ONE
My wife, Maggie, likes to play games. Ever since she found out about my
love of women's clothing, my desires to dress, she's always encouraged
me. Sometimes, it will just be a bit of fun. Other times she knows she's
pushing my limits, challenging me. She thrives on my humiliation and,
for whatever reason, I love it too. Even though I'm deeply ashamed by my
behaviour, and have never really been comfortable with who I am.
Despite this, nothing could have prepared me for the last few days. My
wife has told me to document it publicly. Events spiralled quickly out
of my control, and even though I'm now fully aware of my position in our
relationship, I'm still shocked by what happened and struggling to come
to terms with what might happen next.
TWO
I'm flying out of Manchester to Los Angeles for a meeting with a manager
about representing my screen-writing. I'd had one out there before, but
we never made a sale, so this was a big break for me. A sale would mean
I can quit my day job and provide for my wife the way I always dreamed I
would. But right now, short of money, Maggie told me I wouldn't be able
to stay out too long. Hop a flight, take the meeting and get home.
I'm heading to the security checkpoint before my flight when I first get
nervous. My heart skips several beats. I'd been wearing women's
underwear most of my life - sometimes by choice, sometimes by Maggie's
demands - and I was convinced the sensor would detect my bra. A bit of a
clich?, sure, but a very real fear for a cross-dresser.
Last night, my wife had laughed it off, telling me about the thousands
of women that pass through without detection every day. She explained
they must have some kind of setting for the underwire. Maybe, I thought,
but still checked into it online and, naturally, there are reported
instances of women being inconvenienced - and, worse, embarrassed - by
the check.
I hesitate before going through. Take off my sneakers and place them and
my bag on the conveyor belt to be scanned. Thankfully, Maggie had told
me I didn't have to wear stockings or tights because of the long haul
flight. They would have been clearly visible right now. I remove the
belt from my women's jeans, and hope nobody notices the delicate design
on the narrow leather.
I duck into the sensor and-
-it doesn't go off.
I grin and step through, even laugh to myself. I put my sneakers back on
and thread the belt through the small hoops of my jeans. Confident, I
grab my bag.
I walk off, but only get a few steps.
"One moment," a female voice says.
I stop and look back. The security woman approaches me, wand sensor in
hand. Her name tag reads 'Stephanie'.
Everything's okay, I think. It was just a random check. Don't panic now.
"You seem a little edgy," she says, explaining her reason for stopping
me.
"I just don't like to fly."
"Well, you're not flying yet," she laughs. "Do you mind raising your
arms?"
No, this was not fair. I had beat the main sensor, but now this woman
was going to uncover what I was wearing.
At my hesitancy, the woman checks for her colleagues in case she needs
assistance.
"Sir? Raise your arms now."
"Sure," I said. "No problems."
I put my bag down and raise my arms. The main sensor had not detected my
bra. Neither would the wand.
She moves it up my body and the gadget goes crazy. She looks at me,
puzzled. Moves the gadget again around my chest. People are moving
slower through the checkpoint as they watch. I blush, my cheeks burning
up. She knows. They all know!
"Sir, can you please explain what's setting the wand off?"
I can't see a way out of this.
I look down and mumble: "I'm wearing a bra."
She smiles. "Sorry, I didn't quite catch that."
I'm aware that a few people have stopped to watch now. One woman, who
had witnessed and heard the full exchange, is grinning at me. When her
partner, a big guy, moves off she grabs his arm.
"Hold on. I want to watch this."
I look around for an escape. For help. My heart's pounding. I knew what
I had to say. I look the security guard in the eye. Please don't make me
do this. She smiles. It's a grin, actually. A happy face. She's enjoying
this.
I clearly say: "I sometimes cross-dress. I think the wand is detecting
my bra."
The onlooking woman bursts into laughter. The security guard keeps a
straight face, but declares quite clearly for all to hear: "So you enjoy
wearing women's clothing?"
I wasn't sure if it is a question or a statement, so I keep quiet,
wishing the ground would just swallow me whole.
"Well? Do you enjoy wearing women's clothing?" she demands.
"Yes," I say meekly.
The security woman looks around at the onlookers. "Okay folks, the
show's over."
I breathe a massive sigh of relief. Thank God I was free. I pick up my
bag. She holds out a hand.
"Not you. I need to verify what you are saying."
My shoulders slump as she leads me to a side-room and closes the door.
Inside she doesn't attempt to hide her smile. Nasty little glint in her
eye, too. This is going to be bad. However, I tell myself, in half an
hour or so you'll be on your flight and this will all be over.
I couldn't have been more wrong.
TWO
"Take off your shirt, Miss..."
"I'm a man. My name is-"
"I want your real name," she demands. "Not your fake male name."
Jesus, this woman has me made. How am I going to get out of this?
"Kirsten," I whisper, my voice cracking.
"Kirsten, I need to see your bra so I know you're telling the truth
about what the sensors detected. Please remove your top."
"But, please. Do I-?"
"Remove your top."
She has a strong, dominant personality and I knew from my wife the more
I protested and fought, the worse things could be for me. I fumble with
the buttons and start to unfasten my shirt. My fingers are trembling.
This is really happening and while I sometimes had fantasies like this,
the reality is actually scary. I'm allowing this stranger to control me.
My erection is growing, but how can I be enjoying this?
My shirt is open. The bra, my small natural breasts enhanced by inserts,
clear for her to see. I couldn't look her in the eye.
"And your jeans."
"That's not-"
"Do I have to call a colleague?" she snaps, swiping her radio from her
belt.
"No, please don't."
She watches, paying attention to detail. "Nice belt. And those are
women's jeans, right?"
"Yes," I admit quietly.
I unbuckle my belt and my jeans drop to the floor.
I'm wearing one of my favourite sets from Boux Avenue. Just the
underwear alone makes me feel sexy, sensual and feminine. Throw in the
fact that when it was purchased my wife took me for my first ever bra
fitting and I had to sign for my own loyalty card with the store, nice
and pink in my wallet, and you can understand why they typically make me
feel horny as hell.
Right now, as a damp spot forms on my panties, I just feel pathetic.
I reach for my jeans, hoping to hide the signs of pre-cum.
"Wait a second," she says, indicating the damp spot, my growing erection
that wasn't impressing her. She giggles. "For a second I thought I saw
signs of a penis, but it's just your little clitty. That damp spot? Are
you on?"
"I don't understand."
"I bet you don't" she said. A knowing little smirk. "Does your wife have
you follow a menstrual cycle?"
I turn crimson. My erection pushes out, but she doesn't even notice it.
The damp spot grows larger, soaking and expanding.
The security woman erupts into laughter.
"She does, doesn't she?"
"Yes, but it's not now. I'm not due for another two weeks so and-"
Her glare is enough to silence me, and I wonder what kind of man I am if
I am debating whether I should or should not be on my period.
"Oh, poor Kirsten. Didn't your wife ever tell you that periods can be
unpredictable. You're showing obvious signs of spotting." She thinks for
a moment, considering me. "Get dressed."
As I dress she writes on a pad.
Jeans and shirt fastened, I look at her hopefully.
"Please may I go now?" I ask.
She slips what she has written into an envelope and seals it.
"Sure. But before you go to your flight I need you to take this to Boots
and hand it to a female clerk."
I check my watch.
"You've got plenty of time, Kirsten. After you have visited Boots you
may return here to collect your bag for your flight."
She ushers me from the room, and I head off down a walkway, rushing.
What the hell is happening, and why am I letting it? Couldn't I just
report her? But then more people would know my secret. Should I look in
the envelope? What if she's watching on the cameras?
Okay, I tell myself. You can do this. My wife plays a game called NOTES.
There was probably even one in my luggage. If she particularly wants to
humiliate me I'll find a sealed envelope with instructions where to take
it. There could be anything inside, but it's always designed to cause me
embarrassment. Typically things like: 'my husband is looking for a new
dress, can you help him, please?' Invariably, the women who take part in
her games are unsuspecting and just go along with it. So this was going
to be something similar. I hadn't disappointed my wife once, so there
was no way this security guard would beat me.
Then I would get my bag, get my flight and this would all be over.
At least Boots was fairly quiet when I get there, and the upside is most
of the shoppers were in a hurry so they are in and out and not really
paying attention to anybody but themselves.
I walk the store and find an available assistant. Aroused slightly
because she's attractive. A touch younger than myself. Wavey hair. She
looks nice in her independent uniform. Probably off one of the make-up
counters, I deduce.
"Can you help me?" I ask.
"Sure. I'm normally over on the Smashbox counter, but what can I do for
you?"
I nervously hand her the envelope, dreading what might be inside.
"Security asked me to give you this."
She looks bemused. "I'm not in trouble, am I?"
Not you, I think, as she tore into the paper. She reads the note. Looks
at me, confused. Then reads the note again. She stifles a giggle and
then reads one more time, finally letting a full on laugh escape.
"Kirsten, do you know what's in here?"
Just the use of the name and her reaction means this is going to be bad.
"Listen, can I just go and catch-"
"I asked you a question," she says sternly, raising a finger to hush me.
"No, I don't know what's in the letter," I say quickly, hoping it will
calm her down.
She indicates her name badge.
"I just want to catch my plane, Racheal."
"I see I'm going to have to teach you a lesson in courtesy and respect,"
she says.
"No, please," I stammer. "I just want to catch my plane, Miss Racheal."
"Better," she smiles. "And you will. But no woman should have to go
through her period unprepared."
My face flushes red.
"This isn't fair," I protest weakly.
"Come along."
She leads me down a couple of aisles, reading the note aloud as we went
for all to hear. Some giggle. Some stare. I drag my feet as I listen.
"My sissy friend Kirsten is having her period and she's not ready for
it. A nice new lipstick might brighten her day. And anything else you
think appropriate."
We stop and I look up. No way! I want to get out of here, but my feet
won't move. We're in the feminine care aisle. The bulge in my jeans is
apparent.
"Do you like it here?" she asks, gesturing to all the sanitary products.
I nod shyly.
Two women stop to watch. Both about my age. Holding hands I wonder if
they are together. The thought gets me hot, but my arousal is soon
because of something else.
"When you have your period," Racheal began, and the two women don't even
try to hide the fact that they are enjoying my predicament, "do you
prefer sanitary pads or tampons?"
"Panty liners," I whimper.
Racheal taps her name badge, making a clicking sound on it with her
false nails.
"When I have my period I normally wear a panty liner, Miss Racheal," I
said clearly.
"Good girl," Racheal said, and grabbed a box of nightime Always with
wings. She steals a look at the observers, and flashes them a smile. She
picks up a box of tampons.
"You're in for a treat," one of the women say.
I baulk at the idea of wearing a tampon, lost for words. Finally, a
pathetic: "I don't want to wear a tampon."
Racheal taps her name badge for the last time. "You just don't learn, do
you? I think this will be a case of more what I think is appropriate
than just a new lipstick."
She hands me the panty liners and tampons and I reluctantly take them.
Holding them for all to see.
THREE
She leads me to her make-up counter. Now, I was familiar with what was
about to happen because occasionally I've made enquiries, had little
demonstrations, about techniques and colours - but always by my choice.
Brief encounters that lasted a few minutes. But this was-
"I said, sit down."
I quickly comply.
She teases me for a minute or so, selecting products. Then she settles
on a bright red lipstick, far brighter than I would ever consider; and
if that wasn't enough, she places a shiny lip gloss next to it.
I swallow deeply. I've never worn lip gloss before. It's going to be so
obvious.
"You're welcome to watch," Racheal says.
I look around. The two ladies from the feminine care aisle have
followed. I stare again at the lip gloss.
"That's just to finish," Racheal smirks. "First, I'm going to create a
nice day look for you. Mostly subtle. But then I'll finish it with the
lipstick and gloss."
She goes to work with a foundation, blending it into my skin.
"What colour do you normally wear around your eyes?"
"Neutral," I say, my stomach turning.
"Not today, Sweetie. Let's be a little more adventurous. A nice hint of
blue to match your shirt should work."
"But people will see-"
"Listen, Kirsten. Most men will just notice your lipstick and have a
good giggle. Isn't that what you like? The attention? Being read for the
sissy you are?"
"No. I just enjoy wearing women's clothes. That's all this ever-"
She shushes me, looking down.
"Your little clitty says otherwise. So, that's the men. But all women
will see everything I'm doing to you."
She brushes on bronzer and then picks up a blusher.
"Isn't that right, ladies?"
Both women nod.
"We know a sissy when we see one," one of them notes.
"I'm not a sissy."
"Well, you're not a man," the second woman chimes. "You're just
something for us real women to play with."
I'm silent. Afraid if I protest something even worse could happen. But
what could be worse? Even though customers are generally in and out of
the store, most at least stop for a moment to consider the man getting a
make-over. And in that moment they grin, laugh, smile...They make sure I
know they are amused by what is happening.
Racheal applies my eye shadow.
"That's a great shade on you," she grins, and then finishes with the
mascara, making sure my lashes are long and emphasised. "Now then."
She picks up the lipstick and carefully runs it around my lips. And then
the lip gloss, a coating that will last hours.
"They look gorgeous," she smiles, happy with her work. "Pout for me,
Kirsten."
I follow her instructions. One of the ladies actually claps her hands
together. "Oh, yes. Every glint of light is going to shine off her
lips."
"Delightful," the other notes.
Racheal holds a mirror up and I try to look away. But it's no good. I'm
curious about how I look after such an extensive make-over. I actually
gasp. I hate the way I look, but at the same time I do love it.
"Thank you, Miss Racheal."
She hands me a few samples. "For the flight in case you want to freshen
up."
I stand and nod.
"And when you return home I expect you to stop by and show me how
beautiful you are."
The indication is clear. Regardless of what underwear I'd be wearing on
my flight home: just panties, or a bra as well, despite the trouble it
had caused, I would have to wear make-up and show Racheal how I looked.
"Yes, Miss Racheal."
I fast walk, almost a jog, back to security. I need to get my bag and
get on the plane. Put this behind me. There are a few sniggers, but
because I'm moving fast most people don't notice so much.
I find Stephanie at security.
"Please may I have my bag, Miss Stephanie?"
"Wow. Kirsten? I almost didn't recognise you."
"Come on. My plane leaves soon."
She glares at my lack of respect. "You went for a full make-over," she
declares loudly. People begin to linger at her raised voice. "What are
you wearing today?"
I remain silent. A few women look at me expectantly. Stephanie smiles.
"Foundation. Concealer. Bronzer and blusher. Eye shadow...To match my
shirt. Masacara. Lipstick," I hesitate. "And lip gloss."
"Come along," she says and gestures to the side-room.
I follow a few feet behind, grateful I am moving again. When I'm
standing still everybody can see, I'm on show. But at least moving I'm
passing people by.
Stephanie closes the door.
"You're going to learn some respect, Kirsten."
"But, this isn't-"
"I'm putting this behaviour down to your period, so we'll fix it
accordingly."
She checks my bag.
"I am sorry, Miss Racheal. If I put a panty-liner on will you please let
me catch my flight?"
"Who said anything about a panty-liner?"
I breathe a massive sigh of relief.
"I've got a surprise for you."
She pulls out the box of tampons.
"No. I've never worn them before. They were not my idea."
"This is your shopping, isn't it?"
"Yes, Miss Racheal."
"Then surely you only buy items you intend to use. Now, take off your
jeans."
I check my watch. Then do as I am told.
"Lower your panties."
"But what about-" I say, blushing. What about my erection? It's getting
bigger.
"That tiny thing," she laughs. "Now, lean on the table. This will be
easier if you bend over."
My face is white, despite the colour on my cheeks. I grip the table to
stop my hands trembling. I thrust my bum out for her. And wait. Wait.
Maybe she isn't going to-
I jerk forward as the tampon is inserted, feel it slide into me, my body
tense.
"Welcome it, Kirsten. It will be more comfortable."
I try to relax. Push back towards her and feel the tampon breaking in.
I've never had anything inserted there before. My butt cheeks clench as
they get used to the presence.
"Get dressed."
I slide my panties up. My erection is bulging and I turn slightly.
Notice it, I will her. Look at me. I'm want her to see it's more than
just the clitty she keeps calling it. I am a man.
She laughs at me.
I pull my jeans up.
"One last thing. Sit down."
I sit - and suddenly fidget at the pressing tampon inside me.
Stephanie grins sweetly at me. "Now, imagine your flight. You'll be
sitting for most of it. They'll be turbulence. You are going to feel
every single bump in the atmosphere. Get out of here, sissy."
I jump up and grab my bag. Going out of the door I hear her laughter as
she places a call on her cell.
"I've just had the time of my life. You won't believe the fun you're
about to have when you see..."
I'm out of earshot, jogging for my plane. Who was she talking to? It
couldn't have been about me. There was no way this day could get any
worse.
FOUR
I walk onto the plane thankful of two things: the flight was not very
busy, maybe about half full, and because we are walking in the same
direction nobody can see my make-up until-
"Hello there. I'm the lead Flight Attendant, Pippa. And this is Lisa."
They smile. Lipstick almost as bright as mine.
"Aisle seat, down the way," Pippa instructs me. I head off, breathing
calmly because she didn't make fun of my make-up. "Enjoy your flight,
Kirsten."
I freeze for just a second. How could she know? Stephanie, the security
woman, must have tipped her off. I pray she isn't as cruel and keep
walking. Don't look back. Other passengers will think she's talking to
somebody else.
I reach my seat and quickly jam my bag into the overhead compartment,
aware that the way I am stretching is displaying the outline of my
breasts.
"Could you do mine?"
The lady in the seat next to mine hands me her bag. I smile at her.
She's hot. About my age. I've completely forgotten myself for a second
as I flash her a smile and then it hits me. What my face must look like.
What am I thinking?
I take the bag and hide myself as I lift it up. My body stretches. The
woman smiles, a knowing look. Has she seen the outline of my bra? I do
have small, natural breasts and the bra and inserts I'm wearing
certainly enhance them. It must be painfully obvious what I'm wearing.
I sit down. Try to get comfortable with the tampon in my ass.
"That's a great look on you," she smiles. "The lipstick really sets it
off."
I can't decide whether she is being genuine and kind or making fun of
me.
Pippa approaches us.
"Now that wasn't very nice," she says.
"What's wrong?"
"You didn't acknowledge me when I greeted you."
It's going to be okay, I think, not really believing it. But what can
she do? We're on a plane. There are no shops to send me to. I can't
exactly undress publicly. This is a safe zone.
I actually grin. I've won. Here, she can't touch me.
"What's your name?" Pippa asks me.
My smile drops. I know what she wants to hear, but I don't want to say
it outloud, especially when I'd be sat next to the woman for the whole
flight.
"I'm Pippa." She holds out her hand. I take it. She shifts slightly so
my hand is now in a ladylike position rather than a man's grip. "What's
your name?"
To anybody listening this was a polite exchange, but somehow I knew it
was going to dictate her attitude to me this whole trip. Do I fight her
in a battle of gender wills, or give in? Maybe find, at least, just a
little enjoyment in whatever embarrassments she has in mind.
"Kirsten," I whisper.
The woman next to me leans over. "I'm Cindy," she says in a bubbly
manner. "Didn't quite catch that."
"My name is Kirsten," I say clearly.
Pippa and Cindy exchange a slight look.
"Now we all know each other," Pippa says pleasantly. "It's going to be a
busy flight for me, but I'm sure Cindy will help look after you,
Kirsten."
Cindy nods.
"Kirsten's quiet because she's on her period," Pippa informs my new
travelling companion.
I blush deeply, sinking into my seat.
"Panty-liner?" Cindy asks.
After an eternity I shake my head.
Cindy's face lights up. "No. What then? You're wearing a tampon? By
choice."
"Not by choice. I was made to-"
"Physically attacked and forced. For a man to wear a tampon they must
have tied you down."
"No," I say. Why hadn't I stopped this? What kind of man am I? I could
have...I reluctantly nod. "Yes. I wanted to try a tampon."
"She might need both," Pippa helpfully suggests, "if her flow gets
heavy."
Cindy grins at the possibilities ahead as Pippa returns to her duties.
"It's going to be a very uncomfortable flight for you," Cindy tells me.
FIVE
This isn't so bad, I thought, after the first hour or so. Cindy and I
got to know each other. General chit-chat. Refreshments were served. I
asked for a beer, but was told by Pippa - for all to hear - that real
ladies drank Bellini. I'd never heard of it, but if that was the worst
things were going to get, I'd take it.
Sipping the drink, Cindy told me to hold my glass like a lady; pinky
finger up.
And the tampon, although uncomfortable, was at least familiar now.
The flight really wasn't too bad.
"Open a button on you shirt," Cindy says suddenly.
I snap from my reverie.
"Do I have to?"
She nods happily. "You've had your Bellini. Got a little flush on.
Feeling fresh."
I reluctantly unfastened a button. The gap reveals a little of the lace
of my bra.
"One more," she teases.
"But people will be able to see," I protest.
"That's the idea, Kirsten," Cindy grins. "Sometimes a girl just wants to
show off."
I unfastened one more button, the gap now revealing part of the cups,
the mounds of my small natural breasts enhanced by the inserts.
She notices the bulge in my jeans.
"Is your tiny clitty getting anxious?" she asks, patting it. "I think
you're going to need this."
She reaches into her handbag and holds out a small, square pink package.
I study her nails. Beautiful gel acrylics with stencil art.
"Do you like them?" Cindy asks.
"They're very pretty," I nod.
"Would you like to have your nails done one day?"
I hesitate. This is a trap. It's putting ideas in her head. But I can't
help myself. They're gorgeous and while I've worn nail polish I've never
actually had my nails done.
"I'd love to, Miss Cindy." I take the panty-liner. "Do I have to wear
this as well?"
She grins. "You're going to need it soon. Now, go to the restroom. Don't
hide it in your palm. Hold it nice and clear for all to see. I'll be
watching so be a flirt and put a little mince in your step for me."
"But I'm not wearing heels."
She reaches for her feet. My faces turns white.
"Don't be silly. It's a joke. My shoes would never fit you. But just
because you're not dressed like a woman, doesn't mean you shouldn't act
like one. Now, run along."
I walk down the aisle, aware she's watching. I put a little sashay in my
steps.
The Captain approaches down the aisle, saying hello to various
passengers.
He spots me and smiles. He can't take his eyes off me...Well, my bra. My
breasts, I realise, wishing I could button my shirt.
He brushes by, whispering: "Didn't know we had a sissy on board."
I don't acknowledge his comment.
The passengers nearby hear, though, and look. I rush off and join a
small queue at the restroom.
Pippa approaches. "Having fun?"
I manage a small smile for her. Truthfully, though, I am conflicted.
Physically I was loving what, for some reason, was happening to me. But
rationally, emotionally, on any other level, I despised it - and myself
for letting it happen. What kind of man was I?
"I hate this," I tell her. "Please stop now."
The Captain joins the queue. He would have been handsome and dashing
even five years ago, but he's carrying a paunch and has obviously let
himself go. He studies me. Taking it all in now. The pert breasts, the
make-up, the sexy lips...I can imagine what he's thinking.
"Fancy joining the mile high club?" he asks directly.
A sudden explosion of laughter from Pippa at the unexpected suggestion.
I remain silent. Pippa speaks for me. "Sorry, Captain. This is Kirsten.
Excuse her manners. She's on her period and gets a little moody at this
time of the month."
"I don't mind," he grinned.
I'm mortified. Don't let this happen. Not here. Not now.
"It wouldn't be nice," Pippa assures him.
I consider her. So kind after all she's done...Just then her eyes light
up.
Thinking about what I enjoy Maggie doing for me when she is sometimes
on, I know what's coming. Please don't.
"But how about a blow job?" Pippa suggests.
"I don't-" I stammer.
"Look at those lips. Red and sexy and wet. Give the Captain a pout,
Kirsten."
I do as I'm told. A real sexy siren look. This is going to happen.
There's no way I can stop it. For a fleeting second I even imagine his
cock on my lips. Not this, I moan to myself.
"I actually did fancy a quick fuck," the Captain says, looking at me
hopefully.
"No." I was firm for the first time in this whole endeavour. Now's my
chance. Stand up strong to them. Let Pippa know I'm in charge. I can't
speak.
"But you are happy to suck his big cock?" Pippa asks.
I remain silent. Tell them no. Instead a slight protest begins. "Please-
"
"She's begging," Pippa declares. "Pretty please?"
I give up. "Pretty please, Miss Pippa," I say quietly.
"Pretty please, Miss Pippa, what?"
I look at the Captain. The bulge in his trousers is massive. I'm so
ashamed, but I can't stop this. I have to ride it out.
"Pretty please, Miss Pippa, I'd like to suck the Captain's cock."
SIX
Inside the restroom there isn't much space. He pushes gently on my
shoulders and I find myself kneeling before him. I reach for his zipper,
my brain telling my hands and fingers to stop...But they unleash him.
His massive cock - so much bigger than mine - springs up to attention,
brushing against my lips.
I think about the few occasions I've told my wife I'd consider anal
penetration when she's asked. And sometimes, following on from that,
I've wondered privately what it would be like to perform orally as a
woman. When I breached the matter one day, Maggie smiled over breakfast
and told me that one day she would teach me. I'm happily married, so
what is that? Why would I have those thoughts?
So now, here before me, is my opportunity to find out.
I can already feel pre-cum on my lips. At least it will be quick, I
think. And even though I don't want to, my fingers begin to delicate
stroke the underside of his penis. He can't help but dither slightly.
"Want to taste it?" the Captain asks.
I shake my head, afraid to speak in case it slips inside my mouth. It's
there constantly, the tip probing my lips.
"Your period? That tampon in your ass? I could make this a real smooth
flight for you."
What am I doing? How is this happening? His cock pushes against my lips
as my fingers continue to entertain him. Maybe it won't be so bad. Maybe
I'll enjoy it.
I almost gasp, shocked by the thought, and my red lips part just enough
for him to make a grand entrance. His penis forces them apart and I let
it happen, guiding him him, taking him with my mouth. My head moves
naturally forward and my tongue explores his shaft. My mouth is full and
I gag slightly as he hits the back of my throat.
He thrusts deeper and I know he's about to cum. I brace myself,
wondering how it will taste. Will I like it? I can feel my own erection,
but so small it deserves no attention right now.
I cup his balls in my hand, tickling him slightly. He heaves and-
-explodes in my mouth. Hot, salty cum pours down my throat. I try not to
gag, but it's impossible as I drown in the unfamiliar taste. I push him
back and he mercifully consents, laughing as he eases out.
Cum sprays over my chin and breasts and all I can think is how he's
ruining one of my favourite bras.
He finally relents, his cock starting to droop.
"Just lick it clean, Kirsten," he commands softly.
I swallow deeply. I'm disgusted at myself now the excitement is over.
The rush gone. My own erection is lost to shame and fear. That taste in
my mouth.
"Do I have to?"
He runs a finger over my still heaving breasts.
"They're so cute," he smiles kindly. "Pert."
He holds his hand up to my mouth, cum running on his fingers. I'm like a
vampire seeing blood for the first time. I'm thirsty for it...But I know
it's wrong. I don't want to do this but I can't stop myself-
I almost lunge for them. My mouth wraps around his fingers one at a
time. Sucking them clean. Moving to the next one with a forbidden
hunger.
It tastes so good. I look for more and find his almost flaccid penis. I
bring it back to life for a moment, pulling it back into my mouth,
sucking and licking it clean.
Finished, I let him go and he zips up. My whole body is trembling,
shocked by what I've done.
He shows me a moment of kindness, holding me tenderly. He strokes my
hair.
"It's okay. I know it was your first time. It must have been difficult."
I try not to cry.
"If it's any consolation, you were good. A natural, I'd say."
He left me. I quickly close the door and lean against it. He's giggling
outside with Pippa. The next is said loudly for me to hear. I shiver
with apprehension as I wonder if she means the words, or if she is just
taunting me.
"Let the other crew know how good she was if they need a break."
I stand, my legs like jelly for a second. I wait to catch my balance. I
can't look at myself in the mirror. I can feel a couple of tears and
hope it is not enough to ruin my make-up.
I remember why I was even here in the first place and unzip my jeans.
My panties are damp, my penis, soft now, wet with pre-cum.
"Are you okay in there, Kirsten?" Pippa calls.
"I'm just putting my panty-liner on."
I hear giggling outside as I unwrap the small package. I insert the
liner into my panties. I tuck my small, deflated penis between my legs,
positioning it central on the liner so that it will catch any more mess.
I'm drained. I've come so close to my own orgasm several times now. I
wish it would just happen, but I know if it does I'll feel worse. The
excitement, the nervous energy, the wonder of what can happen when I'm
dressed, wards the shame and self-hatred off. Without that shield I know
I'll feel beyond pathetic. A waste of a man.
I pull my jeans up and step out.
Three men are waiting to use the restroom. They're all smiling wantonly
at me. I'm sure Pippa has told them what I was doing. And they all heard
my panty-liner comment. As I walk by, unable to hold my head up, they
stare at the bra peeking from my shirt, the mound of my breasts that I
was always in a way proud of. But now I wish I had a real man's chest
and not the small boobs that had naturally developed through wearing a
bra most of my life.
Walking back to my seat I hear the occasional giggle. The odd comment.
"Slut."
"Tramp."
"Whore."
It's a walk of shame.
Finally, I sit down.
Cindy lets out a small laugh. "Wow, girl. You know how to party. You've
got a little something..."
She touches her chin.
I quickly run a finger over my own chin, catching traces of cum. She
looks at me expectantly. I don't protest, perhaps secretly pleased that
I'll get one last taste of the sticky juice. I slowly lick my finger
clean.
SEVEN
The next hour or so was uneventful, although I was constantly fearful of
other crew members coming back for me to entertain. I was used to the
tampon so I fidgeted much less. In fact, it was quite pleasant.
Comforting. Pippa and Lisa handed out blankets and pillows. Most of the
passengers were sleeping.
For a while we were silent and I tried to fathom in my mind what I was
doing, why I was letting this happen to me. I think secretly I was
loving it. For a fleeting moment I wondered if it was a game Maggie had
set up, but this was far too elaborate. It was a string of marvellous
coincidences that had left me...Sickened.
"How did you get into this lifestyle?" Cindy asks.
I told her about my cross-dressing since I was a child. Until I met a
girl, Debs, I really trusted at university it had always been
pleasurable and private. Debs enjoyed games. She'd bring sexy underwear
and make me wear it during lectures. Whenever we were together I had to
dress for her. One time she tied me to her bed in bra and panties,
suspenders and stockings, heels...And left me while she and her friends
drank downstairs. Occasionally she would ask somebody to get something
from her room. Just as I heard steps coming up and approaching - she
would look in and laugh. The next morning she told me they all knew,
anyway, and I always wondered if it was true, and what they must think
of me. One day I was out shopping with one of them, and she casually
held up a dress. 'This would look great on you,' she said. They did
know! All through my university life my friends knew about my cherished
secret. Some taunted me and teased me more than others, but they all
knew. On that occasion Deb's friend watched my temptation until finally
I asked if she would let me try it on. 'Don't ask me. Go and ask the
sales clerk now.' So off I trotted, doing exactly as I was told. The
sales clerk got a laugh, but she let me. That night I had to model the
new outfit for Debs and her friends.
Single again, I would buy and buy, and purge. Throwing everything out.
Sometimes I went a month without dressing, but the temptation was always
there. I'd look at women, hot women, but I'd be daydreaming about how
I'd look in their outfits. I was at a point where I probably looked
pretty good, but was afraid to go out fully dressed. And then purge. And
start over. I needed somebody to control me and my desires. So when I
met Maggie and we fell for each other hard, I revealed my secret longing
to wear women's clothing right away.
It was hard in the early days. She didn't want to see me dress. Then she
allowed me to wear underwear around her; then she made me wear it.
Panties first, but then she regularly had me wearing a bra. We made
love, our smooth bodies wrapped in satin, and it was better than ever. I
think that was when she realised the power she could yield.
Maggie asked clearly for my limits. I told her I was a happy man. That
got a snigger, and I knew that some of my fantasies about being forced
feminised might actually happen. It was scary, but what a rush of
possibilities. I was a happy man, but I wanted more. I wanted to dress
more. Behave like a woman, be treated like one. Maggie had smiled. She
had me hooked and after her initial hesitation she was loving it.
Our games became public. Sometimes she'd plan little events; others she
would spontaneously suggest things. And by suggest, I mean I was told:
shop for this, try that, wear women's shoes out today, carry a handbag.
Anything could happen, at any time. Sometimes she was serious, sometimes
she played what she called 'our little sissy games'. Hints of feminism
on a male. If I could still be called that.
I ceded all authority and power in our relationship to my wife. And it
was incredible. After a while of dressing fairly regularly she told me
if I was enjoying the pleasures of looking and and feeling like a woman,
I should also endure some of the inconveniences. And so, she set me on a
menstrual cycle. Ensured that each period I had a couple of ecstatic
'heavy flows', leaving my panty-liner drenched in cum. Which I would
then have to wear for hours.
That was about half a year ago. Was I genuinely being feminised? Was it
a game? How far would I let myself be pushed before it wasn't something
I enjoyed? All my life I'd struggled to deal with my behaviour.
Sometimes I could embrace it. Other times, like now on the plane, I was
truly disgusted by myself.
Humiliations became more frequent. She started the game NOTES. Sending
me to places with instructions or requests I did not know about until a
sales clerk or receptionist, whoever she had deemed, laughed, giggled
and helped me with the task at hand. Much like the game the security
woman had played.
One day she took me shopping for a sexy maid's outfit at Anne Summers. I
had to try it on in the store and baulked when she brought a sales lady
into the fitting room to answer her questions. I had nowhere to hide
while they talked about how the outfit looked, asking me to stretch or
bend over. The sales woman got right into the role, and told me I had to
step out of the fitting room to see how it felt when I walked. I was
paraded around the shop, occasionally being told to stop at other items.
Strangely I could handle the women, several of them, laughing at me. I
think ever since Debs at university I was conditioned to that; but in
front of the few men I saw I felt so utterly worthless.
"So now," I finish, "whenever I have house chores I have to wear the
outfit, and Maggie always reminds me how pretty I looked walking around
that store."
Her latest venture was this: she was convinced that she'd be able to
find me some form of work as a cross-dresser. Nothing had come of it
yet, and I dreaded the day she would come home and tell me I had to be a
secretary for somebody, or I had to go to work in Dorothy Perkins or
something. Dreading it, but probably with a secret smile. The closest
she had come was when she sent me to one of her colleagues homes to work
as a maid for her. One day a month I go and do the laundry, the
vacuuming, stitch repair clothes. Anything she requires. And she sits
and watches and makes derogatory comments about me while I work. One
time she'd scheduled a maintenance job with a contractor and
deliberately timed it for the day I was there. While the real man did
his work, they both made fun of me.
Telling my story has made me hard. Cindy reaches under the blanket and
occasionally applies pressure against my throbbing penis with her
finger. She never strokes it, holds it or finds my length. Simple,
gentle pressures.
I moan several times. It's only been seconds of pleasure, but my body
suddenly bucks after the exertions and delights of the day.
"Miss Cindy, please..."
Her finger presses one last time. "Just like a woman."
I erupt and the panty-liner catches everything. The sticky mess is all
over my penis and crotch area, soaking my butt and the tampon.
"Heavy flow?" she smirks.
I can only nod as my body settles down. Shame is rising in me, but I'm
not yet overcome by it.
"So quick," she giggles.
"What do you expect after today and all I was talking about," I defend
myself.
"If I was naked before you, I bet you would cum just at the sight.
You're nothing but a sissy-"
"No, I'm not."
"-a sissy who can't satisfy a woman."
"No. I enjoy wearing women's clothing. That's all."
"Kirsten, you just gave the Captain of the plane a blow job."
She laughs at me. I fall silent, shame finally taking control.
"I have to get out of this bra."
"Hold up," she said.
"Seriously, this can't be me. Do you have any make-up wipes?"
"Kirsten, honey. You chose to look like that. You enjoy that underwear.
You look gorgeous."
"I look like a man wearing-"
"And that's who you are. I've noticed how much you struggle. Embrace who
you are. Who cares what the world thinks? Sure, you're a toy for us to
humiliate and embarrass, but you're happy, too. I bet this attitude,
this shame, happens fairly regularly."
I nod.
"So, I'm going to help you through it."
"I can change," I say, hopefully.
She smiles. "I'm sorry, Kirsten. I like you just the way you are."
"But please-"
She raises a finger. "In fact, I think we could do something with your
hair."
She reaches into her handbag, rummages and withdraws a flowery Alice
band. A little bow on the side.
"No," I whisper.
"I'm helping you work through your shame and you protested. This is your
punishment."
She hands me the pretty head band. I hold it for several seconds.
"Do you want me to see what else is inside my handbag?"
"No, Miss Cindy. Sorry, Miss Cindy."
I quickly pull my hair back. It isn't very long, just shy of my
shoulders. But enough that when it is drawn back it looks nice and
girly.
"That looks great," she smiles. "Now get some rest. We'll be landing
soon."
"But I need to change my panty-liner," I argue. And I needed to get the
tampon out of my ass. "Please, Miss Cindy."
"No, no, Kirsten. Get some sleep. And don't ask again."
I consider her. She's serious. I'm not going to mess with her.
"And what do you say?"
"Thank you, Miss Cindy."
"For what?"
"For the wonderful head band, Miss Cindy. For allowing my period to
continue, Miss Cindy," I tell her, and then finally, head bowed: ?For
making my appearance more feminine, Miss Cindy.?
EIGHT
I close my hotel room door behind me and lean against it. Safe at last.
The rest of the flight had been fine until we disembarked. As we queued
Cindy asked my hotel, so I told her. She said she'd watch me leave the
airport to be sure I didn't remove my flowery head band.
The Captain saw me approach, my shirt still open slightly, the cups of
my bra still partly on show for all to see. He smiled for me. Winked. I
was flustered and tried to move by, but the co-pilot took hold of my
hand.
?Maybe I'll see you on the return flight,? he said.
I turned white, convinced everybody must know what I'd done.
Pippa placed a discreet hand on my shoulder. Played with my bra strap.
?See you soon, Kirsten,? she grinned.
But that was all. Customs had been fine. There were looks, of course,
but looks were nothing compared to what I had endured during the flight.
I finally changed my panty-liner in a male restroom and left the
airport.
In the hotel room, by myself, I take stock of all that has had happened.
I undress to my bra and panties, the panty-liner peeking out, and stare
at my reflection in the mirror. Faded make-up. Hair pulled back in the
Alice band.
I take the band out and place it on the side. Run hands through my hair.
?How could you do this?? I ask my reflection.
I pull off my panties and unclasp my bra. I kick them away. I am so
deeply, deeply ashamed by what I have done. I shower and wash the last
twenty-four hours away.
I climb under the sheets of the bed, naked, hiding from the world.
Finally I fall asleep, determined nothing of this scale will ever-
-I wake sharply, bolting up at a pounding on the door.
?Okay, okay.?
I climb off the bed, grab a towel and wrap it around my waist.
I open the door.
Pippa and Lisa, the second flight attendant, march by me.
?Come on in,? I murmur.
At least this is my room. My territory. Nothing can happen here.
?Take off the towel,? Pippa instructed.
Lisa went into the side-room.
?Come on. You had your fun earlier. Let me-?
?Take off your towel,? Pippa demanded.
I hesitate...But then let it fall to the floor. My smooth, hairless body
amuses her. She stifles a laugh as she stares at my wilting penis.
?It's so small. Lisa come see,? she cries out.
Lisa peeks out. I will my cock to become erect. Show them both I am a
man. What I am capable of. But it barely stirs under the pressure.
?Nice clit,? Lisa grins and returns to the room. I hear the zip on my
luggage.
Pippa watches as I concentrate on developing an erection.
?Think about my uniform, Kirsten. My tights and shoes. My pencil skirt
and soft, soft blouse.? She teases her hands over her body. ?This
wonderful, girly scarfe we have to wear. Do you like it??
?No, Miss Pippa.?
My erection, making an appearance at the wrong moment, told her
otherwise.
?Do you want to wear it?? she asks.
My eyes light up. Was she serious? I'd love to wear it. Even when I was
a child, while other kids dreamed of becoming an astronaut, I longed to
be a female flight attendant. One of my fantasies was to work as one,
and when my wife talked about getting work as a cross-dresser I'd
confided this to her.
?Really? Yes, please, Miss Pippa.?
She laughed. ?Maybe one day.?
A loud burst of laughter from the side-room.
?You have to see this!? Lisa calls.
I dread what they might have found, what Maggie might have packed for
me. I wonder if there's a note inside, a game, and Lisa is reading it
now.
Pippa walks by, taps my shrinking penis with her hand. She giggles.
?Nice clitty. Now, put on your bra and panties and stand at the window
while I decide what to do with you.?
I dress as she instructed and stand in front of the window, aware that
anybody in the opposing structures could see me. I listen to their
laughter and giggling, can hear them talking excitedly but can not make
out the words. What are they up to?
Waiting, I notice a glint in a window across the way. I study the area I
saw it, and slowly realise somebody is watching me through binoculars.
No way. I cover my breasts with my hands; a horrible feminine instinct
that has somehow gotten wired into my brain.
I look around, wishing Pippa and Lisa would hurry up and save me from
the voyeur. I realise he's probably getting off on watching me and I
slowly lower my hands and pout sexily for him. I might as well have some
fun.
I play with my small breasts. Run my hands over my smooth, shaven body.
They reach my hard penis and I begin to massage myself through the
panties. Lost in the delirious moment I start to pant, my body heave-
A hard smack on my butt brings me back to reality.
?That was so funny,? Lisa grins.
?Do you like putting on a show?? Pippa asks.
?No, Miss Pippa.?
?Sure looked like you were having fun. For the rest of your stay those
curtains are to remain open.?
?I don't want everybody seeing me like-?
?Come on, Kirsten. That's not what it looked like. The more I think
about it, the more I realise you're a good time girl. So while we are
having fun, he'll be having fun.?
?But, Miss Pippa-?
?Deep down,? she whispers, ?I know you're loving this.?
I look around for an escape. Finally meet her eyes.
?Yes, Miss Pippa.?
?Do you know what's in the bag?? Lisa asks.
I shake my head. ?My wife packs for me. She likes to surprise me.?
?This is priceless,? Pippa smiled. ?I've got some calls to make. I'll do
it here. Before the fun really starts, do you fancy a swim, Kirsten??
?Please, Miss Pippa,? I nod eagerly. At least I'll be away from her.
Pippa looks at Lisa. ?Did his wife pack any swimwear??
Lisa grins. ?You bet she did.?
From the happy response I know I'll not be sitting by the pool in my
swim shorts.
NINE
We walk through the hotel. Every step brings a new look, a new
embarrassment, as Lisa deliberately leads me a long way to the pool,
even managing to bring me through the busy reception and lobby.
She looks great in her string bikini. Flat tummy and gorgeous breasts
threatening to escape. A towel wrapped around her waist. And while I
long to look as sexy, deep down I know that I look ridiculous in my
flower print one piece. I too have a towel wrapped around my waist. A
nice pink one. And my sandals are discreet, but glittering stones
decorate the straps and small buckles.
We reach the, thankfully quiet, pool and swim several lengths together.
We emerge into the sun, a real sexy model moment for Lisa, knowing how
good she looks. I try and enjoy the moment, but my heart sinks as the
few onlookers enjoy a giggle.
We recognise one of them from the plane and Lisa guides us to her.
?Hello,? Lisa smiles.
?Hi,? Cindy says, genuinely pleased to see us. ?I switched my hotel when
I heard where you were staying.?
?Hello, Miss Cindy,? I say. At least she was pleasant. Didn't seem to
have quite the cruel streak, like Pippa.
?Do you mind taking care of Kirsten?? Lisa asks. ?That way I can help
Pippa with her plans.?
?No problem.?
?We'll need her back in her room in a couple of hours,? Lisa says, and
hands my keycard to Cindy.
?I can't sit out here that long,? I argue.
?Don't you worry, Kirsten. I've got something special in mind for us
girls to do.?
Lisa leaves and Cindy pats the seat next to her own.
I join her.
?Like a lady.?
I cross my legs. Back straight. I push my small breasts out.
She admires my svelte legs. ?Wax or shave??
?Shave,? I tell her. My wife had me wax a couple of times, but then
decided she liked knowing that I had to maintain that aspect of my
appearance myself.
?You look good,? Cindy commented.
?Thank you, Miss Cindy.?
A couple of jocks wander by and erupt into laughter. One even points at
me.
?Ignore them,? Cindy tells me. And then: ?Check out the bartender.?
The pool has a small bar. The man behind it is young, quite striking.
Muscled chest and tanned. Maybe I consider him a second to long.
?I'm going to play with you, Kirsten, because a real man wouldn't have
even looked.?
My head hangs in shame.
?Do you want to give him a blow job, too??
?No,? I say quickly, but my eyes do wander to check him out again.
?You're crushing, girl. Do you want to feel his-??
?No, I do not,? I say firmly.
?Miss Cindy,? she whispers. ?I love you, Kirsten. I really do. But
sometimes you forget your place so now I'll have to see what I can set
up.?
She stands.
?Miss Cindy, please don't.?
Cindy heads for the bar, chuckling. She's about five minutes. She
gestures to me more than once. I have mixed feelings. I'm dreading what
she might be saying, but another part of me is enjoying the attention.
So when I catch they are looking at me, I stretch my legs out and
massage them. Push my small breasts out.
Cindy returns. Hands me a Mojito.
I sip gracefully from the glass, finger out.
?You little slut,? she accuses.
?No. Why??
?You total flirt. You enjoyed that. Playing up for us. Do you feel
sexy??
I blush. ?Yes, Miss Cindy.?
She laughs. Lisa and Pippa sent me out without any make-up on. Without
pinning my hair back.
?You're just a man in a woman's swimsuit,? she reminds me.
I must look ridiculous. No matter how much I delude myself.
?But he still wants to meet you in the spa. Come on.?
The walk to the spa takes forever. Another tour through the whole hotel
for all to see and all to giggle at.
?Please, Miss Cindy. I don't want to go through oral sex again.?
?Really??
I take a second too long. She smirks.
By the time we get to the spa reception, I am dragging me feet.
The receptionist, auburn hair and sexy as hell in her glasses and cute
little uniform, looks up. Her double-take is obvious at my appearance,
but she professionally maintains her composure.
?What can we do for you, Miss...??
Lisa kicks me.
?Kirsten,? I stammer.
Cindy steps in. ?My friend would just like to get her nails done today.?
I look at her, confused. Breathe a sigh of relief.
Cindy grins. ?I'm not going to waste somebody that good looking on you.
He's all mine.?
?Thank you, Miss Cindy. Thank you.?
The receptionist checks her computer. ?I can get you in right now,
Kirsten.?
?Fantastic,? Cindy declares.
I've never had my nails done before. It was an extremely pleasurable
hour or so. Cindy toned down the games because she instantly read how
kind hearted the nail technician was. Her name was Caroline and she
wanted to know all about me. She commented how brave I was for being so
open about who I was. I blushed a little, but she insisted that it was
pretty incredible for a man to put himself out there like this.
She filed and buffed and trimmed and applied the acrylics. I took it all
in.
Finally, she looks up: ?What colour would you like??
I begin to consider, but Lisa chimes in.
?Your lipstick. The one you had on when I first met you. She's got the
most gorgeous red lipstick and gloss, like...?
Cindy runs her fingers around some choices.
?There,? she says enthusiastically.
I quickly nod. ?Yes. That's the one.?
Caroline works for a little longer. ?This is looking great. Do you trust
me??
I nod. ?Of course.?
?I've got an idea.?
Sometimes when I encounter people they openly laugh or heckle; others
are polite and friendly but probably snigger after I've gone. But
occasionally you meet somebody who genuinely shows kindness and wants to
understand and help.
?All done,? she tells me.
I consider my hands. The nails are amazing. And Caroline has decorated
them with tiny white snowflakes.
For a moment I'm actually lost for words.
?Thank you. They're beautiful.?
?You're welcome,? she says and hands me a card. ?Next time you're out
this way I'd love to get together for a coffee or something.?
?Me, too.? Cindy and I stand. ?Thank you so much. I'll see you again.?
Cindy leads me out.
?Come on, Princess,? she tells me, and I crash back down to earth.
?Let's get back to your room and see what Pippa has in store for you.?
TEN
Cindy tells Pippa and Lisa about our adventures.
?Thank you so much for keeping her busy,? Pippa says. ?Her nails look
great.?
Cindy considers me. ?Maybe I'll see you again one day.?
?I'd like that, Miss Cindy.?
She leaves me alone with Pippa and Lisa. They waste no time, instructing
me to stand near the window for the voyeur.
?Get undressed,? Pippa tells me sharply.
I remove the swimsuit and they laugh at my tiny penis.
?The pool was cold,? I begin.
?Don't even bother,? Lisa says, waving her hand.
?Watch this,? Pippa says to her friend. She runs a hand over her skirt
and blouse. ?Do you like me uniform, Kirsten??
?No,? I lie, knowing she is doing this just to get a laugh for Lisa.
?Are you sure?? Pippa sings.
There's no holding back my small erection. Lisa sniggers.
?Please, Miss Pippa. Can I wear it??
?Kirsten,? Lisa asks, ?would you like to be a stewardess just like us??
She's getting into it, too. Fingers brushing over her light scarfe. They
can see how eager I am and their laughter subsides to looks of
seduction.
?Do you want to join my team?? Pippa asks.
?Yes, please, Miss Pippa,? I beg, giving in to my old fantasies.
She considers me. ?I'm not sure...?
?Please, Miss Pippa, I'll do anything.?
Pippa smiles slyly. There it is. Anything. I was desperate and she knew
it. She had me completely now. I would do anything for them if they
would grant me a few minutes to privately enjoy their uniform.
?I think I can arrange something for you,? Pippa promises. ?I just need
you to follow my instructions until you get home.?
I hesitate. Not just here. The flight home. I believed I was safe on the
flight last time after my experiences at the airport and look at what
they had done. But it couldn't be any worse than that. Could it?
?Anything for you, Miss Pippa,? I tell her.
?Good, then.? She gestures to the bed. ?There's your nightie.?
It's my favourite. Full length. Soft satin and lace. Decorated with tiny
glistening crystals.
?We'll begin early in the morning so get some rest. Then on to your
meeting and your flight home tomorrow evening,? Pippa explains.
I begin to panic. My meeting. This was my big break and I'd forgotten
all about it. It could change our lives and here I was-
My fingers!
?I have to get these off!? I exclaim, prying at the nails.
?Relax,? Pippa eased.
?But you don't understand-?
?Calm down, Kirsten,? Lisa says, handing me a glass of wine.
I gulp it down. And then remember to sip lady-like.
?But what am I going to do??
Pippa sits me down. I naturally cross my legs.
?Good girl,? Pippa says. ?Now, the way I see it you have three choices.
You can miss the meeting-?
?It's too important, Miss Pippa. Please help me. Do you have any nail
polish??
She laughs. ?Those need professionally removing and I'm sure the spa is
closed. And unfortunately, you are going to be very busy in the
morning.?
?Busy??
She waves her hand. ?Don't worry for now. So you must attend the
meeting. That leaves two options. Number one: when I check in with you
at lunch-time tomorrow I promise I will make you as beautiful as
possible so you can try to pass as a woman. Hope nobody reads you. Or
number two: you can accept who you are and I will decide what you can
wear like the sissy you are.?
I begin to cry. Lisa hands me another glass of wine.
?Thank you. I don't know what to do.?
The meeting with the manager in LA was a big break I'd worked towards
for years. And now it was in jeopardy.
?Sleep on it,? Pippa advised.
?I'll never sleep tonight.?
Pippa grinned. ?Go to the bed.?
I stand, feeling woozy. She holds my arm and guides me to the bed.
?Did you-?? I begin, and collapse onto the mattress to the sounds of
their laughter.
ELEVEN
I wake early, to the sound of a voice I don't recognise.
?Time for work, Sleeping Beauty. Don't want to be late on your first
shift.?
I sit up, confused. An attractive sun-kissed blonde stands before me.
Skirt suit and sensible heels.
?Who are you??
?Kelly. Head of Personnel here at the hotel. A highly unusual letter was
found in your room and-?
My wife, I think. This is her game, NOTES. Pippa must have found the
letter in my suitcase and left it out as I would have been instructed
to.
?-I have to say it seems strange. But then I saw your uniform hanging up
and realised that this is a serious request.?
?My uniform??
I think about Pippa's promise to wear a flight attendants uniform. So
I'll have to wear it in front of this stranger? No problems. I start to
get erect at the thought.
?Yes,? Kelly says, opening the closet door to reveal-
-my sexy Anne Summers maid outfit.
?I must admit, it's fancier than my girls get to wear, but for a few
hours it should be okay.?
?A few hours of what??
Kelly picks up an envelope from the dresser and removes the letter. She
reads it out loud, taking great pleasure as she watches me squirm with
embarrassment.
?To whom it may concern: My husband, if you can call her that, has
always believed she'd make a fantastic maid. Indeed, she completes all
our house chores, and once a month she also works for a good friend of
mine. I'd love if you could give her a chance to work for you, even if
just for an hour or two. Genuinely, Maggie.?
My face is white with fear, and I pray that I will only have to clean
this room.
?I don't know if I can do-?
?I was told by your good friend Pippa that you would show me proper
respect. Now, we'll start here. When I return I expect you to be ready.?
She heads for the door.
?Please, Miss Kelly, you surely can't have a man parading in a maid's
outfit in your hotel.?
She grins. ?This is LA, Kirsten. Besides, we have an open policy. Now,
I'm going to see what rooms we have available. I know you have a big
meeting so I'll choose them especially for you to make sure you have
time to get ready.?
She leaves. I sit in shock. If nothing else had happened this trip, I
probably would have been ecstatic at this notion. But I am spent and
exhausted. I am over-dosing on the humiliation I am, for some reason,
addicted to.
I better get moving, though. Pippa seems to have it in for me. I don't
need to be in the sights of another powerful woman.
I quickly shower and apply my make-up, a nice, soft day look. I fix my
hair in the Alice band Cindy gave me. I put on satin panties and bra,
suspenders and lace top stockings. I place the inserts in my bra and
then put on the maid's uniform. Black and soft and sexy with layers of
chiffon; the top quite tight with decorative lacing. I fasten the bow at
the back and finish the look off with a frilly white headpiece and the
four inch heels my wife has packed.
I check the mirror, pleased with how I look.
I'm ready. I start to clean my room and as I am finishing decide to
entertain my voyeur friend, prancing a little. I twirl-
-as the door opens and Kelly steps in.
She laughs at me. Loud and outrageous.
?I'm sorry, Miss Kelly. I am finished, though.?
She smiles. ?Yes, I can see. You've done a great job in here. Now come
along.?
I walk to the door, but each step is getting harder.
?It's okay. It's only down the hall to your first room.?
I hesitate.
?The hotel is typically quiet this time of morning,? she assures me.
?Most people have checked out, or gone out for the day.?
I breathe deeply and step out, the door closing behind me.
As we walk down the corridor Kelly starts to giggle.
?What's wrong??
?I've never seen a...well, a sissy like you before. You obviously want
this-?
?No, Miss Kelly.?
?But yes, you do. You didn't protest once in your room. And, if you had,
do you honestly think I'd be doing this. I have my career to watch out
for. But since you want this so badly, and I have the note to prove it,
I'm happy to play along.?
She ushers me down the corridor. ?Those heels are stunning. You walk
well in them.?
?Thank you, Miss Kelly.?
?And those nails are to die for. Who did those??
?Caroline,? I tell her, marvelling at the way the light glints off the
snowflakes.
A hotel guest approaches and I try to shrink behind Kelly, but she
deliberately exposes me. Despite my best efforts, I am quickly aware I
am not fooling anybody. He tries to keep a straight face, but gives in
to his amusement.
?That's lucky. Caroline's off today and Ronni is fully booked up so
you'll get to enjoy them for a while.?
How can I attend my meeting with these nails. Pippa's words echo in my
mind: go as a woman, or go as a sissy. I'm obviously not passing as a
woman at the moment, but Pippa said she would help me. I'm not a sissy,
I told myself, catching my reflection in a panel wall mirror. I am not.
I was being made to do these things. I am a man.
Another maid emerged from a nearby room. She stifles her laugh-
?It's okay,? Kelly assures her.
It erupts out of her.
?Good morning, Sammi. I'd like you to meet Kirsten. She's joining our
team today.?
TWELVE
My first room is empty.
I make the bed, dust and vacuum. Clean the bath, sink and toilet. Tidy
any bits of litter.
Kelly enjoys watching, offering instructions and giggling. She
particularly enjoys finding reasons to have me bend over so she can see
my lace stockin