A Series of Firsts

Series of Firsts

Julie Dolan was excited. She was starting her first full-time job. Graduating from high school and turning 18 in June had been an awesome start to the summer. She had taken the summer off to spend with Fred, her long time boyfriend, before he went off to college.

She had applied for an entry level position in the local office of a national financial firm. Julie had been interested in the stock market as long as she could remember and hoped this job would enable her to learn more about investing.

She was sitting in the office of the person who ran the office, David Shaw, and one of the financial advisors, Richard Jacobs. Both in their early thirties, they were being groomed for "climbing the corporate ladder." Julie was dressed in a business suit consisting of a jacket with matching pants and a white blouse.

David explained that her duties at first would be limited to answering the phone, running copies and filing, but based on her performance, she might be trained as a junior advisor. Since she would be the only assistant in this small office, it would be imperative that she be efficient and reliable.

"You've met Phyllis, our accountant." Mr. Shaw said to Julie.

"Go to her office and ask her to show you the ropes. She's expecting you."

With that the two men shook Julie's hand and wished her good luck.

When she had left the office and he had shut the door, Richard said to David.

"Holy shit! What a young piece of ass! I'd love to fuck the hell out of her! Are you sure she's 18?"

"Number one, although she looks younger, she's definitely 18, two, she's very bright and did well in high school but decided against college, three we needed a new assistant."

"Who gives a shit! Richard replies. "She's smoking fucking hot!"

Laughing, David points to the door saying, "Go make some money!"

Settling into the office routine, Julie's first few weeks at the office passed quickly. Although she missed Fred, she was really enjoying her job and the tidbits of the financial world she was picking up. At night, instead of going out, she was reading everything she could find on the investments the firm handled.

As she was preparing to leave one evening, David called out to her.

"Got a minute"?

"Of course Mr. Shaw!" Julie answered.

"Mr. Jacobs and I are attending a seminar on new market trends in Puerto Rico next week. We are very impressed with both your work ethic and the aptitude you've shown for the investment world. In short, we've arranged for you to attend also."

Unable to contain herself, Julie hugs David saying, "Thank you so much! I'm so excite and grateful!"

Pleasantly surprised by the hug, David hugs Julie back, feeling her perky breasts pressed against his chest and a stirring in his groin.

"Damn!" he thinks to himself. "Richard is right! She is a prime piece of ass!"

As they separate, David tells Julie, "No need to thank me. You've earned it. By the way, you should pack one nice dress for the opening night's reception dinner. Business casual is fine for the conference. And bring a bathing suit if you like. The conference is at a resort outside of San Juan."

As she leaves, Julie thanks him again.

Driving home, she calls Fred to tell him about the conference.

"That's great. But do you think it's a good idea to go with two men and no other women?" Fred asks.

"What are you insinuating Fred? Mr. Shaw and Mr. Jacobs are both twice my age! And I'm sure there will be other women at the conference!" an angry Julie retorts.

"I'm sorry." replies Fred, feeling bad about raining on Julie's parade.

"Have a great time and call me when you get back."

Calming a bit, Julie tells Fred that it will be all work and that she will call as soon as she returns.

Arriving home, Julie excitedly tells her mother about the trip and asks if she has a dress that Julie can borrow.

Since her mom was the same size 8 as Julie, the snug fitting short black dress fit Julie perfectly. At 44, Mrs. Dolan was the epitome of a MILF, one who was not afraid to use sex to further her career. But that's a story for another time!

That Monday, Julie hardly contain her excitement as you watch Puerto Rico through the window of her first class cabin seat. I was even more excited to find a private limo but took Mr. Sheila Mr. Jacobson her to the El conquistador resort just outside of San Juan.

"It's only one o'clock. Why don't you grab lunch by the pool and then we can relax there maybe have a dip until later this afternoon. Cocktail hour for the reception dinner is not till 630." David tells Julie and Richard.

"Let's meet by the pool bar in about 15 minutes."

When Julie arrives at the beach bar, wearing a translucent cover-up over her bikini David and Richard are already there.

Backflip by the sun behind her, Julie's body is clearly outlined underneath the cover-up.

"Fuck! I've got to nail that!" Richard says to David..

"Relax! We both will. But I'm first!" David says.

As Julie sits down, she says " I have a beautiful room Mr. Shaw! Thank you so much!"

"Richard and David while we're here. We can save the formalities for the office."

David and Richard order drinks. Thinking it sophisticated, Julie orders a white wine.

Mmmmm, she thinks. Much better than the cheap beer Fred and she usually drink.

Knowing she's not much of a drinker, Julie nurses the wine throughout lunch.

When they finish lunch, Richard announces they have a couple of hours to spend by the pool

Reaching the lounge chairs, Julie pulls the cover over her head, displaying her toned thighs, flat stomach and the tops of her perky breasts, still tanned from her summer sun bathing. Diving into the water, she swims the width of the pool, then floats languidly on her back, earning admiring glances from David, Richard and most of the other men there.

"Who is that girl you had lunch with? With the body to kill for?" asks one of the other attendees.

"She's our new office admin. She's shown some real aptitude for finance, so we brought her to the conference," David answers.

"I'm sure that's why you brought her!" says the other man, snickering.

Laughing, Richard chimes in, "Relax. She's young enough to be my daughter!" as he joins Julie in the water.

After a close up look at her nipples poking through the thin fabric of her bathing suit and her pronounced camel toe,

Richard says to Julie,

"Better than the office routine?"

Startled from her reverie, Julie stands up quickly in the waist deep water, affording Richard a short glimpse of her entire breast.

Recovering quickly, Julie replies,

"Although I love my job, this is very nice!"

"There's an island that the resort has. It's supposed to have spectacular beaches. They have a free shuttle. We can give it a try tomorrow after the seminar if you'd like," says Richard, conveniently leaving out the fact that the beaches are clothing optional.

"Sounds awesome!" answers Julie, adding, "I'm going back to my room to rest and get ready for tonight's dinner."

Richard follows her up the pool ladder, appreciating the view of Julie's firm, round ass, inches from his face.

Slipping into her cover up, Julie tells the two men she'll see them at the dinner and walks off.

"I get her tonight. You can nail her tomorrow, " David tells Richard.

Chuckling, Richard answers, "You seem very sure of yourself!"

David just smiles.

Later that evening, the three meet in the lobby then proceed into the space where the dinner is being held.

When they get to the bar, Julie announces that she wants to try a mojito.

"Of course miss!" says the bartender, drinking in the sight of Julie in the form fitting, scoop necked, mid thigh black dress.

Making the rounds of the room, exchanging small talk with the other guests, David fetches Julie her third mojito.

As they sit down for dinner, the two men flanking her, Julie realizes that she is getting a little buzzed and drinks only water during the first course.

The band starts up while the tables are being cleared, playing a song Julie likes. Seeing her move to the music in her seat, David asks if she would like to dance. She gladly accepts and as David leads her onto the dance floor, Richard gets Julie a fresh mojito.

Holding her at a respectful distance, David is thinking about what Julie's body would feel like under his. The song ends and they return to the table.

Richard proposes a toast to an interesting conference and a successful year.

Julie mimics the two men and drinks most of hers in one gulp.

As the dinner progresses, David and Richard make sure Julie's glass is never empty. The dancing continues, with both David and Richard as partners. No more respectable gap during slow dances. Julie's arms are around David's neck, her body pressed tightly to his for the final dance of the evening.

As they leave, David proposes that they all go back to his room for a nightcap. Julie, quite tipsy, agrees immediately.

Richard begs off, as David and he had planned.

"See you all tomorrow," he says walking off.

Julie puts her arm through Davids as the go to his room.

"Have a seat on the couch and I'll pour the drinks," David says as the enter the room.

Julie reclines on the couch, tucking her legs up, her dress riding up to the top of her thighs.

Returning with the drinks, David squeezes between Julie's back and the arm of the couch.

Handing her the glass, David taps his to Julie's and says "Cheers!"

"Cheers!" replies Julie, then downs it in one swallow, nestling back into David as she does.

Rubbing Julie's thigh with one hand, David kisses Julie's neck. Julie responds by turning her face to his and kissing him, her tongue probing into his mouth.

As Julie turns to him, David unzips the back of her dress. Julie shrugs out of the top of her dress, exposing a lacy black bra which David quickly unclasps and removes, freeing Julie's perky young breasts. Her nipples are large and puffy.

David flicks one with his tongue, soliciting a soft moan from Julie.

Sensing her building arousal, David sucks, then gently bites her nipple.

Moving his lips back to hers, David lifts Julie up and carries her to the bed. Laying her there, he quickly kicks off his shoes and leaning over her returns his attention to Julie's breasts as his hand rubs Julie's mound through her panties, open to his touch as her dress is bunched around her waist.

Sliding her panty to one side, David rubs Julie's clit with his thumb while his finger rubs her g-spot. He feels Julie start to move into his finger as one of her hands presses his head to her breast. He takes her to the edge, then withdraws his finger and thumb. Julie moans in frustration. David grasps each side of her waist band and pulls down as Julie raises her hips to help.

David stands, removes his shirt and drops his pants and boxers to the floor while Julie is rubbing her clit and pulling on one nipple.

David slides between Julie's legs and lowers his mouth to her pussy. He alternately licks and sucks on her clit while one middle finger rubs the roof of her cunt and his other had squeezes her tits and pulls her nipples.

Julie is by no means a virgin, but no one has ever eaten her pussy before. There had been one or two before Fred, but all had been fumbling boys who knew nothing about making a woman cum. David is a man with a lot of sexual experience.

His oral machinations drive Julie to the edge and then over. She holds David tight to her cunt as she bucks wildly against his face, cumming and squirting her way through a tremendous orgasm.

As Julie releases her grip on his head, David puts her knees on his shoulders and rams his painfully stiff cock into her pussy.

To his delight, although her cunt is sopping, she is very tight. Sawing in and out, David decides to find out if his hunch about Julie's submissive side is correct.

"You like my cock in your cunt, you little slut?" he demands, holding the tip of his dick just barely touching Julie's pussy lips.

"Yes" Julie moans, thrusting her pussy toward David's cock.

Pulling his cock back a little further, David says, "Beg me to fuck you, slut!"

"Fuck me! Please fuck me!" Julie begs, using her legs to pull her hungry pussy onto David's cock.

Keeping up a litany of verbal abuse, David fucks Julie with a machine-like intensity.

For her part, David's thick cock and his language are taking Julie to the heights of sexual pleasure.

With a loud "Oh Fuck!" David fills Julie's cunt with a prodigious amount of his semen.

Sated, he first collapses on Julie then rolls over onto his back.

Wanting almost desperately to cum again, Julie leans over David, playing with his cock and kissing him.

"Fuck me some more," Julie purrs.

Smiling, David tells her to suck him hard.

Julie hesitates.

"I've never done that. I don't think I can, especially when your dick is gooey."

Firmly grabbing Julie's hair, he pulls her head so she is looking right at him, David tells Julie'

"Listen you little slut! You want me to fuck you, you'd better suck my cock! Now!"

Sliding down David's torso, Julie takes his cum covered cock into her mouth and literally sucks on it.

"Not like that, you dumb bitch! Move your mouth up and down my shaft!" David orders.

Not knowing why, Julie is turned on by David's insults and desires to please him. She moves up and down, feeling it starting to stiffen in her mouth.

"Now swirl your tongue around the tip while sucking, slut!"

Julie does as ordered, David's cock now almost fully erect.

"I knew you would be a good little cock sucker! Now kneel over me and stick my cock into your cunt!"

Julie straddles David's thighs and impales herself on his cock, grinding her cunt into him.

Smacking Julie's ass, David tells her to play with her tits.

"Fuck yeah, slut!" David exclaims, pulling one of Julies hands from her tits and placing it near her pussy.

"Finger your self!"

As Julie complies, rubbing her clit, David slowly works a finger into her ass, while mauling her tits with his other hand.

Bouncing wildly on David's cock, spurred on by David's verbal assault and his fondling, as well as fingering her clit, Julie has a massive orgasm, rolling off David and onto her back next to him.

"I'm not done yet, bitch!" says David as he positions himself between Julie's legs. Spreading them apart, he lifts them and without delay, pistons in and out of Julie's sopping pussy.

As he starts to cum, he pulls out and hoses Julie's stomach, tits and chin with his seed.

Standing, he says to Julie, "Time for you to get back to your room. It's two am. and we have a 9 am. breakfast meeting.

"Exhausted, Julie asks, "Can't I stay here? I'm too tired to go to my room."

Switching to a mode of understanding, David says,

"I know, so am I."

Reaching over, he wipes some jizz from her chin and gently kisses Julie.

Retrieving a robe from the closet, he gives it to Julie, then collects her purse, bra and shoes, handing them to her as she slips the robe on, her cum covered dress still bunched around her waist.

"Your room is only two away. I'll watch to make sure you get there," David tells Julie as he guides her out of the room.

Returning to the bedroom, he retrieves the ipad which has been recording the night's "festivities".

"In case the whore doesn't want to remember," he says to himself as he watches some of the action.

Smiling, he thinks that he can't wait to show Richard.

To be continued.........