Ready For Anything? free porn video

"Pick one." Those two words started everything. Those two words were
the innocent drink that led to my addiction. They're responsible for
my current situation, and the nerves racing through my mind as I
approach the hotel lobby bar dressed as no man does, at least not one
who expects society's approval. I hear my high heels click on the
marble of the lobby floor. I adjust my little black dress and play
idly with my long dangling earrings. As I'm nearing the bar, my mind
goes back to that first choice ...

"Pick one." That's what my girlfriend said, as she stood two tubes of
lipstick on their ends. They were the same brand, both in a dark
plastic case. They looked identical, except for the name, which was
concealed on the bottom of the tube. One of the tubes was a deep red
lipstick that I somehow convinced her to buy earlier that day. The
other was a neutral shade that she preferred. But they looked the same
when they were standing up in front of me like that.

"Pick one," she repeated. "If you pick the bright red one, I'll put it
on and suck little Jimmy so much it will make your head spin."

I hesitated.

"Come on," she continued, "an offer like this doesn't come around very
often. That blowjob you always want is just one touch away. You have
a 50/50 shot. All you have to do is tell me which one is the slutty
lipstick you begged me to buy."

Still, I hesitated. I was obsessed with the thought of that blowjob.
Michelle doesn't like to give me blowjobs. She says it doesn't taste
good, that it's smelly and that she hates to swallow my cum. (Other
than that, I guess it's great.) But here she is, giving me chance.
All I have to do is pick the right color lipstick.

I reach out to pick, my heartbeat racing. I stop. It must be a trap.

"If I pick the red one, you'll wear it?"

"Yes, and I'll wrap those red lips around your cock just like you want.
You'll have the best orgasm you've ever had -- maybe several."

OK, she had repeated the positive a few times. "And if I pick the
other one?"

"That would be fine with me. I'll wear that one, and you will treat me
to dinner at a place of my choice. But little Jimmy won't get anything
tonight. Not even your own hand."

This whole discussion has gotten me excited. Jimmy is full-sized and
hard right now. My heartbeat must be at 130 at this point. I can
visualize the reward I'll get if I pick correctly. It will be so
sweet. But if I pick incorrectly, I'll get nothing. I see the
gambler's dilemma. I understand the rush of the wager. I reach out,
again, toward the lipstick on the left. God I hope I'm correct. I
pause, then lunge and touch it.

"The left it is," she declares. "Now let's see what's in store for you
tonight. Will it be pleasure? Or will you be the pain of lost
opportunities all through our meal?" With that, she holds the lipstick
up. I can't tell what I picked, nor can I read the name on the bottom.
Lipsticks have those ambiguous names anyway. It's always something
sultry like "Seductive" or "Kissable" or "Goddess." Why can't it just
say "Red"? Whatever, just please let it be red.

She pulls off the cap, still concealing the contents. My heartbeat is
at 150 now. She slowly twists the bottom, bringing the lipstick up.
When I see the red tip, I jump up. YES, I think. I knew it!!
Michelle smiles. She's enjoying this, too. Before she paints her
lips, she takes my hand and guides it to her vagina. I begin rubbing
her with my fingers, but she's already soaking wet. "See what you can
do to me?" she whispers. "Now you'll see what I can do to you."

Needless to say, that experience was one of the best we both had ever
felt. I couldn't believe the way Michelle acted. But more than
anything, I couldn't forget the rush of the gamble. The risk-reward of
the choice was enticing.

After that night, we had many more experiences involving game playing.
Michelle always set up the choice. For the first few times, it
involved that red lipstick. When I got that, it meant success. But if
I got something else, it meant disappointment for me. I won about as
the odds would predict -- about half of the time. But the thrill of
"victory" was oh so savory that it made up for the disappointments of
the losses.

Soon, the games migrated to a series of dares. If I won, she would do
something I wanted, or something mildly embarrassing. If I lost, her
choice usually was to have me naked and at her direction. One time,
she even took me out at midnight, wearing only my windbreaker while she
drove us through a fast-food pickup window.

After a while, Michelle changed the stakes. It was after a dinner out
at a restaurant. Fittingly, it involved those two lipsticks again. We
were sitting at the back of the restaurant. It was late, so most of
the crowd had finished and we were one of the last couples in the place
(until the after-hours crowd would arrive). Michelle took out the two
tubes, shuffled them and stood them up on the table.

"Jim, its time for another of our adventures. I hope you're up for the
challenge this time." Hearing her say that, and seeing the array, I
quickly "rose" to the occasion, you might say.

"I have your favorite red lipstick here. I also have that neutral
shade. The red of course is bold and attention-grabbing. The neutral
is so light, so subtle, you can hardly tell I'm wearing it. Now, like
before, if you select the red one, that's what I'm going to wear. We
will head home immediately and I'll pleasure you like you so adore.
All you have to do is select the right color."

Thinking we're playing the same old game, I start to reach out.
Michelle grabs my wrist and stops me.

"Wait a minute there, big boy. We're not done. You see, this time,
there's a little more to the wager. If you select the red one, I'll
wear it and do the things I said. And if you select the neutral one,
I'll wear that, too. But here's the difference: YOU have to wear the
other lipstick. If you pick the red for me, no problem. You get all
the benefits I said, and no one will even be able to tell that you're
wearing anything. However, if you pick the neutral for me, I get to
see what your lips look like in this red color. You will have to walk
out of the restaurant, to the car and wear it all the way home.

"So, pick one. One for me, and one for you."

I try to talk her out of this. "That's not balanced at all," I
protest. "The stakes are very different. If you're wearing the red,
no one thinks differently of you. But if I wear it, I'll be humiliated
by anyone that sees. I think it's more fair if I only have to wear the
neutral one -- and only if I don't pick the red color for you."

"No, there will be no negotiation on the stakes. I get to set them. I
want to see you in the red lipstick -- right here, in public -- if you
lose. That's the bet. If you don't want to play, you can forfeit.
But forfeitting will have a cost, too." I don't bother to ask what
that is; I can see her mind racing already. Quickly, she continues, "I
know. I bought some nail polish at the store this afternoon. It's in
my purse. I haven't shown you it yet. It could be bright, it could be
soft. It could be one of those that only shows a color when exposed to
the sun. Or, it could be the new clear topcoat I've been meaning to
buy. If you choose to forfeit, I will paint your fingernails with that
new polish, whatever it is."

"So there it is, take your chances with the red lipstick, or take a
chance on the nail polish I have in my purse. What do you want to do?
Are you going to be bold and pick a lipstick? Or, are you too wimpy to
risk it and would you rather that I give you a manicure with whatever
bottle I have with me? The choice is up to you."

I couldn't believe what she was saying. Where had these new downsides
come from? Why did she want to embarrass me? Despite my confusion, I
know she is serious. I'm also consumed by the rush of the gamble. I
ponder my chioces. I can't choose the nail polish. It's most
certainly a set-up. Yes, she did remark this morning that her topcoat
was getting old, but did she really buy a clear polish? I doubt it.
This is like those sucker bets in the middle of the craps table: they
sound appealing ("8 the hard way"), but they're really bad odds. No,
I'm certain that the nail polish is colored. It's a hot pink or
something. There's no way I'm falling for that bet.

Besides, I couldn't back out like that. I'd feel embarrassed about
having wimped out of the real challenge, and I might end up with hot
pink nails anyway. No, I had to pick the lipsticks. (Go for the
gusto, I tell myself. Go big or go home.) I reach out, choosing the
left one again. It was lucky that first night, why not now?

But it wasn't. The lipstick on the left was the neutral color.
Michelle painted her lips with it quickly. Then, she took the red
lipstick and outlined my lips generously. She offered me a mirror to
see, but I refused. I didn't want to know what it looked like. I'm
sure it was ridiculous. As we got up, our waitress returned to the
table. She noticed my red lips. She smiled, and said, "Ready for a
night on the town now? Have a great time!" As we walked out of the
restaurant, Michelle held my hand and made me walk slowly. My palms
were sweating, and I could hear my heartbeat. I was thrilled and
mortified at the same time. Worst of all, this feeling showed in the
bulge in my jeans as we walked to the car. Luckily, other than the
waitress, we did not encounter anyone else. Thank God.

Our lovemaking that night was fantastic. Little Jimmy was Big Jim the
whole night. Michelle liked having me put lip prints all over her
body, and enjoyed the taste of my lipstick when we kissed.

We continued this way for another two weeks. My penalties for losing
now involved some form of feminine feature -- lipstick, painted
toenails, panties, even a bra once. Unfortunately, after a couple of
weeks, Michelle lost interest in these games. She didn't really say
anything about it. At first, Michelle didn't initiate the gambles as
often. When she did, it was with less imagination, almost mechanically
repeating the "if you lose, you'll wear red lipstick" downside. I'm
not one to force confrontation, so I didn't really question her
dwindling enthusiasm for the games. I just tried to go with the flow,
figuring maybe she would find that enthusiasm again. My only hint as
to her true feelings was a side comment one time, when she said, "can't
we just try something normal tonight?"

After that comment, our lovemaking continued, but moved back to the
more traditional, passionate lovemaking between two consenting adults.
The kind that is satisfiying but they don't usually write stories
about. I was accepting of this change. After all, we were in love
still. So, everything was OK, I guess. No, it was good, I told
myself. Really. It was good. Better than good ... great.

The Addiction Grows

I should have said something, of course. But I didn't. Instead, one
day, I just succumbed to my unsatisfied desire. My work involves
regular business trips, typically 2-3 days at a time. About a couple
of months after our lovemaking returned to "normal," I was packing for
a trip when I spotted the neutral lipstick of our gameplay. It had
fallen over, tucked in the back of our bathroom closet, next to some
travel size toothpaste. Discarded, like our gameplay had been.
Impulsively, I took the tube and hid it among my toiletries. Twenty-
four hours later, I found myself in a hotel room all alone. I began to
think about our games. Any gambler will tell you what comes next. I
missed the thrill. I missed the excitement, the wonder, the
nervousness. So, I dug out the lipstick from my bag. I put it on. I
could taste the color on my lips, even though I couldn't really see it.
I kept the lipstick on for about an hour. I didn't go anywhere, but
the feeling was thrilling.

The next night, the feeling returned. I put the lipstick on again.
But this time, I needed more. Like the gambler, I guess, I needed the
rush of higher stakes. So, I walked to the ice machine on my floor.
No one saw me, but I was on guard the whole two minutes of the trip. I
pleasured myself back in the room, tasting the lipstick the whole time.

An hour later, the feeling returned again. I painted my lips once more
and headed toward the lobby. It was 11 pm. No one was downstairs
except the night clerk. He didn't pay much attention to me. Craving
more, I walked up to him and asked him where a d**gstore was. Looking
bored, he said, "Outside, to the left. It's open all night." He
didn't even look me in the face, much less take note of my painted
lips.

Taking a deep breath, I exited the hotel and turned left. I'm not sure
what I'm going to do at the d**gstore, but I head there anyway. I look
left and right, but don't see anyone on the street. I get to the
d**gstore without incident and enter. I could have gone anywhere in
the store, but the cosmetics aisle was right up front. I went there.
There was a young woman selecting something. I don't think she even
paid me a second thought. It made me nervous anyway. When she left, I
migrated to the nail polish section. They had a huge display from OPI.
It's the brand Michelle uses. I stand there for a moment, trying to
decide what to do. My eyes scan the various colors. I don't dare
touch any -- that's too obvious. I'm thinking about my excuse: my
girlfriend sent me to get a color for her. Her nails were chipped or
something. No, that's pretty lame, I think. It's 11 pm; what woman is
fixing her nails at 11 at night? The only other thing I can think of
is that it's a dare. Still lame, and it draws attention to me anyway.

Finally, I decide that it doesn't matter. Who's going to quiz me
anyway? You don't need to justify your purchases. I'll just grab
something and go. So, I reach out to pick a red one. They're so close
in color that I almost pick one at random. Out of curiosity, I glance
at the name. Redy for Anything. Cute. Almost appropriate, I think.

I head to the counter to pay. As I get there, I realize this was a
dumb thing to do. Here I am at 11 pm, buying just one item -- red nail
polish. I'll go with the chipped nail thing, I tell myself. But the
clerk, a 20-something girl with three piercings in her ear and a tatoo
of a dove on her wrist, doesn't ask. Instead, she says to me, "I love
this color. It's more conventional than I usually wear, but when my
Mom insists on something respectable, I use this." I start to mumble
some form of "thanks," but she looks me in the face. Her eyes go to my
lips. She must see the shine. Then, in a softer voice, she says, "You
probably want some remover too, honey. It's right in aisle 2. We have
travel sizes, so you don't waste any." I don't respond, and she adds
more. "Do you have a topcoat? It really makes the nail polish shine.
I recommend the Sally Hansen topcoat. It shines more and it's cheaper.
No sense paying top price for the OPI, you know?"

Now's my chance to use the chipped nails excuse. But I don't.
Surprisingly, this thrill is even more intense than at the restaurant.
A woman I don't know just outed me. I could lie, and she probably
would let it go. But she won't believe me even if she let it go. No,
she definitely would be telling her girlfriends (and maybe her
boyfriend) later about the guy who came in to purchase nail polish for
himself.

Instead of lying, I mumble thanks and I turn to pick up the remover and
topcoat like she recommended. When I return, I can't even look her in
the eye. My hands are sweaty. Without even looking, I can imagine her
smiling face. I hear it in her voice, too, when she says, "Have fun
tonight! We're open all night, if you want to show me how it looks."
I'm mortified, but strangely excited at the same time.

I don't paint my nails, however. It's too late and I have an important
meeting tomorrow. I can't afford to be reckless. But I set the nail
polish out on the desk, in plain view. The rest of the night, I kept
running the experience through my mind. Over and over again, each time
thinking about those two minutes with the clerk. I even gave her a
name: Katherine. Katie, for short. That sounded right to me. It was
fun and flirty, but firm and traditional at the same time.

From then on, I was hooked. I was hooked on the adrenaline rush of the
gamble. I couldn't wait for the next business trip, and the next
adventure. Over my next few trips, I purchased a complete outfit for
myself. Buying a dress was intimidating for me, but probably was the
easiest of my purchases. I did a little online research before I went,
then headed right to the department I needed. I selected "my" dress:
a red, 3/4 sleeve dress with a ruffle in the front (it was called a
"rouched" front online). I guessed at the size, using the
measurements from the online site. It looked like the dress was long
enough to reach my knees. My only indulgence was, after glancing left
and right to make sure no one was in the area, I quickly held the dress
in front of me. Not up to me (that was too much), but at body level
and in close. Yes, the length would be fine. I headed quickly to the
checkout. I asked for a box, so the clerk would assume it was a gift.
It must have worked, as the clerk commented how sweet I was to buy a
dress for my wife. Little did she know.

Buying heels was embarrassing. I selected basic black pumps, with a
four inch heel and peep toes. I didn't try it on or anything. Once
again, I had checked sizes using the size charts online. But there is
no hiding who you're buying heels for. No man that I know buys heels
for his wife/girlfriend. And the clerk knew it too, of course. She
suggested I buy some of the tights, which they had at the register.
They were two for one, so she gave me black and nude ones.

Finally, thinking of no way around it, I went to a department store for
undergarments. I bought a bra, panties and shapewear. I waited and
wandered until there was no line at the register. I handed the clerk
the items, and had my cash in hand. (I always selected the line with a
female clerk.) I couldn't make any eye contact at all. Luckily, she
didn't delay, didn't ask me to join their bra club or anything. I
practically ran out of the store, my pretty underthings in tow.

The Discovery

My big opportunity came a month later. It was much longer than usual
between business trips, and I was really anxious to get going. I was
going to be at an educational conference. One with lots of lectures
during the day but no obligations at night. It would last four days,
Monday through Thursday midday. Since I wouldn't know anyone, I
thought I could try on my dress and heels in my hotel room. I'd just
wear them in the room, maybe on the balcony if I was daring. I even
told myself that I would hang the dress in my closet and leave the
heels out on the floor. It thrilled me to imagine what the maid would
think. With only one outfit and none of the makeup and all, it would
be clear that there wasn't a woman staying in the room. I smiled
thinking of the small but very safe humiliation of that plan.

On Sunday morning, I packed for my trip. I secretly put the dress and
undergarments in a small bag and placed it inside my suitcase. The
heels were nestled in the bottom of my luggage. I would put the nail
polish in with my toiletries. I was planning to carry the beige
lipstick with me on the plane. I'm all set.

Right after I packed, Michelle surprised me. "Honey, I have something
special for your trip," she announced. "It's something you might like,
I believe. You see, I recently got another of those gift bags of my
cosmetics. It has a lipstick in it. It's a duplicate of one of my
favorites. A cute soft pink. One of the ones you've liked when I wore
it. " She leaned in to kiss me, and slid the lipstick into my hand
while we exchanged affections. "Take this with you on your trip. When
we talk, you'll be able to imagine me more vividly than normal, seeing
the lipstick and hearing me on the phone." Then she winked and said,
"who knows, I might even want us to be 'twins' one night this week!"
The image got a quick rush out of me. Perhaps my playful and daring
girlfriend was back.

I quickly put the lipstick in my pocket, with the beige one (though
Michelle didn't know that). She then headed out for her lunch with
friends. I don't have to leave for my flight for an hour. After
Michelle left, I started running through my plan again. It would be
perfect. Running through everything, I remembered "Katie," the clerk
at the d**gstore. Impulsively, I dug the nail polish out of my bag. I
have time to do my toes now, I think. I'll be wearing socks at the
airport, but still -- I'll know my toes are painted. So, for the first
time ever, I sit down and paint my own toenails. (You should know,
however, that, during our "adventurous period," I had painted
Michelle's toes a few times. So, I wasn't half bad, even if I was
running the brush in the opposite direction this time.)

Soon, my toes were a bright red. Redy for Anything. Definitely, I
thought. I packed my bag, put Michelle's pink lipstick in with my
toiletries and headed out. The airport security went smoothly. The
screeners don't really care whose bag has heels or a dress in it;
they're legal for travel, so what does it matter? My neutral lipstick
even went through with my keys and change no problem. If anyone
noticed, they didn't care.

My flight had a stopover where I had to change planes. The layover was
an hour and forty five minutes. Not too long, but it would give me
time to get some food if I got hungry. During my first flight, I got
bold. I had an aisle seat, and at one point, I adjusted my position
and felt my tube of lipstick. Impulsively, I thought I would wear it
for the rest of my flight. It was a neutral shade and, except for
Katie, no one had ever noticed when I wore it. Besides, the lady in my
row was sleeping. She probably would never even look.

I went to the lavatory to put on my lipstick. I did my business and
then, getting ready to get out, I pulled out my neutral lipstick.
Except there was one problem. It wasn't my neutral shade at all. It
instead was the soft pink that Michelle had handed me. (I must have
gotten them mixed up when I repacked.) I could have stopped. And if I
did, I wouldn't be walking down to the hotel bar in this black dress
and four inch peep toe heels. But, the gambler in me took over.
"Don't be a wimp," he said, "No guts, no glory." So I put the pink on
my lips -- lightly. Just a light coat would do. I had to steady my
hand, but I painted in the lines, so to speak. There, I thought.
Looks good. No one will notice, I told myself. It's almost the
natural pink of moist lips. Yes, absolutely.

Heart reacing again, I return to my seat. The cabin lights are off,
and no one can really see. I'm fine. Even the lady next to me is
still asleep. But I can't really concentrate the final 20 minutes of
the flight. When we land, I plan to make a quick exit. Luckily, I'm
in one of the premium rows, so there is no waiting. My exit goes
smoothly, except for the flight attendant in front. She sees me and
starts to wish me a nice day. She does a double take, ever so
slightly. Does she see?, I wonder. But she continues on as normal.

Having exited the plane, and entered the mass of travelers, I regain my
confidence. Everything is OK. I'm anonymous again. Everyone is too
hurried to care about other travelers anyway. I'll leave it on until
my meal, I decide. Then I will wipe my lips and see the pink on my
napkin.

I find my gate, enjoying the safe thrill of the moment. I'm shaken
from my state by a familiar voice. "Hizzonor?" I hear. I immediately
know who it is. It's Lizzy, Michelle's roommate in college. Lizzy is
outspoken, bold and uninhibited. She is quite attractive, too. In
college, I remember being a bit too enamored of Lizzy. I tried to deny
it, but Lizzy and Michelle used to tease me about it, saying they
always wanted to try a threesome, if I was up for it. They weren't
serious (I think); they just liked seeing me turn red every time they
playfully suggested having sex together.

Lizzy teased me about how pretentious my name sounded. James Hamilton
Madison Walker, III. She said it definitely was upper crust, what
with two middle names that really were last names, and with my name
being "the third." She said I was destined to be a judge or mayor or
something -- hence "Hizzonor."

When Lizzy called my name, I knew I couldn't escape. She came right up
to me. "Hey, Jimmy! Funny meeting you here!" She came up from behind
me. "I almost didn't recognize you, with your shaggy hair. It almost
covers your ears. Not respectable for a judge, you know."

"Michelle likes it longer," I say, glad she's distracted by my hair.

"I bet she does," she replies. "I love it, too. It would give me
something to grab onto when you're fucking me and I have an orgasm.
Your buzz cut in college would have offered me nothing to grab hold
of." Yes, she just commented out of the blue about having sex with me.
That was Lizzy.

"I'm sorry, I have to catch my flight to Denver," I say, feigning a
rush.

"Denver?" she says, "Small freaking world! That's where I'm heading.
Are you on flight 2415?" I am, I say. "Well that doesn't leave for an
hour and a half," she says.

Then it happens. Lizzy finally notices my face. "Jimmy," she
whispers, "Are you wearing lipstick?" I quickly deny it. "You sure
seem like it. Your lips are a pinkish ... and a little shiny."
Without warning, she reaches out with her left hand. She swipes my lip
before I can even react. My lipstick smeared onto her finger.

"That's definitely lipstick, Mr. Walker." She smiles broadly. "OMG!
You and Michelle are playing some sex game, aren't you? I knew you
were kinky. You should have tried that threesome back in college."
She reaches for her phone, probably to text Michelle.

"No, wait!" I say, hurriedly. "Don't text Michelle! She doesn't
know." My fear made it impossible to lie. Interrogators say that. A
scared man doesn't have the time or the wits to craft a good lie.

"Oh. Sneaky, are you? Naughty and sneaky. No, naughty, sneaky and
kinky. I'm intrigued, your honor."

She pulls me to a seat at the far end of a gate. "If you don't want me
to tell Michelle, you better be honest with me."

"Are you wearing anything else?"

I nod.

"Panties?"

I nod again.

"What color?"

"Red," I whisper.

"Naturally. No sense in going with white. They're satin, aren't
they?" I don't even answer, before she goes on, "A bra?"

"No. In the bag," I say.

"Do you have other clothes in the bag?"

"A dress and some stuff."

"Sweet. And are we wearing anything else girly? Pantyhose?
Eyeshadow? Perfume?"

I shake my head no. "Only nail polish," I say, "On my toes."

"Show me!" But I can't. Instead, I reach into my bag and hand her the
bottle. She inspects it. "That's a bright red. I bet it looks sexy."
Then she looks closely at the bottle. "Redy for Anything," she says,
"I hope you are -- ready, that is. This trip just got very interesting
for me."



Under Liz's Control

"Give me your suitcase," she says. "OK, I'm going to go inspect your
goodie bag. Stay here with mine. ... And hold my purse while I'm
gone."

Lizzy's suitcase is a pink and yellow floral design. Her purse is pink
leather. She makes me sit with it on my lap. ("It's too expensive to
lay on a dirty airport seat," she says.) I sit for at least five
minutes, waiting for Lizzy to come back. I'm staring straight ahead,
trying to pay attention to the TV monitor. If someone is laughing at
me, I don't want to know.

Finally, Lizzy returns. "Your dress is very cute. And I love the
heels. Four inches. I'm impressed, your honor. And they have a peep
toe, so they will show off that pedicure well."

"But your dress is not appropriate for the occasion. It's summertime
now. You packed a winter dress. One that's a touch formal. You know,
it's the holiday party type. We're going to have to fix that while in
Denver. We can find you a nice sleeveless dress. Maybe a little black
dress. You don't have one of those, do you?"

I shake my head no. "Goody. Every girl needs one in her closet. It
is very versatile and goes with just about any heel." Then, Lizzy
continued. "OK, here's the deal. I like your little game, but I want
to play too. So I'll play dress up with you. I get to be the boss. I
make the rules, and you, my cute little puppy, are going to follow
along. Right?"

I nod. She continues. "I thought so. OK, here's your first rule.
For the trip, I'm going to call you, 'Jamie' when I want. That's
sometimes a man's nickname for James, but of course it's girly too.
Just like you: a man, but girly, apparently."

"Second, you are going to have to take this up a notch. You obviously
wanted to be noticed, so I'm going to make you do more. Embrace your
girliness. I will expect you to trust me. And I will demand that you
comply. Otherwise, I'll just stop and let my friend know what you're
doing behind her back.

"We're going to start right now. I want you to go into the men's room
and put on your bra. A girl shouldn't wear panties and not a bra,
don't you agree? Going braless was a thing in the seventies, but it's
frowned upon now. So, go put your bra on. You can leave your light
jacket on if you like. Just so I know that you're wearing your proper
undies. And, freshen your lipstick. It's starting to wear off."

"While you do that, I'm taking your nail polish and going to get a
manicure at the 10 Minute Manicure shop right there. Meet me at the
shop when you finish." When I didn't move, she said, "You better
hurry. If I finish my manicure before you come back, I'm going to tell
the manicurist that they match your toes. And I'll make you show her.
You know better than to doubt me on that."

Confused and scared, I hurried to the mens room. I took over the
handicapped stall -- I didn't care. I can't believe what just
happened. I'm dead, I think. Lizzy won't let go of this. What am I
going to do? What if she tells Michelle? Then I'm really screwed.
Not because I'm crossdressing (I think she would be OK), but definitely
for hiding things from her. No, I have to find a way out of this and
figure out how to tell Michelle myself later. For now, I need to buy
time. Better to go along for a while, while Michelle is not around.
Secretly, the tasks are exciting me. I can't believe I'm going to wear
a bra in public -- and do so at the request of a woman.

So, I take off my jacket, unbutton my shirt, and pull out my bra. It
is red satin, just like my panties. Yes, the red is cliche but I'm not
that original, I figure. I quickly fasten the bra, reaching behind me
like an expert. I put my shirt back on, noticing that the red shows as
a dark shadow under my shirt. Better put the jacket back on. I start
to leave, and remember the lipstick. Lizzy said to freshen up. I'm
not doing it out there, so I try in the stall. I don't have a mirror;
I hope this is close.

Having hurried, I make it out and to the manicure table just as the
woman is putting a clear topcoat on Lizzy's nails. "Hey, honey! There
you are! Do you like my color?" she says, holding her nails toward me.
They look beautiful. And with the top coat, her nails are shinier than
my toes are (at the moment, at least). It was then that I also noticed
the wedding ring on Lizzy's finger. She's not actually married, I
know. We would have been in the wedding. It's just for show, I guess.

After mumbling the "husband-like," "sure, they look fine," Lizzy
continues the game. "Dear," she says, "Remember when you picked up my
lipstick after it fell out at security? I'd like it now." I didn't
pick up on her clue quickly enough. "You know ... the pink one that
you think is so cute? I want that one. Can you get it out of your
pocket?"

Turning to the manicurist, she said, "He's so cute. I sometimes have
him holding a virtual array of cosmetics for me. Maybe I should get
him his own purse to carry them. haha."

Lizzy's nails were sufficiently dry, so she carefully took the lipstick
and covered her lips with them. Then, she pulled me close, leaving her
left arm dangling in front of my shoulder. With her right, she took a
selfie of the two of us. A selfie, I realized, that not only showed
the red nail polish I secretly was wearing, but also showed our
matching pink lips. How am I going to get that from Lizzy?

On the flight, Lizzy has arranged to have us seated together. She's a
bigwig frequent flyer with this airline, so the attendant did
everything they could to accommodate her. When we're on the plane,
Lizzy raises the armrest between us, lays a blanket over the two of us
(she had that from one of her trips) and snuggles close to me. We look
like the loving husband and wife. Just the kind that wear matching
lipstick.

After we're in the air, Lizzy whispers into my ear. "Jamie, time for
you to unzip your pants and show your panties. I would do it myself,
but it might ruin this manicure."

I comply. Lizzy takes my left hand and places it on top of my penis.
I'm hard already. Then, she puts her right hand on top of mine and
begins rubbing me back and forth. Lizzy is stroking me, but not
actually touching my cock. Lizzy extends her left hand forward, to
where I can see it. In my ear, my loving "wife," begins to whisper.
"Jamie, this is such a darling color you have. I'm wet thinking about
how it matches your toes. And I can't wait to see it on your fingers.
You'll paint your own fingernails for me, won't you? Of course you
will. You don't want poor Michelle to find out how you've been
sneaking around on your business trips, so you're going to do whatever
I say. Besides, I think you like it. You're so naughty. Such a
naughty boy. Or should I say naughty girl? Yes, you're a naughty boy
who wishes to be girly. Well, for this trip, I'm going to make you
girly. Very girly. You might even be pretty -- pretty enough for me
to have sex with. I like my boys on the effeminate side. If you
cooperate, maybe we can experiment. Or maybe we can have that
threesome. We three girls, all dressed alike."

Lizzy did not have to go any further. I came all in my red satin
panties. I could feel the wetness for the rest of the flight. Lizzy
didn't do anything more that flight. But she did lay out her orders
for me. She took three pair of her own panties and gave them to me.
Each day, I'm to wear them under my business clothes. I also have to
wear my beige lipstick daily, "fixing" my lips every two hours. Each
night, I'm to meet her at a place she designates. And do what she
wants, of course.

I finally make it to my hotel room late. I check in with Michelle, but
I'm exhausted. She playfully asked if I kept her lipstick in my pocket
through the flight. I tell her yes, but she doesn't know the whole
story, not by a long shot. She wants to have phone sex, but I tell her
I can't tonight. I think she's a little annoyed with me over it. Oh
man, this week is going to be difficult.

Monday

Monday goes fairly well. I'm wearing yellow lace panties from Lizzy.
I carry my neutral lipstick with me all day. I don't think anyone can
tell I'm wearing it, but I try to keep from close contact with anyone
just in case. Lizzy texts me twice, both times saying, "Time to
freshen up, Jamie!"

As instructed, I meet Lizzy at a downtown shopping area that night.
Our first stop is "Heel Heaven," a massive shoe warehouse. It's twice
the size of the place I bought my four inch heels from.

"Your peep toes will work for the dress," she declares. "But I want
you to have some business appropriate shoes as well. We can't have you
wearing stilettos to class, can we?"

I'm not ready for this. I don't want to do this, I say. But Lizzy
tells me to relax. "I'm not going to make you try them on here.
Unlike high heels, a lower heeled shoe is more uniform. So we can get
away without trying them on." I start to relax, until she says, "I
just want to measure you properly." With that, she makes me take off
my shoes and socks right in the store. My red toes are shining
brightly, visible to anyone who might be in the vicinity. I quickly
put my foot on the sizer, but Lizzy makes me stand up. An older woman
turns the aisle as I do this, and sees me and my painted toes.
"Pretty," she says, and laughs.

Thankfully, the woman's comment is the only one I endure in that store.
Lizzy let me put my shoes and socks back on, and we spend a few minutes
picking out "loafers." They're more narrow than a typical men's shoe,
and the heel is shaped differently. It's a block style, but with a two
and a half inch heel, rather than the typical half inch of a men's
shoe, so there is more "air" visible beneath the toe and heel. Women
definitely will know it's a woman's shoe if they pay attention. Men
probably won't notice.

But Lizzy had more in store. Much more. Our next stop was a lingerie
store. We appeared to be the loving couple, shopping for a little
spice in our lives. Lizzy took me to the corset section. A woman came
up to us to help. Everything went smoothly, as Lizzy and the woman
discussed types of corsets, colors, and other elements. It turned bad
when the woman asked what size Lizzy wanted.

When Lizzy said "30," the woman stopped. "We size our corsets based on
the waist, ma'am. We usually recommend that you select a waist size
four inches below your natural waist. You'll probably need a 22, maybe
20."

"I know," Lizzy said, "The corset is for him. I think a 30 will work
right, but you can measure if you like." When Lizzy said this, I
wanted to just run away. But I couldn't. The woman turned and,
without missing a beat, looked me up and down. She agreed that a 30
would work.

"Great," Lizzy replied, "Can you show him how to tighten it? He's been
dying to wear a corset. If he gets one, I think he should know how to
put it on by himself, don't you think?" So the woman took us to a
dressing room. It was large, clearly big enough for two.

"Leave your pants on, sir, and you will need an undershirt. Since you
don't have one, I'll get you a camisole. Company policy." I took off
my shirt and we waited for the woman to return with my camisole. It
was a white, satin camisole. She slipped it over my head and started
to reach for my corset. Unfortunately, she saw my growing member.

"I'll give you a minute," she said, with a slight undertone of disgust,
as she looked at both of us. "When you two are done, come find me."

"Holy crap!," Lizzy shrieked. "You freaked her out! I can't believe
you're so naughty! Getting excited about your first corset, are you?
You should show more restraint, Jamie. I think she expects me to give
you a blowjob or something."

"I'm sorry," I say. "I'll settle down in a moment."

"No, you have to finish the job. Drop your pants and give little Jimmy
a hand job. But don't wet my panties. I like those ones." Following
her instruction, I unzipped my pants and pulled out my penis. I began
stroking it, right there in front of Lizzy.

Lizzy liked the show. She unbuttoned her own blouse and unhooked her
front-hook bra. She slowly began caressing her breasts. "I really
love to have my breasts touched like this," she said. "But for this
week, the hands doing so must have this sexy nail polish on them. Do
you want to touch my breasts, Jamie? Tell me that you do. Tell me how
much you want to paint your fingernails and rub my breasts, Jamie. I
know you do."

She didn't go further, as I quickly reached my climax. I stuck my hand
in front of my penis to capture my load. Thankfully, the room had
tissues, so I was able to clean my hands before Lizzy went to retrieve
the sales lady.

The sales lady was very professional the whole time. She showed me how
to tighten "my" corset, contrasting the procedures when I would have
help, and "when wanted to wear it on my own." I could tell that
she didn't approve of me, and she was constantly on guard to see if I
got another erection. This wager, I thought to myself, definitely was
a loss.

Lizzy made me wear the corset home, under my shirt. As soon as I got
to my room, my cell phone rang. It was Michelle. I had to take this.

"Hey, dear! How's it going?"

"Mmmm. Nice. I miss you, though. In fact, I'm sitting here in our
bed, with no clothes on. I started thinking of you, wishing you were
here."

"Really? And what is on your mind?" I try to be excited, but in
reality, I'm worn out by Lizzy. Plus, I can hardly move with my corset
on.

Michelle switches to the video app on her phone. She makes me do the
same. Although the light is dim, I can see her naked body. She holds
up her lipstick. "Do you have yours, Jimmy?" I do, and I reach for
the pink lipstick on the dresser. In my corset, my movements are
restricted, and I wince slightly while reaching for the makeup.

"Jimmy, what's wrong? You seem stiff."

"Oh ... I just tweaked my back a little tonight. I'll be fine."

"You poor boy. I wish I was there to massage it. I'd give you a full
body massage. You definitely would like it, don't you think?"

Michelle's flirty tone is making me excited. And she's not done.
"Jimmy, you're overdressed. Why don't you get more comfortable?"

"I'm good, baby," I lie, "Besides, I like to watch sometimes."

"But I don't get to watch, then."

"I'm sorry. Maybe later," I offer. Michelle is a bit disappointed,
but she persists.

"OK, I guess," she says. "Anyway, I have this pretty lipstick with me.
It matches what you have in your hands. Open it up and visualize,
while I do my lips." She painted her lips with the pink. That's the
third pair of lips I've seen with that color on them in 24 hours. I
laugh at this slightly.

"What's so funny, honey?" she asked.

"Nothing. I was thinking about our games when I picked a lipstick for
you."

"Did you like that? If you picked right, you got some great action
with these lips, didn't you? I'd like to do that right now, take
Jimmy in my mouth with these pink lips." Then, she started touching
herself. She whispered to me, "touch yourself, Jimmy. I want to see."

Carefully, I unzipped my pants. Suddenly remembering that I'm wearing
Lizzy's panties, I drop the phone briefly. Before I pick it up, I
slide the panties off and slip my pants back up. Michelle thinks I've
gone commando today.

Despite my fears, it didn't take long for both of us to orgasm. All
the while, I kept worrying about whether Michelle could see the
outlines of my corset. Man, if she did, I was in big trouble. No easy
way to explain that. Luckily, if she saw, she did not say anything.

Tired and scared, I ended our session a bit earlier than Michelle
wanted. I pled fatigue, and promised more later. Michelle reluctantly
went along. I'm in trouble, I know. But I'll figure that out later.

Tuesday

I made the mistake of telling Lizzy that I talked to Michelle last
night. "Did you show her your pretty corset, Jamie?" she cooed.
"Maybe I can watch next time. That would make me hot."

"Don't you dare," I say. "I'm in enough trouble without Michelle
discovering you watching us."

"Now don't be silly. I bet Michelle would love that I helped you pick
out your corset."

During the day, I wore another pair of Lizzy's panties, my new heels
and my beige lipstick. My heels terrified me. For one, I could hear
them on the hard floors. I tried to walk slowly, so as not to draw
much attention. Plus, I'm almost certain that every woman at training
noticed my heels. There was a knowing glance I saw that convinced me
they knew. I avoided conversation as much as possible, afraid of where
the topic might turn. Yet, as you might guess, the fear of being
caught kept me excited most of the day.

I spoke with Michelle after training and before dinner. She was again
in a playful mood. We again used the video app. This time, Michelle
had her tablet, so she could stand it up while talking to me. She
asked me to strip naked, which I did. I conveniently "dropped" the
phone again, just as my panties would have been exposed. I stripped
them off and then recovered the phone so she could see.

"Do you still have that lipstick?" Michelle asked. Yes, of course I
did, I say.

"I was thinking about your comment last night -- how we used to play
games with these tubes. Do you remember?

"Well, anyway, I came across the red lipstick this morning. Remember
the times I would wear that color and suck you off? I'm sure you do.
Those certainly were exciting, and you seemed to enjoy the thrill of it
all. Well, I thought of that today, but I also remembered the time in
the restaurant, when YOU ended up with sexy red lips. Remember? That
waitress had such a laugh at you."

"Yes, I remember," I say, thinking of how many time since then I've
risked detection in one form or another. "Why?"

That was a dumb thing to say. It led Michelle exactly where she wanted
to go. "I think it's time to play that game again, that's why."

"I want you to put on the pink lipstick I gave you, and order room
service for dinner. After it arrives, you can call me and tell me all
about your encounter with the delivery person."

"I can't," I say, not thinking things through entirely. "I'm having
dinner with Lizzy tonight."

Michelle looked puzzled and then a bit concerned. "Lizzy? My college
roommate? The one you not-so-secretly lusted after while we were in
school? You didn't tell me that Lizzy was there." Her tone got
accusatory with that last statement. This was starting to turn in a
bad way. I had to do something quickly.

"I'm sorry," I say, "it was a very short encounter. I saw her at the
airport after I landed. It turns out she has business here this week.
She just called me this afternoon, saying that her plans fell through
tonight and wanting to see if I had time to catch up. It was really
casual, you know. I was going to tell you on this call, but things
started going in a different direction quickly, and I didn't want to
interrupt the flow." If I were John Belushi, this is where I would
have done the sincere eyebrow thing he was so good at. I settled on a
bit of the lost puppy dog thing. Michelle backed down -- a little.

"Well, OK," she started. "You shouldn't be hiding things from me. I
don't like the thought that you're not being honest with me."

"I am being honest, baby," I said, "I'm sorry that I didn't mention it
earlier. I just didn't want to worry you." After a pause, I added,
"You know I wouldn't do anything with Lizzy. She's one of your best
friends. I'm just being nice."

Michelle said that she understood, but I could tell I was still in the
doghouse. She backed down on the lipstick threat, suddenly saying that
she wasn't interested in "my thing" any longer. (When did this become
"my thing"? I wondered. But I knew better than to push it now.)
Instead, I apologized again and promised to talk to her later tonight,
after dinner.

I'm now late, so I have to hurry along to meet Lizzy. I'm not actually
meeting Lizzy for dinner. I'm supposed to meet Lizzy at the downtown
shopping area for more shopping. Lizzy told me to wear my corset
again, so I hurry to try to put it on, following the instructions I
received last night. It's not easy, but I manage after a few minutes.
I put a button-down shirt on over the corset, quickly change into my
jeans, and slip into my loafer heels. I tell myself that I still look
masculine, but I'm not really sure. From a distance, I say, I'm just a
guy in skinny jeans and a button down. I'll just have to avoid too
close contact, so as not to expose my corset or my women's heel shoes.

When I arrive, Lizzy is impatient. "You're late. I don't like boys
who are late." I explain that I was talking to Michelle and that
caused me to be late. I even told her that Michelle wanted me to play
the lipstick game (as I called it) but I had to decline. Lizzy said
she was pleased I declined, because I should only take orders from her
this week. "There will be a consequence for being late," she warned.
Suddenly, I'm not so sure I like playing Lizzy's games.

"Your corset also is too loose," she declared. "We're going to have to
fix that. Follow me." The shopping area has a set of restrooms at one
end. Lizzy takes me by the hand and leads me to the family restroom.
Lizzy is a step or two ahead of me, and I'm being pulled by her toward
the restrooms. I feel like a small c***d, being dragged by mommy from
place to place. Inside, Lizzy has me remove my shirt and grab the
handicapped handrail inside the room. She pulls on the corset's
strings, tightening it several times. "Breathe in," she directs, as
she makes the last tug on my corset. When she's finished, my waist is
several inches smaller than my chest and hips, giving me a distinct
hourglass appearance. I put my male shirt back on, but that doesn't
adequately conceal my new figure. The shirt is more tapered than it
seemed just a few minutes ago, and my corset (which is black) shows a
slight shadow under my shirt. One would have to be looking closely,
but if one did, you could discern the corset I'm wearing.

"OK, Jamie," she pronounced, "now you are ready for the rest of our
adventure. I'm going to buy you a cute dress tonight. Let's go." I
follow. (Thankfully, she's no longer leading me by the hand as we go.)

Our first stop is not for a dress, however. We casually walk into a
costume jewelery store. Lizzy looks at several earrings, holding them
up to her own ears each time. I look around, trying to look distracted
as she does this. The store clerk is a teenager, maybe 17. She is
mildly interested in us, probably because there isn't much going on in
the store. I'm doing my best to minimize this whole situation, but
Lizzy isn't about to cooperate. She picks up a pair of large hoop
earrings. They are gold, with a thick band, about three inches in
diameter. Rather than holding them to herself, however, she reaches
out and holds them next to my ears. I should move back, but I don't.
The clerk doesn't say anything but I'm sure she saw.

"They're cute, aren't they?" Lizzy asks me. "They're not your style,
though. Hoops don't look good with shorter hair, do they?" I said
that I agreed. Lizzy picked up some of the dangling earrings instead.
She handed Lizzy a pair of silver dangling earrings. They had a faux
pearl center, with three strands of different length dangling below.
"Something like this compliments short hair, drawing attention but not
looking boyish," she said. Lizzy loved the earrings, so she bought
that, along with the complementary necklace and bracelet.

Our next stop was less eventful. Lizzy bought a purse -- for me. It's
a small black bag, with a silver chain. Pretty standard fare, but
"large enough to hold what you need," Lizzy says. "And, it will go
with your little black dress, which we're getting next." The store put
the purse into a small bag with their logo on it. Lizzy makes me carry
it. While I'm paying for the purse (in cash), I catch Lizzy texting on
her phone. "It's just work," she claims.

We next went into a store called "LBD." Lizzy walked right up to the
sales lady to ask for help. "We're looking for a basic black cocktail
dress," Lizzy declared, "we want something versatile, not too short,
preferably sleeveless."

"We have several that would fit the bill," she responded, "what size
are you?" Then, with a slight glance at me first, Lizzy said, "Oh,
it's not for me. We're buying it for a friend."

"I see," the sales lady responded, "What size is your ... friend?" I
swear the sales lady looked at me first, but maybe I was imagining
things.

Lizzy was not about to let me go, however. If I had been at the
blackjack table, this would have been when the dealer improbably pulls
a 5 to her 16. "I'm not sure," Lizzy responds. She turned to me and
said, "what size do you think we need?" The sales lady turned to me
also.

I'm stuck now. I try to stall and deflect. "I don't really know,
Lizzy. ... Probably a ten, I guess." The sales lady starks to smirk.
Then, I add, "It's for my sister."

"Wow, you two must be close," she replied. "I have three brothers, and
I'm sure none of them know my dress size. You sister is very lucky to
have someone like you." Clearly, I had not fooled her one bit.

"Is your sister about your height too?" she asked me. "We wouldn't
want anything that's too short." Then, she continued. "We also need
make sure it fits up top. Do you know your sister's bra size?"

Lizzy jumped in on that one. "She's my best friend. She's a 38, B
cup."

With that, the sales lady took us to a few different choices. Lizzy
picked out one that was sleeveless and had a boat neck. It had a small
eye hole in the chest area, just above the cleavage. The sales lady
agreed that it was beautiful. "But keep the receipt. If your, um,
sister has any problem, she can come in to exchange it. I'd recommend
that she try on a few, to see the style." Finally, to nail the point,
she said to me, "tell your sister that we're usually not very busy in
the last half hour we're open. She'll be able to get the most
attention if she stops by then."

After we paid, Lizzy asked the sales lady to hold it for a little
while. "We'll pick it up on our way out. We have another stop or two
to make." Again, however, Lizzy is texting someone while I gather my
things.

We did indeed have one more stop. It was the department store at the
far end of the mall. Lizzy drags me to women's suits and jackets. I
thought I had all the clothes I needed. "Not at all, Jamie," Lizzy
explains, "You can't wear a dress every day. I want to get you
something that's versatile. Something that can go from work to a
casual night on the town. This one will be my treat."

When we arrive in the section, Lizzy gives the sales girl a hug.
Apparently, Lizzy visits here more regularly than I thought. Lizzy
introduces me to Beth. "Beth will take care of you. I'm going to sit
here while she finds a cute blazer for you, Jamie." Lizzy sits on the
couch in the department ("where are these couches in the men's
section?" I think momentarily). She picks up her texting conversation
again.

I have a decision to make. Lizzy just clearly told Beth to help me
purchase women's clothing for me. Do I go along with this? Unlike the
rest of our purchases tonight, if I go forward, there is no pretending
that the purchase is not for me. Even with my weak "sister" excuse at
LBD, I at least maintained a pretense of non-involvemnt. This would be
different.

I see Beth looking at me. She's waiting patiently for me to me. I run
the pros and cons through my mind quickly. But in the end, I know
there's no choice. I'm at the blackjack table, and I'm letting my big
bet ride.

So, I let Beth help me find a "cute blazer" for me. Beth is wonderful
and very professional. Unlike that lady in the lingerie shop, Beth
makes me at ease about buying a women's garment. She shows me several
different styles, but recommends a navy three-quarter sleeve blazer.
It has a single button, but is designed to be worn open. The sleeves
look rolled up, and show a white with polka dots pattern. ("The
sleeves can roll down to full length if you need it," Beth explains.)
It only falls to my hips, however. Much shorter than a men's blazer.
It's definitely not passable as a men's garment.

After I purchase my blazer, I look for Lizzy, but I cannot find her.
She's not at the couches like she said. Where did she go? Then, I get
a text. "Put on all your purchases, Jamie. I want to see how cute you
look." Then, another text, "Meet me at LBD's in 10."

Puzzled, I look around. I don't see Lizzy, but Beth is still standing
next to me. For some reason, I tell her what Lizzy said. Beth tries
to reassure me. "Go ahead," she says, "You don't have anything to
worry about. Everyone out there is so consumed in their own world.
They probably won't even look at you. With your heels, your feminine
body shape and the jacket and all, you'll look like a woman. If you'd
like, I can give you a little makeup to finish the job. I worked in
that department for two years before moving over here."

For once, I made my own decision. And I didn't make it out of fear.
There was something genuine about Beth, something that gave me
confidence. If I'm going to keep playing this game, this time, I want
to try to be a woman, not a man wearing women's things. So, I put on
my earrings, and my blazer, and I take out my purse. And, I ask Beth
to make me up. Yes, I asked her; I didn't let her. I text back to
Lizzy that I'll meet her at LBD's, but I have my own errand, so I'll be
there in 20, not 10. That will confuse her.

My next 15 minutes with Beth at the makeup counter is amazing. For
once, I'm not nervous, I'm not sweating. I am enjoying this strange
and foreign experience. Beth is amazingly talented. When she's
finished, I have smokey eyes, defined cheekbones and shimmery, sexy
lips. She gives me all of my makeup as samples. She even puts a small
clip on one side of my hair, making it more feminine and showing off my
earring more. She gently pushes me toward the door and off on my way.
"Be strong, be proud, Jamie," she says to me. "You're beautiful."

When I get to LBD's, I'm changed. Lizzy loves my new look. "Sexy,"
she says, "I want to get in bed with you right now." I boldly pick up
my "sister's" dress. I tell the lady there -- the one who tried to
embarrass me -- that it is for me and that I would try it on first. I
even walked out of the dressing room in my bare feet to show Lizzy. I
didn't care.

Wednesday

That bold girl didn't last. When the morning came, I skipped my last
day of classes. I spent the whole morning in my room with the Do Not
Disturb sign on. I couldn't stop thinking about tonight. Tonight is
supposed to be the night when I wear my new dress and we go to a fancy
dinner. It would be my first appearance other than in a shopping
context. I would have to present as female -- or worse, as a man in
women's clothing. I won't have the cover of shopping, where the clerks
either don't care because a commission is a commission or they are paid
to be professional. Tonight, none of that would be the case. I could
be pointed out, ridiculed, or even abused. Suddenly, I'm genuinely
fearful. The fact that I could be in danger keeps me nestled in my
bed.

Lizzy texts me around noon, telling me to take a selfie. I tell her
that I'm in my room and not playing, and she quickly calls.

"What's going on, Jamie? Last night worked out so well, especially
after Beth helped you out. You were such a sexy babe."

I explain to her that I'm tired of this game. "I don't want it any
longer, Lizzy. I'm just going to sit here the rest of my trip and
order room service."

"Oh no you're not," she replied, "We have a date. You're not standing
me up -- or coming in your blah clothing." I tell her that I won't be
bossed around on this, that I don't care if she tells Michelle. I'm
going to tell her when I return, I vow.

"Jamie, last night changed things. I saw you after your visit with
Beth. I'm not 'forcing' you to do anything. No, little timid Jimmy
changed last night. You're still a man, but I saw a new side to you.
Everyone has a bit of both male and female in them. Your female came
out last night, and she was bold, self-assured and pretty. I just
loved the face on that ratty old hag at LBD's when you told her you
wanted to try on your dress before taking it home. THAT's the person
inside of you. The one who is going to have dinner with me tonight.
The one that -- someday, and if Michelle will approve -- I'm going to
be lucky enough to have sex with. I've wanted you since college.
Michelle knows that."

I'm really confused at this point. I don't know what to say to Lizzy.
On the one hand, she just gave me a pep talk. It was an odd "you go
girl" kind of pep talk, but a pep talk nonetheless. At the same time,
she revealed something about herself and about Michelle that I hadn't
known. Did she proposition me? Most certainly, she did.

"Here's what I'm going to do," Lizzy continued, "I'm going to call
Beth. She will come over before dinner and help you get ready. Beth
will show you. You're ready."

I sort of agree. More like I agreed to think about agree