Fifteen Days, Part One

I have to admit I’m in awe of you folks who’ve managed months on end. I think I would have lost my mind. I’ve pulled off a month or so twice, but the most maddening stretch I ever had was just fifteen days. Perhaps it’s because that happened very early in my time with T&D. Actually, it was with the girlfriend who got me into all this originally.

I know, fifteen days doesn’t sound like much. But for me, it felt like endless torment. Here is what happened:

Jenny and I had been cohabiting for a few months when she started weaving more “kinky stuff” into our sex life over time. Most of it was fairly tame, very “Fifty Shades of Grey.” One evening she asked if I’d be up for trying chastity play, and I agreed without hesitation. It quickly became clear that by “chastity play,” she meant keeping me locked up, not her.

We eased into the routine. At first, I wore the device for a few hours during foreplay. Soon, she had me put it on in the morning, then call me at work to 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 my belt getting ready for action, but she told me I could either let myself out that evening or wait and she would handle it in the morning. I knew which choice she wanted, so I waited, lying there half the night frustrated and horny, wondering if I was an idiot for not finishing myself off. All I had to do was reach down… instead, I waited until Jenny decided I could cum. And of course, during all these times, Jenny came whenever she pleased, usually with my help. “Chastity play” didn’t really apply to her!

After a while, it became obvious that she loved teasing and denying me. Our sessions got closer together. Soon, I was wearing the belt for longer stretches; first day and night, then two days. One weekend she locked me in Friday evening, then tormented me with several heavy make-out sessions on Friday and Saturday. On Saturday night I asked for some relief but she said to wait. She finally let me out Sunday afternoon for a great “nooner,” but after dinner that night, she was already trying to get the belt back around my waist. I managed to hold her off for a few days, but I knew it was only a matter of time before she pushed for a really long period.

The frightening part was that a portion of me was really enjoying all this. Jenny had brought out something in me I hadn’t imagined existed. I knew sooner or later she would push for an extended “chastity play” duration, and despite dreading it, I knew I’d agree. Sure enough, she mentioned it one day while we were eating lunch at a park. She wanted to try for “more than just a few days,” and when I asked how long, she said she didn’t know yet; I would just have to trust her. I thought about it for a couple of minutes, then agreed, but the words barely came out because I was so nervous.

I relaxed over the next week or two since we had agreed that I’d get a break before “the long game” began. During that week she went shopping on a few nights, saying she was thinking about a “new look.” Like an idiot, I didn’t connect the dots until later. I just told her I liked what she currently wore. She has short red hair and a great figure, but doesn’t always show it off. Usually, she wears jeans, sneakers, and a sweatshirt or one of those old flannel shirts from her grunge days. She said that was sweet of me to think so, then headed off to the mall.

Saturday morning we slept in, then started kissing. Eventually, she began kissing my chest, then my belly, before taking my cock into her mouth. After a few minutes of pure bliss, she let go and lifted her face next to mine but kept massaging my cock with her hand.

“I think this should be the day,” she said. My already hardening shaft swelled even more for a minute, and she grinned as she felt it in her palm. She knew she had me exactly where she wanted. I nodded. She said “Okay” then took my cock back into her mouth. Soon after, I came harder than I ever had following any period of chastity play, despite having relatively normal sex for a week prior. Then, just before lunchtime, I was locked in the belt again.

After dinner we watched a movie, then moved into another make-out session; and even with that awesome morning orgasm, by bedtime I wanted more. Too bad for me.

Sunday felt familiar if not always comfortable. I had endured this long stretch before and knew I could handle the horniness and frustration. Jenny teased me often, but it was to be expected. I remained nervous, but so far things were okay.

On Monday, Jenny turned up the heat. I got up and showered first, then made breakfast while she prepared for work. When she walked into the kitchen, I nearly spilled my coffee. There she stood in a very short gray skirt and ankle boots, nicely displaying her gorgeous legs. She wore a white blouse unbuttoned to reveal just a hint of cleavage and breast curves, with the key 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. Rarely had I seen her in a dress or skirt, never anything quite so short. She looked incredibly hot. That combined with nearly two days of pent-up arousal caused me to swell up inside the belt more than ever before, compounding my frustration. All I could think about at work that day was Jenny in that outfit and how much I wanted her. I tried not to dwell on “the long game.” She had just begun, and I wasn’t sure if I would be able to handle it.

She wasn’t done with me for the day though. After we both returned from work, she gave me a long, deep kiss that turned into another make-out session. She stopped short when my hands started wandering and told me she was going to cook dinner. While she cooked, I put on the TV news but couldn’t have told you what happened; all I could think about was Jenny in her skirt, my cock straining against the belt, and how much I wanted to cum. My thoughts settled as we ate dinner and chatted about work, then Jenny went off to do something in the bedroom while I washed 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 her 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 beside me. Before she even leaned in to kiss me, my cock strained against the belt again. When our lips met, my whole body buzzed 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 once more. I pretended to read but wasn’t really focused. All I could do was sneak glances at Jenny next to me while my cock throbbed and my brain swirled.

After her show ended, 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 remove her panties, then her negligee. She gently pushed my head toward her pussy. That was more than enough hint; I enthusiastically began licking her pussy until she came at least twice. Hoping against hope that my turn would be next, when she said, “It’s probably time to go to sleep,” I asked meekly if I could cum first. She stifled a laugh and said kindly, “No, baby, not tonight.” But she looked surprised that I had even asked.

That night was tough for falling asleep. I kept picturing 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 checked the clock and saw it was midnight.

Since Jenny locked me into the belt. And based on her reply when I asked to cum earlier, I had a strong feeling that relief was nowhere in sight. Tuesday morning repeated Monday’s events, but this time Jenny wore a short black skirt with a top that felt tighter and more form-fitting. It felt like I couldn’t breathe properly. Concentration at work became difficult. I had definitely reached a level of chastity play desperation I hadn’t experienced before; my need was growing intense. That evening, I arrived home first and began preparing dinner. Jenny entered while I was busy in the kitchen, gave me a hug from behind, then slid her hand down to my crotch where she tugged lightly at my belt. Instantly, I became erect again—hard as I could get with that cursed belt on. Jenny sat on the counter chatting while I cooked, her lovely short black skirt riding up on her thighs as she crossed her legs. I chatted back, but inside I was going mad. I kept reminding myself not to cut or burn myself while cooking, to try looking at her face rather than her legs when speaking, and to try ignoring my throbbing cock for just a moment. She began cleaning up after dinner, but I insisted on doing it myself. I was nearly finished when she returned to the kitchen wearing another negligee, this one white with a single button placed just below her breasts. She looked incredibly hot, and I felt more horny, frustrated, and desperate than I ever thought possible. I decided honesty was best. “Jenny, you’re driving me crazy,” I said, hoping like hell she would show mercy. Instead, she simply smiled and asked if I wanted to watch a movie. Of course, anything you want, just please let me cum! We watched half the film on the couch; she snuggled against me while I stared down at her mostly naked body and the key hanging from my belt between her breasts. What movie were we watching? I’m not sure I even knew at the time. Later in bed, I tried to step up my game, spending more time between her thighs and attempting to make her cum as well. When it was bedtime, I was disappointed but not surprised to find she had no intention of letting me cum that night. This time I didn’t ask, and she didn’t mention it. Wednesday and Thursday passed similarly: another short skirt, another sexy top. All I could think about was coming. By midday on Thursday, my frustration and desperation were so high I thought I might cry. But then something different happened Thursday night. Jenny came home from work and changed into her old jeans and a flannel shirt. After dinner, she took me to the bathroom and retrieved her key. “It’s time for some maintenance,” she said firmly. “I’m going to unlock you, then we’ll clean the belt. You’ll trim your hair down there, take a shower, and then the belt goes right back on, understand?” I agreed. The moment the belt was off, I got hard as a rock. It had been my first full erection since Saturday morning when Jenny gave me that incredible blowjob. Relief came mixed with embarrassment and frustration. Jenny smirked at it, then we began “maintenance.” She was very business-like and firm, warning me not to touch myself and watching while I shaved and showered. By the time I dried off, she had the belt ready to reapply. I hesitated briefly, but she gave an insistent shake of the device held out toward me, and with a groan, I put it back on. She snapped the lock shut, tossed the keys into the air, caught them with a smile, kissed my cheek, and said, “I have some stuff to do in the bedroom,” before walking away. I wandered back to the living room, tried watching TV and reading a magazine, but the business-like atmosphere of the maintenance session was already fading. I found it hard again to concentrate on anything except cumming. Finally, I went into the bedroom to see what Jenny was doing there. She was seated at her sewing machine in one corner, with a pile of her new short skirts 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 my mind did, but when I felt it swelling within the belt, it hit me. “You’re making them shorter?” I asked, trying to keep strain out of my voice. “Yup,” she replied, just as casually as if we were discussing the weather. “Oh,” I said, though I’m not sure any sound actually came out. I went back to the living room. To be continued