Jillian was sitting on the couch, totally immersed in her own world when suddenly her name echoed through the room like a thunderclap.
“Ah!” she squeaked in surprise, quickly turning around to see who the hell was shouting. And there, standing by the doorway, was Jason in all his glory. Her eyes widened in shock at his sudden appearance.
Meanwhile, the TV was blaring some low-budget horror movie with a couple making out in the stupidest place imaginable, while ominous music played in the background. Jason’s expression was a mix of horror and confusion as he took in Jillian’s appearance.
Her hair was haphazardly tied up, chocolate ice cream smeared all over her lips, wearing an exfoliating face mask that made her look like a wrinkled ghost and her eyes were red from the tears she’d shed.
Jillian stared back at Jason, still processing the situation, when screams erupted from the TV as the guy got stabbed by some costumed serial killer.
Jillian’s attention was diverted from Jason to the sound of the horror film she had on, but she quickly scrambled for the remote and switched it off. She slammed the tub of Rocky Road ice cream on the table in her haste and glanced back at Jason, who was shutting the door behind him, but hesitated coming in further.
“J-Jason, w-what are you doing here?” she asked, surprised and confused. Wrapping her blanket around herself a bit tighter, she stood up to face him. Jason stuttered slightly, trying to find the right words but struggled to concentrate.
“Uh, well, I came here to... talk to you and…,” he trailed off, unable to articulate his thoughts properly. “Sorry, it’s really hard to have a serious conversation when...you uhh, you know, look like that,” he said, gesturing awkwardly at her. Jillian gave him a puzzled look, waiting for an explanation.
“What’s that supposed to mean? Are you really trying to insul-...?” Jillian said, about to get upset at him for possibly coming all the way here to rub salt in the wound. But it slowly sank in what Jason was trying to say when he motioned to his own face.
“Oh, fuck!” she turned and dashed into the bathroom slamming the door behind her. “Just give me just a minute, please!” she called out as she rushed to the sink mirror to check herself out.
“Y-yeah, no problem. Take your time,” he responded.
The wrinkly face mask and chocolate smudges around her mouth were quite a sight combined with her hair that was a barely contained disaster. Her cheeks flushed with embarrassment.
“I look like a soggy scarecrow demon that’s been eating mud,” she grumbled to herself.
Amidst her worries about how she looked, she glanced back at the door and wondered why Jason was even here. Mika had been overly tight-lipped about her morning activities, heading straight to work after returning home and getting settled. Jillian was completely in the dark about what was going on, just hoping that her friend hadn’t murdered anyone.
Jillian took off the mask and washed her face with some facial scrub in record time. She let her hair loose from its ponytail and used a comb to tame the mop of knotted curls. Her teeth clenched as it got stuck on a few knots, yanking her hair hard. Followed up by using some convenient eye drops that were almost empty to soothe her raw red eyes.
What felt like a minute to her turned out to be fifteen in reality as she primped herself to look presentable. Still in her underwear, she wrapped the blanket around herself and quietly stepped out. Jason was leaning against the wall near the door. He didn’t seem happy at all. In fact, he appeared quite upset, with the same familiar sad puppy look that always tugged at her heartstrings.
She tried to calm the heavy thumping in her chest as she closed the door behind her and leaned against it. The sound caught Jason’s attention, and he looked up at her. Without the stuff on her face, he had no trouble meeting her gaze.
“H-hi...” Jillian started softly.
“Hey...” Jason continued, and they lapsed into a long silence, just staring at each other, almost like a silent standoff to see who would break eye contact first.
“I want to—” they both started simultaneously, then paused, realizing they had said the same thing at the same time. After a small pause, the two laughed a little at the awkward moment, but it helped ease some tension.
“Sorry, go ahead,” Jason said, motioning for Jillian to speak first.
“No, it’s okay, you came all the way here, please you first,” Jillian insisted, trying to be polite. After a moment, Jason nodded and began.
“I just wanted to apologize for the other day and clarify what I was trying to say.”
Jillian frowned slightly at the apology.
“No, I’m the one who should be sorry. I didn’t let you finish, and let my own insecurities get the better of me. I said something hurtful I knew wasn’t true.” They exchanged apologies, each eager to make amends now that they were calm and actually thinking properly.
They both pushed off their respective walls they were leaning against and moved a little closer until they were just a few feet apart. Jillian had to tilt her head back to look at him, while Jason had to look down to meet her gaze.
“We both screwed up in our own ways,” he suggested, and she hesitantly nodded.
“I-I suppose,” her voice was a bit timid.
“How have you been?” Jason asked, glancing over at the sofa where there were several balls of used tissues, pillows, and a tub of ice cream melting on the table. Jillian blushed slightly, pulling the blanket tighter around her and feeling embarrassed.
“I’ve been... okay. Not great, but surviving. What about you?” she asked in return.
Jason shrugged slightly. “About the same. I actually just got out of the hospital this morning.” Jillian’s eyes widened in shock.
“What?! Why were you in the hospital? Did you hurt yourself? Did Mika hurt you?” She gave him a quick once-over. Grabbing his arm and lifting it, she examined the small scrapes and bandages all over his arms.
She was expecting some obvious injury, but she found nothing major. The sensation of her soft hand on his skin was like a cool drink of water after being stuck in the desert for several days. He had to push away the thoughts of what it would be like to be without for even longer.
“Long story short, the doctor thinks there might be something up with my heart. I kinda, sorta… passed out right after you left,” he explained. Her expression shifted to one of horror.
“Oh god… did I cause-“
Jason cut her off, raising a hand before she could finish.
“No, no, it’s not your fault. Not entirely, at least.” He didn't want her to feel bad but still wanted to be honest with her. “It wasn’t just one thing. It was a combination. But there might be a deeper issue with my heart, according to the doctor.”
Jillian still felt guilty about him passing out because of the stress she had helped cause. She wanted to ask him more, but she didn’t want to risk upsetting him further.
“I’m sorry Jason… I never wanted to hurt you, I wish I could take everything back… If I had refused harder to come to dinner that night…God I’m going to be the death of you, I just know it,” she murmured, looking down at the floor. But Jason’s hand was suddenly under her chin and lifted her gaze back up to meet his.
“I don’t wish that at all... Even if it’s been painful, I wouldn’t want to go back to who I was before we reunited,” he whispered to her.
Though she still felt a bit down, she gave him a shy smile, her cheeks warming from his touch and sweet words. His hand slowly moved away from her chin.
“What are you going to do about your heart?”
“When I’m back in Florida, I’ll see my regular doctor and get a referral to a cardiologist to figure things out.”
Jillian nodded, but her expression was still filled with concern. “But you’re feeling okay for now?” she asked, still not entirely convinced. Jason chuckled softly.
“Yeah, I’m alright. It’s just something I need to get checked out later,” he reassured her. She nodded again, though a bit timidly this time.
“Speaking of Florida...” Jason began, capturing her full attention once more. “Um, well... there’s something I wanted to ask you...” He hesitated, his nerves evident as he glanced away several times, rubbing the back of his neck.
“O-okay?” Jill said, a little nervous about just what he was about to ask her.
“Jill, I’m pretty much new to...well, all of this, and I’m not sure how things are going to turn out over the distance. But there’s something I have to say. I’ve been trying my hardest to work up the courage…,” he skirted around the issue, avoiding directly expressing his thoughts. “It’s only been a week or so, but we’ve known each other since high school, even though those days weren’t really—”
“Jason… Please, just say it,” Jillian interrupted, her face flushed a deep red as she felt her heart racing in her chest.
Jason finally caught onto her expression, which was a blend of impatience and embarrassment, with a spark of excitement. He took a moment, then took a deep breath.
“Jillian, would you go out with me? Even if it means we’ll have to do the long-distance thing for a bit? I swear I’ll come back as often as possible, or fly you out, and I’ll make sure to call or text you all the time,” he blurted out in one breath. Who knew asking someone out could feel like such a marathon?
Jillian couldn’t believe her ears.
“That’s funny, I could have sworn I just heard you ask me out?” she chuckled, unsure if she heard correctly. Jason rolled his eyes in response.
“Come on, Jillian quit joking around. Just give me a yes or no, or tell me if you need more time or something,” he urged. But before he could continue, Jillian reached up and tugged on his nose.
“Ouch! What was that for?” Jason protested, swatting her hand away.
“Oh wow, it really is you,” Jillian exclaimed, looking surprised.
“I’m not a fucking Scooby Doo villain. Look, if you’re just going to tease me, then I’ll leave,” Jason threatened, rubbing his nose and crossing his arms.
“No, no, no, don’t go. I’m just making sure I’m not stuck in some bizarre dream from eating too much ice cream and slipping into a coma,” Jillian said, sounding serious for a moment before getting distracted.“By the way, I’m mildly allergic to certain nuts, but I still love Rocky Road.”
Jason sighed heavily, feeling frustrated as he realized his efforts were going nowhere.
“I wasn’t prepared before, but give it another shot. I’m totally ready this time!” She flashed a cute smile as she spoke, eager for another try. Jason sighed heavily, looking at the floor.
“Alright fine, Jillian, would you go—”
“Yes!” she interrupted him again with a yell, throwing off the blanket to reveal her underwear-clad form.
With an impressive leap, she launched herself at him, catching him off guard. He barely managed to catch her, his hands gripping onto her thighs. Before he knew it, he was face to face with the grinning redhead, the scent of chocolate still lingering on her breath.
“Really?” Jason couldn’t help but blurt out, taken aback by the enthusiastic response.
“Yeah, really! I can’t believe you actually asked me out! I was almost convinced I’d have to... you know what, never mind. I’m so proud of you!” she exclaimed, wrapping her arms around his neck and planting a deep passionate kiss on him.
The intensity of the kiss caught him off guard, causing him to stumble back against the wall. Their lips locked in a powerful embrace for several long moments before they finally broke apart with a loud pop. She grinned at him, but her expression suddenly shifted.
“Oh, wait, are you supposed to be avoiding heavy lifting with your heart?” she started squirming in his arms, trying to get him to let her down.
Jason’s hands gripped her thighs firmly. “Haha, I wouldn’t really call you heavy lifting, but even if I wasn’t supposed to, there is no chance I am putting you down right now,” he said, smiling brightly at her.
Jillian let out a small giggle, then nuzzled her nose against his, their lips meeting repeatedly as they closed their eyes, lost in each other’s affection.
“I’m sorry, Jason,” she murmured before leaning in for another kiss.
“Hmm, for what?” he asked, unsure of what she meant.
“I know you..” she paused, leaning in to kiss him again. “..Don’t just want me for my body,”
Their tongues intertwined in a passionate struggle.
“Ah-...It was just me being scared,” she confessed after a desperate gasp as he softly bit her lip. Jason released Jillian’s lower lip from his teasing bite, then sucked on it softly, releasing it before speaking.
“I know, Jill. I was scared too. Scared of not being able to handle being apart from you, afraid that I would screw up and lose you,” he confessed to her.
Jillian tilted her head, diving in for the deepest kiss yet, their tongues intertwining again. It seemed their conversation was more revolving around kissing and teasing each other than talking.
“I know, baby. It’s gonna be tough, but we’ll manage, I promise. Ah- Oh god, just like that,” she moaned, going back to using pet names as Jason kissed and nibbled below her ear.“We just have to make every moment count until then. Jason… baby, you’re going to drive me crazy if you keep doing that.” she whimpered as he fervently explored her sensitive neck.
“I can’t help it,” he groaned, his hands moving to firmly grip her bountiful ass cheeks. “You taste amazing,” he admitted, unable to resist the temptation.
“Ngh, then do it baby, drive me crazy for you!” Jillian gasped, feeling the heat spread through her body with every kiss, suck, and bite. She pulled Jason closer, her arms squeezing his neck, wanting more and more. Hips unconsciously moved the best they could to grind her crotch against him.
Suddenly, Jason’s lips sucked hard, his teeth sinking into her neck.
“Ah! Jason, w-wait!” Jillian groaned out her words in intense pleasure as her legs tightened around him, her body not actually wanting him to stop. Jason pulled back, his hot breath blowing against her now moist skin.
“What’s wrong?” he asked, pulling back slowly, confused by her sudden request to stop. Jillian chuckled softly, trying to rein herself in. burying her face into his neck as she recovered.
“Fuck, you might’ve just given me quite the hickey. My skin bruises pretty easily,” she told Jason, legs still wrapped tight around him.
“Oh shit, really?” Jason replied, a hint of concern in his voice.
“Mmmhmm, but it’s okay. I don’t really mind, it was worth it. Just hope my dad doesn’t see it,” she giggled. Playfully she dove into his neck and sucked and bit on it even harder than he did.
“Youch!” he said, trying to enjoy it, but it wasn’t quite his thing.
Her lips and teeth popped off his neck as she leaned back in his arms.
“There, we match,” she said with a grin. Jason chuckled a little and nodded.
“I guess it’s only fair.”
After a few more moments of tender kisses, Jillian leaned her forehead against his, their noses and lips barely touching as they closed their eyes, content to bask in the moment between the two of them.
Their cozy moment together was suddenly interrupted, however, by the creak of the apartment door swinging open. The couple, resting against the wall nearby, each turned their heads to look at the newcomer.
“Hey Jill, Mick mentioned you wanted to... chat...” A strikingly handsome man with a lean yet muscular build said as he walked in.
Standing at least six feet tall, he sported a sleeve of colorful koi fish tattoos on his left arm and two sizable spikes piercing each earlobe. His hair was shaved on the sides, leaving a long, dark blue mohawk cascading down to one side, grazing his shoulder. A few names in fancy cursive adorned the left side of his head. His gaze quickly landed on the pair locked in each other’s arms against the wall.
“Oh, um, hey Jill. Mick said you needed to tell me something?” The guy with the mohawk questioned, eyeing the two of them back and forth. Jason quickly turned a bit to hide Jillian’s body from his prying eyes. Jillian gave the new man a small glare. It seemed her supposed best friend was intent on testing her and Jason’s relationship.
“Uhhhh, no, can’t say I need to tell you anything. Tell Mika she can relax and that I'm just fine. Sorry you got roped into this Darren,” Jill said, surprising Jason, who watched as the guy just nodded, seemingly unphased, understanding the situation quickly.
“Yeah, that sounds like Mick being Mick, I think she just wanted to check up on you without seeming like she was,” Darren whispered loudly.
“My bad for interrupting, dude. Please resume,” Darren said, about to leave, when a voice yelled from downstairs.
“Stay the fuck outta my room!” Mika’s warning rang out.
Darren chuckled, gave a quick salute, then closed the door behind him, leaving them alone again. Jason gently set Jill back on the ground, but she kept her arms around him, just falling to wrap around his waist instead.
“We should talk a little first,” Jason suggested, but Jillian didn’t seem too thrilled about it.
“Talk,” she groaned, sounding a bit whiny. “I don’t really feel like talking. Can’t we just be happy with kissing and cuddling more? Why mess with a good thing?”
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Jason chuckled at Jillian’s reluctance. He could see the worry in her eyes.
“Sure, but I think it’s important to clear up some stuff before we dive back into that,” he said gently, reaching up to run his hands through her hair, giving her a little scalp massage. She closed her eyes halfway, enjoying the sensation as she let out what almost sounded like a purr.
“Hrrrmm, fine, I guess,” she grumbled.
Jason removed his hands from her hair. And Jillian pulled him over to the couch where she was sitting earlier.
“Hang tight for a sec. Gotta stash the ice cream. Want something to drink?” Jillian asked, sealing up the slowly melting tub of ice cream.
“Water would be great, thank you” Jason replied with a grin as he settled into his seat. Jillian nodded and headed over to the bar’s freezer chest to put away the tub. She grabbed a bottle of water from a little fridge, cracked it open, took a swig, and then walked back and handed it to him.
It was a bit unusual for Jason to drink from the same bottle anyone else had drank from. Normally, he was pretty particular about not sharing. But it was easily let go with her after all the kissing they’d just done.
Instead of sitting down with Jason just yet, Jillian hurriedly grabbed the blanket she had tossed aside and wrapped it around her mostly naked body. She shivered a bit from the cold now that she wasn’t pressed against Jason. Eventually moving over to the couch, she quickly climbed up next to him and snuggled up close.
“So, what’s up?” she asked, though she felt a little anxious about what he wanted to talk about. He played with the water bottle for a moment before glancing over at her. It had been just over a day since they last saw each other, but he couldn’t keep his feelings bottled up any longer.
“I missed you,” he confessed, as their eyes met again.
Jillian’s face lit up with a faint blush. “Aw, I missed you too,” she said softly, a gentle smile on her lips.
Her arms emerged from her blanket, wrapping around his arm and pulling it tight against her, landing his hand between her thighs. Jason returned her smile. The warmth and softness of her body felt amazing.
“I’m not sure how I’ll cope with being apart after this week ends,” he admitted, his voice tinged with nervousness. Jillian nodded sympathetically.
“Yeah… me too. I wish you could stay longer, but I know you’ve got work and the majority of your life is in Florida.”
“I wish you could come with me,” Jason added, “but I know it’s too soon to move in together, and I wouldn’t want to take you away from your family.”
Jillian listened patiently before responding.
“Yeah... I’m not quite ready to leave them just yet. But that doesn’t mean I won’t visit you. I love the ocean, and the warmer weather sounds nice,” Jillian said with a smile.
“Yeah, and I’ll come back and visit here when I can. I stayed away for so long because I was afraid of my past. But I can’t leave my mom alone for so long again. It probably won’t be week-long trips for a while, but I could probably do weekend visits from time to time,” she giggled slightly at that statement.
“You’re gonna fly from Florida to here just for a day and a half, then fly back?
He shrugged a little at her observation. “If that’s what it takes, then that’s what it takes,” Jason said as the two continued to talk about how they’d manage their long-distance relationship.
Jillian could feel her cheeks warming at how seriously her new boyfriend was taking all of this. How much effort he was showing just to see her made her stomach flutter. She’d never had a guy go to such lengths for her, and technically for his mom too, but still. It all made her feel so warm and fuzzy, she nuzzled her cheek against his arm.
“You really don’t need to go that far, Jase. I appreciate the thought, but if you just shoot me a text now and then, maybe call me before bed a few times. Perhaps video chat sometimes. I will be happy.” She smiled sweetly at him.
“Sorry if I’m overreacting a bit. I just don’t wanna mess things up. You’re my first girlfriend, Jill… and I would like it if you were the only one I ever have.” When he called her his girlfriend and implied something even more serious, her heart did a little flip.
“It’s alright, I promise. I don’t want you to bend over backward just to make me happy. I’m already very happy. Just promise you’ll be honest and kind to me, and I’ll be loyal.” Her voice softened as she spoke. “And all yours forever,” Jillian murmured as she slowly slid herself onto Jason’s lap, pulling the blanket snugly around her shoulders.
She snuggled against his chest, running her hands up it as she dragged her nails along.
“I want to make you happy,” she added, her voice soft and alluring. Jason’s arms loosely snaked around her back, under the blanket, and rubbed softly.
Jillian eventually looked up and their gazes locked intensely as she moved up his body.
“Care for you,” she whispered, her warm breath now teasing his lips, now only mere inches apart.
“Hold you,” she continued, her words barely a whisper as her lips almost brushed against his.
“And kiss you.”
With that, their lips met once more, bodies pressed together as the blanket slipped away. Their kiss deepened quickly, lost in the heat of the moment, Jason’s arms were wrapped around her tight.
They kissed for several long minutes, completely lost in their own little world. Jason’s hand slid up her back until he found the strap of her bra. He played around with it for a bit, exploring its design, while their tongues swirled around each other. Just as Jillian was about to reach back and unhook it herself, Jason beat her to it. With a quick flick of his fingers, he unlatched her bra. Jillian suddenly pulled back from the kiss, looking at him in surprise.
“How did you...?” she started, suspiciously.
“What? It’s not rocket science. It’s just two hooks on a strap. I just slid one side against the other,” he explained, giving her a confused look, more wondering why she pulled away from their kiss than anything. She gave him a narrowed look, shook her head, and promptly let it go.
Jillian swiftly slid off her bra, revealing her modest chest once again to Jason. Tossing the bra aside, she felt a slight surprise as Jason leaned in to kiss her collarbone.
“Mmmm,” she giggled at the sensation of his lips on her skin, her breathing quickening as he moved lower.
She had to lean back a bit to accommodate Jason’s height. Suddenly, she reached over, grabbed the remote, and turned the TV back on. She quickly found a music channel playing soft R&B and turned up the volume to drown out any other noises that might draw attention. Just in time as she let out a sharp gasp as his lips found an excited hard nipple. They were a bit raw and overly sensitive after running in the fancy bra he just removed.
Jillian’s hands twitched, moving her hands to hold the back of his head. Jason’s arms that were wrapped around her kept her close as he sucked on the lovely pink nub, getting a little rough.
“Nnngh, Jason, not so, Ahh!” She let out a small yelp as his teeth grazed along her nipple.
She shivered and her fist clenched in his hair, tugging it a little harder than intended. To her surprise, he didn’t linger too long, pulling away with an audible pop. Gasping for air, she loosened her grip on his hair as her whole body felt limp. When he looked up at her, she leaned in for another deep kiss, their lips smacking together loudly. Her nails lightly scratched his scalp as they kissed, the sound of their lips and heavy breathing blending in with the music.
When they finally pulled away from each other, Jillian whispered softly to Jason.
“Jase, please. I don’t think I can wait any longer. I need you inside me, baby. Don’t make me beg,” she moaned greedily, flicking his lips with her tongue.
Jason hesitated for a moment before he nodded in agreement at last. Jillian had been feeling his erection long pressing against his jeans and her butt, knowing he must be uncomfortable. Unable or unwilling to hide the wide smile on her face, she got up from his lap and gestured for him to stand as well. Curious, he quickly stood up as she wanted.
Jillian gave him a reassuring smile and gently placed her hands on his chest.
“I’ve got you, Jase. If anything feels off, just tell me, okay? I want to make your first the best experience possible.”
Jason wasn’t exactly thrilled about being fussed over, but he knew she meant well.
So he simply nodded in response as she swiftly tugged his plain T-shirt upwards. She managed to get it most of the way off before Jason had to take over and pull it off the rest. Meanwhile, she quickly unbuttoned his pants. His stomach churned a bit, but her fingers moved expertly, and soon her fingers slid under his waistband, easing both his pants and underwear down.
Jason’s hefty cock sprung free as his pants slipped past his thighs. Jillian couldn’t help but giggle as she caught sight of it. Her mouth watered and her body shook slightly with excitement, a clear sign that she very much liked what she saw. With a grin, she let his pants and underwear drop to the floor, and then he stepped out of the pile of clothes along with his shoes, leaving him fully naked.
Jillian pulled her eyes away from his crotch to beam up at him before turning around and making her way to the couch, pulling at the bottom like a futon to transform it into a makeshift bed. His heart raced at the sight, a flurry of images filling his mind. Almost as if on cue, Jillian climbed onto the makeshift bed on all fours, presenting her plump round behind to him.
“You can keep undressing me too if you’d like,” she purred, her eyes sparkling with anticipation, reaching back and grabbing one of her cheeks, spreading herself for his eyes only.
Jason’s erection noticeably twitched at her actions. His own mouth watered as he nodded to her dumbly. As he got closer, he kneeled down and reached out with both hands and gently hooked his fingers on the lacy black panties that hugged her generously wide hips. Slowly pulling them down, a strand of her sweet, sticky essence clung to the fabric. Her lightly freckled, plump, pale lips, that barely concealed the delicate pink folds that were nestled within, were revealed to him. With her small button peeking out at the bottom and a small patch of regrowing orange hair.
Jason swallowed hard as he felt a rush of anticipation at the sight of her panties slipped down and pooled by her knees. Jillian maneuvered her legs out of the panties and spread her legs a bit more. Her soaked inner labia revealed themselves to him even more. She kept her eyes on him the whole time, body shaking slightly in excitement. The feel of his hungry eyes on her most private of areas made her bite her lip.
“Does it look alright to you?”
It was the first time he had such an intimate view of her pussy in the light. She couldn’t help but worry if he liked what he saw, though the way he was almost drooling as he stared was a good sign.
Jason nodded dumbly, his jaw a bit slack. A relieved, happy expression spread across Jillian’s face.
“Wow,” he murmured, taking a moment to gather his thoughts. “It’s... it’s beautiful,” he finally managed to say. The genuine compliment made her grin widen and her cheeks flush.
“It’s all yours, Jase,” she said in a breathy voice, as he kneeled there, somewhat rudely staring. She couldn’t help but chuckle softly at his dazed expression. She eventually turned and sat down, crossing her legs and leaning back, propping herself up on her arms.
Jason snapped out of his trance, meeting her gaze again.
“Well, are you just going to stare, or are you going to tell me what you want to do with me?” she teased playfully, her crossed leg bouncing softly as it rested on her knee.
His face turned a little red at her comment, realizing he had been stuck just staring at her for god knows how long.
“Sorry, I got a bit carried away. Um, what do you suggest?” He asked, almost as if he were asking for a recommendation at a restaurant, earning another laugh from her.
“Haha, relax, Jase. Trust me, I'm sure anything you say will be good. But I want another kiss first.”
Jillian grinned, leaning forward and opening her arms for him. Jason nodded, leaning in to meet her halfway, wrapping his arms around her as their lips came back together. She lovingly wrapped her arms around his neck. Pulling him deeper into the kiss, she scooted back so he could get up on the folded-out couch. When Jillian was laying back he used his forearms to avoid putting too much weight on her. She lifted her legs, and wrapped them around his hips, urging him closer.
Before Jason even realized it, he found himself pressed against her. Amidst the kisses and the newfound closeness, he had been simply enjoying the moment. Jillian’s hand slid from his neck, down his side, and between them. Her fingers carefully wrapped around the girth of his cock. Her delicate digits tugged and rubbed along his shaft. His whole body tensed up at the sensation, but he relaxed as he accepted it and continued kissing.
His body responded naturally by thrusting forward. Jillian guided his dick towards her already soaked and waiting pussy. As he felt the sensitive head of his erection glide along between her valley, he couldn’t help but shiver with pleasure. The anticipation made him throb in her hand, and he knew he couldn’t resist much longer.
Jason pulled back from the kiss, gazing into her eyes.
“Ready?” he asked sweetly.
Jillian smiled and couldn’t help but giggle a bit.
“I’ve been ready for a while now, but thank you, baby,” she replied, moving a hand up to caress his cheek, which had a rather thick stubble on it now.
His caring demeanor when they were intimate always warmed her heart as he gave her lips another gentle peck. Adjusting their position slightly, Jillian’s hand stroked his firm shaft tenderly, making his tip run up and down between her Labia.
“I want you, Jason.” she moaned out, her nails lightly trailing down his face and neck to his chest.
Jason pulled back slightly, she looked at him oddly.
“I want to make love to you, Jill. I want to claim you for myself in every way,” Jason said as softly as he could before he pressed forward. Jillian’s face flushed with his words, smiling up at him. With her hand guiding him, he felt the pressure of his tip against her slick and soft entrance.
Jillian let out a gasp and clenched her teeth. Wrapping her free arm around him suddenly, she dug her nails into his back, whimpering as her pussy was split wide open. Jason winced in pain but kept pushing forward, feeling like he couldn’t quite make his cock fit.
When he stopped, Jillian urged him on despite the pain, “Please don’t stop, it’ll fit, just… keep pushing!” she moaned loudly, gasping for breath.
After her plea she let out a small squeak as his dick slipped upward, accidentally hitting her clit.
“Sorry, it slipped out,” Jason apologized. Jillian took a moment to catch her breath.
"It’s okay, really." Jillian reassured him. “But thanks for taking it slow. You’re fucking huge, and I’m smaller than most. So it might take me some time to get used to your dick, but I don’t want to give up. I will be your first Jason, I swear,” she said earnestly, looking into his eyes with a fiery passion.
Jason simply nodded at the woman below him. “I want you to be my first, but I also don’t want to hurt you. If things get too intense, just...”
“I will be just fine, Jason. I want this and I will do whatever it takes,” Jillian interrupted, her determination clear in her eyes.
He admired her resolve, as misplaced as it was. Jason leaned in to kiss her again. As he pulled his hips, she guided him back to her already aching entrance. Taking a deep breath, she braced herself.
“Give it to me, baby.” With that, Jason started pushing past her lips once more, stretching her to her limits. Gritting her teeth, she closed her eyes and tried to push her hips down as well. There was a slight burning sensation before, at long last, his tip was past her tight entrance. She hissed in pain, trying to suck in deep breaths.
“Oh fuck... It’s in... Nggh shit, it’s so huge!” Jillian groaned, feeling a bit uncomfortable as her vagina adjusted to his girth.
Sorry...” Jason said, noticing her expression of pain and discomfort. It felt like his tip was being clamped between a wet vice so the pleasure wasn’t exactly there for him either yet.
Jillian shook her head. “Don’t you fucking dare apologize. It’s a part of you, and I want it. Just…Just give me a moment to adjust, baby,” she requested, moving her hand to rub her clit to try and override the pain with pleasure while she got used to being stretched. After a few moments, she nodded.
“Okay, I think I’m ready. Thank you for being patient. Please… keep going,” she commanded, though with a hint of hesitation. Jason leaned in a bit more, his cock spreading her insides more.
“Ahhhugh!” she cried out as she felt herself stretching. Her lower body trembled, and Jason started to panic a little.
“Jill, I really don’t think—”
“Shut up,” she said through clenched teeth, trying to focus on her breathing.
Jason flinched a bit when Jillian suddenly told him to shut up.
“Sorry, sorry. Just...,” She took a deep breath, slow and steady. “I’m a bit rusty and never had anyone so big.”
He wasn’t sure why she was telling him this, but he just nodded.
“It’s okay, take your time. I’m not going anywhere.” Jason leaned in and planted a gentle kiss on her forehead and moved a hand up to lightly caress her cheek. She gave him a strained smile.
Jillian hadn’t expected this to be so tough. She wished she would have prepped herself for his size beforehand. But it wasn’t like she got a heads up Jason would pop back into her life and they would finally have sex after. She wasn’t really complaining, though. This discomfort beat the hell out of the heartache she’d felt just an hour ago. His cock was way more comforting than ice cream, even if it burned like someone had set fire to her crotch.
Luckily, the pain finally started to fade again, and Jillian encouraged him to keep going. They repeated the process three more times, with Jason making a little more progress each time before Jillian had to stop him.
When it finally seemed Jason would get all the way inside of her she suddenly felt a sharp stabbing pain in her abdomen.
“Ow fuck, fuck, fuck!” Jillian cried out, making Jason pull back.
“What’s wrong!?” Jason asked, sounding even more concerned.
“Yeah, that was my cervix. Nnghh… that fuckin’ hurt,” Jillian groaned, clenching her jaw, still feeling shaken by the pain.
“Fuck, I’m so sorry, Jill,” Jason said, feeling guilty.
“Stop apologizing!” Jillian shot back. “I kind of expected it might happen at some point. Just, you know, try not to go past that point next time, okay? I still want you Jason. You hear me?” She looked up at him, meeting his look of concern with one of determination.
“So I shouldn’t go past this point?” Jason asked, seeking clarification.
Jillian nodded in response. Up until now, he had been more focused on not causing any discomfort than on his own pleasure. But the snug feeling around his dick was undeniably intense as her inner walls rubbed against his glans. He could feel her insides twitch as she adjusted to his size.
“Okay, now pull out,” she instructed, and he carefully withdrew. His body reacted to the sensation, sending a shiver of pleasure. Jillian seemed to find some relief too, emitting a soft moan. Once he was completely out, her legs which were spread as wide as possible, shook badly.
“Push back in but keep it slow, but don’t stop completely. And please remember, not too deep,” she reminded him. He nodded in agreement, positioning himself at her entrance once again.
With a slow smooth motion, Jillian let out a moan of pleasure and pain as she felt completely filled even without him being fully inside of her. Jason eased in halfway before pulling back, eliciting a soft groan from Jillian.
“That’s good, baby, keep going,” she murmured, laying her head back and closing her eyes for a moment.
Gradually, the discomfort fully faded, replaced by intense pleasure as they finally made love properly for the first time. Her breath quickened as Jason’s rhythm picked up. She wrapped her legs around him loosely as they moved together at a slow, but steady pace. Her hands held onto his shoulders and soft moans escaped her lips, matching the rhythm of his loving thrusts. Unable to contain his own pleasure, Jason moaned out as her pussy caressed his cock. He breathed heavily. His arms wrapped behind her and pulled her into another deep kiss.
After a while, Jillian did her best to move herself with his thrusts, teasing the fine line between pleasure and pain. She was craving every bit of him. Urging him to go deeper even as risky as it was. Jason’s large body was practically smothering her, but that was just how she wanted it as she moaned happy little whimpers each time he pushed inside her. His speed increased as time went on.
“Fuck, fuck, fuck! Oh god, yes! Keep going, Jason! Fuck meeee!” she cried out, grateful for the music mostly covering their sounds. They found a rhythm that worked just right, his movements just grazing her deepest spot inside her. Her sweet moans urged him to work even harder.
“You feel so amazing!” he groaned, picking up the pace. “I never knew it could be this good.”
The slick sounds of their union were barely masked by their moans and the music. Jill had already cum once already so she was extra soaked letting him move easier.
“Deeper… please go deeper, Jason!” Jillian cried out, even though she knew it was probably going to hurt. She wanted, no, she needed him to go deeper. His next few thrusts were indeed deeper, and her whole body flinched each painful time.
“Ah! Ah! Ah!” she screamed out each time his cock hit deep inside her.
“Hnngg... I’m gonna cum!” He growled as his movements slowed but were much more pronounced in motion. Her legs wrapped tight around his waist, trying to keep him inside her.
“Cum inside me!” she pleaded, “I want you to fill me with your seed! Give it to me, fill my pussy to the brim!” she groaned in pure desperation. Her earlier words echoed in his mind.
“You can’t get me pregnant.” A mix of resignation and honesty had been in her tone. Pulling out in time seemed like an impossible task that wasn’t sure he could manage, anyway.
“Fuck!” Jason exclaimed as he thrust as deeply as he could, causing her to shiver in another painful yet incredibly intense climax of her own.
“Ahhhhhh fuuuuuuck!” Jillian moaned loudly as her legs around him violently trembled as she soaked his cock and the couch beneath them with an explosion of her juices.
As Jason felt her tunnel tighten around his cock in orgasm, he let out a low growl, burying his face into her hair. Squeezing her body tight against him, he released deep inside her. Painting her cervix and walls with an excess of pearly white seed. The warmth spread into her stomach, prolonging her climax with each pulse of his release. Jillian bit down on his shoulder to stifle her cries. There was no way she could contain her screams if she didn’t. Every part of her was trembling with unimaginable pleasure.
As Jason’s climax slowed, the last of his cum dribbling out inside of her, Jillian’s trembling became more noticeable.
“Hey... you okay?” he asked, trying to catch his breath.
Instead of answering verbally, she sucked in and let out long slow breaths and nodded against his chest, her legs still tightly wrapped around him.
“Mmm, s-so full.” Jillian whimpered into his chest. To pass the time as they held each other, Jason peppered kisses on the side of her head and on top. Her shaky breaths turned into soft laughter.
“I can’t... remember the last time...” she murmured, speaking between gasps before she paused, nuzzling her face into his chest, filled with his comforting scent. Taking a deep breath, she let out a contented sigh leaving her sentence at that.
“What can’t you remember?” Jason asked, genuinely curious.
She planted a kiss on the bite mark she left before pulling away from his chest, flashing a smile up at him.
“I can’t remember the last time I could smile after sex,” she admitted.
Along with her smile, her eyes shimmered with unshed tears. He couldn’t help but smile back.
“I love seeing you happy,” he whispered.
Her freckle covered cheeks, flushed with heat and she hid her face in his chest again, mumbling.
“You can’t do that...” Her arms tightened around him.
“I can’t do what?” he asked with a soft chuckle.
She peeked up at him, still blushing furiously.
“Say cute stuff like that, you jerk,” she replied. Jason couldn’t help but find her even more adorable, it felt like their hearts were beating in sync as they gazed at each other. They both leaned in and shared another long, wonderful kiss.