They were co-workers and had been for ten years or so. They were both married. They had even been to each other’s homes and knew each other’s spouses. There had never been an attraction of a sexual nature before, but they did get along really well. When things were getting a bit too serious in the office, they could count on each other to bring in the humor and calm things down.
The funny memes would get shared, the jokes they’d heard, and annoyances about other co-workers would be vented, all via text and messages. When the phone would bing with incoming messages, his wife would simply roll her eyes and ask in a sigh, “Caitlyn?” He would smile and nod, as it had become so common it was a part of everyday life.
Then, something changed. Caitlyn had had an accident and wasn’t able to drive for a while. Being the good friend and co-worker he was, he offered to drive her to work and then home every day. That created extra, personal time where they didn’t have other co-workers, clients, or spouses to interrupt them, and after week or two, he started to play through little fantasies in his head.
It seemed harmless at the time. Most people had fantasies about others, possibly co-workers; it never meant anything, it was just natural to wonder, ‘What if?”
He started to notice how her shirt framed her torso. He had never really looked at her breasts before, but suddenly, he couldn’t help but sneak peeks out of the corner of his eyes as he drove them along their commute. Because she wasn’t in work, she would rearrange her breasts or bra or reach into her shirt to fix a strap, even going so far as to scratch under her tits. They discussed topics they wouldn’t typically discuss in a work environment. A line was being crossed, and he wasn’t sure if he was the only one who was noticing it.
Their conversations were becoming more blunt and risqué as they no longer had to worry about spouses, HR, or offending other coworkers on the long drive. She started oversharing about their sex life, and he began to share about his lack thereof.
They should have been able to simply talk like two adults and friends without it affecting his feelings, but for him, it had been so long not only since he had had sex, but since he had anyone whom he could talk openly to about it. Barriers were being dropped, and they were definitely changing his thoughts about this woman.
One particularly cold day, she got in the car, but not before removing her bulky Winter coat for the drive into the office.
As he turned to greet her, his eyes were drawn to her very prominent nipples that seemed to be straining to tear through her top. She was saying goodbye to her husband over the roof, so her chest was perfectly framed by the passenger doorway. She couldn’t see his gaze as he took in the prominence of her stiff points. Her arms were resting on the top of the car, which pulled her shirt tighter against her breasts, accentuating the curves.
His cock sprang to life and almost screamed to be released. It was the first time in a very long time that he’d been able to get that erect. The feeling was welcome, and warm, and wonderful, and he wanted so much to listen to his demanding member. Unfortunately, she got into the car too quickly.
They exchanged small talk and pleasantries as they started the drive to the office.
He focused on the road as well as trying very hard to calm his overexcited shaft. Praying that she didn’t notice the bulge in his slacks.
They talked and joked and laughed, and he occasionally snuck a glance towards her to see if he could see the pointed profile of her nipples again, even though he knew full well that the sight would make him swell again in appreciation.
When they were about halfway to the office, she finally said, “Can I ask you a question?”
“Sure,” he said, “shoot.”
“Did your wife leave you hanging this morning?” she asked.
He was surprised at her bluntness, but he had never known her to beat around the bush before, so he shouldn’t have been shocked.
“Um, no, not exactly,” he replied. He could feel his face flush with embarrassment, along with his cock flushing with even more excitement, making it twitch and bounce, like a Mexican jumping bean trying to escape.
She calmly waited him out, just staring at him, as well as the mountain in front of his pants.
“Can I be honest with you?” he asked.
“I’d hope you were always honest with me,” she said.
“You have to promise not to hate me or be upset,” he replied.
She paused for a moment, contemplating whether she really wanted the truth. Her curiosity won out, and she said, “I promise.”
He took a deep breath and pushed ahead, “The reason I am so hard at the moment is because of you.”
She just stared at him, willing him to continue.
“As you know, I haven’t really had sex of any kind in a few years. Through one reason or another, I’ve been in not just a dry spell, but a true drought. Then, when you took your jacket off, and forgive me for saying, but your nipples were poking out so hard, it was like we were having a staring contest. I won and lost at the same time.” Here he stopped because he felt his mouth was running on automatic, and if he continued, he might actually say what he was really thinking. There are some lines you can’t come back from.
She was very quiet, staring straight ahead. The silence was killing him.
Very quietly, he heard her ask, “So, what are you saying? Are you saying that I just happen to be a set of tits that set you off like looking at porn? Or, are you saying that you have thought about me in a sexual way, and that you have fantasized about what it would be like to see me naked?”
“Remember that one time you guys came over for a swim, I will admit, seeing you in the bikini was an eye opener. I tried not to stare too hard. But there was definitely some admiration there. It isn’t like I’ve been going to bed at night, jerking off, picturing us having sex. It’s just that it’s been so long for me, and your breasts look great in that shirt, so, naturally, my cock decided to show you respect and salute you,” he said.
She still didn’t reply. He started to worry that the line he shouldn’t have crossed was miles behind him.
“Well, I am flattered. I guess. I’m not sure what you want me to do about that…” she nudged her chin in the direction of his tented pants.
“Honestly, I hadn’t thought about you doing anything. I was hoping it would just go down on its own. It doesn’t seem like it got the message. It has a mind of its own today,” he said.
Caitlyn seemed to get lost in thought for a while. The only sound was the radio set to low volume so they could talk.
Finally, she turned to him and said, “I’ll make you a deal, since it’s the holiday season and all. We will have our own personal Advent calendar. Each day, you will have a job to accomplish by the time we drive home. If you complete all twenty-four tasks, I’ll take care of your problem for you. But one condition is that you can’t take care of it yourself for the duration. I want the full reward for my Christmas present.”
As crazy as it all sounded, he agreed.
For twenty-four days, each day she would get in the car and hand him a piece of decorated Christmas wrap that he would open, and in it would be a note with his daily task.
It started small, with things like stopping to get her a coffee or a breakfast sandwich. One day, he had to simply drive in with her music playing on the radio. Easy things that he would have been glad to do anyway.
Then, week two, things got a bit more personal. He had to give her a massage at a time of her choosing during the day. One day, she requested that he wear a pair of her panties. The feel and heat from those almost made him cum with every step he took. Another day, on the ride home, he had to spend the entire trip telling her what he had thought about doing to her body.
By week three, he was in agony. He both looked forward to and dreaded finding out what the day’s advent task was.
His balls were as blue as a liquid freezer pack. He had to think about all sorts of negative things to keep from cumming in his pants. He had the urge multiple times a day. His underwear was constantly coated in pre-cum and was stuck to his cock by the end of the day.
Her third week, it was her turn to tease him. One day, she described in incredible detail how she would suck his cock and swallow all of his cum, but not before showing him the cream swirling on her tongue. Another day, she went so far as to trace the outline of his hard-on with her fingertips all the way to the office. She seemed to be enjoying the torture. Her breathing actually got faster and heavier as she watched the wetness of his pre-cum spread on his slacks.
Still, he held back from releasing his heavy load. Reciting the alphabet, singing songs in his head, and sometimes quoting whole movies to keep his brain occupied.
He finally made it to day twenty-three. She had been merciless, taking a twisted pleasure in the power she had been wielding over him for the entire month. She would brush up against him, making sure her breasts would slide along his back or his chest, even leaning over him and trapping his arm between them. Sometimes she wouldn’t be wearing a bra, and he could feel her hard nipples push into him.
It got to the point where he was associating everything to do with Christmas with sex. Every song he heard, every tree he saw, even the smell of a peppermint candy cane, was making him get hard with the spirit of Christmas.
On the twenty-third day, she upped her game. He unwrapped his Advent wrapper and in it were the following words, “You will let me give you a blow-job all the way to the office, but you can’t cum in my mouth or touch me in any way.”
There was no way he was going to be able to do this. A part of his brain thought that he wouldn’t really be losing, though. He’d be getting a blowjob, and he’d be able to finally cum. But the competitive side of him really wanted the prize. He’d struggled through the Advent season, making it through each challenge to get the true gift of Christmas.
‘Here goes nothing,’ he thought to himself. He unzipped his fly and pulled his cock out of his shorts. It was almost constantly hard now, to the point of being painful. She gasped when she saw it set free. Her hand slowly reached out and wrapped around his girth. She stroked once, and he stopped her immediately with a sharp tone.
“The wrapper said nothing about a handjob or stroking. It said a blowjob for the duration of the trip. If I can’t cheat, neither can you,” he said.
She agreed, leaning over, opening her mouth, she took the head between her lips and slowly started suckling him. He started to drive, thinking about all the horrible vegetables and terrible things he had ever eaten, running through his mind. Spinach, soft-boiled eggs, tripe, haggis, brussel sprouts. He was going to need to drive as fast as he could without getting caught.
Her lips were caressing the tip while her tongue was licking his slit, sucking all his juices as soon as they rose to the surface. She had amazing skills and put his own wife to shame in the sucking department. He had to resist the urge to put his hand on the back of her head to run his fingers through her hair. He also struggled to keep his eyes open while he was driving. It didn’t help that she kept rubbing her breasts against his thigh as she sucked him deeper and deeper into her mouth, at one point, swallowing him so her lips were buried in the fly of his slacks, and her tongue lapped out to lick his swollen balls.
That almost did him in. Luckily, they were only a few moments from the office, and he let her know so they weren’t caught in the parking lot.
As she rearranged herself and wiped the saliva off her lips, she looked at him with a huge smile and said, “I am very impressed. No man has ever resisted one of my blowjobs before. I think that is a new record. I must say, I am actually looking forward to tomorrow.”
Day 24 of Advent, Christmas Eve. It was just going to be the two of them in the office, and it was only a half day. There was a light snow coming down, making the roads a bit wet. He mentally thought it was good she did the blowjob yesterday and not today.
Before she got in the car, she said goodbye to her mother, who had dropped her at the park and ride. After the car left the lot, she took off her jacket. She was wearing a bright red holiday sweater that had a V-neck, which dipped deeply into her cleavage. He couldn’t take his eyes off her. She had put on some makeup, especially some sexy red lipstick. She was wearing a very short skirt that came to mid-thigh, showing off some rather shapely legs that he never got to see.
She demurely handed him his Advent wrapper. He opened it, thinking it was just going to say that she would suck him to completion today, finally letting him release his twenty-four days of cream.
Instead, it said, ‘Your gift is me. You may open me before Christmas and play with me as much as you desire. I am yours for the day.”
He almost came right then and there. Somehow, he held on. “Are you sure?” he asked.
She smiled at him and nodded, “You earned it. I didn’t think you would even last, especially after yesterday. You must really want this…me. So, I’m sure. As your Christmas gift, you may do whatever you like. I will not say no to anything you desire today.”
His first thing to do was to lean toward her, putting one hand on the back of her head and pulling her towards him so he could kiss her deeply. His tongue, licking her lips, sliding along her teeth, and pushing into her mouth. It wasn’t what she was expecting. A kiss is so much more intimate than a blowjob, but she responded with a fervor she didn’t realize she had. Her own tongue thrusting into his mouth in return. They made out like teenagers at a drive-in movie for a few minutes before he pulled away and put the car in drive.
She felt a flush run down her neck across her chest and bloom a heat between her thighs, like a start of a very slow volcanic burn.
As they got onto the highway, his hand reached over to her thigh, sliding her skirt up so he could touch her bare flesh. He didn’t even bother with trying to go slow. He had been in first gear all month. He slid his fingers up her skin, sliding between her legs, urging her thighs apart. It didn’t take him long to realize that she wasn’t wearing any panties, and his fingers found their home for the drive to the office, buried inside the lips of her steaming, dripping pussy. They were slipping and sliding along her lips, enjoying the silkiness of her folds, occasionally slipping one or two fingers up into her.
Her legs were spread as wide as they could go in the confines of the car. She had put her seat back so she could raise her hips and allow him further access to her depths.
By the time they had reached the office, she had climaxed five times. Her hair was mussed, her skirt was wrinkled, and her face was red as she gasped for breath.
Throughout the day, as they worked, they would touch and brush against each other. He would take full advantage of her lack of underwear, sliding his hands under her skirt to caress her ass or cup her mound, massaging it while standing behind her, feeling her ass grind into the bulge of his cock.
She kept wondering when he was going to take full advantage of her. She had been edging as much as he had all month. She was ready to be taken by him. She wanted him to ravage her. She was even on the verge of begging him to.
There were a few clients to contend with. They always seemed to arrive at the most inopportune time. He would be rubbing her ass or fingering her snatch, and they would see the car pull up. He would finger her till the customer got out of their car and started to walk up to the entrance. At the last minute before they could be seen, he would slide his fingers out and smooth down her skirt, then leave her to attend them while trying to keep her voice under control. Sometimes, she would even have her juices sliding down her thighs as she helped them. He was loving being in control for once, but he knew it couldn’t last. He was dying to have his way with her, and they couldn’t close the doors soon enough.
All this time, he still hadn’t touched her breasts. He wanted that to be his special treat. He’d waited so long to see them, to feel them; he wanted it to be the last thing he experienced.
He heard the front door chime as the client left, then the sound of her footsteps coming towards him. He waited for her, his breathing beginning to quicken.
She rounded the door, entering his office. “I’ve locked the door early. I know we have another fifteen minutes, but I can’t wait another second. That was a cruel thing you did out there just now. I was literally climaxing as I helped the client. It took all I had to not groan while I felt my cream pour out of me and down my legs. It’s a good thing there was a counter between the customer and me…” He wasn’t sure what she was going to say next because he lifted her skirt to see her shiny thighs for himself. Like a man possessed, he dove in, face first, and pushed his tongue into the V of her legs, sucking on her pussy, drinking from her like a man in the desert who finds an oasis.
She climaxed on his tongue, squirting her juices all over his lips, down his chin, even soaking his shirt. His hands slip up the backs of her legs, cupping her bare ass and pulling her towards him so he could bury his tongue deeply inside of her, trying to climb up inside her pussy.
Her hands went to the back of his head, pulling his face towards the V of her legs. It wasn’t that he was necessarily an amazing cunt-licker. He was good, but he wasn’t the best she ever had. It was more than he wasn’t her husband. He was the first other man to lick her pussy in over twenty years. The variations were lovely. The differences in rhythm and areas he paid attention to were enough to make it like it was her first time again. She couldn’t stop climaxing in his mouth, and unlike her husband, he was drinking from her as if he would never be satiated. Part of her hoped he never would.
He felt her body shake for the third time. He pulled his mouth off her, despite her hands on his head trying to plant him there like she was trying to plant a tree. He stood up, sliding her sweater up as he did, his tongue licking up her stomach, taking a moment to ring her belly button, which made her giggle. Her sweater went up and revealed her braless breasts, finally.
They popped and jiggled as the sweater released them. They were even better than he had pictured them in all of his fantasies. Just enough of a hang to them to allow him to lift and drop so they swayed on her chest. They were round and full with dark nipples that seemed to harden even further under his gaze.
He cupped each one, gave them a lift, and buried his face between them. The silkiness of her skin as they surrounded his face was almost too much for him. His hands kneaded them, the fingers digging into the round flesh, trying to experience every millimeter of them. His lips and tongue tasted the perfumed-tinged perspiration in her cleavage. Licking up and down the valley between her breasts, even giving little nips, as if he wanted them for lunch.
His lips finally found her hardened nipples. They latched on to the right one, sucking it into his mouth. It felt so good rolling around on his tongue. Then, he moved to the left one, sucking and popping it out from between his lips, lightly blowing on it to cool the tip with his saliva dripping from it. Finally, he pushed her breasts together and took both nipples into his mouth at the same time. Her body quivered, her back arched, helping to get her sweet gumdrops into his mouth. She fell back against the desk, her hands reaching back to support her, her head leaning back as her eyes rolled up and the lids closed.
Again, the thought that this was another man who seemed to desire her body was what was turning her on. A man who hadn’t gotten so used to it that he seemed to phone in their sex every week, as if he was going through the motions. Even though this was her co-worker, her friend, not someone she was in love with, she applauded his enthusiasm. Her nipples were one of her more sensitive erogenous zones. He seemed to be enjoying them to the fullest. She had lost count, but she thought she had had at least two more orgasms just from his breast play.
What she really wanted was a good, strong fuck. She had given him carte blanche to do what he wanted, though. She hoped his cock in her pussy was on the plan, but she had had more orgasms this day than she had had over the past six months; she really wasn’t going to complain.
He couldn’t seem to get enough of her breasts, but he knew he tended to hyper-focus on the things he enjoyed, so he decided to move on, in a way.
He pulled his mouth off of her succulent nipples, looked her in the eyes, then said, “Would you, please, give me a bit of your incredible blowjob, like you did yesterday? It was, honestly, the best blowjob I have ever had in my life.”
She got a warm feeling at the compliment, and without hesitation, dropped to her knees, unzipped his fly, and released the raging tumescence that had been trapped for so long.
One hand wrapped around his shaft, the other coaxed his balls through the fly, and she cupped them, softly, slowly rolling them around in her hand. Her tongue started to lick at the bottom of his testicles, slowly slathering them in her saliva, then moving up his stalk, following the angry-looking veins around his cock, till it was running around the bulbous, mushroom head.
He sighed, his hands dropped down to her head, not to force her onto his shaft or even to hold her still so he could fuck her luscious, lipsticked, coated lips. Only to run his fingers through her hair and show his appreciation for sharing her skill and her amazing holiday gift.
Within moments after her tongue flicked over the slit of his hard-on, she opened her mouth wide and slid her lips around his penis, without hesitation, dropping down to deep throat him till she had to swallow to get him any further.
His cock shot one load of cum, like a bullet, down her throat, but she gripped his cock and balls, stemming the flow of her reward. She pulled off his cock with a pop, looking up at him with strings of moisture hanging off of her lips, “Is that what you want? Do you want to shoot your load down my throat? Do you want to cum in my mouth?” she asked as she licked her lips.
He thought for about one second, looking down at her on her knees, her breasts catching the drops of drool and cum, and made his decision.
“No, this is what I have fantasized about,” he said as he pulled her up to her knees, sliding his slick and shiny fuck stick between her tits.
He saw a bit of disappointment flash across her face. “I’m sorry, fucking is for my wife only. And as much as I really want you to finish that blowjob, to shoot my huge, month-long build-up of cum into your mouth, to watch you swallow it, I really enjoy the sight of my cum firing out of my cock and splashing down. I want to see it spray all over your gorgeous tits, coating them and dripping off of your nipples.”
With that said, she grabbed her tits and surrounded his cock, wrapping it like it’s own Christmas present, and proceeded to titfuck him with reckless abandon. His shaft was so slick that it glided in and out of her breasts, the head popping out of the top, making light squishy sounds every time it appeared. She leaned her head down and started to lick the head every time it showed.
His hips were pumping like crazy. The warmth and grip of her tits around him was better than seeing the Star of Bethlehem. He was in Heaven, his fantasies finally realized. He knew he wasn’t going to last much longer. The combination of the tit-wrap and her licking his cock head was the final straw.
Three, two, one, and he felt the surge begin in his balls as they tightened. He only got out a grunt before she released his cock from its shroud, grabbing his turgid member, stroking for all she could, and pointing the head at her tits.
Rope after rope of hot, gooey, thick cum erupted from the head of his penis. Hitting her tits with such force, it was like waves crashing onto rocks on the shore. The cream hit her breasts and sprayed upward, hitting her chin, lips, and cheeks, only to drip back down and coat her breasts.
It seemed like his climax was going on forever. It had been so long since he had cum, and even longer since he had been made to cum by someone else. The feeling of release was so incredible that he wanted to cry.
His hips continued to buck and hump her hand as she tried to pump him dry. She even took it upon herself to lower her head and wrap her mouth around him to suck the last vestiges of his deposit into her mouth. She had never told him, but she loved the taste of cum as well as the feel of it sliding down her throat.
Her head slid down his cock till her lips once again rested against his balls, her tongue running around the full length of him, cleaning him.
He felt one or two more huge shots that he couldn’t believe he still had fire down her throat.
Her fingers dug into his ass as she pulled him so far into her mouth that he thought she was going to swallow him whole.
As his ejaculation finished, she pulled her mouth off of him with the nastiest slurping sound he’d heard in any porno movie.
She looked up at him, just a mess of cum and saliva, yet still looking sexy as Hell as it dripped into her cleavage.
He pulled her up by the shoulders, sat her back on the desk, dropped to his knees, and licked up all the juices that had been pouring out of her dripping pussy. He lapped up her inner thighs, delving deeply into her lips, swirling his tongue as deeply inside her as possible, running it around the walls of her cunt, paying special attention to her clit whenever he came up for air. She convulsed, bucked, and shimmied all over the desk top, coating the surface with her fluids as she climaxed over and over. The scent and taste of her was ambrosia to his tongue.
She finally had to pull him off her. Her body simply couldn’t take any more. Every muscle was contracting with her climaxes.
He stood up, wrapped his arms around her, pulled her into him, and rested her head on his shoulder. He felt her body twitch over and over as she came down from her high. He rubbed her back and ran his fingers through her hair.
“Thank you for my Christmas miracle. That was the best present I’ve ever received. It was my pleasure to unwrap it.” Then he kissed her on the top of her head.
She hugged him back, settling but still shaking. “You are very welcome. You earned it. Best Advent calendar ever.” With that, she looked up at him and smiled.
They put themselves back together and got ready to head home. There were light touches and caresses every time they passed close to each other. They knew this wasn’t going to be an ongoing thing. It was the magic of the holiday season. But they would have the memory forever.
Besides, they still had a commute to get through, and it was still Christmas Eve, who knew what they could accomplish with each other on the long drive home.
