The Best Week of My Life Chapter 4 The Final Weekend
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The Best Week Of My Life - Chapter 2 - The First Weekend free porn video
THE BEST WEEK OF MY LIFE
CHAPTER 2 - THE FIRST WEEKEND
Bobbie was sound asleep at 8:00am the next morning when her mother came
in to wake her. "Come along sleepyhead," Mrs. Harris admonished. "It is
8 o'clock and if you are not careful your girly Saturday will slip away
from you!" Bobbie leapt out of bed and hurried to the bathroom. Mrs
Harris called out after her, "Your friend Stan has rung already. He was
wondering if your brother, Rob, could lend him a few clothes for the
week. He says he is sure his sister, Sally, will do the same for you. I
have to say I think it is a very good idea. Loaning each other a few
outfits will save all of us quite a bit of money."
Bobbie hopped into the shower and, whilst she was drying herself off
back in the bedroom, returned Stan's phone call. "Brilliant idea," she
said. "What sort of things do you think you might need?"
"Not much," replied Stan, "a pair of casual trousers; a couple of
shirts; a couple of tees; hoodie; trainers; oh, and one smart outfit for
church should do it. I won't need any of your underwear and socks
because mummy insists I must have my own new ones. Can you come over
here with the things? It is relatively easy for me to put together a
list, but you, as the girl in this deal, will need to choose a lot
more," Bobbie said he would be over in about an hour.
True to her word, Bobbie arrived at Stan's house before 10 o'clock. Mrs
Sanders, Sally/Stan's mum, let him in. "My, aren't you the pretty one!"
she exclaimed. "Stan is waiting for you upstairs. I have told him that
it is alright, on this occasion, for the two of you to try on clothes
together. He has promised me that nothing untoward will take place and,
if you give me your word as well, you can go up."
"I promise Mrs Sanders," Roberta said. "This week is weird enough
already without complicating it further!" Mrs Sanders smiled as Bobbie
hurried upstairs. "That boy should have been born a girl," she thought
to herself, "he is much to pretty for his own good."
Stan gave a girlish squeal of excitement when he saw the bulging bag
Bobbie was carrying. "Oh, I just adore trying on new clothes," he
squeaked, "even if these are boring old boy's things."
"Calm down," advised Bobbie, "you are not behaving in a very masculine
manner at the moment. You need to be cool and bored by the whole
question of clothes." Stan apologised and the two of them unpacked the
grip. In addition to the things Stan had asked for, Bobbie had put in a
pair of smart black trousers, his best brown leather jacket, and
matching leather tie, a pair of black lace-up shoes, and a belt. "I
thought you might need a belt," (s)he explained; "although you are still
pretty slim, you are starting to show a few curves and I guess your
waist will be smaller than mine and your hips bigger." The "Sally" part
of Stan blushed. "Oh, you've noticed have you?" she teased. Now it was
Bobbie's turn to redden.
"Let's make a start," said Stan. "The sooner we get me sorted out, the
more time we will have on the fun bit of choosing your new outfits." He
stripped off the clothes he was wearing down to his constricting-vest,
y-fronts and socks. Bobbie noticed that Stan was displaying a bulge in
his underpants. Noticing Bobbie's glace, Stan coloured up once again.
"Mum thought I should show a little masculinity down there," he
confessed.
"It doesn't bother me," said Bobbie. "I think it's cool; it is no
different from my wearing false breasts and having to squeeze up my bits
inside tight knickers."
It didn't take long for Stan to decide that everything Rob was loaning
him was fine and for the clothes to be summarily put away. The two of
them turned their attention to Sally's wardrobe. "I won't need many
clothes," said Bobbie, looking aghast at the vast array of dresses,
skirts and trousers hanging in the closet.
"Don't be silly," reposted Stan. For the next couple of hours I am going
to revert to being Sally and I'll teach you a few important facts about
being a girl; the first one being, you can never have enough clothes!
She started pulling various garments off their hangers and piling them
on the bed. "These will do to start with I think," she said. "Why have
you still got your sweater and skirt on? Get serious girl! By the way I
think it is a really cute outfit your Mum bought you."
"Do you really like it?" asked Bobbie. "It is very comfortable and I am
starting to feel OK about it myself." She slipped out of her outer
clothes and stood there clad only in bra, panties and hose. Sally - for
whilst still dressed as "Stan", she was all "girl" for the present -
handed her pink tee-shirt with a kitten print on the front and a tight,
black mini-skirt. Once she had managed to wriggle her way into the tight
garments, Bobbie looked at her reflection in the mirror. An excited,
shiny-eyed young teen looked back at her. She really was a natural for
this cross-dressing lark!
The next few hours were taken up with Bobbie clambering in and out of a
succession of outfits. Ones she and Sally approved of were neatly piled
on the bed, whilst the discards were summarily dumped on the floor. By
the time they had finished Sally's bedroom looked as though a bomb had
hit it! "Am I really going to need all these clothes?" Bobbie asked
anxiously, looking at the pile of "approved" garments.
"Probably not," replied Sally with a smile, "but you are going to have
great fun choosing what to wear. There is a fair chance that we will be
encouraged to go out in the evenings this week as part of our gender
programme and you can't be seen wearing the same thing twice!"
There was no way all the clothes were going to fit into Bobbie's grip,
so Sally asked her Mum for the loan of a wheelie suitcase. Once
everything was packed away and the bedroom tidied, Sally turned to
Bobbie and said thoughtfully, "You know, most of the clothes I have
loaned you I don't really wear any more, so don't worry about what
happens to them; you don't have to give them back."
"Are you sure?" replied Bobbie. "They look fairly new to me. It seems a
shame that you aren't going to wear them any more."
"I'm bored with them," smiled Sally "and clearing these old things out
gives me an excuse to buy new clothes!" Bobbie started giggling at this
repost. As "Rob" clothes shopping was a chore not a pleasure; (s)he was
certainly learning about the differences between boys and girls this
morning.
"Now we have sorted out your outerwear," Sally continued, "that just
leaves the question of your lingerie. How much did your Mum buy you?"
"I'm not sure," replied Bobbie. "Not much I think; she said only enough
to get me started so that I could enjoy shopping for myself."
"Well you will certainly need more that a couple of sets," said Sally,
"you are going to be wearing at least two pairs of knickers a day - one
for school and one when we go out in the evening. I think a trip into
town is called for. I'll also need to pick up some more underpants and
vests for myself" - (switching back into "Stan" mode). Bobbie rang home
and her mother confirmed that, indeed, she would need to buy some more
lingerie. "Do you have any money with you dear?" she enquired and, on
Bobbie confirming that she did, gave her permission for the two of them
to go into town.
"As it is Saturday, you need to look trendy going into town," Sally
advised. "The skirt and sweater you wore over here will do just fine.
You can leave the things you are borrowing here until we get back.
Bobbie had cycled over to "Stan's" house and his bike was in the garden.
Stan took one look at it and said, "You can't ride that; it's got a
crossbar and you are wearing a skirt! You will have to use my bike and
I'll ride yours." Accordingly the two young people swapped bikes and
Bobbie swung herself up onto Sally's pink one. She found it much easier
to ride whilst wearing a skirt as, to be honest; she had experienced
great difficulty keeping her skirt from riding up on the way over. Stan
swung his leg over the crossbar of Rob's bike with great aplomb and they
set off for town.
"Where shall we start?" asked Bobbie as they locked their bikes in a
cycle-rack.
"Let's start with Marks and Spencer," replied Stan. "They sell both boys
and girls clothes so we can each get what we need from the one shop."
So they hurried off to M&S and were soon in the lingerie department. "My
stuff will only take a minute to find," said Stan. "Let's concentrate on
getting you some pretty undies." It took, in Bobbies eyes, a remarkably
long time to select two bras, six pairs of knickers, and a few pairs of
tights. "You have got to have the right shade of tights to go with
whatever outfit you choose," explained Stan, "and you simply must buy
that pair with the seams up the back. You will look wicked walking down
the street wearing them with my - sorry "Sally's"! - black velvet
miniskirt and patent heels. I've got a super pair with a four inch heel
that Mummy doesn't know about - I'm not supposed to wear heels over
three inches high; I'll loan them to you - but I will want those back
afterwards!"
Bobbie spent rather a lot of money on underwear that (s)he would only
need for one week. (But, heh, this was a "once in a lifetime
experience", right? So, make the most of it.) As Stan had correctly
predicted, it took much less time to buy him six pairs of underpants,
two elasticated vests, and four pairs of socks. "Now we have the
essentials we can enjoy window shopping," said Stan excitedly - in
danger of slipping back into "Sally" mode. He caught himself just in
time. "What I mean is," he said gruffly, "I don't mind wandering around
with you for a bit if there are more shops you would like to check out."
Bobbie gave him a big grin. "I'm sure I would benefit from any advice
Sally's brother can give me," he said.
"Then let's go to Primark," Stan said. "My sister shops there all the
time and they have great fashion items at incredibly cheap prices."
Primark was a revelation to Bobbie. The store was full of young people -
both boys and girls as the shop also sold men's clothing - but,
naturally Bobbie and Stan concentrated on the racks of girly things.
Stan kept a pace or two behind Bobbie but whispered advice as to things
he thought would suit her. "You just have to get that sequined top," he
breathed, "it is gorgeous and I would love to wear it when you have
finished with it!"
The garment in question was a simple boob-tube type top, cut square
above the bust, and with little spaghetti straps. It was decorated all
over with multi-coloured sequins and even to "new girl" Bobbie it
demanded to be purchased. Stan also directed her to the costume
jewellery section where Bobbie bought quite a lot of bangles and
necklaces for a few pounds. She looked longingly at the earrings. "I
should really get some more earrings," she said sadly. "Mum has loaned
me these clip-ons but they don't go with the new stuff I have just
bought."
"Why don't you get your ears pierced?" Stan said excitedly. "Lots of
boys do these days so you won't look out of place once our gender
programme ends."
"Do you think I could?" responded Bobbie. "What would my mother say?"
"If you've already got it done there isn't much she can do about it, is
there?" replied Stan with a grin. So they hurried off to a jewellers
shop, and before long Bobbie sported a pair of shiny studs in her ears.
By the time they finally set off home, several pairs of pretty earrings
had joined the pile of purchases in her bags.
On arriving back at Stan's house, "his" mother, Mrs Sanders, insisted
that both young people model their new clothes for her. Needless to say
it took Bobbie a lot longer to show off all her purchases than it did
Stan! "Well done dears," said Mrs Sanders when, at last, they had
finished showing her everything, "but Bobbie, you are never going to be
able to cycle home with all the things Sally is loaning you as well as
these new clothes. I'll run you home in my car and you can put your bike
in the back." At this point Stan explained that they had already swapped
cycles for the week so that their transport was more consistent with
their new image. "Brilliant idea," said Mrs Sanders, "so Stan if you
will just load Bobbie's pink bicycle into the back of my car, we will
set off." Stan huffed and puffed a bit as "he" struggled to lift the
bicycle into the back of his mother's 4x4. Eventually, however, he
succeeded. "I didn't realise you boys had it so tough," he whispered to
Bobbie in an aside.
It did not take Mrs Sanders long to drive the two young people across to
Bobbie's house and whilst she chatted with Mrs Harris about what they
each hoped their child would gain from the week-long gender swap, Bobbie
took Stan up to "Robert's" room and offered to loan him a few soccer
posters and other odds and ends so that Stan would constantly be
reminded of his new gender. "Thanks," said Stan, "shame we didn't think
of this before we left my place, or I could have lent you some dolls and
photos of male film stars! I'll drop them round tomorrow."
The two mothers had by now finished their conversation and Mrs Sanders
called out to Stan that they were going home. The two friends promised
to meet up again Sunday afternoon and to continue sharing ideas to help
them make the most of the forthcoming week.
When Bobbie and her mother were alone, Mrs Harris complimented Bobbie on
the way she was addressing the challenge of the gender swap. "I think
you have done extremely well so far," she started, "to have gone out
shopping for girl's clothes on your first day was very brave, although I
can see that it helps when you have a friend like Sally - sorry "Stan" -
to help you. Now, if you are up to it, I think Daddy and I would like to
take our new daughter out for a pizza this evening. How do you feel
about that?" Bobbie shrugged. "I've decided to accept any challenge this
week," she said. "After all it is only for seven days and is a "once in
a lifetime" experience."
"Good girl," said Mrs Harris kissing her. "A positive approach can help
you achieve almost anything, so I applaud your decision."
Mr Harris arrived home from his afternoon on the golf course shortly
after and agreed wholeheartedly with the suggested outing. Mrs Harris
took Bobbie up to her bedroom and helped her chose an appropriate outfit
for the evening. "Smart but not too dressy," she advised. "I think this
might do," she advised, holding up a black and white check kilt, a
simple black tee with silver sequins around the boat-shaped neckline,
and a white cardigan. "With black tights and those two-inch black heels,
you will look lovely. I'll show you how to apply an evening make-up
appropriate for a girl of your age; I'm not letting any daughter of mine
go out looking tarty!" The two of them laughed together and Bobbie
reflected that as "Robert", he had never enjoyed such closeness with his
mother.
Bobbie did indeed look lovely when Mrs Harris had finished making up her
face and brushing out her blonde wig. "Now go downstairs and chat with
your father," she instructed, "whilst I get prettied up myself. I am
going to have to take care or my son will be getting more admiring looks
than I do, and that will never do!" Roberta hurried downstairs. Mr
Harris was already dressed in an open-neck shirt, trousers and sports
jacket. He was sitting in the lounge sipping a gin and tonic.
"How do I look Daddy?" asked Bobbie, giving a little twirl in the
doorway.
"Absolutely beautiful!" her father replied. "Although I knew what was
going to happen this week, I never could have imagined just how quickly
you have settled into your new role. Now, as soon as your mother is
ready, I will be proud to escort my two lovely ladies out to supper."
It wasn?t long before Mrs Harris came downstairs and soon the three of
them we in the car driving to their favourite pizza restaurant. Robert
was well known at Pizza Express and the waiting staff all gave him
amused grins as he walked in wearing "her" skirt and heels. "Don?t
worry; just ignore them" whispered their waitress. "I think you look
lovely and I guess half of those macho blokes wish they were in either
your shoes or your knickers!" Bobbie blushed a deep red and lowered her
eyes. As ever the meal at Pizza Express was very good and Bobbie was
allowed a small glass of red wine. Afterwards they strolled through the
town centre for half an hour before driving home. Mrs Harris enjoyed
being able to window shop with her new "daughter" and to point out
clothes that she thought would suit her.
By the time they got home Bobbie was exhausted by all the excitements of
the day and asked to be excused as she wanted to go to bed. Both her
parents kissed her goodnight, which was something her father never did
any more for Robert. As she slipped into her nightdress, Bobbie ran
through all the things she had done in her mind and fell asleep dreaming
of what might lie ahead on the morrow.
Sunday dawned bright and fair and Bobbie was awakened by her mother
bringing her a cup of tea in bed. "Wake up sleepyhead," she admonished,
"it is already half past eight and you will have to get your skates on
to be ready for church."
Bobbie leapt out of bed and into the shower. It felt strange washing
with her breast forms sitting proudly on her chest. Once she had
finished showering, Bobbie rummaged through her collection of clothes
trying to find something suitable to wear to church. Eventually she
settled on a pale blue skirt suit, cream blouse, navy heels, with
matching navy hat and gloves. Looking at her reflection in the mirror,
she thought, "Gee I don?t look half bad; I could get used to this."
Rapidly shaking her head, Bobbie tried to come back down to earth. This
was for one week only; a lesson in gender differences, not a permanent
change in life style!
Church went surprisingly smoothly. A number of cross-dressed boys and
girls were there with their parents. After the service family groups
intermingled; chatting about the way their offspring were dealing with
the gender experiment. Bobbie managed to catch a few words with Stan,
who promised to cycle over after lunch. At home, Bobbie found that, as a
girl, she was expected to help her mother with the preparation of lunch
? something which as Robert would never have occurred to her. After
lunch she asked her mother if she could change into something more
casual and, having receiver her assent, ran upstairs and put on a pair
of denim jeans ? skinny fitting, and with a pink motif embroidered on
the back pockets ? together with a pink, v-necked, cashmere sweater, and
black flat shoes.
As promised, Stan cycled over at about half past three and the two
friends spent the rest of the afternoon in Bobbie?s bedroom, discussing
how they might handle the forthcoming week at school and swapping tips
about how to best present as a member of the opposite sex.
When Stan/Sally finally went home, Bobbie helped her mother put together
a tray of supper and the family settled down to watch television. Bobbie
found, somewhat to her amazement, that she was really enjoying a
romantic "chick-flick" which, only a couple of days ago "he" would never
have considered viewing.
Monday was "school day" so, after another relatively early night, Bobbie
turned in. The Gender Swap programme was going to start tomorrow in
earnest!
Charlize
- 19.02.2022
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