Meals on Wheels 6 Teaching Ruths Granddaughter
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Sorting Out Part 4 - Ruth's Party free porn video
NOTE: I have been amazed at the nice reviews from Parts 1, 2,
and 3. This is proving to be a great way to finally get all
these events out and onto paper and it feels good to do it. But
I want to be sure readers know that these are true stories that
have occurred during 35+ years of cross dressing. I'll finish
this one if readers want me to.
Sorting Out - Part 4: Ruth's New Year's Party 1975.
It had been more than 4 years since I had been outside the
house, fully dressed as a girl, for the Halloween party in 1971.
Dressing up had been relegated to maybe once every other month
during my junior high years, whenever everyone was out of the
house for the day on a Saturday and I had the place to myself.
I continued to grow taller throughout 7th and 8th grade
(1972-1973) and had hit 5'10" by the end of 10th grade in the
spring of 1975. But I had never really had any noticeable
transition into puberty. I was virtually hairless on my body
nothing on my face or chest, and only a hint of very tiny light
blonde peach fuzz on my arms and legs. I had almost no pubic
hair, and the bit I had was very thin and light blonde.
I weighed in at around 140 lbs. with just a 25" inch waist and
basically not an ounce of fat on me. Along my upper chest and
shoulders, my collarbone was very pronounced, showing through my
skin, and my neck was also very slim up to my chin. My
Anglo-Scandinavian genes gave me super clear light skin and
naturally rosy cheeks (guys often teased me that it looked like
I was always blushing).
I also have blue eyes, very thin eyebrows, but I had very long
eyelashes top and bottom. When I would occasionally dress up
around this time (mid 1970's) we had lots of clothes stored in
the basement from my older sister's teenage/high school years
that were stretch-knits and polyester. My mom had continued to
save various amounts of dresses, tops, skirts, shoes, and
lingerie from my older sister (who was now a junior in college)
and lived away from home full-time.
I can remember putting on a stretchy white-lace bra with foam
padding filling out the cups, and wearing this certain yellow
stretch-knit (very form fitting) long sleeved top that had a
sculpted low-cut collar and embroidered flowers along the
neckline. It rode very wide to the edges of my shoulders and I
had to push the bra straps over farther than normal so they
wouldn't show. In the mirror, my very skinny chest and upper
arms, and my thin shoulders looked exactly like a girl's, as
this very form-fitting top easily showed my collarbone above the
shirt's collar, as well as under the fabric out to my shoulder's
edge.
The bra cups pushing out looked very real and were plainly
visible along with the bra straps through the thin yellow
fabric. From my chin to my waist I looked like any of the girls
I went to school with. I never stuffed the bra to look out of
proportion, instead I always tried to go for a very balanced,
natural looking bust line. I also had learned to not wear the
bra up too high, but to keep the cups at a place where it looked
like a young girl's breasts were supposed to be.
My hair was now grown out into a thick blonde "shag" cut, with
bangs straight down on my forehead and parted down the middle
with wavy hair hanging to just a half inch above my shoulders in
front, and maybe 2" past my back collar. I can remember it like
it was yesterday. All I had to do was push this dark brown suede
hair-band just behind the fronts of my ears and then pull it
back starting above my eyes on my forehead and going back to my
hairline. The little plastic teeth inside the hair-band pulled
my bangs up and back and when I stopped about 2" back on my
part, the bangs were curled back over and the hair on the side
of my head went back and behind my ears and looked exactly like
the most average girl's hair style.
My older sister had left behind several pairs of very stylish
screw-on earrings, so I had all kinds of sterling or gold
dangling jewelry for my ears. I would then put on some pink lip
gloss (no blush -- my cheeks were always flush pink), some pale
blue eye shadow, and then brush up my already long eyelashes
very dark with mascara. In less than 5 minutes I had the
everyday normal look of any teenage girl no wig, and no overdone
"too much make-up" face. Just an "average look" that I knew
could blend in anywhere IF there was a way to work up the nerve
to try going out.
But that never seemed to be an option, as my blue collar town in
the mid-1970's would make no allowances for a guy walking around
town dressed like a girl. If found out, it would automatically
be assumed I was gay (which I knew I was not), and we'll just
say that my neighborhood was not into tolerance or alternative
forms of expression. It would be "beat you up first and then ask
questions later". But in the safety of my house when my parents
and my younger sister were 2 hours away for an entire Saturday,
I would just look at myself in the mirror for 10-15 minutes at
a time just amazed at how quickly (and easily) a 16 year old guy
could take on the near perfect look of a 16 year old girl.
That made me start to wonder just how fine was the line between
"acting" like a guy and "acting" like a girl. It was obviously
all about appearances (clothes, hair, nails, face, breasts/bra,
bare legs) and mannerisms (walking, sitting, hands on hips).
stereotypes that society had decided were for girls.
Sometimes I wore just some high-waisted bell-bottom jeans and
clog sandals, and then did my nails in a bright pink polish, the
look was pretty good. But I always wanted to go for the most
feminine look I could come up with. So with the yellow top I
would put on a narrow cut cotton tan skirt that went about 3"
above my knee, and wear dark suntan pantyhose with basic brown
flats that had a strap around the back of the ankle. And as had
become part of my regular routine, I wore satin panties under
the pantyhose, and a short pink half slip with a 2-inch lace hem
under the skirt.
In the full length mirror in my mom's room I would check myself
out side to side, over my shoulder, bend my knees, put one hand
on my hip, and just marvel at the visual image that looked back
at me. The more I looked, the more convinced I was that there'd
be no way for anyone to think I was a guy if I went out and
walked around. The thin face and clear skin was that of an
average teenage girl. The hair was not a wig and just blended in
perfectly. The earrings dangled down and went well with a few
rings and several bangles/bracelets on one wrist. The yellow top
covered my skinny arms down to my wrists and the bra showed
completely through both in the front, and for all to see across
my back when I turned and looked over my shoulder in the mirror.
I had skipped the "girl costume" for Halloween the last three
years (in 8th 9th and 10th grade) since my fun evening at the
youth hall in 1971 (the year I wore the blue pleated skirt,
white blouse, and white patent leather shoes). I had dated lots
of different girls and always ended up paired off with someone
when I went to birthday parties or dances at the high school. At
the beginning of 11th grade I started to say things like, "I am
absolutely through with the dressing up", and that would last
for 4-5 weeks sometimes and then I'd have an incredible
opportunity open up to be home alone for a Friday night and all
day Saturday 'til evening.
I'd be watching television or listening to music and then
suddenly start thinking how nice it would be to have on a pretty
dress or skirt and all the accessories. And no matter how much
I tried to pass on the thought, I would find myself downstairs
in the basement opening the steamer trunks and looking through
the garment bags. Ten minutes later I was completely dressed as
a girl for the rest of the night or most of the day. It was so
incredibly relaxing to just sit on the couch and cross my legs
and watch television or read a magazine and listen to music.
Walking through the house in heels and pantyhose in a skirt or
dress was just plain fun. So after getting in 8 hours or more,
I would neatly put everything back in the basement and wonder if
I was ever going to completely stop dressing.
I always questioned myself, "Why does it feel so natural and why
do I feel so good when I dress?" I'm sure to others it would be
strange for a guy to 'want' to change his appearance to a girl,
I mean it seems to make no sense. And so many guys I knew and
hung out with had nothing feminine about them, so why was I the
one doing this? Certainly my older sister dressing me from an
early age of 4 or 5 pre-K and regularly for several years must
have contributed to my feelings of comfort. But, I also had
mixed feelings. When I wasn't dressing, I felt like it should
stop and it's wrong. When I was dressed, I felt great and just
sat back and relaxed in the fun of being someone different,
someone new, some one pretty.
Well, right before Christmas 1975, a gal I had dated a few
times, Ruth, announced her parents were letting her throw a New
Year's party at her house while they were on a 3-day vacation
out of town. Her aunt (who was probably around 35 years old)
would serve as the chaperone along with her other girlfriend
(also in her mid-30's).
Ruthie was kind of an alternative free-spirited gal. Average
looking, around 5'9", but always "into some kind of scheme" or
challenge to the norms. Cross-country runner and swim team at
school, and she kept her hair very short in one of those Dorothy
Hamel cuts (her hair was one length all the way around with
short bangs and just over the top of the ears). She announced
that the New Year's bash would be a costume party called
"anything goes". Typical Ruth! And the clincher was she asked me
if we could go as opposites, which I didn't understand at first,
but she then said me as a girl and her as a guy. She explained
to me, very openly, that she had always wanted to dress up like
a guy "all the way" and that her dad had his old tuxedo in his
closet that she would wear.
It was definitely nontraditional and very much in line with
Ruth's personality. She said I would come as her date dressed as
a girl. I had no idea where this idea came from, but she was
really into this. I'd never said anything to anyone, let alone
Ruthie, about my dressing up. And I'd never heard her say
anything about her interest ever during the 3 months we'd dated
on and off. Well when she told me, all I could think about was
how great it would be to be out dressed up again. But I also was
very hesitant about being seen in the girl's clothes I loved to
wear, with make-up and jewelry and all. So I played it cool and
pretended to be very surprised about the idea and tried to look
very reluctant to dress up with her. She asked me if I my mom
could get something together from my older sister's things,
which was probably a very normal question, but to me it
immediately sounded as if she had inside information that I'd
been doing that already (but how could she?). I said I'd
probably be able to get something together and agreed to do it.
I got clearance from my parents to go to the party and spend the
night, because about 8-10 others were spending the night and her
aunt and the other gal would also be staying overnight as
chaperones. I went over to her house around 5 o-clock on Dec.
31st to help get set-up for the evening. I told my parents it
was a costume party but no details.
Before I went over, I struggled back and forth in my mind with
what to bring for my costume. I went down to the basement and
thought about wearing something a girl would wear on a freezing
cold winter night in December. I was wondering back and forth if
I'd get dressed at home and then go over, or should I bring the
costume with me. It had been over four years since my mom had
seen me dressed up, and I think she thought I hadn't dressed up
since. So I opted for bringing the costume with me to Ruth's and
dressing up there.
I picked out my favorite pair of satin panties. They were
turquoise with ivory lace on the front above the legs with an
ivory silk box at the waist. I also picked out the white
flower-embroidered opaque tights my mom had received from the
lady next-door about 5 years ago (and had never worn once). I
also grabbed a white long-sleeved cotton turtle-neck sweater, a
nice stretch bra (probably my sister's from junior-senior year
in high school -- around 36B), a white satin full slip, and a
maroon corduroy jumper. I finished up by choosing the basic
black patent-leather pumps with a 1-2" heel.
I put these things in a large brown bag from the supermarket
along with a white plastic hair band, several bracelets and
rings, and a pair of screw-on earrings. My dad gave me a ride
over to Ruthie's house and I was very conscious of the contents
of the bag on my lap as I sat silently in the front seat with
him on the way over. I believe he knew nothing from my mom about
my years of dressing, and if he did, he probably learned it
years after the fact and wrote it off to when I was a little kid
of 4 or 5 years old playing with my older sister. We said
nothing all the way over, only that I needed to get a ride home
tomorrow.
He dropped me off and I went in the house. Ruth answered the
door and she was already wearing her dad's deep navy blue
tuxedo. Her hair was slicked down flat with Brylcream and parted
on the side in a very basic middle-age guy's style. She had on
hairy black mustache (not very realistic, but it looked okay),
and some classic horn-rim "Clark-Kent" glasses. The tux had dark
satin lapels and a dark satin stripe down the side of the pants.
She had on what I guess were her dad's basic black wing-tips and
black socks. The tux shirt had ruffles on the wrists and down
the front from the collar, and it was tucked into a dark velvet
cummerbund. The look was finished off with black suspenders and
a dark velvet bow tie. It really was a cool looking costume and
she looked great. She had somehow flattened out her chest as
there was no sign of her bust showing through.
She gave me a hug and a kiss and was overly anxious to see what
I had brought for my costume. I said I thought it was too early
to get dressed up because people weren't coming over until 9PM.
So I put the brown bag down next to the couch and said I'd get
dressed later on. Her aunt was already wearing what was probably
an old formal dinner gown from 15 years ago. It was silver and
covered in sequins, full-length, sleeveless on top with a
matching mini-jacket. It was very tacky-gawdy and she explained
that it was from a wedding she'd been in after her high school
years. She later had on the long black satin gloves that go up
to the elbow and a fake diamond tiara, and she was supposed to
be Audrey Hepburn from the movie "Breakfast at Tiffany's". She
asked me about my girl's costume and I played it very low-key
and said it was down in the bag next to the couch and I'd get
dressed just before people came at 9 o'clock.
For the next hour or so Ruth and I and her aunt and her friend
blew up balloons and strung up crepe paper and got food into
bowls and made punch and all. By 7:00 or so we were pretty much
done with the bulk of the party prep when Ruth got very jumpy
and said that it was now time for me to get into my costume.
I backed-off, but her aunt agreed with her and started prodding
me along. Right around this time her aunt's friend (Julie I
think was her name) arrived. She came in from the cold night air
and had a few bags with her. She said she would be dressing as
Santa Claus. She had the full red suit and cap, black boots, and
classic white cotton beard. She went upstairs to get dressed and
that's when I agreed to do the same. Ruth wanted to come with me
and that made me a bit nervous about what I would be changing
into.
I brought the bag up to her mom and dad's bedroom, Julie was
dressing in the other bedroom that Ruth shared with her sister
Brenda. As I opened the bag to pull things out, I decided right
there that I would not wear the panties, bra, and slip just the
turtle-neck, tights, and jumper. It's like I got really
self-conscious about what I would say and all in front of her.
So I would keep my own boxers on underneath.
I got everything out and carefully left the panties, bra, and
slip in the bag and rolled it down as if it was empty. Ruth
looked over the tights and the sweater and jumper, the hair band
and the jewelry and said that it looked pretty good for a
costume. I explained it was some "old stuff" from my sister's
closet. I asked that she turn around while I undressed down to
my boxers and pulled on the tights over them. I pulled the
turtle-neck on and was stepping into the jumper when she turned
around for a first look. She smiled and said something like,
"Isn't this so fun?"
I was putting on the earrings when she asked if I had shoes and
I said they were in the bag. Well it happened so quick I had no
time to react. Ruthie scooped up the bag and was opening it to
get the shoes (just as I was thinking about the lingerie I'd
left in the bag) when she stopped cold looking in the bag,
reached in an pulled out the bra, slip, and panties in one hand
and looked at me said, "So what are these for?"
Well her look was one of complete amazement coupled with sly
mischief. She asked me why did I bring these if I wasn't wearing
them. She smiled really wide while I tried to make up a story
that my mom must've put them in there and how there was no way
I'd put them on.
I think my story was not very believable and not smooth enough,
because Ruth said something like, "Actually I think you brought
these for your costume but chickened out at the last minute". To
make a long story short, I fumbled for more excuses and she
didn't buy any of it. Then came the ice-breaker. She opened a
few buttons on her tuxedo shirt and said she was wearing her
dad's undershirt. And she then unzipped the pants and dropped
them about 10" to reveal she had on a pair of light green boxer
shorts. So next thing I know I'm telling her I can't believe
she's wearing guy's underwear and she's saying that you have to
wear everything if you're going to dress the part. So she walks
over and says, "Please put these do it for me?" I tried to say
no way, but she persisted and said that no one at the party had
to know, just me and her. In the end, you can probably guess, I
agreed.
She practically ripped the sweater off me and was putting my
arms through the bra straps and fastening the two hooks in back.
I stepped out of the jumper and she lifted the full slip over my
arms and pulled it down over my body. I was still wearing the
tights over my boxers when she held the panties my way and said,
"Come on, if I can wear boxers you can wear these under your
tights".
She turned around and I got out of the tights and boxers, then
pulled on the blue satin panties and then put the tights back
on. When she turned around, she smoothed the slip over my thighs
and asked what I would put in the bra. I rolled up one of my
socks in each side and then stepped into the black-heeled
patent-leather shoes. She helped me into the turtle-neck again
and then slid the maroon jumper up and buttoned the shoulder
straps to the bib in front. I remember that she just grabbed the
jumper and pulled it up above my waist and pulled the
turtle-neck down around my hips while she smoothed the slip
again. Then she pulled the jumper back down and said I looked
incredible.
She was so into this it was a little bit scary. Ruth asked me
about make-up and I said I didn't need any and that I'd just
wear a hair band on my hair and be done. She said "no way" and
then took me into the bathroom and did eye shadow, eye liner,
mascara, blush, and lipstick, and she was very good at it.
Once my earrings were screwed on and the silver chain and
bracelets and rings were in place she insisted that she paint my
nails. And she did. And it was a bright Christmas season red
polish. While I sat at the end of her parents' bed waiting for
the nails to dry, she brushed my hair, did some hair spray, and
set the white hair band in place. Just then Julie walked in
wearing the Santa costume and said something like, "Wow, that's
some costume!" We both stood up quickly, Ruth grabbed my hand
and had me take her arm (like a girl would do to an escort), and
she said, "So Julie, how do I and my date look?" After laughs
and smiles and lots of comments about how we looked, we went
downstairs to the kitchen to see Ruth's aunt.
She took one look at me and got very weird, saying things like,
"My my, what have we here? Look at the pretty young lady" and
stuff like that. She was really into it and grabbed her camera
and said let's get some pictures of the two of you. It was one
of those Polaroid Land cameras that shoot the picture out right
away, and then you wait about 5 minutes for it to develop. We
took about 10 shots in the living room. Arm in arm, sitting on
the couch, I sitting on Ruthie's lap, she standing behind me and
reaching with both hands around my waist looking over my
shoulder. And although I felt pretty good about how convincing
I looked in the mirror, this was the first time anyone had taken
a picture of me.
As they developed on the dining room table, I could not help but
be fascinated by the images before me. Anyone looking at these
who didn't know us would obviously assume I was a girl and NOT
in a costume. The outfit was so normal everyday basic for a
teenage girl. The shot of me on Ruth's lap on a dining room
chair showed me as a slender girl, curly blond hair, great
make-up and pretty eyes, bright red nails, legs crossed with
white flowered tights and basic black shoes, with a nice
matching white sweater under a cute jumper. There was not even
a hint that this person could possibly be a guy dressed up. I
could not stop looking at the pictures.
It was around 8:15 or so and people would be arriving soon, so
we finished up with the food and the drinks and got the music
going on the stereo. And I was struggling inside because I
really wanted to get into the role and start acting very
feminine, but I didn't want to look like I liked this and had
done this a lot. But I found myself swinging my hips when I
walked, crossing my legs at the ankles when I stood in the
kitchen, smoothing my skirt under me when I sat, and I think her
aunt's friend Julie was really taking note of me.
She started encouraging me to really emphasize my walk and hold
my wrist up with my nails facing out, and to sit with my legs
completely crossed at my thighs (which was very easy for me to
do). The last picture she took before the first people arrived
was of me and Ruth dancing in the living room, and it was
deliberately Ruth (the guy in the tux) leading me (the gal in
the jumper), and I really liked dancing backward like that. She
had us look at the camera and me lean my head on Ruth's
shoulder.
I had that Polaroid picture tucked in a book on my shelf in my
bedroom for at least 4 months after that night. I would take it
out all the time and look at it because it was the most feminine
and convincing of all the shots taken that night. I eventually
tore it up and threw it out for fear that someone would come
across it one day and I'd be totally embarrassed in trying to
explain it.
But I still clearly remember how great it felt to be dressed
100% as a girl again, and in front of other people after more
than 4 years since the Halloween party in 1971. I felt great.
And with each 15 minutes that passed, I felt more comfortable
than I ever had before. Leaning against the kitchen counter
talking with these three women, while Ruth's aunt finished icing
the cake, I just knew there must be something in my body's
hormones or whatever that had me feeling this way.
I looked down at myself a few times and thought about the
wonderful feeling a stretch bra across my chest and the two sets
of straps from the bra and the slip on my shoulders. The image
of breasts pushing out the top of the jumper was great and it
felt so natural to have a bust on top. The satin slip under the
jumper was laying across my thighs that felt so silky in the
white embroidered tights. The pointed shoes with the ankle strap
looked perfect. I was so small and underdeveloped in my pubic
area, that the panties felt just perfect tucking me in flat back
between my legs, and it was actually very comfortable and let
the jumper lay perfect flat against my hips and thighs in front.
There was no bulge, just smooth and form-fitting from my waist
to me knees.
I knew I had on make-up, my lips tasted of lipstick, and my eyes
felt wonderfully heavy with the mascara on my long lashes. The
earrings dangling against my neck made me think that this is
exactly how girls feel when they're dressed for a party with
friends, and I loved it all. When I took a drink from the cup,
the rings and bracelets along with the nail polish all came
together to make me feel pretty and beautiful and very much a
young woman. But I knew I wasn't and that this evening would end
in about 4-5 hours and I'd be back to school and this would not
be possible again for a long time.
(If you have interest in the rest of the party, I'll add that in
the next installment of "Sorting Out".)
Libbie
- 16.01.2022
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