Elliot: Working for Lioness Investments – 2 Better But Not Comfortable

Elliot: Working for Lioness Investments – 2
Better But Not Comfortable

By Jessica C

Elliot is breaking the Rose colored glass ceiling…
Despite having a master’s degree and working there over seven years…
He’s been kept an ordinary research and finance person…
Now He’s to be the first male Associate…
The men of this company are required to wear unisex clothing.


After dinner, it is the first time, I remember Bonnie sitting quietly with me as I do my business reading. She does her own research, “This woman, Ms. Lourdes is very accomplished; if she’s going to be your client I’m impressed.”

I agree as I read what she’s done and the past corporations that she has worked for. There were six years people actually worked to discredit her work. Though it was mostly by those corporations that have grown using her work to help build their fortunes. Contrary to others, Marjorie was not satisfied with a so-so paycheck from them. What she knew should help people for which is why she became a chemist. She married Thomas Lourdes and technically they’re still married and get together now and then. Daughters Sophie and Rachel live with or close by their mother. Thomas, Jr. is what they call a surprise baby and is now only twelve years old.

Young Tom, like his father, works hard to show he’s a boy in the traditional sense. Marjorie Lourdes likes and encourages Tom’s strong male image. She does prevail in that he’s a healthy male who has good regard for life and respects others, especially women.

Marjorie Lourdes had her name on the patents of her earlier research that allows her now to use them as building blocks for current research and development without paying her prior employers for them. While her corporation hires many women, they only make up some sixty-five percent of its workforce. The fact that some of its scientists, management and product development and salespeople are men, gives some comfort to me as Elliot.

I could have continued to read, but I have a seven o’clock office time and new clothes to wear. I shower and we go to bed as Bonnie suggests. Bonnie is up with me come five in the morning. The clean camisole undershirt also has the padded area for the front of my chest. Bonnie asks, “What are you going to do? You could either wear a regular undershirt or try one of my camis that are white and plain.”

“It didn’t hurt me yesterday and it didn’t really show. I’ll wear this one that I bought yesterday.”

Bonnie says, “Good, I think it will make your front look nice and neat. Your waist actually looks better to me.” She asks, “Did you know your satin panties have shields?”

“I think that is to protect your clothes from dribbling pee. It kind of makes sense for what the underpants probably cost.” I hadn’t really noticed.

It is when I put on the shirt and slacks that I really notice the flat part that Bonnie mentioned. I don’t say anything but my waist actually appears narrower in relation to my chest.

I forgot the socks so Bonnie shows me with the first one how to roll it up and put it on. The socks have no trouble moving up to my knee. I ask and she tells me by pulling them up as she did, it helps them not to ride down during the day. She has a pair of mules that she says I should try. They’re actually a size too big for her. She had not sent them back yet. I like better how they look, reminding me of a square toe pair of shoes I use to have. Like the shoes I bought, they have the two-inch heel. I wear them for now but will change out of them before I go to work.

The area around my eyes are dark from too little sleep and my face has blemishes. Bonnie says, “You really should stop at a good cosmetic place and get someone to help you select and use the male makeup that’s right for you.” I look at her like she has to be kidding me. She says, “It’s up to you, but if it is done right I don’t think even you or I would notice you have makeup on.”

I know that I often have found that true for Bonnie. I don’t say anything nor do I commit to stopping someplace. I eat a small bowl of cereal with fruit that Bonnie fixes for each of us. I’ve brushed my teeth again and check my hair. It’s holding as Bonnie fixed it. She lightly sprays one of my colognes as she has me walk through it. I really like how light the scent is. I grab my sports coat and hurry out the door. I’m tired of the fussing and pleased with how I look. Bonnie catches me at the car, “You’ll need this and your keys. It has a narrow wallet with your cards and money as well. I’m sorry if you think I’m pushing you.” It is my small satchel with a long strap.

I close my eyes, collect my composure, “Thanks, I think I will get the routine, it’s just all new. I really appreciate your help.” We share a kiss and I like the feel of her lips.


I knew I rushed too quickly out of the house as I arrive inside our company twenty minutes before seven. I needed to use my keycard to get inside. My clicking heels must sound different as Katherine and Diane both check whose in the hall. Katherine comes out to greet me and walks with me to my office.

She says, “I’m surprised how well you look today and you are cooperating with the dress code and even being creative.” I’m wondering about the creative part until she mentions liking the shoes. I had not even noticed but I had not changed out of Bonnie’s shoes.


Katherine helps me sharing quick codes for each Associate, such as Diane is 3C and Katherine’s 4G. When she tells me other names like Betsy 1C. I realize I have never met, knew or communicated with some like Betsy. Veronica is R2 one of the partners.” I have met her and done some of her work. I thought Caroline was a partner, not an Associate. Katherine tells me, Hannah Dirks, a person I will meet soon is H1. Caroline is 3B. Sophie Connors is SC3 is a partner which makes sense. But I find out that is not public knowledge. Her ownership presently is only associated with her group within the firm.

I can’t believe it is already 7:45 a.m. as Dottie Jones my Assistant arrives and checks on me. I ask Katherine, “Why am I in at 7:00 if my assistant isn’t due in until 8 am?”

“You will learn to do some of your more confidential work before she and other office people are here. If you see an Office Assistant here much before seven forty-five you are to ask for identification and clearance. If that’s not shown. Call security and shut down her system and those of that and the next two offices on either side. You will be shown how to do that.”

Katherine says, “Young lady, you will learn…” She stops, “Sorry about the ‘Lady’ part, you will probably get that more than once on this floor. You should be proud that you are in with us.” She continues, “You will learn more about how secure our systems are and how we keep them that way. I think you will go through the security process like the rest of us. Some of that will be today. We will have lunch at 12 noon for you to meet your colleagues here. We’ll have fun but it is also learning and training for you. It should be over between 1:30 and 2:00 pm.”


I ask, “Will I have time to call Ms. Marjorie Lourdes today. I was planning to do it around 9:00 a.m.”

Katherine replies, “That is your responsibility, but if it is what you plan you better get it done.”

“This is silly but would any of you know the best place to get makeup for men?” I want to apologize as I say it.

“We’re glad to hear your question. Two Associates that are free come 2:30 will go with you. Please don’t use more than one and a half hours.”

“I won’t need anywhere near that much time.”

“We thought you’d like to get some clothes and be able to charge it to the company. That will be your decision but the Associates with you will plan to be ready. You do have an expense allotment for coming on as an Associate.


I am settled back into my office work when I make a call to Marjorie Lourdes; it is just before 10 in the morning her time. I had hoped to get a machine or no answer giving me more time. It was just after the second ring, we connect, “Hello, Janice Cooper, Sophia’s Earth Oils, Ms. Marjorie Lourdes Assistant.”

I introduce myself, “I’m, Mr. Elliot Sanders Associate of Lioness Investments. I would like to schedule an appointment to meet with Ms. Lourdes.”

She says. “Let me put you through to her. She’s been hoping you would call.”

I try to say, ‘I just wanted to make an appointment.’ But I hear another phone pick up, “Ms. Lourdes here, did I hear you’re Elliot Sanders from LIFe. I like that you are calling promptly, I like that. I have Tuesday as a casual day for me. Could you be here then? Say 10 a.m., give me the day and Wednesday if you would. I am not sure if Sophia will want to meet you yet or not. You can plan to stay with us if you wish.”

Everything is happening much faster than I anticipated. “Yes I agree,” but say, “I need not stay there.”

“You will dine with us and meet into the evening. You should reconsider about staying here. I will talk to you about business on Wednesday. I am not sure what I’m doing Tuesday. Janice will inform you by tomorrow or Monday morning at the latest. Come prepared to have a good time as we’ll get to know each other. Do you have anything you might want to ask me in a hurry? I am ready to go out the door.”

I ask, “Is there something I can prepare to do for you?”

Ms. Lourdes says, “Several, call me Marjorie when we’re together especially on my personal time. I have another half a million dollars to invest and ask that you look over my portfolio and see if there are any changes you would suggest.”

“I will see you Tuesday then.” She says goodbye and hangs up but I know the line is still open. Janice comes back on the line. She has me run through a quick synopsis of the conversation. “Thanks for keeping your conversation short, Ph.D. standing, Ms. Lourdes is a busy woman. I will probably wait until Monday to give you the information about your meeting place. Has Katherine provided you with her present up to date portfolio? They include her private phone numbers, please keep them secure, not easily found on your phone.

“You will need to be very good, men are not her favorite people. Fortunately, Ms. Attwood does highly recommend you. Do not let her down please.” I am soon ending our conversation. Dottie comes in with a template form that is good for debriefing me and getting things down in a reference form.

That done, I spend until noon going over Ms. Lourdes’ present investments. I asked Katherine what other investments they had discussed and what had been ruled out. Katherine says, “She will want a ten percent return or better overall. Research women seeking to start up a company, but it needs to be pretty good if she’s to invest a $100,000 or more. Do not recommend more than $150 thousand with startups nor investments under $25,000. My suggestion, locate companies that have already started and are ready to expand or explode.”

Our conversation ends with Katherine outside my office door, inviting me to lunch. There are beef, chicken and tofu strips ready to add to stir-fry. There are several appetizers and hot and cold teas along with waters. I am famished yet I know to eat wisely, including portion control.

There are twelve Associates present as well as office people being served second and sitting close by. The women are giving me a hard time. Associates Cheryl and Jamie say they’re taking me shopping. A big part of their conversation with me has to do with this floor having been pure estrogen air. I am not to expect those conversations to cease.

We are done closer to 1:30, and only three Associates had taken calls and done business while we’re eating. Most take lunch casually without business calls if they can and encourage me to do the same. I like the relaxed atmosphere for getting to know them.

Like with me, the next hour we find very productive in researching investment possibilities. One woman in New Jersey has taken a cottage industry and is up to ten part-time employees and she wants all to be working full-time and to expand their markets. Their products are good and they have a patent that gives them an appreciable edge in their market. I’m scheduled to talk to Sally the owner tomorrow morning.

Come 2:20, I go down to Cheryl’s office as Jaime is coming down the corridor the other way. They take me to a clothing store that I didn’t know existed in our city. They do have clothing for metro males; it even opens as such. It’s around the block from the main store of women’s clothing apparel. Cheryl says, “Let’s look for shoes you like and we’ll set them aside and then see if they go with the clothes you select. You should get something for a formal dinner, nights out and casual meetings. I select two pairs of shoes one is grey. They are both very nice, though I’m not terribly excited about them. They’re a bit heavy, something that makes me think of an old librarian.

We looked at some slacks and shirts, but Connie had as good or better. We go through a set of double doors connecting to another area. It’s actually the women’s store and I feel like they’re pushing me. But the clothes we look at can be seen as unisex. I like the shirts/blouses I see without any darts for the bust or feminine trim along the edges. I even see narrow satin/silk scarves that could be used instead of ties. I ask a saleswoman about slacks that might be worn more formally by a man.

She shows me what could be a feminine tuxedo, she’s telling me that I’d look good in it. I do try it on to amuse Cheryl and Jaime. I am surprised with the longer waist of the pants and a cummerbund as it looks like a fancy tuxedo. There is a slight flare to the legs. They have some in my size that is white or gray. The saleswoman has me step into a black pair of mules with a closed toe but open on the sides. I complain that a man does not wear such dress shoes. Once I have them on and whether I am sitting up or standing properly the slacks and the 2 ½” heels hide much of my feet.

I talk with Cheryl and she tells me what I need to hear. “If you’re going to be a metro male you need to be happy with whom you are. If you cannot be content with your look, Jennifer will not want you like that. Relaxing and enjoying your look, she and you both will be happier.” I take the gray tuxedo and along with a pair of black and a pair of gray pumps. The gray is a match with the fancy tuxedo. I stay in this department selecting slacks, blouses as shirts and the two scarfs that I like. Cheryl takes the time and shows me three ways to wear the scarves.

It is nearly four when we begin to exit through the men’s shop when Jaime reminds me to get some makeup. We look and they help me select a concealer, foundation and basic makeup. The men’s mascara and the brush are much simpler and sparsely uses much mascara. There’s a blush that can be used to brighten the tone of my skin. A cleanser and moisturizer now become essential as well. Cheryl has more panties, camis and a variety of socks added to the purchase. I call Bonnie as she is out of teaching for the day. Telling her the stores will be delivering my clothes directly home.

I did question, “Cheryl, can we afford to have them deliver them?”

She smiles for $3,000 in purchases they will be happy to deliver them. It is much safer than you situating all them in your car while back to work. Next month we will need to be talking about your car as well.”

I am now excited about breaking into the next level as an Associate and the jump in income. But I’m angry and worried about being feminized. I justify this as a temporary move before I would jump companies. That is if things don’t change in my favor.


Like the other Associates, I’m very dedicated and find myself back working until 6:30 before going home. Getting home after work, there is a funny explosion of all my emotions that I kept bundled inside. Bonnie greets me when I come through the door. “Honey, I love this new you and I can’t wait to see you showing me how some of these clothes look on you. I thought you were going to seek to go the other way on your camis undershirts.”

I wasn’t the one who picked them out. I’m a man so I am only mildly interested in seeing them. I thought they bought four but there are at minimum seven-plus more new tops. There are also two with a lot of lace and two more that are pure satin. The chest pads instead of being a quarter inch or less are now plush smooth and soft.

Bonnie soon has me out of my clothes and is putting one of the camis on me along with one of my new satin panties for men, very different from my usual. With my first silky beige shirt, the camis becomes invisible as long as the second to top button is done.

I do not feel the difference when Bonnie hugs me. She only tells me that it is fine. She loves the slacks that go with the cummerbund and tux. I tell her I think it looks too feminine, but she swears it is a cool metro look. The clothes helped to arouse me, unlike anything I’ve experienced. With the first change of clothes, Bonnie has me relaxing with a glass of wine. We’re sitting around visiting.

I am more than ready to unwind from the day. Bonnie sweeps her fingers through my hair as we share a passionate kiss. She undoes a few buttons for me and I settle down as she’s being supportive. I’m feeling sad as I’ve not been there for Bonnie like she has been for me.

Bonnie has beef stroganoff simmering for our dinner. I tell her of my being able to schedule time with Marjorie Lourdes. We both know the preparation time during the night pays off. I had changed into a different pair of slacks, and a more casual pastel blue camis along with a new pair of slippers that I didn’t remember buying. I shake my head as I was actually feeling comfortable in most of my new clothes.

I am sitting watching Bonnie as she’s correcting school papers. I know some of the students’ names but this is a first where I am taking an interest in how they’re doing, their handwriting and Bonnie’s comments to them. I’m proud of her,

Bonnie, “Do you have off early tomorrow and have this weekend off?”

I tell her, “Most the associates are regularly off by 3:30 or 4:00 on Fridays unless we have pressing work. I will need to go into work for a couple of hours Saturday but I’m sleeping in if you are.”

Bonnie asks, “If I get you a bra and heels would you mind if we go out tomorrow night as two girls out on the town? I think it might help the two of us to relax and have a good time.”

I’m staring, thinking about what she’s asking, wondering if it’s a real question. The last time we did something crazy like this was over a year ago Halloween. The difference now is I would intentionally look like a young woman. I am upset with work pushing a feminine image. Bonnie and I decide to do it with me pressing that it is only for fun. Telling myself it’s different from the pressure I feel at work.

Bonnie doesn’t realize it but her hands are laced together like she’s praying. That plays the deciding factor, “Yeah, but just tomorrow night.”

I am already getting excited to be with her tonight. Truthfully the clothes have something to do with it.


Bonnie’s up early to go power walking, I wasn’t planning to walk with her, but I had got up to use the toilet. When I came back to the bed, there’s a pair of nice workout pants, a top, and band for my head. Bonnie says, “If you want to walk with me please hurry.” I quickly put on a pair of socks and an old pair of cross-trainers, along with the clothes that were out. The cool air and Bonnie’s pace encouraged the brisk walk.

I copy Bonnie with both the warmup stretches and cool down time. Bonnie comments, “I really appreciate you taking time to walk with me. Usually, we’re pretty far apart when we walk.”

“I learned that isn’t really walking together and last night you took time to be there for me. I appreciated that. It was enjoyable to walk together and I it was good exercise.”

The shower and getting ready are going quickly. I decide to go with a white lace camis since it won’t show and it feels extra nice. I put on a pair of black slacks and a white satin shirt with a scarf tied nicely and the black jacket. Late, I decide I’d like to change the camisole but alas I don’t have the time. Bonnie uses my roll-on concealer with makeup that blends in so nicely a person does not notice. The dark areas around my eyes are gone.

I drive Bonnie to her school early and make to my office by 7:00 a.m. There are two trip plans on my computer to fly out to New York City and then drive to Suffolk County. One goes out Monday evening the other very early on Tuesday. Either way, I’m choosing to stay at a nice hotel. I considered driving my own car, but Dottie has a note from Katherine saying ‘No’.

I sit back, reflecting on the week and happy about how well I’ve been received by the Associates and the staff. I see my reflection and lightly laugh at myself. Thinking about tonight brings another light-hearted smile. I decide I will work to be a presentable woman on a night out. I even have it down to one pants outfit or a dress Bonnie had mentioned.

To be continued

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