Date: Tue, 17 Apr 2012 11:26:53 -0700 (PDT)
From: Tony Williams <tonywill9999@yahoo.com>
Subject: Dress Me as a Girl

     "Okay then, dress me as a girl," I said.
     I'd been spending the week at my aunt's house because my mom was in
the hospital.  Brit was my aunt's daughter and that would make her my
cousin, I guess.  At thirteen, she's a year younger than me.  I thought it
would be a pain, having to hang out with a younger girl, but she turned out
to be okay.  That first rainy Saturday afternoon, she invited her friend
Kitty over and we we all in Brit's bedroom, bored out of our skulls.
Sitting around all day with a couple of little girls was not my idea of
fun, but I had to admit they were kinda cute.  Playing on the computer was
music by her namesake, Brittany Spears.  I had to admit that both girls
were quite cute, but fourteen year old guys don't usually spend much time
with girls from lower grades.  Still, none of my friends were around to
scoff at me.  Kitty was wearing a provocatively short skirt and white ankle
socks, and in a reckless moment, I reached out, lifted up the hem of her
skirt and looked at her panties.  White, I noted with satisfaction.  There
was a short pause before she pulled away and said, "Stop it, Tony," not too
convincingly.
     "He does that all the time," said Brit.  "He's one of those weirdos
who likes to look up my skirt to see what color panties I've got on."  I
grinned and threw myself on my back on the floor at her feet so I could see
up her skirt.  Pink, with white trim round the legs.  I'd seen them before.
"See what I mean," she said, but didn't move away.  I lay there, looking at
her underwear for as long as I dared, then got to my feet.
     "What are you wearing?" asked Kitty, "boxers or briefs?"
     "Wouldn't you like to know."
     "Only one way to find out," she said and promptly pulled my shorts all
the way down to my ankles.  I acted as though it was no big deal and
stepped out of them.  "Ahah!" she said.  "White briefs.  Little boys'
underpants.  I thought all you guys wore boxers so you can wear your pants
round your hips and show them off."  I looked down at my Hanes classic
briefs.  I thought they looked much sexier than those fucking baggy plaid
boxers that most kids wear.  I pulled my gray tee shirt all the way down to
my upper thighs to cover my underpants and looked at myself in the mirror.
I think I'm kinda good looking, with my long dark hair falling over my
eyes.  I put my hands on my hips to bunch the tee shirt at the waist and
stood in front of the mirror, swaying my hips from side to side in time
with the music, pretending that the tee shirt was a dress, trying to look
like a sexy girl.
     "Oooh, isn't he cute?" exclaimed Brit.
     "He makes a very pretty girl," said Kitty.
     "He'd look better in a dress," said Brit.
     "No way," I say, but not too emphatically.  A man has to preserve his
dignity.
     "Oh yes!" said Kitty, laughing.  "Tony in a dress!  This I gotta see."
     "I'm not a drag queen," I insist.  Not yet, I'm not.
     "Who's gonna know?" asked Brit.  "We're not gonna tell, are we,
Kitty?"
     "Our lips are sealed."
     "What if I refuse?" I ask.
     "We'll make you.  We'll hold you down and strip your clothes off and
put a dress on you."
     Somehow the idea was kinda exciting, being overpowered by two girls.
In reality, I doubted that they were physically capable of subduing me, but
I could put up a token resistance and go along with it.  There was nothing
else to do that afternoon.  If they were going to rip my clothes off, who
knows what I might do to them?
     "What sort of dress?" I asked.
     "Short," said Kitty.  "You need to show off those long legs of yours."
My legs are completely devoid of hair.
     "Maybe something see-through, so we can see his panties," said Brit,
opening her closet door.
     "I'm not wearing panties for you guys," I said.
     Kitty pushed me back so that I sat on the bed and she leaned down and
murmured in my ear, "Oh yes, you are."
     "Definitely," said Brit.  "You gotta wear panties.  All girls wear
panties."
     To be pefectly honest, I was getting excited by the idea of dressing
up as a girl.  Despite my faked reluctance, the idea of wearing panties was
thrilling.  "Like these?" I asked, lifting Kitty's skirt up again.  This
time she didn't pull away.
     "Exactly," Kitty said, "then we can look up Tony's skirt, can't we,
Brit?"
     "If he'll let us."
     "He has to let us.  He looks up ours."
     "How about his one?" said Brit, pulling a dress of its hanger and
holding it up.  It was a pale blue cotton dress with a flowered pattern, a
scoop neckline and short sleeves.  It looked dangerously short.  She laid
it out on the bed.  "Take your tee shirt off and stand up."  I stood and
peeled the shirt off.  I could see myself in the mirror, my slender
hairless body in my white briefs.  I was starting to get a hard on.  Would
that freak the girls out?  I didn't think so.  I was sure they'd both seen
a stiff dick before.  Brit rummaged through one of her dresser drawers and
pulled out a pair of white nylon full cut panties and held them up.  "These
will be perfect.  They'll stretch enough to fit."
     "Okay then.  Dress me as a girl."
     Kitty knelt down and pulled my briefs down to my ankles.  For a moment
I wanted to cover my cock, now half hard, almost horizontal, but I didn't
want to appear embarrassed, so I just stood there, naked except for my
short white socks.  "Oooh, look at that!" she said, "I think Tony's getting
a stiffy.  He likes being undressed by a girl."  I also like being
undressed by boys, too, but I wasn't about to confess it.  This was the
first time I'd ever been anything other than fully clothed in the presence
of the opposite sex.  They were looking at me admiringly and I felt proud
of my young body.  I put my hands behind my head and thrust my hips
forward.  Kitty took the panties from Brit and held them for me to step
into, then pulled them up my legs and over my hips.  The smooth feel of the
nylon was new to me.  I thought I could get to like it.  I looked at myself
in the mirror and Brit stood behind me, looking over my shoulder.
     "A lot better than baggy boxers, aren't they?" she said.  "Better than
your boy briefs, too.  They suit you, Tony."  She was right.  If the girls
hadn't been there, I'd have put my hand inside the panties and jerked my
cock until they were soaked with cum.  She ran her hands over my butt as
she grinned at me in the mirror.
     "He's got no tits," said Kitty.  "Can you find him a bra?"  Brit
produced a skimpy training bra, just two triangles of white cotton with
appropriate straps.  I held out my arms and she slid it on to me and
fastened it.  Kitty took a couple of tissues from a box on the dresser,
balled them up and stuffed them into my bra.
     "Not too much," said Brit.  "Big tits are gonna look all wrong with
his slender hips.  Okay, that seems about right.  Now let's see how you
look in the dress."  She lifted it over my head and let it fall down,
smoothing it over my hips, pulling the hem where it had caught on the waist
of the panties.  The cotton was sufficiently thin for them to be visible.
The dress flared out from the waist,making it impossible to tell that
underneath the tight nylon panties, my cock was pressed up against my
belly, hard as iron.
     "Holy shit!" said Kitty.  "You're fucking gorgeous."
     "If I were a total lesbian, I'd kiss you," said Brit.
     "You are a lesbian," said Kitty, to my surprise.
     "Not a total one.  I have kissed a boy, you know.  Anyway, listen
who's talking."  Now I began to realize that all that touching and hugging
that they were always doing withy each other was maybe something more than
just friendship.
     "He's a girl!" said Kitty, looking at me, her awe showing in her
voice.  "He's a darling, adorable girl."  I had to agree.  "With your long
hair, Tony, you don't need a wig."
     "And those long lashes don't need any make-up," said Brit.  "We could
trim your bangs a little though."  She went into the bathroom to look for a
pair of scissors.  When she returned, scissors and comb in hand, I sat and
let her comb my hair forward and trim it across just above my eyebrows.  My
ears and neck remained covered.  It was a hairstyle any girl would be proud
of.  I squinted my eyes and looked at myself.  It didn't take any
imagination at all to see me as a girl, with big dark eyes, a tiny turned
up nose and kissable lips.  Kitty was right, I was adorable.  The girls
stood back, admiring their handiwork.
     "Lipstick?" asked Kitty.
     "I think he looks perfect just as he is."
     "We're gonna have to call you Antonia," said Kitty.
     "Just call me Toni with an 'I'" I said.  "You guy's have done a great
job.  No one could tell that I'm really a guy."
     "How does it feel to be a girl?" asked Brit.
     To be honest it was thrilling, far more exciting than I could have
imagined.  I was falling in love with myself.
     "I like it," I replied, smiling at her.  "I feel pretty."
     "He's gonna burst into song any minute," said Kitty.
     "Let's go out and show him off," said Brit.  "Show off our new
girlfriend, Toni."
     "Brilliant!  We can go to the Mall."
     "But his panties are a bit too visible.  Let me find a slip for him to
wear."  She produced a white nylon half slip and I lifted my skirt, pulled
it on and smoothed my dress down again.
     "That's better," said.  "Now you're ready to meet the world.  I'll
call Sam and he can meet us."
     "Sam?" I asked.
     "He's a guy from school, about your age.  He's always commenting on
how the girls dress.  The rumor is he's gay and if anyone can spot any
flaws in your new identity, he will.  He's the ultimate test."
     "What if he 'outs' me?"
     "He'll keep his mouth shut.  He's been bullied so often for appearing
gay that he knows how to be discrete.  Come on, I can't wait to show you to
the world."

____________________________________________________________________________________


     When Sam came into the food court at the mall, we were already seated,
equipped with pizzas and coke.  All around us people were coming and going,
totally unaware that there was a transvestite in their midst.  Some of them
looked at me, mostly men, but nobody stared or reacted in any unusual way.
I sat demurely, my knees together, trying to look feminine, without camping
it up.  I'm a girl, I kept thinking; look at me, I'm a pretty girl.
     I liked the look of Sam instantly.  He was dressed appropriately for a
hot afternoon in a white tank and a pair of short sport shorts, white ankle
socks and sneakers.  Like me, he had long hair, but his was blonde and his
eyes were a startling blue.  I figured him to be about a year older than I
was.  From the minute I saw him, I wanted to get to know him better,
whether I was a girl or a boy.  From whichever viewpoint, he looked hot to
me.  Brit introduced us.  "This is my friend Toni," she said.
     "Hi, Toni.  Pleased to meet you."  He had a dazzling smile.
     "Likewise," I said, shifting my chair sideways to give him room to sit
down.  "Are you hungry?  You can have a slice of my pizza if you like."
     "No thanks, I'll just have a sip of your drink if you don't mind."
The two girls were staring at him, looking for any sign that he might see
through my 'disguise'.  Clearly, he was completely fooled.  We sat and
chatted about inconsequential stuff until Sam said that he needed to pee
and went off to the bathroom.
     As soon as he left, Kitty said, "He's bought it, bought the whole
thing.  You've passed the test, Tony.  Why don't we take him home, and then
you can spring your surprise on him."
     "Yeah, let's do it," said Brit.  "Are you cool with that, Tony."
     "I guess so.  Is he gonna freak when he discovers that I'm a chick
with a dick?"
     "I doubt it.  I'm told he likes dicks."  The idea was quite exciting
but I was enjoying being a girl so much that I wanted it to last for a
little longer.
     "Okay, let's go back to your place, but I wanna keep up the game for
as long as possible."  Sam came back and we left, walking back through the
mall, three girls and a guy, nothing unusual, folks.

_____________________________________________________________________________________


     Back at Brit's house, we went into her bedroom.  She got right to the
point and asked Sam if he thought I was pretty.  He looked at me.  "I think
you're gorgeous," he said.  I blushed.
     "Why don't you kiss her?" asked Kitty.  Sam hesitated.  "Is it because
you've never kissed a girl before?"  Now it was his turn to blush.
    This was getting interesting.  "You don't have to answer that," I said
to him, as kindly as possible.  "You don't have to kiss me if you don't
want to."  We were sitting side by side on the bed and I turned to face
him.  He was in an impossible position.  It would have been grossly
impolite for him not to take up Kitty's challenge, but if he was gay, he'd
have to fake it.  The girls looked on, waiting, each with an arm round the
other.  "On the other hand," I said, "if you want to kiss me, I'd be
thrilled."  I was hoping that the girls thought I was just playing the game
when in fact, I really did want him to kiss me.  I'd kissed a girl to two,
but never a boy and I wanted to know what it would feel like.  Inside my
tight panties, my cock was hard again.  Sam put one arm round my waist,
leaned in and touched his lips to mine.  This was not one of those tongue
battling French kisses, but just a gently caress, his slightly open mouth
brushing mine.  I closed my eyes, responding in like fashion.  Then,
getting more bold, I put my arms around him and the tip of my tongue
between his lips, and we fell back on to the bed.  He rolled so that he was
partly on top of me and his thigh went between my legs, pressing against my
cock.  His body suddenly went rigid.  He broke the kiss and propped himself
up on one elbow.
     "What the . . .?"  He reached down and pulled the hem of my dress up,
revealing my stiff dick inside the nylon panties.  His jaw dropped.
"You're a guy!" he gasped.
     "Sorry.  I hope you're not disappointed."
     "Somehow, I don't think so," commented Brit, a smirk on her face,
giving Kitty a squeeze.
     "I don't know what to say," said Sam.
     "Tell him he's gorgeous again," said Kitty.  "He can't be less
attractive just because you've found out he has a dick.  Whatever you say,
it's cool with us.  We won't tell anyone."
     I lay there on my back, my dress up round my waist, my cock still
obviously hard.  "Am I still gorgeous, Sam?  I think you're pretty hot.
You sure know how to kiss."
     "Kiss him again," said Brit.  "I like to see guys kissing each other."
How many kissing guys had she seen?  "We girls like to kiss, too."  I
looked on amazed as she put her other arm round Kitty and gave her a
lingering kiss on the lips.  Kitty had her hands on Brit's butt.  I took
hold of Sam's hand and placed it on my dick.  He gave it a squeeze.  I
could hardly believe what I did next, as the girls, their kiss now
finished, look on.  I reached out and fondled Sam's cock, just as hard as
my own.  There I was, with one arm round Sam's neck, feeling his cock, in
full view of two girls.  I was intensely aroused by their presence, but I
wanted to take it much further with Sam.
     "Girls," I said, "why don't you leave us and we'll sort this out."
     "Just when the fun's starting," said Kitty.  Both girls left the room,
reluctantly.
     "I think they're into each other," I said.
     "Couldn't you tell.  I've known ever since I met Brit that she was
into girls."  He smiled at me.
     "They dressed me up as a girl, to see if I could get away with it," I
said.
     "Well, you succeeded.  I'd never have guessed in a million years that
you were a boy.  You're gorgeous.  How do you like being a girl?"
     "It's thrilling," I said.  "I never realized how much I would enjoy
it.  I hope you're not too pissed off."
     "It's pretty funny, actually.  You had me fooled."
     "You're the first boy I ever kissed," I said.
     "You're not my first.  How did you enjoy it?"
     "You can kiss me again if you like."
     He leaned over my as I lay there, lewdly showing off my panties with
their hard bulge, and he pressed his lips to mine, this time a lot more
eagerly, his tongue going into my mouth and his hand caressing the front of
my panties, breathing hard through his nose.  After half a minute or so, we
came up for air and I lay there on my back, letting him stroke my cock
through the nylon.  "The reason I was hesitant to kiss you at first was
because the rumors about me are true.  I'm gay."
     "That's cool," I said.  "Dressed like this, I'm feeling pretty gay
myself."
     "You look stunning.  I love your dress and these sexy panties.  Do you
think the girls would dress me up as a girl, too?"
     "I'm sure they'd love to.  Let's get these shorts off you.  I wanna
see what you've got on underneath."  He sat up, lifted his hips and slid
his shorts down and took them off.  In his white briefs and tank, he looked
delicious.  I can't resist guys in their underwear, I just have to stare.
His cock was tenting his briefs and I just had to push my hand down inside
the waistband and grip his cock.  It was absolutely rigid.  He shivered
with delight.
     "What's it like, sucking a cock?" I asked him.  "I have a sudden urge
to suck yours."
     "If you do, I'll cum in a flash, then I won't want to dress up as a
girl.  Can you wait?  We can suck each other, later."  Although
disappointed, I also wanted the thrill of anticipation to last, so I pulled
my hand from his cock and said, "Let's go and find the girls."  They were
in the guest bedroom, where I slept.  They'd raided my dresser because
they'd both removed their dresses and undies and were wearing my white
briefs with their hair hidden by baseball caps.  I looked at their tiny
tits, hardly developed at all as they stood with their arms round each
other, lost in a deep kiss.  They heard us come in and broke apart.
     "We're pretending to be boys," said Kitty.
     "Gay boys, like you two," said Brit.  "Boys who like to touch each
other and kiss."  She pressed her lips to Kitty's again and ran her hand
down between her legs.
     "We need your help.  Sam wants to dress up as a girl," I announced.
     There was a pause while we waited for their kiss to end and then Brit
said, "Sure, let's do it.  Come on back into my room."
     In no time at all, Sam's transformation was complete.  I watched,
enthralled as the girls took his tank off, then slid his briefs down his
legs, letting his hard cock spring out.  For a minute I thought Kitty was
going to suck it, which would have made me jealous, but she passed and
pulled a pair of pink cotton panties up his legs.  A white cami top and a
sun dress completed the outfit, but unlike me, he needed a touch of eye
liner and eyebrow pencil.  Even with a flat chest, he looked stunning.  I
stood beside him in front of the mirror, my arm round his waist.  "I think
I'm falling in love," I said and was rewarded with a huge smile.  "Aren't
we delicious, two sexy girls?"  Brit and Kitty looked on, impressed, as Sam
and I turned to embrace each other, our lips meeting in a hard, grinding
kiss, tongues in each other's mouth, our hard cocks rubbing.  After half a
minute or so, we broke apart to see that the girls had fallen on the bed in
each other's arms, Kitty hand going down inside Brit's briefs.  Although I
was thrilled to see the two girls in action, I was disappointed that they
had stopped watching me kiss Sam.  Being watched as almost as thrilling as
the kiss itself.  I wanted to get their attention again, so I dropped to my
knees, lifted Sam's dress, and pulled his dick out of the leg of his
panties.  The aroma of hot dick made my head spin.  I could hardly believe
that I was about to suck the cock of a boy.  So, I guessed, I was gay.  So
what?  I didn't care, I wanted to be gay and I didn't care who knew it or
who watched.  I took his dick in my mouth and found it was more thrilling
than I had imagined.  Sam trembled with pleasure, which sent an electric
charge through me.  From the corner of my eye, I could see that the girls
had sat up and were looking at us.  I bobbed my head up and down furiously,
masturbating Sam with my lips, putting on a show for the girls.  For half a
minute or so, I continued to suck him as he ran his hands through my hair,
then he took my by the ears and pulled my head away.
     "My turn," he said, lifting me to my feet and dropping to his knees.
I lifted my dress and let him pull my panties down to mid thigh and take my
cock in his mouth.
     "Look at that!" said Brit.  "Couple of fucking cock suckers."
     "But it looks tasty," said Kitty.  "Almost as good as eating pussy.
Let me get these briefs off you."  In a flash, the girls had taken each
other's briefs off and were lying back down on the bed again, head to tail,
their faces buried between the other's thighs, licking furiously.
     "Wow!" I said.  "You girls are just as gay as we are.  What a
beautiful sight.  Go for it, girls, make each other cum."  The sight of
Brit and Kitty licking each other was just too much for me and I felt my
orgasm building.  "I'm gonna cum any second!" I called, thinking that Sam
would pull away, but he put his hands on my butt and pulled me deep into
his mouth.  The girls broke apart and looked at us. I felt my cock pulse
and my cum rush down its length and out of the end into his mouth.  His
lips milked me until I was spent and I pulled my cock from his mouth and
pulled my panties up.  Sam smiled up at me, his mouth open, cum dripping
from his lower lip.
     "Holy shit!" said Brit.  "You came in his mouth.  How does it taste,
Sam?"
     "Probably the same as pussy," he said, "though I can't speak from
experience.  I think you'd like it."
     Kitty lay on her back, a contented smile on her face.  "I wish I was a
boy," she said to Brit.  "Then I could fuck your brains out."
     "We'll just have to pretend, like Tony and Sam are pretending to be
girls.  Lick my cunt again, sweetheart."
     "Sam, I think you just turned me gay," I said, with a smile.  "Give me
a few minutes to recover and I'll let you cum in my mouth."
     "And then I'll let you fuck me up the ass," he said.  "You've no idea
how good that's gonna feel."
     "Can we watch?" asked Brit as she prepared to go down on her friend.
     "Absolutely," said Sam.  I wondered how, as I fucked him, would I
think of him?  Would he be a boy or a girl?  Either way, he was heavenly.
     "Sure, you can watch," I said.  "You can even watch when he fucks me.
If I'm gonna dress like a girl, I might as well act like one.  You can take
my virgininty, Sam.  I'll be proud."
     "You know," said Kitty, laying back with Brits face between her
thighs, "wouldn't they look good in stockings and garter belts?"
     "Or in baby-doll nighties?"  Brits voice was muffled.
     "Or crotchless panties?"
     "Peek-a-boo bras!"
     "See-through teddies."
     "Sheer, lacy chemises."
     I was starting to get hard again.  I reached for Sam's cock, still
rigid and dripping with precum.
     You can dress me as a girl anytime youl like.

The end.

To find the rest of my stories, email me at tonywill9999@yahoo.com.  All
emails will be answered.