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Prior to Saturday, May 2nd, 1998
Imagine this; a day with a handsome dapper man from the U.K., with
all the charm of James Bond, a look and accent that would make any
woman take notice. Then imagine being with that man, dressing for him
to please his visual senses, for a quiet casual afternoon drink, then a
fantastic night when you can get all dressed up for a formal dinner
theatre engagement. Followed by a chance to slip into a silky and
romantic Bridesmaids Dress, matching satin heels and play "Bridesmaid
and date after the Wedding", sipping on a glass of wine in a hotel
lobby. Finally, last but not least, him taking you back to his room and
allowing you to thank him as only a woman could for a wonderful
evening.
Believe it or not, this adventure came true to me in real life and
it will go down as one of the most memorable in my life, for the
purpose of this story, we will call my wonderfully handsome date, Bill.
It all started with an email from Bill in late March, 1998:
Dear Joyce:
I regularly visit on business, many lonely nights spent at a hotel near
the airport. Looking for a convincing, sophisticated and tarty TV date.
I'm 38, attractive, good company and would treat you as a real lady in
any way you want. Interested tell me more!!
That started a flurry of email and once I got a few from Bill, I
knew that he was just the type of date I like, one that wants to date a
sophisticated woman. One that knows how to dress handsomely, and one
that can respect all of my feminine desires and of them is to remain as
feminine as possibly no matter what happened.
Then before I knew it, the date was to be set, May 1st or May 2nd
would be best for Bill, he was arriving in town from the U.K. on the
Wednesday prior and would be available for either evening or both.
However, my schedule would only allow for one evening to be available,
but I after I proposed that we got together in the afternoon to get to
know one another previous to the formal date, the Saturday became the
obvious day of choice, as Bill had business meetings Friday afternoon.
Then how we would meet became an issue and Bill suggested that he
would "hire a car" to meet me and pick me up for the dinner theatre and
whatever, but with cultural differences figured out. Bill meant "rent a
car", and I was not going to have a person used to driving on the other
side of the road attempting to come and pick me up on the roads in my
area. So I made another suggestion, and that was he got me a room in
the hotel he was staying in and we could take a cab to the dinner
theatre, and he liked the idea and that plan was set.
So the meeting and such arrangements were set, now the hard part
any woman faces on a date, and "blind" date as this one was going to
be, "what to wear!", and for me I had to pick two different outfits,
one for the afternoon and one for the evening. So I concentrated on
them one at a time, first was the evening, as I really wanted to look
special for Bill.
Bill had mentioned he likes his women to dress "ultra feminine",
and when I asked him about this he mentioned flowing gowns of satin and
lace and such, and I sent him pictures of me in formal attire to decide
on what he wanted to see me in. He wrote back:
Silky 1st, Floral 2nd, Velvet 3rd, but all wonderful.
So I started to sort through my Silky Bridesmaid Dresses and found
one that would be perfect for a Saturday evening formal dinner theatre
and picked it out of my wardrobe. It was cocktail length, blue satin
and with 4" black patent heels would be perfect, not too
"Bridesmaidish", but classy and elegant. I then started to second guess
myself and grabbed a "little black dress", one that I had purchased
Christmas shopping in November of last year, perfect for a formal
evening. This dress was mid thigh, and combined with sheer black hose
and 4" black patent heels would look killer. Also, I grabbed an Aqua
green off the shoulder, tea length dress that a girlfriend of mine
made, perfect for a formal occasion and hung them up together for a
final decision.
Finally, after thinking that this was going to be a Saturday evening
and elegance usually is what you go for, I pulled out a two piece deep
red print, off the shoulder ensemble. I got this off a girl that wore
it as a Bridesmaid Dress, it had a cocktail length skirt with a thigh
high slit, and off the shoulder top. The buttons down the front were
rhinestone and quite elegant, I planned for a rhinestone necklace,
matching bracelet and earrings and finally a rhinestone anklet to
finish the look off. I reserved judgement until Sharon looked over the
outfits and helped pick out which was most appropriate for a Saturday
evening at the theatre.
Sharon scanned the outfits, and her decision was decisive, "the red
print, with the rhinestone earrings and the matching rhinestone
necklace, you will knock them dead!, have fun girl, I want a full
report!". So with that, the final decision was made, it would be the
red print dress, but I still wanted to wear the silky and satiny
Bridesmaid Dress for Bill as he loved that style of dress.
I then made another suggestion to Bill, and offered that I would
possibly slip into a satiny Bridesmaid Dress when we returned at the
end off the evening. Bill said he would like that very much and decided
that I would plan for that, as it would be the best of both worlds for
Bill, a classy sophisticated lady for the dinner theatre and one in
flowing satin for more quiet times. He thought that was a good idea, so
with that set, Bill, picked the Bridesmaid Dress he wanted to see me
in, it was a lovely satin Alfred Angelo number, with a lovely deep V
back, cocktail length in hunter green.
So with the evening attire planned, I started planning for the
afternoon meeting and was struggling with what to wear, but with a
sudden rise in the air temperature, it was more like summer. So my
wardrobe ideas started to change for the afternoon, from more fall and
winter clothes to the spring and summer part of my wardrobe. I decided
that the first time he was going to see me was a more sexy and short
skirt or dress and high heels.
At first when I planned, I decided to go with a red cashmere
sweater, mock necked and a little black leather mini, sheer black hose
and my 3" black kid heels. As the time got closer to May 2nd, the
temperature started to rise to early summertime levels, in the low to
mid 70's and the sweater idea was not going to be practical even though
we were going to be meeting indoors. So back to the closet I went and
grabbed one of Sharon's little short flowered sundresses, real cute and
thigh high, combined with the 3" black kid heels, would also look
really good. Then I started thinking that I was meeting Bill near the
airport, and if that was the case, there are always a number of
convention goers there, and I also told Bill I would be most likely
dressed "business". With those factors in mind I pulled out my "90210"
skirt and matching jacket, a skirt just many inches above my knees and
a short sleeved jacket that with a camisole underneath, perfect for
"very sexy business wear". With the three outfits chosen, I decided
that I would pack all three and allow my mood/temperature/ambiance to
decide on what I would wear.
The Bridesmaid dress that Bill picked out was one that I had the
exact same dress, Alfred Angelo, one in hunter green and the other
Royal Blue, both with matching 3" heels. I was leaning towards the
Royal Blue as the date approached as it had a little more room in the
waist area and decided that I go with that instead of the Hunter Green,
and I was sure Bill would not mind!.
With all of that decided, the rest was easy right?, wrong... Packing
all of my makeup, jewelry, shoes (satin Bridesmaid heels, 4 " Black
Patent Heels, my 3" black kid heels. Last but not least a pair of 2
inch heels (for when I was getting ready), outfits, dresses, and such
was really a chore, mind you a very enjoyable one. So as the days got
closer, Bill and I kept on exchanging mail, and the anticipation of
meeting this very classy and possibly handsome man started to grow. I
got all of my makeup, purses, and dresses, skirts, lingerie and such
packed, I all of a sudden realized I had forgot some other essentials
that would fill my luggage to capacity.
Firstly I had planned on a lovely faux fur coat to compliment the
elegance of the outfit. However the temperature rising took that out of
the picture, so I had to plan that the weather might be a just a little
cool at dinner and packed my spring coat just in case. I had to plan
that I was going to ruin a pair of my sheerest hose, the style I was
going to be wearing both for the afternoon and evening, and packed a
few more pairs just in case.
Bill and I discussed that possibly if everything was perfect for the
evening we might end up sipping champagne with me in romantic lingerie
and who knows what, so that got packed a romantic and flowing peignoir
as well. Finally when I thought all the essentials were packed, I
forgot one thing, and that was a pair of satin gloves for putting on my
ultra sheer hose, as I packed them I thought, "mmmmm, maybe these will
come in handy?", and stuffed them into one of my bags. Last and finally
but not least, a lighted makeup mirror in case the lighting in the
bathroom at the hotel was not right.
With a travel bag and clothes bag stuffed to capacity I was ready
and just had to wait for the day to arrive to hear from my special
date. He called me the Wednesday before the date, his voice was very
nice and we had a wonderful conversation. I could tell he was looking
as forward to this day as much as I was, and he ensured me everything
was taken care of, and I thanked him for that.
The Friday before the big day arrived and a little surprised arrived
in the mail from a place I purchased it from via the Internet. It was a
lovely clear elaborate rhinestone necklace, very elegant, more than the
one I was planning on wearing, so I packed it. Along with the red and
decided to make a last minute decision on which I was going to wear,
most likely when I was all dressed and doing a final check in the
mirror.
The Big Day, Saturday, May 2nd, 1998
Finally the Saturday morning arrived and I was all excited as I got
up and packed the car for the trip to the Hotel, it was a last minute
thought but I thought it wise. You see, the buttons on the top of the
formal evening outfit have a habit of coming off and decided to pack my
portable sewing kit at the last possible minute.
Then the worst thing could happen, just as I was about to leave, the
phone rang, it was work, there was emergency and I was needed.
Terrified to say the least was what went through my body, but luckily I
got things calmed down remotely and was only about 45 minutes behind
schedule. Bill and I planned to meet at 3:00 pm, and I knew it was
going to be a little late with the circumstances. So I finished loading
things in the car and I was off.
Entering the hotel was a very special feeling, as the hotel was VERY
classy, and elegant, I do travel but never stay in hotels as nice as
the one I was, I knew things would be very special for this day. I
checked in and noticed something right away and that was I saw a number
of women in business attire, ie., thigh length skirts, matching jackets
and heels, and before I even checked in I knew what I was going to wear
when I met Bill, I was not going to be outdone!. I also noticed a
lounge area, the one Bill had told me about in our emails and now that
I knew exactly where I was going when I got changed and came to meet
him. So being all checked in, and a couple of trips ahead of me, I
headed for my room, one floor down from Bill, as we had planned, after
all I wanted him to come "calling on me" for the evening date.
I entered the room for the first time and could not believe how
classy and elegant the room was, as I said, I have traveled quite and
this was nothing like I had ever stayed in, it was so "regal". The way
the bathroom lighting was laid out, the couch in the room, the desk,
antique and very classy, the day got even more special. Finally after
getting all my bags in the room, I gave Bill a call to let him know I
was at the hotel and getting ready for meeting him in the lounge. He
sounded as excited as I was. He asked if there was any problem checking
in and I told him that there was none, he was pleased and anxious me
meet me. I also told him that it would be more appropriate to get
together at 3:30pm. 30 minutes later and Bill and I agreed and he said,
"no problem". So with the initial contact made, I started to organize
the room for the day and evening ahead.
The first order of business was the garment bag that had the
dresses, skirts and such for the evening, I quickly took out my clothes
for the day and hung them up in the main closet to prevent them from
getting wrinkled. With all of those unpacked I decided to head for the
travel bag.
I unpacked all of my clothes and made use of the drawers provided,
packing lingerie in one, other clothes in another, etc, soon they were
all full and my travel bag empty. Then I moved to organize my jewelry
for the evening as I did not want it to get mixed up, so out of the bag
I packed all of the jewelry in came the day and evenings jewelry, I
placed it on a little table in front of a mirror. I assumed this table
was for that purpose as it worked out perfectly for me putting on my
jewelry. The first "pile" was my jewelry for the afternoon, my rings,
long dangly gold earrings and that was about it. The second pile was
for the evening affair, with the new elaborate rhinestone necklace, red
rhinestone necklace, red rhinestone bracelet, matching red rhinestone
earrings, and finally my clear rhinestone anklet. The last pile was for
the Bridesmaid dress I was going to wear for Bill, and that was a pair
of heart shaped crystal earring and a pearl necklace with a tiny broach
in the middle, and with that, the jewelry plans were set.
The final activities in unpacking was to set up my makeup mirror in
the bathroom to get ready and to sit down at the lovely desk and
intricately glue a rhinestone back into place in a button onto the top
of my dress for the evening. One popped off when I packed it away for
the trip and wanted the look to be perfect for Bill.
So with that done, I got into the shower and started getting ready
for Bill to meet him in the lounge of the hotel. After the shower I
slipped on my pink makeup coat and started getting into my lingerie,
not only for the afternoon, but for the evening as well. I decided that
I would wear a silky and lacy pair of hunter green panties and slipped
them on, and continued with a waist cincher, very pretty all lace
conventional bra, camisole and ultra sheer nude hose. The satin gloves
I packed came in handy as I used them when putting on the pantyhose as
I tried not to put a run in them. Once done with the lingerie, I
slipped on the low black pair of heels I packed as not to put a run in
my hose as went about getting the rest of myself ready, then started on
my makeup.
After applying foundation, I stared at my face, decided on what
"look" to go for, "business", "light casual", or "heavy casual". I
decided "light casual" would work best as I wanted Bill to be
pleasantly surprised with me "all done up" when he picked me up for the
dinner theatre. So with that in mind, a light coat of eyeliner, light
brush of purple on my lower lids, and light on my upper lids. Finally
my blush was applied light and my lipstick was my more "business" or
lighter red/pink shade. When I was done I knew he would be pleased when
he first saw me. I decided not to do my nails for the afternoon meeting
and plan to do them for the dinner date.
With the makeup done, it was time to get into my skirt and blouse
and begin the final preparations. I wanted to wear perfume for Bill,
but the type I was going to wear for the dinner theatre, "Obsession",
did not really fit with my mood or clothing I as wearing. I decided
instead to spray a little of my Halstons perfume on my jacket and allow
that to entertain his senses when we met, Halstons is my "office
perfume". The last thing I did was comb out my hair to make it perfect
for when I met Bill, and thanks to a girlfriend who taught me, I did
quite well.
I noticed the time, 3:36pm, I was slightly late, but Bill told me he
would have a glass of wine waiting for me in the lounge. I slipped out
of my low heels and then into my "business" 3" black heels to complete
the professional business look. I then gathered things together, my
purse, hotel key, etc., and once all set I took a final look at myself
in the full length mirror on the outside of the bathroom door. I knew I
looked as good as I was going to get, with one final check of my
lipstick, and a tug at my camisole. I made sure maximum white lace of
my camisole was showing, made sure my skirt was sitting right and slung
my purse over my shoulder and headed out the door to the elevator and
the lobby.
I walked with confidence as I knew I looked just as good as any of
the other women I had seen as I was checking in, and was hoping I would
run onto them as I got into the elevator heading to the first floor. I
saw no other women as I exited the elevator and headed for the lounge I
had spotted earlier when I checked in.
I looked around as I came up a set of stairs, my heels clicking on
the marble floor. I did not see anyone except a number of empty tables,
then after rounding a bar area, I spotted the wine glass sitting there
and my date for the evening smiling and waving at me.
To say I was pleased was an understatement, Bill was dressed in a
casual suit, tie and all, and we matched perfectly, a businessman and a
businesswoman. More importantly, he was handsome and dapper, just like
he had described, I just hoped that he was just as pleased with my
appearance.
He greeted me with a hand towards me, and as I took it, the first
magical kiss happened, it was light and more of a "pleased to meet you
Miss Blake" kiss, I was in heaven. I sat down on a couch and was
sitting just kind of "kitty corner" to him, and had a tough time making
sure my short skirt was not exposing my vaginal area to him, I wanted
to retain some dignity, but I found it hard.
Bill and I sipped on wine and talked about many things, and it was
a very enjoyable time, Bill liked the way I looked and I explained that
I really like dressing that way for him. We talked about many things,
among them was how elaborate or "opulent" I found the hotel, and Bill
explained his experience with the hotel and agreed it was quite lovely.
At one point as we were talking Bill mentioned he hoped that I would
walk up a set of stairs one the other side of the bar were I entered.
There was a parrot there in a cage that whistled out, "pretty lady",
and was hoping he would hear the bird say it to me, I smiled at him and
told him, "maybe soon".
The conversation carried on and I was falling for Bill in a big
way, he was charming, well dressed and could talk a woman into anything
with his accent and demeanor. We talked about everything as time went
by, and finally the glass of wine I started persuaded me to visit the
ladies room, and this visit was none like I have had before. I asked
Bill were the ladies room was and he explained "down over there, around
the corner, etc.", and it was a long way, but as I was to find out,
well worth the trip. I grabbed my purse, and stood up, straightening my
skirt and headed past the parrot waiting for "pretty lady", but did not
hear anything. I knew Bill was staring at my legs in the short skirt
and gave him a look back and he smiled.
Once off of the carpet of the lobby, I started down a marble
hallway, my heels echoing in that "oh so feminine delightful manner",
eventually ending up at the entrance to the ladies room. I opened the
door and was "wowed" at what I saw, a large lighted makeup mirror, 5
stalls, and a vanity. The vanity offered vanity style lighting and an
antique bench to sit down and do your makeup, also a large floor length
mirror as well the whole floor was marble. I was alone, but the
experience was still special. As I entered a stall, I found a place to
hang my purse and they were very clean. As I did my business I noted
that the walls the stall in the ladies room were particularly clean,
unlike other ones I had been in with graffiti all over the place, these
were very well kept. After I finished my business, I gathered myself
together and headed for the well lighted makeup mirror and fixed up my
lipstick and hair, then finally adjusting myself in front of the large
floor length mirror, making sure my camisole was showing enough and my
skirt hanging just right.
I made my way back to Bill, going up the stairs that passed the
parrot, waiting for it to sing out "pretty lady" as I walked by, but it
did not. "Oh well", I thought and headed towards a smiling Bill, I sat
down and we resumed our pleasant conversation, and I caught Bill a few
times trying to peak a look up my little short skirt. He ordered us
another glass of wine and we kept on talking, until I checked the time
and realized that I would need to have some time to get ready for the
evening and asked if he would escort me back to my room, and he gladly
agreed.
Bill escorted me to my room and kissed me lightly as he said
goodbye and said he was anxious to see what I would look like for the
evening and I told him, "you won't be disappointed", he responded, "I
am sure I will not". We planned for Bill to come calling on me at
5:15pm to leave for the dinner theatre. Once back in my room, I changed
out of my skirt, blazer and camisole and left my silky hose and panties
on for the evening, I slipped into my pink satin makeup coat and
started to get things ready for the evening. I also slipped out of my
3" business heels and back into the lower 2" heels to protect my hose.
First order of business wash to wash off the light makeup I had on
and to get ready for a look for the evenings events, which needed to be
much more formal and dramatic. I looked at the clock, and Bill was to
pick me up at 5:15pm for the trip to the theatre and that would give us
enough time to arrive for dinner.
I took out my skirt and top for the evening, along with my heels
and laid them out on the bed, and then headed to the bathroom for my
makeup application.
I always take my time when getting ready to go out for a formal
occasion, but this time was longer than I had ever taken, as I wanted
to try a new look with my eyes. Firstly was my eyeliner, much darker
than the afternoon, basically on the line of heavy and "streetwalker",
but on the lighter side, I was pleased with the look, dark alluring and
seductive. Then the eyeshadow, dark green on the lower lids and a dark
brown on the upper, definitely a new "look" for me!. Then finally a
healthy coat of mascara and my eyes were done, dramatic and perfect, I
was really pleased, and was hoping Bill would be as well. Then to my
cheeks, my darker blush, and after turning the light on my makeup
mirror to "evening", I relied on it to make my cheeks perfect for
evening wear, they looked perfect, a little dark in bright light, but
perfect in low. I decided to save my lipstick application to just
before Bill picked me up so it would be perfect for him when he saw me
for the first time.
With my makeup done, I seated myself at the lovely table in the
room and applied a coat of nail polish that was going to be matching my
lipstick, I carefully applied a nice and healthy coat. Once done I
checked the time and saw that it was approaching 5:10 pm and decided to
get into my outfit for the evening.
The final touch before I put on my outfit for the evening was a
healthy application of Obsession perfume, behind my ears, my neck, my
ankles, and I was all set, then I decided to prepare something special
"just in case" things went well for the evening.
I packed a long flowing white peignoir, and some satin long
sleeves gloves in a carrying sack and left it on the vanity next to the
Bridesmaids jewelry "just in case", once that was complete, I moved to
the special outfit for the evening.
After slipping into the skirt and top, I took about 5 minutes
adjusting the straps of the dress and the straps of my conventional
bra, as the style was off the shoulder and with the right tug here and
there I could get away without wearing an uncomfortable strapless bra.
After tugging here and tugging there, I managed to make the look work,
and I made sure the look was right in the large mirror on the back of
the bathroom door.
I then moved to the vanity that I laid out the jewelry on and put
on my red rhinestone earrings, my new clear rhinestone necklace, and
finally my red rhinestone bracelet and stood back to take a look. The
jewelry totally set off the look perfectly, I was really happy with the
combination of the jewelry, makeup, and dress, and I knew Bill would as
well. I put my rhinestone anklet aside as I was going to need Bill to
put it on carefully, as I knew that if I did, I would probably put a
run in my ultra sheer hose.
Only 5 minutes before Bill would be coming to get me at my room, I
planned to pack my clutch purse for the evening, and the worst thing
happened, a button popped off my top as I leaned over top pick up my 4"
black patent heels. I had packed a sewing kit, just in case this would
happen and was glad that I did!. I called Bill and told him that I lost
a button and would need time to sew it back on and I would call him
when I was ready, and would only be a few minutes. I grabbed my sewing
kit and sat down at the desk and quickly sewed the button back on.
With the button back on I slipped the top on and all the buttons
stayed in place. I then grabbed my black patent clutch purse for the
evening and started putting the essentials for the evening. My darker
blush, blush brush, small Obsession perfume and I was almost ready for
Bill. I applied a healthy coat of my favorite formal lipstick shade,
then applied a brighter shade of red to finish off my lips, and as I
looked in the mirror, I thought I had done the best job ever on my
makeup and attire and was really pleased. I completed the packing by
adding those into my clutch purse.
I went to the phone and called Bill to say I was ready, and I was
only about 8 minutes late. Bill said he was coming right away and I
said I would be waiting for him. I did a final check of myself, and
slipped into my 4" black patent heels for the evening and made the
decision of my coat for the evening. The faux fur was out, and after
checking the temperature again, I decided to go without my spring coat
as well, after all we were taking a cab from door to door in both going
and leaving the dinner theatre.
Before I knew it there was a knock on the door, and as I opened it,
could see that Bill was pleased with my attire, but to drive the point
home spun around and said, "what do you think?", he did like the outfit
and gave me a light kiss on the lips. I smiled and handed him a tissue
to wipe off the lipstick that ended up on his lips.
Bill had changed to a darker suit and tie and looked very handsome
as I knew he would, and with all of the careful attention I took in
getting ready, I knew we would be a lovely couple together.
I told Bill he had one task to perform before we left and sat down
on the bed and hiked my skirt up and handed Bill the anklet to put on
my right ankle. He carefully snapped it on and commented on how lovely
it looked, and I smiled and commented back, "I thought you would like
it". I then gathered my purse and was ready to go. Bill was again very
classy and informed me that a taxi would be waiting for us when we got
to the lobby to take up to the theatre.
We got to the lobby and headed for the front doors, I felt so
special with a very handsome man at my side and hearing my 4" heels
clicking on the marble floor as I walked. As promised, the taxi was
waiting for us, and Bill was the gentleman and opened the door for me
and after I slid in and made sure my skirt was all the way in, Bill
closed the door and went around the other side and slid in beside me.
The trip to the theatre was brief and Bill and I help hands all the way
there, it was quite special, and I was tingling with excitement.
We arrived at the dinner theatre/hotel, Stage West, a place I had
been to several times before, but none as special as this evening. When
the cab stopped, I waited for Bill to open my door and he offered a
hand to me to help me out of the taxi, and of course I accepted. Bill
and I walked side by side into the hotel lobby and I took the lead as I
knew were I was going and guided Bill down the familiar hall towards
the actual theatre. The marble floors made it so special as I heard my
heels clicking on the floor in unison with some of the other women. I
let Bill know the window were he had to pick up the tickets and he
asked me to wait and went to get them. I felt soooooo special as I
looked around and saw all of the other women dressed up for the evening
and was so glad to be one of them.
Bill returned shortly and exclaimed, "I got the tickets, we are all
set, now what?", I then took the lead again and brought us to the
entrance of the actual theatre and let Bill talk with the hostess to
get us seated. We followed the hostess as she lead us to our booth, and
once we got there, it was perfect, a whole booth, just the two of us,
perfect and very, very romantic, she smiled and "said have a lovely
evening", if she only knew.
To explain, the dinner theatre itself is very dimly lit, with a
combination of booths and tables, candlelight lighting is what the
"feel" is. The booths are raised and are positioned to see the stage
perfectly, and this is the perfect scenario for seeing the show. An
isolated area of the theatre is were the dinner buffet portion of the
theatre is.
Once seated Bill and I chatted about how nice it was, and how
romantic the setting was. I could only smile at Bill and comment, "wait
till the lights go down". Bill smiled back, and I knew I was in for a
very special show, both on the stage and in the booth.
Our server for the table came by, and reminded us of the serving
area and asked us if we were interested in some drinks. Bill opted for
a beer and informed Bill that I would enjoy a sling. Bill asked if I
was ready for dinner, and told him, I would be more comfortable going
after the drinks arrived, so we waited and soaked up the atmosphere, it
was certainly a very special time. The drinks arrived shortly after
that and I got my purse and pulled out the strap, converting it from a
clutch to a normal purse with a strap to go up and get some dinner.
Bill and I got out of the booth, and he exclaimed, "after you my
dear", and I lead the way to the serving area, and we ended up standing
in line for the food, not a problem as I got to see what the other
women were wearing, and I would see that I was among the most dressed
up women in the place!, and I felt even more special, if that was
possible.
Bill went one way and I the other and we met at the end as we got to
the last of the buffet. We walked together back to the booth and ate
our dinner and talked about the environment of the dinner theatre,
whether Bill knew it or not, I was already turning to putty in a
romantic way. When we were done our main course, I asked Bill if was
ready for dessert, he was not really up for it, so I took a trip by
myself to see what I could find. I had a feeling Bill wanted to see me
from a distance, in my formal outfit.
Once back at the table I finished my dessert and Bill and I
continued to chat, I was really feeling like I was already putty and
ready to cuddle into him right then and there, but that was to come
soon enough.
With the announcement that the show was to begin in a few minutes,
nature called and I had to use the ladies room. I then converted my
regular purse to a clutch again and with that, I excused myself from
the table and headed to one of the two ladies rooms at the theatre that
I have never used. As I entered the room, it had the same layout as the
one I usually use was used to. The stalls, large lighted makeup mirror,
marble floors, and of course a lineup, for both he stalls and the
makeup mirror, except this washroom one only had three stalls and the
other six. I stood in line and waited for my turn and soaked in the
ambiance of the environment. Once it was my turn, I did my business and
headed for the makeup mirror were I touched up my lipstick to make it
dark and rich again and fluffed out my hair.
Once back at the table, Bill and I continued to talk and I took the
chance to look around and see some of the other women and how they were
dressed and there was a variety. Some dressed up as much as I was and
other in simple skirts and blouses, and other in just pants and a
blouse, it was quite different from the last time I attended this
dinner theatre, but I felt even more special all the same.
Then the moment I was waiting for happened, the lights went down and
the show started, I felt totally comfortable as Bill put his arm around
me. He offered for me to come and "cuddle" in with him, with body
language, and I melted as I slid over and allowed him to drape his arm
around me, I leaned my head onto his shoulder and enjoyed.
Bill made the moves fast and furious with the lights down and I was
melting very fast, he kissed and licked the nape of my neck, my ears,
caressed my shoulders, my breasts, my legs, I was simply in heaven and
whimpered and such on some of his touches. I hardly remember the first
act of the play as Bill continued, and I found my painted fingers
caressing the inside of his leg, every once in a while exploring the
tops of his thighs. At one point one of his fingers found its way
inside my mouth and I enjoyed giving him a demonstration of some of my
oral abilities, you can guess what he thought. The play was a musical
and very enjoyable, I was enjoying it very much, and was enjoying
Bill's advances just as much.
Finally the first act ended, and the lights came back on, and I
needed to use the ladies room, one for nature and the other to ensure
my makeup was not smudged too much after all Bills activity. I knew
that I was in for a large lineup at the ladies room and I was really
looking forward to it. I grabbed my purse and gave Bill a light kiss
and headed for the larger of the two ladies rooms at the dinner
theatre. As expected there was a very long line, right out the door as
a matter of fact, but I patiently stood in line and again, soaked in
the ambiance. The line moved quickly and it was fun to watch the women
go from being in line to the stall, then from the stall to another line
at the mirror, then touching their makeup then leaving. Before long it
was my turn and I followed the lead of the other women and used the
stall, then got in the line for the mirror, until finally it was my
turn. I pulled out my blush brush and touched up my cheeks, then combed
out my hair and finally applied another coat of lipstick. Making sure
everything was perfect, I packed my purse and headed back to the table
were a smiling Bill met me. "Have fun?", was his comment as I slid into
the booth, and I commented back, "we women want to make sure we look
perfect for our men", he smiled back and commented, "you certainly do".
The announcement then came that the second act was going to begin
and then decided to give Bill a little show and opened my purse and
"checked" my makeup with my lighted compact. I then closed my compact
and grabbed my little vile of Obsession perfume and applied another
dose to my neck, and Bill commented, "my that smells lovely, what is
it?", I let him know it was Obsession, and groaned, "mmmmm", I smiled
back at him as I packed my purse up again.
Before long the second act of the show started, and once again so
did Bill. I slid in beside him again and "cuddled" in and as soon as I
did Bill was busy nibbling on my ears, even venturing as far as
sticking a tongue in my ear which made shivers run down my spine and
got a low groan from me. At one point I whispered in Bill's ear that my
silky thighs were available for him, and hiked my skirt a little and
allowed the slit in the skirt to part and expose maximum thigh. We were
safe as the tablecloth hung down very low in back and front of the
table, allowing for maximum "activity" to occur under the table.
Bill took advantage of the opportunity and spent time caressing the
silky hose I wore for him and I could tell he was enjoying it. As the
second act of the show wore on, the attention that Bill was giving me
was getting to me, and I found my hands wandering a little more
aggressively under the table and as Bill continued the teasing.
Now it was my turn, I ventured high on Bill's thigh with my left
hand and knew what I would find as I felt into Bill's crotch, it was a
nice hard and erect member. I took a long time in caressing Bills
crotch through his pants and he groaned in approval as I continued to
watch the show and played with his hard member. Bill's groans and
shifting in his seat continued to get more and more, and I decided to
give Bill a special treat and I slowly found his zipper and undid it.
Bill was quietly groaning as I worked his hard member out from behind
his underwear, exposing it outside of his pants, all beneath the table,
and before I knew it, I had his member in my left hand and I massaged
the tip slowly and with my thumb. I then wiped some of the pre-cum off
the tip of his head and brought my hand out from under the table and as
Bill watched as I licked the sticky liquid from my fingers.
I then massaged Bill a little more under the table to approving
groans from Bill, and not wanting to "push our luck", Bill reached down
and did up his pants. I however did not stop caressing him under the
table through his pants, for the remainder of the show, nor did he stop
his caressing and advances.
Sadly, the show ended and after a few hours of caressing, I new Bill
was quite hot and ready to get back to the Hotel and so was I. We
waited for the "mass exodus" as Bill put it to stop. In the meantime, I
took the moment to check my makeup with my lighted compact and decided
that my makeup was fine for the ride home.
Bill and I left the booth and headed back through the marble hallway
and into the main lobby of the hotel. Noticing that there were no taxis
waiting, Bill asked me to "take a seat, I will take care of this", and
I sat down and Bill went to the front desk to call a taxi. Bill came
back and informed me that "it would only be 3 minutes", and before we
knew it the taxi was there and Bill escorted me out. Once again he was
the perfect gentleman and opened my door and allowed me to make sure my
skirt was in before he closed the door. Bill then went to the other
side and slid in, and as we drove back to our hotel, it was a little
different than the drive to the theatre as my hand rested on his upper
thigh and gently "explored", all the way home. Bill and I discussed
what we might do when we got back to the hotel and I suggested, "well
it is the weekend, shall we play the Bridesmaid and her date after the
Wedding, enjoying a glass of wine in the lounge?", Bill agreed, and I
suggested we go back to my room were I get "dressed for the part", Bill
wholeheartedly agreed. The taxi pulled up front of the hotel and as
Bill was settling things with the driver, one of the valets at the
hotel came and opened the door for me. I slid out of the taxi, where
Bill met me and into the lobby we went, side by side. We headed up to
my room and once inside I told Bill to make himself at home while I
changed.
I slipped out of the top and skirt and removed all of my rhinestone
jewelry, except my anklet, I decided to leave that in place. I was
hoping I could get away with my conventional bra and not have to go
through the hassle of strapless one. So I slipped on the royal blue
Bridesmaids dress, a crinoline, the jewelry I left out, the pearl
necklace and the matching earrings, then finally my 3" matching satin
heels. I looked myself over in the mirror and saw that the bra strap
was showing, as the back of the dress was somewhat low cut, and was
hoping Bill could help me out.
I entered the part of the room that Bill was sitting and watching TV
and could see the look in his eyes when he saw me, "my how lovely", was
his comment. I apologized that it was not the green one he wanted, but
told him it was the same dress, only in Royal Blue, and he commented
that he liked this Colour better, "it suits you more", was his comment.
I thanked him and asked him to give me a hand and see if he could push
my bra down, he tried, but to no avail. So I excused myself and went to
change bras, which was a hassle, but it only took a few minutes. When I
was done, I checked myself in the mirror and could see everything was
perfect, I then went to my makeup mirror and touched up my lipstick and
brushed my hair. When I was ready I met Bill, and asked him to do some
of the snaps up on the dress I could not reach, and he willingly
obliged. I then packed my clutch purse into the sack I had previously
packed and with that, and we left for the lounge.
Bill was certainly enjoying the look of the satiny gown I was
wearing, and I also felt special, as I was to be seen as a Bridesmaid
after a long day and a wonderful Wedding. As we left the elevator, we
ran into a woman heading in, and she looked at me and said, "how
lovely", I thanked her and we were on our way. I seated myself at the
same place I had in the afternoon. Bill went to get the glasses of
wine, and I started looking around and I could see way on the other
side of the bar some other people and two of them were indeed
Bridesmaid's as well, which made the atmosphere very enjoyable. Bill
sat down in the same place he had in the afternoon and with my cocktail
length dress, there was to be no peaking up the skirt this time.
Bill and made small talk about how the evening went, and how
enjoyable it was, and he made a comment about the sack I was carrying,
and I told him, "in time dear". Once we finished our glasses of wine,
Bill invited me to his room for a "toast of champagne", to which I
agreed, and thought it was a wonderful idea. Once Bill had settled the
tab, as always the gentleman, we were on our way to his room, we left
hand in hand and as we entered the elevator, and started up. I could
not resist some light kissing from Bill, the evening up this point was
so special, and I new it was going to be even more shortly.
Bill lead me to his room and opened the door and invited me in, and
as soon as the door was closed offered me a long and inviting kiss, our
tongues danced. I felt so satisfied, Bill got to explore the gown I was
wearing for him and felt for himself how satiny it really was,
caressing my backside and generally enjoying the satin. Bill then took
the lead and offered the room to be lit in candlelight, and got no
resistance from me and lit three or four candles and turned off the
lights. He then offered champagne, and I accepted his offer, and he
returned with a bottle and opened it. I looked around and the ambiance
was perfect, a candlelit room, champagne coming and a hot and handsome
man to please.
Bill, always thinking of his date, brought out a box, handed it to
me and asked me to open it, and inside was two crystal glasses and he
informed me that they were for me, so we could remember the evening. I
of course gave him a long and deep kiss "thank you", and when broke our
embrace he poured the champagne and we toasted the evening and sipped.
I sat close to Bill, and offered him my dress to caress and feel the
wonderfully silky material, and Bill enjoyed. After a couple of glass
of champagne and caressing, both Bill and I were ready for more.
Bill approached me, looking deep into my eyes and our embrace was
intense, kissing deeply, as I could feel his tongue enter my mouth, and
thrust my tongue in his mouth as well, and took the opportunity from
time to suck his tongue up and down. Our embrace grew even more
passionate and I could feel Bill feeling the lovely satin all over,
meanwhile my hands explored to Bill's now very hard member. I explored
it for some time through his pants and eventually thought that now was
the time to really thank Bill for a spectacular and wonderful evening.
As we continued our passionate kissing, I started to help Bill out
of his clothes, firstly removing his tie, then helping him unbutton his
shirt, and eventually Bill took over and started undressing quite
rapidly. First his shirt, then pants, and as I sipped on some
champagne, I watched as Bill was eventually lying on his bed only in
his underwear. I then got an idea and asked Bill if he was ready for a
"satin massage", to which he answered, "I have never had one before",
to which I replied, "well it is going to be my pleasure".
I excused myself briefly and went to the washroom to take care of
nature, making sure not to get my Bridesmaid Dress soiled. After that
applied another thick coat of deep red lipstick and donned the elbow
length satin gloves I had packed.
I entered back into the room and Bill was just finishing a sip of
champagne, then laid back down on his back, and I asked him, "ready",
to which he replied, "oh yes". I moved myself to the side of the bed
and started caressing him oh so slowly, concentrating on all parts of
his body, except the bulging mound beneath his underwear, everywhere
but that on purpose. Every once in a while our lips would meet in a
passionate embrace and he would offer me his tongue to suck, and would
always oblige. The caressing lasted for what seemed an eternity, and
eventually, my curiosity got the better of me and my hands found there
way passing over the large bulge underneath his underwear.
Eventually the caressing got to much for Bill, and he reached down
and lowered his underwear to expose a fully erect and wanting member. I
immediately caressed it with my satin covered hands and could hear Bill
groan. I continued my caressing, but now, every once in a while bending
over and licking the head of Bill's erect member.
Finally it was time and I adjusted the skirt of my gown and kneeled
beside the bed and started to concentrate on Bill's erection. First
with my satin cover hands, then I lowered my deep red lips over Bill's
member and started to flick my tongue over the head and started to lick
up and down his shaft. Then being able to resist no more, I opened wide
and wrapped my lips around him and started to pump up and down. My left
hand caressed his balls as I pumped up and down, and could hear Bill
groan over and over, and could feel him nearing release. As I sensed
Bill coming to the "point of no return", I pumped up and down faster
and faster, and was rewarded with several spurts from Bill that I
gladly swallowed every drop. I kept Bill in my mouth until I could feel
him go soft then making sure he was clean released him from my lipstick
covered lips.
Bill was completely spent, and the evening of drinks, flirting, and
the fact it was 2:30am, had Bill in a state of near sleep. I got up,
sipped some of the champagne that was left in my glass and smiled at a
very sleepy Bill, and commented, "ready for round two?", to which Bill
replied, "I am afraid my dear, the events of the evening will probably
not make that possible". I sipped on my champagne and could see Bill
was slowly falling asleep, he then requested that I give him a satin
massage on his back, to which I willingly obliged and gave him a nude
satin massage from head to foot and he certainly enjoyed it.
After the massage, Bill and I sipped the last of our champagne and
he asked me, "are you sure there is nothing I can do for you?", I
replied, "Bill my Love, you have given me a night out of true feminine
bliss, treated me exactly the way I always want to be treated as a
woman, that is more than anything you can do for me in any physical
way". Bill replied, "alright dear, I am glad you enjoyed the evening".
I looked at the clock and it was approaching 2:45am, and for a girl
that is used to getting up at 4am every day for work, it was certainly
running late. I started to pack things up and Bill reminded that the
glasses were for me and he helped me pack up the glasses in my sack,
Bill was still completely naked, and looked as handsome as ever.
Bill and I kissed one last time, deep and passionate and I continued
to thank him for a wonderful evening to remember, and helped "tuck" him
into bed. I then grabbed my sack and saw Bill for the last time and
blew him a kiss and headed for the bathroom to fix up my smudged
lipstick and decided to wear my satin gloves back to the room. I left
Bill's room, probably just as spent as Bill, and saw no one else in the
elevator and managed to get back to my room.
Once inside I got out of my Bridesmaid dress, lingerie, and finally
jewelry and washed the makeup off my face. Eventually slipping into my
peignoir and finally slipping into bed dreaming of a wonderful and
unforgettable evening ever.
I will never forget this evening "Bill", you know who you are, and
any time you are in Toronto and want to re-create it, I would
definitely love to be your TV girlfriend, possibly we can get to round
2.
Epilogue:
The evening you have read about was totally 100% reality, and was
exactly what I enjoy when dating my dream date,
Imagine this; a day with a handsome dapper man from the U.K., with
all the charm of James Bond, a look and accent that would make any
woman take notice. Then imagine being with that man, dressing for him
to please his visual senses, for a quiet casual afternoon drink, then a
fantastic night when you can get all dressed up for a formal dinner
theatre engagement. Followed by a chance to slip into a silky and
romantic Bridesmaids Dress, matching satin heels and play "Bridesmaid
and date after the Wedding", sipping on a glass of wine in a hotel
lobby. Finally, last but not least, him taking you back to his room and
allowing you to thank him as only a woman could for a wonderful
evening.
Believe it or not, this adventure came true to me in real life and
it will go down as one of the most memorable in my life, for the
purpose of this story, we will call my wonderfully handsome date, Bill.
It all started with an email from Bill in late March, 1998:
Dear Joyce:
I regularly visit on business, many lonely nights spent at a hotel near
the airport. Looking for a convincing, sophisticated and tarty TV date.
I'm 38, attractive, good company and would treat you as a real lady in
any way you want. Interested tell me more!!
That started a flurry of email and once I got a few from Bill, I
knew that he was just the type of date I like, one that wants to date a
sophisticated woman. One that knows how to dress handsomely, and one
that can respect all of my feminine desires and of them is to remain as
feminine as possibly no matter what happened.
Then before I knew it, the date was to be set, May 1st or May 2nd
would be best for Bill, he was arriving in town from the U.K. on the
Wednesday prior and would be available for either evening or both.
However, my schedule would only allow for one evening to be available,
but I after I proposed that we got together in the afternoon to get to
know one another previous to the formal date, the Saturday became the
obvious day of choice, as Bill had business meetings Friday afternoon.
Then how we would meet became an issue and Bill suggested that he
would "hire a car" to meet me and pick me up for the dinner theatre and
whatever, but with cultural differences figured out. Bill meant "rent a
car", and I was not going to have a person used to driving on the other
side of the road attempting to come and pick me up on the roads in my
area. So I made another suggestion, and that was he got me a room in
the hotel he was staying in and we could take a cab to the dinner
theatre, and he liked the idea and that plan was set.
So the meeting and such arrangements were set, now the hard part
any woman faces on a date, and "blind" date as this one was going to
be, "what to wear!", and for me I had to pick two different outfits,
one for the afternoon and one for the evening. So I concentrated on
them one at a time, first was the evening, as I really wanted to look
special for Bill.
Bill had mentioned he likes his women to dress "ultra feminine",
and when I asked him about this he mentioned flowing gowns of satin and
lace and such, and I sent him pictures of me in formal attire to decide
on what he wanted to see me in. He wrote back:
Silky 1st, Floral 2nd, Velvet 3rd, but all wonderful.
So I started to sort through my Silky Bridesmaid Dresses and found
one that would be perfect for a Saturday evening formal dinner theatre
and picked it out of my wardrobe. It was cocktail length, blue satin
and with 4" black patent heels would be perfect, not too
"Bridesmaidish", but classy and elegant. I then started to second guess
myself and grabbed a "little black dress", one that I had purchased
Christmas shopping in November of last year, perfect for a formal
evening. This dress was mid thigh, and combined with sheer black hose
and 4" black patent heels would look killer. Also, I grabbed an Aqua
green off the shoulder, tea length dress that a girlfriend of mine
made, perfect for a formal occasion and hung them up together for a
final decision.
Finally, after thinking that this was going to be a Saturday evening
and elegance usually is what you go for, I pulled out a two piece deep
red print, off the shoulder ensemble. I got this off a girl that wore
it as a Bridesmaid Dress, it had a cocktail length skirt with a thigh
high slit, and off the shoulder top. The buttons down the front were
rhinestone and quite elegant, I planned for a rhinestone necklace,
matching bracelet and earrings and finally a rhinestone anklet to
finish the look off. I reserved judgement until Sharon looked over the
outfits and helped pick out which was most appropriate for a Saturday
evening at the theatre.
Sharon scanned the outfits, and her decision was decisive, "the red
print, with the rhinestone earrings and the matching rhinestone
necklace, you will knock them dead!, have fun girl, I want a full
report!". So with that, the final decision was made, it would be the
red print dress, but I still wanted to wear the silky and satiny
Bridesmaid Dress for Bill as he loved that style of dress.
I then made another suggestion to Bill, and offered that I would
possibly slip into a satiny Bridesmaid Dress when we returned at the
end off the evening. Bill said he would like that very much and decided
that I would plan for that, as it would be the best of both worlds for
Bill, a classy sophisticated lady for the dinner theatre and one in
flowing satin for more quiet times. He thought that was a good idea, so
with that set, Bill, picked the Bridesmaid Dress he wanted to see me
in, it was a lovely satin Alfred Angelo number, with a lovely deep V
back, cocktail length in hunter green.
So with the evening attire planned, I started planning for the
afternoon meeting and was struggling with what to wear, but with a
sudden rise in the air temperature, it was more like summer. So my
wardrobe ideas started to change for the afternoon, from more fall and
winter clothes to the spring and summer part of my wardrobe. I decided
that the first time he was going to see me was a more sexy and short
skirt or dress and high heels.
At first when I planned, I decided to go with a red cashmere
sweater, mock necked and a little black leather mini, sheer black hose
and my 3" black kid heels. As the time got closer to May 2nd, the
temperature started to rise to early summertime levels, in the low to
mid 70's and the sweater idea was not going to be practical even though
we were going to be meeting indoors. So back to the closet I went and
grabbed one of Sharon's little short flowered sundresses, real cute and
thigh high, combined with the 3" black kid heels, would also look
really good. Then I started thinking that I was meeting Bill near the
airport, and if that was the case, there are always a number of
convention goers there, and I also told Bill I would be most likely
dressed "business". With those factors in mind I pulled out my "90210"
skirt and matching jacket, a skirt just many inches above my knees and
a short sleeved jacket that with a camisole underneath, perfect for
"very sexy business wear". With the three outfits chosen, I decided
that I would pack all three and allow my mood/temperature/ambiance to
decide on what I would wear.
The Bridesmaid dress that Bill picked out was one that I had the
exact same dress, Alfred Angelo, one in hunter green and the other
Royal Blue, both with matching 3" heels. I was leaning towards the
Royal Blue as the date approached as it had a little more room in the
waist area and decided that I go with that instead of the Hunter Green,
and I was sure Bill would not mind!.
With all of that decided, the rest was easy right?, wrong... Packing
all of my makeup, jewelry, shoes (satin Bridesmaid heels, 4 " Black
Patent Heels, my 3" black kid heels. Last but not least a pair of 2
inch heels (for when I was getting ready), outfits, dresses, and such
was really a chore, mind you a very enjoyable one. So as the days got
closer, Bill and I kept on exchanging mail, and the anticipation of
meeting this very classy and possibly handsome man started to grow. I
got all of my makeup, purses, and dresses, skirts, lingerie and such
packed, I all of a sudden realized I had forgot some other essentials
that would fill my luggage to capacity.
Firstly I had planned on a lovely faux fur coat to compliment the
elegance of the outfit. However the temperature rising took that out of
the picture, so I had to plan that the weather might be a just a little
cool at dinner and packed my spring coat just in case. I had to plan
that I was going to ruin a pair of my sheerest hose, the style I was
going to be wearing both for the afternoon and evening, and packed a
few more pairs just in case.
Bill and I discussed that possibly if everything was perfect for the
evening we might end up sipping champagne with me in romantic lingerie
and who knows what, so that got packed a romantic and flowing peignoir
as well. Finally when I thought all the essentials were packed, I
forgot one thing, and that was a pair of satin gloves for putting on my
ultra sheer hose, as I packed them I thought, "mmmmm, maybe these will
come in handy?", and stuffed them into one of my bags. Last and finally
but not least, a lighted makeup mirror in case the lighting in the
bathroom at the hotel was not right.
With a travel bag and clothes bag stuffed to capacity I was ready
and just had to wait for the day to arrive to hear from my special
date. He called me the Wednesday before the date, his voice was very
nice and we had a wonderful conversation. I could tell he was looking
as forward to this day as much as I was, and he ensured me everything
was taken care of, and I thanked him for that.
The Friday before the big day arrived and a little surprised arrived
in the mail from a place I purchased it from via the Internet. It was a
lovely clear elaborate rhinestone necklace, very elegant, more than the
one I was planning on wearing, so I packed it. Along with the red and
decided to make a last minute decision on which I was going to wear,
most likely when I was all dressed and doing a final check in the
mirror.
The Big Day, Saturday, May 2nd, 1998
Finally the Saturday morning arrived and I was all excited as I got
up and packed the car for the trip to the Hotel, it was a last minute
thought but I thought it wise. You see, the buttons on the top of the
formal evening outfit have a habit of coming off and decided to pack my
portable sewing kit at the last possible minute.
Then the worst thing could happen, just as I was about to leave, the
phone rang, it was work, there was emergency and I was needed.
Terrified to say the least was what went through my body, but luckily I
got things calmed down remotely and was only about 45 minutes behind
schedule. Bill and I planned to meet at 3:00 pm, and I knew it was
going to be a little late with the circumstances. So I finished loading
things in the car and I was off.
Entering the hotel was a very special feeling, as the hotel was VERY
classy, and elegant, I do travel but never stay in hotels as nice as
the one I was, I knew things would be very special for this day. I
checked in and noticed something right away and that was I saw a number
of women in business attire, ie., thigh length skirts, matching jackets
and heels, and before I even checked in I knew what I was going to wear
when I met Bill, I was not going to be outdone!. I also noticed a
lounge area, the one Bill had told me about in our emails and now that
I knew exactly where I was going when I got changed and came to meet
him. So being all checked in, and a couple of trips ahead of me, I
headed for my room, one floor down from Bill, as we had planned, after
all I wanted him to come "calling on me" for the evening date.
I entered the room for the first time and could not believe how
classy and elegant the room was, as I said, I have traveled quite and
this was nothing like I had ever stayed in, it was so "regal". The way
the bathroom lighting was laid out, the couch in the room, the desk,
antique and very classy, the day got even more special. Finally after
getting all my bags in the room, I gave Bill a call to let him know I
was at the hotel and getting ready for meeting him in the lounge. He
sounded as excited as I was. He asked if there was any problem checking
in and I told him that there was none, he was pleased and anxious me
meet me. I also told him that it would be more appropriate to get
together at 3:30pm. 30 minutes later and Bill and I agreed and he said,
"no problem". So with the initial contact made, I started to organize
the room for the day and evening ahead.
The first order of business was the garment bag that had the
dresses, skirts and such for the evening, I quickly took out my clothes
for the day and hung them up in the main closet to prevent them from
getting wrinkled. With all of those unpacked I decided to head for the
travel bag.
I unpacked all of my clothes and made use of the drawers provided,
packing lingerie in one, other clothes in another, etc, soon they were
all full and my travel bag empty. Then I moved to organize my jewelry
for the evening as I did not want it to get mixed up, so out of the bag
I packed all of the jewelry in came the day and evenings jewelry, I
placed it on a little table in front of a mirror. I assumed this table
was for that purpose as it worked out perfectly for me putting on my
jewelry. The first "pile" was my jewelry for the afternoon, my rings,
long dangly gold earrings and that was about it. The second pile was
for the evening affair, with the new elaborate rhinestone necklace, red
rhinestone necklace, red rhinestone bracelet, matching red rhinestone
earrings, and finally my clear rhinestone anklet. The last pile was for
the Bridesmaid dress I was going to wear for Bill, and that was a pair
of heart shaped crystal earring and a pearl necklace with a tiny broach
in the middle, and with that, the jewelry plans were set.
The final activities in unpacking was to set up my makeup mirror in
the bathroom to get ready and to sit down at the lovely desk and
intricately glue a rhinestone back into place in a button onto the top
of my dress for the evening. One popped off when I packed it away for
the trip and wanted the look to be perfect for Bill.
So with that done, I got into the shower and started getting ready
for Bill to meet him in the lounge of the hotel. After the shower I
slipped on my pink makeup coat and started getting into my lingerie,
not only for the afternoon, but for the evening as well. I decided that
I would wear a silky and lacy pair of hunter green panties and slipped
them on, and continued with a waist cincher, very pretty all lace
conventional bra, camisole and ultra sheer nude hose. The satin gloves
I packed came in handy as I used them when putting on the pantyhose as
I tried not to put a run in them. Once done with the lingerie, I
slipped on the low black pair of heels I packed as not to put a run in
my hose as went about getting the rest of myself ready, then started on
my makeup.
After applying foundation, I stared at my face, decided on what
"look" to go for, "business", "light casual", or "heavy casual". I
decided "light casual" would work best as I wanted Bill to be
pleasantly surprised with me "all done up" when he picked me up for the
dinner theatre. So with that in mind, a light coat of eyeliner, light
brush of purple on my lower lids, and light on my upper lids. Finally
my blush was applied light and my lipstick was my more "business" or
lighter red/pink shade. When I was done I knew he would be pleased when
he first saw me. I decided not to do my nails for the afternoon meeting
and plan to do them for the dinner date.
With the makeup done, it was time to get into my skirt and blouse
and begin the final preparations. I wanted to wear perfume for Bill,
but the type I was going to wear for the dinner theatre, "Obsession",
did not really fit with my mood or clothing I as wearing. I decided
instead to spray a little of my Halstons perfume on my jacket and allow
that to entertain his senses when we met, Halstons is my "office
perfume". The last thing I did was comb out my hair to make it perfect
for when I met Bill, and thanks to a girlfriend who taught me, I did
quite well.
I noticed the time, 3:36pm, I was slightly late, but Bill told me he
would have a glass of wine waiting for me in the lounge. I slipped out
of my low heels and then into my "business" 3" black heels to complete
the professional business look. I then gathered things together, my
purse, hotel key, etc., and once all set I took a final look at myself
in the full length mirror on the outside of the bathroom door. I knew I
looked as good as I was going to get, with one final check of my
lipstick, and a tug at my camisole. I made sure maximum white lace of
my camisole was showing, made sure my skirt was sitting right and slung
my purse over my shoulder and headed out the door to the elevator and
the lobby.
I walked with confidence as I knew I looked just as good as any of
the other women I had seen as I was checking in, and was hoping I would
run onto them as I got into the elevator heading to the first floor. I
saw no other women as I exited the elevator and headed for the lounge I
had spotted earlier when I checked in.
I looked around as I came up a set of stairs, my heels clicking on
the marble floor. I did not see anyone except a number of empty tables,
then after rounding a bar area, I spotted the wine glass sitting there
and my date for the evening smiling and waving at me.
To say I was pleased was an understatement, Bill was dressed in a
casual suit, tie and all, and we matched perfectly, a businessman and a
businesswoman. More importantly, he was handsome and dapper, just like
he had described, I just hoped that he was just as pleased with my
appearance.
He greeted me with a hand towards me, and as I took it, the first
magical kiss happened, it was light and more of a "pleased to meet you
Miss Blake" kiss, I was in heaven. I sat down on a couch and was
sitting just kind of "kitty corner" to him, and had a tough time making
sure my short skirt was not exposing my vaginal area to him, I wanted
to retain some dignity, but I found it hard.
Bill and I sipped on wine and talked about many things, and it was
a very enjoyable time, Bill liked the way I looked and I explained that
I really like dressing that way for him. We talked about many things,
among them was how elaborate or "opulent" I found the hotel, and Bill
explained his experience with the hotel and agreed it was quite lovely.
At one point as we were talking Bill mentioned he hoped that I would
walk up a set of stairs one the other side of the bar were I entered.
There was a parrot there in a cage that whistled out, "pretty lady",
and was hoping he would hear the bird say it to me, I smiled at him and
told him, "maybe soon".
The conversation carried on and I was falling for Bill in a big
way, he was charming, well dressed and could talk a woman into anything
with his accent and demeanor. We talked about everything as time went
by, and finally the glass of wine I started persuaded me to visit the
ladies room, and this visit was none like I have had before. I asked
Bill were the ladies room was and he explained "down over there, around
the corner, etc.", and it was a long way, but as I was to find out,
well worth the trip. I grabbed my purse, and stood up, straightening my
skirt and headed past the parrot waiting for "pretty lady", but did not
hear anything. I knew Bill was staring at my legs in the short skirt
and gave him a look back and he smiled.
Once off of the carpet of the lobby, I started down a marble
hallway, my heels echoing in that "oh so feminine delightful manner",
eventually ending up at the entrance to the ladies room. I opened the
door and was "wowed" at what I saw, a large lighted makeup mirror, 5
stalls, and a vanity. The vanity offered vanity style lighting and an
antique bench to sit down and do your makeup, also a large floor length
mirror as well the whole floor was marble. I was alone, but the
experience was still special. As I entered a stall, I found a place to
hang my purse and they were very clean. As I did my business I noted
that the walls the stall in the ladies room were particularly clean,
unlike other ones I had been in with graffiti all over the place, these
were very well kept. After I finished my business, I gathered myself
together and headed for the well lighted makeup mirror and fixed up my
lipstick and hair, then finally adjusting myself in front of the large
floor length mirror, making sure my camisole was showing enough and my
skirt hanging just right.
I made my way back to Bill, going up the stairs that passed the
parrot, waiting for it to sing out "pretty lady" as I walked by, but it
did not. "Oh well", I thought and headed towards a smiling Bill, I sat
down and we resumed our pleasant conversation, and I caught Bill a few
times trying to peak a look up my little short skirt. He ordered us
another glass of wine and we kept on talking, until I checked the time
and realized that I would need to have some time to get ready for the
evening and asked if he would escort me back to my room, and he gladly
agreed.
Bill escorted me to my room and kissed me lightly as he said
goodbye and said he was anxious to see what I would look like for the
evening and I told him, "you won't be disappointed", he responded, "I
am sure I will not". We planned for Bill to come calling on me at
5:15pm to leave for the dinner theatre. Once back in my room, I changed
out of my skirt, blazer and camisole and left my silky hose and panties
on for the evening, I slipped into my pink satin makeup coat and
started to get things ready for the evening. I also slipped out of my
3" business heels and back into the lower 2" heels to protect my hose.
First order of business wash to wash off the light makeup I had on
and to get ready for a look for the evenings events, which needed to be
much more formal and dramatic. I looked at the clock, and Bill was to
pick me up at 5:15pm for the trip to the theatre and that would give us
enough time to arrive for dinner.
I took out my skirt and top for the evening, along with my heels
and laid them out on the bed, and then headed to the bathroom for my
makeup application.
I always take my time when getting ready to go out for a formal
occasion, but this time was longer than I had ever taken, as I wanted
to try a new look with my eyes. Firstly was my eyeliner, much darker
than the afternoon, basically on the line of heavy and "streetwalker",
but on the lighter side, I was pleased with the look, dark alluring and
seductive. Then the eyeshadow, dark green on the lower lids and a dark
brown on the upper, definitely a new "look" for me!. Then finally a
healthy coat of mascara and my eyes were done, dramatic and perfect, I
was really pleased, and was hoping Bill would be as well. Then to my
cheeks, my darker blush, and after turning the light on my makeup
mirror to "evening", I relied on it to make my cheeks perfect for
evening wear, they looked perfect, a little dark in bright light, but
perfect in low. I decided to save my lipstick application to just
before Bill picked me up so it would be perfect for him when he saw me
for the first time.
With my makeup done, I seated myself at the lovely table in the
room and applied a coat of nail polish that was going to be matching my
lipstick, I carefully applied a nice and healthy coat. Once done I
checked the time and saw that it was approaching 5:10 pm and decided to
get into my outfit for the evening.
The final touch before I put on my outfit for the evening was a
healthy application of Obsession perfume, behind my ears, my neck, my
ankles, and I was all set, then I decided to prepare something special
"just in case" things went well for the evening.
I packed a long flowing white peignoir, and some satin long
sleeves gloves in a carrying sack and left it on the vanity next to the
Bridesmaids jewelry "just in case", once that was complete, I moved to
the special outfit for the evening.
After slipping into the skirt and top, I took about 5 minutes
adjusting the straps of the dress and the straps of my conventional
bra, as the style was off the shoulder and with the right tug here and
there I could get away without wearing an uncomfortable strapless bra.
After tugging here and tugging there, I managed to make the look work,
and I made sure the look was right in the large mirror on the back of
the bathroom door.
I then moved to the vanity that I laid out the jewelry on and put
on my red rhinestone earrings, my new clear rhinestone necklace, and
finally my red rhinestone bracelet and stood back to take a look. The
jewelry totally set off the look perfectly, I was really happy with the
combination of the jewelry, makeup, and dress, and I knew Bill would as
well. I put my rhinestone anklet aside as I was going to need Bill to
put it on carefully, as I knew that if I did, I would probably put a
run in my ultra sheer hose.
Only 5 minutes before Bill would be coming to get me at my room, I
planned to pack my clutch purse for the evening, and the worst thing
happened, a button popped off my top as I leaned over top pick up my 4"
black patent heels. I had packed a sewing kit, just in case this would
happen and was glad that I did!. I called Bill and told him that I lost
a button and would need time to sew it back on and I would call him
when I was ready, and would only be a few minutes. I grabbed my sewing
kit and sat down at the desk and quickly sewed the button back on.
With the button back on I slipped the top on and all the buttons
stayed in place. I then grabbed my black patent clutch purse for the
evening and started putting the essentials for the evening. My darker
blush, blush brush, small Obsession perfume and I was almost ready for
Bill. I applied a healthy coat of my favorite formal lipstick shade,
then applied a brighter shade of red to finish off my lips, and as I
looked in the mirror, I thought I had done the best job ever on my
makeup and attire and was really pleased. I completed the packing by
adding those into my clutch purse.
I went to the phone and called Bill to say I was ready, and I was
only about 8 minutes late. Bill said he was coming right away and I
said I would be waiting for him. I did a final check of myself, and
slipped into my 4" black patent heels for the evening and made the
decision of my coat for the evening. The faux fur was out, and after
checking the temperature again, I decided to go without my spring coat
as well, after all we were taking a cab from door to door in both going
and leaving the dinner theatre.
Before I knew it there was a knock on the door, and as I opened it,
could see that Bill was pleased with my attire, but to drive the point
home spun around and said, "what do you think?", he did like the outfit
and gave me a light kiss on the lips. I smiled and handed him a tissue
to wipe off the lipstick that ended up on his lips.
Bill had changed to a darker suit and tie and looked very handsome
as I knew he would, and with all of the careful attention I took in
getting ready, I knew we would be a lovely couple together.
I told Bill he had one task to perform before we left and sat down
on the bed and hiked my skirt up and handed Bill the anklet to put on
my right ankle. He carefully snapped it on and commented on how lovely
it looked, and I smiled and commented back, "I thought you would like
it". I then gathered my purse and was ready to go. Bill was again very
classy and informed me that a taxi would be waiting for us when we got
to the lobby to take up to the theatre.
We got to the lobby and headed for the front doors, I felt so
special with a very handsome man at my side and hearing my 4" heels
clicking on the marble floor as I walked. As promised, the taxi was
waiting for us, and Bill was the gentleman and opened the door for me
and after I slid in and made sure my skirt was all the way in, Bill
closed the door and went around the other side and slid in beside me.
The trip to the theatre was brief and Bill and I help hands all the way
there, it was quite special, and I was tingling with excitement.
We arrived at the dinner theatre/hotel, Stage West, a place I had
been to several times before, but none as special as this evening. When
the cab stopped, I waited for Bill to open my door and he offered a
hand to me to help me out of the taxi, and of course I accepted. Bill
and I walked side by side into the hotel lobby and I took the lead as I
knew were I was going and guided Bill down the familiar hall towards
the actual theatre. The marble floors made it so special as I heard my
heels clicking on the floor in unison with some of the other women. I
let Bill know the window were he had to pick up the tickets and he
asked me to wait and went to get them. I felt soooooo special as I
looked around and saw all of the other women dressed up for the evening
and was so glad to be one of them.
Bill returned shortly and exclaimed, "I got the tickets, we are all
set, now what?", I then took the lead again and brought us to the
entrance of the actual theatre and let Bill talk with the hostess to
get us seated. We followed the hostess as she lead us to our booth, and
once we got there, it was perfect, a whole booth, just the two of us,
perfect and very, very romantic, she smiled and "said have a lovely
evening", if she only knew.
To explain, the dinner theatre itself is very dimly lit, with a
combination of booths and tables, candlelight lighting is what the
"feel" is. The booths are raised and are positioned to see the stage
perfectly, and this is the perfect scenario for seeing the show. An
isolated area of the theatre is were the dinner buffet portion of the
theatre is.
Once seated Bill and I chatted about how nice it was, and how
romantic the setting was. I could only smile at Bill and comment, "wait
till the lights go down". Bill smiled back, and I knew I was in for a
very special show, both on the stage and in the booth.
Our server for the table came by, and reminded us of the serving
area and asked us if we were interested in some drinks. Bill opted for
a beer and informed Bill that I would enjoy a sling. Bill asked if I
was ready for dinner, and told him, I would be more comfortable going
after the drinks arrived, so we waited and soaked up the atmosphere, it
was certainly a very special time. The drinks arrived shortly after
that and I got my purse and pulled out the strap, converting it from a
clutch to a normal purse with a strap to go up and get some dinner.
Bill and I got out of the booth, and he exclaimed, "after you my
dear", and I lead the way to the serving area, and we ended up standing
in line for the food, not a problem as I got to see what the other
women were wearing, and I would see that I was among the most dressed
up women in the place!, and I felt even more special, if that was
possible.
Bill went one way and I the other and we met at the end as we got to
the last of the buffet. We walked together back to the booth and ate
our dinner and talked about the environment of the dinner theatre,
whether Bill knew it or not, I was already turning to putty in a
romantic way. When we were done our main course, I asked Bill if was
ready for dessert, he was not really up for it, so I took a trip by
myself to see what I could find. I had a feeling Bill wanted to see me
from a distance, in my formal outfit.
Once back at the table I finished my dessert and Bill and I
continued to chat, I was really feeling like I was already putty and
ready to cuddle into him right then and there, but that was to come
soon enough.
With the announcement that the show was to begin in a few minutes,
nature called and I had to use the ladies room. I then converted my
regular purse to a clutch again and with that, I excused myself from
the table and headed to one of the two ladies rooms at the theatre that
I have never used. As I entered the room, it had the same layout as the
one I usually use was used to. The stalls, large lighted makeup mirror,
marble floors, and of course a lineup, for both he stalls and the
makeup mirror, except this washroom one only had three stalls and the
other six. I stood in line and waited for my turn and soaked in the
ambiance of the environment. Once it was my turn, I did my business and
headed for the makeup mirror were I touched up my lipstick to make it
dark and rich again and fluffed out my hair.
Once back at the table, Bill and I continued to talk and I took the
chance to look around and see some of the other women and how they were
dressed and there was a variety. Some dressed up as much as I was and
other in simple skirts and blouses, and other in just pants and a
blouse, it was quite different from the last time I attended this
dinner theatre, but I felt even more special all the same.
Then the moment I was waiting for happened, the lights went down and
the show started, I felt totally comfortable as Bill put his arm around
me. He offered for me to come and "cuddle" in with him, with body
language, and I melted as I slid over and allowed him to drape his arm
around me, I leaned my head onto his shoulder and enjoyed.
Bill made the moves fast and furious with the lights down and I was
melting very fast, he kissed and licked the nape of my neck, my ears,
caressed my shoulders, my breasts, my legs, I was simply in heaven and
whimpered and such on some of his touches. I hardly remember the first
act of the play as Bill continued, and I found my painted fingers
caressing the inside of his leg, every once in a while exploring the
tops of his thighs. At one point one of his fingers found its way
inside my mouth and I enjoyed giving him a demonstration of some of my
oral abilities, you can guess what he thought. The play was a musical
and very enjoyable, I was enjoying it very much, and was enjoying
Bill's advances just as much.
Finally the first act ended, and the lights came back on, and I
needed to use the ladies room, one for nature and the other to ensure
my makeup was not smudged too much after all Bills activity. I knew
that I was in for a large lineup at the ladies room and I was really
looking forward to it. I grabbed my purse and gave Bill a light kiss
and headed for the larger of the two ladies rooms at the dinner
theatre. As expected there was a very long line, right out the door as
a matter of fact, but I patiently stood in line and again, soaked in
the ambiance. The line moved quickly and it was fun to watch the women
go from being in line to the stall, then from the stall to another line
at the mirror, then touching their makeup then leaving. Before long it
was my turn and I followed the lead of the other women and used the
stall, then got in the line for the mirror, until finally it was my
turn. I pulled out my blush brush and touched up my cheeks, then combed
out my hair and finally applied another coat of lipstick. Making sure
everything was perfect, I packed my purse and headed back to the table
were a smiling Bill met me. "Have fun?", was his comment as I slid into
the booth, and I commented back, "we women want to make sure we look
perfect for our men", he smiled back and commented, "you certainly do".
The announcement then came that the second act was going to begin
and then decided to give Bill a little show and opened my purse and
"checked" my makeup with my lighted compact. I then closed my compact
and grabbed my little vile of Obsession perfume and applied another
dose to my neck, and Bill commented, "my that smells lovely, what is
it?", I let him know it was Obsession, and groaned, "mmmmm", I smiled
back at him as I packed my purse up again.
Before long the second act of the show started, and once again so
did Bill. I slid in beside him again and "cuddled" in and as soon as I
did Bill was busy nibbling on my ears, even venturing as far as
sticking a tongue in my ear which made shivers run down my spine and
got a low groan from me. At one point I whispered in Bill's ear that my
silky thighs were available for him, and hiked my skirt a little and
allowed the slit in the skirt to part and expose maximum thigh. We were
safe as the tablecloth hung down very low in back and front of the
table, allowing for maximum "activity" to occur under the table.
Bill took advantage of the opportunity and spent time caressing the
silky hose I wore for him and I could tell he was enjoying it. As the
second act of the show wore on, the attention that Bill was giving me
was getting to me, and I found my hands wandering a little more
aggressively under the table and as Bill continued the teasing.
Now it was my turn, I ventured high on Bill's thigh with my left
hand and knew what I would find as I felt into Bill's crotch, it was a
nice hard and erect member. I took a long time in caressing Bills
crotch through his pants and he groaned in approval as I continued to
watch the show and played with his hard member. Bill's groans and
shifting in his seat continued to get more and more, and I decided to
give Bill a special treat and I slowly found his zipper and undid it.
Bill was quietly groaning as I worked his hard member out from behind
his underwear, exposing it outside of his pants, all beneath the table,
and before I knew it, I had his member in my left hand and I massaged
the tip slowly and with my thumb. I then wiped some of the pre-cum off
the tip of his head and brought my hand out from under the table and as
Bill watched as I licked the sticky liquid from my fingers.
I then massaged Bill a little more under the table to approving
groans from Bill, and not wanting to "push our luck", Bill reached down
and did up his pants. I however did not stop caressing him under the
table through his pants, for the remainder of the show, nor did he stop
his caressing and advances.
Sadly, the show ended and after a few hours of caressing, I new Bill
was quite hot and ready to get back to the Hotel and so was I. We
waited for the "mass exodus" as Bill put it to stop. In the meantime, I
took the moment to check my makeup with my lighted compact and decided
that my makeup was fine for the ride home.
Bill and I left the booth and headed back through the marble hallway
and into the main lobby of the hotel. Noticing that there were no taxis
waiting, Bill asked me to "take a seat, I will take care of this", and
I sat down and Bill went to the front desk to call a taxi. Bill came
back and informed me that "it would only be 3 minutes", and before we
knew it the taxi was there and Bill escorted me out. Once again he was
the perfect gentleman and opened my door and allowed me to make sure my
skirt was in before he closed the door. Bill then went to the other
side and slid in, and as we drove back to our hotel, it was a little
different than the drive to the theatre as my hand rested on his upper
thigh and gently "explored", all the way home. Bill and I discussed
what we might do when we got back to the hotel and I suggested, "well
it is the weekend, shall we play the Bridesmaid and her date after the
Wedding, enjoying a glass of wine in the lounge?", Bill agreed, and I
suggested we go back to my room were I get "dressed for the part", Bill
wholeheartedly agreed. The taxi pulled up front of the hotel and as
Bill was settling things with the driver, one of the valets at the
hotel came and opened the door for me. I slid out of the taxi, where
Bill met me and into the lobby we went, side by side. We headed up to
my room and once inside I told Bill to make himself at home while I
changed.
I slipped out of the top and skirt and removed all of my rhinestone
jewelry, except my anklet, I decided to leave that in place. I was
hoping I could get away with my conventional bra and not have to go
through the hassle of strapless one. So I slipped on the royal blue
Bridesmaids dress, a crinoline, the jewelry I left out, the pearl
necklace and the matching earrings, then finally my 3" matching satin
heels. I looked myself over in the mirror and saw that the bra strap
was showing, as the back of the dress was somewhat low cut, and was
hoping Bill could help me out.
I entered the part of the room that Bill was sitting and watching TV
and could see the look in his eyes when he saw me, "my how lovely", was
his comment. I apologized that it was not the green one he wanted, but
told him it was the same dress, only in Royal Blue, and he commented
that he liked this Colour better, "it suits you more", was his comment.
I thanked him and asked him to give me a hand and see if he could push
my bra down, he tried, but to no avail. So I excused myself and went to
change bras, which was a hassle, but it only took a few minutes. When I
was done, I checked myself in the mirror and could see everything was
perfect, I then went to my makeup mirror and touched up my lipstick and
brushed my hair. When I was ready I met Bill, and asked him to do some
of the snaps up on the dress I could not reach, and he willingly
obliged. I then packed my clutch purse into the sack I had previously
packed and with that, and we left for the lounge.
Bill was certainly enjoying the look of the satiny gown I was
wearing, and I also felt special, as I was to be seen as a Bridesmaid
after a long day and a wonderful Wedding. As we left the elevator, we
ran into a woman heading in, and she looked at me and said, "how
lovely", I thanked her and we were on our way. I seated myself at the
same place I had in the afternoon. Bill went to get the glasses of
wine, and I started looking around and I could see way on the other
side of the bar some other people and two of them were indeed
Bridesmaid's as well, which made the atmosphere very enjoyable. Bill
sat down in the same place he had in the afternoon and with my cocktail
length dress, there was to be no peaking up the skirt this time.
Bill and made small talk about how the evening went, and how
enjoyable it was, and he made a comment about the sack I was carrying,
and I told him, "in time dear". Once we finished our glasses of wine,
Bill invited me to his room for a "toast of champagne", to which I
agreed, and thought it was a wonderful idea. Once Bill had settled the
tab, as always the gentleman, we were on our way to his room, we left
hand in hand and as we entered the elevator, and started up. I could
not resist some light kissing from Bill, the evening up this point was
so special, and I new it was going to be even more shortly.
Bill lead me to his room and opened the door and invited me in, and
as soon as the door was closed offered me a long and inviting kiss, our
tongues danced. I felt so satisfied, Bill got to explore the gown I was
wearing for him and felt for himself how satiny it really was,
caressing my backside and generally enjoying the satin. Bill then took
the lead and offered the room to be lit in candlelight, and got no
resistance from me and lit three or four candles and turned off the
lights. He then offered champagne, and I accepted his offer, and he
returned with a bottle and opened it. I looked around and the ambiance
was perfect, a candlelit room, champagne coming and a hot and handsome
man to please.
Bill, always thinking of his date, brought out a box, handed it to
me and asked me to open it, and inside was two crystal glasses and he
informed me that they were for me, so we could remember the evening. I
of course gave him a long and deep kiss "thank you", and when broke our
embrace he poured the champagne and we toasted the evening and sipped.
I sat close to Bill, and offered him my dress to caress and feel the
wonderfully silky material, and Bill enjoyed. After a couple of glass
of champagne and caressing, both Bill and I were ready for more.
Bill approached me, looking deep into my eyes and our embrace was
intense, kissing deeply, as I could feel his tongue enter my mouth, and
thrust my tongue in his mouth as well, and took the opportunity from
time to suck his tongue up and down. Our embrace grew even more
passionate and I could feel Bill feeling the lovely satin all over,
meanwhile my hands explored to Bill's now very hard member. I explored
it for some time through his pants and eventually thought that now was
the time to really thank Bill for a spectacular and wonderful evening.
As we continued our passionate kissing, I started to help Bill out
of his clothes, firstly removing his tie, then helping him unbutton his
shirt, and eventually Bill took over and started undressing quite
rapidly. First his shirt, then pants, and as I sipped on some
champagne, I watched as Bill was eventually lying on his bed only in
his underwear. I then got an idea and asked Bill if he was ready for a
"satin massage", to which he answered, "I have never had one before",
to which I replied, "well it is going to be my pleasure".
I excused myself briefly and went to the washroom to take care of
nature, making sure not to get my Bridesmaid Dress soiled. After that
applied another thick coat of deep red lipstick and donned the elbow
length satin gloves I had packed.
I entered back into the room and Bill was just finishing a sip of
champagne, then laid back down on his back, and I asked him, "ready",
to which he replied, "oh yes". I moved myself to the side of the bed
and started caressing him oh so slowly, concentrating on all parts of
his body, except the bulging mound beneath his underwear, everywhere
but that on purpose. Every once in a while our lips would meet in a
passionate embrace and he would offer me his tongue to suck, and would
always oblige. The caressing lasted for what seemed an eternity, and
eventually, my curiosity got the better of me and my hands found there
way passing over the large bulge underneath his underwear.
Eventually the caressing got to much for Bill, and he reached down
and lowered his underwear to expose a fully erect and wanting member. I
immediately caressed it with my satin covered hands and could hear Bill
groan. I continued my caressing, but now, every once in a while bending
over and licking the head of Bill's erect member.
Finally it was time and I adjusted the skirt of my gown and kneeled
beside the bed and started to concentrate on Bill's erection. First
with my satin cover hands, then I lowered my deep red lips over Bill's
member and started to flick my tongue over the head and started to lick
up and down his shaft. Then being able to resist no more, I opened wide
and wrapped my lips around him and started to pump up and down. My left
hand caressed his balls as I pumped up and down, and could hear Bill
groan over and over, and could feel him nearing release. As I sensed
Bill coming to the "point of no return", I pumped up and down faster
and faster, and was rewarded with several spurts from Bill that I
gladly swallowed every drop. I kept Bill in my mouth until I could feel
him go soft then making sure he was clean released him from my lipstick
covered lips.
Bill was completely spent, and the evening of drinks, flirting, and
the fact it was 2:30am, had Bill in a state of near sleep. I got up,
sipped some of the champagne that was left in my glass and smiled at a
very sleepy Bill, and commented, "ready for round two?", to which Bill
replied, "I am afraid my dear, the events of the evening will probably
not make that possible". I sipped on my champagne and could see Bill
was slowly falling asleep, he then requested that I give him a satin
massage on his back, to which I willingly obliged and gave him a nude
satin massage from head to foot and he certainly enjoyed it.
After the massage, Bill and I sipped the last of our champagne and
he asked me, "are you sure there is nothing I can do for you?", I
replied, "Bill my Love, you have given me a night out of true feminine
bliss, treated me exactly the way I always want to be treated as a
woman, that is more than anything you can do for me in any physical
way". Bill replied, "alright dear, I am glad you enjoyed the evening".
I looked at the clock and it was approaching 2:45am, and for a girl
that is used to getting up at 4am every day for work, it was certainly
running late. I started to pack things up and Bill reminded that the
glasses were for me and he helped me pack up the glasses in my sack,
Bill was still completely naked, and looked as handsome as ever.
Bill and I kissed one last time, deep and passionate and I continued
to thank him for a wonderful evening to remember, and helped "tuck" him
into bed. I then grabbed my sack and saw Bill for the last time and
blew him a kiss and headed for the bathroom to fix up my smudged
lipstick and decided to wear my satin gloves back to the room. I left
Bill's room, probably just as spent as Bill, and saw no one else in the
elevator and managed to get back to my room.
Once inside I got out of my Bridesmaid dress, lingerie, and finally
jewelry and washed the makeup off my face. Eventually slipping into my
peignoir and finally slipping into bed dreaming of a wonderful and
unforgettable evening ever.
I will never forget this evening "Bill", you know who you are, and
any time you are in Toronto and want to re-create it, I would
definitely love to be your TV girlfriend, possibly we can get to round
2.
Epilogue:
The evening you have read about was totally 100% reality, and was
exactly what I enjoy when dating my dream date,
