"Remedial Education" - Dating where chastity cages are customary

A new writer (using the screen name maybenexttime) posted an interesting story about dating in a near-future society, one where male chastity devices have become a normal part of dating. The first part of Remedial Education occurs when the male protagonist first starts dating in high school:

Then it skips forward ten-fifteen years, when he finds someone who might be wife material. The bulk of the story covers this romance, from the early dates to going away on vacation together:

Unlike a lot of chastity fiction, Remedial Education has a sweet, rather romantic angle to it. There's a lot of teasing, but its all in good fun, and there's no S&M or (explicit) D&S. The setting (and characters) just kind of assume that a good boyfriend/husband will offer to be locked up.

There are currently six parts available at OrgasmDenial.com:

Remedial Education
Part 1: Julie and Me
Part 2: Meeting Claire
Part 3: Claire's Idea
Part 4: Returning the Key
Part 5: Home Alone
Part 6: Vacation Blues

 

And the links have broken . . . Oh well

 

Remedial Education
Part One: Julie and Me
by MaybeNextTime​

I have to confess - It wasn't until I met Julie that I got fitted, which was couple years later than just about any of my peers. But by the time I got mine there were fewer and fewer good ways to explain one's un-caged status. One possibility was bravado - you might invent a girlfriend with hippy parents who didn't require it, or some similar (and equally improbable) story. Or you could just embrace the reality that you were hopeless and probably forever a geek. I was definitely a geek. (At least geeks could masturbate whenever they had the privacy to do so. That's a significant compensation for a hormone-infused teen, to be sure, but I still longed for real female companionship).

[Mod note: this first paragraph has been edited for legal reasons[

Until I met Julie, I never even asked to be fitted I'm pretty sure my parents, and half my friends for that matter, assumed I was either asexual or gay.

Everything changed with Julie though. We met at some after-school thing, and one day in the lunch room she casually rubbed her hand over my crotch. She could obviously tell it was stiff, but definitely unencumbered. She rescued me before I could faint from morbid embarrassment. "So I guess you're not seeing anyone? You want to ask me out?" I was a geek, but not so much of one to not know the answer to THAT question! My whole view of myself changed at that moment. Not only did I not have to be a geek for the rest of my life, an incredibly beautiful girl flirted with me.

And so that night I asked my parents to have me fitted, I think somewhat to their relief. By next weekend, I had a comfortable cage custom fit to my dimensions (or at least as comfortable as something so constraining against where nature is trying to take you can be), ready for Julie and her parents to lock me in. I was ready to start dating for real.

We started officially going out a few days later, which meant meeting her parents, cage at the ready, of course. I had never done anything like this before, which I admitted to Julie on the walk over. She giggled, and said not to worry. She'd had a few boyfriends before and knew the drill. Her parents wouldn't make a big deal of it, she promised. And she had a secret that she'd tell me later.

In fact, I was terrified, but the evening wasn't nearly as bad as I had worried it would be. It was a little awkward making chitchat with them in the living room, but her dad quickly just took me into the bathroom. I already had the cage on; he just had to add the lock. I think Julie and I were out on our first official date in less than 45 minutes.

That's when Julie let me in on her secret. She had made her own copy of the key, which she promptly handed me. I had to promise - swear - to be extra, extra careful, to make sure to always be wearing the cage any time someone might check - at school, and of course, any time I picked her up at her house.

And so I was unlocked that very night, and had a very, very un-frustrating sex life for the two years Julie and I were together. We could have parentally sanctioned sleepovers, with a secret escape to carnal bliss. (This was not unheard of, but it was pretty rare. I was a very lucky teen.)

Basically, it was like I had read about in books about the old days, when kids could just have sex whenever they wanted and before the gesture of being locked was something no woman would ever forgo from her lover, even if it was merely symbolic for the vast majority of couples.

But this story is not about Julie. Our relationship fizzled out, as young lust is wont to, with graduation. Before I moved away, she took the lock back (her parents by then "officially" having given her control of the key), and that was that.

I had a string of casual (and not so casual) relationships in college, and, naturally, all of them expected - and I daresay got - their lock on me by the time things got past second or third base. Perfectly normal, and the cage would, of course, come off whenever we were together. Less a constraint than an article of jewelry, like an engagement ring without the implication that marriage would necessarily follow.

That's how it was, at least, until I met Claire.

To be continued...

 

Remedial Education
Part Two: Meeting Claire
by MaybeNextTime
​

You know those cliches about finding a perfect soulmate? That's how it was the moment I met Claire. I've met my share of women who made my jaw drop in various ways, but there was always something superficial about any relationship that emerged, nothing meant to last.

I met Clare when we were both trying to get tickets to a film festival. It was sold out, and we chatted while waiting for returns to become available. We both eventually scored tickets, but they were singles far away from either other. I spent the whole movie regretting not getting her number. I was pretty sure I noticed here "accidentally" brushing against my crotch to check for telltale signs of a cage, but I couldn't be sure. (Anyway, I was going to a movie alone - how much more single could I have been?)

It was a long shot, but after the film, I waited around outside the theatre hoping to bump into her. And it turned out she was doing the same for me. This time, we exchanged numbers.

I had really never been so attracted to someone in my life. She was interesting, smart, successful (a designer, with clients all over the country), and amazingly, almost unbearably, sexy in both body and attitude.

I brought my cage with me on our second date, which was dinner at a place neither of us could quite afford (we split the check, as always). Bringing the cage along was a bit presumptuous, of course, but I had a real sense that she was The One. And when she invited me back to her place, I was definitely glad I had.

We had a great evening of, well, amazing sex. And then she asked me about the bag I had been carrying all night. I came clean and showed her the cage. "You brought your cage? For me? Already?"

The words might sounded accusatory coming from someone else, but I somehow knew that it was just question. "Yeah, I know it's not been long, but I've never met anyone who I'd rather have lock me."

"That's awesome! I've been hoping you'd say something like that." Then she whispered in my ear, "My lock's in the bedroom, maybe we should go there." Ten minutes later - it wasn't easy getting the cage on as my arousal came back in spades - I was officially hers. I felt lighter than air.

As I kissed her goodnight and made my way to the door, a dumb smile on my face, she stopped me. "Hey, drop your pants real quick", she said.

"OK...". She let me stand there for a moment with my shorts around my ankles, and finally grabbed me, one hand on my butt and the other on my (now straining) cage. And then she started giggling.

"I don't actually need you to wear this, babe. I love that you want to give me this gift, it's amazing. But I want you to have a key of your own. You're a grownup, and already you did your time when you were a teenager." I had hit the jackpot again, just like with Julie.

From then on we devoted our time together to trying every sexual practice ever invented, and enjoying more of them than is probably healthy. A full range of anatomically surprising positions. Bondage, spanking, mixing pain and pleasure. Her on top, me on top. Sex in elevators. Sex in airplane bathrooms (not recommended, by the way). Every now and then, the missionary position, just to be extra kinky.

And speaking of cliches, the longer we were together, the better it got, even as the initial glow of novelty wore off. We learned where each others buttons are, and the infinite ways to push them, finding more and more delightful ways to wear each other out.

A lot of sex means a lot of pillow talk, but I guess it wasn't for a year or so that she asked me about high school. Too painful for most guys, I guess (I'd certainly have wanted to forget it if I hadn't met Julie!).

So I told her all about Julie and her "secret." She laughed, obviously appreciating our subversive measures. Lust conquered all, we agreed.

A couple days later, she brought it up again. "Hey, didn't you feel a little guilty about it sometimes? Like you were cheating?"

"I guess, but the amazing teenage sex more than made up for any misgivings I might have had."

"But what about now? Don't you feel like you missed something? I mean, isn't this something all guys in high school go through?"

"I never really thought about it." I think that wasn't true. I had thought about it, actually.

"Seems kind of the same as getting through high school without taking math or history or something. I'd wonder if it was going catch up with you, or if there's something you never learned."

"I suppose..." For the first time in our relationship, I had no idea where this was going. And I could feel stirring in my groin, although talking to her often had that effect on me.

"Like, maybe you never learned how to delay gratification, to appreciate things along the way."

"I appreciate you." That was certainly the truth.

"Yeah, babe, I know. But that's not what I mean and you know it. Most guys spent a few years learning to focus their hormones on something other than just coming. But you always got what you wanted right when you wanted it, didn't you?" She was smiling sweetly.

"Yeah, I suppose that's true." It felt a like she was scolding me. And for some reason that was very, very hot.

"I'm just worried you might be missing out on something. Aren't enjoying what you have as much as you could. Think about it. Maybe we can do something about it, if you want."

"I'm not sure what we could do. It's a long way from high school."

"I'm sure I could figure something out, if you wanted me to..." Wicked smile again. "Let's get some sleep."

I thought about it. Nonstop, actually. A week or so later, as we were going to sleep, I brought it up. And things haven't been the same since.

To be continued.

 

Remedial Education
Part Three: Claire's Idea
by MaybeNextTime​

There was no denying that Claire had hit something deep and raw inside me. It took me a full week to sort it out in my head and to work up the courage to admit it to her, which was the first and only time I can remember being reluctant to share my inner feelings with her. But she was right. Julie had no way of knowing it at the time, but when she gave me the key to her lock way back when, she was also taking something I'd need later. But I was afraid of what it would take to get it back, and of what Claire might have in mind.

I don't know why I was so scared actually. The road we were about to take would definitely prove difficult (but also very rewarding), but I realize now that wasn't what was bothering me. I was afraid I'd be diminished in Claire's mind, that she'd love me less, or at least see me differently.

"You know that thing we talked about last week?" I must have sounded awfully tentative.

"You mean how you humped your way through high school with the key to your hot girlfriend's lock and never learned the basics of controlling your sexual urges the way every other boy that age does? No, I had completely forgotten about that." Then she stuck her tongue out at me and laughed, which put me right back at ease.

"No, I meant about replacing the dishwasher. But seriously, yeah, that."

"So what about it?

"You said you might have some ideas on how to fix it. I'm interested. I think. I mean, I've been thinking about it a lot. It's kind of scary though." I'm pretty sure I was actually stuttering.

"Aww babe. You know I love you. I just want us to be as happy as we can be together. You're the first guy I've known who missed out on this. To be honest, it sounds like it must have been great for you at the time. But there's more to life and sex than getting an orgasm whenever you want one. Guys don't have great wiring from the factory for this, at least so I hear." Her hand caressed my thigh.

"So you have some ideas about what to do about this, I take it?"

"Let's try something Friday. If it works for you, we'll take it from there. If not, at least we know we tried. And I promise, it will be very hot. Well, definitely for me. But I think for you, too. Deal?"

I had no idea what, exactly, I was agreeing to, but how could I disagree? "Sounds like we have a deal."

"Yippie! This will be fun!" She kissed me, and then whispered seductively, "I'm very wet right now. Maybe you should take advantage of that."

And that would be the last time for a long time we had what we would come to call "high school sex".

Claire went out of town for a business trip Wednesday, leaving me alone for a couple days to think about our deal, whatever it was. By the time she got home Friday I was a bit crazy with curiosity and, well, desire. She texted me from the airport.

"Just arvd. Did u miss me?" She always asked that when we had been separated.

"U know it."

"Rmbr deal for wknd?" How could I have forgotten?

"Yes! But what is it?"

"Youll c latr". No hint, but clearly, at least, she had been thinking about it too.

When we got in, she announced that she had made dinner reservations, and that we'd have to talk over dinner. Then she changed out of her work clothes, which were stylish enough, into something that totally got my attention: a little black dress, cut just low enough and fishnet stockings, which, I'm sure she knew, reliably drive me wild.

"Why don't we just eat in tonight?" I asked with mock innocence, looking her up and down, never one to be subtle.

"Come on babe, I'm starving, and we don't want to be late".

We somehow made it to our table without calling too much attention to the rather obscenely prominent bulge in my crotch, which I think was only because all eyes in the restaurant were on Claire.

Toward the end of dessert, Claire finally got down to business. "OK, so here's what I've been thinking..."

"I was worried you'd never tell me."

She lowered her voice and leaned in close. "When we get home, I want you to take me to the bedroom and undress me. Do it slow, even if you want to rip my clothes off."

"Gladly"

"And I want you to make me come, with your mouth. And then again. And again. Four times. You don't get to come until I've come at least four times. Think you can do that?"

"Yeah, I can do that". Actually, three or four to one was probably about our ratio anyway. But it wasn't a rule, just how it usually worked out.

"You have to promise to control yourself. You might want to fuck me, but you can't, not until I say you can. I get to come four times before you get to fuck me."

"Yesssss, OK." Claire almost never said "fuck", at least not to refer to the sex act, which made it all the more powerful when she did.

"Now get me home before I stain the chair. I'm not wearing any panties." She grabbed my hand under the table and showed me she was telling the truth.

I'm not sure how we made it to the car, and home, without getting arrested. I wanted to start right there in the parking lot, but I got her to the bedroom in record time. I was a good boy though. I took my time undressing here, just like she told me to.

I wasted no time spreading her legs. She came quickly the first time, almost as if my tongue was a vibrator. I took my time for the second round, though. working my way down her body, past her crotch and down to her legs, and then back up again, teasing her with my tongue before settling in. When she finally climaxed, I think she might have woken up the dead, let alone the neighbors.

She crawled over to me wordlessly. She put her hand on my shaft, gently stroking, using her own juices as a lubricant. I was about to burst when she stopped. "Oh, I get two more first, don't I?" She smirked, very self-satisfied.

I slapped her ass, gently but firmly. She smiled, and I did too.

"Oh, babe, I love it when you do that. But I still get two more orgasms, if you're still up to it. That was our deal, remember? Now, do you want to spank me or make me come?"

I settled in back between her legs, me still hard as a rock. I've always loved giving oral sex to Claire. But this was different. There was something about the fact that she was asking me to - ordering me to - that made it more intense.

She came again after about ten minutes, reflexively pushing my head away. But I resisted, kept going. And then she came again, a second wave atop the first one. I thought she was going to crush my skull with her thighs.

"Oh, god, babe, what would I do without you? You need to let me catch my breath. Hold me for a while, OK?"

We cuddled for maybe 15 minutes, maybe an hour. I was still hard as a rock, but I didn't push it. I was a bit spent myself.

"Turn on your back for me, OK?", she eventually whispered.

She slowly straddled me, taking obvious care to dangle her breasts over my face as she got on top of me. Even in my moment of almost uncontrollable lust, it was hard not to appreciate how gracefully Claire moved.

"Let me do the work now, OK babe?" She slid my shaft into her lips and started rocking slowly. It felt wonderful

She took her time, and eventually sped up to a fever pitch. When I finally couldn't hold back, I exploded insider her, and I think I blacked out after that.

"Was that worth waiting for?"

"Oh yes." I barely had the energy to speak.

"Sleep on it, and if you still feel that way in the morning, give me back the key to your cage".


To be continued...

 

Remedial Education
Part Four: Returning the Key
by MaybeNextTime​

"Sweetie, that was amazing last night." I was still basking in the afterglow, after something like 10 hours of sleep.

"Yeah, it was, wasn't it?"

"So, you want me to give you your key back?"

"No, hold on there, babe. I only want you give me the key back if you want to. I'll be happy either way, no pressure. If you do, I think you'll get a lot out of it, but you'll have to let me do things my way for a while."

If last night was what "her way" was like, I'm there. "I want to give you the key."

"Are you sure? Don't just say that because you had a good time last night." As if she read my mind. "We can have amazing sex either way, you know..." She flashed a little wink.

"I want to, really."

"If you mean that, great. But if you do, make sure you know what you're getting yourself into. Sometimes it might be a lot more frustrating for you than you'd like. You know, like your friends in back in high school had it. You're not used to not being able to just get it whenever you want it, but that's what you're signing up for if you give me that key. Are you sure you want to deal with that?"

"Um, I thought it about it all last night. Yes, really. I want you to have the key, even if it means a little frustration sometimes. I'm a big boy. I can handle it."

"I guess we'll see if you can." She took the key from my hand and added a chain, which she put on as a necklace. You'd see other women do this sometimes, with their key dangling seductively their cleavage. It was sexy, but it also let you know they were involved with someone. Territorial symbols had never been Claire's style, at least before now.

"If it gets to be too much for you, promise to let me know, OK? Now let's get you in your cage. You've been roaming wild for a long time, haven't you?"

With that, we somehow got me into the cage, which I hadn't worn in months (and even then, only at parties and other events where it was expected). This time, when the lock clicked, I was as nervous as I was the first time, at Julie's parents.

"Oh, babe, look at your face! Don't worry," she cooed reassuringly. "Here are the rules: everything is just like before. The only difference is for now, I decide when where and how you get to come, not you. It won't be so bad, because I love having sex with you, and think you'll have to agree that I'm a very hot woman." Then she whispered in my ear, "I love that you trust me enough to do this, and I promise to take good care of you. Remember that, even if it gets tough, OK?"

---

The next week was surprisingly normal, except that I was wearing the cage full time, any time Claire and I weren't actually having sex. She wanted me to get used to having it on physically, which I did in a few days, but it remained a constant reminder of my lack of sexual autonomy. But she still let me out every night. We licked and sucked and cuddled and humped each other almost nightly, just like usual. (Work was busy for both of us, but we managed to get in our share of recreation time.)

She teased me a few times about putting the cage back on without letting me come, and she actually did that to me once, after getting me excruciatingly close. But she made it up the next morning, saying she didn't want me to have to go to work frustrated. In all, I certainly didn't suffer from any severe orgasmic deprivation that week. To tell the truth, by the weekend I was almost worried that if this was all there was to her plan for me, it wasn't really going anywhere.

But any concerns I had in that department evaporated one Sunday morning over breakfast.

"Hey babe, remember what we did last week, the night before you gave me back my key? I really enjoyed it. So we're going to do it again." Her tone of voice made very clear that this time, she wasn't asking. That took me aback, but it was also exciting.

"That was fun."

"Tell me what we did."

"You had to come four times before I was allowed to come myself."

"You had to give me four orgasms. At least four. With your mouth."

"Right."

"But this time, I think I'll be leaving you locked until you've finished the deed. You can start when we get home from dinner. I made us a reservation at the new place we've wanted to try.

"Maybe you should wear panties this time, though. I might not be able to control myself," I offered.

She smiled. "You better control yourself. If you get arrested, I'll visit you every day in jail to remind you what you're missing."

Dinner went on, and on. The food was OK (though I wasn't really paying attention), but the service was infuriatingly slow. Claire didn't help matters; she always "needed more time" whenever the hard to find server wanted to take our order or clear our plates. She even asked to hold off the dessert until she was finished with the coffee. We didn't make it home until after 10.

"Should we watch the news before bed?" she asked, as if serious.

"NO!"

"Spoken like a man who knows what he wants. But I'm curious. Are you in a hurry because you really can't wait get your tongue in my pussy, or because you can't wait to get it over with so I'll let you come?"

Ouch. I'd need to chose my words carefully.

Before I could get a word out, she fired a second round. "Babe, have you ever regretted telling me the truth? It's not like I don't know how you're wired."

"Putting my tongue in your pussy isn't exactly a chore. But honestly, I want both."

She smiled. "I do too. So are you going just sit there or are you gonna take my clothes off? It's getting late..."

She was as wet as I'd ever seen her. Apparently she was enjoying this. She came quickly the first time, minutes after as I started.

Once she recovered, I set to work again. This time, she crouched over my face, letting her casually stroke my balls, as if to remind me of the reward at the end of the tunnel. I had never eaten her from this angle, so I was relieved when she started moaning. When she finally came, she fell onto me, her mouth right at my cage, She laughed and gave my cage a slow, seductive lick.

"Babe, you won't like this, but I'm worn out. I need some sleep. We'll have to pick up where we left off."

"I can keep going."

"That's very impressive, but I'm about to turn into a pumpkin. I have an early day tomorrow. Will you hold me while I go to sleep? I'd like that."

It took me a while to nod off, with the strain from my budding erection against the cage making it hard to get really comfortable. Claire woke up first, and I could smell coffee when I opened my eyes. Claire was already showered, wearing her bathrobe unbelted, exposing a line from her neck to the triangle of her crotch. It was, at that moment, the loveliest sight in the world.

"You get some sleep? I'm sorry, I'm running late."

"Yeah, some. What're you doing?"

"Packing. You remember I have a client meeting this week."

What? Maybe she said something about that a while back, but seriously? Now? "Um, no..."

"I'm sure I told you, I'm really excited about this client. And London! I wish you could come with me."

"You're going to London? Now? For real?"

"Only until Thursday. Oh, you didn't come last night did you?"

"No, I didn't, as I'm sure you know."

"Aww, babe. It's gonna be tough for you, but you'll just have to wait till I get back. Can you do that for me?"

Those last two words, for me", somehow made me think I could. But I had to ask. "You planned this, didn't you?"

"No. Not really. Well, sort of. But it's for your own good, and it'll be worth it."

"I'll go crazy."

"Maybe. But you'll get better."

After the taxi picked her up, I found a note on the bathroom mirror: "You still owe me two orgasms, which I'll be thinking about the whole time I'm gone."


To be continued....

 

Remedial Education
Part Five: Home Alone
by MaybeNextTime​

I spent Monday after Claire left feeling well and truly sorry for myself. I was horny, my penis was locked in a cage and Clare and the key were heading to the other side of the Atlantic. There was no chance of relief for at least four days - four days! - and I couldn't even touch her. In fact, she wouldn't be arriving until the middle of the night my time, which meant that I wouldn't even be able to talk to her until tomorrow.

For some crazy reason I spent the evening looking at pornography, which had the predictable effect of just making me hornier, but just as unable to do anything about it.

I brightened up a bit the next day. I had made it through the night, and I had a pretty full workday to distract me. And Claire had emailed to let me know that she arrived safely and to set up a time to video chat that night.

I hurried home from work Tuesday to rendezvous with Claire at a decent hour, before she'd be going to bed on London time. I don't think I had the computer booted for more than 15 minutes when she connected.

"Hey babe! Hope you don't want to murder me yet." Big smile, her face filling the camera.

"Nah. I thought about it, but I'd be worried about Scotland Yard tracking me down. On the other hand, I don't think any jury of my peers would convict me."

"That frustrated already? Poor boy." She pulled back from the camera, which gave me a wider view. I could see she was wearing what looked to be one of my shirts, and, as far as I could tell, nothing else. She was lounging on her side on the hotel bed.

Time to change the subject before she gets me even more frustrated. "How's your client?"

"I'm so excited - it went really well, and it's just the kind of project I've always wanted. Plus with any luck, it could be a good break for us financially.. And, the best part, if this works out, I'll be able to do most of it from the studio at home. So a lot less travel."

"That's great. So you're working pretty intensely I guess?"

"Yeah, but it's good Actually, I've been having just a bit of trouble concentrating sometimes. Because I've been thinking about what we'll be doing when I get home, and I am so horny you have no idea. I think I'm turning into a sex monster."

"I think I have a pretty good idea how horny that can make a person, actually," Changing the subject didn't last long.

"So funny story. I made sure to pack, you know, my vibrator. And I was even smart enough to pick up an adapter for British plugs for it. But it turns out the voltage is higher here, and when I plugged it it, lots and lots of smoke came out if it. I set off the smoke detector and the fire alarm and everything. This was a few hours ago."

"You can't possibly imagine how little sympathy I have for you about that."

"Ha. Actually, it's OK. After they evacuated the hotel - did I mention that part? - I found a nice little shop a few blocks from here, and they're open late. So I went back there right before I called you. The girl set me up with a new vibe that works on batteries. So you don't have to worry about me. Now I'm internationally prepared."

Naturally. "You're nothing if not resourceful."

"I haven't tried it yet. So... wanna watch while I give this thing a test ride?"

She didn't wait for an answer. I stared intently at the screen as Claire positioned her laptop at the end of the bed, between her legs down at her feet, giving me a view that confirmed that, indeed, she was wearing nothing but one of my shirts. Her new vibrator was purple, and it made an audible hum when she flicked it on.

"Were the batteries included or did you have to buy them separately?" For some reason, that seemed like an important question at the time.

"Sold separately, but I got her to throw them in out of sympathy. Damn, this feels nice." And from the expression on her face, it clearly did.

I had, obviously, been there a fair number times while Claire climaxed, but I had never actually watched her masturbate. Or any other woman, for that matter.

It's a very different view than the closeup you get when you're involved. I realized that I was getting what was, in some ways, a more intimate picture of what feminine pleasure looks like than you get when you have your face stuck in the business end of her sex.

I guess couples in long distance relationships sometimes have video sex this way, masturbating on camera for each other. Of course, not quite this way, since there was no way for me to reciprocate. All I could do was watch.

Claire looses herself as she comes, though I had never appreciated how it affects her whole body. She grabbed a pillow with her left hand and pounded it on her chest, the way she'd sometimes pound my back when she'd have a good one with me. This must have been a good one.

"Oh, babe, I don't know what yours feel like, but I have to say, I almost feel a little bit bad for you that you can't have one right now, too."

"I could get the emergency key out of the envelope," I offered, trying to sound helpful. Hey, can't hurt to ask.

She regained her composure. "Oh, is this an emergency? Remember, I just had an entire hotel evacuated, so make it good."

"No."

"Then I guess you'll just have to wait. Poor boy." She licked her lips. "What's it been, three days since you had an orgasm? Hopeless. You might die."

"You're enjoying this, aren't you?"

"Maybe a tiny little bit, yeah. Try to console yourself by imagining what you're going to do with me when I get back."

I was in for a long couple of days.

---

Claire's flight on Thursday was mercifully un-delayed, and the airline meal must have been sufficiently filling to dissuade Claire from torturing me with another long dinner. After unpacking and taking a quick shower, she announced that she was "ready for bed".

"Two more and I'm all yours, babe," I could hear from the bedroom as I was taking my shower.

Claire was already naked, lying on her stomach in a way that accentuated her curves, her head turned away from my side of the bed.

"You look ready for a spanking." She really did.

"Have I been naughty?"

"You have, but not for making me wait. For tricking me about the London trip. If I had known, I could have gone with you, and you could have made me wait in person."

"Aww, that would have been nicer, wouldn't it? I wasn't thinking." She wiggled her butt, and I rubbed her backside and legs, finally giving her a couple gentle, but definite, spanks.

"I should be naughty more often then."

I continued to spank her slowly, a little harder, just enough to sting a little and get her blood flowing. I let my hands wander between her legs between slaps. She was very wet. I spread her legs just wide enough to give me good access, rubbing around, but not quite touching, her clit.

After a few minutes of this, she started moaning, and slowly humping up to meet my hand as I reached between her legs. "Do everything you're doing, but harder, please."

I obliged. Once her cheeks reached a more uniform shade of red, I started directly rubbing her clit. She quickly started moaning louder and louder, climaxing within a couple of minutes of this.

"Oh, babe. You know exactly what to do when you want to."

"I'm motivated."

She turned to look at me. "So that's one down, and just one to go now."

"No, two to go."

"Didn't you notice? I came pretty hard there."

"You said with my mouth. That was with my hand. I still owe you two. I'm not cheating like I didn't in high school here."

She sat up, looked at me skeptically for a moment, as if to see if I was serious. Then she kissed me harder and deeper than ever before.

"Maybe you're not so hopeless after all. I love you, babe. I'm ready to get started whenever you are."


To be continued...

 

Remedial Education
Part Six: Vacation Blues
by MaybeNextTime​

We both knew that Claire's trip to London had been a turning point for us. She had proven to me that I could survive a little (well, a lot of) frustration, and I had proven to her that, with enough prodding, I'm capable of seeing sex as something other than the shortest distance between me and an orgasm.

A week or so later, she announced the new plan. "I think we're ready to get serious with this. So from now on, I'm going to keep you locked on weekends. No orgasms for you from Thursday until Monday."

"No sex on weekends? Did I do something wrong?".

"No, no babe. I'm not punishing you. And did I say no sex on weekends? Actually, we'll have LOTS of sex, I promise you that. You'll just have to find a way to enjoy it without coming. I don't think a day or two here and there has been enough time for you to figure out how to do that."

"I have to say, this sounds like a pretty harsh way to learn."

"Be honest, wasn't the weekend after I got back from London amazing? I want more of that, don't you? And don't teenage boys have to deal with a lot worse? At least the ones who didn't cheat the way you did, that is?"

"Yes, I do want that, and I know this is what I agreed to. I'm just saying it's going to be really hard on weekends."

"Are you making a really bad pun?" She grabbed my erection, evidence that I might actually be a bit more enthusiastic about her new plan than I was letting on.

"OK, I mean difficult."

"It's just weekends. I don't want you so frustrated you can't concentrate at work. See, I'm not so cruel. I've thought about this. I hope you appreciate that. And I'm sure you'll find a way to make the best of it."

---

She went out of her way to make my locked weekends as frustrating as possible. At first, I tried to fill the time with unsexy distractions, but Claire made that strategy all but impossible. Starting each Thursday, she'd barrage me with every temptation she could muster, up full blast. Her clothes, her movements, the way she'd touch me and talk to me all sent unmistakable signals of sexual possibility. She broke down my defenses as quickly as I could erect them, if you'll forgive the pun.

Don't get me wrong. It was definitely fun to play with her so intimately and intensely. And I did love exploring her body and finding new ways to please her. But by Friday night I'd be counting the days and the hours until the weekend was over. I tried not to let her notice.

She noticed. "Babe, you know how lucky you have it, right? Come every Monday, I've been letting you fuck me. Normal teenage boys have it much harder, you know. They don't get weekly relief the way you do."

"Yeah, but their girlfriends aren't as sexy as you are, so they aren't suffering as much as I am."

"Aww babe, you're so sweet sometimes. Anyway, it's Saturday, so you'll just have to suffer through this for a couple more days. Can you do that?" Then she kissed me, starting with my mouth but working her way down to an extended session of sucking and licking my cage. It was cruel, no question, but I suppose I wouldn't have wanted to be anywhere else, either.

---

In spite of all the time we spent having (or, depending on how you define it, not having) sex, Claire and I both worked intensely enough to need some real time off. But between the two of us, scheduling time that we could both miss work seemed almost impossible. So when we found two weeks in January that we could both take off, we did what we had never managed to do before: scheduled a real live vacation. We booked a somewhat extravagant beach resort, exactly the kind of thing we both talked about often but that had never been a reality for us before.

When we arrived, we both wondered what had taken us so long. We had our own bungalow, private from the other guests and with the bedroom facing the ocean. The resort had a pool and a private beech, and we were close enough to town to be able to hit restaurants if we didn't want the resort food every day. The weather was perfect, not hot, but warm enough that you could spend all day in a swimsuit if you wanted. And no Internet or other real-world distractions. It felt like we were on our honeymoon.

"Sweetie, I hope the weekend rule doesn't apply here, because even though it's Friday, I really want to fuck your brains out right now." No sense beating around the bush.

"Actually..." I'd learned to worry whenever she'd start a sentence that way. "I've been thinking. How long has it been since you gave me be back the key? About half a year, right?"

"Yeah, I think it was." Where was this going?

"There's something I'd like us to do. but I won't do it unless you agree." She took the key necklace off her neck. "I think this is a great opportunity for us, so hear me out."

"OK..."

"I want to keep you locked for our vacation. I know two weeks seems like a long time, and I know you've been looking forward to the prospect of having wild, orgasmic sex in this wonderful place. But I this is a great chance for you to really learn how to appreciate what sex can be. Our weekends have been good, but every Monday, you go back to your old self, don't you?"

"Maybe, but two weeks? And on our only vacation? This could easily ruin our trip for me."

"Ruin it? Maybe, but I doubt it. Don't you enjoy our weekends together, even on Sunday? Even when you can't come? You seem to have adapted pretty well."

It was true that I had pretty much stopped counting down to Mondays, and on I had indeed learned to appreciate weekend sex with Claire as something other than an exercise focused on me coming. But I also still needed and enjoyed the weekday sex. And two weeks? "I don't know, do I have a choice?"

"Yes, of course you have a choice babe. I wouldn't have asked if I didn't mean to give you a choice. But I hope your choice will be to trust me here. I think you'll surprise yourself. And have I been wrong about any of this yet?"

She did have a point. Deep breath. "OK, you can keep me locked. But how about this? If it's not working out after a week, we renegotiate?"

"Actually, no, that won't work. I don't want you thinking you you have an out. I want you committed. So if you say yes, I'm mailing the key home today. If you're in, you're in. You'll have zero chance of an orgasm for two weeks, and there's nothing either of us will be able to do about it. Just like we were two teenagers."

"You really have thought about this, haven't you?" I didn't want to admit it, but I had been waiting for her to do something like this since I gave her the key in the first place. But ailing the key back? This was serious. And I think I loved her for it. "OK, if you think it's the right thing, we can do it. Send the key back." Part of me couldn't believe I actually said that, but part of me couldn't imagine saying anything else.

She had packed an express delivery envelope, the slip already made out, in her suitcase. She put the necklace in and we walked it to the dropbox in the lobby. Once it was safely in, beyond retrieval, she grabbed me, whispering in my ear, "Now for the next two weeks, there's nothing else to think about. I'm yours to do whatever you want with." I strained at my cage.

By the time we got back to the room, I desperately wanted what I now had no way of getting. Had I just made a huge mistake? It didn't matter. We were now committed.

---

Claire had, of course, planned her vacation wardrobe to include outfits that filled me with as much raw desire as possible. And she pulled it off expertly. It's funny the way that works. I know very well what every inch of Claire's body looks like, and I love looking at her naked. Yet covering herself in certain ways is still somehow sexier. Even with no mystery in my mind about what would be found underneath, Claire can dress with an effect that draws me to her in ways that even nudity can't approach. Every time I'd look at her, at the pool, at dinner, wherever, I'd immediately think of how badly I wanted to be fucking her.

Bathing suits do not hide cages well, so we amused ourselves by trying to catalog the status of the various couples. A few honeymooners and dating couples, clearly there to focus on sex. with the guy caged and the woman prominently wearing the key around her neck. This was not for chastity - their expressions were clearly too relaxed for that - but as a public statement of their couplehood. You knew the cages would come off as soon as they'd get back to their rooms. Then there were the teen couples, with a boyfriend or girlfriend brought along on a family vacation. The girls, who didn't have the keys on their necks, of course, were varied in their attitudes. Some, you could tell, really wanted to break their boyfriends free the way Julie did with me. (I wondered if any of the girls at the resort were that resourceful or daring.) Others were clearly enjoying their position as unattainable objects of their hapless, helpless, boyfriends' desires, cock teases with a captive audience. I wondered which kind of girl Claire had been at that age. In any case, it was clear what kind she had become. And here I was, as helpless as any of the boys.

The teen boys in those couples were all caged, of course. Their expressions all betrayed the same confusion. On the one hand, they were obviously, visibly, profoundly frustrated. On the other, at least they were with their girlfriends. So close and yet so far. Was it cruel to put a kid through this? Maybe, but they say it's part of growing up.

And then there was me. Teen situation, adult body, And unlike the kids, I knew exactly what I was missing.

---

Our first couple of days actually went pretty well in spite if my growing sexual frustration. There were enough fun activities to make it hard to resist having a good time, And we spent a lot of time in the privacy of our bungalow, with Claire climaxing loudly enough to make us grateful we didn't share any walls with our neighbors.

By Thursday or Friday, I started to loose it. We were making out in the couch, in front of the fireplace, sipping a bit of wine we had ordered from room service. It was great, until it became unbearable. "Claire, I can't take this. You have no idea how frustrating this is."

"What do you want to do babe?"

"I want to get out of this damn cage. I want us to have normal, grown up sex. I want to fuck you. I want to come inside you." I was suddenly desperate and almost out of control,

"I love that you want that babe. I miss that sometimes, too, and I love it when you tell me what you want. It gets me even hotter."

Hearing that didn't help. "They why can't we?"

"I don't have the key. We sent it back, you know that."

"This is really getting impossible for me."

"Oh babe, I'm sorry. There's just not much we can do though." I think she realized I wasn't kidding.

"I know you can't do anything, I just need to tell you how hard this is getting for me."

She looked at me intensely. "I have an idea. I know what we can do. We can go to the emergency room. We explain that I don't have you key and that you're never learned to control your urges so this is a life and death emergency and would they please cut your cage off so that we can have sex right there on a stretcher. How's that sound? I wonder if our insurance covers that."

I looked at her, and she looked at me, serious and wordless for an long moment, Then we both laughed hysterically.

"Let's just go to bed and hold each other, OK, babe?" There was genuine comfort and sympathy in the way she said it.

She cuddled me, I and cuddled her, until we both fell sleep hours later. I woke up first, around dawn. Neither of us had gotten much real rest. Looking at her I realized how especially lovely Claire was in the morning light, the sun skipping over the ocean to illuminate her curves. I could stare at her for hours like this. She eventually stirred awake, and opened her mouth to say something. I kissed her before she could get any words out.

As intense as my frustration had been last night, I somehow felt luckier to be there, with Claire, in my cage, than ever before. I ran my hands over her body, and she over mine. As the sun rose We had, that morning, the first real sex of our trip. Not just me giving her an orgasm, but mutual exploration. If I hadn't been caged, I'd have penetrated her, no doubt. But that wasn't an issue that morning. I just wanted to be there in bed with her, and to make her as happy as she was making me.

---

Afterword:

The rest of our vacation went pretty well after that night. I had moments of intense frustration, to be sure. the physical urge to climax becoming stronger with each day. By the time we got home, I felt literally ready to burst.

What I had learned was that the frustration comes in wave, and that, with Claire, I could get past them, to a different kind of satisfaction that I had never before experienced. I wanted an orgasm, don't get me wrong. But had I found ways to focus that energy on Claire. I had several more episodes of wild, angry frustration, but that were followed by some of the best, and most exhausting, sex that we had ever had.

When we got home, the key was waiting for us. But it was Saturday, still the weekend, and Claire reminded me that I wouldn't be unlocked for another couple of days. I knew I could wait.