The Tinder Match Affair

[F4M] The Tinder Match Affair.

Tags: Gentle Fdom, Cheating, Age Difference, Older Woman, Lots of Good Boy, Call me Mommy, Voyeurism, Riding, Handjob, Breast Play, almost uncontrollable lust, teasing, Big Ass, worship. Cumplay

Summary:

A young man matches with an older woman on Tinder, he's looking for a fun experience, she's looking for a boy-toy to have an affair with. A match made in heaven, or at-least Tinder.

This story was written on commission.

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'It's a match!'

Those words flickered on Andrew's phone.

It had been several months since he had installed Tinder on his phone. His friends had all convinced him to give it a try, recounting stories of 'spicy' hookups and 'loving' relationships. With the help of his friends, he made his profile.

'Andrew, 21'

'Hi, I'm Andrew, I'm a College student, Looking for something new. I'm a little quiet at first, but I promise I'll take you somewhere fun. I enjoy art and cool things, as well as meeting new people'.

A rather bland and innocent profile, but Andrew thought nothing of it. 'Just be himself' he thought as he uploaded the profile. Eventually, he would match with someone, and that's when the real fun begins.

At least, that's what he hoped would have happened. Much to his dismay, he had very little luck with the app since installing it. Most of the time he wouldn't get a match at all, he was prepared to wade through the long list of silent rejections, though every day it continued to ground slowly on his self-esteem. Added to that, the few matches he did get in the past usually ended up being very short-lived conversations, or worse, bots.

By this point, Andrew was sick of it. It was a pointless waste of time that only made him feel worse about himself. He was going to delete it, move on with his life. Hopefully, meet women in 'the wild.' But before he did any of that, he decided to swipe right, on everyone.

Swiping again and again in frustration, Andrew no longer cared what they looked like, or who they were. He just wanted a single connection to make this all worthwhile, or to hit the end of his limit and use it as the final excuse he needed to delete the stupid app.

'It's a match!'

Andrew did a double-take. He didn't expect it to actually work. He was immediately greeted by this new profile description.

'Alison, 37'

'1 Mile away

Not looking for anything serious. Don't want any commitments.

If you're simply on here to hook up and have some no-strings-attached fun swipe right.'

Andrew was skeptical, very skeptical. The photos showed off a very shapely woman, posed in a variety of different outfits. Her thick, curvy thighs displayed the type of large ass that would make a man sweat over. While not quite the slandered definition of a 'thick girl,' with her flat stomach and hips making her look rather thin by comparison to her legs. She did, however, have sizable breasts to complete her 'heavenly' figure.

Added to that, her slightly curly, brown hair fell to her shoulders and a smile that was almost as eye-catching as her body. This Tinder profile was the proverbial 'white whale' of Tinder profiles. A gorgeous woman, 'Thick' with two C's, with a beautiful smile and fantastic cleavage. She was actively looking to hook up, no strings, no commitment and has purposely swiped right on Andrew's profile.

He didn't believe it, he couldn't believe it. There was no way in hell this 'Alison' was real. Further proof to this claim came from the very obvious examples in her photos, once Andrew could pull his eyes away from her body, that in every photo of the woman, the top half of her face was hidden. Either cut off at the top or scribbled out in an attempt to censor herself. Alison had made sure that her face was not visible in any of her images. An outstanding red flag for Andrew.

Andrew sighed with frustration, his phone thrown to the bed. He wouldn't entertain the idea that this woman was real. It was the very definition of 'too good to be true.'

"Stupid waste of time..." he whined, falling to his bed.

He spent a good several minutes laying in bed. Sulking and debating in his mind. After a while, he picked up his phone again and scrolled to the app. His finger held down, the options for it popped up on the screen.

Uninstall.

His finger hovered over the section of the screen but before he could commit to the app's deletion, his phone buzzed.

A notification from the app he was about to remove. It taunted and tempted him until Andrew couldn't take it anymore. Against his better judgment, he opened the app. A message from Alison waited for him.

"Heyyy" The message read, the extra y's creating an illusion of a real and excited person on the other end. "It's nice to meet you, Andrew." Adding a smiley face emoji to the end of it.

Andrew considered his options, to the best of his recollection, he had never seen a bot use his own name. Usually, they'd give a few generic responses before sending him a link to some horrible looking website.

This felt different, or at least part of Andrew wanted to believe it was real. He felt like an idiot, hoping that this was a real person, but after several long minutes, Andrew sent a reply.

"Hey, Alison. It's nice to meet you too."

Andrew waited for the inevitable generic response. The final, damning piece of evidence that proved that 'Alison' wasn't a real person and that Tinder was the waste of time Andrew knew it to be. His phone buzzed again as he braced himself for the disappointment to come.

"I hope you don't mind the age difference between us." Alison replied, "Personally I think matching with someone so young is, exciting." This time a winking face emoji ended the message.

Andrew realized that was too specific a comment towards him to be a bot. He couldn't help but smile as the hope that this was a real person grew.

"No, not at all." Andrew texted, "I don't mind it at all."

"So Andrew, Tell me about yourself? What are you looking for here?" Alison probed, very directly which kept Andrew wary.

"Just like it says in my bio." he messaged nervously, "Meeting new people, Looking for something new... something fun."

Andrew became painfully aware of how bland his profile looked. He winced at his horrid attempt at being flirty.

"Haha, sorry." He quickly apologized, "I'm too used to getting bots on this app, I don't have great experience at messaging actual people."

He immediately regretted sending the message as soon as it was sent. Not only did he admit that he thought she was a bot, but he also pointed out his lack of experience. It took several long agonizing seconds before Alison responded.

"Fun is good." Alison returned, "And don't worry, I like the shy quiet type. Especially if they're as cute as you."

Andrew was blushing, never in his life had he seen a woman be so aggressively forward with him. As the two exchanged messages back and forth, two things became apparent. Andrew had no idea how to flirt through text and Alison didn't care. To Andrew's surprise, she actually found his inexperience to be, as she put it, 'quite adorable.'

As flirty as Alison was, and as direct as her intentions with Andrew were, she didn't appear to want to meet up as soon as possible. She wanted to get to know Andrew first, which was understandable. Andrew himself was apprehensive to meet up with a complete stranger, regardless of how attractive she appeared to be.

Once the awkward introductions were over and the 'ice' relatively broken, the two started to share basic details about one another. Andrew was very forthcoming when talking about himself. He talked about his current living situation, life at college and his bad experience with Tinder.

Alison on the other hand, for all her flirty and forward nature, was very reserved in talking about her personal life. Andrew learned that she worked at a pharmacy, but wouldn't say which one. She had a fondness for drawing as she once wished to be an artist in her youth. It was also her first time using Tinder, she also didn't have much experience with the app, she mentioned that she received several matches, however, Alison claimed that Andrew was the 'most promising match' she had.

It was obvious that Alison was hiding herself, her photos all avoided showing her full face, along with her avoidance of talking about her current-day personal life, even refusing to give her last name. Andrew however chose to ignore this fact, as the excitement of talking to someone real overrode any gnawing curiosities he might have had.

Even after an hour or two of messaging, Andrew didn't want the conversation to end. With some trepidation in his fingers, he sent Alison his phone number, with the hope that they could continue to get to know each other outside the app.

She didn't respond. One hour went by, Andrew began to worry. Another hour went by, worry turned to regret, Andrew read back over their conversation, trying to work out where he went wrong. He debated sending her another message, apologizing in the hopes to start over, but he decided against it. Defeated, he put his phone down and went on with his day.

That night, as Andrew laid in his bed considering the events of the day, his phone buzzed. The tune one he immediately recognized as a text message. He spun around as fast as he could and grabbed his phone. A short text from an unknown number greeted him.

"Hi Andrew," the message read, "It's Alison, sorry about going silent on you, but some things came up in life that distracted me. I hope you're still up to talk?"

The bouncing ellipsis on the screen told him she was still writing more.

"My life can be pretty chaotic, so I might not always be able to text back. To be honest, I didn't think anyone would swipe on me, or that I'd get a cute boy's number."

Andrew read the message with a giant grin on his face. He tried

his best to respond casually, attempting to hide his excitement.

"Hey, I'm up," He responded, "And don't worry about it, I know life can be crazy at times. I never expected to get this far either, Not exactly sure what to do. Haha."

Andrew had spent several minutes considering what emoji to end the text with, but ended up sending it without one after realizing how sweaty his hands had gotten, he chuckled to himself about how worked up he was getting.

"Also..." The message from Alison replied, "In regards to our earlier conversation. Here's some proof that I'm not a 'bot' or a scammer."

Alison ended the message with a 'tongue out emoji' and capped it with a photo. The photo in question made Andrew's jaw drop.

It was a selfie, Alison sat on her bed, phone held above her. This time her face was fully in the frame, her beautiful, brown eyes completed her already gorgeous smile. More distractedly though, was her very risque, white lace corset lingerie, complete with a matching thong. The angle that Alison had taken the photo highlighted her deep cleavage and made sure to fit as much of her body as she could.

The only words that Andrew could think of texting back were, "Wow..."

His brain was too focused on burning the image into his mind to think of a more appropriate response.

"Oh, And please don't share that photo with anyone." She added on to the message, "I'd hate for people who know me to see it."

"Yeah, of course," Andrew replied, "Though I'm starting to feel way out of my league, haha. You're so beautiful, How'd I get so lucky? Like what's the catch?"

Andrew also added a 'tongue out emoji' to this message, he sent it as a sarcastic, innocent joke. He didn't actually expect there to be a catch, or for Alison to actually answer the question. It took several minutes before she replied.

"Well actually..." The first message said, "There is a catch."

Andrew braced himself after reading that message, his immediate thought went to money. Had this all been a long con to pay for sex? He dismissed that thought, Alison had specifically stated that she wasn't a scammer.

"The reason why I've been so elusive with my personal life." Alison began, "Is because I want this little 'relationship' of ours to be a secret. And the reason I want it to be a secret is..."

There was another pause between messages, Andrew watched in silence as the little ellipses bounced. His eyes occasionally jump back up to the image of the beautiful, half-naked woman on his screen.

"There's no easy way to say this, so I'll just say it and you can decide if you want this to go further." Andrew was confused, intrigued and anxious as the final message came, "The truth is, I'm married."

"Oh," Andrew responded, unsure of what exactly he could say to that. He was partially relieved that her interest in him was still genuine, while also thinking of all the ways this could blow up in his face.

"Yes..." Alison continued, "So I'll understand if you don't want to continue you. I know it's a lot to ask of someone, especially someone so young."

"No, I want to see you!" He responded, his fingers typing faster than he could think.

Andrew had made a snap decision, he knew that he was 'thinking with his dick' and that the tantalizing photo Alison had sent prior had made a large impact on that decision, but he was willing to risk it.

"I'm fine with it, honest." He continued, "Just let me know when you're next free and we can meet somewhere. Discreetly of course."

Andrew wasn't sure what he had gotten himself into, but all he knew was that he wasn't going to let a woman like that slip through his fingers.

"Great!" Alison replied, "I'm free tonight if you're not busy? I have the house to myself for a few days."

The sudden invitation threw him off balance, he hadn't expected it all to happen tonight. He's looked at the clock in his room, 10:47pm. As a poor college student, he didn't own a car, often relying on public transport to get him from place to place. His chances of getting a bus were low, and an Uber was sure to be expensive depending on how far away she lived.

"That depends." He said with hesitation, hoping that he could find a way to make it all work. "What's the address?"

As Alison's response came, Andrew was surprised for the millionth time today. As Alison's address was a very familiar street. Another wide smile grew on his face, as Alison lived not five buildings down the road. This mysterious married woman had been so close this entire time.

"I'll be there in 15 minutes." Andrew texted. Tonight was going to be a memorable one and Andrew had to get dressed for the occasion.

Thirteen minutes later, Andrew stood in front of Alison's door. He'd thrown on a dress shirt and some slacks in the hopes to appear more mature. Fiddling with his hair all the while he approached the door. The adrenaline rush of the anticipation beat out the rising anxiety in his stomach as he knocked on the door.

Alison opened the door, revealing Alison, the exact same woman as the photos had indicated, he was relieved to see that she was who she said she'd be, and also a little surprised to find her ever so taller than he was. She was wearing a dark purple dressing gown, with the faint scent of something floral emanating from her. Upon locking eyes with Andrew, she smiled, before taking a quick peek behind him. Once she was certain that no unwanted eyes were on them, she pulled Andrew inside.

"H-hey." Andrew said excitedly, "It's nice to finally meet you."

He chuckled nervously as he inspected the room, the place was much larger than what he was used to, and the furniture looked far more expensive than he felt comfortable being around. He quickly turned his head away, not wanting to gawk for too long, Alison then closed the door and walked past him.

"Do you want some wine?" Alison offered, pointing to the bottle that was already prepared on her dining table, two glasses ready for pouring. "I think that's what people do in this situation, to loosen up."

Andrew nodded in affirmation as Alison opened the bottle of wine and poured herself two glasses. The two stood at either end of the table, unsure if they should sit down or stay standing.

"Thanks," Andrew accepted the glass, he'd never gotten a taste for wine but he wasn't going to let that show now. "It's a real nice place you got here."

Alison smiled in reply, the chosen topic seeming to strike a nerve.

"Yes," She grumbled dismissively, her fingers fiddling with the ring around her finger. "It's a fine place, but far too large for my taste, especially the days when I'm all by myself."

Andrew noted her annoyance was not towards anything he said but spoke more to whatever situation had led her to seek an affair in the first place.

"Um, Not to dampen the mood," Andrew probed, wanting to get clarification on her husband's whereabouts, "Where is your... uh, husband? He's not gonna like, walk in on us or anything?"

He cringed a little after mentioning it, the last thing he wanted was to bring up a sore topic and ruin any chance of things continuing.

"No." Alison replied, returning to her glass of wine, "He's away, business trip or some such nonsense. I don't actually know what he's doing."

Andrew could hear the slight tinge of anger in her voice towards her husband.

"But he won't be home for the week, leaving me alone in this house, in this city... away from everyone else I cared about." Realization flashed across Alison's face as she shook herself out of her bad mood.

"Sorry, it's been a while," Alison continued, "Since I've done this, I may be a little rusty. Not that I've done this before..."

Her assertive personality online had now softened, the way her finger danced around the glass made Andrew realize that Alison was just as nervous as he was.

"That's alright," Andrew said, taking a sip of the wine and trying not to react to it. "It's alright, it's my first time doing this."

Panic set in as Andrew realized how that might have sounded, "Uh! I mean, it's not my 'first time' but it's like, my first time meeting up with someone... online that is."

As Andrew stumbled over his words, he chose to shut himself up by taking a larger swig of wine, before stifling a cough, he felt himself digging deeper and deeper into the proverbial hole. Much to his surprise, Alison simply giggled at his panicked rambling, as she gave Andrew a calming gaze.

"Well then." She chuckled with a playful smile, before sculling the rest of her wine, "Since we're both such 'virgins' at online hookups..."

She placed her glass down gently, the wine giving her renewed courage.

"Why don't we just take this slow." She walked off towards a nearby couch, not wanting to be left behind, Andrew quickly followed, similarly sculling his wine "Get ourselves, comfortable."

As she sat down on the couch, Andrew could see partially between her dressing gown. The same white lingerie could briefly be seen as she adjusted herself, the mental image of the photo flashed in his mind. Coupled together with her now exposed leg as she sat sideways on the couch, Andrew could feel an erection growing.

"Sit down." Alison purred as she pats the couch seat next to her.

Andrew noted that the couch was smaller than he initially assumed and knew that with the way she was sitting, the two would be very close. His assumption was proved correct as he sat down, as Alison's leg gently kicked right next to his, not quite touching but inching closer with every movement.

"Good boy." She praised Andrew as he relaxed into the couch, "I like a boy who does what he's told."

This sent a shiver down Andrew's spine, along with a huge blush across his face.

"Oh?" Alison perked up, "You like that did you?"

Her leg moved slighter higher as she leaned closer toward Andrew, her perfume radiating from under her dressing gown. Andrew instinctively followed his nose towards the