Sissy, Secretary. Too close to be just.
Co workers. Hi, Hi, I'm Alana.
Yes, that Alana. The black haired one with the
shy smile, crossed legs and the way too tight grip on my little
notepad. And before you ask, yes, Sierra
and I used to be boys. Teehee.
That's kind of our secret, where the sissies in town is whishing
around in dresses, heels clicking, giggling behind our
hands, and most people don't even realize it isn't that
delicious. Anyway, this is how that whole
Mr. Hancock thing happened. So one evening, while Sierra was
lounging around, looking effortlessly gorgeous as usual,
I told her I had landed an interview to be a secretary for
the most dreamy, handsome man I had ever met, Mr. Hancock.
Tall, confident, smooth voice. I was already halfway in love.
He's going to put me through my paces, I said, trying to sound
professional and mature even though my heart was doing little
cartwheels in my chest. Sierra barely looked up.
Typical. But later that night, I
panicked. What if he thought I was just
some silly little bimbo? I mean, I am a silly little
bimbo sometimes, but still. So I decided to dress older,
more serious, longer skirt, less leg, very grown up Secretary
energy. The next morning as I walked out
the door, Sierra gave me this weird look.
You know the one, the oh honey, you're making a mistake, look at
the office. I marched right up to Mr.
Hancock, nerves buzzing, heels wobbling, and blurted out.
I'm ready for whatever you want to do to me.
Why did I say it like that? Before I could melt into the
carpet, he smiled and said, well I was going to test your
dictation skills, but we have a last minute applicant.
Then he called out. Come in dear.
And in walked Sierra in the tiniest little dress I had ever
seen, on her legs for days. Smug smile.
Total Sissy sabotage. Says Sierra.
I squeaked. Mr. Hancock looked amused.
Oh, you 2 know each other. I'll let you catch up while I
grab some coffee. And just like that, we were
alone. What are you doing here?
I hissed. No swearing, got to stay
feminine. She smirked.
I have just as much right to apply as you do, plus that I had
to see this man you're drooling over.
You can't even do this job. I whispered fiercely.
You've never worked a day in your life.
She giggled, actual giggled. Oh please, men don't ask for
dictation to many here words. They ask so they can stare at
legs. Then Can you believe it?
She lifted my skirt like she was searching for my legs.
I nearly combusted. You can't run a business on
legs. I protested.
Mr. Hancock returned just then and asked Sierra to sit.
And oh, did she sit. Legs crossed, just right, heels
pointed, posture perfect, like she was born for this.
He started dictating. I scribbled like my life
depended on it. Meanwhile, Sierra did nothing,
absolutely nothing except distract me.
She kept brushing my skirt, tugging it, teasing right there
in front of him. I was blushing so hard I thought
my makeup would melt off. Why did I wear this boring
dress? Sierra was right.
I should have worn something sexy.
She posed, she smiled, she pretended to write, she showed
leg. Lots of leg.
I wanted to scream and also cry and also steal her dress.
When it was finally over, I went out and typed the letter
perfectly. Of course, Sierra just waved,
said goodbye and sashayed out like she'd won something.
Good riddance. When I brought the letter back,
Mr. Hancock checked it and nodded.
Perfect, he said. Then where's Sierra?
My stomach dropped. Why were you going to offer her
the job? I would have liked to see her
work. She changed her mind, I said
quickly. The job wasn't for her.
He sighed. Too bad I liked her.
Her, I said softly. Or her legs?
He smiled. I don't see why a secretary
can't have nice legs and show them off.
You could learn a thing or two from her.
Oh. Message received loud and clear.
He offered me the job, and the very next morning I reached into
Sierra's closet and took that dress, the short one, the
dangerous one, without asking. Hey, she's done it to me often
enough. Because one thing is very, very
true. Sierra isn't the only Sissy in
town with nice legs. And now, now I know exactly how
to show them. Where were the secret sissies
legs? Lead meeting, sweetie.
Notes ready, Skirt shorter. Hired already.
Giggling confidence unlocked. Where are the secret sissies in
town? Legs talk louder than resumes,
darling. Watch me learn.
Heels click. Confidence rising now.
Join the Secret like follow and subscribe.
He can't look away. Guess I will stay in short.
Dresses. OK, quick little rewind before I
squeal my way forward. So far Sierra and I2, former
boys now the best, kept Sissy secret in town, played dress up
job stealing games and leg wars right under Mr. Hancock's nose.
I got the job, stole Sierra's tiniest dress, and learned a
very important lesson. Legs matter like, deal a lot.
And now, now I'm officially Mr. Hancock's secretary.
His very dedicated, very leggy, very fluttery secretary.
I really, really love working for Mr. Hancock.
Every day I feel more sparkly when I walk into his office,
heels clicking, skirts swishing, heart doing little Bunny hops.
And I swear, the way he looks at me, he feels it too.
Well, almost. Because there's this one thing I
already told you about my first day.
How I borrowed, OK, stole Sierra's mini dress and wore it
to work. I can still hear his voice in my
head, all calm and dangerous. I don't see any reason why a
secretary can't have nice legs and show them off.
You could learn a thing or two from her.
Giggle, shiver, blush. What I didn't realize back then
was how seriously he meant it. It wasn't just that he liked
legs. Oh no, it was an obsession.
If my dress was even a tiny bit too long, it didn't matter how
pretty the fabric was or how carefully I curled my hair.
He'd go all cold and distant, quiet, Moody, almost mean.
And worst of all, he stopped calling me in for dictation.
He'd just scribble letters by hand and drop them on my desk
without a word. No staring, no soft smiles, no
eyes slowly tracing my pantyhose.
I couldn't stand it. I needed that look, the one
where his gaze lingered just a second too long.
So experiment time. The next morning I slipped back
into a mini dress. Shorter, tighter, dangerous.
My knees felt the air when I walked and my heart was pounding
and oh, it worked. Suddenly I was back in his
office, notebook in hand, taking dictation while he stared at my
legs like they were the most important documents in the
building. I nearly forgot how to spell my
own name. I guess that's when it hit me.
Little Alana was trapped in tiny dresses forever.
Some mornings, standing in front of the mirror, I'd stare down at
my skirt and whisper, I'm not just a bimbo with pretty legs.
I'm a woman. Well, not exactly a woman, but
he doesn't need to know that, teehee.
Because then I'd get to work, feel that look crawl over me,
and suddenly it was all worth it.
There's power in this. Real power.
The kind that makes a strong, confident man turn nervous just
because you crossed your legs the right way.
And honestly, it was probably no coincidence that I was always
dropping my pen or adjusting my shoes when I wore minis.
Knees bent, skirt riding up, heart fluttering.
Oops. The other women noticed.
Of course they did. They started calling me Minnie
Mouse. Nice dress, Minnie, One teased.
Short enough for Mr. Hancock. Then she laughed.
If I had legs like yours, I'd wear Minnie's too.
Really pretty legs, you know, for a man.
I nearly died. SH.
Don't let any of the men hear that, especially not my boss.
She just smiled. Relax, we're jealous, Gorgeous
boss. Front row seat and all that
attention. I wanted to cry and giggle and
hide and twirl all at once. Then came the day.
The day everything changed. I was kneeling in front of the
filing cabinet, mini dress stretched tight, knees pressed
together, fishing a file out of the bottom drawer.
I heard footsteps. I looked up.
It was him. Without thinking, I held out my
hand. I could have struggled up on my
own, but why, when there's a strong, handsome man right
there? He helped me up.
His hand was warm, steady. I smiled sweetly and said thank
you so much. I suppose you men must get tired
of girls like me always being so helpless.
I'm just a girl, you know. He looked at me, really looked
at me so intensely I almost melted right there in my heels.
Alana, he said softly. You are not just anything,
except maybe just incredible. My heart exploded.
It was the first real compliment he'd ever given me, and suddenly
I didn't mind the tiny dresses, or the teasing, or being his
little secretary on display. I didn't mind at all because in
that moment he wasn't just my boss anymore and I had a feeling
this was only the beginning. Like, follow, subscribe Sissy
secretaries. At this point, I knew the truth.
I wasn't just typing letters anymore.
I was part of something fun, secret, and deliciously silly.
Mr. Hancock didn't raise his voice.
He didn't bark orders. He smiled, and somehow that was
much more powerful. It started so casually I almost
missed it. I was standing beside his desk,
wearing my silky dress, the hem resting perfectly on my thighs,
my slip just barely peeking underneath.
When I moved, Mr. Hancock leaned back in his chair, watching me
with that thoughtful look of his.
You know? He said, amused.
I've been having the strangest idea lately.
I tilted my head, pretending innocence.
Oh. He smiled wider.
I find it rather charming when a secretary plays along.
My heart skipped. Plays along how, exactly?
He gestured lightly toward my skirt, laughing softly.
Something simple, something fun. Lifting the fabric a little.
Nothing dramatic. I giggled.
Like this? I lifted my skirt just a touch,
revealing the soft edge of my slip, smiling up at him
playfully. He laughed outright.
Yes, exactly like that. After that, it became our little
game. Later, while he dictated a
letter, he paused mid sentence and glanced at me.
Alana, I didn't even ask. I lifted my skirt again, slower
this time, holding it for a moment before letting it fall.
He smiled. Very good.
Each time was different, by the filing cabinet near the window,
standing at my desk. Sometimes he didn't even say the
words, just raised an eyebrow or gave a small nod.
And every time I responded instantly, just as I was
supposed to, playful and eager. Each time he rewarded me
differently, a gentle touch at my waist as he passed, a soft
kiss on my cheek that made me blush and squeal quietly, a warm
hand guiding me back to my chair with a satisfied smile.
I loved every second. Eventually, he said it plainly,
but still laughing. Alana, he said.
I think we should make this official.
I swallowed, smiling. Official.
Oh rule. He explained lightly.
When I ask you lift your dress immediately.
Sweetly, I grinned. Yes, Sir.
From then on, the commands came softly but clearly, now again,
once more. And I obeyed every time, lifting
my skirt just as I'd learned, matching the playful confidence
in his eyes. Every lift earned approval,
every smile made me glow. And as I walked back to my desk,
cheeks warm, heart fluttering, I knew exactly who I was.
Not just a secretary. A Sissy secretary.
Happy, playful, and perfectly trained to make him smile.
By now, everyone at the office knew Alana.
Not the boy I used to be, but the woman I presented as every
single day. My voice softened automatically,
my posture careful and trained, my hands always finding a polite
place to rest inside. I still felt that fluttery mix
of nerves and excitement, the knowledge that I was a Sissy
learning womanhood, one outfit at a time.
That afternoon during lunch, I perched on a small stool with my
notebook balanced delicately on my crossed legs.
I was wearing one of my shortest work outfits, a tight floral
mini dress with cap sleeves, the fabric hugging my torso and hips
before ending far too high on my thighs.
Sheer pantyhose smoothed my legs, and my black heels kept my
feet angled just right. Every time I shifted, I felt the
hem threatened to ride up, making my cheeks warm.
Alana, what's wrong? Martha asked gently.
She looked effortlessly confident beside me in her short
purple floral wrap dress, long sleeves flowing loosely, the
wrap emphasizing her waist. She held her notebook casually,
smiling in a way that made me feel both seen and exposed.
Oh, nothing. I said too quickly, lips forming
a small pout before I could stop myself.
It's my own fault. She waited, knowing I'd spill.
I'm just so tired of these tiny dresses.
I admitted, tugging uselessly at the hem.
Every day they feel shorter, I feel trapped in them.
And does he choose them for you? She asked.
No, but he always knows when I wear something he doesn't like.
I glanced down at my bare looking legs and swallowed.
I feel ridiculous, like I'm almost naked.
Martha leaned in and whispered. You could wear something grown
up, something sensible. I shook my head, hair brushing
my cheeks. He gets mean when I do.
Why do I let him treat me like this?
She smiled knowingly. Because you like being wanted.
Please. I hissed, blushing hard.
Someone will hear. Later that day, I was called in
for dictation. I changed into a more severe
outfit, a sleek black pencil skirt that hugged my hips
tightly and ended well above the knee, paired with a sheer floral
blouse. The sleeves were translucent,
the fabric soft and floaty against my arms.
My pantyhose were perfectly smooth, my heels clicking softly
as I stood before his desk. I could feel his gaze linger as
I shifted my weight. When he joked that the deadline
was tighter than my skirt, I straightened and replied Yes,
Sir, even though my knees trembled.
Then he said my name slowly and glanced down.
I followed his eyes to my skirt, fingers curling instinctively at
my sides. No, I said suddenly.
I'm a secretary, not a stripper. The words poured out, my voice
shaking but earnest. Oh, sure.
If a man has to go through what we women go through every day,
that's ridiculous. To women, it's just life.
You're humiliating me just because I'm a woman.
Before I could blush or squeal, I turned and left.
On Monday, I arrived dressed carefully and deliberately.
I wore a pastel blue chiffon dress, long sleeves softly
puffed at the shoulders, the skirt falling well below my
knees. The fabric floated modestly
around me as I stood in simple white heels.
I felt calm, adult, proper. He looked at me and frowned.
What is that? This is called a dress, I said
quietly. Women wear them.
I'm a woman. You look like old Mother
Hubbard, he snapped. I don't want to see you at all.
The next day I tried again, choosing something feminine but
restrained. A dark floral dress, knee
length, softly cinched at the waist, long sleeves gathered at
the wrists. I felt pretty without feeling
exposed. He called me in immediately.
Alana, he said coolly. I think you'd be more
comfortable working for a woman, and I need a secretary who can
better anticipate my needs. My heart dropped.
I stepped closer, hands clasped in front of me.
Please, I whispered, I'll do anything.
I'll wear whatever you want. I'll be your submissive little
secretary again. He studied me for a long moment.
We'll see. The very next morning I was back
in the short red dress he'd hired me in, softly draped at
the neckline, the skirt barely covering the white slip peeking
beneath. Red heels completed the look, my
legs smooth and on display. I felt exposed and oddly
relieved. By the end of the week I was
wearing something even bolder, a black glossy dress with sheer
panels, clinging closely as I found myself posed low to the
floor after a stumble, knees tucked, hands placed just so.
I giggled softly, hoping it showed I was trying on on
Friday, when he looked at me in that red dress again and
motioned subtly toward my skirt. I didn't argue.
I stepped closer, cheeks blazing, heart fluttering, and
followed the unspoken instruction without a word.
Back to business as usual. Mr. Hancock never forced me to
change. He simply expected it.
A softer voice, better posture, dresses that became part of my
work day. Somewhere along the way,
Temporary turned into routine, and routine turned into
identity. I stopped correcting people when
they called me Alana. By the time this evening
arrived, I wasn't pretending anymore.
By then I understood what my role really was.
It wasn't about typing or scheduling or obedience.
It was about presentation, and Mr. Hancock never let me forget
that the invitation came late in the afternoon.
I need you with me tonight. He said, I still on his screen
as my secretary. No explanation, no room for
questions. I nodded immediately.
Yes, Sir. When I arrived, I felt the room
react before I did. The gown shimmered in deep
purple sequins, hugging me with deliberate elegance.
Long sleeves, clean lines, fabric that caught the light
with every step. My hair fell in smooth waves,
polished and intentional. My makeup was darker than usual,
confident, controlled. I felt stunning and acutely
aware of it. Mr. Hancock finally looked up.
He didn't glance. He looked slowly from my heels
up my legs, along the curve of the gown to my face.
His eyes lingered just long enough to make my pulse quicken.
You clean up well, He said quietly.
A pause. That's useful.
As we moved through the venue, he guided me with the lightest
touch at my back, barely there, but unmistakable.
Not a grab, not a pull, a placement.
Here, stand there, half a step behind.
At one point he adjusted the folder in my hands, his fingers
brushing mine as if by accident. Another time he straightened the
edge of my sleeve, smoothing it down slowly.
You represent me tonight, he murmured.
Remember that. My stomach fluttered.
Yes, Sir. All evening he kept me close,
but never equal. I held documents while he spoke,
leaned in when he asked for details, stood still when his
hand rested briefly at my waist during introductions.
Alana, he said once, fingers still there.
My secretary. The way he said it made my knees
feel soft. He corrected my wording gently,
right into my ear, lowered his voice so I had to lean closer,
smiled faintly when I blushed. His comments were casual,
precise, about confidence, about knowing when to speak and when
not to, about how women who understood their role were
always noticed. Each remark wrapped itself
around me, each one pulled me in deeper.
Later, for a moment, we were alone.
He looked at me again, this time closer, slower.
You chose this, he said quietly, The dress, the roll staying.
I swallowed. He reached out and smoothed a
single sequin flat against my gown, the touch deliberate,
unhurried. Don't pretend you didn't.
I lowered my eyes, hands folding neatly in front of me.
Yes, I said softly, standing there, glittering under the
lights, his attention warm and unmistakable.
I felt the truth settle in. I wasn't just his secretary.
I was exactly what he wanted me to be.
And the most dangerous part? I wanted it too.
By the time this week began, I already knew the rules, even if
no one had ever written them down.
I was Alana now, not just by name but by posture, by
clothing, by the way my voice softened automatically whenever
someone spoke to me sharply. My days were measured in skirts
and glances, approvals and corrections.
And the worst part? Everyone noticed I was wearing
one of my safe dresses that morning, a fitted floral mini
dress with short sleeves patterned in warm cream, blue
and red tones. The fabric hugged my hips
tightly, stopping high on my thighs, paired with sheer
pantyhose and white heels. My wig was carefully styled,
makeup neat but understated. Martha caught me alone near the
copy room. She leaned in close, her voice
low and sharp. You ever do that again?
She hissed, fingers brushing the edge of my wig.
I'll pull this off and I won't give it back.
Then I'll tell Mister Hancock everything.
My stomach dropped. Fine.
I whispered quickly, eyes down. I understand, I'm sorry.
She stepped back, then tilted her head, suddenly smiling.
By the way, that's a cute dress, Mr. Hancock bought it for you,
yes? I admitted, cheeks warm.
She smirked. You look adorable.
The word lingered longer than it should have.
The next dress arrived that afternoon.
I knew the moment I saw it that something had shifted.
This wasn't soft or playful. This was deliberate.
The dress was brighter, tighter, cut higher, yellow with a bold
floral print. Short sleeves puffed just enough
to draw attention, the skirt ending well above mid thigh When
I slipped it on. Later, standing in front of the
mirror, I barely recognized myself.
The way it clung, the way it demanded attention.
We were no longer in cute territory.
We were back to being obvious. I wore that dress into his
office the next day, white heels clicking with every step.
My legs felt completely exposed. I stood straight anyway, hands
clasped. Mr. Hancock?
I said carefully. This isn't normal behavior for a
man. You're buying dresses.
What will the other men say? What if you get a reputation for
knowing things about women's fashion?
He leaned back in his chair, amused.
I'll take that risk, he replied calmly, eyes traveling over me
without apology. You look very good in that
dress. My face burned that afternoon.
Martha grabbed my wrist, harder this time, and dragged me into a
conference room. Several other women were
waiting. They all stared.
Alana. Martha said urgently.
You have to call off your boss. He's giving the other executives
ideas. They all want to buy clothes for
us. Now you should see what my boss
picked for me. Makes your dress look modest.
I folded my arms, suddenly defensive.
Oh, now you care. I shot back quietly.
If I were a woman like you from birth, you would have stopped
this already. She softened.
Please just tell him to stop picking out your clothes.
I hesitated. If I do, he'll reassign me, I
said, then, after a pause. Type up a petition.
We'll all sign it together. They typed fast, nervous,
desperate. A formal request.
No executive could choose clothing for their secretary or
require her to wear it. Every name signed.
When they handed it to me, I felt strangely important and
strangely afraid. I wore a darker dress when I
went to see him. A sheer sleeved black outfit
with a floral bodice and soft skirt.
Conservative by comparison but still unmistakably feminine.
Black heels, careful makeup. He read the petition silently.
Then he looked up at me. Alana, he said quietly,
disappointed. I expected better.
I buy you clothes, I take care of you, and all I get are
complaints. My heart twisted.
Mr. Hancock, I said softly, stepping closer.
You know I'd do anything to make you happy.
I love being your secretary. If it makes you happy to have me
show off my legs in a short dress, I'll do it.
I just, please let me choose sometimes.
This isn't just about me anymore.
He sighed. Very well, he said.
You have one more dress coming this afternoon.
Wear it tomorrow if you want. After that, I won't choose your
clothes so long as you keep showing plenty of leg.
My stomach flipped. I nodded.
The next morning, I stood in front of the mirror, wearing the
new dress. Soft pink light fabric, flirty
without being harsh, short but sweet.
My hair fell in gentle waves, heels pale and delicate.
It was cute. I wore it to the office because
even when I had a choice, I still wanted to please him and
that, more than any dress, told me exactly who I had become.
Stay with me, like, follow, subscribe.
More episodes coming. Oh, Mr. Hancock, I would do
anything. By now, my life had settled into
a rhythm I never planned. I dressed like a woman.
I answered to the name Alana. I blushed when my boss looked at
me too long. And I liked it far more than I
ever admitted. Sometimes, usually late at
night, I still wondered if I was just a boy in a dress, But more
and more often, the thought didn't scare me anymore.
When Mr. Hancock asked me to come to his house on the weekend
just to take dictation, I told myself it was professional,
neutral ground, a chance to reset after all the tension at
the office. I arrived at 10 sharp.
He opened the door wearing jeans and a soft sweater, relaxed and
casual in a way I'd never seen at work.
His eyes dropped immediately, because of course they did.
I was dressed exactly how Alana always was, a tight fitted dress
that hugged my waist and hips, pale fabric pattern softly,
paired with sheer pantyhose and high heels that clicked when I
shifted my weight. My hair was styled neatly, my
makeup careful but feminine. I looked intentional.
What else would I be wearing, I thought, cheeks already warming.
Was I still a boy in a dress, or just a woman who liked being
seen? He stepped aside to let me in.
Alana. He said, almost amused.
You didn't have to wear a dress. It's the weekend.
I smiled sweetly, folding my hands in front of me the way I
always did now. Oh, there are so many things you
men get to do that we women don't.
I said lightly. Why give up?
One of the few things that's just ours.
Life short, Live it in a dress. I smooth the skirt down just a
bit, and you'll notice it's not quite as short as you usually
make me wear. He exhaled, clearly trying not
to smile. Let's not argue, have a seat and
we'll work. I glanced at the chair he
indicated and tilted my head. Dusty.
Before he could respond, I bent slightly and brushed the seat
clean with my hand. I felt the dress pull snugly as
I leaned forward, the fabric reminding me exactly how little
room it left to move. I straightened slowly and tugged
the hem down again. When I looked up, he was
staring. I raised an eyebrow, playful and
innocent at the same time. Why, Mr. Hancock, you aren't
checking out my rear end, were you?
Of course not, he said quickly. Please sit.
I was just about to win. Oops.
My steno pad slipped from my fingers and landed on the floor.
Butterfingers. I giggled.
Reaching for it wasn't easy in such a tight dress.
I had to move carefully, deliberately, conscious of every
inch of myself. By the time I finally sat, my
face felt warm and my heart was fluttering. 2 hours passed in
silence, broken only by his voice dictating letter after
letter and my pen scratching steadily as I wrote.
I stayed perfectly still, legs crossed, posture proper.
I knew he was watching, I could feel it.
That was my boss. When we finished, I stood and
stretched subtly, then wandered to the window seat to take a
short break. I slipped off my heels and
wiggled my toes, relief making me sigh softly again.
His eyes followed. I smiled without turning.
My goodness, I teased. First my legs, now my feet.
I had no idea you admired them so much.
Don't be ridiculous, he replied. I glanced back, lifting my feet
just slightly. Here they are.
Since you're already looking, Alana, he said sharply.
Stand up. The tone made my stomach
flutter. I obeyed immediately.
Come here. I padded across the hardwood
floor, barefoot, aware of every step, every sound, every
sensation. I stopped in front of him, hands
folding neatly in front of me again.
Come closer. He said quietly.
I did. I leaned in and let the moment
linger, close enough to feel his breath, close enough to know
exactly what he meant. It wasn't rushed, it wasn't
rough. It was deliberate.
When he pulled back, his expression unreadable, he said
evenly. Show me you understand what this
moment means. My breath caught.
If I went too far, everything would change.
If I crossed that line, he might see what I still sometimes tried
to forget. I swallowed, thinking fast,
heart racing. I don't need to change anything
to prove myself. I said softly, eyes lowered.
I promise I won't disappoint you.
I looked up at him then, cheeks flushed, lips parted, Standing
there barefoot in a dress I had chosen to wear.
Whether I was still a boy in a dress or something else
entirely, I wasn't sure anymore. But I knew one thing.
I wasn't ready to stop being Alana.
Stay with me. More secrets coming like follow,
subscribe. Mr. Hancock, isn't it a perfect
day for a walk in heels? You look beautiful.
Alana. By now, my life no longer
belonged to the person I used to be.
At work, I was Alana, Mr. Hancock's polished, elegant,
quietly devoted secretary. Outside of work, I was something
even more complicated. Somewhere between whispered
compliments, long glances, and moments that lingered just a
little too long, my boss and I had drifted into something that
wasn't just professional anymore.
We went out together, we sat close, we kissed, And through
all of it, I stayed in my dresses because they were my
armor. If I kept the illusion intact,
he could never know the truth I was hiding underneath.
But lately his looks had grown more curious, more searching,
and my heart had grown dangerously soft.
The elevator had been broken for days.
Of course it had to be on this morning, the day Mr. Hancock
insisted I wear one of my tiniest dresses and those
elegant, painful 3 inch heels he loved so much.
The fabric of my dress brushed my thighs with every step as I
climbed the stairs. It was a silky flowing little
thing in warm leopard patterned tones, light enough to flutter
with each movement. My sheer pantyhose caught the
light, making my legs glow softly as I lifted 1 aching foot
after another Click, step, click, step.
By the 2nd floor my calves were burning.
By the third my toes were trembling inside my heels.
I told myself I was strong, that I could do this.
Every other woman in that building would have, so why not
me? Still, a tiny voice in my head
whispered, you don't even belong here.
You're just a boy in a dress pretending to be a woman.
The thought made my chest heighten.
Finally, halfway up the third floor, I had to stop.
I lowered myself onto the stair, carefully smoothing my skirt
over my knees. My breath came in small, shaky
size. A man I didn't recognize passed
me on his way down. He slowed just a bit, his eyes
lingering on my crossed legs on the way.
The dress hugged my figure on how small and vulnerable I must
have looked sitting there. I flushed and looked away,
suddenly feeling very exposed. When he disappeared, I slipped
one heel off and rubbed my aching foot, then the other.
The relief made me sigh softly. That was when I heard footsteps,
slow, confident, I looked up. Mr. Hancock was standing a few
steps above me. My heart skipped.
There I was, sitting on the stairs, shoes off, dress riding
just a little higher than it should, hands pressed gently to
my tired feet. I must have looked so delicate,
so very Alana. For a moment neither of us
spoke. Then forcing a smile, I leaned
back against the wall and said in my sweetest voice.
Why hello Mr. Hancock, what a perfect day for a little walk in
heels, don't you think? His eyes flicked to my bare
feet, then slowly back to my face.
You look worn out. He said quietly.
He held out his hand, I took it. His grip was warm and steady as
he helped me to my feet. I quickly slipped my heels back
on, even though my toes protested.
I couldn't let him see weakness, not now, not when I wanted him
to keep seeing me as the woman I was trying so hard to be.
We climbed the rest of the stairs together, close enough
that I could feel the warmth of him beside me.
I was falling for him, truly, foolishly, hopelessly.
And all the while I carried the most dangerous secret of all.
That beneath the soft dress, the painted smile and the fluttering
heart, I was still someone he could never know yet.
Will he ever find out? Find out what.
My Valentine surprise for. Him.
By now, my double life feels almost normal.
At work, I'm Alana, Mr. Hancock's polished, loyal
secretary. Outside the office, my feelings
for him have grown deeper, quieter and more dangerous.
We've shared long looks, gentle touches and moments that felt
too real to ignore. But through all of it.
My secret remains. He still doesn't know the truth
about me, and somehow that makes every feeling stronger.
I'm still Alana, still a boy in a dress, and Mr. Hancock doesn't
know I love him so much. And I think he loves me too.
Valentine's Day felt different this year.
I didn't buy a card, didn't write a note.
Instead, I did something braver. I sat on my bed wearing a red
polka dot dress, the fabric soft against my skin.
The neckline was gentle, feminine without being loud.
Black stockings hugged my legs, and my heels waited nearby.
My wig fell in loose waves over my shoulders, framing my face.
My makeup was sweet, rosy lips, soft eyes, just enough shimmer.
In my arms I held a small brown teddy bear.
I had bought it for him, not flashy, not expensive, just
honest. The room glowed in warm light.
I crossed my legs, carefully smoothing my skirt the way I
always did, even when I was alone.
Old habits die hard. Someone took the photo for me.
I tilted my head slightly, shy smile on my lips, clutching the
teddy bear close to my chest. The red background behind me
looked dreamy, almost heart-shaped, like it knew what
this moment meant. This wasn't just a gift, it was
me. Later that evening, I slipped
the bear into a simple gift bag and placed it on his desk before
he arrived. No name, just a small tag that
read for someone special. When he came in, I watched from
my desk. He picked it up, smiled, then he
looked at me. Alana.
He said softly. Was this you?
I nodded. I wanted to do something
personal. He walked over slowly, holding
the bear like it was fragile. That's very sweet, he said.
Thank you. Our eyes met.
Not boss and secretary, not roles, just two people.
I'm glad you're in my life, he added quietly.
My heart nearly broke open. I'm glad too, I whispered.
He squeezed my hand once. Nothing dramatic, nothing
obvious, but it felt like everything.
That night, alone in my room, I replayed his smile in my head,
the way his voice softened when he spoke to me, the way he
looked like he wanted to say more but didn't.
I hugged my pillow and laughed softly.
Still Alana, still hiding, still scared, but more in love than
ever. Did you feel it too?
Like subscribe, follow for more? How could you keep this from me
until now? I wanted to tell you, but I was
afraid you would leave me. I never planned any of this.
Like at all. I was supposed to be a
secretary. Then I was wearing skirts just
for work, then heels, then lipstick, then kisses, and
somehow, somewhere between coffee runs and blushing looks
across the desk, I fell completely, hopelessly in love.
And then he knelt down. Yes, that moment I said yes
before my brain even caught up with my mouth.
My hands were shaking, my knees were weak, and when he slid the
ring onto my finger, I felt something warm and fluttery deep
inside me. I didn't tell him everything,
not yet. But the wedding.
Oh, the wedding. He wanted something elegant and
traditional. I wanted something pretty.
Guess who won? On the morning of the ceremony,
I stood in front of the mirror wrapped in ivory lace, the dress
hugging me just right, the veil floating softly around my curls.
My makeup was perfect, my lips glossy, my heart pounding.
I didn't recognize myself, not because I looked like a bride,
but because I finally looked like me.
When the doors opened and I walked down the aisle, I felt
every step. The swish of my dress, the click
of my heels, the way everyone stared.
And him. He just looked at me like I was
the most beautiful thing he'd ever seen.
No shock, no confusion, just pure, quiet awe.
When I reached him, my hands trembling in his, I leaned in
close and whispered the truth I'd carried for so long.
There's something you should know.
I was born a boy, I swear. The whole room stopped
breathing. He didn't pull away, He didn't
flinch. He smiled.
I know, he whispered back. I always have.
Tears spilled instantly. Ugly crying, maybe.
Mascara still perfect. I didn't fall in love with who
you were, he said softly. I fell in love with who you
became. We said our vows.
His lips touched mine, gentle, real, sure.
And when we walked back down that aisle together, hand in
hand, it wasn't as boss and secretary anymore.
It was husband and wife on our terms.
From me to you. Some secrets don't break love.
They prove it. Some dresses don't just change
how you look, they change who you finally allow yourself to
be. I didn't lose myself, I found
myself. Thank you for following my
journey from the very first skirt to the very last veil.
Comment if you believed in me from the start, like if this
ending made you smile. Subscribe for more girly
stories, surprises, and sparkle. This may be the end of Sissy
Secretaries, but it's only the beginning for me.
Thank you all so much for watching the final episode.
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