The Adventure of the New Apartment

Retired, I had too much time on my hand with my family so far away. I found an apartment in the city with a history of successful short term rentals. My agent said it was a sure thing, a package – the owner had contacts with maintenance people and a cleaning company that knew the special requirements for AirBNB – quick response if clients were on the way, even quicker if someone was in the unit. I’d pay more but the key to the game was the reviews people left.

It was an ancient building of old brick and stonework unavailable at any price in this century. The apartment had been remodeled a number of times but the neighborhood association and the local historical preservation society maintained strict oversight for authenticity and critical details. What finalized my decision though was the neighborhood which reminded me of the small town in which I had grown up. People were friendly and communicative but with the addition of the twenty-first century open-mindedness that welcomes persons of varied backgrounds and levels of economic means.

My worries were few – the place was recently painted inside and out and the only dated section was the kitchen which unfortunately was way too nineties for current tastes. My agent found an architect-constructor to handle the needed renovation but there was one already-commited rental within the month which meant construction would be delayed.

To familiarize myself with the place I loaded up a weekend suitcase and several boxes of cleaning supplies and planned to do the basic preparations for the upcoming rental by myself rather than calling the cleaning service. ‘Last time’ I promised myself but the truth was I was a bit tapped after the expense of the closing. One weekend of grime wouldn’t hurt me – I bought the place to be more occupied, didn’t I? As there would then be a two week vacancy prior to the rental I’d have the service do a quick turn right before to freshen things for my guests.

I unloaded the cleaning supplies and the heavy duty vacuum I owned and went down to get my suitcase. Instantly I realized that I’d taken it out in my garage at home to re-arrange the other stuff so I could get the vacuum in the car. Of course I forgot to re-load my suitcase! I had no change of clothes or bathroom supplies for my visit. Linens were supplied by the cleaning service so were no problem, but I couldn’t spend the weekend wrapped in a towel.

“Convenient shopping nearby’ I remembered from the fancy brochure my agent provided. That was up in the apartment with the details. I locked the car and headed back up.

Inside, I thought “Rental Unit”. People are always leaving stuff behind. There must be a cache somewhere inside that might at least keep me from having to shop so late in the evening – even a grandmother’s nightgown would do – there was only me. I looked high and low and in the “Owner’s Closet” which all such places have – not accessible to clients. I found no cache of left-behinds and discards. Finally in the yawning Master Bedroom walk-in I noted the fine design of the modern closet – shelves and cubbyholes and racks for a couple of adults’ clothing for a full week in the city, all free of dust or anything useful to my dilemma.

I noticed the shelf unit at the rear of the closet was not quite square to the wall. It stood out in contrast to the otherwise fine appointments. I walked up to it and pushed and heard a weighty ‘click’ as the shelves slid into perfect alignment with the wall. What the hell? I pushed again and this time heard a ‘clack’, then the shelves hinged outward as a unit. It was a door! Wow, I thought, this is cool. Why didn’t the property description elaborate on such an interesting fixture?

I opened the shelves further and found a light switch beside the door on the inside. I wondered if anyone knew about the room? It was dusty as if the cleaning service hadn’t found it and this was the cache I’d been looking for. A clothes rack with dresses and women’s clothing, several suitcases including a makeup case and boxes of cosmetics and perfume bottles and other female paraphernalia, and an old fashioned trunk which opened to display a very modern collection of ladies’ shoes of all kinds and styles – grubby to casual to office chic to elegant formal heels.

Curious, I opened the suitcases and was enchanted by a collection of lovely and expensive lingerie, a variety of pajamas, nightgowns, and blouses, basically everything a woman would need to live here for a month. That was the springboard to my next thought – maybe I didn’t need to go shopping after all? I remembered long weekends years ago and the joy I found dressing as a woman day and night on certain rare occasions. I quickly pulled together several casual jeans-pants-tops outfits that looked as if they would fit. This must have been a larger gal as she and I wore like sizes. I was set for the weekend!

‘Allison’ I thought, remembering my female name. What fun I had in my twenties before I met my future wife…

I looked into the vanity mirror seeking some kind of affirmation. Decades had passed – would I still love it? The slightest twinkle in the mirror from one of the boxes of creams and lotions caught my eye. I turned and found the shiny top of a bottle had caught the light. It was an expensive bath oil that I remembered loving, one that filled the bathroom with a relaxing fragrance that always put me in the weird mood of combined relaxation and stimulation before I slipped into something feminine.

Back at the mirror, I raised an eyebrow and Allison smiled back at me. ‘Allie, silly’ she mouthed to me silently with a flirtatious smile before I turned away to fix my bath. Grasping the taps I thought I heard a soft “Thank you” so I turned to the mirror but it had fogged over, my reflection indistinct. As an enchanting scent filled the room my thoughts wandered to memories of warm water and the candlelight with a pretty robe, chemise nightdress, and slippers waiting for me.

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Allie rose from the bath some minutes later, refreshed and inspired but ready for bedtime. She dried herself in a huge towel she found and made a mental note to freshen the linens in the dryer. Covering herself with the towel she returned to the secret cache of lovelies and found a nightgown, matching robe and slippers. Allie was fully aware of the long list of grooming chores she’d have to do to feel ready to go outside shopping in the morning but also felt her eyelids growing heavy and the large bed beckoned. Sliding into the fresh sheets in the master bedroom was heaven and she soon drifted away to dreams of lace and candlelight and a view of the world decidedly her own.

Our princess woke up starving – she’d skipped dinner last night. Her first dilemma – what is the least to do to get ready so as to go out to find some breakfast? Happily she had another flash of inspiration Allie pulled on the robe and slipped on her slippers and dashed downstairs to the big blue notebook on the table next to the huge easy chair in the living room. The third page was entitled “Restaurants that Deliver”.

Allie quickly found a diner and one short phone call later had only to pick out an outfit to meet the delivery person. Twenty minutes? Could she do a face that quickly? From somewhere she remembered getting ready in a hurry – satisfying to her businesslike efficiency, annoying to the artist that did her makeup. A quick facial then bra, forms, panties, and some skinny jeans and a top. Next eyeliner, nothing else, wait – mascara! – a bit of blush…a bit more…lipstick, no lip gloss! She laughed at herself and remembered she wasn’t twenty-two any more – the decades that passed needed more attention not less! She decided she was delivery-guy-presentable anyway just as the doorbell rang.

Except it wasn’t a delivery guy but a delivery girl. A woman almost her age. The lady wore denim and a beautiful coat of white and black. Her makeup looked a bit hurried as well. The lady smiled broadly and said, “Karla from the Diner. Welcome to the neighborhood! Thanks for ordering from us – it’s a bit spare on the short-term rentals right now so we’ve not been busy. This is Malcolm’s place, isn’t it? Or rather, I should say, ‘Sherry’ – another woman just like us!”

Us? Allie blinked and couldn’t believe her eyes. “I, uh – had no…well,” she replied, flustered by the odd familiarity from a stranger. Her face must have been a mixture of confusion and embarrassment.

The lady laughed heartily. “That’s the greatest compliment we can get, isn’t it? Fooling one another! Thank you, thank you, thank you, you have made my morning. But double welcome because you are going to love it here. We special girls are part of the passing parade here and you’ll be welcome in every shop and restaurant. You might want to look into a different palette on that makeup, though – you’re more a Summer in my estimation.”

Allie laughed. They hadn’t invented such things when she was dressing in her younger days. She remembered hearing some sort of discussion between her wife and daughters in years past. She’d have to check out a real makeup store to find out what the delivery girl was talking about. She tipped Karla, paid for the meal and thanked her for the friendly welcome.

Karla invited her to a weekly get-together of local ‘special girls’ at one of the church’s common rooms and left her phone number in case Allie needed anything else – “Advice, shopping recommendations, where to eat, anything, love! Just call!”

So began her first weekend in the new place.

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As she grew more comfortable in her new life Allie enjoyed life in the apartment and the new neighborhood so well she decided to stay a few more days. She faced the world as her new/old self and came to terms with life as an older but vital woman in a world where she was accepted and known only as Allison and to a growing number of friends as ‘Allie’ or ‘Miss Allie’.

One morning the doorbell rang. The gentleman revealed himself to be Malcolm, the old owner – they’d not met as modern closings are affairs of email-sign-scan-email and so forth. Malcolm had been out of the country the entire time.

At first formal and a bit coy, they discussed the dilemma that the contents of the secret room were not really supposed to be part of the sale but became Allison’s property as Malcolm was unable to retrieve them prior to Allie’s possession.

Both parties did their best to give everything to the other in a growing spirit of friendship, the conversation facilitated by the lady and the gentleman sharing a bottle or two or three of Korean Soju while they chat. Neither realized their afternoon was brightened by a beverage that looks like a beer but is more akin to whiskey in alcohol content.

Allison revealed she’d already heard that Malcolm is ‘Sherry’ to the neighborhood and that she would very much like to meet her. In response Sherry suggested the ladies dress up for a night on the town. Both a bit tipsy, Sherry animatedly listed all the restaurants and bars they must visit and the conversation moved to the secret room where Sherry began to pick out dresses and lingerie and shoes and jewelry and makeup for each of them.

Allison loved the irresistible charm of her new friend and accepted the sudden familiarity but wondered if she could keep up with such a force of nature. Without a single item of feminine attire, Sherry was inarguably ‘the female of the species’ and so feminine in her manner as to be intimidating. As Sherry prepares her face and begins a quick but elaborate makeover for our princess, Allie is aroused but worried…

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Allie narrates their encounter –

It is my first meeting with another crossdresser. When she came to the door, dressed in drab, me in feminine but very casual attire – top and jeans, flats, no jewelry, the lightest of makeup. My hair is parted in the middle and held with a young girl’s hairband (tiny unicorns) since the others I’d found were a bit on the dressy side.

We got a bit drunk and as all the goods I’d found were arguably hers, how could I resist when she suggested we dress up and go out for a drink? She took the lead from the beginning – picking out an outfit for me, almost totally doing my makeup while fixing her own face, chatting non-stop of the restaurants and bars that we ‘must’ visit, complimenting me on details of my appearance in the most charming way.

“Heels, of course,” Sherry says emphatically, radiant despite being half-dressed. “Don’t be shy. And if some gentlemen take an interest, just follow my lead. The sweetest drink is one purchased for you because of your beauty, but here’s rule number one: The sweetest touch for you tonight, my dear, will be mine.”

I shivered at this blatant reference to sexuality. I’d dressed unreservedly in my youth, gone out, partied, and known boys who if they hadn’t asked for my number were at least reliable escorts once they found me at a bar. I’d gone as far as a furtive kiss or two, the touch of their fingertips or palms on my body, but never once anything beyond except in my imagination.

My mentor in those days was a maiden aunt who’d discovered my secret hobby as well as my fascination with femininity. Far from discouraging me as my parents might in hopes of future grandchildren, my aunt embraced my desires, tutoring, criticizing, supplying pretties and cosmetics, watching me learn to walk in heels in her front parlor. She insisted I do the book-on-my-head thing! Demeanor, deportment, posture – over and over until her broad smile showed how pleased she was, how proud of my transformation. I loved her as I loved none other.

Returning from my reverie I found Sherry pulling a dress over her head. Her lovely fingernails danced over the fabric as she smoothed it in place over what I knew were exquisite underthings. Realizing I’d been quiet she turned to me.

“What’s the matter, my darling? You seem lost in thought…”

“I don’t know how -” I began, then “I don’t know how women make love, I mean, to other women.”

She smiled kindly, stifling a giggle. Her eyes dancing, she said, “Let’s make it a date, then. I’ll be your escort and your role is simple. Be a girl on a first outing. Let me open the doors, make all the strategic moves, all you have to do is to keep your eyes open and try to complement my efforts whatever they may be. It’s all foreplay, it’s all about the fact that later tonight you will be mine completely. Sorry if I’m so forward but I know it’s been years and by the way, that red is a bit understated for the vamp you are tonight.”

Another reminder I truly must visit a real makeup store.

Sherry poked and prodded through the box of cosmetics and inspected one lipstick, then another, then another, rejecting them again after again. Finally, she laughed and opened one to dab it on the back of my hand, the red a perfect match to my nails, which she had painted herself this very afternoon as we sipped our drinks.

“There, darling, put this on and I’ll do my best to resist kissing it off until after midnight,” she said as her broad smile and mischievous eyes reduced me inside to a virgin quivering before her. To calm me she leaned over and whispered what she would do to me, ‘after Midnight’, punctuated by a sexy lick of my earlobe that jangled the earring I wore.

“But don’t be afraid to kiss the boys between now and then,” she said. “Sweet drinks, right?”

I nodded enthusiastically, following her lead.

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We held hands all the way home, a bit high still, but sobering in the cold air. Our mood was still exuberant, two girls laughing at their exploits for the evening. As expected more than one gentlemen bought drinks for us in exchange for a dance or two and the right to touch either or both of us and once two of them asked us to kiss each other while they watched! Sherry looked at me and I smiled shyly and then she just did it – kissed me passionately to the appreciation of our benefactors. I felt guilty, knowing the boys wanted more than what they asked for and started an apology but the guy just laughed and looked at his friend, then said, “We’re together, too.”

At the door Sherry didn’t ask, either, embracing me and taking my lips by storm. Her warmth felt nice against me and I hoped I was doing what she enjoyed, responding but permitting her to take us where she wanted to go. She opened our door and lead me in and when I readied myself for another kiss, she took my hand and pushed it where she wanted me to touch her, the firm mound below her belly.

I’d never touched another person’s sex other than the girls I dated and the woman I eventually married. This felt deliciously forbidding, exotic, and over-the-top exciting. I looked to her for affirmation and she placed her hands on my shoulders and exerted a gentle downward pressure. The look on her face was kind and loving, not needy at all, more than a bit confident. We’d kissed all our lipstick off, I noticed as I knelt before this woman I’d come to adore.

She raised her skirt slowly revealing the lovely sheer slip she’d worn, which she then began gathering in her palms as well. I raised my hands to help and she nodded but whispered, “Slowly.” I felt her silky thighs under my fingertips and shivered at the thought I was touching her so intimately. I heard a pleasured sigh in return.

This was unlike any lovemaking I’d ever experienced. We were both so gentle, so measured and careful in our movements. Was it the perfume? We smelled delicious and erotic, the scents oh so carefully selected by my darling before we left that evening. I wondered why she took so long, why she had to test each one, only letting me smell her wrist once she’d decided. Her scent was an amalgum now, the inevitable smell of noisy bars and the ocean air outside mixed with the sweet honey of her perfume, jungle-exotic mixed with that her very own.

The panties were very brief, her pale thighs and belly in stark contrast to a dark red patch of satin decorated with lovely black lace at the edges. She’d put herself away carefully and sported a very feminine shape I’d not expected. I looked at her perplexed at what was obviously a female vulva. She smiled down at me and said, “You must kiss me, my love.”

I pulled the panties down her thighs over the beautiful hosiery she’d worn, down her calves to her ankles. She must have stepped out of them but I was transfixed by her sex. Shaven except for a strip above what was an exquisitely female set of vaginal lips. Two long fingers slid down her belly onto either side of the crease, her fingernail polish shining in the one lamp we’d left lit for our return. She motioned with one finger to a spot low down in the crease.

“Lick me here,” she ordered.

Inside the crease I found the tip of her clitoris and I began licking and exploring with my lips and tongue. She showed me the glamour later, her male parts folded inside her body, the clitoris held down by folds of flesh pulled over and glued together with surgical glue until just above the head. This arrangement permits peeing while sitting down, accommodates erection, leaves the lovely sensitive tip exposed, and creates a tunnel underneath that with a bit of lubrication allows fingering and with care, fucking from front or back although accommodating a lesser length than a natural vagina.

Her hands held my head in position as I discovered the various elements of my beloved. It was unusual but I learned to coax the various sighs and cries of pleasure from my darling Sherry. When I’d made her come one time, then another, with my mouth, she pulled me to a standing position and freed my erection from my underthings. She offered no detailed direction, simply a “Fuck me.”