My Twin
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Carole's Twin free porn video
Carole's Twin
Being a somewhat confused 16 year old high school student who had no
real relationships with girls of my own age, I soon found myself
overtaken with a serious case of puppy love for the woman I had recently
began babysitting for a few nights a month. Her name was Carole
Douglas, and she was about 35 years at the time, in the midst of a
second marriage to Jack, who was a few years older than her. Jack was a
Greyhound bus driver with frequent extended overnight trips up and down
the East Coast, and he was rarely home when I was called to babysit.
Carole looked a lot like Doris Day in my view, and she was simply
amazing in style and personality, with a very sweet manner. She always
seemed to dress in an alluring, yet understated style that would later
become defined as the perfect MILF look.
Carole had a son about 8 years old from her first marriage, while Jack's
kids were in college and did not live at home. Just before I started
babysitting for her, Carole and Jack had adopted two infants, so there
was definitely a need for someone to care for them on the nights that
Carole and Jack had other commitments. While Jack was driving, Carole
was also managing a deli owned by her family in Boston a few nights a
week, as well as most weekends. As a result, there was a recurring need
for someone to babysit the children, and my parents had arranged for me
to begin babysitting for them when the Douglas' previous babysitter had
graduated from high school and headed off to college.
The first night that I was to babysit had me anxiously waiting to be
picked up by Carole for the drive a few miles across town to her home.
When her car pulled up and the horn honked, I said my goodbyes to my
parents and was soon sitting beside the object of so many fantasy
dreams, and the magic began almost immediately.
After some brief chatting during the drive where I was relishing every
second of being there beside her, drawing in her perfumed scent,
admiring the outfit she was wearing, and glancing at her profile without
looking obvious, Carole explained, "Our last sitter was with us for
almost four years, and we even went to his high school graduation, so
I'm hoping this will work out with you, too."
"That'd be really nice, Mrs. Douglas."
She parked at the curb in front of her home, and I noted it was a split
level colonial in a pretty nice area of town. The status of the home
was an indicator of a fairly well off middle class family, and I was
already looking forward to seeing how she had decorated and furnished
the inside. As I walked behind her along the walkway toward the home, I
couldn't help but admire how she looked from even that view. Not
exactly gorgeous, but obviously the type of woman that I knew I would
completely fall in love with, and I regretted immediately the age
difference between us...she would always be unobtainable for me.
As we reached the door, I waited while she used her key to unlock the
door, and I noted that I was probably only an inch taller than her. I
had a fairly lean build, so I was already wondering if I would be able
to fit comfortably in her outfits. For the past few years, I had
dabbled with trying on women's clothing, with most of my pieces
liberated from charity clothing drives from my scouting troop. Nothing
sexy, but I had so far collected a few skirts, blouses and two dresses.
If Carole was a size 8 or larger, I knew that I would be able to fit
into her things, and I was already longing to check her hamper to see
what was there.
I managed to control my desires for the first several times babysitting
for Carole, but one evening I discovered a very alluring black bikini
left to dry on a rack in the laundry/utility room. Of course, other
than imagining how it looked on Carole, I was next wondering how it
might look and feel on me, and it seemed like hours had passed before I
was certain her children were sleeping soundly. Satisfied that now was
as long as I could wait, as I wanted to be sure that I would have enough
time to experience wearing the bikini before carefully restoring
everything as it was. I was nervous as I made sure the den drapes were
fully closed, which was next to the laundry/utility room, and in a few
minutes, I was naked and holding the bikini in my hands, admiring the
texture of what I realized was a leather-like fabric. It certainly gave
me a new appreciation for the sexiness of Carole.
After slipping into the bikini, I was happy that it fit my waist and
hips, and the top was equally form fitting, although I clearly was
missing the essential flesh to fill out the cups. Even so, it was an
incomplete feeling, as I knew I needed to truly be as feminine as
possible, to include hair, makeup and even a hint of Carole's perfume.
Of course, I satisfied my urges, and was careful to not get my wetness
on the bikini fabric. From that point forward, I was intent to make my
transition to Carole as complete as possible, even if I had to bring my
own wig in the form of a Halloween fright wig that was not too bad
looking once it was brushed out. However, that turned out to not be
necessary, as my next guilt ridden babysitting job led me to a thorough
inspection of Carole's bedroom, which revealed two of her wigs. As a
result, from that point forward, I would always have the benefit of
Carole's hair style when I dressed as her.
Carole also had so many wonderful makeup and beauty products in both the
upstairs full bath and the downstairs half bath. In actuality, the half
bath had a nicer and more complete assortment, and it was the room where
I did most of my transformations. I began to practice my makeup skills
virtually every time I was babysitting, even if her son was there. He
was a pretty sound sleeper, and being in the half bath made it easy to
lock the door and not fear an unexpected visitor. The very rare times
he awoke during the night always could be resolved by me simply calling
upstairs for him to go back to bed. If he ever saw how I looked, I knew
my dressing would be ended on very difficult terms.
Since my intent was to emulate Carole, I took care to notice the way she
wore make up for regular functions, as well as when she dressed up for
what was obviously a special event or function, such as New Year's Eve.
I also had the family photo albums from the den to use as guides, and
these sometimes inspired me to capture the exact look, such as a photo
from when she was out with a girlfriend, with both of them wearing the
classic little black dress at an upscale bar.
Carole was consistent with never once arriving home earlier than she
stated before leaving, and often she would call to give me any update as
the evening went on, so on those evenings, I knew almost to the minute
how long I could stay in character. It was always so amazing to answer
the phone while I was dressed as her and talk for a few minutes, giving
her every assurance that the kids were great and were now sleeping
soundly. How could anything bad happen to the kids when "mom" was so
close to come immediately to address every need?
The evening when everything changed for me was a chilly Friday in
January. The older son was away at a hockey camp for the entire
weekend, so after putting the two young children to bed at 7:00 PM, I
had absolute freedom to perform my transformation into Carole. Although
the forecast had been for otherwise, snow started falling at a rate
where it quickly began to accumulate. However, I did not notice that as
I selected that night's outfit and settled in at the makeup table in the
downstairs bath. As the snow fell, I was totally unaware of the change
in the weather, as every moment brought me to look more like the woman I
adored.
My feminine transformation began with undressing completely from my boy
clothes and then slipping on a pair of Carole's black satin panties and
a lacey black underwire bra. I then stuffed the bra cups with faux
breasts made from an old pair of stockings filled with about a cup each
with bird seed and then tied into soft balls. The bird seed gave my
"breasts" firm yet flexible shape, weight and substance of what I
thought real ones might have, since I had no experience personally with
a woman's breasts. Carole was a size 34B, and I happily emulated her by
matching the breast forms to fit comfortably in her bras. I also wore a
pair of nude pantyhose augmented with the set of foam hip pads that I
had created months ago to give me a more curvaceous and feminine body,
and it really gave the impression of wider womanly hips once I put on a
dress or skirt.
I gingerly began my makeup ritual of foundation preparation. Having
literally no facial hair and little signs of acne gave me a good
platform to work with. I used a somewhat lighter liquid foundation than
my actual skin tone, but it was only a subtle difference, and I then
used a light dusting of powder to set it. Since I had enough time to do
a thorough makeup removal, I applied black eyeliner to frame my eyes,
then delicately applied mascara to my lashes, not too much, just right.
Then I finished the eyes with a touch of light blue eye shadow, that I
feathered to a nice effect before leaning back to assess my efforts.
I was very pleased and smiled as I reached for a cranberry red lipstick.
Pulling off the top, I turned the stick and smiled even more as I saw
the well used shape of the lipstick emerge. I loved the idea that the
last person to have used this lipstick was Carole, herself, and each
time I used her lipsticks, it was a loving touch of her own kisses that
adorned my lips.
After carefully applying a coating of the lipstick, I used a tissue to
imprint the lipstick, and set the kissed tissue to the side as I deftly
used a brush to add blush to my cheeks. Looking at myself in the makeup
mirror, I could not help but smile as I turned side to side to inspect
my results. All in all, a bit understated, as Carole, herself, would
do, and I slid the chair back and turned to glance at tonight's outfit.
A 3/4 length sleeved patterned top with an emerald green and black
leopard spot pattern, and a black pencil skirt were the main elements,
with a pair of 3 inch strappy back black heels to complete the look. By
this time, I was totally at ease wearing high heels, and loved the way
they set off my legs, as well as how the heels forced me to assume a
much more feminine gate with a subtle hip sway when I walked. I slipped
the skirt up and zipped the back, and then fastened the button tab to
keep the zipper in place. It fit perfectly, as I already knew it would,
as I had worn it a few times with other tops, but tonight was to be my
first time wearing the green and black top. I then slipped on the heels
and fastened the buckles and stood.
Next, I took Carole's medium length wig and adjusted it into place,
perfectly framing my face and falling to just above the shoulder line.
I felt almost complete as Carole at that moment and only needed earrings
and jewelry to finish the look. I put on a pair of dangly screw back
earrings, three gold bangles on one wrist and single, heavier bracelet
on the other, finished off by two rings on my wedding finger, wishfully
thinking of them as an actual engagement ring and a wedding band...
oops, one more thing, since I would even have time to shower to clean up
after my time as Carole, two light spritzes of a flowery perfume.
Oh my god, I thought as I turned and looked at my reflection in the full
sized mirror. I saw in the reflection a younger version of Carole, me!
As any good wife and mother, I knew that I should take a quick check on
the children, and I easily moved up the stairs and turned the corner
which is when I noticed the accumulation of snow. Easily four inches
had fallen, and it was still coming down heavily, and the snow plows had
not yet even touched the street. I sensed that Carole would not be able
to travel home that night with the snowy weather, and at that very
moment the phone rang.
I stepped quickly to the phone, "Hello, Douglas residence," I answered
in my boy voice, but in all other respects I was the woman of the house.
"Hi, honey," Carole replied, "I just wanted to check on things... and, I
know this is unexpected, but it looks like the roads aren't going to be
clear until tomorrow morning..."
"I know, I was just looking outside."
"Well, I already called your parents and they're okay if you could spend
the night."
My heart leapt with joy, "Uhm, I guess that's okay then. I don't mind."
"Are you sure? I could ask Thelma to come over, instead." Thelma was
Carole's single older sister who lived nearby in the next town. While
generally a very pleasant woman, and sometimes quite funny, she had
somehow not been blessed with the beauty that Carole had inherited, but
she definitely had a much more shapely and full figure.
"Oh no, the roads look pretty bad, I'm worried she might have real
trouble..."
"Okay, you're sure, then?"
"Totally, the kids and I'll do fine," as I admired my reflection in the
picture window with the snow continuing to fall outside.
"Just in case the babies need anything, would you mind sleeping
upstairs... you can stay in my bed."
"Wow? I just figured I'd use your son's bed."
"Oh no, that's too small for you. It's fine. The sheets are fresh, and
it'll make me feel better knowing you are there, okay?"
"Well, okay, I guess."
"Alright, I'll call you in the morning. You won't mind feeding the kids
and getting them cleaned and changed before I get there, will you?"
"Of course not, and they'll be as great as always. You don't have to
worry."
With an obvious tone of relief, Carole quietly said, "I feel so much
better knowing you're there, and please, just make yourself at home."
"Okay, Mrs. Douglas, see you tomorrow."
"Night, night," and she was gone. Breathlessly, I considered how
perfect it would be to actually sleep wearing one of her negligees or
night gowns in her own bed! Oh, this was heaven!
I peeped into the children's bedroom and saw them both sleeping soundly.
I quietly stepped into the room and checked on them both, such sweet
babies. Satisfied that the children were fine, I slowly backed out and
gently closed the door. I was actually weak kneed at that moment, and
felt in awe about Carole's ability to be the perfect mom.
With the whole evening now totally uninhibited by any need to transform
back to my boy mode, I decided to emulate being Carole as the hostess of
an imagined get together with her neighbors. I thought my choice of
outfit was nicely suited to that type of social engagement, and as I
passed by the kitchen, I took a can of ginger ale from the refrigerator.
I intended for the ginger ale to be my white wine, and headed down the
stairs to the entertainment room that was opposite to the den.
The entertainment room had a modern theme, with sleek black leather
furniture, a large console TV and a very nice stereo system. The room
also had a bar set with five bar stools and all of the fixings for
proper entertaining, and the lighting mood could be set to a softer tone
for what I imagined to be a more intimate setting.
As I poured the ginger ale into a champagne flute I noticed the only
flaw with my transformation to Carole, my nails. My finger nails were
drab and hardly feminine looking. I knew that Carole had several
packages of press on nails, and while I had never used them before, I
decided tonight required perfection.
I seated myself again at the downstairs makeup table and carefully read
the instructions on one of the packages. Pretty simple, and the nail
polish remover would make it easy to remove them in the morning. I
picked the French manicure style, since it was the most numerous of the
packages, and after a few false steps, finally had each of my hands
transformed into much more feminine looking style. The false nails
extended beyond my normal length, and I was surprised at how different
it felt to pick things up while wearing them. I thought briefly about
how hard it would be to unzip the skirt or do almost anything else in
the morning, but figured that I would remove the press on nails the
first thing before having to do anything.
Of course, the first task at hand was to reposition my full hardness,
which had become uncomfortable as I had worked on applying the press on
nails. I usually tucked when I dressed, but somehow, I had slipped out
of place.
I loved the look of my now totally feminine left hand holding the hem of
the skirt as my right hand slipped into the pantyhose. As I touched
myself, the feeling of the nails had an amazing effect on me. They
really changed the sensation of touch, and it was a bit awkward forcing
my hardness back into position, but as I finished, I once again had a
nice smooth feminine front.
Pleased with the now total transformation, I decided that I would hold
off masturbating until I changed into whichever negligee or nightgown
that caught my eye later in the evening. I was actually quite proud of
my ability to resist the usual temptation, but my sexual satisfaction
was secondary to me fully assuming the role of Carole as the hostess,
and I hurried back to attend to my "guests."
Holding my champagne glass of ginger ale, I turned the stereo on and
dialed in one of the local pop stations and 'Heartbeat, It's a Lovebeat'
by DeFranco Family was playing. I couldn't resist starting to twist and
dance to the music the way real women and girls would do. Hips swaying,
mouthing the words, and playfully brushing at my hair as I moved, I was
so taken in the moment that I never heard the front door open, the
stomping off of the snow, or the steps on the stairs. But I definitely
heard the questioning word that came from Jack, "Carole?"
I almost dropped the champagne glass as I otherwise froze in place.
"Hon, what's going on, I thought..." and then the realization hit him, I
wasn't Carole.
I turned to face Jack, tears starting to well up in my eyes, as I
murmured, "No, Mr. Douglas, it's me."
The sound of my voice was the only thing that gave identity to the
person who in all other respects looked like Carole from across the
room.
"What's going on, why are you... I mean, why?"
Tearfully, the crying started immediately as I clutched the champagne
glass with both hands to my faux bosom, my body racked with sobs. I
couldn't bear to look at his face, to realize the sense of betrayal of
trust I felt my actions had caused.
I stood there, sobbing, for about the longest minute of my life, my mind
racing with thoughts of the anger my parents would have, as well as the
public humiliation that was surely to come. The one thing I never
expected was the gentle touch of Jack's hand as he slowly lifted my chin
with the tip of his finger. My eyes turned up to meet his gentle gaze.
Rather than hate or even disappointment, all I saw was a sense of real
caring.
"Would you like to talk about this? I'm not angry, but I don't
understand."
My only response was to suddenly press myself against his chest and to
continue sobbing. His arms wrapped around me and he held me close,
tenderly, and let me finish my crying. I felt so safe in his arms, and
realizing he was not angry allowed me to regain a little of my
composure.
"I'm really sorry, Mr. Douglas, I just, I just...", but he cut me off,
with a softly spoken, "You really do look like her."
"Really? You think so?"
"I wouldn't say it if it wasn't true." He paused, then said, "You've
been doing this for a while, haven't you?"
"Yessir, I'm sorry, I don't...," but he cut me off again as he looked at
my face.
"You're her right now, aren't you?"
"Yessir." I whispered.
"Then call me Jack, and can I call you Carole?"
"I guess."
"Come on, Carole, let's sit you down," as he gently guided me to the
large black leather sofa. I sat next to him, primly with my knees
together and wiped away the remnants of a tear.
"I'm amazed at how much you look like her... so close to how you, I mean
she looked ten years ago."
My heart leapt with joy, "Really?"
"Absolutely, but I'm not sure I approve of you drinking champagne,
though."
I giggled, "It's only ginger ale, I knew I shouldn't drink real alcohol
while I was babysitting."
"That's right, not when you're babysitting, but since I'm home, I think
we can say you aren't babysitting anymore, would you like me to fix you
what I usually make for you?"
"Really?"
"Really," a slight pause, "You won't tell anyone though, right?"
"Oh, no, Mr. Douglas, I would never..."
He cut me off with a gentle touch of his finger to my lipsticked lips.
"Carole, you need to start calling me Jack, okay?"
"Yes, Jack, I won't say anything to anyone."
"This is our secret."
I couldn't stop what came out in my most feminine tone, "Yes, darling."
Jack smiled as he took the glass of faux champagne from my hands and he
headed over to the bar. As he prepared my drink, he continued a light
exchange with me, which accomplished three critical things confirming
first that Carole was not coming home tonight; that I was 16 and legally
able to give sexual consent, even though that's not how it was asked;
and lastly that I really enjoyed my role playing as Carole.
I was totally unprepared for everything that was happening, but as I
watched Jack prepare my drink, I quickly came to appreciate everything
that Carole must also have felt about him. Strong, confident, handsome,
and caring. What more could any woman ask for, or even hope for in
spouse?
Since I couldn't see the preparations being made behind the bar, and
realizing my eye makeup was probably a total mess, I called out, "Jack,
would you mind if I freshened up?"
"Go right ahead, hon, but don't take too long or I'll have to come after
you." I answered with a giggle as I stood and walked, swishing my hips
as subtly as possible, as I headed to the bathroom.
As I closed the bathroom door, my right hand laid so naturally on my
bosom as the thoughts and emotions rolled through my mind. Foremost, I
wondered briefly if I was misunderstanding Jack's response to finding me
dressed as his wife, but inside I was still a guy and realized that Jack
was going to make the most of this situation... I smiled as I, too, knew
I was going to do the same. For this night, I am Carole.
Now certain of my own intentions, I sat at the makeup counter, and one
glace in the mirror confirmed my worst suspicions. My mascara had run
terribly. I promptly set about fixing everything to my satisfaction,
which was now a very high standard, as my "husband" was expecting his
"wife" to reappear shortly looking as beautiful as possible.
Although no direct words were exchanged, the tone of Jack's words and
his manner confirmed for me that I would be expected to be Carole in
every sense possible. Obviously, no one knew that he'd be arriving home
early, I had confirmed for him that Carole was not coming home, and he
was making me "my" drink. I decided to fully embrace being Carole, and
confirmed this by choosing the bottle of Chanel No. 5 and applied it
sparingly to my neck, just behind my ears, on my inner wrists, my
elbows, my shoulders, and a drop right where my real cleavage would have
been. The change in scent brought a burst of confidence in my spirit,
and I certainly felt more attractive with the Chanel allure. A much
more romantic scent than the comfortable flowery perfume from earlier,
and I wondered if Jack would notice the change.
Almost ready to return to my "husband," I also freshened up my lipstick,
but did not blot it on a tissue this time, as I wanted to leave a very
noticeable imprint of my lips on my waiting drink glass... or on my
husband's lips if the drink could not wait.
I could have stopped everything right there, but I had no desire or
intention of not exploring my role as fully as possible. I didn't care
that I might simply end up being used by Jack, as his tenderness and
caring was truly genuine in my mind... no, my heart.
Glancing at my reflection in the full mirror on the wall across from me,
I smiled, and saw Carole totally in her element, ready and willing to
respond to her husband's every need, want and desire. I confidently
made my way back to the entertainment room, pausing briefly in the
doorway to smile at Jack where he sat with our drinks.
Whether it was fate or otherwise, at that very moment the radio began
playing Ringo Starr's "You're Sixteen." As I slowly walked toward Jack,
I swayed and moved for him, mouthing the words. From his expression, I
knew that I was doing everything right. He could clearly see my makeup
was freshened, and my youthful, feminine shape begged to be held.
Jack stood and beckoned for me to come to his waiting arms, and I moved
coyly towards him trying to look seductive and innocent at the same
time. As I reached him, his arms enveloped me, and I melted against my
strong, handsome husband, and we slowly danced together as my mind
prepared me to be the best wife possible for my dear "husband."
Vera
- 10.08.2020
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