Embarrassing Moments-- Anonymous #1
This happened when I was just about to
turn eighteen and graduating. My mother's girlfriend, Karen, gave birth
to a beautiful baby about a year before. A baby girl - her name is
Christine. Karen and my mother get along like soul mates, so they say.
They do just about everything together. I'd swear at times they're
Well, Karen got this job offer and was to
start in two weeks. The job that was being offered to her at the time was
running the bar and restaurant at the Hilton Hotel. To her surprise she
needed a baby setter. I remember her trying to find some one, but just
couldn't find some one she could trust. So, she and my mother were
talking in the kitchen. I was in my bedroom trying to take a nap and heard
Karen asking my mother if it would be possible if I could baby set Christine.
I thought for sure my mother was going to say 'Are you crazy?'. But, to
my shocking ears, I heard her say, "That's a great
I must remind you. I was sort of in my first full
year of cross dressing. I was looking forward to that whole summer of
becoming feminine. I remember getting rushes just thinking of playing in
my mother's clothes every chance I got all summer long. I also must tell
you that I was not into any kind of sporting event of any kind. My
interest for that summer was becoming a young girl at every chance I got.
My mother, on the other hand, loved the fact that I wasn't into sports, that I
always wanted to stay home. She loved it so much that my chores was to
do all the housework. She taught me everything I know as of today.
I can cook, bake, do laundry, iron, fold. She even taught me how to sew - for
my thirteen birthday she bought me this beautiful singer sewing machine. I
You must be wondering where my father was. Well, he took off with this
other woman when I was eight. I remember that breaking my mother's
heart. All I wanted to do was to help her through that very painful
time. I have to admit, my mother and I became very close.
Well, that following evening during supper, my mother brought it up to
me, about babysetting all week, every week during the day, all summer long.
My heart dropped to my feet. I could feel my feminine side melt within.
I couldn't imagine not having the young girl come out for that whole summer.
I was shocked. I didn't know what to say.
Well, that following Monday morning my mother
took me over to Karen's and dropped me off. As I watched her drive away, I
felt so empty - lost is a better word. Then suddenly I heard Karen
asking me to come - in and she'd show me everything I need to know. I
must tell you, I've been over Karen's house many a times, visiting her with my
mother a few times and there was a few times that I babysat for her so my
mother and she could go out and party and be with adults. I remember
them saying that every time they went out. So, I must tell you that this
wasn't my first time with Christine. Matter of fact, she really liked me
and I have to admit, I got very close to her.
As I entered the house, I was shocked. There
were dirty dishes every where, the Sunday paper was scattered from the kitchen
to the dining room into the living room. Baby formula was on the
counter, kitchen table and the kitchen sink. Now Karen walks me to the
bathroom to show me where all the dippers are and, to my surprise, that, too,
is a complete mess, with all her make-up scattered on the counter-top. Then I
noticed something that gave me hope, to make me think that this isn't a bad
idea after all. I noticed two pair of her panties laying on the floor
next to the tub, plus a pair of her panty hose that she took off, apparently
because of a run. Then she took me directly to Christine's room, and I noticed
her fast asleep, and that this was the most neat room in the house. Than it
hit me. I see that Karen was in one of her full slips. She walks
me to her bedroom and continues to get dressed.
As I watch her finally working her pair of pantyhose on and noticed her
dropping her slip, she tells me the house is mind all mind do what I wish. Now
she ask me to help her with her heels. As she sets on the edge of her bed, I
slip them on. Than she ask for me to get her satin blue dress out of the
closet. As I'm helping her in this beautiful dress, I just about
fainted. Now to my surprise, she wants me to help her with her curlers, so I
did. Then I brush her hair till she loved what she saw. I was
totally shell shocked - I thought I died and went to heaven.
Well, as Karen was heading for the door, she
stopped and turned. I could see the excitement in her eyes. Having a chance to
prove herself at this job. A job she always wanted, It's what she studied for
through out college. Than she gives me a little peck on the cheek.
Telling me thanks and that she loves me like her own child. Just
as she was about to go outside. She stops again, as she turns, she ask. If you
don't mind touching and going through my undergarments I would really
appreciate you doing my laundry and maybe some house
work. At that moment, I know I died and went to
heaven. It seems like I couldn't say yes fast enough.
As I watched her back out of the drive, I could feel my feminine side
working her way out. I could feel my emotions changing, from my voice, to my
walk it was beautiful. It was a month away from my Eighteenth birthday
and summer is on it's way out and fall is stepping in.
Across the street there's this park. Where all summer long the boys and girls
would play all their games. Now, I see the boys getting ready for football. At
times as I feed Christine, I gaze out the kitchen window watching these young
men preparing for football. I caught my self many a times watching this one
good looking Spanish guy. He would always come onto the field with just
his tank-top and these very and I mean very tight shorts. He was very
dark, with long hair and very muscular. I couldn't keep my eyes off him.
As summer past by and I got to know most of Karen's clothes. I was being very
confident in dressing up. I must say I felt a little uncomfortable
when Christine was up so lots of times I was in one of Karen's many
spring jackets. I got to know more of her clothing than my mother's. I knew of
every colored panty she owns. Her bras, there were some that pinch me, than
there was some that fit so right, I'd swear I wasn't in a bra. Karen's
wardrobe was much more feminine than my mother's. Karen loves dresses more
than my mother.
So with that said, there was many more half and full slips. Plus she
loved her garter-belts, along with her sheer stockings. I don't think I
have to tell you, but I loved babysetting for Karen.
I noticed that I couldn't turn off my feminine
feelings as quickly as I used to. It seemed my feminine side wanted to stay
out and enjoy the life she was being offered and I'm wondering if Karen or my
mother ever noticed. Down deep I don't think so. But, it was getting to the
point where I even didn't notice.
Well, it was a very busy weekend night, Friday to be exact. My mother and
Karen were asked out by two very young men, Karen claims they were just
a few years older than me. But, old enough to party. They met them across the
street, where they were playing some touch football the weekend before. And it
so happens that my mother and Karen were jogging by and that's where they met.
Before you know it, they had a date. I got to admit, my mother and Karen back
then were some pretty woman. To be asked out by these two young men was no
surprise to me.
At this club where my mother and Karen frequent a lot, that weekend was one of
those very sexy nights. Where all the woman would dress up in very sexy
clothing. I remember Karen and Mother going shopping for there clothes. Well,
it was going to be one of my very feminine nights for me, Especially
babysetting for Karen. I found her beautiful wedding dress in the back of her
closet. It was in a large box, but it wasn't vacuumed. The day I found that
dress I started looking for her under garments and found each item. Knowing
where each Item was and that I was going to be a bride for the first time in
my life, that night could not come quick enough.
finishing my chores at home and my mother was ready to go. We were finally on
our way to my wedding day. As my mother and I entered Karen's house,
like always she wasn't ready. All we could see was Karen running around in her
bra, garter-belt, stockings and heels. Than she yells at me to help her with
her hair, than finally with her dress. Finally, off they went. It
was something like nine o'clock p.m. I had Christine fed, washed and dressed
Now it was my time. Feeling my excitement within, I could feel my feminine
side wanting desperately to step out. As time passed by, it was around
ten-thirty. I looked in Karen's full length mirror she had in her bedroom next
to her bed. All I could see was a woman that is always wanting to come out and
feel life. I felt so different, I felt like I always should . I could feel the
softness of every square inch of Karen's undergarments. My hair was
perfect, my make-up, I finally got my eye shadow just right, my lip
stick, it followed my lips perfectly.
Suddenly, I could hear keys at the
front door. My heart starts to pump, I started to feel light headed. Looking
at her clock on her dresser, I could see it was only eleven-fifteen. Karen and
my mother were not to be home till two or three in the morning. Now I could
hear the front door opening and Karen talking to someone. Now I was
desperately trying to think of where to hide, but then I was hoping that maybe
she was not going to come in her bedroom. So I tip-toed to her bedroom door
(feeling her undergarments rubbing up against my sheer stockings), I heard her
say something again. But this time it wasn't my mother, it was her date. Now
as I'm up against her door I could hear her say to him that she's got to
change in something more comfortable. With my heart racing, my eyes were
starting to tear, so as Karen opens the bedroom door I jump under her covers.
Feeling the wedding dress all around me, I try to flatten it out so that it
doesn't puff up the sheets so much. Suddenly I think of my make-up and the
lights go on.
Well, with not a very surprised look, Karen
turns to her date and says that she'll be out in bit. Than she shuts the door
slowly. As she turns towards me she has this very promising smile. Karen sees
me crying like a baby and comes and sits on the side of her bed, to comfort
me. I never felt so embarrassed in my entire life, I told her.
I told her I don't know what over came me and I'm asking her not to tell my
mother. With that promising smile, she leans in towards me and gives me
a kiss on my cheek. As she stands up she says. Honey, your mother
and I knew about your dressing in our clothes. There's nothing wrong
with it. You are who you are.
Than she asked me to get out of bed so she can see
who I really I'm. Than ask me to stop crying, so that I don't ruin my mascara.
That's when she told me, with a very surprised look, that I'm very pretty and
that I'm very good with make-up. So as I calmed down, she ask me to help her
with her dress, that she had to change it along with her undergarments. I
asked why - she wouldn't tell me. After she was cleaned up and changed.
She turns from the door and says. Don't ever be ashamed of yourself, you are
who you are and you're very pretty at that!
"Embarrassing Moments" Main page
Return to Homepage