Prelude

"Think about it this way" she whispered as she clicked the lock shut on the new chastity cage she bought just for the special occasion, "31 days, 744 hours, 44,640 minutes -- that's not too long when you think about it." The lump in my throat made it impossible for me to speak. My mind was racing but I couldn't help wondering if agreeing to Locktober was going to be something I'd regret or not -- I've never gone that long in chastity, a couple of hours at best. The smirk on her face made me wonder how serious she really was about all of this. After all, it was my idea to begin with and she usually lets me free after a few days of teasing anyway. I could tell she was waiting on me to say anything at all. I was standing in there completely naked with her kneeled in front of me while she slowly stroked her hands all over my locked cock as if she was admiring her captive prize. "No, not at all." She said to herself with a grin as she bounced up and fixed the keys to her necklace and started out of the bedroom. She paused for a moment in the doorway and looked back over her shoulder to see if I was watching. All she was wearing was a short, cropped hoodie, some black lace cheeky panties, and some fuzzy socks. I could feel my cage tightening. "Happy Locktober!" she said with a laugh as she smacked her ass cheek and took off down the hallway to make her morning coffee. "Happy Locktober..." I thought to myself, "Happy Locktober."

We haven't always been this adventurous in our sex lives by any means. Since she and I first started seeing each other several years ago, a lot has changed. It started with what most would consider to be a vanilla relationship to what now is the kind if sex life I only fantasized about, things that I never had the courage to tell any of my partners before now that I was interested in. For one: when I first admitted to her that I wanted to watch her have sex with other men, she didn't fully believe me. All her exes were the jealous type and before me, she had never considered anything but monogamy. After a lot of role-playing and long conversations about our desires and boundaries -- we have finally taken the plunge and started exploring our sexuality together.

Chastity was a by-product of us exploring my submissiveness in a lot of ways though. Although it's rare, when we are watching certain types of porn together it's nearly impossible to not eventually come across a video of a man wearing a chastity cage. We both were eventually curious and influenced enough to finally buy a cage online and see what it was like, but it never really ended up being something that stuck for us -- at least not for a long period of time. I'm embarrassed to say that even buying one of the smaller chastity cages was ultimately still too big for me. I didn't even fill the cage up halfway, so I was still able to get fully hard and it didn't seem like all the fun we thought it would be. We still used it from time-to-time when she felt like teasing me -- but after a bit, we would just unlock the cage and move on. When I half-joking mentioned Locktober to her however, she took matters into her own hands and surprised me with a new purchase.

Unlike the cheap, too long, and bulky cage we had sitting in the bottom of a drawer for the better part of 2 months -- she unboxed next to me in bed a solid stainless steel chastity cage that looked way too small for even me to even fit. "Think this one will work better, or should I have gone smaller?" She said with genuine curiosity as she held it up to the old one, closely examining its dimensions. "Looks a bit small to me" I chuckled as I snatched it out of her hands to get a closer look at it myself. With almost no hesitation, she flung back my side of the bed covers and started tugging down my boxers -- "let's have a look and see!" After a bit of play fighting and struggle from me, I eventually let her take my underwear down to see for herself but as soon as her hands came near me, I started to get semi-hard. "Now how am I supposed to see if this tiny cage fits this tiny cock of yours like this?" As soon as those words came out of her mouth, my dick shot up, fully erect and throbbing immediately. "Oh, you like that too don't you, you little pervert."

As much as I didn't want to admit it, there was no denying how turned on and excited I was by even the thought that I would need to wear such a small cage and she knew it. "It is the last day of September" she whispered as she slowly traced her fingertips up and down my aching cock "Maybe I should be nice and let you get off one more time while you still can." She stopped for a few moments and reached into the bedside drawer where we keep most of our sex toys. "There we go" she said as she pulled out her new favorite dildo, "you didn't think you're having all the fun tonight, did you?" When she looked over and saw me stroking myself, she swatted my hands away from my dick with her toy and reminded me that I needed permission to touch myself. Her favorite dildo is bigger than me in both length and girth, by a lot, and she loves to tease me about that.

As I sat up over top of her and started pulling the covers down from her side of the bed, she was already touching herself and starting to get wet. She grabbed me by the hair and pulled my face up to meet hers and blew me a kiss before pushing my head down towards her crotch -- but I already knew what she wanted. Ever since she started sleeping with Jordan and on nights he wasn't able to come over, she loves to have me go down on her while fucking her with the dildo closest to his cock. Sometimes they sext during and other times she looks through the pictures I've taken of them together while I make her cum, but he's been out of town on business for the past three nights and in the spur of the moment she didn't even have her phone with her to be able to look at their photos.

She told me to hold on for a second and sat up to look for my phone so she could browse the photos I've taken of her with Jordan. I tried to get up to grab my phone first, but she beat me to it and seemed surprised to unlock my phone to find that I already had recently been watching porn. She sunk back down into the bed and told me to get back to work while she looked to see what I've been up to. After a few more minutes me licking her clit and fucking her with "Jordan", she grabbed the hair on the top of my head, pushed my face in harder against her, and told me she was about to cum -- which was a lot quicker than how fast she normally gets off. Once her legs stopped quivering and her breath was not as heavy, she looked through my phone for a few extra moments and locked the screen back before motioning me to come up and lay next to her.

My mind was racing, trying to remember what videos I had been watching, but I had no idea. She kissed me on the lips to taste herself on me while she rubbed my dick like she was going to let me cum too, but she abruptly stopped. She left her hand wrapped around my dick and gave it a few playful squeezes while she bit my lip. "You are such a little pervert, aren't you?" she said under her breath before jumping out of bed and going to the bathroom to start the shower. I laid there on the bed for a moment trying to gather my thoughts while I was dripping precum in frustration, trying to remember what in the world I had been watching last. I may not have remembered at the time, but as Locktober goes on -- I'll realize she won't soon forget and won't let me either. She called out for me to come join her in the shower and to hurry.

"Someone's still horny," she laughed as I pulled the glass shower door back close to join her and she saw that I was still fully erect. She turned back away from me to let the hot water run down her face for a while. After a few moments, I came up behind her and wrapped my arms around her waist and started kissing her neck. She could feel my dick starting to rub between her cheeks in desperation to cum, but she only entertained it for a short while before turning back around and handing me her soap and wash cloth. Without having to say anything, I knew she wasn't going to let me cum just yet, so I hoped that by doing a good enough job of washing her that I would have some relief soon. It was erotic torture for me. I washed her head to toe, slowly admiring every inch of her body along the way and fighting the urge to grab myself and cum while I still could. She slid the shower door open and got out without closing it back. "Go ahead and shave and trim yourself to get ready for your new cage before the water runs cold" she said as she stood before me drying off. I started to slide the door back closed, but she stopped me and told me to leave it open - probably to make sure I don't touch myself without her permission. If so, she was right about that, but I accepted my fate eventually as we laid down to go to sleep.

The next morning went as planned. "Happy Locktober!" she said with a laugh as she smacked her ass cheek and took off down the hallway to make her morning coffee. "Happy Locktober..." I thought to myself, "Happy Locktober." As I threw on my robe and started making my way to the kitchen, I could hear her singing while she made her coffee -- she was in an awfully good mood. As I reached above her to grab myself a mug, she grabbed my cage from over my robe and asked me how it felt compared to our old one. "Good I guess, it's more snug than the old one but we'll see how it goes." I said with a laugh. She and I both have work from home jobs, so we quickly moved on, grabbed some snacks for the day, got dressed, and made our way to our computers to get the day started.

She and I both join occasional virtual meetings, and I must admit that it was a rush having my secret -- knowing my dick was locked up while I chatted with the team. I couldn't stop thinking about how badly I wished I could have gotten off last night while I still had the chance and for how long she was going to make me go through with this. We try to take our lunch break at the same time and had the opportunity to today, thankfully. I needed to ask her how much longer I had to keep this thing on. It must have been on her mind too because I could tell when she asked me how my day was going, she really was asking how well I was handling blue balls and my new cage. "It's been long" I said with exasperation, but she quickly interrupted me to say, "unlike that little dick of yours." We laughed for a minute, but I quickly got back to the matter at hand, "But seriously though, how much longer do I actually have to wear this thing?"

"Oh, come on, you're not even halfway through day 1 yet!" she laughed. "Well, it's kind of hard sitting there all day like this" I said pointing down to my crotch. "If it's bothering you sitting there all day, why don't you come meet me in the bedroom after you eat, and I'll fix it before we get back to work." She smiled and finished her drink and made her way to the bedroom. That was a lot easier than I thought it would be, but I was relieved. I wasn't even 5 hours into the day and even though I had enjoyed the tease, I was absolutely aching and ready to take this tiny cage off. When I made it into the bedroom, she was sitting on the edge of the bed twirling the keys around her neck with one hand and patting the spot on the bed next to her with the other. "Pull your pants and underwear down and I'll take care of you" she said with a bit of a mocking tone. I was so eager for relief that I dropped my pants and sat down next to her without realizing that she had a butt plug and bottle of lube sitting on the nightstand next to her.

"No, I don't want you to sit down right here -- I want you to bend over right here." She giggled at first from the confused look on my face, but her tone quickly went from teasing to a more commanding and assertive tone. "You said that you had a hard time sitting there all day and tried to get out of Locktober early. Now I'm giving you something else to think about while you're sitting there." I tried to say anything, but before I could she interrupted me while picking up the plug. "Keep talking and we'll make it No-Nut November too, now bend over." This wasn't the first time we'd done anal play, so I wasn't unaccustomed to it, but at the same, I didn't expect it now -- not as a punishment and not with just a few minutes left on my lunch break. As I laid bent over the bed, she ran her fingers across the tip of my cage to feel the precum leaking out and she slowly pushed the plug into place. I let out a deep breath when it was in, and she followed up with a very firm smack against my ass and chuckled as she walked out of the bedroom to get back to work.

I could feel her eyes watching me walk across the room and back to my desk to get back to work. I was having a hard time walking normally from the pressure of my dick trying to get hard but having nowhere to go, the fullness of the plug, and the stinging I felt from her hand. I didn't know if I wanted her to know how much I was enjoying this. My feelings were conflicted because on the other hand, I wanted nothing more than for her to unlock me. For the rest of the workday, I found myself shifting around in my seat trying to find a way to be more comfortable but also thinking about what had happened in the bedroom.

As if the day hadn't already gone by even more slowly than usual, I was asked to stay a couple hours over to put some finishing touches on a presentation before our quarterly business review -- just my luck. On the Brightside, this looming deadline has kept my mind busy enough that I wasn't thinking about how horny I was constantly. The house was quiet. After she had finished her work for the day, she and a couple of her friends went out for drinks and some dancing downtown for a few hours. I tried waiting up for her to get back, but I was exhausted and decided to call it night. While I was washing my face, I heard my phone buzzing from the nightstand by the bed. The text read, "I'll see be a few hours so don't wait up, but I guess you can go ahead and take out the plug ;)"

Before bed, I went to put the butt plug back in the nightstand but was shocked to see some keys left in the back of the drawer. The only reason I could think she would leave them behind was to avoid having to answer questions from her friends while they were out. I had a lump in my throat and my mind was racing with the pros and cons of taking it off. I tried to put the thought in the back of my mind but the more I tossed and turned in bed trying to get comfortable enough to sleep, the more it seemed like a good idea. Would she notice if I just took it off for a little while? I could make myself cum in no time and put it back on and she would never know. It felt so wrong but the more I sat with the temptation the more I could feel my cage tightening with the prospect of release. Fuck it -- I said out loud to myself and I hopped out of bed to grab the keys.

I was fumbling around with the keys so nervously that I couldn't seem to fit the key into the lock. Frustrated, I went to turn on the overhead light so I could see what I was doing better, and it was then I realized these were the keys to my old cage -- this wasn't going to work. Of course, what was I thinking -- she knew better than to trust me with the keys at home anyway. With a deep sigh, I sat back down on the bed to think for a moment and couldn't help but laugh to myself about the irony of it all. The light mood ended quickly when I heard the front door and her start to take her shoes off. I quickly turned off the light, threw the keys back in the drawer, and jumped over the covers. I could tell she was trying not to wake me by how quietly she opened the bedroom door and softly she was walking to the bathroom.

"Hey babe" I said to her as I sat up in bed -- I could tell she was startled. "I didn't think you'd wait up. I didn't wake you, did I?" she said back softly as she made her way to sit on the bedside. I could see the shine of the keys around her neck, and I placed my hand on her thigh and smiled as I shook my head no. She was wearing the short black dress I like and asked me to help her out as she spun around and moved her hair away from the zipper. When she stood up, she shimmied her body around and let the dress fall to the floor. Underneath she was wearing a matching set of underwear I bought her for her first night with Jordan. "I don't think I need help with these" she said seductively as she unclasped her bra, slowly pulled her thong down with a tease, and made her way to the bathroom to start a shower.

While she was rinsing off, her phone that she had left of the nightstand buzzed 3 or 4 times in a row and I watched as the screen lit up each time with Jordan's picture in the chat bubble. I couldn't make out what he had said but I could only assume he had made it back to town from his business trip.

After her shower was done, she made her way back into the bedroom wrapped in towel and left on the bathroom light behind her. "Are you still awake?" she asked quietly while dropping her towel to the floor, but she had noticed from the light shining in that my eyes were still open. "Good" she said to herself with a smile as she straddled herself on top of me, took the keys off from around her neck, and set them on the nightstand. Before either of us could say a word, her phone buzzed one more time and she reached over to grab it. After reading through the messages for a moment, she rolled off me to her side of the bed and spread her legs wide to start touching herself. "Even though you can't cum, there's nothing stopping you from making me" she said in a sly tone.

"Is Jordan back in town?" I asked as I made my way down to start kissing her thighs. She let out a soft moan when my mouth met her clit and said, "His plane just landed a few hours ago and he's on his way back." She placed one hand on top of my head and started grinding herself on my tongue then and I looked up to see her playing with her nipples with the other. I was grinding my cage into the bed while she used my mouth and I felt like the movement and friction alone could almost make me cum. The base ring of the cage was pulling tight as my cock was trying to get hard inside its metal prison. "Grab my favorite toy" she whispered as she let go of the handful of hair she was holding and patted the top of my head. As I stood by the bedside and before I could get the drawer open, she reached out her hand to catch the precum leaking out from my cage and pulled me in closer by the hips. "I bet you want to fuck me so bad right, don't you?" She said as she ran her fingers across the cage and felt my twitching. "Maybe you should just watch me fuck myself tonight, what do you think?" She opened the nightstand herself and paused for a few moments as she stared into the drawer.

I looked back to see the keys sitting on her of her dildo instead of in the back where they were left. Without saying a word, she reached in and picked up the keys, held them up towards the light shining in from the bathroom, and started comparing them to the ones she had left on the nightstand. I had no idea how she would react, and time felt like it was completely frozen. After a few moments that felt like an eternity, she turned back to me with a smile and said, "Aw you tried, didn't you? Too bad...I guess someone didn't learn their lesson earlier. Don't worry -- I have an idea already." She grabbed her phone and started typing a very long message -- her face completely lit up from the screen showed a look of someone who was determined, she was chewing at her bottom lip. She tossed her phone down and I could see Jordan was already responding. She grabbed the dildo and handed it to me with a grin on her face and said, "Happy Locktober!"