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From: Ann Douglas <ann_douglas@hotmail.com>
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Subject: {ASSM} AnnD"Dear Prudence"MF(3/4)
Date: Tue, 17 Oct 2000 22:10:17 -0400
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	Dear Prudence
	by Ann Douglas
            (ann_douglas@hotmail.com)

Part  Three


	"What shall we drink to?" Brooke asked as picked up
both drinks.
	'To a really wonderful evening,"  Gregg said as he took
his glass from her and held it up, looking at the amber liquid
within.
	"And the company that made it such a good evening,"
Brooke added as she tapped the edge of her glass against his,
before talking a large swallow.
	Gregg followed suit, immediately gagging as the fiery
liquid burned his throat.
	"Easy, honey,"  Brooke said, patting him on the back.
"This is all new to you.  Just take little sips."
	Regaining control, Gregg did just that, only letting a
small taste past between his lips.  This time, he managed to
handle it much better.
	"It was a fun evening,"  Brooke said as she put her now
empty glass back on the countertop.  "I really had a good time."
	"Me too,"  Gregg agreed as he put his glass next to hers.
A glass still half full.
	They stood there for a long moment.  Gregg looked like
he wanted to say something else, but instead looked down at his
watch.
	"It's pretty late,"  he said when he saw the time.  "I guess
I'd better get going."
	"If you want,"  she responded, thinking that it was hardly
late at all.
	She walked Gregg to the door and was about to open in
when she felt him stop.  Turning to look at him, she saw the
same look on his face that had been there before he looked at
his watch.
	"Gregg, is there something that you wanted to say?"
she asked.

	His face turned red with embarrassment, causing
Brooke to wonder what could cause such a reaction.  Finally,
gathering up his courage, he said what was on his mind.
	"I was wondering if, ... I mean I wanted to ask if it,... if
it was okay if I gave you a kiss goodnight?"
	Brooke almost laughed but managed to keep from doing
so.  It was such a charming moment.
	"Oh course you can kiss me goodnight,"  she finally
replied.  "What sort of date would I be if I denied a nice young
man like you such a simple gift."
	A bright smile on his face, Gregg leaned forward to
bring their lips together.  His kiss was soft and warm, Brooke
thought, just as a young man's should be.
	As their lips pressed together a second time, Brooke's
eyes opened wide as she felt Gregg's tongue slip between her
lips, pressing against her own.
	Her first reaction was to put a stop to it here and now,
but something held her voice.  It was after all, just a kiss.  Was it
so much to let him have a moment's enjoyment.
	A heartbeat later, Gregg took an action that couldn't be
ignored.  The touch of his hand upon her breast caused her to
call out his name in surprise.
	"Gregg!"  she cried out.  "What do you think you're
doing?"

	"Oh God, I'm sorry!"  Gregg said as he pulled away from
her.  "I wasn't thinking, it just seemed like the right thing to do."
	"The right thing to do?"  she repeated.  "Gregg, I'm old
enough to be your mother!"
	"I've never thought of you like that,"  he quickly added.
"old I mean.  I've always been so attracted to you, spent so
many nights thinking about what it would be like to be with you."
	  "I don't know what to say,"  Brooke answered.  "Haven't
you ever been with a girl your own age?"
	"I've never really been with any girl,"  Gregg said
surprisingly.  "Mother always told me that if I was with a girl and
something happened, it could damage my career."
	"Not to mention loosen the hold she has on you,"
Brooke thought as she looked into his eyes and saw a mixture of
both sorrow and longing.
	A few months back, when Gregg had turned eighteen,
Harry Hamilton has told her what he really would like to do for
the kid is take him out for a night on the town and get his ashes
hauled.  Brooke had talked him out of it at the time, assuring the
actor that she was sure a good looking kid like Gregg had no
problem in that department.  Now she wasn't so sure that might
not have been a good idea after all.
	"Gregg, honey,"  she said in her most reassuring voice.
'I'm not angry at you, but you have to realize that it really
wouldn't work out between the two of us.  Think about it a
minute, I'm twice your age.  What kind of relationship would we
have?  You've seen the way the tabloids tear people in our
business apart.  Your mother is right in that aspect at least,
much as I hate to admit she's right about anything."
	"I really never thought about having a  relationship,"
Gregg admitted.  "I just thought about me and you doi...."
	He paused in mid-word, realizing that the way he was
saying it felt so cheap and dirty.
	"You just thought about you and I having sex?"  Brooke
completed his sentence.
	"Not sex, making love,"  Gregg corrected her. "I wanted
you to be my first.  You've always been so nice to me.  Always
making sure that I was part of everything. You helped me with
my acting, teaching me all the things you've learned.  I love you
so much, I just wanted it to be you."
	"Gregg, that's such a sweet thought, but don't you think
it would be better with a girl your own age," the older woman
suggested, almost adding, what would your mother say.
	"If that's what I wanted, I would've gone to the party with
Paige," he answered.  "She's always telling me she has
girlfriends who'd love to pop my cherry."
	"And probably sell the story to the tabloids the next day,"
Brooke thought.

	Brook's thoughts flashed back to her own first time.  She
had been sixteen and her boyfriend eighteen.  It seemed to her
at the time that he was twice her age, as far as experience went.
 From the perspective of years, it would undoubtedly have been
nice for that first time to have been with someone her own age.
Someone she was truly in love with and could learn about sex
together.  Failing that, she considered, having had an
experienced and caring teacher who made the experience
memorable was the next best thing.
	In the public eye as he was, and with the type of girls he
usually met, Brooke thought it unlikely that Gregg would ever
get the chance at that first choice.  Hell, there was little chance
he'd find the second, at least someone who wouldn't take
advantage of him.  At least in this town.
	"I don't believe I'm really considering this,"  Brooke
thought to herself as she found herself considering options.  "I
could be his mother, for Christ's sake."
	The thought of Juliet brought another factor into her
thinking.  If she did this, and the possibility that she might
seemed to grown with each passing breath, then there was
another question to be asked.  Would she be doing it to help
Gregg, or to hurt Juliet.  Taking her place at the Awards was one
thing, deflowering her son something else.
	"Brooke ...?"  Gregg asked, seeing that his hostess was
lost in her thoughts.
	"Gregg,"  she replied, snapping out of her musings.
"Are you sure that this is what you want?  I mean really sure?"
	"More than being on the show, or doing that movie, or
anything."  came his reply, in a voice full of youthful passion.
	"Then I guess it's good that we live in a city where
dreams are supposed to come true."
	With that, she took his hand and guided it under the top
of her gown.  His outstretched fingers, pressing against her
naked breast.  Their lips met once more, this time it being
Brooke's tongue that sought out his.

	Taking Gregg by the hand, Brooke led him into her
bedroom.  It was the first time he had ever been there.  Next to
the living room, it was the most spacious in the house.  The
evening's natural light filled the room, provided by twin skylights
and a large glass patio door that led to the deck and beach
beyond.  The vertical blinds along the door had been left open to
admit the nightlight.  If you were to look up out of the skylights,
you'd see a large full moon filling the star-studded sky.
	In the center of the room stood a large platform bed.
Close to the floor, it was covered with a soft mattress and bright
black satin sheets.  A small reading lamp was attached to the
head, although Brooke was sure she wasn't going to get much
reading done tonight.

	Sitting on the edge if the bed, Brooke undid Gregg's bow
tie and used it to pull him close, their lips colliding once again.
Gregg had left his jacket and vest in the living room so all he
had left was his shirt and pants.
	One by one, the buttons of his designer shirt opened
under Brooke's skillful fingers and as their mouth and tongues
continued their erotic interchange.  As the last button came
loose, the redhead grabbed the sides of his shirt and pulled it
down across his body and off his arms.  His undershirt followed
just as quickly as Brooke slipped her hands under the bottom
and pushed it upward, exposing the lightly haired chest beneath
it.  As the cotton top slid up and over Gregg's head, Brooke ran
both her fingers and her mouth across his chest.  The dark
haired teen was surprised to find that a man's nipples were no
less sensitive then he'd heard a woman were supposed to be.
Especially when they were caressed by an eager, wet tongue.
	"Oh wow!"  Gregg gasped as Brooke licked his small
tips.  "That feels really nice."
	"It only gets better,"  Brooke promised as she reached
down and groped his cock through his pants.  A cock grown
quite hard.
	With her lips still planting kisses across his chest,
Brooke ran one hand up along his equally smooth back, while
the other continued to lightly pump his cock.  She paused for a
moment to look up into his face, only to fine the smile she wore
reflected there.
	Breaking contact, Brooke sat Gregg next to her on the
bed and then stood up herself.  Pointing out the zipper on the
back of her dress, she asked him to pull it down.  A favor he was
more than glad to do.  Once open, the evening gown lost it's
form fitting nature and would've fallen free had the older woman
not use one hand to hold the front tight against her chest.
	Still holding the covering in place, Brooke sat on
Gregg's lap, pressing his cock against the folds of her ass.  With
her free hand, she guided his hands to take the place of her
own.  His fingers tight against the material, Gregg cupped each
of her mounds as Brooke began to gyrate back and forth, again
pumping his cock, this time with the cheeks of her ass.
	"Slide them under my dress,"  she instructed him as he
let go of the material and replaced rich fabric with even softer
flesh.  No longer held in place, her dress dropped down to
around her waist.
	Spurred on by the pleasing pressure against his cock,
Gregg played with her heavy globes with an almost childish
delight.  His fingers massaged and squeezed the warm mounds,
pressing against her thick, hard nipples again and again.  Letting
out a long, soft moan of appreciation, Brooke leaned back and
reaching her head back over her shoulder, gave him a long,
loving kiss.
	She let him play with his new toys for a while longer,
then stood up just long enough to slide her dress the rest of the
way off.  Turning around, Brooke climbed back onto his lap, this
time face to face.  With only her thin panties now between his
cock and her ass, the sensations for both of them grew in
intensity.
	Gregg reached out and took her breasts in hand,
continuing to sample their delightful feel.  Leaning as forward as
he could, he added an oral examination of their softness as well.
Brooke again purred as he tried to duplicate the caress she had
given his tips a thousand or so heartbeats before.
	An idle thought entered her head, a curiosity as to
whose breasts he considered more attractive - Paige's or hers.
As soon as the thought had been formed, she tossed it aside as
an unfair comparison.  She knew enough about young men, and
all men were still young men in some aspect or another, to know
that they never forgot their first look at a naked breast.  It didn't
matter if it belongs to their sister or even their mother, as it had
in many cases, a naked boob was a naked boob.  The
excitement of that moment wasn't something their would ever
forget.
	"Well if I couldn't be first,"  Brooke told herself as she
helped guild his mouth to her most sensitive spots, "I'll defiantly
make sure I'm at least as memorable, even if he lives to be
ninety."
	Shifting her position off his lap and onto the bed in a
way as to still allow him access to her charms, Brooke reached
down and undid Gregg's own zipper.  Her hand slipped into his
pants, returning a moment later with his stiff and fully erect cock.
Long deft fingers glide up and down it's six and a half-inch
length, wrapping around its not unimpressive girth as they loved.
	"A lot nicer than I expected,"  Brooke considered as she
looked down at her prize.  "A lot better indeed.
	Sliding off the edge of the bed, the short haired woman
dropped to her knees and kissed the head of his cock.  Her
nimble tongue running across the top, wiping away the small
droplet of pre-come that had formed there.  Then her lips moved
up and down its length, her tongue darting back and forth as she
moved.
	Gregg was in heaven as she orally massaged his cock.
He'd spent countless nights wondering how this would feel,
overjoyed to discover that the reality outdid his imagination.
What he didn't realize was that this was only an overture to what
came next.
	Gregg's mouth abruptly opened wide in exclamation as
Brooke took him whole into her mouth.  He didn't have the words
to describe what he was feeling.  All he knew was that however
far fetched the claims he'd heard about how great a blow job
was, at this moment they were now as good as gold.
	If there was one thing that Brooke had learned on her
rise among the ranks of Hollywood elite, it was how to give a
first class blow job.  A talent that Gregg was now the prime
beneficiary of.
	With a practiced skill, the star of Dear Prudence" moved
his cock in and out of her mouth, drawing the very life out of his
young manhood.  She alternated between sliding her head back
and forth along the length of his cock, and simply taking a tight
hold on it and pumping it in and out of her mouth.  Through it all,
Brooke couldn't help but be impressed with Gregg's self control.
Most men she'd been intimate with, never mind one his age,
would've blow his load a long time ago.
	A second stray thought flashed through her mind as she
continued to send her young lover on a voyage of erotic
discovery.  A few months back, a friend had forwarded to her a
fan fiction story he'd found on the Internet.  The story had
depicted sexual relations between Prudence Greer and her son,
Carter.  With Gregg's cock in her mouth, and soon to be deep in
much more intimate places, Brooke wondered what that author
would say if she knew that her fantasy was, after a fashion,
coming true.
	Gregg's cock slipped from her mouth and rather than
just guide it back in, Brooke instead lifted both her breasts and
pressed them against his cock.  Moving her entire body up and
down, she gave him what her first husband liked to describe as a
"titty fuck".  After a few moments, it was clear that Gregg was
just as appreciative of the act as husband number one had
been.
	Releasing the hold on her mounds and letting his cock
slide free once more, Brooke stood up and pressed her breasts
this time against his face  As she covering it with her flesh,
Gregg kissed and licked her softness, taking as much of her
nipples into his mouth as he could.
	Brooke pressed forward, pushing the slightly taller young
man down flat on the bed.  She pressed her body against his,
then rolling off just long enough to quickly take off the rest of his
clothing.  Now between the two of them, only her panties
remained.
	"Want to see what else you can use that talented tongue
for?"  she laughingly asked as she moved up over his body until
his head was resting  between her legs.  It had been a rhetorical
question, one that she hadn't expected an answer to.
	However, Gregg did answer, muttering a reluctant
agreement.  Of all the sexual acts he'd heard guys on the show
brag about, this was the one he'd had the least enthusiasm
about learning.  The reluctance was one that Brooke had heard
before, and one that she was going to set straight in his
impressionable mind right now.
	"Trust me, Gregg,"  she said in a soft, caring tone.  "You
learn how to do this right, no woman is ever going to want you to
leave her bed."
	With a promise like that, Gregg decided it was at least
worth a try.  After all, Brooke had been right about everything up
to this point.
	Dropping down a little lower, Brooke pressed her now
stained panties against his face, filling his nostrils with the strong
aroma of her sex.  Gregg was taken by surprise for a moment,
then delighted to learn that it was a pleasing perfume.  His only
other experience with the scent of a woman had been with a pair
of his mother's panties that he had stolen out of the hamper one
night.  Mixed with other odors, it hadn't encouraged him to try a
second pair.
	Reaching down, Brooke undid the clasps that held her
panties together and they fell on his face.  She picked them up
and tossed them onto the night table, thinking that perhaps
Gregg might like them as a souvenir later.
	Faced now with the real thing, Gregg pressed his face
hard against it and made the mistakes most young, and some
not so young, men usually made.  Brooke was quick to correct
him, showing him exactly where to use his tongue.
	"Right there,"  she said as she struck home. "Oh yes,
that's the place.  It might be a little different on each woman, but
if you just pay attention you should have no trouble finding it."
	Brooke's words of encouragement gave way to little
squeals of delight as Gregg applied the lessons she had just
taught him.  Once he got into it, and especially when he saw the
effect it had on the woman above him, the young man no longer
had the least hesitation about going down on a woman.  Or in
this case, was it going up?
  	After a while this too came to an end, this time it was
Brooke who was reluctant to end this phase of instruction and
move on.  Gregg on the other hand,  was worked up and excited
because he knew there was nothing much left other than being
inside of her.
	Falling back onto the wide bed, Brooke directed Gregg
into what he knew was the classic missionary position.  For the
basics, Brooke knew there was nothing better for a first time.
Then again, who ever said she had to stay with the basics.
	Holding the head of his cock, she placed it at the
entrance of her pussy and whispered into his ear to press
forward.  At this point, Gregg hardly needed instruction, having
thought about this moment almost from the day he'd had his first
hard on.  He pressed into her with all of his weight, only worrying
at the last possible moment that he might be hurting her.
	Brooke was quick to dispel that thought as she
responded to his thrust with a passionate yes and encouraged
him to do it over and over.  Her sugar walls were so lubricated
by their earlier play that it took no time at all for the two of them
in develop a quick rhythm.
	Her hands pressed hard against his ass, pumping his
body into her with a rising strength.  Gregg had his arms
wrapped around her as well, pulling them together even more.
	They went on for a while until Brooke suddenly pulled
him tight against her and then rolled the two of them on the bed.
Gregg was startled for a second to find himself suddenly on the
bottom, but not as much as he was to discover that now Brooke
was fucking him.
	Moving into the female superior position, her personal
favorite, Brooke lifted her entire body into the air, before
slamming it down again on his cock.  Again and again, faster
and faster, she rode him, unlocking new sensations that he had
never before imagined.  Her hand moved up to her breasts,
playing with them as she moved.  At one point, she was able to
stretch out her tongue and lick her own nipples.  Something that
almost made Gregg lose that impressive self control.
	Perhaps sensing that he would indeed not be able to
hold it much longer, Brooke decided she had time for one last
lesson.  Climbing off Gregg, she got down on all fours and had
him enter her doggie style.
	Holding onto her hips as he slammed his balls again her
as hard as he could, Gregg decided that this was his favorite of
the three positions they had tried.  A fact that wasn't lost on
Brooke as she could feel his increased enthusiasm.  She
wondered for a moment how he might react to anal sex, but then
decided that some things might be better left to another time.
Some men reacted to anal, even with a woman, as an indication
of homosexuality.  Now wasn't the best time to explore such
things.
	Besides, already she could feel his body tensing, a
condition that she had been feeling within herself as well.
Neither of them was far from a climax.
	Grabbing hold of her swaying breasts, Gregg held them
tight as his sweat covered body slammed into her once more.
This time, his cock exploded as bolts of whiteness splattered
within her pussy.  And with them, his virginity.
	That thought, if nothing else, was enough to set off
Brooke's own orgasm.  One as pleasing as she had ever know.
This, despite the fact that Gregg had pulled out of her at the last
moment as he began to come, splattering a second and third
wave of whiteness across her ass and back.  Is hadn't been
enough for him to want to feel his climax, he'd wanted to see it
was well.
	Drained, Brooke dropped down on the bed, with Gregg
right on top of her.  She didn't have to look to know he had the
widest of grins on his face right now.  Reaching back, she ran
her fingers across her ass, wiping up some of the aftermath of
his eruption.  Bringing her fingers to her mouth, she carefully
licked them clean, savoring the trophy of his first time.

	They lay there on top of each other for a while, listening
to the twin echoes of their heartbeats and the splash of the surf
down on the small beach.  Brooke wondered what Gregg's
thoughts were at this moment, but decided it best not to intrude.
If he wanted to share them, she'd know soon enough.



(missing parts may be found at)

Ann Douglas Web Page

http://www.asstr-mirror.org/files/Authors/Ann_Douglas/www/

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