Taking a Chance on Love

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Chapter 11

After a week of waiting for his next date with Jess, Henry’s excitement level was high as he entered the door to the lobby of her building the following Saturday night. Instead of buzzing her apartment, he pulled out his phone and texted her.

Hey. I’m here. he thumbed in.

A few moments later, a loud buzz sounded and the inner door to the apartments was unlocked for him.

He let himself in, got in the elevator and rode it up to her floor. A beat after he knocked on her door, she opened it with a ‘hey’, and a smile as wide as his own.

“Hey.” he echoed.

He stepped forward, his gaze travelling her from top to bottom, taking in her hair - soft and loose around her face and shoulders - the T-shirt and jeans she wore.

How did she make casual look sexy?

She shut and locked the door while he toed off his shoes, then lead him into the living room.

“You guys have fun?” she asked over her shoulder.

The ‘guys’ being his teammates. After winning all of their games in their tournament this weekend, and taking first place, they’d gone to Frankie’s after their last game tonight to celebrate with some beers.

Normally, Henry really enjoyed hanging with his teammates, especially after a win... but he hadn’t this time. He’d spent the whole time at the bar waiting until he could leave, impatient to get to Jess.

She’d been at their last game, and before they’d left the diamond, she’d managed to furtively approach him and invite him over to her place when he and the guys were done at Frankie’s.

“Yeah.” Henry replied now, in response to Jess’s question, not sounding like he totally meant it.

Since he didn’t.

Jessica sat on the middle seat of her sofa and he sat beside her. The TV was on and she reached forward, grabbed the TV remote off the coffee table and turned it off.

They chatted for a little while... but, words faded fast. Neither of them were in the mood to talk.

Henry could see the same want he was feeling, the same desire to pick up where they’d ended things on their date Wednesday, reflected back at him in Jessica’s eyes...

... and seeing that, only added fuel to his own desire.


Her gaze fixed on Henry’s, Jessica stretched toward him, raised her mouth to his. The first touch of their lips was brief. Henry pulled back for some reason, and she opened her eyes, saw that he hadn’t gone far... his mouth was mere inches from hers.

Was something wrong?

She lifted her gaze to his, reading his expression.

No, nothing was wrong. The heat she saw in his eyes, reassured her of that. Apparently he was checking that she was with him, that she wanted what he wanted.

She so was. She so did.

The corners of his mouth tipped up in a soft smile. He lifted a hand to her face, caressed her cheek with the backs of his fingers, riding the slope up to her temple.

He brushed her hair back from her face, then slipped his hand around to the back of her neck, and lowered his mouth to hers once more.

This kiss wasn’t brief.

This kiss went from zero to sixty in seconds.

Pressing closer, Henry’s arms came around her, even as hers went around his neck and shoulders. The thin, cotton T she was wearing offered no barrier to the heat pouring off of him.

He was a furnace.

He was gonna burn her up.


Energy coiled in Henry’s body, thick and hot.

Jessica sucked on his tongue and that energy spiked, triggering action.

He shifted forward, took her backwards down to the couch, came down on top of her - mindful of not giving her too much of his weight.

In this new position, she adjusted her hold on him, her arms slipping from his shoulders, going under his arms and around his back.

He settled between her legs, slowly rocked his growing erection against her core... just once.

There was no rush.

Breaking their kiss, he raised his head and gazed down at her... committing the way she looked; her skin - flushed with arousal, her face - slack with passion, to memory.

“You’re so beautiful.” he murmured.

The smile that his soft words brought to her face only made her more so.

She raised her head, coming after his kiss, and he lowered back down to her.


Jessica practically growled when Henry rocked himself against her for the second time.

It had been a long time since someone other than herself had undertaken the task of pleasuring her body...

... Henry wasn’t going to have to work hard to get her to the finish line.

Wanting to feel him - any part of him - without a barrier between her skin and his, she gripped his shirt near the waist of his jeans, pulled it free with a few tugs, and slipped her hands underneath the cotton.

He was so solid, so smooth, so warm.

His mouth pressed harder against hers when she brought her hands around to his front. She smiled, feeling his stomach muscles jump in reaction to her fingers skimming below his belly button.

He pressed his hips forward again, more firmly this time, and - of their own accord - her hands abandoned his front, sought out his ass, her fingers digging in, urging him even more tightly against her.


Jessica’s passionate grip on his ass, the pleasure his own movement generated, had Henry groaning.

Pleasure demanded repetition, and he retracted his hips, surged forward once more. In response, Jessica arched against him. Her head jacked to the side, and her mouth was ripped from his. The gasp she sucked in had him gritting his teeth, had his energy meter spiking high again.


He was going up in flames and he wasn’t even inside her yet.

He shifted and his foot slipped off the edge of the sofa, hit the floor. He quickly righted himself, braced a foot against the arm of the sofa.

“Maybe...” he murmured, in between dropping kisses along Jessica’s jaw. “... maybe we should move this into your bedroom...?”

Jessica’s sound of agreement was quick.

Pushing up from his forearms to his hands, he shifted his weight back on to his knees, got to his feet, and extended a hand down to help her up. Her eyes dark pools of desire and steady on him, she sat up, slipped her hand into his, and stood. No hesitation in her step, she lead him from her living room, around and down the hallway, toward her bedroom.

At the bathroom she stopped.

“One sec...” she murmured, letting go of his hand.

He waited, enjoying the view from the doorway as she bent over and retrieved - what he assumed was a condom - from the cabinet under the sink.

Straightening up, she turned and came back to him, a shiny, foil packet in her hand.

He stepped back into the hallway, giving her room to move by him, followed her into her bedroom... his heart going a mile a minute.


Jessica left her overhead bedroom light off.

The sun had set, and darkness was leaning harder on the end of the day, the shadows in her room blending together.

She padded across the floor toward her queen-sized bed, stopping at the foot, tossed the condom she’d grabbed to the mattress.

Seeing that condom on her bed, gave her pause, really bringing it home for her what she and Henry were about to do.

They were about to have sex.

They were about to cross that line.

It was a big frickin’ moment in their relationship.

Henry’s hands landed on her waist, gently guided her back a step, pulling her into his body.

He didn’t seem to notice that she’d stiffened up a bit.

One of his hands left her waist, moved up and brushed her hair out of the way, exposing her neck for his mouth. She tilted her head to the side, giving him better access, and he took full advantage, tasting the column of her throat with sensual swipes of his tongue.

Muscles that had tensed, started to relax again.

His licks and kisses climbed up to her jaw and she turned her head, bringing their mouths within inches of one another. Henry crossed those inches, sealed his lips to hers, gave her a kiss that curled her toes...

... a kiss that, as it continued, extinguished her nerves.

Turning in his arms, she wrapped her arms around his neck and shoulders. Her breasts flattened against his chest as she lifted herself up and into him.

Henry’s hands skimmed down her body, cupped her ass, pulled her even tighter against him, and their kiss took a sharp turn towards the voracious, their tongues dueling, exploring every tiny taste bud.

The only noise in the room was the swelling sounds of their passion, their moans quickly growing in volume and frequency.

Henry picked her up, quickly scooping his arms under both her legs. He hitched her legs around his hips, then returned his hands to her ass.

Jess was impressed with the nice move.

She locked her ankles behind his back, squeezed his hips with her thighs. She didn’t have to do so for long though because he turned and sat on the edge of her bed.

With her now straddling his lap, his hands were free to roam where they may, not having to hold her anymore, and roam they did - immediately slipping around to her front and covering her breasts.

She arched reflexively, pushing herself into his touch... moaned at the little bursts of pleasure that his kneading and massaging had pinging from her breast to her core.

Oh, he was good with his hands.


Through the material of Jessica’s bra, Henry could feel her nipples poking at his palm as he squeezed and fondled.

He had to free them.

Removing clothes became priority.

Unfortunately, that meant he had to remove his hands from Jessica... but only temporarily.

His fingers made quick work of undoing the buttons of his shirt. He was shrugging it off when Jessica broke their kiss, quickly whipped her shirt off over her head, tossed it away.

Being ever so helpful, he reached around her, undid the clasp of her bra, pulled the straps down her arms and off.


... he stared.

He’d imagined what she looked like naked countless times. He’d never gotten close to how beautiful she actually was. The reality of her was better than any fantasy.

Her nipples were dusky pink kernels riding the heavy curve of her full breast.

His mouth watered for them.

He promptly latched onto one, sucking the bud into his mouth and drawing on it.


Jessica gasped at the feel of Henry suckling her. The tantalizing sensation had her moving restlessly in his lap, had her inner muscles clenching around nothing... looking for something to squeeze.

When he released the nipple in his mouth with a pop, she stopped him before he could recapture it, or its twin, with a hand on his shoulder.

He frowned at the interruption, but all was forgiven when he saw what she was about.

And what she was about, was getting naked.

She climbed off his lap, slipped her hands to the fly of her jeans, popped the button, lowered the zipper, and shoved the denim to her ankles and off, along with her socks.

When she straightened up, Henry’s gaze went to the only piece of clothing left on her body, her panties.

Slowly, his eyes lifted to meet hers.

Oh... my...

Her breathing quickened.

... the way he looked at her... scorched her.

He stood and her gaze left his, dropped to the bulge behind his fly. She watched, riveted, as he started undoing his belt buckle and fly, appreciating the masculine flex of sinew in his hands and forearms as he worked to free himself.

At her first good look at him, her panties, already wet, dampened further - his cock was even more impressive than she’d pictured in her dreams.

She studied the length of him, the thickness... the veins standing out along his shaft... the darker pink of the head of his cock.

Her inner muscles clenched again. It was a few moments before she raised her gaze from his erection to his eyes. When she did, Henry’s gaze pointedly dropped to her panties. She snuck her thumbs under the waistband, slid them down her legs and off, completely baring herself.

All was quiet as they both took each other in.

A nervous giggle tickled the back of her throat. She tried to stifle it but failed.

She was standing naked in front of a naked Henry Carter!

The moment was a little surreal.

“What’s so funny?” Henry murmured, smiling, though he didn’t know the answer to his question yet.

“You... me... us.” she replied, her amusement still in her voice, despite her trying to clamp down on it.

Henry’s expression became questioning, almost worried, and she hurried on, not wanting to hurt or offend him unintentionally.

“It’s just, I never would have imagined that you and I would be here... like this.” she explained. “Naked.”

Her words had the worry clearing from Henry’s expression. He stepped closer, his cock bobbing with his step.

“And now that we are?” he asked, staring into her eyes, his expression soft, tender, and maybe a little unsure still.

She sobered, her moment of giddiness - a glitch in nerves - fading away, the heat of the moment returning to her.

“Now that we are...” she murmured. “... I’m so glad that we are.”

Henry smiled.

“Me too.” he murmured.

He stepped closer, slowly lowered his mouth to hers.


Lips pressed to Jessica’s, Henry turned them so he was facing the bed, blindly walked her backward toward it. His knee bumped the mattress, and he lifted his mouth from hers, wordlessly urged her to get on the bed.

As she crawled up to the pillows, he found the condom she’d had earlier, tore it open.

Jessica stretched out on her back - a fucking goddess in repose - and watched him roll the latex over the head of his cock and down his shaft.

On hands and knees, he walked up the bed and over her.


Henry hovered above her for a beat before Jess felt the welcome weight of his body press hers deeper into the mattress.

He didn’t enter her right away... he found her every last erogenous zone and lit it up.

She reciprocated every touch... every kiss... until she couldn’t wait any longer. Reaching between their straining bodies, she found him. He promptly lifted his hips and, with her guiding him in, mounted her, pushing his way into her core until he was fully embedded inside her.

She went absolutely still at the feel of his penetration. Her eyes found his and she saw by the look of awe on his face that he was as affected by the moment as she was.

She almost wished she didn’t have to move. That she didn’t crave the sliding, grinding friction.

But she did. She craved it. She wanted it. Needed it. Ached for it.

She gave into her body’s demand and moved, rocking against Henry. She slid her hands down his back, down to his finely curved ass and bit into its taut curve with her fingers.

Henry’s eyes closed, his head sagged forward on his neck. She waited for him to open his eyes again and when he did, she smiled up into his face.

“Feel good?” she asked and clenched her inner muscles around him.

He huffed out a laugh.

“I think I just blacked out a little.” he replied.

She chuckled, loving that Henry showed his sense of humor even in the bedroom.

Her amusement was choked off by a gasp a heartbeat later when he pulled back... then thrust into her strong and quick.

Oh, god...

“Feel good?” he asked, echoing her question with a smug grin on his face.

He didn’t give her a chance to answer, pulling his hips back and thrusting forward once more, grinding his pelvis against hers.

Oh, god!

She lost sight of him for a moment, her lids drifting closed... but only for a moment.

“Sooo good.” she murmured, her words drawn out on a sigh.

Henry lowered his mouth to hers, rolled his hips, plunging forward and holding himself deep inside her this time.

They both groaned, the sound muffled between their fused mouths.


Determined to take things slow for as long as possible, Henry kept up a smooth, but slow, rhythm.

He’d wanted this for so long... had thought it would never happen...

... a part of him still couldn’t believe it was happening.

He slid himself out of Jess’s tight heat and back in again.


He wasn’t going to be able to hold this pace for long.

The pleasure was just too acute.


Jessica held tightly to the only anchor she had in this maelstrom of pleasure, her hands splayed wide across Henry’s back. She felt herself on the verge of orgasm and was so ready for it.

Henry lifted his mouth off hers, panted her name. She opened her eyes, stared up at him. His eyes were closed, his face contorted into what looked like a grimace of pain, but was, she knew, a mask of ecstasy.

His hips picked up speed... and things started to blur... her connection to anything other than pleasure fragmenting.

A few more delicious strokes and she came undone... lost all control of her body... twisting, writhing, spasming... taken away in the tides of her orgasm.

She heard screams, knew they were hers, and was helpless to stop them.


Mindless with pleasure, Henry pumped himself in and out of Jessica’s body.

Hearing her reach orgasm, feeling her inner walls milking him, pushed him over the edge into his own orgasm... and he groaned his way through his release.

Thoughts were not achievable for many moments while his brain processed such a large concentration of pleasure.

Hundreds of heartbeats later, he floated back down from the peak of ecstasy. As his faculties came back online, he realized that he’d collapsed on top of Jess, that he was crushing her with his weight.

Slipping his arms beneath her, he held her to him, keeping them connected, and rolled onto his back, bringing her on top of him. She hummed contentedly with the new position, her legs falling to either side of his, rested her cheek against his chest.

The two of them quietly basked in the afterglow. Henry idly trailed his fingers over Jessica’s skin, following the indentations of her spine, until... several minutes later... she shifted and his spent cock flopped inelegantly against his thigh.

“Where ya going?” he murmured sleepily.

Tilting her face up to his, she looked up at him, gave him a shy smile.

“Nature calls.”

She rolled off him, and got up, and he watched her walk around the bed... feasting his eyes on all that beautiful bare skin.

Alas, she pulled her shirt and panties back on, headed out of the room.

While she was in there, he took care of the used condom.

Jessica had a small box of Kleenex on her bedside table and he swiped a couple, removed the condom, wadded it up in the tissue. Swinging his legs over the side of the bed, he got up, found his boxers on the floor and stepped into them.

He was just stepping into the hallway when the toilet flushed. The faucet went on and off, then the bathroom door opened and Jessica stepped out.

She noticed the tissue in his hand.

“Garbage is under the sink.” she told him.

He ducked into the bathroom, got rid of the used condom, and the two of them returned to the bed, and to each other’s arms, nestling against one another once more.

Henry sensed when Jessica fell asleep by the change in her breathing, by the way her muscles relaxed, her weight completely sagging against him.

Softly, he pressed a kiss into her hair, then closed his eyes, and drifted off.


Jessica woke in the middle of the night to the feel of Henry’s hands and mouth on her.

His hand, already on a path to her core, arrived, sneaking under the elastic waistband of her panties. He found and circled her clit with a finger.

That brought her out of the fog of sleep quickly. Stirred by his touch, she opened her eyes. He met her gaze... his hand circling and circling, pausing only to delve down to her entrance and collect some of her cream before returning to her clit.

Biting her lip, she rocked into the beautiful touch.

A finger slipped inside her.

She reached down, seeking the erection she felt pressed against her hip, slipped her hand under the waistband of his boxers and grasped it. Henry hissed in a breath as she stroked his length, let that breath out on a sigh.

A second finger joined the first inside her.

Her eyes falling closed, she tightened her grip on Henry’s cock, focused her attentions on the plump head.

He groaned before suddenly rolling away from her.

Where was he going?

She opened her eyes and found him.


He was sitting up on his knees... reaching over to her bedside table. He grabbed up a condom he’d apparently retrieved from the bathroom, and ripped it open.

As he ditched his boxers, she removed her panties, shed her top.

Once he’d donned the latex protection, he came over her, aligned the tip of his cock with her passage and pushed up inside her, her cream making his entry easy.

There was no slow and smooth this go-round... there was just rush, rush, rush.

Planting her feet in the mattress by Henry’s hips, Jess braced herself, met him thrust for thrust. Higher and higher, he pushed her. He had her clutching at the sheets, fisting the cotton.

Her climax broke over her, pulled her under, tossed her about inside her body like she was a piece of fluff in the wind.

From a distance, she registered Henry’s throaty groan as he reached his own peak.


Seized in the grip of a powerful orgasm, Henry cried out. His head snapped back, his spine arched as he thrust into Jessica again and again.

Fuuuck. He couldn’t stop.

He was no virgin, but the level of pleasure he reached with Jess was new to him.

Being with the woman he’d always wanted to be with...

... redefined sex.

He slumped against Jess after he plateaued from his climax, but didn’t give her his full weight this time.

Finding her mouth with his, he kissed her, slow and leisurely... all traces of the hurry they’d just been in, gone.


Jess let Henry go as he gradually eased back from their kiss. He shifted off of her and dealt with the condom.

He didn’t bother throwing his boxers back on for this trip to the bathroom, so Jessica enjoyed the nice view of his bare ass as he left the room, and the lovely view of his front as he returned to bed.

Once he was beside her again, she draped an arm across his waist, cuddling into his side, her legs tangling with his under the sheets.

With a hearty sigh of contentment, she closed her eyes and fell asleep.


The sun’s soft, early light, was peaking into Jessica’s bedroom around the edges of her blinds when Henry woke up. Jessica’s head was still on his chest, her arm was draped across his waist, and his arms were still wrapped around her.

Uncomfortable, fuzzy tingles in his left arm told him it had fallen asleep.

Trying not to disturb her, he shifted, and Jess lifted her head.

She was already awake.

“Morning.” she smiled, meeting his gaze.

Stretching freely, he returned her smile, taking in her slightly mussed hair, her sleepy-eyed gaze.

She stretched toward him, pressed her mouth to his.

“Mmmm.” he hummed into their kiss. “Morning.” he echoed once they’d parted.

Jess moved off him, propped herself up on an arm, supporting her head on her hand.

“Did you sleep okay?” she asked.

“Mm hmm.” he replied. “You?”

“Mm hmm.” she echoed, the reason she slept so well turning her smile sultry.

She leaned into him again, taking another kiss. This one stretched on for a substantial amount of time. So long, that when she pulled away from him, Henry expected she was either going to go get a condom, or ask him to get a condom.

“You hungry?” she asked.


It took his brain a second to digest those two words because it wasn’t what he’d been anticipating.

He supposed, now that she mentioned it, he was feeling hunger pangs... but... that could wait...

“Yeah.” he replied.

“Me too.”

She rolled away and out of bed.

Guess round three wasn’t happening just yet.

He got up and threw on his boxers while Jess threw on her shirt from yesterday and her panties, and they made their way to the kitchen where she cooked them up some eggs and toast.

They ate at her small dining table, kitty-corner from each other.

“You have any plans today?” he asked, and shovelled some scrambled eggs into his mouth.

Hopefully she didn’t and round three was in the offing after breakfast.

“Nope.” she replied, and squeezed a large pool of ketchup onto her plate next to her eggs. “Just dinner tonight.”

Right. It was Sunday. She was having dinner with George and Linda... and Josh.

After the events of last night, Henry felt more pressure to tell his friend about him and his sister.

He paused, looked over at Jess, and came to a decision. As long as she was okay with it, which he knew she would be, he would tell Josh about them.

Jess must have felt his eyes on her, because she looked over at him, met his gaze. He told her what he was thinking and encouragement entered her eyes.

“I know you’re worried about his reaction,” she said. “... but I’m sure he’ll be fine with us.”

She bit into her toast, confident in her opinion.

He hoped she was right.

He’d find out if she was tomorrow.


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