Samantha s Journey To Discovery With Her Roommate
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The Roommate V free porn video
"The Roommate"
(Pt. V)
I heard Ted get up the next morning and head for the shower. I took off
my outfit from the night before and put everything away. I wrapped
myself in a bath towel then looked for something to wear for the day but
at seeing only women's clothing in the closets and dressers my stomach
tightened as I realized I had just graduated to living as a woman on a
24/7 basis!
"All done honey!" he said as he came back into the bedroom from the
master bath. "After you get freshened up how about putting on a pretty
dress then whipping up a little breakfast? There's some pads under the
sink in the bathroom for you. Better put one on so you don't mess your
lingerie or your pretty dress," he said as he quickly dressed then left
the room to get his morning paper.
I took a hot bath and my head still spun from the night before at all
the changes Ted had implemented. He knew what I liked but he was being
very patient and methodical in coaxing me farther and farther into woman
hood. I still wasn't sure I could handle it at this point but for now I
did the best I could.
Back in the bedroom I started dressing. I put on a white lace trimmed
nylon garter belt and added a pair of sheer, beige opera length nylons.
I put a pad in a pair of matching panties then tucked myself tightly and
slipped into them. The tight panty briefer I needed to wear to give me
a convincing woman's outline came next. I picked a fresh brassiere from
my new larger collection that was neatly folded in the top dresser
drawer and added the forms then finished with a white waist cincher to
hold in my waist. A lace trimmed white nylon full slip came next. I
then quickly did my hair then got some more practice by applying my
makeup once again, this time a lighter look for the day but still with
noticeable eyeliner, eyeshadow, blusher and red lipstick. After
powdering my face down I added a splash of perfume, slipped on a pearl
necklace and earrings then put on an updated polyester house dress. It
was done in a springtime yellow and done up with eyelet lace trim at the
collar and the short cuffed sleeves. I slipped into a pair of matching
ankle strap sandals and found the 4 inch heel a bit more comfortable to
walk in than the skyscrapers Ted had me wearing the night before. After
I made the bed I could hear Ted already in the kitchen so I checked my
look then went to prepare Saturday morning breakfast.
"See, you're taking to it just like I told you Laine, no problem!" Ted
said as he watched me swirling around the kitchen getting breakfast. He
noticed I was wearing one of those frilly vintage aprons ladies used to
wear. "I found six of those in Terry's trunk, they're all yours now.
You look nice!" He finished as he sipped his coffee while I brought
eggs, toast and poured the orange juice. I then sat down to breakfast
myself.
After breakfast as I took away the dishes and cleaned up, Ted finished
his paper and noticed an advertizement. "Milk's on sale today, and
there's a deal on pancake mix and paper towels too," he said. "It's
still early, you can put together a list then run down to the store
while I get the shrubs trimmed and the lawn mowed," he finished.
I was rinsing the dishes and glasses when suddenly Ted came up behind me
and hugged me close like he had done before. "Are you wearing a pad
like I told you dear?" he whispered nuzzling my neck.
"What difference does that make?" I asked as I continued.
"I told you last night I'd take care of you didn't I? I'm keeping my
word," he said softly as he had me dry my hands while he shut the sink
faucet off and pulled me close.
"Ted, I ...I have to get these dishes done and Ooofff, ooommmmfff!" I
gasped as he started in again by moving in close behind me holding me
around the waist then quickly cupped his right hand and worked it up
between my legs again. I heard the dress and the slippery nylon slip
swish as he began working his hand into my crotch. "That's it baby
yesssss, that's it, mmmmm, spread those pretty legs for me. Mmmmm, you
know what's coming don't you yesssss, spread them just a little more,"
he said.
I gasped at the sensation as I instinctively spread my legs for him now
and felt his hand enter my crotch. I gasped and became almost giddy at
the sensation. I stumbled on my heels as he held me from falling as he
worked his hand in and out of my tightly tucked, nylon girdled crotch,
working my "ladies" mound! "It's always the best isn't it. When you're
feeling feminine and all dolled up nice and pretty and wearing all that
slippery, frilly lingerie under a pretty dress," he asked in a whisper
but as I gasped again and my eyes began to glaze I knew he didn't expect
an answer.
"Yessss. Feels sooooo good doesn't it? Yesssss," he said as he
continued working me, stroking me as we stood in the center of the
silent kitchen, the early morning light streaming in. "Just relax
Laine, feel those thoughts feel those sensations as they take you over.
Yesss, you feel like a woman don't you. Feels good doesn't it?" He
cooed as he continued swishing his hand in and out of my crotch! I felt
the room getting warm and felt almost dizzy as I swooned and moaned a
girlish moan and then gasped and tensed up momentarily and felt a
shudder as I felt myself twitching deep in my panties and tight girdle
briefer as Ted held his hand tightly to my crotch! He felt me weaken at
the knees, at the sensation and felt me twitching on his hand as I
flooded the panty liner but kept my panties fresh and dry! He finally
steadied me then turned me to face him then gave me a good morning kiss.
"You're going to make the perfect housewife," he said as he hugged me
close then released me.
Still a bit disheveled I told him I was going to clean up then change
into my jeans and go to the store. "Wear the dress!" he asked. But I
had never been out, not in a dress! Not for real! The first time was
that heart pounding trip to the mail box that almost did me in and now
he wanted me to actually go shopping all dressed up!?
"I'll put on my jeans, you've wrinkled the front of the dress all up
anyway," I said telling the truth but in reality I was looking for a way
out of wearing a dress to the store.
"Well, just go to the spare room and run an iron over it. Or you can
pick out another dress, there's at least a dozen more dresses suitable
for day wear and shoes to match in the closet," he finished.
There was no talking him out of it. Within another half hour I had
washed myself off, changed my pad then gotten dressed again. I went to
the spare room and ironed my full slip and then the yellow sun dress,
feeling lucky it wasn't a halter top outfit! I was more than a little
nervous as I stood back in the kitchen with my purse holding the grocery
list. "Oh, pick up some beer would you baby? I have that yard work and
it might get warm this afternoon. We can have a few later this
afternoon," Ted said with a smile as I took the car keys in hand and
stepped out the back kitchen door.
It was Saturday morning and still early but now I could hear activity in
the neighborhood with most everyone now home for the weekend! I heard
my stiletto heels click as they hit the concrete on the back steps and
felt the morning breeze swirling around my nylon hosed legs and flutter
at my dress as I minced to the garage. I felt my pulse quicken once
again. I wasn't out all dolled up like I was on my trip to the mail box
but there was no mistaking that I was now dressed totally like a woman
from head to toe and from the skin out! Then just before I got to the
garage I saw our neighbor, Jack Weston coming out of his house. He saw
me in my dress, carrying a purse and all made up like a woman as I
walked clicking along on my heels as I entered the garage! I got into
the car then without stopping I backed out of the driveway then headed
for the grocery store.
My head spun at the sensation. Ted had gotten rid of all my "Lane"
clothes and now I was living 24/7 as a woman named Laine! Now here I
was on the way to the store in a dress! There wouldn't be any hiding it
now! My stomach churned at feeling stuck in my situation. Was my
makeup on correctly? Did my hair look feminine enough? How about my
mannerisms, my movement and my voice? I was still having to constantly
work on my voice to not sound male! There were a thousand thoughts
about those thousand little details that women took for granted and now
I had to concentrate on each and every one and hope I'd catch on and fit
in before I forgot and slipped out of character!
I gathered my purse and got out of the car at the store and started
making my way inside. I could feel the air around my smooth nylon hosed
legs and feel my slip and dress as they fluttered around my legs. I
took a cart as I entered the store and set my purse in the top basket.
Then as I walked along I could hear my heels click with each step and
felt my hips undulating as I moved through the aisles.
I felt faint at seeing the few shoppers that were there. One man
shopping looking at a jar of peanut butter glanced my way, he looked
closely and I thought he might suddenly point or begin to laugh at the
"man in the dress!" I didn't look at him but then as I started
gathering my things I realized that he wasn't staring at me he was
looking at my legs! The sensation made my head spin momentarily as I
noticed the man still watching, trying to not look obvious. I continued
by not paying him any attention as I clicked on my heels and minced
along pushing my cart until I turned the corner and started up another
aisle!
I shopped a while longer going through my list. I noticed a few stock
boys and a few clerks at the registers then noticed business was picking
up! I was in the breakfast cereal aisle and had reached up for a box of
Ted's favorite cereal and was just about to move on when I felt someone
touch me on the shoulder.
"Excuse me Miss," I heard the woman's voice as she spoke.
I quickly turned around to see an elderly lady that had been nearby. I
was frozen in terror but tried my best not to look flustered as I looked
on wondering what she wanted.
"I thought I might mention that your slip is showing a bit in the back,"
she said as if nothing was out of the ordinary.
I then realized that just a bit of that white lace trim from my slip was
peeking out from under the dress! I quietly thanked the lady then in
remembering where the restrooms were I quickly went to fix the problem.
I found the restrooms at the back of the store, took my purse out of my
cart then went inside. I caught myself starting for the men's room but
quickly turned for the women's room instead. After adjusting the straps
on my slip I checked my makeup and hair then returned to finish
shopping.
I tried to get into the swing of things and relax. I seemed to be
passing! No stares, no commotion, no panic was evident at me being in a
grocery store totally dressed like a woman. I realized of course that
in this day and age nearly all of the women in the store wore jeans and
seemed to care little about their appearance but a few of the older
ladies and some of the younger ones with class still made an attempt to
look feminine. Some of the women would look me over but none gave me a
second glance as I moved about shopping. But I noticed that a few of
the men would look my way. It was a strange sensation feeling their
eyes scanning me, looking me over, studying the pattern on my yellow
dress and noticing the yellow high heeled ankle strap sandals and how my
bust jiggled and how my hips undulated when I walked and how my heels
clicked loudly on the tile floor and how they could hear my nylon
stockinged thighs whisper and zip when my thighs would rub as I minced
along. I played it down but the feminine aura around me now was
apparently quite unmistakable.
I made it to the checkout then noticed that while some of the men were
bagging their own groceries most of the women had bag boys putting their
purchases into bags for them. "That'll be $85.53 'ma-am'!" The lady
behind the till said as I opened my purse, found my pocked book then
handed her Ted's credit card. While she rang up the tab she asked if I
wanted a boy to help with my groceries but I told her I could manage. I
was as careful with my voice as I could be and it seemed to work! The
lady going through her motions at the till printed out my receipt and
handed it back to me along with my card as she then started on helping
the man behind me! I put the receipt into one of the grocery bags in
the cart, Put the credit card into my purse then finally made my way out
of the store.
I was glad to be out of there. I'd spent more time shopping than I
thought. I could see the cars coming and going from the lot and noticed
more shoppers coming in. The weekends were far busier than early on the
weekdays as I was used to. But, so far so good. I could see Ted's car
parked up front so out the large double glass doors I went, relaxed
somewhat at the sensation that I would soon be back home and finally
able to relax!
The wind caught my skirt as I got outside but I managed to keep
everything under control. I loaded the groceries into the car and was
soon on my way home. And then I got a sinking feeling at realizing I
forgot to get the beer that Ted had asked for! I had already driven a
few blocks and really didn't want to make another stop but as soon as I
made it to the last set of stop lights I made the turn and headed for
the liquor store.
I passed the cleaners where Ted took his suits and passed two
restaurants he visited every now and then. I then realized that I had
better get used to going out dressed this way because for the moment
there wasn't any turning back. Another strange sensation! I finally
arrived at the liquor store and made my way inside. There were several
young men and a few older men shopping for spirits and I noticed there
wasn't a woman in sight! It didn't take long to realize I was being
given the long look over. I suddenly felt out of place, I wished I had
worn my jeans in going out, even though they were ladies jeans. Because
now here I was, in a dress with those high stiletto heeled sandals that
raised my height to a statuesque 5 feet 10 inches tall! I wiggled past
two older men thankful I couldn't hear my heels on the carpeted floor
but in the quiet aisle I could hear my nylons zipping with each step as
I wiggled past those men. They could smell the perfume as I floated by
then took casual notice as one man commented to the other. "Now that's
a lady! Nice legs too!" he said in a whisper then added "I wish more
women would dress like that." As the other man nodded in agreement.
I found the 12 pack of beer I needed and picked up some wine coolers Ted
liked then quickly paid my bill with the "Thank you 'ma-am'" from the
cashier still echoing in my ears as I minced out of the store.
But then the wind struck again! As I exited the building a gust blew
past lifting my skirt and slips high into the air! I gasped in open
mouthed surprise but with both hands full carrying my purchases and my
purse slung over my shoulder I could only stop and gasp in shock as I
teetered on my heels looking down. My lace trimmed panties, the tops of
my shiny tightly gartered stockings now exposed in full view showing off
long and feminine legs as I gasped, looking like a vintage pin-up
picture. But I wasn't alone in my experience, I knew it the moment I
heard the gasps and the male voices.
"Holy Shit! Check out the chick in the yellow dress there!" the young
man from a group of three gasped as he pointed at seeing the full show
of all my now exposed lingerie. I heard the wolf whistle and saw the
smiles as I glanced at them with an embarrassed look. Flustered I
quickly struggled to push the dress down. Luckily the gust of wind
passed and finally gravity took over allowing most of the dress to swirl
back down. However it was still folded up on my right leg showing my
white lace trimmed slip and part of my upper thigh as I put the packages
in the back seat of the car. I then quickly smoothed the dress down as
the three men, still slowly walking into the liquor store kept their
eyes on me.
"Damn, them's some long legs!" one of them said to another as the
comments continued. "See them lacy white panties on that pretty ass of
'hers'!? She even had on a garter belt too!" they continued as I
entered the car and gathered the dress around me so I could close the
door. I finally pulled out of the lot and noticed the three guys
finally entering the store as I drove away and headed home.
It was another strange sensation, maybe it was my new learning curve of
sorts. I wasn't being ridiculed, I was being leered at, ogled by those
men! Was I actually passing!? Maybe Ted had known all along I thought
as I felt my confidence begin to build on the way home. But there was
another hurdle to jump that I didn't yet know about. It was Jack
Weston, the next door neighbor who had seen me in broad daylight and in
full view as I left Ted's house that morning wearing a dress!
Charlize
- 12.12.2021
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