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DISCOVERING MYSELF
STORY INFO
Wanting to do more than just fantasise.
2.2k words
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Delia365
Delia365
17 Stories84 Followers
I've been dressing up in women's clothing for as long as i can remember.
It started with wearing my sister's underwear at a very young age. As i
got older i started to explore my mother's lingerie, stockings and
basques etc. I would wear tight dresses and high heeled shoes at every opportunity. As time went by i experimented with makeup and hair styles,
i loved putting on makeup, it made me feel so feminine.

When i finally moved into my own place, i found that i had the time and
space to really explore my girly side. I would visit charity shops and
buy dresses and skirts and other items. buying shoes was easier as i
could make out that i was buying the shoes for my non existent
wife/girlfriend. I was only a size 6 shoe so it didn't raise much suspicion.

I became bolder as time went on, to the point of going out late at night dressed fully as a woman. The fear of getting caught made it all the
more exciting. Id walk around the block mostly, but every so often I'd
venture further.

I got such a thrill out of dressing completely feminine, putting on
makeup and doing my hair in a sexy style, then looking at the girl in
the mirror never failed to excite me. I started to fantasise about being
with guys and playing the female role, thoughts of giving a man pleasure
would invade my fantasies and i soon found myself masturbating to such thoughts.

Eventually i decided to explore the internet, coming across many porn
sites of crossdressers, shemales, trans and just about anything else
along those lines. Id imagine being them, fantasising about giving guys pleasure, being made to please them. After some time i knew that i had
to go further, i wanted to be taken, to be made to please a man.

I went online, found a crossdressing dating site and set up a profile. I
got lots of responses, being young and eager to learn seemed to get me a
lot of attention. I found a lot of people to chat with, similar
interests and ideas, before finding Peter. He was a lot older than me,
nearly 60, was handsome with short grey hair and kept himself relatively
fit. The more we chatted the more i felt at ease, the urge to fulfil a
fantasy taking over. Peter excited me and i decided to agree to meet
with him. We made plans to meet at my place, both agreeing to have no expectations and to see how we got on.

It was Friday evening and Peter was coming round about 7.30ish. As i
showered, excitement and nervousness was building up inside me. I had
picked out some black tights and yellow lace knickers and matching bra.
I chose a silver/green velvety dress, it felt tight on my neck and is sleeveless. It hugs my body and stops just above my knees. The green
strappy heels looked incredible, exposing my toes and making my calfs
stand out. I decided to wear a jet black Bob style wig and dark green
eye shadow and thick black eye liner, bright red lipstick completing the
look. A little perfume and i was ready.

At exactly 7.30, Peter knocked on the front door. Nerves flooded my body
and my breathing became heavy. I took a few deep breaths and opened the
door. Peter stepped inside, a big smile on his face. As i closed the
door Peter gave me some flowers and a bottle of wine. Not entirely sure
how i should react, i smell the flowers and say thank you, then shakily
invite Peter to follow me through to the living room. My heels were
clicking on the wood flooring in the hallway, and i was aware that my
hips swayed a little, and i sensed that Peter was checking me out. He
was wearing grey trousers and a light blue shirt and a dark jacket. He
was about 5 inches taller than me, and he matched the pictures he had
sent me, not over weight but a little extra padding. He was better
looking in real life, a kind of rugged handsome man, and his smile lit
up his face.

I told Peter to take a seat, then placed the flowers into a vase. I took
a couple of glasses and gave them to Peter, asking him to pour us both a
drink. I sat on the edge of the sofa, not far from Peter, trying to
behave like a woman. He offered me a glass and we clinked glasses. He
told me how lovely i looked, commenting on my makeup. He told me that i
had great legs and i blushed as i said thank you. Conversation was slow
at first, but i could feel myself relaxing and enjoying Peter's company.
Peter asked a few questions about why i liked wearing female clothing,
how long had i been doing it etc, the usual things. Halfway through my
second glass of wine i felt at ease and moved closer to Peter, our knees touching.

It wasn't long before Peter put his hand on my leg, i didn't say
anything or try to move. His fingers started to stroke my tights, i
loved this, the feeling was amazing. I allowed Peter to carry on, the
strokes getting longer and higher up my thigh. I tell him that i like
him stroking my tights, he shifts slightly, facing me. Peters hand slips
under my dress, getting closer to my knickers, i still don't try to stop
him. Peter gets very close to me, his arm on the top of the sofa. I look
in his eyes, then lean forward, our lips just inches apart, then i kiss
him on the lips gently. As i start to pull away, Peter places his hand
on my head, pulling me back to him.

I pull away, telling Peter that i hadn't done anything like this before.
I tell him about how nervous i am, that it's my first time with another
man. Peter asks if im ok, that everything is fine, trying to reassure
me. I say to him that im not sure of what im doing and ask him to be
patient with me. Peter is very understanding and i start to feel at ease
and comfortable in his company. We pour another drink and i relax as we
chat again. I take his hand and place it on my leg, moving a little
closer to Peter. I place my glass down, then lean forward and push my
lips against his.

We start to kiss, our lips touch and i feel his tongue gently enter my
mouth. I respond instinctively, meeting his tongue with mine. Peter
doesn't rush, softly and gently kissing me. I move my hand onto his leg
as the kissing intensifies, Peter's hand in turn sliding up to my
knickers. I quickly move my hand to his crotch, the kissing obviously
turning him on by the fact that he is rock hard. As i start to stroke
his bulge, i notice that he feels quite large. We continue to kiss as i
find his zipper, sliding it down and slipping my hand inside. Peter
breaks the kiss as my hand touches his manhood, he sighs and calls me a
naughty girl, being called a girl for the first time makes my stomach
turn excitedly. I bite my lip as i look him in the eye, my hand stroking
his cock, then i ask if he would show it to me.

Peter smiles as he keenly unbuckles his belt then fiddles with the
button on his trousers. I watch as he opens his trousers and slips his
boxers down to expose his very hard cock. He looks at me and asks me if
i like what i see. I stare at his throbbing manhood, nodding as i
whisper a yes. He is very straight and about 8inches long, not really
thick but definitely not thin. His helmet is not really wide but it is
shiny and looks ready to burst. I shift around on the sofa, im side on
to Peter, then go back to kissing him again. The kissing getting more
and more passionate, getting me excited.

Still locked in the kiss, i move my hand down to Peter's cock. My
fingers wrapping around his shaft, i feel him throb. Peter breathes in
sharply through his nose, and i begin to rub his length, im a little
clumsy in my efforts to stroke his manhood. Peter let's me know that my
hand is holding him too tight, telling me to slow down, i do as he says, apologising. I've never held another mans hard on before and i welcome
Peter's advice. I find myself looking at his long cock as i watch myself masturbate him, Peter talks to me, encourages me, calling me a good
girl. I look at Peter and ask if he would like me to try and give him a
blow job. He tells me that i should only do it if i am happy to. I
continue to stroke his length for a minute or so, then i decide i want to.

I get up from the sofa as Peter starts to push his trousers and
underwear down, i help, tugging them down to his ankles. I kneel between
his legs, his manhood standing to attention as i take him in my hand.
His cock is long and straight, i move my head until my lips almost touch
him. I can smell his musk, i close my eyes and kiss Peters shaft,
instantly my tongue licks him. Unsure about what im doing, i lick his
full length. Peter let's me know that it feels nice, he even calls me a
good girl, hearing him refer to me as a girl again really excites me.

I move my tongue to his helmet, swirling it around the tip, making him
gasp. I want to suck it, im a little apprehensive, but excited aswell. Eventually i guide Peter's cock to my mouth, clumsily trying to suck
him. I have my lips around just his helmet for a while, then i give in
to the urge to fill my mouth with his cock. Peter sighs as i start to
bob my head, giving me guidance, telling me to slow down and letting me
know when i seem to get things right. After what seems like a long time,
i stop, still holding Peter's cock, i look at him and apologise for
being clumsy, saying that i had never done this before. He smiles and
tells me not to say sorry, telling me how nice it felt.

After a few more minutes Peter stands up, I'm on my knees as he puts a
hand on my head and guides his manhood to my mouth again. He slowly
starts fucking my mouth, calling me a good girl and talking to me. I
have my hands on Peter's thighs as he pumps his long cock, filling my
mouth and almost making me choke from time to time. About 10 minutes
later Peter pulls out and gives a deep sigh, he tells me that he was
close to cumming but didn't want to cum in my mouth as it was my first
time. I say thank you, then i ask if he would like to cum on my face. He
smiles and nods, again I'm called a good girl as I start to suck him again.

Its not long before Peter withdraws and starts to masturbate fast. With
one hand he holds my head, keeping my face close to his helmet, then he
gasps loudly as cum erupts from his throbbing cock. I close my eyes as
warm cum shoots over my nose and lips, over my face and even under my
chin. As Peter breathes heavily, still standing over me, he lets go of
my head. I open my eyes, and start to wipe the cum from my lips with my fingers. Peter pants heavily and sits down, trying to regain his breath.

I'm still on my knees, a big smile on my face as i look at Peter,
knowing that i am the reason he is panting. He asks me if i am okay and
i nod enthusiastically, his cum still on my face and fingers. Peter
stares at me and smiles, and an urge overcomes me. I raise my fingers to
my mouth and lick them, tasting Peter's cum. He continues to watch as i
lick and suck them clean, enjoying the taste of his man juice. I'm
called a naughty girl as he encourages me, this excites me even more.

Eventually i finish and i get to my feet, telling Peter that i need to
sort my makeup out. I hand him his drink and quickly go to sort myself
out. I reapply my makeup and do my hair, adjust my dress and eagerly
return to the living room. Peter tells me how nice i look as i sit down
beside him, i blush again as i thank him. We drink and chat and he is
very complimentary, telling me how much he enjoyed me sucking him. I
tell him again that i had never done that before and he smiles, saying
how pleased he was to be my first.

To be continued...

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