Two Weeks Onward: Episode Five

After dinner, we headed to a lot near a playground for some “parking.” Jenny felt wonderful in my grasp, and I managed to bring her off multiple times using just my fingers. Meanwhile, my cock was straining against the cage, eager for release. I thought I already knew what she’d say, but my desperate state made me ask anyway.

“Jenny,” I asked during a pause in our kissing, “do you think I could cum tonight?”

She actually pondered it for a second before shaking her head with a smile. “No, I don’t think so,” she said simply. This was the big question of my life right then, and she decided it as casually as if I’d asked about ice cream. I felt thrilled yet appalled by this new dynamic.

We headed home, but she wasn’t finished with me. She told me to wait on the sofa while she changed. When she returned, wearing a blue teddy and dangling handcuffs, she said, “Turn around.”

Soon we were kissing again, my hands cuffed behind my back, pants and chastity belt lying on the floor. She massaged my cock and balls for a bit, then called “break” to let me cool down. After two cycles of this, I had to control my breathing; after five, I was going mad. In some ways, it was more maddening teasing than usual because her rhythm of ramping up the pressure and letting it drop was more frustrating than a constant tease.

It didn’t help that I was fighting against it. I tried thinking about other things to keep from getting hard, but she rarely took more than a few seconds to get me fully erect again. I might have made it harder on myself. Once, as my cock stiffened, I whispered “Damn” loudly enough for her to hear. Her eyes widened and she smiled. She likely realized I was resisting and gave me a couple extra cycles as “victory laps.”

During one break, I decided to make one last attempt at cumming that day. It probably seemed futile, but the pressure from my cock was immense.

“Hey, Jenny,” I said. “Come on. I’m going insane here. Please let me cum now. I’ll do anything you ask. Please.”

She took hold of my cock again; it stiffened at her touch. “Oh? Anything?”

I nodded. She began teasing earnestly. “Would you pay money to cum?”

“Yes! Yes, of course,” I said.

“Would you give me all the money in your wallet?” she asked.

I nodded eagerly. “Oh, yes.” I felt like I was on the verge of finally getting release.

She paused her teasing to reach down and fish my wallet out of my pants. Opening it, she took out all the cash—three twenties.

“Sixty bucks?” she scoffed. “All this time, effort, and money I’ve put in over the last few days, and you want me to end it all for sixty dollars?” She tossed the wallet and cash onto the floor and returned to teasing my desperate cock.

“Of course, you could always write me a check,” she added.

“Sure. Okay.” I was practically shivering with frustration by then.

“How about a hundred dollars?” she asked.

I nodded enthusiastically. “Okay.”

She seemed to consider it. “How about two hundred?” I only hesitated for a second before nodding again. Her fingers on my cock put me in a very weak negotiating position.

“Hmmm. I think three hundred would be reasonable. Don’t you?” The thing is, I did agree. Three hundred was a significant chunk of my weekly pay back then, and parting with it meant cutting back for the next two or three weeks. But in that moment, it felt like the most sensible offer.

“Really?” she asked. “You’d pay me $300 for a thirty-second handjob with a happy ending?”

I nodded again. “I’d pay you $300 to let me do it myself.”

She laughed. “That’s fantastic.” She stopped teasing, stood up, and retrieved my belt. Sitting on the edge of the bed with it in her lap, she said, “I’m afraid I must decline your generous offer.”

I was devastated.

“I’m just not ready for you to cum yet,” she continued. “Besides, I have a couple of new skirts I want to try out this week.” I groaned. “New skirts” meant work clothes, and it was only Saturday night. It would be at least three more days in the belt.

Speaking of which, she soon got me back into it. I cooperated as best I could, partly from not wanting to repeat my earlier pathetic performance and partly to avoid having my time extended. After releasing me from the cuffs, she fetched us glasses of wine. I slumped on the couch, staring glumly at the belt.

“Oh now, don’t be that way,” she said. “It’s not that bad.”

I smirked. “We’ll see what you say after I’ve worn this for a couple of weeks,” I replied.

She laughed. “I don’t think so. Remember? Chastity is for you, not for me.” She sipped her wine. “In fact, once we finish this stretch, I think we need to try one that lasts longer. Say, a month?”

I could have protested it was unfair or said no. But I knew I would agree. Because as frustrating as the experience had been, it was also turning me on more intensely than ever before. Somehow, Jenny had unlocked something in me. Had it always been there, waiting to be freed? Or had she imprinted that desire onto me for her own kink? Either way, I craved being tormented just as much as she enjoyed doing the tormenting. A month? The idea was horrifying yet thrilling.

It got late so we went to bed. Jenny fell asleep immediately. Why not? She’d had several orgasms, two good meals, and plenty of heavy petting that day. Me? I’d been ruthlessly teased most of the time, nearly lost my mind, and still suffered from another record-breaking case of blue balls. So it took me longer to drop off.

The next morning, Sunday, I was up before Jenny. I was in the kitchen making coffee when she came in completely naked.

“Come on, I have something for you,” she said, leading me back to the bedroom. She unlocked my belt and tossed it onto the floor. Then she made me sit on the edge of the bed while she knelt before me.

“Same rules,” she said. “If you touch me or your penis before I say so, I’m putting you back in the belt for long enough that you’ll forget what an orgasm feels like. Got it?”

I confirmed I did. As she gave me a slow blow job, leaning back on my arms, I wanted to cum again after only a minute and was desperate after five. I grunted and moaned with frustration, causing her to giggle as her tongue worked over my cock.

Then she stopped. Still kneeling, she picked up the cutoff jeans she’d worn yesterday while “we” cleaned, earlier on Friday night when she tried to get me to touch myself. She pulled a piece of paper from a pocket—the one where she had re-calculated the time on my extension—and held it up for me to read. There were many numbers scrawled across it; along one edge, she’d written “Sunday 11:00 am” and circled it. She pointed to the clock; it was exactly 11:00.

“Time for you to cum,” she said brightly, then leaned forward and took my cock deep into her mouth. Her tongue, an instrument of torture only a minute prior, sent wave after wave of pleasure through me. I felt an orgasm building right away. For a second, I worried it was just another tease, but she brought the climax closer.

When it finally happened, it was the most incredible thing I’ve ever experienced.

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Things settled back to normal for a while. I think Jenny realized I needed a break and probably did too. It occurred to me that she must have been planning and saving up for this “long game” for quite some time before we started. Plus, the effort of being such a creative and persistent cock tease had to be hard work on her, regardless of how much she enjoyed it.

Occasional chastity play remained part of our sex life. One time she locked me in the belt in the morning and said it was “just for a day or two”

”. I was quite anxious, worried that this would become the month-long “stretch” she had mentioned so casually. She really got to me and built up the teasing; by the next morning, just about five minutes before my usual departure for work, she presented an offer: I could slip out of the belt and cum now, or wait until the following morning at that same hour. The catch was being late for work, which I despised. She clarified that this option held true only during those specific weekday mornings. Although I wanted to cum right then, my pride kept me from giving in immediately. Plus, I knew she enjoyed it when I pushed back (as long as she ultimately prevailed), so I managed to hold out for a couple of days. Since it was Friday morning by then, the choice was clear: surrender or endure the weekend frustrated in the belt, and I chose to give in. My desire always triumphed over my ego eventually.

But life intervened. Not long after that incident, Jenny received a promotion at work, which meant she spent extended periods away from home. Early on, there was a time when she locked me into the belt before leaving town for four days. It had its own appeal but wasn’t as intense as when we were together in person. Afterward, things gradually wound down. Eventually, Jenny’s transfer became permanent and our relationship ended. We cooled to the point that discussing my moving with her never even came up.

I didn’t spend that entire month in chastity while I was with Jenny. Later partners kept me locked for longer stretches; they weren’t easy either, but none affected my body and mind as deeply as those two weeks of playing Jenny’s “long game.” Perhaps it was because I was older, or maybe I had come to desire the teasing and denial more intensely than before. Those later women certainly drove me mad at times in their own way, yet with Jenny’s “long game,” that feeling seemed constant.

The End