Friday morning we were back on our routine, Jenny coming out in her newly-shortened skirt. I couldn’t actually tell if it was shorter or not, but it seemed like it. She could have just told me it was shorter and my brain and cock would have done the rest. Once again, I had to force myself at work to think about anything besides Jenny’s thighs and the ache in my balls.
That night, she turned up the heat even more. She came out before dinner in the blue negligee again, poured herself a drink and sat next to me. After sipping slowly on the wine for a minute, she told me she was getting warm, then she reached down and slowly slipped off her panties. My mind was whirling again. I felt like I couldn't stand it anymore. I went down on her right there, desperate to make her cum as hard and as often as I could, hoping against hope that she would allow me some small relief in return.
Two hours later, we were naked in bed. Naked, that is, except for my chastity device. I had spent most of that time between her legs, trying every trick I knew with my tongue and fingers. Now she sat up in bed, eating a plate of long-cold dinner, while I lay next to her, my cock throbbing in my belt. I was ready to burst.
“Jenny,” I said, trying to keep my voice calm, “Do you think I could cum tonight?”
She chewed another bite, then she rubbed my chest and smiled. “No, not tonight,” she said with a smile. It wasn’t even a wicked smile, but a very pleasant one. She took a last bite of dinner and said thoughtfully, “It’s funny how easy it is to say that.” Great, I thought, just great.
Saturday I gave her more oral sex, then breakfast in bed. I was obsessed with cumming and determined to do everything I could to keep her in a good mood so maybe she'd let me. She asked me to go shopping with her and, while I normally would have declined, I said I would. I would have done anything to keep her happy. So we got dressed — the skirt she wore, this time, was definitely shorter than it had been before — and went off to the mall.
We checked out a couple of shoe stores, but this turned out to be just her way of getting me to let my guard down because next thing you know we were looking at some more short skirts and tight tops. She'd take a few outfits into the dressing room, then come out and ask me what I thought of each one. I was going crazy, trying to keep a lid on in public but wanting to howl in frustration. I'm pretty sure a salesgirl in one of the shops knew what was going on; not that I was in chastity, necessarily, but that Jenny was cock teasing me. I caught her grinning as she asked Jenny if she could bring her anything else to try. "How about that cute little blue skirt?" The shopping trip ended at the lingerie shop tucked discreetly into a corner of the mall. Jenny wasn't able to model anything for me there, but just glancing around at the various sexy items while I waited for her to come out of the dressing room was enough to keep my mind exactly where she wanted it.
On the way home, seemingly out of nowhere, Jenny asked me “Have you ever gotten car head?”
“No, I never have,” I answered calmly, trying to keep my eyes on the road. Suddenly there was nothing in the world I wanted more than car head. I couldn’t see how we would manage to get the chastity device off so we could do that, but I was more than willing to give it a shot. But Jenny only 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 way home was car head, as I put all my effort into keeping my eyes on the road and off the skirt riding up her thighs.
It had now been a week since I'd cum, a week I'd spent all of with my dick locked in a chastity belt, except for those ten or fifteen minutes of maintenance time. And Jenny wasn't just letting me build up the pressure with time, she was actively teasing me and making me want to cum more. I felt like I couldn't take any more, especially after a late-afternoon make-out session on the sofa which ended up with me giving her yet another orgasm with my fingers. She asked me to get her a glass of wine. As I handed her the glass, I got down on my knees in front of her and put my hands together like I was pleading (or praying!).
“Please, Jenny,” I begged, “I can’t stand it. Please let me cum tonight. Please!”
She just looked at me for a few minutes, then her head cocked to one side like she was studying me. She took a sip of wine, then said, “Wow, you’re really getting desperate, aren’t you?”
I nodded, then tried a little 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. It’s just what I was hoping for.” My own hopes soared. Briefly. “The begging is great, too. But I’m not ready to let you out just yet.”
“No,” she firmly. “I said ‘no.’ And I do like begging, but too much of that or any arguing will just get your time locked up extended. Do you understand?”
I nodded meekly, incredibly frustrated and disappointed. But also, turned on. I found it arousing that she could keep me in this state for as long as she wanted just on a whim.
Soon I realized that confessing my desperation, instead of making it more likely I was going to get relief, had only encouraged Jenny to ramp things up even more. It started that night with Jenny coming out of the bedroom in a sheer black corset, with matching panties, thigh-high stockings, and garters. We had a long make out session. This time, Jenny let me touch anything I wanted, but wouldn't let me undress her. After a long time, she slid off my pants and boxers and began caressing my balls, which hung out a bit to either side below the chastity belt. It felt incredible but was also incredibly frustrating. It was the first time she had touched me down there in over a week. But she kept it up for an hour, all while chewing on my ear and making my cock strain agonizingly against its cage. I was going insane.
Sunday I got a bit of a break, a least for a while, and if by break you mean she spent the day in a short kimono that nicely showed off her legs, and which she left open just enough to give me tantalizing glimpse of her breasts while clearly displaying the key to my belt that hung around her neck. That afternoon we were watching TV when she got up, went into the bedroom, and came back with a rather large looking vibrator. She undid the sash on her kimono then sat down next to me on the sofa, letting 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 stopped for a while at the key; it made a distinct rattling sound. Then she continued down until the vibrator rested between her legs. She moaned and writhed and came at least 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 how many times she’d orgasmed in the last eight days, while I’d endured a throbbing cock and a world-record case of blue balls. That night we had another heavy make out session with her teasing my balls for what felt like hours.
Monday we were back on the weekday routine. One of the new skirts she'd bought Saturday was as short as the ones she'd hemmed last week, with the added feature of a slit up the front of one leg. She made sure I got a good look at breakfast, then called me at work mid-morning to ask how I liked it. Of course, that's all I thought about the rest of the day.
Monday after dinner, she appeared again in her jeans and flannel shirt and announced it was time for more maintenance. We went into the bathroom, she unlocked me then watched like a hawk as I trimmed and washed. I toweled off after showering, and she held the belt out to me just like before. But I couldn’t do it. I couldn’t put it back on.
“I can’t, Jenny, I just can’t. It’s too much.”
She said nothing, just shook it at me like before.
“No, I won’t do it,” I said. I was practically crying.
“You will,” she said. “You said you would let me decide when you got out and when you could cum, and I have decided it’s not time yet.”
“Please, Jenny, you’re too good a tease.” I instantly regretted using the word, afraid I’d offend her, but I saw her suppress a smile. She was trying to be a tease. “And with all the sexy new outfits, I can’t stand it.”
The smile was gone instantly. “Those clothes aren’t cheap, you know,” she said. “I spent a lot on those. And I’m going to get my money’s worth. Now…” She didn’t finish the sentence, just held the belt out to me again.
Unbelievably, I actually felt kind of guilty. Like the money she’d spent entitled her to keep me aching and desperate. I already knew I was going to give in, but I tried one more tactic.
“Okay, but can’t we at least talk about this?” I pleaded, trying to sound reasonable.
“Sure,” she said. “We can talk about anything. But after you put your belt back on.”
I nodded and started putting the belt back on. As I felt it slide over my penis, I realized there was no point in talking. As soon as the lock snapped shut, I had nothing to negotiate with. She held they key, and with it all the power. A while later I heard the sewing machine in the bedroom going again. She was taking up the hems on a couple more of the skirts.
The next day at work, my usual obsessions with cumming and whatever hot outfit Jenny had been wearing that morning (yes, the skirt on this morning's had definitely been higher) were joined by a mental kicking myself for being guilted back into the belt. But I also knew that part of me wanted to be back in the belt, as much as part of me was ready to scream with the need for physical relief. I dreaded what the two competing drives might lead me to.
That night Jenny said she wanted to talk to me. “I’ve decided to give you a chance — just a chance — to cum tonight.” I eagerly said I’d be happy for even a chance. She said she’d show me what she had in mind, then led me into the bedroom.
“It’s a little test of endurance,” she said. We were going to have a teasing contest. I would get to tease her with my tongue while she teased me with her hand. She’d broken out a pair of handcuffs from our pre-chastity play period (although I was having a hard time thinking about what I was going through lately as “play”). She cuffed my wrists together, then tied them to the rail at the foot of the bed. I was on my knees, my cock and balls hanging down, while my face was between her legs. My tongue had easy access to her pussy, while she could tease my cock and balls at will. The rules were pretty unfair. She would set her alarm for one hour. We would tease each other during this time, but she got three five-minute “timeouts,” which she could take any time, while I got none. If I gave up before the hour was up, I lost. If I could make her give up before the hour was up, I won and would get to cum.
I knew I had little chance of winning. I’d be continuously teased for an hour after a week and half of being teased and denied while she, who’d had more orgasms in that time than she usually had in three months, could take a break whenever she wanted. In addition, she could see the clock and I couldn’t. My strategy was to concentrate on teasing her as much as possible, hoping that would distract me from my cock being teased. I figured the longer I could keep from getting hard in the first place, the better off I’d be.
So much for Plan A. I may have held off an erection for all of forty-five seconds before her teasing fingers had me hard as a rock. After that, I may have got distracted for a few seconds here and there, but the long, slow strokes of her fingertips along my shaft soon brought my attention back there. My own body turned traitor, leaking precum which she used to make her strokes slicker and my cock that much more sensitive. I worked my tongue slowly around her pussy, carefully avoiding her clit. She moaned and writhed under me, which gave me some measure of hope, but while I sometimes got too distracted to tease her for short periods, her fingers were relentless; they never, ever left my cock and never, ever, stopped.
After ten, or fifteen, or twenty minutes (I really had no idea) I was already thinking of giving up. Then she said, "Time out." I pulled my head out from between her thighs and rested on my elbows. For a few seconds, I was happy for the break. But her fingers still gently played over my cock, and now I didn't even have the task of teasing her to distract me. I tried all the usual tricks to calm an erection — think about bills, think about ice water, tell yourself a joke — but everything she'd done in the last week and a half had been about making me think about my penis all the time. Also, no one, including me, had touched it in all that time, and now she was giving it a first-class teasing. I was having trouble thinking straight, but I knew I had at least another half hour to go, and probably much more than that. My whole body hummed with each stroke of each finger along my shaft.
“Start again,” she said after a while. I was sure it had been more than five minutes, but no way was I going to accuse her of cheating: I’d for sure not get to cum then. I went back to teasing her with a new enthusiasm, grateful for something to take my attention, even a little bit, off my throbbing, needy cock. For a time, it seemed as if things might even be going my way. My frustration seemed to plateau. Meanwhile, I figured out a technique to bring her close to orgasm, only to back off again. I heard her moan in frustration. She could have stopped me at any time with another time out, but she was willing to risk more frustration for the chance at an orgasm (my dilemma exactly).
Finally, I must have got to her because she called another time out. She just lay there for a time, breathing heavily. She even stopped stroking my cock for a minute, just holding onto it gently. Then her fingers started to move again. I was back in Hell. When she ordered me to start again (after what I was again sure was more than five minutes), her voice was calm. Her legs opened to my mouth again, almost welcoming the attention. Meanwhile, I would have given anything to get my cock away from those teasing fingers. I was going to lose this game.
My intention was to go back to the previous technique and get her frustrated again, but by this point, her own teasing was having a real effect, and I was having trouble concentrating on the task. I kept having to stop and take a deep breath, it was tough to get a rhythm going on her pussy. She wasn't reacting nearly as strongly either. My cock, my balls, my whole body were screaming for relief.
Suddenly, she stopped teasing, again just holding my cock in her hand. Then she called time out. Everything stopped for a minute except our breathing. She shifted a little under me. Then her hand slid down my shaft until she was just holding it by her thumb and little finger. Her three middle fingers started teasing the underside of my cock. Then I felt the fingers from her other hand start teasing the head of my cock, now well-lubed by my own precum. I should have known something like this was coming, that she'd have some technique ready in case I got close to making it the full hour. I gritted my teeth and tried to withstand it, but I was ready to scream from the frustration. Finally, despairingly, I choked out, "Stop. I give." She kept up the teasing. After a minute, I said, "I said I surrender." She kept up for a few more seconds then finally released my poor, abused cock
She laughed. “I know. I was just taking a victory lap.” I moaned. She laughed again. Then she untied my handcuffs from the foot of the bed and moved them to the headboard, where she secured them again. “Can’t risk you touching until you’re safely back in your belt.” Then I watched as she moved her hands down between her legs and made herself cum. Miserably, I watched and listened to her moan and cry out. Finally, she settled back with a satisfied purring.
“You’re actually pretty good at teasing, you really had me going there for a while,” she said sleepily.
I laughed. “Just wait until I get you in a chastity belt.”
"Oh, no," she said. "There's no chastity for me . There's only chastity for you." Then, as if to emphasize the point, she reached down and got herself off again. After that, she drifted off to sleep for awhile. When she woke up, I'd calmed down enough and she put me back in the belt. During this whole time, I had gradually learned to sleep with both the belt and the frustration, but it took me even longer than usual that night.
To be continued.
Tell me a story!
1 post • Page 1 of 1