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Ben looked at his watch. He couldn't wait for the day to be over and to
finally get home. He'd had enough of school for this week and didn't want
to waste another second in the classroom. Thankfully he didn't have too
much longer to wait as five minutes later the bell sounded and he was on
his way home. His friend Peter was waiting from him at the gate, as
usual, and the two boys walked together towards their homes.
"Glad that one is over with," Peter muttered as he took a bite out of an
apple. He hadn't eaten all day so was hungry.
"Yeah, me too. Was so bored in English just now, I swear I nearly fell
asleep," Ben replied.
It didn't take long for talk to turn to the weekend, and what each
other's plans for it were. They both had an idea of what they wanted to
do, but were not prepared to say it out loud whilst in ear shot of people
from their school.
"Do you want to come over? My Mom hasn't said if she's going out or not,
but she might do. If not we can just hang out in my room or something."
Ben was usually the one to make the offer to hang out, which suited both
of them as Peter liked going over to his friend's house, and Ben liked to
host.
"Sure. Hopefully your Mom will need to go out for something, but if not
it's cool." And with that, the deal was done.
"Come over about 12?"
"Yeah, ok. See you then!"
The two boys came to a turning in the road, Ben went one way, and Peter
went the other. The rest of their evenings were fairly uneventful, they
watched some TV and ate some food. Both were looking forward to tomorrow,
the start of the weekend, and hopefully some time alone together.
The next day, Peter got to his friend's house for just after 12pm, he was
met at the door by beaming smile and an excitable Ben. He was ushered
inside and the door was quickly closed behind him.
"Guess what?!" Ben didn't give his friend chance to reply. "Mom's gone
out, we have the place to ourselves!"
"For how long?" Peter replied.
"Four hours!"
"Really, four hours?!" Peter was getting excited now too, as he began to
imagine what they might be able to do with that much time to themselves.
"Where has she gone?!"
"Oh that doesn't matter. What's important is that we have the place to
ourselves now," The two boys looked at each other for a second, Ben then
said what the both of them were thinking. "You wanna dress up?!"
"Yeah, let's do it." There was a little nervousness in Peter's voice, but
he managed to smile too. Even though they had both done this before,
there was still the lingering feeling of guilt, and also a fear of
getting caught. But this was greatly outweighed by the feeling of
excitement for what they were about to do.
The two boys went up the stairs, with a definite eagerness to get to the
top quickly. Ben led the way and headed straight for his mother's
bedroom. The door was already open, not that it being closed would have
stopped them from going inside. As the boys entered, their attention was
immediately caught by a beautiful red dress, hanging up from the outside
of the closet.
"Wow, look at that!" Peter was the first to comment.
"Yeah, I wonder why she left that out..." Ben ran his hand over the
sparkly bodice, and then down the soft poufy skirt.
"It's gorgeous!" Peter instantly fell in love with it and soon joined his
friend for a closer look "You gonna try it on?!"
"Maybe..." Ben took a step back from the hanging dress and went back to
close the bedroom door. It seemed a little pointless as they were the
only people in the house, but he did it anyway. "You should wear it, it
would suit you better... with your darker hair."
There was no knowing who the dress would suit better, but Ben was happy
to make the offer. While Peter was very much a dark brunette, Ben's hair
was much lighter. Both boys had grown their hair over the past few
months, and while not yet at the length they were aiming for, both had
plenty to play with when it came to creating a style.
"Shall we do make up again?!" Peter gazed over at his friend's Mom's
dressing table, various beauty products scattered across it.
"Yeah, I'll do yours if you do mine?" Ben smiled at his friend. "I think
we should get dressed first though, no point wasting any time. Are you
going to wear the red dress? I think you should."
"I'd love to, it's so pretty! Thank you!!" Peter returned the smile.
"What are you going to wear?"
"I haven't decided yet, will have a look in the closet. Here take this."
Ben carefully lifted up the red gown from the outside of the closet, and
handed it to his friend. It really was a beautiful dress and truth be
told, he was starting to feel a little envious that Peter was going to be
the first to try it on, rather than him. But he knew there were lots more
beautiful dresses to choose from, and his excitement levels rose as he
slowly opened up the closet to reveal all that was inside.
Ben immediately pulled out a couple of dresses to look at, a blue and
white floral one and a pale green one. Both were stunning in their own
right, but they weren't what he was looking to wear today. He chose
another one, a long pink gown, and carefully took it out to have a closer
look. He held it infront of him for a few seconds, glancing over at the
mirror on the wall across from him, before putting it back into the
closet again.
"You better be careful to put them back in their right places, I mean
your Mom might have an order!" Peter was watching from the other side of
the room, still holding onto his red gown.
"Order? Nah, Mom doesn't do that. I mean, what kind of order could they
possibly be in? It's certainly not by style, or age; this is one of her
newer ones and it's in the middle..." Ben didn't know it yet, but his
relaxed attitude to putting his Mom's dresses back exactly where they
came from would ultimately be his, and Peter's downfall.
"You not going to wear pink again?"
"No, I want to try something different today. I want to be a
sophisticated woman..."
"You're going to look amazing, whatever you wear," Peter smiled at his
friend, and then to himself as he took another look at the beautiful gown
he wold soon be wearing. "And I'm going to be a princess wearing this!"
"This one..." Ben had found the dress he was looking for. He had seen his
Mom wear it on a night out earlier in the summer, and had been curious to
try it on ever since. Today was the day. His heart beat a little faster
as he held it out infront of himself, imagining what it would be like to
wear, he was about to find out. The dress was stunning. It was long and
black and sparkled a little when it caught the light.
"Yes, I love it!" There was enthusiasm in Peter's voice, he was genuinely
excited for his friend.
The two boys had now chosen their dresses and so could begin the joyous
task of putting them on. But just wearing the dresses was no longer
enough, they wanted to see how far they could take it, how much like
women they could make themselves look, and feel.
Opening up a drawer to the side of the bed, Ben pulled out a few items,
and laid them out for him and Peter to see. "I think we should wear these
too."
"Wow, are you sure? I mean, will your Mom not know they've been worn?"
"No, it's fine. I'll put them back at the bottom, so she won't see them,
and when she does... she won't know, trust me. You said last time that
you wanted to try stockings, well here's your chance!"
Laid out infront of them, were two sets of stockings, complete with
suspender belts, lace underwear, one black, one red, and two silk vests
to match. Ben had worn his Mom's underwear in secret before, but this was
the first time he had ever shown it to Peter, let alone offered it to him
to try.
"What about shoes?"
"My Mom has like a thousand pairs of shoes, I'm sure you'll be able to
choose something you like!" Ben teased. He looked at his watch, half an
hour had passed since his Mom had left. He knew they only really had
three more hours before they would have to change back, so he was keen to
make the most of it.
The two boys began to undress from what they were wearing, each making a
small pile of clothes they were no longer interested in; they seemed so
boring in comparison with what they were about to put on.
"Are you going to be Bethan again?" Peter asked
"Of course! It'll always be Bethan," Ben replied. "Have you decided on a
name now?"
"Yeah.... Pamela"
"Pamela, I like it. Suits you!"
"Thanks," Peter smiled.
The two boys were now standing almost naked in front of each other, but
it didn't matter at all, they were ready to put on their underwear and
begin their transformation into women. Turning away from each other for a
little privacy, Peter took the red lace underwear, and Ben took the
black. Taking off their boy-boxers, they slipped their legs into the lace
knickers, pulling them up slowly, before turning their attention to the
silk vests, raising their arms to let them down into place. Still
resisting the urge to turn back and face each other, the two boys then
picked up their suspender belts and despite a little awkwardness
initially, managed to fasten them. Next it was the stockings, Ben's were
dark, almost black, Peter's were much lighter. Ben had done this before,
but for Peter it was his first time, both boys stepped into each rolled
up stocking, and slowly pulled them up their legs.
"Wow, these are amazing!" Peter whispered, but loud enough for his friend
to hear.
Soon both boys were ready, and turned to face each other. They couldn't
help but smile.
"Well, what do you think?!" Ben was the first to speak.
"Oh my God, these are so soft!" Peter slowly ran his hand down his soft
left leg. "And the underwear is incredible! Why women don't wear these
all the time, I'll never know."
"Maybe some do?!" Ben joked. He was keen to keep the transformation
moving along though so suggested they move on to the next step.
"Dresses?" Peter was even more excited to wear his red gown now.
"No, put on a robe..." Ben pointed to a couple of silk robes hanging up
by the door "We'll do make up now, the dresses should be last to go on,"
He spoke like an expert, and while compared to Peter he probably was,
this situation was still relatively new to himself too.
Peter did as instructed and slipped into a long white robe, handing the
other, a black one, to Ben. He was somewhat in awe at all the nice things
his best friend's Mom had in her room, why she needed two robes hanging
up when she was the only one using the room he didn't know, but he didn't
feel the need to ask.
"Sit in the chair, I'll do your make-up!" Ben pulled out the chair beside
the large white dressing table which dominated one wall of the room,
gesturing for Peter to sit in it. "Sit still, close your eyes and no
looking until I've done!" His instruction was clear and Peter followed.
What followed next was a masterclass in a simple but effective beauty
makeover. Ben knew all the tricks, which primer to use, the appropriate
foundation for Ben's skin, how to highlight his cheeks and the best shade
of gloss for his lips. The look was completed with a stunning eye shadow
and mascara, giving him long and luscious looking lashes. He ran a brush
through his hair and held it back on one side with a cute red clip.
"What do you think?!" Ben moved to one side so Peter could see his
reflection in the dressing table mirror.
"Oh my.... wow! I love it. Thank you! You're so good at that."
"It's not difficult, and anyway, I've been watching my Mom do it often
enough, I picked it all up from her I guess! Move over, time to do mine,"
Ben smiled as the two boys swapped positions. Despite the earlier
agreement, Ben did his own make up, and Peter just sat on the bed and
watched. Ben's own makeover was just as effortless as Peter's had been,
he chose a different eye shadow and a red lipstick instead of gloss, but
otherwise he used the same products. When finished he stared at his new
reflection in the mirror, and Peter came to stand behind him at the
chair.
"Imagine if your Mom came back now!" Peter giggled.
"Oh, don't say that!" Ben snapped, nervously. "She's not due back for
ages yet". He checked the clock beside the bed; it was just after 1:30pm.
"Would you like to do my hair?"
Peter picked up a brush and began to run it through his friend's hair.
While he was doing this he spotted a set of curling irons on the floor by
the table, without asking he picked them up, plugged them in and turned
them on. A few seconds later he was carefully adding a few subtle curls
to the bottom of his friend's hair, quickly transforming it into a
beautiful new style. He added a black fabric headband, and he was done.
"You said you wanted to be a sophisticated woman, now you will be!" Peter
smiled, impressed with what he had been able to do for his friend.
"Perfect!" Ben loved what he saw. So did Peter. The two boys were fast
becoming beautiful women; they were now ready for their dresses.
Ben went first, carefully stepping into his dress, he pulled it up over
him and stood still while Peter zipped it up the back. It was everything
he had hoped it would be, and more. The look he had created with his hair
and make-up complimented the dress perfectly, all he needed now were
shoes and a few accessories. Heading back to the closet, he picked out a
pair of black sling-back heels, he slipped his feet into them carefully
before taking a few steps across the room as practice. Over at his Mom's
dressing table, from a drawer he picked out a sparkly necklace and
matching bracelet, before completing his look with a black silk shawl,
which he draped over his shoulders. He resisted the urge to take a long
look in the mirror; instead he said nothing and went over to Peter to
assist him with his dress.
Peter needed a bit more help getting into his gown; having so many layers
to his skirt was certainly a new and exciting experience for him. After
stepping into the skirt, he then fed his arms through the sleeves and
stood still while he was zipped up. There was no why he could have
managed this himself, as the zipper was a bit of a struggle for Ben,
almost jamming half way before finally making it to the top. The body of
the dress was stunning, figure hugging with plenty of sparkle. Ben found
some jewellery for Peter to wear too, a necklace and some clip-on
earrings, as well as some red high heels from the closet. The two boys
were now ready for the big reveal at the mirror.
Ben held out his hand, and took Peter over to the large floor-length
mirror on the other side of the room, being careful in their heels and
long dresses as they walked. When at the mirror, they stood quietly in
disbelief at what they saw. They had both dressed as women before, but
they had never looked as good as they did today.
"Oh my God..."
"Oh my..."
They were like stunned but excitable school girls, unable to get any
words out to speak. Both boys swayed their hips gently and moved around a
few steps, examining how their dresses felt and looked when moved. They
found themselves holding hands at the mirror, sharing this beautiful
moment together.
"You look so beautiful, that dress is perfect for you. You look like a
princess. How do you feel?!" Ben asked his friend.
"I feel like a princess!!" Peter giggled. "You look amazing too; you're a
sophisticated woman, just like you wanted to be!"
"I feel amazing." Ben's voice broke a little with emotion. He couldn't
believe what he had just done, how good he looked and how it made him
feel. The best part of it all though was being able to share the
experience with his best friend.
"What shall we do now?" Peter took a few steps to his right, and perched
on the corner of the bed, allowing his big skirt to puff up around him
slightly.
"Well now we are Bethan and Pamela, we should enjoy ourselves. We have
just over two hours until there is any chance of Mon coming home, so
that's at least an hour and three quarters before we need to worry about
changing. That's an hour and three quarters of being beautiful women,
wearing beautiful dresses. It's what we've always dreamed of, right?!"
"Yeah, it really is!" Peter, now Pamela, smiled.
Bethan and Pamela spent the next few minutes in the bedroom, admiring how
they looked, complimenting each other at regular intervals. Pamela found
a couple of fancy clutch bags at the back of the closet for them both to
hold, and they took pictures of each other on their cell phones. They
really were living a dream.
"Thank you for sharing this with me Bethan, I mean, it must have been
quite a risk for you to tell me you liked to do this, wear your Mom's
clothes. You didn't know how I was going to react, or that I would want
to do it with you too."
"Well we've been friends for a long time, I knew you'd be cool with it. I
didn't know you'd end up looking more beautiful than me though!" Bethan
giggled. "Do you never get chance to look in your Mom's closet?"
"No, not really. She keeps the door locked most of the time, when Dad
isn't around anyway, and I would never want him to catch me in there. And
anyway, she doesn't have the nice dresses your Mom has, well, not as
many."
"My Mom spends all her money on clothes; she has an obsession with
designer labels. She did really well out of divorcing my Dad. So I guess
that makes me lucky, having access to all these dresses."
"Does it bum you out when you have to change back to being a boy again
though?"
"Yeah, I guess," Bethan replied, a slight hint of sadness in the
response.
"Do you wish you were a girl all the time?" Pamela dug a little deeper.
Bethan paused. "Maybe." That was as far as she was prepared for the
conversation to go though, so she attempted to swiftly change the
subject. "We should go downstairs, no need to spend all afternoon in the
bedroom."
"Sure ok, you go down, I'll meet you there in a few minutes, I just want
to see my reflection again..." Pamela moved back over to the mirror while
Bethan passed by and headed for the door.
Grabbing her clutch bag, Bethan left the room and descended the stairs,
carefully in her heels and long dress. She went into the living room and
closed the door behind her. She sat down on the sofa for a few moments,
but then stood again, pacing the room a little, for no other reason than
to practice her walk in her shoes. Being alone in the room she felt
slightly vulnerable though, so she hoped Pamela wouldn't be too long
before joining her.
A few minutes passed, Pamela was still upstairs and Bethan was still
alone in the front room, or so she thought. She didn't hear the door open
so had no idea how long her Mom had been stood there watching. Turning
around, her heart sank as all her worst fears suddenly began to come
true.
"Hi Ben." Lauren smiled at her son.
"Oh my...." Bethan, now very much back to Ben, was speechless, his face
began to turn a bright shade of pink.
"It's fine Ben, don't be embarrassed. I'm not angry; I just wish you'd
asked me before borrowing my clothes."
"Honey, you look beautiful, you really do!" Jennifer, Peter's Mom, was
there too.
Ben wanted the floor to open up and swallow him, he was mortified. His
life was over. Why had she come home so early? And what was Peter's Mom
doing there too? He was only upstairs and was moments away from coming
downstairs to be discovered too.
"I must say I'm a bit surprised though, I kinda expected you to be
wearing the red dress I left out..."
"Oh, well erm...." Ben began to speak but his sentence was cut short. As
bad as this was about to be for his friend, part of him was pleased he
wasn't in this situation alone. He looked up and over at the doorway to
the room they were standing in, and there was Peter, still dressed as
Pamela in the beautiful red gown.
"Bethan, what's going on, I heard talking...."
"Oh my God! Peter?!" Jennifer's jaw hit the floor and she realised the
beautiful young woman in the red dress was her son.
"Mom, what are you doing here?!" Peter was equally as shocked to have his
mother stood there beside him. His cheeks too began to redden. He
nervously walked over and stood next to his friend, waiting to find out
what their mothers would do or say next.
This was the situation both boys had feared all along, having their
Mothers find out they liked to dress as women. But in reality, being
discovered was not as bad as they imagined. There was an awkward silence
to begin with, and it was incredibly embarrassing for the two boys,
especially when they were forced to admit to also wearing lace underwear,
stockings and suspender belts, but the two women were never angry, more
curious as to what it was that made their sons want to do this. Ben
couldn't help but smile when he heard about the plan to trap him in the
red dress, particularly as it was Peter who had been caught out by it,
not him. Indeed the zipper on the red dress did get stuck and needed
Jennifer's expert touch to release her son from it.
Being discovered in this way, as difficult as it was at the time, opened
many new avenues for Ben and Peter. Instead of hiding their dressing up
sessions this from their mother's, they would involve them, even having
them help with hair and make-up and fashion advice. Every so often the
women would remind their sons of the day they were first discovered. It
was the day that changed everything, not only for Bethan and Pamela, but
for their mothers too.
Mei
- 05.12.2022
- 26
- 0
