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Perfect secretary
🕑 Added 2020-06-22 07:09:42 +0000 UTCSUMMARY - "A friend told me about a job opening back at Benefit Bros, actually," she said. "I know, I know, but listen. It's for a part-time secretarial position. You could apply as Lisa, not Larry.
Perfect secretary.
"Aw, that's too bad, honey," my wife said. She'd just gotten home from work,and we were in the kitchen, where I was making a penne arrabiata with spicy chicken sausage. She handed me a glass. "Here, have some Chianti."
I took a healthy slug. Some of it went down the wrong pipe, and I choked and coughed and gasped for breath. She thumped on the back, and I managed to breathe again, sort of.
It had been that kind of day.
I was usually in a good mood when I got home on Fridays. The boring insurance work was done, the entire weekend lay ahead, and my lovely wife, Jessica, usually dressed up for dinner, whether we were cooking at home or eating out. We had a cocktail or two before dinner and afterwards retired to the bedroom, where I tried to make her happy.
This particular Friday, though, I came home furious. Not at Jessica, who looked fabulous in her little black dress, but at my new boss, a guy named Brock Hunter. My old boss, who was great, had gotten herself promoted. I would have been a good choice to replace her, but I guess the brass didn't see me as management material. Instead, our VP brought in this guy from outside the department. As far as I could tell, he was a first-class prick, and I wasn't sure how long I could stand working for him.
Brock Hunter was the kind of guy who tended to get ahead at BenefitBros, the insurance brokerage where I worked. I was short, skinny and physically unimpressive. He was a beefy ex-jock who opened our interview with some sports chatter. When he realized I had no idea what he was talking about, he seemed to mentally dismiss me. He showed no interest in me, or my ideas about how our team should work, or anything else I had to say. We had a half hour scheduled, but he ended it after fifteen minutes.
"It sounds like you let him walk all over you," Jessica said. "If you could just stand up for yourself..."
"If I stood up for myself, I'd be eight inches shorter than he is," I said, feeling defensive. "Height matters to guys more than women realize."
"Length matters to women more than guys realize," she retorted.
Ouch. I wasn't what you'd call generously endowed, and had been having trouble satisfying her lately. I'm sure part of it was stress from work.
It didn't help that she knew I was unmanly in another way - which is that I liked to wear women's clothes. She was thankful that I was honest enough to admit it before we married, but she wasn't interested and didn't ever want to see me that way. "You're so petite that you might look cute in a dress," she told me once, "and I don't want a husband who looks cute in a dress."
Jessica was an inch taller than me in bare feet, three or four inches taller in heels. We wore the same size shoes. I sometimes wondered what she saw in me when there were so many bigger, stronger men around. Maybe it was my steady paycheck, or my cute little California bungalow just down the road from Disneyland, or my sense of humor – we were both Monty Python fans. Or maybe it was my willingness to let her take the lead in our relationship. She was an industrial designer and made more money than I ever would, and she liked to run the show at work and at home.
I was still in a bad mood when I returned to work Monday. I was expecting to have a rough week. My expectations were amply fulfilled.
Brock Hunter rode me hard, giving me totally unrealistic deadlines and getting angry when I failed to meet them. He started meeting with me after each supposed failure to discuss how I needed to do better, and I had a strong feeling that he was documenting it so he could fire me for cause. It was ridiculous. I'd always been one of the better analysts in the department. He was treating me like a new hire with no experience. What did he have against me?
On Friday a week later, he called me into his office to tell me that due to my poor performance, he was reclassifying - i.e., demoting – me from Data Analyst II to Data Entry Clerk I, and consequently cutting my salary by half. The demotion would take effect the following Friday.
"This is ridiculous!" I said. "It's completely unjustified! I'm going to go to Mr. Magna!" Mr. Magna was Brock's boss, the vice-president of our division.
"Go ahead, pussy," Brock sneered.
I fumed inside. That kind of personal insult was completely uncalled for - and so typical of him.
I managed to get fifteen minutes with Mr. Magna early the following week. He said he'd reviewed my case with Mr. Hunter, and Mr. Hunter had documented my drop-off in performance in convincing detail. Frankly, he said, I was lucky I'd been reclassified instead of terminated. He hoped to hear better reports of me in my new role.
When I told her the news, Jessica wasn't terribly sympathetic.
"You're not much of a man, are you?" she said. "You can't defend yourself at work. You're having trouble getting it up at home. Sometimes I wish you'd never told me you like to wear girls' clothes. I can't help picturing you in them now. The helpless little girl being bossed around by the big mean man."
"That's not fair!" I said. "This has nothing to do with dressing. Brock Hunter is just out to get me. I wish I knew why."
"From what you said, your VP didn't agree," she said.
"He just accepted everything Brock told him."
"Maybe you'd better do the same," she said.
The demotion took effect. I lost my office and moved into the cube farm, where I typed data into Excel. I was an Excel superuser, I could make spreadsheets dance and sing and fly through the air, but I wasn't asked to do that anymore. I just typed data into them. After a couple of weeks, I felt pain in my right wrist, and started wearing a brace at work. I hated my boss. I hated my job.
Things changed at home, too, but for the better, not worse. Or at least so I thought at the time. Jessica didn't belittle me when the demotion took effect. She seemed happier, calmer, more relaxed. And then one night she gave me a big surprise.
"I've been thinking," she said. "Things are tough for you right now, and I've been so tied up with work, I haven't shown you much sympathy, have I? You need something in your life to make you feel good."
"Mmm," I said, hoping she was talking about a blowjob.
"That's why I've decided to let you start dressing up at home," she said.
It was the last thing I expected to hear from her. "You mean...?"
"In women's clothes. You may wear whatever you like at home. Even if I'm around. Preferably not when we have visitors, but that's your call."
"Wow! Of course not with visitors. Thank you, dear! What made you change your mind?"
She shrugged. "Like I said. You need a way to relieve stress by doing something you enjoy. I shouldn't stand in the way of your happiness."
"You're sure? I don't want to make you feel uncomfortable."
"I promise not to feel uncomfortable. In fact, I'll help you. It'll be good for us to deal with this. Do you have things to wear?"
"Not much. One outfit."
"Where?"
"An old suitcase out in the garage."
"Do you ever wear my clothes, Larry?"
"No! I'd stretch them out. You'd catch me. Disaster."
She smiled. "I don't think you're big enough to stretch out my things, honey, but thanks for not borrowing them. We'll go shopping for you on Saturday."
Friday night, she made me take a bubble bath and shave or Nair myself everywhere below my neck. She showed me how to moisturize myself afterwards, and lent me a long nylon nightgown that was the softest thing I'd ever worn. I was smooth like a girl, I was soft like a girl, I smelled like a girl. It was bliss - and dreadfully embarrassing. Jessica seemed to take it in stride, for which I was grateful.
The next morning, she told me she wanted to see the women's clothes I had. I brought in the suitcase and laid its contents on the bed. A pair of panties, a bra, a full slip and a plum-colored, knee-length dress with a fitted bodice and a full skirt.
"Put them on," she said.
I took off the nightgown and put on the panties, bra, slip and dress. I could feel my face blushing. She tugged at the dress and smoothed it over my torso. I almost fainted from pleasure as the slip and skirt swirled around my knees.
"That's actually a rather pretty dress," she said. "Why don't you wear it shopping today? Iron it first."
"Don't be ridiculous!" I said. "I can't go out dressed as a woman."
"You'll have to try things on, and stores don't want a man using the women's dressing room." she said. "It'll be much easier if you're in a dress."
"I'll look like a man in drag!"
"You'll be surprised how feminine I can make you look. Let me try it, and then let's decide."
I was skeptical, but in the end, I agreed to let her make me look like a woman. I wondered why she'd completely changed her mind about letting me dress up, but decided not to ask. Best to leave well enough alone.
Jessica had me take off the dress. She stuffed the cups of my bra with silk scarves and handed me a new package of thigh-high stay-up stockings. "These are yours now," she said. It felt wonderful to draw them up my smooth, hairless legs. I slipped my feet into a pair of her shoes, sensible black pumps with two-inch block heels.
She told me to sit at her vanity, where she put daytime makeup on me: foundation, powder, eyeliner, eyeshadow and mascara, with plum lipstick and nails to match the dress. She added a pair of clip earrings, a pretty scarf, and a black handbag. A lady's watch went on one wrist, a bracelet on the other. She combed my shoulder-length hair into a center part, trimmed it in a couple of places, blow-dried it, and added two little butterfly hairclips to make it frame my face. A few dabs of perfume completed my instant makeover.
I looked in the mirror and did a double take. Larry was gone, replaced by a pretty woman in her late twenties.
"My God, what have you done?" I said.
"I think I just proved that you're pretty enough to go out in public. Some women might notice if they look at you closely, but men won't. They'll think you're cute."
I did not want men to think I was cute. I stared at myself in the mirror. "You once told me you didn't want a husband who looked cute in a dress."
"That was before I saw you look cute in a dress," she said. "It's a nice cute."
"You can undo all this by Monday, right?"
"Sure," she said. "But you're too pretty to be Larry now. You need a girl's name. What do you call yourself when you're dressed up?"
"I don't call myself anything."
"Really? Okay, how about... Lisa? From Larry to Lisa. Yes! I think I'll call you Lisa whenever you're in girls' clothes. When you're in boys' clothes, I'll call you Larry."
We climbed into her car - she chivalrously opened the door for me - and headed up State College Boulevard. "We'll go to Brea Mall," she said. "It has nice stores and isn't as busy as South Coast Plaza."
I couldn't believe I was doing this. I was about to go out in public dressed as a woman for the first time. I almost died of fright en route, nervously clutching my purse in my lap.
Jessica parked at the far end of the parking lot. As I click-click- clicked my way across the asphalt, she quietly reminded me to slow down, take smaller steps in a straight line, don't swing my arms so much, pull my elbows into my waist, let my forearms dangle, limp wrists thrust out my fake boobs, swing my hips stand up straighter slow down smaller steps.
Inside, I braced for disgrace. It never came. Either I looked feminine enough, or people were cool enough to pretend not to notice. Either was okay with me. What I didn't want was some woman pointing her finger at me and screaming, "Look, it's a guy in a dress!"
Jessica steered me from store to store and did most of the talking. The salesgirls all treated me politely. I won't mention brands, but we bought a week's worth of sumptuous lingerie, nightwear and day dresses similar to the one I wore, with tailored bodices, short sleeves and full skirts. Jessica also bought a couple of crinoline petticoats to wear under them and several white cotton aprons in various styles.
"Why the retro look?" I asked.
"Because it's the most feminine style of the past hundred years," Jessica said. "My grandmother dressed this way every day... she was so beautiful. Full skirts look good on you. They hide your lack of hips."
We hauled armfuls of bags to the car and stuffed them into the trunk, and then returned to the stores for the rest of what I needed. Heels. Hosiery. A scary-looking waist cincher. My own makeup. Perfume. Nail polish. Earrings - Jessica insisted that I have my ears pierced with pearl studs.
"Jessica, this is crazy! I don't need this much stuff. We must have spent a thousand dollars so far."
"Not quite. This is an investment in your happiness, dear. Let's go home and get you all prettied up."
I spent the rest of the day wearing one of my new dresses, a beautiful floral print in purple, blue and green, with a white Peter Pan collar. I loved the swish of the dress and petticoats. I was less enthusiastic about the waist cincher and heels. The strangest feeling was wearing a garter belt for the first time. The garters slid under my panties and over my legs, stretching and tugging at me with every step, constantly reminding me of their presence.
At first, I wore my new female wardrobe only when Jessica asked me to, for example by asking if Lisa would cook dinner tonight. Gradually I began wearing dresses more often - housework was more fun when I was properly attired for it - and after that it wasn't long until I was changing into a dress every evening as soon as I got home. I had two completely different wardrobes now: female at home, male at work.
It wasn't long before Jessica asked me to start wearing panties under my work clothes. I was scared of being found out, but no one seemed to notice. I feared she would make me start wearing a bra at work, bu fortunately she did not. She did, however, throw out all my male underwear, except for a pair of boxers that she kept for doctor's visits and such. I was a fulltime panty boy now.
Brock had bad news for me at work. He called me into his office and said the company was reducing my hours from fulltime to thirty hours a week, the minimum needed to get employee benefits. A quarter of my income vanished. I asked him why. He said cost control.
I nervously reported this development to Jessica, who to my great relief did not take it hard.
"Ten fewer hours a week?" she said. "That's great! Ten more hours a week for your domestic chores. You can start by hand-washing my delicates - our delicates, I should say! - and doing the ironing."
Two weeks later, Brock cut my hours to twenty a week, and two weeks after that, to ten. "Cost control," he said. I'd lost three-quarters of my income and was no longer eligible for benefits. Fortunately, Jessica could add her spouse to her health insurance and did.
Over dinner one night, Jessica asked, "Why don't you just quit that stupid job? We'd save on gas and parking, and you wouldn't need to keep a separate business wardrobe."
"But then I'd be totally dependent on you," I said. "You'd be the breadwinner, I'd just be a house husband. Can you support both of us? Do you want to?"
"Oh, yes," she said. "Though I think you'd be more of a housewife than a house husband. My pretty little housewife, Lisa, gracefully mincing from room to room in her dress and high heels, looking lovely as she does her chores."
The thought made me stiff. "Okay, I'll quit. No more Brock Hunter!"
So I quit my job, and took satisfaction in telling Mr. Hunter I was outta there. He didn't seem that surprised. I didn't care. No more data entry! I threw away my wrist brace.
I was now a fulltime homemaker. I did all the housekeeping, except on the rare occasions when Jessica wanted to cook. She was working close to fifty hours a week, and had no time for housework.
A couple of weeks later, Jessica had a talk with me during dinner.
"It's so nice having you here all the time, and the house looks lovely, but I think you need to start getting out and about and seeing more people," she said. "As a woman."
It was a scary thought. "Is that necessary? I can wear panties under my boy clothes..."
"You don't need boy clothes," she said. "You look good as you are. All you need is practice. I'll coach you on deportment."
"Where would I go? What would I do?"
"A friend told me about a job opening back at BenefitBros, actually," she said. "I know, I know, but listen. It's for a part-time secretarial position. You could apply as Lisa, not Larry. They always hire women for these jobs, and you can easily pass. The work would keep your office skills up to date, and we could save your entire paycheck."
I told her I was a little reluctant to return to BenefitBros because there was a chance I'd run into Brock Hunter, and he might recognize me. Jessica told me not to be silly. It was a big company, there was little chance I'd see him, and absolutely no chance he'd recognize Lisa as Larry.
I wasn't sure why she wanted me to interview for a new job at BenefitBros so soon after quitting my old one, but since I was now her dependent, I took her wish as a command. I updated my resume and sent it to her, and she forwarded it to her friend, and a few days later, I got email from an HR person setting up a job interview for Friday. I told Jessica.
"That's great!" she said. "But you know what this means, don't you?"
I shook my head.
She grinned. "It means we need to go shopping! I want you to go to your interview dressed as the perfect secretary."
"Uh... shouldn't I get the job before I start dressing for it?"
"No! Dress for the job you want, not the job you have."
Jessica took me up to Brea Mall again that afternoon. She selected a black wool pencil skirt so tight that it shortened my steps, which she said was a good thing anyway, and a semi-sheer white pussy bow blouse with puff sleeves. She also bought me a lacy white camisole to wear under the blouse to hide my bra, and a half slip to keep the skirt from riding up. Jessica suggested I take off my wedding ring, to avoid questions about the husband I didn't have.
She took me to her salon to get my hair done, and the stylist trimmed it into a pretty wedge cut with bangs that fell naturally across my forehead. She also trimmed and shaped my eyebrows, making my face noticeably more feminine.
On the morning of the interview, she gave my hair a quick blowout and did my makeup - a professional daytime look livened up by blood-red lipstick and nails. I dressed in my secretary skirt and blouse and posed for her approval. She fetched a bottle of her perfume and touched the nape of my neck, between my breasts and the backs of my knees. With an air kiss, she sent me on my way. "Go get 'em, tigress!"
The receptionist at BenefitBros, a cute blonde in a miniskirt, told me to wait and called HR. An HR person appeared and escorted me back to HR, where the HR people did their HR thing. I ended up in an empty interview room, where I carefully sat in a ladylike way and waited for five minutes. I could smell my perfume.
The door opened. I looked up. In walked Brock Hunter.
I gasped in shock. I reminded myself that he'd never seen me as a female. To him, I wasn't the failed Larry, I was a job candidate named Lisa. I feared my last name would remind him of Larry, but he didn't bring it up. He asked me standard interview questions that were easy to answer, and in half an hour we were done. He openly ogled my legs throughout our discussion, and when we shook hands, he held mine a moment too long.
As I stood and picked up my handbag, Brock looked me up and down. "I hope you won't mind my saying that you are perfectly dressed for this position."
"Why, thank you, Mr. Hunter," I said, simpering. He was such a pig.
He took me back to HR, where the HR people did more HR stuff and told me I'd hear back within a week.
As I drove home, I tried to puzzle out why my interviewer had been Brock, of all people. Was it just a coincidence? He'd shown no sign of recognizing me as Larry. But why would he be interviewing a part-time secretarial candidate? He ran the analytics group. Someone else managed the secretarial pool.
I had a scary thought: What if he interviewed me because the position was to be his secretary? I pictured myself sitting in the secretary station outside his office, answering his phone, having to come whenever he called me, getting him coffee, ordering his lunch, running little errands for him while he leered at my ass. It was a horrible thought.
I'd disliked him enough when I was a male analyst and a data entry clerk. A female secretary would be even lower on Brock's totem pole, and I'd never seen Brock give any consideration to those lower than him on the totem pole.
How did Jessica hear about the job? She didn't know Brock or anyone else at BenefitBros. Maybe one of her online friends told her. I could ask her when she got home. I decided to stay in my secretary outfit to greet her.
She breezed in the door. "Mmm," she said. "You look ready to take some dictation! How did your interview go?"
"You won't believe it. I got interviewed by Brock Hunter."
Jessica's eyebrows rose. "Your old boss? Why?"
"Maybe just a coincidence. Or maybe because the lucky winner will become his secretary."
"Oh, dear," she said. "He didn't recognize you, did he?"
"Not as far as I could tell. He spent more time looking at my legs than my face."
"I wish I had your legs. Maybe he'll be nicer to cute little Lisa than he was to wimpy little Larry."
The phone call came the following Tuesday. By then I was a nervous wreck. I didn't really want to be a secretary. I certainly didn't want to be Brock's secretary. But Jessica wanted me to take the job. She wanted me to spend time outside the house. She was right, it would be healthy to get out and learn to deal with people as a woman.
"Ms. Lisa Curthose?" said the HR voice on the phone. "I'm pleased to offer you the job you applied for." She said I'd be working four hours a day, five days a week.
"Do you know who I'll be working for?" I asked the HR voice.
"No. You'll be assigned to a supervisor before you start work, which will be next Monday, if that's convenient. Ask the receptionist for HR."
I thanked the HR voice, hung up and returned to mopping the kitchen floor in my housedress. After I finished my chores, I changed back into my secretary outfit, just to show off to Jessica. I had to wait, because she now had a weekly meeting that lasted until seven o'clock on Tuesdays. She was not happy about it.
Jessica was delighted to see me in my narrow skirt, frilly blouse and heels. "Congratulations! You must have really impressed them with your outfit! And whatever you said."
"Jessica, why are you so eager for me to get this job?"
She stroked my hair. "I liked it better when you were working part- time. You'll have enough time to do all your housework, but you'll get to spend time outside the house as a woman, as Lisa. And the money will be enough to notice."
"Yes, but... a secretary? It's so humiliating! I was an analyst, and now I'm the office help. In a skirt! And what if I have to work for Brock?"
"Let's not worry about that unless it happens, dear."
I realized that I would now be dressing as a woman twenty-four hours a day. I'd be changing clothes three times a day, into a secretary outfit in the morning, then a housedress with petticoats and an apron in the afternoon, and then ladies' nightwear before bedtime. When I mentioned this to Jessica, she said we needed more closet and drawer space. She had me box up all my men's clothes, seal the boxes with duct tape and move them out to the garage, for emergency use only.
That weekend, Jessica took me shopping again for a week's worth of secretary wear: more narrow knee-length pencil skirts and more frilly, semi-sheer blouses in various pastel colors. She also bought me more camisoles, to hide my bra under the blouses.
On Monday, I got up early and took a bubble bath to calm me down. Jessica did my hair and makeup before I got dressed. The secretary outfits were like a uniform - it hardly mattered which skirt and blouse I chose. In a way, it was like being a man again, when I could wear any dress shirt with any suit.
Of course, my clothes felt completely different from anything I ever wore as a man. I felt like I was a decorative object now, clad in soft, sexy, close-fitting garments that crushed my waist, restricted my movements and made my feet hurt. I was aroused by the susurration of my skirt, lingerie and nylons as they slid over my body.
The receptionist at BenefitBros sent me up to HR for first-day orientation and training. I got my ID and was pleased with the photo. Usually they look like police mugshots, but mine showed an attractive woman in a pretty blouse and perfect makeup. It wasn't until the end of orientation at noon that I found out who I'd be working for.
Curse! Damn! Brock Hunter. Just as I'd feared.
I called Jessica, but she wasn't picking up. I was free for lunch now, but couldn't bear the thought of eating. I locked myself in a stall in the ladies' room, trying not to cry and mostly succeeding.
I reminded myself that Brock didn't know Lisa, that it was a fresh start for me, but I couldn't overcome my fear that it would be like when I worked for him as a man, or worse. He would sneer at me, denigrate me, undermine my status, and there was no way I could resist him physically, mentally or emotionally.
Dressed as a woman, I was far more vulnerable. In my tight skirt and heels, I couldn't run from him, I couldn't escape him. If he chose to grab my ass or play with my tits, I couldn't possibly stop him. What would I do if he tried to kiss me... fondle me... spank me at work because I was a bad girl...?
Stop it! I was starting to think like a bimbo. I had to be a tough career woman, prepared to push back against any in appropriatebehavior. Push back... don't let him pull me toward him... his hands around my cinched waist... grinding his groin against me... pushing me to my knees... shit, I'm stiff again! Stop it!
It was almost one o'clock. I was due to report at my new workstation outside Brock's office. I fixed my makeup in the mirror, left the ladies' room and hurried to my desk to avoid being late. I didn't want to get off totally on the wrong foot with him the way Larry had.
His office door was closed. I hesitantly knocked. "Come in," he said.
I opened the door and presented myself to him. I mean, I didn't curtsy or anything like that. But I straightened up, posed with one knee in front of the other, pointed my fake boobs at him, put one hand on my hip, and hoped he didn't mind if his new secretary had a skinny ass.
"Hello, Lisa," he said. "Welcome to BenefitsBros. When I saw the photo you attached to your job application, I knew you'd be perfect."
"Perfect?"
"You should call me Mr. Hunter, or sir."
"Yes, sir, Mr. Hunter, sir." My mild sarcasm was lost on him.
"You're perfect for me because of your qualifications," he said. "You can type eighty words a minute. You've used Excel. You seem to know how to obey orders. And you are very attractive."
"I don't think you should comment on my personal appearance, sir."
"Oh, Lisa! I hope you're not one of those girls who get all upset if someone compliments them. You look completely professional, and will be an outstanding asset to our company. Please stand up and turn around for me."
Asshole! What was I, a lingerie model? Oh, Jesus! I was getting hard again. Nevertheless, I obeyed. Stood, turned, twirled at his request. One nice thing about twirling in a tight skirt is that you're in no danger of exposing your panties. But...
"Wow! Old-fashioned stockings and garters? Lisa, you and I are going to get along just fine. I like your top, too."
Of course he did. Jessica had me wear my prettiest camisole, and he was leering at it through my sheerest blouse.
"Mr. Hunter, sir, perhaps we should discuss the work you want me to
do."
"Well, I don't need you to take dictation or type letters. I do my job in email, IM and Zip. What I need you to do is support me in face-to- face meetings with current or potential customers. Sort of like being a hostess. We're in a conference room. You serve coffee at the beginning of the meeting. You remove the used cups and saucers and wash them afterwards. Sometimes there are refreshments, little pastries and such, and you serve those. Understand?"
"Yes, Mr. Hunter."
"Now, when you're not serving, your job is to stand near me, as my assistant, and pose yourself in such a way that our customers can't take their eyes off of you. Slowly and discreetly, you display your legs, you stick out your boobs, you swivel your hips, or whatever it is that girls do to attract men without openly flirting with them. You're there to give them something nice to look at while they listen to me talk."
I gulped. "Sir! That is so sexist!"
He snorted. "Sexist? Bullshit! Why shouldn't we use your gorgeous looks to gain a competitive advantage? Don't be ridiculous. We expect every employee to do what she can to help us win."
This felt so wrong that I didn't reply. He expected me to be a corporate bimbo in front of strange men?
"You agree, Lisa?"
I decided to be brave. "I won't let you use me as a sexual object, sir!"
He stared at me. "Did I mention sex? I did not. Frankly, I'd rather customers not touch you, though it won't be the end of the world if a hand occasionally wanders. I'm talking about helping to create a positive mood, making customers feel pleased to be meeting with us, so that they lower their guard and become more cooperative. You serve them coffee to please their senses of taste and smell. You strike an elegant pose to please their sense of sight. It's all the same thing, really."
It was not the same thing at all, but I didn't want to get into a big argument with him right now. I let it go. I would ask Jessica how to handle this. Maybe she could teach me some simple, non-slutty ways to draw men's eyes. Actually, now that I was living as a woman, it would be a useful thing to know.
Somehow I got through the rest of the afternoon. He had Kelli, the buxom secretary for the manager in the office next door, show me my secretary workstation - a small sit/stand desk, chair, file cabinet and rolling chest of drawers. She showed me how to work the phone system. I could put calls on hold and forward them to Mr. Hunter. The desk had a not very impressive laptop locked to it with a steel cable. I wouldn't be able to take it anywhere. I guess I wouldn't be needing it at meetings if all I did was serve coffee and buns - the baked kind, and mine.
The desk didn't have a modesty panel. I would have to remember to keep my knees together or cross my legs. Neither was comfortable, not even with my male bits tucked back inside my panties.
Kelli came across as a total ditz. She, like, spoke fluent Valley Girl. She wore a tight black skirt that must have been six inches shorter than mine, and an equally tight blouse with one too many buttons undone. Too much makeup and perfume. Bleached blonde hair in a high ponytail with a hot pink scrunchie, same color as her lips and nails. Heels an inch taller than mine. She didn't walk, she teetered. Her ass undulated in ways mine could not.
Bimbo or not, Kelli knew how the place worked. She showed me how to log on to the network and where to find and store documents. She looked up my new email address.
"That asshole!" she said. She pointed it out on the screen: legs@benefitbros.com. "Brock's little joke, ha ha. You do have nice legs, but really! I'll have IT change it from legs to lisac."
She filled me in on how the secretaries on this floor shared housekeeping duties - washing coffee cups, keeping the refrigerator clean, ordering and serving food at meetings, and so on. Of course, the men didn't do any of it. She assumed I'd do my share of the work, and I couldn't think of a reason why I shouldn't, now that I was just a secretary.
When we were done, she lowered her voice and gave me some free advice. BenefitBros was definitely about the bro, not the sis. My stupid email address was a typical form of hazing. The bros sometimes behaved as if the company was a frat house and the secretaries were sorority babes. She would teach me which men I should avoid riding with on the elevator. "We girls need to look out for each other," she said.
"We sure do," I said. "Thanks so much, Kelli." Air kiss.
By the time I got home, I felt utterly drained. The shock of having to work for Brock Hunter again hadn't worn off. Nor had the shock of how he described my job. I was basically a waitress and a booth babe, there to serve the boys and draw their attention. It was utterly humiliating.
"Aw, that's a shame, honey," Jessica said when she got home and I told her about my day. "He really wants you to strike sexy poses?"
"He mentioned my breasts, legs and bottom. He said I should use my looks to make customers feel welcome."
"Did he want you to, um, accommodate them sexually in any way?"
"No. He said he preferred that they not touch me."
"Well, then, that doesn't sound so bad, does it? What if I taught you how to capture a man's attention without acting like a slut?"
"Could you? Is it hard?"
She stared at my crotch, hidden under my housedress. "I don't know. Is it?"
I blushed. "Yes."
She smiled. "Well, go put on your secretary outfit, and let's teach you how to produce that effect on men." She described and showed me a number of techniques and made me practice them in front of a mirror.
She taught me to be bold and coy at the same time. Look deeply into his eyes, give him a secret smile, submissively look away. Do this for each male in the room.
She taught me to be happy. Smile always. Be bubbly. Make your personality sparkle.
She taught me to use my hair. Touch it, play with it, pat it, flip it, wind a curl around your finger, tuck a tendril behind your ear.
She taught me how to use my eyes. When to meet his eyes, when to look away, when to look down, when to bat my lashes.
She taught me to wear perfume. Few men could distinguish between perfumes, but almost all of them found scent sexy - and since I was usually the only woman in the room, I didn't need to use much. The men would know it was mine.
She taught me not to cross my arms or legs when standing. Leave your body open and inviting.
She taught me how to do an ironic curtsy. Not a real curtsy, no one did those anymore, but a quick, tiny dip to show gratitude or pleasure. I could follow up by covering my mouth to giggle, as if I'd caught myself being too girly.
She taught me to make tiny adjustments to my clothing. Fix a bra or slip strap that isn't slipping. Play with the neckline of your blouse. Run a thumb inside the waistline of your skirt. If seated, let a shoe dangle from your toes. If wearing a full skirt, keep it in motion. Swivel your hips, shift your weight from heel to heel, swish a fold of the skirt back and forth.
It was so embarrassing to learn how to behave in these stereotypically feminine ways, but Jessica told me to feel no shame. They were stereotypes, she said, because they worked. Men were simple creatures who responded to stimuli in predictable ways. Every woman knew these things, though many chose not to use them these days.
I thanked her for revealing her girly secrets and practiced them in the mirror on Tuesday while Jessica was at her late meeting. When I met with Brock the next day, I started using Jessica's techniques on him without telling him, just as a test.
They worked. I saw the evidence in his eyes and in his trousers. He was not a small man. He treated me more nicely than usual for the rest of the day. I don't think he realized it.
The following Monday, Brock asked me to show him how I would sustain men's interest in me during his presentation. I didn't confess I'd already used the techniques on him. Instead, I told him that I was still learning, and then, as he ran through his slides, I employed most of them. He had to adjust his trousers twice.
"Great progress, Lisa," he said. "Couldn't take my eyes off of you. You're ready to start attending customer meetings. I'll get you added to the invites."
I felt proud of myself - then immediately felt shame for taking pride in such behavior. God, I was a mess. A semi-slutty secretary at work, a submissive housekeeper at home. I was a man, but nothing of my male life remained. I realized that I didn't miss it - not the rough, ugly clothing, not the constant competition with other males, not the implicit threat of violence, not the constant mindless sports chatter.
I began serving as the hostess for Brock's business presentations, greeting visitors, serving them whatever we decided to serve, and then giving them something to look at besides Brock's PowerPoint. It wasn't hard to compete with Brock's PowerPoint. I kept informal track at meetings and knew I captured more eyeballs than his slides did.
Did it pay off in more deals signed? I asked Brock once. He smiled, patted my head and said I didn't need to know the numbers, but he was very pleased with my contributions to his presentations.
"You're a good girl, Lisa," he said. "You make an excellent secretary, even if you don't spend your days typing letters. I've had problem employees in the past, people I needed to manage out of the organization, but you, my dear, are a keeper."
I curtsied and simpered, pleased that he didn't recognize me as one of his problem employees in the past.
He moved closer to me. "I'm very happy with you, Lisa." He reached out and stroked one of my boobs.
No! They were fake! I abruptly turned away from him. He ran his hand down my back and cupped my ass. At least it was real.
I backed away. "Please stop touching me, sir."
"Don't you like it, Lisa? Doesn't it feel good?"
"I don't like anyone touching me without permission."
"Sir," he said.
Argh! "I don't like anyone touching me without permission, Mr. Hunter, sir! Please stop it at once."
He stopped. I knew he didn't care whether I liked it or not. Maybe he thought I'd report him to HR or call the police or something.
"That way you have of being flirtatious without actually flirting," he said. "You do realize it has the same effect on me as it does on the other men, don't you? I'm only human. You can't blame me for reacting the same way they do."
"Yes, I can," I said. "You're my boss. It's totally inappropriate for you to grope me in your office. I'm going to feel embarrassed every time I see you now."
"Well, I'm sorry, Lisa. Why don't you take the rest of the day off? Maybe you'll feel better tomorrow. Are you having your period?"
"Mr. Hunter! How dare you ask me such a personal question!"
"Sounds like you are. Sorry, just joking! See you tomorrow."
What a dickhead! I sighed. "Yes, Mr. Hunter."
Weeks passed. Life at work did not improve. Every presentation with Mr. Hunter was a humiliating experience. I didn't mind serving coffee, but I hated standing there using my girlish wiles to titillate the audience while he did all the talking. I didn't like the way too many of the men looked at me, like a piece of meat instead of a human being.
Things got worse when he called me into his office one day. He asked for two changes in my office attire. He wanted me to shorten my skirts by six inches, to match Kelli's, and he wanted me to wear taller heels.
I talked to Jessica that night, and she said it was legal for my employer to have a dress code as long as it was related to my job. Since my job was basically providing hospitality for Mr. Hunter's audiences, he could argue that the length of my skirt and height of my heels were job-related.
This made no sense to me. If that was the case, I told her, why couldn't Mr. Hunter just order me to strip down to my lingerie during his presentations? That would do an even better job of pleasing his customers.
Jessica advised me not to put ideas in Mr. Hunter's head. It would be safest just to do as he said. If restaurant hostesses and waitresses could be required to wear short skirts, so could I.
But, she said, I should ask to be reimbursed for the cost of updating my office wardrobe. I'd need to have all my skirts shortened or replaced, and I'd need to replace my slips and my work shoes, and might have to change the hose I wore, too. It could easily run to hundreds of dollars - and it would be a subtle way of getting back at Mr. Hunter for changing the dress code on me.
I drastically shortened one of my skirts, bought a sluttier and more diaphanous blouse, borrowed some four-inch heels from Jessica and wore it all to work. I asked Mr. Hunter if this look was what he had in mind. He eagerly nodded. I asked him to reimburse my costs, and he agreed immediately. I had a nice shopping spree with Jessica and submitted the receipts as an expense report. It sailed right through. I should have bought more things!
He left a pretty bouquet on my desk the next morning with a note: "Thanks. Brock." I was totally embarrassed to receive flowers from a man, especially from him. I also got a dollar-an-hour raise, which for twenty hours a week times fifty weeks was another thousand bucks a year. Much nicer than flowers.
The other secretaries instantly noticed the changes in my wardrobe, and some of them got catty about it. They didn't say anything to my face, but there were things like Kelli saying that Anne heard that Fujiko said Maria told her that Lisa looks like she's putting out for Mr. Hunter. Which of course I wasn't. There was nothing I could do about it. For women, gossip seemed to be like breathing: something you did automatically because if you stopped, you died.
I lived as Lisa 24/7 now. I hadn't worn men's clothes for more than a month. The shrinking male part of me had to wonder how and why this all happened.
The big change was in my loving wife, Jessica. For our entire marriage, she'd barely tolerated my love of female attire. Then suddenly she'd decided it was acceptable and, in fact, started encouraging me to dress up. When was that? Right after Brock Hunter became my boss... about the time he demoted me from analyst to data entry clerk. In fact, as I recalled, Jessica let me start dressing when I was being demoted, as a way of reducing stress and cheering me up.
It worked. Jessica was still working overtime, so I was happy to play the housewife's role. I was much less happy working as a secretary, thanks to Brock Hunter, but it was only twenty hours a week, eight to noon, so I had plenty of time for housekeeping. I liked wearing a housewife dress while doing my chores, and Jessica liked coming home to a clean, tidy nest.
It was curious that I'd ended up playing feminine roles both at work and at home, because it was for completely different reasons. At work, it was because I'd just quit as Larry and they certainly wouldn't rehire him, so I applied as Lisa for a traditionally female job. At home, it was because my wife let me indulge a long-suppressed desire. It was just a strange confluence of events that resulted in me dressing as a woman in both parts of my life.
Or was it?
One evening, after I finished doing the dishes, Jessica called me into the living room and handed me a present - three presents, actually.
She told me to open the medium-sized box first.
It contained a light pink satin dress trimmed with white lace. The bodice was tailored, but the skirt was quite full. A dance costume? Bridesmaid's dress?
"Thank you, Jessica. It's very pretty. What...?"
"Now open the big box."
I set down the dress and opened the box. It was giant mass of white taffeta that turned out to be a ruffled petticoat, fuller than the net crinolines I wore at home. It made a rustling frou-frou sound as I held it up to look at it. It obviously went with the dress. I loved it. I stiffened.
"And the small box."
Inside it, I found a white cotton pinafore apron with a ruffled hem and shoulder straps, and a little white cap decorated with ribbons and lace.
"Oh! A maid's uniform!" I said. "You want me to be your maid?"
"Only on special occasions," Jessica said.
I ran my fingers over the pink duchesse satin. Mmm. "Is there a special occasion coming up?"
"Yes. I'm having a dear friend over for dinner on Friday. I'd like you to wear this uniform to serve cocktails and dinner. Set the table for two. You can eat in the kitchen later."
"I'd rather not dress as a maid in front of anyone else, even if it's a woman," I said.
She ignored my weak protest. "Cocktails at seven-thirty, dinner at eight. I'm thinking a tomato basil soup, pan-seared scallops, lamb chops with rosemary, a Caesar salad and tiramisu. Sauvignon blanc with the soup and fish, pinot noir for the entrée and salad, coffee and port with the dessert. You don't have to make the tiramisu, you can buy it."
"Yes, ma'am. Um, should I call you ma'am when I'm dressed as a maid?"
"I rather like the sound of that," she said happily. "Very appropriate for a maid."
On Friday morning, I went shopping for ingredients in my housedress. I took a bubble bath in the afternoon and then started to get ready for the evening. After moisturizing and powdering myself, I put on my lingerie and hose and the new taffeta petticoat. Jessica did my hair and makeup, and I redid my nails in the same shade of pink as the dress.
When I was perfect, she lowered the maid's dress over my arms, pulled it down my body and zipped me up. The skirt slid deliciously over the taffeta petticoat, which I decided was the most feminine garment I owned. The princess seams of the bodice added curves that my body wished it had.
Jessica helped me into the apron, tied it tightly behind me, and fluffed up the shoulder straps. She pinned the frilly white cap into my hair. I stepped into four-inch white pumps and I was done, a pretty pink maid for the evening. I felt absurd... but I was fully erect under all the prettiness.
Jessica left to get dressed, and I started working on dinner. Right at seven-thirty, the doorbell rang.
"Get it, Lisa," Jessica called from the bathroom.
I opened the door and froze. There stood Brock Hunter.
"Hello, Lisa," he said with a wicked smile.
Oh, my God. "M-Mr. Hunter!" I blurted out. "What are you doing here?"
He smiled. "Isn't the maid supposed to invite guests in?"
"Uh... please come in, sir." I curtsied automatically.
"Thank you, Lisa," he said politely. "I must tell you that you look absolutely delicious in your maid's uniform. Is it new?"
Totally confused now, I tried to figure out what was going on.
Jessica didn't know Mr. Hunter, except as a name I complained about at home. Mr. Hunter didn't know Jessica. So how and why was he here?
Jessica came down the stairs and walked up to Mr. Hunter. "Hi, Brock, baby," she said, and kissed him.
He kissed her back, enthusiastically. His hands slid down her back and squeezed her bottom. She squealed and wriggled in his grip.
Holy crap. They did know each other!
Oh, no. Oh, no. I'd been owned, big time. They'd probably known each other all along. They were obviously having an affair. I wondered if I'd been cuckolded. And now they were turning me into their maid.
Which - oh, shit! - meant Mr. Hunter almost certainly knew that I wasn't a real girl. He'd probably known that all along, too. When did Jessica's mysterious Tuesday night meetings start? Right about the time Brock hired me as his secretary. Was she meeting with him? Like in a bar... or a hotel room?
How and when had they met? I didn't know. But the rest of the story now seemed clear to me, and it was scary.
Jessica must have met Brock early, around the time of my demotion. They had an affair. They presumably talked about ways to get me out of their way, and decided to feminize me and make me their servant. I wonder whose idea that was.
And this was why Jessica suddenly gave me permission to dress up - which had always struck me as odd. She bought me a women's wardrobe, and she - no, I - started feminizing me. I did it to myself. The shameful truth was that she didn't have to coerce me into wearing dresses.
Then Brock started reducing my hours, so that I started spending more time at home, in the dresses Jessica gave me to wear. She used the time to train me in the feminine arts until she thought I was ready to pass as a woman. Then she made me quit my data entry job, because it was the last place I wore men's clothes.
Brock told Jessica about the secretary job, and she urged me to apply as Lisa. She even dressed me up for the interview. That would have been the first time Brock saw me as a woman, but he kept a straight face. He greased the wheels and I got hired. He pretended not to know that Lisa was Larry. He sexually harassed me while knowing all along that I was a boy. I found this disturbing.
Did Brock really need a secretary? No! I never did any secretarial work. The job was fake, just an excuse to feminize me further. Jessica obligingly took me shopping for tight skirts and tall heels. Brock started using me as a booth babe for his presentations, and Jessica taught me how to pull it off.
And tonight - the culmination of their plan? - it was Jessica who dressed me in a pink petticoated maid's uniform, practically the ultimate symbol of feminization, and invited Brock to dinner. Now I knew why. My wife and evil boss wanted Larry out of their way, and they wanted an obedient, submissive Lisa to serve them and do all the housework. A win-win for them, a lose-lose for me.
I'd been so stupid! I practically deserved whatever was about to happen to me.
"Lisa, you're being very quiet," Jessica said. "A penny for your thoughts."
I took a deep breath. "When did you meet Brock?"
"Ah, so you finally figured it out," she said. "We wondered how long it would take you."
I curtsied, not knowing what else to do. "Why are you doing this to me?"
Jessica smiled. "Isn't it obvious? Brock is replacing you in my life. He'll be moving in this weekend. He's my man now, and you... well, you're our maid. We planned this dinner tonight to make you understand this. Here we all are! Brock and me as a couple, you as our pretty pink maid. This will be our life now. Won't it be lovely?"
"You can't do this!" I shouted. "I'm your husband!"
"Not for long, sweetness," she said. "I'm going to divorce you and marry Brock. Maybe you can be one of my bridesmaids! I'll become Mrs. Hunter, and you'll be Ms. Lisa Curthose, our devoted domestic servant. Oh, you'll get half the community property, but it'll be tied up in legal folderol for as long as Brock and I need it to be. We might even be able to convince you to invest your entire share in BenefitBros - which is doing very well, thanks to its innovative presentations, starring you."
"Or I could just walk out the door," I said. "If you stopped me, you'd be committing a crime."
"Oh, we wouldn't think of stopping you!" Jessica said. "It would give you an opportunity to find out how the world treats sissy boys who run away from home in a pink satin maid's dress and high heels without any money or ID or place to stay. I'm not sure you would enjoy the experience. You can try it if you want, but you might do better to stay with us. Here in a place that's safe, with a master and mistress who love you and want you to dress and serve us as beautifully as you can. If you're a good girl, you'll find that we'll be kind. We can give you real breasts - you'd love them. We can do more than that, if you wish."
I gulped. Things were moving too fast. Jessica and Brock had completely outwitted me, and I didn't see a way out. I wasn't sure they'd even committed a crime. I'd done everything voluntarily. I felt so stupid. I was a bimbo, a sissy fuckwitted bimbo, and I deserved whatever I was about to get.
Brock spoke up. "Lisa. There are certain things I'll expect you to do for me."
He looked at me expectantly. "Yes, sir," I said, and curtsied.
"I like it when you curtsy," he said. "It shows respect."
No, it didn't! Not for him. "Yes, sir." Curtsy.
"If I touch your body," he said, "I want you to consider it a compliment and enjoy the feeling, instead of telling me to stop."
Oh, no! "Yes, sir." Curtsy.
"Also, it turns out that Jessica doesn't like giving me blowjobs, so that will be one of your daily duties as our maid. Weekday mornings at six, seven on weekends and holidays. In the master bedroom. Wear a pretty nightgown and crawl into bed between my legs."
Gulp. "Yes, sir." Curtsy.
"And finally, to show my mastery over you, I need to fuck you. I've already fucked Jessica. That happened the first night we met, when she called my office to complain about how you were being treated. We met after work, we ended up at my place, we made plans, and tonight you see the results."
Adrenaline fizzed in my arteries. Fight or flight - but in my petticoated uniform and heels, I could do neither. My heart pounded. I was afraid of him. I knew I faced certain defeat. I fought to hold back tears.
"Please don't rape me!" I said.
"Absolutely not. Rape is a violent crime," Mr. Hunter said. "I'm going to deflower you, with your consent. Make a woman of you. Fill you with my seed, even if you can't make a baby. I'm not attracted to males, but I am attracted to the girl named Lisa. I need to fuck my pretty pink maid in her sissy pussy and teach her who her master is."
I was horrified - and fully erect. The muscles in my bottom clenched involuntarily.
"Oh, please, no, master!" I paid lip service to resistance, but knew it was hopeless. I could deny him nothing. I could only submit. I was little Lisa, his obedient maid.
"I'm not a rapist, Lisa. I won't fuck you without your consent. Say yes."
"Oh! Sir! I..."
Brock slid a hand under my skirts, touched me through my panties, stroked me, brought me to the writhing edge of release. My taffeta petticoat rustled under my skirt. The sibilant sound almost made me swoon. I squeezed my thighs together, feeling the frisson of nylon on nylon.
"May I fuck you, Lisa?" he said. "Say yes."
"I... I..."
"Say yes," Jessica said.
"Oh! Oh! Oh!"
"Say yes," Brock said.
"Yes, master!" I shrieked.
The End.
Comments
Brett Schuhkraft
Lisa is a analyst and ever one knows if you really want to get a boss you get his secretary on side first So if I was Lisa I'd get them to pay for my SRS but I'd take video of them fucking him and get as much evidence as I could Then after the surgery I'd go public to all the big boss of there companies Brock's work mates and his bosses won't like the gay video of him fucking a sissy plus the bad press will of Brock hiring a sissy to flirt with his customers to get them to place their orders and Lisa's wife will lose her job as she supported in the persecution of her husband Now that's a story I'd really like to read
Jason Dunn
i was thinking something similar, youre idea mixed with Leslie's idea ^^^^^^^ haha. I was literally thinking what i would do if put in Lisa's situation, but with me, in addition to CD, Im also a gun owner hahahaha. Mine might end differently for brock. Just saying lol
alan schuster
It seems like more could be written regarding this one
lunapain
My raw anger at the end of the it made me want to punch my wall. I would LOVE a revenge story... maybe a part two of brock being feminized doesn't sound too bad...
edwin sargent
well well the wife was involved the whole time
Leloine
At first I thought that Jessica was going to try and get back at Larry's boss, but then I realized what was really going on after she started spending so much money on Lisa, then I just had to finish it to see just how it was going to play out. I enjoyed the story, and knew that so many men would like to change places with Lisa.
Leslie Deana
I had a strong intuition of what was coming down the pike... I was just hoping that I was wrong, but no sadly.
Leslie Deana
Wise, no! Traitorous, yes.
Leslie Deana
I remember a man at a party that I was didn't want to take NO. I USED MY R INCH HEELS thru his eye. He never saw it coming. (Grin). *Then* i kicked him where it hurt. Being a woman doesn't mean we don't have our rights.
Julia Miller
How to lose your manhood... Or how I became a Sissy Maid for my Wife and Boss. I almost feel sorry for Larry, but realized at the end of the story, he was exactly where she wanted to be.
Brianna Demonet
A wise but divient wife.
Clive hooks
I stopped listening to this one
