The Challenge

"Your asshole is TINY. Do you seriously never bottom? My man this is going to be a lot of fun. And remember, a month in chastity means no sex, so don't try to train this little asshole of yours, I'll know if you do and just might choose to keep this key long-term. Do you understand?" I nodded, unable to make the words come out.

SLAP. He smacked my ass, hard. The stinging sound rang throughout my apartment, the sensation hit directly into my psyche. "I asked you a question, Peter. Do. You. Understand." He punctuated each word with another smack on my ass cheek, I imagined that their glowing redness matched the embarrassment on my face.

"I understand...sir." I wanted to throttle myself for adding that last word. How could I deepen my own humiliation like this?

"Good. I expect you to text me a picture of your cage every day. I know you lawyers like to wiggle out of your obligations but believe me, I'll know if you cheat and there will be consequences." To reinforce this, I heard him jingle the chastity keys. He owned my cock; I would have to do whatever he commanded.

With that I heard him move away. I remained in my position, bent over with my ass facing towards him as I heard Caleb dressing. In another minute or two I heard him open the door "Enjoy pissing sitting down, I'll be back in a month." He left without another word, abandoning me to my fate, locked, humbled, shamed, and extremely horny. I had hated every moment of what happened but couldn't help but be incredibly turned on. Caleb's power was immense, it dominated my will, made me want to serve him. I felt my cock start to get hard in the cage, it swelled a tiny bit and then hit the confines of its prison. I looked down and saw that the flesh was popping out of anywhere it could, trying to expand through any tiny slit or opening. It was to no avail; I was extremely turned on but there was nothing I could do. I tried to jerk myself a bit in the cage, it did nothing. I was trapped.

I decided that the only thing I could do was distract myself. So, I sat my computer and started on my work again. My cock was caged, my mouth still tasted like his musk, and my own load was dried and crusty on my chest and legs. I hated that I loved this feeling.

****************

That night I had trouble sleeping. The cage was uncomfortable in every position. On my side it sat uncomfortably on the top of my thigh. Lying on my stomach, I felt it protrude between my legs. On my back it sat there, tenting the sheets and reminding me of my situation. On sleepless nights I would usually jerk myself and pass out. My mind still seemed to want the ritual to be possible, every few minutes my brain would think of something dirty and I would feel the blood start to flow to me nether regions. Just a few seconds after that I would be stymied, my magnificent erection foiled by this infernal cage. I hated Caleb in those moments, I knew he must have cheated somehow. Maybe he used a pump, maybe he had some kind of numbing spray, maybe he used drugs to make his load bigger. That had to be it, he was doping, it broke the rules of the game. I rationalized for hours but in the end, I always came back to Caleb.

His cock had been incredible. It was a work of art, the greatest physical display of male-power I had ever seen. These thoughts just made me even hornier. I hated the idea that I was submitting to his power, but I found my thoughts of Caleb so enthralling, so entrancing. He was like a drug to me, I couldn't help myself.

Around 4AM I couldn't take it anymore. I couldn't just lie in bed trying to fall asleep while obsessing over this man. I got up and put on some loose sitting sweats and fired up my computer. I was a corporate lawyer; I was quite adept at functioning on little-to-no sleep and in the end decided that my brain was best served by putting itself to the task of working through complex M&A issues.

In the back of my brain, I never stopped thinking about Caleb though. Every time I moved the cage would shift slightly, bringing thoughts of my key-holder to the front of my mind.

*************

My balls ached. I hadn't gone more than three days without cumming since I was 11 years old. It had now been a week. Despite the fact that I was not having sex, not looking at porn, not trolling the apps, and avoiding any sexual temptation, I was hornier than I had ever been. Everything reminded me of sex. I imagined that the tallest skyscrapers were Caleb's cock. I saw a man drop a large yoghurt on the ground, the mound of splattered whiteness sent a chill up my spine, reminding me viscerally of his mega-load. 'I'm so fucked' I thought. 'Yogurt is turning me on.'

Every day, I dutifully took a picture of my caged member and texted it to Caleb. For hours afterwards I held my breath waiting for his reply. I found myself waiting on our text screen hoping to catch a glimpse of those three little dots that would indicate that he was typing a response.

After seven pictures he had said nothing. I panicked at first, paranoid that I was sending not just a dick-pic, but a chastity dick-pic to some random number. I checked and rechecked, I was indeed sending it to the right person. He just wasn't replying. The bastard, he was acting like this wasn't important. This was everything.

On day ten I finally got a response. "Nice balls, they look nice and full. Send me a pic from your office tomorrow." This request made me visibly anxious. I didn't play in the office. I kept my professional and personal lives separated by thick walls. Now he was breaking them down.

I didn't hesitate to fulfil his request though. It made me feel really good to do, actually. He had asked for something, I was responding, I hoped desperately that that would please him. Around lunchtime when many of my colleagues had left the office I shut my door and unzipped my pants, plopping my caged cock out of my fly. I took the picture and fired it off, quickly re-dressing myself. Once again, he didn't respond. I was sending these pictures into dead air it seemed. But never once did I consider stopping, this was my one connection to this incredible, powerful, sexy man and I couldn't give up. Plus, I needed out of this cage, I couldn't risk him keeping me locked for longer.

At the two week mark I started to feel something I had never felt in my life, my ass was horny. For me, sex had always been about my cock. Always. I never understood why it seemed like every other gay man was in love with bottoming, it had just never felt right to me. Which is why I was initially concerned when my butt started feeling so frisky, it was a foreign feeling. I decided to test this a bit.

In that shower that morning I soaped up a finger and reached between my cheeks. Slowly I started to draw little circles around my butthole. It felt incredible. I didn't dare penetrate myself, Caleb had ordered me not to. But he didn't say anything about me tickling the rim a bit. I looked down to see precum dripping from my cage. Oddly enough my cock wasn't straining in its confines, I felt soft, almost smaller than usual yet this tiny bit of sexual touching with my finger was turning my sex-addled mind into overdrive. I stayed in the shower for almost an hour, gently diddling my butt.

When I emerged from the shower, I saw that I had a text from Caleb. "I want to see your asshole today." Did this fucker have my house bugged? Was he spying on me? This was bullshit, this wasn't part of the deal.

I responded immediately. "That isn't in the rules."

I waited for his response, an eternity seemed to pass in the minute or two that I waited. Finally, I felt the phone buzz in my hands and read his message "Around the two-week mark I find that sluts like you start to get really horny in their asses. Send me a video of your butthole twitching. I know it's not in the rules, but I think that you will do it for me anyway."

How did he know what I was feeling? Had he done this before? I thought for a moment. Maybe I could use this as leverage, he clearly wanted something, maybe I could deny him to get my sentence reduced. An entire plot formed in my head, I planned out all the contingencies. Then the strangest thing happened, I found myself on my bed, legs spread high in the air, phone propped on a pillow with the camera pointed directly at my asshole, and the video screen up. I just needed to press play.

I wanted to go with the plan. I wanted to stick it to this guy, try to knock him down a bit. Instead, I just pushed play. I looked at the screen, all that was in the shot was my tight, almost virginal asshole and my swollen balls. I winked my ass a few times, the feeling that he would enjoy seeing my butt twitch in anticipation of our upcoming session was too strong, I wanted to please him. I kept the video running for a full two minutes. Just a video of my butt, squeezing and unsqueezing. I sent it to him as soon as it was completed. A few minutes later I got a simple reply, it just said 'Good boy'.

I didn't hear from Caleb again for weeks, but I went back and read that single text exchange hundreds of times. I knew that he was enjoying this game and the idea that I was pleasing to Caleb drove me wild.

That night I dreamt of Caleb. I had a literal sex-dream about my tormentor. We made sweet, passionate love for hours in the very bed I was sleeping in. It was the first sex dream I ever had where I was the bottom. In the morning I woke up a sticky mess, my cage and crotch soaked in precum. It was the best night's sleep I had had in weeks.

**********

Exactly one month after this all began, I woke in a mess of divergent feelings. On the one hand, I knew that today was the end of it. This ordeal would soon be over, I'd be free. On the other hand, I had grown mentally very attached to everything that had happened. I spent hours a day thinking about Caleb. I barely knew the guy, I didn't know anything about him personally, I didn't even know his last name. But his power drew me towards him, I was an asteroid trapped in his planet's gravity. More than anything though, I felt horny. I had had to start wearing thick underwear to bed because I seemed to dream of sex all night long, every dreamed starred Calebs cock and my asshole. The first few times I needed to wash my sheets in the morning, it seemed easier to just catch all my goo in my underpants. A few weeks ago, I would have been utterly humiliated at this state. Now I found it oddly comforting to wake up after dreams of being butt-fucked with a load of precum soaking my underwear.

I looked over at my phone and saw a text from Caleb. I scrolled through our exchange, it was a lot of pictures of my caged dick and a lot of non-responses from him. I felt honored to be getting a response from him. I read it through a few times to make sure I had all of it down. It read "Good Morning boy. Tonight's the night. Feel free to douche yourself if you want but don't spend any time stretching yourself out - I want you tight as a clam for tonight. I've been waiting all month for this. See you at 7:00. Caleb. P.S. Got my test results yesterday afternoon, no need to bring condoms."

A month ago, this text would have sent me into a rage. How could he disrespect me that way, how dare he not pay proper homage to me? But in that moment, the only thought I had was elation. He had been thinking about me. He had been waiting for me. I felt so special, so blessed. I imagined him watching the video I sent, scrolling through my photos, I loved the thought that I was turning him on, I secretly hoped that he was jerking himself off to me.

I worked from home that day. It was common, a lot of folks did that on Fridays. Although I was fully going through the motions, my mind was definitively elsewhere. I had never been this randy in my life, I was champing at the bit, I would do anything to get off at this point. I could count the minutes until my release from this cage, I could almost count the seconds until this ordeal was over. In the first few weeks I really only had one emotion to describe my predicament -- anger. Rage that I had been bested by this other man, anger that he had caged me. As time went on, though, my emotions began to blur. I still felt some shame that my cock had been dominated, but I also felt oddly at peace. Despite the fact that I was denied sexual release and orgasm, I was also quite calm. This position almost felt... natural. It felt like I was supposed to be serving Caleb this way. My old-brain told me that that was nonsense, that the hormones and the horniness were scrambling my mind. The new-part of my brain told me that I was enjoying the denial, enjoying having my sexual independence taken from me by this powerful man.

At 5:30 I decided to douche myself. I had bought one online a week ago in anticipation. It was the first time I ever used one, before this point the work bottoms put in was just never my concern. The sensation was unfamiliar but once again oddly comforting. I felt a transformation was coming over me, one ushered along by a literal cleansing of my insides.

By 6:30 I was ready. I went back and forth on what to wear. I started something casual, some slacks and a decent shirt. In the end though I settled on just wearing a jockstrap. It kept my cage in place and would give him full access to my ass. A month ago this would be unthinkable, now I was scouring my brain for anything I could do to please Caleb. What had happened to that once dominant exclusive-top? In that moment I honestly didn't care, I just knew that I needed his cock, and I needed it badly. Had all the men that I had bested felt like this? Had I eroded their wills this way? Dominated their psyche so powerfully? The thought made my start to harden in my cage. In the past that thought would have focused on my dominance. Now I was focusing on how sexy it felt to submit, how those other men must have felt so vulnerable, so eager to please. That turned me on more until my cock was practically bursting through the cage. I shook the thoughts off, my cock softened in the cage and looked at the clock. 6:58. Showtime.

At 7:02 he knocked. I was at the door welcoming him in within seconds. He strutted in with an amazing amount of confidence, he looked like he owned the place. He gave me a once over, naked except for a jock strap, as I closed the door.

"Lose the panties. I want your caged cock to rattle around while I fuck you." I obeyed instantly and stood before him naked. I was so incredibly horny, but my cock remained limp in the cage, this night was about Caleb's cock and my ass. My cock wouldn't play a role. For once my mind was firmly encamped in being the bottom.

He started to loosen his tie, slowly disrobing. "I've enjoyed the pictures you have been sending to me, I watch that video you sent me a few times a day. I love to see a strong, dominant, cock-sure thing like yourself taken down a few pegs." My breath fluttered in my chest as he bore his hairy chest, his pecs rippled with each motion, my insides felt gooey in anticipation. He was so insanely attractive to me in that moment, I wanted to do everything to please him. I merely nodded in response to his musings.

"Cat got your tongue?" He seemed to notice me staring stupidly at his rock-hard body. "Oh, um yeah. I've liked sending you those pictures, it made me feel good to know that you were looking after me."

"You're probably horny as an antelope right now." He walked towards me, naked but for his underwear, the outline of his massive trouser snake leaving me quaking in anticipation. Caleb gently took hold of my balls, weighing them, assessing them. He looked over the tube that encased my cock. "Turn around and bend over, I want to inspect your butthole."

I did so without hesitation. I even went so far as to reach my hands around to spread my cheeks. A month ago, I was a dominant, now I was spreading my ass cheeks to let my cager get a clear and perfect view of my most sacred entrance. He leaned down behind me, getting eye-level with my brown eye. He reached out his tongue and gave my anus a single slurp. The feeling was like a bolt of lightening to my very being, it was heaven. As soon as it was there, it was gone. He stood back up. "You still look as tight and puckered as you did last month. Good job, some sissies try to relieve themselves with dildoes or prostate massagers after a week or two in a cage, I applaud that you fought off the urge and kept yourself chaste for me. You will definitely be rewarded." His tone drove me a wild, a mixture of deep, reassuring baritone with some positive reinforcement. I would do anything for this man.

I straightened myself and turned around to face him. At those last words the keys to my cage had appeared in his hands, I salivated looking at them, he held my freedom between his fingers. "You get these when I'm done with you."

I then felt his hands on my shoulders, he was pushing me towards my knees. I practically fell to the ground, coming eye-level with his beauty. I hooked my fingers around his underwear and slowly pulled them down until I had unleashed his monster. It was somehow more beautiful than I remembered, his gigantic mushroom head leading down to nearly a foot of smooth, thick shaft. Below that a massive set of hairy balls looked like two eggs hanging off his abdomen. He was magnificent. I couldn't help myself in that moment and I planted a kiss right on the head of his cock. I kissed it again, moving down the shaft, worshiping his powerful cock. I took each testicle in my mouth in turn, swirling them around on my tongue.

I felt his cock start to stiffen and grow, I let his balls fall from my mouth and licked all the way up his shaft, when I reached the head I took it between my lips and thrust my head towards his pelvis, taking as much into my mouth and throat as possible. His pubes tickled my nose as I stayed there, my throat fully impaled on his not-yet-fully-hard member. "A month in chastity does a lot to a man. A month ago I bet you would barely even give a guy a reach around, now you're gobbling my cock like a pro." With those last words I felt his fingertips on my chin, he pointed my face upwards so he could look into my eyes as I impaled myself on his cock. All I wanted in that moment was for him to feel good. I started to bob and suck, moving up and down on his cock, often gagging as its immense girth forced its way down my throat. I tried to keep looking into his eyes, I could tell that he was enjoying this and that gave me even more enthusiasm. I threw myself into the blowjob, enjoying every last second of it.

After ten or fifteen minutes he had had enough. "This has been nice, but I'm here for your ass. Go bend over the coffee table. Where's your lube?" As I crawled over to my coffee table I said over my shoulder "in there, bedside table, it's already out." In no time I was in position. The coffee table was the perfect height for someone to bend over, that's actually the very reason that I bought that particular coffee table. I had fucked dozens of men as they bent over this table, though this was my first time in this position. I stretched my arms and shoulders straight out, laid my head sideways on the cool surface and took a wide stance with my legs that would allow him to easily get behind me. It was the exact position I forced many of the encaged men I had bested into, now I assumed the position willingly.

Caleb returned in just a moment, his cock fully standing at attention, a bottle of lube in his hands. He put something between my legs, from my position I couldn't see what, truthfully I didn't really care as long as he started the show soon. I needed my ass filled. "I'll warm you up a little bit, but I'm not going to take too much time before I sink this whole cock up your butt." With those words I felt a cool slickness on my butthole. Almost at once I felt a finger push fully inside me. The sensation was otherworldly. He pushed right past my sphincter and was now quickly fucking in and out of my ass, spreading the lube around my rectum, gently pushing my prostate on every stroke. I started a low moan, this was the first time I had had sex in a month, the first time I had had sexual release of any kind other than dribbling in my wet dreams. His touch sent sparks up my spine, mingling in my brain and shooting out to all my extremities.