Panty Secrets
By Gingerfred Man
Chapter One - Carded
Timmy. My parents named me Timmy. Timmy Garconette. They didn't hate me
or anything. In fact they loved me very much. And they're good parents.
They probably thought Timmy was a nice name. But it just gives you an
idea of the flavor of my life. Timmy is not the name of a guy who scores
the winning touchdown or scores with the winning babe. It's kind of a
wimpy name.
My one-year-older sister Clare got a pretty good name and some pretty
good looks too. She's actually tall, blonde and gorgeous. With big, firm
boobs.
I didn't think my looks were very good, but that turned out to be a
matter for much discussion. I thought of myself as small and scrawny.
And so did the girls at my school.
And it didn't help any that I was hung like a mouse. Probably the
smallest penis in Western Civilization.
By the time I was a senior in high school, I had pretty much abandoned
hope of becoming the next great American ladies' man. As my 18th
birthday closed in, I was wondering if I would be a virgin all my life.
Fate didn't just jab me, it threw combination punches at my jaw. You
would think that someone born on Valentine's Day would be a great lover.
Hah! It was just an irony piled on an irony.
But things took a turn in a brand new direction for me on February 13,
the day before my 18th birthday, when the mail arrived.
The only thing about that day that I was grateful for was that Clare was
at her friend's house when it happened.
I remember it vividly. It was a Saturday afternoon. Mom went to the door
and came in with the mail. Dad was on the couch watching a basketball
game. Since I didn't have anything better to do, I was sitting next to
Dad.
The arrival of the mail meant little to me. I was getting a lot of stuff
from military recruiters, but that didn't interest me. I guess you're
getting the idea that I was just sort of bored and saw little hope for
relief.
Then Mom said. "Timmy, you got a Valentine."
And the whole world began to spin backwards.
I couldn't be getting a Valentine. Who would be sending me a Valentine?
Did I have a secret admirer? I was totally baffled. And extraordinarily
curious.
Until Mom said, "It's from a man!"
What??????
My neck got red and my stomach threatened to reject its contents. What
sort of a malicious creep would play a joke like that on anyone? Who
would insult another person like that - a new low?
My first reaction was to grab for the unopened envelope, then rip it
back into its molecular structure. But curiosity about my tormentor's
identity seized me. I had to know.
I looked at Mom, whose extended arm offered me the instrument of my
humiliation.
Mom didn't seem sympathetic to my pain. Instead, she seemed?hopeful. How
odd.
The question flashed through my head, how did Mom know it was from a
man? And a Valentine?
The envelope told the tale. It was pink, with tiny red hearts all about.
And the return address said: Richard Hardwood.
Mr. Hardwood. My favorite teacher. The guy who was almost a mentor to me
until he mysteriously quit teaching at the end of the previous school
year. Leaving without a reason or a goodbye or a forwarding address.
Creating what became a hole in my heart. I mean, he was the only reason
I enjoyed school. Then he was gone.
And then he was sending a Valentine's card.
Surely Mr. Hardwood didn't mean what Mom was acting like he meant by the
card.
Mom and Dad were looking at me as I stared at the card. "I'm not gay!" I
blurted out. Just for the record. "And I didn't encourage this. It's
probably not at all what you think."
Mom and Dad made little noises of comfort and agreement. They really are
nice people. But it was still pretty humiliating, you know?
Dad pretended to watch TV and Mom pretended to putter as I slinked off
to my room to read the card.
I was trembling as I opened it.
If it was a joke, it was an over-the-top one.
It was a pink monstrosity loaded with hearts and flowers. And there, in
the center, the words, "Be my Valentine. I love you!"
My heart sank. Mr. Hardwood was gay! And he thought I was gay.
I wasn't. I mean, I liked Mr. Hardwood, but not "that way."
Oh no. There was a message.
"Dearest Timmy," it began. "I have great affection for you. So sorry I
left without explaining. Please let me tell you everything at a birthday
dinner at Chez Nancy on Valentine's Day - your 18th birthday. I'll pick
you up at 7. Love, Richard."
I was trembling with rage and embarrassment. So much so that I almost
missed the P.S., which said, "Don't worry. I'm not gay and neither are
you. 'R.' "
Well. That should take some fancy 'splainin.' He's not gay and neither
am I. He has great affection for me. Practically asked to fuck me. Wants
to take me out for Valentine's Day. And we're both men. But neither of
us is gay.
Hmmm.
I should have ripped the card and note, then flushed it. But I didn't. I
just calmed down a bit, slipped it into my underwear drawer, and
returned to my parents to set the record straight.
I boldly entered the family room and announced to my parents, "Mr.
Hardwood is obviously crazy. If he calls me, please tell him I'm
unavailable. And please, don't tell Clare any of this!"
Mom and Dad readily agreed.
I did an about face, then marched back to my room. Turned on a
basketball game. Loudly, so the parents would know that I was involved
in a manly pursuit. Then I extracted the card and read it again. I felt
a vague, unfamiliar stirring in my gut. What did all that mean? Well, I
was nipping it all in the bud and that was that.
Chapter Two - A Panty Proposal
I didn't sleep very well that night. It's difficult to set your mind at
rest when your dull world develops a point and stabs you.
What the heck was Mr. Hardwood up to? Had he lost his mind? And why was
I the object of his craziness? Had I encouraged him in any way? I didn't
think so.
I knew I wasn't gay. I mean, in the shower at the gym, all I ever felt
was humiliation at my teeny weenie. And fear that some of my naked,
moronic classmates would ridicule me.
Mr. Hardwood had been the bright light in a miserable high school
experience. Now even that was ruined.
Wasn't it?
As I tossed and turned, I wavered about what I should do if he showed up
to take me to dinner.
The possibilities ranged from not even being home when he showed up to
dumping a bucket of cold water on him to going to dinner with him to
tell him why I could never do or be what he wanted.
My compassionate side won out.
Mom and Dad took Clare to dinner that night so that she wouldn't be
around when my "date" came for me. Clare thought it was awfully fishy
that the whole family, less the birthday boy, was going out to celebrate
my birthday. But no one enlightened her, thank goodness.
I wore a sweater and khakis - casual - heterosexual. And I made sure my
cell phone was charged in case I needed to call the police.
I was nervous, even though I had rehearsed a very compassionate refusal.
Of course, I wasn't sure what the proposal was, but I was ready to
decline it, nevertheless.
At precisely seven p.m., the doorbell rang,
I took a deep breath and opened the door.
There he was. Mr. Hardwood. Exactly as I remembered him. A nice, steady,
thirtysomething, regular guy. Who obviously needed mental treatment.
Thank goodness he didn't try to kiss me or anything. But he did hug me.
Which I didn't mind all that much.
I searched my mind for my brushoff speech, just in case I needed it
sooner than I thought. I mean, if he tried any funny business. But he
didn't.
He just said, "Happy Birthday, Timmy. I've been looking forward to your
18th birthday and I'm sure you have been too. It's going to be an
incredible turning point in your life?and mine. You'll see."
Didn't know what he meant by that. As far as I knew, my life was going
to be more of the same. Unless it got worse. Which Mr. Hardwood's
actions so far suggested that it would.
He released the hug, then held me at arm's length to look at me.
"Wow," he said. "You've gotten even more beautiful in the past eight
months. I've missed you so much!"
I don't know why, but I blushed at that. And sort of felt good.
He had been a good mentor and friend. Before his mental illness.
Still in charge of the agenda, Mr. Hardwood said, "Let's get going.
Don't want to miss our reservation. Not easy to get on Valentine's Day."
That made me balk a bit. It suddenly occurred to me that I would be
sitting in a restaurant with a man on Valentine's Day. What would people
think?
Then I thought, what do I care what people think? The world hadn't been
very good to me. Why should I worry about the world?
So I got into the car with him and listened to him prattle on about how
all that time he had been living in the bigger city 30 miles away,
working on his "business plan."
"What business?" I asked.
"I'll tell you at the restaurant, Sweetheart," he said.
I wished he wouldn't call me that. Then I thought, was he going to be
giving me a sales pitch to sell Amway products or something? Well, at
least it wouldn't be gay.
We didn't raise any eyebrows at the restaurant, even when he took my
coat and held the chair for me. I guess everyone was too lovey-dovey
with their dates. I had a crazy man as my escort.
After we ordered, Mr. Hardwood opened the folder he had brought in with
him. "Timmy, I want you to look at this picture. I took it of you back
in June and you've developed since then, but tell me what you think."
I remembered when he took the pictures - about a week before he left
town unexpectedly. He handed me an 8 by 10. I looked at it.
Huh?
It wasn't me. It was some gorgeous, glamorous, dick-stiffening babe in
perfect make-up, with fantastic blonde curls.
Wait a minute. It was me. With a lot of computer enhancements.
What kind of sick trick was this?
Still, I had no idea that my face, with some changes, could be anything
but ordinary. That babe was beyond extraordinary. And she was me!
I looked at Mr. Hardwood. He was smiling broadly and expectantly. But I
didn't say anything. I was sort of angry, but curious too. So he went
on.
"You have the greatest feminine potential of any boy in the history of
the world. I've tried lots of boys' pictures in that computer program
and only you come out so spectacular. As a pantyboy, you will be a
superstar. You'll make us both rich and yourself famous. Together, with
our investors, we're going to open a chain of boutiques around the
country, then later, the world. Boutiques where 'daddies' will bring
their pretty boys to buy them expensive lingerie because they saw you
wearing it in our nationwide advertising. The boutiques will have
milking stations where overheated pantyboys can empty their testicles so
they can continue shopping without injuring themselves. It'll be big!
Bigger than big. And we'll call it, 'Timmy's Girlish Secret.'"
Chapter Three - Screen Test
But I didn't have a girlish secret.
Why did Mr. Hardwood think I did?
Although my teeny weenie did twitch a little when I saw my picture as a
gorgeous babe. That was because I was a heterosexual guy, right?
Plus, who says I would really look like that crazy computer simulation
anyway?
It was all silly and stupid and I was about to end it when Mr. Hardwood
pulled out a larger, thicker envelope.
"Timmy, I know you're skeptical and you should be. But I'm not alone in
my belief that this is a huge financial windfall waiting to happen. I've
found an investor - a very rich venture capitalist named Norm Creamer.
He believes in you and in Timmy's Girlish Secret. In fact, he's put up
the money for our entire startup, but only if you - only you - will be
our spokesmodel. He believes in you so much that he's giving you this
and all you have to do is a 'screen test.' Go ahead. Open it. It's
yours. But don't flash it in the restaurant or we'll be mugged."
Oh my, I thought. It must be a significant amount of money. Maybe $500.
That was a lot of money. More money than I had ever had in my life.
Well I wasn't dressing in girl's clothes and doing 'things' while I was
wearing them. Not for $500, not for any amount of money. Proudly and
heterosexually, I put the envelope on the table and pushed it toward Mr.
Hardwood.
He looked at the envelope, then at me. "You may want to open it. It's
$25,000."
My mouth hung open. I looked at Mr. Hardwood. Then the envelope.
I took the envelope.
I'm principled, but not stupid.
Mr. Hardwood smiled. "I'll take you home. I'll pick you up after school
tomorrow for your screen test, OK?"
As reluctantly as someone who had just made $25,000 could be, I said,
"OK."
He returned me home without incident. When we pulled into my driveway
though, he said, "One more thing, Honey."
I was terrified that he would try to kiss me or something. But all he
said was, "I'll need your signature on this waiver."
I was so eager to get out of there before he "tried something," that I
just signed the waiver without reading it.
Which, as you might imagine, eventually turned out to be important in
this story.
All that night and all the next day at school, I wondered if I had made
the wrong decision. The only reason I was going forward was that I
trusted Mr. Hardwood. And the $25,000.
More money that I could have imagined.
I didn't tell my parents about the money. Let's see. It would be, "Mom,
Dad, I have $25,000 in an envelope in my closet. Mr. Hardwood gave it to
me so I could dress up in girl's clothes and get men to buy their gay
little sissyboy lovers expensive lingerie at Mr. Hardwood's store. Is
that OK?"
Of course, when I bought my sports car the day after graduation, they
might still get suspicious.
Well, $25,000 was all I was getting, because the "screen test" was the
beginning and end for me. That I knew for sure.
True to his word, Mr. Hardwood was there to pick me up from school. He
seemed really excited, the pervert. He was a perv, wasn't he?
We drove silently to an unpretentious-looking photo studio in a nearby
strip mall.
An hour or two, I thought. Just grit my teeth, suffer these crazy people
for an hour or two, and I'll be rich.
I was trembling though as I entered the studio. Mr. Hardwood wouldn't
hurt me. I knew that. But what about that Creamer guy? Was he there?
He was. Standing inside. With a huge smile on his face and [horrors] a
big stiffie in his pants. Just what I needed - pervs in stereo.
He was a pretty nice-looking man - normal looking. Mid-30s. Fit. With a
really expensive suit. And he wasn't alone.
There was a VERY beautiful young woman there. With big titties. A really
short skirt. Stockings and heels.
Mr. Hardwood made the introductions. "Timmy, this is Norm Creamer, the
man whose investment will make us all very rich. And this is Freda
Fraumacher, the world's greatest femininity coach. She's coached many of
the country's top competitive femininity athletes, including her
'brother' Francine, who coaches the Saint Travestia University Stocking
Boys."
Wow. I knew all about "compfem." Everyone did. It wasn't for me, of
course, and Mom wouldn't allow "that trash" on our television. But it
was on the sports pages every morning and I read about it?sometimes.
Teams of pretty boys dressing up and competing with other colleges for
lots of endowment money for their colleges. Sad, really. But a lot of
people liked that sort of thing, I guessed.
Why was she there? I wasn't going to be a compfem athlete.
"Freda will get you ready for the screen test, Sweetheart," Mr. Hardwood
said. "Follow her instructions while we get things ready."
What "things?" Were they going to take pictures of me in girlish
clothes?
Panic.
Three things calmed me. The thought of $25,000. My faith in Mr.
Hardwood. And the fact that no one would recognize me in girlish
pictures.
Maybe this would take more than two hours.
Freda took charge. "Follow me, pretty one. I'm going to make you into
someone you will always ache to be."
I knew that wasn't true.
Boy was I wrong.
Freda smelled great. And did I mention that she had really big boobs?
And long, sheer-stockinged legs accented by her skyscraper heels. So,
despite my fear, I already had a stiff willie when she led me into a
small room and told me to strip down to just Timmy.
My work ethic told me that I should at least put out a minimal effort if
I was to earn $25,000. So, blushing fiercely, I complied.
Freda made me relax a little when she looked at naked me and said,
"Don't worry, Honey. The money you already received is yours. And you
don't have to do anything you don't want to do. But I must say, Honey,
you are an incredible beauty."
How was I supposed to take that? I was naked with a gorgeous babe and
she was admiring me as a fellow gorgeous babe.
My body reacted normally. I blushed. My cock got stiffer and began to
drip.
Freda commented, of course. "Oh, Timmy. Look at the good time your
'little person' is having. Your 'pink things' are perfect. So tiny and
pretty."
That made me lose my stiffie. A four-star babe had just called me tiny-
dicked and girlish. That appeared to be a script for my future. Except
for the part where beautiful babes were looking at my exposed penis.
To complete my humiliation, Freda giggled.
"Sorry," she said. "I didn't mean it as an insult. It's a compliment,
really. Of all the pretty boys I've trained to be pantyboys, your face
and body, especially your sissypole and little peanuts, are the
prettiest."
Shockingly, that made me stiff again. For the first time in my life, I
was excelling at something.
Freda seemed to understand my every emotion and thought. "This is only
the beginning for you, Honey. Your life just went from a D minus to a C.
In a month, and for the rest of your life, it'll be an A plus. Just
follow my lead."
Was she sincere, or was I being hustled? If she was sincere, was what
she said about me possible?
It was worth a bit of trust. I relaxed half a smidge and was about to
ask what was next when Freda placed her warm, soft hand on my bare
bottom. Oh, it felt so good! Was she going to do something naughty?
Not yet. Freda gently steered me to a full-length, four-way mirror on
the other side of the dressing room. She stood behind me and showed me
my naked body. And for the first time, I really saw myself.
I did have a lovely body.
Not a manly body.
But lovely.
I always hated looking at myself in a mirror because it never met the
manly standard I convinced myself was best.
Freda showed me a new standard.
A standard that I was setting. Not trying, impossibly, to meet.
"Look at yourself, pretty one," she said. "Look at that slim body. Your
perfect, pink skin. Those slim hips. And your nipples - so big and
puffy!"
My nipples? I can honestly say that until that moment, I had never
noticed or given my nipples one passing thought. They WERE big! For a
guy, I mean. Maybe even for a girl. And stiff. Was that from arousal?
"Oh," Freda said. "Look at your little popsy! Its pretty pink head is
coming out of its tiny cave of foreskin. So much pre-drool. Do you play
with yourself, Timmy? I'll bet you do and you make a lot of cum. Pretty
boys often do. And look at that lovely, pink purse of yours, with your
sweet peanuts throbbing from your excitement! Men will dream of kissing
and sucking your pink bits until you shudder and cum all over them."
Was that possible? Was I that beautiful? Wasn't that all gay?
I groaned softly at the thought of being adored. Though the fact that it
was men who would be the adorers was very unsettling.
"Look at this other mirror behind you, Darling," Freda said. "I want you
to see your pretty bottom. Look how pink and plump and pretty it is."
It was all that. Not manly. But those three P's, definitely.
What did it all mean?
Freda told me.
"You will rule the world, if you want to. When I train you and you
accept yourself, you will be the object of billions of men's fantasies.
And a man will do anything for the personification of his fantasy."
I trembled at the thought. Even if she was right, wouldn't I have to
become "gay" to realize that so-called destiny?"
Freda didn't leave me an ample opportunity to wallow in my angst. Still
standing behind my naked body, Freda said, "Look at this, Pretty Boy."
And she cruelly produced an item that complicated things.
Freda draped a tiny, silky, pink, shorty nightgown over my trembling
torso. Just held it there?by its white spaghetti straps. Showing me how
it would look if I put it on.
I stared at my reflection. Open-mouthed. Admiring the nightie's pinkness
and frothy white lace at the bodice.
I groaned softly as Freda slid the delicious garment softly across my
erect, sensitive nipples.
"Try it on," Freda whispered.
I couldn't. The humiliation. The gayness.
But I had to do SOMETHING for that $25,000, didn't I?
I whimpered and nodded my consent. Already I was acting like a pathetic
little nancyboy.
I held my arms over my head and gasped as Freda slipped the little
confection through my arms and head and settled it on my body. Afraid to
open my eyes at first, I finally gathered the courage to peer at "the
new me," as Freda called me.
Oh.
I was a boy in a supersexy nightgown. With my enraged penis sticking out
beneath the pink hem. Pink bag dangling saucily; little plums swollen.
No I wasn't. Not a boy exactly. Something else. Something feminine AND
boyish.
"You look divine, Darling," my so-called femininity coach gushed. "And
we've done virtually nothing to you. When we paint femininity in its
fullness on your pink canvas, you'll stop the earth's rotation."
What was she talking about? I was only there for that one day. Earning
that ridiculous fee. Doing Mr. Hardwood a favor.
Freda pressed on. "We won't shave your legs or paint your toenails or
anything?today. And no make-up. Well, maybe a little lipstick. Let me
show you how? Wait. How insensitive of me. You're in need of relief.
Look at your poor popsy. The head is positively purple. Let me help
you."
I panicked. Was she going to jerk me off? Well, that wouldn't be that
bad. She was, after all, a magnificent babe.
But no. I'm not making this up?what happened next, I mean. Without
further how-dee-do, Freda Fraumacher got on her stockinged knees - her
knees - in front of me and began to suck my cock.
And I was getting paid for her to do it!! So far, the deal wasn't half
bad.
No one had ever sucked my cock before. No one had even touched it except
my mom and dad when they bathed me as a small child. I had, of course,
tickled my own pickle. But that was a poor substitute for what was being
done to and for me at that moment.
My poor peener was already in a state of extreme arousal from the
nakedness and the humiliation (an amazing stimulant all in itself) and
being around Freda and seeing a small hint of my potential femininity.
Looking down to see myself wearing a pink nightie and a fabulous babe
sucking my cock, with full eye contact as she did it, was fantastic.
Feeling her hot, swirling tongue licking my sensitive parts was
indescribably delicious.
Freda gave a very good blowjob. At the time I had no basis of
comparison. Now I do. That was a very good blowjob. It was amazing that
I didn't cum in the first 30 seconds. Or the second. When she pressed
her right index finger between my bottom cheeks and grazed my anus with
just the pad of her delicate digit, I gasped, cried out and came a
bloody flood. Right down her throat. As she skillfully sucked and
swallowed until I could stand no more and begged her to withdraw.
She complied, smiling like the cat with a bellyful of canaries. Then she
arose and gave me a deep, tonguey kiss. I was a quivering wreck when she
broke the kiss, wondering what was next.
"That was nice," Freda said. "So much sissy cream! And so delicious. Do
you always cum that much? Anyway, back to work. Now here's how you put
on lipstick."
I guess I could forgive Freda for asking me questions and then not
letting me answer. I mean she had just swallowed my boyish juices. But I
was not happy about putting on the lipstick.
Until I saw the result.
OK, I've already told you that at least one crazy man, Mr. Hardwood,
thought I was beautiful. I guess that on an ordinary day when I looked
at myself in the mirror, all I saw was a boy who didn't look the way a
boy should look. My hair was a very light blond and a bit too long for
most boys. My features were too "delicate." My eyes were a brilliant
blue. Not much manliness there.
But put me in a nightie, add lipstick and apply a feminine standard, not
a masculine one?Mr. Hardwood was right.
I was a balldrainer! Men who were attracted to someone who looked like
me weren't weird. I would want to fuck me too. I mean, if I were a man
and if the girly me were a real girl. Know what I mean?
But I didn't want men to want to fuck me. I wanted women to love me,
Beautiful, big-titted, wet-pussied women.
I was straight!
A heterosexual male. Who looked like a man's soggiest dream.
Freda moved me along. "You look pretty good, eh? Wait till you see what
I show you over the next few days. Full make-up. Shaved legs.
Stockings!!! High heels. Manicures. Pedicures. And lovely lingerie. I'm
getting excited just thinking about it. Now wipe that horrified look off
your face and let's continue your 'screen test.' You did take Mr.
Creamer's money for it."
Oh, right. Duty called. I would finish that and that would be it. Never
to speak or even think about any of this again.
Though I did steal another look at myself in the dressing room mirror.
And my limp cock twitched and stiffened a bit.
Freda led me from the dressing room down a short hallway to what she
called "the studio," though to me, it just looked like a bedroom. It was
an ordinary teenage boy's room, with traditional furniture - a single
bed, dresser, desk, desk chair, comfy chair, full-length mirror. It also
had an "en suite" bathroom - tub/shower, small sink, big mirror over a
countertop.
Where were the cameras? Where were Mr. Creamer and Mr. Hardwood?
Freda didn't give me a chance to ask. "All, right, Timmy. Off with that
nightie. Wash off your lipstick and put your boy clothes on again."
Was I finished? Already? No more femmy things? No more money? No more
cumming?
Not really.
I complied, but not entirely willingly.
As I dressed, Freda sat in the comfy chair, hiking up her skirt to show
me her beautiful thighs. I loved looking at her feet in those impossibly
high spike heels.
When I was all "boyed up," Freda said, "OK. Let's start the screen test.
Go out of the room, come in and follow my verbal directions."
I nodded. "No cameras?" I asked.
"Just do as you're told, Honey."
I could do that.
I left the room, entered and listened to what she said.
"Don't look at me. Just listen and comply," she said. "You've just
gotten home from school. No one else is home and you're going to indulge
your girlish secret."
I thought yet again, "But I don't have a girlish secret." Didn't say it.
"You take off your clothes, slowly sensuously. Then you reach under your
folded undershirts in your top, center drawer and take out what you've
been hiding - a lovely white nightie with pink ribbons."
Another nightie. Oh.
I did as Freda said. Strip teasing. For her. And then it hit me. Mr.
Creamer and Mr. Hardwood were watching me. Through that big, floor-
length mirror, I imagined.
Men looking at me. I was naked. And they had seen me strip.
I almost covered my dickie. But then I thought, that would be cheating
on my screen test fee.
It was SO humiliating though to think that men were looking at me naked.
The teeniest part of me wondered if they liked what they saw.
And that made my dickie hard.
And drippy.
Which, I imagined, had those pervs in a regular dither.
And the thought of exciting them with my body made me gasp
involuntarily. I hurried my strip show a bit and walked, a little
sissily perhaps, to the dresser. I opened the proper drawer and reached
under the undershirts to find the white nightie. With pink ribbons. And
I gasped again.
It was adorable. And feeling the satin made me wonder what it would feel
like on my body.
I slid it over my head and wiggled it onto my body, making sure that I
gave the full-length mirror a nice view of my "privates" and my by-then-
very-erect nipples.
Freda spoke. "Excellent. Again, don't look at me. Stand in front of the
full-length mirror and put on your lipstick - just the way I showed you.
That's it. Good. Oh, you're spectacular."
I was eating the praise in big gulps. And the nightie was a sensual
delight.
"All right," my "director" said. "Now reach in your top right drawer and
take out two things - a small tube of lube and a framed picture."
Lube? A picture? Of whom?
The lube was K-Y. The picture was of Freda. Naked from the waist up.
Exposing her magnificent, huge titties and their two-inch diameter
nipples.
Wow.
"All right, Baby," my taskmistress said. "Prop up two pillows on your
bed, then lie on your back."
I did so, setting the lube and the picture to my right.
"Now lift your pretty nightie all the way up to your neck. Show me your
nipples, your little pink bag and your pricklet. Oh, it's all naughty
again, isn't it?"
It was that.
I could see what was coming next.
"Now I want you to slowly and lovingly lube up your popsy and your
testicles. Lots of slick stuff. Take your time. But don't cum yet."
Easier said than done.
I took my time. I slicked my pretty parts up nicely. Three times I had
to stop, lest I spurt my gooies. At Freda's direction, I also lubed my
nipples. Mmmmm. That was very nice too.
When was I going to be able to "ease my pain?" Hadn't the two men had
their look?
Freda must have thought so, because she said, "All right, Sweetie. Now
hold the picture in your left hand, play with yourself with your right.
Look at the picture as you play with yourself. Cum whenever you want."
A very welcome order.
Freda's picture was nice, but the real Freda was there with me. She said
not to look at her. And I was an order follower.
That didn't stop her from talking to me. "You're so beautiful, Timmy.
You make me jealous. I'm already half in love with you. If you stay with
our enterprise, I'm sure you and I will be lovers. And Mr. Creamer will
pay you big. $5,000 for each after-school session. $10,000 for a Friday
afternoon and night or an all-day Saturday or Sunday. You'll be rich!
And beautiful! And serially orgasmic!"
The thought of being Freda's lover was intoxicating. The excitement of
the day. The humiliation of it all. I squeaked, most unmanfully, and
pumped out six, thick strings of cum. All over my greased pubic area.
And girlish nipples.
I was exhausted. Heaving, desperate for oxygen. And shamed beyond words.
I was a little faggot sissy nancyboy. I wanted to crawl in a hole and
pull the dirt over my head.
But Freda would have none of it.
"Nice work. But there's so much for you to learn. Here's your $5,000 for
tomorrow's modeling session. I'll pick you up after school by the south
entrance. Here's a towel. Get dressed. Mr. Hardwood promised your Mom
you would be home for supper every night. And you have homework to do.
I'll drive you home."
Mr. Hardwood and Mom had colluded on this? Did I have any say in what
was happening to me?
Despite my serious reservations, I had to come back the next day.
Praise, sex and money are the world's greatest incentives.
Freda drove me home, pulling into a spot four houses from mine at 6:10.
She gave me a deep, tonguey kiss. Then she handed me a plastic bag and
said, "Here, put this in your backpack."
"What is it?" I dared ask.
"Your first girlish secret. Wear it to bed tonight and you'll sleep
well."
Mom gave me the usual "How was your day?" As if nothing happened. So did
Dad. Clare was considerably more suspicious, but didn't have enough to
indict me yet. I mumbled something to her about looking for an after-
school job, but wasn't very convincing.
Looking at Clare, my one-year-older sister, that night, I realized that
she looked very much like the "girlish me" I had begun to see that
afternoon. The rare times when she had girlied up, she was a real dish.
No wonder she had all those young men stalking her all the time.
Clare didn't have a lot going for her at that time. After graduating
from high school the previous year, she decided to take a year off to
"find herself," though I didn't know what she would find asking people
what they wanted in their lattes.
After supper, I did my homework, said good night to everyone and locked
my bedroom door.
Then I opened my backpack to discover Freda's "gift." It was a black
nightie. Tiny. See-through.
Oh.
I wondered if I should cut it into small pieces and flush it down the
toilet. Destroy the evidence. If I kept it?and it was discovered?
What would my family think? Would I be sent off to Gayness Prison? Would
I be excluded from all family gatherings until they attended my funeral?
The smart thing was to destroy or dispose of the girlish item at the
earliest opportunity.
But I wasn't very smart.
I stripped naked and put it on.
My goodness, I looked good in lingerie.
My prickie certainly agreed.
I was terrified of discovery. Which made it all the more exciting. And
dirty. I turned out the lights and got into bed. Covering myself from
with sheet and blanket.
I have to admit. I felt very girlish in my pretty lingerie. And aroused.
I put my knees up, lifting the sheet and blanket to give myself
unfettered manual access to my pretty privates. With the thumb and
forefinger of my right hand I skinned my little hood. With my brain, I
recalled my astounding afternoon. And thought about the next afternoon.
Would Mr. Hardwood be there? What would he do? What would he want me to
do?
Unnnhhhh!
I spurted for the third time that strange day. Hard. Then fell into a
sweet, exhausted sleep.
Chapter Four - Basic Girlishness
The next day was also weird.
Why are you not surprised?
And it began long before Freda picked me up after school for modeling.
At breakfast, I kept sneaking peeks at Mom for clues to what she knew
and what she thought. She knew Mr. Hardwood had sent me a Valentine and
taken me to dinner on my birthday. She knew I had seen him after school
the day before and was seeing him again. At least he saw me - I didn't
really see him.
Mom clearly did not disapprove. Which was also darned disconcerting.
Clare was bursting with curiosity, but had learned long ago that
observation is a better way to gain information than interrogation.
Dad had already left for work, but what did he think?
We were not great communicators.
Then there were the oddities at school.
I was a boy who was fully accustomed to being ignored. I had come to
embrace it, really. But that Tuesday, I began to be only partially
ignored.
Which was disconcerting too.
Barry Broadback, a football star who would soon be going to one of those
thug universities on an athletic scholarship, had been in school with me
since the fourth grade. I was willing to bet that he didn't know my
name, first or last.
It wasn't meanness on his part, really. I was invisible.
That day, coming out of English class, Barry locked eyes with me - and
held the lock.
I shuddered when he did it.
It amazed him as well. He seemed to grasp for my name and then?and I'm
not making this up?he said, "How's it going, Timmy?"
I was so stunned that I said nothing. But THEN?THEN?he held the door for
me and said, "I'll see ya. Have a good day."
Where did that come from?
I wasn't wearing anything the least girlish. Even under my clothes.
I was the same person I had always been. Wasn't I?
But wait. There's more.
That afternoon, in biology class, Mr. Darwin looked at me several times
during his lecture. After class he spoke to me for the first time,
saying, "Nice lab work last week, Timmy."
Nice lab work?
He had never said that to anyone, especially me, before.
Men were already noticing me.
Just as Freda said.
I shared all that with Freda as she drove me to "the studio."
She beamed with pride. "Already it's happening and you aren't even
wearing panties yet. You have powerful feminine juju, Honey. Killer
juju."
Panties?
Juju?
Freda was in a great mood as we entered the studio and she explained the
day's activities. "Today we'll introduce you to foundation to go with
your lipstick. I'll show you how to shave your legs and you'll wear your
first stockings and a garter belt. Then I'll give you a little
homework."
I was trembling. Was it fear? Or sexual excitement?
Would Freda and I be - doing the nasty?
We would see.
We went to the studio, where Freda had lined up some appropriate
cosmetics for me.
"Strip naked for me, Sweetheart," she said.
"For her," she said, but I knew it was for those two men too. Were they
there? Looking?
I was betting on it.
I peeled my boy things off as sexily as I could. Then stood naked in
front of the full-length mirror. I admired my body, looking right and
left, up and down. I even turned to give my audience a nice view of my
pink bottom.
By that time, my pricklet was in a state. Which I hoped, when I joined
Freda in the bathroom, would give her the idea that she should relieve
my suffering.
Not yet. Freda was all business. When I caught on quickly with the
foundation and lipstick, she added to the day's agenda by teaching me
about eye liner, mascara and eye shadow.
My makeup was nowhere near perfect that day, but seeing the full effect
of essentially full makeup made both Freda and me gasp.
Freda moved behind me as I looked at a beautiful, truly beautiful me in
the mirror.
"Take a good, long look, Darling," Freda said, as she reached around my
right hip and skinned my peeny up and down?up and down. "Is there any
doubt that everything I've told you is true?"
I cried out in sexual agony, spurting my creamy load.
"No doubt," I groaned.
When I had recovered a bit, Freda said, "Let's make you even sexier.
Wouldn't you love to have smooth, hairless legs to draw your silky
stockings across?"
I was pretty much with any aspect of Freda's agenda at that point. I
nodded assent.
"Goodie. Let's shave those legs."
Freda showed me how to lather up my legs and then carefully draw my
ladies' razor across each sensitive spot. I wasn't really hairy to begin
with, but I had to admit that it was thrilling to feel Freda's warm hand
slide sensuously along each now-silky leg.
Nighties were one thing. But if I wore stockings, was I doomed to
becoming a lifelong pantyboy?
Probably. But at that moment, I was willing to believe that Lee Harvey
Oswald was Osama bin Laden's cousin if Freda suggested it.
Stockings.
How can I describe my first feelings when I rolled them into doughnuts
and slowly slid each black teaser up a smooth leg?
You know how it felt, girls. And how it feels now. It's one of the many
wonderful things that make us love our girlishness.
I hadn't framed it in those grand terms at that time. I was LOVING the
sensations, while fighting the unsettling notion that two men were
probably creaming their boxers watching me slip into a frilly, ruffled
garter belt and lovingly hook each stocking clasp.
Life's all about good and bad, isn't it?
Freda asked me how I felt as I stared at my lovely, cosmetic-enhanced
face and stunning, stockinged legs.
I was too overcome to speak. I could only blush.
Which told Freda all she needed to know. She had me?for the whole
project?whatever it would be. And she knew it.
"All right Sweetie. Just a couple more things to do today and then I'll
give you a big treat. I want you to lie on your back on the bed. Oh
wait. Make that on your knees. Prop yourself up with your left arm.
That's it. You're on 'all threes.' Now I want you to tickle your pickle
with your right hand until you cum. I know you can cum, Baby."
No problem there. My ears were on fire.
I thought about those two men looking at my pretty, plump, pink bottom,
framed by black stockings and garters. Pointed right at their hiding
place.
No picture to look at, but that was OK. Freda was telling me how
beautiful I was and how Barry Broadback and Mr. Darwin were probably
home in their beds, right then, rubbing their big, stiff, hot cocks.
Dreaming of me. Thinking about how they wanted to make love to me. And
stick their big rammers in my tiny pussy."
For an instant I said to myself, "But I don't have a pussy." Then I
realized what she meant.
And that triggered a starburst of cum. Heaving spurts. And the girliest
little squeals.
I was humiliated at what I had already become.
But even more eager to find out what would happen next.
Freda gave me a few minutes to return to the earth. Then she said, "Time
for your rewards, then we'll go home."
Rewards? More than one?
"Here's your first reward. Tomorrow's $5,000."
Oh. That. Well, there had to be more.
"I know your want a second reward and here it is."
Freda removed her blouse. I gulped. She unhooked her bra, releasing two
spectacular specimens. Really spectacular.
But there was more. Freda shimmied out of her skirt. I saw her garter
belt, panties and stockings. She kept her stiletto heels on. I liked
that. Were the panties next?
Not that night.
"I'm having my period, Sweetie. But make yourself at home in my
cleavage."
I was having a good day. A nice heterosexual day, once again.
I sat on the side of the bed as Freda stood in front of me. I licked and
kissed and sucked Freda's huge nipples. And her big, warm, glossed lips.
She really seemed to enjoy it. I know I did.
Then she got on her back on the bed and invited me to lie on top of her.
No problem.
More kissing and titty sucking. Mmmmm.
Then Freda took it up a notch. As I was snogging away, I noticed that
Freda was lubing up some fingers on her right hand.
Why would she?
Oh.
I didn't know people did that.
Freda slowly and thrillingly entered my bottomhole with the middle
finger of her beautiful right hand. And wiggled it. And found a spot I
didn't know I had.
But my cock knew what she was rubbing.
My tender little "anal walnut." So sensitive.
Her slick finger rubbed and teased.
Encouraged by my helpless squeals, Freda drew her finger in and out..in
and out. Then - something new! She added a second finger.
Aaaaaah. More insistent rubbing on my prostate. More stretching of my
virginal bottomhole. I was in heaven.
Freda rolled me over onto my back. Kissing me deeply, with an overactive
tongue, Freda added a third, lubed finger into my stretched pootie.
"Doesn't that feel wonderful, Baby?" she asked rhetorically. "Your pussy
is so hot and tight. Just imagine how delicious it will be when a man's
fat, hot cock is in there, not just my fingers. A man's cock spurting
his thick cream."
I arched my back, screamed and exploded. All over my pretty tummy.
A lake of boy's cream formed on my flat stomach, with strings as far as
my nipples.
I had just experienced the deep, shuddering pleasure of my first anal
orgasm.
And the notion that had pushed me over was a very gay one.
Freda brought me back from the dead, insisting that I take a shower
before we go home so that I didn't odorously announce to my family how I
had spent my afternoon.
Before we left the studio, however, she gave me $5,000 and my homework.
"Wear these stockings and this garter belt under your boys' things until
I pick you up at school tomorrow."
I agreed, only semi-reluctantly. Wearing girlie things was making me
rich and orgasmic. And they made me feel good too. They made me feel
pretty?oh so pretty.
That evening, it was three for supper. Clare had a date with someone Mom
described as a "very nice man."
Man, not boy. I should have picked up on that, but I was too delighted
that she wouldn't be around to ask dumb questions.
After homework, I locked my room, stripped down to my stockings and
garter belt and inspected myself in the mirror.
Wow. Was I getting femmier by the minute or what?
The tan, seamed stockings and white garter belt looked natural on me. As
if I had been wearing them all my life. I wondered what my legs and
[blush] bottom would look like if I wore big heels like Freda.
My conclusion was - fantastic.
Then I remembered the plastic bag Freda had given me and fished it out
of my backpack.
Oh my.
It was a magazine.
A very dirty magazine.
Called "Panty Boy."
Where had I seen it before?
Oh, yeah. I caught my Dad reading an issue of it one day about a year
ago. He seemed very embarrassed when he knew I saw him. He asked me
about something he knew I would talk a lot about as he tried to hide the
magazine. I had forgotten about it.
Panty Boy!
Was that was I was becoming?
And why would a man like my Dad want to read about boys like me?
The cover photo seemed normal enough. It was a pretty, eighteen-year-old
boy and a fortyish man going into an "intimate apparel" store. "Shopping
with 'Daddy'" was in the bottom right corner of the cover.
The words "Panty Boy" were across the top of the magazine, with a pair
of pink panties draped over the "P."
I decided to get comfortable before I opened the magazine.
I lay on my bed, head propped by two pillows. Stockinged knees up. Popsy
stiffening as I opened to pages 2 and 3. It was a double page picture of
the young man, identified as "Peter" and the man, identified as 'Daddy,'
but not Peter's biological father" shopping in a wonderful, very large
lingerie store. They were the only two men in the place, which didn't
seem to bother "Daddy," but Peter seemed embarrassed, bordering on
humiliated.
Next page, a saleslady was helping "Daddy" and Peter pick out loads of
intimate dainties. A crowd of ladies had gathered, and Peter seemed
mortified. But "Daddy" stayed the course. The two carried seven or eight
shopping bags of stockings, nighties, teddies, bustiers, bras and
panties to "Daddy's" car.
"Daddy" and Peter were sitting in the car. "Daddy" asked Peter, "Was
that exciting for you?"
Peter said, "Oh, 'Daddy,' I was mortified. And I've never been more
excited in my life. Please take me home and fuck me!"
My pricklet throbbed and drooled a thick drop.
I turned the page.
Peter and "Daddy" arrived at a very nice house - did they live together?
Peter kissed "Daddy," took the bags upstairs, and Daddy puttered around,
waiting for Peter's call.
The call came quickly. "'Daddy,' I'm ready," Peter called.
Daddy took the steps two at a time and entered the lovers' bedroom.
Peter was stunning!
Almost as pretty as me.
He, I mean she...or he?Peter was all in pink. Stockings, garter belt,
bra and five-inch stiletto sandals. Perfect makeup (I had to work on
that). Lying on the bed with pink panties down to his mid-thighs.
"Daddy" undressed in a picosecond. Nude, he climbed onto Peter and for
the next 40 full-color pages, "Daddy" and Peter exchanged sperm. In
Peter's mouth. All over Peter's pretty face. And three large loads in
his plump, tiny bottomhole. Peter came twice for every one of "Daddy's"
orgasms.
Sperm was everywhere. In the pictures. But especially, all over me.
I was fatally excited by what I saw.
What an eye-opener it all was.
That exact magazine issue had to be Mr. Hardwood's inspiration for the
"Timmy's Girlish Secret" stores. A place where "daddies" can take their
pantyboys without being ridiculed. A place where pantyboys can stock up
on their girlish needs. Then model them for their randy daddies.
I had no idea that big-dicked daddies could fit their johnsons into a
pantyboy's tiny pootie.
I had no idea that a pantyboy could enjoy his "daddy's" big cock in the
pantyboy's "pussy" so much.
I guess I had already known that Mr. Hardwood wanted to do all those
things with me.
The question was, what did I want?
After all that cumming, I was exhausted and just wanted to go to sleep.
But at least I had the good sense to clean myself up before I went to
bed and had to explain cum-drenched sheets to Mom.
I began to wonder, though if that would surprise Mom all that much.
I washed out my stockings and hung them to dry, since I had promised
Freda to wear them under my boy clothes the next day.
Back in bed, I tried to sleep. But couldn't.
So much to think about.
Clearly, I loved exploring my femininity. Clearly I loved playing slap
and tickle with Freda.
But how would I deal with the issue of Mr. Hardwood's infatuation?
After a restless night, I cleaned up and dressed, ready to face a day
with a true girlish secret - stockings and a garter belt under my
clothes. I had no panties - hadn't worn any yet. Boxer shorts seemed
inappropriate. So I "went commando."
It was terrifying to walk around school all day hiding stockings and
garters under my trousers. Mortification was prevented only by the thin
material of my boy's pants.
But it was horribly exciting too.
No one actually saw my stockings that Wednesday. But three more boys and
two more male teachers "gave me the time of day." Something about me was
connecting with the deepest male instincts. Something they didn't
understand, but were compelled to act on.
Freda picked me up on time after school and we had another great
afternoon. Though Mr. Hardwood and Mr. Creamer were still no-shows.
I wore my first panties! My tiny testicles and pink knoblet felt their
silky embrace. And, of course, I filled a tiny, pink pair of teasers
with a big, gooey load of sticky cream.
Freda schooled me more on makeup and began to teach me how to walk in
three-inch heels.
She also gave me a long, lovely slurpy, on-her-knees cocksucking and
tons of sweet kisses.
Then she gave me my homework.
"This is an anal probe, Honey. I want you to lube it up and explore your
pussy when you get in your bed. Wear this lovely lemon yellow babydoll
nightie and imagine as you're "probing," that a nice sweet man is
fucking your pretty bottom. Can you do that?"
I was mildly horrified. But you didn't say no to someone who's emptying
your ball bag on a regular basis.
Clare was on another date that night. Again, I was glad to avoid her
scrutiny. And didn't think through why or where she was out.
That night, I dressed in my lemon babydoll and admired myself for
several minutes. Which had the usual effect of putting my peeny in
severe distress.
I was a bit nervous about using the anal probe, but I didn't want to
disappoint (or disobey) Freda. Following her instructions, I lubed the
probe head thoroughly as I admired its design. It was a foot long, with
a thick, five inch handle, a thin, five-inch tube and a two-inch long,
one-inch diameter, curved head.
Freda had explained that I should lubricate my bottomhole thoroughly
with my finger(s), then ease the lubed head in. I should then probe
around a bit until I located my prostate.
"What do I do then?" I had asked Freda.
"You'll know, Honey," she said.
Delaying the "probing" a bit, I decided to review the literature that
Freda had given me earlier - Panty Boy magazine.
I lay on my back, placing the lubed probe and the tube of lube by my
side, then reopened the magazine.
I opened to a random page. Peter was receiving one of "Daddy's" thick
creamy loads all over his beautiful, carefully made-up face. His pretty
features were sopping with sperm. He should have been disgusted. Or
mortified. But he wasn't. He was?delighted.
He should have been humiliated for many reasons. Even forgetting the
horrible gayness of it all, that, that?man was emasculating poor Peter.
Peter was being used. He was giving himself to the man as his
receptacle?for all the man's disgusting needs. Peter was so submissive
to the man that he called him, "Daddy." Giving the man complete
authority over the boy. He even let the man mortify him in public at the
lingerie store.
And yet, Peter loved his "Daddy." That was obvious.
Peter wanted to be emasculated. He wanted to serve his "Daddy." He
wanted to give "Daddy" the greatest present of all - himself.
Peter had surrendered himself and his masculinity to his "Daddy."
Could I ever do that? Would I want to? Who would be the lucky "Daddy?"
Well, it wouldn't be Mr. Hardman, I could tell you that. Or Mr. Creamer.
They had abandoned me. Not that being with Freda was bad. It was
fantastic. But shouldn't Mr. Hardman be?well?there for me?
My little pickle was in powerful peril. I put the magazine down and
lubed my penis gently, careful not to cum too soon.
Then I lubed the fingers on my left hand. I had never entered my bottom
with my fingers. How bad could it be?
Oooh.
It was very nice.
Why hadn't I discovered that before?
I lay back and enjoyed wiggling two fingers in my tiny pooper.
My nipples erected, which made them rub against the satiny material of
my nightie.
Double oooh.
Reluctantly, I removed my fingers. They made the cutest pop as they
exited.
Replacing the fingers with the probe, I slowly eased it into my wrinkled
hole.
I was still a tiny bit worried that it would hurt, but after seeing all
those TV public service announcements from the LDP (Lubricate, Dilate
Penetrate) Foundation about painless anal sex, I was pretty sure I would
be OK.
OK is too mild a word.
I was delighted.
Freda was right.
When the head of the probe found my prostate, I knew just want to do.
Rub.
Rub.
Gasp.
Pant.
Squeal.
Cum.
Wow. Was that what being fucked was like?
Chapter Five - Intermediate Girlishness
I woke up on Thursday morning in a bit of a panic. Rather than covering
my tracks as I had earlier in the week, culpatory evidence was
everywhere.
My nightie was still on, though I had pulled it up to my neck. My
[blush] nipples and privates were fully exposed. Dried cum seemed to be
everywhere, especially on the pages of my Panty Boy magazine. There was
even some on my chin.
But worst of all, the anal probe was still in my bottomhole.
I liked it there.
Cum was also all over the sheets.
Oops.
Mom would know I was whacking my weenie. And spurting it copiously and
indiscriminately,
I panicked.
Briefly.
Then it hit me.
Everyone whacks their weenie.
Mom wouldn't even blink, would she?
So, all I would need to do was clean up the girlie things.
Whew.
I wasn't prepared to let anyone know about my apparent girlishness.
Not yet.
But that didn't mean that I was going to wear icky boxers and a tshirt
under my boy clothes. Not when I could wear pretty white panties, black
stockings and a white garter belt that day.
I was causing a bit of a stir at school. For reasons they barely
understood, about 20 boys and male teachers who had never before
acknowledged my existence found an urgent need to speak to me that
Thursday.
Barry Broadback, the jock whose finely-attuned sissy radar was the first
to connect with me, had gotten positively chummy. Despite the
disapproving stares of his thuggish fellow jocks and his legion of
female admirers, Barry sat with me at lunch and told me about his
family.
He was, it turned out, quite human.
And, though he only dimly realized it, eager to get into my panties.
Well he could just forget that. I had a girlfriend, Freda Fraumacher,
who knew about my girlish secret, and still loved me in a healthy,
heterosexual way.
Still, it was awfully flattering. And it took a bit of effort to avoid
flirting with him and the others, particularly Mr. Darwin. I shivered
when I thought that, had I actually flirted, one of those beasts would
have probably thrown me on a lunchroom table and had his disgusting way
with me.
Why did that thought make "Little Timmy" so stiff and drippy?
Anyway, after school, it was the usual, except that we began the session
by Freda showing me how to paint my toenails a bright red. I loved
wiggling them. It all felt so sweet and girlish.
Then I earned my $5,000 by trying on various pretty outfits, learning
how to "volumize" my eyelashes, improving my makeup and high-heel-
walking skills, lying on my back, tickling my pickle until I made sissy
cream and enjoying a fantastic cocksucking, with anal stimulation from
my lovely Freda.
I was eager to lick her "pink pie" in return, but Freda said, "My period
will be over tonight. Tomorrow, you'll get what you want and need. A
real fucking."
Oh, joy! Freda was going to let me fuck her on Friday, and we wouldn't
have to be home until 11 p.m., my Friday curfew.
That was what she meant, wasn't it?
As we drove home, I took roll call of the missing - Mr. Hardwood, Mr.
Creamer and my sister Clare.
Oh well. I had Freda. And my girlish things. The others would turn up.
That night, at bedtime, I girlied up in a lovely red nightie with white
bows. I loved looking at my pretty toes. Then I lubed up my popsy and my
probe and opened Freda's latest gift - another copy of Panty Boy
magazine.
This one featured a pretty boy named Terry, who was a college student.
He came home from school, got undressed and then redressed as a
delicious pantyboy. He did his make-up perfectly and his lingerie was
spectacular. In the end, he excited himself so much that, with slick
fingers in his bottom and his other hand rubbing warm oil on his "pink
purse," he drenched his tummy with a half gallon of girl's cream.
The big difference for Terry was that, unlike me and the pantyboy in the
other issue, Terry had a VERY large cock! At least eight inches! And
very thick.
The lesson from Freda, I think, was that you don't have to have a teenie
weenie to have girlish secrets.
As I probed my pooper, I thought about Terry. What would it be like, I
wondered, to make love to another pantyboy? What if Terry and I were
making love and he wanted to put that big, thick, hot thing in my tiny
bottom? It would rip me open. I would be permanently shamed and
emasculated.
And that made me spill my girlish load in six, thick globs all over my
stomach.
Then I did something very naughty.
I tasted my spendings.
Be honest. We've all done that. But it was my first time.
And I didn't die.
It wasn't bad. It wasn't particularly good. But it wasn't bad. Kind of
like a raw egg.
Rocky drank raw eggs before doing his roadwork.
So it was kind of manly.
I fell asleep, eager for the next day.
I awoke that morning and realized that it was the only day in my life
for which I had been promised fucking.
It was bound to be a turning point in my life. A big turning point.
Actually, it was a series of turning points - making a revolving point.
Beginning with me, in my boy outer clothes (girlish secrets underneath)
heading for breakfast in the kitchen. And running into the first
"missing person" - my sister Clare.
I think it was my sister.
When I had last seen Clare, she was wearing no make-up and no jewelry.
Her hair was a disheveled mess. She was wearing a grey "hoodie"
sweatshirt, men's plaid pajama bottoms rolled-up to expose her unshaved
calves, and dirty slip-on sneakers. In other words, her usual outfit.
That Friday morning, Clare, if she had been flat-chested, could have
been on the cover of "Vogue." She was wearing a lovely, stylish, navy
blue dress, with perfect accessories. Four-inch-stiletto fuck-me pumps.
Tan stockings. And her face and hair were perfect.
Wow!
All I could say was, "Clare?"
Clare smiled. I erected. I know she was my sister, but she was a big-
boobed, gorgeous eleven.
"Timmy. I'm sorry I haven't been there for you these past few days, but
I hear you're doing great."
"There for me?" "Hear you're doing great?"
Huh?
Who was she talking to?
But Clare was in a hurry. And she had a small suitcase.
"I'm in love, Timmy. He's perfect. A bit older, but rich. And he adores
me. We're going to Paris for a few weeks. I'll call you on Monday or
Tuesday and tell you everything. Feel free to borrow any of my things
when I'm gone." Then she kissed my cheek, hugged me, and ran out the
door to a waiting limo.
Huh? Huh?
I went to the kitchen to ask Mom for an explanation, but she was
evasive.
"Isn't it wonderful, Timmy? Clare's in love with a wonderful man. Maybe
you'll fall in love soon too. Hurry up and eat your breakfast. Don't be
late for school. I have to run," she said. And she did.
Strange.
School was getting weirder every day. Thirty-five boys and teachers made
friendly gestures to me and Barry, my lunch "date" yet again, brought me
a sandwich he made at home. The sandwich wasn't very good, but I must
admit, I enjoyed the attention. And was frightened by it. What would all
those horny guys do when they found out I was purely a ladies' man?
After school, I was wildly excited about my impending intercourse.
And?since it would be a double training session, I had already received
$10,000 instead of my usual $5,000. That made $55,000 I had received so
far. Wow!
Freda had told me that a taxi would be picking me up because she wanted
to have some time to make herself beautiful for me. The cabbie was on
time and he delivered me to my little lovenest. Freda opened the door
for me and took my breath away.
She must have spent the whole day on her hair and make-up and it showed.
She had taken the eye make-up all the way to "trampy." Her pretty
brunette hair was styled deliciously. And her clothes? Wow!
Freda was all in black - silky stockings over her long legs. Strappy,
mule, five-inch-stiletto sandals. Skimpy panties. No bra encumbering her
magnificent mammaries. And the sheerest black peignoir.
Freda defined sex.
And she was all mine.
But not right away.
After a deep tonguey kiss that had me in a stiff state, Freda said, "I
want you to get girlied up first. Then the fucking. All you want!"
Sometimes life is good.
I showered first in the studio's bedroom, cleaning myself all over and
shaving my legs. Then I made my face up in the sultriest way I knew. I
stepped into the bedroom and saw Freda laying out my clothes.
She was doing the minimalist thing that night. I eagerly put on skimpy,
pink bikini panties, an open-nippled, pink bra made from two ruffled
triangles, and strappy, pink, stiletto sandals.
As was my new habit, I admired myself in the mirror. And tented my
panties. Were those men watching? Were they still alive? I decided that
I didn't care. Ignoring the new me had become a capital crime.
As I was posing, Freda said, "You're magnificent, Darling. Prettier than
me. Prettier than anyone. I'll be right back and then I'll show you how
wonderful you are."
Freda left the room. I was enjoying the view of myself so much that I
didn't mind. I was a little nervous about whether I would fuck her well.
But I knew it wouldn't be from lack of effort.
I could see what the boys at school were so riled up about. I was
probably the prettiest girl I had ever seen - except for maybe Clare. I
was prettier than that Peter in Panty Boy and that Terry person too.
Maybe someday, if that Barry was still nice to me, I would let him kiss
me. No tongue. Well, maybe just a taste. It would have to be in secret,
because we wouldn't want people to think we were gay.
I was sort of speculating about all kinds of things when the door opened
and Freda returned.
At least I thought it was Freda. I looked in my mirror to see Freda
behind me and saw?.
Oh, no.
It was?
Mr. Hardwood.
Fully dressed in khakis and a long-sleeved polo, but with a HUGE,
vertical, iron pipe in his pants!!
He came up behind me and held me by my trembling shoulders. I felt his
hot breath.
"You're spectacular," he said. "I love you. I've loved you since I met
you. And before the night is out, I think you'll love me."
I gasped.
Where was Freda?
Had she left me alone with that?that man?
And what about the fucking she promised me?
The fucking?
Oh.
Was THAT what he intended to do with that big, fat pole?
Oh.
I looked at Mr. Hardwood in the mirror. He had a sappy, lovestruck look
on his face. For the first time in my life, it appeared that I had
caused someone to actually fall in love with me. And he really did love
me.
What w