Not Looing for Love Vol. 01

Introduction

The world of online dating sites and apps is the place to be if you are looking to expand your sexual experience and live out your fantasies.

Single, attached, straight or gay, you can find what you are looking for from the comfort of your couch.

Not sure what you are looking for? Have a browse and see what catches your eye.

This is the age of cheating, of having multiple partners, of experimentation.

No longer are one night stands with strangers frowned upon. It has become the norm.

Volume 1.

Jon and Trina

At 23 years of age, Jon was into the normal things that all heterosexual males are. Females. And in the age of dating apps, this was a fun time to be around. Swipe and like apps were the choice of most people. The ease with which you can flick through profiles and have a look to see what catches your eye, makes looking for partners quick and easy. No longer did you have to leave the comfort of your house, get dressed up, head to a bar or club and spend money on trying to find a partner. You can literally sit naked on your couch at home and chat to numerous potential partners at the same time.

And this is where we find Jon.

Jon is your typical male in his early twenties, he regularly works out and looks after his appearance. He is around six feet tall and has an athletic physique. Sounds like any other 23 year old male of today, you say. But Jon has an advantage in the dating game. His baby face. Jon looks a lot younger than his twenty three years.

Why is this a secret weapon you ask? Because Jon likes a particular type of female. He likes to go after what should be the unattainable. Married women. Married Cougars, MILFS and GILFS. Whatever acronym you want to use for older married women. Age doesn't worry Jon, the thought of fucking someone's wife is what turns him on. And the baby faced twenty three year old is just what a married thirty or forty something year old is looking for.

Jon has just started an online chat with a 38 year old using the name Funtime38. Her pictures show a fit looking brunette with what are clearly enhanced breasts. There is a bikini shot of her on a beach wearing a pink string bikini where her two purchases appear to be the focus of the photographer. They aren't ridiculous porn star type enhancements, but rather, they look to be the perfect handful. But they weren't what attracted Jon. What Jon saw was how the photo had been cropped. Cropped to cut out whoever it was in the photo with her. Hopefully, it was her husband, thought Jon.

Jon began;

...Having a funtime38?

Not at the moment, you? Came the reply a minute or two later.

No, me neither, just keeping quiet at home.

Nothing wrong with that. Are you really 23yo like it says?

Haha... Yes, I always get asked that. Want to see my ID?

Hehe... no not your ID...

Not my ID?

No. Wouldn't mind seeing something else though...

Jon smirked; this game is too easy.

A movie?

Depends what the movie is I guess... and who's in it.

I'm sure we can find something we both like...

I'm sure we can. Now?

Sounds good to me, yours or mine?

Jon knew the answer to this already, but thought he would ask it anyway to be polite.

Yours? My place is getting renovations done.

Sure it is, thought Jon.

Jon and Trina, as he later found out was her name, continued some small talk until Jon gave her his address and invited her over. Trina said she doesn't live too far away and will be over in the next thirty to forty minutes, if that suited Jon. Jon told her that it would be fine, it would give him some time to clean up his place and freshen up with a shower.

About fifty minutes later there was a knock at the front door of Jons apartment. Jon wearing only shorts and a t-shirt, headed over to the door, excited to see if the photos of Trina were as good as the real thing. Although, it really wouldn't matter, he'd be keen to fuck either way.

On opening the door, Jon found Trina standing there looking just as good, if not better than her photos. She was wearing a pair of black gym leggings, which showed off her shapely, toned legs. Her top half was covered by a loose fitting white jumper, which allowed the perkiness of her enhanced breasts to be still visible through the material. She had her hair in a loose bun at the top of her head and a devious look in her eye. Jon looked her up and down and gave an approving smile.

"I'm guessing you're Trina?" Jon said.

"And I'm guessing you're Jon?" replied Trina.

They exchanged smiles and Jon invited her inside. As he shut the door and followed her into the living area, Jon took the chance to examine her ass through the leggings. She had a perfectly shaped ass, it hardly moved as she walked. Jon got half hard thinking of having those ass cheeks in his hands and on his mouth.

As they entered the living room, Trina placed her handbag down and took a seat on the couch. Jon gave the token polite offer of a drink, before sitting down beside her.

"So what movie we going to watch?" enquired Trina.

Jon looked back at her with a blank look on his face, he hadn't thought that they'd actually watch a movie, so he had no ideas ready to go. "Ahhh, not sure. What sort of movie do you feel like watching?"

Seeing the expression on his face, Trina laughed. "It's alright, I was only joking. I didn't come over for a movie night. And judging by that little bulge in the front of your shorts there, you've got other things on your mind also."

Jon looked down and saw that his half hard cock was clearly visible through the thin material of the shorts he was wearing. He had no underwear on, so it could be seen clearly and unrestricted by Trina.

"Yeah, sorry about that, but that ass of yours in those leggings looks amazing!"

With that, Trina stood up and turned around in front of the seated Jon. Her ass was now level with his face. "This ass?" Trina said as she ran her hand over each cheek slowly.

Jon sat there and admired Trina's ass, it looked firmer up close and personal, like it was now. He could see the slight outline of her thong underwear at the top of the cheeks. The perfectly rounded ass led down to two perfectly shaped legs, making Jon think that she clearly works out and looks after herself. There was a nice gap between her legs where her pussy was hugged by the small thong underwear she had on underneath.

Jon couldn't just sit there and watch anymore, he took both his hands and cupped each cheek through the tight black leggings. The shiny material hugged her body tightly and felt amazing as he ran his hands over her ass. He moved his face in closer and kissed each cheek in turn, this bringing a slight moan from Trina. Jon felt her slightly push back into his mouth as he continued to kiss the cheeks through her leggings. He moved his mouth downwards and began to kiss between the cheeks, cupping each cheek in his hands and pulling them apart. Trina slightly bent forward, allowing Jon to put his mouth between her legs, kissing and licking her pussy through the tight shiny material.

Trina was clearly enjoying this, she was pushing back against his mouth now with more force. Jon kept his mouth on her pussy though the leggings and reached up and under the loose fitting jumper to explore what was there. He found that Trina was wearing a sports bra, which he easily slid his hands under, and began to play with the firm breasts that it contained. He pinched the hard and stiff nipples and squeezed what was the perfect handful of breast.

Jon then brought his hands back to the top of her ass and began to slide the leggings down. He slid the leggings over her black thong and pulled them down to expose her whole ass. Now his lips were on her bare ass cheeks. The cheeks were firm and smooth, he licked and kissed his way down towards her pussy. As he neared, Trina bent over to expose her pussy more to him. First, Jon kissed and licked her pussy over the thin material of her thong, then he slid the thong to the side and kissed her now exposed pussy lips. Trina was clearly enjoying the treatment, Jon could visibly see her wetness in front of his eyes, so he plunged his tongue into it. He flicked his tongue in and out before he grabbed her ass again and spread the cheeks apart so that he could plunge his face and tongue deeper into her, now very wet, pussy.

Trina was pushing back into his face with more force now, almost falling into him with each rearward thrust. She tasted so good, so Jon kept licking and sucking on Trina's dripping wet pussy, her moans became louder and louder. Trina reached a climax as Jon fucked her deeply with his tongue over and over again, lapping up her juices.

Trina, recovering from her orgasm, stood upright and removed her top and leggings. Now, standing in front of him in her black thong and black sports bra, she looked at the enlarged bulge in the front of Jon's shorts. Saying nothing, Trina got onto her knees between his legs and began to rub Jon's cock through his shorts. She moved her hand up and down the shaft, wrapping her hand around his firmness. She then moved her hand to the waist band on the shorts and pulled them down, Jon raised his hips at the same time to assist in the shorts being pulled down and off his legs. Trina then took his bare cock in her hand slowly slid up and down the length of it. Looking at Jon in the eye, she moved her head downwards and placed the tip of his cock into her mouth.

Trina began to lick the length of Jon's cock, moving her tongue up and down the length of the shaft. She licked all the way down to his balls, taking one, then the other into her mouth and sucking on them, before moving back up the shaft again. Once she reached the tip again, Trina put her whole mouth over his cock and began to take it in. She moved down and up his now rigid cock, sucking and slurping her way as she went. She tried to take his whole length in, but gagged, which stopped her abruptly. Trina regained her composure and got back to work sliding her wet lips and mouth up and down Jon's hard cock. On reaching the head again, she ran her tongue around the tip of his cock in a circular motion, before enveloping the cock again with her mouth.

Jon has his eyes shut and was enjoying the attention Trina's mouth was giving him. He looked down at her and said, "I bet your husband would love to see you now!".

Trina paused for a moment, her eyes moving up to meet Jon's. She didn't say anything, but gave a mischievous smirk that gave Jon the answer he was after. He had done it again, another horny wife looking for some side action.

As Jon shut his eyes, even more excited now than before, he continued to enjoy the attention his cock and balls were receiving from Trina's mouth and tongue. He moaned softly and held Trina's head in his hands, pulling on her hair as she worked on him. He followed the movement of her head with his hands, coming up with her as her head moved upwards, and going down with her as she slid further down his shaft. As she neared the bottom of her movement, Jon pushed down on her head, making her go deeper on him. Making her gag. Trina caught her breath and went straight back to work licking and sucking.

After what seemed like hours, Trina removed her mouth from Jon's cock. She stood and straddled Jon sitting on the couch. As she did this, Trina pulled her thong to the side and grasped Jon's long hard cock. Trina lowered herself, as she went, she slowly put the tip of Jon's cock inside her wet entrance. At first, it didn't want to go in, but Trina held the shaft and slowly rubbed her wetness against it, as she slowly lowered herself onto it. Having successfully got the tip of Jon's cock inside, Trina then allowed it to go deeper and deeper inside her, until the full length of Jon was inside.

Jon moaned and softly swore as he felt the tight, wet, warmth of Trina's pussy. There is nothing better than the feeling of the cock's first entrance into a pussy. The way the pussy was resistant prior to allowing the cock to enter. The feeling of tightness as the cock entered for the first thrust of many. Jon was in heaven. Trina had taken his cock without one mention of using protection, she had taken charge so who was Jon to argue? The danger of going bareback with a random, a random married woman. It was so hot Jon thought he was going to burst then and there.

Regaining his composure, Jon focused back on Trina who was now riding him in a rhythmic manner. Sliding her pussy up and down his cock, arching her back and fucking him with her eyes closed. Her arms were around his neck and her head was thrust back as she rode him. Jon put head between her breasts and pulled the sports bra up to expose one of the hard nipples it contained. He put his mouth over the nipple and lightly bit on it, hearing a moan of pleasure from Trina, he bit it again, a bit harder this time. Jon then moved his mouth off the nipple and sucked on the side of the breast. He laughed on the inside as he sucked hard, hoping to leave a hickey there on her breast for her to try and explain to her husband. This was his calling card of sorts. Jon tried to do this to all the married or taken women he fucked.

Trina showed no resistance to his mouth, she was too involved in the feeling of his cock deep inside her pussy as she rode up and down on it. Jon, feeling himself getting a little too excited, decided it was time to change positions before he lost control. So, pushing Trina off him, he stood and turned her around and bent her over the couch. Trina was more than willing to place her body where Jon wanted it. With Trina bent over in front of him, Jon ripped her thong down and pulled it off, he then slapped her right ass cheek hard, leaving a hand imprint there, before stepping towards her and rubbing the head of his cock along her pussy. Trina was pushing back into him, willing his cock inside, but Jon wanted to tease her for a bit, rubbing his cock up and down her pussy.

Just when Trina was beginning to get frustrated, Jon thrust his cock hard and deep into her, causing her to gasp. He went as deep as he could go then, holding her hips for support, he began thrusting in and out of her with force. Loud slapping noises were being made as Jon's body slammed into the firm, round ass cheeks of Trina. As Jon slammed into her, Trina began to squeal with delight.

Trina was willing Jon to go harder and harder, as both were coming closer to climax. Trina came first. As Jon was slamming into her from behind, Trina lost all control and screamed with pleasure. Jon, feeling Trina contract against his cock was then brought to the point of climax himself. Sensing Jon reaching the point of no return, Trina collected herself, caught her breath and told Jon to cum inside her. For Jon, hearing those words was the tipping point, he was turned on beyond control. In no time he reached a climax and emptied himself into Trina as he thrust deeply into her in a fit of orgasm and pleasure.

They both collapsed onto the couch, catching their breath and attempting to regain composure. No more than thirty minutes ago they were complete strangers, not anymore. They had just finished what is one of the most personal experiences two humans can share.

And that's what Jon loved about the modern dating game. With his phone he is able to meet, and within a matter of minutes, catch up with potential partners. It was an exciting time to be single and looking to mingle.

Jon was already looking forward to his next conquest.

But first, he might see if Trina is ready for round two.