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coldfanbou · 15 days ago

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Kinkcember Day 3: Tentacles

Day 3 gets a little weird with tentacles making their return to the kinky month

Length 1.9K

Jessi & Jennie X tentacles

“You said this was going to be an easy hike,” Jennie complains, running out of breath. Her eyes follow the barely used trail as it winds up the mountain.

“Oh, shut up; it’s going to be worth it. There’s a really nice view at the top.” Jessi said as she continued moving up the overgrown path. She bit her lip, happy to be returning to the mountain. Her experience the last time she had come was one she couldn’t get out of her head. Something told her to come back. Every step up was one closer to the top, and Jessi couldn’t help but rub her slit every so often, just out of sight of Jennie. Their march through the mountain moved slowly, each woman grateful that they had begun hiking in the early morning when the temperatures were cooler. They reached the top soon enough, a plateau covered in a heavy forest.

Jennie stopped and looked around, seeing the city in the distance. She sat down, enjoying the wind as it passed through her and into the forest. “You were right; this is a nice view,” she said before lying down.

“There’s something even better in the middle; there’s a lake where we can swim and cool off,” Jessi said, glancing deeper into the forest and biting her lip before turning back to Jennie. “Let’s go.” She whined, becoming more pushy the longer they waited.

Jennie groaned, wanting to spend more time resting. The thought of a lake in the middle of the forest intrigued her, though she thought it would be nice to take a dip after such a long walk. The younger woman stood slowly and turned to her friend, following her as they headed into the forest. Light broke through the scattered leaves, allowing a good amount of sunlight as they continued. The walk didn’t last too long, five minutes at most, Jennie thought as they reached a clearing and their eyes came upon a placid crystal blue lake. Jennie smiled, excitement surging through her as she saw the lake's beauty. “Wow, you weren’t lying. This looks amazing.”

Jessi wasted no time, kicking off her shoes and stripping down in front of Jennie. “I’m heading in first,” she said, walking into the cool water and lying back. The older woman kicked her feet, getting further into the lake before coming to a stop.

Jennie didn’t want to miss out, so she stripped out of her sweat-filled clothes, dropping them beside Jessi’s before joining her in the water. It was cool but not unpleasant. She swam to join her friend, moving toward the center while kicking up a lot of water. Jessi looked toward her friend, smiling as she saw how much she was disturbing the water. “You were right; this is great,” Jennie said as she swam around the older woman.

“I told you,” Jessi said with a smirk on her lips as purple haze began rolling onto the lake from the far side. She ran her hands down her body rubbing her slit in front of the younger woman without care now.

“Jessi! What are you doing?” Jennie screamed with a surprised smile. She was used to having fun with the older woman but didn’t expect her to want to do it while swimming. Looking past the older woman, Jennie finally noticed the purple haze as it reached them. She became lightheaded. Jennie held her head as the haze filled her lungs.

“Don’t worry, this is fine,” Jessi groaned, shutting her eyes and pulling away from the younger woman. Jessi laid back in the water, floating along the top as she ran her fingers up and down her slit. The water around them began to shift, and while Jennie panicked, Jessi smiled.

Soon, the haze blocked all sight of the beach, leaving the women alone. From beneath the water came tendrils that slowly closed in on the older woman who kicked at the water. They found their first target, wrapping around Jessi’s tanned legs and arms. Another tendril soon poked through the water near her head; Jessi craned toward it without hesitation, running her mouth along its slimy surface. The tentacle bent in on itself, its bulbous head rubbing against Jessi’s mouth before the rap star opened her mouth and allowed it inside.

Jennie was stunned at the sight and began to swim away, only to be stopped. More tentacles held her in place, and they continued to appear, keeping the young woman. Whatever beast held her wasn’t mindless; it turned Jennie around, forcing her to watch the older woman.

Jennie’s mouth dropped as she was turned around. Jessi was getting fucked by the beast. In the time she had been facing away, Jessi had gone from sucking on one tendril to having her entire body toyed with. The beast was filling Jessi, its tentacles moving inside her cunt and ass. It looked like it was going to break her. Jennie gulped and felt herself getting wet as she watched the tentacle moving inside Jessi, bulging the rapper’s stomach. As her eyes moved up, she saw Jessi taking another tentacle down her throat, watching it bulge, too. Jessi’s muffled moans became the only thing she could hear, her body the only thing she could focus on.

The rapper was having the time of her life, her body being pumped full of pheromones that increased the pleasure she felt; every thrust by the tentacles made her cum. She didn’t resist at all as she felt another rub against her ass whole; she reveled in the pleasure as the tentacle stretched it out. The slimy tentacle provided its own lube, easily sliding deeper inside. Jessi’s muffled moans grew louder as she felt the tentacle inside her ass grows thicker. Her eyes rolled into the back of her head as both holes were filled to the brim. Each movement made Jessi’s toes curl; as wave after wave of mindnumbing pleasure crashed over her, the rapper fully gave her body up. Something she wished she had done the first time she felt this way.

Jennie watched on as the beast continued to toy with the older woman, a couple of tendrils opening at the ends and attaching themselves to the rapper's tits. Jessi’s continuous moans floated into Jennie’s ear, continuing to turn her on. She began to question how good it must feel. As the thought crossed her mind, one of the beast's tentacles began to rub her slit. Jennie moaned the amount of pleasure she felt coming as a shock to her. Her eyes fluttered, and she struggled to keep her mind clear.

More tentacles came from beneath the water, each lashing at the younger woman and slapping against her body; two smaller ones toyed with her breasts, and as much as Jennie wanted to struggle, her body was giving in. The smaller tentacles were flicking her nipples. She tried to catch the moans before they came out, but as the tendril by her cunt began to creep in, she had to release her moans. It snaked its way inside Jennie; she felt it slowly growing thicker inside of her, stretching her tight cunt like never before. Jennie began to groan. Looking down, she saw the tentacle make a visible bulge in her stomach. It slowly dragged itself out of her before moving back in at a painfully slow pace.

“Faster,” Jennie muttered, surprised at her own voice. Like it was following orders, the tentacle picked up speed, ramming into Jennie’s womb before beginning to thrust into her. Jennie’s body tensed as the sudden movement rocked her; she felt herself on the verge of cumming. Another deep thrust made her cum, her walls squeezing down on the tentacle's shaft. It continued to move at the same pace, uncaring that the woman in its grip was becoming more sensitive by the second.

Jennie began to understand how Jessi was feeling, and her will to escape soon faded as the beast began to train her. More tentacles appeared, rubbing the thin woman’s body; one rubbed between her ass poking and prodding her asshole, while another slapped her face, its scent drowning Jennie. She involuntarily opened her mouth, and it slid inside; the bulbous head stretched Jennie’s throat to its limit before sliding in and out. The young woman used her tongue, trying her best to lap at the side as she felt it hit the back of her throat. Jennie's view of Jessi becomes completely blocked, but the older woman is given a perfect view of her. The tentacles pulled her from the water, raising her.

Jessi took in the sight of the younger woman’s body bulging as the beast slammed itself into her womb. The beast pulled itself from Jessi’s mouth, allowing the older woman to lap at the head like it was an ice cream as she watched. “Your friend is taking it nicely,” A voice said before pausing; the older woman looked around but saw no one. “Just like you did the first time, this time, I’ll make sure to mark you.”

With those words, it clicked who was talking; it was the beast. Being marked as the beast’s companion was something that intrigued the older woman; the thought of being pleasured every day was something wonderful to her. “Do it, I’m yours.” The tentacles inside Jessi began to pick up the pace, slamming into both holes. The older woman’s body was a toy for this beast, one that took full advantage now, slapping her body with its tendrils, leaving it red all over as it spanked her roughly and continued to stretch her. Jessi continued to cum with every thrust, her body giving out as she felt it becomes flooded by the beast's cum, her belly bloating as it marked her. The last thing she felt before passing out was a stinging sensation on her abdomen.

Jennie was next; the poor woman had been cumming nonstop for the last few minutes. She felt the beast’s tentacles begin to throb. Jennie wanted it; she wanted this thing to cum inside her. As the beast continued to move quickly, she tried to flex her muscles, tightening her walls around the tentacles. Whether it worked or not is questionable, but either way, the beast came. Jennie felt its hot cum pour into her cunt and down her throat. The taste was horrid but addictive. After the first drop, she was hungry for more and drank every drop, barely noticing her belly bulge from the amount of cum that was dumped inside her.

As the young woman passed out, she was also left with a mark. Both women awoke on the shore near their clothes, their bodies seemingly left unharmed, a trail of cum the only signifier that something had happened. That was what they thought until they noticed they had a mark on their stomach. Each woman looked at it warmly, remembering the events that transpired. “Bring me more, and I will bring you more pleasure.” They heard the voice ring out in their heads.

“Yes, Master,” Jessi said, licking her lips. She looked over at the younger woman, who nodded in agreement. The two would have to find more people to show them what true pleasure was.

#kpop smut #blackpink smut #jennie smut #Jessi smut

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hgfictionwriter · 2 months ago

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Discovery: Part Five - First Time

Jessie Fleming x Reader

Summary: With the truth revealed, Jessie and you now have a chance to fully build an authentic, honest relationship. And maybe, the physical intimacy that's plagued your relationship - and Jessie's past - can finally be healed.

Warnings: G!P content. First time; oral (J receiving; R receiving); body image issues; lingering internal conflicts and themes of rejection; language.

A/N: This is SO long. I just got carried away - there was so much I felt would be going through Jessie's mind that I couldn't just skip over during their first time together, combined with all of the previous baggage. It felt much more natural to pace it this way.

"So, if I ask you to spend the night, do you think you would?"

Jessie couldn't believe the contrast between this morning and now. She'd come over to your apartment with absolute certainty that this would be the end; she'd maybe get to hold you once more and then it would be the inevitable goodbye.

Instead, here you were, cuddled into her on the couch, fingers of one hand intertwined with hers and her arm wrapped around your shoulder. Rather than a painful and heavy goodbye, you'd sat together for hours; conversation renewed, deeper, sincerer, and you were asking her to stay.

Jessie smiled at you.

"I'd love to," she told you before giving a quiet, bashful laugh. "If you asked, that is."

You chuckled and nudged her with your shoulder. "Well I'm asking."

"Then I'd love to stay," Jessie replied with a resolute nod.

"Now that I know why you were so hesitant to spend the night before," you told her with a smirk, leaving Jessie in awe that you could be so relaxed about this and that things felt so natural between you.

While Jessie's mind had been wrought with questions and worries for months, now the only question that remained was, 'What took her so long to tell you?'

You fidgeted slightly and scratched at your temple, eyes cast downward momentarily before you looked up at her.

"Just as before, even more-so now, actually, you're welcome to sleep in the bed. I-I'd like you to." A beat passed and you rushed on. "But only if you want to."

Jessie's heart felt like it was lodged in her throat, but in a good way. She would've never pictured this.

"Y-yeah," she managed to reply, voice almost wavering. "I'd like that."

You clearly were anticipating a decline, because your reaction was delayed and was one of momentary surprise before smiling broadly at her.

"Oh! Fantastic!" You said before shrinking into yourself slightly, seemingly embarrassed at your enthusiasm. Jessie found it adorable and kissed you. Your cheeks were burning pink when she pulled back. "You can, um, wear some of my clothes to bed. I'm sure I have something that'll fit."

"Sure, that sounds good," Jessie said as she gave your hand a reassuring squeeze.

Soon you led her into your room and dug through your drawers for some sleepwear for her. Jessie had been in your room a handful of times, but really only in passing. Given how physical aspects of your relationship had been so taboo prior, the bedroom had become unspoken, forbidden territory. She took this opportunity to look around and really take it in; all of your belongings, the way you had things arranged, all the things big and small that made it yours.

"These should work."

Jessie was pulled from her observations by your voice. She turned to you and gave you a belated smile as she took the items.

"Thank you."

Silence fell over you two, but it felt very different than ones previous. This time, Jessie wasn't scared.

"I know we've talked about a lot today, tonight, but I, um, just want to say again that I'm really grateful you told me everything," you said softly as you looked at her.

"Me too," Jessie returned with a gentle smile. "Again, I'm really sorry it took me so long. I can't tell you how amazing it is to have this openness with you and to be given another chance. I really do love you, and I'm so grateful that I can tell you that and to not have to hide."

You looked at her with the warmest eyes and reached out to gently take the clothes you'd just handed her and set them down on the bed. You took a step towards her, closing the space between you two and wrapped your arms around the back of her neck. Your waist pressed against her’s and Jessie inadvertently swallowed though she held your gaze.

"You shouldn't have had to hide in the first place," you said as you cupped her cheek. "Thank you for trusting me with this." Jessie nodded.

"I'm trusting you with this. My heart. My past. All sorts of things," she finished lightly, hoping for some levity but failing to come up with something witty. She settled for a silly smile that contrasted the weight of her words. You weren't fooled and continued to look at her in earnest. Jessie dropped her smile and allowed herself to sit in this moment with you instead.

Soon your lips were on hers in a slow, deep kiss. Instead of tensing up and coaching herself through it, she finally gave herself permission to relax into your kiss.

Her eyes fluttered open belatedly when you subtly pulled back from the kiss. She looked to you with mild confusion only to see a soft smile crossing your lips. You caressed the back of her neck briefly before kissing her again even deeper. Jessie barely managed to hold back a moan. She tightened her arm around your waist, pulling you closer.

That small act of confirmation seemed to spark something in you. Suddenly, your fingers were running through her hair and you kissed her harder.

It didn't take much for Jessie to feel the telltale signs of her cock starting to stiffen. You were pressed flush up against her - her movements stilled and she shifted her hips back slightly to create space.

"You don't have to," you said slightly breathless as you pulled back just enough to look at her. A moment passed and you shook your head subtly. "I don't want you to."

Jessie inadvertently swallowed. She searched your eyes, a stubborn hesitancy and doubt still lingering in the back of her mind. You caressed her cheek with your thumb and it quieted her thoughts. She pulled you close to her once more and rest her forehead against yours.

"I told you I find you very attractive," she said in a low voice with a smirk. "So much so that it's been a problem."

She saw you bite the inside of your lip.

"I don't see a problem here," you affirmed before giving a smirk of your own. "I like it."

You kissed her again and though Jessie wanted nothing more than to reciprocate, she had to ask once more.

"Are you sure? I mean - you weren't anticipating...this," Jessie finished with a near mumble as she glanced down between you purposefully before looking at you again. "And you said you preferred a strap."

You blushed, dropping eye contact, but caressed the side of her neck still.

"Well, at that time I didn't exactly know that you had anything more than a strap," you said sheepishly before forcing yourself to look up at her. This time, you spoke assuredly.

"And you're right that I wasn't anticipating this. But, I love you. And this," you gave a look mirroring Jessie's a moment ago, "is part of you, which means, I'm all for it." You gave a slight shrug. "And, you know, it's pretty sexy. Knowing...feeling, or seeing, what effect I might have on you." You finished with a shy chuckle. "I'm not upset about it. Let's put it that way."

Some other girls had made fun of her for visibly being aroused, but there was nothing malicious about your reaction. In fact, your reaction was far from it. She smiled gratefully and nodded.

"Okay. Well, I'm glad. And, um, I'm sorry in advance if there are moments - like this - where I get a little too...excited. I don't mean to ruin a moment or anything," Jessie explained as she glanced back down at the slight bulge in her pants - it wasn't anything too overt right now, but if you two carried on it certainly would be.

"You don't need to apologize," you said, mildly chiding her. "I just told you I like it." You slowed, cupping her face once more and speaking softly. "I like it," you repeated.

Any lingering concerns were snuffed out as you began kissing her once more. Slow and patient at first, before deepening. She wrapped her arms around you fully and met your kisses with equal, growing passion. Your hands began to wander down her back and after a moment of hesitation, Jessie allowed her hands to explore as well.

What was an initial arousal was now becoming full-on as your hands played with the hem of her shirt, your fingers grazing ever so lightly against her skin, and when she heard you faintly moan into your kiss, there was zero chance of her hiding the way her cock now strained fully against her boxers and pants.

When you didn't pull away, and instead pulled yourself closer to her, her fingers dug into the small of your back through your shirt, pulling another muffled moan from you.

Jessie opened her eyes, blinking rapidly as she gently broke off the kiss, only now realizing she was short of breath.

"Sorry," she breathed. You frowned at her in confusion.

"What for?"

She frowned in return as she tried to conjure up some coherent thoughts.

"I'm, um, getting carried away," she eventually managed to say.

"I'm not remotely bothered," you assured her. "I'm getting carried away as well, then, too," you added with a faint grin. You looked away briefly before resting your hands on the front of her chest and pushing upwards, your hands feeling their way up her neck and into her hair as you spoke. She nearly shivered.

"I know we just said today we'd take it slow," you looked away again, "but, um, we also don't have to."

Jessie swallowed, studying you intently. "I don't want to pressure you at all. I mean, I dropped a lot on you today. I'm very happy to go at whatever pace you set. I have no expectations."

You nodded, seemingly lost in your own thoughts.

"Mhmm. And, well, we've also been together for months. And...I'd be lying if I said I didn't want you. And, maybe, based on what I'm feeling right now...you might want me, too," you finished with a tentative, but hopeful look on your face.

Jessie blushed with a lopsided grin. "I think that's safe to say."

You both looked at each other, gauging one another and waiting for the other to make the first move. It was several seconds before you grabbed her by the shirt and pulled her in for another kiss, which she readily met.

Hands wandered even more ravenously this time and you were very subtly grinding yourself against her bulge and Jessie swallowed a moan that threatened to escape. She exhaled heavily and found herself pulling you tight against her, her hand now sneaking under your shirt and you moaned in approval.

Surprise flooded Jessie system as suddenly you were pushing her towards the bed, not breaking the kiss until you pushed her down on the edge. When she looked up at you, your eyes were dark with lust and her cock throbbed at the sight.

"Wh-" Jessie's question was cut off as you lowered yourself onto your knees in front of her, not dropping her gaze the entire time. You placed your hands on her thighs and moved your hands upward until your fingers snuck under her shirt to graze her abdomen.

"Is this okay?" You asked. Jessie could only nod, unable to find the words. You toyed with the hem of her shirt again. "Do you prefer clothes on or off for this?"

"I, um," Jessie stammered. "On, for now, I guess." She shook her head. “Wait, I should do stuff for you.” She went to switch places with you but you denied her.

“There’s time for that, too. I want to do this for you,” you said as your thumbs idly caressed her skin. Jessie let your words settle in and a slow smile formed across her lips. She nodded.

You smiled and began to massage her hips, your hands moving inwards until you started to unbutton her pants. She was absolutely aching with anticipation by now. Jessie's eyes were trained on you and she breathed through her lips as her mind tried to keep up with what was evolving.

"You're sure?" You asked one more time, fingers ready to unzip her pants. Jessie let out a breathy laugh.

"Yeah. I am. Um, if you are. You know you don't have to do anything, right?" You didn't break eye contact.

"I know. I want to do this. I want you," you stated and Jessie felt a flutter go through her entire body at the declaration. She frowned as you grew bashful. "I, um, haven't done this in a while though. So...bear with me. I apologize in advance," you finished with a sheepish laugh. Jessie frowned deeper.

"Don't apologize. At all. I-," she wracked her mind for the right words to say. "I'm positive it'll be great. You'll be great. I, um, just want to be with you. That's what's most important to me." You looked up at her from your spot on the floor between her legs and gave her a grateful smile. Your earlier comment caused Jessie's mind to start envisioning you in front of other people in a similar position. She didn't like it.

"And...we don't really need to talk about, you know, other times or people...at least right now," she added gently.

"Oh. Right," you said as you flushed pink. You sat back on your heels and cleared your throat before raising yourself up again and kneading her thighs. "Okay, well, what I mean is, feel free to tell me what you like...and tell me if you don't like what I'm doing."

Jessie felt a tightening in her throat and she forced a series of nods. "Okay, I will."

It probably shouldn't have been a big deal, but she was left in awe to some degree. Other girls didn't care what she liked or didn't like. It was about them - satisfying their curiosity or having a story to tell after. But that wasn't you at all.

She cleared her throat and went on. Now was not the time to get emotional.

"But please don't worry. You can see already that you're doing everything right," she said with a slight chuckle as she tucked your hair behind your ear and caressed your cheekbone with her thumb. "And same goes for you, please tell me if I'm doing anything you don't like. And please know you don't have to do anything that you aren't comfortable with."

"I know, baby," you said as your raised yourself up to kiss her on the lips.

Jessie was kissing you back, eyes closed, when your hand returned to her zipper and began to pull it down and over her aching erection. Her efforts to kiss you back stalled as your hands pushed the fabric of her pants aside and you began to caress her through her boxer briefs.

You began to kiss her neck and Jessie did her best to swallow any impending moans as you continued to feel her through the fabric. Her eyes remained closed as your fingers traced over the head of her cock before gently feeling and exploring what you could of her length.

Next, she felt you trace along a seam of the boxer briefs and her whole body stiffened as your warm hand reached in through the slit of the fabric and your delicate fingers first made contact with her cock.

"Is this okay?" You whispered into her neck as your hand stilled. She nodded. That fleeting touch alone felt incredible and she could hardly believe it was happening.

"Yeah," was all she could manage.

Assured, you gently wrapped your fingers around her length and pulled it through the slit. Now, unencumbered, her full length sprang upward in your grasp and, intentional or not, you sat back and Jessie opened her eyes to see you looking at her cock.

She registered this image of you looking down at her length that stood proudly up within your hand, a large bead of precum pooling at the tip. She wasn't 100% sure how to read your expression, it wasn't negative for sure, curiosity maybe? Either way, a rush of apprehension went through her and she pushed herself back a bit and began to stammer.

"We, um, we don't-"

You seemed to belatedly clue into Jessie's mounting anxiety and you sat up again, one hand coming to cup her cheek as you kissed her mid-sentence, effectively shushing her.

"It's okay," you whispered, kissing her sweetly once more. You urged her to look at you and she did, shoulders visibly rising and falling as her heart raced. “Do you want to stop?” You asked gently, free of judgement.

She studied you, seeing nothing but concern and care in your eyes. She began to relax and she shook her head. “No.”

You kissed her again, letting it linger this time and only pulling away once Jessie's breathing had evened. "You're beautiful," you said. You leaned in so your lips nearly brushed against her ear. "Please don't worry. I love you. And please tell me at any point if you’re uncomfortable and want to stop. That’s perfectly okay.”

“I don’t want to stop,” she told you. She swallowed her residual worries and leaned into your ear. “I want you, too.”

Jessie's jaw fell slack as the hand around her length, which had remained still the past few moments, began to slowly, lightly caress her, your thumb now patiently circling her tip.

Her shoulders rolled back as she felt your tongue flick her earlobe and your breath was hot and teasing against her ear.

"I can't wait to taste you."

She didn't know what she was expecting, but it certainly wasn't for you to say that. She belatedly realized that her fingers were digging into her thighs. She relaxed them along with the rest of her body and you began to kiss your way down until you were resting on the back of your heels once more.

She watched as you looked up at her. You released her momentarily, eyes locked on her still as you licked your hand before wrapping your fingers around her girth again. Jessie didn't drop your gaze, but her shoulders fell at the sensation.

"You can tell me to stop at any point," you reminded her as you began to stroke her up and down. Jessie silenced another moan deep in her throat and swallowed audibly instead as she nodded.

Jessie's mouth fell open further as you dropped her gaze and bent your head towards her waiting arousal. She moved her hands to the edge of the mattress and gripped it tightly as she felt your hot tongue give a slow, teasing flick across the head of her cock. Her breath hitched in her lungs as your tongue languidly circled around the tip.

Her head fell back and her eyes focused on the ceiling as you continued to slowly explore her. Your tongue teased her head, your tongue grazed down her length and back up, your hand gripped her gently, then firmly, you stroked her and circled her.

When your lips wrapped themselves around her tip and you gave a soft, slow lick before sucking and releasing her, she white-knuckled the mattress and set her jaw so harshly it nearly hurt. When your mouth fully sank down on her length, her cock now surrounded by the warmth of your mouth, she couldn't hold back a faint gasp.

Encouraged, you continued, soon bobbing your head up and down on her length and Jessie's breathing became quick and shallow over the incredible sensations that radiated from between her legs and throughout her body.

She curled her fingers inward more, her nails audibly digging into the mattress as you took her further into your mouth, her tip now nudging the back of your throat. Her thighs flexed intermittently as she resisted the urge to move her hips in time with you - she didn't want to be pushy at all.

Her eyes snapped downward as suddenly your free hand found one of hers. She interlaced her fingers with yours and you looked up at her - an absolute sight for Jessie, seeing your mouth wrapped around her swollen cock, your other hand at her base. Again, she was caught off guard as you took her hand and guided it to the back of your head.

The look on her face must've relayed the hesitation or doubt she felt, because you gave a subtle expression of affirmation and pushed her fingers through your hair.

Jessie's breathing was uneven as you refocused on the task at hand, closing your eyes and sucking and licking her once more. Her eyes closed and her head fell back once more as the overwhelming sensations sparked all over again.

She tentatively played with your hair, her hand barely resting on the back of your head as you moved up and down her length. This carried on for a short while until your hand came back up to hers and pushed her hand firmly down on your head, her length going deeper into your throat than ever.

Jessie groaned and clutched your hair instinctually before her eyes flew open in brief panic at allowing herself such a reaction. The feeling ebbed as you continued, undeterred, your thumb actually caressing the back of her hand. She relaxed, sinking into the bed a bit and eyes falling shut once more as she now guided your head up and down.

The sensations that had been building, not just now, but a culmination really of the past several months with you, were about to reach their peak. Jessie's breathing was rapid and she bit the inside of her mouth as a familiar tightening formed between her legs. She opened her eyes, blinking a few times as she tried to center herself.

"I-I'm, I'm gonna cum soon," she told you.

You continued to suck her off and Jessie had to bite the inside of her cheek hard to not groan or curse in pleasure.

"Y/N, I'm not going to last," she tried to warn you, panting as she spoke. "I'm gonna cum."

She expected you to pull back from her, but you remained steadfast, keeping her warm in your mouth until Jessie gripped your hair tightly and tensed up underneath your ministrations. She snuffed out another moan as she began to spill herself into your mouth and down your throat. Her breath hitched as she spurt several times inside your waiting mouth.

Jessie breathed heavily as the twitching of her cock slowed and so did you. It took a few moments for her to come through the haze of her climax and when she did she looked at you in concern. You, however, simply sat back and covered your mouth briefly before swallowing. Jessie just stared at you, stunned.

You wiped your mouth and sat there on your knees before looking up at her. Jessie was still catching her breath as you both looked at each other.

"You taste good," you eventually said, causing Jessie to flush red immediately.

"You-you didn't have to do that," Jessie responded. "Um, swallow, that is." She frowned and flushed further. "Any of it, really."

You frowned in return before giving her a light shrug. "I know. I wanted to." You looked away briefly. "So, um, was it okay?"

Jessie gave you a bewildered look.

"You're joking. You couldn't tell?" She asked, unable to help but laugh a bit. She just shot a huge load down your throat, relatively quickly too - of course she liked it. Instead, you blushed.

"I guess. You were very quiet though," you said somewhat tentatively. You went on quickly. "Maybe that's just how you are - and that's totally fine. I guess I just- I don't know."

Jessie wanted to curse, and moan, and groan with pleasure as you pleasured her, but again, she'd been made fun of before. She'd been the subject of teasing and mocking in hallways or a classroom and it caused her to hold back. She studied you wordlessly for a couple of seconds before nodding.

"I really loved it. You were," she shook her head as she tried to find the words, "beyond incredible." This seemed to relax you and you rose up onto your knees and she wrapped you in a hug as you kissed her.

"Shit, sorry," she said, another blush creeping up her face as she realized her deflating cock was directly on your shirt, staining it with your spit and whatever little remained of her cum.

"Oh, don't worry," you said. You chuckled coyly, gaze flitting away for a second before returning. "We were going to get changed anyway, right?"

Oh right. She'd forgotten all about that already.

Yet again, for the nth time today, you surprised her by locking eyes with her and slowly lifting your top off in front of her. Her jaw dropped slightly and her eyebrows lifted as she took in this stunning visual of you.

"Is this okay?" You asked, your shirt now discarded next to you and your hand behind your back, poised to unhook your bra.

Jessie nodded with a goofy grin. "Yeah, completely."

You smirked and gave her a small nod. "What about you?"

Jessie didn't falter under your watchful stare. She could feel her confidence continuing to build as the barriers she'd firmly placed between you two were rapidly destroyed to discover that there was love and acceptance on the other side.

She lifted her top over her head and tossed it by yours. She reached for your arms and gently guided you up onto the bed with her, your hand still on the back of your bra. She reached behind you, adoring the smile you gave her as she did, and undid your bra for you.

Not thinking twice, Jessie dipped her head to begin trailing kisses down your chest. She cupped one of your breasts and pulled the nipple of your other in between her lips to tease it with her tongue. She grinned into you as your hands wandered and dug through her hair.

She continued to attentively discover your breasts and soon you started shimmying out of your pants and were tugging at hers. Her cock now fully alert and ready to go once more, making her even more grateful that you'd started with a blowjob; it took the edge off for her.

Jessie chuckled softly as she lifted her hips so you could remove her clothes. Yes, she was still nervous, but more than anything she felt an undercurrent of safety and affection and it was such a change. One she more than welcomed.

"Holy shit, you're gorgeous," you said as you took in her naked form. Jessie snorted and gave you a frown.

"You're gorgeous. My God, look at you," she said. She glanced down pointedly at her stiff member. "In case you needed proof that you are so fucking sexy."

Your eyes darkened once more and you pulled Jessie into a heated kiss. The kisses between you two earlier were slow and passionate, but these were hungry and needy.

Soon, you tugged gently on her arm, coaxing her up the bed and she allowed herself to be pulled down on top of you, but made sure to position herself not so precariously against you. She took this as her opportunity to start kissing down your body towards your core.

Your grasp tightened on her, urging her to not move further down.

"Stay with me up here," you said.

"Let me take care of you," Jessie said as she began kissing her way downward once more. "You got to taste me," she looked up your torso at you as she laid slow, lingering kisses down your stomach, "I should get to taste you."

You bit your lip and released her, a smirk on your face as she continued to kiss down your body. She shifted down the bed so her head was nestled between your legs. She felt a buzz, lightheaded even, as your scent filled her senses. Her cock was pressed flat against her torso as she lay on the mattress and she had to readily ignore the hints of pleasure from the friction any slight movement of hers created.

She saw the way your fingers dug into the sheets in anticipation and at a glance she could see the way your arousal pooled at your entrance. Another boost of confidence went through Jessie at seeing physical proof that the act you just performed for her wasn't a turn off, and evidently, even turned you on.

Your knees were raised, feet on the bed and she began to kiss her way down your legs, slowly, teasingly - down one side and then the next. She felt affirmed by how your hips subtly bucked up towards her mouth as she got closer and your fingers dug further into the sheets in frustration every time she pulled back.

She showed an ounce of mercy as she traced her tongue along the junction between your legs and core; staying purposefully away from your inner lips and keeping her tongue light and fleeting. She glanced up your body with a grin, pleased with how your chest visibly rose and fell already under her drawn out attention.

When she saw a bead of cum drip past your entrance and down towards the sheets, she finally delved in. She dipped her tongue down and slowly dragged it upward, capturing your dripping juices and finishing with a soft lick at your entrance. Your body tensed up and a small gasp escaped you and before you had even relaxed she placed her tongue flat against your entrance, before tracing diligently upward through your folds.

You squirmed and writhed as she took her time circling around your clit, giving it a playful flick now and then and finally latching her lips around it and sucking as she lapped at you.

"Oh fuck," you panted as you rolled your hips up into her mouth. She loved your reactions and she grinned into you, sufficiently pleased with herself.

Soon your moans grew louder and you clutched the sheets tightly in your hands. Again, Jessie smiled as she felt your legs tighten and flex around her head.

"Oh God, Jess," you breathed as your hips bucked into her face. "I'm so close." Your hands now clawed blindly at the bed.

Jessie stayed steady, ignoring how her cock absolutely throbbed with need. Every movement and sound you made, along with the way you tasted on her tongue, was driving her mad. She hated to think what state she'd be in if you hadn't given her some reprieve earlier.

Your moans reached a fever pitch and your hips began to jerk against her until you froze mid-grind, your back arching off of the bed and juices flooded Jessie's mouth. She stayed with you, wordlessly coaching you through your orgasm until you hips fell back to the bed and gave a few lingering, stuttering movements. Finally, a heavy, satisfied moan left your lips as your body relaxed and Jessie pulled back.

"Oh my God," you breathed and she smirked as you brought your hands up to your face, eventually draping one arm across your eyes and stretched one leg out as you began to recover.

Jessie watched you coming down, clearly content with her performance. She was filled with satisfaction and pride, but it also sparked a need in her to make you feel that way again. She wanted you to reach that high once more, to feel as amazing as you could, and she wanted to be the one to do it.

Old habits died hard.

This is what she did. As the years went on, one way to defend herself was to make certain there was nothing to make fun of. To be good - damn good. To know exactly what to do and how. But she learned this also had drawbacks of its own. It didn’t change how those girls felt about her. She just went from the butt of a joke to a late night call and little more.

So in time, she more or less stopped altogether. Going into this, she was worried about how rusty she was, but those concerns were quelled by the orgasm she just gave you. And now, she wanted more and to give you more.

She kissed the inside of your thigh. Soft and feathery at first before kissing her way inward again.

She gave you a tentative lick, cleaning up the juices that remained on your lips and your body twitched, an immediate whimper escaping your mouth.

Yes, she definitely wanted more.

She took her time, easing you back towards ecstasy as she gently licked and sucked at you until you were rocking up into her mouth yet again.

This time, as your hands began to grip the sheets once more she reciprocated your earlier move and grasped one of your hands and placed it on the back of her head to give you free rein. She smiled as your fingers immediately dug into her crown and gripped her hair tightly.

You didn't change her pace, and instead simply gripped her tightly as if to anchor yourself as she brought you to another high.

At one point, she pushed your legs back to give her greater access. The shift in position elicited a wanton moan from you and you palmed helplessly at your face with your free hand as she sent mounting waves of pleasure through you.

By the time your moans heightened again, Jessie starting to identify the signs of your nearing release, she had to consciously stop from grinding herself against the mattress for some hint of release.

You gripped her hair so tightly as you came that she winced, but she ducked her head to ensure you didn't see. Not that she felt you could notice even if you tried with how your cries filled the room and you writhed against the bed. Besides, she considered it a compliment.

Your body shuddered as she slowed her licks in time with the way your breathing began to calm.

"Oh-oh my God," you panted as you lay there dazed, eyes closed, the movement of your breasts catching Jessie's eyes as you worked to catch your breath. "I need a moment."

Jessie bit back a chuckle, very pleased with herself and simply laid a soft kiss on your thigh before wiping her face and moving up to lay next to you.

"Holy shit," you said when you finally managed to open your eyes and peek over at her.

"So...was it okay?" Jessie asked. She very likely knew the answer, but, you'd asked earlier and she wanted to reciprocate. And if there was something else you wanted, she wanted to know that too.

You shot her a withering stare.

"Come on," you said. Her expression must've betrayed her, because you next comment was, "Oh yeah. I see your little smirk. You know damn well how much I enjoyed that." You gave a light huff of a laugh. "And if not, I'm sure the cum on the sheets or whatever was surely dripping down your chin should've been a telltale sign."

Jessie blushed at your language and candor, but she liked it.

"Well, you asked me the same earlier and I thought it was pretty obvious how much I liked it," she countered.

You chuckled, closing your eyes once more for a couple of seconds before responding. "Well, I guess I didn't know how to read your reactions throughout. I'll learn though. My reactions? My neighbours could tell you how good you were. Which will be totally embarrassing if I run into them anytime soon, but, worth it."

Jessie tried to tamp down her smile to avoid appearing smug, but felt her face growing warmer despite whatever satisfaction she felt.

"I see you're ready to go again," you said with a lilt in your voice and a purposeful glance down at Jessie's erection.

"Oh." Jessie's face burned hotter. She shook her head mildly. "That's fine. It'll go away eventually. Or whatever."

Jessie's curiosity piqued as you studied her face for a couple of moments, before suddenly she found herself on her back with you straddling her waist.

"I can help, you know," you said lightly with a gleam in your eye. You pushed your hips back, making brief, teasing contact with her length to prove your point.

"Oh," Jessie voiced as a rush of anxiety went through her while she inadvertently dug her fingers into your hips. You took it as affirmation as rocked against her once more. If the fleeting contact with her cock wasn't enough, having your hot, wet heat rub against her abs was sending her into a daze.

"I, um," she stammered as she tried to think through the pleasure and distraction of you rocking against her body, "I didn't bring any condoms with me," she said as she stared at your waist, mesmerized by how your hips were moving. She forced herself to look you in the eye. "I had no idea this was happening tonight."

You stilled entirely and a puzzled expression slowly crossed your features.

"Condoms?" You asked. Soon you nodded as though reasoning with yourself. "For like, safety. Staying clean - all that, right?" You rolled your eyes at yourself. "Obviously. That makes total sense."

"Well...yeah," Jessie shrugged. As she started to elaborate, she found her gaze flitting away, newfound nervousness rising through her chest. "But, probably the bigger thing is, you know, birth control and all that."

"What?" You asked, clearly surprised. Jessie felt herself growing meek, but she resisted as best she could.

"Yeah," she responded, trying to sound nonchalant. "That aspect is...anatomically accurate as well."

She could practically see your mind reeling. She subconsciously began kneading your hips in some attempt to calm you.

"So, um. Yeah," she said, unable to find the right words.

She watched you carefully, vigilantly looking for any hint of what you were thinking or how you might react. The seconds passed and her heart pounded louder and louder in her ears. She looked at you with a concerned frown.

"Say something, please."

A/N: It was FAR too long to fit into one chapter. I'm working on the next part - if you've read my stuff, you know where I'm leaning with this condom situation lol - let me know your thoughts; I can still go a couple of different directions.

Tag requests: @multifandomlesbianic @marvelwomen-simp @kathleenmikaelson

#jessie fleming #jessie fleming x reader #woso x reader #woso imagine #canwnt x reader #smut fic #woso smut #g!p

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