Day Fifteen: The Teasing Continues (Part Two)

By Friday morning, Jenny and I were back in our usual rhythm. She came out wearing her newly hemmed skirt. It was hard to say for sure if it actually looked shorter or not; maybe she just told me so, and my mind (and cock) filled in the blanks.

I had to fight myself at work from daydreaming about Jenny’s thighs and that persistent ache deep in my balls.

That evening, she cranked up the tension. She appeared before dinner again in her blue negligee, poured a drink, and settled beside me. After sipping her wine for a minute or two, she mentioned feeling warm, then slowly reached down to slide off her panties. My thoughts started spinning once more. I felt like I couldn’t take it anymore.

I dropped to my knees right there, desperate to give her multiple climaxes as hard and often as possible, hoping with everything in me that she’d grant me a little relief in return.

Two hours later, we were naked under the sheets—well, almost. My chastity device was still firmly attached. I had spent most of those two hours between her legs, employing every trick I knew with my tongue and fingers. Now she sat up on the bed, eating her dinner which had gone cold a while ago, while I lay beside her, throbbing in my belt. I felt like I was about to burst.

“Jenny,” I said, forcing calm into my voice, “Do you think I could cum tonight?”

She chewed another bite, rubbed my chest with one hand, and smiled. “No, not tonight.” It wasn’t a cruel smile; it was quite pleasant. She took her last bite of dinner and mused thoughtfully, “It’s funny how easy that is to say.” Great, I thought. Just great.

On Saturday, I gave her plenty more oral sex, followed by breakfast in bed. I became obsessed with the idea of finally cumming, determined to keep her happy so she might let me release. She asked if I’d go shopping with her, and although I usually would have said no, this time I agreed. I felt like I could do anything just to keep her content.

So we got dressed—the skirt she wore was definitely shorter than before—and headed out to the mall.

We visited a couple of shoe stores, but it turned out that was just her strategy for lowering my defenses. Suddenly, next thing you know, we were browsing more short skirts and form-fitting tops. She would take several outfits into the dressing room, then step out to ask my opinion on each one. I was going mad inside, trying to maintain composure in public while wanting howl with frustration.

I’m fairly certain a salesgirl at one of the shops figured it out—not necessarily that I was locked up, but that Jenny was actively cock-teasing me. I caught her grinning as she asked Jenny if there was anything else she could try. “How about that cute little blue skirt?”

The shopping trip concluded at a lingerie shop tucked discreetly into a corner of the mall. Jenny didn’t model much for me in there, but just glancing around at the various sexy items while I waited for her to emerge from the dressing room was enough to keep my mind exactly where she wanted it.

On the drive home, seemingly out of nowhere, Jenny asked, “Have you ever gotten car head?”

“No, never,” I answered calmly, trying to keep my eyes fixed on the road. Suddenly, nothing in the world mattered more than getting a blowjob in the car. I couldn’t figure out how we’d manage to get the chastity device off long enough for that, but I was more than willing to try.

But Jenny just said, “Oh,” then crossed her legs and turned to look out the window. Of course, all I could think about for the rest of the ride home was car head, as I put all my effort into keeping my eyes on the road rather than watching her skirt ride up over her thighs.

It had been a week since I last cummed—a whole week with my dick locked in that chastity belt, except for those ten or fifteen minutes of maintenance time. Jenny wasn’t just letting pressure build through time; she was actively teasing me and making the need to cum more intense.

I felt like I couldn’t handle any more, especially after a late-afternoon make-out session on the sofa which ended with me giving her yet another orgasm using my fingers. She asked for a glass of wine. As I handed it to her, I dropped to my knees in front of her and clasped my hands together as if pleading (or praying).

“Please, Jenny,” I begged, “I can’t stand it anymore. Please let me cum tonight. Please!”

She just looked at me for a few minutes, tilting her head slightly as she studied me. She took a sip of wine and said, “Wow, you’re really getting desperate, aren’t you?”

I nodded, then offered a bit of flattery: “Oh, yes. It’s been a week, and you really know how to keep the pressure on.”

She nodded back. “That’s awesome to hear. That’s just what I was hoping for.” My hopes soared briefly.

“The begging is great, too,” she added. “But I’m not ready to let you out just yet.”

“But—“

“No,” she said firmly. “I said ‘no.’ And while I do like the begging, if you beg too much or start arguing, your time will get locked up even longer. Do you understand?”

I nodded meekly, incredibly frustrated and disappointed, yet turned on at the same time. It was arousing to realize she could keep me in this state for as long as she wanted with just a whim.

Soon I realized that confessing my desperation hadn’t made it more likely I’d get relief; instead, it had encouraged Jenny to ramp things up even further.

It started that night when Jenny came out of the bedroom wearing a sheer black corset, matching panties, thigh-high stockings, and garters. We shared a long make-out session. This time, she let me touch anything I wanted, but refused to be undressed by me.

After quite some time, she slid off my pants and boxers and began caressing my balls, which hung out slightly on either side below the chastity belt. It felt incredible, yet was incredibly frustrating. It had been over a week since she’d touched me down there like that. But she kept it up for an hour, all while chewing gently on my ear and making my cock strain agonizingly against its cage.

I was going insane.

Sunday offered a bit of a break—at least if by “break” you mean she spent the day in a short kimono that nicely showed off her legs. She left it open just enough to give me tantalizing glimpses of her breasts while clearly displaying the key to my belt hanging around her neck.

That afternoon, we were watching TV when she got up and went into the bedroom, returning with what looked like a rather large vibrator. She undid the sash on her kimono, sat down next to me on the sofa, and let the robe fall open to reveal that she wore nothing underneath.

She turned the vibrator on and ran it slowly down her front between her breasts. She paused for a while at the key; it made a distinct rattling sound against the metal. Then she continued downward until the device rested directly between her legs.

She moaned, writhed, and came no fewer than four times. I tried ignoring it at first, then gave up and reached for her, but she slapped my hand playfully and said, “Hands off.”

I could only sit there in frustration; I’d lost count of how many times she’d orgasmed over the last eight days, while I endured a throbbing cock and what felt like a world-record case of blue balls. That night we had another heavy make-out session where she teased my balls for what seemed like hours.

On Monday, we returned to our weekday routine. One of the new skirts Jenny bought on Saturday was as short as those she’d hemmed last week, featuring an added slit up the front of one leg. She made sure I got a good look at it during breakfast, then called me at work mid-morning to ask how much I liked it. Naturally, that’s all I thought about for the rest of the day.

Monday after dinner, she appeared again in her jeans and flannel shirt and announced it was time for maintenance.

We went into the bathroom; she unlocked me, then watched like a hawk as I trimmed and washed. After toweling off from my shower, she held the belt out to me just as before.

But I couldn’t do it. I couldn’t put it back on.

“I can’t, Jenny, I really can’t,” I said. “It’s too much.”

She didn’t say a word; she simply shook the device at m

“Like before.”

“No, I won’t do it,” I declared, on the verge of tears.

“You will,” she countered. “You promised to let me decide when you get out and when you’re allowed to cum, and my decision is that it isn’t time yet.”

“Please, Jenny, you tease too much.” The word slipped out instantly, and I worried I’d offended her, but I caught the hint of a smile she tried to hide. She was definitely playing the part. “Plus, with all these new sexy outfits, the tension is unbearable.”

Her smile vanished immediately. “Those clothes aren’t cheap, you know,” she reminded me. “I invested heavily in them, and I intend to get my money’s worth. Now…” She left her sentence hanging as she held the belt out toward me once more.

To my surprise, a wave of guilt washed over me. It felt like her spending justified keeping me aching and desperate. I knew surrender was inevitable but attempted one last strategy.

“Fine,” I pleaded, striving for reasonableness. “But can we discuss this first?”

“Certainly,” she replied. “We can talk about whatever you want, provided you put your belt back on afterward.”

I nodded and began reattaching the belt. As it slid over my penis, it became clear that talking was futile. The moment the lock clicked into place, I had no leverage left; she held both the key and all the power.

Later, the sound of her sewing machine drifted from the bedroom. She was taking up hems on a couple more skirts.

The following day at work, my usual preoccupations—cumming and wondering what hot outfit Jenny wore that morning (yes, today’s skirt was definitely shorter)—were compounded by mental chiding for letting myself be guilted back into the belt. Yet I knew part of me wanted to remain confined, even as another part screamed for physical relief. I dreaded where these conflicting desires would lead.

That evening, Jenny announced she wanted to talk. “I’ve decided to grant you a chance—just one—to cum tonight.” I eagerly accepted this opportunity. She promised to show me her plan and led me into the bedroom.

“It’s an endurance test,” she explained. We were engaging in a teasing contest: I would use my tongue on her while she used her hand on me. She retrieved handcuffs from our pre-chastity days (though lately, what I’d endured felt less like play). She secured my wrists together and tied them to the bed’s footboard. Kneeling with my cock and balls hanging freely, my face nestled between her legs gave my tongue easy access to her pussy while she could tease me at will.

The rules favored her significantly. Her alarm was set for one hour of mutual teasing, but she received three five-minute “timeouts” available whenever she chose, whereas I had none. If I yielded before the hour ended, I lost. If I made her yield first, I won my release.

I knew winning was unlikely. After a week and a half of constant denial while she enjoyed more orgasms than in three months, I would be teased continuously for an hour on top of that. She could check the clock; I couldn’t My strategy relied on focusing intensely on teasing her to distract myself from my own arousal. The longer I avoided erection initially, the better.

Plan A was sound enough until forty-five seconds into it when her fingers had me rock hard. Although I lost focus for brief moments here and there, her long, slow strokes along my shaft soon retracted my attention. My body betrayed me by leaking precum, which made her movements smoother and heightened my sensitivity.

I worked slowly around her pussy, carefully avoiding her clit. Her moans and writhing gave me hope, but while I occasionally paused in teasing due to distraction, her fingers were relentless—they never left my cock or stopped their motion.

After ten, fifteen, or perhaps twenty minutes (time was unclear), I felt ready to quit. Then came the words: “Time out.” I pulled back and rested on my elbows for a few blissful seconds. However, her fingers continued gently playing over my cock, removing even the distraction of teasing her.

I tried standard tricks—thinking about bills or ice water—but everything she’d done lately kept my mind fixed on my penis. No one had touched it in ages, and now she was giving it premium attention. Thinking clearly became difficult, yet I knew at least another half hour remained, likely more. Every stroke sent a hum through my entire body.

“Resume,” she said later. It felt like more than five minutes had passed, but I refused to accuse her of cheating; doing so would cost me the chance to cum. Redoubling my efforts with new enthusiasm, grateful for any distraction from my throbbing need, things seemed promising for a while. My frustration stabilized as I developed a technique to bring her close to climax only to pull back just in time. Her frustrated moans confirmed she was struggling too; like me, she risked more discomfort for the sake of an orgasm.

Eventually, I must have worn her down because another “time out” was called. She lay there breathing heavily, even pausing her stroking for a minute while gently holding my cock before resuming movement. Back in Hell I went. Her voice remained calm when she ordered me to restart; her legs opened invitingly again.

I would have given anything to escape those teasing fingers. Defeat seemed certain.

Intending to return to the previous technique and frustrate her further, I found it hard to concentrate as her own efforts took their toll. Pausing for deep breaths became necessary to maintain rhythm on her pussy, whose reactions were weakening. My cock, balls, and entire body screamed for release.

Suddenly, she stopped teasing, holding my cock in one hand, then called time out again. Silence fell except for our breathing. She shifted beneath me, sliding her hand down until only her thumb and little finger held the base while her other three fingers teased the underside of the shaft. Then, fingers from her free hand joined in on the head, now slick with my precum.

I should have anticipated this tactic to prevent a full-hour victory. Gritting my teeth against frustration that bordered on screaming, I finally choked out, “Stop. I give.” She continued teasing for a moment before I clarified, “I surrender.” After a few more seconds of persistence, she released my battered cock.

She laughed. “Knowing me? Just taking a victory lap.” Moaning in resignation, I watched her untie the handcuffs from the footboard and secure them to the headboard. “Can’t risk you touching yourself until you’re safely back under your belt.”

Then she slid her hands between her legs and climaxed.

I watched and listened as she moaned and cried out. Eventually, she relaxed back with a contented purr.

“You’re actually quite good at teasing,” she murmured sleepily. “You really had me going for a bit there.”

I laughed. “Just wait until I get you locked up in a chastity belt.”

“Oh, no,” she replied. “There’s no chastity waiting for me; it’s only for you.” As if to drive the point home, she reached down and relieved herself once more. After that, she drifted off to sleep for some time. When she woke up again, I had calmed down sufficiently, so she put me back into the belt. Throughout all of this, I gradually learned how to sleep with both the device and the frustration it brought, though that particular night took even longer than usual.

To be continued.