You begin to roleplay...

Having gotten yourself clean and dry, you turn back to the pile of clothes on the floor, and feel a slight sense of ick. You're not a germaphobe, but you're not excited to be putting on the clothes you wore the day before, especially the underwear.

"Hey James" you call out as you slowly pick them up, reluctantly getting dressed. "I think I'm ready to head back."

"Awww man" he replies in a melancholy tone in response "Really? I was hoping we could spend the day together."

"What did you have in mind?"

"Just a lazy Naked Thursday. Sit on the couch and watch a Star Wars movie...or all of them"

You let out a small reflexive laugh, this was not what you expected. "Thanks James, but I think I'm nerded out. I do like your company though."

"That's great to hear. I don't hear that often." He said as he drew close. You feel your heart race up as he puts his hands on your hips and reaches down to give you a slow, seductive kiss. You're worn out, but you can't deny the desire you still feel. How is it that both of you can still be this excited, after everything you've been doing? James pulls away before it can escalate further.

"I know you said you're kind of done with nerd shit for the day" He said as he walks away, getting himself dressed as well "but I was hoping I could trouble you for one last favor. "

"Sure, what is it?" You ask, with an answer immediately presented, as he hands you a couple of large books, with some pieces of paper and a precariously placed flash drive on top.

"Look over some stuff and try to make a D&D character, at least a rough sense of what you'd like to make." You hold out your hands to take them from him, but your words are a slight protest

"Jesus James, is all this really necessary just to make one character?"

"Not really, I guess." He admitted "The one on top is the one you need to have, the rest just provides extra options. The flash drive has all the books, as well as some online bookmarks for extra resources. Webforums for builds, discussing characters and plothooks, all that good stuff."

"This all sounds like a bit much." You say "push someone into the pool and make them learn how to swim kind of approach," You take another look over the stack in your hands "Still, last night doesn't make it seem that hard to understand."

"Ya, there's lots of stuff that you can kind of skip around on. Like if you're a fighter, you could completely ignore the chapter on Magic, and that's like half the book."

"Oh, okay" You say, encouraged that the expectation isn't to read all of these hundreds of pages. "When is this due?"

"Due?" James asks humorously "This idn't homework babe"

You laugh too, seeing how trained in your ways you still are, but you also see an opportunity. "Maybe not, but you're still my teacher," you say in a seductive voice "and I may need some private tutoring..."

James responds with a peculiar mix of a laugh and a groan "You better get out of here if you're going to head back to your dorm. You keep that up and you'll never leave."

With an agreement on that, you leave James apartment and make your way back to your dorm. The books get heavy in a hurry, and you plop them unceremoniously as soon as you get through the door. In a hurry, you get yourself out of yesterday's clothes, having an internal debate about what next to wear, and whether taking yet another shower is necessary. Unable to make a decision, you think back to James' idea of a Naked Thursday, and while he's not around to enjoy it, that does sound like a tempting option. It's a fun and naughty idea without actually really doing anything. Locking the door behind you, you take a few moments of reckless and youthful abandon, dancing around your dorm in your nudity, relishing in the thrill of nobody knowing and nobody being able to stop you.

You feel kind of silly as you stop, not because of what you just did, but at how it's taken you this long to recognize certain things. You've been out of your parents house for half a year now, you still act like you're living them and bound by their rules and their standards. They do keep an extremely watchful eye on your spending and your social media, but there's still a great deal of freedom that you have now, that you're only now seeing exists. You're not going to get ahead of yourself; there's still the rules of the school, and society as well, but for now, you're going to flout expectations of yourself and relax in your bed naked with your laptop, looking over James' silly D&D books.

Like you thought, this stuff isn't terribly hard to understand, but the amount of possibilities is overwhelming. You're sure you could get a handle on this on your own, but you don't even really know where to start. His friends all seemed to have backstories and concepts of who their characters were and what they were about, albeit amateurish and somewhat reductive. You think that might be the answer; if you have a character concept, the rest should fall into place rather easily. At least, that's the idea. You peak through the bookmarks James saved for you. He didn't think this through, clearly, as there is no sense of organization or logic to them. It's like he just exported all of his bookmarks onto his flashdrive and called it a day.

Including some he probably didn't mean to share with you.

Clicking randomly, you find a very different sort of roleplaying avenue. One where people play out their adult fantasies with one another through the anonymity of a forum persona. Your curiosity is highly piqued as you look through the public pages, people discussing what they want to do. Unless James was stupid enough to make his username be his actual name, you would never be able to find him, and you know he's not that stupid. That also means that nobody would ever know it's you as well. You bite your lip as you look up at the ceiling in thought, trying to recall some of the kinky fantasies and dirty dreams you've had in the past and tried to repress. You naturally recall the tease you gave James earlier about needing 'private tutoring' earlier. You were never at risk of failing a class, and wouldn't have normally fucked a teacher to make for a better grade, but the idea is a turn on. Of course, there's even wilder ideas you could explore, maybe the character you bring to the table with James and his friends is a more constrained version of the character you make here.

You also feel a tinge of guilt and remorse. Would James think about this as cheating, if you roleplay-fuck online with total strangers? Should you pretend you never saw this and continue on as you were? You could also tell him what you found, and hope he isn't overly embarrassed by his secret.