Date: Fri, 11 May 2012 23:29:34 -0700 (PDT)
From: Kenneth Matts <pixiekim5@yahoo.com.au>
Subject: Playing a Guy Becomes Hot

When I was given the part, I didn't know how to react. I was in an all-girl
school and someone had to do it, so I guess why not me? But how would I
play the part of a teenager approaching manhood when I didn't know much
about guys? There had been little chance to get to know how boys carried on
as I was an only child and although I had met some boys while out with
girlfriends, few had impressed me to the stage where I had a real
relationship. Besides, being considered a bit of a nerd, I had my school
work, acting and music to keep me occupied. So I needed to do some research
to play the part. I just had to succeed in this character as I always want
to be the best, just as I wanted to get into the university course I
desired. My school drama teacher was of little help, only saying to get to
know the character and how he would react. How could I do that when I knew
little of a guy's mind anyway.

I talked to the director of the playhouse near home where I had been acting
since I was a child. Miss Smith was a strange woman, not overly liked by
most of my friends, but I managed to get on with her. She had taught me a
lot about theatre as I grew up and she was the only one I could think of
talking to. She was more than obliging, even had a sparkle in her eye when
I said I had to play a boy and had to give a pretty good account of myself
as it meant so much for my final year results.

She was the one who suggested I literally step into the shoes of a male to
experience what they went through. I was gobsmacked but she showed me how,
with a little make-up and a wig, and a few costume changes it could be
done. Over several weeks I learnt the stagecraft that would transform me,
leading to the time when I would step out as a male for the
research. Little did I realise just how it would transform my life
completely.

I selected a night out at a rock concert in a nearby town to put the
changes to work and used the dressing room at the theatre to get ready
after Miss Smith gave the permission. The transformation involved wearing a
wig over my ginger hair that I had already cut shorter and temporarily
darkening my natural ginger eyebrows into a dark brown. Some padding in my
shirt gave me broader shoulders and the jeans and sneakers could have been
worn by any sex. I did take the extra precaution of binding my breasts by
wearing a skin tight, sports compression t-shirt that flattened them
perfectly. It would give me the look of having worked out, resulting in
great pecs, as long as my nipples controlled themselves.

The transformation shocked me when I had one final look in the mirror. I
was nothing like my former self. I was reasonably tall and long limbed for
a girl as it was, but I had filled out recently without being fat, so I
fitted reasonably well into the guy clothes I had borrowed and scrounged
from seconds shops.

I headed to the concert where I intended to simply be an observer, watching
guys and their reactions. Walking through the door and past the security
was a bit scary as I expected them to frisk me, but nothing happened and I
joined the throng. I didn't expect to meet any of my friends as the concert
was in the next town, requiring me to drive more than an hour in my mum's
car to get there.

I got into the groove of the concert and was dancing away with the massive
amount of people, enjoying the silliness of the guys and their antics as
they showed off to each other, not even worrying about picking up girls. It
was then an older girl bumped into me, and she was right out of it. She was
either drunk or high and I tried to steady her when some boof-head of a guy
pushed me away and said: "Get your hands off her, she's with me." I
couldn't believe the reaction by this jerk, angered by something as simple
as her running into someone else and then construing I was "picking up his
property." I was about to tell him off when the girl put her arms around me
and gave me a passionate, if wet and sloppy kiss on the mouth. I was
stunned. "I'll do what I want. You don't own me you jerk," she screamed out
at the guy over my shoulder. I pushed the girl away and turned to the jerk
when all of a sudden I saw him throw a punch in my

 direction.

Now, I have done lots of courses at school and one of them was self
defence. So being sober, I easily avoided his drunken, wild swing, which
resulted in him being thrown off balance, falling to the ground with a bit
of help from my outstretched leg. But before I knew what was happening
security was hustling the three of us out of the venue. I was protesting my
complete innocence but they were stoney faced. "Don't fuck with me
mate. You are out. I don't care who started it." So there I was on the
pavement with this stupid bimbo and her boyfriend who then tried to fight
with security only to be quickly bundled away from us.

"Fuck, fuck, fuck, how do I get out of here now," the girl said as she
staggered along the pavement. She was as I imagined a stupid blonde bimbo
to be, pushing the boundaries with her short skirt and very revealing
top. "He seemed so nice, then he turned stupid and clingy," she
slurred. "Shit. Prick must have spiked my drink, I'm out of it." I suddenly
felt sorry for her, but realising the night was wasted for me, I started to
walk away. She came staggering after me, grabbing my arm, pulling me
around.

"You were great. I saw it all. You dropped him. What a lump he is. He said
he was going to get me home. Please help me." I turned and started walking
away, not wanting to get involved. "Bastard, a girl can't trust any of you
guys."

It was then I realised I was, in her eyes at least, a guy and
stopped. Well, if I can't do the right thing for a fellow female in trouble
what sort of person would I be. I turned and stepped towards her with my
hand held out. "Come on then, where do you live? My car is around the
corner," I said in my deepest voice. She smiled and leaped into my arms,
again giving me a wet, passionate kiss, this time sticking in her tongue. I
pushed her away. "I'll give you a lift, that's all," I said.

"Great, let's go," she said putting her arms around me. Holy shit, I
thought. What is going on here. What an idiot I am by getting involved in
the first place. I was supposed to be heading home, now I'm helping her
out. I started walking, pulling her quickly to the car, wanting this to all
end as soon as possible. She hopped in as I held the door open for her. "A
real gentleman," she said smiling at me as she sank into the seat, her
short dress riding up to her crotch. She caught me accidentally looking at
her blue-coloured panties, spreading her legs a bit more to give me a
better view as I looked away. I felt myself turning red with embarrassment
and shut the door. She didn't seem to worry much about it and gave me
directions without trying anything else. Luckily I vaguely knew the way and
we safely arrived at her place.

I helped her out of the car, putting my arm around her waist and struggling
with her to the front door as she leant against me. She couldn't use the
key so I grabbed her hand and held it in the lock. The door opened and we
fell inside. It was a beautifully-kept small apartment, very feminine and
certainly not what I was expecting. I asked her where the bedroom was and
helped her until I was able to flop her onto the bed. She lay there all
arms and legs, with her dress riding over her hips and the top askew
exposing her lace covered breasts. I turned to go, glad I had at least got
her safely home. She grabbed my arm suddenly and pulled me down. I landed
on top of her.

"Please don't go, every guy I have been with has treated me like shit and
would have been jumping me by now. Not you. What are you gay or something?"

"Of course not," I said not wanting to expose myself and be caught out. "I
just don't want to take advantage of you like this. It's not right."

"Oh you are just so different, aren't you," she said. "Where have you been
all my life? Please, just stay." She began gently running her fingers over
my face, then playing with my hair, wig. "Wow, you have had a really close
shave, like a baby's bum," she laughed.

I smiled at that, thinking if she only knew what was before her. Before I
realised what was happening, she kissed me, a soft gentle embrace, nothing
like the sloppy drunken mash from earlier. I tried to pull away, but I was
pulled in, entranced by my situation as the closeness and the heat
generated by our two bodies started to arouse me. I was a girl, acting as a
guy with a girl who wanted me. Wow.

Before I knew it I was responding to her kiss, my tongue playing with
hers. I started to enjoy it, enjoy her. Her smell, her touch, her
softness. I was really turned on by the situation, feeling moist between my
legs. She grabbed my hand and led it to her breast. I tried to fight her
but I had lost control of the situation as, I must admit, I really didn't
know what to do. Expose myself, as a girl of course, or just try and escape
somehow.

I was really starting to enjoy kissing this girl, I had become somebody I
never knew existed. I had never, ever, thought of being attracted sexually
to a woman, only admiring beautiful girls from afar, as any girl would
do. But this was taking me to places I never realised existed.

With that thought I suddenly felt a chill pass through my body. The message
it carried was get out of there now. I was kissing a girl, a woman
obviously older than me, at least in her 20s, but something kept me there
in the embrace. I should walk out on her knowing I would never see her
again and everything would return to normal. She wouldn't remember me as
she was so high on whatever had been forced on her. But I stayed. I wanted
the abnormal in my life all of a sudden. I wanted this. My fingers worked
their way past the lovely, lacy bra, enjoying its soft satin feel until I
started playing with her erect nipple.

"Your bra is so lovely. I haven't seen one so nice," I said as she pushed
my head down and I started kissing her velvety soft skin.Â

"Funny thing for a guy to notice. You guys just normally want a look then
take it off."

"No, I really like it, the blue suits you," I said lifting my head.

"You've already seen what else I have," she said, smiling in a wicked
way. I began kissing her between her breasts as she had moved my hand down
her body to the waist of her panties. The soft material gave way to the
ever so gentle covering of hair leading to her vagina where her wetness
covered my finger. She moaned and forced her mound up to meet the pressure
I applied and I was lost. I should get out of here, I thought, but she
opened her eyes and looked at me with such lust. "Oh that is wonderful,
please, please ..."

My fingers moved as they had done the night before in my own pussy. I found
her nub, gently caressing it and this sent her over the edge, as she moaned
louder in total enjoyment. So I continued, playing with her, running my
fingers along her opening, and coming back again to the hard clit,
gradually entering her until she came with such a rush my hand was
absolutely covered in her cum.

"Oh my sweet, oh that is so wonderful. You are great." She pulled my
cum-covered hand to her mouth, licking it then offering it to me. My tongue
had a mind of its own and started tentatively at first licking her sweet
tasting nectar. We kissed and I was lost in a whirlpool of emotions,
sinking so deep into woman love that I didn't know how to escape. She
started working her way to my pants undoing them.

"Here let me get you off," she said in a rasping voice. I was about to let
her reach inside my pants as I desperately needed a release, oh how I
needed it. But I grabbed her hand pulling it back. "I would rather please
you more," I said.

"OK," she said a little too quickly as she pushed my head down past her
breast to her hips, my tongue leaving a trail all the way, tasting her
salt-sweatened skin. I reached her blue bikini panties, obviously part of a
set with the bra I had spied earlier in the night. "You were right, I love
these, they're so lovely, but..." I said as I grabbed either side and
pulled them off as she raised her legs. She then spread her legs before me,
revealing her pussy, glistening through the light covering of hair that was
now inches from my mouth.

I didn't mean this. I intended to again have used my fingers to get her off
and to get out of there. I tried very hard to pull away but she put her
hand forcefully on my head: "Please, make me cum, lick me to heaven." Her
smell was overpowering. I had already tasted her and enjoyed it like a drug
and now her pussy was in front of me, the lips oozing in anticipation.

Thoughts of damnation were screaming through my head as my tongue again
took over, my first tentative attempts gently licking her sweet, soft
lips. She moaned again, rising her hips to meet my lips and I immediately
kissed the soft folds, sucking her, wiggling my tongue against her nub
which stood out like a sentinel. She started to writhe like an out of
control beast under me and I worked harder, my tongue flicking in and out,
up and down.

Oh how I was enjoying this. I didn't care that what I was doing was wrong,
against everything I had been brought up to believe in. I had walked over
the threshold into woman love and was enjoying every minute, except I
wanted to cum as well. With one last scream she came and her juices again
flowed freely as I licked then drank every drop. She just lay there as I
moved back up to face her, her eyes closed with the complete look of
satisfaction that I had produced. She opened her eyes and I realised l was
in love, as our mouths joined, our tongues flicking and playing, swapping
the juices I had just lapped up.

"What's your name?" she asked. I was stunned. We had just shared one of
life's most intimate moments and we didn't know who we were. "Jen," I
dreamily said, then realising my error quickly said, "Ben, Ben Smith." "Hi
Ben, I'm Steph," she said smiling. "You are the best. I have never cum so
much. Most guys don't want to go down on me. They want me to do it to them
though."

We cuddled and she started feeling me, working her hands over my back to my
arse, then towards my crotch. Though I loved it and wanted more, I realised
I couldn't let it happen. "I really have to go. My folks will be expecting
me." She laughed. "Are you still living at home?" I wanted to say, of
course yes, I am a girl in my last year at high school and heading to
university next year. "Of course I am living at home. Saves money," I said
extricating myself from her clutches.

"I want to see you again," she said and before I had a chance she grabbed
my mobile, that had fallen from my trousers, entering her number. She then
pressed dial and it called her phone which she picked up. "Now we have our
numbers," she said. She kissed me and I responded with such intense love
that I didn't realise I could ever feel. In the car I lowered my pants and
brought myself off. It didn't take long, I was so fucking horny.



I should have deleted the phone number then and there. My life had been
turned upside down and I should have stopped it from getting worse. I now
looked at my close circle of girl friends through different eyes. Even at
the other girls at my school. I was sure I was not interested in them
sexually, but appreciated their bodies a lot more. One friend caught me
looking at her a bit longer than usual, throwing me a questioning look
which I smiled at. I got through my theatrical performance, giving the
leading lady a big surprise when we had to kiss. Instead of the expected
hesitant coupling that had been happening before at rehearsals, I grabbed
her shoulders with both hands and planted my lips on hers with fervour. She
was a bit taken back, but like a true actor she carried on and we received
good applause for our efforts. I was given great compliments for the way I
had responded to playing the young man's character. But I was troubled and
within days

 had to sit the first of the practice exams before the real tests the next
month. Expecting to pass with flying colours, I just managed to scrape
through, my mind that had been so focussed and never let me down, was
elsewhere.

Steph rang several times, leaving messages for me to ring her but I
didn't. Then one day she caught me and I stupidly agreed to see her
again. We made a date at a club. I intended to let her down, tell her I was
not interested in her so I dressed as a guy again. Meeting her at night was
good as it helped with the disguise. We met hesitantly, I kissed her cheek
and we went in, ordered some drinks and started to chat. My intention of
dropping her was lost as the time flew by. We had so much in common as I
quickly found out and then we danced, not too close but responding
sensuously to each other. It was late when we left and I really had to get
home for sleep because of study. She talked me into driving her back to her
place. We stopped outside and turned to each other. I thought now is the
time, tell her and end this, but when I looked into her eyes I hesitated
and before I knew it she was kissing me.

We made it into her apartment, kissing each other, struggling to her
bedroom running our hands over each other's body. I was so high on lust I
bent down and lifted her up, carrying her the last metre to the
bed. Luckily she was lighter than what I imagined, and we flopped down onto
the bed laughing like crazy people. I kissed her lips then moved to her
neck, working my way to her breasts. I undid the buttons on her shirt,
lifting it away revealing a red lacy bra, even fancier than her blue
number. "Wow, you have great underwear. It is so lovely," I blurted out as
I rubbed my face into the bra pushing it aside with my chin to find her
nipple. "There is more to come," she giggled. There was no stopping me this
time as I sucked on each nipple, Steph moaned enjoying every bit. I then
kissed my way down to her jeans, stopping as I looked back at her and she
had this wicked look on her face. I undid them pulling them off as she
raised her butt off

 the bed revealing red panties, a match to the bra. I had never thought
much about lingerie, never being able to afford it but it was so lovely
that I exclaimed, "Oh Steph, these are just so lovely," as my mouth sucked
on them over the wet spot made by the juices from her pussy. The reaction
was immediate as she bucked, thrusting her hips up so I sucked again,
drawing her lips into the soft material.

She played with my hair and my hands reached up and played with her
breasts, squeezing her nipples as I continued sucking her and the
panties. She moaned and bucked as I pushed by mouth, chin, everything
against her, and then the flood started. She came with wild enthusiasm,
squeezing her legs against my head, but I refused to stop. I didn't need to
finger myself, I came just after her, the tightness of my clothes and the
enjoyment I had in pleasing her sending me over the edge.

We lay beside one another exhausted. All of a sudden I realised she had
worked her way down my body and was starting to undo my trousers. I
immediately came out of my reverie, sitting up and grabbing her pulling her
back to up to me. "What are you doing? It's your turn to cum," she said.

If she only knew. "I can't," I said. "I really have to go."

"No, no way, not after what you did to me. That was just so wonderful."

I pushed her gently to the side as I stood up, looking back on the
disappointment shown on her face. I leant over and kissed her, then grabbed
my things and left before anything more happened. I had failed in my quest
to be honest with her. I just couldn't bear to let her down.



My school work was suffering so much, even my parents realised that
something was wrong. I was just not concentrating, so I decided I had to
sort it out or the year would be gone and my aspirations for university
lost. I would front Steph at her work, she had told me where when we were
having our drinks. The only way I could find the time was after school, so
dressed in my school uniform and with no disguising make-up or wig, I would
somehow tell her Ben could no longer see her or was no longer around. With
that in mind I went to the store and was wandering around looking at the
lingerie when she approached me. "Can I help you miss?" she said. I turned
to her looking into her lovely eyes but couldn't say a word, lost in her
beauty. "I, I'm looking for some matching set lingerie, similar to that a
friend wears. She has these lovely blue and red sets." Whether she thought
I couldn't pay for them or somehow thought she recognised me and was

 trying to figure out where it had been she saw me, she hesitated a
bit. "We have some nice sets over here," she said wandering away. I
followed her, realising I had little money in my account to pay for
anything if I bought it.

We looked through the lingerie as I recognised a similar set to the what
she had worn, fingering them thoughtfully, "You can try on the bras, but
not the panties, as they should be regular sizes. Try these, they should
fit you. There are changing rooms over there. What's your name?" she said
pointing to rooms at the rear of the store. "Ahh, J..Jen," I managed to get
out. I didn't know what to do. I went inside, removing my school shirt and
old white cotton bra, slipping on the lacy, red bra first.

I was thinking it did look nice on me and the right size when there was a
knock and she asked: "Can I come in, perhaps I can help."

Before I knew it Steph was in the cubicle with me, looking me over. "Looks
lovely on you. I have a set exactly like this," she said. I went cold. Had
she recognised me? She put her fingers on the bra, pulling the sides so
they fit tighter, then she touched my breasts. "Sorry about that. But you
have probably been wanting me to do that for some time," she said looking
me in the eyes. "Are you sure your name is Jen. Not Ben as well is it?" I
was busted, but how?

"I'm so sorry. How did you know? I couldn't find a way to tell you."

"I realised your face was too soft the other night. Then you had to race
away again before I could touch you. Then there is one other major
thing. You have a little mole where your adams apple should be, as a guy
would have. What is going on?"

I was dumbfounded not sure what to do when I realised she still had her
hands on my breasts and was fingering my nipples. I weakened at the
knees. "So how old are you then?"

I swayed as I melted under the enjoyment of her touch. I told her and said
I was in my last year at high school, then explained about pretending to be
a boy for the play and how things got carried away.

"Well you were pretty convincing, I can tell you. You had me coming," she
laughed. I relaxed, realising I was not in that a bad situation, but
perhaps in something I might end up enjoying.

"We need to get together and have a talk. What are you doing tonight?"

"I, I can't. I have a really important exam tomorrow. How about Friday?"

We set the time at her place and she let my breasts go and left, pausing to
say loudly as she left the cubicle, "That colour really suits you miss."

I took the lingerie to the register where she asked, "Have you enough to
pay for this?" I shook my head no. "Well when you come on Friday I will
tell you how you can earn enough to buy it and more."

She took the bra and panties from me and placed them in a nearby trolley.

I couldn't believe what was happening. Here I was, a normal girl without a
worry in the world, heading for a planned career and life, when all of a
sudden everything had been flipped upside down by this gorgeous woman.



I don't know why, but I was a little more settled at school for the rest of
the week getting through my work, but I still couldn't get Steph out of my
mind and our planned meeting. Friday came and I found an excuse to stay
overnight at a schoolfriend's house and went to her house. I don't know
what overcame me but I put on make-up for the first time in ages, and was
wearing the newest undies I could find, hoping I wouldn't be having them on
for too long. She answered the door in a slinky one-piece catsuit leaving
little to the imagination as her nipple poked through the material that
clung tightly to her body. I hesitated and my jaw must have dropped. "Stop
drooling and get in here," she said. Before the door had shut she grabbed
my arm, pulling me to her. "Well lover, I didn't expect you to be a fiery
redhead but it probably answers how you turned me on so much."

We kissed passionately, our tongues gently playing and our hands moving
ever so gently over each other, I thought I would come straight away.

"Now enough of that," she said breathing heavily as she forced herself from
me. "We need to talk. I have a proposition for you." We sat and Steph
explained how she was always interested in other women, but had never found
the right one, until perhaps now? She said the night at the concert she was
picked up by the guy who was friendly enough and must have spiked her
drink, hence her willingness to end up wanting to have sex with me.

Although she worked in a store, she also did some freelance modeling and
working for a lingerie company that sold its goods through home parties.

She talked to me about the women's groups she had in mind, all older
lesbians or bi-sexuals who met regularly for fun, and she wanted me to join
her - dressed as a guy.

"What do you mean, I would have to be a guy. Everyone would know anyway if
you ended up picking it."

"That's all part of it you see. The women I plan to introduce you to would
enjoy the novelty of a girl dressed as a guy and it will lift our
sales. You will be a hit, believe me. And there's a lot of commission for
us both on sales. After all, you are such a lovely guy," she laughed.

Well I was surprised to say the least. This was one thing I didn't expect.

"But you are so beautiful. I'm just ordinary. I would mess it up. Besides,
I have my exams to worry about." She reached over, took my face in her
hands and kissed me, oh so tenderly. "You, my love, are beautiful and such
a sexually charged chick that you will be a hit. These women we will meet
will see that, I'm sure of it. They too will love you. Just remember we'll
be together. Besides, we will start after your exams so you will be ready
to take on the world."

A thrill went through me when she said we would be together and any
thoughts I had that our relationship was wrong were forgotten.

The zipper on her catsuit was hard to find but I helped her peel it off,
revealing her wonderful boobs. I latched onto her nipples straight away
first one side then the other. She told me to slow down, but I couldn't I
was relentless.

I don't know why I worried about my fresh panties, as they were gone in
seconds and she was there greeting my pussy for the first time.

She then gave me an orgasm I had never even dreamed about, using her tongue
with such great effect I thought there would be no end to it. Then she
attacked my other love hole, sending me around the world all over again.

Needless to say I stayed that night and our lovemaking took me to another
dimension in my life.



My exams were barely over when we organised our first party. We worked on a
routine where I was to be the waiter handing out drinks and nibbles before
the show began. Then I would disappear coming out after Steph had run
through several outfits and she would strip me to reveal another set of
underwear.

The party went perfectly, with my disguise working well enough though I had
never run into such an aggressive pack of women before. I am sure several
women knew I was a girl, sidling up to me in a suggestive manner, with one
actually pinching my bottom. Of course I smiled and spoke to them as if
they were children, "Naughty, naughty, I will have to smack you if you do
that again." Of course most did try and I had to smack their hands. My
striptease was a hit as my body was revealed. Steph kissed me and ran her
hands all over my body, taking clothes off as she did. It was very, very
sexy, even from my perspective and my panties were the worse for wear. But
by then I was not worried and just went along with the fun as the women
cheered as each piece of clothing revealed more body and lingerie.

We made a killing with sales, as most of the lingerie was sensible briefs
and bikinis wanted by the older women and very lovely lacy bras of
course. We were talking to the party organiser and she wanted us to do our
show on a regular basis, and was even prepared to cover costs if there were
not enough sales. She loved the fact I was so young. I was explaining I was
aiming for university hoping to get into law when she said "Say no more. If
you are equally as good at your studies as you are thinking up a show like
this I want you on my team." She offered me work immediately as a clerk at
the law firm where she was a partner. "My dear, I can see we are going to
have a great relationship together," she said, putting her hands around me
and kissing both my cheeks. She didn't let go before a feel of my arse. I
didn't know what to think, but if I could control her urges, my life was
certainly on the up.

I told Steph and she laughed, "She is sex madd. You will need your wits
about you."

"With you as my partner, I won't have any problems," I said.



I hope those who emailed me after my first story enjoy this.

Copyright 2012 pixiekim5@yahoo.com