Date: Thu, 16 Feb 2012 03:22:36 -0800 (PST)
From: pixiekim5@yahoo.com.au
Subject: Tomboy Becomes a Boy

I would like to tell you about myself, Toni, and my friend, Sasha. I've
always been a bit of a tomboy but at 16 thought I knew where I was sexually
and although quite plain looking I was always strongly feminine in whatever
I did. My room is dominated by pink and there are plenty of cuddly toys
still hanging about. My favourite is my teddy bear, with her pink ribbon
around her neck, taking pride of place at the head of my bed, and I still
snuggle up to it every night.

But nearby are my hockey stick and a catcher's mitt from softball that both
play an important part in my life. Last year I won the best player in my
hockey team. I move like a cat on the field getting to those hard to get
balls and passing them to my team mates. Rosie, Jackie and Robyn have been
my friends since juniors and we hang out all the time. We muck around with
boys but nothing serious.

I like to wear my mousie-coloured hair short like a boy because when it is
longer, it only gets in the way when I run, so the shorter the better. I
reckon it looks great brushed forward. I'm happy with my body. I still
haven't much in the way of breasts, but I feel them every chance I get when
I enjoy myself in my room and hope they will grow.

My relationship with my 17 year old brother, Tom, is different to say the
least, being only a year apart. He treats me like a brother should, well
sometimes it's pretty rough at least. There are no beg pardons from him and
we have had plenty of wrestling matches over the years after I have stood
up for myself whether it is at home or at the park. I guess I have
responded to his digs developing a rough and tumble attitude and this only
makes him more aggressive as I get older.

We also run a lot together, pushing each other to improve our fitness for
our sports. That includes workouts in our home gym, pushing weights to
develop muscles needed to excel in our team sports. I must say I love the
muscle definition of my arms and legs, I am so much stronger than many of
my sport friends.

Trouble is our familiarity becomes too close at some times. I don't know
whether he still looks at me as a "brother" or he has a weird fascination
for me. Sometimes it's lots of fun when he gets himself into embarrassing
situations with me. Like the other day he just walked into the bathroom
while I was taking a shower and took a piss. There he was only a couple of
feet away from me where I was behind the shower glass. He just seemed
oblivious to me being in the shower nearby, with his stream heading towards
the bowl.

"What are you doing in here," I screamed at him. "I'm just taking a piss,
won't be long."

"Get out of here," I screamed, can't you see I'm in here taking a shower."

"Yes, I can see that," he laughed obviously picking up my outline in the
fogged-up glass. Mum and Dad were out so I couldn't scream for their
help. Well, that was it. I picked up the loafa filled it full of water,
opened the door and threw it at him before slamming the door shut. Hit him
right in the back. He not only felt the full force of my pitch but he ended
up dripping wet.

"Get out you perve," I said.

"It's not as if I haven't seen it all before," he said before finishing up
and getting out.  Well. He was right. We have been pretty free and easy
with our nakedness as we've grown up, starting with sleeping in the same
room when younger, then as we've been given our own rooms, running from our
rooms to the bathroom and back without a stich on and protected only by the
flying towel and I have caught some good glimpses of him and his wobbly
dick and his nice little bum.

Anyway, that's what it is like with my brother so it might help explain
what happened next. We were watching a movie about a transvestite, you know
the one where the actress plays a man becoming a woman. It was so hard to
tell her from the guy and I said to my brother, "That's not her. It can't
be. She looks lovely in real life."

But my brother said of course it is. Then we had an argument after I hit
him telling him he was wrong. So we made a bet that whoever was right would
have to dress up as the opposite sex for a time at the discretion of the
winner, or something like that. And of course I lost. I thought nothing
more about it until a couple of weeks later when he said he was going to a
friend's birthday party and I could go along as a boy.

"You could be my cousin from out of town," he said. "No way," I said. "That
is not going to happen. What happens if someone finds out. My friends will
kill me. I won't be able to go to school, I will be so embarrassed."

"No problem," he said. "It's over the other side of town where the toffs
live and nobody will know you. It's my mate from footy." I was shaking. I
didn't know what to do. I had promised when we made the bet thinking I was
right, but thought nothing of it when I lost the bet.

"Don't make me do this. I'll do anything for you instead. Clean your room,
wash your car, anything." I said.

"There is no way out of this," he said. "You lost. You can wear some of my
old clothes mum has kept in the garage."

So the die was cast. It was in two weeks and I had to find a way out or
dress up as a 15 year old boy. I couldn't believe how stupid I was to make
the bet with him. Stupid movie. In the end it was easy or so I thought. It
was getting on to winter so I would be able to dress in bulky clothes
hiding what curves I had. The clothes in the suitcase would just fit and it
was a matter of working out what boys wore as a fashion statement. Tom was
over the moon, laughing every time he saw me but I couldn't find a way
out. Mum and Dad were going out that night and Tom told them I could hang
out with him.

I selected the clothes I was going to wear. Baggy jeans, of course, a
striped shirt and a tracksuit top that was all the rage. It was going to be
cold outside so I would wear a big jacket over that. But once inside I
would have to rely on the bulky top to hide behind. Then there was the
matter of my hair. A lot of guys are wearing it spiked up so with my short
hair I could manage that. But one look in the mirror and I realised my
wispy hair, where side burns should be, would give me away. So I took the
step of cutting them and making it look more boyish, brushing as much hair
back and giving it a light application from mum's hairspray to hold it in
place without it turning stiff. After it was all over, I could brush my
hair down and cover the cut portion helped by a hat that wouldn't take long
to grow.

Mum and Dad left for their party and Tom said I had an hour to get ready. I
was shaking. The bastard putting me through this, I thought. He was
enjoying himself. I took out one piece of insurance and wrapped a bandage
around my chest, flattening my boobs. The rage built up, but by the time I
had finished and looked in the mirror, I couldn't believe what I saw. There
was a boy. A bit effeminate but still I could get away with it, in the dark
of course. To improve the boy look, I put some zits on my throat with
make-up pencil and thickened and darkened my eyebrows.

"If I get caught you're going down with me," I said as I walked from my
room.

"Holy shit," was all Tom could say. He looked me over, turned me around and
gave me a high five. "I was thinking it wouldn't work," he said. "But you
could easily pass for a boy. Just remember to deepen you're voice and
swagger a little. Don't just stand around like a girl."

"If it looks like someone will find out, we come straight home. OK? No ifs
or buts or I don't leave the house."

"All right by me. I want to keep my friends as well. Before we go I've got
a present for you." Then from behind his back he produced a pair of
y-fronts.

"Are you joking? I'm not going to wear them. And besides I'm already
dressed and I've got my knickers on."

"Look closer, these are different," he said as he passed them to me. He was
right. There was a bulge in the crotch where the penis would sit. "They
come with your own slug," he said laughing.

"No way. I'm not wearing them. That wasn't part of the deal."

"Hey, if you are going to look like a boy you need a bulge there. Never
know who you might get close to. It's all part of the deal. Come on, put
`em on. You know you will have to have something there," he said.

By this stage I was broken. I was now completely humiliated. "OK, but I'm
not taking off my knickers.

"Whatever, just put them on."

I went onto my room and put on the y-fronts. It was a weird feeling as they
were a size small and the "slug" touched my pussy. Concentrate I said to
myself. Let's get this over and done with. I walked out.

"There you look great. Let's go." Tom had just got his license and we drove
to the party taking more than 40 minutes and I was scared a policeman would
get us at any time. Tom promised not to drink alcohol. He would be a fool
if he did as a probationary driver. He wouldn't get his license again for
years if caught.

The house was a fancy two-storey and despite the darkness, looked like it
had plenty of surrounding gardens. Tom rang the bell and Mrs Smith answered
the door. Tom introduced himself and I nearly shit myself when he
introduced me as his cousin, Tony, that he had to look after for the night
as his parents had gone out.

"I hope that's OK Mrs Smith," he said.

"You're both welcome Tom. You'll find the boys in the playroom, there's
drinks and food just enjoy yourself. Put your jackets in that room. Tony
the younger children are down stairs where there is a juke box. You'll find
someone to chat to there." But I followed Tom upstairs where the party was
in full swing and he was in his element grabbing guy's hands and hugging
them. The testosterone was thick with all these young guys trying to be
men.

"Whose the short fry," one said.

"This is my cousin. I had to look after him for the night."

"No juniors up here, go downstairs."

I hadn't expected to be separated from Tom and looked pleadingly at
him. But he shrugged his shoulders and said, "See you later kid."

So I wandered downstairs trying to look like inconspicuous and like a
boy. There were people everywhere and no one took any notice of another
young person. Just then the front door opened and a family walked in giving
hugs and kisses to the Smiths. I didn't think much of it until I saw her. I
stopped in mid step, one foot off the bottom of the stairs. She was so
beautiful, about a year older than myself and with beautiful flowing blond
hair. She had a body I would kill for, which she was showing off as she
took off her coat. It was then she looked up and caught me staring at
her. I didn't know what to do. I turned red with embarrassment, I'm sure I
looked strange, my tongue hanging out like a drooling dog wishing I could
look like her.

She smiled and I then realised who, or what I was. She thought I was a guy
coming on to her. Oh shit, I thought then turned away and looked for an
escape. Regaining my confidence, I followed the sound of the music to a
darkened room which had a door to the garden and where there seemed to be
lots of under 10s bopping away. It was going to be a boring night but I
grabbed a soft drink and some nibblies and headed to the juke box to see if
it had any of my favourites.

I smelt her before I realised she was standing next to me. I was
concentrating so much on the song list that the perfume took me by
surprise. It was lovely and as I turned to see where it was coming from I
looked straight into the loveliest eyes on a girl I had ever seen. She was
a bit shorter than me, and she was just lovely with her blond, curly hair
framing her face. I just stared lost in the moment. I didn't know what to
do. She was the one who spoke.

"See anything better than what's being played," she said in a chirpy
voice. As I was still staring she said, "Hello, anyone in there?" I shook
my head.

"Sorry, you took me by surprise creeping up like that. Hey your perfume's
lovely. What is it."

"That's a strange thing for a guy to say. But it's one of my mum's and I
love it. It's ... for your information," she said with a grin. "By the way
I'm Sasha."

What the fuck are you doing I thought to myself. Keep cool. Remember you
are a guy for the night.

"Sorry. I'm Toni. I was trying to put some decent music on. I hate these
boy bands. Give me Pink or anyone like that."

"You're right there," she said. "Time to find something better." We both
then turned our attention to the list and I selected a song and she
selected the next one and we did that until we had racked up about six.

"You've got the same taste as me in music," she said. "Let's hope it takes
over from the teeny-boppers stuff soon or I'll go out of my mind." We
talked about different things, school work, movie stars, then I blurted out
my prowess playing sport, saying I was in the grand final for Redbacks the
next weekend that we had a very good chance of winning. All of a sudden the
music changed and our second selection came on.

"Come on, dance with me," she said, backing away from the juke box to a
vacant spot in the room, beckoning to me with her hands outstretched.

Oh shit, I thought, what do I do now. Do I reveal I am really a girl
dressed up after losing a bet with my brother. Or that I don't dance, like
most guys would. What to do? She had this warm, friendly smile on her face
as she looked at me and we had been getting on really well, that I thought
there would be no harm, we are not going to touch anyway, like when I
normally dance at parties or at home with my friends.  So we danced and
talked and talked and danced, having a great time until all of a sudden
there was a slow number. I hadn't thought of that while I was enjoying
myself with her.

Sasha just put her arms around me, rested her head on my shoulder and said,
"Mmm, that's better. I love a strong guy as she felt my muscles." I
stiffened. Shit, are those her tits rubbing into me. She is going to feel
my tits, or at least my nipples which I could feel were hardening under the
bandage from her touch. Luckily though, as I was a bit taller than her, she
wouldn't feel the "bumps". We danced and she snuggled in closer. I must
admit I relaxed when I realised she hadn't worked out I was faking it as a
guy. I even loved the sweet smell of her as she rubbed up against my crotch
where she must have felt the "slug".

"I'm glad you like me as I like you too," she said. "Every guy I meet just
wants sex, but I feel so comfortable with you she said as she gently
stroked my face. I didn't know what to say, her touch caught me by
surprise.

Suddenly I blurted out, "I love talking about stuff with you. You are
beautiful, but I love you as a person." I knew it was wrong as soon as it
came out. What an awful line. I would have laughed at any guy silly enough
to say that. We moved in unison to a dark part of the room and she looked
into my eyes all of a sudden and kissed me.

"No!" I was screaming inside. "No, you can't do this." But she was and all
of a sudden I could feel her tongue forcing its way into my mouth and her
hands moving over my back, gently caressing my arse. Then something strange
happened. I got caught up in the moment. I could feel my pussy getting wet
and I responded to her kiss, opening my mouth and letting my tongue play
with hers.

We must have been like this for minutes, lost in our embrace. She was
planting the most passionate kiss I had ever received upon my lips and I
was loving every bit of it. I was lost in my deception. Had the
testosterone of my brother rubbed off into these guy clothes? She kept her
moist mouth against mine for a few more seconds before removing it.

"Let's go outside before someone catches us," she said looking around. I
nearly didn't move, ready to tell her what was really happening here, but
she dragged me to the side and we opened a door and stepped outside. It was
cold, but no one was there and we moved to a darkened corner out of the
way, finding a cane couch and lying down facing each other. She started to
kiss me again and I responded, I was lost and I didn't know what to do but
go along with her. What else could I do? It was too late now. She then
started moving her hands over my body, to my bum and back then started
feeling for my groin. Her hand made it to covering the "slug" before I
pulled away.

"Better not, you are making me too horny," I said.

"I'm already horny," she said grabbing my hand and leading it down under
her skirt, lifting it up until my hand was resting on her soft, nylon
panties. They were wet and she wanted to be wetter.

I said, "We had better not, we'll get caught," as I tried to pull away, but
she was already guiding my fingers under her panties and past her soft and
delicate pubic hair to her wet pussy. It was like being caught in a
dream. She ground my hands into her soft pussy folds and I couldn't help
myself as my hand just took over. She gasped as I touched the bud of her
clit and kissed me harder, grunting with every move of my fingers.

She pushed her hip into my crotch and the "slug" started to work its way
against my pussy as I felt my own orgasm building. Help.!! All of a sudden
I felt her shudder and she almost screamed, "Oh my God." Her orgasm sprayed
cum over my hand which was saturated but I didn't stop playing with her. I
then pulled out my hand, careful to avoid wetting her dress and held it up
to see the glistening liquid still dripping.

"Wow. That has never happened to me like that. You are just so wonderful,"
she said taking my hand and licking the cum. She then put it to my
mouth. The wonderful aroma was the first thing I noticed. It was not like
my cum after masturbation. It smelt like nothing I had ever experienced,
but like everything I loved in this world. I was just so turned on -- still
on my own close-orgasm high. I licked the fingers clean. I kept licking
until the cum had gone, leaving the fingers glistening still, but in my
saliva. What can I say it was just so overwhelming. The taste was
something I had never expected, it was just spinning me out like a drug. I
kissed her as hard as I could. It was wrong but I didn't care.

"Wow. I love my cum. But I didn't think a guy would love it that much," she
said. I smiled at her and put my hand in her panties again as I pressed my
crotch against her trying to satisfy myself. I gently played with her clit,
and then, didn't mean to do it, but my finger penetrated her, like it was
acting on its own.

"Oh, no, no, yes, yes, yes," was all she said as she stiffened against me
and came again. She just grabbed me as tight as she could. It was out of
this world. What an amazing thing to do, I thought, to have so much control
over someone by giving them the pleasure that I now craved myself. But at
the same time I was out of control. This was a girl. Trouble is she was in
control over me as she ground her hips against my crotch and the "slug"
moved its merry dance against my pussy.

Her lips left mine as she pulled herself closer to me, if that was
possible. I had completely forgotten who I was. I was overtaken by a lust I
had never felt before. I had kissed a couple of guys in fun, but nothing
felt as wonderful as this. Her mouth moved to my ear.

"Oh my God, this is great," and I increased the tempo of my finger inside
of her. My hand was drenched, slippery liquid oozing between my fingers. We
looked into each other's eyes, not wanting to lose that connection, a
longing that seemed to reached inside both of our souls.

We suddenly came back to reality as everything was quiet. "Time for the
birthday cake," I heard a distant call all of a sudden. It was Mrs Smith
calling out inside to everyone to get together for the birthday
celebration.

Sasha said, "Oh shit. My folks are going to expect me there." We stopped
clinging. I removed my hand and licked it clean as Sasha tidied herself.

"Well, I'm not going to waste it," I said to her as she smiled coyly at me.

"I've got to go before we get caught," she said.

"OK," I said. "You go and I will follow." With that she planted one last
loving kiss on my lips.

"We'll have to do this again," she laughed. Then she was gone. What the
fuck just happened, I thought to myself. Am I a lezzie or what? Did I just
finger fuck a girl and enjoy every minute of licking her cum off my hand?
No, no, no. I bought my hand to my nose still smelling her as I moved my
hand to my crotch. All of a sudden she was in front of me again.

"Hey, I want to play down there," she said moving her hand to my
crotch. "Quick, give me your mobile cell number," she said instead. I
blurted out my number without thinking. She put it into her phone then my
own phone, still in my back pocket, rang. "There, answer that and it's in
your directory -- we're connected." She kissed me again and left. I did as
she ordered.

The enormity of what I had just been through started to sink in. I had to
get out of there. I went in search of my brother, saw him at the back of a
room and grabbed him. "Quick, we have to go. I have got to get out of
here."

"No don't be silly, it's only starting." "No now. You promised. Someone
knows I'm a girl. I got sprung. You promised let's go." I grabbed his arm
tight and he could see the panic in my eyes.

"OK. Only because I promised and you went through with the charade."

Once home I threw myself on my bed, burying my head in my pillows. I think
Tom went back to the party, I didn't know and didn't care. What have I
done. This nice person I just met thinks I am a guy and I, I had sex with
her. No, no, no. This couldn't have happened. I'm happy being a girl, I
love guys. I'm sure. My hand went instinctively to my face and I smelt her
still there. That lovely aroma, and I thought of her touching me and our
tender kisses. My other hand went to my pussy as I absently played with
myself. No. I stopped. Get this out of your head. But it didn't go as I
dreamt of her, bringing myself to a climax just thinking of what I had
done. To make matters worse, I thought of our pussy juice mixing together
as my hand rubbed my clit.

The next week was a nightmare. I was like a bear with a hangover. Nothing
was right for me and I was cranky with everyone.

"What is it, that time of the month for you?" Robyn said one day at school.

"You've got a bad dose." Sasha rang, several, no many times, but I didn't
answer until one night I just relented and said hullo.

"Where have you been. Why didn't you answer me. I was worried about
you. You left and I couldn't find you," she said.

"I've been busy. Look, we can't see each other again. I am no good for
you. I will only create problems. You don't know who I am."

"What do you mean." I just told her I was bad news. I couldn't tell her I
was a girl, it would be too much, she was so nice. I said to forget about
me, and hung up. I stuck my head in my pillows and cried. I couldn't
believe it. Here I was sad and crying over a girl I had told I didn't want
to see again. I cried myself to sleep but not before touching myself,
climaxing with thoughts of her touch and smell.

I was on fire, switched on and playing the best game of my life, just at
the right time during the grand final. I had decided to concentrate on my
hockey to get me out of my depression and it was working, to the point that
I was in the zone and nothing was going to get past me, and I had set up
three goals. Half time came and we had arms around each other as we walked
off, confident we were heading for a win. I let my gaze wander and there
she was, one hand to her mouth looking directly at me. My heart sank. Why
is Sasha here, what brought her to my game. Then I remembered in our
conversations on that fateful night I had told her how great I was at
hockey as part of my team, the Raiders, and we were heading for a grand
final berth at our home ground.

I nearly stopped dead as I looked at her and saw the shock on her face. I
had on my skirt as part of the team uniform, but the short hair and the
fact my team mates were calling Toni every time I got the ball must have
added up pretty quickly for her.  My team mates realised something was
wrong as they dragged me along. I lost sight of her, and when I caught
sight of her again she was running across the oval to the car park. I
wanted to follow, to explain to say how sorry I was, to organise a
date. No, no no. I didn't want that. Shit.

To say the least, my second half was atrocious but we won and I went to my
celebrations in a daze. I phoned her. It was the least I could do. Her
phone went straight to voicemail. I left a message saying that I needed to
talk to her, to explain, to tell her I was not a bad person, I left a dozen
messages by the end of the night. I tried again next day, doing the same
thing.

By the third night I was just about to give up when my phone rang and it
was her. She gave me a mouth full of abuse. Such a lovely person, I didn't
think four letter words would flow so easily from her mouth. When she
settled, I again apologised and went through the explanation, saying that
by the time we started kissing, it was too late to say anything, that I got
caught up in the moment. She stayed on the line, saying nothing. I then
started crying. I couldn't believe it. What was going on with me.

I blurted out that what we did was so wonderful, I had not thought such
tenderness was possible. That I had never done anything like that or had
even thought about it before, especially with another girl. That I couldn't
get her out of my mind, especially when I went to bed every night. That I
could still smell her gorgeous perfume, still taste her, feel her. That I
was revealing my deepest feelings for her, something I had never, ever,
considered for anyone before. She hung up. I was devastated. I cried myself
to sleep again. The next night the phone rang again and it was her.

"What you did to me was deceive me. Besides, I have never, ever allowed
anyone do that before, to touch me. You got to me, the way you talked to
me, your tenderness, and then your fire. What have you done to me. I think
about your touch every night. I just don't know what is going on." She
started to cry.

"I'm sorry, so very sorry," I said. "But at the moment all I can think
about is holding you. We have to see each other again. If for nothing else
but to end these thoughts. It's the only way." We agreed to rendezvous and
I waited in the café after school where she had suggested. I had put on
some make-up after leaving school, calling into a Maccas. Well, I didn't
want to look as awful as I felt. Just wanted to pretty myself up for her to
show I was a female too. She walked in, kind of apprehensive, then saw me,
giving me a half smile.  "Can I get you something," I asked as she sat down
opposite me.

"A juice will do. Any sort." We drank in silence, trying not to look each
other in the eye.

"I didn't want to hurt you. I am not a bad person. But when we started, I
couldn't stop," I said. Then she surprised me.

"What did you have in your panties? I definitely felt a lump." I explained
my brother had given me the y-front with the additional "slug" for fun.

"Well, it felt real enough, not that I touch guys down there," then she
laughed. "You looked so believable. Now I can see differences, I can see
how beautiful you are."

"Nobody has ever said that to me," I said feeling embarrassed. "I have
never considered myself anywhere like good looking."

"Well, you are. In my eyes anyway." Was she coming on to me? I reached out
my hand to touch hers. No stop this you can walk away now, I thought
stopping short of her hand. Her fingers then reached out and started to
play with mine. We looked into each other's eyes and I knew I was lost
again.

It was very public and I looked around concerned we would be seen. Sasha
said we should go for a walk. We found a quiet spot in a nearby park,
walking hand in hand and just talking. She said she had gone through denial
like me but kept coming back to the same thing. For some reason we clicked
and she wanted to be with me, to have a relationship. She didn't care if I
was a girl or not. We just had so much in common. I said I wanted the same
thing. We stopped and kissed. Once again her soft lips opened letting our
tongues play together. I was aware that my panties were getting wet.

I told her that and she said, "So are mine."  "I want you."

"We'll have to wait. We might be seen, even here by someone we know." We
walked to the bus stop. We let our hands go at the last moment, but kept on
bumping into each other, laughing and giggling like young kids.

"Until next weekend my love," I said after we arranged for a sleepover at
her place.  Her mum, "Call me Helen," greeted me with a hug.

"Well Toni, you are the first person since Sasha was a little girl, who has
come over for the night. You must be special."

"I don't know about that, Helen. Just nice to have a friend." "I don't know
if Sasha told you, but she has double bed in her room and you will have to
share. We couldn't get a spare mattress in."

"I'm sure we will be OK," I said, as long as Sasha doesn't snore." She hit
me on the shoulder. "Ouch," I said and she dragged me away.

"Come on I'll show you my room." "I'll give you girls a call when dinner's
ready, OK?"

"Yes Mum, thanks."

As soon as the door was shut we were all over each other, kissing fondling
everything we could think of until we ran out of energy and fell onto the
bed.

"Share this with you, eh?" I said "Should be fun. "Oh yeah, you bet."

We started snogging again, my hands touching Sasha's boobs and her hands on
mine. I wanted to go further, but then her mum called that dinner was ready
and we reluctantly stopped.

"After dinner," Sasha said kissing me so deeply I didn't think I would
breathe again.  ends

- 2012 copyright K.I.M.