Valentines Day Train

Letting out a long low sigh Caleb looked out the window of his office as the sunset and darkness started to set in wondering whether everything he had done over the last twelve months to earn this office had been worth it.

All those long days and late nights, going above and beyond, stepping on whoever he needed to and generally making more enemies than friends and he'd figured it would all be worth it he got the job he had wanted, yet here he was, Valentine's day night, sat alone in his office, wishing he had a date or someone to go home to, he would have took a flirty Facebook encounter at that exact moment.

Caleb wasn't a bad looking guy, 6ft 2, wavy dark haired that he tried to style like Bradley Cooper, brown eyes, a nice tan thanks to his Mothers roots and he always ensured he had time for a visit the gym, despite his commitment to work, so he had a nice body too, overall, he had never had any complaints from the opposite sex.

The problem was he'd just made a decision when he got into his late twenties that he wanted to focus on his career and making partner at his company before he was thirty had validated his decision but those years of focussing on his career also meant his dry spell was the longest he had since he was a teenager.

Glancing down at his phone, more in hope that expectation, Caleb flicked over his Instagram account, scrolling through the pictures, image after image of friends declaring their love for those nearest and dearest, yet there was no messages awaiting him in his inbox or secret declarations of love in his messages, sighing once more as he put his phone back down Caleb thought about heading home for the day and just putting this day behind him.

Suddenly he was snapped out of his thought process as he heard the sound of footsteps in the corridor outside of his office, expecting to be alone at this time of night in the office, he looked up at his door, the corridor only visible through the small window in his door, waiting to see who would work past only to be surprised when the handle of his door moved and the door swung open.

Despite being sat in his own office and not being up to no good, Caleb still felt startled as if he was doing something wrong being in at this time of night, sitting up in his chair not sure who to expect as he looked up and saw his long time rival, Cheryl Stevens, stood in the doorway.

She had a tight fitting pencil skirt, which hugged the curves of her hips and her slightly plump ass, with a low cut top tucked into her skirt, pressed against her breasts that Caleb would have guessed were a 32b and a pair of black heels on which had been the sound that had alerted Caleb to her presence. Her dark black hair was tied back in a pony tail as it always was and her pale skin seemed pale in the dim light of the dark office.

Caleb had known Cheryl since he had started in the company, they were similar ages, they'd both worked their way through the ranks and she had gone for the job he was in now and had barely said two words to him since he got the job, he knew she hated the sight of him sat behind this desk in the office she felt she deserved and the look she was giving him as she stood in the doorway said exactly that.

Walking into his office Cheryl moved towards his desk as she spoke, "working late again eh Caleb."

Looking her up and down again as she walked towards his desk Caleb just smiled, "You know me Cheryl, can't get enough of the place."

Slowly moving towards a grin on her face that Caleb couldn't help but be a little nervous about she continued, "Oh I know alright, look where it got you though, finally got the office you've always been after."

Now Caleb and Cheryl had known each other for a number of years now but they've never been close or friendly and that comment from Cheryl was probably the closest she had ever come to being nice to him and it threw Caleb and Cheryl knew it.

Flustered, not sure how to respond, Caleb just watched on as Cheryl moved around to his side of the desk and sat her plump ass down on the desk in front of him, her pencil skirt riding higher as she sat down.

Cheryl just kept that wicked grin on her face as she looked down at Caleb, his face a picture, grabbing his attention once more as she asked, "You enjoying the power of the office Caleb, that's why I always wanted it, the power."

Looking up at her from his seat, his brain a mess of confusion so uncertain about what was going on as he looked up at her, Cheryl's face sporting the same grin, "What power, I'm just doing my job, nothing....."

Cheryl interrupted him before he could continue, "Do you now think you have power over me Caleb? You're my boss now."

Caleb's cheeks turned rosey pink as he kept his gaze up at Cheryl, "I, er, well, I, er....."

Enjoying watching him suffer this was everything Cheryl had hoped it would be as she let him struggle with his words for a moment before speaking over him once more, "Most guys in your position, well, they'd probably want to abuse their power.....and well......"

Slowly but noticeably Cheryl parted her legs, just enough to make her skirt ride over her knee and her bare knee press against Caleb's hand which was gripping the arm of his chair, "Most guys would have used their power to take advantage of their office......if you know what I mean."

Feeling her knee press against his hand but keeping his eyes up on her, Caleb knew exactly what she meant and of course the thought had ran through his mind every day since he got his office but the lack of a female companion had ended those thoughts prematurely, but was his arch rival really suggesting this.

Once again giving him a few moments with his thoughts and herself a few moments to enjoy making him squirm before she continued, "I suppose the real question Caleb, you've got the office and you are definitely my boss but do you really have the power?"

Waiting till just the right moment, watching Caleb open his mouth about to say something, Cheryl lifted her leg up and over on to the arm of his chair, her legs spread wide, her skirt riding up and revealing her bare pussy to Caleb, grinning once again as she watched the words drain away and just stare down between her legs.

"Know who has the power?" asked Cheryl as she leant back slightly on his desk.

Finally, looking up at Cheryl but still looking bewildered, opening his mouth to say something but still lost for words Cheryl let out a little chuckle, "I thought so."

Leaning back on his desk, Cheryl fixed her skirt so it was bunched almost around her waist now her pussy glistening in the dimly lit office lights, her legs spread, looking down at Caleb who was just sat there taking it all in, "Why don't you be a good boss and come lick my pussy."

Caleb looked up at her and then down at her spread legs hesitating for a moment but then his dry spell came to mind and the fact that if he and Cheryl hadn't become rivals he definitely would have asked her out. he knew he couldn't resist as he slowly moved forward on his chair, his eyes flicking from up at Cheryl to down at her glistening wet lips.

Licking his lips, he leant forward, resting his hands on the desk either side of her and softly let his tongue tease forward and lick along the length of Cheryl's lips, tasting her wetness as he licked from bottom to top.

Closing her eyes and keeping her balance as she leant back with one hand, Cheryl reached forward, stroking her hand through his ruffled well kept hair, pressing a little firmly encouraging his tongue deeper, "mmmmm, that's a good boss, eat my pussy."

Encouraged by her moaning Caleb pressed his tongue deeper between Cheryl's lips, quickly finding her clit and circling, lapping hungrily. He'd always enjoyed going down on a woman and had been told by every woman he'd been with how good he was at it, which Cheryl was quickly finding out.

Biting her lip, Cheryl grimaced and fought her urge to groan as Caleb went to work on her pussy, his tongue circling her clit, lapping at it like a hungry dog, it felt so good, as she kept her hand on his head gripping his hair tighter, never wanting him to stop.

Caleb pressed his tongue deep into her pussy, until he found just the spot he had been searching for, tickling at her g-spot with his tongue, feeling her hand in his hair gripping tighter as her ability to deny her moans was getting weaker, feeling her hips start to quiver under him.

Cheryl was almost humping his face such was the incredible feeling he was giving her, she looked back for anything behind her, pushing it out of the way, as she lay back, her legs spread wide for him still as her now free hand reached up and groped at her breasts, tweaking her nipples through her top, feeling her orgasm getting closer by the second with every teasing lap of his tongue.

Her hand tight on his head Cheryl gripped his hair tight as she could as her body stiffened her hips stopped quivering before she suddenly started shaking wildly moans she had been fighting escaping her lips echoing around the empty office building as her orgasm crashed over her, "Ohhhhhhhh fuck yes boss, eat my pussy....fuck yes!!!"

Sliding his tongue out of her pussy, moving back to her clit, lapping hungrily, sucking it between his lips, gently tugging at it, Caleb's face was covered in Cheryl's juices as she held his face in place tight to her quivering body.

Gripping his hair, Cheryl pulled him back as she sat up on his desk, gasping for breath as she slowly recovered from her orgasm, "mmmm, thank you boss, now how about we properly break in this new desk?"

Pulling at his shirt, more passionately than aggressive, Cheryl sat on the edge of the desk, her skirt still hiked around her waist, her top and hair dishevelled from where she had grasped at them, she looked up into Caleb's eyes as she unbuckled his belts, unzipping his pants and gasping to him, "Fuck me boss, fuck me right here on your new desk."

Caleb still couldn't quite believe this was happening as he looked down at Cheryl laying there, desperate for him but he wasn't one to look a gift horse in the mouth as he pushed his pants and boxers down, his rock hard 7" cock springing free, not especially long but what it lacked in length it made up for in girth as he heard Cheryl's groans of appreciate, "Oh fuck boss, stick that fucking tree trunk inside me."

Wrapping his fingers around his cock, Caleb carefully rubbed the head of his hard cock along her dripping wet lips, getting the tip nice and wet, wanting to take his time and enjoy breaking his dry spell but didn't get a chance as he felt Cheryl's leg wrap skilfully around his waist and pull him into her, both of them groaning out in unison as his cock plunged deeper into her soaking wet pussy.

Both of Cheryl's hand gripped at her breasts through her top as she grimaced and moaned out "Holy shit boss, yes, fuck me, fuck it's so big, fuck yes!"

Reaching down grabbing hold of her thighs, Caleb started to pull her back against him, groaning with her as he thrust into her, deep as he could, all the years of competition, pent up sexual frustration between them both coming to the hilt in that moment as he slammed his fat cock deep into her soaking wet pussy, the sounds of their fucking only joined by Cheryl's moans.

"Yes boss, yes, that's it, keep going, am gonna cum all over your big dick boss!" Cheryl was lost in the moment now, her only focus was her orgasm.

Watching her breasts barely contained by her top bouncing up and down, Caleb never slowed thrusting deep and hard, her pussy gripping his cock as his thickness slid in and out, feeling her pussy gripping his shaft more knowing she was close.

Cheryl couldn't control herself any longer as she screamed out, her body stiffening and then shaking wildly once more as her second huge orgasm crashed over, her legs wrapping tight around Caleb holding him deep inside her as she shuddered, grimacing and gasping for breath as the huge orgasm rocked through her body.

Opening her eyes as she tried to gather herself, she reached forward pressing a hand on Caleb's chest, pushing him out of her soaking wet pussy, still struggling to catch her breath as she moaned to him, "Fuck me from behind boss, show me who's in charge."

Getting to her feet Cheryl's legs shaky under her as she turned around and bent over pressing her hands against Caleb's desk as she felt his hands grab onto her hips and his fat cock rubbing against her parted thighs.

In unison they both let out a yelp as they heard, "I'm not interrupting am I?"

They both looked up in horror as Carol the office manager was stood at the doorway looking at them both.

Without another word being said, Caleb pulled out, quickly pulling his pants up, his cheeks as red as they could go, whilst Cheryl quickly pushed her skirt back into place and rushed for the door, looking up at Carol as she tried to squeeze past, "I'm so sorry Carol, it....."

This time it was Carol's turn to stop Cheryl in her tracks, "I will speak to you in the morning Cheryl." A stern tone to her voice that had put her in the position she was. Cheryl nodded, squeezed past and disappeared out of Caleb's office as quickly as she could.

Caleb stood there for what felt like an eternity tried to hide the bulge in his pants from his raging hard cock which hadn't had time to go down yet, feeling Carol looking at him and looking around at the mess of his office.

Moving a little closer to his desk, Carol was dressed in skin tight jeans, that clung to her long legs, black heeled boots which made her even taller despite already being over 6ft and a loose fitting black top which clung to her heavy 34e breasts and tucked a stray strand of her long blond locks behind her ear as she continued to move around his office.

There was no denying that her looks had certainly helped her climb the ladder in the office and Caleb had always thought she was hot but would never dare even flirt with her, she was twenty years older than him for a starters but that didn't mean he didn't fantasize about her.

Finally breaking the silence Carol looked up at him, "So this is what you do with your new office is it Caleb, first quiet night in the office and this is what I find you doing."

Panicking at what this could mean for his job Caleb was quick to open his mouth, "No, Carol it's not like that, it's...."

Still moving around the office, stepping around to his side of the desk as she listened to him try to make his excuses, Carol quickly interrupted, "Don't, I don't want to hear it, guys like you are all the same."

The panic only increasing in Caleb, completing forgetting about the bulge in his pants that refused to go down as he raised his hands in defence, "Honestly Carol, I would never....."

Moving around the desk to the position Cheryl had been in moments later, Carol turned away from Caleb before looking back at him, her tone once again stopping him in his tracks, "You would never? Did I not just walk in on you with a girl in this exact position?"

Caleb gulped as he looked up at Carol turned around looking at him and then couldn't help himself as his gaze travelled down her back to her ass squeezed into her tight jeans, the jeans showing the curves of each cheek, he opened his mouth to speak but couldn't find the words.

Looking back up he saw Carol was facing away from him once more now and hoped this awkward situation was almost over only for his mouth to fall open in more surprise as he heard the sound of a zip and watched as Carol bent over further and slowly pushed her jeans down to her knees, her bare ass revealed to him, clearly not wearing any panties, as she looked back once more, "Would it help you remember more if I was in the same position as the other girl was?"

In complete shock looking at Carol bent over before him, any hopes of his cock calming down completely vanishing, Caleb tried to focus on his apology again starting to explain as he mumbled, "Carol, am sorry, it will never..."

Not listening to him Carol just continued, "I think you had your hands on the other girls hips, maybe you should get in position that may help you remember."

Hesitating as he looked down at Carol bent over before him, Caleb ran through the options he had, say no and potentially get fired, say yes and potentially get fired but leave the next day having fucked Carol, he wasn't sure if it was him or his cock making the decision but he slowly stepped forward and pressed his hands gently to the slender hips of Carol.

The moment he pressed his hands on to her hips, he felt Carol gently sway back from the desk, her ass pressing against the hard bulge in his pants as he listened to her, "You were saying Caleb, how you would never."

Biting his lip feeling Carols ass rub back against his hard cock as he gently held her hips, again hesitating with his response as he muttered, "I, well Carol, I meant..."

Cutting across him once more, Carol continued, "Does my ass not look as good as hers from back there? Is that what it is?"

Caleb this time didn't have to think, he probably should have but instead he instantly replied, "Oh god no Carol, your ass is incredible," his cheeks blushing as he realised how quickly he had blurted that out.

Staying bent over resting on her elbows never looking back at him Carol calmly responded, "Why are your pants still on then Caleb!" With the same tone that had sent fear into Cheryl moments earlier.

Knowing he was in too deep to back out now, Caleb took his hands over Carol's hips, nervously undo his pants and let them fall to his knees once more his hard cock pressing forward and before he could grab it slapped against Carol's bare ass.

Gulping as it happened not sure what was going to happen next, Caleb stood there, looking down at Carol, watched as her hand reached down between her legs, positioned his cock at her pussy and then slowly her body rocked back, taking his cock deep into her pussy as she did, her other hand gripping the desk as she moaned, "Oh fuck Caleb that's a good dick you've got there."

Caleb was still frozen in his position stood there, as he watched Carol slowly start to rock back an forth, taking his cock nice and deep before sliding almost all the way out again her pussy was dripping wet and loving every inch of his cock as she eventually moaned out to him, "Fuck me Caleb, fuck me till I forget what I saw!"

Seeing a light at the end of the tunnel, Caleb knew what he had to do now and he had had worst punishments in his life, as he reached forward, gripping Carol's hips and pulled her back hard onto his cock their bodies slapping loudly together as he did.

Carol fell forward her breasts pressed against the desk, as Caleb started to pound into her hard as he could, her body pressed between his fat cock slamming into her and the desk, every deep thrust sending a tremor like an earthquake to her core, feeling so incredible.

Pressing himself over her, Caleb, pressed his cock deep as he could before pulling out almost the tip and slamming in again letting her feel every inch of the thickness of his cock, reaching forward gripping her shoulder pulling her back onto his cock as her moans echoed around the office.

"Ohhhhh Cheryl was right, this dick is so good, don't stop Caleb, making me cum on this big dick, fuck yes!" Carol's moans were filling the air now as Caleb never relented once more.

Never slowing his thrusting or his grip on Carols shoulders, Caleb felt the familiar feel of her pussy gripping his cock, knowing her orgasm was close, thrusting into her focussing on fucking her through her climax as he groaned out, "Oh god yes, cum for me Carol, am getting close too."

Only to be startled by her immediate stern tone, Carol almost yelling between her groans and gasps for breath, "Don't you dare cum Caleb, you hear me!"