Some Starting Notes:

The basis for this fic's universe is the MCU, but there are a few deviations here and there. For instance, both Kirsten Dunst's red-haired Mary Jane and Zendaya's Michelle Jones exist in this universe, as does Emma Stone's Gwen Stacy. Aunt May is Marisa Tomei. Laura Harrier is Liz Allan. The other changes — whatever they may be — should be obvious when they're introduced.

Peter is 18 and just starting his senior year when our story begins.

I think that's all for now. Leave any questions or thoughts you might have in the comments below and be sure to check out the end of this chapter for additional links and info about posting schedules, etc. etc.

Enjoy!

Peter Parker knew how he should feel. As he swung in one pendulum arc after another through the streets of New York and felt the wind whipping against his Spider-Man suit, he knew that he should feel free. He knew that most people would give up everything they had to be able to see and experience life the way he could. Most of the time, free was exactly how he felt swinging through the city he called home. But not right now.

Right now, Peter felt frustrated.

It had been two years since he'd been bit by that radioactive spider and his Uncle Ben had died. In that time, he'd made a name for himself as New York's Friendly Neighborhood Spider-Man. He'd held his own against Captain America of all people and had joined the Avengers — if on a part-time basis. (Mr. Stark had once called it a kind of superhero "internship," but Peter wasn't sure if that still applied now that Tony was gone.) He'd even helped save the world from Thanos. He had, by all possible definitions, accomplished more than any other 18-year-old in history.

And yet… he still hadn't slept with a girl.

Peter knew how ridiculous that sounded. Even admitting it to himself made him roll his eyes. But it was the truth. A few years ago, that fact might not have bothered him as much as it did now, but Peter wasn't the scrawny, acne-covered teenager he used to be. Ever since that spider bit him and gave him powers, he'd been in, well, amazing shape. His acne had cleared up. He'd had a growth spurt and, by all objective standards, he looked better than every other guy in his school now.

But he still hadn't figured out how to convince a girl to sleep with him. It was like the one math problem he couldn't seem to solve, and his powers were making it worse.

Recently, he'd developed a theory that his spider powers had boosted his physical attributes in more ways than he'd originally thought. He was horny all the time now, and masturbating was starting to feel like an increasingly less fulfilling way to satisfy himself. He could barely look at an attractive girl in person now without getting hard and briefly considering bending her over and taking her right then and there. It was, to put it simply, a distracting problem, and one that he couldn't seem to shake.

He felt pent up, and if he didn't find a way to finally lose his virginity soon, Peter was starting to think that he might go crazy. Or explode. Either outcome seemed equally likely at this point.

It was these thoughts that were racing through Peter's head as he swung his way to school Friday morning. He'd stopped taking public transit to MSST (Midtown School of Science and Technology) years ago, and he'd gotten his own route there down to a tee.

Sure enough, he arrived on his school's rooftop with 20 minutes to spare before first bell, and he was changed and down on the ground floor just five minutes later.

As usual, Peter tried to keep his head down as he made his way through the school's halls. He may be a superhero, but he still preferred to keep his profile low and fly as far under the radar as possible. Maybe that's why no girls have noticed you yet, his own voice muttered to him in his head. Peter shrugged it off, even though he knew it was probably right.

As he walked toward his class, he couldn't help but notice, yet again, two of his school's hottest girls. Gwen Stacy, as always, stood out the most. With her blond hair, mischievous eyes, and habit of wearing skirts that perfectly showed off her long, milky legs, Gwen was like every schoolgirl that every guy had ever fantasized about. Peter looked at her a little too long as he walked past, but Gwen didn't seem to mind when she caught his lingering gaze. She just smiled and waved. Peter smiled back and couldn't help but briefly wonder if her wave meant she was interested in him. She's probably just being nice, that damn inner voice said again.

Standing next to Gwen was Peter's longtime neighbor, Mary Jane Watson. With her fiery red hair and busty chest, MJ was everything Gwen wasn't. Whereas Gwen was demure but alluring, Mary Jane was loud and sexy. She carried herself as if she didn't have a care in the world. She knew how hot she was, and she wasn't afraid to show that off — as her tank tops and tight jeans always made clear. She wanted men to look at her, and she also wanted them to know they'd never have a chance unless she deemed them worthy of one. Despite their differences, she and Gwen had been unlikely best friends as long as Peter could remember.

Peter chanced a quick glance at MJ, but unlike Gwen, she didn't notice him pass by. He took that as a sign of luck, given how openly he'd stared at her chest and ass for a few seconds there. So he just put his head down again and continued on to first period.

When he got there, he sat down next to his best friend, Ned, and looked around the classroom. That's when he noticed her. Liz Allan, the former subject of all of Peter's adolescent fantasies, was sitting quietly in one of the room's back corners. The past year hadn't been easy for Liz. Ever since her father, Adrian Toomes, had been outed as the villainous criminal known as the Vulture, Liz had become a bit of an outcast. Many of her classmates unfairly held her responsible for her father's actions. Peter didn't, of course, but given the role he'd played in her father's incarceration, he'd never again worked up the nerve to try and rekindle their once-burgeoning romance.

Most of Liz's friends had abandoned her, except for a few. One of them, a prissy brunette with perpetually pursed lips, was sitting protectively next to Liz at this exact moment — as if daring anyone else to try to bother her friend. Peter had no intention of doing so, but that didn't stop him from looking at Liz longingly from across the room.

Liz may have had a rough past year, but you'd never be able to tell that just by looking at her. She was as beautiful as ever — light brown skin and big doe eyes and all. Over the last few months, she'd taken to wearing looser and more casual clothing. It was a lot of crewneck sweaters and yoga pants, but Peter still caught himself fantasizing about her on a regular basis. In fact, as he looked at her, Peter's eyes drifted to Liz's soft, plump lips, and he began to wonder what they'd feel like on his… what they'd look like wrapped around his—

"Yo, man, you here?" Ned asked, interrupting Peter's train of thought.

"Yeah, just had a rough morning is all," Peter replied, turning away from Liz and facing forward again.

"Had to screw up some bad guys on the way to school?" Ned whispered, totally oblivious to what was actually going on.

"Yeah, sure. Something like that," Peter said with a forced smirk. A moment later, class began, and Peter did everything he could not to think about the swelling in his groin or what Liz would look like bent over in front of him or on her knees begging for his…

Suffice it to say, Peter was finding it hard to focus these days.

When Peter climbed through the fire escape into his apartment later that afternoon, all he could think about was jerking off and finding some relief after a day's worth of unfulfilled sexual fantasies. Matters weren't helped when he stepped into his and May's living room only to see his aunt bent over in front of him — her shapely ass looking like it was on the brink of tearing her jeans apart. She had a full laundry basket held against her waist and was busy picking up a loose sock when Peter decided to make his presence known.

"Hey, May," he said as nonchalantly as possible.

May shot up and turned around, clearly startled by her nephew's sudden appearance. "Oh, Jesus, Peter!" She shouted. "I didn't here you come in."

Peter just gestured to the fire escape, prompting May to roll her eyes. "I don't know when I'll ever get used to that," she said with a sigh. It had been almost a year since May had learned that he was Spider-Man, and aside from a few F.E.A.S.T. appearances that she forced him to make from time to time, everything had more or less returned to normal.

"Would it kill you to come in through the front door?" May asked with a slight smirk. "I mean, it could," Peter responded with a shrug. "Could get hit by a car coming in. Fall through a sink hole. I think my shortcut is safer, actually."

May scoffed. She walked toward him and cupped his cheek. "Don't joke about any of that," she said. "I don't know what I'd do without you."

"Probably marry a millionaire," Peter joked.

"You think you're the reason I haven't done that? Not my type, I'm afraid."

What is your type then? Peter thought to himself as his eyes involuntarily glanced down to look again at May's ass and the shape of her curvy waist as she turned away from him.

"You taking the laundry down?" Peter asked.

"Yeah, I shouldn't keep putting it off," May said.

"I can do it for you," Peter offered, trying not to sound too anxious.

"Yeah? Are you sure? You just got home?"

"Of course. Take a break. I'm sure you've had a long day," Peter said as he walked over and took the laundry basket from May's hands.

"Okay, but only if you insist," May responded — feigning at disappointment even as she went over and laid down on the couch, clearly relieved she wasn't going to have to make the trek down to their building's laundry room.

"Happy to do it," Peter said as he walked toward their front door and opened it.

"Like I said, I don't know what I'd do without you," May called after him just before the door closed.

Peter's laundry offer wasn't, of course, wholly altruistic. Indeed, before he even put any of their dirty clothes into the washer, he'd fished through the basket and pulled out a pair of May's panties. He picked a lacy black and pink pair, took a quick whiff of his aunt's aroma, which still clung to the garment, and then stuffed the underwear into his pocket. When he walked back into his and May's apartment, she didn't notice the slight bulge in his left jean pocket, or the hard-on that had been raging for what felt like 10 straight minutes. She just thanked him again before he told her he was going to go lay down for a little bit.

What he actually did surprised even Peter.

He'd planned all along to jerk off the first chance he got. But, as he stepped into his room, a reckless impulse suddenly coursed through his body. Maybe it was a rare bit of boldness. Or maybe it was just the natural result of years of sexual frustration. Maybe he just needed something, anything to finally happen. Either way, Peter decided to leave his bedroom door cracked open rather than shutting it all the way.

The act caused an extra level of excitement to overtake Peter's body as he began to strip off all of his clothes, leaving him with nothing on and his rock hard, 8-inch boner on full display. He usually didn't get completely naked when he masturbated, but he felt a desire to put on a real show… just in case May decided to take a peek inside.

With those thoughts racing through his head, Peter laid down on his bed and brought May's panties to his face. He inhaled his aunt's scent as he began to slowly jerk himself off. Maybe it was the daringness of doing such a thing when there was a chance he could be caught or maybe he was just even hornier than usual today, but Peter felt like he could have cum immediately.

He didn't, though. Instead, he kept his orgasm at bay and waited, stroking himself up and down at a steady rhythm while keeping his eyes closed and May's underwear pressed to his face.

After a few minutes, Peter wondered whether he was stalling for no reason. After all, there was always a chance that May was busy doing something else.

Those thoughts died when Peter heard May softly call his name from their apartment's bedroom hallway. For a moment, he considered stopping. He considered shutting his door before his aunt saw anything. But that moment of ice-cold fear melted almost as suddenly as it arrived.

Peter kept going. A few seconds later, he heard a creak just outside his room and the faint sound of his door being pushed open just slightly. He then hear a sudden gasp and could sense his aunt standing frozen in his doorway just a few feet away. Peter's stroking immediately quickened and, before May's rationality took hold of her again, he decided to give her a reason to keep watching.

"Oh, god… May," he groaned. He'd never talked while jerking off before, but he wanted to make sure his aunt knew exactly who he was thinking about in that moment… as well as whose panties he was sniffing while he pleasured himself.

"Keep going, May," Peter groaned, and he faintly heard with his increased senses the sound of May gasping in surprise again. He could also hear her heartbeat suddenly pick up. Whether it was because of excitement, fear, embarrassment, arousal, or all of the above, Peter couldn't be sure.

Regardless, he didn't want there to be any chance of May missing the grand finale, so he picked up his pace. His right hand gripped his cock and started jerking off with reckless abandon as he inhaled the smell of his Aunt May's panties again. For a moment, it felt like every nerve on his body was sparking with electricity. He'd never felt this excited before. Never felt this closer to sex before.

"Oh, May… May, here it comes," he announced. Sure enough, his orgasm hit him like a giant wave and he peeked his eyes open just enough to watch his cock shoot out his cum with such force that several spurts hit the ceiling. As he kept cumming, he heard his aunt whisper, "Oh."

Peter saw out of the corner of his eye May clamp a hand over her mouth. He also saw her remain frozen in place and keep watching as her nephew moaned her name a few more times and released his final few ropes of cum. Once he was finally spent, he let his right hand fall down to his side, but used his left to scrunch May's panties against his face one final time.

He saw through his half-shut eyes May still standing in his doorway. He waited to see what she would do. Would she say something? Admonish him? Apologize for barging into his room?

The answer turned out to be none of the above. Instead, May quietly turned and walked away, returning his door to its previous, barely open state. As she did, Peter could swear he saw a red flush on her cheeks. Did that turn her on as much as it did him?

Peter wasn't sure. But he intended to find out.

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Next chapter coming next week! In it, Peter makes his move on May...