Date: Sun, 16 Oct 2011 04:25:43 -0700 (PDT)
From: Jack Herold <jackherold73@yahoo.com>
Subject: Girlboy Diary Day 2

			    Girlboy Diary Day 2

				by Hartford

When I went to bed that night I wondered how I would feel in the morning
when I woke up for the first time to my new world.

It felt great. I felt amazing. And after a couple of minutes it scared me
right back into bed.  Was I nuts? How could I go on pretending to be a
girl? My screwball parents weren't the only people in my life. What was I
going to be after college, an airline stewardess? Perhaps at fifty I could
become a nun.  After a few minutes I calmed down and forced myself to put
on the clothes Mother had laid out for me, which included panties and a
skirt. Thank you for the wig, Mom. And for not forgetting the lipstick. But
when I was dressed and made up and considered myself in the mirror, the
excitement kicked in again. I looked like a piece of ass if I did say so.
The falsies had been there with the rest of my outfit but I left them. I
was conceited enough to think I could pass the sexpot test without them,
and in my unhumble opinion I did.

I sashayed into the kitchen, having heard Father's voice, but it wasn't
mother he was talking to.  It was Mr. Davis and Junior who lived across the
street. Junior was my age. We had been pals on and off since
kindergarten. The friendship faded in high school when Junior gravitated to
sports and girls while I got into drama and poetry and being a loner, also
a loser in Junior's opinion, or so I interpreted it, but in my own opinion
as well. Junior took after his Dad in the muscle department. Both were
strong looking guys. They looked at me like I had just arrived from Mars.
Better make that Venus, I thought, after more fully registering Mr. Davis's
expression.

"Jesus!," he said.

"Hey, Jerry. Not bad," Junior said in a relaxed way that didn't exactly go
with his gaze.

"Mmmm, nice to see you," I said. I tried using my girl's voice but it
flopped. I tried again and this time it was better. "Are you joining us for
breakfast?"  If I was going to be a boygirl the neighbors might as well
know it.

The amazed faces were helping me find my own bearings. Had they been more
self assured, I probably wouldn't have done as well. I actually began to
feel amused.

"So, you're a fag, huh?" Junior said matter of factly.

"No, Junior, not a fag. Are you a fag?"

He reddened.  I saw the muscles tighten in his neck. Mother got up from the
table and put a hand on his shoulder.

"What Jerry means is that he's a girl now. His new name is Tiffany,
remember?"

"He ain't a girl. I admit he almost looks like one but....he's not? This is
a stupid idea. Don't call me a fag again, Jerry. Okay?"

"Okay, Junior. And please don't call me one. What's a stupid idea?"

Mother took Junior by the arm and sat him down, facing away from the
table. Mr. Davis seemed to take this as a cue and he sat, too. Father was
already at the table with his coffee and newspaper paying no attention to
either. I stood and waited, wondering what was going on. Mother began to
tell me.

"Mr. Davis and I have been conferring, Tiffany. I told him a couple of
weeks ago about your upcoming transformation, seeing as how the Davis's are
friends and neighbors and all. I felt they should be forewarned, that is,
advised. Ahem. Anyway, after I told them they confided in me that Junior
has an issue regarding girls."

"An issue?"

"Yes, an issue. Junior, would you tell Tiffany why you're here."

Junior's eyes were lasers. "I'm a virgin, Jerry. That's the fucking issue."

Mother sighed and shrugged her shoulders. "This is Tiffany, Junior. You
must think of him as Tiffany...of her as Tiffany. It will make things much
easier. And look how pretty Tiffany is."

"Yeah, he is pretty, gotta say it....Tiffany."

"Thank you, Junior. I'm sorry you're still a virgin. I always thought you
were getting girls left and right."

"Never happened, Jerry."

"Mmm hmm. So if I get this completely unbelievable situation I'm finding
myself in you and your father have come over so you can have sex with me
and lose your virginity. Is that it? Are you people out of your minds!?"

Mr. Davis cleared his throat and smiled.  "You're one heck of a treat to
the eyes, Tiffany. Can you blame us if you're as desirable as you are."

He was putting on the charm, which I appreciated, but... "I'm sorry, 'us'?"

"That's right, honey. First Junior, then me."

Mother cut in at this point to explain that Junior had been talked into
fucking me provided that his father fucked me, too. Under no condition
would Junior risk becoming the only fag target in the family.  "It's so
sweet when you think about it dear, because you're a virgin, too, that is
Tiffany is, so you and Junior will lose it together. And then you should be
broken in at least a little which will make you better able to take
Mr. Davis's cock. He has a biggy."

"Does he really? Of course, Mother, you would be fully informed on the
subject."

"Don't get smart ass with me, Jerry, Tiffany, both of you, or I'll add your
father to the list and when the rubbish men come by, it's Saturday, we'll
invite them in for turns."

Mother was blazing, which is the way she gets angry. She's never slightly
or moderately angry.  The blazing kind is the only kind she knows. I didn't
care. I was pretty upset myself, but then I saw it. Mr. Davis had opened
his fly and liberated his biggy. It wasn't quite the biggy that Father's is
but it was plenty big and more impressive than its size was its form. It
was an Adonis cock, positively mouth watering.

"Oh," I said.

Mr. Davis watched me gape. "Guess what it made this way, sweetheart."

"Me?"

"Yes indeedy. Always had a weakness for pretty boy cunts, pardon my
French. Don't think I ever saw one better than you, cutie, even in a
picture."

"Well...," I blushed. I couldn't wrest my eyes from the missile poised for
take off in the man's open fly.  If that wasn't enough to prove to me the
starch was gone from my resistance, I felt my knees asking permission to
find the floor. It's amazing how quick a handsome and ready cock can turn
things around for a reluctant girlboy. Mr. Davis read my wicked mind.

"You can have this after you make Junior happy."

I giggled sort of and smiled at Junior, taking note of his lap. He was
wearing loose fitting jeans with nothing disturbing the folds.  I
remembered for some reason when I was ten or eleven playing basketball with
Father against Junior and Mr. Davis in the Davis's driveway, if you could
call what we did playing basketball. "So you and you Dad are still a team,
huh Junior," I said, trying out a grin on him.

"Yeah, a fuck you team, Jerry," he muttered.

"Junior, that attitude isn't going to get you anywhere. I hope this isn't
how you are when you try to make a girl." I used my girl's voice on him and
I stood in front of him like a girl stands when she is teasing, and it had
an effect.  Junior looked at me. He blushed.

"I thought you had fake tits that you used," he said, softly.

"I do wear them sometimes. I could put them on for you, Junior. Would you
like that?"

Junior swallowed.  "I don't know."

"I don't think fake things are what we want right now, Junior. I think we
want real things. I have some real things you might like, two actually. And
you have one real thing, one pretty great real thing if you'll give him a
chance, if you'll let me help you give him a chance. I bet after all this
time he would like a chance."

Junior twisted his mouth.  He was listening, so I said, "Even if I'm not
completely a girl, I'm enough like one that we can pretend. I bet we can
pretend with no problem, Junior. I bet we can pretend like anything."

Junior blanched and then he blushed and then he blanched again. He looked
around and for a second I thought he was embarrassed at being watched by
his Dad and my parents but then I sensed that he wanted them there for
support, crazy as that sounds.

He cleared his throat and tried to smile. "Yeh, heh heh, don't expect me to
kiss you, Jerry."

"You mean, Tiffany, Junior."

"Yeah, yeah."

"I don't expect it. It might hurt my feelings but I won't expect it if you
don't want me to, Junior." I had the voice going to perfection.

"Jesus, I don't want to hurt your feelings, but, I mean..."

I gave him a pout but it ended with a smile. "It's okay, Junior. Maybe I
should show you how I look without my skirt on."

I shot a glance at Mr. Davis. Don't think I'd forgotten what he said about
me being a cute boy thing, or that I wasn't interested in confirming for
him his good judgment. Of course, I had been acutely aware of my
audience. They had reminded of when I was in high school and Mr.  and
Mrs. Davis came over to listen with my parents to me rehearse my
declamation of The Gettysburg Address, right here in the kitchen on a
Saturday morning just like now, except this was a rather different sort of
presentation.

Anyway, Junior nodded his permission for me to ditch the skirt so I
unhooked it and let it fall down my legs. I stepped out of my sandals and
the skirt and posed in my panties for the two gentlemen who had dropped in
to fuck me, and Father if he cared to watch, which he did. Mother watched,
too, but I wasn't doing it for her.

Junior approved. I could tell by the way he swallowed and by his ears
turning red. He and Mr.  Davis spoke to each other about my legs and my
thighs and my bottom in the silk panties and about my smooth skin and about
the fact, as they saw it, that if it weren't for the lump at the front of
my panties I could pass as a model in a Victoria Secret catalogue. It
seemed an opportune moment for my panties to join their friends.  I sighed
so Junior and Mr. Davis would hear it and then, while they watched, I
worked the panties down my girlish legs and away they went. My dick was
half hard, and there it was. I watched Junior and Mr. Davis consider it.

"Dick girls are a joy to behold, Junior, when they're like her," Mr. Davis
said, winning whatever parts of my heart remained for him to win.

Junior only nodded, but his pants were doing more. They were steadily
tenting. Oh, my.

I figured I should strike while the iron was hot, as they say. I wasn't
sure what Junior's problem was with girls but I had a suspicion. If his
approach was like his approach to most things, he would have been the
proverbial bull in a china shop. And gotten nowhere probably, maybe not
even with himself. I wondered if he had ever taken the time to get himself
worked up like he was worked up at then. He had been reticent with me only
because he didn't want to be here, but now he did want to be here. Was I
piece of ass or what!?  That's not to say Junior was completely won
over. He stared at me like he was trying to put it together. How could I be
this way and have a cock sticking out in the middle of the picture, like a
mustache on Nicole Kidman. But he seemed to making progress. Before we were
done I wanted him to have his father's perspective: that Tiffany was a joy
to behold.

I posed some more, a few seconds worth, putting my hands on my hips as I
swiveled my ass and smiled, one last little show for Junior. Then I softly
suggested his cock might have a better time if it left the confines of the
jeans. Junior bit his lip, looked around, took a deep breath, and undid his
pants. When they were around his ankles, I bent down and removed
them. Mother reached across the table and tapped Junior on the
shoulder. She passed him a tube and Junior coated his cock, and there it
was, poised in his lap, glistening its invitation. I took my own deep
breath, braced my hands on Junior's shoulders, and lowered myself. Junior
held his cock for me, directing it, and in it came, nice and smooth, not
far but far enough for me to see stars with my eyes closed. I kept myself
where I was, getting up my nerve, feeling the cock inside me, oh man!, but
Junior wasn't waiting. He gripped me at the waist and pulled down at the
same time that he pushed up. Uh huh, that's what Junior did. I heard myself
gasp. It didn't feel so good, it felt like something you might read about
in the history of the Spanish Inquisition. Then it felt better, then it
felt a lot better, then a lot, lot better. I have no idea of the time. I
was in a different zone. When I opened my eyes and saw the kitchen and the
people in it going up and down, whoops that was up and down me not them, I
was seriously in my element. Mother had a video camera going. I chose not
to look at my deflowerer or at my stiffy jouncing in front of him. I kept
my head turned. But I couldn't help hearing Junior's impassioned sounds and
it was wonderful knowing I was the cause of them.

"Look at his eyes, look at the way he's panting!," or something like that,
I heard Mr. Davis say. I didn't know if he meant Junior or me.

I thought I was going to have an orgasm but before that event could get its
act together Junior had his, a major eruption no less. The geyser might
have jettisoned me all by itself if Junior hadn't assisted. Either he
forgot someone else was involved in the enterprise or he didn't care
because he thrashed about with arms and legs and dispatched me. My abused
but humming backside hit the tile floor just before Junior's last gushes
rained down. Mother hurried over with the camera.

Well, that's about it. Mr. Davis decided to reserve his turn for another
day. His son's accomplishment and the show we had put on were enough for
him for one morning, he said.  Mother thought it a wise decision all
things, including tender me, considered. Junior was proud of himself. I
half expected him to have mixed feelings at best toward me as he got
himself wiped off and dressed. But he was sweet. And as he went out the
screen door following his Dad he looked back at me and grinned the kind of
grin that said let's do that again. My return look was non-committal. I had
come on to him as hot to trot after warming up to the situation, and hot to
trot I had been, but now he was not to presume I was just an easy romp in
the hay. Girlboys can be so flighty.

See you next time.