Undercover Secretary 2

by Alana

 

Since relating my experiences as an Undercover Secretary back in the Seventies, I've received a lot of questions from readers about what I went through, and I thought I'd take a moment to answer some of them. If you have any more questions, don't hesitate to ask.

 

Q: I loved that floral dress you tried on. The one that you told Mary looked like something you would wear to a picnic. Did you ever wear it to work?

A: I wore it to work a few times. It was a relief to take a break from Mr. Robbins' groping and leering. Mr. Robbins mostly left me alone when I wore that dress. It was pretty, but it wasn't sexy.

I'm not saying he didn't grope me a little bit, but his heart wasn't in it. He'd go to grab my butt, and more often than not he couldn't even find it in those voluminous skirts.

Nothing of any note happened on the days I wore it. I went out to lunch with the girls in that dress, and at one point I forgot what I was doing, and I held the chair for one of the ladies. Women don't hold chairs for other women. I forgot that. I'd only been wearing dresses for a few days, at that point.

 

 

 

 

 

Q: What do you like the most about being feminine?

A: I didn't like anything about being feminine. But why should you believe me? No one else did. The theory was, if I didn't like wearing dresses and pantyhose I would've quit my job rather than go through that humiliation. Well, you don't just quit a job in Washington that you've been training for most of your life.

OK, what I liked most about being feminine was that it only went on for a month. There were times when I was afraid I'd be spending years in a dress.

 

 

 

 

 

 

 

 

Q: What styles does Mary like you to wear?

A: Well, she has a lot of smocked dresses.

 

 

 

 

 

 

 

 

 

 

 

 

 

She liked dresses with bows at the neck.

 

 

 

 

 

 

 

 

 

 

 

 

She had a lot of dresses with full skirts. I remember once when the air conditioning was not working, Mr. Robbins had a fan going on the floor, and every time I went into his office the fan blew my skirt all around. I was annoyed at first, but by the end of the day it got to be a nice relief from the heat.

 

Q: How do you manage to stay so slim to fit into a size 6??? I would love to know your secret. Are you a jogger?

A: No. I never exercised, unless you count wearing high heels and being chased around the desk by Mr. Robbins, which could be quite a work-out. I was just naturally thin. If it makes you feel any better, that was back in the Seventies, a long time ago, and now I weigh a lot more. I couldn't get my big toe into most of those dresses, now.

 

 

 

 

Q: Ever have any trouble with your slip showing?

A: No. The slips I wore were all fairly short. There was one black-and-white dress I wore that kind of embarrassed me. When I tried it on in the morning and checked myself out in the mirror, I didn't notice anything wrong with it.

 

But it wasn't until I got to work that I took a good look at my skirt and noticed.

My gosh! My skirt was completely sheer! You could totally see my slip!

 

 

 

 

 

 

 

 

 

 

 

 

 

 

I know that's not the same thing as a slip showing, in the conventional sense. But still, I was embarrassed all day. I kept walking with my hands in front of my skirt, hoping no one would notice. Finally, a woman asked why I seemed so embarrassed, and I told her.

She shrugged. "Well, you're wearing such a pretty slip. You might as well show it off," she said.

Why is a slip showing below the hem of my dress embarrassing, but apparently it's perfectly OK to wear a sheer skirt, or even a completely sheer dress, so that you can totally see my slip? Some of the rules of femininity I just will never understand.

 

Q: How did you get such a great looking set of legs?????

A: Please don't say that. I got enough of that talk from Mr. Robbins.

 

Q: How did things work out between you and Mary? Did you ever get married?

A: We never married, but we were together for about a year. By together, I mean we had sex a few times a week, but we never dated and we were never seen in public together. The trouble is, she had no interest in me when I wasn't dressed as a woman. She talked about marriage, but it was always with me in a wedding gown.

I can honestly say I never wore another dress after I finished my one month as an Undercover Secretary, but I had to wear plenty of lingerie in order to go to bed with Mary. Nylons, garter belts, teddies, split-crotch panties. You name it. I put up with it for a year for the sex, but finally I had to get out.

 

Q: I loved that cute short red dress you wore to work that one day. Was that the cutest dress you ever wore to work? Was it the shortest dress you ever wore to work?

A: I wish I could say that it was the shortest dress I've ever worn to work, or the cutest. But I can't.

This is what happened. One day I was wearing my magenta and white dress with the full skirt. I was taking dictation.

 

Out of nowhere, Mr. Robbins starts complaining about my dress, saying it's too long and he can't see my knees.

"Mr. Robbins!" I said. "The dress code says nothing about the length of my skirt! Company policy does not require me to wear a miniskirt to work every day!"

"It should," he said. I stood up.

"There's nothing wrong with my dress!" I said. "I've gotten a lot of compliments on this dress!"

 

 

 

 

 

 

 

"Not from men, I would imagine."

"I'm just a pair of legs to you, aren't I? That's all I am."

"On the contrary, you're also a nice pair of boobs and a great ass."

I couldn't believe he would talk to me that way, and I was used to some sleazy talk. I was mad about it all day, and I complained about it in the evening when I went home to Mary. She laughed and said, "Well, Melissa, if you really want to teach him a lesson, I've got the perfect dress for it."

She showed it to me. I put it on, and looked at myself in the mirror.

 

"My gosh! I look just like Minnie Mouse in this thing!"

"Well, Melissa," she said, "do you have the nerve to wear this dress to work tomorrow?"

"I think it would take a dress as ridiculous as this to make him realize how ridiculous he's being."

I don't know why I thought giving him what he wanted would punish him. Reverse psychology, I guess. Whatever satisfaction I was able to derive by going into his office in that dress and saying, "Well, is this short enough for you?" was more than undone by the way he treated me that day. I thought I'd seen groping and pawing before, but that was nothing compared to what I went through that day.

I wasn't used to taking dictation in a dress that short, or doing anything in a dress that short. I nearly wrote on my pantyhose a few times.

 

 

 

 

 

And then there was the time he called me into the office and said, "Melissa, I dropped some change under the desk. Would you pick it up for me, please? I've got a bad back."

As you can imagine, I had a hard time buying this.

"Really? Exactly how long have you had this bad back?"

 

 

 

 

 

 

"Oh, for quite a while, now."

What could I do? I squatted down and got his damn change for him, while he leered and got himself an eyeful.

 

 

 

 

 

 

 

 

 

 

I was a nervous wreck. And the men staring at my cleavage all day didn't help. I went into the lunchroom to get some coffee, and there was a young paralegal in his twenties. He tried to look away, but his eyes kept dropping down to my chest.

Finally, I just said, "Fine! Go ahead and look! Take a good look!" And I struck a pose for him.

 

 

 

 

 

He mumbled his apologies and quickly left. I was really treating him unfairly, but like I said, I was a nervous wreck.

I couldn't get any sympathy from any of the ladies, either. Apparently, if I wore a dress like that I was just asking for it.

So the next day I wore a more reasonable looking dress, and as soon as Mr. Robbins saw me he started complaining about it.

"Yes, I'm wearing another long dress!" I said. "Why don't you just spank me for it?"

 

 

 

 

 

 

He made a move toward me. He was actually going to spank me! No other man would've done that, but he was beyond shame, beyond chastisement. But I backed away from him in time.

"I thought we talked about this," he said. "I really liked that dress you wore yesterday. Why don't you wear something like that again?"

"You actually expect me to wear another short dress after the way you treated me yesterday?"

He laughed.

"OK. If you wear another short dress tomorrow, I promise to keep my hands off of you."

"You promise?"

"Promise."

So I went home to Mary's place, looking for another short dress to wear. She only had one dress as short as the red polka-dotted dress. I put it on and checked myself out in the mirror.

 

 

"It's worth it if he keeps his hands off me," I thought.

I slipped on the dress in the morning, and went into Mr. Robbins' office to make it clear that I'd lived up to my part of the agreement, happy that I'd be free of his groping for one day, at least.

 

 

 

 

 

 

 

 

 

 

 

And that was when it became clear that a promise to a woman meant absolutely nothing to him. He treated me just like he had before, groping and pawing me. When I reminded him of his promise, he just laughed.

I'm so glad I was instrumental in making changes to the law, so that creeps like Robbins get what's coming to them.

Q: Would you consider doing this time of undercover work full-time?

A: Never ever. I've done undercover work as an investigator since then, but always as a man. Thankfully, they've hired plenty of competent female investigators, so I hope no man will ever again have to do what I did.

Q: Why didn't you wear any jewelry?

A: Because Mary didn't.

Q: Did you ever get a run in your nylons?

A: No, I was pretty lucky. One day, when I was wearing my plum-colored silk dress, I thought I might have a run in my pantyhose, but it turned out to be just a shadow on my legs.

Q: Your lunchtime conversation with the women makes you seem to be something of a woman-hater. Are you?

A: On the contrary, I love women. But I don't always admire them. Still, since being an Undercover Secretary, I've come to realize that what seems to most men to be female incompetence is merely a woman having a hard time doing something in a tight skirt and high heels. Tasks that I would've had no problem with in loafers and a pair of pants proved to be next to impossible to do in a dress and high heels.

Q: Did anyone ever find out that you're a man?

A: Yes. Oh, I really didn't want to be telling this part of the story. This never came up in my testimony, and it was never publicly revealed. But, I've told the rest of the story, so I guess I might as well tell this.

I was wearing my short, colorful dress, going into the Ladies Room to pee. I really had to go. I know it was stupid to take this risk, but my dress was so short, and I just thought how easy it would be to just lift it up and pull down my panties and pantyhose and pee standing up. So I did.

A secretary named Jane came in and caught me at it. When she noticed me standing and peeing, she yanked open the door of the stall to confirm her suspicions.

"You're a man!" she cried out.

I got dressed as fast as I could and came out, tugging down my skirt.

"Yes, I'm a man. Please don't tell anyone."

"Tell anyone? I'm calling the cops!"

I explained, as quickly as I could before anyone came in, what I was doing there and that I was working for the government. She laughed.

"So you can see why I need you to keep quiet about my investigation."

"Fine. I'll keep quiet on one condition. I want you to go on a date with my brother Steve."

"A date?!"

"He's a womanizer. He deserves a date with you. Wear something formal. Something beaded, in white. White or gold. You two will have dinner in a nice place, and go dancing later."

"Dancing?! I can't! I can't do that!"

"Suit yourself. Ladies, you'll never believe what I just found out about Melissa," she said to two women who'd just entered.

"Fine! One date!" I said, and left.

When I got home I explained the situation to Mary. When she finished laughing, she said she had the perfect dress for me. A beaded dress, in white and gold. I tried it on.

It was attractive enough, but looking at myself in the mirror, I began to feel nauseous at what I would have to do in it. I put one hand to my stomach.

It was bad enough wearing dresses and going to work in them every day, but now I'd be going on an actual date! Dancing with a man and doing who knows what else.

I took off my dress and tried not to think about it ( I had been used to thinking of Mary's dresses as my dresses ).

The next day, at work, I was wearing my plum-colored silk dress. Jane came up to me with a camera while I was getting coffee. We were in the lunchroom. It was late afternoon and no one else was around.

"My brother wants a picture of you. He doesn't believe me when I say you're pretty. It's a little hard for ME to believe, tell you the truth, knowing what you're packing in your pantyhose."

"Please," I pleaded, near tears, "please don't make me do this."

 

 

 

"Oh, you're doing it, alright. And he'd better have a good time. You'll flirt with him and throw yourself at him and be all over him, or your secret is blown, Mister. Now smile!"

I smiled.

 

 

 

 

 

 

 

 

 

 

 

A few days later it was Friday night and time for the date. I took off the dress I was wearing and looked around for the beaded dress I was supposed to wear. I couldn't find it in Mary's closet. In my slip, I went out into the hallway and asked Mary where the dress was.

 

 

 

 

 

 

"I had it dry-cleaned," she said. "It's hanging up in the bathroom. You want to look nice for your first ever date!"

I got into that tight white beaded dress, and Mary kept saying things like, "My little Melissa, going on her first date! It seems like just a few days ago you were trying on your first pretty dress, and now here you are going out with your boyfriend Steve! He's going to make a real woman of you!"

I got out of there as quickly as possible.

I drove to the restaurant and parked. Fancy place. I waited around for him out front. I leaned forward a little, scanning the crowd for anyone with a photograph who might be looking for me.

"Hello, beautiful," I heard from behind me. I turned and smiled.

 

 

 

 

I knew what I had to do, though it made me sick. I turned and faced him and assumed the pose.

"Hello, handsome," I said.

 

 

 

 

 

 

 

 

 

 

 

 

 

I would describe him, but if I did I'd have to say how attractive he was, and I'd rather not make myself sound any gayer than I already have. We went into the restaurant. He held my chair for me and was charming and did and said all the things that womanizers do when they want to get laid. I smiled and flirted back. Jane hadn't said so, but I was pretty certain she was somewhere in the restaurant, and I had to give her a good show if I wanted to keep my secret. When we finished dinner, the music started and several couples headed out to the dance floor.

It looked like he wasn't going to ask, so I got up and asked, demurely, "Would you like to dance?"

 

 

We danced. He tried to kiss me several times, but fortunately I was able to give him my cheek each time. I have to say that, all in all, the date was not that horrible. I don't know what he'd done to make his sister so mad at him, but I thought he treated me pretty well. I'd take a hundred dates with Steve over one single day in the employ of Mr. Robbins, any time.

When we sat down, sure enough, there was Jane heading to our table for the big reveal. And it wasn't enough for her to just tell him I'm a man. No, she had to rip my wig off in front of everyone!

I was mortified. I grabbed my wig and my purse and ran out of there as fast as my high heels would take me. I got my wig on and got to my car as quickly as I could. I sat in the front seat, breathing heavily. I pounded on the steering wheel a few times in anger, and when I calmed down I drove home.

On Monday, when I saw her at work I wanted to get angry at her but I didn't dare. When she saw me, she said in a lowered voice, "My brother loved going out with you. He says he'd like another date. He doesn't even mind that you're a man."

"Shhh!" I said. "Be quiet."

No one heard her, but after that she kept saying things like, "Oh, Sir! That's an attractive dress you're wearing! Very manly!" Fortunately, it was always when we were alone.

Then one afternoon I was sitting at my chair, near my desk. That was the day I was wearing my shiny, tight, aqua-colored dress. I was exhausted, and taking a little break from typing. I was sitting in a kind of slovenly position, my hands resting on my skirt between my knees.

Jane came passing by, and said, "Oh, good idea, Sir. Better cover up that penis."

This with Mr. Robbins not four feet away, and the door to his office wide open! Lucky he was on a phone call, and didn't hear her.

I got so angry, I got right up and grabbed her by the elbow and took her into a conference room.

"Look," I said, "I did everything you wanted. I humiliated myself for your amusement, now you've got to live up to your end of the bargain!"

I was as angry as I've ever been.

 

 

 

 

 

 

 

 

 

"I haven't told anyone," she said.

"You might as well, the way you talk! Knock it off with the calling me 'Mister' and 'Sir' and talking about what I'm packing in my pantyhose!"

 

 

 

 

 

 

 

 

 

 

"Or what? Gonna hit me with your purse, tough guy?"

I tried to calm down. I talked about what I was there to do, how I hoped to make a difference in the law, make it hard for men like Mr. Robbins to treat women the way he did.

"I didn't ask for this job. Do you honestly think I wear dresses and pantyhose because I like to?"

"Well, maybe not. OK, you win. From now on, you're a woman. I'm promoting you from Mister to Miss."

"Thank you."

"And Melissa, that's really a lovely dress you're wearing, and I mean that sincerely and without any sarcasm. I wish I had your figure."

"Thanks."

After that, things were OK between us, and she never called me 'Mister' or 'Sir' again."

Q: Were there any things that were harder to do in a dress and high heels?

A: What wasn't?

I'd say the hardest thing to do in a dress and high heels was to bend down and pick something up off the floor. Mr. Robbins always made me so nervous with his leering and groping that I would drop my pad after taking dictation, and I'd have to pick it up.

 

 

 

Mary had drilled it into me that I couldn't just bend at the waist to pick something up, or I might reveal my underwear, and that wouldn't be ladylike.

 

 

 

 

 

 

 

 

 

 

I had to squat down to pick it up, which was a killer on the knees. And Mr. Robbins could always be counted upon to leer at me, hoping to see up my skirt.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

I have a feeling that in some of my dresses I wound up showing my underwear, regardless.

 

 

 

 

 

 

 

 

 

 

 

 

Q: Do you have any regrets about your assignment?

A: I regret that I ever had to do it in the first place. But I don't regret that my testimony was instrumental in getting the law changed. Some of the things that Mr. Robbins did and said would be unthinkable for any boss to do today, and I'm glad. I'm happy to have made a difference in the lives of women. Having walked a mile in their pumps, I know that their lives can be difficult, and if I've played some small part in making things easier for them, then I guess it was worth it.

  

  

  

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