The Secretary Experience

Each night I did the memory exercises Doctor Helene had recommended. Mostly they were fun, and I liked some more than others. The ones that seemed less clinical were best of all. I spent about forty-five minutes a night doing those brain games. I can't say they helped but they didn't hurt, and they helped pass the time. Time is what I had a lot of and as the note on my refrigerator reminded me, I needed a new job. Or at least something to help pass the long, endless days.

Bonnie visited me every day, checking up on me. We chatted about everything and lately we spent more and more time pouring through women's magazines from Marie Claire to Cosmopolitan to Glamour and the like. We talked about fashion and makeup. It was lovely to have someone to share that part of me. I wasn't fully recovered from my lapse in letting her make that uncomfortable discovery, but she seemed accepting and I needed acceptance. She kept hinting that she wanted to take me shopping fully dressed up "how I wanted to dress" but I was more than reluctant.

"Okay," she relented. She didn't seem upset or disappointed. Just accepting.

I finally let Bonnie see me dressed up about three weeks following that first shameful discovery. We were sitting at the kitchen table, Bonnie sipping a cup of hot tea from an olive-green coffee mug while I drank a large glass of orange juice. We were flipping through an Ann Taylor catalogue where I pointed out the dresses I liked, and Bonnie would do the same. We laughed when one of us would make a noise of disgust over some of the less flattering outfits.

"You have good taste," Bonnie commented as I pointed to a pin-stripe skirt and blazer combination that I really liked.

"Thanks," I said, feeling a bit of joy at her praise that was immediately swallowed by embarrassment. "I have one just like it."

Bonnie nodded, "I remember. Why don't you put it on? I'd like to see you all dressed up."

I created faster-than-light travel with how quickly I balked at that idea. I shook my head. "No. No. That's okay."

Bonnie smiled, her brown eyes taking me in, "why not?"

"It's embarrassing."

"Why?"

"Men don't wear women's clothes!" I didn't mean to raise my voice. It just happened and I felt a little guilty about it, but that guilt didn't last.

Bonnie argued that I was a man and if I wore women's clothes than I was lying to her and she didn't like being lied to. She said it in a way that told me she was playing but I still felt a little bit like an ass. "I've seen your closet, George. You have more women's clothes than men's and yet every day I visit you I find you wearing the same thing."

"What's that?" I was wearing khaki shorts and a pink Ralph Lauren T-shirt. I looked good in pinks and reds. The day before I'd worn jeans and sweatpants the day before that. She hadn't seen me in the same thing for at least a few days.

"What you don't want to wear."

She had me there. Around the house I wore skirts and dresses almost exclusively. A few times I'd been surprised by some uninvited guest coming by the house forcing me to change, but typically as soon as I arrived home from work, I'd doff my suit and tie and put on a dress or a skirt and blouse. I'd replace my camisole with a bra that held a pair of very expensive breast forms. Depending on how late I worked would decide if I wore makeup or not. After years of practice I was pretty good at makeup. It's amazing what you can learn from YouTube. And it is a bit humiliating to reveal I learned how to do makeup from watching young girls, barely in their teens, doing makeup lessons for their friends as I practiced right along with them.

I protested. Bonnie would smile and make another reasoned argument until I finally relented. It wasn't her badgering me, it wasn't her curiosity, it wasn't how she kept scoring logical points. No, what made me finally agree was the same thing as every time before. It was her acceptance. Until Bonnie I never know that was what I'd needed the most.

As before, when I finally agreed, Bonnie clapped her hands together and squealed, "Oh, goodie!"

"This might take a bit," I said.

She laughed, "it does take us women longer to get ready, doesn't it?"

I felt a rush of joy in the way she absently called me a woman. I couldn't help but agree. "That it does."

"Take your time. I'll clean up."

I nodded, taking a final sip of my orange juice. I needed it; my mouth was dry. I rose from the table and slowly left the room. I had relented but I still wasn't anxious to show another person how I looked dressed as a woman. No matter how much I liked it, how much it was a part of me, it was something that I had hidden my whole life fearing ridicule, embarrassment, derision and hatred. How though, could something that was such a part of who I was, something that made me feel wholly human, be wrong and cause such worry? Was it society or was it me?

I started in the shower. Naked, I ran a razor over my legs and arms, pits, ass and chest. I keep myself clean shaven from neck to toe; I was getting rid of stubble. I like the way my skin felt when I added lotion or put on a tantalizing pair of high denier stockings. Wrapping the towel around my chest like women did, I stood in front of the mirror and ran my hand over the glass, clearing a space so that I could see my reflection. I fished my tweezers from the top drawer between my twin sinks and proceeded to clean up my eyebrows. They were not that thick to begin with and I would love to make them thinner but when I went out, I had to represent my male self. I hated it but we all do what is expected of us.

Dry and freshly shaved I stepped into the closet that I'd accidently let Bonnie see. Standing amidst my skirts and dresses, my blouses and my heels I opened a small dresser tucked into the corner and donned my favorite bra. It was white, decorated with violet orchids. I pulled on a the matching full-cut panties. My pulse, already racing from what I was about to reveal, seemed to slow a bit as I settled into my happy routine. I put my breast forms into the cups of the bra and settled them into place. I had some glue I could use but that wasn't great for the skin. I only used the glue when I was going to be wearing them for a while. I liked the way the forms pulled on my chest when I wasn't wearing a bra. The glue made them feel more real.

I slipped a white camisole over my bra and then made my way back into the bathroom. The mirror was clean enough that doing my makeup was easy. I started with a light concealer. I rubbed it in, happy that I wasn't feeling any stubble on my face. I let it sit for a few moments before adding some rouge to my cheeks and blending it in, moving my brush higher and higher up my face. I turned left and right, evening out the sides. I wanted this to be perfect.

With my face done I began to work on my eyes. I was dressing for the office, so I proceeded with some sexy subtlety. I added a bit of teal to my eyelids and then added eyeliner, highlighting my own green eyes. Mascara came next, thickening my eyelashes, making them pop. Lipstick came next, a color halfway between the red brick of a firehouse and the subtle pink of cotton candy. It was called prom night and I had found the link to order it from one of those pre-teen makeup videos I'd watched on YouTube. I puckered my lips, blotted them against some toilet paper, and finished them up with a tube of liquid lip gloss, making my lips shine.

Entering the closet again I opened another drawer of my hidden dresser and pulled out the garter belt that matched my bra and panties. It felt good to be dressing up again. With Bonnie visiting me every day and coming at unpredictable hours I'd been reticent about going all out and now, even though I was afraid of Bonnie mocking me, that fear was cast aside as I dressed exactly how I wanted to dress. Bonnie had been right about that. I had not been dressing for me. I grabbed a pair of jet-black stockings and bunching them up into a tight ball, I pulled a stocking up each leg, savoring the tantalizing feeling of the stockings on my freshly shaved legs. I affixed the stockings to the garter belt loving the taut pull of the garter tabs against my thighs.

I grabbed a white blouse and buttoned it in place. The buttons were easy, finally appearing to be on the correct side. Men's shirts for some reason had the buttons turned the wrong way. I grabbed the pinstripe skirt I'd just mentioned and stepped into it. I pulled it in place, fastening it behind my back. I tucked my blouse into the waistband, smoothing everything as I went. The skirt toyed with the top of my knees; anything higher wasn't appropriate for the office and when I dressed in my business attire that is where I wanted to be working. At an office. As some businesswoman's secretary.

I'm not sure where my fascination with secretaries came from. I'm sure it came from my youth. Aren't we all just victims of our past? Isn't every decision made just one more thread in the tapestry our lives? I remember watching TV as a teenager, after that warm day when I found my treasured magazine still hidden among the cobwebs, and seeing the secretaries scurrying about in their tiny skirts and too-tight blouses just added to my adolescent fantasies. It was a job that only women seemed to do. I imagined myself getting coffee for some demanding boss, feeling her hand upon my ass, and knowing that I had no choice but to accept those unwanted advances, or I'd lose my job. I know from experience how horrible being fired can be.

Maybe it was the heated thoughts of being stuck in that job, making barely enough money to make ends meet, that made the idea of being a secretary so exciting. That putting up with harassment was necessary to keep food on the table and a dry roof over my head. I think it was the "have to" that made my fantasy "want to" so exciting. Countless times I'd find myself rubbing that excited part of me imagining going to an office, wearing a skirt that was too short because my boss demanded it of me, deciding that I was to be eye-candy to anyone who would visit. With the fascination I had with women's clothes, I desperately wanted to be seen in them. Not that I really wanted that to happen, but the thought of it made me bubble with aroused excitement.

But it was more than that. Every TV show that I watched showed the secretaries to be almost invaluable members of the office staff. Work would grind to a halt if the secretaries were absent. It was the dichotomy of being unnecessarily needed that fueled my fantasies and the idea that I would have to endure every harassment that came my way just to eat that tripped me over the edge. My thoughts would set back feminism a billion years but those were the fantasies that carried me from adolescence into college and into my adult life.

Those were also that thoughts that got me in shape. I grew up short and quite stocky. I grew up wearing pants and shirts that were larger than the ones my peers wore. Finding that magazine lit some fire in me. I started watching what I ate, and I started jogging. My dad grinned at me the first morning he caught me at five A.M., leaving the house in a t-shirt and a pair of shorts. "Where are you going?"

"Running," I admitted.

With that grin on his face, he could only nod. "Good for you."

I didn't need his encouragement. I had all I needed from a simple magazine. If I was to fit in those dresses, the sleeker ones, the sexier ones, I would have to be much thinner. I wasn't overly tall, and I couldn't control that anyway, but I could lose weight.

It took a while, nearly two years. During that time, I grew a little, but lost all the fat I carried. I didn't lift weights; I didn't want to be made of muscle. I wanted to be skinny. Jogging turned into running coupled with yoga. Going into my senior year I was at my full height of five foot eight inches with barely any fat on me. My mothers' clothes still fit, and I still snuck into her closet every time they left me alone. I looked forward to their date nights. Now I had my own closet of clothes.

The blazer came next. Once, long ago, I happened upon a magazine that led to my current desire to dress as a woman. At that time, I was a chubby kid, probably thirty or so pounds overweight. Studying the lingerie those pretty women wore in that mud coated magazine I had imagined dressing like they did, inside and out. I had accomplished that goal. Now, I was dressing for someone else to see. I wasn't going to be some bosses' eye-candy this time but that thought was there.

Bonnie called out, "are you almost ready. You're killing me!"

I chuckled and yelled back, "almost!"

Lastly, it was time for my heels. I slipped my feet into a pair of black pumps with a three-inch heel. I could walk in them with practiced ease. Four-inch heels were simple as well. I had a bit of a problem with heels above five inches, but I only owned one pair that high that I bought from the internet in some masturbatory fueled shopping extravaganza.

I stepped from the closet to study myself in the mirror that was now free of steam. I turned left and right, running my hand over my skirt to smooth any rough edges. My blazer hung perfectly; my blouse looked crisp. My skirt shook as I shifted left and right. I smiled and the feminine face in the mirror smiled back. I looked good. Not perfect, there was always something that gave me away. Maybe that's the reason I never went out in public or maybe I was just too hard on myself. My shoulders were a little wide; my Adam's apple a little too pronounced; my fingers a little thick. There were many, tiny imperfections that told the story of my true gender. I was simply a man in a dress.

I returned to the closet and opened my jewelry box. I needed a few accessories. It was one of the things I'd studies when I was learning what it meant to dress as a woman. Women accessorized. They added necklaces and bracelets, rings and broaches. Little things to draw the eye away from imperfections and towards parts they thought looked good. I put three golden bracelets on my right wrist and two on my left. I put small golden hoops in my ears and a doubled over long chain around my neck.

Back in the bathroom I ran a brush through my hair. I kept it longer than most men, usually pulling my hair back into a small ponytail. That length allowed me to brush my hair and have it hang almost to my shoulders. It wasn't completely feminine, but it didn't give me away either. It was an acceptable compromise. Like I said, I have an image to maintain when I go out. I gave myself one more glance before calling out, "promise not to laugh?"

I heard Bonnie give a good-natured laugh which gave me the answer.

I licked my lips, tasting my lipstick and lip gloss. I could feel a small knot in my stomach like I'd eaten my Thai food far too hot and was paying for it with a bout of uncomfortable indigestion. I swallowed twice, trying to ease my discomfort. Why had I agreed to this? I pondered that for a moment, and it came down to the same answer as before. Bonnie had accepted everything she had learned. Didn't that entitle her to know even more. There was a trust between us, one that started when my befuddled self had hired her and that trust had grown. We were becoming friends if we weren't there already. That led to other, more discomforting thoughts.

From the kitchen I heard Bonnie, "I promise."

Bonnie pulled me from my musings. "Okay. I'm coming."

I walked out of the bathroom, feeling my legs trembling like that one time I'd returned from a cruise to the Bahamas. On that trip I got of the ship and felt the ground under me moving slightly as my legs continued to compensate for some motion that was no longer there. Sea-legs transforming back to shore-legs.

I swallowed again as I left the bedroom. My heels made that enticing sound as I stepped onto the tile from my bedroom. Bonnie could now hear me coming. I turned into the kitchen. Bonnie was standing at the island, leaning against it. Her hands came up to her mouth; her eyes went wide. I watched her, ready to run if I thought she was going to ridicule me. I wasn't sure I could handle that.

"My God, George," she said, dropping her hands to show me the huge grin on her face. "You look like a woman."

"Thanks," I said, feeling my own face turn up in a smile. I turned to the left and right and when Bonnie asked me to spin around, I did a little pirouette.

"And you never go out dressed like this?"

"Are you kidding?" She had to be kidding.

She shook her head, the smile never falling from her face. "No. Not at all. If I didn't know any better, I would never know. Stay there."

I stopped moving and watched as she moved to the bay window to take a seat at the simple kitchen table. She studied me, directing me to move about the kitchen. She watched how I walked and how I moved my hands. "It's uncanny," she said. "Your makeup looks great."

Beaming at her compliment I admitted, "I've had a lot of practice."

"Where did you learn?"

"YouTube."

That made her laugh. "You don't move your hands enough," she said. "You're a little rigid. I'm looking for signs and there are a few that I'm going to help you with but, George, really, you could go out right now and nobody and I mean nobody would notice a thing."

I stopped moving and grabbed onto the marble island in the middle of the kitchen. "Yeah, I'm not going out like this."

"Why not?"

The answer to that was simple. Fear. I was afraid. I tilted my head as if to say that she had just asked the dumbest question ever. "What if someone found out?"

She shook her head. "Impossible."

I beamed at that, too.

"I so want to go shopping with you. God, it would be so much fun."

"No," I protested, too terrified of the idea to consider, but equally enamored by the idea to just cast the thought away. I wanted to be a secretary. It's not like I could do that from my living room. If I were to become a secretary, and satisfy that life-long fascination I had, then I would have to leave the house at some point, and wouldn't it be better to have an accomplice when I went. Someone to help me if things turned bad? I'd taken a huge risk showing Bonnie how I looked, and she was more than impressed. She seemed to be in awe. Still, I'd kept my secret hidden every bit as long as I had a secret. It would take more than a little goading to get me to risk more than I already had. "I can't."

She eyed me critically and shook her head. "Yeah. You can. Nobody would know."

"I would." I wanted to. I really did but fear is a powerful thing and so is habit and I'd kept myself indoors from the first time I tried on my mother's clothing.

"I promise, George, nobody would notice and if they did, so what? You look great. But it's your choice." She gave a little laugh, shaking her head. "You look like a professional woman. God, you could go to any large downtown office in America looking like that and everyone would just know you're..."

"A secretary," I said, interrupting her far too quickly.

Her eyes went up. "A lawyer. A CEO." She eyed me, looking at the embarrassment rising to my face. "Is that how you see yourself? A secretary?"

I'd said too much. "I'm going to change."

"Please don't. Come," she motioned to the empty chair at the little wooden table. Sunlight filtered in through the blinds, leaving thin lines across the dark surface of the table. "Sit with me."

I hesitated.

"Please. I can see your uncomfortable, but I don't want you to be. I really don't." She waited as I decided what to do. Finally, I took a seat. I think it was the look of amazement on Bonnie's face that had made the decision for me. "George, God, I can't call you George. Do you have a name you use?"

I shook my head. In my fantasies I was always Ms. McNeill. "Ms. McNeill, can you get me a cup of coffee," or "Ms. McNeill, I need you to type up a letter for me." I had never needed a first name. "No," I finally said.