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How Deep Do I Go? free porn video
How Deep Do I Go?
By Deanna Lea
Life in the seventh grade was a living Hell. That's why I
had hoped the summer away from home would be a welcome
relief.
Mom agreed, and allowed me to stay with Aunt Addie on her
farm in Kentucky. Aunt Addie was a tall very pretty woman
who ran the farm without a husband. Since she had no
children, having one war worn, soon to be eighth grader,
spend the summer with her would be a time we would never
forget.
I have always been a mama's boy, and as I grew, I have
developed into a very "fem" kind of kid that has learned to
appreciate the softer, more feminine side of life. Mom
accuses me of having a "girl's" room. And I do. She doesn't
say it in a criticizing way, but points up the fact that
I'd much rather have my life filled with lace and trim than
football, and dating girls.
A week before we were to leave for the summer Mom sat me
down and said she needed to have a "heart to heart" with
me. We've had very few of those over the years, so when she
wanted to talk to me I knew it must be important.
"You know of course that I'm looking forward to this trip
as much as you, don't you?" Mom asked, and then continued.
"I'd like to try something if you're open to it." Now she
had my curiosity. "You know I've never made a fuss about
how much you like to act as "fem" as you want, and anytime
you feel a need to dress up, It's always been okay, right?"
"Sure." is all I could muster, but somehow I knew there
would be something more coming, and it wouldn't take all
night to get there.
Mom started speaking very slowly, then in her own way asked
if I would like to spend the summer as her daughter, rather
then her son. I gasped!
"Do you really mean it?" I asked, and then with that smile
that only Mom could produce she said, "Yes."
My head was filled with so much giddiness that I didn't
know what to say. By the expression on my face it was easy
to tell that I would love to be Mom's daughter. Quickly the
thought occurred to me that this could be something I'd
like to go on for more than a few months.
"Would that be possible?" I asked. Mom said that we'd take
one day at a time and when the time was right, we'd make
the right decision.
The first order of business was my name. No longer did I
want to use my male name, Daniel, but I had another name
that I'd kept hidden under my pillow for many years.
When Mom asked what it was I said, "I've always wished my
name was Deanna."
"Deanna is such a pretty name" Mom offered, "and it's easy
to say. I like it!" and with that she pulled me towards her
and gave me a hug that was a way of saying welcome home
Deanna! I could see a tear falling from Moms eyes, and it
wasn't long until I knew the feel of tears falling from my
eyes as well.
That night was filled with all kinds of strange feelings.
First, the idea that I could be open and honest about who I
felt I was, secondly, the feeling of release, I would get
to experience life for the first time as a thirteen year
old girl, and hoping too for all the joys that puberty
would offer.
The week before we left for Kentucky was filled with doing
everything needed for the trip. Buying clothes. Wow! I
didn't realize how much fun shopping could be. Lucky for me
that Mom had a good sense of style and color, not that I
don't but she's been around a lot longer and has more
experience. It was fun trying on clothes. We did it all.
Mom bought clothes for every occasion, casual everyday wear
from blue jeans and tops to shorts, tennis shoes, ankle
socks, blouses, skirts, dresses, and night wear. This was a
big deal for Mom as well. She found a few new outfits for
herself, and the greatest part of the shopping experience
was when we bought the lingerie. Panties, Bras, Camisoles,
Teddies, and every other feminine under thing available for
a forty year old Mom, and her newly found thirteen year old
daughter.
I already had long hair, so styling was no problem, but the
fun part was all the accessories available. Ribbons,
scarf's, and all the attachments that could make me look
more like a girl then I'd ever dreamed.
Two days before we left Mom said that she had a surprise
for me and that I'd better get myself together fairly
quick.
We were at "Stephanie's" Mom's hairdresser. Stephanie was
really Steve, and everyone knew it, but he was always more
like my big sister, and best friend, that when Mom told me
he was going to give both of us makeovers, I felt as if I'd
died and gone to heaven.
Stephanie treated me just like all the other girls in the
shop. And the whole time was spent talking "girl talk". We
talked about clothes, hairstyles, boys, and dating men. We
also talked abut how much most of the women in the shop
thought men were one notch down from useless, except for
using them as sex objects. All in all it was an afternoon
that I would remember for a long time to come. I thought to
myself that I had arrived. Little did I know how far I had
to go.
Chapter 2
The trip from Oregon to Kentucky took two weeks. Mom
decided to drive rather than the train or plane. Mom felt
that it would be a good time to bring me up to date on how
things would change for me. She reminded me that there were
certain things that started happening for girls around my
age and that between her and Aunt Addie they had a way to
make me feel those same things. Mom showed me how girls
would respond to things differently than boys, and I was
expected to follow suit.
One night while in our motel room we saw something that
brought her point home to rest. A car pulled into the
parking slot next to our room and Mom said, "What do you
think of that car?"
I had to think for a second then said, "Mom, isn't that car
adorable? I love the color."
Mom smiled and said, "I think you get the point. A boy
might respond by saying, 'Hey that car is really cool.'"
That night in the room Mom introduced me to something else
I'd need to know. I thought it was strange that she got a
single bed, but soon learned the method to her meaning. We
both dressed for the night. She in a sheer nightgown that
fit her to a tee, and me in a baby doll that she bought as
a surprise. Her breasts are so full and beautiful. Her
nipples quickly hardened at the first exposure to cool
night air. Her panty covered a beautiful cunt that I had on
previous occasions had had the privilege of touching and
tasting.
This was not the first time Mother and me had lain together
in the same bed, but it was the first time I did it as her
daughter. I was filled with a rush that was totally
unstoppable.
Even though I still had the male part of me on this trip it
would not respond in a male way. As we lie next to each
other, she started touching me in places that she would
whisper, "We like to be touched here, and here, and
especially here."
She showed me that very wet spot between her legs and it
didn't take much effort for her legs to open and she gently
pulled me towards her waiting body. My first stop was her
wonderful boobs. Her nipples came to attention in a
moment's notice. The feel of her breasts and my tongue
stopping to love were more then a girl could expect. I
slowly moved down to her waiting bush and without
hesitation, went to places that I'd only imagined.
Mom whispered once again, "Don't you want a taste?" and her
fingers gently split her fold to what was going to be a
wonderful journey.
I had watched Mom and Sue Elliott do this enough times that
I felt I knew as much as they did in making love with
another woman and that somehow it all seemed so natural. My
tongue went in without hesitation. It moved slowly, then
when I felt a spot that Mom responded to, by the quiver of
her body, and the moan that she sent throughout the room, I
gave her exactly what she had wanted, a full orgasm in my
mouth. And when we were done the first time, she looked at
me, smiled and said "like Mother, like daughter." That was
just what I needed to hear.
We could have easily made the trip in four days but the
education I received would help me forever.
Chapter 3
Simsonia, Kentucky is a small town not far from the Ohio
River. It's rural, and sparsely populated area made privacy
a valuable tool. It wouldn't take long to understand why.
When we arrived at Aunt Addie's I learned several things
right away. The first was that Aunt Addie wasn't an Aunt in
the family way, but one of Mom's college roommates that
decided farming and privacy were more important than lots
of other things in life. The other thing I learned was that
we weren't the only visitors to Aunt Addie's Farm.
There were two other Mother/Daughter teams there and the
one thing we all had in common was that we were all boys
who loved being girls and that our Moms were totally in
favor of our feminization.
Sarah and Lynn were from Chicago. Annie and Alice were from
Houston. Sarah, Annie, and I all got along wonderfully. We
discovered that we weren't alone in our love for all things
feminine. Over the next few weeks we bonded in ways that we
were sure would last a lifetime. Lynn, Alice, Addie, and
Mom were in second heaven. Lynn and Alice paired off and
Addie with Mom brought back memories from years in the past
when they roomed together in college.
In the mornings we would all gather in the kitchen for
breakfast before doing our daily chores. I had the pleasure
of handling the ponies. This was not a hard task. All I had
to do was twice daily go to the corral and walk the ponies
around this deep well that was in the center of the corral.
I'd take a few sugar cubes and straw, feed them
individually, and then make sure they walked first one
direction, then the opposite. Once a day I would bring
along a brush to pretty their manes, it seemed they looked
forward to that as much as the sugar cubes, and straw.
When I was through with that chore I was free for the day.
The entire summer was spent allowing us to be as female as
we wanted. On the first day we were told that if at any
time we wanted to revert to our male roles, it would be ok
with no one saying a word.
One day when it was really warm, Sarah, Annie and I were
down by the pond just relaxing when Sarah asked, "Did
either of us feel like we wanted to go back to the other
way?" For a moment there was dead silence then I spoke up
and said, "go back to being beat up every day for doing
nothing wrong?" "No way!" Annie said that if that were the
only option she'd just as soon run away or die. Then Sarah
said she had had a dream that she didn't understand, but
wanted to share.
It seems that Sarah had a dream about how the summer
vacation would end and it had to do with a trip to a
strange place. This trip would not take long, and yet,
appeared to involve going deep into some kind of cavern. It
all sounded strange, but she then echoed our sentiments.
She loved her new role and hoped it would never end. She
went on to say that hopefully, one day she could go so far
as to experience the ultimate. Annie and I knew instantly
what she meant. Sarah wanted to have a baby. I have to tell
you up to that point the thought had crossed my mine, but
never seriously. Three girls becoming best friends and not
wanting the summer too ever end, but we knew it would.
Chapter 4
That night at dinner Mom said that Friday we would have
leave but we needed to make a decision about something.
She looked first at me and said "Do you remember what you
said before we left Oregon about how you might want to
spend the rest of your life?" I said "yes, what if I want
to be a girl forever? What would we do then?"
Somehow I knew the answer was soon to arrive.
Addie stood up and announced that if we really wanted to
spend the rest of our lives as girls, experience all the
joys and heartaches of being female, and if we really meant
it, she had a plan to make it happen. Addie stopped behind
each of our chairs and asked if we knew already what we
wanted, or did we want to sleep on it.
Annie stood first and looked first at her Mom then at Addie
and said she had never spent a more wonderful time in her
life. Not once had she wished she could go back to the old
way loved every moment of being a daughter as compared to a
being a son.
Sarah stood next and held her Mom's hand then with a tear
falling she said that her greatest joy would be to give her
Mom a baby granddaughter, and Sarah wanted desperately to
be the Mother.
By then we were all crying tears of happiness and I looked
at Mom and said that this summer had given me a chance to
really understand what my life was truly meant to be. I
therefore could never go back to being a boy and pretending
that I was feminine but that I was a girl and always would
be. We hugged and cried then Addie said, tomorrow we would
take a special trip.
In an instant, Annie and I looked at Sarah, wondering if
she really knew what was going to happen. Sarah just stood
there and blushed.
That night lying in bed next to Mom, I asked her if she
could touch me the way I touched her. She sat up on one
elbow and looked over at me and said "Honey, we'll have
plenty of time for that on our trip back to Oregon." Mom's
smile had a way of saying trust me. I closed my eyes only
wondering what tomorrow would bring.
In the morning we found something strange going on. Instead
of one of my cute outfits to wear, Mom had laid out a pair
of my old jeans, and a tee shirt that I had worn many times
as Daniel. My old tennis shoes with sweat socks that
reminded me of days gone by. Worst of all, there was a pair
of my underwear that I hadn't seen or wanted since leaving
Oregon. Mom said, "Hurry and get dressed." She went on to
say, "please, don't ask questions, we know what we're
doing." I was not amused by what I thought was a mean trick
and when I saw Sarah and Annie dressed the same, and
looking at the expressions on their faces, it was not hard
to tell that we were truly upset.
Addie spoke first. "Boys, and I mean that in the softest
way possible, last night you made a decision that will
affect you for the rest of your natural lives. We need to
be sure this is what you want." Annie looked up and said,
"I'm sure" Sarah and I did the same. Without another word
each of our Moms took us by the hand and led us to one of
the ponies harnessed to the well in the center of the
corral.
The ponies were outfitted with saddles, bridles, and
harnesses to keep them in check. A small pinto, a roan, and
a beautiful pony that would one day be a gorgeous stallion
just waited to for one of these very confused "girls" to
mount them for a short but memorable ride.
I chose the young Stallion, Annie took the Roan, and Sarah
mounted the Pinto. As we were sitting on the ponies they
moved on tethers' about 25' from the well. As the ponies
slowly pranced around the well, the tether brought them
closer to the center. Finally, in an instant as each pony
was right next to the well, each of us was moved magically
from the saddles, down the well, into a deep channel that
seemed to have no end. Each girl was falling freely, there
was no apparent fear, but it seemed we were out of our
bodies, and each moment was met with peace and harmony with
ourselves.
Almost as soon as we had taken flight in the well we were
once again brought back out of the well, placed back on our
pony of choice, riding in the opposite direction that we
started from and very pleasantly surprised to find that we
were indeed what we wished. We had become our Mothers
daughters.
After complete examination, we were shown that indeed we
had been provided with all we needed to prove we were
female. Our growing and budding breasts were ours. Our
vaginas were real, and each of us were shown that we had
every thing needed to be "real women."
There would be proof of my new life, and it wouldn't take
long for it to be brought to fruition. On the way back to
Oregon we stopped for the night in the same motel we had
spent that wonderful time in ecstasy. "Now" Mom said this
is where it all begins. The touch of her fingers on my very
sensitive nipples, and moving slowly to my excited bush,
she said that this was the moment she had hoped for from
the day I was born. We made incredible love that night, but
the next morning is when the full surprise arrived.
Mom woke up before me, packing and showering, preparing for
our trip west, when I woke to find a surprise on the
sheets. "Mom!" I screamed, "look" and there were spots of
blood that I had spilled during the night. Mom smiled and
said just think five days out of every month you'll get to
experience this wonderful happening, and it could never
happen if you had remained Daniel.
"Now," she said, "this is where your real life begins."
That was the most exciting summer of my life. As a matter
of fact, that was the summer my life really began.
This is the first stop of Deanna's incredible journey.
Hopefully, many more will follow.
If you like this story and have comments please forward
them to [email protected]
Trisha
- 05.03.2021
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