they wouldn't come off!
"Be careful with your new breast-forms sweetie," Ruth said as I
looked them over still in a stupor from the chloroform.
"He'll get used to them," Madge giggled as she looked over at me in my still perplexed state, "feel like a pretty little girl sweetie? You will in a little while," she giggled.
I could feel their weight, noticed the size of the areola and
saw how the large nipples jutted out as the forms jiggled just
like they were real. I pulled at them again but found they were
indeed stuck tightly. I realized they were securely glued to my
hairless chest filling me out just like a woman!
Ruth then came over, sat me up then sitting behind me took a
white satin brassiere and wrapped it around me! After putting my
arms through the straps she lifted the brassiere, fitted my new,
jiggely breasts into each of the cups then hooked the bra
securely at the back. She finished by adjusting the straps. As
she tightened them my bust began to lift as the brassiere began
to support the heavy forms. When she finally finished fussing
with the straps my bust stood straight out!
Before I could mumble a question Ruth helped me to my feet. I teetered on the heels as Madge set an old fashioned white satin corset on the bed and put a cloth tape around my waist. They continued on as before, all matter-of-fact like nothing was out of the ordinary.
"We'll have to get him down by almost eight inches! And he's not
going to be able to stand while I lace him into the corset,"
Madge said with a bit of angst at my waist size and in still
being groggy.
She found a solution by clasping and then buckling fleece lined
leather cuffs around each of my wrists and moving me away from
the bed towards the side of the room. As Ruth held me, Madge
attached a clip to the cuffs to keep my wrists together then got
on a sturdy chair and looped the long clothesline rope through
the large metal eyelet and pulley arrangement in the ceiling!
My head was spinning as she got down from the chair, put it
aside and started pulling the rope tight. Soon my arms were over
my head! Ruth stood back as Madge pulled again until the rope was
tight and I was standing there teetering on the stiletto heels!
Madge went to the bed and gathered the corset and returned to me
as I stood there in my brassiere, my garter belt with the white
glossy nylons and the pretty white satin panties I was now
tightly tucked into that she had used on me before. I wobbled on
the heels as I felt my legs shake but couldn't fall because I was
tightly tied and suspended from my wrists.
As I hung there I felt Madge put the corset around my waist! "Like my addition to the ceiling princess? Now it will be much easier to dress you," she said as she began.
She carefully hooked all seven of the front busk hooks and
centered the long satin corset on my waist and hips making sure
it came to just below the white satin brassiere.
"I... I'm sorry aunt Madge," I gasped still dizzy, fearing a new and even worse punishment this time. Especially since I was now wearing breast-forms! I couldn't imagine what these two women had in mind, but they were so calm in working on me. It felt strange, surreal.
"Plea... please don't punish me again! We'll just leave and take
that plane and I won't come over for summers any more. I'm sorry
auntie!" I was sincere but this too had little effect.
Madge moved around behind me as Ruth looked on and began working the white silk laces and adjusting the corset making sure it was centered on my slight frame. I heard the swish of the laces moving through the sturdy metal eyelets at the back of the corset as Madge began gathering them, pulling them tight!
"Yessss!" She gleamed "we'll have you looking like a little
feminine beauty in no time!"
I was caught off guard at first feeling the corset start to
tighten as it centered around my waist. I had never worn one
before! The second pull caused the laces to sing through the
eyelets and tighten the corset even further. I let out a
surprised "Oooofff" as Madge pulled the laces again.
"Don't you like this pretty corset sweetie?" Madge said as she
paused for a moment giggling at my plight. "Don't you worry,
you'll be getting used to lots of corsets, and lots of pretty,
frilly things from now on," she said as she continued.
I started getting scared! I remembered again back to her saying
she was going to dress me up like a girl then take me to the
dress and lingerie shops! Could this be it this time? Maybe I had
gone too far! I begged her not to make me go through that
embarrassment, I panicked and pulled at the wrist cuffs that held
me from getting away as I teetered on my heels. I pleaded with
Madge and begged for her to let me go but she only said, "not
this time dearie, there's no shopping for dresses, not just yet
anyway," she giggled then finished by
saying, "simply dressing you doesn't seem to have an effect so
there's been a change of plans!" she said as she continued lacing
me into the corset.
Another pull made me gasp! I noticed the corset was now
beginning to form me to its shape, pulling me in at the waist,
giving me a more feminine shape! I looked down past my tight,
white shiny satin brassiere and my glued on, jiggly breasts and
noticed how small my waist had become. Madge stopped for a moment
then wrapped the cloth measuring tape around my waist. "Hummm,
another three inches and he should fit the dress perfectly!" She
said and then continued. Another pull cinched the corset tighter
still! The creamy, glossy, white satin began to gleam in the room
light as it became tight and every wrinkle vanished! I began to
sob at my predicament and Madge took notice.
"You just quiet down now 'sissy boy' you know why you're here,
don't you? You need a smaller waist to wear my old wedding gown
so I am making the adjustment by lacing you into this corset."
"You just take your medicine and things will go much easier for you. Just so you know though that we are just getting started today, just getting started. And if you ruin your pretty makeup you will really be in for it. Or do I have to gag you again!?" She said as she then tied off the corset at the base of my back then started pulling the laces at the center of the corset to give them a second phase of tightening! She worked for a minute to get the laces out then put her knee at the small of my back and continued!
Not wanting to be gagged I got quiet in a hurry but she could
still hear my sniffling sobs!
"See? This is what happens to swishy, little sissy boys!" Madge
said as she worked the laces until the corset started to creak!
Another few stiff pulls and she wrapped the laces around my now
tiny waist, then finished by tying them into a sturdy knot at the
back!
She moved back and sat back on the bed, looking on as I twitched
and struggled. Ruth then went to the side of the room and pulled
over that big floor mirror, the one Madge had used before in my
punishment! She put it along the wall in front of me and adjusted
it. I couldn't believe what I saw!
They had been busy while I was out. Although I hardly did have
any body hair what little I did have was now totally gone! My
hair, which had grown out a bit over the summer was even longer
but was now a bright blonde and had been cut and curled into a
feminine style. My eyebrows had been thinned and plucked into a
high, feminine arch and my face had been totally made up with
false eyelashes and everything. I noticed that the earrings they
had me wearing were now the real variety as they had pierced my
ears as well! I looked like a little woman now in nearly every
way! My ample bust jiggled in the white satin brassiere as I
struggled. The gleaming white nylons held tightly gartered
swished a bit as I struggled to get loose. The corset was now
very tight and molded my shape even further into a feminine form.
I pulled at my wrist straps and grimaced as I teetered on the
white stiletto heels. I began to openly sob at my fate!
Madge then came over for another look. She stood behind me, then
began running her hands over me, checking every detail. Ruth
brought over a frilly garter and handed it to Madge. She slipped
it over my shoe and pulled it up my left leg until it was high on
my thigh. She fussed with it until the little blue satin bow was
at the front and the frilly lace was properly fluffed. She
then checked my garters and felt the new smoothness of my legs
now in gleaming nylon hosiery.
She felt my tight, corseted waist and marveled at my new
feminine shape. Now satisfied at my progress it was time for
more, much more.
"Help me take him down Ruth," Madge said, "it's time to finish
dressing him!"
As Ruth steadied me, Madge unhooked the white clothesline rope
from the sturdy hook near the window frame. As the rope slipped
through the pulley I felt the weight returning to my feet. Ruth
quickly removed the wrist cuffs, then moved me to the bed. She
gathered a floor length, white satin slip and had me put my arms
up through the straps as she swished it over my head. She pulled
it down into place. When she helped me stand I felt it swish all
the way to the floor! Madge then came over with a mound of white,
frothy lingerie.
"Hold that slip tight at his ankles Ruth and we'll get him into
this petticoat," Madge said as she fluffed the voluminous white
garment open with a swish and set it on the floor in front of me.
Madge pulled me over and forced my feet through the waist of the
petticoat then quickly pulled the frilly, nylon chiffon garment
up over the slip and began tying the ties tightly around my now
tiny corseted waist! It swished loudly as she made sure it was on
properly and tied tightly. She gathered another petticoat and as
Ruth held the bottom close to my legs Madge made me step into it
too! It didn't take long but soon Madge was tying the third
petticoat tightly around my waist. The petticoats swirled and
swished as she fluffed them out.
Now satisfied with her work she continued, "now, let's get you
into that pretty gown!"
Ruth took the dress out of the garment bag. I heard the swish of
satin as she brought it over. I tried to get away but Madge held
me tight making me watch as Ruth gathered up the dress.
"What's the matter dear? I thought you'd love such a pretty dress!" Madge said as she helped gather it up. "Arms up sissy boy!" Madge ordered.
I felt sickened, I wanted to run away and never come back. But I
was more than sure that I wouldn't get far. I was in Madge's
bedroom once again. I could smell the perfume, and the only sound
was the swishing of the satin and all that lingerie as they
really worked me over. I put my arms through the long sleeves of
the dress and felt the satin swish smoothly around me as they
worked it down over my body. They had me stand and as I held one
of the corner posts of the bed they pulled the wide skirt of the
dress down over the wide, fluffy petticoats. I felt Madge adjust
the dress in the back as Ruth buttoned the four satin buttons at
each of the wide white satin cuffs at the sleeves. I heard the
zipper being pulled up and felt the dress become tight around me
as I was fitted into it. Madge did the hook at the back of the
high, lace trimmed collar and began buttoning the long row of
buttons at the back. She finished by tying the wide satin sash at
my waist into a large fluffy bow at the back of the dress.
They then cuffed my wrists once again and took me back and stood
me under the pulley arrangement hanging from the ceiling. A few
pulls on the rope and Madge had me standing straight up once
again, teetering on my heels as the gown and petticoats swished
around me. Ruth then added a double layered white chiffon veil
and pinned the cap to my now feminized hairdo. Once she was
finished Madge gave another pull on the rope. The rope whistled
through the pulley causing my feet to barely touch the floor.
Another pull and my feet left the floor altogether! With one more pull my feet were over a foot off the floor. Madge then tied off the rope securely so it wouldn't slip. She then gathered a few other objects I had never seen before and then both ladies began working me over.
Madge fluffed up my dress, then pulled my white satin panties
down. They swished easily over the nylons I was wearing and once
they were completely off she tossed them on the bed. Ruth started
adding ankle straps to my legs which included a shiny metal bar
then tied me so my legs were spread and hooked the
center of the bar into a metal ring under the carpet bolted into
the floor which kept me from flailing my legs. Madge added a
similar contraption with a metal bar and strapped my thighs and
cinched them down. A few adjustments later and my thighs had been
stretched and forced wide. I sobbed in a scared voice
begging to be let down and asking what was going on.
"That's so you can't close your legs dear" Madge said. When I
asked why, she said, "You'll see sweetie, you'll see!" She then
gave the rope at my wrists another pull and didn't stop until I
was cinched tight, suspended helpless in the air! After making
sure the mirror was directly in front of me, Ruth began
gathering the dress and all the petticoats and pulling them up
around my waist, exposing me as Madge put the bath towel under me
and spread it out on the floor! I now knew what was next! Madge
giggled as I twitched trying to get away!
Madge moved behind me and wrapped her arms around me then
giggled at the sight of my tiny flaccid penis and little hairless
scrotum. I noticed they had dyed my little patch of pubic hair
blonde too and had trimmed it into a little muff. It was
embarrassing to notice the little pink satin ribbon they had
added on for further feminizing effect! She ran her fingers down
the soft shaft causing me to squirm but with my feet off the
floor and ankles tied wide and with that thigh spreader
contraption holding me wide I could only gasp and squirm. Ruth
held the dress out of the way as Madge continued.
"Such a pretty boy," she cooed. "I thought you would just be
ready to explode with excitement dressed as pretty as you are
Timmy dear. What's the matter?" she said with a giggle. I grunted
as she started to gently work my little penis.
"Just relax now, let auntie Madge do allllllllll the work
sweetie," she said. And in moments I could feel myself blushing
as I struggled, with Madge working me she was getting me hard!
She then began stroking me! I gasped and grunted trying to get
lose but it was hopeless. I could only hear the ropes creak and
the satin of the dress swish as both ladies now looked on at what
they were doing to me! I began to struggle even more as Madge
picked up the pace.
"Doesn't this just feel delicious Timmy? Such a precious little
sissy!" She cooed and giggled as she worked me. It didn't take
long this time and finally I felt myself spasm, my little hard-on
twitching in Madge's hand as she worked me, and watched the
little spurts of come spray out and fall to the bath towel
on the floor. Ruth giggled too at the pathetic little display and
asked Madge. "You tied him down for that little bit?" Madge then
smiled "We're not done with little Timmy, not yet!" She said as
she left the room and quickly returned.
Madge brought in a little package then pulled my veil up. She
then took a strapped contraption with some type of gag and began
trying to force it into my mouth. I tried to get her to let me
down, saying I had learned my lesson as I hung there in red faced
embarrassment but she only continued as she forced the
rubber bulb past my glossy red lips and into my mouth! I was
whimpering as she quickly pulled the straps tight around my head.
"We're not done yet Timmy!" she said, "we just need to keep you
quiet so we can have a lot more fun. We wouldn't want to have the
neighbors hear now would we?" She said as she cinched everything
down.
Once she had the gag tightly buckled she hooked up a little tube
with a squeeze ball and began pumping it, squeezing it in her
hand. I felt the rubber bulb begin to inflate in my mouth! Madge
continued pumping until my mouth was filled and my cheeks were
puffed out making me totally silent. She unscrewed the pump bulb
then put the veil back down.
"Why did you have to gag him?" Ruth asked. Madge, now pulling on
a pair of white latex gloves finished by opening a tube of
lubricant and applying a good measure to two fingers of her right
hand.
"I gagged the little sissy because I was getting tired of his
whimpering, and you'll soon notice we will need little Timmy
gagged because he's not going to like this. It's going to be a
little intense for him." She came over. "Hold the dress up Ruth."
I felt her move in and put her arms around me and then felt her
cold latex fingers probe my behind! I grunted as I felt Madge
find the opening and struggled but it was no use. I gasped as I
felt her work two fingers inside, twisting them back and forth,
forcing them in deeper! I tried to pull my legs together but it
was no use. She held me closer probing, working her lubricated
fingers in deeper and deeper. My little penis still hung spent
and flaccid but I could feel something strange happening. Madge
found my little prostate and started massaging it! She then
reached around with her left hand and after fumbling behind my
little nut sack she squeezed the inner root of my penis and
began massaging it!
I gasped and struggled pulling at the creaking ropes and
"glubbing" into the gag as Ruth looked on and started to smile as
Madge giggled knowing exactly what she was now doing!
"There! That got his attention!"
I tried to scream out but could only make muffled grunts and
"mmmuuphhhsss" as Madge worked me. The room was silent except for
my twitching which caused the ropes and leather straps to creak
and the satin of the gown to swish slightly but Madge held me
tight and kept going as Ruth looked on.
"What's that supposed to do?" she asked.
"Little Timmy evidently didn't get enough stimulation last time,
so now I am going to make sure he does. I'm going to make him come until he can't take anymore!"
I wasn't getting hard but could feel the pressure building
inside me as Madge worked and massaged me.
"There, just a little longer and sissy Timmy here will be getting a good 'milking', yes a gooooood 'milking'!"
I then felt the first twinge as a little spurt of sperm shot from my flaccid penis! I gasped and grunted but Madge continued with a smile and a satisfied giggle.
"Poor little sissy." Ruth listened as she spoke. "You see, your
little orgasm was only the beginning! I am massaging you, forcing
your little testicles and all your little glands to make more
sissy cream! Once you start dribbling little sissy boy I can keep
working you for hours if I have to!" She giggled with
excitement as she looked over at my still flaccid little penis
and another spurt happened that was quite involuntary! Then a
clear drop of liquid formed at the tip of my penis! It dripped to
the towel below as Madge kept up!
"Yessss, now we can really start the 'milking!'" In a few
moments my little penis began to drip even more, each drop
feeling like an ejaculation as she forced my little boy system to
perform beyond its limit! It was too much to endure! I struggled,
gasped and writhed as the ladies held me. Madge was now having
her fun and her payback at my getting into her things.
"Yesssssss, 'milking' my little sissy boy, 'milking'! It just
feels so intense, doesn't it Timmy dear? Hummm?" she said with a
giggle as she continued on!
I tried to fight it but it was no use! My body twitched and
spasmed as she worked me. I began seeing stars, my ears rang! My
hips began bucking wildly, almost humping as they held me,
forcing me to endure the 'milking'! The satin gown swished as my
thighs trembled and I gasped and "glubbed" helplessly into the
gag! This went on for nearly an hour until finally my little
penis and lower insides felt like they were going to seize up!
Finally my penis stopped dripping, my insides totally spent!
Madge worked me a while longer, but once sure I was totally
drained and dry she released her hold behind my nut sack then
took her fingers out of me with a lubricated 'splork!' She stood
back and took off her rubber gloves with a loud snap admiring
her work as I hung thre barely conscious!
I hung motionless and limp as she lowered me on the rope just a
bit, then took away the thigh spreader as Ruth untied my spread
ankles. Madge took the white satin panties from the bed and took
a pair of briefer panties from her dresser and came back to me.
She took my sore little manhood and pushed my little testicles up
inside me and tucked my little penis tightly back. She pulled
the little white panty briefer up tight over my hips and made
sure I was properly tucked, my little mound now looking just like
a girls vagina!
She then pulled the white satin panties up my legs and smoothed
them into place over the briefer! She giggled as she worked her
fingers between my thighs feeling my new little "V" mound as I
squirmed! Ruth then tied my ankles back together and hooked the
rope through the eyelet under the carpet and cinched me down.
Madge pulled my wrist ropes once again until my body was
stretched tight once again.
Madge fluffed the gown out and all the petticoats until they were
wide and sweeping. Ruth gathered the bath towel from the floor
and made sure the mirror was directly in front of me as they
finished. They straightened the room and paid me one last visit.
"Are we having fun yet sweetie?" Madge chuckled at seeing me
totally drained, totally feminized and under her complete
control!
"You just stay in here and enjoy yourself for the rest of the
afternoon while Ruth and I finish up a few things. You just stare
into that mirror and marvel at how pretty a little sissy you've
become!"
I shook my head and closed my eyes tightly in defiance.
"Well now, that simply won't do!" Madge said as I refused to
look into the mirror at the new me. With that, she went back to
her bag of tricks and took out some cotton surgical tape. As Ruth
lifted my veil and held my face Madge took four strips of the
tape and, holding my eye's open, taped both the top and
bottom lid's open wide so I couldn't close my eyes! She fluffed
my veil back down then finished by saying. "there sweetie! Now
you'll have to look at yourself! You have a pleasant afternoon
now!"
Both ladies left the room closing and locking the door behind
them.
I grunted and twitched in the silence of the room but couldn't
get loose! Hanging there in the silence of Madge's bedroom I only
had the smell of perfume and the swish of the satin gown for
company. It was sickening to see myself in the full length mirror
all dolled up like I was. Total makeup, pierced ears and a
feminine hairdo and I could even notice my painted toenails in my
open toed, stiletto heeled shoes under the mass of frothy
petticoats and the satin gown! I wondered what Madge and Ruth
were doing as I began hearing them moving around the house but
could only imagine as I hung there, helpless, forced to look at
the sissy boy in the flowing, white satin gown!
I was so spent and tired I either fell asleep or blacked out a
couple times but finally late in the afternoon I heard the
bedroom door open! Madge seemed to take delight at seeing me
still enduring my latest punishment. She came over and ran her
hands over my body, feeling my curves under all that creamy
satin as it swished.
"Such a little princess!" She exclaimed as she then went over to
the rope and then let me down. Too weak to stand, I collapsed in
a swirl of satin and lay on the floor. Madge undid my wrist
cuffs, took the tape from my eyelids and removed my gag after
letting the air out of it while Ruth undid my ankle cuffs.
After putting everything away they helped me to my feet and took
me over to the bed. I tried to talk but after being drugged,
forcibly 'milked' and dressed like I was wobbling on the heels I
was groggy from the experience. I pleaded with them to forgive me
and let me go.
"Now don't you worry your pretty little head," Madge said as she
unpinned my veil and took it off. She then produced a few pairs
of panties and stockings once again and started working the
panties into my mouth. Once my mouth was brimming with the lacy
nylon she then pulled one of her nylon stockings tightly over my
head just like before. She then gathered another stocking and
began working it over my head as well. It felt tighter but
swished and zipped easily over the first stocking until she had
it pulled down tight and was smoothing the bottom around my neck!
She finished by taking another stocking and tying my wrists
securely behind me.
They then laid me in the middle of the bed. Madge fluffed out my
gown as Ruth put one of the satin pillows under my nylon nob of a
head. They then sat on the bed beside me as Madge filled me in on
the rest of the plan.
"Such a little darling. I am sorry we had to put you out but we
wanted to make it as easy as we could to get you dolled up once
again. And that little milking was to make you easy to handle and
more relaxed. What we have decided Timmy is that you won't be
going home with Ruth after all! You'll be staying here from now
and on and get a good home schooling by your dear auntie Madge
and learn how to be a proper lady-of-the-house! Isn't that just
wonderful?"
I "mmfffed" into the gag in surprise and tried to move but they
held me down on the bed, making sure I heard the whole story.
"Remember those two little bottles on the table sweetie?" Madge
cooed. "Those were female hormones! After you were out from the
chloroform I gave you two large injections! You'll start growing
your own real breasts in no time. The doctor assured me that with
you being only twelve, you'll never grow whiskers or have a deep
voice to worry about. Isn't it wonderful we got to you at such a
young age? You will just be the perfect little lady and nobody
will ever know you weren't born a real girl!" Madge said beaming
a smile.
The story continued. Madge had gotten with Ruth weeks before and
told her what had happened. They decided it was no use to try and
cure me so they decided to change me into a girl! Ruth had gotten
rid of my things and cleaned out my room. She had also moved out
of our apartment so she could go to college full time now. And my
little suitcase sitting by the front door? Madge
would see to it that all my clothes would soon be tossed out as
were all my other things. They were getting rid of Timmy once and
for all. I was now going to be known as Tamara!
I glubbed into the gag and tried to sit up but Madge straddled me, sitting on my chest.
"Such a little Princess" she said with a smile as she lifted her
skirt and frothy, lace trimmed, white nylon slip then moved up
over my bobbing, nyloned knob of a head!
"Do you like my pretty vagina Tamara sweetie?" Madge said with a
giggle, "you always seemed to like looking at my legs," she said,
"and I know you like all my pretty lingerie," she continued as
she held her dress up showing off her tightly
gartered nylons held by her tight, white panty girdle! "Look at
my vagina, yesssss isn't it pretty?" she said as she got closer.
I felt Ruth straddle me and hold me down as Madge fluffed her
skirt and slips over my head! I could smell her perfume and smell
her excitement as she moved up over my face! I could hear her
nylons brushing against my cheeks and her slips swish as I stared
up, my nyloned nob of a head bobbing struggling to get
away! But soon my bobbing head quieted as Madge let out a sigh
and settled her girdled mound directly onto my face!
"I hope you like my pretty vagina sweetie, yesssss, because it won't be long until you'll have one just like it!" She said with a giggle as she wiggled down tightly onto my face!
I could tell Madge was excited, she had enjoyed feminizing and
dominating me. She liked the control and seemed to be enjoying it
even more as she began rubbing on me, humping my face! The room
then went dark as she pulled her slip and skirt tightly around my
head then pulled it from both sides forcing my face
deeper and deeper into her girdled crotch! She wiggled and
started rocking back and forth until she was tight and then
started rubbing on me! I could hear the material of the nylon
swishing on her tight panty girdle as she rode me! Her nyloned
thighs gripping my head became warm as she worked herself against
me. I could hear her starting to breathe heavily and then gasp as
she clenched her thighs around my head tighter and pressed her
girdled vagina to my face. I could smell her perfume in the heat
and then began to smell her musk!
I then heard her gasp again and then moan a satisfied moan as
her thighs began to spasm and her vagina began to twitch. She
held me tight and shook as wave after wave of pleasure overtook
her.
I was on the verge of blacking out when she finally relaxed her
thighs and let out a sigh. She made sure to rub my head still
under her skirt and lace trimmed slip and cooed with
satisfaction! She then swished her slip and skirt up and got up.
She put her skirt back down then smoothed it out like nothing
had happened! And as she checked her look in the mirror Ruth
began undressing me!
It wasn't long until I was once again standing naked in the
bedroom and Madge and Ruth were finished with my little lesson.
"Toddle off to your room Tamara sweetie and get dressed, we'll have supper soon and then take Ruth to the airport later, okay?" Madge said as I left the room.
I went straight to my bedroom to grab my clothes and get out of
there anyway I could but noticed something different now, and how
things had changed!
There were flowered drapes on the windows now and a frilly, pale
pink satin comforter on the bed! I checked the dresser for my
clothes and found the drawers filled with lingerie all in my
size! I then checked the closet to see it was filled with
dresses, skirts and blouses without a pair of pants in sight!
That was what they had been doing all afternoon while I was
secured in Madge's bedroom! Madge appeared at the door! "I hope
you like your new wardrobe Tamara sweetie! I have ordered you
some pretty new furniture and a vanity and later this week we're
getting that blue color on the walls changed to maybe a pretty
pale pink color with maybe a flowered wall paper too, and I am
having this room carpeted in a soft pastel color so you'll have a
complete girl's room, won't
that be just delicious Tamara dear?" Madge said with a smile.
"You go shower off and auntie Madge will help you get dressed for
supper."
I went to the bathroom and scrubbed off all the makeup and
washed my hair but as soon as I was done I was back in my room
with Madge combing my hair out and adding a pink satin bow in my
pony tail then, putting just a little makeup on me. She added a
training bra with just a little padding, then after tucking me
in a briefer put me back into those white satin panties with the
ruffles and lace and the pretty blue bows at the front of the
legs. She then put me in a garter belt and nylons and then added
a white nylon full slip. After putting me in some low heeled
ankle strap pumps she zipped me into a floral patterned dress!
We had dinner as planned then it was time to say goodbye to
Ruth. She said she would be visiting from time to time then Madge
was set to take her to the airport. I was shocked to see her hand
me a little coat and a purse!
"Come along Tamara, you're going to the airport with us!" Madge
said with a smile. I begged not to go saying I couldn't go out in
a dress! But Madge only giggled, "you're tucked into that tight
briefer and have on a pretty brassiere and I've fixed your hair
and makeup nice and pretty just like a proper little lady,
of course you're going along!"
"You just act like the proper little lady and you'll get the
hang of it in no time!" She put the little coat on me and handed
me the purse and then we stepped out of the house and crossed the
sidewalk to the car in the driveway. It felt strange to feel all
the nylon lingerie I was wearing and the breeze swirling
around my smooth nyloned legs and up my dress!
Madge made sure I sat ladylike in the front seat on the ride to
the airport and told me my new feminine nature would be taking
over in no time!
I was scared to get out of the car at the busy airport. I walked
with Madge and Ruth inside where she got her tickets and then we
then waved goodbye as she left for the boarding area. Madge took
my hand and walked me back to the car. I noticed the hustle and
bustle of the place and saw a few women look our way. Several
noticed me but passed by without a strange look or comment. I was
just a little girl with her aunt now walking along. Several men
looked on as well but they were mostly looking mostly at Madge,
her ample bust jiggling as she minced along on her high heels,
her hips wiggling under her skirt as her nylons zipped with every
step. A few people noticed me but didn't see a little
boy at all, only a little girl in a dress. Then I noticed my
nylons were swishing too as we made our way to the car!
I didn't say much as Madge drove home then became a bit nervous as she took a light detour and pulled into a little shopping center. I could see the lights from the dress shop as she pulled into the parking place.
"Come along Tamara dear!" She said as she took her purse and
opened the car door.
"I...I can't go in there. You said there wasn't going to be any
punishment like this auntie Madge!" I sobbed. But Madge only took
my arm and pulled me out through the drivers door with her then
started walking me to the shop.
"Punishment?" She said with a smile and then giggled "this isn't
a punishment for you dear, not now! You're going to need lots of
pretty dresses and things from now on, so we might as well look
around, don't you think sweetie? I will have to teach you how to
shop like a lady!" With that she pulled the door open led me
inside.
I could smell the perfume in the air and hear the soft music in
the background as we made our way to the girl's dress section.
The place was all feminine and done up in pastels and was a place
boys should never be. Madge led me past the hosiery counter then
took me past the rows and racks of lingerie and dresses then
began looking through the racks for something in my
size.
"Can I help you ladies?" the proper, older sales lady said as
she approached with a smile.
"Why, yes!" Madge said. "We would like to try on a few dresses
and pick up some pretty lingerie for my little nephew here!"
With that, most of the dozen or so ladies shopping in the store immediately turned and looked at us. Madge continued "It seems that my little nephew is some sort of little sissy. I keep catching the naughty little boy in my lingerie so I thought it might be better since he seems to love pretty, feminine clothing to get him some of his own!"
I could already hear several of the ladies that were shopping
now whispering and pointing at me. Madge handed the sales lady a
couple of frilly dresses and with that they took me in the back
to the changing rooms!
The sales lady seemed perplexed but began by having me take my
coat off. She unzipped my dress and had me step out of it and
once she saw my frilly lingerie she commented to Madge. "I've had
this happen a couple times before. Mothers or aunts catch their
boys in their lingerie so they bring them in here
wondering what to do. I find a little embarrassment goes a long
way," she explained. Madge seemed interested then mentioned that
although what she said was mostly true there was more, then went
into the fact that she was changing me into a girl for real
because I wouldn't stay out of the clothes and already seemed a
bit feminine anyway and that with her constant tutelage and the
help of modern medicine I would be "cured" in no time!
"Well, little girls can't be cross dressers, now can they?" The
sales lady giggled as she talked with Madge. "But in the mean
time we can give your little sissy boy here a real thrill and one
that he won't soon forget, what do you think?"
"Yes, that's exactly what we need" Madge said with a satisfied
smile. With that the lady left the changing room and returned
minutes later with a load of lingerie and several more dresses!
Madge watched as the lady put me into a full slip and then a
frilly petticoat then zipped me into a dress that looked like
one of those kind fussy mothers put on their little girls when
they enter them in beauty pageants! She added a pink bow to my
hair and added a dash of perfume then clasped on a pearl
necklace. Madge then took the cue to add more makeup to me making
me look like a totally feminized sissy! The whole look was way
over the top and I could tell by the way Madge and the sales lady
were giggling as they worked me over and watched me squirm. Then
the sales lady took my hand and led me out into the store!
"Let's see your pretty look in front of the mirrors sweetie,"
she said as she pulled me a long giggling at my hesitation.
They brought me into the store and had me mince like a girl back
and forth swishing the petticoats and curtsying in front of the
row of mirrors. Several of the other lady shoppers saw what was
happening and moved through the racks of clothing towards us to
get a closer look. I started hearing giggles! My pink chiffon
dress swished and rustled loudly with each turn and wiggle of my
hips as Madge and the sales lady made me perform.
"What do you think ladies?" The sales lady said loudly. "This
little boy was caught by his aunt in her lingerie so she thought
he must want to wear pretty lingerie and dresses. Isn't little
Timmy here just the most precious sissy you've ever seen!?" She
said as they continued making me move back and forth, swishing
in front of the mirrors giving all the shopping ladies a good
show! A couple of ladies seemed a bit put off as they recognized
I was really a boy but most of the others seemed to enjoy seeing
me punished!
The sales lady then unzipped my dress and took it off right
there then gathered a blue one this time. Laughter and giggles
echoed through the store as the ladies saw my little brassiere,
lacy nylon full slip and frothy petticoats and giggled further as
the sales lady forced me into the dress and zipped me into it.
She and Madge then had me model the dress making sure I
swished the skirts with limp wrists as I minced along, totally
embarrassed and red faced. Then the sales lady quickly spun me
around and fluffed up my dress and skirts in a loud, silken
swish, holding them high to all the ladies now watching to reveal
I was now dressed in a lacy garter belt and sheer hose and
wearing frilly, pink, lace trimmed satin panties with little blue
bows for that extra feminine trim! I could feel my face redden
deeper and was now visibly shaken and all the ladies knew it.
Gasps and then loud feminine laughter filled the corner of the
dress shop at what they saw. I ran back to Madge but she only
giggled. They made me model three more dresses and several pairs
of high heeled shoes until my ankles ached. The ladies got a kick
out of seeing me wobble as I tried to walk in the heels for the
first time. "Don't worry sissy, you'll get used to them!" One
lady yelled out and then heard the giggles and laughter that
followed. Finally, they seemed to have had enough and I was taken
back to the dressing room in tears.
"Like I said, that is usually quite enough to discourage most
sissies," the sales lady said to Madge.
"Yes, I suppose it would be for most unruly boys, but poor
little Timmy seems to want it all. We'll take that pretty pink
dress with the petticoat and all the ruffles," Madge said with a
smile.
"Fine, I'll box it up for you." The lady said but was
interrupted by Madge.
"No, it's so pretty and feminine, I think we'll just wear that
one home, and we'll be needing those others too!"
By then even the sales lady was giggling. She then zipped me back into the frilly pink dress. It was the most embarrassing experience I could ever have imagined and I knew that even worse, this was only the beginning!
I had begun to sob as I wobbled and minced on the pink, stiletto
high heels and my dress and petticoats swished and swirled as we
made our way back through the store with the sales lady leading
the way with an armload of frilly dresses. Madge stopped at the
hosiery counter and selected several pairs of pantyhose and sheer
garter stockings making sure to ask me which kinds and shades I
liked best as the still pointing and giggling ladies looked on.
After a trip past the brassiere and panty rack for a few more
selections we stopped at the slip display where Madge made sure
to pick out the most frilly, lacy and feminine things she could
find and then held them up to me to make sure of my size and to
imagine them on me! It seemed to take forever as she
slowly made her choices, and all the while the ladies looking on
continued with their satisfied laughter and giggling as what
Madge was putting me through.
We then swished to the counter. Madge took out her credit card
and paid the bill as the sales lady and her helper then began
boxing up and bagging up the dozen or so pairs of hosiery,
panties, brassieres and all those frilly slips. Madge made me
gather the many boxes and packages all decked out in pink
cardboard and fancy lettering showing they came from the
exclusive dress and lingerie shop. After the sales lady thanked
Madge for the business she said to bring me around as I 'changed'
and that she would be happy to have me as a new
customer.
"Oh, I have a feeling we'll be doing a lot of shopping here!"
Madge said with a smile as she led me out of the store still
swishing in the pink dress and mincing on the heels with all the
makeup on and the pink ribbons still in my hair as I carried all
my packages. "Come along Tamara!" She said as we then left for
home.
My 'boy' clothes were now gone. Once safely back home I was
exhausted! I laid in my bed and could feel the satin sheets as
they slid against the pink frilly nightgown I was now wearing. I
knew that I would be doing whatever Madge told me, because I had
been warned on the way home that even though I wouldn't be
a boy for long, another 'sissy' treatment could always be just
around the corner if I didn't mind her! I wondered what would be
in store for tomorrow.