A Hollywood Equation

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Alyssa Milano decides to rethink her dating strategy.
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cdog21
cdog21
16 Followers

Starring: Alyssa Milano

Codes: MF, Oral, Con

Disclaimer: The following story is completely fictional. The events that take place within are entirely make-believe.

Los Angeles was a city where you could turn your dreams into reality. For the rich and powerful, it was a playground of opportunities. In the case of movie and TV star, Alyssa Milano, L.A. was proving to be an inhospitable desert to her dating life.

"Amy, you have no idea how hard it is for me to meet someone real." the brunette actress said to her close friend.

Amy Hartley had known Alyssa for nearly 20 years. After guest starring on several episodes of Who's The Boss? the two had struck up a friendship that had lasted the test of time. After retiring from acting, the 32-year-old blonde had recently opened up a dating service in the Los Angeles area with another friend named Tiffany Blake. While their service hadn't helped any of LA's more famous inhabitants yet, their business had quickly proven itself to be a huge success when it came to matching up their clients with the right person for them. Last week while having lunch together, Alyssa had made an offhand comment to her about maybe having better luck if she'd signed up for the service. Though she had meant it jokingly, that offhand comment eventually led to today with the two close friends lounging around the pool of Alyssa's Bell Canyon home discussing her flailing love life.

"During the week I'm on the set of Charmed all day long. On the weekends I'm home alone memorizing the scripts we're shooting the following week." Alyssa explained. "It's gotten to the point that it's become impossible for me to meet anybody except for the guys working as extras on the show and they're always too scared to come and talk to me like a regular person."

"Well, you are Alyssa Milano." Amy said playfully. "Is it really so surprising that guys tend to get tongue-tied when they're talking to one of the 'sexiest women' alive?"

"Ah. Alyssa Milano." she said with a wistful tone to her voice. "I know what I look like, Amy. I've got no problem being desired by guys. All I want to know is if finding someone that sees me as just 'Alyssa' too much to ask for?"

"No, sweetie. Of course, it isn't." Amy replied. "But I guess that answers the question as to why you asked me to help you find somebody outside of the industry."

"Exactly!" Alyssa exclaimed. "If I want a chance at building a lasting relationship, then I need to start looking for guys outside of my comfort zone."

"Got ya. So, tell me about your last boyfriend."

"Fling, not boyfriend." Alyssa clarified. "I haven't had a lot of luck in getting my relationships to last long enough to get to the boyfriend/girlfriend phase. I was hoping that things could have gotten to that point with Stephen, but I guess fate had other ideas."

"What was Stephen like?" Amy asked.

"Tall, blonde, a body like Adonis." Alyssa described in fond reminiscence. "He told me that he was an accountant, which believe it or not, was actually kind of a turn-on for me. After we had a few nice dates, Stephen decided to visit me on set one day and we wound up having a long... 'talk' in my trailer."

************************************************************************************************************

Ray-Art Studios

Three Months Ago

Near the set for Charmed, the sounds of pleasure-filled moans and lewd slurping noises could be heard emanating from Alyssa Milano's dressing room trailer.

Inside the trailer, Stephen Moore sat spread out across a leather couch. His head of short-cropped blonde hair lay against the back of the couch while he sat there with his legs spread wide and his jeans and boxers pooled around his ankles. Knelt between his legs, Alyssa Milano used every trick in her arsenal as she displayed the full range of her oral ability. Full red lips kissed and caressed the engorged pillar emerging from Stephen's lap as her mouth worked him over. Moans of encouragement issued forth from his open mouth while the actress's hands slid up and down his saliva-coated shaft, her tongue teasingly flicking back and forth across the tip of his cock.

"Look at me, Stephen." Alyssa said while she slowly stroked him.

Stephen lifted his head to look at the brunette with a pleasure-addled gaze. The beautiful actress grew even more aroused by the slack-jawed and wide-eyed look he held. Once she was sure that his eyes would stay locked onto her, Alyssa lowered her head and dragged her tongue from the base to the tip of her lover's cock. Precum leaked into her mouth, sweet and salty as she kissed him, licked him... tasted him. The agile tip of her tongue toyed with his slit, eagerly seeking out the delicious fluid leaking from him and smearing her tongue and lips in it.

"Do you like that baby?" Alyssa asked after she pulled back. Her voice was low and husky with passion and undisguised need. "Do you like how good my mouth feels on you?"

"Fuck yeah." Stephen moaned.

"Then hang on tight, baby." Alyssa said with seductive eyes. "This next part is where the real fun begins."

Without any more preamble, Alyssa opened her mouth wider and dropped her head down, devouring him in one smooth motion. Stephen moaned in bliss as his manhood slid between her soft lips and found himself lodged deep within Alyssa's throat. Stephen's girth, thicker at the base than at the tip, stretched her lips wide, but she forced herself further downward until his curly nest of pubic hair tickled her nose.

Alyssa held him there for several seconds, her tongue writhing around him as she sucked him, her cheeks hollowed and flushed by her efforts. Stephen's cock throbbed and leaked precum straight down her straining throat. Then she slid back up, releasing his cock with an audible pop that sent it swaying back and forth in front of her.

"Jesus Christ, Alyssa!"

Alyssa grinned for a moment and then swallowed him again. Her lips swept up and down his thick member as her head bobbed in his lap. Her tongue and throat caressed him, urging him on. Stephen's fingers wound through the tangle of her thick brunette hair and pushed Alyssa's head downward, forcing more of his cock into her mouth. His hips lifted up in rhythm to her movement, fucking the Charmed actress's mouth just as much as her mouth fucked him. Her pink halter top was pulled down around her waist allowing her large, braless tits to swing free. The engorged pink nipples that capped her heavy orbs brushed back and forth across Stephen's thighs as she devoured him.

Alyssa looked up into Stephen's eyes, enjoying the look of pure lust that contorted his face almost as much as she enjoyed the feel and taste of his cock sliding between her lips.

Her tongue felt the flutter at the base of his cock as his arousal increased. His strokes grew quicker and shorter. Gently but insistently, Alyssa pulled Stephen's hands away from her head. She pulled her lips off of him, strings of saliva linking her lips to his cock, and gripped the base of him tightly. Alyssa stuck out her tongue and laid his plum-sized cockhead against her tongue as she stroked him fast and furiously. She couldn't fight back a smile as she watched him squirm under her touch.

Stephen gritted his teeth, trying to hold back the inevitable, as he stared in lustful wonder at what the famous actress was doing to him, but it was for naught. Stephen's cock twitched and throbbed angrily in her hand as he exploded. Several jets of pearly white cum sprayed inside Alyssa's open mouth, coating her tongue and lips with his white frosting. His load quickly filled her mouth, and when she was forced to swallow, his cock spurted another rope across her lips and cheek. Her mouth was open again a second later and neatly caught the next few spurts.

Once his orgasm finished, Alyssa swallowed her present greedily and looked up at her lover with a mixture of astonishment and passion. Stephen's cum was thick and delicious, and he came in sizeable amounts. She sucked the head of his cock back into her mouth, cleaning him off, licking up every last drop of his seed, before swallowing it down. She dragged a finger across her cheek and collected the errant strand of semen before popping the appendage between her lips and licking it clean.

Despite his powerful release, Alyssa was pleasantly surprised to see that her lover had not gone flaccid in even the tiniest bit. His cock still towered over her; long, rigid, and powerful. Alyssa's lips quirked up into a smirk.

"I guess I've got my work cut out for me."

Alyssa stood up, reaching beneath the fabric of her skirt, and peeled the wet, black thong away from her pussy. She slid the underwear down her long legs, her fingertips brushing across her black stockings, then awkwardly kicked them free of her feet.

"Stand up." Alyssa ordered.

Obligingly, Stephen got to his feet and moved out of the way. She took his place on the couch, leaning forward with her heavy breasts hanging beneath her as her ass rose in the air. Bracing her hands against the back of the couch, she tossed her wild brunette mane over her shoulder and gave him a smoldering look.

There was no misinterpreting its meaning.

Stephen pulled his legs free from the tangle of clothing around his ankles as he moved to stand behind his lover. His large hands pushed her skirt up and out of the way before they squeezed the full globes of her curvy bottom. He kneaded the soft flesh of her ass, fully enthralled by the sight before him. His fingertips left burning trails across her flesh as they touched and caressed her. Alyssa panted with lust as Stephen's fingers moved over her naked body. She let out a whorish moan when they finally found her searing opening. Agile fingers teased her pink, weeping folds stoking the flames of her lust.

Alyssa felt his fingers pull away from her before being replaced by something hard and thick nudging against her labia. A strong hand gripped her waist tightly as the other guided the engorged head of his cock into her leaking tunnel.

In an almost instinctive manner, Alyssa arched her back into a deeper S-curve, raising her ass further and spreading her legs wider. Her pussy widened as well, desperate to accept the intruder preparing to plunder the most hallowed part of her body.

"I'm going to fuck you so good, baby." Stephen said teasingly, a wicked shiver going up Alyssa's spine at his words. "You've been thinking about this dick all day, haven't you?"

She had never been more ready for anything in her life. "I need it, baby. I need you to fuck me so bad." Alyssa moaned. She cried out as Stephen complied and thrust forward. His thick slab of flesh buried deep within her, piercing her, nearly driving the breath from her as his wonderful cock spread her flesh as it made its way inside of her. She had already been worked up from the blowjob she gave him and the sensation of him sliding inside her sent Alyssa over the edge almost immediately.

Stephen stood hunched over her for a moment, his thick cock embedded deep within her as he waited for her to recover. Alyssa shook beneath him from aftershocks of her orgasm, soft moans escaping from between her pouty lips as her muscles clamped tightly around his cock. Even with all that she had just experienced, he was still not entirely within her. A few inches of his manhood remained outside. He took several deep, sharp breaths, then slowly eased himself forward until the soft curves of her full ass flattened against the chiseled muscles of his abdomen.

For the next few minutes, Stephen entertained himself with Alyssa's reactions as he would slowly pull out of her clasping tunnel before reversing his movements and burying himself inside her once more. This slow, methodical tempo had Alyssa crying out and thrashing underneath him. His pace started to increase as it became easier for him to move inside of her. The couch wobbled under the force of their sensual movements. Stephen was certain that her cries could be heard from outside the trailer, but at that moment, he didn't care. He reveled in the feelings of absolute pleasure, and tremendous power, as his cock throbbed hard and happy deep within the actress's soaking pussy.

Stephen flexed his cock and Alyssa's vaginal muscles flexed with him. Her labia were spread wide by the girth of his cock, fluids leaking out to coat his swinging balls as they crashed against her. With a grunt, Stephen slowly withdrew, dragging his heavy cock out of his lover until only the head remained trapped inside of her delectable flesh. Then, savagely, almost brutally, he began to pound into her. Where before, what they were doing could have been classified as love-making. Now, it was pure unadulterated fucking. Stephen sawed his cock into her over and over, slamming her hard against the couch and driving himself to the hilt within her on every thrust.

Alyssa's moans slowly transformed into a steady wail, as the pleasure overwhelmed her. She couldn't tell when one orgasm began and another one ended. With every thrust, her lover stoked the raging inferno that had consumed her loins and her heart. Stephen ravaged her and she loved him for it.

For Stephen, every inch of his cock felt like it had been swallowed by fire and only Alyssa's sweet pussy could quench the flames. Again and again, he drove himself into her, gripping her waist tightly as he buried himself inside her.

"A-Alyssa..." Stephen grunted as he became aware of the familiar tightening in his balls. "Baby, I'm about to cum!"

Alyssa moaned and shuddered. "Give it to me, Stephen. I want to feel you cum inside of me!"

Stephen groaned as he pulled out, then brutally slammed back inside of her. They both felt his already immense cock expand even further inside her and then with a shuddering throb, he sprayed Alyssa's womb with his seed. He felt each powerful spurt as it traveled up the long column of his throbbing flesh and shot itself deep within his lover. Alyssa moaned loudly as she felt it splatter against the walls of her womb. The sensation of Stephen releasing inside of her pushed her into her biggest orgasm yet. She saw spots. Her fingers and toes curled from the ecstasy that had swallowed her. Tears of joy and pleasure dripped from her closed eyes as a wordless moan left her lips.

And still, Stephen continued to empty himself into her. His mighty cannon fired over and over, unloading a copious amount of his viscous, white seed into her depths. It filled her, seeping out past her stretched labia, and leaking onto Stephen's contracting testicles.

Once the last spurt had left his body, Stephen curled himself over top of Alyssa, gasping for air. Alyssa's strength finally gave out and she slid to the floor. Stephen followed her, still buried inside her spasming channel.

Alyssa lost consciousness, stirring only slightly as Stephen pulled himself away from her. His cock came free with a slurping sound, followed shortly after by a rivulet of semen leaking out of Alyssa's ravaged pussy and staining her thighs and the floor beneath her.

Gasping to try and recover his breath, Stephen slumped backward on the floor of the trailer. A wide smile spread across his lips as he basked in the afterglow of their lovemaking.

************************************************************************************************************

Present Day

Alyssa closed her eyes as she enjoyed the memory of the antics she and Stephen got up to that day in her trailer.

"The sex was fantastic." She said to Amy before opening her eyes again and frowning. The memory of what happened after their lovemaking that day soured any enjoyment she had reminiscing about Stephen. "No, my sex life with Stephen wasn't the problem. The problem that we had was that Stephen was a liar. He wasn't an accountant, Stephen was an actor looking for an 'in'."

************************************************************************************************************

Halliwell Manor Set

Three Months Ago

Shooting had finally finished for the day and Alyssa was on the hunt for her lover. He was supposed to be waiting here for her, but somehow he'd hidden himself away. She was just about to call out his name when she heard his voice talking to someone. Curiosity getting the better of her, she quietly approached the corner to the Foyer set where Stephen was standing and ducked behind a nearby prop so she could hear more of the conversation.

"I swear to God, dude." he said, practically bouncing on his heels. "Alyssa was all over me."

...

"You'd think so, but trust me, none of those movies can even come close once you've seen her naked in person."

...

"After what we did, I'm sure she wouldn't mind if I asked her to drop my name in a couple of producers' ears."

...

"I don't know how I managed to pull it off either." Stephen replied. "I'll tell you one thing though, that woman really knows how to put in some work." Suddenly, Stephen's phone beeped with an incoming call. "I got another call on the line, so I gotta go. I just wanted to catch you up on things."

...

"Alright, dude, I'll holler at you later."

Alyssa turned and walked away, any attempt at a stealthy exit abandoned by her disappointment as she disappeared around a corner.

************************************************************************************************************

Present Day

"I don't hate him for what he did. Hell, under the right circumstances, I might have done something similar." Alyssa sighed dejectedly. "I just want to be free to be me, you know? I don't want to feel like I always have to question the motivations of the guy that I'm sleeping with or be worried about the private details of my life getting plastered across the fucking internet."

"I completely understand, sweetie." Amy replied. "So, what type of guy do you think would make you happy?"

Alyssa looked at her close friend with a frown as she wondered about the same thing.

************************************************************************************************************

West Coast Cupid

Two Days Later

A handsome man wearing wire-framed glasses sat patiently at a wooden table. His inquisitive gaze wandered around the expertly decorated room while he waited to be seen by one of the dating service's representatives. On the way over and even while he waited to be seen, the man had gone back and forth over whether this was the right move for him to make. However, nothing he had done so far seemed to work when it came to trying to find someone that he could make a connection with. That doubt started to creep back up and he was about to just call the whole thing off when he heard the sound of footsteps approaching. Turning around, the man had expected to see the visage of the older woman who'd shown him inside earlier returning with his drink. Instead, he found a stunningly beautiful brunette woman with two drinks in her hand walking down the hall toward him. Dressed in a black lace top that left her arms and lower torso exposed to view and a pair of hip-hugging jeans, the woman was definitely dressed to catch the eye.

"Your iced tea." the woman said as she placed the drink in front of him before she sat down at the table with him. "My name is Tiffany Blake. I'm one of the co-owners of West Coast Cupid. How can we be of service Mr..."

"Harris. David Harris." he replied a little nervously as they shook hands.

"It's nice to meet you, David." Tiffany replied. "Why don't you tell me a little about yourself so I can figure out how to help you."

"Well, I'm uh... I'm a math professor. I teach calculus courses at the University of Michigan. I've been on sabbatical for the last year so that I could finish writing my book on chaos theory."

"Oh! You're a writer as well as a professor." Tiffany said with genuine interest at his revelation.

cdog21
cdog21
16 Followers