Undercover Chapter 1 - 5 (Patreon)

Chapter 1

Ethan Baughman entered Captain Hoganmeier's office.  He had been informed that the captain had wanted to see him.  Ethan couldn't imagine what the captain would want with him.  Ethan had rarely a meaningful conversation with the lieutenant, let alone the captain.

Ethan was an exemplary officer and couldn't imagine anything wrong with his performance.  His career began several years ago, before he could get his figurative feet wet.   Ethan was chosen right out of the academy for a special undercover assignment.  His young looks made him the perfect choice to play the teenage son in a family of four (all undercover police officers) which were investigating a man posing as a family therapist which was doing some very bizarre things with his patients.  At first, they thought he was a real therapist, but by the time the man disappeared, the truth was determined that he had never been a psychologist at all.  Whether the faux family therapist had gone to college or not, he certainly didn't have any degrees or training in therapy.

The 'family' considered of himself, two older detectives who were posing as his parents and another office directly out of the academy who posed as his younger sister.

At five foot seven and relatively slight of build, Ethan could pass at that time as a seventeen-year-old boy for the operation.  The other younger officer, Fiona, was five foot three and posed as his fifteen-year-old sister.

The undercover assignment went on for some months.  During which time, Ethan and Fiona got to know each other very well.  Even though the doctor got away, and Fiona decided she didn't have the stuff to be a police officer, the one good thing to come of this was that Ethan and Fiona got married.  They are still married today.

"Yes, Sir," Ethan stood at attention in the Captain's presence.

"At ease, Ethan," the Captain said indicating that he should take a seat.

Ethan sat down.

"Ethan, there has been trouble in the Fillmore district and I want you to go undercover."

"Me, Sir?" Ethan was surprised at the request.  he wasn't a detective and the Fillmore district wasn't even in his precinct.  The Fillmore district was also notorious for its homosexual prostitution problem.

"Yes, we suspect there might be police officers involved and we need a fresh face to go undercover and see what is happening.  The victims, transsexual prostitutes, won't talk to us.  Getting inside and gaining their trust is the only way..."

Ethan couldn't believe what he was hearing.

"...We want you to go there undercover as a transsexual.  Get to know the people, establish friendships and gain their trust.  You'll tell them, you have a secret life from your wife, that you like dressing up, things like that.  You have to make them believe you are one of them.  You won't ask about what is going on, you'll just keep your eyes and ears open and let the information come to you."

"You want me in drag?"

"Well, yes.  You have to make them believe you.  When you first go there, I don't expect you to even talk to anyone.  Just walk around and be seen.  This assignment could take months, but we don't think we have any other alternatives."

Ethan tried to process what he was hearing.

"You, of course, will be promoted to detective with a raise in salary.  The salary will begin immediately, although the actual promotion won't be recorded until after the assignment is over.  It's important that no one at the department knows about any of this.  Actually, you will be listed as on suspension during this assignment."

"Can I tell my wife?"

"Of course, but you have to let him know she can't tell anyone.  You really couldn't keep it from her anyway.  As officially you will be on suspension, you can't come here to change into your costume.  You will have to do all of that at your home.  There won't be any way to keep Fiona from knowing.  She can probably help you out."

"How so?"

"We don't expect you to pass as a woman immediately, but you will have to make progress as time continues.  If you don't they will get suspicious and the undercover won't work.  She can help you pass as a woman."

"Can I think about it?"

"Sure, go home.  Talk to your wife.  See what she has to say."

"OK."

"One other thing," the Captain said as he handed Ethan a piece of paper with an official seal on it.  "This is your letter of reprimand."

"My what?"

"I told you we are going to officially suspend you during the time of the undercover.  Anyone who checks the records will see your status as suspended.  It all has to look completely legitimate.  It starts with this.  A copy of which has been put into your file.  We'll remove all records of the reprimands and suspension if you don't take the assignment or when the assignment is over."

Ethan took the paper.

"It'll be fine.  Don't worry about it."

Ethan looked over the paper.  It looked official.  It had all the appropriate legalese.  Ethan read through it.

"....on such and such day, Officer Ethan Baughman was out of uniform when while performing his duties.  Under his uniform jacket, instead of wearing a regulation shirt, Officer Baughman had on instead a woman's white bodysuit.  (Let it also be known that he was also wearing a bra, but that isn't against department policy.)  The penalty of this infraction is that  Officer Baughman is officially reprimanded and a letter of this reprimand will be placed in his official folder.  If another infraction is noted within three months, a temporary suspension could result."

"It looks real."

"As far as anyone outside this room is concerned, it is real.  Please sign it on the line where you agree not to contest the reprimand and accept the official penalty.  To wit, me talking to you and placing this form in your office file.  To be official, consider yourself 'talked to'."

There was a second like on the reprimand.  The one where Ethan could contest the findings.  Ethan liked the idea of the promotion and becoming a detective.  He was about to sign the form on the appropriate line.

"One second," The captain stated.

Ethan looked up.

The Captain used his intercom to summon his secretary into his office and a second officer.

When all three were in the office, The Captain said to Ethan, "Raise you hand."

He did.

Continuing, "Do you swear that what is contained in this form is true?"

"Yes."

"Please read it then and then sign in."

Ethan signed the reprimand.

"OK, you two sign in the space for witness's signatures."

Ethan trusted the Captain.  But signing an official reprimand he was acknowledging that everything in the form had happened.  From now on he would have an official record stating that he worn women's apparel.  He had signed the form in front of witnesses he couldn't deny that fact later.

Chapter 2

Ethan was given the rest of the day off to make up his mind.  On the way home, Ethan had already decided, he would take the assignment.   He wanted to be a detective so badly he could taste it.  Then there was the bump in salary and the promotion too.

All in all, this undercover wasn't as dangerous as many.  There were whole movies like Donnie Brasco where the detective not only stayed undercover for years and was in a great deal of danger if discovered.  If Ethan was discovered, it wouldn't look good for him, but at least he wouldn't be killed by mobsters.

It killed him that he couldn't tell his fellow officers, but those were the breaks.  When it was over and everyone knew what had happened, he was sure he would be kidded about it for years to come, but he'd be a detective sergeant making twice what he was making now.  "Let them kid!"

"You're home," Fiona called out.

"Yeah, and I have some news."

"What?"

Ethan didn't explain. Instead, he handed her his reprimand papers.

She looked it over.  A look of shock and horror appeared on her face.  "WHAT IS THIS?" Fiona shouted.  She couldn't believe what she was seeing.  "Have you been wearing my clothes?  How long has this been going on?"

Ethan started to laugh.  "Calm down, it's all fake.  They're putting me undercover.  The reprimand is part of it."

"But this is an official reprimand.  It looks real."

"Tell me about it.  The Captain had me go through this whole act.  He made a big production of out telling me never to be out of uniform while on duty.  That if it ever happens again, I'll be suspended.  Then he brought to witnesses in to watch me sign the papers.  If I didn't know better I would think it's real too.  They made it up.  I need to look like I'm in trouble.  It's all part of the undercover."

"It says you were wearing women's clothing.  Did you really do that too?  To you know make it look real?"

"No.  But I'll have to soon.  Where women's clothing that is.  They want me to go undercover as a transvestite.  They want me to gain the confidence of transsexuals.  They believe that police might be involved in the harassment.  It has to seem as real as possible."

Fiona looked it over.  It was a copy (the original was in Ethan's official file).  But it looked completely legitimate.  It was on official letterhead, it had all the right signatures and seals.  The story had specific details.  It had names, dates and phone numbers where witnesses could be reached to confirm the story.  "Did you read this?"

"Sure."

"It has a picture of the bodysuit you were wearing."

"It does."

"Yeah, here on page two.  You know that is pretty cute," Fiona told him with a smile.

On page two was a picture of a white cap sleeve mesh (semi-transparent) bodysuit.  It had a V-neck and a two-button snap crotch.  Under the picture was a description and a notation that it is being held as evidence.  To be returned to Officer Baughman, if said officer doesn't receive another reprimand in the next six months.

"Says you'll get it back.  When you do, can I borrow it?"

"Funny!"

Fiona started to snicker.

"They want me to start dressing up and frequenting in the Fillmore district."

"What about us?"

"What about us?" Ethan repeated.

Are you going to move out and live full-time as a woman?"

"No, but they will suspend me to make it seem more genuine."

"A suspension with pay?"

"Not only that, they're giving me a raise starting immediately."

"How much?"

"My salary will be bumped by 25 percent."

"Wow! We'll be able to make a down payment on a new house earlier than I expected."

"I've already got it.  You'll see when you deposit my next paycheck."

"My husband is going to be a detective!"

"Yes, he is."

"My husband, the detective in a dress," Fiona mused.

"I'll be the same man under that dress I promise.  Let's go to the bedroom and not only will we celebrate, but I'll show you how much of a man I can be!"

"Want to put on my chemise?"

"Clothes who needs clothes?"

Chapter 3

Ethan returned home.  He was carrying a garment bag over his right shoulder, grasping it by the protruding hanger top.  In his left hand was a brown paper shopping bag.

Fiona ran up to him.  "Is that it?" she asked.  She was fixated on the garment that he held over his back.  She knew quite well that it had to be Ethan first dress.  The shopping bag didn't concern her.

"Uh-huh"

"Can I see it?"

"Soon."

"I want to see it now.  Better yet I want to see you in it," she couldn't help but to giggle.

"Come on.  You can look at  it later."

"No! Now!"

Fiona was dying to see her macho, policeman husband in a pretty dress.  Ethan was curious too.

"OK, OK."

Ethan headed towards his bedroom to change.  Fiona followed suit.

"No, let me put it on first."

Fiona acquiesced and let Ethan close the door.  She waited in the hall outside.

Once alone, Ethan took the dress out of its protective covering.  This was the first time he saw it  The Captain gave him the outfit already wrapped.  Ethan left the station with it quickly.  He didn't want the guys to see what he had.

Ethan unzipped the garment bag exposing the dress.  His first thought when seeing the dress was "Oh my god!  Am I really going to be wearing this?"

Ethan beheld a black mini-dress with a  three-tiered skirt.  It had a stretched waist, round neck, and sheer flutter sleeves. The very feminine dress was bespectacled with metallic gold flakes throughout.  He should have suspected that the dress would be very dainty.  Ethan wondered how he would fit into it, especially the waist and the shoulders.

Ethan removed it by the hanger from its plastic casing.  Turning it over, Ethan saw the dress's hidden zipper.  He unzipped it, then he noticed that the neck was fastened with a hook-n-eye closure.  With the fastener opened, the dress stood  agape from the neck to the elasticized waist.

Ethan took off his shirt and pants leaving him in only his briefs.

"Here goes nothing," he thought.  Then for a second he wondered if he was supposed to pull the dress over his shoulders or step into it like a pair of pants.  he tried to remember how Fiona would put on a dress like this.  He usually didn't pay much attention when she was dressing.  Especially if she was getting all dolled up.  Ethan decided that since it had a long zipper he should step into it.

Ethan strode into the dress and then pulled it up.  He had never worn a garment like this before.  He held the bodice out in front of him and then put his left hand through the sleeve, followed closely by the right hand.  Soon the dress was on his body although it stood open in the back.  The flutter sleeves had plenty of room for his broad shoulders.  He reached behind himself and found the zipper.  He pulled it up to the small of his back.  Now the elastic waist clung to his body.  It could accommodate waists many sizes smaller than his own and maybe one a couple of inches larger too.

Now that the zipper was half the way up.  Ethan didn't know how to get it the rest of the way.  He scrunched the dress trying to get the zipper higher.  He needed it high enough so that he could reach it from over his shoulder.  He got it up maybe two more inches, but it still wasn't high enough.  He needed help.

Ethan reached behind his neck and fastened the hook-n-eye.  He thought that would help. Frustratingly, it didn't make a difference.

"Maybe if I used a pencil to push the zipper up," he thought.  He wanted to get the dress on all by himself.

He found a pencil in the drawer and tried to hook the zipper with it.  He didn't know that he was making pencil marks on the back of the dress.  It was a good thing the dress was black to begin with.  If it was white or a lighter color he would have to dry clean the dress before wearing it now.

Regardless, he couldn't push the zipper up far enough.  He had found himself in a no-mans-land where he couldn't push the zipper up any farther, nor could he reach it to pull the zipper down to get out of the dress.

"Honey, what's taking so long?" Ethan heard from the other side of the door.

"Just a minute," he shouted.  He didn't want to give up.  He was determined to get the dress on all by himself.

"I'm waiting."

After a couple more minutes of frustration, Ethan opened the door and asked Fiona to come in.

"Help me!" he pleaded.

Fiona didn't even bother to suppress her laugh.  It was funny to see her husband partially in a dress.

"What's wrong?" she said while still giggling.

Ethan turned around.  "I can't get the zipper up.  I don't know how you do it?"

Fiona seldomly asked him to 'zip her up.'  What Ethan didn't know was that Fiona rarely wore dresses that zipped right to the top.  Most of the dresses she owned had a keyhole back with a button or hook-n-eye closure.  She didn't need to zip it all the way up for it to close properly.  Fiona was having too much fun to tell Ethan her secret.  Instead, she just did as he requested and pulled the zipper to the top.

"Want me to secure the hooks?"  The dress had a pair of hooks and apparently Ethan place the bottom-most hook into the top-most eye.

"No, I can fix it."

"Suit yourself."

Ethan reached around his neck and tried to fasten the proper hook into the proper eye.  But not only were his fingers bigger than Fiona's they weren't as dexterous as hers.

"I can do it for you."

"I can do it.  Give me a chance," he pleaded.

"Alright, if you insist."

Ethan was proud of himself when he finally got the dress fastened.

"How do I look?"

"I don't think black socks go with that dress.  Maybe some black tights instead?"  Fiona was smiling from ear to ear.

Ethan had forgotten to take off his socks.

"Are you wearing panties," Fiona asked.

"No."

"I think you should."

Without waiting for an answer, Fiona went to her drawer while saying, "I have a better idea."

She then searched for a shaper.

"Try this?" she said handing him a black Spanx high-waisted pantie.  "This will hide all those nasty bulges," Fiona informed Ethan as she stared at his crotch.  The tiered nature of the dress helped hide his package, but there was still a little bulge showing.

Ethan looked down and saw what she meant.  "Give me that."

"Here put on some tights too."

"How did I get into this?"

"You wanted to be an undercover detective.  Don't you remember?"

"Yeah, but who would have thought I would be...I would look like this?"

Ethan pulled up the hem of his skirt and then pulled off his briefs.  Then he sat on the foot of the bed and pulled up the shaper.  It rose all the way up just below his chest.  It was very tight.  He had to adjust his penis to get it as 'comfortable' as possible.  Ethan never thought of tucking his penis between his legs to give himself a totally flat stomach.

Once the shaper was on correctly, Ethan pulled his dress down into place.  Between the shaper, the tiers, and the dark color of the dress itself , Ethan's bulge was mostly hidden now.

"I'm going to show you how to put on tights," Fiona said without being asked.  She then snaked her fingers down one leg of the tights while explaining the procedure on how to put them on.

"Once you have it on one foot, you pull it to the calf and then to just below the knee, then you repeat with the other leg."

"Do I really have to wear them?"

"Would you rather shave your hairy legs?"

"I guess not."

Ethan slipped his size 10 feet into the hose and did as his wife explained.  The material wasn't very sheer so there would be little problem with getting a run in them.

As with the shaper, He then had to pull the skirt of his dress-up to get the hose into place.  He pulled the hose taut and it rose to almost the same height as the shaper which surprised him since Fiona was much shorter than he was.  She was only five foot three.  He was five foot seven.

Once again, Ethan smoothed the dress into place.

"How do I look?"

"Well firstly when you do this for real, the tights go on first and then the shaper.  But besides that, I think you need some contrast."

"Contrast?"

"Yeah, a nice gold necklace and some earrings to contrast the black dress and tights."

"Oh, god," Ethan sighed.

"There will be more to it than that."

"What?"

"Well you know you'll have to wear makeup."

"I suppose"

"You will also have to shave your arms and with this dress, shave your armpits too."

It was also obvious and both Fiona and Ethan knew that he would have to shave off his mustache.  But Fiona didn't mention that.

Ethan looked at his hairy arms and knew she was right.

Continuing Fiona said, "you will also have to paint your nails and you should probably wear a wig."

"I have a wig."

Fiona didn't notice what else Ethan was carrying when he arrived home, she was fixated on the dress.  Inside the paper shopping bag was a wig and a pair of shoes in Ethan's size.

"Let me see."

Ethan showed her the wig, it was long in an auburn brown color."

"Not blonde?"

"No!"

One other thing, you should wear a bra."

"I don't have boobs."

"I'm not big in that department either, that's why I wear a padded bra.  You should also."

"I'll think about it."

"If you've had enough fun, I'd like to get back into my regular clothes."

"Awe you're not coming to dinner all dressed up?  You'll add a little bit of elegance to the spaghetti and meatball dinner I prepared."  Fiona was having a lot of fun at her husband's expense.

It was only after Fiona left the room, that Ethan realized he couldn't get out of the dress without her help.  Not if he didn't want to rip the dress that is.

Taking off the dress was in some ways harder than putting it on.  Not only did the zipper have to be pulled down for him, but he had to make sure that he didn't crease the dress and put it back on its hanger.  Then he have to replace the plastic protective covering.

The news of Ethan's reprimand got around the station.  Ethan, as he was instructed, told anyone who asked "It's no big deal.  I don't want to talk about it."  It was hard to hide as he was placed on 'restricted duty'.  It was during this time that he shaved off his mustache.

Chapter 4

On the day his assignment was officially to begin, an excuse was made to send him home early.  He had to prepare which would take several hours.  It all started with a shower and a shave.  His mustache was already gone, this time he shaved his upper chest, arms, and underarms.  He didn't need to shave his legs as he was going to wear black tights and no one would be able to tell.  But with the dress he was going to wear, with its sheer flutter sleeves, his arms and shoulders had to be bare.  It's not like anyone would notice the rest of the time.  A regular t-shirt would hide his shaven upper body.

Ethan had shaved thousands of times over the years, but he had never shaven his arms. He nicked himself quite often, even though he thought he was being careful.

"Damn," Ethan thought, "If I'm going to shave my legs which seemed harder, he would use one of those hair removal creams instead."

After showering, Ethan shaved his face as closely as he could.  He had to hide any trace of five o-clock shadow as well as any stray hairs from his neck to his chest.

Ethan exited the bathroom wearing only a towel around his waist.  He didn't want to get blood on his clothes from his bleeding arms.  Fiona was waiting for him.  She promised she would help him get dressed, and more importantly help with applying his makeup.

"Here put these on how I showed you," Fiona handed him a pair of black, opaque tights.

"Should I put on some underwear?"

"You mean like panties?"

"Yeah."

"You don't have to wear anything under tights.  But if you want to?"

"If you say I don't need them."

Putting on tights wasn't too hard if you knew what you were doing.  Besides, since they were thicker than pantyhose, there wasn't much chance of getting a run in them.  Ethan rolled the hose up his fingers and then snaked them up his legs.  He was careful that they didn't get runs and that there weren't any wrinkles in the tights.  Ethan had been practicing for this moment.

Ethan pulled the Spanx over the tights.  It would give his lower half the proper shape and would keep his penis as hidden as possible.  The garment was tight, but Ethan manned up and didn't complain.

"Turn around.  Let me see."

Ethan did as Fiona requested.

"One second."

Fiona retrieved something from her pantie drawer.  "Turn around," she said.

Then she reached under the Spanx and the tights and left something clinging to Ethan's butt cheeks.

"What's that?"

"I put some scrunched-up panties on your backside.  It'll make you seem like you have a rounded butt.

"What?"

"Believe me, it'll work."

Ethan looked over his shoulder to see his butt sticking out farther than it should.  "Are you sure?"

"You said you would listen to me.  OK, and now a bra," she informed him.

The bra bothered him, but he knew Fiona was right, he needed something on top to show he was serious.  The padding would give an illusion of some breasts.

Ethan put his arms through the shoulder loops and Fiona fastened the hooks in the back.

"So I need to stuff my bra?"

"You could, but I don't think so.  You're 'well built' with the padded cups it should be OK."

Ethan didn't really want to do it anyway.

"OK, sit down and I'll put on your makeup."

"Shouldn't I put on my dress first?"

"No, that comes later."

Fiona gave Ethan a cream.

"What's that?"

"It's foundation, silly."

"What do I do with it?"

"You put it everywhere."

Ethan took it from her and put it on his cheeks like it was blush.

OK, now use this brush to work it in.

Ethan did so.

"Use more."

"Isn't this too much?"

"Not for you.  Believe me, you need it."

Soon Ethan's entire face was covered in foundation.  It made his skin tone a little lighter.

"You aren't finished."

"What's left?

She took the bottle of foundation from him and then applied it to his neck.

"Hey."

"You need it there too, your face and your neck have to be one continuous shade.  Foundation gives you a smooth and creamy appearance.  It hides a lot of sins.  Even that shadow you get."

"I shaved that off."

"That won't last forever."

"I'll be out at night."

"Just believe me."

Fiona from that point on applied most of Ethan's makeup.   She even used some makeup to give the illusion of a smaller nose.  Fiona had never needed this type of thing.  It was the one flaw in her application of makeup.  Once applied, she taught Ethan how to fix any problems.  Which most meant how to redo his lipstick and adjust his blush.

"What do you think?"

Ethan looked at himself.  He knew that no amount of makeup would make him not look like a guy in some ways.  His chin was too square.  His cheekbones too low.  But that was the point, he wasn't supposed to look exactly like a woman.  He was supposed to look like a man who was stepping out for the first time en-femme.

Once finished, Ethan slipped into his dress.  He turned around for Fiona to zip him up.

"This is why so many of the higher neck dresses have a keyhole with a button or a hook-n-eye closure.  That way you can fasten the dress yourself without needing someone else to assist you."

Ethan had never thought about such things before.

Fiona handed Ethan a gold necklace with a thin chain and a couple of bracelets.

"What's this for?"

"I told you.  You need contrast.  It'll make you look better."

"Come on."

"I only wish you had pierced your ears.  Then I can send you out with dangling earrings."

"You're enjoying this."

"Of course I am.  Aren't you?"

"I don't know."  Ethan wanted to start his assignment, but dressing up and all was ruffling his male pride.

The final steps included the wig.  It was a brunette straight bob with bangs that curled in at the end to partially hiding his face.  It descended to his armpits.  He put it on which made a big difference in many ways.  It framed his face and de-emphasized his lower cheekbones and partially hide his relatively flat upper chest.

The last step was his shoes which were pumps with two and a half-inch heels.  He stood five feet ten for the first time in his life.

"Now what?"

"You know, maybe we should have put you in white tights instead of black?'

"Why?"

"I told you, contrast: black dress, black tights, black shoes.  You need contrast."  Fiona also thought that by the end of the night, Ethan's feet would be hurting badly with those shoes.  They weren't appropriate for walking a great deal which was what Ethan was expected to do.  Fiona didn't have replacement shoes for him so she didn't say anything.

"I'm not changing."

"Suit yourself."

Ethan picked up his clutch purse and was ready to go.

"You're not going to carry that are you?" Fiona asked.

"Why shouldn't I?"  The purse and the shoes were supplied to Ethan by the Captain.

"It doesn't go with your outfit."

"It doesn't?"

"No, wait I have something that'll work better."

Fiona picked out a bigger purse that suited the dress better.  "Now let's see."

Fiona took Ethan's wallet, cellphone, and keys out of his former purse and put them into the new one.  "Look, you'll need some things."  She got some tissues, some makeup, a mirror, a hairbrush, an extra pair of tights, and other items that she thought that Ethan would need and put them into his new purse.  She even threw in some ibuprofen and water to help his soon-to-be-pained feet.

The contents of his wallet had been sanitized. It contained his ID, but any mention that he was a police officer had been removed.  He certainly didn't take with him his badge and gun.

"Do I really need all those things?  You do, believe me."

Ethan hesitated.

"You want to seem authentic don't you?"

Ethan got into the car, put his purse down beside him, then quickly exited the car.  He had to smooth the dress under him.  Something he never had to do before.

Ethan could feel the scrunched panties under his butt cheeks and he was very aware of the tightness in his crotch caused by the tights and Spanx.

Ethan was ready to go.  He was a little frightened, but not of being dressed as he was.  he thought this was just an undercover assignment and once he got to Fillmore, he would be fine.  What frightened him was someone in his own neighborhood seeing him dressed like this as he pulled out of his garage.  Since he couldn't explain what he was doing, he didn't want to be seen.

He opened his purse and fished out his phone.  he called Fiona.

"Hi, Sweetie."

"Fiona, go outside and make sure no one is around."

"What?"

"I don't want our neighbors to see me like this."

"Ten minutes a woman and you are worried about your looks?  You look pretty."

"You know what I mean."

"Darn, I should have taken a picture!"

"Don't you dare!"

"But I want to."

"Stop fooling around.  See if anyone is around so I can pull out."

"Fine, if you insist."

Fiona left the house and positioned herself at the end of the driveway.  "All is clear."

Ethan pressed the button that opened the garage door and drove out slowly.  He saw Fiona at the end of the driveway.  She was waving him on.

Ethan pulled out and backed onto the street.  But before he could pull away, Fiona took several pictures of him in the car.  There wasn't any doubt that it was Ethan dressed in drag with a face full of makeup.  Ethan drove to his assignment.

Chapter 5

As he drove down the street, Ethan noticed how different it felt to drive in heels.  His foot contacted the gas pedal at a strange angle.  The second thing he noticed was how his legs felt differently wearing tights.  He had never worn clothes that clung to his body as much as he was wearing now.  Even the wiggling of his toes felt strange.  It felt like his toes were encased in silk.  Every once in a while, Ethan couldn't help but look down to see his nylon-covered leg peeking out from under the skirt of his dress.

It didn't take too long for the tightness of his shaper to start bothering him also.  Ethan found it impossible to adjust his penis.  Especially while he was sitting.  Between the dress, Spanx and hose, he just couldn't get access to it.  Out of all he was wearing, it was the dress that felt the least odd on his body.

On the way, Ethan thought about what he was going to do.  Today, he decided to just walk around.    He didn't need to do anything special, he just wanted to see the people and have the people see him.  He would stay on the street.  He didn't want to go into a bar or a shop, though he might window shop if he found the right store.

Ethan parked his car a couple of blocks over from his assignment.  He thought it would be best not to park too near.  He took his cell phone out of his purse and called Fiona.

"I'm here," he told her.

"How is it?"

"I haven't left the car yet, but I'm ready to go."

"Don't break any hearts."

"What is that supposed to mean?"

"I mean the men won't be able to resist you.  You're so pretty now."

"Stop fooling around."

"OK, then good luck!"

"It's time to go.  I'll call you when it's over."

"Bye."

Ethan checked his face in the vanity mirror.  He looked fine. His makeup survived the ride over here.  But he thought a little touch-up of his lipstick couldn't hurt.  He was just being a bit over-cautious.   Ethan put his cell back into his purse and then pulled out a tube of lipstick.  He freshened his lips and then put it away.

Ethan exited his car and stood up straight.  He tried to adjust his penis.  But that wasn't easy.  He couldn't put his hand down his pants like he normally would.  He was wearing a dress, thus it was impossible.  The hem of the dress dropped to his knees and the Spanx underneath rose to the bottom of his ribs.  He knew he couldn't reach under his dress to relieve his discomfort.  He tried to pull the dress, Spanx, and hose away from his penis to adjust it.  That didn't work very well.  He really couldn't do anything.

Without any other recourse, Ethan gave up and started his walk towards the Fillmore district.  He was conscious of his walk.  He tried to 'move like a woman'.  He knew he wasn't succeeding very well but it didn't matter too much.  He just had to look like he was trying.   This was his first day.   Ethan tried to think of himself as he was.  He was a 'man' who was going out in public in drag for the first time.  He was supposed to look nervous and out of place.  That was certainly the case at this point.  With some practice, he knew he would 'get the hang of it.'

He wanted to look like a transsexual, but his appearance was more like a drag queen than a true woman or even a true transsexual.

Once in the district, Ethan tried to walk casually.  He tried not to stare at the people.  He didn't know if he should want people to stare at him.  He took glances at the people around him instead.  He wondered how many of the women were actually men.  There were some who were obvious, although not as obvious as himself.  Other's were harder to tell.  Ethan did know that all those 'working girls' were guys no matter what they looked like.  This district was famous for such things.

Ethan resisted his instincts to put on his 'don't mess with me' face.  he had to project, in a way, I'm just a person taking a walk.  I belong here.  He let some of his true emotions slip through though occasional.  The ones that made him look unsure of himself.  This was the proper look for this assignment.

Ethan walked up and down the blocks, stopping every once in a while to look in the store windows.  Many of the stores catered to men in drag and the complete spectrum of gender.  Ethan didn't want to go into the stores.  His plan was to be seen, not to make contact.

He spent a lot of his time trying to keep his bra straps on his shoulders.  They kept sagging until they would fall down.  Ethan thought he had to reach down his shoulders to pull those damn straps up more than on a typical day he had to put his hand down his pants to fix his penis.  Somehow his penis had actually found a comfortable spot in his tights.

At first, his adrenaline was flowing so much that he didn't realize how painful it was to walk.  His feet weren't used to shoes with heels.  Especially shoes that hadn't been broken in yet.  When his feet became extremely painful, he was glad that Fiona had packed him the ibuprofen.  He downed a couple with a swig of water.

After a couple of hours, Ethan had to find a place to sit.  His feet ached too much.  From this vantage point, he took the time to look over the street more openly.   He started to study how the people were dressed and how they moved.

While sitting, a very pretty working girl came over to Ethan.  Due to the neighborhood, Ethan knew this must be a trans-girl although if he didn't know better he would have never guessed.  The working girl was a white woman well over six feet, but she was wearing heels much higher than Ethan's own.  She had dark eyes and long dark hair that fell loosely down her shoulders.  Her dark complexion was highlighted with severe makeup as was usual with a person in her profession.  Her dress was very red and very short and her boobs spilled over the top of the dress.   She probably didn't bother to wear any underwear underneath her dress, but there wasn't any way of telling.  All in all, she was still very pretty.

"First-time honey?"

"No, I don't want to."

"I didn't mean that.  I meant this is your first time in public dressed like this?"

"Is it that obvious?"

"I've been here a long time.  I've seen a lot.  I can spot a first-timer right away."

"Oh...I guess it was something I just had to try."

"Are you going to keep it up?"

"I think I have to."  Ethan had to pull his bra strap back into place.

"If you do, you should lose the wedding ring."

Ethan hadn't thought about that.  He wore it for so long, he didn't even realize he had it on.  Ethan slapped his head with the palm of his hand.  I guess I forgot."

"Everyone forgets hundreds of things the first time.  You should have worn more comfortable shoes and  worn a more casual outfit."

"I'll remember for next time.  Although to tell you the truth, it's this damn bra strap that is driving me nuts.  It keeps falling down."

"We all have our crosses to bear.  I wish I could get away with wearing flats.  But I have to wear these for my job," the stranger lifted his foot to show his heels.

Ethan had made contact with his first person on the street.  He hadn't meant to, but things were going great.

"It's getting late, I think I should go."

"I'm going too."

"It's early for you."

"I have an early evening today.  Even in my line of work we don't always work until the wee hours."

"OK, see ya next time."

"Bye honey."

It was at this time that Ethan realized that he didn't know her name.  "I'm Ethan by the way, what's yours?"

"It's Lily-Rose.  Don't you have a femme name?"

"I hadn't thought about it."

"OK, bye Ethan Honey."

Ethan watched as Lily-Rose walked to the bus stop.   "You're taking the bus?"

"Yeah, I don't live around here."

"I can drive you.  My car isn't far off."

"Thank you."

"I'll go get it, wait here."

Ethan quickly got his car and drove to the curb to pick up Lily-Rose.

Lily-Rose signaled that Ethan should roll down the window.

"Look, I can take the bus.  It's no big deal you don't have to do this."

"Don't be silly.  It's no problem."

"Are you sure?"

"Yeah, get in."

Lily-Rose reached for the door handle and the door started to open.  It was then that Ethan saw the flashing lights of the squad car behind him.  Everyone froze.

Less than a minute later, a police officer was at Ethan's window.  "Step out of the car...Sir," the officer demanded.

Soon both Ethan and Lily-Rose were being frisked.

"HEY, DON'T DO THAT!" Lily-Rose screamed.

Ethan by instinct moved towards Lily-Rose and was wrestled to the ground by a pair of officers.   Both Lily-Rose and Ethan were arrested.  Ethan's car was towed.

Go to Chapter 6-10