Sam finally tries Tinder

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Sam had finished college a couple years ago and now worked at a place that didn’t fulfil him. In addition to that, there were barely any women at the company and he wasn’t the type of guy who went out to meet new people. Going out was boring anyway and he knew he would be too shy to hit up girls anyway. So what would be the point?

To get around that, he decided to jump on the train of Tinder. He wasn’t a fan of that either, but it would be better than becoming a 40 year old virgin.

So Sam had set up his profile and started swiping. Unsurprisingly, he didn’t get any matches. He wasn’t handsome, but neither ugly, and he didn’t know what the girls wanted to see when they read his profile. He modified some sentences here and there, but it didn’t seem to make a difference.

After about a week, he finally got a match. It wasn’t a cute girl, but rather a mature woman. Her name was Cindy and her pictures were absolutely out of this world. She had blond hair, often tied into a tight pigtail. In the main picture, she wore a business outfit: Tight, white blouse that seemed too small for her chest; a dark grey blazer; and a dark grey pencil skirt with black high heels. She looked like out of a movie, or porn…

Sam’s first thought was that this must be a scammer. No woman who looks like this would use Tinder, much less swipe right on him. After sitting there for a few minutes, he got a message from her. The last piece of evidence he needed to label her as a scammer.

“Hey there. I think you’re really cute and would like to get to know you better if you are interested as well. Kisses, Cindy”

Well… doesn’t sound too scammer after all. So Sam decided to craft a reply.

He had been on that message for at least ten minutes and it still sounded like a shitty reply. But it was better to just reply than sit around and let the opportunity go to waste.

“Hey Cindy. Thank you, I think you’re beautiful as well. Where would you like to meet?”

A few seconds later, he got the reply.

“Great. I’ve got to finish some work at the Odeon Law Firm. Would you like to come over there at 5:30 pm? Then we could head for a walk and a café from there.”

The Odeon was on Sam’s daily commute, so he was familiar with it. But tonight already? It was 3 pm on a Saturday and he had set his mind on gaming through the evening again. But maybe he could make an exception this time and change his plan.

Definitely didn’t sound like a scammer, now that he knew that Cindy worked at a law firm.

“Yeah, that sounds chill. Let’s do that.”

“Fantastic. So I’ll see you soon. Xoxo”

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The last time Sam had been so nervous was for his last exams during college. He had showered, shaved himself everywhere and even put on some aftershave. He had never put on aftershave but had some because his mother liked to give it to him for christmas.

Anyway, he had been ready for the last half hour and was excitedly waiting in his apartment. It would still be a few minutes until it was time for him to leave. He’d take the bus, which would stop almost right in front of the Odeon.

Eventually, he made his way down his apartment building and towards the bus stop. He saw the previous bus just turn away around the next apartment block, so he’d still have to wait another seven minutes until his would arrive. Well, better too early than too late.

During the bus ride, Sam kept shifting around. He was full of anticipation and couldn’t sit still. He became overly conscious of his thudding heartbeat. Small droplets of sweat started forming on his forehead. Maybe closing the shirt all the way to the top was a mistake. He opened the first three buttons to let some air on his hairless chest. Luckily, he arrived within only ten minutes.

He passed through the rotating glass doors of the Odeon and just as he stepped inside, he saw that gorgeous woman step out of an elevator behind the security post. There were surprisingly many people coming out of the elevators for a Saturday, but Sam barely had eyes for them. He was busy trying to look good and not creepy.

“Wow, you’re even cuter than in the pictures.” Cindy said when she got close, making Sam blush. As Cindy got closer though, Sam slowly realised that this woman was way taller than him. He was 5’10’’ tall, a good size for a man. But Cindy looked like she was around half a foot taller than him, massive for a woman and for Sam.

And then she just hugged him, as if they already knew each other. He didn’t mind though as he brought his arms around her feminine frame. It felt weird that she put both her arms around his head and shoulders. But he decided that he liked it. Some part of him might have liked it because Cindy’s bust pressed into his face. It reminded him how much of her bust was hidden beneath her tight clothes.

“Would you mind coming up to my office for another few minutes? I didn’t manage to get everything done as expected. It would only take 10 or 15 minutes,” Cindy asked.

“Oh, of course. No problem,” Sam shily replied.

Together, they walked through security, took an elevator up and went down a hallway to Cindy’s personal office. All the while, they chatted about various things. Usually, Sam didn’t enjoy such talks, but it came so easy with Cindy. Maybe she was just a pro at that, being a lawyer and all.

As they enter Cindy’s office, Cindy walks around her solid mahogany desk and motions for Sam to sit down in a comfortable recliner on the side. They keep on talking about the weather, sports, Sam’s work, family, and so on, totally forgetting time.

Eventually, there is a ring that goes through the whole building. It’s the law firm’s 6 pm ring, signalling all employees to stop their work and go home for the day. A few years ago, they had some labor issues that them to employ such a unique system. Employees were no longer allowed to work past 6 pm on Saturdays and Sundays.

Cindy cut off their conversation and immediately went to finish the work she still had to get done. Sam, meanwhile, just sat in his recliner and studied her office and the city’s skyline more closely. From up here, he got a fantastic view that he didn’t want to miss out on.

After just a few minutes, they heard the faint ding of the elevator stopping at their floor, followed by heavy footsteps that got louder and louder. Cindy suddenly looked up with a panicked expression. She wasn’t supposed to be here, much less with somebody who didn’t work there.

“Oh no. That’s the security guard. Quick, we have to hide you. Maybe I can make an excuse why I’m still here, but there’s no way I can explain your presence here past 6 o’clock.” Cindy said hurriedly.

“Shit. Get under the desk here, there’s no other spot to hide you.” Cindy was almost whispering now, not wanting to alert the guard that there was somebody else besides her.

Sam quickly got up from the recliner and jumped over to her. He got on all fours and eyed the tight space beneath the mahogany desk. There were drawers at both ends of the desk, only leaving enough space for the chair and legs to fit under. He anyway crawled under there and turned around towards Cindy.

She gave him a reassuring smile and drove her chair closer to the desk. She had to spread her legs, though, to make it appear like she was sitting comfortably. This, of course, made her skirt slide wide up her legs.

She scolded herself for having taken off her panties before she went down to meet Sam. She was sure it would just allow her big girl to take a breath. Never would she have imagined that her date would land between her legs under her desk. But there was nothing she could do about that now. Hopefully, he wouldn’t find out about her little surprise too soon. She first wanted him to get comfortable around her.

Sam was now enclosed by two legs that seemed to be a mile long. At the end they just disappeared into the dark. He immediately got hard from arousal. Things progressed way too fast. Though he assumed that she hadn’t planned that either. And it was kind of uncomfortable in that tiny space. And it got hot and musky quickly. He hadn’t even heard the guard enter the office yet and he was already starting to sweat.

After a few seconds he really needed to get a bit of fresh air. He put one hand on Cindy’s leg and leaned forward to get closer to that sweet fresh air. This really surprised Cindy and she reflexively opened her legs even wider, allowing him much more space than before. But he heard how both her legs hit the drawers on the sides.

When he leaned back again and looked between her legs, he saw that there was a new outline that wasn’t there before. He leaned closer to it and saw the outline of something massive. After several moments of staring at it, it dawned on Sam: Cindy had a massive dick between her legs!

Cindy sat all the way back in her chair and her dick flopped almost on the corner of the chair. If she scooted forward a bit, her dick would visibly hang down.

When Sam’s eyes got more adjusted, he also realised that this monster was draped over two orange sized balls. He was lost in amazement, admiring this girl's package. No, this wasn’t a girl’s package, this was a woman’s parcel.

After several moments of admiration, Sam finally heard the guard step into the room and talk to Cindy. She explains that she’d be done in just a few minutes and that this is not something that can be put off another day. It needs to be done today. The guard is very understanding. He keeps talking to Cindy and she answers politely, not wanting to make him angry and change his mind. This keeps going on and on.

Sam eventually tunes off the conversation and refocuses on Cindy. Just now, he remembered that he had never seen a girl with a dick. And he had expected Cindy to have a juicy pussy too. How he remained so calm was even weird to him. But he had to admit, this monster cock kinda fit her personality. And the longer he looked at her parcel, the more feminine it seemed to look.

He had always imagined what it would be like to work on such a desk and having a girl give him a blowjob beneath. Sometimes also while he was talking to some imaginary subordinates or superiors. Now, he was kneeling before someone superior.

He inched forward on his knees and approached Cindy’s cock with his hands. Gently, he lifted it up, making Cindy pause mid sentence. She quickly recovered tho and even shifted forward on her seat, giving Sam easier access to all she had to offer.

He gladly took the offer, marvelling at how soft her parcel felt and how much heat it radiated. He also noticed how it grew slightly. He kept moving his hands over and under her dick. He lifted up her balls. They were almost too heavy to lift without him falling forward.

He pushed back the foreskin on her dick and looked at her exposed cock. Saliva started collecting in his mouth and he barely hesitated before pushing out his tongue and giving her glans a lick. Cindy’s monster jumped in response and she shifted forward even more, signalling to Sam that he should go right ahead with his plan.

Sam didn’t have a plan though, he just went with the flow. And apparently, the flow dictated that he should savour the drop of precum that had formed on her dick. He licked it off and marvelled at the sweetness of her nectar. No more reason for hesitation, he put his mouth around her head. He had to stretch wide to make it all fit. It must be the biggest cock in town, truly gigantic even for porn standards.

He inched further forward, but didn’t have to do much more to get more meat into his mouth. Her dick was quickly growing in length, looking to get more of itself into his moist orifice.

Cindy started having trouble holding up the casual conversation with the security guard. Sam had taken her by complete surprise when he grabbed her girl. And now he had put her in his mouth. She sure seemed to have made a good catch.

Cindy made the impression of adjusting herself on her seat. And she adjusted, but not in the way the security guard assumed it. Instead, she rolled her skirt up completely and shifted to the very edge of the chair.

Her balls now hung far off the chair and Sam had much more light to admire the size of the parcel he had received. With some of the semi-hard dick already in his mouth, he saw that it stretched on for much further still.

Eventually, the security guard left, clearly noticing that Cindy is preoccupied with whatever she’s working on. In reality, she was working hard on keeping her composure. The boy beneath her was trying to get her off, and he was doing a damn good job at it. But she knew that she eventually needed much more than what he was doing now.

Sam took as much of her cock in his mouth as he could. But he barely managed to fit more than her cockhead. It proved way too thick and large. He wanted to try and take her into his throat, but reflexively knew that this would make unpredictable sounds that would be heard by the security guard. He hadn’t realised that the guard left some time ago.

He kept at it, moving his mouth and tongue along her cock. All he wanted was to get out more of that sweet sweet nectar. It almost got him hooked the second he had tasted it. Now he massaged her balls and pumped her monster. The reward was large amounts of precum. It almost flowed out of her cock like a sink that was not dripping, but flowing a thin stream. Obviously, he had to swallow every few seconds. He felt like he was already getting kind of full. Just from drinking her pre-juice.

Cindy was reclined in her chair. The guard had left minutes ago and the boy down below kept working on her meat with vigour. He pumped and massaged her. Judging by his movements, all he wanted was her cum. She didn’t mind. She’d give him plenty.

Eventually, though, she wanted more. She rolled her chair back and pulled Sam along. He had to crawl on all fours, but his mouth never left her cock. She loved him for his commitment and the ridiculous scene. She smiled back down to him as he looked up. She loved how he looked, so disproportionate. He was a frail boy by her measure and her lady was thick and veiny. It looked stronger than this boy. And he wrestled with it, trying to devour something that was larger than a cucumber.

Cindy grabbed Sam’s head and gently pulled on him, wanting to sheave herself in his throat. But it proved resistant. So she pulled harder. Sam put his hands on her legs and assisted her, but his throat was too tight and unused.

“Take a deep breath through your nose and relax as much as you can”, Cindy told him. She released his head and observed him relax.

When he had taken a few breaths with his mouth stretched over her cock, Cindy suddenly put both hands around his head again and yanked him forward. Half of her massive dick magically disappeared and Sam started gagging like mad. His body wanted to resist further and kept convulsing. Tears started flowing down his face, only to collect around Cindy’s dick.

Cindy could barely control herself. The pleasure from that thrust was immense. She squeezed her thighs together and flexed her cock, trying to suppress the orgasm. She barely kept it at bay, but still flooded his throat with a gush of precum.

Sam couldn’t breathe anymore, but he achieved more than what he had hoped. It was painful as fuck, but he thought he had seen worse. Cindy seemed to be close to orgasming, but wasn’t quite there yet apparently.

So he did all he could to get her there. He held onto her and vigorously moved his head back and forth. To his surprise, it did the trick within a few seconds. Cindy was shaking and grunting but finally relaxed her tensed legs. The floodgates opened and Sam felt it. Her orgasm came and it shook his body.

He first felt her cock flex stronger than before. Her thighs started vibrating and her hands gripped his hair more aggressively. Then he felt how her urethra expanded over his tongue, clearly delivering massive amounts of baby batter.

He felt how it flowed into his stomach. It only took a few seconds to give him a full feeling, but he instinctively knew that there was much more to come. Panic started building up. He was running out of air and space in his stomach. He suddenly didn’t want more nectar in his stomach, but rather have that hose leave his throat.

Sam started pushing and wiggling, trying to free himself. But Cindy’s grip and thighs wouldn’t let him go. She was too lost in ecstasy. He started slapping her thighs and stomach, but still didn’t get a response. When the panic got over a threshold, he started hitting her. On her thighs, stomach, and even her dick.

This finally got the attention of Cindy. She looked down and saw Sam’s purple face and ridiculously extended belly. She had been so lost in her orgasm that she forgot that this time, she was using a living fleshlight, not some plastic gadget. Right after that realisation, Sam’s body went limp. He had fallen .

It was the hottest thing that ever happened to Cindy. But she would really have to take her dick out of her new cock-lover now.

She looked down on him. She hadn’t come this hard in ages. The poor boy fell only halfway through her orgasm. After pulling out, she had to dump the rest of her load into a nearby bin, also filling that one halfway up.

And she had had a lot, she knew that. She hadn’t had time to masturbate for the whole day. Maybe that had played a role in entrancing Sam. And it certainly played a major role in filling him up like that.

Getting a wider picture of the scene, Cindy cringed inwardly. The cleaning lady had told her multiple times that cleaning cum off the carpet and the desk was a pain and that she should get a hold of herself or visit a therapist. Now, there lay a boy on the floor, leaking cum out of his mouth and there was a trail of jizz between Sam and the trash can.

Cindy got out some tissues from her purse, wiped down her now-flaccid dick and restored her outfit.

There was no way she would be able to sneak past security with Sam. Especially if he walked funny with a belly unnaturally extended. It would prompt questions that she wasn’t comfortable with answering.

So she wrote a note on a piece of paper. You fell asleep after you treated me so wonderfully. Unfortunately, I see no way to sneak you out past the security. The best I can think of is if you stay and sleep here. I’ll come back first thing in the morning to pick you up. Xoxo my cutie

She placed it in front of Sam and left. Cindy was deeply satisfied. She found herself a cute boy that seemed to like her unusual appendage. And it seemed that he wanted to keep her loads in. Not something that any of her other romances wanted to do.

Now she would go home, enjoy a relaxing evening, maybe have a glass of wine to celebrate her success and the next morning, the first thing she would do is get her new boy out of there and to her place.