Allegra
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It All Started With A Question free porn video
A guy having an early breakfast at a small diner, meets a lady and then
unexpected things start to happen. Things he would have never thought
possible.
IT ALL STARTED WITH A QUESTION!
Part #1
It started out like any normal Saturday morning. It was a nice cool,
bright sunny day in early October. The year 1971, and I was sitting
alone, at the far end of a counter, in an old-style diner. The diner is
not my normal breakfast hang out. I was mainly here, because one of the
best and largest hardware stores in the area was right near by, and
that's where I was headed next.
After I finished my breakfast, I paid the waitress, and gave her a nice
tip. The waitress left to ring up my payment as I took my last sip of
coffee and stood up to leave. I was turning to head out the door, when I
heard a really nice sounding female voice from behind me. However, what
she said shocked me, and had me in a slight panic, as I heard the lady
say, "I really like those lavender panties you're wearing. Tell me are
they the real lacey kind?"
I quickly turned around, and at the same time put my hand behind me,
checking to see if my panties were actually showing. Sure, enough my tee
shirt had ridden up, and my jeans were hanging down a little, so that my
lavender panties were showing way above my belt line. I started to fix
and adjust my shirt and pants, making sure the panties weren't showing
anymore. At the same time, I looked over to where I heard that soft,
sultry voice. My eyes came to rest on a very pretty lady, who looked to
be in her late 20's, or early 30's. She was seated almost right behind me
in the last booth, and as our eyes met she gave me this really nice warm
inviting smile and then she winked at me.
I finished fixing myself up, and readjusting everything, but still in a
slight panic. I now turned my attention to see who if anyone was nearby.
I first looked at the other booths, which were nearby, and to my relief
they were all empty. I then looked down to the other end of the dinner
and counter to see if anyone else was close enough to see or hear what
she had said. I was hoping no one was near enough to have overheard her
remarks about the panties! I was also embarrassed to think that everyone
may have seen me adjusting my clothes. Luckily for me, everyone in the
diner were at the far other end of the restaurant, including the
waitress. They were all busy talking about something or other.
That's when I heard the same woman ask me another question. So, I turned
my attention back to her as she asked, "Do you wear panties all the time?
"If you do, what's your favorite color, and what style to you like the
best?"
"Maybe you like the full brief?" No!
I think you're more of a high cut pantie style person, right?"
Not wanting anyone else to hear what she was saying, I quickly walked
closer to where she was seated. Figuring my secret was already out, I
looked her right in the eye and told her, "Yes, I do wear them all the
time."
I'm not sure why I kept talking, but I went on to explain that I've been
wearing panties on and off since back when I was about seven-years-old.
As for my favorite color what else, I liked pink or lavender the best,
and my favorite style is the high cut nylon spandex that are trimmed with
nice lace accents. I figured this would throw her off balance and stop
her from asking any more embarrassing questions.
Boy was I wrong about that!
She looked at me with a surprised look saying, "Wow!" I like a guy who is
honest, especially someone who would admit that he likes wearing lacey
panties all the time. Then she gave me another big smile saying, I never
met a guy that I knew for sure wore panties, but I guess most guys who
do, would try to keep that a big secret right?
I'm now standing right in front of her booth and was a little taken back
by her statement! I mean a lady who is okay with a guy wearing panties?
Really!
She then asked me if I was going any place important, or did I have time
to sit down and talk a while.
I was now a little curious about this lady. So, I told her that I wasn't
in any big rush, and that I could hang around a while to talk. I then sat
down across from her in the booth, as she called down to the waitress,
and ordered me another cup of coffee, telling her to put it on her tab.
We made small talk for a while, sipping on the coffees.
It was then that I said, "You know we have been talking for almost ten
minutes now, and I still don't know your name?"
She replied, "Oh! My name is Jennifer, what's yours?"
That's when I told her that my name was Jack.
Jennifer said, "Glad to meet you Jack," as I answered, "Same here
Jennifer."
We did some more small talk, with questions, like my age, if I had a job,
and what type of work I did?
I told her I worked at a nursing home as the head of maintenance, and
that I was 26 years old.
The Next thing I hear her say is, "No Way!"
For some reason she had a hard time believing I was that old. With a
smile on her face she said I figured you for fourteen maybe sixteen at
the most. Jennifer then asked me if I ever dressed up completely or did I
just like wearing undies and lingerie? She also wanted to know if I was
married and if so, what my wife thought about my dressing,
Wow this gal is right up front with her questions!
I told her that I wasn't married, and that currently I didn't have a
girlfriend. I went on to explain that I do dress up completely about
twice a month. I also mentioned that I belonged to a cross-dresser's
support group, and that once a month we have meetings. I informed her
that I would go to the meetings and change there, because we had a room
to change in for the guys who could not come dressed. I went on to tell
her how sometimes I would get dressed at home to go to the meeting, but
that it all depended on how dark it was outside, and if anyone was home
next door. I explained how I have some very young kids living on both
sides of me, and I wouldn't want them or their parents to see me dressed
as a lady. I felt the kids were way too young to understand.
Jennifer replied that it was a good point and she could understand how I
felt. We talked some more, and she was very interested in my cross-
dressing, as she asked more & more question. Like do I have a feminine
name? To which I replied yes, when dressed I use the name Jillian, or
Jill.
I realized while answering some of her questions I was almost telling her
my life story. I have never told anyone about my dressing, so why am I
telling her everything? I decide if she is that interested I would tried
explaining how being a crossdresser feels, and how long I have been
hiding my dressing from others. I went on to try and explained why I felt
so good when dressed. I figured if she is that interested in cross-
dressing; I wanted to let her know how a crossdresser feels. The more
people know and understand us, the better it is for all of us cross-
dressers.
Next thing she wanted to know was, if I had any pictures of myself
dressed, because she was curious about how I might look all done up. I
reached for my wallet and took out my ID card for the support group and
another picture I carry with me. I mentioned that when driving dressed,
if I should get pulled over, I would hand this ID card over with my
license. I told her that the card had a picture of me dressed from the
chest up, but most important was on the back of the card it explained
that I was a cross-dresser, and dressing for my own pleasure. This way
the cop wouldn't think I was trying to hide my identity.
She took the card and the other picture giving them the once over, while
also checking me out. After about two minutes of checking the card, the
picture, and me. She said, "I like what I see. You look really cute in
that photo and you almost pass. The Only problem I see is you look more
like a young girl, who is maybe ten or eleven years old, rather than an
adult in these pictures."
I said, "Thanks, but you're right! I know I don't pass that well as a
woman. I'm way too short, as I'm only 4ft- 6-inches tall. Plus, besides
being small, I don't weight that much at 105 lbs. and I have very slim
shoulders and arms. Plus, I have a very, very, young and feminine looking
face. Like you said when I'm dressed up I look more like a little girl
trying to play dress up, in her mother's clothes, rather than an adult
woman."
I went on to explain that because of my size I have such a big problem
finding things I can wear, as the clothes in the lady's department kind
of hang on me. Then if and when I do buy an outfit; most times I need to
get it tailored to fit, which makes the cost almost double the price of
the outfit. That's one of the reasons a lot of the times I will end up
buying my clothes in the Junior Miss department, or even the Kids
department. The problem there is the Junior Miss and kid's departments
really don't have anything that looks grown up, which is another big
problem for me. It's also one of the reason I don't go out in public
that much. That in a way leads to another problem.
Jennifer asked, "Oh! And what kind of problem would that be?"
I said the problem of staying home while all dressed up.
She looked at me with this questioning look as I started to explain.
Think of it like this, just like any lady, when you're all dressed-up;
you want to show off how great you believe you look. It's like any lady
would feel. Here you are all dressed up pretty and feeling great inside
ready to go out and show off how great you look, but you can't."
I call it the "Pretty Girl in the Cage Syndrome." You are dressed to the
nines, feeling oh so pretty and happy about how you look, and wanting to
show yourself off to the world. Only there's no place to go that you
could pass, and even worse, you could end up being made as a guy who's
dressed as a girl. Okay let's face it, a guy walking around in a junior
miss outfit, can cause some stares, and create serious problems if you
don't look just right. So, to be safe, you end up just hanging around
your house, or apartment, wishing you could really pass.
Imagine how it feels being stuck in a room at home, feeling like you are
in a cage. You start feeling really down about yourself, and hating that
God made you this way. Next thing you know you start hating how you
look, even though you just spent an hour or more, with your make-up and
wig getting yourself all dolled up. That's when the Jealousy kicks in,
and you start wishing you could be like some of the other Gals / Guys,
who really look so great, with more shapely bodies and faces that can
pass with ease. Those gals get to go out dress in great looking outfits,
in public anytime they want. That's when you really start getting mad at
yourself for thinking you could pass like they do. Then you start to get
mad at yourself and how you look. So, you start taking everything off,
feeling really mad, depressed, guilty, and thinking just how unfair the
world can be.
Jennifer looked at me saying, oh-my! That's so sad! So, what you're
saying is, when your dressed you're never really happy about how you
look?
I went on to say, not really, I think I'm like any other cross-dresser. I
love getting all dolled up any chance I can. You could say that when
dressed we all try to really look as feminine as possible. No matter what
shape or size our bodies are. Once we are dressed and look in the mirror,
our minds will see ourselves as beautiful ladies. As for myself I kind
have learned a few tricks and ways to feel much better about my small
size and figure over the years. I think now it's easier for me when I'm
home alone and dressed, but it's very complicated to explain to someone
who's not a crossdresser.
Jennifer said, "Oh, please go on, explain, I would love to listen and
understand. This is so very interesting to me, and I have the time. So,
please don't stop go on, explain."
I was a little shocked that Jennifer actually wanted to hear more.
I started off saying that I just hope you don't think of me as being too
weird or strange, with what I'm about to tell you?"
I had the feeling that Jennifer seemed very interested in what I was
about to tell her. So, I went on to explain. I told her that when I'm
dressed I feel like any lady that is dressed up nicely. I feel that I
need to go out someplace, anyplace, maybe just for a drive, or walk, even
if just to a drive-in-movie. Only in my mind I know I really can't pass
as a woman, because I look so young. Plus, like I said before, there are
other reasons I don't leave my house dressed. There are two really nice
families, with kids, who live on each side of me. How do you explain why
I'm dressed as a lady to them? Would they really understand why I am
dressed like a female?
I knew deep down that I had to find a way to feel good about myself,
while dressed at home. That's when I remembered what it was like, when I
was small and growing up. Back in the early fifties I had fun at home
playing dress-up in one of my sister's dresses. My sister and I would
play dress up some times and I would wear one of her dresses. I think
that's how I got hooked on dressing. When my mom and sister would be gone
for a while I would dress in one of my sister's outfits, right down to
the undies and all. I was having fun and there was no need for me to
leave the house. I was able to play with my sister's dolls and things,
while dressed in one of her frilly party dresses, with the crinoline, and
the cute rumba panties. I knew no one was going to be home for a while,
so I had full run of the house pretending I was a little girl, playing
with my sister's stuff.
So, I decided I was going to try to relive that time when I felt good.
Seeing that I'm so short and small in size I decided to check into the
size charts for little girls. I found out that I was actually pretty
close to the same size as an eight-year-old girl. Knowing this I started
to go to some thrift shops, and Salvation Army stores to look for any
cute little girl's outfits in an eight-year-olds size. To my shock I
found a couple of real cute frilly little girl style dresses that would
fit me. Matter of fact in one store I found what I now call my dream
dress. It was a fancy little girl's "Beauty Pageant Outfit." You know
the kind that a little girl would wear to compete in one of those, little
miss beauty pageants. I found out that the outfit came complete with
matching crinoline, rhumba panties, socks, and even a cute hat all in a
size that would fit me.
It was my lucky day, because it was near Halloween. So, I told the lady
running the store that I was there to find a Halloween costume. I led
her to believe my girlfriend and I were going switch rolls, and that I
would be going as a little girl because of my size, and my girlfriend as
a little boy. Anyhow while the lady was helping me look for something I
could wear; we found this pageant outfit. I said, "Wow I know it's a
little dressy, but it does look very girlish, do you think it would fit
me?"
She held it up against me saying it just might? I was in heaven when the
lady then said well there's only one way to find out. That's to go and
try it on. She led me over to a dressing room saying go ahead and try
the dress and crinoline on. About three minutes later I came out of the
dressing room wearing the outfit. She had me turn around so she could
zip it up. All I heard her say was wow it fits you prefect and looks
great on you. You almost look like a little girl, with your long hair in
that outfit. All you need to do is put your hair in pigtails and I bet
you could pass as a little girl in that dress. I said, really wow I guess
I have a Halloween outfit.
I thanked her and told her I would take the whole outfit right down to
the frilly little girl's bonnet or hat. Once I paid for it, I thanked
her for her help. She then made me promise to take pictures and bring
them in so she could see me all done up, which I must confess, I did take
some pictures and showed them to her.
Later that same day in another thrift shop I found two pair of Mary
Jane's in my size, which came in different colors. So, you guessed it, I
bought both pair. The next day I went out and found myself this real
pretty 18-inch doll, plus a dolls baby carriage, and to boot some clothes
to dress the doll in. I also picked up some other items I thought a
little girl would play with, like a couple of coloring books, crayons,
and even a tea party set.
I was hoping that now I would no long be bothered by wanting to go out
while dressed, because dressed as a little girl I would feel good about
staying home alone. You know I was right as I started to feel much
better, when I was dressed as a little girl. Sometimes I would even
watch a TV show like Sesame Street, while holding my doll, and sipping
juice out of a Sippy-cup.
Other times I would just sit and color in a princess coloring book, or
play with my dolly, while drinking from the Sippy cup. Now I no longer
feel trapped in that cage like I felt, when dressing as a woman. I can
now dress as a little girl and play in my home, because there is no
reason for a little girl to go out, as she has all she wants in the
house. There are some drawbacks like not interacting with others, but I
do feel better.
As I was explaining this to Jennifer, she was looking at me with this
funny gaze. Seeing the look on her face, I said, "Okay, I told you that
you might not understand, and think I'm a little weird and strange."
That's when she said, "OH NO sweetie! I do understand where you are
coming from, but wouldn't you like to have a friend or someone else there
too, perhaps another person as a playmate to play with? How about
someone who also likes to dress as a little girl, or maybe someone to
role play as the person in charge, like a mommy figure or Nanny type
person. It's got to be very lonely dressing and role-playing all by
yourself? I mean having someone else there to role-play, wouldn't that
make it more real feeling, so you would feel like you are little girl?"
I said, "Sure that would be great, but most of the people I have met or
know, who dress, don't dress as little girls. Plus let's face it; it's
not easy finding a lady, who would want to role play as a Mommy or Nanny
to some guy, who dresses as a little girl. I do have one friend name
Mike, who likes to dress as a little girl, but he has a girlfriend and
they do their own thing together."
Jennifer said, "Well I guess you are right about how hard it must be
trying to find someone, but have you looked?"
She had a point, as I said not really, mainly because I have no idea how
to look for someone like that. What would I do? Place a personal ad in
the paper?
YES! I can see it now!
"Lady wanted to role-play as a Mommy or Nanny to adult male, who likes to
dress and pretend to be an 8-year- old little girl."
Yep that should go over really great in the want ads?
Jennifer gave a big giggle to that statement. After which she said, well
I guess you're right about that.
We talked some more and I could tell she was definitely interested in
knowing more about me, and my cross-dressing.
We must have talked for another hour or more when she looked at her watch
saying; oh- my Jack look at the time, I real have to go. While getting
ready to leave Jennifer mentioned that she comes to this little diner a
lot, and hopefully she would see me again sometime.
I told her that I would look forward to the next time we should meet, and
we both got up and left.
As I drove to the hardware store I kept thinking about Jennifer. I
couldn't believe I spilled my guts to some person I just met, telling her
all my secrets. Hopefully we will meet and talk again. Who knows maybe I
found a new friend.
(That was going to happen a lot soon then I thought)
Hester
- 01.02.2022
- 10
- 0
