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Delia365

https://www.literotica.com/s/just-friends-37
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.

On 3/31/23 19:26, a425couple wrote:
> be sure to check out
>
> https://www.literotica.com/stories/memberpage.php?uid=5744708&page=submissions
>      Delia365
>
> https://www.literotica.com/s/just-friends-37
>     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.
>
That story is all on OP.
The BABYSITTING story is just one page,
it is a first ti8me CD, blow-job, and complete fuck.

here is JUST FRIENDS,
has CD, and Blowjob, has just been written and posted,
indicates more to come, but nothing yet.

JUST FRIENDS
STORY INFO
Two friends have the house to themselves.
3.2k words
4.69.7k214
PUBLIC BETA
Note: You can change font size, font face, and turn on dark mode by
clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience
during our ongoing public Beta testing. Please consider leaving feedback
on issues you experience or suggest improvements.

Click here
Delia365
Delia365
16 Stories84 Followers
I have known Phil most of my life, we went through school together, was
always around each others house's. He was a little taller than me,
slightly bigger build. Phil was blonde and i would have to say he was
handsome.

Phil fancied my sister, Sally, was always going on about her and made
any excuse to chat to her. She was 18 months younger than me and had
just left school. I have to say that Sally was attractive, blue eyed and
blonde. She always dressed nice, i could see why she was popular.

So i had the house to myself for the weekend and Phil decided that he
would stay over. We got some drinks and snacks in, rented some videos
ready for Friday night. Phil arrived about 6ish and we got started on
the drinks. We were sitting in the living room, drinking and chatting,
and Phil decided he needed the bathroom.

After about 10 minutes i started to wonder where Phil had gone. I went
upstairs and saw Phil in my sister's room. He was holding a pair of
Sally's knickers and going through her underwear draw. I shouted at him
but he just smiled at me, i had to pull him out of Sally's room as he
protested.

Finally back in the living room, i start to tell Phil that he is out of
order and how much trouble he could get me into, he just laughs and acts
like nothing has happened. We sit in silence for a while, drinking and
watching television. Phil again starts to talk about Sally, he tells me
that he thinks im lucky as i get to see her all the time. I tease him by
saying that i get to see her in her underwear or wearing very little.
Phil sits up, asking me to describe what I've seen.

I indulge him and tell him a few stories about seeing Sally in her
knickers and bra, going into detail. Phil hangs on every word, wanting
more and more details, i know that he is aroused and i keep talking.
After a while, and a few more drinks, Phil looks at me and asks if i
have ever been tempted to try Sally's clothes on. I pause a second and
then stutter as i tell him that i haven't. Phil quickly sits up, calling
me a liar. I continue saying no and telling him to shut up but Phil
continues to probe.

Eventually i tell him that i had thought about it, but Phil keeps
pushing, sensing that there is more to the story. I could feel my cheeks
blushing as he kept on at me, then i blurted out a yes. A few seconds of
silence followed before Phil shouted out that he knew i was lying. I ask
him to not go on, but even i knew that that would be impossible.

Phil starts asking questions about what things i had tried on, i stand
up and start to pace backwards and forwards, asking him to shut up. Phil
tells me that it's okay, that he would not say anything to anyone. He
tells me to calm down and that he doesn't think badly of me. I sit down
again, embarrassed and nervous, i start to explain that i had been
dressing up in Sally's and my mother's clothes for a long time. I tell
him that i couldn't help myself and dress up when ever i can.

Phil gives me a drink and tells me to relax. I sit there, not quite sure
what to do next. Phil says nothing for a long time, then asks me again
what i wear and why. Slowly i start to tell him about wearing tights and
knickers, mainly for pleasure, that i love the feel of the underwear. As
we talk i start to open up, and i go into more detail, explaining about
dressing up in dresses and high heels, even telling Phil about wearing
makeup. Phil asks more and more questions, even asking if i was
interested in guy's, i shake my head, explaining that i was definitely
interested in girls, that i dress up just for pleasure.

After a while Phil looks at me and asks if i would dress up in my
sister's clothes and show him. I tell him no, shaking my head,
explaining that i have only dressed up when im alone. Phil asks again
and again, saying that we are friends, that it would be a bit of fun,
that no one else would know. Eventually i give in, i tell him that i
will put on some of my sister's clothes but not makeup. Phil agrees,
asking me to put on a dress and high heels.

As i enter Sally's bedroom i start to shake a little, i can't believe
that i had agreed to dress up in my sister's clothes, let alone agreeing
to show Phil. I took a deep breath and opened Sally's underwear drawer,
a smile spreading across my face as i run my fingers over the pretty
female garments.

I pick out a pair of dark tan tights, always loved wearing tights. Next
i chose a pair of pink knickers with a lace front, i also picked out a
black bra, id worn it before and loved how tight it felt. Sally had lots
of dresses to choose from and i knew the one i wanted. It was a short
sleeved navy dress, velvety and soft, high neckline and stopped just
below my knees. The shoes were an easy choice, 3 inch heel, black and shiny.

I took the clothes to my room and laid them out on the bed, excitement
building up inside me as i stared at the feminine garments. I suddenly
became aware of what i had agreed to do, but couldn't stop myself. I
stripped quickly, gathering the tights and slipping them over my foot. I
held my breath as i slowly pulled them up my leg, then slipping them
over my other foot and pulling them up over my waist. I took a minute or
so to calm myself, then pulled on the knickers. The pink lace front
looked so sexy and feminine.

I then put on the bra, always loved wearing a bra, it felt tight but
comfortable. I slipped on the dress, almost gasping with pleasure, it
hugged my body and felt so soft. I tugged it down, just covering my
knees, enjoying the feeling of the dress against the tights. I slipped
on the high heels and went to my sister's room to see how i looked. I
felt wonderful, my stomach turning excitedly as i stared at myself.

I finally walked downstairs, stopping at the living room door. I tell
Phil to close his eyes and that he is not to look until i tell him to, i
tell him that he is not to tell another sole about this. Phil tells me
to stop talking and just show him what i was wearing. I take a deep
breath and walk into the room, standing just in front of Phil. I tell
him to open his eyes.

Phil sits there, looking me up and down, mouth open and saying nothing.
I ask him what he is thinking and he just shakes his head and smiles.
Finally he tells me that the clothes look good on me, i say thank you to
him, my body trembling. I ask if he has seen enough and tell him that i
should go and change. Phil tells me to sit down and chat for a while,
asking me to stay dressed the way i am.

After a nervous few minutes i decided to sit on the sofa with Phil. I
sat on the edge, legs together, tugging the dress over my knees. I can
feel myself shaking as i look at Phil. He tells me again that i look
good, telling me that my legs look amazing in the tights. I say thank
you to him, then i ask if he is ok, asking what he really thinks. Phil
leans forward, he looks me in the face and says that he is perfectly
fine with me being dressed as a girl, telling me to relax.

After a while, and lots of questions, i start to feel at ease. Phil asks
me if i would walk around the room, saying that he would like to see the
clothes properly. I do as he asks, walking from side to side then around
the living room. He tells me that i have great legs and the heels make
my bum wiggle nicely. His comments make me smile and i start to enjoy
the fact that i am dressed up as a girl and showing myself to someone.

Phil asks me to sit down next to him, patting the sofa close to him. I
do as he asks, sitting very close to Phil, my stomach turning as my
heart beats faster. Im nervous, staring at the floor, hands fidgeting on
my lap, then Phil asks if he could touch my legs. I nod, not looking up,
Phil puts his hand on my knee. I take a deep breath, electricity
shooting through my body, Phil slowly starts to stroke my tights.

I'd never experienced anyone seeing me dressed as a girl, let alone
touching me. The feeling of his hand on my leg was incredible, so
thrilling. We were both silent as Phil stroked all the way down to my
ankle then back to my knee. I don't make any protest as his hand slips
just under my dress, touching my inner thigh. Phil stops and asks me to
stand up in front of him. Without thought, i do as he asks, standing
right in front of him. My whole body starts shaking, nervousness turning
to excitement.