Dear Prudence

"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 eighteen and her boyfriend twenty-two. 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 an eager, wet tongue caressed them.

"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 blown 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 known. 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.

Time passed ever so slowly and Brooke was about to say something when Gregg beat her to it. He opened his mouth, said her name and was then abruptly cut off by the ringing of the telephone on the night table.

"I have to get that," Brooke apologized as still weighed down by Gregg's weight, she couldn't reach the phone. "Only a half dozen people have this number so it must be important."

In way of understanding, Gregg rolled off her to the empty side of the bed, giving her the chance to reach the ringing phone.

The voice that blasted her ear as she put the receiver to her head told her that the number of people with her private number had now grown by one.

"Where the fuck is my son?" the shrill voice screamed.

"Why hello, Juliet," Brooke answered calmly in a voice that gave no indication that she had just spent the better part of the last two hours fucking her son. "How are you this fine evening?"

"Don't fine evening me you bitch," Juliet yelled loud enough for Gregg to hear from where he laid on the bed. "Where is my son? The Awards Dinner has been over for hours."

Brooke glanced first over at the alarm clock next to the phone, it had indeed been hours since the Awards had ended. Then she looked to her neophyte lover, the expression on her face asking if he wanted her to lie and say he had left long ago.

"I've been calling all over town these last two hours," Juliet went on, oblivious to the fact that no one was really paying attention to her words. "When I got that little cunt, Joyce on your official number, I told her that if she didn't give me your private number right that minute, my next call was going to be to the police."

Gregg paused for a moment, then reached out for the phone. As if conscious that he was about to talk to his mother bare ass naked, he pulled on the sheet next to him until it covered his exposed manhood.

"Would you mind holding on for a moment, Juliet?" Brooke said in that same sweet tone in which she had answered the phone. There were times that being an accomplished actress did have its advantages.

Gregg took the cordless phone from Brooke and held it up to his ear. He listened for a second as Juliet was still telling Brooke that no, she wouldn't hang on a moment.

"Hello Mom," Gregg said, cutting her off in mid-rant.

"Gregg, honey," the voice on the phone said, shifting to a tone that was full of sweetness and kindness. "I've been so worried about you. What are you doing there so late?"

Able to hear what was going on, Brooke mentally translated the meaning of what Juliet had said to, "I've been so worried that you're out of my sight and control. What has that woman been doing to you?"

"I'm fine, mother," Gregg said, looking at a still fully naked Brooke as he spoke. "I've just been hanging with Brooke for a while. It's not like I have an early call or anything tomorrow."