The Secretary Experience

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I imagined a single man with impotence had the same problem when he started dating someone new. Bonnie had been right, or at least my unconscious mind had been. I had to tell her before we both got too attached to break away free without tears.

Catelyn followed me to my house, parking her Toyota behind my Silverado. "This is going to be fun," she said.

I doubted she'd feel the same after my terrifying disclosure. This wasn't like TV where the big reveal was made with happy, joyous squeals. No, this one would be met with derision, the same I'd encountered on the city sidewalk as an old man told his wife to pay me no mind. To ignore the crossdressing freak talking to himself.

I led her into my house, giving her the same room-by-room tour I'd received when Bonnie had been real, and I'd driven to my own driveway for a lunch date with her and Paul. We went from room to room, pausing just long enough before moving on. As we stood in the master bathroom, my closet door hanging shut, I asked, "are you ready?"

"Yes, please."

She sounded giddy and I was about to take that away. Only I didn't need surgery or a pill; I just needed to be me. I opened the closet door.

Catelyn went in and examined my clothing. On the left hung my male clothing; the things I normally wore, like the jeans and maroon and white button-down shirt I was wearing now. Along the back wall and the right-hand side were Autumn's clothes: dresses and skirts, blouses and blazers. Below Autumn's clothes, my clothes, were my heels. I had nine pair now thanks to my shopping excursions. They were stacked left to right from lowest heel, at nearly three inches, to an exaggerated platform with a six-inch heel and a four-inch platform. I had to duck leaving doorways wearing those.

Autumn cycled through the hangers like she was shopping at a mall. "Oh, this is nice," she said looking at a deep-blue blouse with tiny felt buttons down the front. She kept looking making appreciative comments at some things and laughing at others, "Oh, now this is slutty," she said looking at a red dress that had the right-hand side held together by nothing more than tiny golden straps. "You can't wear panties with this, can you?"

"You can," I said, blushing, "but they're visible if you do."

She laughed at that. "You've got great taste."

"Thanks," I said, drawing the word out as I looked for something else to say. She didn't seem disgusted; she wasn't running from the room. She wasn't making derisive comments full of hate. She was smiling as she pawed through my closet. I wasn't sure how to take it. I thought back to dinner and how she'd said 'ooh, finally.' What had she meant by that? I tried to ask her but couldn't seem to get the words out.

Catelyn flipped through everything and glancing at the shoes she asked if I could walk in them.

Blushing, still rendered confusingly mute, I nodded.

"Can I see?"

It was then that she noticed me. No longer distracted by the clothes in my closet she looked into my terrified and befuddled eyes. I couldn't tell if she was angry or sad, teasing or teasingly accepting. It was one thing to say, "what a sissy," your voice full of derision and another to say the same thing in a tone of playful support tinged with merriment. My confusion was evident as was the fear that I was ruining what could be something great between us, all because of Autumn, someone important that I'd kept hidden. Bonnie had been right, though, I had to tell her before she and I became an us.

"George," she reached out and took my hand.

I looked down at my feet, at the heels lined up like soldiers, afraid to look anywhere else for what I'd see on her face.

"George," she said again. She tugged my arm, pulling me from the master closet and into my bedroom. She had me sit on the bed. I kept looking down, now at my knees clad in their denim and my white tennis shoes. "Look at me," she said.

She waited until I complied, never letting go of my hand.

"I knew about this, okay. I knew."

"How?" I couldn't understand and if she knew then why did she accept the date with me in the first place?

She sat next to me, holding my hands. I felt the warmth of her skin. I smelled the lovely floral bouquet of her perfume and wondered briefly what it was called and if it was her favorite.

"You came in by ambulance wearing a dress. I was working an ER shift that day; we rotate through," I remembered her telling me that on our first date when she told me all about her job and I told her I had recently been fired and had found a new job that would start following my recovery. "I couldn't believe it when your dad told us your name was George. You certainly didn't look like a George at the time."

I took it in, hearing her words and not truly believing them. Still, the warmth in her tone and the playfulness in her brown eyes told me more than her words. She wasn't mocking me. "It's funny," she said, "I remember standing outside your room, looking in on you as you slept when my friend Susan, you'll meet her soon enough, came by and asked what I was doing. I told her nothing. She glanced into your room and smiled, calling me a stalker and telling me that I should ask you out. I protested, saying it wasn't appropriate. I was happily surprised when you asked me."

I thought of Bonnie and how she had said she had her ways. "I think I heard you. Maybe not consciously, but I think, yeah, maybe."

"I can't wait to see you dressed up. Can you do that? For me?" She practically whispered those final two words.

Mouth dry and shaking slightly I nodded. I think she was as nervous as I.

"Goodie!"

An hour later I told Catelyn my name. We made love for the first time that night, with Catelyn unzipping the back of my skirt and my own trembling fingers unfastening the buttons on her blouse. Her bra was plainer than mine a fact that both tickled and delighted her. "You're such a girlie girl, Autumn," she said, her hands in my hair and her lips on mine. She kissed me. Hard.

I admitted that I was. That was important. Being truthful. My parents taught me that; Doctor Helene confirmed it.

When Catelyn removed my bra, she laughed at my tan lines and I had goose bumps race down my spine as she ran her finger along the fringe between light skin and dark. "I love it," she said, before kissing me even harder than she had before.

Afterwards, both of us lying sated on my disheveled bed, Catelyn learned the story of Autumn, from those first tentative days stealing into my mother's bedroom to raid her closet, being oblivious to the fact that my mother knew, to the times I bought clothes online, slowly learning my size and being too terrified to go out in public, to having my accident and my post-coma hallucination, a manifestation of that hidden part of me pushing me to finally be myself, to finally naming myself. She learned it all, asking questions and laughing at the parts she found funny. I blushed. I gasped. I continued being truthful.

And I was accepted. I hadn't expected that.

We lay there until the day went to bed and the night was almost gone. I told her everything.

The next morning, after another round of bliss, Catelyn made breakfast while I sat at the breakfast nook table. She was wearing one of my shirts, one of George's shirts, and nothing more, and she looked sexy as hell. Her hair was disheveled from our early-morning tryst and her skin had a nice glow. She looked happy. She was scrambling eggs when my phone rang.

I grabbed my cell, "Hello." I listened, "okay." Then, "Tomorrow is great. Thanks. Bye."

"Who was that,"

"Doctor Helene's office. They want to move my next session to tomorrow. I see her twice a week."

"She's great," Catelyn said.

I disagreed. She's better than that. Doctor Helene is a treasure. Even with the few sessions we've had, she's helped me with so many things. The loss of part of myself being the biggest, but she's helped me understand some things, too. We talked about that older couple that Bonnie and I had met on the street, and how the old man had muttered, pay her no mind. He had meant me, of course.

It was Doctor Helene who suggested I write this journal, to both help my brain recover and to put my thoughts and feelings to the page. "It'll help, George," she said. "Trust me."

I did trust her, and I began writing my story, starting with losing my job and the accident that followed. I left nothing out. Not the shame or the fear or the doubts. None of the negative got omitted, but none of the positive things either, like hope. I wrote it all down, thinking of everything that had happened, putting the weight of my reality onto the printed page. Writing everything kept Bonnie alive; that was another positive thing.

I wrote it all down, feeling shocked at some of the things I've done and what I was still going to do. Writing helped me reassemble myself.

I thought of the remote that Bonnie had picked it up off the floor on the day we met. I thought maybe that was the first thing she did to start putting my life back together. That was the day I started putting my life back together. I couldn't recall picking up the remote. To this day I would swear on a billion bibles that Bonnie had picked it up, but that had been impossible, so it had to be me. I wrote that, too.

Catelyn finished making our eggs. They were good. She sat, gazing into my eyes, a smile on her face. "You still have some eyeshadow on," she said.

I smiled, took a bit of the tasty eggs, and shrugged. "We can shower after breakfast."

Catelyn smiled in agreement and later, after I did the dishes, she helped me wash my body and my face after I washed her hair. We spent the day together, talking and laughing. Having fun. I promised to go shopping with Catelyn, as Autumn, after my bandage was fully removed and my hair had grown back. The part they had shaved looked horrible and I didn't own a wig.

"I can't wait," she said, offering me her lips.

I took them.

Epilogue

"Ms. McNeill," Linda Chapman said, holding her hand, "It's so good to have you aboard." She glanced at my head and at my new, shorter hair, coiffed into a cute little bob. I had added some auburn highlights since she'd seen me last. I had had to get my hair cut short; it wasn't grown out near fast enough. "Nice haircut."

"Thank you and thank you for having me," I smiled, taking great delight in hearing her call me Ms. McNeill. I doubted I'd ever get tired of hearing it.

She led me through the building, our heels clicking in unison on the tile. She led me through the process of starting my new job, working with me to fill out the appropriate forms to start my insurance and my direct deposit and all the myriad company polices I'd be expected to follow. I loved signing Autumn's name on every single form. I must admit, because Doctor Helene stresses honesty above anything else, that I had practiced that signature, working out the loops and whorls. I even tried putting a little heart above the "I" in my last name but gave that up as too childish. Every time I signed Autumn McNeill, I felt a tinge of joy.

I was wearing a crisp white blouse, a black skirt that stopped just below the knee and a sharp blazer. Underneath I was all girl with black panties, a black half bra, my breast forms glued on, and a white camisole. My stockings, jet, were held up by a black garter belt. Catelyn had shown up early to help me dress, promising that she couldn't wait to help me disrobe when I got home.

"And I can't wait to hear about your day," she beamed.

"It'll be boring," I said, then smiled, "it'll be great."

She shook her head, "why a secretary?"

I gave the truthful answer. "It's who I am."

"Girlie girl."

"Yep!"

For the first time since I can remember I had been looking forward to going to work. As I settled into my new job, sitting at my new desk and logging into the computer system as Autumn, I finally felt like the life I had been putting back together had finally become complete. A girlfriend, a job, and Autumn. The only thing missing was Bonnie. But she was a part of me.

That was enough.

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36 Comments
AnonymousAnonymous7 months ago

What a fabulous story. I can't say more other than I absolutely loved it. I am a crossdresser and it was so real to me.

AnonymousAnonymousover 1 year ago

I absolutely devoured this story and it has completely taken over my spare time over the last few days.

It makes a great change to find a story that explores the desire of a man to dress as a woman, and the thrill of doing so, without the story being taken over by pornography.

George's psychological journey makes an absorbing backdrop to the story.

I would love to read more.

Kathryn65Kathryn65almost 2 years ago

I loved every single word you have woven for us to follow. Had to have two days to finish it but loved every minute I spent reading and following and falling in love with all of your characters.

I only read a small part of the other hospital drama . Not me sorry.

If you have anymore of these tucked away I’d loved to read it . Thank you kindly once again.

AnonymousAnonymousabout 2 years ago

Sad about Bonnie though.

AnonymousAnonymousover 2 years ago

Carefully constructed and emotionally compelling with a clever and surprising ending.

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