Crossdressing with my Girlfriend and Boyfriend
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Cross-dressing Days with my Girlfriend and Boyfriend
By Cindybelle
"Come into my room Timmy, it's time to start getting you dressed,"
said Cathy, my eighteen year older sister. It was the day of Janette's
wedding -- she is my eldest sister, twentytwo years old and she is
marrying her college boyfriend Mike at 2 o'clock this afternoon.
I'd better explain that I'm Timothy, eleven and a half years old and
I'm going to be the ring bearer at the wedding. It didn't start out
that way though. Janette, as well as wanting four bridesmaids, had
also wanted four flower girls -- all of whom were my cousins. Then
two weeks ago Sharon, one of the flower girls had an accident when
riding a horse and broke her leg -- and it would have to be in
plaster for three weeks. So Janette got all panicky about her four
flower girls. There were no more nieces and she already had the
costumes, mom had made them. Thus it was that Cathy, Janette and my
mom called me into the lounge and said they had something they wanted
me to do.
"Timmy, we wouldn't ask you this if it wasn't that Janette is
desperate", said my mom, "but we want to ask you a big favour."
"OK, let me hear it," I replied, cautiously.
"Well, you know how Janette wanted to have four flower girls at the
wedding, well since Sharon's accident we have tried to find a
replacement -- so we can have four girls to balance with the four
bridesmaids -- but we can't find anyone who is available and who
could fit into the dress we had made for Sharon," mom explained.
I started to get a sense of where this was heading. "But you can't
mean..." I started.
"Now, hear me out," said mom. "You are the same height and build as
Sharon, and you know how well you played the role of Dorothy in your
schools Wizard of Oz play last term."
"You really were so cute -- nobody would have known you weren't a
girl," said Cathy who had attended the show.
It had been bad enough trying to live the Dorothy part down at
school, now they were bringing it up to try to make me dress up
again. My minds eye flashed back to last term when I was press ganged
into the role after a call for volunteers drew no response.
"Right then," said Miss Cartwright the Drama teacher. "I will pick
someone," and she looked around the class and her eyes rested on me.
Now, I know I have a soft rounded face and long eyelashes and longish
blonde hair and some of the boys had in the past called me girly --
so I dreaded what might happen. Sure enough, she walked up to me,
cupped my face in her hand and said, "Yes, I think we've found
Dorothy, - Timothy -- congratulations, you have the role." The rest
of the class sighed with relief as I cringed.
So it was six weeks later that I stood on the school stage in a blue
gingham dress, white socks and glittery red shoes, two blonde braids
pinned into my hair, and wearing stage makeup, singing 'Somewhere
over the Rainbow' in front of 500 people including all my giggling
classmates. Worse, my mom was into dressmaking and amateur drama so
she had taken care of the costumes and makeup herself, so I really
did get the full treatment. She made me rehearse at home in the
costume, "to get used to it". With both Cathy and Janette watching
and giving me tips on how to act like a girl. This was a period in my
life I was trying to forget.
So now I stood in front of the three of them, I realised I had to
stop this right there and then. "There is no way I am going to dress
up as a girl ever again, I still get called Dorothy at school by some
of the kids, so if you think I'm going to put on a dress in front of
the whole of our family and friends and everyone who is coming to the
wedding, no, you are mistaken, I won't and you can't make me."
Janette looked crestfallen, but didn't say anything. Cathy just
looked disappointed - she was always needling me about my size and
how pretty my hair was.
My mom came back with, "No one will force you Timmy -- it was just
that it will spoil Janette's wedding -- don't you want to help your
sister on her big day?"
"Mom, I'll do anything to help that I can, but please don't ask me
to wear a dress, it is just something I won't do in front of
everybody."
"Well I have to say I'm very disappointed and so is Janette. Do not
expect any help from me next time you want something. You had better
think this over very carefully -- we will talk about it again
tomorrow. Now perhaps it's time for you to go to bed."
It was only 8.30pm, but I took the hint and went up to my room. I
could hear them talking for ages afterwards and even some laughter
- from Cathy and mom after a while, so I thought maybe things weren't
quite so serious after all.
Next day, Janette came up to me. I always got on well with her. She
was very different to Cathy, always kind and considerate.
"Look Timmy, I'm sorry about yesterday," she said, "I realise it was
too much to ask. I've rethought what we can do, instead of four
flower girls, I could have the three and you could be a ring bearer."
I thought back to my cousin Charlotte's wedding last year where a
boy, he must have been about seven, had carried the ring on a satin
pillow in the service. He was wearing a boys tuxedo, he looked a bit
overdressed with bow tie and black shoes, but at least it was not a
dress.
"Well I suppose that will be alright, I do want to help you have a
nice wedding," I said
"Oh, thanks Timmy, that will be wonderful, you will make a great
ring bearer," upon which she grabbed me and gave me a peck on the
cheek.
I guess I should have been alerted when 3 days later Cathy came by
my room and said, "Moms nearly finished your ring bearer costume --
you are going to look very smart."
"Well, it will be a lot better than a dress," I replied.
"Oh, yes, a lot better," she chuckled.
So now she was calling me into her room. "Why can't I get dressed in
my own room?" I asked.
"Because you will need help with one or two things," Cathy replied.
"Oh, OK then have it your way," I said
"Now, I want you to promise not to complain about anything, you got
off wearing a dress and you promised Janette you would wear the ring
bearer costume, right?"
"Yes, I promise not to complain - I want to help Janette have a nice
wedding."
"Good boy," said Cathy, "now strip down to your underpants and we'll
get started."
When I hesitated, she said, "Timmy -- you run around to and from the
bathroom in your underpants, I see you in your swimming costume,
what's the problem?"
"Oh, nothing, I guess -- it just feels odd doing it in your room," I
said as I slowly took off my T shirt and jeans, socks and sneakers.
"Oh boxers," she said, when I had finished, "don't you have any Y
fronts or briefs?"
"No, I only wear boxers."
"Well, with this outfit you will have to wear these," she said,
walking over to her dresser and picking out a pair of yellow panties
edged in white lace.
"No way," I said. "I'm not wearing those," I yelled
"Timmy what did you just promise? Not to complain, right, you don't
want to spoil Janette's wedding -- No one will see them, what's the
problem?"
"Oh, alright, give me them." I turned round, removed my boxers and
slowly drew the panties up my legs. They felt very snug and smooth as
I pulled them on.
"Right, that looks nice," she smirked, "now let's try these." She held
what I thought were white girls stockings , but as she unrolled them
it became clear they were tights, white and shiny.
I started to complain, but before I could speak she said, "Not a
word. You made a promise, lets just hear no more complaints."
"I was just going to say that I had said no dresses, you wear
tights with dresses, what's going on?" I asked.
"Don't worry little Timmy, you are wearing pants not a dress," she
told me.
"Come on let me help you to get these tights on." She rolled up them
up and unfurled the tights on to each leg while I sat down, then she
told me to stand up while she pulled them up around my waist.
"Now, pull them up tighter, while you jiggle around, till they are
comfortable under your bum. You might want to push your little boy
parts underneath you a bit," she said smiling.
I turned away and wriggled into the tights and pulled myself tidy
underneath by tucking myself in. I looked down at my legs -- they
looked so long and sort of shiny and very, very girly -- but at least
they would be covered by my pants.
"I don't see why I need to wear tights if I'm wearing pants," I said
to Cathy.
"You'll see why, right now," she replied. She held up what looked
like a pair of shorts. But they were made of a shiny satin fabric,
were a kind of apricot orange colour and had a lace fringe around the
bottom of the legs. "They are what is called Knickerbockers -- or
pantaloons, they are what men wore in the 1800's. They are made out
of Sharon's dress material. All the flower girls are wearing orange
satin dresses so you will match in with them and look really cute."
"But they are terrible, they have lacy bits and it's an awful
colour," I wailed.
"Timmy, I won't say this again -- no more complaining, we need to
get moving, put these on," she yelled at me.
I took the garment from here and reluctantly stepped into it. I was
appalled at how silly it looked and as I pulled it up around my
waist, I saw that it only came down to 5 inches above my knees so
that I would be showing most of my legs in the glossy white tights --
this was becoming awful. The waist was elasticized and there was a
row of tiny buttons around the top.
Cathy knelt down in front of me and started tying up a belt of
orange ribbon which laid under the white lace fringe at the bottom of
the leg. This brought the material which was otherwise quite baggy
close into my leg.
"There that looks really sweet and everyone can see what nice legs
you've got. Actually you'll be showing a lot more leg than the girls
in their dresses will," she chortled.
My morale hit rock bottom at this point, and I offered no resistance
when she brought out the white shirt. But it wasn't a shirt -- she
pulled it over my head and put my arms through the large puffed up
sleeves and then started doing up a row of small buttons up the back -
- it was really a blouse. It had a row of frills around the neck at
the front and down the middle, and lace around the end of the
sleeves, just like on my legs.
"There that looks really nice, and again it will tie in with what
the girls are wearing under the top of their dresses -- Janette will
be so pleased you can make up the foursome, even though you didn't
want to wear a dress," Cathy said.
I then began to realise why there had been the laughter after I
refused to wear a dress, this was their way of getting revenge. I was
annoyed at my stupidity, I even began to think it might have been
better going along with the girls dress idea rather than put on this
ridiculous outfit, but it was too late for that now. When I was
dressed as Dorothy the audience didn't laugh, people actually came up
afterwards and congratulated me.
"Right, nearly finished," said Cathy. "Just your waistcoat to put
on." She held out another piece of the apricot orange satin, now
fashioned into a sort of waistcoat -- but who ever heard of an orange
waistcoat.
"It's made from the top of Sharon's dress," Cathy explained, "all
we've done is cut it off at the waist and add a row of small buttons
down the front and then the buttons on your pantaloons will tie the
two parts together. So, from the waist up you'll look just like the
flower girls, and it goes nicely with your satin pantaloons," she
said triumphantly.
I slumped forward and sat on the bed looking very unhappy. Cathy
said, "Good, now I will tidy up your hair a bit." She took out one of
her large combs and a brush and proceeded to back comb my hair. It is
very fine and thick and I have been growing it long.
"There, how's that?" she asked putting me in front of the mirror. My
hair was now piled high and as it tends to be naturally curly, it
looked as if it had been styled in a very feminine way. "Hold it,
while I give it a spray to hold it in place and give it some shine."
So saying she proceeded to liberally spray it with some sweet
smelling perfumed spray.
By now I was very unhappy and thought I couldn't feel any worse. But
then Cathy said, "Just one more thing, your shoes."
With that she went over to her wardrobe and brought out a shoe box
and lifted out a pair of shoes, girls shoes, covered with shiny
orange satin which buckled over the foot and around the ankle --
there was even a small bow on the foot.
"Come on, let's get you finished." So she proceeded to put on these
ghastly shoes. "You'll need to be careful how you walk in them, they
have a nearly 2 inch heel which you'll have to get used to. Just
take small steps and you'll be alright. It's lucky Sharon's shoes
size was the same as yours," said Cathy bubbling with laughter.
I stepped over in front of the full length mirror and looked at
myself. Girls white glossy tights (with panties underneath), a girls
frilly, lacy blouse, the top of an apricot orange girls satin dress,
and the satin pantaloons with their puffed up legs and the lace
frills, and the awful prissy girls shoes with the silly bows. With
all that and my hair done up in curls -- I realised it was worse than
being dressed as a girl, I was dressed as a sissy -- with my legs in
the shiny tights making me look absolutely ridiculous.
"I can' go out like this," I whimpered, "please let me change, other
ring bearers wear proper boys clothes, these are just awful -- and
they are girls clothes."
"All you said was 'no dresses' and you are not wearing a dress. But
you will match in with the flower girls and that's what Janette will
like and you do want to make her happy, don't you?" Cathy questioned.
"Yes, but I think you have played a trick on me, and it's not fair."
"It may not seem fair to you but that's the way it is. Now go
downstairs and wait while I get dressed and be careful not to mess up
your costume."
It was then I realised that around the house there were other people
getting ready including five cousins, Rosemary, Aubrey and Belinda
who were the flowers girls and also Robert and Jason who had arrived
last night.
Cathy shouted down the stairs, "Rosie, girls, here's Timmy coming
down to join you, he is already in his ring bearers costume come and
have a look."
With that Cathy pushed me out of the room and I stood at the top of
the stairs in my ridiculous costume. Rosie and the other girls came
out of the lounge to have a look. They stood there as I held on to
the stair head rail and first they all gasped, then put there their
hands to their mouths -- and then squealed and then they went into
fits of laughter.
"Come on down Timmy and let's have a closer look -- you look
absolutely darling," said Rosie.
"OOOH what great legs you've got -- golly they are the same tights
as I'm wearing," said Aubrey.
"But look, look," said an excited Belinda, "he's wearing our satin
dress top and the blouse and aren't those pantaloons just so dainty --
I love the lace around the legs," she squealed.
I came slowly down the stairs, being careful in the strange
footwear, so I took slow dainty steps -- normally I whizzed down two
stairs at a time.
"I don't believe it, he is wearing our satin Mary Janes as well,
doesn't he look just darling?" said Rosie repeating herself.
They gathered round me having a closer look at my stupid outfit. "I
like they way you've done your hair," said Belinda.
I went through into the lounge and sat on the sofa.
"How did they get you to dress up like this Timmy? Do you like
wearing girly things?" asked Rosie.
"Wait a minute, didn't Cathy tell me you had played Dorothy in the
Wizard of Oz at your school -- and your mum made you dress up like
her and practise?" queried Belinda.
"I did it because Janette wanted me to. They asked me first to dress
up like a girl in Sharon's dress. I refused, so Janette said I could
be a ring bearer instead," I explained.
"But all the ring bearers I've seen have been nearly half your age
and were wearing little boys black tuxedos or just a dark suit, not
girls clothes and orange satin pants with frills," squeaked Aubrey,
before collapsing with laughter.
"I know that now, but they never told me what the costume was going
to be, I only saw it for the first time this morning as I was putting
the things on. By then it was too late, I've promised Janette I would
do it and I can't go back on that. It's my mom and Cathy who have
dreamed up this idea. These shoes are already hurting me," I
explained.
"Well Timmy," said Aubrey, who although my age was 2 inches taller,
"I think you are being very good and very brave to dress like this
for your sisters wedding in front of hundreds of people. We will all
be wearing our costumes for the ceremony and for the photographs
afterwards and then we go onto Garthwaite Hall for the meal and
speeches and then there is the dance -- so you better get used to
your pretty shoes you are going to be wearing them and your lovely
costume for the next 12 hours," said Rosie.
Oops, I had not thought of all that. I was just thinking that I
handed over the ring and then could change and get back into my
normal clothes. But the church was 20 miles away and the Hall was
another 15 miles beyond that.
Mom then came downstairs in her full wedding outfit and hat. "Right
girls, are you all ready -- oh sorry Timmy, I only saw your top half,
you look just like the girls, my your hair is lovely, did Cathy do
that? Stand up and let me see you and the girls as well."
She looked us over, as we stood in line. "My you all look lovely,
really beautiful, the orange satin really suits you all, and Timmy,
I'm so pleased the way your pantaloons have turned out. I was
thinking off making them longer and with two or three rows of lace,
but I think they are nicer with the shorter length -- it shows off
your legs much better. Perhaps I should have made the dresses shorter
-- but no, -- three inches below the knee looks right," mused Mom.
I stood there with the girls, with my silly short frilly satin
pantaloons and thought 'can this get any worse?' Later that day I was
to find it could, much worse.
Then Janette came down, she came in through the far door and as we
were all standing behind the sofa she could only see the top half of
the other girls and myself.
"But... what has happened... I've got four flower girls... wait a
minute, is that you Timmy?" she said coming behind the sofa.
She looked down at my pantaloons and tights and gasped. "I thought
you were getting a suit for him," she said as she turned to Mom.
Mom jumped in. "Well I thought as we had Sharon's costume made, it
was a pity to waste it, so I fashioned the pants out of the skirt and
kept the top half with just a slight alteration. Doesn't he look
gorgeous?"
"Well he does look sweet, but I think I would have preferred to see
him in a suit, woudn't you have preferred that Timmy?"
Mom, was standing behind Janette and by signals she indicated I had
better agree to prefer the costume -- the girls did not see this.
I didn't know what to do, I didn't want to spoil Janette's wedding
by making her think I was unhappy, by now also, Cathy had come
downstairs and she had heard what Janette had asked and was looking
threateningly at me.
So I said, "No Janette, I don't mind the costume, it means you have
a ring bearer and you also have a stand in fourth flower girl." Mom
and Cathy beamed, the three girls looked at me in amazement and
Janette came over and gave me a big kiss on the cheek -- and I
blushed down to my socks -- oops, no, the soles of my tights.
"That is so sweet of you Timmy -- yes you can be my extra special
flower girl." All the girls were sniggering now, and Mom and Cathy
looked very pleased with themselves -- so there it was, I was off to
the wedding looking like the biggest sissy ever. All my relatives,
friends from the town, guys and girls from my school would see me --
photographs taken, boy was I doomed.
The cars came an hour later, during which time I endured the
questions and taunts of the girls. Do you like the feel of the
tights? Is it true what Cathy told us that you are wearing lacy
panties? Do you do your hair yourself? What's the perfume smell? Oh
it's only hair spray. Do you want to borrow my perfume, it's in my
handbag? You will need a handbag, your pantaloons have no pockets. So
they went upstairs and got a white satin handbag from Cathy.
Are you wearing any makeup? You can borrow mine. Just a little
mascara and a touch of blusher, oh, you are already blushing a lot as
it is. Cathy came down at this point with things for my handbag, and
proceeded to make up my eyes with mascara and put some blusher on my
cheeks and just a touch, she said, of pink lipstick on my lips, then
she put the things in my handbag, "So you can freshen up later."
Then, to add to my torment in from the garden came Robert and Jason,
my nephews. They were in trousers and shirts, ready for the wedding,
maybe just with a jacket still to put on. They looked at the four of
us in our orange costumes and Robert said, "Wow, you sure have
prettied up nice, but I though there were only three flower girls."
Jason had walked round the side of the sofa and now saw my pantaloons
and my legs encased in the tights.
"Bob, I think one of the girls is a boy, well just maybe, have a
look," said Jason.
Robert came round to see. I cringed as he looked me up and down. "Oh
my god, is that who I think it is -- what an outfit, what a sissy,
you're not going to the wedding dressed like that are you Tim?"
Cathy interrupted before I could answer. "Tell the boys what you
just told Janette, Timmy about how you want to be a ring bearer and a
stand in flower girl."
"Yes that's true," said Rosie, "he is going to be our fourth flower
girl, don't you think he has lovely legs, come out and show the boys
your tights Timmy."
I walked out into the middle of the room, as I passed Jason I noticed
he sniffed and smelled my perfume and grimaced. So I stood there in
my satin and lace and frills while everyone commented.
"Do you really like dressing up all girly?" asked Jason who seemed
really interested in my appearance.
Again, before I could answer, in jumped Cathy, "Well just look at
Timmy in the photo above the fireplace -- that's him dressed as
Dorothy, the little girl in the Wizard of Oz -- you were really good
in that role weren't you Timmy?"
"Oh, how sweet," said Robert, "well I'm sure you are going to be the
centre of attention today in your pretty clothes -- come on Jason
let's leave the girls to gossip, we'll go back out into the garden."
I endured all this without complaint, somehow I realised that
reacting to their taunts would make it worse so I just went along
with it and after a while they started just to gossip amongst
themselves.
We all, that is I and the flower girls, travelled in the same car.
The chauffeur holding the door said, "Come on girls - hop in," he
then did a double take when he saw me in my sissy outfit. "Why aren't
you in a dress like the other girls?" he asked, causing them all to
fall about with laughter.
"I'm a boy and my name is Timothy. I'm the ring bearer," I squeaked
in embarrassment.
"Well , you could have fooled me sweetie -- it takes all sorts..."
It felt weird sitting with the three girls, they were all encased in
their dresses which had large white petticoats underneath, while I
sat squashed between them with my satin pantaloons and long white
tights showing.
We arrived at the church and had to stand in a group as the wedding
party assembled. The four bridesmaids were already there and rushed
over to greet us. Their dresses were orange as well and they
complimented us on our dresses. I had been sort of hidden behind
Aubrey and it was only when I stepped out that Angie the chief
bridesmaid gasped and said, "I thought you were all flower girls, who
are you?"
"I'm Timothy, I'm the ring bearer," I stuttered.
"But what a lovely costume, although it's a trifle unusual -- who
made it for you?" said Angie.
"His mom made it," said Rosie. "He wanted to be the fourth flower
girl so his mum took Sharon's dress and made it so he could be a
flower girl and a ring bearer."
"Well that's lovely of you, what a wonderful boy," said Angie, "you
can walk with me down the aisle with the bride and groom carrying the
ring and when they come back down the aisle you can be the chief
flower girl and carry my bouquet."
And so it was when Janette arrived we formed a procession and
followed her down the aisle. There were stares, figures pointing and
hushed conversations as I walked gingerly down the aisle in my
uncomfortable sissy shoes.
Then I had to stand with the other girls as the ceremony took place.
I was aware that as I stood behind a low barrier with the girls only
the top half of my dress showed and which was identical to the other
three girls -- you could see people smiling at us and taking pictures.
After what seemed an age the music struck up and Angie grabbed my
hand and we walked in procession back down the aisle -- she told me
to wave to people I knew -- but I was too scared and embarrassed
concentrating on taking small mincing steps to keep pace with the
procession and conscious all the time off those orange satin shoes at
the end of my exposed legs.
The photographs took for ever. We were posed sitting, standing,
holding flowers, in small groups, in family groups. Everytime I was
right at the front being told to smile. One time, when I was with
Janette and Mike, they actually took photos of me sitting on Mikes
knee.
Mom wanted lots of photos with her and with Cathy and insisted on
the photographer taking many pictures of me alone -- at one point
Cathy came up and using my handbag, touched up my makeup so he could
take some close up portraits. What I didn't realise until later is
that she had put on much heavier blush and lipstick and emphasised my
eyes with mascara and eye shadow, so I looked really girly.
"Gosh, Timmy, my mom won't let me use that much makeup -- you are
lucky to have a sister like Cathy," said Belinda.
"I think we should call you Tammy now -- you are more girly than we
are anyway," said Rosie. So from then on it was 'Tammy' whenever I
was called. Cathy soon picked up on this and from her it spread
around the wedding party until I think some people thought it was my
real name.
After the torture of the photos it was off to Garthwaite Hall. As I
got in the car, the chauffeur looked at my painted up face and shook
his head -- muttering "Little Pouf".
"Come on in Tammy, let's get to the food and drinks," said Rosie as
we bundled into the car. The driver looked bewildered.
When we got to the Hall we found that the tables all had place names
on them. I thought initially I would be with the other flower girls.
But Janette had placed me with Robert, Jason and the other young boys
-- something I didn't want to do while wearing the very girly outfit.
So I went up to Janette and told her.
"Gosh Timmy you have gone a bit overboard with the makeup -- so I
can understand why you don't want to sit with the boys anymore. Now
let's see, the girls table is already too full." I looked across at
the table where Rosie and the others were sitting -- it was designed
for 10 but there were 12 girls already sitting there.
"Tell you what Timmy, why don't you go to table 7 over there, you can
help look after the little ones as well." I looked across to table
seven. On it were a dozen, at least, of young kids, some were in high
chairs, between the ages of 3 and 7 or 8 all in party dresses or
little romper suits being looked after by a young girl of 18 or so.
Janette took me over. "Tammy this is Timmy, there isn't a seat at
his table and he would like to help you look after the youngsters, he
has been my ring bearer and a very special flower girl."
"I can see he is special all right," said Tammy, "yes I could do
with some help, why don't you sit over there Timmy and help me pass
round the food."
I sat down, just then Rosie came by and called out to me, "I see
you've found the right table Tammy."
Tammy turned to me and said, "Did she just call you Tammy?" I nodded.
"Well, boys and girls, from now on I'm Tammy One and this pretty
girl over here is Tammy Two," she said.
That started it, "Are you really a girl?" said one.
"Of course she is silly, can't you see she is wearing girls clothes,
tights and look at her dainty shoes -- and she is wearing makeup."
"Yes," said Tammy One, "you do seem to like a lot of makeup."
I gave up fighting it at this point and just said, "Yes well it's a
special day and I wanted to look nice -- the bride is my sister."
"Well you look very pretty," said another little girl, "but why
didn't you wear a dress like the other flower girls?"
"Because I was also the ring bearer and that is usually done by a
boy," I weakly replied.
"So that means you were a girl pretending to be a boy," the
youngster came back. Tammy one was watching this interchange with an
amused smile.
"Well, yes, I guess I was pretending," I said.
"I think you make a better girl than a boy," said Tammy one with an
even bigger smile.
And so it went on. Actually after a while I really enjoyed it, as
the kids were funny and weren't unkind to me like some of the others,
so I joined in the fun and ate and drank and played with them.
Then came a problem. I needed to go to the loo. Where did I go and
how did I get these pants off? I shuffled around for a while until I
couldn't stand it any longer. So I walked over to Cathy's table and
whispered in her ear.
She said loudly, "Oh Tammy needs to go the little girls room, excuse
us everyone." So she grabbed me by the hand like a toddler and walked
me out of the room, I was so embarrassed I did not see her gesture to
Rosie and the girls to follow us.
"Well Tammy, there is not room to do this inside the cubicle so we
will need to take your pretty pants down in here." Here being the
large room where several ladies and girls were already washing their
hands and redoing their makeup in front of a large mirror.
So she made me stand in the middle of the room while she undid the
bows around the legs on my pantaloons. "We are going to have to take
your pretty shoes off as well so we can get the pants off
completely," said Cathy.
Just then in walked Rosie, Belinda and Aubrey who watched while
Cathy took of my shoes and pulled down my pantaloons and I stepped
out of them. By now there was an audience of about 16 women and girls
watching me, I don't think anything could be more embarrassing.
I stood just in the room wearing just my tights and the blouse and
dress top. "Tammy is wearing panties, look," said Rosie pointing at
the yellow outline under my tights.
"Yes, pretty lacy yellow panties," Cathy said. "Mind you pull up
your panties and tights properly when you have finished Tammy and
remember to sit down," she added.
I went into the cubicle. It took me ages to perform, I was so
uptight and humiliated. Eventually I had finished and I readjusted my
panties and tights and walked out. If anything there were more people
in the room now, including the other girls. But Cathy had gone. Rosie
said she had told the girls to redress me.
So then I had Rosie, Aubrey and Belinda fussing over my pantaloons
and retying the ribbons, then putting my shoes back on -- watched
again by a throng of other people all laughing and making jokes.
Then Rosie said, "Cathy said you also have to freshen up your makeup
before you go back, here is your handbag."
"But I've never done my own makeup," I whined.
"Well now is the time to learn," said Belinda.
So I took out the blush and lipstick and tried to redo my makeup.
What I didn't realise is that Cathy had substituted much brighter
makeup, a bright red lipstick and a really strong rose blush -- so
even though I only touched up a bit -- the effect was dramatic.
"Wow, girl, you really know how to pile on the war paint -- you will
be pulling in the boys from all over the county," laughed Aubrey.
So, back I went into the dining room, but not before Rosie had
sprayed me heavily with perfume. "Now you really will pull in the
boys," and they all laughed.
I caused a minor sensation as I walked back in the room -- the story
of my undressing in the ladies loo had done the rounds plus my
reinforced makeup and the powerful wafts of perfume which followed me
around caused smiles from the ladies, but I noticed many of the men
were shaking their heads.
"Why don't you come back to our table now Tammy?" said Rosie. "A
couple of the girls had to leave early so there is plenty of room now
and we could have lots of girly talk." I looked across at the kids
table, but Tammy one was sitting there with just two kids, as parents
had retrieved most of the other kids.
So I sat down with the girls. First they wanted to borrow my makeup,
asked me what perfume I used, what kind of boys I liked and talked
about their favourite boy band pop stars and asking me my opinion. I
tried to join in but it was hard to keep up my spirits with all the
constant reminders that I was trapped in this costume.
After the speeches -- "and 'thank you' to our four beautiful flower
girls," was one line, the dancing started. In a while some of the
boys came over and asked the three girls if they wanted to dance.
Rosie spoke up and said yes but one of you has to ask Tammy for a
dance as well.
"Oh come on," said Robert, "I know he looks like a girl but that
doesn't mean we have to dance with him."
"Tammy has taken a lot of trouble to look like a pretty girl and
someone has to ask her to dance," said Belinda.
"OK then," Jason stepped forward put out his hand and pulled me up
and walked me onto the floor before I knew what was happening. Jason
is 13 and very well built and about 5 inches taller than I. The other
guys picked up Belinda, Aubrey and Rosie and we were soon all on the
floor. I attracted some quizzical looks but let it go by me. In a way
I was enjoying it. Jason was a good dancer and I followed his lead --
we stayed on the floor for about 15 minutes.
As we walked back he asked if I wanted a drink, I said I'd love a
diet Coke. He brought one from the bar and instead of walking me back
to the table suggested we go out on the patio for some fresh air. I
hesitated but then said OK, I was a trifle hot. Then he did a strange
thing. He took my hand and led me outside, I don't know why but that
gave me a tingle -- a really weird feeling. While we danced we hadn't
really been touching -- it wasn't that kind of music. But as he held
my hand I suddenly felt a change had taken place within me -- and
perhaps also with Jason.
I looked across at him. He had a broad handsome face, a strong jaw
line, really intense blue eyes and a shock of brown hair. He was
looking at me strangely.
"Timmy,Tammy, what should I call you?" he asked.
"Tonight everyone seems to be calling me Tammy, so stay with that --
if you like," I replied.
"Yes I like the name Tammy, it suits you. Are you enjoying today
dressed like that?"
"To be honest no. The reason I'm wearing this stupid outfit is that
I refused to wear a dress and stand in for Sharon. So they tricked me
into wearing this outfit pretending it was a ring bearers costume," I
explained.
"I think you would look better in a dress," said Jason.
"Given everything that's happened so do I," I joked.
"Tell you what," said Jason. "Just wait here a moment." He went back
inside and came back with Aubrey, his sister.
"Look Tammy -- Aubrey has her clothes in the boot of my dads car --
we are leaving later tonight. She can loan you one of her proper
dresses and you can get out of that silly outfit."
"Would you do that Aubrey, anything would be better than these silly
pants and stuff?" I said.
"Yes of course Tammy, just give me a minute to get the car keys from
my dad," she said and hurried away.
So, a few minutes later Jason, Aubrey and I were out at the car. "I
have these two other dresses, one is a summer frock, but it's really a
daytime thing and mummy also made me bring this party dress," she
said, pointing to a white dress with pink trimmings on a hanger. "It
was in case I wanted to change, but I'm OK staying in the flower girl
dress, you can have it if you want, it's actually getting a bit small
for me. I got it for my eleventh birthday party. Do you want to try
it?" Aubrey asked.
"Anything is better than what I'm wearing now," I replied, "what
about shoes? I want to get rid of these terrible shoes," I groaned.
"Don't forget I'm wearing them too -- but yes they are silly. You
look about my size, and I brought a pair of white shoes which should
fit you. You are going to look really neat," said Aubrey.
We picked up the new kit and walked back to the main lounge. "I need
somewhere to change -- I'm not changing in the ladies room again," I
said.
"Doesn't the bride have a room to change in, before she goes?"
suggested Aubrey.
"Right, good idea." So Jason came with me, while Aubrey waited
outside with the clothes, I went up to Janette and whispered in her
ear about borrowing her room for a moment to change my clothes.
"No problem Timmy, you must be really glad to get out of that
outfit, mom went a bit far with the lace and frills," she said.
I took the key from her, and as I left I heard her whisper to Mike,
"He wants to get out of those clothes -- poor kid,"
"Yes, they really were just too girly -- he must have been very
embarrassed," he replied.
Aubrey and I went up to the room and she helped me out of the flower
girl clothes and then picked up the party dress. She placed it over
my shoulders and it slid down -- at this point I looked in the
mirror. "I can't wear this, it's so short and it's got no arms," I
cried.
Indeed it did not have sleeves, it had shoulder straps, otherwise my
shoulders and arms were bare, it ended just about 3 inches below the
top of my legs and it had a sort of built up bosom section which made
it look like I had boobs -- small boobs, but nevertheless boobs. But
again it was seeing my legs encased in white shiny tights that made
me feel very odd -- the dress was so short, much shorter than
Aubrey's flower girl dress.
"I said you would look really neat and you do -- you certainly look
a much more convincing girl than you did in that other silly outfit,"
said Aubrey, who seemed a bit upset I didn't like her dress.
"Yes, I guess you are right, it is just a bit of a shock seeing
myself like this," I replied.
Just then there was a knock on the door. It was Janette, coming up
to see how I was doing. She did a double take when she saw me. "Gosh
Tim, I thought when you said you wanted to change, it was into some
boy clothes not into a party dress, you do look lovely though."
"It's just that Aubrey offered me some clothes. If I had some boy
clothes I would have changed into them." But as I was saying that, I
realised I had never thought of changing back into boy mode -- if I
had, I could have asked Jason for some of his, which were presumably
also in the car. Wow, this was getting really weird.
"Well, if that's the way you want to dress, you need some more
accessories, luckily I have things here in my cases, just a moment,"
said Janette.
"Here are some bracelets, a ring and you'll need a necklace with
that dress and I have just one pair of clip on earrings -- you can
keep the earrings if you like them Timmy," said Janette.
Aubrey was helping me put on the jewellery, then Janette touched up
my make up and re-combed my hair -- putting in also a small flowered
hairpiece.
When I looked at myself I was astonished. I looked like a 16 year
old girl, a bit on the short side maybe -- but definitely a teenage
girl and definitely on the hunt.
"You look great girl, why don't you go out and see your boyfriend?"
said Aubrey, Janette looked astonished at this.
"No, no, he is not a boyfriend, it's just he is the one person who
has showed a bit of concern about the way I have been treated today --
and yes, I like him for that -- but I don't like him because he is a
boy -- he is just a lot nicer than the others I've met today -- but
not including you Aubrey, you've been kind as well -- thank you," I
cried.
"Well, if it helps Tim. I think you are a really nice natured and
good looking boy, and I've always thought that. Doing what you did
today was a wonderful thing, I can't think of any other boys I know
having the guts to do that." With that she came over and gave me a
kiss, right on the lips. This time I really felt a tingle and the
feeling of our lipstick covered lips touching was just wonderful.
This was turning out to be a really confusing day!
"Time to go children," said Janette. So we picked up our handbags
and left the room. Jason who had been standing outside nearly fell
through the floor when he saw me.
He was so surprised at my appearance he literally couldn't speak,
just turning to look at me and gasping. He tried to get hold of my
hand again, but with Janette and Aubrey watching I felt shy, plus I
needed to concentrate walking in yet another pair of heels.
Jason's reaction was multiplied a hundred times over when I walked
into the main room and over to the table and Rosie, Belinda and the
other girls. They gathered around me and asked a load of questions.
I just said I wanted to get out of the silly costume my mom had made
and Aubrey offered me a dress of hers -- "It is comfy, it fits and at
least I look like a human being, yes, like a girl, but at least not
like some pansyfied sissy. I just wanted to show mom -- and Cathy --
that from now on, I was in charge of how I dressed as a boy or even
as a girl and I was not going to take part in any of their games."
Unknown to me both mom and Cathy had come over to the table as I was
making the speech and heard what I had to say. Mom came up to me and
grabbed me and said, "I'm sorry Tim, it was the wrong thing to do --
I was upset when you wouldn't take Sharon's place, but it was wrong
to ask you in the first place -- the outfit was a bad idea, I've had
quite few people tell me that here tonight -- so I apologise."
Cathy came over at this point. "Tim, a lot of the dress up was my
idea, I'm sorry -- I think you are a very brave and talented kid to
do what you did and what you've just done now -- I'm sorry. Just
don't please come near any of my boyfriends dressed like that." That
broke the ice a bit and the tension dissolved. We went back to
chatting -- the boys came over and joined us.
Everyone was much nicer to me now -- although I did get some weird
looks from some of the other guests, but the young crowd were cool
about it. The boys came over and joined us at our table, we chatted
and some of the group occasionally got up to dance.
Jason came over to me and asked me again for a dance. I was a bit
shocked, no one had suggested he should do it this time.
I said, "Don't let this dress fool you Jason, I am a boy under all
this clobber -- are you sure you want to dance again?"
"You are as pretty as any of the girls and you are nice to dance
with, so why not? Some of the girls are already dancing together," he
replied.
This was true, most of the boys were sitting around talking, but the
girls were all up dancing, so as I was the only "girl" not up and
dancing it seemed unreasonable to refuse.
"Yes, I'd like to dance with you Jason, let's go," I said and we
went up to the dance floor.
Janette and Cathy were both up dancing and as she passed Janette
asked, "Are you enjoying yourself, Timmy?"
"Yes," I replied, "this is a lot better than that other silly
outfit. Although I would prefer trousers."
"Well you look really nice, and thank you again for being my flower
girl and ring bearer."
Cathy also came by with her partner. "This is my little brother
John, doesn't he look cute in his party dress and you've found a
boyfriend I see," she needled me, yet again.
"It's your fault I'm dressed like this Cathy, if you and mom had let
me wear a proper ring bearer suit -- I wouldn't have ended up like
this. Jason is just my cousin, he is not a boyfriend."
"Wow, your sisters are very different, aren't they," said Jason as
they moved away, "is Cathy always so mean to you?"
I explained to Jason how we were always arguing and she was always
running me down. We went on to talk for quite a while, again sitting
outside away from the noise. He is an interesting guy and like me is
a keen swimmer and seemed to like the same kind of music I do.
While we were chatting, Aubrey walked up and said, "Hey Jason, stop
monopolising Timmy, I'd like it if he had a dance with me. You don't
mind me asking, do you Tim?"
I blushed and said, "We were just chatting and yes I'd really like
to dance with you."
So then we spent the next few dances together. "Have you ever danced
with a boy before?" she asked.
"No, and I've never danced in a dress before -- and I never will
again," I said with emphasis.
"Tim, I meant what I said before about liking you and admiring you
for what you've done, I'll understand if you want to go back and chat
with Jason, but I would like it if we could talk for a while," she
said looking straight into my eyes.
I have never had a girl speak and look at me that way before and
again I felt that tingle.
"Look Aubrey I think you are the nicest, prettiest girl in the room.
I'm just bowled over that you'll even talk to me, especially when I'm
in a dress. Jason and I were just chatting about things, like
swimming and music, there is nothing more to it, if that's what you
were thinking." I looked straight back at her, now holding her hands.
"I know you are champion swimmer at school, you even tried for the
county juniors, that you do voluntary work for an old persons home
and you are in the top two or three in all your subjects at school,
that you like music and drama and play the piano and the guitar and
you've won prizes for your singing," she said.
"Where did you get all that from?" I said astonished.
"I told you I liked you and I've been talking with Janette -- she
told me a lot about you, and I saw how you helped Tammy look after
and entertain the small children today," she replied.
"Well now I need to know about you then," I countered. So we talked
animatedly for the next hour. Aubrey was fun to talk to and time just
flew by until my mom came up and said it was time to get ready to go -
- the car to take us back home was waiting.
I said to Aubrey, "How can we meet again, do you go into Bramfield?"
I asked. Bramfield being the nearest large town, I knew Aubrey lived
25 miles away on the other side of the town.
"We will have to meet again, if only for you to return my dress and
shoes!" she said. "Yes I visit Bramfield to shop -- we can meet there
if you like."
"Yes that would be great, I have a swimming competition at the
Bramfield leisure centre a week on Saturday, I could meet you after
that, we could go for a snack and maybe go on to the pictures," I
replied.
"Can I come to watch you swim first? I'd like to see you, I could
cheer you on," Aubrey asked.
"Wow, my own supporters club, I'd like that. I'll call you and we'll
fix up when to meet," I moved closer to her to say goodbye, at the
same moment she moved towards me and it seemed natural that we came
together and kissed.
"Well isn't that a pretty sight, two beautiful girls having a long
lingering kiss -- time to go home Tammy -- are you saying goodnight
to Jason as well." This was Cathy, jumping straight in, in her
characteristic manner.
I did not deign to reply, other than to glare at her. "She IS awful
to you, we will have to find a way to get back to her," said Aubrey.
"Really it's not worth the trouble, I just wait for the time she goes
off to college and I don't have to mess with her anymore. Anyway, I
must go, see you in Bramfield next week," I replied.
"I'll look forward to that, but who shall I meet Timmy or Tammy?"
she joked.
"That's for me to know and you to find out", I replied. "Perhaps I
should go and say goodbye to Jason, he has at least been kind to me,
as well."
"You really are such a thoughtful and good natured boy aren't you,
what a contrast to your sister. Just be careful with Jason, he may
want to kiss you as well," she said.
"The sooner I get this dress off the better, then," I joked. But
there was something in the way Aubrey looked at me as she talked
about Jason that made wonder if she was trying to tell me something.
As I went over to Jason, he jumped up and said, "I wondered if we
would get a chance to say goodbye. Thank you for the dances and I've
enjoyed talking with you. What would you think if we met up in town
and went to the arena next time they have a good concert?"
"Great idea, yes let's get in touch and thanks for giving me time
when I've been dressed like a weirdo," I replied quickly, not really
wanting to get in too deep but not wanting to be rude to a guy who
had been kind to me. We slapped hands and I turned to leave, but I
could see in the mirrored wall in front of me he watched my every
move as my dress swished round and I minced out on the of room in
Aubrey's heeled shoes.
As I sat in the car on my home I thought back on my day, spending
nearly 12 hours in girl's clothes -- it had been a long day, and my
feet really hurt but I had made two new friends both of whom seemed
to like me and wanted to meet me again. But I did need to find out
- from Aubrey what she meant in that remark about Jason.
++++++++++++++++++++++++++++++++++++++++++++++++++
To be continued