I have to say I'm awed by you guys who've gone months and months on end. I think I would have gone insane. I've managed to go about a month a couple of times, but by far the most crazy-making stretch I ever did was a mere 15 days. Maybe it's because it was very early on in my experience with T&D. In fact, it was with the girlfriend who got me into all this in the first place.
I know, fifteen days sounds a little wimpy. But for me, it was fifteen days of insane torment. Here's the story:
Jenny and I had been living together a few months and she had introduced more and more "kinky stuff" into our sex life as time went on. Most of it was pretty tame, "Fifty Shades of Grey"-type stuff. One night she asked me if I'd be willing to try chastity play, and I readily agreed. It soon turned out that when she said "chastity play" she meant chastity for me, not so much for her.
We eased into it. First I'd wear the chastity device for a few hours during foreplay. After a while, she'd get me to put it on in the morning, then she'd call me at work and talk dirty to me. By the time I got home I was ready to jump her bones, but she'd make me wait until later. One night I took off the belt ready for action, but she told me I could either get myself off that night or, if I waited, she would take care of me in the morning. I knew that's what she wanted me to choose, so I did, then I lay there half the night frustrated and horny, wondering if I was a damn fool for not finishing myself off. All I had to do was reach down and take my dick in my hand...instead, I waited for the morning, until Jenny decided it was time for me to cum. And, of course, during all these occasions, Jenny came whenever she wanted, usually with my help. "Chastity play" did not apply to her!
After a while, it was clear she was really enjoying teasing and denying me. Our chastity play times got closer and closer together. Soon, I was wearing the belt for longer periods; first a day and night, then two. One weekend she locked me in Friday night, then tormented me with several heavy make out sessions Friday and Saturday. Saturday night I asked her for some relief but she said I'd have to wait. She finally let me out for an awesome "nooner" on Sunday but after dinner that night she was already trying to get me back in the belt. I managed to put her off for a few days, but I knew it was only a matter of time.
The scary thing was that part of me was really getting off on all this. Jenny had brought out something in me that I'd never imagined was there. I knew it was only a matter of time before she pushed for a really long "chastity play" period and, as much as I dreaded the idea, I also knew I would agree. Sure enough, she brought it up one day while we were eating lunch in a park. She wanted to try for "more than a few days" and when I asked her how long she said she didn't know, I would just have to trust her. I thought about it a couple minutes, then agreed, but I could hardly choke the words out, I was so nervous.
I relaxed over the next week or so; we'd agreed I'd get a break from chastity play before "the long game" started. During that week she went shopping a couple of nights, saying she was thinking about a "new look." Like an idiot, I didn't put two and two together until later. I just told her I liked her current look. She had short red hair and a great body, but she didn't show it off. She usually wore just jeans, sneakers, and a sweatshirt or some old flannel shirt left over from her grunge phase. She said I was sweet to think so, then went off to the mall.
Saturday morning we slept in, then started making out. Eventually, she started kissing my chest, then my belly, then she took my cock in her mouth. After a few minutes of pure bliss, she let it loose and brought her face up next to mine, but continued to massage my cock with her hand.
"I think this should be the day," she said. My already hard cock swelled even more for a minute, and she grinned as she felt that in her hand. She knew she had me right where she wanted me. I nodded. She said, "Okay" then took my cock back in her mouth. Soon I came harder, even after a week of relatively normal sex, than I ever had after any period of chastity play. Then, just before lunch, I was back in the belt.
After dinner, we watched a movie, then moved into a make out session and, despite the awesome orgasm that morning, by bedtime I was ready for more. Too bad for me.
Sunday was familiar, if not always comfortable territory. I'd gone this long before, and knew I could endure the horniness and frustration. Jenny teased me frequently, but I had come to expect this. I was still nervous, but so far, it was going okay.
Monday, Jenny turned up the heat. I got up and showered first, then made breakfast while she got ready for work. When she came into breakfast, I about spilled my coffee. There she stood, in a very short gray skirt and short boots, nicely showing off most of her gorgeous legs. She had a white blouse unbuttoned to show just a hint of cleavage and curve of her breasts, and the keys to my belt dangling from a gold chain around her neck.
"What do you think of my new look?" she asked, twirling around. I was speechless. I had rarely seen her in a dress or skirt, and never in anything so short. She looked incredibly hot. That and almost two days of pent up arousal caused me to swell up in my belt as I never had before, only compounding my frustration. All could think about at work that day was Jenny in her outfit, and how much I wanted her. I tried not to think about "the long game." I knew she was just getting started, and I wasn't sure I was going to be able to handle it.
She wasn't through with me that day, though. After we both got home from work, she gave me a long, deep kiss that turned into a make out session. She stopped it short when my hands started to wander and told me she was going to make dinner. As she cooked, I turned on the news on TV, but I couldn't have told you a single thing that happened that day; all I could think about was Jenny in that short skirt, my cock straining against the belt, and how much I wanted to cum. My thoughts calmed as we ate dinner and chatted about work, then Jenny went off to do something in the bedroom while I did the dishes and cleaned up. By then the buzzing in my head had faded, and I picked up a book to read. I didn’t get very far.
Jenny came back into the living room. She had changed out of the skirt and top and was wearing only a dark blue, very sheer teddy negligee and panties. All I could say was "wow" as she sauntered over to sit next to me. Before she even leaned over to kiss me, my cock was straining against the belt again. When our lips met my whole body was buzzing with desire. I let out something between a moan and a whimper. She pulled back and grinned, then picked up the remote and turned on the TV again. I pretended to read my book, but my mind wasn't on it. All I could do was sneak peaks at Jenny next to me while my cock throbbed and my brain swirled.
After her show was over, she said, "Let's go to bed," then took my hand and led me back to the bedroom. It didn't even occur to me to resist. We started making out again, and after a while she let me take off her panties, then her negligee. She gently pushed my head toward her pussy. That was more than enough hint; I enthusiastically started licking her pussy and kept at until she came at least twice. I was hoping against hope that my turn would be next, so when she said, "It's probably time to go to sleep," I asked her meekly if I could cum first. She stifled a laugh; “No, baby, not tonight,” she said kindly. But she looked surprised that I had even asked.
That night I had a tough time getting to sleep. I kept thinking about Jenny in the short, gray skirt; Jenny in the see-through blue negligee, all while my cock strained against the belt. At one point I looked at the clock and saw that it was midnight. It had been three and a half days since Jenny put me in the belt. And, from her response to me asking to cum earlier, I had the feeling I was not even close to getting any relief.
Tuesday morning was a repeat of Monday, but this time, Jenny was wearing a short, black skirt and the top was a little tighter and more form-fitting. I felt like I was having trouble breathing. I could hardly concentrate at work. I was definitely at a level I had never been to before during our chastity play; I was getting desperate.
That night I got home first and started making dinner. Jenny came in while I was working in the kitchen, gave me a hug from behind then slid her hand down to my crotch, where she gave my belt a little tug. Instantly I was hard again, or at least as hard as I could get with that damn belt on. Jenny sat on the counter and chatted while I cooked, that lovely short, black skirt riding up on her thighs as she crossed her legs. I chatted back, but inside I was going insane. I kept telling myself to be careful not to cut or burn myself as I cooked, to try and look at her face and not her legs when I talked to her, to try to ignore my throbbing cock for just a second.
She started to clean up after dinner, but I insisted she let me do it. I was just finishing when she came back into the kitchen in another negligee, this one white with a single button just below her breasts. She looked so hot, and I was more horny, frustrated, and desperate than I'd ever imagined I could be. I decided to just be honest. "Jenny, you're driving me crazy," I said, hoping like hell that she'd have mercy on me. Instead, she just smiled and asked me if I wanted to watch a movie. Of course, I thought, anything you want, just please let me cum! We watched half a movie on the couch, she snuggled up against me, me staring down at her mostly naked body and the key to my belt dangling between her breasts. What movie were we watching? I'm not sure I even knew at the time.
Later, in bed, I tried to up my game, spending longer between her thighs and trying to make her cum even more. When it was time to go to sleep, I was disappointed, but not surprised, to discover she had no intention of letting me cum that night. I didn’t ask this time, and she didn’t bring it up.
Wednesday and Thursday were more of the same: another short skirt, another sexy top. All I could think about was coming. By the middle of the day Thursday I was so frustrated and desperate I thought I might cry. But Thursday night, something different happened. Jenny came home from work and changed into her old jeans and a flannel shirt. After dinner, she took me into the bathroom and took out her key. "It's time for a little maintenance," she said firmly. "I'm going to unlock you, then we're going to clean the belt. You'll trim your hair down there, then take a shower, then the belt is going right back on, understand?" I said I did. As soon as the belt was off, I got hard as a rock. It was my first full erection since Saturday morning when Jenny had given me that incredible blowjob. It was a relief, but also embarrassing and frustrating. Jenny smirked when she looked at it, then we got down to “maintenance.” She was very business-like and firm, warning me not to play with myself and watching while I shaved and showered. By the time I was dried off, she had the belt ready to put back on. I hesitated briefly, but she gave it an insistent shake while holding it out toward me, and with a groan, I put it back on. She snapped the lock shut, then tossed the keys into the air and caught it with a smile. She kissed me on the cheek and said, "I have some stuff to do in the bedroom," and walked off.
I wandered back into the living room, tried to watch TV, tried to read a magazine, but the business-like atmosphere of the "maintenance" session was already fading, and I was again finding it hard to concentrate on anything except cumming. I finally wandered into the bedroom to see what Jenny was up to. There I found her seated at the sewing machine she kept in one corner, her new, short skirts in a pile beside her.
“What are you up to?” I asked.
"I'm just taking up the hem on these an inch or two," she said casually.
My cock understood before I did, but when I felt it swelling up in my belt it hit me. “You’re making them shorter?” I asked, trying to keep the strain out of my voice.
“Yup,” she said, again as casually as if we were talking about the weather.
“Oh,” I said, although I’m not sure if any sound actually came out. I went back to the living room.
To be continued
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