Jack's enjoying his now regular dalliances with Diane. She's accustomed now to what "going over the numbers" means when summoned to Jack's office. She loves it because a good fucking by his big cock takes some of the stress out her day. So much so, that she's gone ahead stored a few items in his C-suite bathroom for their afternoon quickies: bralettes, thongs, thigh highs and heels; as well as some appropriate cosmetics, lipsticks and the like. She also has her own towel to shower after she's done fucking him.
Anna, Jack's gorgeous twentysomething staffer, is summoned by Jack to also "review some numbers" in his office. She arrives dressed as "professionally hot" as always: beige blouse, big white bra slightly visible underneath, black skirt, black belt with a pretty silver buckle and black pumps. She's had her hair done and looks fabulous. Her make-up is exquisite, eye shadow and lip gloss just perfect.
Anna puts her folders on Jack's desk and asks if she can use his restroom right quick.
"Sure!" Jack says before he remembers Diane's things are in there. Hopefully Anna won't open any drawers.
Unfortunately, unbeknownst to him, Diane's left her "come fuck me" heels out on top of the towel hamper.
"Ah ha," muses Anna, "I thought he might be fucking her. Might be time for some friendly 'girl competition,' see if I can outperform that bossy bitch."
With that Anna returns to his office, sashays up to his desk, and without saying a word opens the folder.
"Where would you like to start, Mr. Daniels?"
"You can call me Jack, Anna."
Anna giggles and says, "Alright JACK, where do we begin?"
After reviewing the numbers for a while, Jack surprises Anna and asks her to go do some more research and come see him around 3:00PM. This surprises her, she thought for sure he'd make a move on her during the review. However, Jack wants the sexual tension to build a bit, not to rush things. When he finally fucks her, he wants it to be memorable and bring her back for more, just like it did for Diane.
After Anna leaves the office, Jack gets his rock-hard cock out and edges it, pulling semen up from his sack. Feeling his cum swelling inside his shaft, he works his dick to near ejaculation then backs off. Everything in him says to cum right now, shoot his wad; however, the load he's preparing is for Miss Anna's pleasure, not for his lustful relief.
At 3PM, Anna returns. "Got the numbers for you!" she chimes.
Jack looks them over and says, "Great work, Anna, excellent research, this will be useful in preparing my report for the CEO."
With Anna close to him, Jack swears he can smell her sex. Had she been masturbating before coming to see him? The thought intrigues him, "Let's find out if she's horny."
Jack starts by massaging Anna's shoulders from behind to see what her response is to his touch.
"Ah, that feels sooo good!" purrs Anna.
Good sign! Neck, upper back, Jack's big hands feel wonderful to Anna, so stress relieving. He decides to try unbuttoning her blouse. He meets no resistance, another good sign. One button, a second one until all buttons ware now undone. Jack opens her shirt and starts massaging Anna's big, bra-encased tits; gradually sliding one hand inside a cup, then a second hand inside the other. Anna closes her eyes and moans as her big breasts fit perfectly in his large hands.
He takes both nipples between his thumbs and forefingers and continues massaging. Anna moans heavily as Jack gently pulls them, stretching her nipples and areolas out.
"Oh, fuck that feels really good!"
"I've always felt a woman's breasts deserved more attention during a massage, particularly large-breasted women like you, Anna."
"I like how you think, mister!" purrs Anna as she loosens her skirt and Jack unhooks and removes the big white bra.
This is Jack's final signal that Anna is DTF-down to fuck. Tossing her bra aside, Jack removes her skirt revealing a matching-colored thong underneath. Sliding one hand inside, his fingers find her slit, already wet. He keeps working her right breast with his right hand, while his left hand works her tight pussy. Anna moans as he slips his index finger into her now very wet cunt, then a second finger. The fapping sound starts building. Anna closes her eyes and moans.
Jack pauses the fondling and fingering just long enough to slip her thong down her perfectly round butt and hard legs, then gets Anna to help him by lifting a foot at a time to get the material over her heels. He then tosses the thong over with the bra and resumes the breast massage and cunt fingering. Anna moans and groans thoroughly enjoying her "massage."
Jack thinks, "She looks as good naked as I imagined. What a babe!"
His cock's hardened and now straining against his trousers for release, but he keeps fondling and fingering her toward orgasm. It takes a while but finally Anna is ready to cum.
"Oh fuck, I'm cumming, Jack. Oh fuck, FUCK! Fuck YES!!" Her bare ass presses against his hard cock as she closes her eyes and moans, mouth contorting in the familiar "O" shape and she comes in waves of womanly pleasure.
"Oh gawd, that was sooo good!" Anna purrs as her body starts to settle down after orgasm.
"God, was that hot!" thinks Jack as he slowly turns her around and kisses her. He muses, "How cool is this. I'm in my nice plush office, totally clothed, even still got my tie on, and this young bombshell is completely naked except for her heels. This is living the C-suite life!"
As they kiss, Anna reaches down to unbuckle his trousers. She really needs his hard boner for her horny mouth and pussy. Fumbling a bit with the belt buckle, he helps her get it loosened so she can remove his cock.
Upon eyeing his huge erection, Anna grins. "Oh wow, Jack, you're quite the manly man now aren't you? Look at this big handsome cock of yours!"
With that, she kneels down, slides his trousers down his thighs, creates working space for fellatio, and starts stroking his shaft, finally putting his cock head in her mouth.
Pausing momentarily, Anna says, "Your dick is so fucking big, Jack, I love how it curves. And your balls are just perfect. I love how your scrotum hangs low like that, so manly, mmm!"
"Suck it, baby: head, shaft and balls!"
Anna proceeds to work his cock over, just like he asked, head, shaft and finally each ball, one at a time. Jack feels in heaven as he looks down on her nakedness, so beautiful with her firm round ass and big fucking titties. Anna puts a finger in her pussy as she continues to fellatio her boss. Soon it's Jack who's the one moaning, then groaning in ecstasy about to cum.
"Oh fuck that's good! Keep sucking my dick, baby!"
Feeling close to ejaculating, Jack stops Anna's sucking, raises her up to a standing position and starts kissing her tongue-to-tongue. He's buying a little time to let his swollen shaft to subside a bit. He doesn't want to shoot his wad before he gets a chance to fuck her with his gun "fully loaded."
Jack walks her over to his big desk, places Anna's butt right where Diane's had been, and then bends down and starts tonguing her sweet, wet pussy. Anna moans as Jack finds her g-spot with the tip of his tongue. She grabs the back of his head, presses her pussy as firmly against his mouth as she can and starts moaning some more as Jack works her clit over.
"Oh gawd, Jack! Eat me! Mmm. Oh yes, that's it, right there baby, oh fuck yesss!!"
"Cum girl, cum for daddy, you're right there, baby doll, let loose!"
With that, Anna does let loose, hips bucking as her pussy spasms with waves of pleasure, accompanied by plenty of moans and groans.
"Atta girl, Anna!"
As her orgasm subsides, she says to Jack, "Fuck me! I need your big cock inside me! RIGHT NOW!!"
Jack spreads Anna wide, lays his big cock astride her wet slit, playfully slaps her cunt lips a couple times, then slides the his dick in slowly. Anna groans heavily as his nine inches slide deeper into her cunt until his balls are resting firmly against her labia. He then starts to pump, slowly at first, then harder until he's pounding her tight slit senseless. Anna grabs his firm arms and holds on for dear life.
Then he adds some dirty talk.
"Are you my dirty little slut, Anna?"
"Yes!! Ahhh, oh shit yes. Your dirty little slut, Jack!"
"Is daddy fucking the shit out of your hot pussy, baby doll?"
"Gawd yes, fuck my pussy, daddy! Oh shit, yesss!"
Feeling the cum swelling in his shaft and nearing ejaculation, Jack pulls out of Anna's cunt with a "popping sound." He isn't quite ready to release his load yet; he has a few more things he wants to do with his vixen first.
Lifting her up off the desk into a standing position, he turns Anna around and has her lay her arms on the desk. He then spreads her legs a bit wider and has her arch her ass a bit in doggy position.
"Wait there just a second," Jack says as he walks around to the front of his desk, cock sticking way out like a gladiator's sword, opens a drawer and takes out a butt plug and some lube.
"Let's get your ass involved in this, baby."
"I've never done anal before!"
"You'll love the butt plug. I'll go easy, get you used to having something in your ass."
Jack shows Anna the butt plug, lubes it up in front of her eyes, then walks behind her, spreads her ample ass cheeks and slowly inserts the head of the plug into her rosebud. Anna yelps, then gasps as the head of the plug works its way in.
"Aghhh, ohhh, mmm...that feels really good!"
Jack bends down, gives Anna's labia a couple of good licks, then slides one finger into her pussy, then another. Anna moans. Positioning his cock for cunt entry, he slides his head in, then a bit of the shaft, finally the whole nine inches until his balls hang beneath her slit; then he starts pumping, slowly at first, then picks up speed as he goes.
"Gawd ,that feels sooo good Jack!" Fuck me, fuck my pussy hard! HARDER! Oh gawd, mmm."
"Time for your anal OJT, baby!"
"What?"
Out comes the butt plug from her anus with a nice little pop. Jack lubes her rosebud up and then his cock.
"Your cock?!? I don't know if I'm ready for that yet? You're probably too big for me."
"You'll love it, baby. I'll start off nice and easy."
"Okay. I guess, okay," she stammers uncertainly.
His head goes in first, she moans; so far so good. Shaft goes in next, then some more shaft, she groans. Full cock now in, painful yelp, then subsiding into pleasure. His bitch is plugged really good now!
"Oh my god, that feels wonderful! You made it in mister!"
"Told you you'd like it. Now let me rock your ass a bit with my dick."
"Okay. Not too hard! Aghhh, fuck, oh gawd....that's it baby, oh my god, that feels good! Fuck my ass, Jack!"
Jack fucks her ass a while until she's had enough, and then he gently pulls his swollen cock out.
"I liked it, Jack! Guess I'm no longer an anal virgin, huh?"
"No baby, you're a three-hole whore now."
"I thought I was a slut?" Anna teases.
"No baby, when a woman loses her anal virginity, she goes from slut to whore!" Jack laughs.
"Guess I'm your young whore from now on when I'm in your office. Haha! Oh, you still need to cum, don't you, baby?"
"Suck and jack me off, baby girl. Make me cum hard!"
Anna gets down on her knees and goes to work, mouth and hand working in perfect unison. She pauses to put his cock between her big tits and fucks him with them. Anna completes the tit fuck and then goes back to sucking his hard schlong. Before long Jack is ready to explode and does so in her mouth--large blasting ribbons of "baby batter." She shows him the cum on her tongue and then swallows it. Even how she did that was hot!
"Okay baby, time to wrap up for today."
"Do I get a drawer?"
"Huh?"
"I noticed Diane got TWO drawers. Where am I going to put my cosmetics and lingerie, huh, mister? Hehe."
"You saw her stuff? Oh shit, busted."
"Sure did, but it's okay, I had a pretty good idea you were fucking her."
"How?"
"When she would leave your office, I could tell. It's an intuition thing. She looked TOO satisfied for just a numbers review. Haha."
"Alright, when you and I review the numbers, you'll leave that way too."
"Promise?"
"Promise!"
Anna grabs her clothes and heads to the bathroom.
"I'm going to shower off, guess I'll have to use Diane's towel. Think she'll mind? Haha!"
With that, Anna sashays off to the bathroom, accenting her hips as she walks. Her butt looks spectacular and well worked out for one afternoon's playtime.
"Two staff pussies down, one to go!" muses Jack.
