Motherless Vintage
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1956, The Vintage Years free porn video
"1956, The Vintage Years"
I'd been sneaking into Madge's house for the past two years by having a
spare key made for her back door. Madge, a family friend lived across
the alley and two homes down from me and my foster mom Ruth. Madge
always wore very feminine clothes and her hair was always in a feminine
hair set that was lacquered tight. She wore heavy makeup, powder and
perfume and always had her nails long and painted gloss red. Her smooth
legs always sheathed in tightly gartered nylon stockings that shined in
the light and zipped when she minced and wiggled along in a dress or a
tight nylon lined skirt always wearing high stiletto heels. Her ample
bust always bouncing and jiggling as she moved as well.
It started by seeing her shiny nylons on the shower rod. I then began
trying them on and wanting to try more until finally I had a key made and
began visiting the house after school with usually two hours to enjoy
myself until Madge got home from her job as a hairdresser. It was late
summer, just before my sophomore year at college the day she caught me!
And as soon as it dawned on her and she learned from my confession that
I'd already done this many times, I was really stuck now!
The day I was to leave for school I packed and my foster mom Ruth dropped
me off at the bus station. I waved as she drove away telling her I'd be
back for Thanksgiving. All seemed in order. And then instead of going
into the bus station I waited. Five minutes later Madge pulled up in her
car. She rolled down the passenger window. "Put your suitcase in the
back seat then get in." I did what I was told. We soon pulled into her
garage and the door closed behind us. I opened the back door and reached
for my suitcase. "Set that suitcase over in the corner of the garage,
you won't need it now," she ordered as she made her way to the back door
that led to her kitchen. "I have another suitcase for you that's already
packed. Do what you're told and then get into the house," she ordered.
And then, a mere three hours later I knew she was serious! Her lady
friend Agnes had come over and was looking on, waiting to help Madge out
just in case.
"Pick up your suitcase prissy!" she said as we stood in the bedroom as
she looked me over with a satisfied smirk pointing to the large pastel
pink suitcase and the matching pink overnight case sitting beside the bed
along with a stylish black patent leather woman's purse that laid on the
bed.
"What for!? Where are we going!? I have to get on my way to college,
school starts in three days!" I gasped but she didn't blink. "My chest
feels heavy, the girdle is too tight, this corset hurts, these heels are
too high!" I whimpered in panic as I could taste the heavy gloss red
lipstick and smell the floral perfume as it floated around my head as I
caught my new look in the vanity mirror and was stunned at how I looked
now.
"Let's get going. Out the front door and into Agne's car, get going,"
Madge ordered as she pushed me along. Agnes minced in front and said
she'd be waiting in the car. Madge locked things up as I waited. And
then, she met me at the front door. "Ok Timmy, out we go, and into
Agnes' car, get moving," she ordered sternly.
"P...plea...please aunt M...Madge I c...can't g...go out all dressed up
like a woman like this!?" I stammered wide eyed. "You can and you will,"
she said as the door opened and she pushed me out on the entry steps.
The large pink suitcase was filled and heavy. Madge made it a point to
mention that it was packed full of nothing but women's clothing and
lingerie and things! I wouldn't have any more access to any man clothing
at all!
"But everybody will see me!" I gasped again.
"Well then, since you're dressed like one now you'd better act like a
proper young lady don't you think? If you move feminine enough you might
just get by," she said not really caring either way. I gasped as I
lugged my bags, wobbling on the high stiletto heels as Agnes waited at
her car by the open trunk with a satisfied smile on her face.
I'd never had my hair done, never worn makeup. I mean, I'd tried Madge's
gloss red lipstick once or twice but it was the clothes I was interested
in. The silky, feminine things she always wore. I started with her
nylons. When Ruth and I would visit or when I'd mow her lawn or shovel
snow I'd sometimes take them from the shower rod and marvel at how shiny
and slippery they were. Once I started sneaking in when Madge was out I
began trying panties and garter belts and learned to walk in her highest
heels. I enjoyed her vintage layered nylon chiffon baby doll nighties
and robes. But I rarely tried on her bras or slips and dresses. I was
content just to sample a few of her silky things, and, in trying to dress
fully I felt it might disrupt her closet or dressers with so many items
to have to return as I'd found them, and the time involved to dress fully
and completely would have put me at risk too. But now my secret was out.
My ears rang, I could feel my heart pounding as I gasped and choked a
swallow with a dry throat as I left the house and minced along as I moved
outside, wobbling on the high black patent leather stiletto heels. And
now it was my smooth, nylon stockinged legs that were zipping, and my
breasts that were jiggling with each mincing step, just like I'd
experienced in being around Madge! But, being on the other-side now I
could feel the cool breeze swirling around my smooth, hairless nylon clad
legs and fluttering at the hem of my dress and slips. The black purse
straps dangling from my right forearm. I noticed my white gloved hands
and felt the ladies floral patterned silk scarf that Madge had put over
my fresh, tightly curled hair set and tied it into a tight bow at my
chin. Agnes watched as I put the pink case then the suitcase into the
trunk. "Okay princess, lets be on our way," she said as she got into the
driver's seat and Madge held the passenger door waiting for me to get
into the center of the front seat. Once inside, Agnes started the car,
backed out of the drive and off we went. My head spun and my stomach
tied in a knot, I felt faint.
"I...I don't f...feel very good aunt Madge!" I gasped as I squirmed in
the seat, smoothing my dress hearing the slips rustle and my nylons zip,
feeling the tightness of my curled hair set and tasting my gloss red
lipstick as the floral perfume floated around my head. "D...don't make
me go to Agnes' house, not for the whole school year!" I begged. "I...I
want my boy clothes back, I ca...can't do this, please aunt Madge!? I
said I was sorry," I whined as my voice broke.
"What's the matter princess? Hummm?" She glared at me. "You sneak into
my place to play dress up in my things when I'm gone and mince around my
bedroom in my nighties and lingerie and try on my dresses and nylons and
heels. Well, how do you like it now? Isn't this exactly what you
wanted?"
I swooned as I held my black purse on my lap clutching it with my white
ladies gloved hands and began to sniffle slightly. My mind reeled! I
wasn't just dressing up a bit, Madge had me dolled up now, the whole way!
I'd been bathed in a perfumed bath and shaved totally smooth. She'd cut
my hair then styled it and set it in curlers and added a highlight and a
perm solution. After being under the dryer Madge styled my hair in a
tightly curled vintage style complete with a pink satin hair ribbon at
the front of my tightly lacquered bouffant flip. A hairdo suitable for a
girl my age of the day but the way the hair had been cut and styled and
then curled and then set there would be no way I could ever comb my hair
out into anything a young man would ever wear. The curls were permanent
and would have to be cut off, my hair cut short to start over. But now,
that was only one of my problems. She'd also made me dress, not just
nylons and garter belt and heels and maybe a nightie to mince around in.
This time it was everything from head to toe and from the skin out.
She started with white, lace trimmed ladies nylon briefs came first, with
my testes pushed up tight like ovaries, my flaccid manhood pulled tightly
back. Vintage Hanes Alive nude support pantyhose came next. After these
were pulled up my legs and the panty pulled up high and tight on my waist
the white, six strap garter belt was clipped around my waist. The sheer
nylon stockings I'd always fascinated about came next and now I was still
nervous but it was more like being scared now and not in a good way!
Madge soon had the stockings up all the way, high on my thighs, the dark
welts of the seamed beige stockings pulled taught, the garter straps
straining.
A heavily paneled, white, long leg panty girdle was next. It had well
padded hips. That too was soon worked up over the nylon hose and pulled
up high and tight on my waist. After fitting me into a pair of black
patent leather stiletto heeled pumps with a full five inch heel she
continued.
A white long line brassiere came next. Madge had me lean forward as she
put me into it, pulling the wide white satin straps up my slender
hairless arms and over my shoulders. I felt the weight of the heavy
silicone breast forms in the pockets of the mastectomy bra as she did up
the four sturdy hooks at the back and adjusted the straps until the large
heavy bust jiggled in front of me. I could feel the weight and how the
bra straps pulled at my shoulders. The special bra and padded girdle a
special addition from Madge to make me even more shapely from a feminine
perspective. Then, the last piece of special attire, a tight, boned,
back lacing white satin waist-cincher! Madge took delight in swishing it
around my waist and hooking me in.
She then began pulling at the white silk laces as I held the corner of
her bed post teetering on the high stiletto heels. And soon my head spun
I watched my waist shrink smaller and smaller with each whirring zip of
the laces through the stainless steel eyelets at the back of the cincher
as it became tight and the wrinkles came out of the material and the
white satin began to gleam in the room light.
I grunted and gasped, writhing as I wobbled on the heels holding the
corner bed post. "I...I ca...can't stand it M...Madge!? It's t..too
much!" I gasped in panic. "You better get used to it princess!" she said
sternly, "we're just getting started!" She assured with a satisfied tone
in her voice. I felt faint when she yanked the final pull of the laces
and felt her tie them off at the back in a tight double knot!
A white, lace trimmed nylon full slip came next. She then sat me down at
her vanity and got out the makeup assuring me I was going to get the full
treatment. She quickly trimmed and then plucked my eyebrows into a high
and feminine arch, she then finished them off with an eyebrow pencil to
assure anyone seeing them that this was a feminine look. She'd already
given me a gloss red pedicure then added long, gloss red salon nails to
my buffed fingernails. And now, she began with the liquid foundation and
continued on with a practiced hand with false eyelashes, eyeliner and
mascara.
I felt Tim slipping away as my head spun and Madge worked with the colors
and brushes and pencils and powder puffs, the boyish look quickly being
ramped up into a feminine one, the makeup strangely enough adding a
couple more years to my appearance by being a more mature feminine look.
She added a lip liner then rouged my cheeks into a blush then did my lips
in a high gloss red which she took pleasure in by rolling up the tube of
lipstick then took her time applying it to my lips in broad heavy
strokes. She added more than enough of a floral feminine perfume to my
face, neck and wrists. She then pierced both ears then added pearl studs
and finished by clipping a matching pearl necklace around my neck.
She had me step into a white, layered nylon chiffon petticoat. Done up
in four tiers the bottom one had a white lace trim the most layers here
to fluff out the skirt of a dress. She tied it tightly around my
corseted waist then unzipped the floral patterned shiny rayon dress and
took it from the hangar. I finally hesitated stepping into it.
I heard the zipping, rustling swish as she fitted my arms into the short
white cuffed sleeves and heard the swish as she pulled the dress up. I
felt the dress tighten around me as I heard the whirring of the long back
zipper then felt it reach the top at the back of my neck. Madge then did
the hook at the back then rolled the white collar over, the small white
lapels in front of the Peter-Pan collar leaving the top of my upper chest
exposed and my pearl necklace clearly on view in a very feminine fashion.
Finally, Madge took satisfaction by putting a wide silk scarf over my
ladies hair set and then tying the ends into a tight feminine bow at my
chin.
"Plea...please M...Madge. I said I was sorry, I won't sneak into your
things anymore. Let me change back. I'm supposed to be on the bus
heading back to college," I gasped as I nervously fidgeted in my seat,
the slips and nylon and the rayon dress shining in the light and rustling
with frictionless ease.
"Well, you'll now be going to a different college this year won't you
sissy," she hissed with satisfaction with me all dolled up sitting
between her and Agnes I was truly stuck!
But I continued my complaints, complaints Madge was no longer interested
in hearing. As far as she was concerned this was a done deal and it was
going to happen. "Are you going to be quiet and still and start acting
like a proper young lady sissy?" She said angrily. But I only
continued.
"P...please M...Madge!?" I pleaded.
"Drive around the block Agnes. I've had enough of this sissy," Madge
said.
"What!? What are you doing!?" I blathered as my head swooned in panic.
Agnes then turned right at the corner, went to the next block then turned
right again. Now she was driving up my street! After passing two blocks
we were on my street, then my house came into view! I could see Ruth out
front, trimming the flower bushes.
"Pull into the driveway, I need to have a chat with Ruth," Madge said
dryly as I squirmed, begging her not to pull into the drive. Ruth would
see me then!
"The corset's t...too tight. I f...feel f...faint," I choked and felt the
long false eyelashes flutter as Agnes drove closer! Then Madge leaned
over.
"Stop that whimpering! You are going to do what you're told Timmy. And
if you run your mascara and I have to redo it you're going to really get
it, understand!?" she said angrily.
"Yes, but Plea...please aunt M...Madge," I gasped.
"You're going to be ladylike and do what you're told!" She whispered
angrily. "Otherwise we can just dump you off in Ruth's driveway all
dolled up like you are and you can explain to your foster mom just what a
little cross dressing sissy you are," she added then continued. "Make up
your mind priss! Are you going to be ladylike and do as you're told?
It's your choice Timmy," she hissed as Agnes pulled into the driveway.
Ruth was changed into baggy jeans and flat tennis shoes, scarf and blouse
and was trimming flower bushes. She stopped when she heard and saw the
car pull to a stop in the driveway. She put her basket and clippers
down, smiled and waved and then crossed the lawn heading right for the
car!
"Last chance princess," Madge hissed with satisfaction as Ruth
approached, my head spun in total defeat.
"Y...yes, yes, ok! I'll do what I'm told. I'll do what I'm told, I'll
do what you say!" I gasped in panic just as Ruth stepped onto the
concrete drive.
"Remember what I said then prissy," Madge whispered sternly. "You start
acting like a lady and you may just get by."
When Agnes rolled her window down my heart was pounding and my ears were
ringing. "Hi ladies!" Ruth said with a smile. Madge started the
conversation with a smile as I cringed.
"Hi Ruth!" Madge said with a bright smile. You remember my friend Agnes?
And this is her little niece Joyce. Agnes nodded and then I felt as if
laser beams were hitting me as Ruth looked me over with a friendly smile
as I smiled back, squirmed slightly in my seat then nodded then turned to
look away. She'd quickly looked both Agnes and me over, noticing my
dress, my shoes, maybe my smooth nylon clad legs as they shined in the
light, and she saw my gloves and purse and the tight silk scarf tied over
my tightly curled hair set. Her attention then turned back to Madge.
"Agnes was in town and invited me out to stay with her for a few days. I
was wondering if you could take in my mail and my papers until I get
back?" Madge asked as both ladies talked.
"Sure. I was just trimming some of the flowers. I have more free time
now that Timmy's gone back to school," Ruth added.
"Ah, Timmy's gone?" Madge feigned causing me to squirm in my dress
"He's gone back to college, his second year now. I dropped him off at
the bus station this morning," Ruth said without a clue that there,
sitting only three feet away I was totally unrecognizable now with me now
all fully feminized and dolled up as Agnes' "little niece Joyce!"
Madge's smile beamed, her voice even more feminine and relaxed now.
"They say that school starts to get harder the second year. I hope Timmy
will be able to handle all the new things he's going to learn this year,"
Ruth wondered.
"I'm sure that Timmy will be fine. I mean I'm sure that he'll have to
learn some new and difficult things but I'm sure that all the new things
he learns will soon become second nature," Madge assured, seemingly
talking to Ruth and me at the same time but with two obvious and very
different meanings. A hopeful tone for Ruth, a threatening one for me,
for my sins of sneaking into Madge's house and into her things when she
was gone. "Anyway, we should get going. We have a three hour drive.
Thanks for taking in the mail and the papers! Take care Ruth, see you
when I get back, we'll have coffee," Madge assured as she waved. Agnes
then smiled, waved goodbye then started the car and backed out of the
drive.
She rolled up her window and soon we were away from Ruth and my house and
away from my block. My head spun and I swooned tilting my head back as
both ladies chuckled at my predicament.
"Do you know why I didn't tell Ruth that niece Joyce was actually sissy
Timmy?" Madge asked. "Because you did as you were told and acted like a
proper young lady. That's why Timmy," she cooed as she smiled and
pinched my rouged cheek! "See? You already know how to dress in a few
ladies things but now you're wearing it all aren't you? You already know
how to move in a dress and heels and your act at being niece Joyce was
pretty convincing. I assure you by next summer you'll be much more
convincing at it and quite accustomed to being niece Joyce!" She
giggled.
"Next, next summer!?" I stammered. "But, but I have Thanksgiving and
Christmas break before the second semester!" I gasped as I squirmed in my
seat, feeling my nylon stockings and my silky, lace trimmed nylon slips
slithering under my floral rayon dress!
"You can call your foster mom anytime you like, only you'll be calling
from Agnes' house. Tell her about your school year, but be convincing.
You'll mention an intrim course over the holidays that will keep you too
busy to come home. You'll tell Ruth you'll see her in the spring once
the school year is out. I am sure she'll understand. I'll even help
explain. Of course I'll tell her we're pen-pals because I want to know
how well Timmy is doing in school. But only us three will know when I
call and Agnes tells me how you're coming along as niece Joyce," Madge
finished with a giggle.
"A whole year!?" I gasped in another half hearted complaint. But Madge
once again exerted her authority once again. "Is that lovely dress shop
still open? The one in that town that we turn at to continue to your
place?"
"Yes, I stop there now and then. I'm sure it's open," Agnes returned.
"Such lovely feminine things," Madge mocked. "Maybe we could stop on the
way and do a little shopping, try on a few dresses. Would you like that
sissy Timmy, hummm? Stop and try on a few dresses?" She asked as I sunk
into my chair silent, my head spinning once again.
"Well, maybe some other time then? So, like I said. Yes, a whole year
princess," Madge assured. "You sneak into my house and play dress up in
my ladies things and seem to like acting like a lady when you're dressed
up. So now, you're getting your chance.
You'll live out with Agnes for the whole school year. She's going to
make sure you're always made up and your hair set and nails are nice and
that you're always dressed up nice and feminine and that you are always
very ladylike. She's going to teach you to be a proper vintage
housewife!
You'll only wear ladies things and only do ladies things from now and on
for the next year at least. We need to find out if you'd be better off
as a young woman than as a young man. If that's the case we'll both be
more than willing to help you to become the pretty Joyce for real. I'm
sure that you'll be quite ladylike in another year. And I think that
Ruth would be understanding. And if she isn't? Well, she is after all
only your foster mother, and you'll soon be twenty-one years old and
capable of being out on your own. So maybe it doesn't really matter if
she doesn't go along with what we'll both tell her was your idea," Madge
said as she spelled out her plan.
"Maybe you could teach him to be a hairstylist Madge?" Agnes said with a
smile. "If not, I have a good friend at home who owns another very nice
dress and lingerie shop. She could become a pretty sales lady,
constantly around feminine and ladylike things," Timmy choked a dry
nervous swallow as he swooned and his mind reeled once again!
Madge smiled with satisfaction. "That's right Timmy dear. We're going
to get to the root of your little problem. What kind of boy likes to
dress up in ladies things. Certainly no normal boy. Sickening," she
scoffed. "Because you can't seem to stay away from ladies things you're
going to be getting your fill of them and then some, the full ladylike
lifestyle, each and every day, all day long princess," she assured. "A
suitable punishment for a cross dressing sissy don't you think? In
wearing makeup all day every day, full time it won't be long until you
simply don't see Timmy anymore. Joyce will take his place. And you're
going to be in lingerie and hosiery and skirts and dresses and high heels
for so long that when your year is over I really doubt if you'll even
remember what it was like to wear men's pants or flat shoes," Madge
assured. "Maybe by then you'll finally have gotten your fill of women's
things. But we'll be watching closely and if it seems that you're getting
along better as niece Joyce than as little Timmy, well then, more changes
will be needed won't they princess?" Madge finished as the three "ladies"
continued on down the highway.
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