The next morning I sat sipping an extra-strong batch of coffee when Jenny came into the kitchen. She was wearing the same gray skirt she'd worn that first Monday morning, but it definitely looked like it was shorter. Instead of bare legs she wore sheer black thigh-high stockings, held up with bright red garters. The garters were tough to see while she was standing up, but when she sat next to me the skirt rode up nicely, showing the garters and a few inches of bare thigh. It took a physical effort to tear my eyes away, only to see the same white blouse, which if anything looked tighter, plus I could swear she had another button undone. At least I didn't need the coffee anymore; seeing Jenny in her outfits every morning was like getting a big shot of adrenaline and testosterone first thing.
“What do the people at work think of your ‘new look’?” I asked her.
She smiled. “I’m definitely getting some attention, but no one’s said anything yet.” I was suddenly very jealous of the guys at her office. At least they could go home and jerk off at the end of the day.
There was no jerking off for me that day. That night we went out to dinner with another couple. It was informal, so Jenny wore a pair of cutoff jeans and a tank top. I'd seen the cutoffs before, but they were obviously shorter now. The guy, John, couldn't take his eyes off Jenny all night. I tried keeping the conversation light, but my balls were boiling and I couldn't keep the thread. I'd always thought John's girlfriend, Wendy, was cute, but in my current state, I found her absolutely stunning. At one point she asked Jenny about the key on the chain around her neck.
“Oh, it’s just a reminder,” she said. As if I needed one; I thought about that key constantly.
The next night, Thursday, Jenny appeared wearing a sexy school girl outfit. It consisted of a very short plaid skirt (more of a kilt, really) and a waist-length white top that rode up at times for a tantalizing glimpse of her bare midriff. She'd finished off the ensemble with one of my ties and a pair of fake glasses. This was something new; she'd worn sexy clothes before but had never put on a costume. It was incredibly hot. Then she surprised me by announcing it was maintenance time. I wasn't embarrassed by my erection anymore, in fact, I kind of liked it since every minute I had a hard on was a minute I couldn't be put back in the belt. After maintenance was done, however, she brought the handcuffs out, locked my hands together in front of me, and led me into the kitchen.
She had a rope tied to one of the kitchen table legs, and a pad of paper and a pen lay on the table. She told me to sit down opposite the rope, which she then tied to the handcuffs. She sat down next to me and took my cock in her hand. It was hard again in seconds.
“Now, it’s time to do your homework,” she said. “You’re going to write an essay explaining why you think I should let you cum. You’ll be graded on neatness, spelling, grammar, and content. You have forty-five minutes.” She stood up, took an old kitchen timer from the stove and set it for 45 minutes. “Begin.”
This was going to be tough. My hands were cuffed together so I could reach the pen and paper (but not my dick and balls). That was going to make writing awkward (so much for “neatness”). Jenny standing there in the schoolgirl outfit was going to be a distraction, as well. It turned out that was not going to be a problem, however. After a minute, she left, then I heard the door to the apartment open, then close, and she came back in with a box of old work clothes and tools that had been in the storage unit right outside the door. What was going on? I wondered, then looked at the timer. A few minutes had already gone by, it occurred to me I should get started on my essay.
It was tough to concentrate, though, Jenny was bent over the box while she looked through it, affording me a nice view of the red g-string panties she had on under the kilt. I tried tearing my eyes back to the paper but it was difficult. After a minute she stood holding a pair of knee pads I’d used for a summer job with a contractor a couple years before. She set them on the table and looked at the blank pad of paper under my cuffed hands.
“You haven’t even started writing,” she said. “And the clock’s ticking.” She put her foot up the other chair. The schoolgirl skirt rode up nicely, proving a glimpse of the panties beneath. She strapped one of the knee pads to her knee, then repeated the process with the other one. I can be a little slow to catch on sometimes, but by then I realized the implications of what she was doing. It was going to get much more difficult to concentrate on my “essay” very soon. I kicked myself for letting her distract me this long.
I started writing desperately, I don’t even know what. Jenny got down on her knees and crawled under the table. A few seconds later, I felt her gently pushing my knees apart, then felt her breath on my cock. Next, I felt her tongue start at the base of my shaft and very slowly lick all the way up to the head. Oh god, it was both incredible and agonizing. And it was only the beginning. There were still almost 35 minutes left on the timer.
After a few minutes, I couldn't stand it anymore, and I tried putting my legs back together. Jenny grunted as I squeezed her, then said sternly, "Pull your legs apart, or it will cost you a full letter grade." I spread my legs again, with an effort of sheer willpower. Jenny went back to her slow, agonizing blowjob for a minute, then said, "If you do that again, it'll cost you another week in the belt." There was no doubt in my mind she would do it, either.
With trying to concentrate on keeping my legs open and with Jenny’s tongue playing 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 I was getting tunnel vision and it was hard to breathe. I did manage to scrawl out what was not so much an essay as an unconditional surrender:
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. But, she said, I failed. It wasn't really an essay. "‘I really want to cum' is not exactly a thesis statement," she said. I would have felt worse, but I was pretty sure the whole exercise was just a way to torment me more. I told her that, 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 so exhausted from the last couple of days. I woke up in the middle of the night, though, my cock straining to get out of the belt. I could still feel Jenny's tongue running slowly up and down my cock. It was like getting a blow job from a ghost. Meanwhile, she lay next to me sleeping away. And why not? I'd given her two more orgasms before going to sleep that night.
Jenny didn’t have to work until later that morning, so I was all up and ready to go by the time she climbed out of bed. She came into the kitchen wearing the kimono with her hair messed up. She looked sexy as hell. I, however, was feeling a little cranky, what with not sleeping well the past two nights on top of 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 the matter?” I said.
She turned on me, her eyes blazing, staring at me intently. Before 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 me last night?”
Give her this: she knew how to push my buttons. My irritability vanished, replaced by my male ego's need to never be wrong. "Of course, I can handle it," I said. Stupidly.
"Well, that's good to hear," she said, settling back. She stretched and, despite myself, I felt a twinge in my crotch as the kimono tugged at her breasts. She casually started pouring herself another cup of coffee. "You know, I was thinking of letting you out tomorrow. But since you're handling it so well, you won't have any problem spending an extra week in the belt."
Have you ever heard the expression, “my heart sank?” That’s exactly what I felt like in that moment. I gritted my teeth and growled quietly in frustration. Had I just blown my chance to cum tomorrow? “Fine,” I said through clenched teeth. But I didn’t feel fine.
On the way to work, it occurred to me that this was all part of the game, that Jenny had never really intended to let me cum tomorrow, that she was looking for an excuse to “extend” my time. But I was desperate beyond belief. I tried calling her several times that day, leaving messages telling her how sorry I was for losing my temper. She never took my call. Finally, I left her a message repeating my apology, and asking her to please reconsider making we wait another week.
That night I figured a little ass-kissing might be in order, so I already had dinner going by the time she got home. She had worn jeans and a sweatshirt to work, but changed into the cutoffs and a cropped black tank top. The cutoffs were if anything shorter than before, they barely covered her ass. After dinner, as I was washing dishes, she came over and stood next to me.
“I’ve been considering your request,” she said.
My mind raced. Request? “My request to cum?” I asked hopefully.
She smiled. “Oh no. Your request to reconsider my extending your time in the belt. We have to get that straightened out before I’ll even consider letting you cum.”
For a second, I considered a snarky comment, but the ass-kissing has started so well with dinner and I didn’t want to blow it. “I’d be grateful for any opportunity to make up for my behavior this morning,” I said formally. She brightened.
“Good! Come into the bedroom when you’re finished with the dishes,” she said.
I slowly finished the dishes, stalling. You can’t get them too clean, you know. Also, I knew that whatever she had in mind was going to leave me more frustrated and desperate than ever before, and I was already about to burst. But I also knew better than to keep her waiting too long.
I went into the bedroom and saw the handcuffs tied to the headboard. Jenny ordered me to strip and lay on my back, then she handcuffed my wrists. She slowly started sliding a finger along my cock; I was hard instantly.
“ Okay, here’s the rules,” she said. “The longer you let me play with you penis, the more I shorten your extra week in the belt. Got it?”
I nodded. Her finger was already driving me crazy.
“You can tell me to stop any time, but then we’re done. You don’t get another chance to shorten your time. Understand?”
I nodded again.
“And, if you touch your penis or me at any time, you automatically spend two more weeks in the belt. Okay?”
I was confused for a moment. How could I touch my…? Then she stopped teasing me, picked up the handcuff key from the nightstand, and unlocked my right hand. Then, she began teasing my cock again.
It was diabolical. My hand was free, I could have easily reached down and grabbed my dick for some much, much-needed relief. I doubt she could have stopped me. This was like that night way back when first started "chastity play" when I could have easily gotten myself off, but didn't. Except this was ten thousand times worse, after almost two weeks of ruthless teasing with no relief. I grabbed a handful of the bed sheets and held on for dear life, not daring to let my hand get any closer to my cock, which she teased and teased with her fingers.
My mind whirled. One second, I thought about how easy it would be to reach down and jerk myself off, and that I was a fool for not doing it. The next, I realized this was a test and that failure meant two more weeks in the belt, maybe longer if I managed to make myself cum. Then, I futilely tried to think of a way to get Jenny to make me cum, maybe trick her into doing it. Then I was back to thinking about grabbing my dick again. For all that Jenny had messed with my cock the last couple of weeks, she had messed with my mind even more.
After a while, Jenny started playing with my balls with her other hand. “Wow, these are full," she said laughingly. "You must really want to squirt some of this out."
She continued tormenting my cock and balls with separate hands.
"God, I'll bet it would feel soooo good to feel some of this coming out the end of your dick." She twirled a fingertip round and round on the end of my cock. "I can just imagine all that cum shooting out right here."
I could imagine it, too. I could almost feel the cum rushing up through my dick and out the end. Almost. I tightened my grip on the sheets in my hand, desperate to keep it away from anguished cock.
Jenny moved her other hand away from my balls and grasped the base of my cock with her thumb and forefinger. She continued to move them just a little, but mainly they were holding my cock still. Meanwhile, the fingers of her other hand had all gathered at the head, teasing only the area right at the tip.
"You know, there's plenty of room for a third hand on your dick right now. Wouldn't it feel so good to reach over and take it in your hand?"
Oh god, of course it would! That's the one thing I wanted to do more than anything right now! I groaned in protest and gripped the sheets even harder with my free hand.
After a minute she said, "Okay, then," and returned to teasing my whole cock, and sometimes my balls as well. A couple more times she'd leave most of my dick alone, just teasing the tip and the base, and invite me to touch myself. The last time she almost got me to do it. She asked "Are you sure?" three times, then slowly licked the length of my shaft with the tip of her tongue. I nearly caved; suddenly the chance to just touch myself for a few seconds seemed well worth another two weeks in the belt. I was nearly crying with frustration. But just enough of my brain was not thinking with my dick, and I decided to cut my losses.
"Please stop," I said. "I give."
"Aw, too bad," she said. She stopped teasing me for a moment while she locked my free hand back in the cuffs. Then she went back to licking my cock.
"Hey --" I began. I tried to squirm out from under her.
She paused. "Victory lap, remember?" She licked me a few more times. "And just for that, I'm taking an extra long one." And she did.
Then she said, "Let's see how much time you earned back." She took a piece of paper and a pen off the night stand, then sat cross-legged near the foot of the bed. With one hand she started writing on the paper. She held my dick in the other and slowly stroked the underside of it with her thumb.
"Okay," she said after a couple of minutes. She stopped teasing me for a few seconds while she folded the piece of paper. She held it up with one hand while she went back to teasing me with the other.
"On this sheet of paper I've written the day you'll 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 you annoy me again ."
I winced in frustration. It was Friday night. Could I stand another eight days -- or even longer -- of this? But she wasn't finished.
"Or." I opened my eyes. "Or, you can cum tomorrow -- guaranteed -- in exchange for spending two more more weeks in the belt."
But I could tell there was more. "Or...?" I began.
She smiled. "Or...you can cum tonight -- in fact, you can cum in the next five minutes -- in exchange for staying in the belt for a month."
I thought for a minute. The idea of coming right then sounded really good, especially with her thumb still teasing my dick. But another month, or even two weeks, in the belt? What if she made me go the whole time without cumming? It was still shy of two weeks this go-round and I was about to go insane. Then I remembered my letter.
"What do you want?" I asked.
"Me? I'm not the one with two weeks of cum backed up in my balls. It's up to you."
But I knew then what she wanted. The second two options, while they extended my time in the belt, had definite end dates and let me cum either tonight or tomorrow. By picking the first I not only gave up the option of coming indefinitely, I also, under Jenny's extension clause, gave her back the right to decide when I got out of the belt and when I came next. "I'll take whatever's on the paper," I said.
"Good!" she said brightly, then she leaned over and hugged me like I'd just given her the best birthday present ever.
To be continued
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