Taking a Chance on Love

All Rights Reserved ©

Chapter 6

“Let’s go, Jess!”

Cheered on by her team mates, Jessica eyed the pitcher, waited for him to lob the ball.

It was the first weekend in August, and this was her team’s last game of their tournament. If they won, they’d take third place in their league.

It was the bottom of the fifth and her team was up by four and wanted to keep it that way.

The pitcher sent the ball to her and Jessica tensed, gripped her bat a little tighter. She swung, made solid contact, and immediately dropped her bat and ran for first base, getting there a few seconds before the ball thwacked into the first baseman’s glove.

The ball was returned to the pitcher and her teammate, Mel got up to bat. Knowing how good a hitter she was, Jessica was ready to run. When Mel sent the ball careening low and fast between first and second base, she took off. She had to hustle because the other team recovered the ball quickly, but she made it to second, and Mel made it to first.

Standing at second base, the sun beat into her eyes from behind home plate, so she shielded her gaze with a hand so she could watch Greg take his turn at bat.

Though the sun was out, it wasn’t as hot and humid like it had been the last while, thanks to a storm that had rolled through the area a couple of days back.

Greg let the first ball sail by him.

“Good eye, Greg.” teammates hollered from the bench.

The pitch had looked low and inside, but Jessica wasn’t surprised when the ump called a strike.

This wasn’t the first game they’d had this guy as an umpire. He’d been making bad calls all season. The guy was apparently blind as a bat.

Greg and the ump shared a couple of mumbled words, before Greg faced the pitcher once more.

The next pitch was right down the middle. Greg swung and smashed the hell out of the ball, launching it way out to left field.

Jessica took off. Legs and arms pumping, she headed for third, flew by it and charged for home to the sound of her team’s cheering. Mel came in right behind her.

The two of them moved off to the side, slapped a high five, turning their attention to Greg, who was rounding second, one eye on where the ball was at. He put the brakes on, backed up to second when the outfielder threw the ball to the short stop.

Smart. He might have made it, but it would have been pretty damn close.

Missy got up to bat while Jessica and Mel joined their teammates. Jess went back to where she’d been before her turn at bat, standing next to Laura, leaning against the fence that separated their bench from the diamond.

Missy laid off on the first two pitches she got, swung at the third. Unfortunately, she hit a pop-fly, the ball arcing up and over and straight into the pitcher’s glove.

Eric was up next. With the first pitch, he got a good hit, getting himself to second and bringing Greg home.

If Jessica’s math was correct, the score was now nine to two, for them.

A few minutes later, when the inning ended after John’s pop fly was caught, and Margo was struck out, her math was confirmed. The ump called out the current score - nine to two.

The teams switched places. Jessica grabbed her glove, jogged out to first base, while Laura quickly threw on her catcher’s gear.

“Let’s go, guys!” her friend, hollered as she squatted behind home plate. “Three up, three down.”

As nice as it would have been to keep the other team from scoring, to hold them at two runs, they weren’t able to do it.

Despite good pitching and quick reflexes on their part, they lost the nice lead they’d had. The score called out at the end of the inning was nine to seven.

A bad turn at bat for their team didn’t improve their situation.

First Mike hit a pop fly, which was caught by the short stop, then Laura got to first with a bunt, but got no further because the two players after her were struck out.

At the top of the seventh, the other team took the lead for themselves, getting three more runs.

Jessica’s team needed to get two runs to win, or at least one run to tie, and push the game to another inning.

They pulled it out and got the runs they needed, tipping the final score in their favour, eleven to ten.

Third place was theirs.

The teams lined up and shook hands, the words ‘good game’ repeating between players for several moments.

Sportsmanship courtesy paid, Jess and Laura went to collect their stuff.

“Good game you guys.” Mel said as she passed by them, ball gear in hand. “See ya Friday.” she smiled, referring to their awards banquet which was happening next Friday.

“Good game.” Jess and Laura echoed. “See ya.”

Jessica turned her attention to Laura as they stopped by the bench.

“You feel like coming over?” she asked as she picked up her glove, tucked it under her arm. “Watch the last episode of ‘The Case’?”

Collecting her own stuff, Laura replied with a ‘sure’.

The sun was just starting to dip behind the tallest of the trees in the park as they headed from the bench over to where their folks were chatting together near the stands, waiting for them.

“Good game, you guys.” George and Linda complimented.

Laura’s parents, Diane and Freddy, echoed that.

It had been a good game, a close game.

Jessica and Laura both smiled a ‘thanks’.

The small bunch of them chatted for a bit, eventually starting towards the parking lot where they parted ways and went to their respective cars.

A few minutes after driving away from the diamond, Jess and Laura met up at her place.

“You want some popcorn?” Jess asked, once they were in her place, their shoes ditched by the front door, the two of them heading for her living room.

“If by popcorn, you mean ice cream,” Laura replied. “... then, yes.”

Jess chuckled.

Ice cream it was.

She headed into the kitchen for the Ben and Jerry’s and two spoons while Laura continued on to the living room. Frozen pint in hand, she plopped down next to her friend on the sofa.

The small container of Chunky Monkey was passed back and forth as the two of them watched the last episode of ‘The Case.’

This was the third season for the show and, since it was a Netflix original, unfortunately probably it’s last.

Jessica hoped ‘The Case’ would get a fourth season, but not many Netflix shows got more than two or three seasons. If this was it, she was satisfied with the show’s possibly final episode. They’d wrapped things up nicely.

Suggestions for other shows to watch appeared on the screen when the episode ended.

Jessica ignored them, returned to her ‘Continue Watching’ list, and passed the remote off to Laura as she got to her feet.

“I gotta go to the bathroom.” she announced. “You pick something for us to watch.”

That Laura chose ‘Friends’, didn’t come as a surprise to Jess when she rejoined her friend.

Her friend was a ‘Friends’-aholic.

They were into their second episode, the one where Phoebe and Mike meet after she and Joey set each other up with dates and Joey forgets, when Laura turned to her.

“I’ve been meaning to ask you,” she started. “... are you still on that dating site?”

Jessica shifted her gaze from the TV to her friend.

“I meant to delete my profile, but I keep forgetting. I haven’t been back on since that guy stood me up.” she replied. She tilted her head. “Why?”

“I was thinking of giving it a shot.” Laura shrugged.

Jessica scrunched her nose.

“I wouldn’t bother.” she advised. “Most of the guys that contacted me were just looking for hook ups.”

Laura ‘hmm’d’, obviously disappointed to hear that. Jessica had been dismayed when she’d had more guys looking for hook ups, than something serious. It hadn’t seemed to matter that she’d marked off ‘looking for serious relationship’. They’d still contacted her for hook ups.

Laura passed the ice cream back to her and she scooped some into her mouth.

That her friend was thinking of joining a dating site surprised Jessica. Her friend hadn’t seemed interested in meeting anyone the last little while.

Laura had been in a serious relationship for over a year, and when it had dead-ended a few months ago, she’d seemed happy to be single again.

But, if she was interested in dating again...

“You should ask out Greg.” Jessica suggested. “I think he likes you.”

She’d kept that suspicion to herself while her friend was proudly waving the single flag.

“Greg? From our ball team?” Laura asked, brows lifting with surprise at her suggestion.

Jess nodded.

“What makes you think he likes me?” Laura asked, brows furrowing now.

“Just the vibe I get.” Jessica shrugged. “He chats with you more than anyone else on the team.” she pointed out.

Laura didn’t respond to that. Judging by the look on her friend’s face, Jess presumed she was looking back over their season, reflecting back on Greg’s behaviour with her.

“He’s cute, don’t ya think?” Jessica asked after a moment, breaking into her friend’s thoughts.

Laura agreed he was.

“You should ask him out.” Jess encouraged.

“You really think he’s into me?” Laura asked.

“I think he is, yeah.”

Her friend looked intrigued, was obviously pondering this new information.

The two of them tuned back into the show, just in time to see Phoebe lay into Joey for setting her up with a stranger. That stranger would go on to be her husband, Mike.

The episode ended and Netflix was counting down to the next episode when Laura asked her if her feelings for Henry were still there.

“Yeah.” Jess sighed.

They were still there.

She wanted to talk to Henry again, but kept putting it off. For how many times she told herself to talk to him, she told herself just as many times that maybe she shouldn’t. Maybe she should just let it go, move on.

She’d never been so indecisive about something in her life.

“You gonna talk to him again?” Laura asked.

“Yeah.” Jess replied. “I think so.”

But... maybe she shouldn’t.


Saturday morning, Henry woke up hard and aching, the feel of Jessica wrapped around him still imprinted in his skin, his muscles.


He rolled over on to his back, kicked the sheets off. He’d been on his stomach, dry humping the damn mattress.

He slipped off his boxers, took himself in hand.

He could let his morning wood subside, but he wasn’t gonna. Didn’t want to. He wanted to finish what he’d started with dream Jessica.

Well, if he was talking want, what he really wanted was to be with the real Jessica.

But that was never gonna happen.

Since he couldn’t be with her, he had to settle for enjoying the dream version. He had years of practice.

A part of him felt guilty, like he was being disrespectful, getting off to thoughts of Jessica, but that part faded in the face of his stirred desires. As it always did.

Closing his eyes, Henry pulled up one of his go-to fantasies.

In his mind, he was splayed across his bed, waiting for Jessica to join him. She’d gone into the bathroom to change into some new lingerie she’d bought.

His dream self was impatient, couldn’t help but give himself a rub and squeeze through his boxers... the minutes he spent waiting interminable.

The door finally opened and Jessica stepped out.

In his fantasy, Henry pictured Jessica with her brown hair down, soft and loose around her face and shoulders. She was smiling at him. A sensual smile, her lips unpainted.

The new lingerie she’d bought to wear for him was a lacy, red delicacy.

Henry’s cock kicked at the visual of Jessica in the nightie he’d imagined for her this time, her breasts pushed together, exposed by the deep V-line neck of her outfit.


He wasn’t even imagining them doing anything yet, and he was ready to finish.

Fantasy Jessica slowly walked toward him, a hand coming up to that steep neckline, a finger skimming leisurely up and down the lace. Her nails were painted the same shade of red as her outfit.

His imagination was keen on even the little details.

Henry’s grip on himself tightened as he imagined Jessica climbing onto his bed and onto him, straddling him.

Those beautiful breasts of hers were right before his eyes.

Henry stilled... a realization hitting him.

In his fantasies, he often put him and Jessica in this position, her in his lap...

When he almost kissed her that Sunday months ago, that’s how they’d been... her in his lap... his fantasy, made real.

Maybe his brain had taken that familiar situation and lowered his inhibitions, resulting in a glitch in his willpower.

No wonder he’d had a moment of weakness.

Henry disregarded his thoughts, his hand moving again, up and down his cock.

The reason he’d slipped up didn’t matter. What mattered was that he made sure it didn’t happen again.

Eyes closed, hand full, he imagined that it wasn’t him stroking his cock, but Jessica. She lowered herself down, trapping his cock between his stomach and her core. There was no crotch to her nightie.

Henry imagined that all he felt, as she rocked forward and back on him, was her slippery, warm, folds.


In his daydream, Henry slipped his hands to the neckline of Jessica’s outfit, pushed the material to the sides, setting her breasts free.

Her nipples were already stiff peaks, a result of arousal and the abrasion they’d received from the lace. Henry envisioned them to be a lovely, rosy pink colour. His fantasy self latched onto one, taking the hard nub into his mouth and worrying it gently.

Pleasure shot up Henry’s cock, a drop of pre-cum beading at the tip. His stomach muscles jumping and clenching, he hurried his strokes, tightened his grip as he imagined Jessica letting out little gasps and moans above him.

He suckled her more strongly and pulled a growl from her throat. Lifting away from him, she demanded he fuck her. Rising onto her knees, she grasped him with one hand, pointed him straight up and lowered herself onto his rigid length.

Henry groaned into the quiet of his room as he neared climax, the physical and visual stimulation bringing him closer and closer.

As he pictured Jessica riding him, taking her own pleasure even as she bestowed pleasure on him, he started pumping himself, his free hand fisting the sheets at his hip.

Jaw clenching, toes curling, he came, painting his lower stomach with streaks and drops of creamy white.

He grunted and groaned his way through his orgasm, his muscles tensing... and slowly releasing, leaving him boneless.

It was a long while before he cared to move. Not just because of the energy he’d just expended. But because of the sadness, the loneliness that came over him, post pleasuring.

He wanted to be with Jessica... but the reality was, that wasn’t going to happen. The chance that they’d eventually split up was too high.

He didn’t want to end up like his parents had. He didn’t want to end up hurting Jessica.

And the thing was, he was aware that he was a lot like his dad. He could be stubborn, immature, inconsiderate, selfish. All things his mom had accused his dad of being when they’d been slinging insults.


Henry sighed.

... though he didn’t want to end up like his folks, he also couldn’t ignore the fact that if he didn’t take a chance at love because of the possibility of pain and loss later...

... he was going to be alone the rest of his life.

He really didn’t want that either.

Frustrated with himself, he grabbed his discarded boxers, angrily swiped at his stomach, cleaning himself off and got out of bed, went to shower.

The question was, which was he more afraid of...

... loving and possibly losing...

... or a life of loneliness ending in regret?

It had been thirteen years, and he still couldn’t decide which scared him more.


Continue Reading Next Chapter

About Us

Inkitt is the world’s first reader-powered publisher, providing a platform to discover hidden talents and turn them into globally successful authors. Write captivating stories, read enchanting novels, and we’ll publish the books our readers love most on our sister app, GALATEA and other formats.