Fifteen Days Episode Three

The following morning I was sitting in the kitchen nursing a very strong cup of coffee when Jenny walked in. She had on that same gray skirt from our first Monday together, but it appeared noticeably shorter than before. Rather than bare legs, she wore sheer black thigh-high stockings secured with bright red garters. The garters were hard to spot while she was standing, but as she sat beside me the hem lifted nicely, revealing both the clips and a few inches of her exposed thigh. I had to force myself not to stare, only to notice that her white blouse seemed tighter than usual, and if anything, another button had popped open. Honestly, I didn’t need my coffee anymore; seeing Jenny dressed like this every morning felt like getting an immediate hit of adrenaline and testosterone.

“What do your coworkers think about your ‘new look’?” I asked.

She smiled. “I’m definitely catching some eyes, but no one has said anything yet.” I suddenly found myself incredibly jealous of the men in her office. At least they could go home and relieve themselves at the end of the day.

But there was nothing for me to do that day. That evening we went out to dinner with another couple. Since it was casual, Jenny wore cutoff jeans and a tank top. I’d seen those shorts before, but they were clearly shorter now. John couldn’t keep his eyes off Jenny all night long. I tried keeping the conversation light, but my balls felt like they were boiling over and I struggled to follow along. I had always thought of Wendy as cute, but in my current state, she looked absolutely stunning. At one point she asked Jenny about the key hanging on a chain around her neck.

“Oh, it’s just a reminder,” she said. As if I needed another; I was thinking about that key constantly.

The next night, Thursday, Jenny showed up in a sexy schoolgirl costume. It included a very short plaid skirt (more of a kilt really) and a waist-length white top that rode up occasionally to give tantalizing glimpses of her bare midriff. She completed the look with one of my ties and a pair of faux glasses. This was new; she’d worn sexy attire before but had never quite put on a full costume. It was incredibly arousing. Then she surprised me by announcing it was time for maintenance. I wasn’t embarrassed by my erection anymore, in fact, I rather liked having one because every minute with an erection meant another minute outside the belt. However, after the maintenance was finished, she brought out the handcuff and locked my hands together in front of her before leading me into the kitchen.

She had a rope tied to one leg of the dining table, where a pad of paper and pen were waiting. She told me to sit opposite the rope, which she then attached to my cuffs. Sitting next to me, she took hold of my cock. It became hard again within seconds.

“Now it’s time for your homework,” she said. “You need to write an essay explaining why you believe I should let you cum. You’ll be graded on neatness, spelling, grammar, and content. You have forty-five minutes.” She stood up, grabbed an old kitchen timer from the stove, and set it for 45 minutes. “Begin.”

This was going to be difficult. My hands were cuffed together so I could reach the pen and paper (though not my dick or balls). That would make writing awkward (“neatness” is out the window). And Jenny standing there in her schoolgirl outfit would surely distract me too. Fortunately, that didn’t turn out to be a problem. After a minute she left; I heard the apartment door open and close as she went out, then returned with a box of old work clothes and tools from the storage unit just outside. What was happening? I wondered, glancing at the timer. A few minutes had already passed, so it occurred to me I should get started on my essay.

Concentrating was tough because Jenny was bent over the box looking through its contents, giving me a great view of the red g-string panties she wore under her kilt. It was hard tearing my eyes away from that sight back to the paper. After another minute she stood up holding a pair of knee pads I had used during a summer job with a contractor a couple of years prior. She placed them on the table and looked at the blank pad beneath my cuffed hands.

“You haven’t even started writing,” she pointed out. “And the clock is ticking.” She propped her foot up against the other chair. The schoolgirl skirt lifted nicely, proving another glimpse of the panties below. She strapped one knee pad to her knee, then repeated with the other. I can be a bit slow on the uptake sometimes, but by then I realized what she was doing. It was going to get much harder to concentrate on my “essay” very soon. I kicked myself for letting her distract me so long.

I started writing desperately, not even sure of what exactly. Jenny dropped down onto her knees and crawled under the table. A few seconds later, I felt her gently pushing my legs apart, then felt her breath against my cock. Next, I felt her tongue start at the base of my shaft and lick very slowly all the way up to the head. Oh god, it was both incredible and agonizing. And that was only the beginning; there were still almost 35 minutes left on the timer.

After a few minutes, I couldn’t take it anymore and tried bringing my legs back together. Jenny grunted as I squeezed her, then said sternly, “Pull your legs apart again, or it will cost you a full letter grade.” I spread them wide once more with an effort of sheer willpower. Jenny returned to her slow, agonizing blowjob for another minute before saying, “If you do that again, it’ll cost you another week in the belt.” There was no doubt in my mind she would follow through.

Between trying to keep my legs open and having Jenny’s tongue working along my dick the whole time, I wasn’t able to write anything coherent. By the time the timer bell pinged, I could hardly think straight; I was so desperate it felt like tunnel vision had set in and breathing was difficult. I managed to scrawl out what was less an essay than an unconditional surrender:

Dear Jenny, I think you should let me cum whenever you are ready. I am horny, frustrated, and desperate. You should keep me that way as long as you want. I really want to cum. I’m begging you to let me cum. Please let me cum. But only if you wish it. You should only let me cum if you feel like it.

The letter was pathetic and desperate, but she loved it. However, she said I failed. It wasn’t really an essay. “‘I really want to cum’ is not exactly a thesis statement,” she remarked. I would have felt worse, but I was pretty sure the whole exercise was just another way to torment me. I told her so, and she just laughed. “It would have to be a pretty convincing essay, that’s true,” she said.

I fell asleep quickly that night; I was exhausted from the last couple of days. But I woke up in the middle of the night with my cock straining against the belt. I could still feel Jenny’s tongue running slowly up and down me as if it were a ghost giving me blowjobs while she slept beside me. And why not? I had given her two more orgasms before drifting off that night.

Jenny didn’t have to work until later, so by the time she climbed out of bed I was already up and ready for whatever came next. She entered the kitchen wearing a kimono with her hair all messed up. She looked sexy as hell. Me? I was feeling a bit cranky from poor sleep over the last two nights combined with my sexual frustration. When she said good morning, I just grunted and slammed my coffee cup down on the counter.

“What’s the matter?” she asked.

I snorted. “Really? You want to know what’s wrong?”

She turned toward me, eyes blazing, staring intently. Before this moment she had looked sexy; now she looked magnificent. “Oh, you agreed to play this game and now you’re telling me you can’t handle it? What about that nice note you wrote last night?”

Give her credit: she knew exactly how to push my buttons.

“My male ego couldn’t stand being wrong. ‘Of course I can manage,’ I said, foolishly. ‘Well, that’s reassuring,’ she replied, relaxing back into place. She stretched out, and against my will, a sharp pull in my groin as the kimono fabric tugged at her breasts. Without much fuss, she poured herself another mug of coffee. ‘I was thinking about releasing you tomorrow. But since you’re coping so well, I don’t see why an extra week in the belt would be difficult.’ Have you ever experienced heart sinking? That’s precisely what happened to me right then. My teeth ground together and I let out a low growl of irritation. Had I just missed my window to cum tomorrow? ‘Alright,’ I said through tight lips, though I didn’t feel alright. During the commute, it hit me that this was part of her strategy; Jenny never truly planned for me to cum tomorrow, she was merely seeking an excuse to “extend” my confinement. Yet I was desperate beyond measure. I called her repeatedly throughout the day, leaving messages apologizing profusely for losing my temper earlier. She didn’t answer a single call. Eventually, I left another message reiterating my apology and pleading with her to reconsider making me wait one more week. That evening, feeling that some flattery was warranted, I had dinner already cooking when she arrived home. For work she’d worn jeans and a sweatshirt, but changed into cutoff shorts and a cropped black tank top afterward. The shorts were perhaps even shorter than usual, barely concealing her backside. After we ate, while I was cleaning up the dishes, she approached and stood beside me. ‘I’ve been reviewing your request,’ she said. My thoughts raced. Request? ‘To cum?’ I asked with hope. She smiled. ‘No. Your request to reconsider my decision regarding extending your time in the belt. We need to resolve that before I even consider letting you release.’ For a moment, a sarcastic remark hovered on my tongue, but since dinner had gone so smoothly and I didn’t want to ruin it, I held back. ‘I would appreciate any chance to make amends for this morning’s behavior,’ I said formally. Her expression brightened. ‘Excellent! Come into the bedroom once you finish washing up.’ I washed slowly, procrastinating. You can wash dishes just enough without making them too clean, after all. Also, I sensed that whatever she had planned would leave me more frustrated and desperate than ever before; my patience was nearly at its limit. Yet I knew better than to make her wait. Entering the bedroom, I spotted the handcuffs attached to the headboard. Jenny directed me to undress and lie on my back, then secured my wrists with the cuffs. She began slowly dragging a finger along my cock; hardness came instantly. ‘Okay, here are the rules,’ she stated. ‘The longer you allow me to play with your penis, the more I will reduce your extra week in the belt. Understood?’ I nodded. Her finger was already driving me mad. ‘Though you may tell me to stop at any moment; if you do, we are finished. You lose another opportunity to shorten your time. Clear?’ I nodded again. ‘Also, should you touch either yourself or me at any point during this session, you automatically incur an additional two weeks in the belt. Agreed?’ For a second I was puzzled. How could I possibly…? Then she ceased her teasing, retrieved the cuff key from the nightstand, and unlocked my right hand before resuming her gentle stroking of my cock. The situation felt diabolical. My free hand hovered nearby; it would have been simple to reach down and grasp my dick for some desperately needed relief. I doubted she could have prevented me even if she tried. It reminded me of that night years ago when we first began “chastity play,” where escaping self-pleasure was easy but unnecessary. Yet this felt ten thousand times worse after nearly two weeks of relentless teasing without release. Clutching the bed sheets, I held on tightly, afraid to let my hand drift closer to my cock as she continued her finger work. My mind spun wildly. One moment I considered how easy it would be to reach down and jerk off, thinking myself a fool for hesitating. The next, I realized this was a test; failure meant two more weeks in the belt, perhaps longer if I managed to cum anyway. Then I futilely tried devising ways to coax Jenny into making me cum, maybe tricking her into doing it. Soon enough, my thoughts returned to grabbing my dick again. While she had tormented my cock for the last couple of weeks, she seemed to be tormenting my mind even more. After a while, Jenny began massaging my balls with her other hand. ‘Wow, these are quite full,’ she said laughing. ‘You must really want to release some pressure.’ She continued working on both my cock and balls simultaneously. ‘God, I bet it would feel wonderful having that come out of the end of your dick.’ She twirled a fingertip in circles over the tip of my cock. ‘I can just picture all that cum shooting right here.’ I could imagine it too; almost feeling the pressure building up through my shaft and bursting forth. Almost. I tightened my grip on the sheets, desperate to keep my hand away from my anguished cock. Jenny shifted her attention from my balls to grasping the base of my cock with thumb and forefinger. She moved them slightly but mostly kept my cock steady. Meanwhile, the fingers of her other hand gathered near the head, teasing only the very tip area. ‘You know, there is plenty of room for a third hand on your dick right now. Wouldn’t it feel so good to reach over and take hold?’ Oh god, yes! That was exactly what I wanted most in that moment! I groaned in protest and gripped the sheets even tighter with my free hand. After a minute she said, ‘Alright then,’ returning to teasing along the entire length of my cock, occasionally including my balls. A couple more times she left most of my dick alone, focusing only on the tip and base, inviting me to touch myself. The last time almost broke me. She asked “Are you sure?” three times before slowly licking up the shaft with her tongue’s tip. I nearly gave in; suddenly the chance to just touch myself for a few seconds seemed worth another two weeks in confinement. Tears of frustration pricked my eyes. But enough logic remained that I decided to accept the loss. ‘Please stop,’ I said. ‘I surrender.’ ‘So pity,’ she replied. She paused her teasing long enough to lock my free hand back into place before resuming her licking of my cock. ‘Hey —’ I started, trying to squirm out from under her. She halted. ‘Victory lap, remember?’ She gave me a few more licks. ‘And just for that, I’m taking an extra-long one.’ And she did. Then she said, ‘Let’s see how much time you’ve earned back.’ She took paper and pen from the nightstand, sat cross-legged near the foot of the bed, and began writing with one hand while holding my dick in the other. Slowly stroking its underside with her thumb… ‘Okay,’ she announced after a couple of minutes. Pausing briefly to fold the paper, she held it up with one hand while continuing her teasing with the other. “On this sheet I have written the day you will be allowed to cum. It is no sooner than Sunday and no later than next Saturday. Also, I reserve the right to extend that time if your behavior annoys me again.’ I winced in frustration. It was Friday night. Could I endure another eight days — or even longer — of this? But she wasn’t finished. ‘Or,’ I opened my eyes. ‘Or, you may cum tomorrow — guaranteed — provided you spend two more weeks in the belt.’ But I could tell there was more to come. ‘Or…?’ I prompted. She smiled. ‘Or…you can cum tonight — indeed, within the next five minutes — provided you remain in the belt for a full month.’ I pondered this option. The idea of coming right then sounded very appealing, especially with her thumb still working my dick. But another whole month? Or even two weeks extra?”,“subject”: "", “post_id”: 114686 } ],

What if she kept me locked up the entire duration without letting me release? We were just under two weeks into this cycle, and I was starting to lose my mind. Then it hit me—the letter.

“What’s your wish?” I inquired.

“Mine? You’re the one sitting on a backlog of two weeks’ worth of seed. The choice is yours,” she replied.

But I understood what she really meant. While options two and three prolonged my time in the chastity device, they had clear expiration dates and allowed me to cum either that evening or by tomorrow morning. By choosing option one, however, I didn’t just forfeit an indefinite release; under Jenny’s extension clause, I also surrendered her authority over both when I would be unchained and when my next release would occur.

“I accept whatever is written on the paper,” I said.

“Wonderful!” she exclaimed cheerfully. She then bent down to embrace me as though I had presented her with the perfect birthday gift.

To be continued