Locktober's End- Chapter 5 [chastity] [tease and denial] [slow burn]

NOW

When I came back with the icepack, the blindfold was still in place. He was still sitting with his hands behind his back. He seemed quiet and still with anticipation, listening for every one of my movements. He was a good boy. I set the ice down on the couch for a moment and turned around so my back was facing him. I positioned myself over his knees so he could feel the hem of my dress brushing them. "Would you unzip me, Ben?"

"Y...yes, Miss Jessica."

I heard him take a deep breath as he reached up and, after a few incidental touches along my lower back (he was a good boy and didn't let his touch linger), found the zipper on the back of my dress and brought it down. "I hope you don't mind that I'm taking off my dress", I told him, stepping out of it as I moved away from him. I gently kicked it to the far side of the couch and glanced down at what I had on underneath. "I think I feel a little more relaxed in bra, panties and pantyhose. Especially now that you can't see."

He reacted as if I'd struck him: groaning, pressing his fists into the back of the couch, pressing his knees together, curling his toes, lifting his hips off the couch and almost humping the air in a hopeless attempt at some kind of relief. Lower lip trembling. Was he close to crying already? Who knew that words could have such power?

I sat down next to him, close, reaching up to run my hand through his hair. I kissed his shoulder through his undershirt. His hands were still behind his back, clenched into balls and pressed desperately into the couch.

Such a good boy.

The fact that I knew he would be obedient made me in turn so much more comfortable, giddy, even light-headed. I didn't have to bind him to be assured that I was in complete control, and that was a beautiful thing. His desire for me made him infinitely more helpless than rope or cuffs would've. "Yeah", I added as I leaned my chin on his shoulder and continued to stroke his hair, "I bought some new lingerie a couple of months ago. Maybe I was even thinking about Locktober, about getting some nice obedient boy in my clutches. I really like this purple set that I've been wearing tonight, lots of floral patterns. It's really pretty. I almost want to show it to you..."

"Please, Miss. Please..." He squirmed on the couch. You'd have thought I was torturing him. I guess I was, in a way.

"Hmmm." I kissed his shoulder again, running a hand softly up his arm. "But do you think that would help you get soft? Do you think that would help your adjustment to NOvember? Or whatever we're calling this game?"

"Well...I mean, ah..."

I didn't think I would ever get tired of his stammering.

"I mean...ah...well, no, I guess not exactly, Miss, but..."

"See?" I was giggly again, kissing him on the jaw. "I'm just trying to help you."

He groaned again, shifted on the couch. It seemed his legs couldn't quite sit still.

"You're evil", he whimpered.

I giggled and kissed him again. "Didn't I warn you, silly boy? Didn't you tell me you wanted to be teased? And didn't I promise to remind you at the best possible moment?"

"Y...yes, Miss", he whimpered hopelessly.

"Besides", I giggled with another kiss on the jaw, "you haven't earned lingerie yet. I still haven't even locked you up! Did you really think I was going to let you see it while you were still free?"

Another groan, another helpless little thrust into the empty air.

"But we'll fix that in just a second. Unbuckle your belt for me, Ben. Unzip yourself, and slide your jeans down."

He obeyed immediately, his hands shaking. He unzipped his jeans gingerly, making sure the zipper didn't hurt his desperate, throbbing erection, and then raised his hips off the couch so he could slide his jeans all the way off. Now it was just a cute pair of black boxers. I liked the fact that I could enjoy the sight of him in undershirt and boxers, while he couldn't see me at all.

I reached behind me for the soft, flexible icepack (it had only been a minute or two since I'd gotten it, and it was still ice-cold), and with my other hand lifted the elastic of his boxers. "And now we'll just..."

I tucked the icepack in beneath the elastic, and immediately giggled at his BIG reaction. Legs kicking into the air, hips thrusting, exclaiming, whimpering...and finally settling back down on the couch with a mixture of groans and sobs. The beginning of acceptance.

"That's it", I whispered, letting one of my boobs brush his forearm and stroking his forehead. "No cumming for you. No climaxing. Just getting soft. Just getting locked." I kissed his ear, his neck.

"Please Miss, please", he whimpered almost incoherently. He was still squirming, but his movements had grown a little more placid. His body was beginning to submit, even if his mind was lagging behind.

"Now you need to concentrate on getting soft", I whispered. "So tell me more about Chandler. What was the first book of his you read?"

I was never going to get tired of the way he stammered when I abruptly switched the topic on him.

With a forlorn tone in his voice, he began with some difficulty to form a sentence.

THEN

Forming sentences even over the phone had been proving challenging for him.

"I...I didn't even know that I could..."

"Stop touching and then cum anyway?" I giggled. I couldn't help basking in the glow of what I'd just made him do. "Yeah, as long as we know each other, you should probably get used to that."

"God", he groaned miserably, his voice breaking a little.

"Why, Ben? How do you usually like to cum?"

"Well, I..." He stammered.

"Don't tell me you like to keep stroking all the way to climax?"

He sounded incredulous. "Well I mean...well...yes!"

"Goodness, how indulgent!"

He moaned.

"Yeah", I said quietly, "we're going to have to put a stop to that. Boys don't get to do much of that on Planet Jessica."

Another moan, delicious.

"I like limiting your pleasure", I chimed happily. "I tried to warn you, Ben. How did it feel, by the way?"

"...Very, very frustrating."

"Awww."

"Like there was such an intense build-up, and then...it all kind of faded away. I mean, it wasn't totally without pleasure, it felt good, but nowhere close to..."

"To how it could've felt if I'd let you keep touching yourself?" I couldn't keep the giddiness, nor the giggles, out of my voice.

He groaned again. "Yes."

"If I hadn't made you stop at the last second?"

"Y...yes."

"Well, that's no longer your choice to make, Ben. Not for now, anyway. And you kind of like that, don't you?"

"I...I love it, Miss."

"Mmmm-hmmm. I'm glad."

I listened to the sounds of him shifting around over there, in the apartment I hadn't yet seen. I imagined wood-paneling, books and DVDs, a couch, a painting more naturalistic than surreal (perhaps mountains or a body of water), maybe a cat. That was how I pictured it, anyway. But he was still something of a mystery.

I asked, "Do you have a cat?"

"Sadly, no. I like cats, but I don't have one." He chuckled. "Maybe I should get one. Maybe I should...I don't know. All of a sudden, I feel like I can do anything. Wow. Wow! You being in control like this, I...and the way you made me...I...I really feel like I could use a cigarette right now."

"Do you smoke?"

"No, not really. I buy a pack maybe once a year and take my time getting through it.

You?"

"For a little while in my 20s. I quit a long time ago, though."

"That's good."

"I started The Long Goodbye, by the way."

"How do you like it?"

"It's almost unbelievably well-written."

"Yeah."

"Marlowe can be a bit of a dick."

"He can, that's true."

"In addition to being a dick. A private dick, I mean."

"And having a dick."

"I bet he got to touch it however he wanted." I couldn't resist. "Unlike some people I know."

Another satisfying groan from the other end, though a bit subdued this time.

"But so far I'm enjoying it", I continued. "Terry is a really interesting character. That friend who you know is kind of doomed, but you stay friends anyway."

"I do like those kinds of stories. Maybe it's a little like The Great Gatsby in that way."

"Remind you of someone?"

"Yes. Except I don't know if I'm the friend who's relatively with it, and only doomed in the long-run in the same way we all are, or the friend who's more immediately and tragically doomed. I don't know whether I'm going to fade away or burn out."

He seemed quite unguarded in this moment. Vulnerable. I'd never heard him talk quite like that before. Then again, we'd known each other less than a week. "Well, stick with me for a while, and I'll try to tell you."

"Sounds like a plan."

"Haha...ahem...so listen, I have two questions for you. One is kind of sexy, and the other is totally mundane. Sexy one first?"

"How can I say no?"

"Hmm. I didn't think you would. Okay then, non-sexy question first!"

His voice was aggrieved. "My god, you are such a tease!"

"Oh, you love it."

"I do."

"Ahem. Non-sexy question commencing. Utterly, completely, totally absent of any sexual content. Do you have any plans for Halloween on Friday?"

"Not really. Not aside from watching Michael Myers chase around some teenagers, and answering the door if any revelers come around."

"I don't have any big plans, either. Maybe you'd like to come over and watch Michael Myers with me?"

"I'd love to."

"Great! Talk to you Friday, then?"

"Wait, wait!"

I tried to play it straight, but couldn't help giggling. "Ben, I'm right here! What's wrong? There's no need to panic!"

"What about the...the, um, sexy question?"

"The what? Ohhhhhhh, oh, oh. Right. I did mention a sexy question, didn't I?"

"Yes, Miss."

"I did, didn't I? Gosh, what a shame, now I can barely remember..."

"God...you're so good at this. I'm in so much trouble."

I giggled at his ostentatious agony. "You sound like you're having some kind of spasm over there."

He cleared his throat. "Ahem. No, no, no, I'm just...just fine over here, Miss..."

"Okay, okay. Sexy question. Here we go. Sexy question, but also serious. Are you ready?"

"I've never been more ready in my life."

"That night we first met...you kind of made a reference to November being just around the corner...as if that held some special significance. As if you were aware of the connection between October and femdom. So what I mean to ask is you is..."- now it was my turn, surprisingly, to feel just a little shy and tentative- "do you know about Locktober and all?"

He hesitated for a second, seemingly a little embarrassed, but then he chuckled a little. "Ah... yeah, I know about it. And it did seem to me that that was what we were dancing around. But I had always just assumed it was mostly this internet thing that didn't exist in real life..."

"Well, the border between those two worlds is becoming more porous every day."

"You're telling me."

"So meeting a real practitioner out in the wild was pretty unexpected?"

He took a deep breath. "You are a practitioner, aren't you?"

"Yeah, Ben, I am. I've done it a number of times, with a few different partners. Not this year, though. But when you said that November was another month...were you suggesting that you would like to participate? In whatever the November equivalent would be?" I laughed. "I mean, I know they already have NOIRvember...you're probably into that, right?"

"Oh yeah, I am. November is always a good month for watching noir, thrillers. Movies with, uh, beautiful femme fatales who wrap hapless guys around their fingers..."

"Uh-huh. I'm so surprised you like that idea."

"But maybe this could just be called NOvember", he suggested, emphasizing the first syllable. He didn't sound quite as twitchy as I might have expected, discussing all this, perhaps because he'd just had an orgasm- even if a ruined and unsatisfying one.

"Mmm. I like it. It's simple but effective, makes its point. And it's something I'd look forward to saying to you a lot over the course of the month."

"No?"

"Yes."

Slight whimper from the other end, gratifying. "I...I love the idea, Miss."

"Hmmm. I'm not sure you know what you're getting yourself into. And on one hand I like that. But on the other hand..."

"May I...may I ask a question?"

"Of course."

"If I agreed...does that mean I'm agreeing to...to an entire month...you know, without...?"

I bit my lip. Truthfully, I wasn't sure how far I wanted to push him, how fast. I liked him and I didn't want to scare him off. Then again, I had a feeling that wasn't going to happen...and missing out on Locktober had put me in an especially dominant mood.

"I would say...that that is for me to know...and you to find out."

Sharp inhalation from the other end. "That...that sounds good to me."

"Does it? I like you, Ben, and I don't want to scare you off. And I know that you're a beginner. I would say that if, in the course of the month, you're having a real problem with...um..."- I giggled- "being distracted from important things in your life, you of course have the freedom to let me know, and we can probably work out some kind of compromise. But yeah, if we go down this path...I'm in control, you know? There's no rule that says I have to let you cum, say, once a week. Unless you...want there to be? NOvember on, you know, easy mode?"

"I...I don't think so."

"Good!"

He whimpered, recovered. "We'll have a...a safeword, just in case?"

"Of course."

"I almost can't believe this is happening."

"I'd say our meeting was most fortuitous."

"I...I'm in."

"Yay!" I clapped a little, so he could hear over the phone. I felt like we'd just agreed to take a little vacation together. A little vacation to la-la land.

"May I ask how it works? Is there a cage, or...?"

I smiled. "Yes, Ben, there's a cage. I promise it won't be too onerous. You'll be able to shower, clean yourself, and you won't have to wear it in public if you don't want to. We'll be totally safe. But yes", I repeated, lowering my voice, "there's a cage."

"I've never..."

"Don't worry your little head about all the details. I'll take care of everything. Before you know it, you'll be nice and soft and helpless for me. Won't that be nice?"

Gratifying whimper from the other end. "Y...yes, Miss Jessica."

"Good boy."

"So...see you on Halloween night?"

"Actually, can I...ask one last quick, sexy question?"

"By all means."

"Seeing as we're next going to see each other in a couple of evenings...and November doesn't start for another 60 hours or so...am I, um, restricted until the next time I see you?"

"Restricted. Oh. Oh." I laughed, suddenly realizing what he meant. I thought about it. And as I thought about it, I realized that at least a good 51% of him probably wanted me to say that he was. But maybe it would be fun to make him wait a little longer even for more denial. And to find out what he would do, if given the choice. "Um. No, Ben, I don't think so. I leave the matter entirely in your, um...hands."

"Ha."

"You're free to do whatever you like for the next 60 hours or so. Give or take, depending on what time exactly we meet up." He could either try to brace himself for the upcoming month with a last-minute orgasm or two or three, or he could take his chances with me on Halloween night. I wondered which he would choose.

"I guess I'll text you on Friday, then."

"Great. We'll meet up Friday evening, maybe get some food. Watch a movie or two. Then we can discuss what's coming next." I paused. "Which won't be you."

He groaned and laughed at the same time, on the other end. "I was waiting for that."