Announcement

**Transgender Stories** · 05-20-2008, 01:34 PM

Thursday October 10th, 1996

It had been a long time, and my friend Earl, emailed me to let me
know he was coming into my neck of the woods for a Seminar and wanted
to know if I was interested in getting together with him for a second
date. The first was a great success and we got along great, ending up
sharing each other's passion as only a woman and a man could.

I had a meeting at work the day of the planned date, but decided
that a date with Earl was just too good to pass up, and decided to
make an excuse to get out a little early and get ready for Earl. He
was finished what he was doing in my area around 4, and could we get
together for around 4:30, to which I agreed was perfect.

Earl and I talked back and forth regarding the date, and
initially the plans were a dinner, then back to a motel so that I
could give Earl a private fashion show of some of my silkiest
bridesmaid and prom dresses. However, after re-thinking some of the
email I had sent him, requested that that would spoil the spontaneity
of the evening, and make the whole evening, and "end to the means",
and Earl and I decided that we would start with a nice dinner and go
from there.

Well, with my work, I can never guarantee that I can be in one
place or the other, so I made the plans and informed Earl, that things
may or may not work out. Well as luck would have it, a huge emergency
came up at 1pm the day of the date, and thankfully it was resolved
around 3pm, and I came racing home to get ready for Earl to arrive.

Prior to this happening, I had to decide on my wardrobe, Earl
informed me that he was to be wearing a jacket and tie, and asked that
I wore my semi-formal, extremely pretty blue silk blouse. Well, on a
Thursday night, the blouse was a little "too" formal, especially for a
woman coming from the office, but I decided that since I had never
worn the blouse out before, I would work with it and started to think
of which skirt to wear. I first thought of the most appropriate skirt,
which is my knee length black leather skirt, but decided that if I
were to wear that skirt that it would not be appropriate enough for
Earl to enjoy the silky sheer black pantyhose I was planning on
wearing. I had only one other choice that I was interested in and it
was a polyester black A-line skirt, about 2" above my knees. The
skirt, in combination with the blouse and silky black hose, was
definitely semi-formal looking, but it could pass as career-formal,
with the skirt. The heels were the next thing that had to be decided,
would it be my "career 3' pumps"?, my "formal 4' patent pumps"?, I was
not sure and decided to leave that decision to the final day when I
was in front of the full length mirror.

So with all of that set, and the day of the date arriving, the
plan was simple, Earl would pick me up at around 4:30pm, and we would
go for dinner and then he would take me home, and during that time we
were going to get better aquatinted. Now that I had my wardrobe set,
and I arrived home in time enough to possibly get ready in time. I was
set for another wonderful and magic time with Earl, who loved going
out with women that dressed to please their men. For Earl, that meant
lots of silk and lace.

As I arrived home, I had only 45 minutes to get ready for Earl,
and knew I needed at least an hour to get ready for him, so off I
went, showering, and such to get ready for him. I managed to get out
of the shower, dry off and started to at least slip into my lingerie
for the day. First it was my strapless bra, argh!, the bra from hell,
but it was the only one I could wear with this blouse, as it had sheer
panels right on the shoulders and the bodice, so I put it on. Next,
silky sheer lace and satin dark blue panties, they were my favorite
and thought of Earl's hands only inches away as he felt my silk
covered legs and started to get excited. Next, the pantyhose, and I
call these the pantyhose from HELL, they are ultra sheer, 10 denier,
and fussy as hell, so a pair of satin gloves ensured that there were
no runs and such with them, and they went on smooth. The bonus with
these hose is that they are ultra shier and make your legs feel like
satin, and will drive any guy crazy. When I was done, I slipped into a
low pair of heels, so I would not cause any runs by catching the hose
on anything on the floor. I finished the dressing with my warm terri-
cloth blue robe on, and moved to the well lit bathroom to start my
makeup.

Makeup application; and I decided was going to be a little
different, as recently my spouse introduced me to some new colours and
such, so the regular purple and pink on my lids was soon to change to
more rich earthy colours. After my foundation was all set, I moved to
the bedroom and a lighted makeup mirror for close application, for a
more dramatic application of my eyeliner, and eyeshadow. The new
colours were deep purple on the lower lids, deep brown on my upper
lids and dark brown for the outside edge of my eyes, quite different,
and as I looked at myself in the mirror. I liked the more dramatic
look of the eyeshadow, and knew that Earl would like it as well. I
then moved my way back to the bathroom, and applied a "business"
coating of blush and mascara, with a slight touch more and stood back
to admire the looked I created, and smiled as I knew Earl would like
it was well. The finishing touch of my makeup was a lipstick I knew
Earl would like, it was my favorite for formal wear, and knew Earl
liked the taste, and I applied a healthy coat, it was deep reddish
pink.

The phone rang part way through my lipstick application, and I
knew at the time the phone rang it was Earl, and as I answered he
sounded confident and such and I felt warm as I heard his voice and
knew the date was on. I informed Earl that I was running late and not
quite ready and he informed me that he had a little running around to
do, and I told him "perfect". We made the new time for him picking me
up as 5:30, so I slowed down the pace I had going, and continued to
get ready. The last piece of makeup I had to add was my nail polish,
and I chose a colour that match my lipstick closely, and after
sculpting my nails, and applying the polish my makeup application was
complete.

I then went back to the bedroom, where I had laid out my clothes
for the evening, all nice neat and ready on the bed. I then took out
my Obsession perfume, the perfume requested by Earl, and I knew it was
his favorite and dabbed healthy portions, behind my ears, on my neck,
wrists, and even on the ankles, I wanted Earl to smell the Obsession
even if he was walking behind me, or heaven forbid, he wanted to
worship my stocking covered feet!. With the perfume on, it was time
for the clothes, so off came my robe, and the first thing I slipped
into was my silky and very beautiful blouse, it so silky, I could
imagine Earl's reaction when he saw it, or potentially touched it for
the first time. Next the skirt, black, A-line, crisp and neat, it
falls just about 2" above my knees and it almost considered a mini,
but not quite and rides up nicely when I sit down.

Once my skirt was on, I completed my look with my gold anklet,
long dangly white pearl earrings, and formal gold watch. Now it was
time for the choosing of the heels. I started with my 4" black patent
heels, and used the well lighted mirror in the hallway to determine if
they were right. The 4" heels looked good, but they put the whole look
of the outfit "too formal", so I slipped on my 3" "career" black
heels, but they did not do the look of the outfit justice. So I
decided a compromise was in order and got my 3" pair of black suede
heels and tried them. PERFECT, they complimented the blouse and skirt,
and the overall look I had, and at the same time were low enough not
to portray a look that was too formal.

So with all of that set, I went about packing my purse for the
evening. I decided that since I was wearing the "pantyhose from hell"
that I would pack a spare pair of regular nude nylons in my purse just
in case I put a run in the silky sheer black hose. I also made sure I
had keys, and appropriate makeup packed, lipstick, blush, etc. While
packing those things, I was closing one of my drawers and noticed one
of my camisoles was sticking out of a drawer, and got an idea, I
bunched it up and stuffed it in my purse just in case things got
interesting during the evening.

Well, when I was all packed up, I went and got my coat for the
evening, my light spring coat and put it in the kitchen along with my
purse and then checked the clock and realized that Earl would be
arriving any second. I dashed to the washroom to check my final look,
and touched up my lipstick, and just then, I heard Earl pull up and
come to the back door looking for me. I looked out the bathroom window
and told Earl that I would be right there, and finished up and made my
way to the back door were I let Earl in.

Earl immediately smiled as he saw me, and I knew my look was
perfect, he complimented me on my outfit and told me that I looked
pretty, and I smiled and thanked him. Earl was also dressed perfect
and knew that I would not be out of place being at his side, he was in
a nice jacket, tie and slacks. I then grabbed for my coat, and Earl,
being the perfect gentleman, helped me put on my coat, and after I
grabbed my purse we headed out the door for the evening.

Earl was the perfect gentleman, he opened the door for me, and
allowing me to slip into the car, and as I did, he reached in and
handed me a little teddy bear that had a card that read "you're
special", and smiled and thanked him. As I got settled Earl closed the
door. Now, it was not my fault, but the skirt's, as I sat down, the
skirt rode up, and I did not attempt to adjust it, but rather, opened
my jacket so the passing trucks could see my legs. Ultimately it was
to please and tease Earl, but I knew that he would be the perfect
gentleman for the ride to the restaurant.

Earl and I shared idle talk as we made our way to the restaurant
which is a favorite of my spouse's and Is to go to, it is quiet and
the food is good, and is in a perfect location, right on the border of
my city and the next. The ride took about 15 minutes and Earl and I
shared casual talk about his trip and the seminar and such, he was the
perfect gentleman and it was really nice, I was feeling very
comfortable being with Earl already. Before I knew it, we were at the
restaurant, and Earl was being the perfect gentleman again, asking if
I would like to be dropped off at the door while he parked the car. I
said no, but before I knew it, he found a place right in front of the
restaurant. Earl then got out of the car and came around to my side of
the car and opened the door for me, again, the perfect gentleman.

Earl took the lead and opened the front door of the quaint
roadhouse and allowed me to enter, and once I got inside I looked
around, saw the fireplace, and felt the warm atmosphere that my spouse
and I have so often got when we came to this place. I pointed out to
Earl a booth at one end of the restaurant, we were greeted by the
waitress and Earl took the lead and requested the table, and lead to
our seats. I slipped off my coat and placed it on the bench and as I
sat down, made sure my skirt was down as far as it could go, as I did
not want to give the couple seated in the perfect position a show.

Earl and I looked over the menus and I ordered a drink, then
excused myself as I used the ladies room, and as I left Earl, I could
feel eyes looking at me, but admiring eyes, those of Earl, and I felt
warm inside. The ladies room was always as I had remembered it, soft
feminine and such. I took care of my business and came out and used
the long full length mirror to ensure I looked perfect, then went to
the full length mirror, and on the counter top was a fresh bouquet of
flowers, very sweet and feminine. I proceeded to apply another coat of
lipstick, as I wanted Earl to always see my lips perfect and inviting.

Earl and I looked over the menu and decided that we would order
an appetizer first, and we decided on Mozzarella sticks, and then we
would order dinner a little later, as I think both of us wanted the
night to be enjoyed and dinner last as long as possible. Once the
mozzarella sticks came our light conversation continued, and then the
question by me, "would your wife ever go through the trouble to make
sure your wishes were granted?, I mean perfume, lace, satin and
lipstick?", to which a smile and a "no" came over his lips. I then
decided I would see if Earl was paying attention, and grabbed a
mozzarella stick and SLOWLY allowed the stick to slide into my lips,
all the while savoring it with my eyes closed, and of course glancing
over at a smiling Earl. After each "bite" of a stick, I would carry on
the conversation as if nothing had happened, and noticed that Earl
smiled each and every time.

Earl and I ordered dinner, I was not really hungry and settled
for a salad, and Earl ordered something light as well. Dinner was
uneventful, well above the table at least Earl and I carried on casual
conversation, I slipped my left foot out of my suede pump and
proceeded to find Earl's leg, and the bottom of his pant leg, and
started massaging his leg with my sheer stocking covered leg. The
humorous part was that in full view of a table just located a few
yards away was a family dining, and a boy, maybe 15-16 was in full
view of my footsie show, and I could tell that he was most likely
enjoying this as much as Earl, and gave the eventually smile to him as
I snaked my sheer stocking covered leg up Earl's pants, against his
bare skin, and he quickly would glance away, what a tease!.

The family eventually finished their dinner and I made another
trip to the washroom to fix my lipstick, add another healthy spritz of
Obsession perfume to my wrist and neck and use the facilities. When I
returned, Earl and I ordered coffee (special coffee for me), and
continued to talk, this time a little more personal. I continued to
massage Earl's bare leg with my stocking covered foot, and this time,
looked at Earl and asked him if he liked it?. His response was, "I am
having a hard time to stay comfortable", to which I smiled and knew
exactly what he meant, and pictured the "beast" straining against his
pants, and knew at some point the evening, due to the events so far, I
would get to "tame" the beast.

It was nice and dark and Earl and I decided it was time to leave
the restaurant, and proceeded to wrap thing up, I finished my drink,
and Earl his coffee, and after one final trip to the ladies room to
fix my lipstick I was ready to go. Earl paid the bill, as the perfect
gentleman once again, and before I slipped on my coat, I asked Earl
what he wanted to do. He suggested we find someplace quiet to continue
our "conversation", and I agreed, knowing full well what kind of
"conversation" both of us wanted to carry on.

Earl and I walked back to his car and once he opened the door for
me, and I slid in, I made sure that my skirt would do what I thought
it would, and slide up far enough without exposing my vagina, allowing
for maximum leg and stocking exposure. Earl asked for directions and I
gave them to him, and the directions I gave him would allow us a
longer trip home, along the lake, and if the opportunity arose, a nice
quiet place to stop.

As we started driving, Earl knew that the exposed leg was for
him, and proceeded to place his hand on my thigh and started caressing
my sheer stocking covered thigh as he drove, and continued to enjoy
the offering I had put before him. We continued to chat, and Earl
continued to enjoy my leg, and before long, we made our way to a
gardens area I knew was along the way, and I pointed it out to Earl
and we pulled in. There was a vehicle in the parking lot when we drove
in, and it was a big parking lot with areas that were completely in
the dark. Earl and I looked around and decided to wait for the vehicle
to leave. When it did, proceeded to find the quietest and darkest
corner and "parked".

Once Earl turned off the car, it did not take words to express
what both of us wanted, and in a flash we were necking and Earl's
hands were all over the silky blouse I had worn for him. Our kissing
was intense and our tongues intertwined and I allowed Earl to fully
enjoy the blouse as he caressed almost the whole thing, and even my
breasts. I was also exploring and eventually found that there was a
rather large bulge in Earl's pants that I started to massage through
his clothing. At one point we broke and I suggested that we get more
comfortable in the back seat and Earl and I both opened our doors and
slipped into the back of the car, I felt like a teenager again, a
young horny one that is!.

Once in the back seat, Earl continued to caress my blouse and
stare into my eyes, and I asked him "what do you want?", and his reply
was, "I want you to do to me, what you did to the mozzarella sticks",
to which I smiled and knew exactly what he meant, he WAS paying
attention. I then started kissing Earl and at the same time, undid his
belt and pants and when it came to pulling down his pants and
underwear, he helped and before I knew it, the "beast" was free, and a
full erect 8" of pulsing manhood was before my feminine lips. I
quickly took charge and "tamed" the beast and took it in my hands and
started to play with it, much to Earl's delight, it was truly a sight
to make any woman hungry!. I leaned over and opened my lipstick
covered lips and briefly wrapped them around the head and sucked a
little, flicking my tongue around the head. I then made my way to his
balls and gave them a little attention. I guess a little too much as
Earl got a little uncomfortable.

I then sat back up, still caressing Earl's member, and asked him
about protection, and when the answer was negative, knew that my
backup plan would have to be used. I reached for my purse in the front
seat and pulled out my slip and showed it to Earl, and he groaned. I
circled Earl's solid member with the slip and started pumping him, and
he enjoyed the attention, and threw his head back and groaned. He
continued to enjoy the blouse I wore for him, and from time to time,
we would kiss, passionately, tongues dancing, and I knew Earl was
getting very excited. Earl stopped me at one point and asked me to get
a tube of lubricant, and it had a sweet smell to it as I poured it
into the palm of my hand, "pina-colada" was the "flavor". After
pouring it into my hand I started to pump Earl up and down, all the
time talking about how I dressed for him and such and how silky my
legs and blouse were, and eventually I used my free hand to massage
Earl's balls as I continued to pump.

Earl was in total ecstasy, he groaned and moaned and I enjoyed
watching my lover get hotter and hotter, and eventually he started
getting louder and I knew he was going to cum. I watched as streams of
cum left his hard and erect member, shooting high up, over and over.
Eventually, he was spent, and came at least 5 good spurts. Earl was
prepared and brought paper towel, which I got and used to clean up him
and the spots on the car seat were he made a mess; as I explained to
him, it is the woman's responsibility to clean up the mess, and I also
explained that one day, there would be no mess, also it was such a
waste for all of that cum to end up in a paper towel, and he agreed
that one day.......

After, Earl and I started to get dressed again, for Earl it meant
putting his pants back on, and for me, it meant slipping back into the
front seat and applying another coat of lipstick. Earl and I then left
and decided that we would stop at a roadhouse on the way back, as he
still had time to spare before Earl had to leave, and I really had to
get my hands washed.

Earl and I entered the roadhouse, and once again he was the
gentleman and took the lead and found us a table, and we order
something to drink. I excused myself and took a trip to the washroom,
and washed my hands and did my business, and afterwards came out of
the stall and went to the mirror to touch up my lipstick.

Earl and I carried on chatting over our drinks, and occasionally
I would spot a woman or two admiring the blouse I was wearing, and
smiled back at them, and it was all so warm and comfortable. Once we
were finished our drinks, Earl once again was the gentleman and picked
up the tab, and we left the roadhouse.

Earl caressed and enjoyed my leg all the way back to my house and
on the way back, we stopped briefly and kissed good bye before we got
to the driveway of my house, and I thanked Earl for a wonderful
evening, and he thanked me as well.

I got out of the car and watched Earl pull away, and thought what
a lucky girl I am to have such a sweet and caring man like Earl. I
went to bed that night in a long white sheer gown, dreaming of Earl
and his soft and gentle hands caressing my stocking covered legs.

Epilogue:

Earl still calls and emails me from time to time and hopefully soon
enough we can get together soon, which will be another great evening I
am sure.

**Transgender Stories** · 05-20-2008, 01:34 PM

Wednesday October 17th, 2001

I have had many exciting and wonderful and memorable trips out,
but this one is one that I will never forget.

Earl and I have been emailing each other back and forth for a few
years and have already had a couple of wonderful dates. He certainly
loves the idea of Brides and white lingerie and clothing, as well as
satin and lace Bridesmaid's. We have always talked about one day him
coming to my town, taking me someplace while I was wearing a white
Wedding dress and "getting married", having a "honeymoon" and the
whole experience.

A recent trip to a city nearby had him contact me to see if I
could join him for an evening, which I readily agreed!. We chatted
back and forth via email and the evening was starting to take shape. I
told him I had recently gotten a nurse's uniform and he asked if it
was possible if we could have an early dinner. I then could model the
nurse's uniform, and possibly my French Maid's uniform and finally a
Bridesmaid dress all in the privacy of his hotel room. I told him as
long as we had enough time that it would be possible and he told me
that he would make the arrangements so that we would have enough time.
I thought it would be fun if he came up with names for the characters
that were going to be wearing the outfits, and he did. "Jolene", was
going to be the French Maid, "Margaret" was going to be the nurse and
"Stephanie" was going to be the Bridesmaid. The clothes were picked,
the French maid and nurse were easy, but he chose a pink Southern
Belle Bridesmaid dress that required a very large crinoline slip
underneath, and that required some special packing. I also asked him
what he wanted to see "me" in and I offered sexy or more conservative
and he chose sexy for the dinner out.

When he told me sexy I knew exactly what I was going to be
wearing, and that was a very short black skirt (barely covering my
bottom), matching jacket, white blouse with white silk lapels, sheer
black stockings and 3 1/2" black patent pumps. The suit I chose was a
present from a former boyfriend that bought it for me, but has since
disappeared and has never seen me wear it, so I thought it would be
nice for another boyfriend to appreciate it. The plan was set that he
was to pick me up at around 4:30pm and then we would go to a quiet
place for dinner then back to his hotel afterwards and then I could
model the different outfits and he could "meet" the different
characters. As the date approached he mentioned that we would like to
"snuggle" up with me in some silky lingerie at the end of the evening.
I told him that I would definitely enjoy that and suggested that he
supply the lingerie to enhance his enjoyment at the end of the
evening. One email that he sent me had me intrigued he asked me, "what
is your ring size?, if we are going to be married, we should be
properly engaged first". I answered him but did not think anything of
it, as I have had dates in the past that ask rhetorical questions and
nothing happened, so I brushed it off.

So with the itinerary set, and the date approaching, I decided to
take the entire day off from work of the big date to make sure I was
nice and ready. I spent most of the day packing and taking a couple of
showers to make sure my body was smooth and silky. I emptied out one
of my Wedding dress bags to pack the clothes for the trip back to the
hotel room. I pulled out each outfit and carefully inspected each one
and grabbed a tote bag and started backing accessories, shoes,
stockings etc. For the nurse's outfit I decided to make sure it was
going to look sexy inside and out and decided on some very special
accessories. I chose a very sexy and lacy merry widow with garters and
sheer white stockings and of course white 4" heels. I decided that the
first outfit that I was going to wear in the hotel room was to be
"Jolene", the French maid, as I would not have to change out of my
sheer black hose from my "sexy business look". Earl and I talked and
he told me that he wanted to see the Bridesmaid as the last outfit, so
with the Nurse's lingerie and such, everything was going to work out
well. I went over everything 3 and 4 times and made sure it was going
to be perfect, there was no room for an error, as everything had to be
packed.

Earl called me the night before to firm up the details, we kept
our conversation civil and made sure all of the plans were set. I
could tell by the quiver in his voice that he was excited and I was as
well, but we managed to plan the next day and the final details. He
was going to try and get off work a little bit early and one final
request was that I wore my "straight hair" rather than "curl hair". So
the final arrangements were done and I was tingling as I went to bed
Tuesday night getting ready for the next day.

Wednesday morning came and I was starting to get excited, once
the house was clear one last quadruple check of the outfits, I had the
bags right by the front door as well as my light spring coat. During
the day I slowly started getting ready an around 1pm, work got in the
way and I had to spend about an hour and a half on the phone, and
before I knew it, it was 2:30pm!!. I quickly jumped into the shower
and did the last of the cleaning I needed to do and made my way to my
bedroom to slip into my lingerie. I grabbed my favorite lacy white bra
and slipped it on, and then a pair of lacy and silky white tap pants.
I then grabbed a brand new pair of sheer black pantyhose and carefully
slipped them on, I used white satin gloves to make sure I did not put
a run in them. The house was still warm and I did not bother with a
robe and just slipped into my low 1 1/2 black pumps and made my way to
the mirror to start putting on my makeup. I put on a "business" style
of makeup, my eyeliner was not that heavy and I chose my new style of
purple for my eyeshadow. I highlighted the edges of my eyes with a
charcoal colour and then applied a health dose of mascara to highlight
my eyelashes. I used my darker blush to highlight my cheeks, but made
sure it was not that much, and hoped it would be perfect. I decided on
not putting on my lipstick until he arrived so it would be perfect and
not smudged.

I was still in my panties, pantyhose and bra when the phone rang,
it was Earl, he told me he was just on the highway entering my town. I
was floored!, not only was he going to be about on time, but I was
still not dressed and had not even done my nails!. So we set a later
time for him to pick me up and I started scrambling to make sure I
could meet the time I told him to pick me up. I quickly grabbed my
nail polish and sat down and did my nails. When they were done and
dry, I grabbed my Obsession perfume and doused my body, from my ears
to my ankles. I was just putting on my skirt when the phone rang
again, it was Earl, and he was about 5 minutes away and I asked for a
little more time. I then grabbed my white blouse and slipped it on,
then the jacket and finally my 3 1/2" black patent heels. I went to
the bathroom mirror and applied a healthy coat of my dark reddish
lipstick, and as I smiled at myself, I knew it was Earl's favorite. I
grabbed my purse and headed upstairs to the full length mirror to see
if the look was right and nearly died. It looked perfect, the skirt
was very short, the whole look was professional and the silky hose and
3 1/2" heels made it even more perfect. I was admiring myself and
making sure the skirt was adjusted right when the doorbell rang, it
was Earl!.

I quickly checked to be sure that my lips were alright and
grabbed my purse and headed for the door. I opened it and there was
Earl, looking as handsome as ever in a suit and tie. I invited him in
and told him where the bags were that needed to be packed and he took
them out immediately to the car. When he came back he smiled at me and
told me that I looked gorgeous and as I grabbed my light spring coat
and he helped me slip it on. He walked me to the car and opened the
door for me and I slid in. As I sat down, I made no attempt to adjust
my skirt as it rode almost to the edge of my panties, showing maximum
leg. When Earl entered the car I opened my long coat to allow him the
view my silky black stockinged legs. He drove to the area that his
hotel was in and was exchanged pleasantries as he did. He did not make
any advances towards me as he drove and it was comical as the place he
had chosen he could not remember exactly where it was and we spent a
little bit of time trying to find it. Eventually he found it, it was a
bistro, a little restaurant off the entrance to a hotel.

We parked close and he came and opened my door for me, I slid out
and was surprised by the wind, it was literally "howling". My hair
flew around as we walked to the entrance to the bistro, I knew I would
need to use the ladies room when I got in. As we got inside the front
door I used my hands to try and make it presentable. I followed Earl
into the restaurant, and we where greeted by a waiter that asked where
we wanted to sit, and Earl told him, "someplace quiet". He found us a
place and then offered to take my coat and helped me off with it and
went to hang it up, but before he could leave, I needed to find the
ladies room and asked where it was. He told me to wait for a minute
and after coming back from hanging up my coat he told me to follow
him. I left Earl at the table and followed him and we left the
restaurant area and straight into a construction area!, he lead me to
the ground floor ladies room and then walked in!. I thought "what the
heck?", but followed him and in there was a guy working in the
stalls!!. I quickly turned and left and he followed and told me,
"right this way Miss I am terribly sorry" and tried to use the
elevators, and he was told they were not working, that there was
temporary washrooms upstairs, room 214 and 215. He turned to me and
showed me the stairs and said, "I am really sorry for the
inconvenience Miss, please use the washroom in the room upstairs." I
walked up the stairs and could not help but notice the amount of dust
that was everywhere.

I was looking around everywhere for this room 214 or 215 and kept
on passing a Chinese woman that that on the phone screaming at
someone. I found a room that had a piece of paper with "men" on it,
but the rooms were not labeled right!, then I noticed on the floor a
piece of paper that had "women" written on it. I had to go and did not
care and picked up the piece of paper and put it on the door. The door
was open and I went in, and quickly found the washroom. I locked the
outer door of the washroom as well as the inner door, as I sat down to
do my business. When I was done I made my way to the mirror and
adjusted my fussy hair and touched up my lipstick. I then headed
downstairs, back to the restaurant to a smiling Earl.

Earl and I got caught up and eventually the moment happened and I
extended my hand and he held it for the first time during the day, we
smiled back at each other and it was special. He told me that I had
gotten dust from the construction on my black jacket and help me clean
it off. Earl and I had a wonderful time catching up on things and the
sun was coming in the window right beside us, made the mood so
romantic. We ordered dinner, he ordered lamb and I ordered a Greek
Salad and a glass of wine. Except for a couple of other people, we
were the only ones in the restaurant and it was really nice and quiet.

Then he totally surprised me and got out of his seat and held my
hand and dropped to one knee and asked me to Marry him!!!. He pulled
out a lovely silver engagement ring and slid it on to my ring finger
and it fit perfectly!. I was floored, but the ring looked so lovely
and the setting was so perfect, I definitely said "yes!". Then the
first kiss of the evening happened, and it was a passionate one, his
tongue was in my mouth and I reciprocated, it was heaven. He sat back
down and I had to giggle a little and told him to fix his lips as my
lipstick was all over his lips. Dinner came and I was on "cloud nine",
I kept on staring at the ring, not thinking that what happened
actually did!. My smile stayed with me the whole dinner, and I could
not believe what Earl had done, I was an "engaged" woman!, AGAIN!.

I barely remembered my dinner and munched away at it and could
not stop staring at my finger. Earl was worried that it did not fit or
something and I just smiled back at him and told him, "it is perfect".
We held hands during dinner and exchanged pleasantries and I could not
stop smiling. I tried a couple of times to play "footsie" with him and
rub my silky stockinged legs up his pants, but the table was too wide.
Eventually we were both done our dinner and I ordered one last glass
of wine and we soaked up the atmosphere. The waiter was slow with
bringing us the check and I could tell Earl was anxious to get going
back to the hotel. I had to use the "ladies room", again and saw that
the waiter was talking with some of his friends at the bar and told
Earl that I would be right back. I had a big smile on my face as I
grabbed my purse and headed for the washroom. I walked up to him and
held out my finger and said, "I just got engaged!!". He smiled back
and said, "congratulations Miss", I then asked if we could have the
bill and then walked into the construction area and upstairs to the
room that was designated as the "ladies room". I did my business and
freshened up and checked to make sure my lipstick was perfect and
headed back downstairs.

I met Earl who was just settling up the bill and the waiter was
still there and he was leaving us, he said, "congratulations again on
your engagement", we both thanked him and I started looking for my
coat. It was hanging up in the back and Earl and I walked toward it,
and he grabbed it and helped me slip it on. He then lead the way and,
out into the howling wind we went. He opened the car door for me and I
slid in, and the same as the last time, allowed my skirt to ride up to
wherever it wanted to go and showed maximum leg. The ride to the hotel
was short, and Earl's hand was all over my silky legs and enjoying
them as he drove. At the hotel Earl grabbed the large garment bag and
the tote bag from the trunk and I followed him into the hotel. Then
for Earl, the unthinkable happened, he ran into some coworkers, they
made a comment about the bag he was carrying, and he started to walk
much faster. At first I did not know why, but then clued in real fast
and slowed down my pace to put some distance between the two of us. At
one point I was a little scared as he made the turn around one corner
and then another and I thought I lost him, but thankfully I spotted
him in the distance and walked that way.

We eventually made it into his room and after hanging up the
clothes bag and dropping the tote bag, I joined him on the couch for a
long and inviting kiss. He opened a bottle of delicious wine and
poured us each a glass and we toasted our engagement, I also noticed
on the bed was a Victoria Secret's box and 3 beautiful red roses. Then
he gave me another long kiss, with our tongues intertwining, he was
feeling up my legs and then finally my breasts, I had to reach down
and find "the beast", that was straining against his pants. At that
point he broke our kiss and said, "I think I want to see 'Jolene'
now". I stood up, smiled at him and went towards the bathroom and
opened the garment bag and pulled out the French Maid's uniform and
the tote bag.

In the bathroom, I fixed up my severely smudged lips and then
slipped out of the jacket skirt and blouse and into the French Maid's
uniform. I also applied more Obsession perfume to my neck and wrists
and finally slipped into a 4 3/4" pair of heels that I packed for the
outfit. I put on the white satin apron for the outfit and looked
myself over and then finally entered the room. I could tell by the
look on Earl's face that he was pleased with the look and slowly made
my way to him. I immediately went into character and curtsied in front
of him and said, "what can I do for you sir?". He motioned for me to
lean forward and gave me a long probing kiss and then broke it and
asked me to sit on his lap. I did and he felt me up as we continued to
kiss and he certainly was enjoying the black satin of the uniform and
the frilly "sissy" panties I was wearing under the skirt. I kept using
the words, "yes sir, no sir", and asked him at one point, "and what
else can I do for you sir?", He said flatly, "undress me now". I took
off his shirt, jacket and tie, then moved to my knees to undo his belt
and pants. Once they were off, I was staring a large bulge in his
underwear and started rubbing it. It was at that point that he asked
me to stand and said, "I would like to see Margaret now, I have
something that needs a nurse to look at". I smiled and stood up,
curtsied him and then left for the bathroom.

I slipped out of the maid's uniform and my black pantyhose and
grabbed my lacy white merry widow and slipped it on. Next were the
stockings, sheer white and I slipped them on and did up the garters.
Before I slipped on the nurse uniform I had to again fix up my smudged
lips. I then put on the nurse's uniform and then into a pair of white
4" heels and went back into the room. Earl was still sitting there,
bulge and all, and as I walked towards him he said, "nurse Margaret, I
have a problem in my underwear, can you help?". I turned around and
gave him a little fashion show and pulled up my dress so he could
enjoy the garters and stockings, which he did. I turned back around
and kneeled before him, then gently caressed the front of his
underwear, he was hard. I then peeled back his underwear and there it
was, "the beast", a solid 8" of thick manhood. I leaned over and
kissed the large head, leaving a lipstick mark on it. Then after
grabbing it and admiring what I had done, I started licking the head
and the pre-cum that had formed. I put the head in my mouth and licked
and could hear Earl groaning, he then put his hand on my shoulder to
stop me and told me "I want to see Stephanie now".

I stood up and kissed Earl again and then headed for the
bathroom. I grabbed the very large crinoline and the pink Southern
Belle dress and went into the bathroom. As I was changing into the
role of "Stephanie", I did notice some KY lubricant and some rubbing
lotion on the bathroom counter, and wondered what it was for. I
touched up my lips again and then slipped into the large crinoline and
then slid the dress over my head and down. Then grabbed the matching
pink satin 3" shoes and my elbow length white satin gloves and put
them on. I adjusted my bra to the sides so it would not show and then
went back in the room. Earl was certainly pleased and said, "nice to
meet you Stephanie, you look love then this evening". After a long and
probing kiss, I paraded around for him and he loved the satin material
and could not get enough. At one point he turned me around and walked
me to the edge of the bed and gently pushed at my back, which I knew
was a signal to bend over and I did. He then flipped up my skirt and
started thrusting his hard member against the crinoline and was
groaning all the while. At one point I felt a hand go to my crotch
area and gently whispered, "no", and he backed off. After enjoying the
dress and crinolines for some time, he then said, "I want to see
Jennifer now". I stood up from leaning over the bed and he handed me
the Victoria Secrets box and told me, "please keep the satin gloves
on?". I just smiled and walked into the bathroom with the box and
could not wait to see the lingerie and what he had chosen.

I carefully got out of my dress and then slipped off the
crinoline and before I changed out of my lingerie, decided to see what
colour the lingerie was, as I may have kept on the Merry Widow and
stockings. I opened the box and saw that it was black and at that
point decided that I might as well change back into my silky black
pantyhose. I got out of the merry widow and grabbed the lacy part of
the black lingerie, which was a camisole and slipped it on. Then I
grabbed the second part, which was a pair of long satin pants and
slipped them on. I topped the outfit off with my 3 1/2" black patent
heels and looked at myself in the mirror. Except for the fact my
lipstick was a mess, the look really was not "me" and was glad that
Earl had saved the receipt as it was still in the box.

I fixed my lips and touched up my blush and then opened the door
to the room and noticed Earl had dimmed all of the lights. He was in
bed and pulled the covers back for me and I slid in, heels and all. We
immediately started kissing and he had his hands all over the silky
lingerie, I then asked him to suck my breasts and he peeled back the
camisole to expose very pert and ready nipples and he did. I reached
down and could feel he was still hard and ready and then eventually
slowly kissed my way down to "the beast". I started immediately to
lick and suck it and used my satin covered hands to caress his balls
while I did. He was groaning and really enjoying the feminine
attention that I was giving him. At one point he tried to stop me and
told me that there was lotion in the bathroom and could I get it. I
quickly realized he wanted me to jerk him off and I said in a husky
and sexy voice, "oh no dear, tonight the beast is mine!", and started
to pump up and down with my lips even more. He then groaned, "but it
has never happened before", I stopped and I was still pumping with my
hands and asked, "what has never happened before?". He said, "to cum
like this, it has always just been a part of foreplay". I knew I had
my work cut out for me and I wanted his oral virginity!, so I worked
even harder and tried a few tricks to increase his stimulation. One
was to use a little bit of teeth, but he groaned at one point, "watch
teeeeth", so I stopped.

He started to groan and groan in between my lips and I could feel
the beast get harder, then softer at times. At one point Earl put his
hand on the beast and started stroking it furiously, he asked me to
rub his balls with my satin covered hands while he did. He started
grunting louder and louder and then finally between his grunts he
said, "now, now!". I opened my lips and started pumping and then he
shot two little loads that I swallowed, then about ten seconds later
he shot about 5 loads that I eagerly gobbled up. I kept him in my
mouth until he started to go soft and as he popped out of my mouth, I
licked him clean then looked up at him and said, "yummy". His head
fell back on the pillow and I got up and had a sip of wine as he
recovered.

I left him in the bed as I went to the bathroom to change back
into my skirt, blouse and jacket. I did and then had to once again fix
my lips as they were ruined. I gathered all of the things that I had
brought and double and triple checked the room to ensure that I had
not forgotten anything and then left and checked the garment bag. Earl
was in the process of putting back on his suit and I went and gave him
a little kiss and helped him clean up a bit. When the bags were packed
and Earl was dressed, I relaxed on the couch and sipped on more wine
while Earl was looking over some of my photo albums. I made sure that
my legs were good and exposed and he certainly enjoyed them. It was
about the time to go and Earl grabbed the bags, but not before adding
the beautiful red roses to the bottom of the garment bag, and then we
headed back out to the car.

This time, Earl asked me to right off the bat to stay a fair
distance behind him as we walked to the car, and I totally understood
and did that. Everything worked out well, and as I walked to the car
to join him, I noticed the howling wind had not stopped. After packing
the bags in the trunk, he opened my door and I slid in, and this time
I actually had to adjust my skirt to expose maximum leg!, and opened
my coat and used the mirror on the visor to adjust my hair.

We held hands all the way home and every once in a while he would
let go and feel my silky covered legs. When we got close to my place,
I noticed we had a few more minutes before I was expected home and
asked if he wanted to go parking to, "enjoy my sexy legs". He said yes
and I directed him to a mall near my house that I knew had a few dark
corners in it. He parked and then we kissed a little, but he wanted my
legs, so I sat back and slid my legs up on the dash for him to enjoy.
I asked him to suck my toes and he took off one of my shoes and did
it, and the feeling was incredible, but after a bit he slid my shoe
back on and told me that it was not really "his thing", which I said
that was fine. He continued to enjoy my legs and every once in while
we would kiss. In the distance we saw car lights and the past once,
then twice, then again, then finally in the distance, just pointed to
us. Earl was worried it was the police, but I reminded him we were not
doing anything lewd or illegal. He was uncomfortable, so we left the
mall. On the way back to my house, I directed Earl to a side street
and we parked and started kissing. Then the lights came back, and we
figured it was a group of teenagers out to ruin someone's romantic
fun, or to watch. We then decided it was time to end the wonderful
evening that we had just had, and Earl started the car and took me
home. I took one last look at my lips with my lighted compact and made
sure they were perfect, as my spouse was probably sitting up waiting
for me.

We kissed lightly in the driveway and he then went for the trunk
and the garment bag and I searched my purse and found my keys to the
house. He opened my door and handed me the garment bag and the tote
bag and we ended the whole evening with a light kiss and we both
agreed, "we could not wait for the actual Wedding day (night)". I
heard the car back up as I walked across the driveway, trying not to
fall in my heels on our gravel driveway.

I dumped everything downstairs and saw that the lights were still
on upstairs and went and saw my spouse, who was sitting down and
reading a book. She looked me over and smiled and asked me if I had a
good time and I told her I certainly did and it was really nice
getting out. She told me that "she was glad", and I asked her what she
thought of my outfit and she told me, "well you would not catch me
wearing a skirt that short ever!". I showed her that I was planning on
having the skirt shortened more and she laughed and said, "it does not
even cover your stocking tops!, and look at the run in your nylons". I
looked down and dropped my skirt and said, "perhaps you are right". I
still cannot figure out how that one got there, so much for a pair of
$8 pantyhose!. For this evening I was staying in my own room and
sleeping in lingerie and I asked her what she thought I should wear
and she suggested one of the matching baby doll sets that we have. I
smiled and thanked her and headed downstairs to my room to relax and
unwind after a wonderful evening.

The evening you have read about was totally 100% reality, and was
exactly what I enjoy when dating my dream date,

**Transgender Stories** · 05-20-2008, 01:35 PM

Wednesday December 5th, 2001

My fiancee called me a week ago to see if I was available to get
together while he was in town for a business visit. Even though
correspondence was spotty we managed to arrange to get together on a
Wednesday evening. One of the first things I asked of my new husband
to be was what he wanted to see his fiancee wearing. At first he
mentioned that he wanted to see me in a special blouse that I wore on
our second date, it was a silky blue blouse with lace on the top and
requires a strapless bra to be worn. At first he wanted me to wear a
short leather skirt, but in the next email be sent me, he wanted me to
be in a long velvet skirt with possibly a silky slip underneath, and I
emailed him back and told him that I could definitely comply and
judging by his response, he was excited!.

We talked back and forth and all we really knew was that we had
only a little time, he was going to pick me up by 6pm and I told him
that I needed to be home no sooner than 9pm. He asked me to pick a
quiet and romantic restaurant and one that was economic, and I had the
perfect place in mind and it was only about 5 minutes away from my
house.

So the big day arrived, and I was getting nervous, not about
meeting my fiancee Michael, but the fact we had house renovations
going on and the fact they may not be gone in time for Michael to pick
me up. To add to the mix, we had no bathtub due to the renovations, so
I took the afternoon off work and managed to use a little wash tub to
do my legs and make them smooth and clean, I managed, but it was fun
trying!.

The workmen finally left around 4:45pm and I got as ready as I
could without getting dressed or makeup and at that time, and finally
started to get ready. Michael called around 5pm to say that he was on
the way and I asked him for a little extra time and to pick me up
around 6:15pm, and he told me that would not be a problem.

I had already picked out my wardrobe for the day and had it laid
out ready to go. The look was going to be a little too formal for a
Wednesday evening out, but I decided to stick with it as all we were
really going to do was have dinner at a place that I knew was going to
be empty and a quiet romantic walk. My fiancee asked me not to wear a
girdle for our date, but unfortunately I had to for my hips and
padding. I decided to wear a pair of silky white panties on the
outside to allow my fiancee clear access to my rubber vagina, and the
hard clit that it has.

I started with my makeup and decided that my eyeliner was going
to be a little heavier than normal business wear, but not as heavy as
a formal evening out. My eyeshadow was purple and was applied to both
the upper and lower lids, I thought it looked great. My blush was
applied a little darker than normal business, but again, not as dark
as a formal night out. I decided to wait for just before he was going
to arrive to apply my lipstick, it was one that he totally enjoyed and
was a dark reddish pink lipstick. After my makeup, I fussed with my
hair and applied a couple of hair clips that my spouse showed me how
to put in my hair and eventually I got it to a point I thought it
looked great. After my hair was set I doused my body in my fiancee's
favorite perfume and that was Obsession.

I grabbed the lingerie for the evening and started putting it on,
first was the strapless bra, and once that was in place I put on the
girdle with the garters attached and slid it into place. I carefully
put on the latex vagina and carefully "tucked" myself into place and
made sure everything was tight to give my fiancee a look and feel of a
real vagina. I then slid on the pair of silky white panties and fitted
them into place, and felt my hard clit just beneath them and knew my
fiancee would like it as well. Next were the stockings, sheer and
black and would be a perfect fit for the evening.

I checked the clock and saw that I had lots of time before my
fiancee arrived and decided to do my nails in a colour that matched my
lipstick. Once they were dry I grabbed my favorite blue silk blouse
and started to get dressed. Once the blouse was on, I tucked it into
my girdle and then slipped on the long velvet skirt, it was a few
inches below my knees, not my kind of length, but my fiancee requested
it and I wore it for him. I zipped up the skirt and grabbed a black
silk slip and slid it up underneath, it was not necessary, but again,
my fiancee wanted it, so I obliged him. Once I was dressed I looked
myself over in the mirror and was pleased, I looked exactly as my
fiancee has described he wanted me to be. I double checked my hair and
then finished off my look with pearl drop earrings, a gold ankle on my
right leg and 3 1/2" black patent heels. The last thing I put on was
my engagement ring, and admired it as I slid it on, and thought about
the actual Wedding day and what it was going to be like.

I checked my purse and the time and saw that I certainly had
timed it right and as I checked over my purse I grabbed the pair of
silk gloves that I used to put on my stockings and stuffed them into
my purse. The last thing I did before a final check at the mirror was
to apply my fiancee's favorite lipstick to make my lips perfect and
then made my way to the front hall to get my light spring jacket. As I
was doing that the doorbell rang and it was my fiancee coming to pick
me up for the evening. I opened the door and he immediately
complimented me on how I looked and smelt and loved what I had done
with my hair (thanks Sharon), I then grabbed my coat and he help me
slip it on and then escorted me out to the car. He opened my door and
I slid in and as he requested, pulled my long skirt up to expose my
legs and slip. We talked a little on the way to the restaurant, but
what he really wanted was to caress and enjoy my silky legs and I did
not stop him.

We got to the restaurant, and he came and opened my door and
helped me out and we walked in hand and hand. He took the lead and
asked for a quiet table, well, the place was pretty much empty, so
that was not a problem. Like a gentleman he helped me off with my coat
and pulled out my chair as we got comfortable for dinner. The waitress
came to take our order and I had an iced tea and a garden salad and
just smiled at my fiancee as he ordered. We held hands as much as we
could and talked about a number of things including the Wedding and
which dress he would want to see me in, which is one that I was
originally married in. Dinner came and we continued to talk, and me
teasing him by licking my lips and such, and every once in a while he
would tease me back and put a hand under the table and tell me how
hard he was. Except for us, a group of men were sitting and talking
and we pretty much had the place to ourselves, it was very romantic
and quiet. After dinner I excused myself and went to the ladies room
to touch up and use the facilities. The washroom was not that feminine
and quite frankly disgusting. After fixing my lipstick I headed back
to the table to join my fiancee and he was in the process of getting
the attention of the waitress to settle our tab.

When that was done, he helped me off with my coat and helped me
on with my coat and we left the restaurant hand in hand. He escorted
me to the passenger side and opened the door and before I slid in, our
first kiss of the night happened and it was a long one with our
tongues dancing together. After we broke our kiss, I slid in and
again, hiked my skirt up and exposed the silky slip for him to enjoy.
After he got in the car, we exchanged another kiss and this time his
hands explored my legs all the way to my crotch and for the first time
in the evening he explored the silky white panties I wore for him. He
stared at me in the eyes and said, "where to now my love?", I asked if
he wanted a stroll by the lake on such a wonderful evening, and he
did. As we drove to the lake, his one hand could not help but explore
my silky legs, garters and silky covered latex vagina. We parked close
to the lake and he came to open my door, I did one last check of my
lipstick before he actually opened the door.

The night air for December was really, really mild, except for a
light breeze off the lake, I really did not need a jacket, but wore
one anyway. He took my hand and lead me to the end of the pier towards
the lighthouse at the end of it and we really had nothing to say,
except staring back and one another. We passed some people out for
strolls and people walking their dogs, and of course I was the only
woman in heels and a skirt!. I could hear the gentle swishing of the
waves and it was definitely a romantic stroll.

We got to the end of the pier and behind the lighthouse, my
fiancee took me in his arms and passionately started kissing me, his
tongue was almost down my throat as we made out. All the while he was
caressing my velvet covered backside and feeling my breasts through
the satin blouse. We paused a few times for pictures to savor the
moment (which is a reminder to this girl, that if you make out heavy
with a guy, make sure to check your lipstick before pictures are
taken!!!). Needless to say the pictures turned out, but my lipstick
job was a total mess, I looked like a clown in them.

Our kissing continued and it was very passionate and we would
pause from time to time, and then, my fiancee grabbed my right hand
and put it down to his crotch, and lone behold he had undone his fly
and the "beast" was in my hand. We continued to kiss while looking
around, but we were alone, and I stroked the beast that was HUGE and I
used my thumb to spread the pre-cum all over the huge head. As I got
more and more excited I felt I needed to at least pay the "beast" a
visit with my lips and after breaking off one of our kisses I looked
around and saw we were completely alone. I leaned over and gently
started to lick and suck on the large head of the "beast", enjoying
the pre-cum that had formed. Eventually I opened my lips wide and
slowly started pumping up and down, but for only short periods of time
as I feared someone was going to come walking around the lighthouse
and we would be caught.

Eventually it was getting too much for my fiancee and he stopped
me and asked if I knew a place that was perhaps appropriate for me to
"tame the beast" that was not too far away and I told him I did. I
smiled widely at him and in a sexy voice said, "you mean someplace I
can have my dessert?", he smiled back and said, "yes, your dessert".
He then walked me back to the car, holding my hand the whole time and
we kissed deeply again as he opened the car door for me. As I slid in
I hiked my skirt up all the way to my silky covered latex vagina and
as my fiancee drove me to a park nearby he took advantage of the
opportunity and felt it up and enjoyed the stockings and garters. The
park was only about 5 minutes away and before I knew it we were there,
as soon as the engine was turned off, we were making out heavily, his
hands were all over my breasts and latex vagina.

I searched for the "beast" and found him, he was straining
against his pants and in a flash my fiancee had them down and the
beast was in full view, and looking very tasty. My fiancee looked at
me and smiled and grabbed it and said, "come get your dessert my
love". I leaned over and licked up the pre-cum that had formed and
then licked up and down the shaft and he certainly was very big and
very strong. As I massaged his balls I opened as wide as I could and
started to slowly start to lick up and down, flicking my tongue over
the head as much as I could. I thought I was doing well, as my lips
and everything was stretched as far as it could go, but again my
fiancee gently mentioned, "teeth" as he groaned. To say I was
disappointed would be an understatement, but my fiancee said, "here
let me help" and grabbed the beast and started to very quickly pump up
and down. I went and opened my purse and found one of the satin gloves
and slipped it on. As my fiancee pumped away I gently caressed his
balls with his favorite fabric, satin and in my sexiest voice started
talking to him about all things satin and silky and could tell he was
getting hotter and hotter.

Eventually he was panting and moaned out, "now Jennifer, now". I
quickly leaned over and opened as wide as I could and please my lips
over the head of the "beast" and started pumping as well. I could hear
him groaning louder and louder and then finally exploded in my mouth
and I swallowed all he had to offer. For the moment has was spent and
I sat up, and just as I did, he was still pumping, and groaned,
"darling there is more", it was too late and he wiped himself up
clean. He asked if I enjoyed my "dessert" and I told him that I
certainly did and it was delicious. He did his pants back up and we
started to drive home, it was a short evening, but an enjoyable one.
As we drove home, he continued to caress my latex vagina and legs and
was commenting on how he enjoyed my lips sucking on the "beast".

Before we got too close to my home, he pulled off to the side of
the road and we exchanged and long and passionate "goodbye kiss". As
he kissed me he explored my crotch more and enjoyed the silky fabric
of the blouse, and then unfortunately, the evening had to come to an
end. We pulled into the driveway and he gave me one last kiss goodbye
and I got out of the car and headed into the house, hearing my fiancee
pulling out of the driveway. When I got into the house I looked in the
mirror and saw that my lipstick was smeared all over the place and
sure was glad that I did go and see my spouse first!!!.

One of the lessons this girl has learned, is to know the size of
your man, especially if you love giving oral. So, we will see what the
future holds, I have asked my fiancee for the circumference of the
"beast", not only at the head but the shaft when he is fully aroused.
I certainly want to please my husband to be on our Wedding night,
rather than to hurt him!!!. As they always say, "practice makes
perfect", and no matter what it takes, I will "practice".

**Transgender Stories** · 05-20-2008, 01:35 PM

Late November 2002

It would help to read "Careful what you wish for", both parts, as well
"Dress shopping with Brenda", to totally understand this story.

Note, this a true story, some of the names have been changed, but
certainly not the events of the days!, this is taken right from my
diary entry of the time, please read the first part to understand this
one.

My name is Joyce Devries and it was a real life adventure
I will tell you about, Brenda, the woman I made love to as Joyce, had
an idea about her and her husband's Christmas party, well, here is
exactly what happened. My spouse knows about and totally supports me
as "Joyce"; she is an incredible woman, as you will see. I am 5'2",
TV, live near Toronto, Ont., Canada, pass quite well as a woman and
have done tons of "real life" things as a woman, this was a really fun
and romantic adventure.

Tuesday after the wonderful day that Brenda and I got together, I
got an email from her, and this is what it said:

"Joyce,

Thanks for the wonderful Friday out shopping to find my dress for
the Christmas party, now, I have a proposal for you. Brad has a co-
worker, his name is Eric, and he is not planning on coming to the
Christmas party because he does not have a date. Brad and I got
talking and I was just wondering if you would be interested in being
his date?. The party is on December 14th, and if you say yes, I will
talk with Brad and he can talk to Eric.

Let me know,

Love Brenda"

We exchanged a number of emails after that, I was asking her
about what he was like and if he knew who and what I was. Brenda told
me he was 22!!!!, yikes!, but Brenda told me I did not look that old
and I would be fine for him. She told me he was slightly overweight,
5'5", but a really nice guy, and Brad thought he might be gay or bi-
sexual as he had never seen him with a woman.

I spoke with my spouse Sharon about it and she said, "well you
have a closet full of formal dresses you will never get a chance to
wear out, and as long as he knows who you are, I would say, 'go for
it!'". I told Brenda on Wednesday evening via email and she emailed me
right back and told me, "Brad has already told Eric all about you and
I am going to have him tell Eric to contact you tomorrow, have fun
planning!".

Eric sent me an email that I got on Thursday after work and this
is what it said:

"Dear Joyce,

I would like to introduce myself, my name is Eric and I was
speaking with Brad from our company and he has told me that you would
accompany me to the annual company Christmas party on December 14th. I
am flattered and would really like your company, Brad has shown me
your website and you are a very beautiful and attractive woman. I am
5'5", 185 lbs, have a baby face, and am 22, and I hope my age does not
scare you. Would like to talk with you more to get to know you better.

Eric"

I answered Eric and we started meeting on-line and talking back
and forth, as well as a few phone calls. Over the next couple of weeks
we really got to know one another, I found a bunch about him and
really got comfortable with him. He sent his picture and he was
exactly what he described and explained that he never really got out
to meet women as he was so busy with work. He knew who and what I was
and did not care, he thought of me as nothing put a pretty and sexy
woman and would respect that and wanted me to be a woman the entire
evening.

I though about my dress for that evening and decided I was going
to wear the dress that I modeled for Brenda, it was a black silk
dress, with beading all over it, it was above the knee length. I
decided on a pair of ultra sheer black stockings, a black garter belt,
and my black lace bra and matching panties. I also decided that even
though I would not be able to dance in them, my black 4" patent heels.
I looked over my jewelry carefully and decided on a sparkly rhinestone
necklace and a gold and rhinestone bracelet that Sharon got me for my
birthday a year or so ago. The earrings were the tough part, as I did
not want to go "overboard" with the "sparkly" look. I found a pair of
short, rhinestone earrings and decided to go with them. So my outfit
was set and I told Sharon about it and her comment was, "perfect!, you
will fit right in, just remember to take off the heels for dancing".

Wednesday of the week leading up to the Christmas party came and
I was getting all excited, but that was about to change to be even
more exciting. I came home from bowling (as my male self), and my
spouse told me to be sure that "someone" went to her room. After I
showered and cleaned myself up, I went down into my "Joyce" bedroom
and I initially saw nothing. It was when I went into the bathroom,
hanging up on the curtain rod of the shower was a pink garment bag and
a big red bow, attached also was a card. I opened the card and it was
from Eric and it read exactly:

"Dear Joyce,

I Have thoroughly enjoyed our conversations and such over the
last while and I really am looking forward to taking you to the party
on the 14th, I have taken the liberty of providing you with a dress
that I really look forward to seeing you wearing for the evening.

Hugs,

Eric"

I dropped the card and immediately unzipped the bag, and there it
was, the red silk/sequined dress that I tried on when Brenda and I
went shopping, in my size, 13/14. I was floored, I knew the dress was
really expensive, and I already had chosen a dress to wear, and I knew
that it was not necessary!. Before I did anything I picked up the
phone and called Eric, he was not home, but I left him a long message
thanking him and that I would not disappoint him on how I looked for
that evening. I then checked my email and there was one from Brenda
waiting there, it said:

Dear Joyce,

By now you have found out that Eric has bought you your dress for
the Christmas party. When he found out you were going with him, he
wanted to do something so bad for you, and Brad knew about the dress
and one thing led to another, and there it is!. I picked it up, and
when I did, the sales woman remembered you, and when I told her it was
for you, she just reminded me about the bra and the fact you needed to
get appropriate shoes. I told her that I certainly would pass on the
information, and Sharon knows all about it, so expect to be going
shopping shortly!. See you at the party, and remember to wear the
right bra!".

Love Brenda

The other email sitting there was from Sharon and it was pretty
similar, just hers stated that I should be ready to go shopping for
accessories Friday evening and she would meet me after work and would
have a "girls shopping trip out" then dinner. She said she saw a
blurry picture of the dress and was not sure, but she thought of a
place that might carry the shoes that would match the dress or at
least compliment it.

Friday evening came and I was first home from work and started
getting ready for the evening out shopping. I checked my email first
and there was one from Sharon that told me to pick my outfit, but
change into my lingerie, hose and bra and panties and such, but
nothing more, she wanted to take a digital picture of the dress on me
before we went shopping.

I then went to my room and slipped out of clothes and started
dressing, I had a few outfits in mind on what I would wear, but I
decided that at the last minute I would let my mood dictate what I
would be wearing. I started with my favorite white lace, front closure
bra, a pair of green lace and satin panties and a pair of sheer nude
pantyhose. I used a pair of satin gloves to ensure that I did not snag
them, and afterwards, I put on a pair of 2 «" black pumps. I slipped
on my pink satin makeup coat and started looking through my wardrobe.
I was leaning towards a business suit, but I decided on a short purple
leather skirt and a purple sweater that I got from my spouses wardrobe
to match the skirt, many years ago, and with my 3" black "business
heels", this was definitely a "business casual" look. I took out the
skirt and sweater, and laid them on the bed.

I was just starting putting on my eyeliner and I heard Sharon
come in the back door and she called out "hello", and I called back up
to her that I would be a minute. She let me know she had to freshen up
and that there was no hurry, the stores were open till 9pm anyway.
After I did my eyeliner, I applied a "business application" of eye
shadow, blush and I applied a coat of light pinkish red lipstick. I
then slipped into my 3" black heels, put on my gold watch, and long
gold dangly earrings and checked my purse, then went upstairs to meet
Sharon.

I was still in my silk makeup coat and again asked Sharon wanted
the picture, and she said, "I want to take a digital picture of you in
the dress so that we can show the sales people what accessories we are
looking for you to wear". I told her I would be right back and went
and got the dress from my bedroom and then joined Sharon in the living
room. I pulled the dress out of the bag and Sharon said, "oh my God,
that dress IS gorgeous!". I slipped out of the robe I had on and then
after removing my shoes, into the dress. I zipped it up and turned
around and modeled it for Sharon. She showered me with compliments and
asked about my bra, and I told her I had a convertible one that I was
planning on wearing, but I would need her help in making sure the
straps would not fall off my shoulders. Sharon told me that she would
help, and then took a few pictures of the dress with a digital camera.
She then put the camera in her purse and told me that I should get
dressed so that we could go. I grabbed the garment bag and then went
downstairs to my room and slipped out of the dress and then into my
skirt and sweater. I then checked my purse and then went upstairs to
join Sharon.

Sharon looked me over and said, "nice, I like the sweater, looks
familiar", with a smile on her face, and said, "ready to go?", I said
I was and asked her about the driveway and if heels or boots were
needed. She told me that she backed the car up to the front sidewalk
and that I would be fine in heels. I looked her over and she was
dressed for work in a long dark floral skirt, a pink blouse, nude hose
and low, 2" heels. She told me that it was really cold and I went and
grabbed my long winter coat and put on my pink gloves and scarf and
followed Sharon out the door to the car.

The mall that Sharon thought we would have luck at was only 1
minute or so away from the house, the same mall that the salon we both
used. Sharon told me, let's check out, "Sinbad Shoes", which was a
shoe store that specialized in unusual shoes, one of the last places
other than the internet to find 4" heels and stilettos in any size. We
entered the mall and Sharon lead the way to the store, but on the way,
we past the salon, and Sharon said, "let's check in with Lianne, I
made you an appointment for tomorrow". I looked at her and said,
"what?", she then smiled and gently grabbed my hand and said, "I took
the liberty, you should look your best tomorrow night!". I knew that
she was right and we entered the store and Lianne was working the
front and recognized us and welcomed us. Sharon spoke up and asked if
my appointment was set for tomorrow, and she confirmed it was and told
me that she was looking forward to seeing me. The appointment was set
for 2pm and she was going to do to me what she did previously.

Sharon and I left the salon and headed to the shoe store that she
thought would be our best place to find shoes that would match the
dress. As we walked I reminded Sharon that I had a pair of 4" silver
sparkly heels and a matching purse and she said, "there has to be
something better". We entered the store and a woman about our age
greeted us and asked if we were looking for something in particular,
Sharon immediately pulled out the digital camera and showed her the
pictures of me in the dress. The sales woman looked at the dress and
said, "my that is lovely", and started looking around. Sharon and I
also started looking around and even though there was tons of shoes,
and some really sexy looking ones!. However, none really were any
better than what I had. Sharon and I thanked the sales woman and
walked out of the store, we got about 200 ft from the store and the
sales girl came running after us, her heels clicking wildly. We turned
around and stopped and she was panting a little but said, "the store
owner came in while you were leaving and I told her about your dress
and she might have something'. We walked back into the store and the
store owner was there, a 50-something woman and she asked to see the
dress picture and Sharon showed her. She then looked at me and said,
"what is your size dear?", I told her a 7, and she went into the back.

She came out with a box and a pair of red sequined shoes, they
only had a heel about 2 1/4", and kind of looked like the same shoes
"Dorthy" on the "Wizard of OZ" wore. She asked me to sit down, and
told me they were a size 8 «, but that is all she had. She then went
and got a pair of foam inserts and put them in them removed my heels
and slipped them on. I removed my coat and walked around in them and
posed in front of the mirror with them on. The height was way too low
for me, but all three of the other women agreed they looked nice and
would look nice with the dress. I looked back at Sharon and she gave a
nod, and I decided to buy them. I slipped them off and then put back
on my 3" black heels and the sales woman put them back in the box. I
then asked if they had a purse to match the shoes and told me that
they did not, but to try the accessories store in the mall. I followed
her up to the front of the store. She rang up the shoes and I paid for
them, $56, but that was alright as I knew the dress cost Eric a heck
of a lot more, and I wanted it to be special for him. The sales woman
put them in a bag for me and I thanked her and Sharon and I left the
store and back into the mall.

Sharon took the lead and told me were the accessory store was and
we walked to it, the salesman in the store came to us and asked if we
needed any help and I told him what I was looking for. He told me that
they had nothing like that in the store. I looked over at Sharon and
she suggested we keep looking. After we left the store, Sharon
suggested we go for dinner and then afterwards perhaps keep looking
for a purse to match the dress and heels. Sharon and I went back to
the car and she asked where we should go and I just said "Kelsey's",
which was a road house just near the house, but the risk was that
someone might recognize Sharon and figure me out, but she said, "sure,
who cares". We talked about the purse on the way to the road house
restaurant and she asked me about the sequined purse that I had. I
told it was silver and possibly could be appropriate and she said that
the heels were the most important part and that the purse I had was
more than appropriate.

We got to the restaurant and I took the lead as we went in. We
were met by the hostess and she lead us to a comfortable booth and we
both slid in, after removing our coats. Our waitress came and we both
ordered, myself, a salad and Sharon a club sandwich and both of us
ordered coolers. We chatted about the dress and the shoes and she told
me, "you are going to look spectacular and Eric is not going to be
able to keep his hands off of you". I reminded her that Eric was only
22!!, and she just smiled back and said, "oh in his sexual prime?, I
suggest you pack condoms in your purse". I told her she was being
silly and she got serious and looked at me and said, "no, I am not". I
asked her if she thought he would make a move on me and she just said,
"are you kidding?, a sexy woman in a sexy dress and all dressed up, a
horny 22 year old, what do you think?". I had to admit she was right,
and told her I was a big girl and that I could handle it and she just
giggled a little and said, "don't lead him on and tease him". I sipped
on my drink and smiled back and told her that I would not. She then
told me, "if you like, when he brings you home, I will make sure I
'stay out of your way'". I assured her that was not going to be
necessary, but she smiled back at me and said, "oh we will see".

We ate dinner and she asked me about where the Christmas party
was and I told her that it was at the Holiday Inn right in Oakville,
and she giggled and said, "I will be at my Christmas party there the
week after!". I was feeling kind of awkward, but Sharon grabbed my
hands and said, "don't worry you will have to scope out the place for
me!". Sharon asked me about my dress and I asked her about helping me
to making sure that my bra was going to stay in place and she told me
that a couple of little safety pins on each shoulder would be perfect.
After dinner I excused myself and Sharon was settling the bill and
headed to the ladies room. I was the only one in the room and headed
to the stall to do my business and after I was done, I came out and
went to the mirror and freshened my lipstick and fluffed out my hair.
I met Sharon back at the table and she was standing up and said how
lovely I looked and was slipping on her coat and I did the same and we
grabbed our purses and headed out to the car and then back to the
house.

When we got back to the house, Sharon and I changed into some
comfortable lingerie and then snuggled in and watched a movie before
retiring to bed together, I snuggled into her and fell asleep on her
breasts, it was lovely.

The week leading up to the Christmas part I spoke with Eric a
number of times and at one point he told me that he was going to be by
to pick me up around 5:30pm, as the Holiday Inn was not that far away
and drinks were being served at 6pm and dinner was at 6:45pm.

Saturday arrived and a minor crisis as well. Sharon was called
into work and would not be home until well after 6pm, so she could not
drive me to my salon appointment, which meant I was walking to it, as
I do not drive dressed. Before she left for work, she had me try on my
dress and showed me what had to be done with the little safety pins to
ensure my bra straps would stay in place and assured me that I could
do it myself. She then gave me a light kiss and told me to "enjoy the
evening and do not provoke anything you are not prepared to deliver".
I smiled back at her and told her I would not, and would take care of
any "problems" that I caused. Sharon smiled and reminded me that my
appointment was for 2pm and there was lots of snow on the ground, and
to wear as little makeup as possible to the appointment. She gave me a
little kiss and left for work saying, "most of all, enjoy!".

The appointment was for 2pm and I started getting ready around
12pm, getting "squeaky clean" and then headed to my bedroom to get
ready. I slipped into my favorite white lace bra with front enclosure
and then a pair of navy blue satin and lace panties and I put on a
pair of white satin gloves and carefully slid on a pair of sheer nude
hose. I put on my pink satin makeup coat and started thinking about
what to wear for the trip to the salon, and I knew it had to be a
button up blouse and decided on a blue flowered one with a cute collar
and then grabbed a denim, knee length skirt. I then started thinking
about all of the snow on the ground and that the fact I was going to
be in boots, and only for the third time in my feminine life, I
decided that I would wear pants out in public.

I grabbed a pair of female denim jeans and slipped them on. They
certainly felt weird, but I knew it was the right choice. I then put
on a pair of 2 «" black heels for the time being and made my way to
the bathroom for my makeup. I knew what was going to be happening at
the salon and put on a light coat of foundation, a tiny bit of blush
and a light coat of lipstick, just to give my face a feminine look. I
fluffed out my hair and then went and checked my purse for the $40 I
was going to need and then checked the time. I had a few minutes, as
the walk was only going to be about 15 minutes and started getting
things ready for the evening. I laid out my lingerie for the evening,
which was going to be a white garter belt, a brand new pair of sheer
nude stockings, and a pair of red silky and lacy panties. I went and
grabbed my jewelry, which was going to be rhinestone, with red
features in it, all three pieces, my necklace, bracelet and earrings.
I decided on a simple gold anklet to compliment the entire look. With
15 minutes to the appointment, I grabbed my purse and slipped on my
winter boots and then into a bomber style winter jacket, a pair of
comfy earmuffs, and my pink gloves and headed out to the salon
appointment.

The sky was clear and blue and there was no wind, but it was
FREEZING!. The sidewalks were not plowed, as the snow came just the
day before, so walking to the mall was an adventure to say the least.
All I kept thinking about was, "thank God I did not wear a skirt and
heels!". I got to the mall and was thankful for the warmth and made my
way to the salon. Lianne was just walking back from the front and she
spotted me and said, "Joyce, so nice to see you, right this way". I
took my coat off and hung it up and followed Lianne to the chair she
was going to be working on me. I slipped into the chair and she
immediately put a smock on me and started asking me questions about
the evening and what it was all about, and my outfit and such. I had
fun as she worked on my eyes and lips and hair, etc., Anita came over
and did my nails and this time, I provided the nail polish, as I
wanted it to match my lipstick as it was dark and red and would go
perfect with the dress. Lianne asked me for the lipstick and I grabbed
my purse and gave it to her. The time it took Lianne this time was
slightly less, but it was about 1 « hours before all was said and
done. Lianne came with a mirror and showed me what she had done, and
again, I was totally blown away!. I could not believe what she had
done to me and loved the look, I gave her a big hug and thanked her,
and she told me, "have a fun evening", and I told her I would. I
followed her to the front and paid her, then carefully slipped on my
coat and earmuffs and then left the store and the mall and started
walking home. Again the temperature was FREEZING, and the snow deep at
times, but I made it back and noted that it was 4:50pm, and Eric was
going to be by at 5:30pm to pick me up, I took off my coat and boots
and went downstairs.

I went to my bedroom and slipped out of the jeans and blouse and
bra and started getting into my dress. First was the convertible bra,
this bra is one that has a strap at the back that goes down very low,
it was white and I slipped it on and adjusted my breasts. Next was the
dress, and I loved slipping it on, it felt so nice and silky. Once the
dress was on, I spent about 15 minutes trying to take the little tiny
safety pins and put then through the bra straps and then on the inside
fabric of the dress to hold the straps in place. It was a challenge,
but I managed to get them done up, much to my amazement!. I looked at
myself in the mirror and knew that I already look like a million
bucks!. I applied a very healthy dose of Obsession perfume to my
wrists, ankles and neck, and knew I went a "little overboard", but it
would last the entire evening. I then put on all of my jewelry and
then slipped on the new heels and checked myself out in the mirror.
Right then and there I knew I was in trouble. The dress, my makeup and
hair done by the salon and the whole look, I knew any date would not
be able to resist it, as it was a complete sexy and pretty look. I was
modeling the outfit for myself and then the doorbell rang!.

I looked at the clock and it was 5:20pm, Eric was early!. I had
not even packed my clutch purse yet!. I grabbed it and headed upstairs
to greet Eric. I opened the door and there he was, holding a single
rose. I invited him in and accepted the rose and gave him a light peck
on the cheek. I told him that I was not totally ready and he took off
his coat and I invited him to settle down and make himself
comfortable. He took off his shoes and sat on the couch and we talked
while I put the rose in a vase and in the kitchen, I took things from
my regular clutch purse and packed the silver one for the evening,
lipstick, blush, Kleenex, some money for a cab. Eventually I was done
and came into the living room, and Eric's jaw dropped, he looked me up
and down and said, "oh my God you look amazing". I twirled around for
him and then looked back at him, he did not look bad either. He was in
a gray suit and a pale blue tie, I sat down beside him and held his
hand and he told me that I smelled amazing. I gave him another light
peck on the cheek and told him that it was about time that we should
be going. I took the lead and got up and went to the closet and
grabbed my faux black fur coat and handed it to Eric, Eric then
assisted me to slip it on. I made sure I had my keys and then we
headed out the door for the Christmas party.

We got to the car and Eric was the perfect gentleman, opening the
door for me and allowing me to slide in. My dress rode up really high
on my thighs but I did not do anything to cover them up. As Eric got
into the car, I could tell he noticed, but did nothing other than
being the perfect gentleman. As we drove to the place of the Christmas
party, we went over the rehearsed routine that we had talked about for
almost a month and made sure that the stories and such were agreed
upon to make us a couple. We got to the hotel and Eric dropped me off
at the front entrance, coming around to open my door, and then went
and parked the car while I waited in the warmth of the hotel. I looked
around and could see TONS of other women dressed up, not one in pants,
all in skirts and dresses!.

Eric came back and I got into "girlfriend mode" and grabbed his
hand and we walked towards the location of the Banquet rooms. We came
to an area in the hotel that was packed with people. Off to the side
was a coat check and Eric lead me to it and was helping me off with
the coat when one of his co-workers, dressed in a really pretty black
dress, standing next to me, said, "what a gorgeous coat!". I smiled
back and thanked her and Eric tipped the coat check girl and grabbed
my hand and we went to get a drink and mingle in the crowd, at that
point I opened my clutch purse and took out the chain that was with it
and slung it over my shoulder. I held Eric's hand the entire time and
sipped on the wine that he got me and only let go to shake hands with
all of the people Eric introduced me to. At one point Eric said he had
to use the washroom and left me standing near the entrance of the
indoor pool of the hotel. I took the opportunity to look around and
saw that there was three banquet rooms and three company parties
happening at the same time. There was TONS of women dressed to the
nines for their Christmas parties, I saw some incredible dresses and
sexy young women in high heels, low heels, but NONE were in anything
but a skirt or a dress, which made me feel so much better. As I stood
there, I knew I was getting checked out by other women, and of course
guys!. I looked away, but was relieved when Eric came back and gently
took my hand, I was starting to feel really comfortable with him.

He lead me back into the crowd and I met so many people, I lost
track of names, a number of women and a few men I might add, told me I
looked amazing and that they loved my dress. At one point Eric lead me
to an area that they had a photographer and we posed as a couple and
got our picture taken (I cherish that picture to this day). It was
right before they announced it was time for dinner and I heard,
"JOYCE!", I spun around and there she was, Brenda with Brad!. Brenda
looked amazing, she too had her makeup and hair done professionally.
She looked stunning and her dress was perfect, she took my advice and
went with sparkly earrings and necklace, and she was wearing the same
stockings and strappy black 3" heels as when tried on the dresses
together. She grabbed my shoulders and looked me over and told me,
"now that is how you accessorize my dear", and gave me a little kiss.
Brad looked really handsome and just told me that I looked great and
was talking with Eric. Brenda came close to me and said, "has he made
a move yet?". In a funny way, I pushed her away and said, "not
likely", Brenda grabbed my hands and said, "dressed like that I think
he will". Brenda then pulled me towards the entrance to where we were
having dinner and told me it was time, and that we were sitting at the
same table. I followed her and left Eric talking with Brad and went
into the banquet room, as we walked I quickly converted my purse from
over the shoulder to a clutch.

We entered the banquet room and it was huge and beautiful, with
large chandeliers, and low lighting, large round tables with large
centerpieces and candles in the middle of them, it was really nice.
Brenda and I were hand in hand and she showed to the table we were
sitting at and there was a name tag there with my name, and right next
to mine was Brenda's. I looked at mine and it said, "Joyce Wright",
and I looked at her and whispered, "where did you come up with that?".
She giggled and said that it was one of the first girls she made love
to and thought it might be nice. I laughed and we both put down our
purses and slid into out seats. Brad and Eric came in and Eric came
and game me a little kiss and Brad went to Brenda and did the same.

Dinner was a 4 course meal, minestrone soup, a garden salad, and
finally chicken Kiev and cake for dessert. That allowed for allot of
conversation to happen. There was 5 couples at the table and I got
many questions about what I did, how Eric and I met, how long we had
been dating, etc., but the long planning and conversations Eric and I
had previous to the evening made everything go smooth. I checked out
the other women at the table, as I knew they were checking me out, and
they were all basically in "sheath" style dresses and spaghetti strap
style dresses, definitely younger styles. Brenda and I were the only
ones that really had any sleeves on our dresses. During dinner Eric
was a sweetheart, he would gently rub my arm when we were not eating
and we held hands, he really was a gentleman. Brenda saw this and
would casually look over at me, and smile. When dinner was over and
before the speeches started, Brenda picked up her purse and looked at
me, I knew that was a sign to go to the ladies room and I grabbed mine
and we excused ourselves.

As we walked out, I could tell that we both were being checked
out by again, both men and women and I ignored it. The ladies room was
right beside the coat check and we both were blown away when we
entered!. First of all the washroom was huge, but the other thing was
that it had a lounge area in it with 2 leather couches!!!. There was
women sitting on the couches, and I guessed they were waiting for
their friends to finish their business. There was no problem finding
an empty stall and Brenda and I went in at the same time. After
finishing my business and making sure my dress was right, I headed to
the long and large counter and mirror to fix my lips. Brenda was
already there and she was just closing her lipstick and I was just
touching up mine and she said, "so I see you and Eric are enjoying
each other". As I closed my lipstick, I looked at her in the mirror
and said, "I think we are". She smiled and said, "Brad has told me
that as far as he knows, he is still a virgin". I looked back at her
and smiled, "so?", she closed her purse and started to leave and said
quietly, "it is always nice to 'pop a cherry', that is what I did to
Sharon". I followed her out and quietly said back, "we will see, and
enough about Sharon", all she did was smiled at me as we walked.

We got back to the table and both Eric and Brad got up and being
the perfect gentlemen, pulled out our chairs for us, as we sat down.
The speeches were long and boring and eventually they came to handing
out door prizes. They handed out a bunch and then came to the point
were 4 guests of the employee's names were drawn. I was talking with
Eric and did not hear, "Joyce Wright", they called it twice and then
Brenda poked me and said, "that is you". I got up and started walking
to the front, and I realized that EVERYONE was looking at me. I made
sure I was walking perfectly and smiled and the gentleman at the front
shook my hand and I got a lovely "romance package" that had fruit and
champagne, etc., in it and walked back to my table and I knew I was
being checked out.

About 5 minutes later they dimmed the lights and the music
started and the dancing. Eric was the perfect gentleman and took my
winnings to the car and came back to join me. In the meantime, Brenda
and I again took a trip to the ladies room and I did not have to go,
but she did and I fixed my lipstick and then sat on one of the couches
and waited for her. One of the women sitting next to me told me she
"loved my dress" and asked where I got it and I told her and she also
commented on my makeup, and I assured her, I had some help. Brenda
finally came out and touched up her lips and then came and collected
me and then back into the party we went. Both of us did not sit down
before our dates asked us to dance. We both put our purses on one
chair and tucked it in under the table to be out of sight.

The songs we danced to were slow songs, and Eric held me slightly
away from him, and it was a very relaxing dance, he kept staring me in
the eyes and I stared back. There was 3 slow songs in a row and we
never left the dance floor and Eric was the perfect gentleman the
entire time. After the 3rd song, I went back to the table and Brenda
had just returned as well, then Brad and Eric went up to get us
drinks. Brenda and I were alone, and she just smiled and gently
grabbed my hands and said, "if you want 'it', you WILL have to make
the first move". I kind of knew what she was talking about, but
decided to play along and said, "it??", she smiled back and with a sly
grin said, "his cherry silly". I smiled back and told her that she was
totally mistaken about my intentions. She took a sip of what was left
her drink and then put it down and looked at me and said, "I saw how
you took care of Brad, it has been almost 3 months, a woman that sucks
with that much passion needs more". Right then and there I KNEW she
had been talking to Sharon in the background and the comments Sharon
made, all started to make sense. I blushed and calmly sipped my drink
and said, "well we will see.".

Brad and Eric came back, with drinks and we all sat for a bit and
talked, and then Eric wanted to dance more and I told him that would
be nice and he lead me to the floor. We danced for almost 30 minutes
straight and then I told Eric I had to sit down for a bit to take a
break and then he went and got another round of drinks for he and I.
It was almost 11:30pm and I knew Brenda was right, and decided to take
matters into my own hands. When Eric came back we sipped on our drinks
and then I suggested that he and I go for a walk to get away from the
music. I grabbed my purse and then he took my hand and we wandered out
of the area that had the parties and to the pool area of the hotel. At
this time it was closed, but we walked to the far end, well away from
people and found ourselves all alone. We were hand in hand and then I
looked up at Eric and thanked him for the lovely dress and the
wonderful evening and he looked at me and blushed and said, "it was my
pleasure". I took the opportunity and gently moved my head towards his
and he leaned forward and our lips met. I was slow and easy as we
kissed gently, but I started picking up the pace and we eventually
were making out fairly heavily. His hands were at my shoulders, and I
moved them slowly down to my backside. He was gently caressing it, I
noted that the bulge in his pants was pushing them way out. We
continued for a while and then I broke the kiss and told him that we
should be getting back to the party, and he agreed.

Before we left the area, I pulled out my compact and made sure
that my lipstick was not that smudged as I knew I had to go and touch
it up. I walked back to the banquet room with Eric hand in hand and
before I got to the entrance, told him I had to use the ladies room.
He gave me a light kiss and told me to hurry as he already missed me.
I went in and the makeup mirror was fairly packed and the couches were
full of formally dressed women, but there were open stalls. I sat down
and did my business and made my way to the mirror to adjust my
lipstick and Brenda came right next to me and said, "told you so", I
smiled back and said, "it was just a kiss", she looked at me in the
mirror as she did her lipstick and said, "oh no it was not, I would
call that, 'the first move'". We both packed our lipstick in our
purses and headed out to go back to the banquet room, I just smiled
back at her.

When we got back to the table, Eric was waiting and asked me to
dance again, and this time we stayed out for almost 45 minutes,
dancing to slow songs, fast songs and during the slow songs,
exchanging little kisses, and he held me close and I definitely could
tell that he was very excited. The last song was played and my calves
were killing me, I met Brenda back at the table and we excused
ourselves for one last trip to the ladies room. Brad and Eric said
they would get our coats and meet us after we were done. I checked the
time and it was 1 am, but I was not tired. The ladies room was not
crowded at all and I did my business (even though I really did not
have to go) and joined Brenda at the mirror as we applied another coat
of lipstick. She looked at me in the mirror and smiled and said,
"so?", I smiled back and said, "so what?", she nudged me and said
quietly, "are you popping his cherry tonight?", I closed my lipstick
and looked at her had simply said, "perhaps?" (but knew full well I
wanted to take care of him). She giggled a little and said, "I am sure
I will hear all about it, just do not lead him on". I assured her that
I would not and we left the ladies room to a waiting Brad and Eric
with our coats. Eric helped me on with my coat and Brad with Brenda's,
and once on, she gave me a hug and a little kiss and whispered in my
ear, "I bet he is yummy, young cocks usually are". I jokingly gently
pushed her away and grabbed Eric's arm and we headed to his car. The
night air was freezing, but Eric was quick to put on the heat to warm
up the car. We held hands all the way home and I could not stop
thanking him for such a wonderful evening.

Once in the driveway Eric came and opened my door and then helped
me out, grabbed the basket, and we went to the back door. I looked at
him and thanked him for the dress and a wonderful adventure out. I
then took the lead again and moved my head to his and we started
kissing. The kiss was long and I took the lead and started pushing my
tongue into his mouth and he pushed back, we continued kissing for a
while and then the cool winter wind started getting to my legs and I
broke the kiss and asked Eric if he wanted to come in for a bit. He
was a little reluctant but eventually he said he wanted to and I lead
him in by the hand. The house was dark and judging by the time I knew
Sharon was already asleep, so I took Eric into the living room and
asked him to get comfortable on the couch and went and took off my
coat and got a glass of wine for Eric and I. I sat down next to Eric
and we started chatting about the evening, and then I decided to again
take the lead and slowly moved my lips to him and we started kissing.
This time was a little more him than me, then he took the lead and he
started kissing me and was gently stroking my silky legs. He then
started on my breasts and I knew that the dress would not take that
and broke our kiss and hold him that I would be right back as I had to
change, as during the evening I had lost enough sequins.

I quickly went downstairs and slipped out of my dress and bra and
then into the lingerie that Brad had got me a couple of months
earlier, which was a pure white, silk and lace peignoir, and wrap. I
slipped on a pair of 3" white satin heels and went back up to greet
Eric. Eric almost choked on his wine as I walked in, I sat next to him
and he was all over me, his hands caressing everywhere. I very slowly,
moved my hand to his crotch (which was soaking wet), and slowly
started feeling his obviously hard member. We kissed for about 3
minutes and I started caressing harder and harder on his member.

I knew I was "in the drivers seat", and after we broke our kiss,
Eric was lost and did not know what to say. I gave him a light kiss
and then gently squeezed his crotch and said, "let me take care of
that". He said nothing and I reached down and I slowly unzipped his
pants and gently reached in and worked through his underwear and I
grabbed his throbbing member. Eric almost jumped about 2 feet in the
air and broke our kiss. Brenda was not kidding when she said he was a
virgin, but obviously he was, as the fear in his eyes told the story.

I saw this and told him to relax and I would take care of
everything. I slowly undid his shoes and then slowly started to slid
off his pants and underwear, which revealed a hard and wanting cut
member, not huge and not small, just average. I saw the look in his
eyes and it was of pure lust. As I slid off his pants so that he was
naked from the waist down, I slowly stroked his member and came up to
slowly kiss him. I then broke the kiss and then started gently kissing
his neck as I kept stroking his member. He was stroking my legs and
then my breasts and then I whispered in his ear, "tell me what you
want". He just groaned and I started stroking him harder and softly
said, "come on Eric, what is that you really, really want?". He had
his eyes closed and was enjoying my stroking and then groaned out,
"those lovely lips!, those lovely lips!". I then asked, "where,
where?", he groaned, "where you hand is". I then played hard to get
and said, "you want a blowjob?". He groaned, "yes, oh Gosh yes", I
made him wait longer and said, "that was not very convincing, how bad
do you want it?". He then gently grabbed my arm and said, "please do
not make be beg, I want your lips really bad on my cock, please give
me a blowjob".

I stepped up and slowly made my way to my purse and very, very
slowly applied a fresh coat of lipstick and then slowly walked towards
Eric. I sat next to him and slowly started stroking his very hard and
wet member. I smiled at him and then slowly lowered myself down and
then opened my lips and started licking and sucking on his member.
Now, I knew Sharon was asleep, but Eric was very vocal and was almost
screaming as I slowly licked and sucked his very hard member. I really
did not care and just continued to lick and suck, all the while slowly
stroking him up and down with my left hand. Eric never went soft, he
was hard the whole time and then eventually he started screaming, "oh
my G*d, oh my G*d!!!" and then thrust his hips up and boy oh boy, did
I get a mouthful!!, he came and came and came. I swallowed all of him
and came up for air and was slowly stroking him and he pushed my head
back down and screamed, "please don't stop, pleaeaasse", I went back
to his member and started licking and sucking and within 2 minutes he
was hard as a rock again!, about 10 minutes later he cried out again
and then he came like a cannon again!. I came "up for air" and then he
pushed my head back down and screamed out 'no, one more, one more!!!".
I thought "what the heck?" and started sucking and licking again, and
once again, 2 minutes later he was hard again (oohhhh youth!), this
time it took a bit longer, but he eventually got harder and harder and
then started to grunt and thrust his hips then screamed my name a few
times and then he came. This time was not that much, but I swallowed
all of him as he started to become soft. This time he pulled me up and
told me that he needed to rest, but wanted to do that again, at least
one more time. I smiled and told him that I needed to take a break
anyway and got off the couch and grabbed my purse and headed to the
bathroom.

I went in and turned on the light, then carefully sat down and
was doing my business, when my spouse Sharon walked in, and was
squinting due to the lights and casually said, "sounds like you are
showing Eric a good time?". I told her that it was the least I could
do for the wonderful time he showed me and for buying the dress. As I
cleaned up and was applying another coat of lipstick, Sharon was
sitting down to do her business and said, "I take it the party was
really good?, judging by the screaming in the living room, he has cum
twice already?". I told her, "no three and he wants more!". She smiled
as she left the washroom and said, "have fun, I am taping the action
and will see how you did in the morning". I closed my lipstick and put
in my purse and headed back to the living room and noticed, the closet
door slightly open and the red light of the camera. I just smiled and
went to Eric who was already hard and sat next to him, I gave him a
long kiss and slowly started stroking his already hard member. I broke
the kiss and was starting to move down to lick and suck his member
when he stopped me and was slightly panting and said, "please keep
stroking it and I want a hickey on my neck".

I smiled and then told him that he was going to have to undo his
shirt collar and remove his tie, which he did in a flash and as I
slowly kept stroking him, moved down and started to bite and nibble on
his neck and sucked hard as well, for at least 5 minutes. When I was
done, he had a VERY large hickey and was panting. I then lowered
myself to his member and started slowly sucking on it and licking it,
and then picked up the pace as he kept crying out, "oh yes!, oh yes!".
I was not sucking for that long and then he came for a FOURTH time!.
This time was about the same as the last and I easily swallowed what
he had to offer.

That was it for Eric and he pulled me up and gave me a light kiss
and told me that it was time to go and that even though we did not
make love, I was the first woman to make him orgasm and he was so
thankful for the wonderful experience. I told him that it was my
pleasure and that the entire evening was so enjoyable to me. I got up
and sipped on wine and watched, as Eric got dressed. I then got an
idea and quickly went to my bedroom and removed my panties and sprayed
them with Obsession perfume stuffed them in my hand and then went back
upstairs. When he was dressed, he grabbed his overcoat and came and
grabbed my hand and lead me to the door, He only gave me a light kiss
(I suspect he did not want to taste his own cum) and then thanked me
for the wonderful evening and I reached in his pocket and put the
panties in and said, "for you to remember the evening by". He smiled
and gave me another little kiss and said "thanks", but I did not think
he knew what I did.

I cleaned up the wine and the glasses and then turned off the
lights and headed downstairs to bed. I snuggled in and removed my
latex vagina and then gave myself some much needed relief.

Epilogue:

Eric called me the next day and figured out what I placed into
his pocket and thanked me so much for that.

Brad and everyone at work saw the hickey and I gave and was
teasing Eric about it, and everyone kept telling him how pretty and
lovely his date was for the party.

The video did work, it was a little dark, but I got to see the
passion and what I did to Eric that evening and Brenda got a copy.

Eric called me in early June 2003 and asked if I would accompany
him to a friend of his Wedding as a guest in September 2003. I
accepted, so for the first time I will be going to a Wedding as a
guest rather being a part of it.

Another story to come later in 2003....

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My Fiance Earl (1 - 5)

My Fiance Earl (1 - 5)

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