Halloween Trilogy of Transformation
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Halloween For Life free porn video
Jordan and Anna packed up their belongings, they left their small
apartment in Bangor Maine and moved to Phoenix Arizona in the beginning
of October.
The couple were high school sweethearts, having their first date at a
sophomore dance and Since then they were inseparable. Even through
college they stayed close with phone calls and visiting each other as
much as possible. Once they both had their degrees,Jordan in
manufacturing and Anna in accounting, the two were married. They were
going on their 2 year wedding anniversary, and still nothing had
changed. They were still inseparable.
So when the chance came for Jordan to be a manufacturing engineer in a
needle processing plant on the other side of the country, they both
jumped at the offer of making double what he was making now.
Even though they both had very successful jobs at 24 years of age, made
good money and most importantly they enjoyed what they did. This was an
offer that they couldn't pass up.
Anna had lined up a weeks worth of job interviews. And although it had
taken a couple of weeks, they had finally unpacked and were settliing in
their new apartment.
The good part was that Jodan was already lined up for his position and
didn't even need to interview. His longtime friend Jason had been a
recruiter for the company. He waited for the position to be open and
once it was he threw Jordan's name in there. Jordan submitted his resume
to the company, and it made it's way to the president of operations and
he was very impressed. He hired Jordan without an interview just because
of their trust in Jason.
His start date was still a week away, in fact he was to start on
Halloween, October 31st.
Jordan was just out of the shower, he was still drying his long black
hair as he walked into the bedroom where Anna was just finishing up at
her makeup mirror.
Her first interview was today with large bank. It was an hour ride from
their apartment but Anna didn't want to turn down any interview because
even though Jordan was set, she still needed a job.
Jordan had really lucked out with the apartment tower that they lived
in. The needle company had helped them with their apartment hunting and
offered a half a year rent free. The job was only a 5 minute commute for
Jordan. He would be able to walk there because he knew Anna would need
the car for her job.
Jordan sat on the edge of the bed and stared at Anna.
Anna saw him looking as she glanced at him through the vanity.
"Wow! You look beautiful,"he commented.
Jordan felt like the luckiest guy in the world. He had a great job lined
up, a beautiful wife who traveled across the country for him and she was
his best friend.
Anna was a beautiful woman. She had blonde hair cut shoulder length in a
professional style, she had a sexy body. She had a great playful
personality on top of her beauty.
Jordan also had a playful personality. Although Anna was still more
outgoing than he was.
Jordan was a confident man, he was very successful and was a great
supervisor in his previous position. He just wasn't a very tall man. He
was thin as a rail and had long straight black Italian hair. This made
him a little self conscious at times.
Anna liked to push his buttons being an inch taller than him and make
short jokes at his expense.
She did love him dearly it was just her playful manner.
"Thank you babe," she replied finishing up applying her lipstick and
putting the tube into her purse.
She stood up and straightened out her buisness suit. "I better get a
move on if I don't want to get held up in traffic."
But as she walked passed Jordan to walk out of the room, Jordan grabbed
her around the waist and both feel back onto the bed.
"Ahhhh" Anna scremed, "Don't mess me up!" She was being serious but had
a smile on her face. She loved when Jordan was turned on and she loved
situations like this where he would have to wait for sex.
"Comon, I've got nothing to do all day," Jordan said as he held her
tightly.
Anna stopped struggling and looked at Jordan in the eyes. She played
with his hair that was a wet mess all over the bed.
"Well, you could go and get a haircut." Anna smiled because she knew
this was a sore subject.
Jordan rolled his eyes. He had grown his hair long and had it this way
since he was 21. He knew with the job coming at the end of the week he
would need to get it cut short but he was trying to prolong it for as
long as he could.
Jordan turned down his lower lip and made a sad face.
"I know it means a lot to you babe, but you've got to think
professional," Anna reminded Jordan. This was probably the fifth time
they've had this conversation already but Jordan didn't care, he liked
his hair long.
Jordan sighed as he sat up on the bed. "I just want these new guys to
like me. I mean, I've been in charge of people at the other job, but
that was 3 guys. Jason said that I'll be in charge of the whole
department which is about 12 guys." Jordan explained nervously.
"I know honey, but first and foremost you've got to make a good first
impression. Once you look the part, they'll soon see why your position
won all those quality awards and why the other guys liked working for
you so much. You are friendly and fun and know how to get the job done.
We've come a long way for this position. You've got a chance to go into
a new place and just impress the pants off these people. Show them your
Professionalism, show them your friendliness, show them your humor and
most of all show them that you're one of them. They'll soon forget that
you're their manager and think of you as their friend just like the
other job."
Jordan smiled.
"That speech just totally turned me on," Jordan said as he grabbed
Anna's side and started to rub up against her.
"Ahhhh babe, you're still wet," she screamed as she scooted off the side
of the bed. "I have to go. Get the haircut today." Anna said as she
grabbed her purse and zippered it. She put on her sunglasses and grabbed
her keys.
She made sure she didn't come close to the bed again so Jordan wouldn't
grab her again and she blew him a kiss.
"Love you!" she yelled as she headed towards the door.
"Love you too, good luck!" he yelled as she closed the door.
As it turns out Jordan and Anna would have this conversation a few more
times this week as Anna continued to get up and go on interviews. Jordan
still hesitated cutting his hair. He would still do things during the
day as his job didn't start until Friday.
It was Wednesday afternoon and Jordan was sitting playing Playstation.
He recently spoke to Anna who called and said she was coming from an
interview and was bringing home chesseburgers.
Twenty minutes later Anna walked through the door with a smile only to
lose the smile a second after seeing Jordan.
"You still didn't cut your hair? Babe, it's tomorrow or nothing. You
have to go in Friday with it cut. They'll take one look at you and
wonder what Jason was thinking hiring you," Anna explained.
"I know, I know" Jordan said as he put the playstation controller down
and started going through he fast food bags. He started to set the paper
plates on the table while Anna put straws into their fountain drinks.
"Oh my God! I have to tell you about this interview today," Anna said as
she took her shoes off and headed into the bedroom to get changed.
"You didn't call the interviewer mommy, did you?" Jordan asked.
"HA! You're funny! No but listen to this," Anna continued to talk while
she was changing from the bedroom.
"Remember back when Saturday Night Live had all your favorites on it. In
the 90's. Chris Farley, Adam Sandler, Chris Rock, that whole crew?"
"Yeah, I loved those characters growing up," Jordan replied.
Anna came out of the bedroom in a long pink tee shirt and just panties
and sat at the dinner table where Jordan was already at.
"Well remember the character "IT'S PAT!" she asked.
"yeah, the character by Julia Sweeney. The joke was that no one knew if
Pat was a man or a woman," Jordan reminded Anna.
Her eyes widened and she grabbed Jordan's arm. "I met Pat today."
"Julia Sweeney?" Jordan asked.
"No, no, my interviewer was the Pat character. I couldn't tell if it was
a man or a woman," she said as she started laughing.
"The best part was, is that the interviewer's name was Pat!"
"No way!" Jordan replied.
"I shit you not. But Jordan, you had to be there. This..this person had
what looked like a woman's buisness suit, but no breasts, had no makeup
on, and talked sort of nasally. Longish hair but in a short pony tail,
and had a few hairs on the upper lip. It was insane, and that's all I
focused on. I couldn't tell you a thing the person asked or what I
replied," Anna continued.
Chris started laughing. "Oh man, imagine if you got the job?"
They both laughed, "I wouldn't be able to do my work, my job would be to
find out the sex of my boss."
They continued laughing.
"And your boss would open a file on your computer and all that would be
on it would be your investigation about Pat's true sex," Jordan
continued.
They both had a good laugh and finished their meals and then watched a
little tv.
They stayed up a little later and fooled around. Jordan had waited a few
nights for this, as Anna had gone to bed early all week because of her
job interviews. On Thursday, Anna had no interview set up because they
were going to spend the day together before Jordan started his job. They
still had to pick up Jordan's suit from the cleaners, and now most
importantly get a haircut for him. Then a nice lunch and then call it an
early night so that Jordan could get a good nights sleep.
Anna was laying in bed and started to think about Jordan's haircut
tomorrow. It was going to be weird seeing him with short hair again, but
she knew it was long overdue. He would look really good with his suit
and short haircut going into this new job.
Again Anna thought about her interview earlier that day, and started
laughing again about "PAT" Then her mind switched from Pat to Halloween.
She thought the "PAt" costume would make a great costume.
"Ya know, this will be the first year that we don't dress up for
Halloween," Anna said to Jordan out loud.
Jordan was fading in and out of consciousness and just mumbled, "Uh
huh."
She lay there thinking about it and thought that maybe on Friday night
they should hit a bar in costumes. She brought up the idea to Jordan,
but again he was half asleep so he answered slowly and just mumbled his
answer again.
"Can we go look at costumes tomorrow after we pick up your suit?" she
asked.
This time Jordan didn't answer. She figured he had drifted to sleep.
About a minute later Jordan said, "We should see if there's a PAT
costume."
This made Anna laugh out loud as she hit his backside.
"Oh my God wouldn't that be funny if you went to your job in a costume?"
Anna said.
Jordan turned over and faced her "You want me to dress as Pat?"
"No, not as Pat, although that would be really funny. But just something
that they wouldn't be expecting. It is Halloween, I bet they have a big
company party where everyone brings in a dish and wears a costume and
then they judge best costume. With a company this size, they must do
something," Anna explained.
Jordan started to get nervous. "Oh yeah, what if they do, and then I go
without a costume and immediately I'm labeled as a lame boss," Jordan
replied.
"We can fix that, we've come up with some good costumes through the
years. So you want to do this? We can get you a good costume and shock
the hell out of them and then have a good laugh about it," Anna replied.
"I'm in, yeah, it is Halloween, but what could be my costume?" Jordan
replied.
"Remember now, you were hired without an interview. You were hired just
on paper, no one has seen a picture or anything. In fact a resume only
has your professional information on it, no personal things. So the
company has no idea what you look like. The possibilities are endless,"
She explained while laughing.
Jordan started laughing too.
"That's true, I could go in with a whole face load of fake piercings. On
my eyebrows, nose, mouth and dye my hair another color. This might be
fun. Lets do this tomorrow," Jordan replied.
Anna was excited. "I'm glad we're doing this. Can I pick a costume out
and then maybe after work we could hit up a bar in our costumes."
"Sounds good. I'm in," Jordan replied.
The two kissed goodnight and then cuddled up together.
"Babe," a voice spoke. Jordan was startled but then realized it was
Anna's voice. Was it in my dream or did she say that awake.
Jordan rubbed his eyes and focused his eyesight.
Sure enough there was Anna kneeling next to him on her side of the bed
with her eyes bright and wide awake.
"What time is it?" Jordan asked while yawning and also pulling his hair
out of his face.
"Six," Anna replied.
"Six? Aww honey, why did you get me up so early. You know it's my last
day to sleep in," he said still tired and whining.
"I have an Halloween costume idea that's just going to blow away every
other idea," Anna said excited.
Jordan had already turned over and was trying to fall back asleep, but
Anna was going to make sure that didn't happen.
"Don't you want to hear my costume idea?" She again interfered with
Jordan's sleep.
"Tell me at eigh,t" Jordan replied from his corner of the bed.
"Babe, comon it's such a good idea and it's going to take all day to
plan," Anna continued while shaking Jordan's side and the bed along with
him.
"My plan also involves you not getting a haircut today," she added the
last comment to sweaten the pot and it was working as Jordan turned back
over facing Anna.
"Yeah?" he asked unsure.
Anna had a huge smile on her face and Jordan could tell she was super
excited about her idea, but she also had a hesitation like face.
"Weeelllll," Anna started to drag out her explaination.
"What if you went to work not as Mr. Jordan Ross," she started and then
dragged out the second part of the sentence as Jordan waited for the
continuation of the sentence.
"..but as Miss Jordan Ross," finally getting it out.
Jordan had a blank look on his face.
"So a woman, you want me to dress up as a woman?" he asked.
Anna never lost her smile as she was trying her hardest to sell this
idea.
"You wouldn't have to have your haircut for 3 days if you dressed up as
a woman. You figure, you go to work in the costume with your hair
styled in a woman's style. Then once the joke is over, you go the
weekend and then we'll get a haircut Sunday night," Anna tried to really
push the hair situation. She knew it was important to Jordan so she
figured she would try that angle first.
"Babe, I can't be in a supervisor position in charge of other people and
on my start date show up dressed in drag. I would never get back any
respect from my workers. I'd be the butt of the joke and I don't want to
start a new job like that," Jordan explained.
He saw Anna's expression go from happy to blank.
"but it's not like you'd be doing it on just a regular Tuesday. That
would be weird. It's Halloween. I think you're going to be the one
standing out like a sore thumb not taking a risk and not pushing the
limits with a daring, exciting costume like that. Everyone is probably
expecting another stuffy boss. One who doesn't get involved in their
employees personal lives. If you did this, I think they would have a lot
of respect for you. What guy shows up on his first day dressed as the
opposite sex. To me that's someone who has a lot of balls and isn't
afraid to show everyone," Anna really wanted Jordan to do this. It was
going to be awesome if he agreed to this.
She could tell her speech was working as Jordan looked like he was in
deep thought about it. He didn't say anything he just looked at her
again.
"Aww, I'm really not sure about this Anna," he replied.
"Just think about the day we would have today, we wouldn't have to go
pick up your suit, we wouldn't have to go cut your hair, and we wouldn't
have to go to the costume shop." Anna was still trying to sell this
idea.
Jordan made a confused face. "Why wouldn't we go to the costume shop,
what would I wear?" he asked.
"Well we are about the same size, you could get away with fitting into
one of my dresses, skirts or business suits," Anna replied.
"Dress in your clothes? This is getting too weird," Jordan replied.
Anna again bounced on the bed. "No, babe, there's nothing weird about
it. Consider it a costume. If we did go to the Halloween costume shop
and bought a belly dancer outfit, that would still be a dress. So what's
the difference if the dress is a costume dress or a dress out of my
closet," Anna explained.
Jordan still thought it was weird and tried to talk Anna out of it.
"What about I go as a heavy metal guy. Long hair, I could rip up a pair
of jeans, maybe wear a leather vest," Jordan continued.
"Pleeease do this for me, babe." Anna was the one whinning now. She
loved this idea and thought it would be a lot of fun seeing her husband
dressed up as a woman.
Jordan's face was a man's face, but he still had sort of soft features.
He had long lashes, big beautiful blue eyes and of course his thin
frame.
Jordan hesitated again, but then looked at her and smiled.
Anna bounced again on the bed and then hugged Jordan tightly.
"Oh my God! This is great! We have some things to do today so jump in
the shower and then lets get going," Anna jumped out of their embrace
and off the bed.
She pulled Jordan by the hands into the bathroom which was in their
bedroom.
Anna started Jordan's shower and then looked throught he cabinets in the
bathroom as Jordan removed his clothes.
"Here, use this on your body, don't let it get on your head," Anna said,
handing Jordan a bottle.
Jordan read what the bottle was. "Hair removal? Why am I removing my
hair? Babe, this is only for one day, you know that right?" Jordan said.
"I know, I know. But if we're going to make a costume, I think we need
to go in full throttle," she replied.
Jordan just stared at the bottle, and got into the shower with it.
Jordan kept the hair removal bottle at the side for the moment and
decided to wash his hair first and then do the hair removal.
Taking a shower for him was long already with his long hair but it went
even longer as he was finished with his usual showering routine and now
he was reading the directions on the bottle of hair removal.
He applied it over the parts where his hair was thick. His chest, arms,
even though that was probably the lightest spots of hair, he thought.
Lastly he covered his legs with it.
He waited the allotted time and then washed the cream off of him.
Jordan watched as the cream left his body along with his body hair.
"Oh man, this is fucked up Anna," Jordan yelled out of the bathroom.
He got no reply.
Minutes later when he was sure everything was off of him, Jordan shut
the water off and grabbed his towel. As he dried himself off he looked
at his body and saw that he was totally hairless except for the hair on
his head that reached midway down his back.
Anna appeared in the doorway and pulled Jordan into the bedroom again.
"Oh My God, your body looks amazing without any hair, this is going to
be so much fun," Anna said as they entered the bedroom and Jordan saw
that Anna had laid out clothes for Jordan to wear.
"What's all this about?" He asked confused. "I don't start until
tommorrow, I'm not dressing up today, right?" he asked.
Anna made a guilty face like she had something else to tell him.
"Right Anna?" he again asked.
"Well, not exactly," Sse said softly.
Jordan looked at her. "What are we doing today Anna?" He asked getting
angry.
Anna hesitated again, but then finally just came out and told him.
"We're just throwing on jeans and a t shirt, putting your hair in a
ponytail and I uh..made us appointments at the hair salon," she said.
Jordan's eyes widened. "You've got to be kidding me?" He was pissed.
"Anna, this is only going to be one time, one day. Halloween. I'm going
to wear the costume to work, and then probably bring my male clothes
with me to change at lunch time. I'm not getting all dolled up for one
day," Jordan sat on the end of the bed and pushed the women's jeans off
the side.
Anna approached him causiously.
"Babe, I figured if we were doing this, we would go all out. I promise
nothing too extreme. You'll just get a hair wash, style and makeup. I
can't do that here, and it would just look like a mess if I did it,"
Anna explained.
"But to go out in public as a guy and explain that I wanted a woman's
style with my hair, that's just embarrassing," Jordan replied.
"But that's what my clothes were on the bed for. I wanted to put you in
something casual and stuff my bra to give you the illusion of breasts,
make your face up a little and have your hair in a ponytail, no one
would think you were a guy," Anna explained.
Jordan sighed.
"This just feels like it's getting too involved. I was thinking of just
wearing a dress, smear a little makeup on my face and I would be one of
those drag queens," Jordan explained.
"But I thought this was about Halloween, and Halloween costumes are a
surprise. You're supposed to make your costume believable and then shock
everyone when they realize who's under the costume," said Anna.
"well, I just don't want to be embarrassed. Remember, I have to work
with these people for a long time," Jordan explained.
"I promise, it's going to be good. Would you please just trust me. I
wouldn't do anything to hurt you in any way," pleaded Anna.
Anna moved up to Jordan and kissed his bare chest. She looked up at his
face.
"You're killing me," Jordan replied, as he pulled Anna onto the bed and
the two of them passionately kissed and then they made love.
About 45 minutes later, the two had started over. Again Jordan did some
hesitation and again Anna talked Jordan into putting on her clothes.
She put the Victoria's Secret bra and panties onto his body. She grabbed
two of his socks and stuffed them into each cup. SHe squeezed the socks
to make a rounded but firm shape.
Jordan kept rolling his eyes after each piece of clothing was put on
him.
Jordan couldn't believe he was actually doing this and was going to
dress as a woman and go to a salon. Let alone go to work the next day
dressed the same way. He knew it was going to be funny, that he agreed
with Anna. It's just the embarrassment of not knowing anyone at the new
job when he took off the dress that was going to be hard.
Once Jordan was dressed, Anna pulled him over to her makeup mirror.
"Now sit babe, I'm just going to put on some light eye makeup and a
little gloss on your lips. Once we're at the salon we'll let them do a
full makeup and then we'll just follow their lead before you go to work
and copy what they did," Anna explained as she started to coat Jordan's
eyes with mascara.
This felt weird for Jordan who had never had any makeup on his face.
He watched Anna as she had him turned away from the mirror so he
couldn't see himself. She put down the eye makeup and picked up a tube
of lipstick.
She uncapped it and soon he felt his lips being coated with a pink
shade.
Anna grabbed a hair scrunchie from the top of the makeup table and
pulled Jordan's hair back. She then wrapped the scrunchie around the
hair and pulled it up to make a high Ponytail. She fiddled around with
it a little and then back away from him smiling.
"You look amazing!" Anna said as she pointed at the mirror.
Jordan was finally able to turn and face the mirror.
He looked at his reflection and opened his mouth in shock.
He couldn't believe how he looked. Everything was really casual, the
clothes, the makeup, the hair, but still, he looked like an attractive
woman.
"Pretty good, right?" Anna said as she made Jordan smile.
"Ok, it's good. I'll give you that, but if I can look this good without
a trip to the salon, then why bother going. Can't I just make this my
costume?" Jordan asked.
Anna smiled. "FIrst off, no respectable woman is going to start her
first day at a new job with her hair in a ponytail. She's got to have it
done up and make it look good. That's what we're going to do," Anna
explained.
"You just can't take no for an answer, can you?" Jordan smiled.
"Comon, lets get going I don't want to be late," Anna said as she
grabbed her purse. She then raced to the closet and searched the top
area. When she came out of the closet she was holding a small clutch
purse. She handed it to Jordan.
"I hate this!" was all Jordan said as Anna rushed them to the door.
The drive to the salon was a 20 minute ride. ALong the way Anna scared
Jordan with talk of disguising his voice to sound female.
"Soft and whispery" Is how Anna put it.
So all the way to the salon, Anna had Jordan practice. This made Jordan
even more worried about someone realizing that he was a man.
Jordan was relived once they arrived at the salon. That is until they
actually entered the salon.
As the two walked in it felt to Jordan like all eyes were on them
He whispered to Anna, "Do you think they know?"
"We're fine, don't freak out," she whispered back.
The two approached the front desk receptionist. The young girl looked up
an smiled. "Can I help you?" she asked.
Anna spoke up. "Hi, we have an appointment for two under Ross."
The receptionist looked in the appointment book and read what was
written there. "Ok, we have the blonde with just a wash and style and
nails and the brunette will have the full treatment, right?" She asked.
"Right!" Anna replied.
Jordan stepped into the conversation and using his practiced female
voice asked, "Full treatment?"
"Yes," the receptionist replied. "You get a wash, style, nails, facial,
makeup, the works."
Jordan slowly turned and faced Anna. He widened his eyes and if he could
make fire shoot from them he would.
But his death look was short lived as one of the salon women walked
over. "Hi, uhh Jordan? You're with me."
Jordan felt helpless and couldn't do anything but follow the salon
specialist into unknown territory. As he did he looked back with a
worried look to Anna.
Anna smiled and waved goodbye.
Cheryl
- 10.12.2022
- 20
- 0
