Loctober Send-Off

This story is related to the 'Roommate got my key' series, although it's not necessary to read that before this.

Anywhere in the following story, if it basically says that's 'another story', then that's something you'll be seeing later...

Hope you like it!

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"May I come in, Mistress?"

I stood outside her door, patiently, waiting for her command. She was standing in her doorway in a black robe with red borders, her eyes focused on me. She leaned against the frame, watching me like she was trying to judge whether or not to let me in.

"Are you ready?"

In four hours, it would officially be October 1. It would signal the start of 'Locktober', the month-long chastity challenge that's well-known amongst those who indulge in the lifestyle. Ever since my chastity journey took a turn overnight from solo to two keyholders, I've been thinking about this. I'd never managed to do Locktober properly when it was just me, the temptation to unlock myself just too strong. But this time, my willpower was not needed, for I was under command...

"Yes, Mistress. I am ready".

In preparation for this night, I had been unlocked from my cage last weekend. My master and mistress have been putting me in longer and longer lockups, getting me used to keyholding. And so, one week is far too long to go without a lockup. Of course, I wasn't allowed to cum, and I followed that order strictly. I was instructed to be here tonight on time, for a big 'send-off' into chastity.

"You may come in"

She turned and walked inside, disappearing into her bedroom. I quietly followed her inside, removing my shoes and closing the door behind me. I followed her into the bedroom, where she was now lying on the bed, scrolling on her phone. Without looking up, she addressed me.

"Get into position, slave".

The 'position' was simple. Whenever one of them would ask me to get into position, I'd take my clothes off, turn my back to them, and get down on all fours. I would then keep my ass raised, while folding my arms on the ground and putting my head on them. In this way, my head would always be down, and my ass would be presented to them. This wasn't the usual slave position you'd see, but it was thought out by them, and so, had a 'personal touch'.

I followed her order and got into position. I waited and waited, for what seemed like ages, but must have been about twenty minutes. I heard a knock on the door. I head her speak from behind me.

"Go open the door. Do not cover yourself up".

About two weeks ago, she had given me the same order. I was dreading the task, and just hoping it was Master at the door. Unfortunately, my luck didn't favor me, and it was her friend. I think it would be an understatement to say she was shocked. But that story is for another time. I went to the door, once again hoping it was Master. This time, my prayers were answered.

I let him in, closed the door, and followed him to the bedroom. He flopped onto the bed beside Mistress and pulled out his phone. Since I wasn't commanded to stop, I had to get back into position, and I did. After another excruciating wait, they finally broke the silence.

"I think it's time", he said.

"Yes, it seems so. Let's get on with it. What do you say, I take the first shot, or do you want to start?"

"I'll start. It's been some time for me".

"Okay, the other room is ready. Get up, slave!"

The last command was clearly for me, and I got up, breaking my slave position. I turned round, kept my head down, and put my hands behind my back. Master got up from the bed and went out of the room. He clearly went to the other room - the 'sex and bondage dungeon' room, another story - because he returned with a pair of handcuffs, a collar and a leash. He took the handcuffs first and secured my hands behind my back. Next to go on was the collar, and the leash.

"Follow me, slave."

This was another one of my 'slave commands'. It meant I would have to get down and move on all fours while he led me by the leash. I did as instructed,  and with my head towards the ground, followed him out of the bedroom and into the other one. Once we were inside, I looked up and he motioned for me to get up.

"Get in there", he said, pointing towards a wooden contraption that I hadn't used until now. It was a wooden plank, with semi-circular cuts, and I was pretty sure what it was meant for. I bent over, so my waist was in the large cut. It was low, so my ass was a little bit raised.

I felt Master's hand on my ass, and his light touch made me shudder.

"Good boy. Now stay still, and don't move", he said. I did my best to stay still as he brought another wooden plank identical to one I was on, and it fitted it over my body. And with that, I was locked into place, unable to move from there. He then moved over to my hands. My hands were already locked, and he just fixed the handcuff to something above me, so they were suspended.

I couldn't see what he was doing behind me, but soon, I felt restraints being fastened on my ankles. It was a spreader bar, so I couldn't close my legs. He must have secured them to some other place too, because I couldn't move my legs forward or backward either. My ass was nicely spread now. But the next place I felt his touch were my balls. His touch made he hard, and he laughed.

"Looks like someone is excited.."

He came up in front of me, and clearly, he had undressed. He was completely naked now, and had a ball gag in his hands. He secured it around my head, and went back behind me. Suddenly I felt him put some sort of string or rope around my balls. Without warning he yanked on the rope hard from between my legs, and the sudden pain made me cry out through the gag.

He eased his pull and ran his hand over my balls again. He left his spot behind me for a second, as I felt his absence, and I heard the sound of a bottle opening. In a few seconds I felt his hands and I something cold being applied on my asshole. It was lube, and he applied a quite generous amount of it, because soon, I heard him smirk in satisfaction. He began by pushing one finger in, but soon, it was two and even three. It was becoming more and more difficult to stay in my position, but I was helpless. He could sense my struggling, because he kept increasing the pace of his fingers.

He stopped just as suddenly as he started, though.

"Are you ready?"

It wasn't my first time answering this question tonight, and I was beginning to sense it wouldn't be my last. Of course, he knew I couldn't answer him.

"Aw, gag got your tongue? Well, don't worry, your asshole looks pretty ready for me. And that's all the answering I need..."

I prepared myself, and soon, I felt him enter me. I had discovered long back that he was bigger than his underwear made it seem from outside, and I felt all of it go into me slowly. I gasped, although it just came out like a muffled groan. Slowly, he pulled back out, and went back in, faster this time. He got into a rhythm, slowly in and out, but then, suddenly enough, he began thrusting quickly. I screamed into the gag as I felt his hard cock reach deep into me, and it wasn't long before I felt close to an orgasm.

He wasn't about to let that happen, though. He slowed down, sensing my situation, and then just stopped with his dick still inside. He moved slowly in me for a second or two,  before then thrusting with pace again. Quickly, I was brought to orgasm, and as I felt it, I begged to be released from my restraints so I could feel it properly. But no, I experienced the waves helplessly fixed. He pulled out, suddenly and I saw him reach in front of me. He was about to orgasm, and he did it on the floor right in front of me.

He closed his eyes as he shot a huge load on the floor, and then came closer to me. He put his hand on my neck and roughly raised it towards his own.

"You see that? You're gonna clean it up like a good little slave, aren't you?", he said, pointing at his cum.

He opened the restraints and pulled me out of the wooden plank. As I got out of it, I saw my own cum was dripping from the bottom side of the plank. He grabbed my hair and pushed me into the cum.

" Let's clean this side first before we go over to the other side, yes?"

He roughly took off my ballgag, and I licked the wood and the cum on it with my tongue. Soon I felt a tug on the leash I had simply forgotten I was wearing, and he dragged me to the front, where his cum formed a little pool. Once again, he pushed me towards the floor and I stuck out my tongue in obedience.

"Ugh, on the floor?"

It was Mistress' voice, and clearly she was behind me.

"Why, what's the problem? It's not like you have to clean it. Every mess on the room is his mess, and he'll clean it all up like an obedient slave, even if it takes him all day..."

I kept my eyes down, as I heard Mistress approach me.

"I suppose you are right. Well, is it my turn yet?"

"Oh you can have him", he said. And he must have handed the end of the leash to her, because this time when it was yanked so I would face upwards, it was her face I saw.

" I guess it's my time now, huh? Well, why don't you follow me to the bed right there", she said and walked towards it with the leash. I followed her, sat beside my bed as she got up.

"Call for me when you're done", Master told her and left. She nodded, and looked at me.

"Come on up here", she ordered.

I got up on the bed and she opened the drawer on her side. I couldn't see what was there inside, but clearly, I wasn't supposed to. At least, not yet, because she looked inside and then turned to me without closing it.

"I will grant you one of your greatest wishes now, slave. Tonight, you get to enter me".

I couldn't believe it. Was this really going to happen? My desire for months had been to have sex with her, from much before the start of this arrangement. Was she really going to let me do that?

"Put your mind to rest for now, because first, it's your mouth that will do the work."

She removed her robe to show me that she had nothing on inside. She moved to the centre of the bed, spread her legs, and put her arms on the bed rest.

"Let's play a game. If you can't get me off in thirty seconds, you'll never see these again." She gestured towards her amazing breasts as she said that and covered them up with her robe. "Time's running out, slave.."

Immediately I reached for her vagina and started working my tongue. I started licking her clit first to get her started off. Time was against me, but I had worked on her enough to understand exactly what she liked. Thirsty seconds was very less, though. Usually, I'd take my time, slowly bringing her to completion, but I skipped that, and it was just a barrage of my best moves. I could feel her getting wetter and wetter, and though she must have been trying to stop herself, she had taught me too well. The wave hit her just as the alarm clock rang out, but it's sound was drowned out by her.

She smiled and looked at me. Breathlessly, she spoke. "You have learned well, slave. Come, get your reward". She opened her robe, revealing her breasts in their full glory, and I dove into them. I sucked them and caressed them while she grabbed my hair and pushed me into them.

Soon, she pushed my face away and reached into the drawer. Out came a sleeve, and I realised, painfully, that her promise of letting me enter her had an unfortunate catch. I would have to put on the sleeve, which meant I wouldn't feel her inside.

"Aw, got a little too excited, did you? Well, never lose hope..."

She reached out to my dick and pulled it towards her. I moved in as I felt the pain, and soon I was right in front of her. I was on my knees, with my dick level her neck. She put some lube on my dick and fitted the sleeve over it. She took a key from the table and reached behind me, unlocking the hand cuffs. She proceeded to push me down on the bed. I lay on my back now, and she reached back into the drawer for some rope. She tied my hands to the bed posts and spread my legs. Slowly, she positioned herself on to my sleeve-covered dick and lowered herself on it.

I felt the sleeve go inside her, but it was a distant feeling. She slowly began moving up and down, and my goodness was it enchanting sight. I forgot everything else as I watched her thrust, her gorgeous breasts dancing in joy, one hand playing with her pussy as it welcomed the huge sleeve, and the other behind her, holding on to the bed for support. Oh, I would have given everything to be able to hold on to her tits as they bounced up and down. Soon, she was close to her second climax of the night, at least as far as I knew. My dick might have been shielded, but as she orgasmed with it still inside, I felt her shudder as it hit her.

She just stayed like that for a few seconds, her hands on my thighs for support, and her head towards the ceiling. She wasn't done, though. She took her hands off my legs, leaned towards me, and placed them on my chest. She pinched my nipple hard, and I tried hard to not shout. She began thrusting again, and this time, my nipples were being pinched. She took a bit of cloth hanging over the frame, stuffed it into my mouth, and continued, more vigorously. It took her slightly longer this time, but soon she was there again, shuddering to an explosive orgasm.

Smiling, she put on her robe and got down from the bed and went outside the room. I craned my neck and looked down. Now, my dick isn't very small by any means. When I'm hard, I can easily hit easily hit seven inches, but this sleeve was at least an inch or two more than that.

I heard footsteps, and both Master and Mistress were here. He untied my hands and I got up to sit.

"Get into position, slave", he ordered.

I did the same, but he came up to me and put my head up. "Just on all fours this time, keep your head up"

I felt some lube being applied again to my asshole, and Master was in front of me, disrobing and getting on to the bed. He was on his knees and he thrust his dick towards my mouth. Understanding my assignment, I opened wide and welcomed him in, sucking him like an eager slave. As I was doing that, I felt a finger up my ass, that was soon removed by something harder, longer, wider. I guess, they were ganging up on me.

Words will fail to explain just how I felt as they thrust into me from both sides. Rhythmically they fucked my holes, and I wasn't able to make a sound. The sleeve was still on my penis, and I must have ejaculated into it twice. Master was soon to pump his load into my mouth until I gagged, and he just carried on again. After a long, long time being filled from both ends, Master's second load signalled the end, and they both pulled out, leaving me exhausted on the bed.

"Use the shower, clean everything up, and join us in the other room", Mistress told me.

I don't know if they were gone immediately, because I just lay there, unmoving, on the bed. After some time, I slowly got up and got down from the bed. I took off the collar and the sleeve, and picked up the strap-on from where Mistress had left it after fucking me. I slowly walked to the bathroom, and washed the toys. I forgot about the gag, and I went back to retrieve it from the floor. After washing everything and leaving them to dry, I took a shower. I washed the cum and lube off my face and ass, and cleaned everything. Once I had thoroughly dried myself, I went on the bedroom.

They were sitting on the bed, and looked up from their phones when I came in. Between them, a brown box lay on the bed. Master gestured me closer, and Mistress picked up the box. From inside she took out a cage that I hadn't seen before, one that was smaller than any I'd ever work before. It was a darker pink than the one I was wearing until last week, and she handed it to Master. He signalled for me to move in closer, and I obeyed. He took my limp dick in his hands and fitted the cage over it. It was much tighter than I'd experienced and the little hard-on that I got immediately made me understand just how small it was.

"Welcome to Locktober, slave".

I looked down at the cage, and it looked so much smaller.

"You'll be locked at least October 31. There will be cleanings, supervised by one of us. We might ask for verification anytime during the day, even though we know you don't have the key. When we do, a picture is expected within 10 minutes, understood?"

I nodded my understanding to him.

Mistress continued, "You'll be cleaning out your underwear drawer and keep it all in the other room. From now on, at least until the end of the month, you will only wear panties I pick out. Of course if you feel there is a need for you to be unlocked or wearing regular underwear for health reasons or work, we should be notified one day in advance. Well, that should be it. Welcome to your chastity fest."

"Yes, Master. Yes, Mistress".

As the clock struck twelve, I knew this was going to be a month like no other.