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Delia365

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JUST FRIENDS
STORY INFO
Two friends have the house to themselves.

BABYSITTING
STORY INFO
I'm caught dressed in Jan's clothes by her husband.
2.9k words
4.638.1k207
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Delia365
Delia365
15 Stories64 Followers
I'm 18 years old and I've been babysitting for Jan and Tony for the past
3 years or so. Jan is in her late 30s but could pass for 10 years
younger. Blonde and big blue eyes, very attractive and with amazing
legs. Tony was probably the same age, nearly 6ft, handsome and kept
himself fit. They were a great couple, and very popular.

Little Lucy was 5 and a dream to look after, never getting out of bed
and never crying out during the evening, in fact i would have to check
on her as she was so good. This was perfect for me, as i loved to
crossdress and would often try on Jan's clothes. I've been a
crossdresser since i was very young and wore my sister's clothes at
every opportunity. Jan had some lovely dresses and some very sexy
underwear, i would dress as soon as they left the house. Her underwear
drawer was like a treasure trove to me, tights and stockings, knickers
and bras aswell as corsets and see through nighties.

One particular night, just after they had left, i went straight to Jan
and Tony's room and picked out a black dress that i had been wanting to
try on. Jan had a huge selection of underwear and i eventually picked
out a black, lacey, padded bra and knickers to match. I decided on black
tights rather than stockings, as i really enjoy how they feel on my
backside and loved the sound of them rubbing together as i walk around.
I went to the bathroom and stripped quickly, enjoying every second as i
dressed up in the beautiful sexy clothes and underwear. Slipping on the
dress made me feel incredible, it was tight against my body and stopped
just before my knees. The sleeves finished at the elbow and it had a
sheer front, from the chest to the shoulder. Doing up the button behind
my neck, i gave a long excited sigh, i felt so sexy. I wasn't going to
bother with makeup, just in case Lucy woke up.

I felt so good as i looked at myself, then went and picked out a pair of
low heeled shoes, they were a little tight but felt comfortable enough
to wear around the house. Looking down, i couldn't help admiring how my
legs looked in the tights, i could feel the excitement building up
inside me. I went downstairs and walked around, loving how the dress
felt, walking into the kitchen so i could hear the heels clicking on the
tiles. If I sat down to watch television id stroke the tights, if i
stood up i would open my legs, feeling the dress, tight against my thighs.

After about an hour or so, i felt the urge to play with myself taking
over. I knew where Tony kept some porn CDs and i picked a couple out. I
put one in the machine and pressed play, using the remote to fast
forward to the action scenes. On the screen was a young girl dressed as
a maid, kneeling on the sofa and sucking the huge cock of the man she
worked for. I sat down and watched in awe, wanting to be that girl. I
couldn't take my eyes off the screen as the action got hotter and
sexier. I was getting harder and harder as i watched, getting to my
feet, i rubbed my hands up and down my body. Stroking the tights sent
signals straight to my groin. I lifted my dress, exposing my knickers,
and touched my throbbing cock, breathing heavily as i did so.

I couldn't resist anymore and i pushed my knickers down to my knees,
looking at my cock stretching the tights. I slid my hand inside them and
wrapped my fingers around my shaft, and slowly started to masturbate as
i watched the maid being pumped hard on the TV. I was totally lost in
the moment, dreaming of being the maid and having to please the guy,
when i heard someone cough behind me. I spun around and there was Tony,
hands on his hips and staring at me. I dropped to the floor, trying to
hide behind the armchair.

I just keep telling Tony that im sorry, over and over again. hoping the
ground would open up and swallow me. Tony tells me to calm down, that
I'm not in trouble, but my embarrassment is plain to see. He approaches
me with his hands outstretched, telling me everything is ok. He offers
me his hand, telling me to get up and sit down on the sofa. I'm shaking
as i sit down next to Tony on the sofa, he places a hand on my back and
strokes up and down in an effort to calm me. There is a period of
silence before i gather my thoughts, i say that i should get changed but
Tony tells me to stay where i am so that we can chat for a minute.

As we talk, Tony gets a bottle of wine and pours two glasses. He gives
me a glass and asks me to tell him about my crossdressing, i start
answering his questions, explaining about the feeling and the need to
wear women's clothing. I was on my third glass of wine when Tony said
that i looked good in the dress i was wearing. I blushed and shook my
head. Tony told me to stand up and show him properly. I did as i was
told, pulling up and sorting out my tights and knickers then smoothing
out the dress. He nodded his approval, telling me to turn round a couple
of times. Tony looks me up and down, telling me that i had nice legs and
the heels suited me. Maybe it was the wine, but i said thank you,
excited at being told that.

I sat back down next to Tony, a strange feeling flooding my body. He
looks me in the eye and says that he thinks that i have feminine
features, saying that i look sexy in his wife's clothes. I just stare at
him, blushing, unable to reply. He then asks me if i have had
experiences with any guys, i look at the floor and nod. Tony puts a hand
on my knee, He tells me not to be embarrassed, that it's okay to be
honest with him. His hand slowly starts to stroke my tights, the feeling
is overwhelming and fills me with excitement. I keep looking down at the
floor, parting my legs a little, as Tony's hand slides further up my leg
and under my dress. I knew that i should stop him, but i offer no
resistance, enjoying the feeling of his touch.

My breathing becomes heavy as Tony softly strokes my inner thigh,
instinctively i put a hand on Tony's leg. No words are spoken as i move
my hand to the bulge in Tony's trousers, his fingers caressing my
knickers, making me gasp and my whole body tingles. I look at Tony and
ask about his wife coming home, he tells me that he had come home early
as she had met some friends and wouldn't be home until much later. A
wave of excitement flooded my body and without any thought, i slipped
off the sofa and onto my knees and made my way between Tony's legs.

I didn't look up at him as i pushed his legs apart, lust taking over as
i start unbuttoning his trousers and tugging them open. Tony's cock was
rock hard and stretching his underwear, i stared at it for a few
seconds, then looked up at Tony. He just smiles back at me as i slip my
fingers over the top of his boxers, then, pulling them down, revealing
his throbbing cock. I smile and say a wow at the sight of his impressive
manhood, long and thick and cut, with a rather large helmet. I wrap my
fingers around the shaft, producing a groan from Tony. He looks huge in
my hand as i gently start to stroke up and down, im totally absorbed in
the moment until Tony awakens me from my trance and starts to get up.

I move back a little, letting go of Tony as he stands in front of me,
then he takes his trousers and underwear off. I look up at him and he
tells me to carry on with what i was doing. I do as im told, taking him
in my hand. I can't resist anymore, i kiss his helmet, i do it several
more times then i lick his long shaft. Tony groans as i lick and kiss
his length, running my tongue up to his helmet then down to his balls.
Tony then calls me a good girl, hearing him call me a girl thrills me,
really excites me. I stop licking him and immediately wrap my warm lips
around his shiny helmet, i feel him throb as i tease him with my tongue.

Tony puts a hand on my head, he gasps and groans as i suck and tease. I
gradually take more and more of him into my mouth, soaking his cock with
my spit as he fills my mouth. Tony's thick cock is too big to take all
of it, but i try, gagging with the effort. Soon Tony puts both hands on
my head and starts to face fuck me, i offer little resistance, placing
my hands on his legs as he continues to pump my mouth. It's not long
before Tony tells me he is close to cumming and releases my head, but i
don't pull away, letting Tony know that it's okay to shoot his load down
my throat.

Tony grips my head again, gasping as he keeps pumping. A minute or so
later he stiffens and groans loudly as he shoots his thick, warm cum
down my throat and into my mouth. He stops pumping, so i take over,
bobbing my head back and forth as i drain every drop of man juice from
him. Tony pulls out of my mouth and drops back onto the sofa. I stay on
my knees watching him regain his breath, savouring the taste of his cum.

He pats the space beside him on the sofa and i get up and join him. He
says that the blow job was incredible and i thank him. Tony pours us
both another drink, i ask him if i should go and change but he tells me
not to. We chat about some of my experiences and he asks lots of
questions, his hand finding my leg again. We talk for some time and
after a while i notice that Tony is getting aroused and i let him know
that i am willing to pleasure him again. He asks me to stand up and show
him my knickers, i happily do as im asked.

He makes me walk around with my dress lifted up, and i have to bend
over, showing off my knickers, giving him a good view of my backside. I
look behind me as im bent over, he smiles and tells me that im a tease.
Tony gets up and stands behind me. He puts a hand on my back and starts
to stroke my knickers, squeezing each cheek before sliding his hand
inside my underwear. I stay bent over, enjoying the sensations filling
my body. Tony tells me that i look good dressed as a woman, saying how
sexy i looked in his wife's clothes.

Tony strokes his hard on as he continues touching my arse. I can hear in
his voice that he is turning himself on, getting worked up. I tell him
how nice it feels having him stroke my arse through the tights, im
willing him to continue. It's not long before Tony tells me to stand up
and to go around the back of the sofa. Tony opens a draw in the wall
unit and takes out a tube of cream as i stand excitedly behind the sofa.
He walks up to me, asking me to lean forward and to put my hands on the
sofa. I do as I'm told and bend forward, eagerly anticipating what he
has in mind.

My dress is lifted up and over my back, i bite my lip and say nothing.
My knickers are taken down, Tony tells me to step out of them, and i
begin to pant. Moments of silence pass as he strokes my tights, then he
pushes them down to just below my cheeks. Tony's fingers find my tight,
warm hole and a little squeal leaves my throat. Something cold and wet
is gently massaged around my hole, then i feel his finger pushing
against it. As his finger enters me i gasp loudly and shut my eyes, Tony
gives a satisfying moan as he pushes deeper, shushing me as i give a
whimper.

Tony is gentle as he starts to finger me, telling me to relax and making
me bend lower. He removes his finger and moves behind me, smearing the
cream over his length. Tony pushes me forward and tells me to step
backwards, my chest now touching the sofa. He slides his helmet between
my cheeks, finding my pussy and starts to push. I hold my breath and
clench the top of the sofa as the pressure builds. My knees bend
slightly, as i feel the tip of Tony's helmet penetrate my tightness, and
i groan loudly.

Tony hushes me as he continues to enter my tightness. My eyes shut tight
and my mouth opens as i silently pant and gasp. Finally my pussy
stretches enough to allow Tony to enter me and a satisfying moan leaves
his throat. His hands grip my hips as he calls me a good girl, he
doesn't rush, just slowly inches deeper into me. Tony asks me if i am
okay when he is about half his length inside me and i nod my head. He
stops for a few seconds then starts to withdraw, the feeling is intense
and i can't help but let out a moan of pleasure. Tony tells me how tight
i feel as he gently pushes back in to me, i just groan and gasp for air.

Tony slips deeper and deeper into me as the minutes pass, his thick cock
stretching my hole and forcing me to squeal and cry out every so often.
Eventually Tony is pushing his full length into me, almost forcing the
breath out of me. He keeps talking to me as he gets harder and faster,
this really excites me and i find myself moving my hips and pushing back
to meet Tony's thrusts. I encourage him to fuck me, telling him how
great he feels inside me. I tell him to cum inside me, that i want to
feel his throbbing cock explode deep in my pussy. A few minutes later
Tony growls loudly and he pushes as far into me as he can, then stiffens
for a second as his long, thick cock begins to pump thick, warm cum in
my hole.

Tony gives 5 or 6 hard thrusts, each time unloading his man juice and
filling me up. I groan with delight, happily accepting all that he gives
me, grinding myself against him, trying to drain every drop of cum from
him. I feel Tony relax a bit as he gasps for air, he withdraws from my
aching hole and i quickly drop to my knees and take his manhood into my
mouth. I can taste the sex on his cock as i lick and suck him clean,
continuing until Tony can't take it anymore and stops me.

Tony walks to the sofa and sits down, i get up and pull my tights up. I
slowly walk round and stand in front of him and ask him if he is okay.
He smiles and says yes, telling me to sit down, i tell him that i could
feel his cum oozing out of me so i should change before i get cum on
Jan's dress. He smiles and nods, asking me to have another drink with
him when im changed, before i go home. I pick up the knickers and go
upstairs to the bathroom. I take Jan's clothes off carefully, replacing
the dress and shoes as carefully as i can then putting the bra and
knickers back. I clean myself up and put my clothes back on, putting the
tights in my pocket as Tony's cum had leaked into them.

I go back to the living room, Tony is still naked on the sofa. I sit
down and take the drink that is offered, nervously looking at Tony. He
says that he really enjoyed what just happened, telling me how good i
was at giving him a blow job. I just smile and whisper a thank you as he
continues to talk. Tony mentions how tight i felt and how much he
enjoyed having sex with me, asking if i was okay and how i felt. I let
him know how much i loved having him inside me, how i enjoyed making him
cum. Tony looks me in the face and asks if i wanted to have sex with him
again and i almost shout as i tell him that id love to. He asks me if i
would wear makeup next time and i agree. As i get up to leave, he tells
me that he is looking forward to seeing me again very soon.

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Delia365
Delia365
15 Stories64 Followers