Cougars and Kittens and a Cub

I woke up some time later to various sounds and bright lights. The first thing I was aware of was a fit of giggles erupting somewhere close by between quite a few girls. Then I felt a hand caress my face and the weight of a massive breast resting on my chest. I opened my eyes and instantly smiled into two beautiful blue shimmering eyes looking down at me.

"Good morning Cubby." She said in a soft Australian accent. "How did my baby sleep?"

It took me a moment to remember I was in prison. I wanted to glance around to see what was happening but this woman was so gentle and her breasts were so big and she had such a serene look in her eyes, I was mesmerized. "Really good."

"Really really good?" She nuzzled her face on mine and then stroked my hair. "I heard about your little smuggling attempt yesterday. Such a naughty boy aren't you?"

"I don't try to be. Who are you?"

"That is a good question." She said softly. "You have so much to learn young Cubby, and we all have so much to figure out. You can call me Zoey if you want, or Mommy if you prefer."

Honestly, I had several mommies at this point. It was getting to be my thing. I smiled and tried giving her a kiss on the lips which she accepted. "Zoey is a hot name."

"Oh thank you little Cubby. You're causing quite a stir around here this morning." She just smiled and kept stroking my hair. I glanced down at my hardening cock and then back up to her.

"So are you." She giggled and rested her hand on my cock through my shorts. Apparently I had been dressed at some point in my sleep. I glanced over out of the bunkbed and saw where the giggles were coming from.

I was in a room of about 5 or 6 bunks from what I could see. They were all pushed to the edge and the middle of the room was very colorful and full of bean bag chairs and rugs and little tables. Sitting on some of the lower bunks were larger, more well endowed women in various states of play. Some were kissing, others fondling, others were just sitting and watching the center of the room. They were all dressed in very beautiful sundresses that showed off their breasts and legs perfectly. The woman holding me was wearing something similar.

In the middle of the room, gathered around a table were a few other girls. These girls were much smaller, more petite, and dressed in very colorful and skimpy outfits. I could see two of their pussies facing me as they bent over the table. They were playing some kind of card game and taking turns kissing and giggling and tickling each other.

The walls were decorated with posters and colors and the floor was a thick cream colored carpeting. Nothing at all like any prison I had heard of. I felt a finger under my chin gently guide me back to the two gorgeous blue eyes. "You wanna play with the other kittens, you need some breakfast first."

I reached up to her dress and pulled one of her big breasts out. She **** me back against the bed in one solid motion and then gave me a stern look. "Cubby, you wait to be fed. You don't get milk until you earn it." She moved her hips up and straddled my face. "You get my pussy until you learn to behave."

I just smiled up at her. "Even better." She dropped her stern attitude and returned to her gentle caressing. I leaned up to her pussy and then she lowered herself to my lips. Her juice tasted so fucking good.

I drove my tongue up into her and felt a gush of juice fill my mouth and nose. It was burning in the best way and each taste filled me with energy. She was using my nose to grind her clit but I moved my mouth to vacuum her little button into my mouth and then I sucked it hard. She bit her lip and sharply gasped as I gave her clit a little nibble. There were less juices around her clit but it filled me up more for some reason.

"Oh good Cubby." She moaned and I started to hear moaning across the room too. I was trying to glance over but her thick thighs were keeping my Cubby head firmly in place. I watched her grab her massive tit and give it a lovely squeeze as I pleasured her. She shuddered around my face and her thighs tightened as she came on my tongue. "Ahhhh fuck fuck! Oh FUCK that's so good. I have the best cub the whole prison."

I heard from around the room, a series of slaps and yelps coming from the other bunks. I heard similar moaning and I even heard one woman say "do better."

After my mistress's third orgasm, I moved my tongue back and stared rimming her ass. "Oh! My goodness such an eager little cub." She quivered. "So... dirty."

I used my thumb to massage her clit while I pushed my tongue up into her ass. I was about to drive it in all the way when a loud BANG was heard from the entrance to the cell.

"Alright line up!" My goddess climbed off me and I followed her into a line. It was staggered Cougars and Kittens so I stood directly behind my bunkmate and followed her out of the cell. We came out to a much more traditional cell block on a metal walkway and a big open section in the middle. I could see across the way a few more rooms like the one we had come from and cougars and kittens emerging from them.

"Line up." I glanced to my left and right and made sure to follow what the women were doing. I stood between two large cougars and it was amazing just how tall they were. I was over 6 foot but they each had a few inches on me at least. The kittens were about a foot shorter than me. "Let's see those fingers moving whores!" The guard called out.

The women all parted their legs and began masturbating. I grabbed my cock and followed suit, stroking myself along with everyone. The guards would walk along the line, pause, kneel down to put their faces at level with a random pussy, and then get up and keep moving. My cock was getting about the same attention as any of the other women.

"Rub that precum around your cock head. I wanna see it glistening." A redhead guard barked at me. I obeyed and watched her lick her lips in approval. "That's much better. Very good boy."

Throughout the cell block, moaning could be heard getting louder and more ****. I was getting close to cumming myself but the guard held up a hand and blew a whistle. "Stop! Cumming is for good girls and you certainly are not them. Orgasms have been denied."

"Ha ha!" One of the guards mocked.

"Don't cum. Don't you fucking cum." One of the other guards taunted. I was flustered from the denial but it invigorated me for sure.

"Alright, move along." I followed the women to a big cafeteria.

"What's your name?" I whispered to my cougar as we walked.

"Zoey, but you'll call me Mistress if you wanna survive here." She said softly. I nodded and smiled.

"Yes Mistress." Zoey beamed and reached back. She rubbed my stomach affectionately and then lead me to one of the lunch tables.

I watched as the kittens all got up and headed for the food line and their Mistress's stayed behind. I followed suit, obtaining a spank from Zoey playfully.

"My boy learns quickly." She said with pride. As I stood in line, I glanced around at the kittens who were glaring at me. One of them pushed me out of the way and cut in line and then three others followed.

"Hey, what the fuck?"

"Shut up, loser." A small redhead spat at me and then smeared it on my face. They all giggled with self satisfied smirks and got in line. I stood there for a few seconds before I remembered this morning. I made Zoey cum harder than the other women so these girls must have been punished for it. Did I wanna be a cougar ass kisser or a bad little cubby? Didn't feel like I could really lose either way.

"Psst!"

I was lost in thought and didn't hear the lunch lady trying to get my attention.

"Psst!"

Suddenly, a loud crash could be heard in the kitchen and a big tray of food went flying across the room. The lunch lady threw her hands up and looked at me. "Oh shit.... you did... you knocked all this over you're gonna be... in trouble."

"Haha what the fuck?" Her delivery was so unnatural that it instantly made me laugh. She sounded like Rick and Morty.

"Don't laugh! You have to come with me for a... spanking!" She announced. I looked around and most of the girls were getting their food and giggling at my fuck up. I shrugged and followed the lunch lady. I noticed she was dressed in an apron and nothing else. She had a big round ass and nice legs, she looked like an absolute fuck doll.

I followed her to a pantry and she closed the door behind me. "Holy shit, I can't believe it's you!"

"It's me. What do you mean?"

"You the... the whole... oh fuck this is so weird. You keep getting punished sexually right? Is that weird to you? Haven't you noticed?"

I stared blankly at this woman. "What the fuck? You can.... tell? It's weird to you too?"

"It is! The world changed around you like... I remember two worlds now. We have to... here." She bent over the counter and spread her ass. "Fuck me."

"Wait I..."

"Just... fuck me so we can keep talking." I lined up my cock with her pussy and shoved it in. She was very lovely. "Good. Oh fuck. I can remember two worlds in my head. Don't thrust! Just keep it in me so you don't explode."

"Sorry."

"I think... most peoples' lives didn't change much so they just adapted to the new world. Or I can just see through it. It must be insane for you right?"

"Well it was at first. It's so good though I don't want it to stop."

"What? But everything you do is punished with sex! You must cum nonstop. Your cock is probably sore as hell."

"Not really. Everything feels amazing. I love every minute of this to be honest."

"Ohhh of course. You're not thinking straight either! I'm so sorry you're at the middle of all this."

"Do you know anything about this world?" I asked. I wasn't that curious to be honest. Whatever mystery was keeping this universe together, I didn't feel like questioning it.

"All I know is, one minute I'm sitting next to my dying husband in a hospital in San Francisco, the next moment I'm stretching my asshole with a double sided dildo in preparation for coming to work here."

"You don't remember how you got here?"

"I remember everything. I went to training, I learned proper punishment technique, I learned how to deep throat your cock. Always you. Everything to do with you. I also happen to have memories of being an accountant at a law firm in San Mateo and getting my Masters in Finance."

"Did you always have a bimbo ass and big udders?" I thrust into her more and she moaned.

"Ugh can you stop? This is just cover so we can talk."

"I don't know what's hotter. The fact that you had a much more professional life and continue to be a bimbo lunch lady in this world, or the fact that you're still offering me your holes knowing what you know."

"I think you're focusing on the wrong... ugh... aspect of this."

I thrust into her and stopped. "Wait what did you say? You trained to punish me? What do you mean?"

"It was a segment of my training to work here."

"I didn't think that sexually punishing someone required training."

"Oh sure. There are courses women have to take all across the world that teach them the best techniques to fucking you. Of course, they can start much earlier than that and they kind of know what to do before they take any formal classes. Punishing you is something that's ingrained in us girls our whole lives."

My mind was racing. "I would love to volunteer for one of these courses."

"John listen to me!" She tried to push back against me but my cock just drove deeper into her. "Ughh fuck. This is obviously some kind of cosmic trap for you. You have to resist this world or something bad might happen."

"What I have to do, is fill you with cum and get back to my mistress with food." I sighed hearing myself. "Whatever this is, it's an adventure. I suppose a part of me knows that it's probably not gonna end well, but I just don't care. What life ends well? This way, I get to have a ton of sex all the time and the world takes care of me for it. If this is hell or heaven or whatever, I'm not going anywhere. Just be thankful you're well trained to be my fuckdoll."

I came inside her and returned to the cafeteria. I could see on her face that she wasn't satisfied or finished with me, but she gave me a tray of food and I was back to my mistress.