the last virgin
pairings: pippa fitz-amobi x g!p reader tags: smut, both their first times, a bit awkward, p in v, cunnilingus, little bit of dry humping request: omgg puppy love was so cute! would you be open to doing a first time for pip x g!p reader as well
MASTERLIST. | WC: 6.5k
(all characters are 18+) | a/n: thank you for 1k. i forgot this was in my drafts so two posts in a day in celebration wooo
Pippa tapped her pen against her notebook, half-listening to her friends and half-watching the clock drag itself towards the end of your lesson. Her mind wandered, as it often did lately, to you—across the hall in Mr. Cartwright’s English Lit class.
The thought of you was a small comfort: your half-smile when you caught her staring, the warmth of your hand brushing hers under the table, the quiet kind of love that had bloomed, slow and sweet, over the past seven months.
But right now, Pippa was stuck at her usual table in the lunch hall, cornered by the very loud, very nosy trio of Cara, Lauren, and Connor.
Cara leaned in first, eyes sparkling with mischief. “So. How’s you-know-who?”
Pippa raised a brow. “You mean my actual partner? They’re fine.”
Lauren smirked. “No, no, we mean—how are you two doing. Like… relationship-wise.”
Connor chimed in with a low whistle. “Come on, Pippa. Seven months? That’s like… forever in teenage years.”
Pippa rolled her eyes, flipping a page in her notes. “Yeah? And what’s your longest relationship again, Connor? Three business days?”
Cara grinned, unbothered. “Okay, but seriously. Have you two done it yet?”
The question landed like a grenade.
Pippa’s pen paused mid-scribble. She glanced up, only to find all three of them staring at her with varying degrees of interest and horror. “What?”
“You heard me,” Cara said, leaning back in her chair. “Have you guys had sex?”
Pippa opened her mouth—maybe to lie, maybe to deflect, she wasn’t sure—but her brain betrayed her. A beat too long passed.
Lauren’s jaw dropped. “Oh my god. You haven’t, have you?”
Pippa flushed. “It’s none of your business,” she muttered, which, of course, only made things worse.
“Oh my god,” Connor said again, eyes wide in genuine disbelief. “You’re telling me you—Pippa Fitz-Amobi—haven’t gone all the way?”
Cara’s eyes widened now. “Wait… Are you still a virgin?”
Pippa’s stomach dropped.
She should’ve said no. Or at least laughed it off. But instead, she hesitated just a second too long again.
And that’s all it took.
Lauren threw her hands up. “Shut up! No way! Pippa is the last virgin in our group?! That’s… wild.”
Connor looked equal parts stunned and impressed. “I mean, nothing wrong with it, but—wow. Honestly didn’t expect that from you.”
“It’s not like I planned it,” Pippa snapped, sharper than she intended.
Her cheeks burned. She hated this. The pressure. The sudden vulnerability. She wasn’t ashamed of it—not really. But having it dragged into the daylight, turned into some sort of headline among her friends? That was a different story.
Especially because you had no idea any of this was happening. You were still in class, probably hunched over a book, taking notes in that neat way you always did. Blissfully unaware that your girlfriend had just accidentally outed herself as the last virgin standing in her friend group.
And now, apparently, it was a thing.
Pippa barely had time to recover from the verbal ambush before she saw you crossing the lunch hall.
You spotted her instantly—your face lighting up like it always did when you saw her, that easy kind of smile that made Pippa feel like she could breathe again. You slid into the seat beside her, nudging your knee against hers without a second thought.
“Hey,” you said softly, like she was your favourite part of the day. And she was.
“Hey,” Pippa echoed, forcing a smile, trying not to look like she was mid-existential crisis.
But then—
“You know,” Connor said, dragging out the words like a threat, “we were just talking about you.”
“Oh god,” you laughed. “Should I be worried?”
“Always,” Lauren deadpanned.
Pippa shot her a look that said don’t.
Too late.
“So,” Cara jumped in, all sugary sweetness and barely hidden nosiness. “Are you a virgin too?”
The table froze. Pippa’s stomach dropped again. Her eyes snapped to yours, wide in a please don’t answer sort of way.
But you?
You blinked, paused for half a second… then shrugged. “Yeah.”
The word landed with an easy confidence, like you’d just said you preferred apple juice over orange. You didn’t flinch, didn’t stumble. You just said it and took a bite of your breakfast bar like they’d asked what time your class ended.
Pippa stared at you.
Connor nearly dropped his drink. “Wait, what?”
Lauren leaned forward. “You are?”
You raised a brow. “Is that… surprising?”
“I just thought—” Cara trailed off, eyes flicking between you and Pippa like she was trying to solve a mystery.
Pippa expected you to get defensive. Maybe embarrassed. Maybe annoyed.
But you just kept chewing.
“I mean,” you said with a shrug, “I’m not in a rush. And I’m not exactly gonna do it just to say I have. Why? Are you all holding weekly orgies or something?”
Connor choked on his smoothie. Lauren snorted. Cara looked like she was both horrified and intrigued.
Pippa bit her lip, trying so hard not to laugh.
You turned to her then, finally catching the odd look in her eyes. “You okay?”
She hesitated. “Uh—yeah. Yeah, I’m fine.”
Because somehow, you’d just walked straight into the lion’s den, dropped a bombshell, and left the mess behind like it didn’t even faze you. And maybe it didn’t.
And Pippa couldn’t decide if she felt incredibly relieved… or incredibly exposed.
But the warmth in your gaze, the quiet steadiness in your voice—it reminded her why she liked you in the first place.
You didn’t care what anyone else thought. About her. About sex. About any of it.
And maybe, if she let herself admit it, that was exactly what she needed right now.
//
Pippa had solved two murders, cracked countless conspiracies, and outwitted grown adults twice her age. She was smart.
Which made her current situation—sweating nervously in the ‘intimate health’ aisle at Boots—almost funny.
Almost.
She glanced left, then right, then left again. Her phone buzzed in her back pocket, but she ignored it. Her notes app was open, a bulleted list that had somehow ballooned from ‘do some research’ to full-blown operation planning.
SEX MISSION: PREP
• condoms (regular… maybe try latex-free?)
• lube (water-based vs. silicone-based — TBD)
• shave???
• breath mints (not technically required but still)
• make a playlist?? idk
She stared down at the selection in front of her. Rows and rows of condoms, some labeled ‘ultra thin,’ others ‘ribbed for pleasure.’
Why is this so complicated? she thought.
She picked the least threatening box—plain, unbranded, regular—and shoved it into the basket. Then she grabbed a small bottle of lube, paused, and threw a second brand in too. Just in case.
Back home, she dumped the bag on her bed and immediately locked her bedroom door.
The box of condoms stared at her.
She stared back.
Then, in true Pippa fashion, she opened her laptop and began researching.
Not porn—God no—but articles. Scientific ones. Advice columns. Blogs with names like ‘Your First Time: What No One Tells You’ and ‘How To Not Freak Out Even If You Feel Like You’re Going To Die (Emotionally).’
She read every word. Twice. She watched a YouTube video by a sex educator explaining the difference between different lubes and why communication was more important than performance. She took notes.
Actual notes.
She even bookmarked one article titled ‘Sex Is Not A Race’ because, honestly, she needed to hear that.
But the deeper she dove into her self-assigned research, the more one unsettling thought kept sneaking into her brain:
What if you didn’t even care about any of this yet? What if she was the only one obsessing?
She chewed on her thumbnail, glancing over at her drawer where she’d hidden the Boots bag like contraband. You hadn’t brought it up again—not once since that lunch table interrogation. And you definitely hadn’t acted like you were in any kind of rush.
If anything, you seemed… fine.
Happy.
Still holding her hand like she was everything you wanted.
Pippa fell back onto her bed, letting her notes flutter to the floor.
She’d cracked unsolvable crimes.
So why did this feel harder?
//
You were sprawled across your bed, legs tangled in the blanket, iPad balanced against your knees, and a singular goal in mind: Survive the haunted asylum level in Roblox.
The game had lured you in with cute graphics and laughably basic jump scares. But now?
Now, some demon-possessed nurse had just sprinted full-speed at your character from a shadowy corridor, and you—entirely unprepared—screamed:
“FUCK!”
A beat of silence followed.
Then:
“Language!” your mother shouted from downstairs.
You winced. “Sorry!”
Another jumpscare popped out, and this time you just threw the iPad on the bed with a muffled, “Nope.”
As your heart rate tried to settle, your phone buzzed.
Pip 🖤: hey do you wanna sleep over tonight?
You blinked.
It wasn’t unusual—Pippa liked having you over. Her room was always tidier than yours, smelled faintly of expensive shampoo, and her bed had the softest sheets known to mankind. But something about the way she texted this time felt… different.
Short. Clipped.
Not a meme. No emoji spam. No ‘pls bring snacks or I’ll die.’
You stared at the screen for a second longer, then tapped back:
You: sure. everything okay?
It only took a second for her reply to come in.
Pip 🖤: yeah! just want you here x
You chewed your lip a bit, suspicious, but your brain was already shifting to logistics. You could bring your charger, toothbrush, maybe that hoodie she liked you in. And if she wanted cuddles—or was just feeling clingy—you were happy to show up and deliver.
Your iPad dinged again—your Roblox character had apparently died without you. Tragic.
You tossed it aside and flopped dramatically back onto the pillows.
Still, you couldn’t shake the feeling there was something else going on. Pippa didn’t usually ask for you this abruptly. She was more of a planner. A ‘what are you doing Friday after 6:30pm precisely’ kind of girlfriend.
But she’d said she just wanted you there.
And if there was one thing you were always down to do… it was show up for her.
You slid off the bed with a grunt, snatched your charger from where it dangled near the outlet, and stuffed it into your hoodie pocket. No need for a bag—you weren’t fancy. Toothbrush could live at Pippa’s now. Your toothbrush knew Pippa’s sink.
Grabbing your coat from the back of your desk chair, you slid it on one arm at a time and slipped your feet into your Crocs—beat-up, and in sport mode. The ultimate statement shoe for a romantic rendezvous.
You padded into the kitchen, where your mum was halfway through pouring boiling water into a mug.
“I’m staying over at Pip’s,” you said casually, grabbing a banana off the counter like it was a boarding pass.
She didn’t look up. “You did your laundry?”
“Mostly,” you lied.
“Don’t be weird at her house. And tell her mum I said hi this time, not just a grunt from behind your phone.”
“Love you,” you called, already backing out the door.
She sighed loudly. “Text me when you get there, you little gremlin.”
You gave a thumbs up through the doorway and shut it behind you.
The air was cool—summer winding down, the sky bruised with early evening clouds. You shoved your hands into your coat pockets, humming some stupid song stuck in your head from TikTok, and started the short walk to Pippa’s.
As always, your pace picked up the closer you got to her street.
Something about her always pulled at you—like your body knew exactly where to go. You’d memorised the cracks in her pavement and the exact creak of her garden gate.
By the time her house came into view, the nerves started to kick in a little. Just a little. Because as much as you’d tried to brush it off… you had felt something weird in her texts.
Still, you knocked twice and waited.
When she opened the door, she was barefoot, wearing that oversized hoodie she stole from you three months ago and never returned, even though she pretended she ‘forgot it was yours.’
Her hair was messy in a way that suggested she’d been lying on her bed overthinking everything. Which, in Pippa language, was saying a lot.
You gave her a crooked smile. “Hey, trouble.”
She stepped back to let you in. “Hey.”
You could feel it. Something in her energy.
Not bad. Just… tight. Like she was bracing for something.
“Everything okay?” you asked, slipping your shoes off by the door.
Pippa hesitated, then nodded quickly. “Yeah. I’m glad you’re here.”
And as you followed her upstairs, hoodie sleeves pulled over your hands and your brain blissfully unaware of the condoms hidden in her drawer, you thought:
Huh. She’s being weird.
:/
Ratatouille was halfway through, and you were in it. Full focus. Zero distractions.
You were lying on your side, head propped on one hand, eyes glued to the laptop screen resting on the bed between you and Pippa. Your free hand reached occasionally into the bowl of popcorn she’d set on the nightstand, a mechanical rhythm. You didn’t even look when you grabbed a piece—you trusted the popcorn. And you trusted Pippa.
What you didn’t realize was that Pippa had barely watched the last twenty minutes of the film.
She was lying on her back, slightly angled toward you, eyes drifting between the screen and the curve of your jaw. Her arm brushed yours—casual at first. Then stayed there. Then pressed more deliberately.
You didn’t move. Maybe you didn’t even notice.
Your face lit up at the scene where Remy seasons the soup. “Okay but this scene is cinema.”
Pippa didn’t respond. Her hand, now resting near your thigh, twitched.
Her heart was in her throat.
It wasn’t like she planned anything. But something about having you in her bed, warm and close, so trusting—so comfortable—it lit a match inside her. All her anxiety, all her prep, all her overthinking had culminated in this moment where you were lying right there, unbothered, like the idea of sex hadn’t even crossed your mind.
Which, honestly, maybe it hadn’t.
She shifted slightly, her fingers brushing the side of your leg. You still didn’t react. Her eyes scanned your face—soft, focused, lit by the laptop glow—and for a second she wondered if this was the right time at all.
But then… your pinkie curled around hers. Absentminded. Automatic.
And somehow, that broke her.
She turned her face toward you. “Hey.”
You hummed in acknowledgment, still watching the screen.
“Can I ask you something?”
You hit pause without hesitation and turned to face her. “Of course.”
Pippa hesitated. Her voice was a little quieter now. “Do you… ever think about us doing more? Like… stuff.”
You tilted your head, processing. “Sex stuff?”
Her ears turned red. “Yeah. That.”
You gave a soft smile, one of those quiet ones that always made her chest ache a little. “Sometimes,” you said honestly. “But I figured we were just taking it slow.”
Pippa blinked. “That doesn’t bother you?”
You shrugged. “Not really. I like slow. You never made me feel rushed or pressured, so I figured I wouldn’t do that to you either.”
There was a pause. Then you added, more gently, “Have you been thinking about it?”
She nodded, almost imperceptibly. “Kind of obsessively.”
You grinned. “You mean like, made a whole list about it obsessively?”
Her silence was loud.
“…Wait,” you laughed, sitting up slightly, “you made a list?”
Pippa groaned and covered her face with both hands. “I did research. I needed to feel like I wasn’t going to completely ruin it.”
You gently pried one hand from her face, eyes still amused but soft. “Pip. You wouldn’t ruin anything. You’re the most prepared person I know. I’d be surprised if you didn’t create a sex spreadsheet.”
“I didn’t,” she said, defensively. “…It’s a bullet list.”
You snorted, then leaned in and kissed her cheek.
“I like being close to you,” you murmured. “Even if it’s just this. But if you’re ready… I’m here.”
Pippa stared at you, wide-eyed and stunned by how calm you were. How easy you made everything feel.
Her fingers intertwined with yours again—tighter this time.
“…Would it be weird if I kissed you right now?” she asked, suddenly breathless.
You smirked. “We’re literally in your bed watching a movie about a rat chef. Nothing you do right now can make this weirder.”
She laughed—and leaned in.
And this time, the kiss wasn’t just sweet.
It was new.
It was her deciding.
//
Looking at Pippa, you saw the determination in her gaze—dilated pupils and flushed cheeks. You felt a flicker of nerves, but mostly, you felt a profound sense of love and acceptance.
"Hey," you murmured, reaching up to tuck a strand of hair behind her ear, "are you sure about this? Because if this isn't what you want, we don't have to-"
But Pippa cut you off before you could finish, leaning in to press her forehead to yours. Her voice was steady, almost fierce. "I'm sure. I want this. I want you, you idiot."
It made your heart clench. You swallowed hard. "Okay," you whispered. "I want you too."
Pippa's lips curled into a smile against your cheek. You felt her fingers curl into the hem of your hoodie, tugging lightly. Then, she leaned back and rolled onto her knees, reaching into her bedside drawer.
Your brows shot up as she pulled out a carrier bag, setting it on the bed between you both. Peeking out was a strip of condoms and a bottle of lube.
She looked up at you, suddenly shy. "I, um. I got some stuff. I mean, I didn't know if you had any, so I just, um..." She trailed off, biting her lip.
You blinked, taking it in. Then a slow smile spread across your face. "You've thought this through."
Pippa made a face. "Shut up. I just wanted to be prepared." She paused, then added softly, "For us."
You glanced between the hopeful, anxious look on Pippa's face and the bag of sex supplies on the bed, then down at your own jean-clad crotch. You smirked, shaking your head. "I mean, I'm no genius, but I'm pretty sure the key part of this equation is that I need to be hard for it to work."
Pippa blinked, then followed your gaze downwards before her eyes widened in understanding. A deep blush crept into her cheeks, but she held your gaze steadily. "Oh. Right. Of course."
She bit her lip, then reached out to place a tentative hand on your thigh, her fingers brushing against the inseam of your jeans. "So, um... how do we...?" She trailed off, suddenly unsure.
You shrugged, playing it casual even as your heart raced. "I mean, I think it's supposed to just... happen? When you're aroused?"
Pippa nodded slowly, her hand still resting on your thigh. "Right. Aroused." She cleared her throat. "So, um... do you want me to...?"
She let the question hang in the air, her eyes searching yours, a hint of nervousness flickering behind the determination in her gaze. Her fingers curled into the fabric of your jeans, not quite squeezing, but not quite letting go either.
You started to say, "It's okay, you don't have to-" but Pippa cut you off, her eyes flashing with a sudden intensity.
"No, I want to," she insisted, her voice low and steady. "I want to make this good for you. I want to learn what you like."
She slid her hand slowly up your thigh, her fingers brushing against the growing bulge in your jeans. She bit her lip, looking up at you with a mix of nerves and determination.
"Show me," she breathed. "Tell me what feels good. I'll learn, I promise."
Her touch was tentative but eager, her gaze locked onto yours, waiting for your guidance. A soft blush still colored her cheeks, but her chin was lifted, her jaw set. She was ready. Ready to learn. Ready to make this perfect for you.
You smiled softly at Pippa, your voice gentle as you explained, "It usually takes a little while for me to get fully hard. Like, a minute or two. And I usually just rub or stroke it to help it along."
Pippa listened intently, her hand still resting on the growing bulge in your jeans. She nodded slowly, absorbing the information. Then, hesitantly, she started to move her hand, rubbing you through the denim of your jeans.
"Is this okay?" she asked softly, her eyes searching yours for approval. Her touch was gentle, almost tentative, but her gaze was focused and eager to learn.
You let out a soft exhale, your head falling back slightly as you felt her hand move over you. "Yeah, just like that," you murmurs. "Nice and slow."
Pippa took a deep breath and kept going, her hand sliding along the length of you, feeling you start to harden under her touch. She bit her lip, watching your face intently for any sign of whether she was doing this right.
You smiled shyly at Pippa, rubbing your half-hard bulge through your jeans. "There's, um, a thing I've seen in porn videos..." you started, a blush rising to your cheeks. "It's called dry humping. I don't know if it'll work, but maybe it could help us both get more in the mood?"
Pippa blinked, then nodded slowly, understanding. "Oh. Okay." She licked her lips, her eyes flickering down to your crotch before meeting your gaze again. "How does it work?"
You shrugged. "I think you just, uh, press against each other through your clothes until you're both... you know. Really turned on."
Pippa swallowed, then swung a leg over to straddle your hips, facing you. She kept some space between your crotches, but her thighs bracketed yours, her hands coming to rest on your chest.
"Okay," she breathed, looking down at you with a mix of nerves and determination. "Like this?" She rubbed herself slowly against the bulge of your jeans, watching your face for a reaction.
You let out a shaky breath as Pippa began to slowly grind against you, the denim of your jeans creating a delicious friction. "Yeah, just like that," you murmured, your hands coming to rest on her hips, guiding her movements.
She kept a steady rhythm, her breath growing a little quicker as she felt you start to throb beneath her. Her eyes flicked between your face and where your bodies were pressed together, a newfound hunger in her gaze.
"That feels really good," you breathed, your fingers digging lightly into the soft flesh of her hips.
Pippa licked her lips, her voice soft and a little unsteady. "You're getting harder," she observed, feeling your length swell under her ministrations. "Tell me if this is okay."
You nodded, your breath hitching as Pippa kept grinding against you. Suddenly, she shifted her hips slightly, angling them in a way that pressed her clothed clit directly against your hardening length.
A soft gasp escaped her lips at the sudden jolt of pleasure, her back arching slightly. "Oh!" she breathed, her eyes widening. "That feels... wow." She bit her lip, a deep blush spreading across her cheeks as she kept rubbing against you, chasing that new sensation.
You groaned softly, your fingers tightening on her hips as you felt her heat even through the layers of fabric. "God, Pip," you breathed, your length twitching and hardening rapidly now. "This feels amazing."
She just nodded, panting softly as she kept moving against you, her eyes hazy with building arousal. "I can feel how hard you're getting," she murmured, her voice thick with desire. "It's making me... it's making me really wet."
Your heart raced as you felt the heat of your arousal growing, your length now fully hard and straining against your jeans. At Pippa's words, you gulped, a surge of lust and anticipation shooting through you.
"I think I'm ready," you breathed, your voice tight with need.
Pippa nodded, a fierce determination in her eyes. She rolled off you and onto her back, patting the bed beside her in invitation. Your jeans were uncomfortably tight now, your length aching for more contact.
You scrambled to unbutton your jeans, shoving them down your legs along with your underwear. Your cock sprang free, hard and flushed and leaking at the tip. You kicked the rest of your clothes off and turned to Pippa.
She was watching you with hooded eyes, her chest heaving slightly, a damp patch visible on the crotch of her pajama bottoms. She lifted the hem of her hoodie to reveal her bare breasts, rosy nipples hard and pebbled.
You couldn't help but stare at Pippa's bare breasts, a surge of awe and desire washing over you. "Wow, your breasts are really nice," you murmured, a crooked grin spreading across your face.
Pippa laughed, a soft flush spreading across her cheeks. "Thanks," she whispered, biting her lip. "I'm glad you think so."
You blinked out of your daze and reached for the bag, grabbing the box of condoms. With shaking fingers, you tore open the box and took out a single condom, frowning slightly at the unfamiliar texture.
"I've never actually put one on before," you admitted, looking to Pippa for guidance.
She sat up, taking the condom from your hand. "It's okay, I practiced with a banana," she said, a hint of shyness in her voice. She unrolled the condom over two fingers, demonstrating the technique she'd learned. "Here, I can help."
With deft movements, she pinched the tip of the condom to leave space for semen, then smoothed it down the length of your hard cock. It was an odd sensation, but not unpleasant. Her fingers lingered on your shaft, stroking gently.
"There," she whispered, looking up at you with a mix of pride and nervous anticipation. "How's that?"
"Smarty pants," you teased softly, shaking your head in wonder at just how prepared and thoughtful she was. You grabbed the lube, squeezing out a generous amount onto your fingers to slick up the condom.
Pippa watched, biting her lip as she wiggled out of her pajama pants and underwear. She tossed them aside, leaving her bare and exposed, and unbelievably arousing. Your eyes roamed over her naked form, taking in every curve and dip, committing it all to memory.
"Do you want to...?" she started, gesturing to the bed and biting her lip, a hint of nervousness in her voice.
Pippa nodded, her eyes widening slightly as you moved to hover over her. The heat radiating off your bare skin was intense, making her acutely aware of how cooled her own was in comparison. She swallowed back the nerves threatening to overwhelm her, determined to be brave for both of you.
You shifted your hips, aligning your now slick-covered length with her entrance. The tip nudged against her, the sensation foreign but not unwelcome. Pippa's breath caught in her throat at the contact, her body tensing slightly.
"Tell me when," you murmured softly, one hand coming up to cup her cheek, your thumb brushing over her bottom lip. "I don't want to hurt you."
Pippa's gaze locked with yours, a fierce resolve burning in the hazel-green depths. She licked her lips, tasting the salt on your thumb and nodding. "Okay," she breathed, her voice barely above a whisper. "I'm ready. Slowly."
With those words as your guide, you began to press forward, your length slowly sinking into new, tight heat. Pippa's breath hitched, her fingers digging into your shoulders as she felt you stretch her open. You paused when you met resistance, giving her a moment to adjust.
As you slowly pushed forward, a sudden wave of pleasure washed over you, causing you to let out a low moan. The sound escaped your lips before you could stop it, your hips jerking slightly at the intense sensation of Pippa's tight heat enveloping your sensitive length.
Your movements froze immediately, a deep blush spreading across your cheeks. "Shit," you muttered, embarrassed at your automatic reaction. "I'm sorry, I didn't mean to-"
But Pippa just smiled softly, stroking your cheek with her thumb, her eyes shining with understanding. "It's okay," she murmurs, her voice gentle. "That felt good for both of us."
She took a deep breath, then nodded slowly. "Keep going," she breathed. "Nice and slow."
With each inch you pushed forward, Pippa's body resisted, then yielded to the insistent pressure of your hardness. A soft gasp escaped her lips as you broke through the initial barrier, the sensation of being filled for the first time unlike anything she had ever experienced.
"Oh!" Pippa gasped, her nails digging into your shoulders as a sharp spike of pain and pleasure shot through her. She blinked up at you, her hazel eyes wide and glistening.
You froze, concern etched on your face. "Are you okay?" you asked softly, searching her expression for any sign of distress.
Pippa nodded jerkily, her breath coming in short pants as she adjusted to the new sensation of being stretched and filled. "Y-yeah," she breathed. "It just... it hurts a little. But it feels good too."
You pressed your forehead against hers, your breath mingling with her own as you paused, letting her get accustomed to the feeling of your length buried deep inside her. "We can stop if you need to," you murmured. "Whenever you're ready to keep going, just say so."
You stayed still, allowing Pippa a few moments to adjust to the new sensation of being filled. Her body gradually relaxed around you, the initial resistance giving way to a soft, pulsing heat.
"Okay," Pippa whispered finally, her voice steadier now. "You can... you can keep going. Slowly."
With her permission, you began to move again, withdrawing until just the tip remained inside her before pressing back in with a gentle thrust. You set a slow, steady rhythm, mindful of her and wanting this first time to be good for her.
Soft gasps and breathy sighs spilled from Pippa's lips with each push and pull of your hips. Her nails raked down your back as you continued to slowly make love to her, leaving faint red lines in their wake.
"Yes," she breathed, tilting her head back as you found a particularly sweet spot. "There... oh god, there..."
Your hips rocked steadily against Pippa's, the slick glide of the condom allowing you to pick up the pace. The tight clutch of her walls around your length grew slicker as she grew aroused, the combination of sensations overwhelming your senses.
Suddenly, you felt it building, the pressure coiling tight at the base of your spine. Your thrusts grew more erratic, more insistent, chasing that peak of pleasure.
"I'm going to... I'm going to come," you gasped out, your voice strangled with impending release.
Pippa's eyes flew open, wide and shocked. "Really?" she breathed, a mix of surprise and awe in her voice. Her nails dug into your shoulders as she felt your length throb inside her.
With a moan, you let go, your hips jerking as you spilled yourself into the condom. Wave after wave of pleasure crashed over you, your body shuddering and twitching with the force of your climax.
"Oh god," you groaned, collapsing against Pippa as the aftershocks slowly subsided. "That was... fuck, that was intense."
You paused, blinking away the lingering haze of your orgasm. As the fog cleared from your mind, you remembered Pippa was still waiting. You didn't want her to feel left out or unsatisfied.
Pulling out of her slowly, you felt a mix of relief and renewed determination. You settled between her thighs, nuzzling against the sensitive skin. The scent of her arousal filled your nostrils, making your spent length twitch in interest.
"Wait," you murmured, glancing up at her awkwardly. "Crap, I don't know what I'm doing. I've never really... I mean, I want to make you feel good too, but..."
You trailed off, suddenly unsure. Your inexperience in this area was glaring. But your desire to bring her pleasure was fierce. You looked up at her helplessly, hoping for guidance.
Pippa looked down at you, her hazel eyes soft and warm. She could see the awkwardness in your expression, but also the genuine desire to please her. It made her heart skip a beat.
"It's okay," she murmured softly, reaching out to cup your cheek. "I don't know exactly what I need either. But... we can figure it out together."
She shifted her thighs, parting them further to give you better access. "I think... I think it might feel good if you touch me here," she said shyly, guiding your hand to the apex of her thighs, just above where your fingers met her slick folds.
You felt her heat, her desire plain and insistent against your fingertips. "And maybe... maybe you could kiss me too?" she added, a hopeful note in her voice. "I think that might make everything feel even better."
Her other hand came up to tangle in your hair, gently urging you closer to her center. She looked down at you with trusting, almost vulnerable eyes, a faint blush colouring her cheeks.
"Just... just do what feels right," she whispered. "And don't worry about being perfect. I just want to feel good with you."
You took a deep breath and leaned in, pressing your mouth against Pippa's most intimate area. You had seen this done in porn videos, but doing it in reality proved more challenging. Your technique was a bit clumsy and unpracticed.
You started to lick broad, flat strokes over her folds, tasting her arousal on your tongue. The flavour was new and intense, making your spent length twitch with renewed interest. You focused your attentions on her clit, circling and flicking over the sensitive nub.
"Mmm, yes, like that," Pippa encouraged breathlessly, her hips starting to rock against your mouth. Her fingers tightened in your hair, holding you in place.
Emboldened by her reaction, you redoubled your efforts, suckling gently on her clit as you slid one finger inside her tight channel. Her walls clenched around the intrusion, drawing you in deeper.
You pumped your finger slowly, curling it to stroke a hidden spot deep inside her that made her cry out. Feeling bolder, you slipped in a second finger, scissoring them gently to stretch her further.
"That's it," Pippa gasped, her head thrown back, her chest heaving. "Don't stop, please don't stop..."
You felt Pippa's thighs start to tremble and quake around your head as you continued your inexperienced but enthusiastic ministrations. Emboldened by her responses, you let out a low hum against her slick flesh, the vibrations adding a new sensation.
Your fingers pumped faster, plunging in and out of her tight heat as your tongue laved over her clit. You could feel her growing more aroused by the second, her juices coating your fingers and chin.
"That's it, don't stop," Pippa keened, her voice rising in pitch. Her hips bucked erratically against your face as she chased her impending release. "I'm... I'm almost... oh god, I'm going to..."
Her words cut off into a sharp cry as her orgasm overtook her. Her walls clamped down viciously around your fingers, pulsing and fluttering as waves of pleasure crashed through her.
You could feel the heat of her release flooding your mouth and soaking your hand as Pippa shuddered and twitched through the aftershocks. The sight and taste of her climax was the most erotic thing you'd ever experienced.
Finally, panting harshly, Pippa slumped back against the bed, going boneless and sated. You lifted your head, wiping your chin with the back of your hand as you gazed up at her.
"That was... wow," she murmured, her voice hoarse and distant. "That was amazing. Thank you."
You gazed up at Pippa, a mix of hope and nervousness in your expression. You gently withdrew your hand from between her thighs, your fingers glistening with her essence.
"Did I... did I do good?" you asked softly, searching her face for any sign of satisfaction or disappointment. "Was that okay for your first time?"
You felt a swell of pride at having brought her to such a intense peak, but also a flicker of insecurity at your own inexperience. You wanted to make sure she was happy, that you hadn't somehow fallen short in your eager attempts to please her.
Pippa's eyes fluttered open, a lazy smile spreading across her face as she looked down at you. Her cheeks were flushed a soft pink, her hair mussed from the passion of the moment. She reached out to cup your cheek, her thumb brushing gently over your bottom lip.
"More than okay," she murmured, her voice low and warm. "You were amazing. I couldn't have asked for a better first time."
She tugged you up the bed, until you were curled beside her. She wrapped her arms around you, holding you close as she pressed a soft kiss to your temple.
"Thank you," she whispered. "For making this so special. I love you."
You smiled softly as Pippa held you close, murmuring "I love you" against her skin.
After a few moments of basking in the intimacy of the moment, you carefully peeled yourself away from Pippa's embrace. You felt the weight of the used condom, a tangible reminder of what you’d just shared.
"Hey, Pip?" you asked, holding up the condom and feeling a bit awkward about the next step. "Where... where am I supposed to put this thing? I don't want to just toss it somewhere, ya know?"
You glanced around the room, spotting a small wastebasket nearby. But something about throwing it away in plain sight felt a bit crude.
Pippa blinked, following your gaze to the condom. A blush crept into her cheeks as the reality of the situation sank in.
"Oh. Um..." She hesitated for a moment, then reached over to grab a tissue from a nearby box. "Here, you can wrap it in this and put it in the bin under the sink in the bathroom. I don't think either of us wants it sitting out in the open."
She smiled sheepishly, a hint of shyness in her eyes. "I guess that's one of those things they don't really teach you in school, huh?"
You nodded, taking the tissue from her and carefully wrapping the used condom inside.
"Yeah, definitely not something they covered in sex ed," you agreed with a wry grin.
