Based on The Amazing Spider-Man (2012) deleted scene. I tried to make it as canon-compliant as possible, but some alterations had to be done.
Peter stilled, his hand cupping Gwen's chin to encourage her to make eye contact, a smirk slowly spreading across his features, and his gaze flickering down to her lips momentarily before meeting her eyes again. "Your parents aren't going to see you leaving."
Gwen dragged her gaze back up towards his, the realization of what he was saying slowly dawning on her. He could tell he convinced her by the quirk in the corner of her mouth, and he slowly leaning forward to press his lips against hers only to feel her pull back, a gleam of mischief in her eyes as she pressed her finger to his lips.
He raised his eyebrow at her in silent question. "Not until you have a shower. Dating a bug boy is one thing, kissing a sewer boy is another." she reminded him, grinning softly.
Peter grinned at her boyishly, making her cheeks flame. Gwen got up to her feet, and Peter practically sprung up after her. Gwen checked the hallway to see if it was clear. Considering it was after 10 pm it was pretty dark and quiet.
Peter was able to shower, and Gwen got ready. Changing out of her nightgown and robe, and taking her hair down. She was practically giddy as she got dressed in a basic lilac mini dress, a tan-colored waistcoat, and knee-high boots. She'd never snuck out of her room before, and as scary as the idea was, she was looking forward to it.
Gwen still had reservations about dating someone with such a dangerous life. And, while a part of her was really proud of him for his efforts, another part of her was a mess of emotions over the thought of something happening to him. It was a lot to consider, having to stand on the sidelines, worrying herself day and night over his safety. But she couldn't stomach the idea of actually leaving when Peter needed her the most. That poor doofus couldn't even manage the first few weeks as Spider-Man on his own.
Peter eventually returned, dressed mostly in black, looking significantly better than when he literally crawled into her window earlier. "How's your injury?" Gwen inquired, as she packed his bag with a couple of pillows, candles and some blankets for them. She wasn't shy at all to take some initiative with their date.
"Much better now, thank you." Peter replied, suddenly feeling more nervous about their date, noting the bag she was packing. The awkward silence that followed was quickly ended when Peter's stomach growled, making Gwen giggle and Peter blush, slowly gesturing downwards to himself awkwardly.
"I missed dinner." Peter admitted quietly with an awkward chuckle. "I can make us some sandwiches?" Gwen tried, making her way back towards him, her hands hooking loosely onto his shirt.
"I have a better idea." Peter replied, not breaking eye contact with her as he shot a web at his backpack and hoisting it over his shoulders as he headed towards her window, his hand clasped firmly in hers as he opened the window to climb out. "You ready?" Peter asked, and Gwen nodded, climbing out onto the fire escape with him. He hopped up onto the railings gracefully, balancing himself by the wall, and extending his hand for Gwen's again.
Gwen clambered up less than gracefully after him, steadied easily by Peter. "I hope you're not too afraid of heights." he tried playfully, pulling her against his side firmly. Gwen wrapped her arms around his waist tightly, replying with a "Urgh." as she buried her face in the crook of his neck, Peter grinned at that, running a soothing hand down her back for a moment and kissing her hair before he extended his arm and shot a web out, dropping them a couple of stories before shooting another web out to catch them and propelling them forward.
Gwen's stomach dropped, her nerves were practically rattling as Peter web slung them through New York City. She kept her face buried against his chest for the time being and desperately tried to calm the rapid beating of her heart.
As exciting as an experience it was, Gwen was grateful when Peter finally stopped by a local take-out place, for some Chinese food. Gwen was basically clinging to the countertop as they waited for their late dinner. Peter noticed Gwen's stance, chuckling a little. "You'll get used to it after a while." Gwen replied with a playful snort. "I wasn't bitten by a genetically enhanced spider, FYI." she replied lowly, making Peter chuckle again.
"Don't worry. The place I have in mind isn't too far away." Peter continued, paying for their meal and taking their bag.
"And where that would be?" Gwen inquired, leaving hand in hand with Peter as he took them down an alley. "Can't it be a surprise?" he teased, pulling Gwen against him again as he shot another web out towards a building, yanking them upwards and web-slinging again. She felt uneasy about it still, but as he said, she was getting used to it. By now, she was able to hold her head up as she clung to him, taking in the sights of the glittering lights passing by as they soared through the city.
As promised, it wasn't a long journey, Peter stopped outside a large white clock, and Gwen let out a sigh of relief as her feet settled on the ground, staying in his embrace, glancing up at him and sighing in content. "You're onto a pretty good start so far, bug boy." she teased, smiling up at him.
He dropped his backpack to the ground, and carefully set their food down. "Well, you patched me up tonight, I wasn't going to let you make dinner after that." Peter smiled, making Gwen's grin widen.
"You're cute." Gwen commented playfully, entwining her fingers with Peter's. Neither made any effort to set their late picnic just yet or even try to take in the scenery. Peter's grip loosened in hers playfully, twirling her in her spot, making her laugh as they fell into a little dance together. "Only cute?" Peter countered, his eyes alight.
Gwen beamed up at him cheekily, hooking her arms around the back of his neck firmly. "Adorable." she continued, and Peter scoffed playfully, looking away with a 'tsk', but his hands settling on her lower back, still moving to nonexistent music.
"Are you sure you don't mean 'rugged'?" he asked with faux confidence.
Gwen shook her head assuredly, maintaining eye-contact.
Peter let out a defeated breath, trying to resist the urge to laugh, spinning her again slowly before reluctantly letting her go.
"You're mean." he teased, taking the blanket out of his backpack and laying it down. "Awww." Gwen teased, taking a seat as he set the pillows down. Gwen lit the candles for some extra ambiance, even though the skyline, moonlight and large clock already illuminated their late-night picnic. They took their coats off and laid another blanket out across them.
Gwen opened the bag of food, handing Peter his chopsticks and his container.
Peter showed off, eating with his chopsticks, and Gwen ate with a fork.
"Top of her class, and can't work chopsticks." Peter taunted, and Gwen elbowed him playfully. "Shut it, Parker."
Gwen snuggled against his side more firmly despite that, and they ate in comfortable silence, observing the view before them. Horns honked in the distance, and pretty lights flickered ahead of them across the dark purple skyline.
"Your aunt isn't expecting you?" Gwen asked, breaking the silence, Peter shook his head as he chewed his food. "I called her before I saw you." Peter began, and Gwen watched him with a bemused expression., her eyebrows raising quizzically. "You were half dead when you climbed in my window."
"I didn't want her to worry." he deadpanned before chuckling. "I told her I'd be late, trying to get some pics for the Bugle. And that I'd grab dinner before heading back, so she won't wait up tonight." Peter further explained, easing Gwen's conscience.
Checking her phone for the time before chucking it back with her coat. "Got to go to bed early tonight?" Peter asked, hoping otherwise.
It was pretty late already, and a school night. But she'd finished her assignments early, and she was in no mood to end their date.
Gwen shifted on her side to lay her head on his shoulder. "Most likely." she murmured. "But I'd rather not." Gwen said, setting the rest of her dish down as Peter ate.
Another hour would go by, and it was nearing Midnight, but the young lovers showed no interest in going home at all. Talking, laughing and sharing anecdotes about their lives.
Peter learned that Gwen had taken a year of ballet when she was younger, but dropped out to focus on biochemistry.
"I shouldn't have even told you, I'm never gonna live this down now." Gwen muttered, she was now sitting across from Peter and resting her head in her hands, shaking her head idly.
"I think it's precious. You, in your little pink-"
"Turquoise."
"Turquoise?! Outstanding!" Peter teased, laughing.
Gwen brought her gaze back up towards him, a fresh determination in her eyes. "When am I going to meet your aunt?"
"Today's the 21st? So.. Never." Peter shook his head with false sincerity. Ben only spoke to Gwen for 6 seconds, Peter couldn't imagine how Aunt May would embarrass him further.
Gwen stared at him for another moment, tilting her head to the side, slowly narrowing her eyes playfully. "Why?"
"I'm afraid to say that she won't like you." Peter lied, and Gwen swatted his arm quickly. "You're lying!"
"I'm not lying." he tried, his eyes glittering with amusement at the blonde's mock outrage. "That's bull! I'm adorable."
"And what are you even talking about? How can it go any worse than your first impression with my dad?" Gwen asked suddenly. "Just waltz into his home, eat his food, insult his career and corrupt his daughter?"
Peter threw his hands up in mock surrender before trying to defend himself. "To be fair, there was very little eating."
Gwen's stomach was starting to hurt from laughing so much, shaking her head at him. "You're a doofus."
"But a hot one, right?" Peter tried, wiggling his eyebrows.
"Don't put words in my mouth. I said 'cute'." Gwen lied.
Peter's fingers ghosted across her cheek, his barely-there touches giving Gwen all sorts of butterflies. He finally cupped her jaw in his hands, and seconds ticked by agonizingly slowly as they slowly leaned forward now, their eyes slowly drifting shut as their lips finally met in a soft and sweet kiss.
Gwen's heart raced in her chest as the kiss progressed, and by now it felt like Peter was too far away from her, and like he was afraid to touch her too much and/or cross a line.
She shifted on her knees, moving to straddle his lap. Peter's hands settled on her waist almost nervously before rubbing her lower back as they kissed.
Gwen's ridiculously short dress made it all too easy to press herself against him. They'd never gone this far before, together or with anyone else, and as nerve-wracking as the idea was, Gwen felt like it was right. And maybe it was fast and reckless, but she was certain she wouldn't regret Peter Parker being her first. She could feel him pressing against her inner thigh, and a shiver ran up her spine.
Breaking the kiss with a few more heated pecks before leaning her forehead against his, taking a moment to catch her breath. "Do you have a condom?" Gwen asked, just to be certain this was something both of them wanted.
Peter nodded, swallowing hard. Like any hormonal teenage boy these days, he always had one or a few in his wallet. He leaned forward, holding Gwen more firmly on his lap as he fished his wallet out. Settling back with Gwen straddling his waist comfortably as he took one of the condoms out, holding it up in silent confirmation.
Gwen grinned at that, chewing on her bottom lip, and blushing by now. "Okay. Can I just- stay on top? At least for now?" Gwen asked suddenly, feeling a little awkward now, and Peter nodded emphatically, not wanting to pressure her either. "Whatever you want."
Gwen kissed him again, more heatedly and deeply this time, pressing her body against his. Any pain he felt from the start of the evening suddenly didn't matter anymore, now that her chest was pressing against his. Setting the foil package aside, for now, they decided to focus on each other for the time being.
Sliding her hand down in between their bodies to stroke him through his jeans. He took this as an invitation, his hands sliding up from her waist slowly to cup her breasts through her dress, giving them an experimental squeeze- careful not to be too rough.
Gwen released his bulge at this, to press her hips against his more roughly, her arms hooking around the back of his neck, shuddering on top of him again, arching her back and moaning loudly against his lips.
Breaking the kiss, tugging at the material of his shirt, he took the hint and pulled back to help her remove it. Before she could ask about his injury again, he lunged his lips at her neck, and all of Gwen's questions died on her tongue. She rolled her head back, giving him easier access, and sighing softly as he massaged her breasts again. His kisses sunk lower and lower, making a trail down her chest slowly.
He tugged the material of her dress down, exposing her white lace bra underneath. Following his lead, she reached behind her to unclasp her bra, any hesitance she felt before was long gone by now. Discarding the material, the chilly night air pebbling her nipples, and Peter leaned down, closing his lips around her nipple, and she groaned, threading her fingers through his hair and grinding against him again, needing to quell the ache in between her thighs.
Gwen had never felt so wet and so alive, her chest heaving as he divided his attention between her breasts, suckling and massaging her sensitive flesh. Peter made his way back up her chest, stealing another kiss before pulling the material of her dress up over her head and discarding it. Gwen unbuckled his belt now, yanking the material out through the loops of his jeans.
Gwen got off his lap so he could take his jeans off more properly, chucking the material aside with the rest of their clothes. Before he undressed any further, he had to confirm again if she really wanted this, halting his movements awkwardly, flustered as he asked. "You're still sure, right?"
Gwen watched him adoringly. She, personally, felt like the embodiment of the heart eyes emoji right now. "I'm sure." she replied with the utmost confidence. "Are you?" Gwen asked suddenly, and he let out a small chuckle. "Definitely." She grinned at that, leaning forward on her knees and kissing him on the lips, softly and passionately, helping him pull the material of his boxers down.
He sat back down, pulling her onto his lap, their movements slowed down some in comparison to how they started, suddenly wanting to savor the rest of this experience. She shifted on his lap so she could finally remove her panties before she rearranged herself to straddle his waist again.
Peter's hands slid down to grab her ass, squeezing her playfully as they kissed. Gwen moaned against his lips in response, her tongue flicking against the roof of his mouth, sliding her hand down in between their bodies to stroke his shaft from the base to the tip, shuddering a little internally as she explored him.
He groaned against her lips, squeezing her ass again in response. She broke the kiss, nuzzling her nose against his, trying to catch her breath before she reached for the condom. She was a little nervous, but overall excited. She ripped open the foil packet carefully and placed the condom over the tip of his cock, rolling it down over his length, remembering to pinch the tip of the condom as she rolled the rest of it down his shaft.
Their eyes met as she guided the tip of his cock to her entrance before finally sinking herself down onto his length, half whimpering and half moaning as he finally filled her. She gave herself a moment to get used to his size and leaned her forehead against, breathing heavily.
"Are you okay...?" Peter asked, uncertainly and she let out a breathy chuckle, nodding, and swallowing before replying. "Yeah.. Don't stop." she grinned softly, recapturing his lips in a passionate kiss. She rocked her hips against his again before moaning out loud, finally adjusting to his size enough to move against him a little faster on top of him.
Peter had no experience with sex, but he didn't want this to be something she'd regret at all. Leaving her lips with a final peck, kissing along her jawline leisurely before kissing her earlobe. She moaned more loudly, and her thighs tightened around his waist and moved her hips more roughly against him and he grunted, meeting her hips enthusiastically with his own rough thrust. He made a mental note of that turn-on of hers, almost bursting at the sound of her shuddering moan that passed through her lips. Gwen's hands gripped his shoulders, eyes practically rolling back from that simple kiss of his, her nails digging into his flesh. Her movements were more certain by now, and he was growing worried he wouldn't last much longer.
His hands slid up from her hips to massage her breasts again and pinched her nipples, making her moan, her head lolled back, and sweat glistening her skin by now. Judging by her pleasured moans, Peter felt more confident to thrust himself upwards into her, teasing her g-spot with the tip of his cock with ease. He definitely wasn't going to last long tonight.
Heart stuttered in apprehension, refusing to let her down during such an experience, he moved his hand between their bodies, hand on her hip now and his thumb teasing her clit. (Thank God for Sex Ed!) Her body shuddered again, a fission of electricity moving through her body, and a whimper escaped her lips. "Oh, my God, Peter!"
Gwen gripped his shoulders more tightly, and the walls of her pussy began to clench around his cock, rocking her hips more roughly against his, heart hammering in her chest, and her lips crashing into his in a fierce and hungry kiss as they climaxed together, crying out in ecstasy as a wave of euphoria washed over them, their movements slowing, riding out their orgasm together.
Peter buried his face against her chest, kissing at her warm flesh and Gwen sighed in satisfaction, brushing her fingers through his hair. "Oh, wow!" Gwen breathed with a small chuckle. "I know." Peter murmured, nuzzling against her. He fell back against the blanket and the pillows, pulling the blonde with him, making Gwen giggle quietly. Peter pulled the blanket up over them. The blonde snuggled against him securely, sighing in satisfaction and draping her thigh across his waist, her head resting against his chest. They stayed like that a while longer, wanting to savor the moment for as long as possible.
Peter soared through the night sky, web-line to web-line with renewed energy with Gwen still on his arm. He landed outside her window on her fire escape, and Gwen yet again made no rush to leave his side yet, grinning up at him and trying to catch her breath. "Thanks for such an amazing night."
"Well, they don't call me 'amazing' for noth-" he was cut off by Gwen suddenly kissing him deeply, making him lose all train of thought as Peter returned the kiss. Parting was the last thing in the world these young lovers wanted to do, but they had no choice. Breaking the kiss with several more heated kisses, her skin flushed as they parted, nuzzling their noses together, sighing softly.
"I'll see you at school tomorrow. And I'm meeting your Aunt soon." Gwen reminded him, raising a finger threateningly.
"You're willing to take that chance?" Peter teased with a smirk.
"Shut it, she's gonna love me!" The blonde retorted, turning to open her window. "I admire your optimism. And your ass!" Gwen rolled her eyes playfully, trying to mask a blush as she climbed back into her bedroom. "Thank you." She retorted dryly, turning back to face him, and he crouched down to be at eye level with her. "Yours isn't so bad, either." Gwen smiled fondly at him, tugging at the lapel of his coat and stealing one more passionate kiss.
Peter returned the kiss with as much passion, feeling like he dodged that old Parker luck for the first time in a long while. "Goodnight, Gwendy." Peter grinned softly, caressing her cheek with his thumb. "Goodnight, Man-'O-Mine."
And with that, he finally left, web-slinging into the night seemingly without a care in the world. Gwen watched after him, sitting her window frame with a warm, fuzzy feeling in her chest.
A 'Wooo!' echoed out into the night, making Gwen laugh, shaking her head. Peter was showing off as he left, somersaulting mid-air before finally disappearing along the skyline.
It was stupidly late, but she doubted she'd get much rest tonight.
Fun Fact: Some a-hole wrote a story over thirty years after Gwen died and claimed she never slept with Peter, and I call bullshit. She adored Peter with her whole heart, there's no way she never slept with him. Or cheat on him, but whatever, ruin canon with your bs. #RetconSinsPast