The Outsiders
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Caught Outside free porn video
Caught Outside
By SONIA
(e-mail [email protected] - Please send comments)
My name is Tom and I am aged 13 and for as long as I can remember
I have fantasised about wearing girls clothes!
With a younger sister aged 10, called Mandy, and an older sister
aged 15, called Jackie, I never had a lack of role models to copy
or clothes to experiment with.
The problem I had was opportunity! With my family, the house
seemed to be never empty and I was restricted to dressing up for
a few minutes when I was supposed to be having a bath and this
depended what happened to be in the washing hamper. Even still
I had many blissful times admiring myself in the mirror wearing
my sister's panties, slips etc.
After months of frustration, my change in opportunity happened
when my mother decided to go back to work and this meant that we
were at home on our own until she got in at about 6.00. This was
not a solution on its own as my sisters were still around but
even this was solved when they joined the school cheerleader team
and this meant that on Wednesday at practice I had the house to
myself from 3.30 until my sisters came home at 5.30 - bliss!
Each Wednesday I would rush home from school and as soon as I was
in the house I would lock all the doors and windows so I could
not be discovered and then head for my sister's rooms and spend
an hour of dressing up before changing back well before they were
due to return.
I experimented with both my sisters clothes. Jackie, my older
sister, had wonderful sexy lingerie in lace and satin as well as
her boring cotton everyday underwear and I probably enjoyed her
clothes most. She had a wonderful set of bra, panties and
matching short waist petticoat in lemon yellow satin with white
lace trim and I loved to put this on with a skirt and blouse or
dress.
My youngest sister, Mandy, was quite big for her age and I could
fit most of her clothes. The things I enjoyed most was her party
dress which was spectacular in cream satin with layers of lace
and trim and several layers of net petticoat built into the dress
and, almost better, her school uniforms.
Mandy had three school uniforms which she seemed to wear almost
on rotation. She had a grey gymslip which was fairly plain, with
no sleeves and a slightly tapered skirt with a single pleat at
the rear which she wore over a white blouse. She had a short
pleated grey skirt which she wore with a blouse or sweatshirt and
grey a-line skirt which she wore with a sweatshirt. I loved the
gymslip and the pleated skirt best of all as they were both short
on me and felt wonderful to wear. Although I loved the satin
panties of my older sister, I adored Mandy's navy blue school
girl knickers. Mandy had three pairs of these knickers so there
were always some in her drawer. They were slightly elasticated
full briefs in a soft material and I thought they looked
fantastic on.
As soon as I got home I used to go to my room and strip off my
clothes and then put on my dressing gown and head to Mandy's
room. I would drop my dressing gown and open her drawer, take
out her navy blue knickers and put them on. I had just
discovered the joys of masturbation and my penis would tent the
front of the knickers forward as I admired myself in the mirror.
Quite often I would then go downstairs just in the knickers
loving the feel of how I was dressed. I would stand in the
doorway to the living room where I could see out of the window
and loved the excitement of being exposed if someone happened to
look.
I would then return to Mandy's room and put on her blouse and
either the gym slip or pleated skirt along with white knee high
socks and trainers. My hair was fashionably long, at about
shoulder length, and this meant I could put it into bunches.
Once dressed, I though I looked like a very convincing school
girl. I would then spend the rest of my time dressed as 'Paula'
which was my name when dressed as a girl. I was sufficiently
confident in my appearance that I used to wander around the house
as Paula without hiding in the shadows. I think these times were
some of the happiest of my life.
Next to my sessions on Wednesdays my favourite time was Tuesday
and Thursday when mum had a home help in to clean and do the
washing. Mrs Russell was about the same age as mum and had a
son, Tom, of about my age who came with her sometimes.
Mrs Russell did the ironing in our breakfast room and I used to
sit with her as I loved seeing all the clothes as she ironed
them, especially the lingerie. I got a real thrill seeing a pair
of panties ironed that I had worn.
I don't know whether I showed too much interest in panties but
after a few weeks Mrs Russell started holding up items of
clothing after she had ironed them and commenting on how pretty
they were. I'm sure I blushed when she held up a pair of satin
panties I had worn but I loved looking at them as she held them
and when she put them down she always seemed to put them close
to me and I would have my hand on the table and 'accidentally'
touch them as I sat there.
Mrs Russell used to cook us supper and I used to help her in the
kitchen and as I helped she made me wear an apron. Even though
we had a plain apron she always gave me mum's apron which had a
flounce on the bottom.
One day when it was hot and I was wearing shorts Mrs Russell
stated what I had thought, "That apron looks from the front like
you are wearing a pretty dress."
Probably I should have ripped it off in protest but instead I
just looked down at it and when I looked up at her she had a half
smile on her face.
With the hot weather I started getting a little adventurous when
I was dressed as Paula. I used to go into the garden and sit on
the garden bench, loving the feel of the air on my legs and
sometimes I would take off the skirt and sit there in my navy
blue knickers like the girls at school doing gym. I may well
enjoy pretending to be a little girl but the erect penis in my
knickers left no doubt of the sexual thrill I got from dressing
up and my sessions always ended up with me masturbating to a
fantastic orgasm.
One day my daring escapades in the garden went very wrong.
I had dressed in my favourite outfit of the short pleated skirt,
blouse and navy blue knickers but had added a white bra of
Jackie's which I had stuffed with some socks to give me breasts.
It was a lovely day so I unlocked the kitchen door and, as usual,
glanced around to make sure the coast was clear and then walked
out into the garden. I sat on the bench and was feeling my
erection through the knickers when a gust of breeze blew and I
heard the kitchen door slam shut - and I had not put the catch
on the latch!
I ran to the door and my worst fears had happened - the door was
locked! I checked all the windows at the back of the house and
this only confirmed that I had closed them all and what is more
I knew that I had locked all the other doors.
I looked at my reflection in the mirror and saw Paula looking
back at me - at least I had my skirt on and had not gone into the
garden wearing just lingerie as I had on some previous occasions.
With my heart pounding I went around to the front of the house
to see if I had missed a window but alas the house was locked
tight. Why had I left my key in my trouser pocket in my room.
What on earth could I do?
I thought about breaking a window to get in but the noise would
have brought the neighbours running and what could I say to my
parents. I thought about waiting until my parents or sisters
came home but the thought of trying to explain how I was dressed
to them was unthinkable. The only idea I could come up with was
to get the key from Mrs Russell.
The only problems with that idea was firstly that Mrs Russell
lived about 10 minutes walk away and I was dressed as a school
girl! Although I was terrified my penis was straining at my
knickers, pushing the skirt out in a very unladylike way. I went
back around the house to the back garden and well out of sight
of anyone I lifted my skirt, took my penis from my panties and
masturbated to a fantastic orgasm. My predicament seemed to have
excited me even more than normal!
I tucked my now limp penis between my legs and pulled my knickers
up tight. I checked my appearance once more in the reflection
in the window and with a pounding heart started walking towards
Mrs Russell's house. As I walked I tried to think up how I would
explain myself to her and decided that my only option was to
admit my love of dressing up. As I walked along I was relieved
to see other young girls in similar outfits although my skirt
seemed shorter than any other I saw. Luckily I seemed to pass
well and attracted no undue attention.
I arrived at Mrs Russell's house and feeling faint with worry
about what would happen I walked up to the door and rang the
bell.
Mrs Russell opened the door, looked at me first with a blank
expression and then she registered who I was and how I was
dressed and the reaction that followed was not what I had
expected.
"Well hello, dear. Come in, come in. To what do I owe the
pleasure of your visit and what's your name at the moment?"
I was stunned. How come she accepted my predicament as if it was
normal. After the fears I had imagined as I walked of how she
would react this knocked me totally off balance and instead of
accepting her reaction I did what any self respecting girl would
do - and burst into tears.
Mrs Russell put her arm around me and took me inside and into the
living room. She told me that Tom was out at the moment and so
we were on our own and between sobs I told her everything.
"I knew you dressed up," she said at the end of my saga, "I could
see in the way you looked at the girls clothes. Do you want to
know something?"
I nodded and she went on, "My Tom does exactly the same."
This was a day of revelations! Mrs Russell explained that when
she had first caught Tom in her panties she had been very cross
and had immediately taken her son to the doctors who in turn
referred her to a psychiatrist. Rather than treating Tom the
psychiatrist had explained that a lot of men had the inbuilt
need to dress in women's clothes and that provided it was not
allowed to become an overriding obsession it was for them
'normal'. She went on to say that Tom's alter ego was Susan and
that she had her own selection of clothes and existed maybe once
a week.
It seemed almost natural sitting beside Mrs Russell in my skirt.
We discussed whether I should tell my parents and she suggested
not to as not everyone was as open minded as she was. What she
did suggest was that I could come round to her house whenever I
wanted and dress up and I could meet 'Susan' and play with her
if I liked.
I glanced at my watch and saw it was almost 5.00 and I had to get
home and change. Mrs Russell offered to run me home in her car
and let me. As soon as I was home I rushed upstairs and changed,
putting everything back straight and I had just got back to my
room when Mandy and Jackie arrived home - rather close!
The next day when Mrs Russell arrived we were sitting together
while my sisters were watching television and Mrs Russell said,
"I have a present for you."
She handed me a bag and I took it and opened it. Inside was a
short navy blue pleated skirt, a short sleeved soft woollen
jumper and a set of bra and matching panties in pink satin with
white lace trim and white ribbon details.
"I hope this is what you like."
I thanked her profusely and gazed at the lovely clothes and then
slipped my hand into the bag to feel the soft lingerie.
Mrs Russell then told me that her husband was away this weekend
and if I wanted I could come to her on Saturday and spend the
night so that Tom and I could play together and I could introduce
'Paula' to 'Susan'. This was a fantastic idea and I immediately
accepted.
I decided to wait to try on my new clothes until Saturday at Mrs
Russell's. On Saturday I arrived at 10.00 and Mrs Russell took
me to her spare room and said for me to change in there.
I stripped and put on the panties. They felt fabulous! The bra
was next and then the jumper and skirt. A few minutes later
there was a knock on the door and when I answered it was Mrs
Russell. She came in and complimented me on my outfit. She then
sat me down at the dressing table and styled my hair and applied
some makeup. She then gave me a pair of black tights and showed
me how to put them on without laddering them. She opened the
wardrobe and inside was a full length mirror and when I looked
at myself I could not believe how good I looked.
Mrs Russell then took my hand and said for me to come and meet
'Susan'. I was very nervous and when I entered the kitchen I
almost chickened out but her grip on my hand tightened and she
guided me in. Tom was sat at the table with his back to me and
as I entered he stood up and turned around - it wasn't Tom - it
definitely was Susan!
Tom had on a black jumper, a red tartan mini kilt, black tights
and black knee high leather boots. His hair was brushed into a
neat bob and his makeup was immaculate.
"Hello Paula, I'm delighted to meet you," he said.
We spent the rest of the day chatting about how we started cross
dressing and then going on to coach each other in how to behave
as a girl. Mrs Russell gave me the shock of my life when she
said she would take us both to see a romantic film at the cinema
as apart from my forced trip to get the key I had never before
been out as 'Paula'. After the film we went for a burger and no
one seemed to even notice us - just two girls out with their Mum.
At the end of the day when bed time came Mrs Russell showed me
to my room and on the bed was placed a baby doll nightie.
I changed, got into bed and fell asleep dreaming the most
wonderful dreams.
Safiya
- 07.09.2021
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