When I woke up on Sunday, I reached down as I usually did most mornings and grazed my happy trail as I continued further down. I reached into my boxer briefs and hit something unfamiliar. That helped wake me up pretty quickly, when I looked down all I could see was the pretty pink chastity cage I’d been locked in since Friday evening. My balls were aching already, part of my morning routine was rubbing one out. Now here I was unable to even get hard because Pete had put me in time out.
I got out of bed and threw on my shorts and tshirt. Went downstairs and grabbed a cup of coffee, I was still groggy but as I looked around I realized that my roommate was gone already. Turned out to be a good thing because I had some preparations to do before I went over Greg’s house later that afternoon. Once my coffee was gone I jumped into the shower and cleaned out, shaved my butt and balls, and soaped everything up still wishing I could jerk off.
After the shower I shot Greg a message and asked if he was still good to hang out this afternoon. Before I even set my phone down I had a message from Pete. “Hey bitch, how’s that cage treating you? Oh and don’t forget the jockstrap when you come over. I already told Greg I had a surprise for him.” I responded with “Yes Sir, excited to see you later!”
I wasn’t sure where that came from but figured I was excited at the thought of getting my cock back. I’m glad he reminded about the jock though. I grabbed the towels from the bathroom so I could wash them all and went down to the basement. Once those were in the washer I turned to grab the clothes out of the dryer after washing the jockstrap yesterday. When I opened the dryer it was empty though. I turned and grabbed the laundry basket from under the table and there right on top was the fluorescent pink jockstrap with the smallest pouch I’d ever seen, still hard to believe that it managed to cover much.
As I carried the basket up stairs, I finally realized that I hadn’t taken those clothes out. It had to have been my roommate, thoughts began to race around my head. “Had he seen the jock? Why was it on top of the basket? Why wasn’t his clothes in the dryer? Could I pretend it was from a hookup? Then how did I explain it being in my clothes pile.” I shook it off and decided to deal with that later. Now I needed to get ready for my day out with the boys.
I checked my phone as I folded the clothes and finally the text came through from Greg. “Hey yeah I’m down, apparently Pete has a surprise for us today too.”
“Oh? Wonder what that could be.” As I’m holding up the pink jockstrap. I stripped out of my normal clothes and slid the jockstrap on. It seemed like my balls would bust out the sides but the way it compressed the cage was amazing. It was like there was nothing there. I headed down the hall into the bathroom and looked at myself sideways in the mirror. The straps seemed to lift my ass just right and I realized how good I looked. “Maybe I should get a few of these, I wonder if they have ones with bigger pouches?”
Just then I heard the front door open and I panicked, I slammed the door to the bathroom. I looked around for a towel but realized that I had just taken the ones from in the bathroom down to wash them. The other towels were in the hall closet, so there I was in just the tiny jockstrap. My roommate Alex must have heard the bathroom door slam because he yelled down the hall. “Bro stop jerking off and help me put the groceries away.”
“I’m doing my morning stuff, I’ll be out in a few minutes.” I heard the sound of his shoes as he walked away. I was trying to figure out an escape plan. “I could take the jock off, no because then the cage is exposed and being pink makes it highly visible. Maybe I could run down the hall and make it to my room before he sees me. I have to run through the dining room which is where he is at putting away groceries. Fuck there’s no good options here. Maybe he has more groceries in the car.”
I pressed my ear against the door and heard him moving around inside, which meant he had them all in already. Then came a knock, “I have to pee let me in” I started to panic again when he knocked again, “come on I’ve been holding it.” I walked up and opened the door hiding behind it as he squeezed in around it. Luckily for me he just ran straight for the toilet, I darted out of the bathroom and pulled the door shut. I ran through the dining room and into my bedroom and threw on my shorts and shirt. Then I was back out in the dining room putting stuff away when he finished up in the bathroom.
“You could have stayed and finished up, we’ve seen each other naked before. How long have we lived together? Like 6 years at this point. Two gay guys living together that long in a one bathroom house are bound to see each other naked haha.”
“I was done and wanted to give you privacy.” I stepped around him and bent over to grab the last 2 bags off the floor. When I turned around he was right behind me and had this smile on his face like he was holding back a laugh.
“No fucking way, those pink undies really are yours.”
“What are you talking about?”
“Bro you can’t deny it, they are sticking out of the back of your shorts.” Just then he pantsed me and as I went to go drop the bags and pull them back up he put his foot right between my legs on top of my shorts. I realized I couldn’t get them back up with him standing on them and he was too big for me to force him off of them. “Let me see you in them.”
I stood up slowly and used my hands to cover the pouch. “Step out of your shorts.” As I did that he grabbed the front of my shirt and pulled it over my head so it was up and out of the way. He kicked my shorts back behind him and stepped around me. “Damn dude I never noticed that you were caked up. But I thought you were a top?”
The question hung in the air as I continued covering my pouch and he was completely behind me at this point. Then he stepped up against me and I felt his clothed package on my bare ass cheeks, I finally said. “I’m versatile top.”
“Well since you are wearing these I’m assuming that the guy you went to see Friday must be a top and you’re planning to see him again today. But that still leaves me to wonder when you got this jockstrap?”
“He’s letting me borrow it because he said it looks good on me.”
“It does, are you two dating or is this a hookup kind of thing?”
“A fwbs I guess, we haven’t really talked about that yet.”
“You’ll have to let me know because if you’re switching into bottom mode then I want to take this cake for a test drive.”
He backed away and thought it was over but as I went to grab my shorts he got in front of me. “As long as you are wearing that jockstrap you should strut around in just that.” He reached out and tugged on my shirt. I allowed him to pull it up and by doing so moved my hands away from the pouch long enough for him to see. I went to cover it back up but he grabbed my wrist and pulled it away. “Holy shit, it looks like your balls are about to fall out of that thing. Where’s the rest of the material?” He laughed again and let my hand go. I pushed past him and went into my room.
I decided to get dressed early and head over to Greg’s. When I left my room I found my shorts and shirt in a neat pile outside my bedroom door. He peeked around the corner of the living and looked sad when he saw I was clothed again. I walked out without another word. But when I opened the garage door I realized his car was blocking me in. I walked back in and asked him to move it so I could get out. “I’ll make you a deal, get back in just that jock and give me a quick dance then I’ll move my car while you get dressed.”
I had seen Alex flirt with his exs like this but having that energy directed at me felt weird. “I’m not sure that’s a good idea. We live together and I don’t want to ruin that.”
“Trust me nothing has to be weird between us, you are my bro. You know Sam, he and I are fwbs and we hang out almost everyday. Things won’t get weird I promise. You just look so good in that jockstrap that I want to see more. Plus I won’t be fucking you…yet!”
I decided it was fastest to just do as he said. I took off my shirt first then my shorts and he put on some fast beat music and I did a half ass dance. He sat down and I mainly tried to face away from him. As the song was almost over he said, “bend over and grab your ankles.” I decided to do it and through my legs I could see him adjusting his crotch. “Reach back and spread them for me!” I did as I was told then he stood up slapped my ass hard and walked past me grabbing his keys and walking out the door.
I threw my clothes on and got in my car. He was backing out as I did and then pulled into the other side of the driveway where he usually parks. I made my way to Greg’s and wondered how this would affect my living situation. As I pulled up i realized I was 45 minutes early. I thought about pulling back out and going to sit in a parking lot nearby but Greg had already seen me. He opened the door and beckoned for me to come in.
He was still straightening up, “you’re early, everything okay?”
“Yeah I was just excited to hang out, I should have text first.”
“No it’s fine, Pete said he was coming over early too.”
For the next 15 minutes I helped Greg clean up then he walked away and came back with Pete who looked at me and said, “you’re early, come help me grab something from my truck.”
We walked out to his truck and he opened the back door. “Get in pants off bitch.” I hopped up and he pushed me face down and undid my pants himself pulling the back down. He stuck two fingers in and began to go pretty rough starting out. Then his other hand slid between my legs and squeezed my cage. “God this is so hot. You were born to be bred and turned out.” Then he tried for a third finger before saying, “ not loose enough yet but we can work on that. Now get your ass out and your pants back on.”
Once I was out I shimmied my pants back up and he grabbed something out of the back seat. He turned around pushed a box into my arms reached in his shirt and pulled out the necklace with chastity cage keys on it and put it on the outside of his shirt. Then slammed the door and started heading for the house with me in tow. Once inside I put the box down while Pete helped Greg move the love seat to the corner of the room to get it out of the way.
Greg went into his bedroom to change into comfy clothes and grab his box of goodies. As soon as he disappeared behind the door Pete walked up behind me and whispered, “I want you to go into the bathroom and strip down to your jockstrap. Then when I text you, I want you to come back out wearing just that and get face down ass up presenting your ass to Greg and tell him that you want to repay him for showing you the ropes.”
“Yes Sir, I’m a bit nervous though. He hasn’t really seen my submissive side.”
“Don’t worry we talked about it and he wants to train you together. He even said when he went to the bathroom on Friday he had to shift his cock around and put on more restrictive underwear because seeing you all strapped up and rubbing your face on his crotch really got him going. Now go do as you’re told boy.”
I rushed off to the bathroom and stripped down, once again checking myself out in the mirror. I was brought back to the moment by the sound of my phone buzzing. “Get out here and bring your clothes. Put then on the loveseat when you enter the living room. Then get into position.” The text shot sparks through my body and I feel my stomach start to shake as nerves kicked in.
Opening the door to the bathroom turned out to be harder than I thought but I took a deep breath and walked out. The living room felt cold as I walked across it and placed my clothes on the love seat. I heard Greg say, “holy shit, what is he doing?” Followed by Pete chuckling, “he’s just embracing his inner sub.”
As I knelt down I was glad that I was facing away from them because I was shaking. I bent over and placed my cheek on the ground and reached back grabbing my ass and pulling it apart. “I wanted to thank you for giving me the opportunity to learn the ropes from you Sir. Now I offer you the opportunity to enjoy the fruits of your labor.” I stayed in that position and it felt like I was there for 10 minutes before I heard Greg speak and realized that he had gotten up and was standing right behind me. “You really did break him you bastard. Where did he get the jockstrap? It’s my favorite color and looks like it is tailored made to hold those globes.”
Before I knew it 2 fingers were in my ass and I thought Greg was taking me up on my offer. Until I heard Pete right next to me, “yeah I’m telling you this bitch was waiting for someone to take charge of him. He was so easy to break and has such hungry holes.” Just then he started fingering me harder and I moaned as he did it. “Hand me the lube I need to stretch him before we get started on this hole.” Just then I felt the cold liquid as he squirt some directly on my hole and began smearing it around. Those two fingers kept going at my hole before I saw Greg’s feet beside my face.
Greg said “get up on all fours, you’ve got two holes to train don’t you boy?” As I got up and looked up I saw that Greg already had a rather large dildo in his hand. He suctioned it on to the floor and pushed my head down on it. As I started to go myself and get used to the size things went dark as Greg slid a pair of black spray painted goggles over my eyes and kept shoving my head down further and further on to the dildo.
Soon 2 fingers turned into 3 fingers in my ass and Greg told me to look forward. As I did he grabbed the dildo off the floor and started using it in his hand to face fuck me. I could feel the saliva dripping down my face as he kept going. He shoved it half way in and told me to hold it there. Then slid on those big noise cancelling headphones and I heard classical music start playing. He started the face fucking back up and being unable to see or hear what was happening made me really focus on the feeling of the three fingers in my ass and of him face fucking me with the dildo. He stopped suddenly and all of the sudden I felt it coming at me again and as I swallowed it down my throat I realized it was warm and that’s when the pubes hit my upper lip and the balls slapped on my chin. It was someone’s cock and it was big.
I didn’t have much time to think about it before it was throat fucking me. Then I felt something bigger than fingers slide into my ass and start slowly sliding in and out. I was so overwhelmed by both going at the same time that I forgot for a minute that I was near the coffee table and ended up bumping into it because of the force of the cock down my throat.
Everything stopped for a minute and then the cock slipped out of my mouth but the one in my ass stayed for a minute. Then it was pulled out and the earphones were pulled down. Pete said, “we’ve decided that since you want to enjoy tying so much that we are going to tie you up. How’s that sound bitch?”
“That sounds like fun to me Sir.”
The Headphones were put back on and Pete picked me up like a baby and carried me somewhere. When he set me down he kicked my legs wide open and I felt ropes around them then I was bent over and something soft was between my hips and the surface and then something else soft was under my face. Each arm was pulled in opposite directions and ropes were attached there as well holding me tightly in place then I felt a rope go around my stomach and slid up to my chest. That too was cinched down and I couldn’t move much.
Headphones came off again. Pete, “so we are going to play a fun game. So here’s how it works, we are going to fuck you with different objects for two minutes. Then you are going to try and guess what it was that fucked you. We also think that there should be a prize if you win this game. So, if you guess correctly we will remove one of the ropes holding you in place for each correct answer. If you manage to get them all removed then we will let you be involved in some of the decisions.”
Greg piped in at this point, “we were thinking you could have the blindfold removed and decide where you want to get fucked(the bed, over the couch, the shower, wherever), how many loads you take tonight and even who’s cock gets to enjoy what hole and where we leave those loads. But for each one you get wrong we will keep track and after the 5 rounds we have punishments for certain goals. Like if you miss 1 then we will leave the middle rope on but remove everything else, if you miss 3 times then we leave your hands legs tied too and we get to decide how many loads you take. But if you miss all 5, we will have to really amp up the punishment but we haven’t decided on the full extent of that just yet. We’re going to put the headphones back on and get started. You get to guess after each 2 minute period. We will let you know the results at the end.”
With that the headphones were secured back in place. Then all of something there was something in my ass and it slid in and out stretching my hole for about 2 minutes then it sat there for a minute before it was removed. Headphones came off, “so what’s your answer?” “I’m going to guess that was Pete” That guess came from the fact that it was pretty girthy like the one that fucked me on Friday. “Ok, I wrote that down.”
Headphones back on and a few seconds later something slid in but it felt thinner this time. I tried to focus on it but it was really long and hit weird spots. Then it stopped moving for a bit before it pulled out. “Guess?”
“Double ended dildo.”
Headphone on, this time as the classical music played a much thicker one went in and I figured it was a dildo maybe? So that was my guess. Fourth one felt a lot thinner this time and I figured maybe Pete’s had stretched me out so much that Greg’s felt thin. So I guessed Greg’s. This time I heard a scoff from I assume Greg. The fifth one was once again thicker but seemed like he was holding back and only putting in like half of his cock. Again it stopped moving then was pulled out. This time I decided to say Greg again so that even if I was wrong I wouldn’t get all 5 wrong.
“So bad news, you didn’t get a single one right.” Greg said
“What? But I switched the last one just in case Greg was the girthier one.”
“Oh, no you misunderstand. We didn’t use our own cocks for this. These were a way to warm you up for our cocks. We used other items. Hm maybe we should have been more clear. Ok we will be nice and give you another chance to guess each object. You ready?”
Before my mouth even opened there was an object in my hole, thick and long. “That has to be an 8 inch dildo.” We went down the line of objects with me guessing, “5 inch butt plug, 7 inch dildo etc.” but they switched out the 3rd item and said they would do that one last. Once they inserted it and I took my guess. They pulled the goggles off as one of them held the item inside of me. I tried to look back but couldn’t see well enough.
“I’ll give you a hint, it’s Mario and Luigi’s favorite item.” Greg joked. He took a picture then brought it around to show me that sticking out of my ass hole was the plunger from the bathroom. The handle was almost completely inside of me. “See I have a fetish for using household items. That way no matter where you are you can find ways to have fun. But don’t worry they all had condoms on them and I tried to use ones that wouldn’t hurt you. Just a bit of humiliation, that’s all. Now let’s go over the rest of the items. He showed another picture of a zucchini clearly sticking in my hole, then a cucumber, then the plunger handle, followed by a banana and then last it was the very bottle of lube they’d been using on me.
Those two were still fully dressed and I felt humiliated. The thought that so many household items had been inside of me and felt so good. “We will have to discuss the proper punishment but for now I’m horny and need to use my own cock this time.” Greg told me as he threw a towel over my face. This time I could hear them and see the inside of the towel and realized the soft object under my head was my shirt and I was bent over the kitchen table. Pete was back to fingering me and I could hear them mention “hiking, collars, a tail(which got a laugh from them both) and then Pete said something about a guy name Keith.”
After a few minutes of three fingers, they were pulled out and this time I recognized Pete’s cock enter me. He moaned the same way he had when he came in me on Friday. “Fuck that hole feels so good.” He thrust in and out of me for several minutes then he slowed down I felt him pull out and the something warm hit my hole and I felt some drip in. Before my hole could recover I felt something else push inside. This one felt even thicker somehow. “Shit you weren’t kidding, that hole does feel amazing.”
That’s when I realized he wasn’t moving. Greg took his time getting his whole cock inside of me. Slowly sliding himself in a few inches then pulling out slightly only to add a few more inches. It was so hard to tell his size because I didn’t know how much he left in and how much he pulled out each time. Then the towel was moved and I could see him over top of me. He took the banana and pushed it between my lips before putting the towel back over my head. I guess he didn’t like to hear me moan.
Either he had incredible stamina or he knew how to slow down enough to make it last. But finally he grabbed my hips and pushed in letting out a sigh and tensing his whole body. Then just like that my hole was empty once again. That lasted maybe 7 seconds before Pete had his 3 fingers inside of me, “damn dude this hole is spacious now haha.”
A few minutes later the ropes holding my arms were undone followed by my chest and then my legs. When I stood up both of them were wearing just a pair of basketball shorts. Pete kissed me and then led me into the living room. Greg had sat down on the couch. With his hand on the back of my neck Pete stepped up behind me and told me to put my hands on the back of my head.
“I have one more surprise for you Greg.” He went down grabbed the jockstrap and pulled the pouch to the side exposing the cage.
“Jesus, remember one week ago when we were showing him how to tie guys up thinking he was a fellow Dom?” The two of them started to laugh. Then Pete walked up and stuck the dildo to the floor. “Go ahead and ride that for us while we discuss the punishment.”
I mounted the dildo and started riding it. Then Pete walked over to his box and grabbed a few things. He had me put my arms behind me and cuffed them so my hands could be on the ground. Then he attached a ball weight around my balls. Grabbed my shoes and helped me put them on then he untied the laces, had me get comfortable and ride the dildo several more times then had me lift up so just the tip was in and pulled the shoelaces tight on my right shoe and grabbed one end looping it around my balls just above the weight and tightening it so it pulled on them to an uncomfortable level.
Once I was set up they had me ride the dildo and their discussion began.
Greg, “I’m thinking that pink cage is perfect on him, let’s make that part of the punishment.”
Pete “my thoughts exactly, plus the longer he’s caged the better he will listen. I’m also thinking we set new rules when he is here.” At that point Greg looked at me and got up. Bringing the headset back and turning up the music so I couldn’t hear. I kept riding it and stopped bothering to understand what they were saying. After a while Greg walked over again and took the headphones off.
“Go ahead and relax and sit all the way down on it. We want to discuss things with you.”
As I sat down I felt it really fill me up. Pete started, “so we would like to train you as a proper sub. Is that what you are looking for boy?”
Even though I had been humiliated and degraded, I realized that I was really enjoying the experience overall. “Yes Sir, I’d like that very much.”
“Alright good, so from now on when you show up at either of our houses. Once you walk in you are to remove all your clothes and fold them up and place them in a designated area. For my house it will be the stool in the kitchen.”
“For my house it will be the chair in the corner of the dining room.” Greg told me.
“If we allow you any clothing it will be waiting in that spot when you get there. Otherwise you are to remain naked. For the most part it will be just the three of us. But we do have a friend that we’ve shared subs with in the past. We usually go with him on a cabin trip in the spring. If you sleep with anyone else you are to inform me and we will get you tested as needed. That dildo you are riding is going to be your best friend, you can name him accordingly. I’d suggest calling him superior since he is so much bigger than you.”
This got another laugh from Greg who cut in. “We might size him up as needed but that’s a great starter dildo.”
“Do you have Snapchat?”
“Yes Sir.”
“Good because we will have tasks for you to accomplish as part of your punishment and you will send us both video proof. None of it will be saved but this way we know you did it live. Another part of the punishment is that the cage stays on.”
“For how long?”
“Well we decided that for now we will do one week for each incorrect answer. So for starters it will be 5 weeks.”
“Can I earn my freedom quicker somehow Sir?”
“Hmm we will have to discuss that, it will probably be pretty costly though. So don’t go into that lightly boy. Next point of business. That jockstrap is yours now and should be worn anytime we go out together. You will also start going to the gym with me at least 3 days a week. We can discuss which days later.”
Greg piped up, “we will meet once a week minimum, we can set a certain day or play it by ear. When we get together you are expected to be ready to be fucked at the drop of a hat. Speaking of hats, I have one just for you. You have to wear this for the next 5 weeks.” He pulled one out from behind the couch and threw it at me. It had a rainbow lock on the front logo and on the inside of the rim it said locked on one side and boy on the other. I put it on backwards. Pete walked over and undid the tie on my shoes and let me get off of the dildo. He stood me up and pulled off the jockstrap.
He had me get in doggy in the middle of the couch facing Greg. Then he sat behind me and his fingers began to probe my hole, again starting with 3. Greg asked if I was ready to worship my Daddy’s cock. I shook my head yes and said “Yes Sir.” He pulled his shorts down and when I tell you this man had a thick 9.5 inches of veiny cock I mean every word of that. It was uncut but the foreskin slid down and he just grabbed my head and guided me to his balls. They were massive orbs and the musk coming from them made me so horny. I began to lick each ball individually and then sucked them both into my mouth. Then I picked up his shaft and realized that it was his cock I was sucking earlier and began to fuck my face on his monster cock. He just put his head back and enjoyed.
Meanwhile Pete was fingering me then pulling them out and shoving them right back in. I was surprised when he actually pulled them out and something wet touched my hole. I look back long enough to see that he was rimming me. That lasted only a few minutes then Pete asked if I was ready to finally see the cock that owned me. I pulled off of Greg’s cock long enough to say “Yes Sir!”
He told me to turn around and sit down on Greg’s cock first. I was surprised when the tip popped in but before I could adjust I was pulled down and impaled. Pete stood up on the couch and I could see the outline of his cock but it wasn’t until he got closer that I reached out and slid down his shorts. He had 8.2 inches of cut cock that I immediately fell in love with. This is what I imagined the perfect “boyfriend dick” looked like. Once it went into my mouth it seemed to belong there. My mouth was like the scabbard and his cock was the sword.
He pushed it all the way in and Greg shifted his hips forcing his cock deeper into my ass. Then Greg told me to get in doggy so he could control things better. That night I learned what 17 inches of cock inside of you felt like and I couldn’t imagine being anywhere else at the moment. Then Greg grabbed my hips and thrust two more times before holding it there and emptying his balls in my ass.
Greg left to grab a shower and Pete had me mount him on the couch. It was like he hit every spot inside of me because not even 2 minutes in I felt myself building up and for the very first time I came hands free. Still locked in the cage that this man, whose cock was inside of me, had placed on me only 2 days before. He grabbed my face and started kissing me while holding my ass and forcing me up and down. Then he had me get back in doggy on the floor and started really fucking me like a whore.
Right as he came he grabbed me by the hair and whispered in my ear. “What happened to that Dom who came to us a few months ago? Now look at you, caged, soon to be collared and cumming while getting fucked by guys whose cocks are bigger soft than yours is hard. You will learn your place bitch.” Then he pushed me forward and pulled out of my ass at the same time. His cock left with a wet “slurp” sound. Then he shifted forward, grabbed my head and forced his cock down my throat. “That is the taste of your sour ass mixed with two Alphas seed. You should get used to that taste boy.”
He got up and walked into the bathroom, leaving me there spent and gaping. Pete emerged from the bathroom and he picked me up pulling me towards the shower. He turned on the warm water and climbed in beside me. Pushing me against the wall he started to kiss me again. Then I felt something warm start to trickle down my lower stomach. He was pissing on me right there. “Need to mark you in every way possible.” Then he turned me around stuffed his semi hard cock in my ass and started pissing again. “Thought I’d help you clean out too. In case there’s a round 3. Now squat down over the grate and void yourself.” He pushed me down and I was mortified as I squat over the grate and started to push. My mouth was open in my state of shock and then I saw him grab his cock and start pissing again. He nearly got it in my mouth but I shut it just in time.
Once I was cleaned out, he stood me back up and we washed each other. He got to my hole and slid two fingers in easily. “This will be a fun few weeks but don’t forget that if it gets to be too much just say so. We will both respect that.” I couldn’t help but smile as my new Dom fingered me clean in the shower.
