The Retrodresser Pt. 01

Preface: The Swishflash Underground, 2037

When the door suddenly opened and Mr. James walked into the office, I quickly smoothed down my skirt and then moved my hands to the keyboard to resume my typing.

He paused as he walked by, regarding me, looking at my hands and then at my legs. His eyes lingered over my blouse, my dress, my footwear, and because we had spoken more than once about appropriate office attire, I was glad he seemed to approve of my choices.

"Good morning, Doris," he said, his eyes returning to my face. "Already busy, I see." I felt a blush cross my cheeks and forehead. His voice had a twinge of wryness in it that made me shiver. Was it sarcasm? Had he seen me push my hem back down?

Maybe he was always like that, dry and ironic and a touch cynical. I didn't know him well, yet.

I didn't know him at all, really.

He picked up the Times from the reception table, went into his office and closed the door. I had noticed, as well, his dark gray conservatively tailored business suit. We were both dressed for our appropriate parts in this little improvised office drama.

Sitting there alone, typing non-sequitur stream of consciousness, I felt excited, and not a little apprehensive. I stopped typing and listened. Quiet. I wondered what Mr. James was doing. Even more, I wondered what he was planning. I looked down into my lap. My knees touched, and I pressed them together. I shifted my bottom a little in the desk chair, and lower down its carriage wheels creaked a little as they rotated on the vinyl chair pad that protected the beige office carpet. Under my pleated dark-blue skirt, I felt a moistness in my panties. Illegal panties.

We had "met" online, and chatted a few times with instant messages. We had spoken by phone only once, to set up this day's meeting.

We hadn't really gotten too deep in a cyber way, or even by phone; I think we were both saving up for the real-time first meeting. But I had shared that I liked retrodressing; he had said that he had always wanted to meet a retrodresser. I said the curiosity was reciprocal, that I was curious to meet an admirer of retrodressing. I remembered how he sort of had to wring the confession out of me; he used a combination of directness, shielded humor, and reverse psychology, and a little bit of condescending authority that made me shiver a little when I reflected back on it. It took a bit of skill I think, to break through my reluctance to admit to something becoming increasingly frowned upon and legislated in our modern society. He also seemed to be aware that I was feeling a little relief and satisfaction in admitting something, well, considered quite naughty.

He asked me if I wanted to "try out" as his "1960" retrosecretary. I took a long breath and I think he could tell, through my reluctance, that the question gave me a bit of a tingle that I tried to hide. I ended up telling him that, well, that I even had a retro name...Doris. Doris Dee. He didn't ask my real name, even my first name, and I didn't volunteer it.

So when I got there, "Doris" hadn't really arrived yet. I was dressed in my regular things, the drabby clothes I think we both thought were so boring, an attitude perhaps shared by many but expressed, these days, by almost nobody. At least in public, anyway. We started off sitting together over a cup of coffee. We sat in his kitchen. His wife was away on business for a few days. I had my Doris dress-up bag with me. He was nice looking, mid forties, clean shaven, gray-blond hair, about 6 feet tall and about 180 lbs.

He looked me over and smiled. "You'll make a nice secretary," he said. His bold gaze was scrutinizing me quite thoroughly, lingering a little too long on my hips, my legs. I glanced down. I was dressed, of course, in the boring way women dress these days. Dark slacks, flats, a monotonous and curve-cancelling sweater, a bulky jacket. Yes, I'm slim and on the petite side of average. 130 pounds, 5' 6" tall. I have a cute face and my legs are my strength, along with my hips.

I have minor physical flaws; my front teeth aren't quite straight, and when I look over my shoulder into the mirror I always wish my bottom was smaller to match the rest of me. I'm a size 7, A-cups, 32-22-35. I'm...let's just say...about 30. Young enough to feel the excitement of the forbidden or discouraged female decoratives, yet old enough, just old enough, to have grown up when such things weren't yet "off the list", were still sold in specialty stores and intimates sections at most department stores.

When my coffee was nearly empty, I sipped the last, lukewarm swallow and I looked over the cup's brim at him. I noticed something in his eyes that wasn't there before, something hungry, maybe even a little bit shrewd, or calculating. I looked away from his eyes, and took a breath to shake off the shiver of nervousness that came from his long and thoughtful stare. "You'll make a good boss," I said, echoing his phrasing, but it felt a little weak.

"Well," he said, getting up and guiding me to my feet with a hand on my shoulder. "Let's get started, shall we?" It was our first actual contact, and it had some feeling in it, somehow both gentle and with a touch of firmness as well.

Mr. James showed me his home office, said he'd be back in awhile, and left me in the small reception area. I got dressed, using the powder room I found in the outer hallway. And, of course, ten minutes later he surprised me by coming in suddenly. Now I was a little flustered, wondering what he had thought, how much he had seen.

In recent days, in the privacy of my apartment I had, of course, tried on some of my secret collection in anticipation of our meeting. I had secretly appreciated the feeling of fine satin under my fingers and hugging my waist, admired, in the mirror, the swish of a pleated skirt. And yes, with a full-length mirror nearby I had stepped strappy high-heeled sandals into a vintage garter belt, shivering slightly with illicit pleasure as I pulled it up, felt that distinct, gently roughened sensation of its lace-edged elastic sliding up my thighs and across my bottom. Centering it above my hips, my thumbs working the waistband to get it placed just so, front and back garters centered thighs-wise, the little satin bow centered just below my navel.

As I was daydreaming, the intercom on my desk phone clicked and Mr. James spoke:

"Doris, can you bring in that Dextell report?"

I pushed the button, "Yes, right away, Mr. James."

I stood, smoothed my skirt, gathered some papers and walked to his office door. I opened it and walked in, crossing to his desk, a large walnut conference-style model with a matching credenza set against the office wall behind his chair. I noticed that it was a nice office—quality prints on the walls, of nautical scenes and European vistas; a stuffed tan leather sofa stood against the wall opposite of where his desk was.

Mr. James looked up from his work, and eyed me up, and down. Then up again, a little slower. I stood still, holding the papers in front of me, a few feet in front of his desk. His eyes twitched and twinkled, and met mine. Then his businesslike manner resumed.

"Sit down," he motioned to the sofa with a hand. "Why don't you proofread it while I finish here?"

"Yes, I'll do that Mr. James." I turned in my heels and walked over to the sofa. I added a little swish to my walk, and felt the pleats of my skirt brushing my thighs. Feeling his eyes lingering upon me as I moved, I thought I heard a little hum, like an involuntary, half stifled grunt of pleasure, from Mr. James, but I didn't make any sign that I had noticed. I stopped in front of the sofa, primped my light brunette hair a little, turned, smoothed the back of my skirt and sat. I looked up at Mr. James as I crossed my legs, right knee over left, and saw his eyes drop to glance down and observe. He seemed to take a needed breath.

I got out a pen and began proofreading. I kept a sly eye on Mr. James, and when I felt him raise his eyes again to glance my way, without looking up I uncrossed my legs and recrossed them in a single fluid motion. I know he got a glimpse between my knees. The thought gave me a little, naughty shiver.

I had chosen my outfit especially for this day. I wanted to be very "secretary," of course. So I had on my gray-blue chenille pleated skirt, hemmed just a few inches above the knee. A nice simple full slip, white satin. And nice maroon pumps, with a much lighter tan saddle inlay for a feminine flourish, and 3 1/2 inch spike heels.

My stockings were sheer black nude, so my shaved legs showed their smooth skin through the thin black nylon. They (the nylons) had wide 5-inch black welts starting about 10 inches above my knees, and I had them held up with a fairly plain ivory white satin garter belt with thin elastic garters, two in front and two in back. My panties were light-blue satin, brief cut, with a tasteful trim of cream-colored lace around the legs, and similar cream stitch embroidery of roses patterning the front panel in a trapezoid chevron design. Behind, they were just the sheer blue satin.

My blouse was white, long puff-sleeved, simple really, buttoned up to my neck. Under it I had a white lacy bra. And I wore a maroon jacket, almost the same shade as my heels, with padded shoulders and ivoroid buttons. I had on a string of small faux pearls, and clip-on pearl studs on my earlobes. I had some makeup on, and pale blue eye shadow, and a deep red lipstick.

Was I a flawless slice of 1960 office fashion? Perhaps a social historian specializing in the period, or a Hollywood costume designer could have found some slight anachronisms, but I'm pretty sure I was solidly pre-1963, and of course there's nothing technically anachronistic about predated items. So my stocking seams were perhaps odd, perhaps a tad old old-fashioned, but not chronologically impossible.

I turned the page of the document I was reviewing, and uncrossed and recrossed my legs. I heard a stir from Mr. James, and looked up over my glasses and saw him looking at my legs again. I'm sure he had just seen between my knees when I had uncrossed, so I shifted in my seat, letting my skirt ride up a little, and pointing my knees at Mr. James. I could see him almost shiver. He took a deep breath and I saw him look at his own lap. He adjusted a little, and I had a feeling he might have touched himself through his pants. And I could tell from his energy and growing agitation, that he was gearing up for something; something beyond the passive.

"Doris," he said. I looked at him over the tops of my glasses. I uncrossed my legs and rested the papers in my lap. I let my knees part slightly, but the papers and my hands still obscured most of my lap from his view.

"Sir?" I said. I raised my head, reached up with one hand and felt my hair, primping, assuring myself that it was still pinned in its loose bun. I saw his eyes dart downward to my waist and lower, and I deliberately gathered up the papers in my lap and I quickly crossed my legs, but I was pretty sure his gaze could momentarily gather in a tantalizing glimpse, if I timed it right. During the brief moment my knees were about to cross, I watched his eyes peering up my skirt, thru the shadow between my thighs; he may have seen a quick flash of the white lace ruffle of my half slip, and perhaps the edges of my white frilled garters stretching across the fronts of my upper thighs.

And then I knew he did see something, because this time, he moaned. It was quiet, but I heard it. Then he realized he was in the middle of an instruction.

His moan quickly evolved into a clearing of his throat, then Mr. James said, "Um, Doris, please get me those journals over there?" He nodded toward the corner of the room, next to the sofa, and to the left side of his desk. A pile of magazines was stacked neatly on the low side table, in the space between the arm of the sofa and the corner.

I set the papers aside on the sofa, stood and walked over to the corner. I let my hips swing a little more than usual. I hadn't smoothed my skirt down when standing, so the hem was still riding a little high. I glanced back over my shoulder at Mr. James, smiled quickly, then I leaned over without bending my knees and gathered up the journals, perhaps half a dozen total. I stole a quick glance back at Mr. James. He was looking at me, but not at my face. One of his hands was under his desk, in his lap, and his arm was moving a little.

I think he might have been adjusting himself in his pants as he looked at my legs. I was bent over just enough, so he must have been looking up the back of my skirt, too. I'm sure he could see the tops of my stockings, a little thigh, maybe some of the back garters even. I wondered if, in either of his quick peeks, he had yet seen the pale blue gleam of my panties' satin crotch. The thought of his eyes on my panties made me shiver, and I felt myself moistening there a little further. The feeling made me press my knees together a little bit under my skirt.

I gathered up the magazines, straightened up, walked briskly back to Mr. James's desk, and lay the pile of magazines on the corner.

"Come over here, Doris," he said. I took the long way around his large desk, desk and stopped, standing with my feet together, still half a dozen feet from the narrow lane between Mr James's desk and his credenza.

"Let me take a look at you," he said. "I may need an assistant on some of my business trips."

"Oh sir, I would love that."

"But my assistant must look good, dress well, present a professional appearance."

He motioned me over, closer, looking me up and down. Less briskly, using small, careful steps in my high heels, I ended up another half-yard closer to where he sat in his deluxe upholstered desk chair. He gestured a little twirl with a finger, and I gathered that he wanted me to turn.

With a smile, I took another full step toward him, stopping about 2 feet short. I put my feet close together, letting my high heels click on the floor. Then I turned slowly around. Once, then twice. When I could, I watched his face. He was looking at my legs, and my skirt, my hips, my waist.

"So you've been working hard,"

"Oh yes, sir."

"Maybe you need to take a little break."

"That would be fine, sir."

"Come here." His voice was curt, and commanding. My eyes darted to his, but his face remained calm, inscrutable.

After pausing to inhale a quick breath that didn't quite calm my nerves, I went to him. I walked the last little bit, two steps, and stood next to his chair. He swiveled his chair over, so now he was facing me. He took hold of my hips, gently, and turned me a little, and I started to turn further, but his hands stopped me and turned me back. I giggled a little, my nervousness escaping forth audibly, and felt his hands tighten on my hips. I looked down at him over my shoulder, and he wasn't smiling. I felt a little chill. And goosebumps.

His hands were still firm as he turned me completely around, facing away from him.

"Don't look at me," he said. I felt another chill.

I felt the air get cooler on my thighs. He was lifting my skirt in back. I turned my head, reflexively, to look at what he was doing. His hands stopped.

"I said, don't look..."

"Oh," I mumbled and feeling told, talked down to, I lowered my eyes, held still and quivered a little, uneasily. I felt his hands on both sides of my skirt, lifting it. I couldn't look, but I could feel what his hands were doing with my clothes; he held the hem of my skirt up with his left hand while he pushed my white satin slip up too. There was a tremble to his hands, I thought, or maybe it was me.

"You dress...enticingly, hon," he said. Aware that his eyes were on my bared skin and my revealed underthings, my mind teetered between the present, exposed reality, and remembering a parallel moment early that morning when I'd been assembling and trying on the very items he was peering at now, when I held my own skirts up and looked over my shoulder at my legs and bottom in my bedroom mirror at home.

"And where did you acquire this clothing, honey?" he said. His fingers. I felt the tips of them slide down the side of my right hip, slide across the satin of my panty bottom, and very lightly linger at the edge of elastic.

"Um, oh..." I stammered a little. I knew my retro tastes, my secret collection was taboo. There was judgement in his voice, amusement too, attitudes reflecting my guilty little secrets, and his own discreet appetites. Feeling his eyes on my bared thighs, my garters, my nylons and panties, hearing his breathing and the rustle of the layers of my clothing bunched in his big masculine hands, holding them up for his viewing pleasure. He waited for my reply, appreciating the view.

"Well, sir, um, most of my...things...well, when my grandmother passed away, I was cleaning out some of her belongings..."

"So this is original vintage?" he said. "Hmm."

"Yes, sir."

My skirts fell back down and his hands rested at my waist.

"So you think you've earned a little break?" he asked. His hands tightened on my waist, and I felt him pulling me back.

"Oh yes sir," I said.

And he was pulling me down. I resisted for a moment, then relaxed. He pulled me down toward his lap. I smoothed the back of my skirt and sat on his knees. I felt his breath lightly, but warm, on the back of my neck.

His hands ventured a little lower, sliding down from my waist to my thighs, but still over my skirt. His hands slid back to my hips and up across my tummy to just under my breasts. Sitting on his lap, under my bottom I felt his member through his pants. It was like a long, soft sausage there in the middle, nesting between the cheeks of my bottom. I wiggled a little and he gasped softly and I felt it stiffen a little more in its resting spot.

Suddenly, he grabbed a handful of my hair and turned my face toward his. I thought he was going to kiss me. Instead, he spoke.

"Look at me," he said. I looked at him and gulped. His face was angry. "You've been a very naughty girl," he said. He let go of my hair, and I looked down, suddenly ashamed.

"You haven't earned a break, Miss Dee, not yet," he said, coldly. I felt another chill flow over me. Mr. James placed his hands firmly on my hips again and pushed me off his lap and to my feet.

"At least, not the kind of break you may have been thinking of. I know what you've been doing, when you were supposed to be working." I stood and felt for my balance, feeling a little swoony, but also the strength and authority in his voice, and in his hands and direct attitude. His hands hadn't let go of my hips. With gentle force he turned me, and I moved my feet, looking briefly down at my high heels, so my left side faced him. Then he pulled me in close, spreading his thighs, and placing me between them, then clamping his legs around mine.

"Please sir, I'll get back to work now," I said. My voice rasped, cracking and fracturing slightly under the stress I felt.

"You'll go back when I tell you too," he said. And I felt his hands again, behind me. Mr. James was again gathering the the hems of my skirt and slip in his left hand and lifting them. I could already tell, the way he breathed, the way his hands moved, the way his body moved behind mine, that this act, this upward un-draping, was something that he liked to do, and indeed, to repeat. This time, he pushed my skirt and slip up more slowly, but somehow more intently, and I knew he was studying the backs of my thighs, my nylons, my garters, and then my pretty panties, inch by inch. Then, while his left hand held my skirts up out of the way, his right hand slid down again, coming to rest softly on the back of my left thigh, the palm and fingers cupped, feeling the sheer nylon, then sliding up to my bare thigh and garter strap. He slid his fingers under the strap and back out again. His big, warm hand then crossed to my other thigh, and under the garter strap again. A soft low grunt emitted his pleasure audibly. Then his hand glided in between my upper thighs, and I could feel his cool fingers sliding between them. I felt his single-handed touch on the insides of both my thighs. I felt my hips twitch. I gasped.