OOPPSS The Pageant
- 3 years ago
- 15
- 0
Tina's Tale : An 'OOPPSS' Story free porn video
Tina's Tale: An OOPPSS Story
By Maria Ski
Hello I'm Tina. You may have read some of the stories about my brother
John and his journey which led to him becoming Jennifer. But the story
begins before the night she/he got caught by our mother. In fact our
mother wasn't the first person to catch John wearing a skirt. That
honour happens to be mine and all because I had a suspicion that someone
had been in by clothes cupboards and drawers.
Now John and I are not that far apart age wise which meant we were
pretty well the same size, with John being just a little taller. This
little fact meant we could trade clothes if we had so wished. I admit to
'borrowing' a couple of his funky sci-fi themed t-shirts.
But I suppose that could have led to his sojourn into cross-dressing.
Even today I am unsure as to when John started, all I know was that I
was first to make the discovery. And I beg your indulgence with my use
of gender pronouns I sometimes still get them confused.
So it all began, well my involvement in helping John, on a wet Saturday
afternoon.
"John...! Tina...!" our mother called out, "I've got to go out. You two
behave yourselves and try not to annoy each other." Mum had given us her
usual warning. Usually we were pretty good in that regard in that we
didn't annoy each other unless it was over what to watch on the
television.
"Tina went out Mum," John replied, "she's gone to Julia's to get a CD
back."
"Ok John. But try not to annoy your sister," she answered, "I should
only be a couple of hours." With that the front door closed as mum left.
I don't know how long John waited but I know what he had in mind. After
all he was on his own in the house. He went into my room.
I arrived home about half an hour after mum had gone on her errand. And
I was totally unaware of what to expect when I got home. But I was
alerted to a sound coming from my bedroom, so I slowly crept upstairs
wondering who was in my room. I opened the door to my room slowly and
keeping quiet as I could I peered round the edge of the door. What I saw
was something I didn't expect...
A young teenage girl with a short hairstyle about my age was standing in
front of my full length mirror. She was wearing an outfit that had been
carefully put together. I can remember to this day what she was wearing.
From top to bottom she wore a purple t-shirt, which I hated, a dark
denim skirt which ended just above the knee, tan tights which hugged her
legs giving them a delightful feminine shape and a pair of knee high
black boots with a 3 inch heel. I continued to watch as walking in the
heels as if she were born in them she picked a denim jacket to match her
skirt. I have to admit the ensemble suited her. Even if she didn't truly
have the figure to carry it off. I stepped into my room.
"Caught you...!" I exclaimed, "Whoever you are."
She turned to face me with the look of a deer caught in headlights.
"OOPPSS...! Tina..!"
"John...?"
"Sis... I can... Look..."
I just smiled at him. I know I should have read him the riot act but
she... he looked so cute I couldn't bring myself too. I just walked up to
her and enveloped her into a hug.
"I've always wanted a sister." I paused. "And it looks like I've got
one."
John was close to tears. He was shaking slightly so I hugged him again.
Smiling I took another look at her. "That's a good look for you. You've
obviously put a lot of effort into your choices. But I think you could
use a few improvements." I looked at John, "We need to sort you out so
those clothes fit you properly." I giggled, "Let me work my magic on
you. So the ugly duckling can be the beautiful swan she's meant to be."
And so it began. I thought that if my brother wanted to be my sister I
was going to help her be as convincing as possible. The fact we were
almost the same size was going to help. I told her to strip down to her
tights. Laughing as she wiggled her toes after being released from the
confines of the boots. I couldn't help but notice that John was wearing
panties when asked I discovered they were her own and that she had
tucked her boy bits away. And that her whole body and legs were hair
free which came as a surprise. I was beginning to realise that she had
done this before. Being tactful I didn't bring the subject up. Although
as she stripped we discussed what name my new sister should have. We
settled on Jennifer.
"Here you go Jenny. Put this on," I said handing her a padded panty
brief, "It will give you some shape around you bottom. And help the
skirt sit properly."
"Should I remove the tights first?" Jennifer asked. "Or just put it on
over them?"
"Put it on over them for now," I replied. "Now you get to wear your
first bra"
I found one which matched her panties and watched her work out how to
put it on. And from a box in the same drawer I produced some 'fillers'.
"These should give you some shape. But we'll have to get you your own at
some point."
Jenny put them into the separate bra cups and I could see an
improvement. I wondered why my brother wanted to dress as a girl. But
that was a question for another time.
With the foundation garments on Jenny started to look like a girl her
own age. There were a few more tweaks that I needed to do. But first I
got her to put the clothes she had picked out back on. She started with
the skirt which once she zipped it up showed her newly feminine figure
to perfection. The T-shirt followed and slowly my brother disappeared.
The T-Shirt now fit her correctly and I must admit it suited Jennifer
better. She added the boots and stood up; even without makeup I could
only see a little bit of John. Her mannerisms had also changed to those
of a girl.
"Now you're not finished yet Jenny." I guided her over to my vanity and
got her to sit down, "I'll explain everything I am doing. And when we
get you your own make up you'll be able to do everything yourself.
Jennifer I'm going to teach you all the tricks I know. And when I'm
finished I doubt even mum will recognise you."
"Mum... mum..." Jennifer said with a slight catch in her throat.
"You'll be fine Jenny. Trust me?" I said in an effort to reassure her,
"Besides she gone out. So it's just the two of us, just sisters
together."
Jenny smiled. "I trust you sis. Work your magic."
I covered all the mirrors in my room. As I wanted to do a big reveal.
And so I set to work explaining each step, first I used a facial wipe to
cleanse John's face, following that up with a tissue to remove anything
I'd missed. A light layer of moisturising foundation and blemish cover
was followed by a dusting of face powder in a similar shade. I explained
that to make a face beautiful you needed a blank canvas and any
blemishes needed to be hidden. I proceeded to work on Jennifer's eyes
using a white eye shadow followed by eyeliner and then a mix of shadows
to match what she was wearing but being careful not to go over the top.
Mascara was applied to both her upper and lower lashes. I would have
added false lashes but that would be for another day. I added a light
blush to Jenny's cheeks. And I had to smile as she looked beautiful. I
selected a ruby coloured lipstick and applied it to her lips. But she
wasn't finished yet. Telling her to keep her eyes shut I looked in my
wardrobe for a wig I knew I had. It was light auburn in colour and
matched my hair colour as I placed it on Jenny's head I noticed that it
would be shoulder length on her. Getting her to stand up I handed her
the denim jacket to complete the ensemble. She adjusted her hair as if
it were her own. It was as if I was watching a different person standing
before me.
"Jennifer? Are you ready for the big reveal?" I asked as I stood before
the full length mirror, "Do you want to see what you look like as a
girl?"
Jennifer slowly nodded and looked down at her boot covered feet. She
really did look right dressed as a girl. I smiled and slowly removed the
towel from the mirror. "Ta-Dah!"
I watched as she slowly looked up and took a good look at her
reflection. There was a slight look of disbelief as she watched the girl
in the mirror but all I saw was a beautiful girl. John as I watched him
strike different poses was as female as she appeared. I knew then that I
had a sister, albeit a temporary one, I could share things with. And
after all he had shared his big secret with me.
I went and stood next to her and we looked at the reflection, we looked
like sisters. There was no doubt in my mind. Jennifer turned and hugged
me, "Thank you Tina," she said in a softer voice, "Thank you very much."
"You're very welcome Jennifer. And I think my sister deserves a
present," I said with a smile. "You can keep what you are wearing. Of
course we'll have to get you some other female clothes, underwear and
your own make up. But for the time being we can share clothes, and all I
ask is that you ask first." I paused in thought. "Let's go downstairs
and have a drink. And then maybe we can go for a walk as sisters?"
Jennifer chewed her lip; it was something John did when he was nervous,
"A walk? I'm not sure..."
"Jennifer you are a beautiful girl. You walk in those heels as if you've
been wearing them for years. No one but us will know the truth. Besides
you are going to want to go out at some point. So why not now?"
Jennifer smiled. "I guess you're right sis. I am all dressed up with no
place to go. I'll go and put the kettle on. We'll have a drink then go
for a walk. But we have to get back before mum gets home." She paused
again. "I don't want mum to see me dressed just yet."
"Ok Jennifer. I agree. A drink, a walk and get home before mum." At the
mention of mum, my mobile phone rang.
"Hi Mum. What's up? I thought you would've rung the land line?" I
listened as mum explained what had happened, "Ok Mum I'll tell him," mum
hung up and I turned to face Jennifer, "We've got a bit longer to spend
as sisters. Mum is stuck in traffic. So we can go for a slightly longer
walk. And I'll make sure we'll be back before she gets home. She said
she'll ring when she's closer to home. And she also asked why your phone
is off. As it went straight to voice mail" I laughed, "But we both know
the answer to that question."
Jenny bit her lip again. I would be nervous too. Mum would have a go at
him for having his phone switched off.
I found a black leather handbag that she could use putting tissues,
lipstick, a purse with money from John's wallet and his mobile phone.
Jenny smiled at me when I handed it to her. "The bag is also yours to
keep," I added, "Every girl has a favourite handbag."
Jennifer became more confident as we walked. I decided to go to the
local store thinking that Jennifer needed some social interaction. But
she was ahead of me there. So as we were in the store she purchased a
copy of Elle with Andrej Pejic in a dress on the front, some Dr Pepper.
And walked up to the counter and paid for them. I was very proud of her.
My faux sister had passed her 'pop quiz' during her first real outing
whilst dressed. I then had an idea. I would take Jennifer to meet Julia.
Julia knows John and I thought this would be a good test for him. Ok it
was a lot for him to do on his first true outing en-femme. But
everything she had done so far she had passed with flying colours. And I
was sure Jennifer could handle meeting Julia.
Jenny looked at me and said, "Tina I've come this far. I'm sure Julia
will see through this mask but let's give it a go. We can always say
that I lost a bet if it goes wrong."
Did I mention John can be pretty smart when he needs to be? But then
again he is my sis... brother. And I do love him.
Julia is one of my best friends and we've known each other since junior
school. And that is why I chose her to meet Jennifer. Although I knew
that we had to be careful if her mother was home, she was a friend of
mum's, but I was sure Jennifer would handle herself well. At the time I
don't know why I suggested that we go and see her, but she was a good
friend and could be trusted with secrets. And meeting my new sister
would be some secret she could be asked to keep. And I began to wonder
if this would be a step to far for Jennifer? But then again she had
taken everything I had thrown at her in her stride. It was as if
Jennifer and John were two separate people.
As we left the store Jennifer passed two boys in her class they didn't
even take a second look. For all they knew Jennifer was a girl their age
who went to another school. I hid a smile as one of them stopped to
check Jenny out. I seriously thought about telling her, but I would keep
that little fact to myself.
I found Jennifer waiting for me as she looked into the window of a
woman's clothing store which was next door. She was looking at the prom
dresses they had on display. That also bought a smile to my face, my
brother looking at prom dresses who would have thought?
"Baby steps Jen," I said breaking her train of thought, "Baby steps.
Although that dark green sheath dress would look fantastic on you with
the right foundation garments," smiling I continued, "We better get
going."
The click of our heels against the pavement had a calming effect on
Jennifer with each step she appeared to be a little more confident. I
found that surprising and to be honest I was expecting her to make a
break for home. But Jennifer was hanging in there, I could hardly call
her John the way she was dressed now could I?
We reached Julia's home and walked up the path to her front door. As I
pressed the door bell Jennifer smoothed imaginary wrinkles from her
skirt. Jennifer turned to look at me as if to say 'What?' As far as she
was concerned her actions were normal. Of course I held back a laugh.
Julia's mother answered the door and the smell of cooking and freshly
brewed coffee danced with our senses.
"Hello Tina." She allowed us to enter. "Who is your friend?" she asked
with a smile.
"Hello Mrs. Johnson. This is my cousin Jennifer. She surprised us this
afternoon by coming to visit."
"It's a pleasure to meet you Jennifer." Mrs Johnson looked at her. "I
can see the family resemblance." She paused. "Come on through to the
kitchen. Julia is cooking and I am sure she would like to meet you
Jennifer."
Jennifer smiled. "It's a pleasure to meet you too Mrs. Johnson. It was
Tina's idea I come with her to meet Julia. I don't think she wanted me
to be left alone with my cousin John."
I hid a look of surprise, and Mrs. Johnson laughed. "John can be a bit
of a handful. But he is a nice boy. You could have bought him round."
"John was busy when we left," I added. "He was doing something on his
computer. What I don't know. But it keeps him out of trouble."
As we entered the kitchen Mrs. Johnson left us and went off to the
lounge. I smiled and said, "Hi Julia I'd like you to meet my cousin
Jennifer."
"Hi Tina and hello Jennifer." She looked at Jenny. "I can see the family
resemblance. She looks a little like your brother." She smiled. "Please
don't take that the wrong way Jennifer."
I heaved a sigh of relief. Julia hadn't recognised John. Jennifer just
shrugged adding, "My mother has said that I do look like John." She
giggled, she actually giggled, "But then again we all have our crosses
to bear. Mine is I have a slight resemblance to my cousin John."
Jennifer poured us a mug of coffee each. Jennifer took a cautious sip
and placed her mug down. "Julia?" she asked. "Did Tina ever tell you of
time that John and I swapped places? It was when we were both a lot
younger."
Jennifer had dropped a hint, I wondered if Julia would pick up on it.
"No. I don't think she has. Did it cause any trouble?"
"They were both told to change back," I told her. "Our mother and aunt
found it very funny. But our father lost his sense of humour and John
got a..." I looked over at Jennifer. "John got a good hiding from Dad. And
he was told never to do it again." I smiled at Jennifer. What she told
Julia had actually happened but John had swapped clothes with our cousin
Catherine. I often wonder whose idea it was as I look back.
"I didn't know that," Julia replied. "Where any pictures taken? I bet
John looked cute dressed as a girl."
"He did," Jennifer added. "Both my mum and Aunt Catherine thought so.
But John's dad is one of those macho types. Boys should be boys; girls
should be girls and no middle ground."
"It's one of the reasons mum divorced him," I said, "I think when he
beat John was the start."
"It also explains why John is so quiet. I'd love to get him to open up a
little." Julia smiled. "I like John. Mum would approve. But he does need
to open up."
I signalled to Jennifer to remain quiet. "You like my twerp of a
brother? I don't believe it," shaking my head, "It's Ok Julia your
secret is safe with us."
From there we started talking about all sorts of things. Mostly about
Jennifer's interests, if she had a boyfriend, who she fancied etc. I was
surprised as Jenny answered all questions asked. I was scared that she
would accidently 'out' herself.
But I needn't have worried. Especially when Julia's mother joined the
conversation. The time came to leave. And Julia saw us out handing Jenny
a note telling her to give it to John. Jennifer said she would as she
put the note in her hand bag. We said our goodbyes and made our way
home.
Jennifer took one final look, for that day, in the mirror at the girl
he, John, had become with a tear in his eye. He slowly got changed.
Jennifer got put into a cupboard to come out again.
I then remembered the note Julia had given Jenny. I rushed up stairs to
ask John about it. He was sitting on his bed, the note by his side. He
had been crying. As I came up to him he slowly handed me the note. I
took a look...
Dear John,
You looked beautiful today as Jennifer. And you made a very convincing
girl.
Do not worry. Your secret is safe with me. As I know Tina would kill me
if I let it slip.
I would love to see Jennifer again. As long as she is on her own. But
there is no rush. Just take your time.
Love and Hugs
Julia xxx
Julia had also added her mobile number.
I sat down next to him giving him a hug. I knew that Julia would be true
to her word. But I felt sad that John as Jennifer had been read. We
never did learn what gave John away. He may have made a slight slip and
not noticed.
"John, Tina!" Mum called as she came through the door. "I'm home."
"We're in the kitchen mum." John answered, "I've just put the kettle
on."
"So what have you two been up to this afternoon?" she asked.
"We just talked mum," I told her. "We just talked."
Mikhaela
- 19.04.2020
- 21
- 0
