As Girly As It Gets - The Dress Code - Part 7

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Sunday morning, Moira dropped by to check on Terry. Terry answered the door barefoot, wearing his new jeans and a sweatshirt.  Surprisingly, he had lipstick on and his hair looked pretty good.  He had it in a ponytail and the full curls gave it a good look.  Terry was surprised, “Moira, what are you doing here?” Moira pushed into his apartment as she began, “Last night I realized, we need to get you some shoes that meet the dress code.  I thought we could pop into one of the shoe stores and get something early in the afternoon before the crowds hit the stores.” Terry was taken aback, “I don’t want to go out anywhere.

Besides, I have shoes.” “Terry, I thought it was pretty clear yesterday that your shoes probably don’t meet the dress code.  I think we should see what is out there and make sure we have a backup plan.  Why don’t you wash your face and shave if you need to?  Then we’ll get some clothes and go shopping.” “Moira, I’m not a child, I can dress myself.” Moira nodded.  “OK, I’ll wait here.  You get ready and we’ll see.” A little later, Terry returned wearing his new jeans, a sweatshirt, gym socks, and running shoes.  Terry bowed to Moira. Moira shook her head. Terry was stunned, “What?  What could possibly be wrong?” Moira said, “We are going to shop for shoes for you to wear to work.

Therefore, you need to wear a hose.  Trouser socks will be fine.  Gym socks will not.  Try putting on a nice pair of leather shoes.  And, that sweatshirt is designed for you to hide.  Grab one of the new shirts and roll up the sleeves to your elbows.  You’ll look like an executive out for an afternoon.  We’ll loosen your hair because, why have it if you don’t show it off.” Soon Terry was standing there in an oxford blouse with sleeves rolled up.  His hair was down and the curls gave it life.

Moira ran a brush through his hair and helped fluff it up a bit.  Moira told him he looked like some adventurer from the wilds of South America.  He had his trouser socks on and a pair of casual leather walking shoes. Terry’s phone chimed.  He quickly applied a fresh coating of lipstick.  Terry grabbed his clutch/briefcase, slipped his lipstick into the case and they were on their way.

Moira was thrilled to see that he was trying to stick to the lipstick regimen they had devised.  She was even happier to see that he was apparently just assuming he needed lipstick when the alarm went off.  In this way, he would eventually develop a habit of continually reviewing his lipstick and constantly reapplying it.  Terry thought he looked a little different in his new clothes that were man-style.

Moira knew Terry looked like a woman in man-styled women’s clothing.  In fact, with his prominent bust, no one would begin by assuming Terry was a male.  They arrived at the mall and walked together to one of the shoe stores Moira liked.  Moira quickly found a clerk she had dealt with in the past and explained that her “friend” needed some new shoes. Moira and Terry glanced at different styles and the clerk measured Terry’s feet and grabbed several sample shoes.

The clerk went back and forth getting different colors and styles for Terry to try on.  They had close to fifteen pairs of shoes on the floor and the clerk had just left again.  Terry’s phone prompted with his special chime.  Moira turned to observe Terry.  Terry grabbed his bag, pulled out his phone, and clicked on the app Moira had given him.  Terry brushed his hair behind his ears and looked at his face.  Terry casually opened his lipstick and brushed his ring finger across the tube before applying a light coat of lipstick to his lips.

He wiped his finger on a tissue in his bag, closed the lipstick, and returned everything to his bag.  Moira felt a real level of satisfaction in succeeding to get Terry to take the lipstick checkup seriously. Terry ended up buying two matching pairs of loafer-styled shoes in black and brown.  The shoes seemed a little more fitted around the sides of his feet and since he was not wearing socks they were slimmer than his normal shoes which had to accommodate thicker socks.

The front top of the shoes was a little closer to the toes and off of his instep than his older loafers.  The heel was about half an inch high.  The heel was slightly different than a normal heel.  Most men’s heels are straight up and down.  These shoes had a heel that tapered very slightly.  A person would have to look carefully to realize that the heels are tapered.  But once they noticed, it would be clear that the shoes were women’s.  Terry was reluctant to get the shoes, but Moira insisted they were very generic looking and that no one would notice.

Moira also insisted that Terry buy a pair of black shoes with a one-and-one-half-inch boxy heel.  She insisted he might need heels at some time and she assured him, he would prefer to learn about heels with a boxy heel instead of a typical ladies' pump with a two-inch heel tapered to a point. Terry slipped the black loafers on and put his old shoes in a bag with the new shoes.  As they left the store, Moira guided Terry to a local restaurant with a bar.

Since it was Sunday, the number of people in the bar was minimal.  Moira selected a booth and slid in.  She and Terry ordered a couple of beers and the waitress left to get their drinks. Moira looked at Terry, “Terry, we need to talk about this crazy situation.  Can we do that?” Terry nodded, “Sure.” Moira stated, “Terry, I like my job.  I know we got off to a slow start.  But, I feel like we have hit a rhythm lately and like everyone else, I want to succeed at my job.” Terry stared at her and nodded that he understood.

Moira continued, “I have been trying to help you in any way I can.  But, if you get in trouble, I will probably be penalized along with you.  I’d like to try and build some successes in case that happens.  Don’t you think that is a good strategy?” Terry agreed, “Probably.” Moira paused before she began her proposal, “I was thinking that you could let me take the responsibility for one or two projects we are handling and you could tell anyone that asks that you believe in working as a team and that you want to help me to succeed.  What do you think?” Terry thought for a moment.  “You’ve helped me out a lot with my problems.

I think I can give you a project or two.  I know you are capable and I’ll still be there to help if there are any hurdles that need to be handled.” Moira smiled.  “I am happy to help you out.  And, I’m glad you like my idea.  I may need your help with the projects or with other things.” Terry asked, “Like what other things?” Moira smiled again, “I may not be able to be as attentive to all your needs and you may need to do some of the things I do normally.

Can I count on you?” Terry assured her it would be no problem.  Moira suggested that Terry try to get to work before many of the other people in the office to avoid being observed by everyone who was sitting around prior to getting down to work.  It was common practice for the first people to arrive to gather their first cups of coffee and gossip while observing the outfits and behavior of the last to arrive each morning.  Moira said she would get in earlier and they could make it look like something they were doing as a team.  Terry agreed to try to get in earlier.

Monday morning, Terry took much longer to get ready than he expected.  After donning a bra, something that still felt foreign every time he did it, Terry could not deny the obvious feminine characteristics of the camisole.

He put on a blue broadcloth dress shirt from his new blouse collection and with the bright lights in his bathroom the shirt seemed to hide the secrets underneath. After putting on his pants and tie, Terry’s phone beeped reminding him about his lipstick.  Terry retrieved his bag and went to the bathroom.  As he applied the neutral-colored lipstick, he could not rid of the feeling that it was obvious to everyone.  Then he thought back to Sunday and reminded himself no one had said anything.

Moira didn’t mention it.  But, he ended up wasting 15-20 minutes just staring at himself in the mirror trying to work it out. Then there were the new shoes.  Terry had to wear knee-high trouser socks to get his feet into the new shoes.  Somehow, though he had worn them in the mall yesterday, they seemed obviously female.  Then he looked down while standing and his pants legs seemed to hide his shoes.  Maybe no one would see them. Moira was near her desk watching for Terry.

He had not arrived early.  In fact, he arrived at the last minute and as people do, everyone glanced at him as he made his way past the cubicles to his office.  Terry arrived at work wearing his gray suit with the new pants Moira had purchased.  A striped tie hung down from a crisply tied knot in front of his blue broadcloth dress shirt.  His hair was in a relaxed ponytail.

Hair hung down a little looser than normal dipping near his ears to try to cover the small earrings.  The bottom of the ponytail was tucked in the back like he usually did.  However, his hair had a body and was full of curls from his hair treatment.

Terry had on loafers with dark trouser socks which some of the men might think were men’s dress socks.  Men may have wondered why he looked different.  The women all noticed that Terry’s hair now had waves and body.  As he walked to his car and rode into work, Terry was aware of many new feelings.  His pants slid along his hairless legs as did his camisole which seemed to shimmer along his back and stomach.  He had not needed to shave this morning which was strange.  But he really hated shaving so he was not bothered about it.

Moira noticed the slight shine on his fingernails as he carried his notebook case/purse like a clutch this morning.  She was also pleased to see that he had on neutral lipstick which was similar to his own lip color.  Of course, with lipstick on, the little creases in Terry’s lips were gone and his lips had a shine to them.  Moira was very pleased with Terry’s efforts.  She followed him into the office and sat down across from his desk.  “Terry, you look great.  How do the new clothes feel?”  Moira asked. “I have to admit, everything seems to fit well.  The new shirts do seem to be the right size and style to help accommodate my assets while de-emphasizing them.

Can you tell any of the little things?”  Terry was clearly concerned that his feminine additions were clearly visible.  “Terry, you look just like any other employee showing up for work.  People are not looking for the unusual.  They just see what they want to see.  And yet, you are totally in compliance with the dress code.  So, you have nothing to worry about.” Moira did not mention that looking like any other employee might include looking like an employee such as one of the administrative assistants.  At first blush, Terry looked pretty much the same as any other day.

But, Moira knew he was dressed in clothes more consistent with the administrative assistants than the other guys in the executive offices.  None of them were sporting a bra, camisole, and professional-looking blouse.  The other men weren’t hairless below the chin and probably were not wearing panties and trouser socks.  And Terry was the only male carrying a purse to the office every day.  His hair and nails along with his jewelry were in total compliance with the dress code for the executive administrative assistants.  Terry’s replacement suit pants were from one of the more expensive women’s professional shops where Moira liked to shop.

The new pants accommodated Terry’s expanding derriere and reduced waist.  Besides his coat, Terry didn’t have any male clothing on except for his necktie.  But, the clothes were well suited to his new body shape.  “Terry, it’s probably a good habit to always check your lipstick as soon as you return to the office from an extended absence or first thing in the morning.  Pull out your phone and check your lipstick, your face, and your hair.”  Moira directed. Terry opened his purse and retrieved his telephone with its cover that matched his purse.

He checked his look on the phone's application and then quickly rubbed a finger across his lipstick and applied a light lipstick coating update with his pinky.  He ran his hand over his hair to flatten down a few stray hairs that stuck up.  Finished, he quickly returned his lipstick to the purse and placed his phone on the desk.  Moira smiled at him and reminded him to take off his coat.  “Terry, you didn’t take your coat off.  You never wear it sitting down.  You don’t want to get it wrinkled.” Terry stood up and took his coat off.  He hung it on the back of his chair and sat back down.

Without the coat, Moira knew his attire was totally consistent with the administrative assistants since they always worked in their blouses and did not wear coats or blazers at their desks in the office.  He was clearly self-conscious about his chest and how it looked.  His tie kind of went forward a bit to go over his breasts and then hung down.  It was a little away from his shirt which was not how men’s ties usually hung.  But most people would never notice.

In this shirt and underwear combination, Terry was probably safe from anyone but a woman who was trying to find clothing anomalies.  No man in the office would notice, at the moment.  Terry got to work and the morning was like any other morning.  Moira brought Terry his coffee and refilled it when needed.  At lunch, Terry asked Moira to bring him something to eat at his desk and she retrieved lunches from a local restaurant.  After lunch, Moira reminded him to check his lipstick.  Later that afternoon, Moira again reminded him to check his look.

By the end of the day, Terry had all but forgotten his attire as he became involved in his work.  He was aware of the bra, but it had slipped into the background of his thoughts.  He grabbed his coat and briefcase and headed home.  Moira reminded Terry to try and get in earlier the next day. When he got home, Terry loosened his tie, hung up his coat, and sat down in front of his TV to watch the news.  Terry’s mind wandered and his thoughts wandered to work and behavior at the office.

Terry was pondering the changes in his Friday work schedule and the time it was taking him to get ready.  It was only after Terry had learned about the scheduled salon appointments that the odd thing he had noticed made sense.  There were certain gaps where assistants in the executive area seemed to disappear for extended periods of time.  Terry thought maybe they were all out taking long smoking breaks or extended lunches.

Terry now realized this must be the time for their appointments.  They couldn’t all be gone at the same time. At least Terry felt lucky that his and Moira’s salon appointments were at the end of the day on Friday so he would not have to go back to work afterward.  Since no one scheduled important meetings on Friday afternoons, he thought that would work out well.

Tuesday morning, Terry was a little faster getting ready.  He wore his black suit and another broadcloth blouse.  He wore the black shoes again and pulled into the lot at work a full thirty minutes early.  Moira had beaten Terry to work by about 15 minutes early.  She was pretty sure Terry would make it in early on his second day.  Moira watched Terry slip into the mostly empty office space and make his way to his personal office.  She again noted that he had worn the correct clothing and shoes.  The new pants Moira had bought Terry for his suits all fit his figure well.  In fact, they almost looked fitted.  Moira noted to herself that the panties she had purchased for Terry which had some nice spandex seemed to be eliminating any unsightly bulges in his new pants.  The pants she had purchased for him were fitted and were slightly tight in his crotch.

Due to the stretchy material, Terry probably felt they were comfortable.  But she wanted the crotch to look the same as everyone else wearing similarly styled pants.  And the people wearing similar pants in the office where many of the administrative assistants, all of whom were women.  As Moira’s thoughts drifted away from his pants, she realized that he was not wearing the naturally colored lipstick.  That worried her.  His hair was not done as nicely as yesterday.  Terry seemed to have pulled his hair tightly down into a ponytail and that had flattened the hairstyle.

Moira followed Terry into his office.  Terry slipped off his coat and placed his bag on the desk.  He looked up to see Moira staring at him.  She did not look happy. “Is there something wrong,” Terry asked. “Two obvious things are wrong.  That of course causes me to wonder if there are more things wrong that I don’t know about.  Terry couldn’t figure out what he had done wrong.  “What are you talking about?” Moira pointed at his face.  “Where is your lipstick?” Sudden realization crossed Terry’s face.  He quickly grabbed his bag, pulled out the lipstick, and unselfconsciously applied a fresh coat of lipstick.  He seemed disappointed in himself.

So, Moira decided not to ride him.  She was also surprised he did not use a finger or hide in a corner to apply the lipstick.  “Terry, we have to make sure that you don’t forget.  I need this job.  I’ll think of something.  The other question I have is, what happened to your hair?” Terry reached up and felt around on his scalp.  He started muttering, “I wanted to get here on time as we agreed.  So I hopped out of the shower, slapped a band in my hair, and let it air dry on the way to work.” Moira now understood the problem.  “Terry, you can’t do that with the way they cut your hair.  You should actually be brushing it and drying it with a hair dryer.  It looks totally lifeless. Let me see if I can do something.”  Moira turned and exited the office.

Terry stood there not knowing what to do.  Moira returned with a brush, a comb, and a small spray bottle from her desk.  She closed the door and told Terry to sit in one of his guest chairs.  Moira pulled Terry’s hair out of his shirt collar and removed the band.  She started brushing his hair.  She identified the curves and worked some life back into his hair.  She used the comb to define a part on the top of his head.  She allowed the hair to drape slightly on the sides and slipped the band back into his hair and tucked the tail back into his collar.

Stepping back, Moira seemed satisfied to have restored some of the life to his hair.  It now hung near his ears and looked much better. While she was brushing his hair, Moira ran her hand across his shoulder and felt the distinctive strap of his bra.  Terry asked, “All fixed?” Moira smiled, “Yes. That’s much better.” Terry moved back behind his desk and sat down. Moira looked at Terry and asked, “Remember what we talked about on Sunday? Do you think I could work on the Jefferson proposal?” Terry thought for a moment and said, “Sure. That is a good project for you to begin with.” Moira said, “I thought that when we come in early maybe I could concentrate on that and you could help with anything that needs to be done.

How does that sound?” Terry thought that was a good way to start.  They could begin to get her up to speed outside of normal hours and then it would not distract them from normal activity.  “Good idea.  You gather information today and we can discuss it tomorrow morning.” Moira had already gathered a lot of information and she was already putting the proposal together.  By tomorrow morning, she planned to be well into the meat of the proposal, writing up the plans and requirements.  Throughout the day, Moira repeatedly reminded Terry to check his lipstick.

Near the end of the day, she grabbed his phone and reprogrammed the app to start reminding him during business hours on a sort of fixed schedule that would be right after breaks and lunches.  That way she would not need to keep reminding him.  She put the alarm application on his main phone screen.  She explained that every time, Terry checked his hair and lipstick, he should simply touch the alarm application icon.  If he clicked the application icon, it would not provide any alerts it was scheduled to provide for at least 30 minutes.  So if Terry was diligent about checking his lipstick and his hair, he would never hear the reminder application.

Terry agreed this was a goal he could work towards.  As Terry was leaving, Moira told him to brush his hair before going to bed.  She also reminded him to use a hair dryer in the morning and avoid flattening his hair.  While Terry watched TV that evening, his phone reminded him to check his lipstick on an irregular schedule.  He stayed sitting on the couch and used the phone mirror app to check his looks.  He had removed the hair tie when he got home and when he checked his look he found himself unconsciously brushing his hair off his face and behind his ears.  Moira was sitting at home and she carefully observed the video updates of his lipstick and hair checks.