The Drop-Off

"Where's my comb, Mommy?"

Margo sighed. Sissy could be so needy at times. And was there even a brain underneath that pile of blond curls?

"I'm sure I saw it on your nightstand. But if you can't find it in all the junk you've piled up there, I'm not surprised!"

Yes, Sissy's nightstand was a clutter of lipsticks, rouge, mascara and numerous other skin care products, all amassed in the search for a more perfect face. The quest was never-ending and Margo, who preferred the natural look, was not much help.

"Mommy, I can't possibly fit everything into this dinky little bag. Can't I please take two?"

With another maternal sigh, Margo climbed the stairs up to Sissy's bedroom. "Look Sissy, you're only going away for the weekend. One travel bag should be fine. I mean, how many kimonos do you need?"

The reference to one of their favorite movies made them both laugh. They had spent countless hours snuggled on the couch together, binge watching and girl talking. Margo loved these hours. She would always remember them fondly.

Sissy flounced over and threw her arms around Margo's neck. "Oh Mommy, are you sure I should go? Whatever will you do with yourself?"

"Now Sissy, we talked about this. It's important that you go out on your own. I can't always be around. And you know Uncle Randy is so looking forward to your visit. We simply can't disappoint him."

"Oh, but we can. We can run away together, just you and me, and not care a flip for the rest of the world. Please say we can!"

The stare of Sissy's big, pleading eyes was powerful, though its persuasive effect was somewhat undermined by her still amateurish application of eyeliner and mascara. Sometimes Margo just had to laugh at her little raccoon.

"Oh-ho, you think it's funny, do you? Well, try this then!" Sissy dug her nails, her painstakingly manicured, turquoise nails, into Margo's ribs. "Tickle fight!"

Usually an easy mark for such games, Margo would not let herself be distracted today. No, they really had to get going. Drawing back with a cry of "Stop!" she firmly placed restraining hands on Sissy's shoulders. In her haste, one hand pulled at Sissy's golden hair, knocking the wig slightly askew. For a moment, she caught a glimpse of Steve, the man she had married so many years ago.

************

"Mommy, are we there yet?"

They really hadn't been driving that long, but Sissy's nervous energy simply could not be contained.

"No, sweetie. I told you it was an hour's drive out of town and we are still in the city. Uncle Randy has a beautiful house in the country. Very quiet and secluded. You are just going to love it there."

The look on Sissy's face told Margo that it was going to be a long ride for both of them.

"But am I dressed all right? Are you sure we shouldn't turn around? I could still change."

The very idea made Margo shudder. There was no way she was going to add yet another act to the drama that had been choosing what to wear for the weekend. Sissy's initial concept had been full-on nympho-fetish-slut doll. The black latex maid's uniform did go well with the red posture collar, but the platinum wig was a bit jarring and the 6" heels simply did not look sustainable over a long weekend or even for a walk up the cobblestone path to Uncle Randy's front door.

Once again, Margo proved herself the adult in the room as she coaxed Sissy down off her towering heels and into a much more sensible pair of Mary Janes. Topping things off with a short plaid skirt and white blouse created a sexy schoolgirl look that had a bit of heat without being hopelessly vulgar.

"This is the first time you two are meeting, after all," urged Margo. You wouldn't want him to think you are too easy, would you? A good girl wouldn't do that, would she? Don't you want to be a good girl?"

"Oh yes, Mommy, more than anything! I'll wear just what you say." And for a time Sissy seemed truly pleased with the ensemble, preening in front of the mirror and practicing lisping little compliments and chit-chat.

Now that they were in the car, however, nothing was right. Margo noticed how Sissy pulled on the hem of her skirt, as if it were too revealing. There was of course no hiding the slight bulge behind the pleats. Even caged and locked, the little man made his presence known.

Waiting at a stoplight, Margo looked down at Sissy's legs. Long and straight and not particularly shapely. No, they were certainly not her best feature. But in those white stockings they did look rather girlish and so would do. They would have to.

The light changed and the pair continued on their journey.

"What if he doesn't like me, Mommy? Did you show him my picture?"

"You know I did, darling, and he was very pleased and eager to meet you. I told you this already."

"But I wasn't in this outfit, was I Mommy, in the picture?"

"No, of course not, but that doesn't matter. Uncle Randy isn't looking for a dress, he's looking for a girl - a good girl, like you. Didn't you just tell me that you were a good girl?"

"Yes, Mommy. I try to be, anyway."

"You don't just try, you succeed wonderfully. So tell me, what is the first rule of a good girl?"

Sissy looked straight ahead as her eyes focused in an intense yet oddly vacant stare. "A good girl must please her man in any and every way she can."

"Your little recordings have taught you well," affirmed Margo, placing a hand on Sissy's knee. "But don't you see dear, you can't spend your whole life just listening and watching. You have to get out there and do it! Isn't that what you want?"

"Yes Mommy, I do," replied Sissy in a soft voice barely above a whisper. Seemingly exhausted by the admission, she fell back onto a bed of silence.

Margo used the resulting lapse in the conversation to reflect on her life with Sissy. Sometimes it amazed her how such outdated, distorted ideas of what it meant to be a woman had been planted into her head. How had they gotten there? Steve had shown no sign of such notions before they got married. He was kind and considerate and above all respectful. He respected all women, especially her. That was one of the reasons she had decided to marry him.

But then came the day of the great revelation. The day he just had to tell her about his true feelings and desires and what he really was - a she. Margo had heard about this type of man, whose masculinity was just a shell, or rather a cocoon enclosing a beautiful female butterfly just dying to come out and flaunt its fabulous paisley wings in the sunshine of a loving and admiring world.

And what sort of woman had emerged from the shell of her husband? A girly girl, sweetly submissive and eager to please. That made the transition easy, at first, as the new Sissy threw herself into cooking, cleaning and other household chores like a hot babe in sex toyland. Even the most menial task was new, fun and exciting, especially if it could be performed in a maid's uniform or, even better, skimpy lingerie.

Good sport that she was, Margo had played along. And why not? It was kind of like having a kid sister, who needed to be schooled in the ways of a woman's world. Surely there was never a more willing pupil than Sissy, who took it all in with her big eyes and newly-pierced ears. Yes, it was fun - for a while.

It was those newly-pierced ears that began the time of troubles as Sissy insisted on wearing her little gold studs to work "so the holes won't close." This little foray was followed by other feminine accoutrements that soon made it obvious to her coworkers that the quiet fellow in the end cubicle was not quite the man he used to be. Nothing was said, but when the next wave of corporate restructuring hit, Sissy was among the workers let go. No provable bias, no actionable claim. Just one gaping hole in the family budget.

Sissy did her best to make up for it, working extra hard around the house and trying her darndest to find a new job. But jobs are scarce in the best of times, which these are not, for applicants so obviously ill at ease in their interview clothes. And finding a woman's suit - Sissy swore that she would never dress as a man again - that would fit her stubbornly masculine frame was no easy or cheap task. Margo's salary as an elementary school teacher was hard pressed to cover their basic needs, let alone a new wardrobe for her transformed partner.

Had it been worth it? Margo looked over at Sissy sitting beside her. She could barely see Steve any more.

The car began making unpleasant noises as she thoughtlessly let it slip too far above the speed limit. It was long overdue for a tune-up, another expense deferred.

"C'mon, old girl. Just hold together a little longer. We're almost there."

************

"Well hello, little lady! It is an honor and a delight to meet you." Uncle Randy bowed low over Sissy's awkwardly extended hand. He was a round man, bursting with jovial energy and looking like he might roll away at any moment did he not so much enjoy the pleasure of your company. At that particular moment his energies were focused on Sissy, in an effort to thaw the ice between them with the warm sunshine of his attention.

Such a large, expansive man needed plenty of space and Uncle Randy had it in abundance. Sissy gasped when they were buzzed in at the gate and the house came into view as they rode up the drive. House? A mansion, white, sprawling and with a slightly Southern touch - just like its owner.

To be sure, even Uncle Randy wasn't large enough to fill the entire estate. He had a staff to help him. Three of them stood near the door and Uncle Randy introduced them.

On either side stood Svelte and Catnip, the two maids, who were beautifully but tastefully made up. Svelte's red curls flowed down over the shoulders of her uniform in contrast to Catnip's brunette hair that was cut off in a severe bob. Both were magnificently endowed with endowments that the tight fabric of their uniforms just barely kept in check. Black nylons with straight seams enclosed their legs, which even Margo had to envy as simply gorgeous. Only the size of their hands brought a faint touch of masculinity into the mix. Still, Margo thought to herself that Sissy could definitely learn a few tricks from this pair. She imagined the three becoming friends and gabbling away deep into the night about dreamy boys, make-up tips and how to tuck away the awkward bits.

In the middle of the trio was Omar, the butler. Towering over the two maids even in their high heels, his formal black suit hardly concealed the muscles bulging underneath. Uncle Randy liked his house kept orderly and Omar was clearly the enforcer of his master's orders. He bowed briefly in the direction of the new arrivals, like a sumo wrestler might bow to an opponent before moving in to break him in two. His intense gaze rarely left Sissy.

Sissy's eyes dropped to the floor. A meek "hello" was all she could manage in response. Margo stepped in to fill the awkward silence.

"Thank you so much for inviting Sissy. She really is looking forward to staying with you, even if she is a bit shy at the moment." Sissy took this as her cue to look up and force a smile.

Yes, thought Margo, it was so nice of "Uncle Randy" to take Sissy under his wing. She was lucky to have found him - online, of course. As her relationship with her husband became increasingly difficult, Margo had turned to Dr. Google for advice. Sure, a lot of couples faced financial and emotional challenges, but this was different and not something that her girlfriends could help her with. She needed the counsel of a specialist.

It wasn't just the strangeness of watching the change, the "transfemation" as she liked to call it. That part of the journey could be kind of fun and it was comforting for Margo to be the acknowledged expert in all things feminine. But the change went further than she had expected. Sissy wasn't just Steve in a pink teddy and lipstick. Steve had never been the most macho of men, but Sissy was such a little girl, desperate to be petted and fussed over and, most of all, disciplined. Oh yes, however much Sissy wanted to be a good girl, she knew she was bad and needed to be punished, a lot!

This had been the hardest part for Margo. She had done the research and knew that there were submissive guys who craved discipline and punishment. She also knew that Steve/Sissy was one of them. His physical reaction every time she bent him over her knee and gave it to him with the back of her hairbrush proved that point. Yeah, some guys were into that. The problem was, she wasn't.

Margo tried, but something just didn't click. You think hard limits and safe words are just for subs? She was the one who really needed them as she fended off all sorts of Sissy's ideas for "funishment." Even when Margo agreed to try something new, she just didn't seem to be very good at it, as Sissy made clear from her disappointed looks and detailed suggestions for improvement. That was the worst part, her repeated sense that she was failing her man - or what used to be her man, anyway.

That's when she went looking for advice and found Uncle Randy. He was so kind, and understanding, and helpful. He knew how to play this game and was willing to teach her. And when it still wasn't working for her, he offered to play it for her. Oh yes, he would take young Sissy in hand and give her what Margo couldn't.

All these memories flashed by Margo's distracted mind as if it were the last moment of her life. Until suddenly there was Sissy, pulling at her arm. "Mommy," she whispered, "we need to talk."

Margo looked up in embarrassment. "Could you give us a minute alone?"

"Of course, my dear. Take your time to say a proper good-bye." With that, Uncle Randy led his staff out of the room.

As soon as they were gone, Sissy blurted out: "Mommy, I don't think this is a good idea."

"Why ever not, pumpkin?" replied Margo in her best coaxing tone. "They all seem so nice. And did you see how beautifully the maids were dressed? I'll bet you could learn something from them. If Uncle Randy did that for them, think of what he could do for you. I thought you'd be pleased."

"I am, Mommy. I know you worked hard to make this possible. It's just . . . just . . . oh Mommy, I'm not sure I like men!"

There, she said it. Or had she? Sissy felt like she was only listening as someone else made this startling announcement. Whatever the source, she now slowly began to realize the consequences. All her silly hopes and hazy dreams of being a good girl began falling down around her, accompanied by a single tear that traced a black line down her rouged cheek.

Margo wiped it away. "Sissy, you can't give up now. You've come so far. It's what you've dreamed about, isn't it? Remember what you told me, and showed me? You'll never know unless you try. Be my brave Sissikins! Anyway, it's just for the weekend."

Sissy tried to smile, but even the artificial hostess smile she had practiced so long in the mirror was beyond her present strength. She looked up at Margo, waiting for a decision.

A final weary sigh escaped Margo, who knew what was to come. She had previously visited Uncle Randy's house to have a look for herself before agreeing to bring Sissy. Naturally she had asked to see where Sissy would be staying. Uncle Randy hid nothing from her. He took Margo downstairs to the basement and explained that he was a great believer in the transformative powers of darkness and isolation. Sissy would be completely wrapped in latex with tubes, regularly monitored of course, to serve her biological needs. At times, portions of her body would be unwrapped to receive carefully chosen ministrations of pain and brutality. Eventually her mummified flesh would learn to crave these stimuli and even to beg for more with a genuine desperation that could not be feigned and an unreserved submission that could never be withdrawn. Only then would she be ready to emerge from her artificial cocoon as a broken butterfly. But until that happy day, she would be consigned to the dark, timeless reaches of inner space. Sissy was in for a long, long weekend.

Margo looked at what had been her husband and would have spoken had not Uncle Randy appeared and tactfully suggested that it might be time to show Sissy around and let her get settled into her new accommodations.

Margo, tight lipped, agreed. "Yes, I really must go."

Omar showed her to the door. The envelope he discretely slipped into her purse was clearly well-stuffed. No need for counting.

Stopping at the threshold, Margo put on a brave face and said farewell to her girl. "Good-bye then, dearest. I know you'll have the bestest time." Sissy did not reply. Her throat was too tight and she feared that any sound she could make at this point would have been most unladylike.

Margo then stepped through the door that Omar so graciously held for her. Her teacherly advice to first-day parents came back to her now. Don't turn around, just keep walking.

"Mommy?" Sissy had found her little girl voice again, but too late. The door clicked shut as Margo walked out into the sunshine of a normal life.