Young Stepmother Part 2
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Young Stepmother Part 5 free porn video
Young Stepmother Part 5
By Mark Dayette
I went to head upstairs and put on one of the maid outfits, I didn't want
to, but after the good news my Stepmother had given me about the very
real possibility of me marrying into the super rich Lancaster family, I
felt compliant toward both my Stepmother and her mother. My Stepmother
said, "I will help you bring that box of maid outfits upstairs, and I
will place each maid dress on a hanger in your closet, but there's
something we need to discuss first."
I said, "Okay, what do you want to talk about?" she said. "Nathan, I can
see that you are excited at the news of Mr. Lancaster being interested in
you marrying one of his children, but you have to understand the key
aspect I mentioned to you or else it isn't likely to happen." I asked,
"What key aspect?" she said. "The detail I told you about Mr. Lancaster's
children not being sexually normal, my boss Jonathan has said they are
quite eccentric. If you don't look and act a certain way, the 'right
way', you can't get your foot in the door with them."
I asked her, "Do I have the 'right' look?" she said. "You are getting
there but there's still some work to do. I've heard you are required to
have blonde hair. Furthermore, the way you walk has to be changed,
practice walking in a more feminine way, be dainty, move your hips, and
delicately flip your wrists. Also, speak in a softer, high pitched voice
or if you prefer it a lisping voice. For tips on how to do that watch the
early seasons of Mad Men when Don Draper's daughter Sally was younger,
she had such a terrible lisp, she sounded ridiculous, but completely non-
threatening, you must sound non-threatening. Any display of intimidation
or aggression from you will not be tolerated by the rich and powerful
Lancaster family."
My Stepmother said, "Let me run upstairs and get my hair dye, I have
several colors, I think honey blonde would look good on you." I waited in
front of the downstairs bathroom mirror for her to return with the hair
dye. She came back and showed me the dye box and the color she had
recommended. Then she said, "But after we dye your hair you will have to
grow it out much longer and for a time period of six months or more. If
your hair is longer and more beautiful you can wear it in one of those
gorgeous updos or a nice ponytail. Of course it would look pretty also
brushed down and draped to be placed over one side of your chest. And if
you get your ears pierced you can start wearing stunning earrings. Mr.
Lancaster will probably want new photos of you soon, so you've got to be
in full makeup by then, from now on I want you in full makeup as soon as
you come home from school each evening."
She wet my hair and started dyeing it, and maybe I wasn't the brightest
bulb in the world, but I could see that a definite pattern was taking
shape. Full makeup? Honey blonde hair grown out longer and hanging down
to my chest? Getting my ears pierced? Wearing earrings? Walking in a more
feminine way? Speaking in a high pitched voice? Lisping? Transforming
into full makeup right when I arrive home from school each evening? I had
to ask my Stepmother to help me understand this because the startling
truth of what I was being transformed into was quite clear, but I wanted
to hear directly from her why the scale of the transformation was
reaching this extreme degree.
I asked her, "Be honest with me, with all of these changes, does Mr.
Lancaster's daughter want me to look like a girl before she will marry
me? Does she have lesbian tendencies or what?"
My Stepmother laughed and said, "Well Nathan, they did grow up with a
father who is worth $800 million, I'm sure that from an early age they've
lived a life of excess involving alcohol, drugs, sex, you name it. If you
are curious, Mr. Lancaster has 3 sons and 2 daughters. One of them is
straight, one of them is gay, one is a furry, the other is a
necrophiliac, and another is a pyrophiliac."
I asked her, "What the hell? What is a pyrophiliac?"
She explained, "Nathan, those are people who are sexually attracted to
fire."
I asked with surprise, "How is fire a sexuality?" She laughed and said,
"Nathan, I warned you that Mr. Lancaster's children are sexually
abnormal."
I went to school that week and didn't worry about the students in the
restroom seeing my lingerie when I went to urinate, I convinced myself
that I would get the last laugh by marrying into a rich family while they
would have difficulty finding a job in the current poor job market. At
night when I came home, my Stepmother would help me get into full makeup:
lipstick, eye shadow, blush. During the week I got my ears pierced which
I didn't think was a big deal because cool male rock stars have pierced
ears and they aren't girls. My Stepmother placed a pair of dangling
earrings on me for the first time.
My hair was growing out and it was the honey blonde shade that my
Stepmother had dyed it. She complimented my beauty and told me I looked
like the pop singer Taylor Swift. I didn't like Taylor Swift or her
music, but I guess this was a step in the right direction if I was going
to marry the perverted and borderline lesbian Lancaster daughter. My
Stepmother put a red bow in my hair. Also, she informed me that week that
she had bought me a new shoe collection which was entirely women's shoes.
It consisted of numerous pairs of high heels in the colors of black,
white, blue, red, pink, and nude, and a style she called 'Mary Janes' but
I had no idea what that was.
I must admit that even though these changes were supposed to lead me to
wealth, I had a sensation of pain in my chest and butterflies in my
stomach from the doubt over whether marrying into a wealthy family was
worth the price of looking and dressing like a girl.
Friday night my Stepmother polished my fingernails red, she said I could
use nail polish remover on Sunday night if I didn't want the students to
see me like that at school. she said she was impressed I was learning how
to apply my own makeup and lipstick. Late Friday night she told me that
she expected me to begin Saturday morning looking feminine from head to
toe, she said several guests were coming to our home that day, and I was
given the task of wearing a maid outfit and waiting on them.
I didn't like the idea, it had all become too extreme. I didn't want
anyone else to see me dressed in women's clothes. While it was true that
the whole crossdressing burden had begun with the event of my Stepmother
finding her lingerie under my bed, it had escalated with the building up
of the prospects of marrying the rich, weird Lancaster daughter. I
figured it was my fault for not drawing the line earlier, perhaps if I
had beaten up Pete on the day we had our big argument, and if I had
forced him to come over to my house and admit to my Stepmother that he
had planted her clothes under my bed, none of this would be happening
right now.
However, in the next thought I realized that if my Stepmother hadn't
believed I was a crossdresser how else would I have gained this once in a
lifetime opportunity of marrying into a super rich family and living in
luxury? On the other hand, at night in my bedroom I would often spend
nearly an hour staring at my own reflection in shock at how feminine I
looked. I could no longer recognize myself.
I knew that as my blonde hair grew out I would not even be spared the
shame of appearing as feminine in public. I asked myself what my college
classmates would say if they knew how I looked and dressed at home? Oh
God, they would laugh their asses off. I asked myself if a normal guy
would put on makeup and lipstick, and wear women's clothes to marry a
seemingly lesbian leaning rich girl because she wanted a husband who wore
women's clothes? She isn't attracted to men in men's clothes so she is
kind of fucked up. Why doesn't she just marry a real woman? I knew I
could always back out on the deal and continue to follow the normal but
less financially rewarding inheritance plan of 'progress toward success',
I mean I didn't have to have a marriage with someone THAT extremely
wealthy. Philadelphia was filled with normal rich people who perhaps
weren't worth $800 million, but if I married one of them they wouldn't
make me look like a girl.
I got up early on Saturday morning and signed on to the internet, I went
to Friendbook and although I hadn't planned it, I looked at old pictures
of myself, pictures of when Mom and Dad were still alive, back in the
time when I dressed only as a boy. Oh well, that past was gone, my life
would never been the same as it was then, but hope remained, I speculated
that being very wealthy might greatly reduce the shame I felt from
wearing women's clothes. In spite of everything though I had already gone
this far, surely it couldn't get much worse? It had to be soon that I
would meet this weird Lancaster daughter and things would turn out
alright.
I got ready to put on a maid outfit, my Stepmother had told me guests
were coming to the house and I had to wear a maid outfit and wait on
them, it was a dreadful new step. I selected a dark blue maid outfit, it
had a white apron and a giant red bow at the collar. I put on the white
gloves that came in the maid box package, I didn't know what purpose
these served, they reminded me of opera gloves I had seen on television
during the Academy Awards, but as they were in the gift box sent by my
Stepmother's mother, I knew I would get yelled at if I didn't wear them.
I put on a pair of the black Mary Jane shoes and I wore white knee high
stockings which had a lace ruffle and white bow at the top toward the
thigh. Underneath the maid outfit I wore a red silk mini slip. I went
downstairs and my Stepmother helped me fix my makeup, and red lipstick,
blue eye shadow, blush, and she put my blonde hair into a ponytail with
blunt bangs. She then placed a pink bow into the right side of my hair. I
won't lie, I knew how completely feminine I looked from head to toe, I
tried to not think about it, but I was definitely aware of it, I couldn't
move a step without feeling the feminine clothes that were forming the
basis of my strange new life.
My Stepmother said she could hear the guest's car pulling into the
driveway, she told me to show good manners by giving the appropriate
curtsey when I opened the door. The doorbell rang and I approached it, I
opened the door and I said, "Welcome to the residence of Molly and
Nathan." I curtsied. Much to my dismay, standing there right in front of
my eyes was my ex-friend Pete. Immediately aware of how extremely
feminine I looked in front of him, it was for a few seconds that I
thought I might faint. At first my worries were unfounded as it seemed I
looked so feminine that he didn't even recognize me. However, when I
invited him to walk into our living room and sit down he detected my
voice and knew I was his old but ex-best friend Nate. My Stepmother had
gone into the kitchen to apparently leave us alone. We both sat down.
Pete said, "Jesus Christ, you have changed, when you told me your
Stepmother caught you crossdressing I never imagined you were addicted to
it this bad. You look one hundred percent like a girl. Dude, you look
more girly than most of the women I know. Think about that!"
My face had turned red with embarrassment as I knew in my heart that his
perspective that I had totally surrendered to crossdressing was true but
he was confused if he thought it began as my decision, it was not my
decision, it was his prank that caused it all. I became angry at him and
I asked, "Did you come here today just to mock me? What do you want?"
Pete said, "Stay calm Missy, I only came here because your Stepmother
called me on the phone last week and told me you wanted to apologize for
accusing me of playing a trick on you to make you look like a
crossdresser. she said you wanted to tell the truth and confess to me
directly that you had been sleeping in that pink slip every night and you
would wake up the next morning and hide it under your bed hoping to never
get exposed for the fundamental crossdressing nature that you have."
I became extremely frustrated and lost my temper, I yelled, "I never
asked you to come here, my Stepmoth...or should I say that BITCH Molly
was lying, I will never apologize to you because I still believe you are
a guilty piece of SHIT."
Pete heard my rant and became so furious he leaped up from his seat on
the sofa in our living room and he rushed over to where I was sitting and
before I could react or defend myself he picked me up like a sack of
potatoes and threw me face down on the sofa. He pressed his body and left
arm against my back to hold me down and with his right hand I could feel
him lifting up my maid dress. He pulled my maid dress up to the middle of
my back and then he lifted up my red mini slip. He began to spank my bare
bottom extremely hard with his hand. The spanking hurt and I was scared
so I shouted, "STEPMOTHER!! HELP ME!!!" But she didn't come into the
room, she didn't help me. Pete spanked me over and over again and my bare
butt was completely burning like fire.
Between my whimpers and whines I pleaded with him, "Pete! Please stop
hurting me!"
He said, "If you want me to stop spanking you, you better start talking,
admit the truth."
I said, "Ouch, ouch, ouch, what truth?"
He said, "Admit the truth of the crossdressing sissy faggot you are and
what you wrongly accused me of. Say it! You say what a silly, lying
faggot you are or this spanking will continue indefinitely, it is your
choice, my spankin' hand is just gettin' warmed up."
It was the most embarrassing moment of my life, my former best friend had
overpowered me and was spanking me, and in order to get him to stop
spanking me I had to fully surrender to the victory of his ego.
In the middle of my whimpering I completely swallowed my pride and said,
"I'm a crossdressing sissy faggot and I tried to blame my friend to
deflect away from the truth of my crossdressing ways. I lied and said he
tried to make me look like a crossdresser but....I am a crossdresser."
Finally he stopped spanking me, but he still had his body and left arm
holding me down. Unfortunately the end of the spanking didn't stop his
insults, in a sarcastic tone he said, "There, doesn't that feel better
telling the truth? Everyone knows it is the year 2015, and if someone
can't be an open crossdressing faggot in 2015 then what kind of nation do
we have? And you might be a spoiled, rich, little faggot, and I've heard
rumors that you could even become richer, but that doesn't remove the
shame you are always going to feel over the victory I just had over you."
Pete continued his verbal abuse, he said, "And come to think of it, I'd
like to add to my victory, now you sit up and sit in the middle of the
sofa on your knees in your maid outfit. Look at those white knee high
stockings with the white bows at the top, what a fucking sissy you are.
My Dad would kill me if he found me dressed the way you are."
The humiliation of my defeat was really setting in, I noticed I was
slightly crying, and my makeup was starting to run. And worst of all,
Pete took out his cell phone and motioned for me to pose for photos on
the sofa. He said, "I think the Liberty Bell High class of 2008 needs to
see how Nate ended up. They are going to see quite a lot of photos of
your performance here today. Now pose for my camera you bratty sissy! And
keep in mind that if you don't do what I say, I start spanking again."
I didn't know what else to do, so while sitting on my knees on the sofa I
arched my back and did the puckering kissyface or 'duckface' look with my
red lipsticked lips. My former best friend was forcing me to act like the
model Candice Swanepoel and the actress Vanessa Hudgens. Pete was
enjoying the hell out of this, as he was snapping photos he ordered me to
make ditzy and bimbo facial expressions and God help me but I did it.
When I obeyed his command he said, "You are nothing but a brainless sissy
doll. You aren't a Nate dude, you are a Natalie."
Then he told me to take off the maid dress and I hurried to appease his
demands. I was down to posing in just my red mini slip and my white knee
high stockings with the lace ruffle and white bow at the top toward the
thigh. That my oldest former friend was making me undress items of
clothing to pose for additional pics struck me as highly bizarre, I
honestly wondered if he was getting a erection from forcing me to strip
down to my lingerie in front of him.
At that moment my Stepmother walked into the room and I could see by the
look in her eyes that she knew immediately who had won the battle between
Pete and myself. My Stepmother saw him taking photos of my feminine model
poses and in a smug tone she said, "Isn't this precious? His oldest
friend is helping him fulfill his modeling dreams."
I started to worry about his threat to send these pics to the entire 2008
graduating class from my high school Liberty Bell High. If he did that it
would be embarrassing as hell, but on the other hand it wouldn't be the
end of the world for me because he saw more of them socially in the
present than I did, since Dad died I had become more of a loner. There
was another small voice in my head telling me that it was an act of major
denial on my part to seek to minimize the reputation disaster of my 2008
graduating high school class finding out I wore women's clothes.
I could tell my Stepmother was angry at me about something for her to
treat Pete's abusive behavior toward me so lightly. She didn't even step
in to stop his forced photo session when he ordered me to turn around so
that my ass faced his camera, and I had to lift up my red slip and reveal
to him my bare ass so that he could capture some photos of my well
spanked beet red ass. When that happened my tremendous shame reached a
maximum height.
I suddenly contemplated that this was a humiliating turning point in my
relationship with my Stepmother. For her to see me submitting so easily
to the dominance of another man, it was going to suggest to her that I
was nothing but a feminized and powerless wimp. She also didn't protect
me or correct Pete when he repeated that dreadful feminizing name change
of calling me 'Natalie' instead of 'Nathan' or 'Nate'. As he was snapping
the pics I could hear the laughter in his voice as he said, "Silly sissy
Natalie loves prancing around in her dresses and lingerie. Silly sissy
Natalie dreams of everyone in the greater Philadelphia area finding out
what a pathetic faggot she is."
Finally, my Stepmother began trying to calm Pete down, she said to him,
"Pete, I think you've taught Nathan a valuable lesson here today not to
tell lies and the need to own up to his actions even when those actions
are embarrassing like wearing his Stepmother's lingerie. I also think
that the lesson Nathan learned today will be more powerful if you would
once again be a friend to my Stepson. And I would like to warn Nathan
that if does not treat you with one hundred respect from this day forward
he will face severe consequences directly from me. Now Nathan, you can
start showing your respect to Pete by giving him a farewell curtsey as
I'm sure Pete has other things to do today." I managed to force myself to
curtsey to him after I put my maid dress back on.
Pete had a euphoric look on his face and he said, "I will gladly be
friends with your Stepson again."
Not only had he spanked and humiliated me, and forced me to pose for
hundreds of feminized photos that he was going to send to my entire high
school graduating class, but now he was agreeing to her awful idea that
we become friends again. I could see right through his motives, he wanted
the satisfaction of me having to see him on a regular basis so that each
time we saw each other I would be reminded of his total domination over
me which had taken place today. And he also knew I wouldn't be able to
tell him to FUCK OFF because if I did that he could run to my Stepmother
and tell her that I wasn't treating him with 'one hundred percent'
respect.
To Be Continued....
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