Date: Sun, 17 Apr 2011 13:04:17 +0100
From: Just Peekin <justpeekin@hotmail.com>
Subject: Andy to Amy - Part 2

This is a story of a boy called Andy and his first steps into the world of
cross dressing with the assistance of his neighbour/best friend/girl friend
Nikki.  Quite a lot of it is autobiographical, but not quite as much as I
would like!  I hope you enjoy it.  This first episode is a scene setter and
has no sex in it.  Well, not much.

If reading this sort of stuff grosses you out, don't read it.  If this sort of
stuff is illegal where you live, don't read it.  If you want to post it
somewhere else then fine, but it is my copyright and please be kind enough to
credit me for my work.  Feel free to drop me a line at justpeekin@ymail.com if
you have any comments or suggestions.

Story codes:  CD TV bg voy b-solo

Andy to Amy, part 2

So there I was. Twelve years old and standing stark naked in my 11 year old
neighbour/best friend's/girlfriend's bedroom sporting a rock hard stiffy
while she knelt there in front of me with her eyes glued to it.

Now I know what you lot are expecting. You are assuming that I am about to
say that Nikki immediately leapt forward and started to suck my dick and
then we went at it all afternoon like a pair of crazed polecats, but you
would be wrong and you have probably spent too much time reading stories on
this site. Like I said, both of us were very naive at the time and I don't
think that either one of us had ever heard of oral sex, much less given
it. In fact, I'm pretty convinced that had someone walked into the room at
that moment and explained oral sex to us we would have been completely
grossed out - I mean putting someone's dick in your mouth?? But that's
where people pee from - gross! And as for licking a girl between the legs -
ew!  Having said that, of course I was so horny that I thought I was going
to explode and my little dick was so hard it was painful. But there were no
blow jobs. What happened was that she spoke. She said "Cool."

I said nothing. To be honest I couldn't think of a thing to say and all I
wanted to do was play with my little cock to get some relief from the
overwhelming desire that I was feeling. I guess I had some vague notion
that Nikki might help or do something or even do it for me, but that wasn't
going to happen!

"It's bigger than I remember," she said. I was at a bit of a loss until I
twigged that she was talking about the playing doctor games and 'you show
me yours' some years before.

"Err, yeah. I guess." Eloquent, wasn't I?

"Is it always hard like that," she asked?

"No, only sometimes."

"Oh yeah, I remember from biology class. So what makes it hard?" she asked.

"Err, sometimes when I get excited it just goes like that." Well, it was an
explanation of a sort and she seemed satisfied.

"Where are your balls," she giggled at the 'naughty' word which she had
presumably picked up in the girls' loos or something. My embarrassment
increased as I pointed to my scrotum, dangling loose beneath my hard
penis. "In there," I said.

"Oh, right." She knelt on the floor for what seemed like about 10 years,
but was probably closer to about 20 or 30 seconds staring at my little bald
package and inclining her head this way and that to get a better
view. Finally she seemed satisfied.

She stood up and turned towards her wardrobe and opened its door. "OK. So
lets see what there is that is nice and soft so you can compare."

She ran her hand along the gorgeous row of flowing dresses and skirts, soft
blouses and trousers that filled the wardrobe until she alighted on a red
and white gingham print dress which was actually the summer school uniform
for girls at our school. The boys had to wear the same uniform as they wore
in the winter but the girls had a choice of either short sleeved blouses
with the usual skirt, or of this delightful (or so I thought) light,
flowing soft dress that came to just above the knee. We had to wear
blazers, long sleeved shirts and ties al year. How was that fair? She
pulled the dress and its hanger from the rail and turned towards me
again. "I think we're about the same size so I guess that my stuff will fit
you, won't it." It was a statement rather than a question. I eyed her up
and down, and glanced down at my own naked body and was pretty sure that it
would. With me a skinny 12 year old with no sign yet of puberty and she a
girl who had started to grow a bit sooner we were actually almost exactly
the same size.

"Try this," she said.

I swallowed. It was a strange moment - a dream about to come true. I could
feel my heart thumping within my chest and my mouth had gone dry. As long
as I could remember I had been fascinated with girls' clothes - with the
way they felt, with the material that they were made of and with the
softness and prettiness that they had. I had wanted so much to try them on
and to experience the sensation of wearing such lovely creations for myself
and now here I was with a real live girl offering to help me realise the
dream of becoming part of those lovely soft clothes. And she was my best
friend.

I reach out a trembling hand towards the dress, but Nikki stopped me.

"No," she said as she removed the dress from its hanger. "I'll do it. Raise
your arms for me." I did as I was told, standing there with my arms raised
above my head, which of course made my rock hard little cock stick out even
more from my hard flat stomach.

She bunched the dress a little from the bottom and then reached up and
slipped it over my hands, feeding my hands through the arm holes. I felt
the soft cotton slide down my arms and then was nearly overcome as my face
was suddenly buried in the red and white gingham of the dress. I felt her
hands brush my sides as she grasped the hem of the dress beneath my arms
and gently pulled it down over my thin body. It fell into place, brushing
softly at my chest, my stomach, my thighs and my hard little penis.

The sensation was incredible. My body was screaming with the tactile
stimulation of the soft, thin cotton touching every part of my body. She
reached up and grasped me gently by the shoulders and started to turn me
around. I was experiencing some form of sensory overload and offered no
resistance to the pressure of her hands. As I faced away from her I felt
her hands at the base of my spine and then both felt and heard the zip
being pulled up. As the zip was pulled slowly upwards I felt the dress
become a little tighter around me, adding to the intensity of the
sensation.

"OK," she said. "You're done." I felt her hand on my arm just below the end
of the short sleeve of the dress as she turned me around to face her again
and I saw myself in the mirror on the inside of the wardrobe door. I was
wearing a dress. It was me in the reflection and I was wearing a dress. I
was absolutely mesmerised by the site. "Your hair won't do," I heard my
playmate say. Now you must remember that this was the 1970s. The era of the
mullet and some of the dodgiest hairdos ever seen on men. Even worse than
the ones that women had in the 1980s. Just think Kevin Keegan without the
perm and you're not far from the truth, but it was what passed at that time
for a boy's haircut and she was right, it didn't quite go with the rest of
the look.

Nikki turned away again, leaving me staring at my reflection in the full
length mirror. When she turned back she had in her hands an Alice band that
matched the gingham print of the dress and a hairbrush. With a determined
look on her face she set about arranging the mop of hair that sat atop my
head, turning me this way and that as she sought to bring order to the
chaos that was my head. Finally satisfied with her efforts, she pulled the
hair back from my ears and fitted the Alice band, making sure that it was
firmly in place behind my ears. She turned me back to the mirror, standing
back to admire her handiwork, and once again I was mesmerised. Now, instead
of seeing me there wearing a dress it felt as though I was now looking at
myself as a girl. Not a boy in a dress but rather me as a girl. The boy
seemed to have gone. Almost.

Nikki giggled. I looked at her and saw that her eyes were fixed on my lower
abdomen. I followed her gaze and saw a gorgeous flat expanse of gingham
print spoiled by a protrusion from my crotch. None of the dressing or hair
arranging had done anything to decrease my arousal, and the shape of my
rock hard little erection was quite obvious, upsetting the line of the
dress and, to be honest, the overall look.

"Oh dear," she said. "That doesn't look quite right!" She had a point. "Can
you make it stop or go away or something?"

I swallowed. "Err...no, not really. It like just comes and goes."

"Wow that must be pretty inconvenient!" We all know she was right, don't we
guys?

"Isn't there anything you can do to make it go quicker?"

"Err, well, sometimes if you like stoke it and stuff you can make it go."
Well, it was worth a change and to hbe honest I would have sold my soul at
that point for her to touch it just once.

"How do you mean?"

"Well, you know like they talk about masturbation in the biology books,
yeah?"

"Yeah," she said, although I don't think she really understood at all.

"Well if you do that to it it goes away."

"Go on then," she said, still looking a the lump in my dress.

I swallowed again, my heart pretty much in my mouth. Slowly my fingers
grasped the front of the dress somewhere around mid thigh. I started to
gently lift the hem, savouring the sensation that dragging the edge of the
soft material across my naked thighs brought. As I drew it higher I felt
the hem rub against my tight hairless scrotum and then the base of my
cock. Nikki's eyes were glued to the front of the dress. Finally I drew the
dress along the (admittedly short) length of my now madly pulsating cock,
revealing it once again in all its glory. I turned back to the mirror and
the image that I saw there was burned into my memory for all time. There
was a girl with tidy hair and a lovely Alice band standing in a red gingham
print dress but she has pulled the dress up to her waist and rather than
reveal a pair of white knickers, she has revealed a three inch or so rock
hard penis and a firm hairless scrotum beneath.

"You could do it if you want," I said. my voice wavering as I spoke. Well,
if you don't ask...

"What? No way, I'm not touching that!" Oh well. I tried. "If you want to
sort it out you can do it yourself!" There was an ironic element to her
protestations. I mean, there I was stark naked under her dress with a
raging hard on, but she couldn't bring herself to touch it!

I began to turn away, but again she stopped me. "No, don't turn around. I
want to watch."

"OK," I said and slowly my right hand moved to my erection and took its
familiar firm grip around the shaft, with my thumb on my foreskin. My left
hand held the hem of the dress above my waist. I stared at the image in the
mirror and a girl with a cock stared back at me. Slowly I began to work my
hand in its well practiced strokes up and down my little cock, savouring
the sensation that I could already feel rising from the base of my
spine. Nikki's eyes were glued to my crotch, fascinated by what she was
seeing, while mine stared at the same image in the mirror in front of me. I
could tell that the crisis would not be long delayed.  The girl in the
mirror's hand worked slowly up and down the hot hard shaft and I could see
her legs start to tense at the coming explosion of sensation. I gripped a
little tighter and rubbed my foreskin against the sensitive ridge of the
head of my penis. I felt my stomach and leg muscles tense and my head went
back a little as the familiar wave of ecstasy rose higher and higher from
my cock and from deep within my body until with grunt the feelings swept
through me from top to bottom. I held my breath, my back arched and my hand
tightened against my cock as my scrotum constricted. Throughout all of this
I managed to keep my eyes open and glued to the girl in the mirror as her
own orgasm swept over her.

"Wow. Did that hurt or something?" Nikki asked.

I said nothing for a moment a I recovered from the dry orgasm. "No," I
finally managed. "It feels great! You should try it some time!" She gave a
non-committal "hmm."

"Will it go soft now?" she asked.

"Yeah, in a minute it will," I replied, and as I watched the girl in the
mirror I could see her erection begin to lose some of it firmness and begin
to transcribe the arc back to its normal position and as I watched it I
savoured the sensation of what had to have been one of the most intense
orgasms I had ever experienced as the afterglow washed over me in ever
decreasing waves. If only Nikki knew how good that felt!

As my cock gradually softened I let go of the hem of the dress and allowed
the material to cover my nakedness whilst I watched my reflection in the
mirror.  After a few minutes my little cock had returned to its regular
position, but there remained a lump in the front of the dress where it
brushed up against the material even when soft. Not much of a lump,
perhaps, but it was definitely visible and Nikki had noticed it too.

"It's still there," she said.

"Duh! of course it is!" I replied. What was she expecting?

"It's because you don't have any knickers on. If you did it would be kept
down." She had a point. "Put some on."

Automatically I reached for my underwear, lying discarded on the floor to
my side, but Nikki stopped me. "No," she said. "Use these."

She half turned and reached down to pick up - of all things - the very pair
of knickers that had started all of this in the first place. A tiny pair of
white cotton knickers with pink flowers printed on them, and a pink satin
bow at the front. I simply longed to touch them.

"But they're yours," I said. I was sharp that day!

"I know. Put them on," she said, holding them out for me to step into as
one might help a small child get dressed. I raised my right foot and
stepped into the garment, putting my hand on her shoulder to steady
myself. Then, after I had repeated the manoeuvre with my left foot, Nikki
drew the diaphanous garment slowly up my claves and past my knees. She
paused only briefly to change her grip as her hand disappeared under my
dress and then I felt the soft fabric caress the cheeks of my buttocks and
then cup my genitals. Had I not just masturbated, I would have been
instantly hard. As Nikki snugged the garment home the back of her hand
rubbed across my still sensitive penis making my jump a little. "Sorry,"
she said with a mischievous grin. "Accident!" Yeah. Right. "That seems to
have done the trick."

I looked in the mirror and sure enough the out of place lump was now gone
and all that was there was a perfectly flat fronted dress. The image was
complete.

"You look great, Amy," she said.