The right way to use a rubber

It occurred to you that Emi must have been busier with a lot more than hopping out of her clothes since you left the room, because her level of preparedness for this lesson seemed above and beyond. At least, that's how you felt as she began to pull several colorful, rubbery items out from the pocket of her apron with an unusual snap between her bare fingers. It was a bit like watching a stage magician-- or a clown-- preparing to perform some feat of prestidigitation, only you suspected that your unfinished sexual education course had a lot more to do with the womanly side of your instructor and less to do with the giggling joker. "Do you know how to make balloon animals, Ren?" Emi questioned, as she put her lips to one of the rubbery items and began to stretch it out to a fuller size.

You blinked stupidly. This was more clownish than you expected. Still, you played along, honestly shaking your head no. That wasn't a piece of wisdom that Benefactor had ever seen fit to groom you with.

"Well, balloon animals are the second best thing you can do with these things. I'm going to teach you more about the best one!" your caretaker teased, as she freed a pair from the string and dangled them in front of you. "Which color do you like? I've got all the colors in the rainbow!"

You wondered where one even purchased a box of rainbow colored condoms. Furthermore, why the heck did she need so many?! You asked that one out loud by accident.

Emi looked a bit flustered for a moment, then scratched the back of her head awkwardly. "I-It was a novelty item, okay? Like a joke! I don't run through that many, if that's what you're thinking! In fact, I just opened the pack," she laughed, although she sounded embarrassed. It seemed she was worried she was coming off as slutty instead of seductive and maybe, on some childish level, this was her attempt to make the oncoming prospect of sex that she hadn't been 100% sure was the right move a little less intimidating.

You assured Emi that the color didn't matter all too much to you. Dealer's choice, you said.

"Okay, but that means you're getting a bright orange condom," the tall, toned lady hero laughed in response, dangling the most garishly colored condom from the pack for a moment, before stretching it out between her fingers. "Do you want me to put it on with my mouth?" You gulped, but she just threw up both of her arms into an X shaped and laughed like she was busting a gut. "Ba ha ha ha! If you want that, we're both going to have to learn something! What, were you picturing something like that?!"

Evidently, your face didn't hide your genuine anticipation very well. Miss Joke smiled warmly and pushed off the counter to stand closer to you, while putting one hand back down to her hip. "Hey, don't worry, kiddo. I'm just teasing. The normal way's fine for now, right? I'll help you with it." Emi was already pretty close to nude, wearing just the apron, so it wasn't fair for you to be embarrassed as she reached down to grab the hem of your pajama pants with one hand and hook her fingers inside, teasing your pubic hair lightly with the tips. "You okay?" When you nodded to reassure her, she accepted the signal, moving both hands to hook each side, then dragging them down along with your boxers, so that you stood in the kitchen with just your shirt on and your pants pooled around your feet. You stepped out of them awkwardly, feeling as though you should cover your raging boner... it was still hard to get used to completely abandoning your modesty around the kind woman who'd helped you out this far, a responsible adult around a decade older than you. Her encouraging smile helped you along, and slowly, you dropped your hands to your sides to let her continue.

"There's an eager student! For your first lesson, I want you to try to stand still while I do this, okay? This isn't the right time for giggling or squirming! We're going to open the ring on the rubber up wide--" Miss Joke explained, pulling it to its full circumference. "Then slowly put it on. It looks like it's going to be a perfect fit!" It was a weird thing to be complimented on, but she did have a point; you seemed to match the size of her hypothetical, multi-colored-condom-wearing boyfriend pretty well. You gripped one hand to the counter to steady yourself as one of the woman's palms suddenly cupped the base of your shaft, while the other steadied itself upon the head of your penis with two fingers and quickly eased on the rubber with the rest of her hand. "Does it feel a little tight?"

You nodded. This was the first time you'd worn one, after all.

"That's good. A little tight is just right! This isn't the kind of thing you want going on loose," she chuckled. "And I do appreciate you wearing one. Sex ed isn't the time for... well... you watched the real sex ed video, right? So you know what happens if you go in raw?" she questioned, sounding uncertain of your real sexual knowledge. You knew at least that much and nodded in support. "Good! As a hero, I'd have to beat you up if you tried to bareback me on our first date~"

It sounded like a joke, but her words set your heart pounding all the same; you could feel your dick twitching in her hands and noted her jolly grin turn into a wry one. She couldn't have missed the response; she might even feel your heartbeat, given the way she was cradling your penis. The promise in those words-- first, that she considered this a "date" and second, that going in without the condom on a later date might be an option-- was as arousing as the sight of her apron-clad body, as her fingers worked their way towards the base of your shaft.

"That look on your face is really cute... I'm beginning to understand why Midnight likes teasing people so much," Emi whispered, her face achingly close to yours on the side as one hand cupped your balls and the other secured the last inch of the condom in place. "There. Nice and tight! You're ready for action, right?"

You nodded so enthusiastically that it felt embarrassing, even in the moment.

"Great! Me too. Now, there's lots of good positions you can go for, even in a situation like this where you're not laying me down on something. One of the best ways to get access can actually be taken straight from the animal kingdom. This apron's the perfect piece to do it in, too," she giggled, spinning to show you her bare buttocks. Your cock was achingly hard, as she placed both hands upon the sink's rim and presented her toned but thick ass to you, completely uncovered. "You know what I mean!"

You answered: doggystyle, standing up, right?

"You passed your first quiz!" Emi joked, grinning over her shoulder as she squared her stance. Unable to stand it any more, you approached and boldly began to run your naked shaft between the softness of her cheeks in preparation. That was a trick you'd picked up in the fake sex ed video you'd stumbled onto first. Emi closed her eyes and bit her lip in anticipation, while wiggling her hips up and down suggestively. You clapped a hand onto each side of her slim, firm waist, feeling around her abdomen-- she wasn't the type of hero where you could count every can in their six-pack, but her biceps, thighs, and waist all showed signs of the physical fitness she trained on the job. Frankly, despite her gender, she was a lot more built than you were. Her ass was especially nice; comfortably soft, yet firm, pushing up against your manhood with encouraging and eager ****.

Wanting to appreciate her more, you snaked one hand from her belly up into her apron, squeezing her bare breast beneath it. It was another target spot of womanly softness upon that well-trained marble of a hero's body. With an unpracticed touch, you jostled her boob in one hand, then began to run a thumb along the nipple. "Mmm... You get an A for effort, but your technique could use some work. You can press and pinch just a little... not too hard. Try circling it with your fingers, too. A smooth motion. That's good!" she sighed, opening her eyes a quarter shade with a pleased expression. "You're a quick learner, Ren."

You wondered if it would always be like this, with Miss Joke guiding you all the way through from start to finish. Seeming to sense your misgivings, she grinned wider and placed one hand upon your wrist. "Hey, I hope it doesn't feel like I'm talking down to you. You'll get to the point where you want to experiment with other things too. Just let me enjoy feeling like a responsible teacher for a while, huh?" she encouraged you. "Now... are you ready to use your penis, or were you going to cum into the condom over just my butt?"

The thought had crossed your mind, but she had a point. It'd be a waste to finish up without getting inside. As if worried your jizz was about to erupt and waste itself if you didn't act soon, you hurriedly worked to line up with her holes and shove it in.

"Woah there, buddy!" Emi gasped, then laughed awkwardly. She'd felt you pushing against the wrong spot. "You can watch what you're doing and line it up slowly with the slit, alright? We're not doing, uuuh, butt stuff..."

Her words hung in the air like a question, although they were really just a statement. It made sense. It wasn't like you were really craving anal; you hadn't even gotten a chance to use her pussy yet.

And yet, Benefactor was suddenly there, watching from the living room like an old lech. "I never took you as the type to yield to authority, Young Ren. You certainly never took my lessons like a good, obedient student," he smirked, while respectfully averting his eyes back to the television. "Oh, please. I can feel your vitriol. I'm not here to tell you that you have to fuck her ass. I just wanted to remind you that if ever you should like to, the power is entirely in your hands. She may think she is the teacher, but becoming the first-time user of that sweet little hole of hers would be as simple as projecting that want into her."

You'd already completely forgone the option of implanting new cravings into her, you reminded yourself. Your subconscious was going to have to do better than that.

"But what if she wants to be surprised? Hm? She wanted all of--" he paused, gesturing towards the kitchen, where you were poised to enter your apron-clad mentor from behind, "this, but she wouldn't admit it to herself. She needed that last little push over the edge. What if she wants you in her ass, too? What if she wants to be spanked or degraded, face-fucked until her mascara runs like in that pornographic video you watched? Do you think she'll ever admit those things to a boy like you straight out?" While making himself comfortable on the couch, the old man looked over his shoulder and grinned at you. "You don't have to make her want it. You could just make her tell you. Don't need to turn her into a slut if she already is one, right? She said those condoms were all just a little joke, but do you believe that? Why not make her tell you? She didn't buy all of those just since you moved in, you know? Ask her just how bad of a craving for cock a slut like her has to have, to buy a box of one-hundred multicolored condoms-!"

"Ren? You okay?"

Emi's voice snapped you back into reality; you couldn't believe you'd actually zoned out while holding her luscious body in each of your hands, with your cock just shy of entering her. You'd expected to have a better hold over Benefactor at this point. After all, you were satisfied, right? This ought to be the turning point in your mental health, the "satisfaction" the old bastard had mentioned, that makes him and Pendulum start to fade from your mind altogether.

"Maybe we were rushing a bit too fast...?"

You shook your head to ease her worries. Why was the Benefactor in your head even rattling on about the possibility that Emi was more promiscuous than she let on, anyway? Was there anything wrong with that? Obviously, there wasn't. Your brain was just looking for new ways to **** you. This was all the confusion of a sexual novice manifesting itself. The thought that your technique was too lacking-- too boring-- came through, goading you to make Emi tell you just what she wanted. The worry that you were a nobody who didn't deserve her battered you, trying to **** her into something that was more worthy of your status. It was just another stark reminder to ignore the words of your fake teacher...

... And another reminder of the constant temptation to use your powers. **** to resist that temptation and show yourself happiness that required only the slightest touch of your Pendulum that you'd already allowed, you finally began to ease yourself into Emi.

"I mean it. If you're not ready, we don't have to do it yet," she reminded you, while hiding her face towards the sink. You weren't sure if she was hiding a silent moan-- a face that would pressure you into further action-- or an expression of worry, one that might dissuade you. Figuring out people was so hard; that was a tool that Benefactor's specter always used against you, encouraging you to tease out the truth.

You proved to Emi that you did indeed want it, by continuing up until a good length of your shaft was submerged inside her womanhood.

"That's good! Nice and easy. You can start to move when you're ready... gently," she instructed, while keeping her expression concealed.

The feeling, even while wrapped in a condom, was unreal. You'd never been inside a woman before and it was infinitely different than the feeling of masturbation. The closeness of her and the heat surrounding your dick as your hands explored her body put to shame even the wonderful feeling of assisting her with her dildo the previous night. Miss Joke had to warn you to take it a bit slower a few times, as you acted like a race car accelerating from 0 to 100. Frankly, you were so close to bursting that you felt yourself trying to climax at every opportunity.

"It's a bit of a Hollywood myth that sex always ends with the two cumming together," Emi informed you, as though she could read your thoughts. "Most people aren't really synchronized that way. Try not to be worried about that and just enjoy yourself. You can worry about getting to the point where you sexually please your partner just right as we continue our lessons," she giggled, sounding remarkably in control of herself despite the motion of your bodies slapping together. It reminded you of her strength and mental fortitude, as a hero.

It also felt just a bit emasculating. You weren't really on the level where you could drive her crazy, like in all of those videos yet. Even though she was clearly sexually starved, you thought, by the sound of her voice, she may have preferred the dildos. She did have a point, though: you were still learning. Eventually you'd be on the right level. Eventually-!

You grit your teeth as, embarrassingly, outside of your control, you began to spurt jizz into the rubber balloon surrounding your phallus. You felt like you'd barely just started and it was already over... She definitely hadn't reached orgasm yet.

Sensing your distress, Miss Joke turned to face you as you pulled out and she placed one hand upon your shoulder. "Hey, hey, don't worry, buddy! I said this was sexual education, right? We're going to train not just your knowledge, but also your technique and your stamina!" she grinned, seeming unperturbed by your premature ejaculation. "Besides, if you ever feel like your partner didn't get where they wanted to be-- and assuming you're possessed of a certain heroic spirit in the bedroom-- there are still ways you can help me finish, even if your dick is spent."

You thought the next lesson probably ought to be about removing and disposing of the condom, but you were willing to hear her out.

"Let's learn about cunnilingus next! Think of this as the cost of your tuition~"

Just then, as you felt your dick throbbing like it wanted to stand back up for another round, the doorbell rang with a high-pitched, unwelcome noise. "I wonder who that could be?" Benefactor chuckled from the couch, then licked his finger as he flipped a page in a familiar newspaper displaying his own arrest portrait. Miss Joke's face looked a bit panicked, revealing that she was still understandably shy about revealing this relationship of yours to visitors.

Should you run and hide? Should you tell her to answer the door without opening it? What was the right move?