first time ─ jessie fleming x reader
in which: you and jessie take the next step in your relationship
warnings: smut (18+), g!p sex, oral (r receiving), penetrative sex (r receiving), dirty talk
wc: 4.6K, used a couple prompts from @delusionisaplace!
a/n: Let's say jessie is still at chelsea here, just to make sense of the tiny bit of plot there is at the beginning of this fic, lol. also, this is... pure filth. I don't know why this was the fic that got me out of my writer's block but yeah, have it. also if the whole g!p thing is NOT your thing, then don't read it! the warning is there for a reason. it's my first time writing this dynamic, so I'm sorry if it's kinda shitty. as usual, not proofread. sorry for any mistakes.
You kept rolling your hips down into Jessie's lap, another whine escaping your lips as you could feel her growing cock pressing into you with every brush against her hips. Your head was buried in your girlfriend's neck, lips parted and softly panting as you fisted your hands in her hair. "Fuck, Jess, if we don't stop now we are not making it in time to Leah's," you said, with the last remaining bit of dignity lingering inside of you.
Leah had invited some of her Arsenal teammates and their plus ones over for a big dinner at her place, to which you'd eagerly agreed when you first got the invitation. After a bit of convincing, you'd managed to get Jessie on board too – the self-consciousness about being the only Chelsea player in a predominantly Arsenal-covered living room quickly washed away with the prospect of a little mingling with old and new friends in sight.
Right now, though, a dinner with friends was the last thing on Jessie's mind. Admittedly, it wasn't really at the front of yours either. Your every thought now laced with pleasure, you tried your absolute hardest to keep a little bit of self-control before you lost yourself completely in Jessie's touch, in the feeling of her burgeoning hard-on pressing against your awaiting core.
"Yeah", Jessie breathed against you, forcing her eyes closed because your blissed out face was pushing her towards an edge she didn't want to be at yet, "yeah, you're right," she said, but made no move to stop or get up, if anything she pushed your hips harder against hers.
You lifted your head from her neck in a vain attempt to regain some control, but seeing Jessie's baby hairs sticking against her forehead that was covered in a sheen layer of sweat, a frown etched upon her face as she concentrated on being good for you with her eyes closed, there wasn't a single cell in your body that wanted anything else but this.
"Fuck it," you mumbled underneath your breath, "we'll make up an excuse later," it was the last bit of encouragement that Jessie needed, already lifting you up from the couch before you even got a chance at finishing your sentence. You squealed as she lifted you up and you put your legs around her waist, hanging onto her while she manoeuvred the two of you up the stairs and into her bedroom.
You and Jessie hadn't gone much further than a few heated make-out sessions on either of your couches yet. The relationship was fairly new and as much as you were completely infatuated by her, you'd promised each other to take it slow. But the past week, anytime Jessie did anything but breathe near you, you wanted nothing more than to jump her bones – you were ovulating, in your defense. So when you rang her doorbell that night, having gotten ready in your own apartment for Leah's dinner, and Jessie opened the door in a white button-up shirt that was tucked into a pair of black slacks that perfectly hugged her muscular thighs, you knew you wouldn't have the self control to restrain yourself tonight.
Jessie's button-up shirt and your dress long forgotten – not without the promise that you'd wear it again for her – your girlfriend placed you on the bed and crawled on top of you. "You drive me crazy, baby, honestly. I need you so bad," she said, pulling a moan from you. Jessie had always been – and still was – quite reserved. She had her moments with you where she would turn into herself, but those were rare. With other people, though, it was rare that they would see Jessie let loose. So when you discovered that Jessie was quite the dirty talker in bed, it's safe to say you more than were surprised. Pleasantly surprised, that's for sure.
Your Canadian peppered kisses all over your face, your cheek and jawline until she reached the base of your neck, where she let her wet tongue glide over the sensitive skin all the way back up until she reached your ear, where she softly nipped on your earlobe. All your senses were overwhelmed with Jessie – you saw, heard, felt and smelled nothing but her. And you loved it.
A couple moments later Jessie still found her face nuzzled into your neck, sucking, kissing and licking all over the skin there. And as much as you liked it and it felt good, you were starting to feel quite the throb between your legs – and you wanted, needed, her to do something about it.
"Jess", you said breathily, to which she lifted her head. "Please, I need you," you continued, to which a small smirk tugged at her lips. "What do you need, love?" she asked. You groaned and threw your head back. "Your mouth, your fingers, your dick. Anything, Jess." A shiver rolled down Jessie's spine as you finished talking, purely due to the excitement of what was about to come.
The Canadian wasn't particularly someone for one-night stands, she simply loved too hard to be able to fuck someone without catching any sorts of feelings for them. That, combined with her busy schedule, meant she hadn't dated in a good while. Meaning that, for the last couple of years, the only relief Jessie could give herself was the pumping of her own hand. Merely the thought of her length being enveloped in your warm tunnel had her almost bursting.
She slowly made her way down, pressing open-mouthed kisses all over your body. You could feel her sucking your skin and marking you up, but you didn't have an ounce of self-control left in your body anymore to tell her to stop. She reached your underwear and teased you by dipping one finger underneath the waistband, but not trailing further.
"Can I take this off?" she asked softly, earning a nod from you. "I'm gonna need words, beautiful," she said, when you didn't speak up further. "I know you can do that for me," she continued, which caused you to blush. "Yeah-, yeah, that's okay. Only if you undress too," you replied. Jessie glanced down at her own body and noticed that she was still half-dressed, her lower body still covered. She stood up quickly and kicked off her trousers and socks – her swollen cock a little less restrained which caused her to sigh a breath of relief – before settling her body between your legs again.
A smile tugged at the corners of her lips when she pulled your underwear down your legs, a string of your arousal connected to the garment. "You're soaked baby, god, you're so hot," Jessie mumbled.
Your girlfriend skipped the teasing and torturing and delved straight in, your scent way too intoxicating for the Canadian to wait any longer to taste you. Jessie licked a long, slow stripe from your entrance up to your clit, gathering your arousal in her mouth and spreading it all over your lips. You couldn't hold back the moan that escaped your lips upon the feeling of Jessie's warm tongue against your heat.
"Fuck, Jess, that's so good," you said breathlessly. You had been uncertain and insecure about this moment for a long time, but you couldn't have wished for a better time to take the next step in your relationship. You were pulled out of your thoughts when Jessie took your sensitive nub in her mouth and teasingly flicked her tongue across it, earning a grunt from you. You tangled your hands in her curls and gave a sharp tug when you felt her teeth graze your clit, the sting subsiding quickly when she started sucking on it again.
It wasn't long before you started to feel a tightening sensation starting to bubble up inside of you. Jessie's tongue was working wonders against your core and you were seriously questioning why it had taken the two of you so long to get to this point. The room was filled with the sounds of your moans and the squelching of your drenched core, riling you up further – if that was even possible. Jessie hadn't even used her fingers yet and she had you teetering on the edge.
"Jess," you breathed, trying to form a coherent sentence while the Canadian was sucking and licking on you at a relentless pace. "I'm close, baby, you're gonna make me cum," you continued. Jessie hummed into your pussy, not relenting by any means. In response, she squeezed your thighs that were resting on her shoulders. Your moans rose in pitch as she brought you closer and closer to your high, not letting her pace waver once you started squirming and bucking underneath her.
"Oh fuck, Jess, fuck, I'm cumming," you mustered, right before you felt the coil in your belly snap. You arched your back off the bed and threw your head back, your thighs locking around Jessie's head whose ministrations kept going. You let out a loud moan as you started to come down, your girlfriend guiding you through your orgasm and eventually releasing your lips with a pop as you started growing sensitive.
You dropped your legs from Jessie's shoulders and rested them on the mattress, trying to catch your breath from the mind-blowing orgasm you just had. "Fuck, that was good," you said, not needing to glance at Jessie to know there was a smug smirk plastered on her face. She rested her head on your thigh and pressed soft kisses, waiting for you to come down from your high.
A couple moments later you managed to catch your breath, and opened your eyes to look at her. "You're amazing", you said, a light smile tugging at your lips. You couldn't miss the small blush that crept upon your girlfriend's cheeks at your words. "Thank you, baby, I love making you feel good," she replied.
Another few moments of silence went by before you spoke up. "What about you?" you said, wanting nothing more than to return the favor but not really knowing how to approach the subject. After all, you were quite nervous, to put it lightly. You had never had sex with a dick before, and you definitely didn't know whether you were going to be any good at it – whether you would like it even. Jessie and you had talked about it countless of times, talked about what you thought you would like and not like, because the last thing she wanted was to make you uncomfortable or to hurt you in the moment.
"What about me?" Jessie quipped back, but you didn't miss the glint in her eyes. She climbed up your body and laid her head on your chest before you replied. "I want you to feel good too," you said softly, to which she let out a little chuckle. "Pleasuring you is more than enough, baby," she said, to which you rolled your eyes. "I'm not having that, Fleming. You know what I mean."
Jessie chuckled and looked up at you. "Are you sure? I know we said we'd take things slow on this regard," she asked. She was right. You had told her that you wanted to take things slow. You were more than comfortable with the Canadian but you didn't want to rush into things. You nodded, taking a deep breath before continuing the conversation. "Yeah, you're right. I did say that. But this feels good. It feels right," you said, tucking a strand of hair behind Jessie's ear. "So if it feels right for you too, I'm more than willing to try some things."
"It feels more than right, you know that, but I just want to make sure that you feel okay with all of this. I'd never want to rush you into doing things you'd rather not," Jessie said softly, tracing patterns on your bare chest. You pressed a kiss against her crown and took her chin between your thumb and index finger, tilting her head up towards you. You gave her an appreciative look before you spoke. "You're perfect, Jess. I love how mindful you are being, but I promise that I'm okay with this. I'd tell you if I wasn't."
Jessie gave you a nod and a warm smile before rolling off your body and sitting up, seemingly a bit nervous about her next step. She looked around hesitantly around the room. "You okay, Jess?" you inquired, now sitting up against the headboard. "Y-yeah, I was just," she breathed, voice slightly wavering. You frowned, wondering what had gotten Jessie visibly upset. "We're on the same page, right?" she asked. You cocked an eyebrow at your girlfriend. "I think so, yeah? I don't know what you mean, but I don't see how we couldn't be."
Jessie seemed to relax a little at your words. "Is it okay if I grab a condom, then?" you chuckled at her question, shaking her head in disbelief before speaking up again. "Of course, Jess, why are you so nervous about that?"
"I don't know, we hadn't verbally agreed on what we wanted next and I didn't want to just grab a condom if I wasn't sure that this is what you wanted," she explained. A small smile tugged at your lips as you leant in and cupped her cheek, pressing a tender kiss against her lips before you replied. "You're adorable. Thank you for checking in. But yeah I can confirm that this," you gestured towards Jessie's hand that was resting on the nightstand and then down towards her still-hardened member, "is what I want."
Jessie's cheeks turned a deeper shade of red and she cast her gaze away from yours, slightly embarrassed at her own uncertainty. Nonetheless, she opened her nightstand and rummaged around until she found an unopened pack of condoms. "It's been ages since I've used these, but I'm pretty sure they're not expired yet," Jessie said with a toothy grin on her face. "Well, we should make sure to get some new ones then next time we're grocery shopping," you said, a teasing smile adorning your lips as you spoke to your girlfriend. "Big plans huh?" she inquired, before bringing the condom packet to her mouth and ripping it open.
You watched on in awe as Jessie slipped the top of the condom over her tip and rolled the rest down her length. It was safe to say that Jessie's member was above average length. It was quite wide and thick. On another day, if your heart wasn't pounding in your chest, you would've probably made a comment about it. You had never had sex with a dick before, so it was safe to say that you were quite nervous about taking her, if you were going to be able to at all.
Jessie made her way back over to you and spread your legs again, settling her body in between yours as she sat back on her heels. She caressed your thighs gently and relented from doing anything, letting you set the pace for now. She could tell you were nervous. She offered you a warm, small smile before speaking up. "I'll be gentle with you, I promise. I wouldn't want to hurt you, ever," you nodded and gave your girlfriend an appreciative nod. She knew you'd never had penetrative sex with a dick before. She also knew you were nervous, so it meant a lot to you that she was reassuring you like this.
"I know. I trust you," you said, before you scooted a little closer to her, trying to wordlessly let her know that you were ready. Jessie got the hint and pushed her body towards you, hovering over you on her knees as she adjusted so her dick was lining up with your entrance. You watched on between your bodies in awe as Jessie grabbed her length and softly pushed it up and down between your folds, repeatedly bumping against your clit. You couldn't suppress the soft whimpers that escaped your lips. A couple moments later, Jessie looked up to you and searched your eyes for any signs of uncertainty. She wanted to make sure that you were fully comfortable before she pushed further. You grabbed her hand that was situated on your hip, keeping herself up, and gave it a tight squeeze.
Jessie took it as encouragement and lined herself up with your entrance, ever so slowly inching forward. She kept her eyes trained on your face as she entered you, making sure she didn't miss any signs of discomfort as she stretched you out. You closed your eyes and bit your lip as you focused on the feeling of Jessie's hardened member entering you. Despite a first orgasm, you hadn't loosened much and you could feel the way she was stretching you out. A frown was etched on your face as you tried to compose your breathing. You tried your best to relax and to loosen up for her, but Jessie couldn't push further.
"Just let it happen, baby, don't think about it too much. I can feel you tightening around me," Jessie spoke up softly. You nodded wordlessly, taking a deep breath in and trying to relax further. Jessie was still on her knees between your legs, patiently stretching you out. She, too, was having a hard time at remaining composed. Not so much because of discomfort, but mainly because she lost herself in the feeling of being wrapped up in your heat. She wasn't in deep, by any means, but your warmth was enveloping her tip and she loved the feeling.
A couple minutes, a lot of trial and error and deep breaths later, Jessie's hips were finally flush against yours. It hadn't been easy, but the feeling of being filled by your girlfriend was nothing like you'd ever experienced. Jessie was hovering over you now, wanting to be close to you instead of on her knees between your legs. "Does this feel fine?" Jessie whispered in your ear, not wanting to disturb you too much while you were adjusting to her length inside of you. You nodded wordlessly, letting your nails rake over Jessie's back. "Yeah," you breathed out. "Yeah, this is okay."
A couple more moments passed before you spoke up again. "I think I'm ready for you to move," you said tentatively. Jessie lifted her head and looked at you, searching your eyes for any discomfort. "Okay," she breathed, pressing a tender kiss against your forehead. Jessie slowly pulled her hips back, pulling out of you just until she reached the tip. She moaned softly at the sensation, pushing back inside of you and filling you to the hilt. "Fuck," you whimpered, "do that again, please."
Jessie eyed you curiously and pulled back once more, making sure her tip stayed inside of you. "Like this?" she asked, earning a wordless nod from you. She grinned slightly, pushing back inside of you and letting your warm tunnel envelop her length. "You feel so tight around me, darling, you're so hot."
By now, you had comfortably adjusted to Jessie's length. Even though you could still feel her stretching you out with every thrust, most of the uncomfortable feeling was now replaced with pleasure. Jessie found a steady rhythm that felt good to both of you, pushing in and out of you while making sure you were comfortable.
The room was now filled with the sounds of your shared moans and the squelching of your core every time Jessie pushed inside of you. You were undeniably wetter than you'd ever been. Not only the feeling of being fucked by your girlfriend and being so close to each other, the thought of her filling you up again and again was doing things to you too.
Jessie's breathing became slightly ragged the longer you continued. You could feel her thrusts were becoming a little less regular and you wondered if those were the telltale signs of her growing closer to her orgasm. You wished you could say the same, though. Although it felt good, you didn't know whether this was doing it for you. You realized that you should tell Jessie, because she wouldn't forgive herself if she came and you didn't.
You pressed your hand against Jessie's chest which caused her to halt her movements, looking up at you worriedly. "I don't think it's going to work like this, Jess. This feels good, but I don't know if it's going to get me there," you said, an inevitable blush creeping up your cheeks. "I'm sorry."
Jessie shook her head and spoke adamantly. "Don't be sorry, please. We have all night, okay? No need to rush," she said, while leaning down and pressing a loving kiss against your lips before she sat back on her heels and slowly pulled herself out of you, watching on amazedly as your core tried to suck her back in. "Like what you see?" you teased, a smile tugging at your lips. "Yeah. I do, this is hot."
Jessie pulled out of you completely and took your hands in hers. "Is there anything you would like to try? Something you think might feel better?" Jessie inquired. You shrugged, dropping the eye contact and looking away from your girlfriend. You had an idea, but you were slightly embarrassed to voice it. She frowned, grabbing your chin between her thumb and index finger and tilting your head towards hers again. "It's just me, baby, please tell me what you've got on your mind."
Your already-red face turned a shade darker, another blush creeping on your cheeks as you locked eyes with her. "Do you maybe want to, uhm, try a different position?" you asked softly, uncertainty laced in your voice. Jessie chuckled lightly and smiled brightly at you. "Of course I want to try a different position, love," Jessie reassured you, giving your hands an appreciative squeeze as you looked up at her.
You didn't really know how to progress further. You could tell that Jessie expected further explanation from you, probably an insight to what position you wanted to try. You were still feeling quite apprehensive about the whole situation, but you mustered up the courage to go further. "Maybe... uhm, do you maybe want to try from the back?"
Jessie's face lit up at what you said, a smug smile tugging at the corners of her lips. "Yeah," she chuckled, "I'm more than down to try from the back," Jessie sat back a bit to give you more room to work with, you shuffling from underneath her. You rolled your body over and pushed yourself up, holding your body up on your hands and knees. Jessie moved too, positioning her body behind yours and making sure the both of you were comfortably in the middle of the mattress.
"God, I wish you could see how good you looked from this angle," Jessie whispered. Her eyes were trained on your entrance, that was clenching around nothing. Your folds were sopping wet, your arousal smeared out all over them adding to the sensations. You turned your head and looked at your girlfriend over your shoulder, chuckling as you noticed her staring at you in awe. "You're a dork, you know that?"
Jessie let out a breathy laugh and shuffled closer to you, her dick lining up with your entrance again. "I know I am, that's why you love me" she said, not wasting another second and pushing herself inside of you again. "Oh," you said, your breath hitching in your throat at the feeling of being filled again. "Oh, yeah, that's good."
"Fuck, that's so much better, Jess. Keep going, please," you whimpered, Jessie's dick hitting your sweet spot repeatedly from the renewed angle. The Canadian propped one of her legs up next to your body for extra leverage and held your waist and started pushing in and out of you at a relentless pace. Now that she knew for sure that this felt good for you, there was no longer that mental barrier.
Your moans and whimpers only spurred her on, pleasure taking over her thoughts as her dick was enveloped in your warmth. "God, you feel so good inside of me, Jess, fuck," you got out. "Nothing will ever come close to the feeling of you around my dick, baby."
You started moving your hips back against Jessie's in time with her thrusts as a long moan escaped the Canadian's throat. "Fuck, you're incredible," she said, as you were adding to her pleasure. "You look so good like this baby, taking me so well. You're doing so good.
Her praise did inexplicable things to you. To know that you were making her feel good was working wonders on your ego. You'd been worried that you weren't going to be good enough for her, especially in the beginning as you'd have to find your footing in sex with Jessie, but tonight had blown all your doubts away.
Just as before, you could tell that Jessie was growing close to a release. This time, though, you could feel the same for you. The familiar tightening sensation started boiling up again, your breaths becoming uneven and your thrusts back against Jessie losing their strength.
"Are you close, baby? You wanna cum for me?" Jessie asked, seemingly reading your mind. You groaned deeply and mustered up a response. "God, yes, please Jessie, let me cum," you begged her. "Begging already, huh? I wasn't even denying you of anything," Jessie said with a touch of degradation in her voice which turned you on further, if that was even possible.
You threw your head down against the mattress and groaned again, not having the strength to muster up a smart response. "Go ahead, baby, cum for me, cum all over my cock," the Canadian said, finishing you off with a few harsh thrusts before you bursted all over her length, spitting out moan after moan. It wasn't long before Jessie came too, rutting harshly into you as she spurted ropes of cum into her condom. She groaned as she pulled your body flush against hers, now both of you on your knees as she fucked you through both of your orgasms.
Jessie brought of you down against the mattress when you had both come down. She laid wordlessly on top of you as she tried to compose herself and regain her breath, her dick softening and falling out of your still-drenched core. She rolled over onto her back and opened her arms for you to fall into, your head resting on her chest. You listened to her heart that was rapidly pumping.
You were the first to speak up after a couple moments. "God, that was amazing. You were amazing. I love you so much," you accentuated her words with a couple tender kisses against Jessie's lips. She smiled into the kiss. "If anything, all credit goes to you. You told me you'd never had sex with a dick before, but honestly I couldn't tell. You're everything and more," Jessie said, pulling you closer to her.
After cleaning each other up, you spent the rest of the evening in comfy clothing in each other's arms, sprawled out over the bed watching some tv. "We're gonna have to find a good excuse for Leah, by the way. I checked my phone earlier and noticed a couple missed calls."
Jessie chuckled and continued rubbed soothing patterns up and down your back. "Next time we'll make sure not to miss a dinner you agreed to. I just really couldn't withstand you this time," the midfielder confessed. "Well, that makes both of us," you pressed another tender, lingering kiss against Jessie's lips. Before long, you both drifted off into a peaceful sleep.
