In a weird way I grew to really like her. Her demeanour was changing, less overpowering domme and more powerful girlfriend, her treatment of me softened, less hair pulling and more head pats for a job well done.
Two weeks after my first day I was called to the milking room. I’d been dreading this, even after chatting to the guys in the quad for two weeks, no one had revealed what went down in there but the older inmates spoke positively of it, so I knew it either had to be something really bad, or something really good. The whole thing was still a daunting mystery somehow. The name implied things I didn’t like the sound of. Kara escorted me down to some chairs outside the milking room, and with me in cuffs, we sat and waited for the current session to end. It was a sound of male moaning, some of it sound pained and some pleasured.
“What the fuck is going on in there?” I asked.
Kara didn’t reply, but just smiled menacingly. We waited a little longer until an inmate was escorted out feebly, him barely being able to walk properly. What the hell?
My escort stood up and pulled me into the room. Inside was a strange looking chair with a hole in the middle and some sort of drainage device below. Dear god, what the fuck was this?
Kara was about to shut the door when a familiar red-head pushed it open.
“He’s mine, I want to do this to him.” said Brooklyn.
“You know you can’t claim inmates as your own Brook, Chun will kick your ass.” Kara replied, all business.
“I… like this one.” Brooklyn replied, bashfully.
“… Alright.” Kara sighed before leaving the room.
Brooklyn perked up and closed the door behind her.
“Aren’t you lucky! Your first milking with your favourite Mistress!” she said, reaching behind me as she unlocked my cuffs.
Oddly, I did feel a bit more relaxed knowing Brooklyn would be doing this with me.
“Now get in the chair.” she commanded with a devious smile.
It was a strange looking contraption, I’d have to get in face-down and my arms would go in stirrups at the top and my legs in another set at the bottom. My face rested in a ring at the top. Everything had straps on it to hold me in place, directly above the groin was a hole where the drainage unit waited below. It was almost like a masseuse chair crossed with some kind of gynaecology recliner, it was intimidating and weird as all hell.
I slowly climbed into it awkwardly, resting my wrists in the upper stirrups and my legs in the lower ones, I felt Brooklyn strap me in.
“You shouldn’t really need to get strapped in, you wouldn’t disobey me would you?” She giggled.
“No Miss Brooklyn.” I replied obediently, secretly smiling.
Despite how well she had treated me recently, her words were not reassuring, I felt her tug my trousers down leaving my ass exposed and the cage hanging precariously above the drain. At this point it felt like my balls were twice the size they were when I first came here from frustration. I really shouldn’t have guessed that yet again my ass would be the entry point for this weird experiment. I suddenly felt Brooklyn’s gloved and lubed hand probing my ass, I wriggled a little and a firm slap hit me across my left cheek.
“If you don’t stay still you’ll go back to your cell without.”
At this point I didn’t know what I was getting to figure what it would be like to be without it. Nevertheless, I tried to stay still as her fingers reached down further, then suddenly her other hand came up and grasped the cage from below me. I jolted back in reaction of being touched and Brooklyn’s fingers hit my prostrate.
“Ah, there we are.” she said, as she began to massage that spot.
I felt like I was being used, coerced into orgasm as she expertly squeezed my cage and probed my ass. I had no control over what was happening and gripped the contraption I was in even though I already couldn’t move.
“You see, we can’t have you getting unhealthy as a side effect of your little chastity cage, so we’ve got to help you release some built up…frustration.” she said with a wink.
I tried to say something but couldn’t find the words, then it hit me. A wave of pleasure like nothing I’d ever experienced before I felt like every point in my body was engulfed in an overwhelming feeling of ecstasy, cum gushed out of my cock through the open slit in the cage and into the drainage unit. I let out a long wail as the liquid drained from me. I could hear Brooklyn giggling behind me.
“There we go, I knew you’d love it, such a little butt slut you are.” she teased.
“H-holy shit! What the fuck?!” I exclaimed, this felt better than any sex I’d ever had in my life.
“I could make this happen every day if you’re a good boy for me.” she said.
“R-really?” I asked, enthusiastically.
“Ha! You’re turning into an enthusiastic little boy for my girl stick aren’t you?” she replied.
I could barely catch my breath, that was incredible. I felt the straps being undone but I barely had the energy to move, all my muscles felt weak and useless. After a few minutes I pushed myself out of the chair and staggered to my feet. She walked up to me and put her arms around me.
“You were such a good boy, I’m proud of you.” in that motherly tone she would do now and then.
She handcuffed me and the embrace ended. When she praised me, it felt good. She pushed me towards the door and helped me back to my cell, laying me down on my bunk. She uncuffed me and blew a kiss as she locked the door.
“I’ll be back to see you later, get that tongue ready.” she whispered before she left.
I lay there for an hour, mind blank in a state of euphoria. Holy shit.
*
Days came and went and my relationship with Brooklyn deepened, I couldn’t help it, I developed feelings for her. Maybe it was love, submission or even Stockholm syndrome, but that short red-headed girl was always on my mind, I dreamed each day of eating her out and hearing her moan, and in return, she rewarded me with the girl-stick baton. She grew softer towards me, playing with my hair instead of holding me in place and chatting to me during quad time.
Through our conversations I learnt that she was single, shockingly good at maths, collected comic books and figurines and played cello in an orchestra, I literally couldn’t believe she was as nerdy as she was based on how she acted at work.
We were sitting on the floor in the quad, separated by the chain fence. I explained to her how I came about being here and whilst she disapproved, which coming from her felt far worse than anything I’d been subjected to during the my time passing through the justice system, she could tell it was something I felt forced to do to survive.
“You were kicked out of your old job and took up theft and you were good at it. Why couldn’t you just apply that drive to something else?” she asked.
“I guess I only did it because it felt like everything had been taken from me and I wanted to take something back. I thought my life was ruined! I’d spent years getting good at my trade and then suddenly it was out of the question, where else do you turn when the only thing you were good at you can’t do? I’d never be accepted. It felt like the walls were closing in and I’d not be able to go back a normal life.” I confessed.