Little White Lies Ch. 14

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Jessie helps John, Dex helps Donna's family, Don dates Candy.
27.6k words
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Part 14 of the 18 part series

Updated 02/14/2024
Created 11/06/2018
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Mentalcase
Mentalcase
8,317 Followers

Little White Lies

Chapter 14

Jessie

Saturday night...

"Wha...?" Jason mumbled as he sat up.

Naked, Jessie had just then lifted the blanket covering the young man up and had knelt on the couch with one knee when he'd jolted awake, startling her.

"It's me," she said quietly.

"Jessie?" he stammered.

"Yep!" she confirmed happily and moved to straddle him. As she did so, she noticed that he was still wearing his boxers.

"What are you doing here?" He was still waking up, judging from the tone of his voice and slurred speech.

She giggled and put both hands flat on his shoulders, pushing him back down to the couch. Leaning down, she kissed him briefly then focused on working his underwear off with one hand. As she did so, she felt his heart beating rapidly against his chest, her other hand easily picking up the sensation as it rested on his chest.

"What... uh... what are we doing?" he stammered.

"Fucking!" she said simply. "My boyfriend told me that I could help you lose your cherry when he was fucking me earlier today. I'm thinking that now is as good a time as any since you're leaving for home tomorrow."

His heart started to beat even faster against her palm, and a nervous smile came to his face that she could see even in the dim light of the den.

"Oh honey," she commented, "you're so nervous!"

She leaned back down to kiss him again as her hand began to stroke his swiftly swelling cock. He still had his arms pulled away from her and didn't seem to want to use them to do anything to her.

"Wait," he mumbled.

She stopped kissing him and fixed him with a stern gaze as she looked down.

"Don't you want to have sex and not be a virgin anymore?" she asked quietly.

"I just... don't know what I'm doing," he replied.

"That's okay," she assured him, affectionately stroking his chest with one hand and his cock with her other. "I'm not going to be grading your performance, silly! This is my way of letting you get some practice in."

She slid back off of him then, her hands reaching for his as she moved onto her back on top of his crumpled-up blanket. He followed silently, but she could clearly see his hands shaking from nervousness.

"You're not going to do anything wrong, Jason," she said, trying to sound reassuring. "Try not to be so nervous, okay? Don't think about how you're supposed to do it correctly and just do what comes naturally to you."

She pulled him from his kneeling position down to one with him laying on top of her. His cock was as hard as could be and nuzzled her cleft happily.

"Just take your time," she said, and gave him an encouraging nod. "Always be gentle when you enter a girl the first time, especially if she's a virgin. It can be painful if you rush things."

He nodded at her, then moved to a kneeling position and looked down.

"Do... I uh... need to... lick..." he stammered

She smiled and shook her head. "I appreciate the thought, but I'm already wet and ready for you sweetie. You can feel it if you like."

He nodded and she watched as he reached down between her legs and tentatively ran his fingers through her slit and briefly inside. His smile confirmed what she'd said and he pulled his hand free, wiping it on part of the blanket beside him.

She watched him reached down and take a hold of his dick, then lean over her and prop himself up with his other arm, still looking down between them.

"Look up at me," she said, and smiled as his eyes fixed on hers. "Men and women are made to fit together," she said. "You'll be able to find where it goes."

He chuckled quietly, finally showing some signs of calming down.

"In fact, lay down on me," she ordered, gently pulling at his waist with both hands.

"I don't want to squash you," he said, concern clear in his expression as he briefly resisted.

She snickered quietly and pulled again. "Just don't put all your weight on me."

He nodded and lowered himself down on top of her, the weigh growing until she smiled and nodded at his questioning stare. He was still awkwardly holding his hips up though, as if he was worried about hurting one of them.

"Whenever you're ready, sugar," she said sweetly.

He took a deep breath and hesitated. She was about to whisper some more encouragement when she felt his hips lowering and felt his cock nuzzling her pussy again. He thrust slowly, his cock sliding up her slit and away from where it was supposed to be going. She wasn't going to correct him though, knowing that it would do him good to find it for himself. He frowned and slid back again, and she smiled up at him as he closed his eyes.

After a few more tries, he finally pushed tentatively inside.

"OhmyfuckingGod!" he whispered and groaned as she watched him with amused fascination.

He pushed completely in, and she sighed happily as she felt the modest size of his cock inside her. She kept still though, letting him take his time to enjoy the sensations.

He moaned weakly as he began to slowly withdraw, then thrust. Exactly four slow thrusts later, she heard him groan weakly and felt his cock pumping its warm contents deep inside her. She smiled, caressing his arms and back as he grunted and thrust uncontrollably against her a few more times.

With a low moan he thrust a final time and held still, a smile coming to his face as he opened his eyes and looked down at her. She returned his grin and giggled briefly.

"Congratulations," she told him.

"Wow..." he muttered, laughing briefly. "That was... wow."

She continued to watch him quietly, happy that he'd enjoyed it so much. He continued to hold himself in the same position and she was enjoying the feeling of his erection still nestled inside. He closed his eyes again, his smile growing before he opened them again and looked back down.

"Sorry... that I came so quick," he said.

"No apology necessary," she assured him. "Your first time is supposed to be quick!"

He nodded, his smile returning. She felt him start to move to extract himself from her, but she stopped him by pulling at his waist with both hands once again.

"You know, you're still inside me and still hard, this is technically still the first time. Dex told me that I could only take your cherry and rarely lets anyone else but him have my pussy. So..."

He looked down at her, the nervous, hesitant expression returning.

"So," she continued, "if you want to keep going, you can. I just won't be able to have sex with you again before talking with Dex if you stop now."

He smiled widely and paused for a moment of silent contemplation then nodded.

"I... kinda want to feel... what its like when a girl... cums," he said hesitantly.

She giggled and nodded. "Well, start pounding your cock into my pussy and you'll find out, handsome!"

He blushed in the dim light, and she giggled at the endearing sight.

"Are there any other positions you'd like to try?" she asked, smiling sweetly at him.

He looked briefly confused then shrugged. "I don't know many," he said.

"Here," she told him. "This is a good way to get me to orgasm. Lay back."

Moving in time with him, she felt him briefly slide from her pussy as he moved onto his back again. She followed, sliding on top and pulling his shaft back inside before he realized what she was doing.

Slowly, she began to grind back and forth of him, her hips gyrating forward and back and dragging her pussy up and down his hardness. He didn't seem to know what to do with his hands, so she reached down and pulled them up to her breasts. From that point, he happily played with her orbs, squeezing and kneading them and tenderly pinching her nipples.

After a few minutes, she was able to grind a nice, comfortable orgasm out as he watched and played. It seemed that the sight of her cumming was highly arousing for him and as she slowed, he took a deep breath.

"Close?" she asked, drawing a quick but vigorous nod. "You can keep fucking me like this if you like..." she said, but then groaned as she felt him thrust weakly against her, his cock pumping once again inside her. "Oh... fuck," she whimpered, closing her eyes as the delightful sensations of his warm cum filling her swamped her senses. "That's it, baby," she whispered.

A few seconds later he ceased thrusting and fell still, breathing heavily.

Taking a few seconds to recover herself, she held her position and simply watched him.

"All good?" she asked quietly, smiling as he looked up at her and grinned.

"Thank you so much," he said. "That was awesome! I can't believe how good it all felt."

She snickered at him, then gave him a final kiss before he began to get up.

"I'm gonna go clean myself up," he said. "Thanks again Jessie."

She smiled happily and waved at him in the dim light, then watched as he left the room. With a contented sigh, she stood and gathered her clothes back up, then went to try and find a place she could sleep.

Making her way upstairs, she opened the door to Jack's room, thinking she could just crash there and not disturb Dex and Donna, but John was snoring loudly, sprawled out on the bed. From there, she peeked into Dex's room, thinking that maybe she could slip in and maybe they wouldn't notice. Her boyfriend's bed wasn't all that big to begin with, though, and already had two people in it.

As quietly as she could, she stepped back out and shut the door, then turned and looked down at Don's room. The lamp was still on, and she could clearly see his bed was empty.

"He won't mind," she said with a shrug, and walked quickly toward it.

Tossing her clothes to the floor beside the bed, she slipped in and pulled the covers over. It proved to be too hot after a few minutes, though, and she kicked them off. The last amusing thought she had before she drifted off to sleep was what Don would do if he came home and saw her laying naked in his bed.

*****

Don

Saturday evening...

There was no telling what sexual shenanigans were going to be taking place at his house that night. Knowing Jessie, it would probably end up as a full-blown orgy before the night was over. He wouldn't have minded staying and finding out for himself, of course, but he was extremely happy for the distraction he was being given.

His first date with Candy had been amazing. All of his other recent dates had been downright abysmal, but this one had single-handedly restored his faith in the hope of finding someone that he could be with.

She was incredibly sexy, smart, funny, and after Jessie and Dex's sexual display, obviously didn't scare easily. It seemed too good to be true. From the moment the date started to feel like it was going well, he'd been expecting something to happen to ruin it.

After that, he'd started to think that this might be the start of something real but was determined to keep his head on straight and not get his hopes up. Candy's invitation to come eat dinner had come quick, as far as he understood from what he knew of the rules of dating. It was an encouraging sign for her to be just as excited about the prospect of the two of them together as he was.

He'd gotten dressed and left as soon as he realistically could, not wanting to be a potential target for any of Jessie's crazy sexual plans. After stopping to buy some flowers on a whim, he pulled up into Candy's driveway on time and hopped out. After walking up to the front door, he took a moment to collect himself and then rang the doorbell.

A few seconds later the door opened, and Candy smiled widely at him just inside. There were a few seconds of silence between the two as they both stood there smiling and waiting, but then she surged forward and kissed him intensely. He wrapped her his arms and pulled her tight, delighting in the adorable whimpers and sighs.

After a few seconds of passionate embracing, she stepped back and took a deep breath, looking up at him with a frown on her gorgeous face.

"What?" he asked, wondering what he'd done wrong.

"You just look so damn handsome, I couldn't control myself," she said. "Come on in," she continued as he laughed.

"Thanks," he said, and smiled as she slid her hand into his after shutting the door.

"I was trying to keep control of myself too," she said with a brief frown. "I told myself that I needed to behave and not act like a horny teenager."

She slid close to him, her other hand grabbing for his and finding the flowers he was clutching there instead. With a chuckle, he kissed her on the forehead as she leaned her head onto his chest for a few comfortable seconds.

"It's good to see you," he said, drawing her face up to look at his.

She smiled sweetly and rolled her eyes. "God... can't you be inconsiderate or something at least?" she said, looking down as he brought the flowers up between them. She took them from him and pulled them to the side, then kissed him again.

"It's good to see you too," he said, smiling in amusement.

She gave him a quick tour of the house before they ended up in the kitchen where she went to find a vase to put the flowers in. As she busied herself with that task, he drank in the exquisite sight she presented.

She looked even better than she had the previous evening. She was wearing a dress, this one slim and sexy, red in color and tantalizingly low-cut. The skirt modestly ended at her mid-thigh, and despite his failed attempt to not look, he couldn't see panties when she bent down to retrieve the vase.

Watching her as she clipped the flower stems shorter and held them up to the vase, then did it again, he felt a happy, content feeling come over him. He had a vision of his first wife doing that very thing. She would measure the flowers several times before she was happy with the length, then spend several minutes arranging them just so, until the arrangement was just to her liking.

Candy did the same thing, taking her time getting the flower the right size and arranging them perfectly before filling the vase with water.

"Sorry," she said, blushing adorably. "I'm very particular about certain things."

"Like arranging flowers?" he asked, amused.

"Like arranging flowers," she confirmed, laughing easily.

He found himself musing about how much he liked the sound of her laugh. It wasn't anything strange or particularly unique, but there just seemed to be something about how she laughed that he adored. It was like she was laughing with her whole body.

He realized he was staring again and briefly blushed as she brushed a long lock of blonde hair back over her ear.

"Sorry," he said. "I just find myself staring at you and can't stop..."

"Oh... I'm not complaining," she said. "Just finding it hard to behave around you."

"You know, you're going to need to stop massaging my ego," he said, and fixed her with knowing smirk.

"Stop being so handsome and sexy," she shot back, frowning at him. "I'm not trying to massage any ego's around here."

He laughed but didn't press the point. Even if she was spreading it on a little thick, it was nice to hear after being so alone for so long and going on so many bad dates.

"So... what's for dinner?" he asked, telling himself to focus and stop daydreaming.

"Lasagna," she said. "It's easy, but it's something I also do really well, so it seemed like a natural choice." She turned quickly to look back at him as she moved to check the food. "You like Italian, right?"

"I'll eat whatever you put in front of me," he said, but then winced when she raised an eyebrow and giggled at him.

"Is that so?" she asked, cocking her hip to one side.

"Yeah... that didn't come out right," he said, groaning internally. "Why am I always putting my foot in my mouth around you?"

After a few more laughs at his expense, she gave him a wink and resumed checking the food.

"So, is there anything I can do to help?" he asked.

She initially shook her head, then turned and looked at him quietly for a few seconds. "How about you open the wine," she suggested, and gestured toward a bottle on the counter.

"Can do," he said, stepping into the kitchen and reaching for the bottle. Next to it on the counter was the corkscrew, and after removing the seal he worked the cork out and set it on the counter.

Candy had finished looking in on the lasagna by then and had closed the oven back up. Turning, she stepped over to one of the cabinets near Don and opened it, producing two wine glasses that she held out for him to fill.

"Trying to get me drunk?" he joked, winking at her.

"Trying to get you to get me drunk," she corrected, and the two shared a laugh.

She stepped close to him and clinked her glass to his, then moved in even closer and rested her hand on his chest as he put his own around her waist.

"I sooo like this," she said, and sighed comfortably.

"Me too," he assured her. "Feels... good."

"Feels perfect," she amended, and leaned in for a gentle kiss.

Her lips were warm and soft, yielding to his as she timidly pushed her tongue briefly into his mouth before she broke the kiss and smiled happily at him. A few comfortable moments of silence passed between the two as they enjoyed each other's presence, but she eventually stepped back and reached down for his hand.

"We've got a little bit before the food is ready," she said, pulling him toward the door. "Let's go sit and get comfortable."

He followed quietly, silently hoping that the evening went as wonderfully as the previous night had gone. Well, most of it at least. He could have done without Jessie and Dexter interrupting it with an impromptu sex attack in the middle of it. Other than that, of course, everything had been almost magical.

She led him back into the living room and settled down on the couch, the two of them putting the wine glasses on the coffee table in front of them. She turned after leaning back into the couch and hooked one leg over his, propping her head up on the back of the couch with one hand and staring at him silently for a few seconds.

While the lasagna continued cooking, the two settled down and began to converse. The topics were safe, both of them sticking to the basics and making small talk. After a while, Candy got back up and went back into the kitchen to check on the food. A short time later, the two were sitting at the table eating and drinking their wine, the small talk continuing.

Afterward, even though she insisted that she could handle it, the two cleaned up the mess; Don washing the dishes and Candy drying them.

"You weirded out by this?" he asked.

He'd finished washing the last dish and had rung out the scrubber, placing on it back where he'd found it next to the sink.

"Most men that I've gone on dates with wouldn't volunteer to do the dishes," she said, grinning his way. "It's different but in a great way."

He chuckled and shrugged, turning to watch her as she dried the last dish. "I'm not one of those guys that expects his woman to wait on him hand and foot. I know you might have heard that Jessie tends to take care of cleaning up around our house, but I've told her dozens of times that she doesn't have to."

"Still, it's nice of her to do so," Candy said. "I've never minded taking care of my man in that manner, as long as it wasn't something he ever demanded of me, you know?"

"Definitely," Don confirmed with a nod.

"So... want to go relax on the couch with a movie?" she asked, tracing a line on his chest with a single finger.

"Whatever you'd like to do is fine with me," he said.

She smirked at him but didn't move.

"Don..." she said, drawing his gaze up to hers. "One thing you'll learn about me is that I'm not the type of woman that needs to have every date be all about what I want to do. You get to have a choice too."

He smiled and gave her a quick kiss. "That's nice to hear, but I figured since you asked me over, it was your evening to plan."

Mentalcase
Mentalcase
8,317 Followers
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