A Summer To Remember [Mf]

*This one is more story and dialogue heavy, so I’m hoping it’s still good *

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It had been two weeks since Jen said goodbye before moving on her own into the city. The graduation party was a blast, but high school was over and it was time for her to grow up. While everyone else was going to spend the summer having fun, she wanted to get settled and adjust to this new place. Living here was like nothing she’d experienced – it was always busy and everyone seemed to be in a rush. She was still getting lost, but always ran into a kind stranger who showed her the way back.

She developed a routine of sorts, and a path to go on as she explored the area. Her first stop was Drexley’s, a local cafe, where she ordered her usual medium vanilla latte. She’d take a seat somewhere in-between the bar and the window, the best spot to people-watch without being caught. As she sipped her latte she browsed around on her laptop while looking at the other customers walking in. Today seemed the same as any others, with the typical people getting their typical orders, then she noticed someone different.

He was older, but it wasn’t that, it was how he dressed, very plainly, just a white t-shirt, jeans, and sneakers. It’s like someone his age should look more business casual. But more than his clothes, it was his overall appearance – messy hair, a few days of stubble, and this whole “just don’t care” aura about him. For some reason this made her more curious, so she eavesdropped and heard how chatty he was with the barista while ordering his mocha. He was definitely a regular, but why hadn’t she seen him before?

He sat down almost opposite of her, facing her, and got on his laptop. As she continued to stare, he caught her and nodded. “Oh fuck,” Jen muttered, this was awkward. She didn’t know what to do, then he came over.

“I saw you looking,” he said.

“Oh, no, I was daydreaming,” Jen replied.

“Yeah, about me I bet,” he boasted.

“What…I don’t even know you,” Jen couldn’t believe he just said that.

“My name’s Will,” he said, and extended his hand. “Nice to you meet you.”

Jen didn’t know what to do, she’d never been in this situation before. Will chucked to himself and said, “Ya’know, you’re supposed to introduce yourself.”

Jen reluctantly shook his hand and said, “Hi, I’m Jen.”

“Mind if I sit with you?” asked Will.

“Do you have any idea how old I am?” Jen couldn’t believe it again.

“Yeah, you must be like 37!” Will sarcastically replied.

“Oh my God…really?” Jen didn’t know what to think of this guy, “I’m 19, are you saying I look really old!”

“I’m 42, so it’s easy for me to find other old people,” Will smiled. He pulled his phone out of his pocket, then his face changed from upbeat to annoyed when he looked at it, “Ugh, I need to get going, we’ll do this again!”

As he left the cafe Jen said, “Yeah right!” What a weirdo, she hoped he never saw him again.

Jen got back to her laptop and went through her usual routine. She updated her social media, wrote about her day, looked up where to grab lunch and dinner, find some more cool places to explore…but the whole time she couldn’t stop thinking about Will. Just something about him, it was everything she didn’t expect from a guy. She should’ve left this coffee shop for good and found a new one, but she wanted to come back again tomorrow and run into Will again.

Sleeping was difficult tonight because she was still thinking about Will. It was just everything about him, a guy his age shouldn’t be like that – he shouldn’t look like that or dress like that or act like that – it made no sense! One thing she liked about Will is how his muscles were bulging through his t-shirt, and she remembered the bulge in his crotch too, he wanted to be noticed. And when he ran out of the cafe this morning, she couldn’t stop staring at his ass.

This weirdo was turning her on, she felt her panties starting to get wet. If Will had a smart mouth like that, imagine what his tongue could do to her pussy. The stubble would rub against her thighs as he ate her out. It would be rough, but it would feel good at the same time. As she thought about Will licking her pussy, she began to rub her clit. Fuck, she was already wet and sticky down there, her body wanted him.

Jen thought about Will’s cock inside of her. First she’d ride him, enjoying his thick cock as she bounced up and down. Soon she’d want Will on top, she’d want his sweaty, hairy body enjoying her young, warm pussy. Finally Will would do her doggystyle. She’d be on all fours, with her face buried in the pillow as he pounded her pussy. Jen knew her pussy got really tight during doggy and Will would cum, filling her up with his cum.

While Jen fantasized about fucking Will, she was fingering herself. Her panties were soaked and her juices were dripping onto the bedsheets. Fuck, what a mess, she just cleaned these, but at the same time she didn’t care. Her fingers went faster and deeper into her, her pussy clenching onto them, loving how they felt. Soon she couldn’t hold it in anymore and she came. Except this time she didn’t expect it to be so intense, she moaned loud and she was pretty sure her roommate heard her.

The next day Jen waited for Will to show up at Drexley’s, she was both excited and nervous about today’s plan. She didn’t want to make it too easy for him, but she was so horny she was afraid of getting pussy juice on the chair. Finally he came in and sat in the same spot, wearing a black t-shirt instead of white. He briefly looked at her, but seemed to be ignoring her this time. What was going on, why was he acting like this? She continued to stare at him, but he was too busy looking at his laptop to notice her.

Jen couldn’t take it anymore, her pussy was in control, she walked up to Will and said, “Hi, again.”

“Oh, hey,” he nonchalantly replied.

“That’s it, just ‘oh hey’?” Jen didn’t expect this.

“Would you prefer ‘hello’ instead?” he responded.

“You were chattier yesterday,” Jen said.

“I thought you didn’t like that,” said Will.

Fuck, thought Jen, he was making this difficult, “I’m pretty new to this city, I’m not used to how people act.”

“Yeah, you kids today are dumb,” replied Will.

Oh God, he was back, but was she ready to deal with this again? She almost wanted to touch her pussy to make sure if it still wanted Will, but she couldn’t do that in public. Instead she said, “Better to be young and dumb than old and annoying!”

“Oh, a little fiesty, I like that. Well I may be older than what you’re used to, but I promise I’m better!” Will smirked, he didn’t care how brazen he was.

“You can’t be serious, you really think I’d…,” Jen was shocked, but also excited, this was going to happen!

Will grabbed his stuff and prepared to leave, “I’m only a few blocks from here, you coming?” Jen couldn’t think of anything clever to say, she couldn’t think period. She grabbed her stuff and followed him.

He walked fast, like everyone else in the city, but even faster like he was trying to get away from her. Finally she caught up with him, then he said, “I win!” and Jen rolled her eyes. Will led her into the building and up to his apartment. When they were inside he put his stuff on the floor and she put hers on the couch. Will started to say, “So how about – ” but Jen put her hand on his mouth. She wasn’t going to let his big mouth ruin her moment, so she started to kiss him. Surprisingly he tasted good, not what she expected, there was some of the mocha on his breath, but also a bit of sweetness. Already she felt her pussy start to drip, she was going to finally enjoy Will!

Will was a really good kisser, his tongue was slowly swirling inside Jen’s mouth, tasting her. Other boys she’d been with went too fast, like they were starving, Will was savoring her lips. His tongue rubbing against hers, both wanting to wrap around each other. Sometimes he’d back away, then come back in, teasing her and every now and then. Will pulled back from her mouth and began kissing her neck, nibbling on it. “That feels good,” she cooed.

They kissed some more, then he picked her up and carried her to the bedroom. Will didn’t hesitate to take off his clothes, they were quickly in a pile in the floor. And he didn’t give Jen a chance to take hers off, because he started to remove her shirt and bra. As Will sucked on her tits, she pulled her yoga pants down and noticed how damp the crotch was…her pussy juice must’ve seeped through. And her panties were soaked as she hurriedly took them off.

Will was bigger than her, but she didn’t realize how much bigger until they were both naked, she felt petite next to him. The first thing she noticed was Will’s hard cock, it was pointing up to the ceiling, and it was months since she had some dick (it was a messy breakup with her ex). Jen put her hands around his cock, and inserted the tip into her mouth. She stuck her tongue out and licked along his shaft while sucking on his tip. Will was moaning and that made her take the cock deeper into her mouth.

He was so thick inside of her tiny mouth, she loved that his dick could barely fit. Jen started to bob her head up and down, slurping on his cock, letting her spit drip onto his balls. She moved her eyes up and looked at Will’s face, he was loving this and she loved turning him on. His pre-cum tasted different than the boys she’d been with before. Even though he didn’t care about his appearance, she could tell he took care of his body and had a healthy diet. His pre-cum had an almost sweet flavor to it.

The other times Jen sucked cock, she did it to make the guy happy, not really for herself. But with Will, it was different, she was starting to love it. His cock belonged in her mouth, and she couldn’t get enough of it. Up and down, her lips and tongue going all over his dick, all this cocksucking was so hot, and hearing Will moan made her go faster.

“Oh God, baby, don’t stop, don’t stop….” Will moaned. Jen didn’t want to stop, she was meant to taste his manhood, to slurp it up and turn this man on. “Keep on going baby, I’m going to cum!” Will shouted. Jen worked even harder, she sucked Will’s cock like a demon and felt it start to get really hot, get thicker, and felt it pulse. “Oh God, I’m cummmming!” Will yelled. She felt his thick, hot cum going into her mouth, and she did something she’d never done before, she swallowed it. Wow, she never thought she’d swallow cum, but having Will inside of her mouth was such a new experience.

Will was laying down and recovering from the orgasm, and Jen did another first, she crawled over to his face and sat on it. She was pretty shocked that she just took advantage of him like that, and didn’t know how he’d react. Then he grabbed her ass-cheeks, and she grinded her pussy on his face. She felt his tongue inside of her hole, she could tell Will enjoyed how she tasted, he was hungrily licking her. Will soon started to lick and suck on her clit. She couldn’t last long, and soon she felt herself cum without warning.

“I’m sorry, I didn’t mean to cum on your face,” said Jen, feeling embarassed.

“I know how to make you apologize,” said Will.

“Oh yeah, how –” Jen started to say, but felt Will pick her up and lay her down on the bed. Then she saw Will bring his head down to her pussy and lick her. She’d had her pussy eaten before, but never with a guy who seemed to love it as much as Will. He hadn’t even wiped her juices off before he was tasting her again. It was like how she dreamed about, his stubble rubbed against her thighs while his tongue tasted her and lapped her juices up.

Will was a great kisser, but he was even better at eating pussy. When she fucked his face before, she just wanted to cum fast, but now she wanted to relax and enjoy his mouth. He started by licking her pussy lips, then moving in closer to her hot, wet hole. Sometimes he’d tease her by licking on her clit. Then she put her hand down on Will’s head and pressed it into her, he began to suck on her clit. She wanted to cum from this again, but she didn’t think she’d be able to handle a dick inside of her if she came again.

“Oh God, please stopppp,” she moaned. “It feels good, but I want your dick, I want you to fuck me.” Will took her legs and put them over his shoulders, then he slowly put his cock inside of her. She felt her pussy widen as the cock went in, stretching so it could fit, then it was finally in. He started to fuck her slow, to get her used to his cock, but it was still enough to make her moan.

“How does it feel baby?” Will asked.

“It feels good, how does my young pussy feel?” she said.

“So good baby, you’re so tight,” he moaned. She wanted to say something back, but all she could do was moan. He started to go faster and it felt better. Her body was being enjoyed by this man, and it was wonderful. She loved how good she felt and how much pleasure she was giving him. Will went faster and harder, and her body started to shake as he fucked her.

“Your pussy is so good baby, It’s going to make me cum again,” Will said.

“Are you going to fill my tight pussy up?” moaned Jen.

“Yes baby, you’ll have more cum in your pussy than you had in your mouth,” said Will.

“I want you to finish me doggy, baby,” said Jen.

Will took his cock out and Jen got on all fours for doggystyle. Will slid his cock into her, and pounded away. There was no need to go slow this time, he was using her body and pussy to make himself cum. “Oh Will, fuck me hard, I know you love young pussy!” Jen screamed. Will grunted and went harder. “Yes you dirty man, fuck this 19-year-old girl, cum inside my pussy!”

Will went even harder, and Jen had to hold onto the pillow to keep her body from shaking too much. Without warning she suddenly came again, then she heard Will scream, “Oh God, Jen, I’m going to cum. Oh God, baby, I’m cumming!” and he groaned. She felt his cock get thicker and hotter as he came. His cum went deep inside of her pussy, completely filling her up.

After Will emptied his load inside of Jen, she turned around and looked at him. He was sweaty, she was sweaty too, and they were both satisfied. “You fucked me pretty good for an old man,” said Jen.

“I’ll fuck you even better tomorrow,” said Will.

Source: reddit.com/r/sexystories/comments/daf0a1/a_summer_to_remember_mf