The Courtship of Max Robinson - Chapter 2

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Chapter 2

I

As a result of my session at Merle Norman, I had a collection of basic makeup, but more importantly, I had an understanding of how to use it. Pat had said that I'd have to experiment to find a good look for me, and that point was repeated by Marian Gray, the consultant who helped me. She began by sending Pat away – saying the magic would work better that way. Then she created two looks for me.

The first one was dramatic evening makeup. When she said “dramatic” I thought I'd look like a drag queen or maybe Marilyn Monroe in Gentleman Prefer Blonds. Marian was too good an artist for either. Somehow, the result was just me, but better. Concealer and foundation perfected my natural complexion. Blush contoured my face while being almost invisible. My eye shadow, liner and mascara subtly drew a lover's gaze. My lipstick was incredible – promising things even I couldn't imagine. Looking in the mirror made my heart race and panties bulge. Luckily the counter maintained my modesty.

The second look, which I wore out of the store, was day makeup. The best way to describe it was to say it made me look clean and “fresh” – like unblemished fruit with highlights. Strangely, my day lipstick was brighter and my eyeliner darker – just the opposite of what I would have expected. Marian explained that the bright summer sun washed out features, so, they needed more emphasis. On gray days or if I was going to be mostly indoors, I should tone it down, as the light wouldn't be as harsh. Finally, adding gloss would make my lips a magnet for kisses and more.

As our session ended, I felt I had a friend and resource in Marian, and would be a steady customer. I gladly paid the hefty bill. (Fortunately, my dad had made me a partial beneficiary on his insurance.) I left glowing with new confidence. I don't know what Pat expected, but when she saw me, she was speechless. I pulled her head down and kissed her. When I finished, her face was flush and she was panting. I was aroused to, but I also felt a sense of power. I'd turned the no-nonsense manager who'd interviewed me into an animal lusting to get into my panties.

I was starting to think like a woman. Yes, I wanted desperately to have sex with Pat, but I also wanted to be more than her sex toy. What I'd said to Marian was true – I wanted Pat to make an honest sissy of me – her wife. I remembered the old saying, “Why buy the cow, when you can have the milk for free?” I loved Pat, but she wasn't getting free milk.

So, when a flushed Pat asked if I'd to go back to her place, I said I was emotionally exhausted and wanted to go home. When we got to mother's house, I stayed in the car, kissing, fondling and letting Pat feel me up, but stopped short of either of us climaxing. When I got out Pat still had bedroom eyes.

She'd come to think of me as a passive sissy. The initiatives I'd taken with Dorothy and the consultant at Merle Norman made her think there was more to me than she'd imagined. The change was subtle at first, but obvious to me. Before, I was a male bimbo – nicely treated, but a bimbo nonetheless. She wanted me to feel respected, but deep down, she felt I needed “guidance.” Maybe I did, but now I was closer to a self-guiding moral equal – maybe not equal yet, but much closer than before.

I was not a decisionmaker yet, but my opinions were worth considering. Before, I rarely heard from her between dates. Now I got regular texts and calls. Some of it was sexting, but a lot was about her private and professional life, and asking my opinion. I'm not sure how much what I said mattered, but at least I was being asked. I was no longer confined to one compartment of her life.

Meanwhile, a manager from Walmart had called to set up an interview. I'd heard they weren't very particular. As long as you didn't have two heads and were willing to work for peon wages, you were sure to be hired. As the store was on a bus route, I didn't need mother to drive me.

I wore my new loafers, black slacks and a short-sleeved dress shirt. Of course, I was not about to take off my pink pearl earrings or lovely nail polish. I'd learned a subtle makeup that looked good in florescent lighting. I arrived fifteen minutes early and sat patiently with good posture and my hands folded in my lap. About five minutes after the scheduled time a harried manager hustled past me, did a double take and went into his office. He called his admin in after him.

She came out and said, “Mr. Hanson told me to say 'One of the associates changed her mind about leaving, so the job is no longer available. Thank you for your time.'

“Just between you and me, I think that stinks, and you look very pretty. I wish my son looked as nice. I am sorry this happened to you.”

“That was lovely of you to say. Thank you.” I should have known. Still, I was ready to do something with my life, and having a job, any job, meant a lot more to me than it had a few weeks before.

Meanwhile, Pat and I started dating more frequently – three or four times a week. She wanted to consummate our relationship and I wanted a proposal, so however intimate we got, I kept my panties on. One Sunday afternoon, she came right out and asked “Don't you want to have sex with me?”

“Of course I do – more than almost anything.”

“Almost anything? What do you want more?”

“You'll have to figure that out for yourself.” Women can be so dense sometimes.

That led our first argument. Pat thought that I should just tell her what I wanted, and I wanted her to ask me to be her wife her without being told. The argument got hotter and hotter. Finally, she called me "a stupid sissy bimbo." I ran off crying and took a cab home. Mother wanted to know why I was crying, but I just ran to my room, slammed the door and sobbed until I fell asleep.

About 8:00 mother came in with a sandwich and lemonade, and sat on my bed. Without much prompting I told her the story of our argument and how I was a stupid sissy bimbo now. No one wanted to marry a sissy, so my life was over. Maybe it was a little melodramatic, but it was how I felt.

“Maxine, you are a lovely, smart sissy, and Pat knows you're the perfect wife for her. Sometimes it just takes people a while to figure out what they really want. Since you're more in touch with your feelings, you figured it out sooner than Pat. The same thing happened with me and your father. It took him forever to figure out he wanted to marry me. Just give Pat time and she'll work it out.”

After mother left, my cell beeped. I had four texts from Pat. I didn't read them. Later that evening, she called three times, but I was in no mood to talk to her. Monday her texts and voice mails continued to pile up and I continued to ignore them. She should know what I want. After all, me becoming her wife was her idea. Maybe she was having too much fun dating. Whatever it was, I was too pissed to listen to anything she had to say.

It was about 5:30. Mother was watching the news and and I was cooking pasta puttanesca when the door bell rang. It was Pat. I would have slammed the door in her face, but mother let her in. She was crying, making it hard for me to stay angry.

“I'm sorry Maxine. I was horrible, yelling and calling you names. I'm an idiot.”

“Yes, you are!”

“Well, I figured it out.” She took my hand and knelt on the living room floor. “Darling Maxine … Max Robinson, will you be my wife?”

I was already crying “Yes, Patricia Harper, I will love, honor and obey you all the days of my life.” I pulled her up and kissed her as hard as I could. Pat broke our embrace to reach into the pocket of her pants suit for a ring box. In it was a one carat solitaire that she slipped on my ring finger. It fit perfectly. Suddenly, I felt faint. Pat caught me and carried me to the sofa.

II

A couple of months before, I had no idea who or what I was. Now I was a pretty, confident sissy on my way to being the wife of a successful business woman, and, hopefully, a mother. As a prospective wife and mother, I wanted to be more responsible, but my new persona made that difficult. There's a lot of prejudice out there. So, I still had no job or real hope of one.

The Tuesday morning after Pat proposed, I got a call from Victoria Winters. I had no idea who she was.

“You're Maxine Robinson, right?”

“Yes, I am.” How many people knew that?

“I'm Vikki Winters … Dorothy's mother – from the nail salon. Remember?”

“Oh, Dorothy's mother! Of course I remember Dorothy. How could I forget? She was so sweet! I hope she's alright?”

“Well, she is, and isn't. That's why I'm calling. I mean she's physically alright, but emotionally, it's another story.”

“I'm so sorry to hear that … but why are you calling me? Is there something I can do?”

“I'm not sure. She talks about you all the time. You're her heroine. So, I thought … maybe … if we could meet … I don't know.”

“Well, I'd like to see her again … and help, but I don't have a car.”

“That's OK, my sister could pick you up. When are you free?”

“Most any time … now, actually.”

“Oh, good!” She seemed relieved.

I gave her our address and she said her sister would be there in half an hour.

I changed into my burgundy satin blouse, black slacks and healed loafers. There was no time to do more than touch up my face. I had barely finished when Dorothy's aunt rang.

I answered the door to brunette in shorts, sandals and a tank top. She didn't look like she'd even had time to fix her lipstick. I felt overdressed. I could tell from her face that she was struggling between curiosity and respect. She seemed to be at a loss for words.

“Ah … I'm sorry. You must be Mr., … ah, Ms. Robinson?”

“And you must be Dorothy's aunt?”

“Yes, I am.”

“Well, Dorothy's aunt, you may call me Max, or Maxie or Maxine – whatever you're most comfortable with. What may I call you?”

“Excuse me, I'm so sorry! I'm Vanessa Winters. Everyone calls me 'Nes,' Maxie.”

“Glad to meet you, Nes,” I said extending my hand, which she shook warmly. “I understand you're here to drive me to see your sister and niece? She we go?”

As we drove I asked Nes if she knew what was going on and how I could help. She only knew that Dorothy had been been bullied, had few friends and was clinically depressed. His mother was very worried about him. She wasn't sure how I fit in, but Vikki had asked her to pick me up before she got ready for work. She wanted to help, but her job as an airline attendant meant she was often out of town.

She parked in front of an imposing colonial in an upper middle class neighborhood and escorted me in. After exchanging kisses and hugs with Vikki, she left. I thanked her for the ride.

“Thank you for coming, Ms. Robin …”

“Maxie.”

“Thank you for coming, Maxie. I know I wasn't very clear, but I'm at my wit's end. Dorothy left a spot of polish on and was bullied at school. I'm afraid his, … her friends weren't brave enough to stand up for her. Now she's alone and depressed. Yesterday, her counselor told me she's having 'suicidal ideation.' I freaked out. I don't want to leave her alone. I'm wondering would you … I mean she likes you and you were so kind to her …”

“What, babysit her?"

“She's too old for a babysitter. I was thinking … paid companion and, well, … governess?? I mean if you'd leave whatever job you have … I'd make it worth your while. Dorothy is my life since her father left. I don't want to loose her.” Her voice dropped and tears started flowing.

Instinctively, I moved next to her and put my arm around her. “It'll be okay,” I said quietly. I waited while she composed herself. Finally, I said, “A lot of managers are reluctant to hire … people like me. So, I could use a job, but even if you didn't pay me, I'd do what I could for Dorothy. She's so sweet.”

“Oh, thank you! Thank you!” She hugged me, then let go, embarrassed at her display.

To lighten the mood I asked, “If I'm going to be a governess do I need a long black skirt, a puff-sleeved blouse, high-laced stub heels, and a bun?”

She smiled. “I don't think that will be necessary.”

“More seriously, there are some things … First, I don't have a car, and from what I understand, your sister isn't always …”

“We can work it out. I'll buy a car today! How about a Prius?”

“A Prius would be fine … but I was going to say, I need to know how Dorothy feels about me being her, ah … governess. Where is she, anyway?”

“If Donald is being Dorothy, he, she runs up to her room whenever the doorbell rings. Shall I call her down?”

“I'd rather go up and talk to her alone, if you don't mind.”

“If you think that would be best ...”

“I do.”

“Donald's door is the second on the right, and Dorothy's the third.”

“So, which should I try?”

“Dorothy's.”

I knocked on the closed door.

“Who is it?” a quiet voice said.

“Maxine.”

“Max...?” I heard running steps and Dorothy yanked the door open. She was dressed in a sparkly violet tunic, lavender leggings and white wedge sandals. Her unkempt hair and red eyes told a sad tale. She threw her arms around me. I hugged her back.

“We need to talk sweetie.” As we walked over to her canopy bed, I explained that her mother wanted me to keep her company and make sure she was safe. How did she feel about that?

“Oh, Maxine! I'd love it. You're the only one that understands me. I'm such a freak, and I'm so lonely.” For the next few minutes, her tears stained my blouse as I cuddled her.

When she recovered, I said, “So, tell me what happened. I don't believe you accidentally wore polish to school.”

Dorothy blushed. “No, it was a stupid, on-purpose accident. I liked Jonathan Valenti. He's so cute … curly blond hair, blue eyes … big, strong arms. He smiled and winked at me … I thought he liked me. I wanted him to know I was a girl … I thought if I left some polish on … well, maybe … but he … ” She started crying again. I waited.

“What happened?”

“He called me awful names, pulled my pants down to show everyone my panties, and shoved me down. Everyone calls me a sissy, a fag and a cock sucker. Mommy took me out of school. I'm such a freak! I want to die!”

I held her again. “Love is hard, Dorothy, but you can't find it unless you're alive.

“Look, we can't spend all day in your room. You have to help me pick out a ride so we can go fun places. Who knows, maybe there's a cute boy out there looking for a girl like you!”

“You think?”

“Yes, haven't you seen all the same-sex weddings on the news – they're all people who found each other and fell in love. You think any of them found their true love locked in their room?”

“I guess not,” she sniffled.

“OK, go wash your face, and I'll help you look pretty. We have a car to buy!” When she came out I brushed her hair and put a bit of mascara on her lashes.

“Do you have lipstick?”

“Mommy says I'm too young.”

“Well, I'll see if I can change her mind.”

At the dealership, Dr. Winters (she was a heart surgeon), got prompt attention by announcing she wanted to pay cash for immediate delivery of a Prius. The only snag was Dorothy and I insisting it be painted orchid. The dealer would pick me up at 8:00 the next morning to take delivery.

III

When I got home, I texted mom and Pat that I had a job, leaving the details for later. Pat was taking me to her club Wednesday, and we'd have time to talk over dinner, and maybe later.

When mother got home, I told her everything. She hadn't heard about Dorothy before and told me that she was very proud of me for being so kind at the salon. Then, we discussed what my job might be like over dinner. Halfway through, I could see that an idea had struck her.

“Maxine, when you're single and independent, how you look is your own affair. But, when you're responsible for someone else, even parttime, you need to take them into account.”

“I agree, but what do you mean?”

“I mean right now you look like a very pretty sissy, but if you're Dorothy's governess, people are going to look at you and wonder about Dorothy. Do you plan to take her places in girl's clothes?”

“Yes, I thought it'd help build her confidence.”

“Well, then I think you should look either all girl or all guy. Being a sissy is just going to draw attention. You might like the attention, but it will make Dorothy very uncomfortable.”

“You're right, mom.” I imagined all kinds of awkward situations in which Dorothy suffered the fallout from being with a sissy. “Well, I still have all my male clothes, I could just wear them.”

“Scrub and cut your nails, stop wearing the pearls Pat bought you, and get a buzz cut? I don't think that's you anymore, sweetie. Besides, I don't think Pat would like your new look when she takes you to dinner tomorrow.”

“What should I do?”

“Well, if you can't go right, go left. The main reason you don't look female isn't your face. With make up, your not a beauty, but you're certainly passable. The main problem is your flat chest. That makes people look twice and then figure out you're a boy. With a modest bust, you wouldn't get a close examination. People would just assume that you're an average 19 year old girl.”

“A modest bust?”

“Yes, not too big and not too small. Most of us are B-cups. So, you should be too. Then you could work on your voice. You've started speaking softer and sounding more feminine since you have been dating Pat, but you need to work on it more. Right now it's barely passable – OK as long as your don't say much.

“After dinner, we'll go to Target and get you a few bras, and balloons you can fill with water. When we get back. We'll look for breast forms on the net.”

The next morning, a shy boy, dressed in a red blazer like the salesmen at the dealership, knocked at my door. “I'm here to pick up Max Robinson,” he said gaping at me.

“That's me, … Robby,” I said, reading the name on his jacket. “I'm ready.”

Once we were on our way, I could tell he wanted to ask me something, but was too shy. “You look like you have a question, Robby.”

“I don't want to be rude, but Karl, the salesman who sold the car, said you were a guy and snickered. He wouldn't tell me why. Now you look like a cute gal, and you're wearing an engagement ring. Are you gay?”

“No, dear, I'm engaged to a woman. I'm going to be her wife.”

“Her wife!?”

“Yes. She has a good job and wants a family. She needs a wife and mother to take care of her home and children – I'm the lucky guy,” I said, smiling broadly.

“That's awesome! I took care of my mom's house and watched my step-brothers and sister. Now I've got this crappy job working for my uncle. I wish I was you. I even like how you look. … How did you find your lady?”

“She found me.”

Robby drove quietly for a while.

“I wanted to try my mom's things, but I never did. You're really brave.”

“No, I'm not … I mean I got a lot of encouragement from my mom and the lady I'm going to marry."

“Do you still live with your mom?”

“Yeah.”

“Maybe you could tell her how you feel and she'd buy you some things.”

“I'm not that brave.”

“Well, I'm starting work as a caretaker for a 13 year old who dresses in front of his mom. If he can be that brave, I'm sure you can.”

“Maybe ...” Robby was lost in his own thoughts for the rest of the drive.

When we parked, he said, “Thank you for talking to me, Maxie. You gave me a lot to think about.” He offered me his hand to shake, but I kissed him on the cheek instead.

Despite the promise the car would be ready when I arrived, I didn't get to the Winters' until 10:00. Dr. Winters expected me at 9:00 and had to ask a colleague cover for her. She wasn't happy. Fortunately, I called to explain. So her anger was directed at the dealer.

We'd both thought of new questions. I wanted to talk to Dorthy's counselor and know what was being done for her medically. A meeting with her psychologist would be arranged. She was on anti-depressants and testosterone blockers. Vikki was embarrassed to say so, but wanted a criminal background check on me. I agreed that was very sensible. I asked if I could help Dorothy be more feminine. I could as long as she wanted it and it was age appropriate. Did Vikki know Dorothy liked boys? She'd suspected it and added that no daughter of hers would have sex before their late teens at the earliest. I said that was wise, but wondered what would actually happen.

All this was hurried because Dr. Winters was running late. Still, I was encouraged that we saw things the same. Lastly, we agreed that Dorothy needed some fun to help her out of her depression before she'd be ready to start home schooling.

Vikki called her down, kissed her goodbye and left.

“Well, would you like to see the sissy mobile?”

“The sissy mobile?”

“Yeah, our lavender ride!”

“Oh, sure! Let me change into boy's clothes.”

“Why, do you feel like a boy today?”

“No, I just don't want people thinking I'm a sissy.”

“I think that train has left the station.”

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Comments

“I think that train has left the station.”

giggles. I wasn't sure about this one. I am not fond of the term "sissy" I think the negative connotations are too much to overcome, but this is turned into a sweet story about a guy with a feminine personality. And of course, I like Dorothy - wonder why?

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I am glad you are enjoying it

I am glad you are enjoying it. I needed some time to make the story work as I wanted it.

As for "sissy" it should be as positive and endearing a term as "Tomboy."

Love, Andra

I am glad you are enjoying it

I am glad you are enjoying it. I needed some time to make the story work as I wanted it.

As for "sissy" it should be as positive and endearing a term as "Tomboy."

Love, Andra

I thought about your comment

I thought about your comment as I was working in the yard and decided to say a bit more. I think "sissy" hurts because we are hurt by it, That sounds circular, but it is not. If we chose not to be offended, it would cease to be an insult. At least it would be a very ineffective one.

The dictionary is not an authority deciding what words mean. Rather it says how educated people use them. By using "sissy" in my stories, I hope to shift its usage and meaning in a kinder and more loving direction

Love, Andra

I am enjoying your story

Kind of surreal in the beginning yet it does make me want to read more. Please keep writing. Cheers :)

I'm a bit confused by your use of the word Sissy myself

Dorthy is pretty obviously a transgendered kid. It is unfortunate that she isn't allowed to be herself.

As for Maxine, I figured sissy described a person who likes being male and presenting female. I suspect the term around here is gender fluid, I know several people who live as both genders (not androgynous). One of them is a friend.

I would like to see the negative connotation of the word sissy go away, it was an insult all my life. I would like people to stop beating other people up because they (we) are different, but that isn't going to happen soon. I can hope though.

I am enjoying the story, please keep it coming!

I appreciate the time you

I appreciate the time you spent commenting on my story and thoughts.

I try to make my stories at least plausible. Sometimes that means the characters take on a life I did not envision in advance. I started with the premise of a dominant woman and a momma's boy, but Maxine had too much potential not to start taking control of her life. Being a sissy in the sense of being feminine need not involve being a sissy in the sense of being a wimp.

Dorothy started as a bit of local color, but Vikki was too good a mother not to fear for her safety. We see where that has lead.

Love, Andra

I like this story...

...I like the subtility of the story. Most of the stories about this (crossdressing/transgender) are shock literature. It gets very tedious to have to endure the underlying contempt mixed with what the characters in most of these stories try to pass off as love. I mean love is a good thing right?