Fantasy, Blowjob, Bondage and restriction, Consensual Sex, Cum Swallowing, Exhibitionism, Female exhibitionist, First Time, Masturbation, Oral Sex, School, Spanking, Teen, Teen Female Solo, Teen Female/Boy, Teen Male Solo, Young
There exists a semi-mythical boarding school in the mountains of Japan. At St. Anne's, students get an excellent extra-curricular education in sex!
Author’s Note: All my standard disclaimers apply. This is a work of fiction – I made it up. My characters aren’t based on anyone, and I’m not going to try and bullshit you and claim this actually happened to me. And, as always, I can’t help but sink into parody or commentary. This may be too meta for some people’s tastes, and you’re free to down vote me into oblivion or flame me if you fall into that category.
It ended up longer than I intended (don’t they always!), but I think it turned out well. I’m open to any comment, discussion or criticism. There’s a bonus author’s note at the bottom for those who finish.
There are all sorts of private boarding schools out there, each one specializing in something different. When you’re convincing parents to fork out that much money, you need to be different in a distinguishable way.
The boarding school I got sent to was REALLY different. I don’t think my parents meant to send me there. The promotional material is all very coy. It doesn’t really make the purpose clear. To be fair, if they did do that, the boarding school would be shut down pretty quickly. Everyone tends to get up in arms about teenagers having sex.
St. Anne’s is in Japan, in the mountains, which is great for privacy. It also takes advantage of Japan’s laws on age of consent. Everything that goes on in the school is perfectly legal under Japanese law.
And… look, you probably don’t care about the backstory. You don’t care about the detailed survey about my sexuality that I filled out. You don’t care about my trip there, about saying goodbye to my parents. You don’t care about the expression on my face when I realized what I was in for. You’re a sick bastard, and you just want to hear about the sex. And I don’t blame you for that. I’m one of your number now.
But I want you to know they were careful. They all knew that St. Anne’s could have been hell on Earth if they weren’t careful. And make no mistakes. They weren’t perfect. For some people, it had to have been. But for almost all of us, everything was consensual. Nothing was ever done to me against my will, and I never did anything to anybody who didn’t want it done. If there was rape, there was surely no more rape than any other school. And with the sheer amount of fucking that was going on, the administration deserves props for that.
* * *
I was nervous as all fuck when I got to my room. I was still reeling from the revelation of the school’s purpose. Sure, we’d get a full IB education. But we’d also be having lots and lots of sex with each other. The surveys we’d filled out had been used to place us with upperclassmen (here a gender neutral term in our co-ed school). They’d show us the ropes, pop our cherries, and teach us how to fuck. We’d live with them for two years, and then they’d graduate, and we’d take their places.
(Thank all the Gods that I’d filled out the survey accurately).
So I open the door, and a nervous and excited girl greets me – at least I assume it’s nerves and not an earnest need to pee. She’s practically bouncing by the threshold. She’s taller than me by a bit, and she has the most beautiful brown curly hair. It bounces as she moves, and I’m entranced by it from the start. Her face is soft and round, and her auburn eyes peek out from behind thin-framed glasses.
She’s beautiful in the way people are beautiful. She has a few zits, and there are bags under her eyes. She’s not an airbrushed model. But when she’s smiling at her, you don’t notice those things. Her face becomes HER FACE, and you can’t help but fall into those eyes.
All of this I learned later, as I fell in love with her. At this point, all I learned was her name.
“Hello! I’m Val. It’s short for Valerie.” A nervous laugh, a shy smile and an outstretched hand completed the introduction. I took it, and was grateful for the clamminess of her grip. It meant I wasn’t the only one sweating.
“I’m Michael.” I was proud of myself – there was almost no waver in my voice.
“You seem a bit overwhelmed by all this – here let me help you with that.” That last was directed at the bags I was struggling to get through the door. The room was fully furnished, of course, and most of the clothing I’d be wearing was the school uniform. But I still had quite a lot of stuff – posters, my laptop, fancy clothes and the like – that I’d taken with me.
And I clearly wasn’t hiding my nerves as well as I’d hoped.
Once we’d wrestled the luggage in, Val gave me a quick tour of the room. It was generously large by boarding school standards, with one queen bed (hers) and a twin (mine). There was plenty of closet and shelf space for both of us. In an adjoining room was a cramped office with two desks somehow crammed into it. The other door led to a fully appointed – albeit small – washroom with a shower stall (entirely clear glass), toilet and mirrored medicine cabinet.
There were little traces of Val in all the rooms. Some paintings of famous ships hanging as posters in the office, a small library on a shelf at the foot of her bed in the main room, and a few cases of makeup and a straightener (which I hoped she rarely used) in the bathroom.
There were some odd factoids she dropped too.
“The shower has a mechanical plate in it. If one person is in it, you get ten minutes of water. But it there’s two people, you get as long as you’d like.”
The purpose of that one seemed fairly obvious.
“There’s a bowl of condoms in your top drawer. Mine too.”
That also seemed pretty obvious.
After my fifteen minute whirlwind tour (punctuated by awkward, overwhelmed silences on my part), Val guided me to my bed.
“You’re probably overwhelmed.”
I grunted. It was the best I could do.
“I felt the same way on my first day.”
“I just… I didn’t know what I was getting into. I think my parents didn’t know.”
“I don’t think that’s possible. The school is supposed to be very careful with parents. They make sure parents know what they’re signing their kids up for. We don’t want any lawsuits, after all.”
“But, do they just go out and say it? Or do they hint around it like in the booklets?”
“I’m… I’m not actually sure. But surely with enough hints anyone would get it?”
“My parents may be the most obtuse people in the world. I’ve never been able to hint things to them. I’ve always had to say them straight up. It’s incredibly annoying. But perhaps they’re just Machiavellian. I don’t really know anymore. A week ago, my world was pretty firm. Now I feel like I’m in a bad porno. Or what a bad porno is supposed to be like. I’ve never actually really watched one.”
Val laughed. “Well, there’s an easy way to test that. If there’s queefing, you aren’t in a porno.”
“Um… What’s queefing?”
I was treated to more laughter, and a short lecture.
“You really are clueless about this stuff, aren’t you?”
I got defensive.
“We haven’t all had your education.”
That came out a bit more snappish then I’d intended. Luckily, she brushed it off without getting angry.
“I’m sorry. This must be terribly stressful for you.” She patted my knee. “I want to promise you something: we don’t need to do anything you’re not comfortable with. Everything you’ve heard has probably given you the impression we’re all sex starved and about to ravish you at any moment. Or perhaps you’ve picked up the toxic message that men always want sex and can’t refuse it without being less than men?”
“It’s a bit of both, I think.”
“Well you don’t need to worry about either. For your first few months, I’m the only one who’s allowed to sleep with you. After that, I can veto other upperclassmen until the end of your first year.”
This was delivered by rote, but then she looked right into my eyes.
“And I won’t think any less of you if you don’t want to have sex right away. I’ve seen your survey, so I know it’s something you want to do. But we don’t have to rush into it. We can take time to get comfortable with each other first.”
“How… how do we do that?”
She brightened noticeably, and I couldn’t help but smile. Her earlier nerves seemed to have vanished. If only mine could go to the same place.
“First, we correct your lack of porn experience. There are lots to choose from on the school media server. Then I answer any questions you have. Then we work from there.”
“Isn’t it awkward watching porn with someone? When I look at pictures or think about things like that, I normally…” my cheeks were burning. “I normally touch myself. You know, down there.” I pointed vaguely at my crotch.
“It’s properly called masturbating –“ this was in her clinical ‘I’m giving the correct explanation’ tone – “and pretty much everyone does it.”
“Oh. I kind of thought it was just me. Or at least I did before I got here. After orientation, I was a bit less sure.”
“A bit…” She shook her head, but she was smiling so it was all right. “You thought that you’re the only one who’d ever discovered something that felt that good?”
“I didn’t really think it through. I was so embarrassed. Especially when stuff started coming out.”
“Society.” She rolled her eyes. “We could teach people about perfectly normal bodily functions. Instead we leave it to them to figure it out on their own, and hide it behind a blanket of shame. That’s one of the reasons St. Anne’s exists. We aren’t going to shame you for any desires here. It’s called being sex positive.”
“So it’s actually perfectly normal, what I’m doing?”
“Yes. But don’t worry about what’s normal. Before I came here, I thought I was weird for wanting to be tied up, and wanting to tie people up, during sex, or just on it’s own. And statistically, I AM weird. Only a small minority of people want that. But there are other people who want it, and I can give it to them. Diversity of sexual desires is a great thing. It means that there’s always someone willing to try something that most people think is really, really, profoundly odd, but you think is really sexy.”
My mouth was kind of gaping. This was the opposite of every message I’d ever received.
“Now I happen to know from your survey that you also think about tying people up and being tied up. So let’s watch a porn about that!”
“That’s the spirit!”
* * *
The projector is flat to the roof, so I didn’t notice it at first. But soon enough Val has it turned on and projecting on the far wall.
She goes through several menus, and I get the impression that there is a bewildering array of porn available through the school. Diversity of sexual desires indeed!
As she set things up, my nervousness got the better of me, and compelled me into pacing. But once she had things ready, she patted the bed next to her, and I reluctantly climbed into it.
“Before we start watching this, I want to make it clear: you don’t need to be shamed by anything your body does. If you get hard and it’s uncomfortable, adjust your dick. If you get embarrassed, feel free to blush. If it gets so hot that you have to masturbate, by all means, rub one out.”
I nodded. I’m still a bit overwhelmed, and things are moving quickly, but I don’t feel scared anymore. Embarrassed, confused and just a bit curious, yes, definitely those things.
“Now, will you feel better if I put my arm around you and we cuddle, or will you feel more embarrassed?”
I’m touched that she asked. It would be easy for her to assume that I want the contact, and do it without asking. Had she done that I’d probably have frozen up and panicked. But she asked me, and that made it less scary.
I still considered it for a second. Less is sometimes a far cry from none. But in this case, it was close enough.
She nodded approvingly.
“That good that you thought about it. Don’t let anyone – even me – stampede you into something you don’t want to do. You can always take time to think and decide what you really want. I can’t say no one will ever get offended. But no one SHOULD be offended.”
With that, her arm is around me, and the movie starts.
For the first few seconds, I find the arm distracting. I can feel her warmth next to me, and I’m intensely conscious of it. I’m also conscious of the boner I’ve had ever since she started flipping through the porn titles. I take a deep breath, and surreptitiously adjust it. And nothing happens. I get no side eyes, no exclamations of grossness. For a second, I’m shocked by this.
Then the action starts and I’m drawn to the novelty.
‘Bound Babes 5” isn’t big on exposition. It starts with big breasted, hairless blond women with a red ball gag in her mouth, tied to four posts set in a stone floor and struggling attractively. She’s spread-eagled which allows for a close-up of her shaved pussy. I’ve seen still shots of pussies before, but there’s something more visceral about it when it’s in a movie.
The shot pans back out to reveal a dick, and then the man the dick is attached to. Like every dick I’ve seen in dirty pictures, it’s quite a lot bigger than mine.
Val, perhaps sensing my discomfort, squeezes my shoulders.
“I’ve never seen a dick that big in real life. Porn can give you ideas, but it’s no more real than Star Wars.”
Reassured somewhat, I focused on the movie again. The women is squealing past her gag, and struggling even more. It only serves to accentuate her vulnerability. The man can do whatever he wants to her, and she knows it.
He quickly takes advantage of that power to begin fingering her. She tries to get a away from his fingers at first, but pretty soon she’s moving into them, impaling herself on his hand as she moans in pleasure.
“That’s a good slut. Ride my fingers.”
He spanks the side of her ass a few times for emphasis.
Right as her movements begin to quicken even further, he withdraws his hand and licks the juices off his fingers.
“You’re not cumming yet, my pretty.”
I can’t help but giggle. That line was comically bad.
“That’s the other way you can tell we aren’t in a porn. Our dialogue wasn’t written by some two-bit hack.”
The bound girl whines piteously behind her gag.
The man’s cock has become fully hard. He bends down by her head, and begins to rub it all over her face. Some cum is leaking out of the tip, and it leaves shiny patches on her cheeks and forehead.
Abandoning this denigration after a minute, the man focuses on her nipples, pinching them until they are hard and erect, and then sucking on them. The women is squirming in pleasure again, but it’s clear that it isn’t enough to cum.
The man removes her gag.
“Beg me to fuck you!”
“Please! Fuck me! Make me cum!”
The man pauses to consider it. Then he leers at her.
“If you think you’re getting off before I do, you’re one dumb slut.”
With that, he squats over her face and shoves his dick down her throat.
She chokes on it and struggles against her bounds (there’s a lot of struggling in this porno), until he pulls it out. As soon as she catches her breath, he shoves it right back down her throat. He repeats this a few times, until she’s sobbing, at which point he finishes himself off all over her face.
The woman gets a hold of herself, and begins to beg him to fuck her again. He has her lick his balls and asshole until he’s hard again, and then he’s back to her pussy to pound away with his huge cock.
Like Val said, there’s no queefing.
She’s yelling “Yes! Yes! Yes!” and moving into him with every thrust, and pretty soon she’s moaning that she’s coming. The man finishes with another grunt, and he withdraws just enough for the camera to get a close-up of him pumping loads of cum into her vagina. The screen fades to black.
The movie lasted all of ten minutes, but my mind is spinning, and my cock is as hard as it’s ever been. Beside me, Valerie’s face is flushed, and her breathing is deep.
“I have some questions, but I really need to take care of something first.”
Only the fact that she’s obviously as turned on as me makes this less than mortifying.
“How will you feel comfortable doing it?”
That’s a very good question. Every time I’ve masturbated before, it’s been the dead of night, and I’ve been entirely sure I’m alone. I’ve never even considered doing it with someone aware of what was going on. I don’t really want her watching me, but I don’t think her being in the same room will make much difference. It may even make it more thrilling.
“I think I’ll be fine under the covers of my bed. As long as you aren’t staring at me.”
“I can do that. Do you want to watch me though?”
Now there was another question. It didn’t really seem fair, but I was interested in seeing her ‘rub one out’ as she’d said.
I meekly nodded, and she laughed.
“Don’t worry, I like it when people watch me. It makes it a lot more fun for me.”
She opened her dresser, and rummaged around. She handed me a condom, and took out what looked like a pink plastic penis with a few buttons on it.
“The condom is for you. If you put it on clean-up will be a lot easier.”
I’d always used tissues, and so this seemed like a great idea.
“This,” she shook the phallus, “is for me. Fingers aren’t always enough for women to get off on.”
I nodded, unsure about what to say to THAT and retreated to my bed. Once I was under the covers, I took off my clothes. Fumbling in the dark, I was able to put on the condom. I was suddenly grateful for the earlier embarrassment of the “Condoms 101” class we’d all spent an hour in during orientation.
After it was on, I gave my dick a cursory stroke. I’d never had a condom on before, and I expected it to feel more different. From some grumbling I’d heard among my friends, I expected to not be able to feel my dick at all. There was a bit less sensation, but I doubted I’d have any trouble coming. This told me they’d probably been lying through their teeth about their sexual exploits, which put a whole lot of things in a new light.
I wrapped myself in my covers, lay on my back, and then turned my head to the side so I’d have a good view of Valerie. She had disrobed brazenly, and had her legs spread out. I could clearly see the lips of her vagina, glistening slightly with her arousal. Like the women in the video she was completely shaved. She was gently rubbing around the outside of her pussy lips with her left hand, while her right pinched her nipples.
She had smallish breasts that were very perky. Her nipples were quickly responding to her simulation, elongating and standing straight up. As I watched her tease herself, I began to slowly stroke my dick. She had her head thrown back and her eyes closed, which made me feel both more comfortable, and like a voyeur, both of which turned me on.
I didn’t want to come too quickly, so I kept my strokes slow and my hand loose. After a few minutes of tentative probing around her lips, she parted them with one hand, and began to slowly stroke the insides of her passage with the other. I could hear her begin to moan, and I couldn’t help but follow suit. I was rock hard.
The slight lowering of sensation due to the condom was helping me last much longer than normal. Usually, I’d have cum at this point, but I was quite content to draw it out. There was a constant temptation to rush ahead and finish, but I was following Val’s example.
After a bit more exploration, Val removed her hand, and grabbed the vibrator. With a faint buzzing, it came to life.
Repeating her earlier strategy, Val rubbed the buzzing head of the vibe around her lips. She was biting her lip in a most endearing way. He nipples were still solid, even though she’d stopped playing with them. The hand that didn’t have the vibrator was open on her bed. Her hips were periodically humping forward, pushing the very tip of the vibrator inside of her.
She drew this out longer than I thought possible, and it became increasingly hard for me to keep control of myself. I’d never seen something so sexy, and I’d never gone for so long without coming. Val’s pussy lips were engorged, and she was visibly leaking a clear fluid. Despite her bit lip, she was moaning audibly again.
Finally, Val slowly pushed the vibrator inside of her. Her other hand began to stroke the nub on top of her vagina. She was inhaling sharply, and then exhaling as a long moan.
I’d seen enough. I began to pump furiously. I had to have my orgasm. Val’s hips were also pumping frantically on the vibe. As she let out a deep long moan, I felt my cock began to twitch. I fired three or four ropes into the condom. My orgasm felt much stronger than usual, and it left me breathless. Well, the long moan it elicited was the main cause of the breathlessness, but the orgasm contributed some of it.
Stroking quickly became too pleasurable for me to bear, and I relaxed on my back, letting my hand fall away.
Val was still going. I’d heard that women could have more than one orgasm, but it was something else to see it. She’d pull the vibe out, take a deep breath, and then shove it in as deep as it would go, moaning and shaking the whole time. Her other hand was rubbing furiously at what had to be her clit, and her bed was shaking for the ferocity of her trembling and bucking.
She kept it up for maybe a minute before she turned of the vibrator, and collapsed sideways onto her bed. It was still buried in her pussy. Her chest rose and fell rapidly, doing interesting things to her breasts, which I could still see. Val had been considerate enough to collapse on her side.
When the post orgasm lethargy began to recede, I peeled the condom off my dick, and tossed it in the garbage. Val didn’t stir.
“Are you alright?”
Val blew out a long weary sigh.
“Yeah. I haven’t had anyone watch in a while. I forgot how hot it made me, and how many times it lets me come.”
“So you don’t always do it like that?”
“There’s lots of different ways I masturbate. Sometimes I just want to get one out as quickly as possible. Normally I’ll draw it out like that, but I can’t keep them coming for as long, and I have to stop after only a few.”
She opened her eyes and looked at me.
“How was yours? I heard you moaning a bit, especially at the end.”
“I’ve never held it off as long as that. Normally I cum after three or four minutes.”
She grinned at me. “But good things come to those who wait.”
“I’ve just realized that. I didn’t realize that drawing it out made it feel so much better.”
“There are a few things that make it feel better. Drawing it out is one. Toys are another. Coming close a lot of times and then backing off can make it much more powerful when it finally comes. And of course, it feels a lot better when someone else does it to you.”
“Toys? But aren’t those only for women?”
“The flippant answer is to point out that you have holes too. But I know lots of men are cautious of anal play, and I’m not going to pressure you to try it if you don’t want to. But there are other options. Vibrating cock rings or fleshlights for example.”
“It’s a lot to take in.”
“Yesterday, masturbation was something I did when I was sure everyone else was asleep, and wouldn’t have admitted to doing in front of my friends. Now it’s being treated like a normal everyday thing. It will take me a while to wrap my head around the change.”
“I was the same way. My parents never really bothered with sex ed, because they knew I was coming here. That left me to figure out everything on my own. So I get what you’re going through. I didn’t actually end up having sex until I’d been here for a month. So don’t worry if you feel like you need to go slowly. Besides, you being so innocent makes it so much sexier.”
I wasn’t entirely sure how to feel about that. I did sometimes fantasize about a more experienced women teaching me everything. But it was a bit more intimidating in real life than in my fantasies.
“Thanks. I think.”
She levered herself up, and went to my dresser. Her rummaging in the drawers gave me several interesting views, and I was more interesting in artistic appreciation of her than what she was doing. She interrupted my study by throwing my pyjamas at my face.
“Here, you can put these on if you want to get out of your bed.”
I slipped them on under the covers, and then pushed the covers aside and sat up. Val clearly felt no need to cover herself up.
Once I was standing, I realized I had no idea what I was actually supposed to be doing. I was alone in a room with a naked woman who thought corrupting my innocence was sexy. I didn’t have a for this.
“So, um, what now?”
“I was thinking some cuddling? I’m sure you have lots more questions. Like about the movie.”
“Oh. It’s okay for me to cuddle with you?”
She walked back to her bed, and I admired her ass. I’d heard that tight asses were in some way desirable. I was pretty sure her ass was tight. It was certainly desirable.
“Here. Come sit on the bed, and lean against the wall.”
I did as she said. Once I was settled in, she scooted herself over so that she was in front of me.
“Spread your legs.”
I did as she said, and she scooted the rest of the way, so that her bare back was resting on my bare chest. My head fit comfortably on her shoulder. My hands dangled uselessly at my sides. I didn’t know if it was okay to touch her.
“If you’re nervous about touching me, you can wrap your arms around my stomach.”
She was really good at this. She really must have started a lot like me.
“So you started just as clueless as I am. Wasn’t it scary?”
“What do you mean?”
“Well I was always kind of taught to want sex. Like you said, that’s what men are supposed to do, right? But aren’t women always taught to say no? They threw you in with a guy right? Weren’t you scared he was going to rape you?”
She was silent for a few seconds.
“I’m not going to lie and say I wasn’t scared. But he took things even slower than I am, probably because the dynamic is different when it’s a boy teaching a girl. And my parents at least gave me some warning what would happen at the school. I’d already started masturbating before I came here, and a lot of my fantasies were about a man forcing me to feel good against my will, like in that movie. That way I could think about sex, without feeling guilty like I wanted sex, if that makes any sense? This school is good about teaching the ridiculousness of that idea. And now I love sex, in all of its varieties. But I still hold a special love for being tied up and pleasured.”
My dick had started to harden up during her speech. Perhaps it was her proximity, or perhaps it was the content.
“I want you to know that I can feel you dick.”
“Oh, sor – “
“I wasn’t saying it because there’s something wrong with it. I didn’t want to ignore it and make you think it’s something shameful. Erections happen. Just like women sometimes get wet. No one here is going to judge you for having a boner.”
“You’re so casual about all this sex stuff. I’m kind of scared out of my mind. When you say it, it seems so natural. If I were going to say something like that, it would come out all weird.”
“Michael, want to know a secret?”
“Everyone, all the time, is freaking out. Everyone is terrified of what everyone else thinks about them. Everyone thinks that everyone else moves through life so effortlessly. We’re all so worried about tripping up that we feel everything is too deliberate. But guess what? We’re also all so scared of fucking up that we don’t realize when anyone else does. For someone else to actually notice your mistakes, they have to be pretty fucking spectacular. So next time you’re freaking out, relax. Everyone around is also freaking out. And they’re too self absorbed to notice that you’re freaking out with them. They think you’re swimming through life effortlessly, and they’re jealous.”
“It’s really everyone? I thought it was only me.”
“It’s not always the same for everyone. And if you have a lot of experience with something, you can go on autopilot and avoid panic. But in general – and aside from a few aberrations who are genuinely unflappable – yes.”
“I don’t know how to feel about that. On one hand, it’s reassuring. On the other, it’s depressing. I didn’t want to think that everyone is always as scared as me.”
“I’m scared. I’m scared I’ll mess something up and you won’t like me. Or that I’ll mess up and hurt you. But there are things I’m not scared of. I’m not scared of masturbating in front of an almost stranger. I’m not scared of the mechanics of sex. My fears have changed over the years. When you’re where I am, you’ll have similar fears. They don’t go away, but they change. I think that’s part of what becoming an adult is. Having adult fears. You get to know there’s no monsters in the closet. But that doesn’t mean there are no monsters.”
I found myself crying, and I didn’t know why.
She turned around and got up on her knees so she could hug me. I felt her breasts press into my chest, but I wasn’t focused on the sexiness. I was focused on the comfort.
“That’s why we’re cuddling. I wanted the comfort of your arms. And I think you need comfort just as much as you do. There’s something about holding onto someone else’s body that makes the world less scary.”
We slowly slid down the wall until we were cuddling in her bed. She wrapped us in blankets, and turned off the lights.
I cried until the place where my tears came from dried up. After the tears were gone, I felt safe and exhausted. Held in Valerie’s arms, I feel asleep.
It was my first night at St. Anne’s and I slept like a baby.
* * *
I was disoriented when I woke up. I couldn’t remember the last time I’d woke to another body in my bed. Probably when I was a child, and had hid from the monsters in my closet under my parent’s covers.
‘And that’s different from last night how?’
It was good to see that my internal snark was coming back. I must have been all out of sorts the past night for it to have been gone.
Valerie’s body is warm against mine. She’s still naked. In the night, we must have moved. She’s now spooned against me, and I have my arm wrapped around her stomach. Her breathing is deep and easy.
From last night, I have ample grounds to imagine her breasts rising and falling with her breaths. I want to stroke them, but we were all cautioned at orientation not to touch anyone who’s asleep without prior consent.
Instead I nuzzle my head into her shoulder. I think about what she said about comfort. I’m in bed with a girl I’m attracted to. I have morning wood. Holding on to her should make me more scared. Instead, I feel better. She’s pretty clearly on my side. And she’s pretty easy to talk to.
My nuzzling must have woken her, because I feel and hear her breathing speed up, and she stirs against me.
She turns to face me.
She’s adorable in the morning. She’s squinting against the light streaming through the window, and she’s fighting back a yawn.
Then she kisses me.
For a second, I’m shocked, and don’t know what to do. Her lips are pleasantly warm and soft on mine. When she turned, my hand fell around her waist. I pull her too me, and kiss her back. I feel her mouth opening, and I open mine.
I’ve never done this before. I have no idea what to expect. My heart is beating very fast. I can feel hers beating just as fast through her feverish breast. When did she get so warm?
Her tongue enters my mouth slowly. It finds mine, and flicks it playfully. I feel like I’m being called to come out and play. Cautiously, I flick hers back. I focus on what I’m feeling, and I don’t think too much about what I’m doing. I've decided that I don’t want to be one of the people living my life scared of what other people will think.
Making out with her seems to come naturally. It’s easy to make contact with her tongue. To stroke it with mine when it’s in my mouth, and to gently invade her mouth with my tongue as hers withdraws.
She rolls on top of me, and my hand drifts lower, to cup her ass. My other hand joins it on her other cheek. They’re firm, and I give them an experimental squeeze. She breaks the kiss for a second to giggle.
Encouraged, I pull body into mine. There is only a thin layer of fabric between my undiminished morning wood and her pussy. She moans through the kiss as it presses into her crotch, and I almost moan too as the friction sends a wave of pleasure throughout my body.
We quickly find a rhythm, and the kiss intensifies as our bodies move together and our breathing speeds up. I come closer and closer to cuming, but I never quite go over the edge. I’m right at the plateau, but no matter how hard I push her into me, or how fast we go, I can’t quite seem to go over the edge.
Panting, after five minutes of furious humping, she breaks the kiss.
“Not quite cumming I take it?”
My cheeks are burning red.
“It’s nothing to be ashamed of. There are lots of different ways to get off, and some of them don’t work for certain people. For example, a penis inside me isn’t enough to get me off. It doesn’t matter how big it is. I need it to be vibrating, or I need stimulation on my clit.”
“So I should just head back to my bed and stroke myself the rest of the way.”
She gave me a level look.
“That’s one option. Or if you feel more comfortable now, you can let me finish it off for you. There’s no pressure either way.”
I really wanted to come. Yesterday, the idea of her seeing me naked was scary. But now I’d seen and held her in her nudity. I’m much more comfortable with the idea of her doing something like that for me.
“I’d like you to.”
She beamed at me.
There was a bottle next to her bed that I’d assumed was moisturizer. As she squirted it on her hands, I realized it was lube.
When she had her back turned, I took off my pyjama pants. Now I was as naked as she was. She turned back around, and smiled at me again.
“You have nothing to worry about in the size department. That’s plenty big enough to get anyone off.” I blushed at her praise.
“If you need to lie down, or close your eyes, or do anything else to make yourself feel more relaxed, feel free to.”
“What about you?”
“If you want to, I’ll show you how to get me off afterwards. If not, I’ll get myself off and you can watch.”
I took her offer, and lay back and closed my eyes. She put one hand on my upper thigh, and I immediately flinched.
“Sorry, I’m a bit jumpy.”
“Nothing to apologize about. Take deep breaths.”
I breathed in and out to a count of three. Slowly, her fingers trailing along my skin and raising goose bumps, she brought her hand to my dick. MY breath caught as she slowly stroked up its length with two or three fingers.
Very gently, she wrapped her hand around me. Slowly at first, and then gradually faster, she began to move her hand up and down in the classic “jerk-off” motion. What she’d said earlier was true. It felt much better when someone else did it.
I couldn’t help the low moan her touch elicited. I heard the cheerfulness in her voice.
“You like this?”
It was actually hard for me to speak.
Within a minute I was right on the edge of cumming. Figuring I’d save us the mess, I gave a rather garbled warning (I hadn’t counted on how much concentration it took to speak).
“I… thi-think I’m ‘bout to… cum.”
I heard the sound of ripping tissue, but her pumping never stopped. She didn’t grip as tightly as I did, and the lightness and the lube let her move a lot faster, which lead to a much more intense sensation in the long run.
I felt my orgasm building. First my balls squeezed, and then I moaned. I felt an explosion of pleasure overtake me, and for a second I couldn’t think or breathe. I felt ropes of cum shooting out my cock.
Valerie slowed down a bit, but she continued to stroke. In my delicate post-orgasmic haze, the pleasure was overwhelming, like liquid fire. I found myself moaning again.
“That feels so good it hurts.”
“Do you want me to stop?”
The pleasurable pain built with each stroke. It wasn’t like the build-up to an orgasm, where the pleasure is clearly leading towards something, and there’s anticipation. This was just pure pleasure, unfiltered and difficult to contextualize. It was more than I could handle, and if it was me doing the stroking, I’d have stopped. But it felt so amazing.
I gritted my teeth.
“Are you sure you’re okay.”
She still didn’t stop.
“Please don’t stop.”
Unfortunately for my pleasure, I was betrayed by biology as my dick began to soften. She switched her grip, and gently stroked the tip with thumb, and I moaned again. There was so much pleasure that the back of my eyelids alternately appeared white and red.
“Okay! I can’t take anymore!”
She stopped right away.
I slowly opened my eyes. All my muscles were slowly unclenching. I was breathing heavily, like I’d just run a race and I was covered with sweat.
Valerie was beaming at me.
“So how was your first sexual experience with another person?”
“I can see why they give us two weeks for orientation. After two weeks I just might be ready to go an hour without feeling like that.”
“I remember the feeling. I was quite angry that I hadn’t taken full advantage of the first few weeks.”
I managed to prop my body up on my elbows.
“If you show me how, I can do you now? I really want to learn how to make someone else feel that good.”
“That’s the spirit!”
She grabbed her vibrator from her bedside table where she’d left it last night, and placed it on the bed next to us. Then she grabbed my left hand and placed it on her left breast.
“Cup it like so –“ she demonstrated on her other breast “– and then rub it like this.”
The rubbing involved side-to-side rotations of my wrist. She leaned her body into my hand, and moaned it a satisfied way.
“Now try pinching it like this.”
I mimed her demonstration, pinching very gently.
“Harder than that.”
Not wanting to hurt her, I gently increased the pressure.
I pinched as hard as I felt was safe.
“That’s still not hard enough.”
Gingerly, I increased the pressure as she continued to smile at me. Finally, at a pressure level I was sure had to be painful, she told me to stop.
“Doesn’t that hurt?”
“It hurts in the best feeling way.”
Considering I’d just been through something like that, I really wasn’t in a position to judge.
“Now go through those three with that hand, while I show you what to do with you other.”
Absently I switched to rubbing.
Val parted her pussy, and pointed out her inner and outer lips, as well as her clit.
“You’re going to want to stroke the lips to get me nice and wet. Then you can try rubbing my clit, or putting a finger or two inside of me.”
She briefly demonstrated each of those things. It was incredibly hot to watch her casually pleasure herself.
Nervously, I stroked around the lips of her pussy. I could feel a slight dampness from her leaking wetness. She gave a sigh of contentment, which I took as an encouraging sign.
Growing bolder, I slipped a finger inside of her. The inside of her vagina was warm and slippery, and I quickly realized that stroking the sides was the way to go – spurred on by occasional jerks of her hips and moans.
“Rotate you arm, and stroke the top.”
I did, and she let out a long moan. It didn’t feel any different to me, but based on the surge of juices I felt, it clearly made a difference to her.
“With your hand like that, you can also use your thumb on my clit.”
She reached out and gently positioned my thumb on top of the fleshy nub that seemed to bring her so much pleasure.
As I rubbed my thumb across it, she sucked in a sharp breath through her teeth.
“Just like that. Keep doing that.”
She slowly fell still, causing me to look up at her face. She had an expression of the most profound joyful serenity.
“Are you okay?”
She nodded silently.
I realized that my left hand had fallen still. Switching to the other breast, I began to pinch her nipple. Quickly, I fell into a rhythm. Pinch the nipple several times while stroking the clit up and down, and then rub her breast like she’d shown me while rubbing circles on her clit.
Her breathing became ragged, but she never lost the look of profound contentment.
After a few minutes, she opened her eyes, grabbed the vibrator, and handed it to me.
“I want you to hold this right above my clit, and don’t stop unless I say ‘red’. Anything else, literally anything else I say, means keep going. Do you understand?”
I nodded. She lay back, closed her eyes, and spread her legs.
I pushed the vibe to the indicated spot, and turned it on.
She began moaning right away, deep, long moans that almost keened with their intensity. I felt her pressing into the vibe. Seconds later she was yelling.
“I’m coming! I’m coming!”
I saw a small squirt of fluid come out of her pussy. I didn’t know that women did that too.
She started bucking into the vibrator, and I focused on holding it steady, and in position.
After a few seconds, she stilled. Then the cycle repeated itself.
She came three times, complete with squirts and yelling before her moans took on a plaintive tone.
She closed her legs, but I was able to keep the vibe on target.
“No more. Please no more! That’s enough.”
I wanted to stop, but I remembered her earlier instructions. Clearly telling me to stop made it even hotter for her. I noticed her hands had moved from her sides. Now she was pinching her own nipples with savage intensity.
“I’m coming again!”
Her scream was desperate.
“That’s enough! Please! Please stop! It’s too much.”
Grimly I held on as she began to writhe. But it was clever writhing, that never made it too hard to keep the vibrator on target.
Finally, after several minutes of very delicious looking agony, Val called out “Red!”
I immediately removed the vibrator, and switched it off.
Val’s body, incredibly tense, seemed to fold in on itself. She was winded, and breathing shakily.
“Are you okay?”
It took her a long time to answer. Eventually, her eyelids fluttered, and she stretched languidly.
“Never been better. Lets shower and get breakfast.”
* * *
It hadn’t been as simple as that. First we’d kissed for a while more. Our kisses were much more tender and exploratory this time, now that we’d worn ourselves out.
Then there was the business of showering. Val insisted that we shower together, to be able to enjoy the hot water for longer, and I found that I had no objections. I was quickly growing used to her naked body, but I longed to touch it all over. So far, I’d had limited opportunity to. I figured that in the shower I’d be able to soap her up and touch her all over.
“You know, this shower can be even more interesting than you’re picturing right now.”
I blushed. “How so?” There was no real point in denying that I was picturing anything. Not that I wanted to deny it anymore.
“Has anyone ever told you’re cute when you blush? No? Anyways, it’s simple. I pretend to be a possibly innocent little girl, and you play the role of a more experience man. And we see where the acting takes us.”
She smiled at me. “Trust me. It will be so much more fun this way.”
And so I found myself standing in the shower alone, weird and awkward standing in the shower as I waited for Val to come join me. I didn’t know whether to get started or not, so I spent a few minutes fiddling with the water temperature and pressure. The shower was a lot more complicated than I was used to, and it included movable spouts with interesting head shapes.
Finally, the door opened, and I heard Val give a short squeal.
I quickly whirled around to make sure she was okay.
Her eyes were wide and scared, and she was covering her breasts with one arm, and her pussy with the other.
‘Play along’, I remembered. I quickly placed both my hands in front of my own crotch.
“Oh my God! I’m so sorry. I didn’t mean to burst in on you! Here, I’ll leave right now.
“Erm no, that’s okay, there’s plenty of room.”
“But we’re naked! Boys shouldn’t see girls naked! They might get ideas.”
I certainly had plenty of ideas of what I could do to her naked body, so I guess I couldn’t find fault with her logic.
“What if I turn around? We can shower back to back?”
Val was right; this was so much hotter than just trouping in naked together. I knew she was acting, but it was fun to play along, to pretend her a bashful virgin and not an experienced temptress. My hands did a good job of hiding my growing erection, and I managed to keep my eyes on her face, playing the chivalrous man to the hilt.
Her eyes darted to my crotch a few times. She was a pretty good actor. I almost believed she’d never seen a dick before.
“Oh, um, but only if you promise not to peek?”
I turned around and let my hands fall.
“I won’t peak if you don’t.”
She giggled nervously. I heard her soft footfalls in the water as she stood behind me.
The main shower was one of those decadent ceiling mounted units that dumped litres of water on you every second. It was more than wide enough for both of us.
Whistling tunelessly, I began to shampoo my hair. My dick was completely erect. In my mind’s eye, I was playing out all the ways this could end, all the things we could get up to.
“Um, could you please pass me the soap?”
I was positioned closest to the shelf with all the shower supplies, and she clearly didn’t want to walk in front of me to grab soap. Grinning, I grabbed a bar, and held it out behind me.
“I’m holding a bar behind my back. Think you can grab it without peeking.”
There was silence, then a giggle. “Yes. Sorry, I nodded at first, and then I realized you couldn’t see me. Okay, I’m going to grab it.”
Nothing happened for a few seconds, and then I felt a hand on my butt.
“That’s not the soap.”
She squealed, and removed her hand.
“That’s okay. The soap is more to the left. Your left, that is, if you really have your back to me, and aren’t peeking at me and using blindness as an excuse to cope a feel.”
“I would never!”
I chuckled at her tone of righteous outrage. But she grabbed the soap from my hand this time.
I rinsed the shampoo off my hair. There were five other bars of soap on the shelf, but I decided to pretend that there was only one – the one she had.
“If you’re done with the soap, could you pass it back to me? It’s the only bar.”
“Yes? What is it?”
“Well you see, I can’t soap up my back.”
“I can’t actually see you, but I suppose could be a problem. But is your back all that dirty?”
“A lady is never dirty! But I can’t shower without cleaning all of me! That would be a waste. Normally I have one of my sisters do my back when we shower together, but they’re obviously not here.”
Her too innocent voice immediately put me in mind of incestuous lesbian shower orgies, which were incredibly hot to contemplate.
“Well, I guess you’ll just have to go without today.”
“Or you could soap my back, mister.”
“I thought you didn’t want me looking at you?”
“I don’t! But I want my back clean. Maybe you could close your eyes?”
“That seems risky. Without being able to see you, I could end up touching you… anywhere.”
Ye Gods it was fun to play the part of the ambiguously lecherous man! I knew Valerie would understand and appreciate all of the innuendo. But the real question was how much her character would get.
Silence greeted my pronouncement.
“Well? What will it be?”
“You… you can keep them open I guess.”
I turned around and took a step forward. I was almost touching her. She could probably feel my breath on the back of her neck.
“Hand me the soap.”
She shivered, but passed the soap over her shoulder to me. She kept looking dead ahead. I accepted the soap, and slowly lathered my hands up. I didn’t want to use the bar when I could use my hands, and feel her skin under them.
Once I was ready (and I’d given her several moments to anticipate it), I reached out a sudsy hand, and massaged the soap onto her right shoulder. She gasped.
“Is anything wrong?”
“It’s okay… I just feel funny. You know, down there.”
I could hear the blush in her words. And I could empathize; I was certainly feeling funny down ‘there’.
I kept rubbing the soap in. As I removed my hand and replaced it with the other hand on her other shoulder, she shivered briefly.
Her shoulders and neck were first. Her wet skin was firm and feverish under my fingers. I could feel the interplay of her muscles beneath the skin as she tensed and relaxed in response to my ministrations. It may have only been her back, but it was surprisingly intimate.
I soaped up my hands again, and then moved my hands down her sides. I reached far around to graze the sides of her breasts with my finger tips, causing a shocked yelp.
“Is something wrong?”
“You touched… you touched my chest!”
“Oh. Sorry. I was just being thorough.”
“I guess that’s okay then. But don’t do it again! No one’s allowed to touch me there but my sisters.”
“Do your sisters wash more than just your back then?”
“They’re not supposed to… look if I tell you a secret, you won’t tell anyone, will you?”
“Of course not.”
My hands had wandered down to her lower back. I was massaging the soap in just above her tight young ass. I removed my hands and soaped them up. Let’s see how thorough I could get away with.
“Well, my sisters wash all of me, especially my privates. It started by accident, but it made me feel so good that I asked them to keep doing it. And I do… things… with them in return.”
“You wash their privates too?”
“No. They do that to themselves while they wash mine. Then they make me kiss theirs. I asked them to kiss mine too, but they say they don’t want to, and I’m the youngest so I have to do what they say. And their washing does feel nice, so I don’t really complain.”
“Oh my. You’ve been quite naughty.”
My hands drift down to her ass. I slowly massage the suds in. She squeals again. But doesn’t pull away.
“I have been?”
“Are you going to spank me? That’s what my parents do when I’m naughty.”
“I could. Or you could decide that you like being naughty. Then I could do what your sisters do. And you could pay me back in the same way.”
“It wouldn’t feel right for me to get away with being naughty. But I really want you wash me in my privates. I’ve wanted it ever since I got in. Can you do it, and then spank me?”
“I suppose I can.”
“Oh thank you!”
She turned around and embraced me. My stiff cock poked her in the leg.
“Oh my! It’s gotten so big. Can… can I touch it?”
“You can do more than touch it. You can kiss it. How about you do your part first? Then I’ll reward and punish you after.”
Val batted her eyelashes at me.
“Oh thank you mister!”
She kneeled down in front of me. She gently took my dick in her hands. She ran her fingers up and down the length. I breathed out heavily.
“You like it mister?”
She’d gone deliberately doe eyed, her innocent charade belying experience far greater than mine.
“Yes. Continue, if you will.”
(Okay, so maybe I was enjoying this too much. But I hadn’t taken even a single drama class. Eventually, I managed to get less hammy when roleplaying.)
She went cross-eyed starring at it, before she leaned forward and planted a delicate kiss right on the tip. I felt a jolt of pleasure, and I involuntarily curled my toes. She backed up and looked into my eyes. I realized that hers were a particularly dark and beautiful brown. I stroked her wet hair with my hands.
“There’s a good girl.”
She leaned forward again. This time she took the tip in her mouth after kissing it. This was completely unlike masturbation. Her mouth was warm and soft, her lips firm on my shaft, and her tongue strong and supple as it teased the bottom of shaft. I couldn’t help the catch in my breath. It was hard to remember to breath when you felt this good.
She must have taken my breath as encouragement, because she didn’t back off or stop. Instead she began to bob her head up and down on my cock. I was rapidly approaching the point of no return. The novel sensations were that amazing. It was all I could do to keep my knees from buckling. I didn’t have the presence of mind to think, evaluate, or say anything. I just encouraged her with cooing noises, and gentle stroking of her hair.
And then my orgasm was upon me. The wave started with her lips, locked tight around my shaft. It spread out, shaking me from the tips of my hair to my curled toes. My knees almost did buckle, and standing became extraordinarily difficult. I felt a delayed second wave radiating from my nuts, and then my dick jerked in her mouth as I filled it with my hot cum.
Val bobbed up and down a few more times, milking the last of the cum from me. Once I was finished, she stood up in front of me. I saw her throat bob as she swallowed.
“My sisters make me swallow their juices. I thought you’d like it if I did the same thing for you.”
“Thank you, I do. Now, I’d like you to lie down on your back with your eyes closed.”
“You’re going to clean my privates now mister?”
“Yes, I am.”
With a beaming smile, Val lay down on the floor of the shower. Pausing only to grab a shower attachment with the Venus symbol on it, I sat down cross-legged next to her.
“You’re so dirty that I don’t think soap would do. We’re going to have to power wash you.”
Hoping I wasn’t about to make a fool of myself, I aimed the head of the nozzle at her exposed pussy, and pulled the trigger.
She screamed almost immediately as a stream of fast water landed right on her clit. Her hands jerked towards her exposed slit, but with an effort she arrested them.
The attachment shook in my hands as it pulsed water towards her pussy. I couldn't tell if her pussy was wet, but it did have the same swollen look it had gotten whenever she’d been feeling pleasure.
Any doubts I had were assuaged moments later when she began screaming in pleasure.
I held the flow on her, as I watched her eyes flutter, and her heartbeat frantically under her breast (her nipples were completely erect, I noticed).
I gave her fifteen seconds of pleasure. Then I switched the nozzle off.
“Please don’t stop mister!”
“But you said yourself you had to be punished for your naughtiness. And now I think it’s time for your spanking.”
She whimpered, but didn’t protest as I draped her over my lap, with her ass facing up and at the mercy of my hand.
I took a deep breath. I didn’t know how far to take this, or how far I was supposed to take this. And I didn’t want to actually hurt her. Should I go for a real spanking? Or should I fake it for effect?
“Mister? Are you going to spank me? Or have you decided I wasn’t that naughty? I’ll be good, I promise.”
Her writhing ass made an appealing target. But I erred on the side of caution regardless. My first blow could barely be called that.
She giggled. “You’re a lot weaker than my dad, mister.”
Weak, eh? I’d show her.
My next blow was considerably harder, and was rewarded by a sharp “Eek!”
Having found the correct power, I wasted no time bringing blow after echoing blow down on her unprotected ass. She squirmed throughout them, but the squirming seemed to be more about rubbing her pussy on my leg than any serious pain.
After about ten, Val spoke to me as Val again.
“Okay, that’s enough of that.”
She got off my lap, and grinned at me.
“You’re a natural!”
“That was so hot!”
She winked, and then threw herself at me. Her lips found mine, and it was quite a while before we got around to finishing our shower and going to breakfast.
A/N The Second:
There was a question I was trying to answer with this work: can erotica teach something useful (beyond simple mechanics of sex) while still being hot? Many people, myself among them consumed erotica during our formative sexual years, and it’s shaped our sexual development. To what extent do the authors of porn have a responsibility to lead young horny readers towards ethical sex? Is this even a useful goal? Is any moralizing inherently unsexy, or can we balance the two and create a tension that improves the story?
Before you think I have pretensions of being literary, I would like to point out that I also wrote this to jerk off to. The idea of being taught by a more experienced woman, or more generally, the idea of the corruption of innocence is really hot to me. All of my stories are some sort of riff on this theme. And I find erotica much hotter if there’s some dialogue and exposition between scenes where people fuck like rabbits. That is how this story ended up so bloody long. I hope you enjoyed it. Let me know in the comments if you’d like me to continue. I can’t promise a speedy sequel, but if enough people enjoyed this, perhaps I’ll revisit St. Anne’s at some point in the future.
Val and Michael have a lot more they can get ‘up’ to.