Up the River

I was stripped of my clothes by the bailiff. She ran a finger over my still quite drippy cock and she tasted her in her big lips. "Mmmm, I love me some guilty cum." She moaned. I laughed.

"Have all you want." I offered. She raised an eyebrow.

"You came so hard the fucking moon almost fell out of orbit and you offering more? Well shit, your bus doesn't get here for 20 minutes." She started taking off her clothes and her massive black tits fell out of her bra. Despite her sturdy appearance in her uniform, she was actually more fit than I was expecting. Her stomach was still a little chubby but not obscene. She got down on her knees and took my cock into her mouth. It actually felt nice.

"Mmmm that cock is so fucking big, baby. Guilty, not guilty, I would suck this dick any day." She giggled and attempted to take me all the way down. Her tongue was wonderful and it flicked and ran all over my shaft and even tickled my balls a bit. I heard a small laugh above me and I looked up to see the judge.

"You earned that cum today, Ms. Killeen." The judge said proudly to her bailiff. I leaned back against the wall and looked up at the judge.

"You earned some too, your honor." I teased. She bit her lip, her white gown flowing around her perfect body. "I'd love to make you a mother before I left."

She really considered it. "If...if we have time after Shanice is done, then I might indulge. I feel bad about the prosecution though, is this taking advantage of you?"

"Isn't this 6 months straight of punishment? If anything you are helping out the prison." I said. She seemed to relax.

"You're right. It doesn't matter how we got to the truth, now we're here." She got down on a chair and spread her long, gorgeous legs. She licked her hand and started rubbing her clit while she watched. She was so hot. Now that I could cum whenever I wanted, I let myself fall right over the edge and I started to buck my hips into Shanice's mouth.

"Mmm mmm mmm!!!" She tried to protest but I just let her have it. I didn't cum a lot because I was still refilling from the trial. She still licked her lips and wiped some excess off her chin and ate that too. "Delicious." I got up and walked over to the judge.

"Here, let me help with that." I lowered myself and my cock found her pussy instantly. Despite being taller than me, she was almost the tightest pussy I had ever felt. "Oh, how are you so tight?"

"I workout and I rarely have sex. Mmmm makes...big cocks like yours feel extra amazing." She moaned. Gone was the confident goddess of the courtroom, this was a slut for my cock. Her moans were cute and submissive and she held me while I pistoned into her.

"You got a man at home?" I asked her. She shook her head.

"No I have...a...woman." She moaned. Another lesbian? I smiled.

"Really? Is she tall and powerful as you?" She shook her head.

"Well she's powerful. She's only 5' 1" though. She says I only look pretty under her heel. She owns me." My cock was so fucking hard now. Like harder than hard.

"She dominates you? You are a foot taller than her and she makes you her little bitch? What would she do if you got pregnant?" I moaned.

"Ugh...she would still...own me. Own my daughter too. God fuck you are making me...cum"

"Are you supposed to cum without her permission?"

"No! OH FUCK! FUCK FUCK FUCK!" Her pussy gushed all over my cock and my legs and I closed my eyes and focused on pumping her full of a big load. My baby batter shot through her pussy and I watched as it spit out around my cock once it overflowed.

"Ohh you're gonna be in big trouble when you get home. I wish I could see it." I said grabbing handful of her breast.

"Oh fuck that was so good. Oh my god that was good." She moaned. She shook her hair and tried to regain her composure. "Woo! Wow, I needed that. Thank you John." She stood up and walked away, her gown looking like a wispy cloud caught on a mountain.

"Time to go." The bailiff said. "Get naked." That wasn't hard, my pants were already gone. Once naked, she lead me out of the office and into the Southern California sun. The bus in front of me was like a white school bus with nothing on it. I got in and sat down, there were only like 3 rows of seats, the rest of it was empty. Suddenly, two hands covered my eyes from behind me.

"Guess who?"

"Uh..." I thought about it. Her scent, her hands... "Isabel?" I asked.

"Heyyy that was a good guess. How did you do that?"

"I remember your scent you naughty little cop!" I said turning around. "Are you riding with me up north?"

"Yep. My family lives around there and the station offered and it was you so I thought why not?" She shoved some fabric into my mouth and I immediately tasted her flavor on my tongue. "Now shut up and get in."

The ride consisted of her sitting behind me, pumping my cock with her feet and whispering how they were gonna fuck me nice and good up in prison. She kept kissing my neck and licking me and she rubbed her thumb on my cock head which felt incredible. I came on myself about 20 times during the trip and she scooped it up on her little fingers and sucked them off slowly.

We finally pulled up the dusty road into a large gate and then the bus stopped. A woman walked onto the bus in the smallest little slutty uniform I could imagine. She had big soft breasts spilling out and her shorts were being eaten by her ass. Despite her voluptuous assets, she was still quite slender and her legs were toned to perfection. "Out piggy."

I got up and as I walked toward her, she grabbed my hair and pulled my head back until I was looking up at her. She spit down on my mouth and then rubbed it in. "Such a sweet little piggy boy. Out!" She shoved me out of the bus into another woman of an almost identical build except she had auburn hair instead of blonde.

I walked along a chain link fence and saw a crowd of girls. They were in skimpy little outfits that showed off their stomachs, legs, and thighs. I hoped my new endurance would be enough.

I walked into the entryway and an official looking guard reached between my legs and gently fondled my balls. "Feels like you're smuggling something here. First day and already a troublemaker?"

"You're gonna have to take it from me." I moaned.

"I love a tough boy. Bring him here." She waved to a person behind a window and I was lead to a cheap metal table and made to lay back on it. A woman walked out with a pair of cuffs with a stiff metal link in the middle. They were spread far apart and she started locking them around my ankles. I was very new to things going up my ass but this world had a way of making things more palatable.

"Alright, just hold still baby. Momma's gonna extract whatever it is you're smuggling and you'll be in your cell in no time." She walked around the table to my face and leaned down. I could smell the perfume and sweat off her body and her big full pink bimbo lips were inches from my ear. "I'm about to punish my boy, you should show some gratitude."

"Thank you Momma. I'm a bad boy." I was rock hard. She leaned over my body to fondle my balls, her big breasts pressing into my face. She squirted some warm liquid on my ass and rubbed it around, poking a finger inside a few times. She clacked her big heels over to the front of the table and held up a bright pink strap on. My ass was tingling as she fitted it around her big hips.

"Mmmm I love breaking in a new boy." I felt the plastic press against my ass and felt a pressure. I tried to relax and immediately I felt the invasion. My body instinctively tensed up but a few guards descended on me and started kissing my neck, ear, and stroking my hair.

"Relax baby boy, it's okay. Relax... shh Momma's got you."

"Mmmm it feels so tight."

"You're such a tight baby." My blonde domme cooed. "Hold him."

The girls put their weight down on me and the blonde woman thrust into me deeply. She started fucking me in a constant rhythm and pain and discomfort lead to pleasure after only a second. "There you go, nice and broken in. Are you my ass boy?"

"Ohhhh fuck I'm your ass boy. Fuck Momma."

"What do you say ass boy?"

"Thank you thank you thank you." I was moaning and my body was convulsing from pleasure outside of my control. I felt an incredible tingling build on the tip of my cock and my cum shot out onto my stomach and face. All I could do is moan in agony.

"Ohhhh there it is, my dirty little smuggling boy. You can't hide hot delicious cum from me baby." She kept thrusting and I felt my cock reharden and continue pumping out more cum. I felt a gentle hand caressing my hair and a nibble on my ear. I glanced over to see Isabel naked and smiling sweetly at me.

"You are gonna have so much fun here. I hope this teaches you a valuable lesson."

"Uh huh."

"Are you ready to head to your cell sweetie?"

"Uh huh." The guards uncuffed me and helped me to my feet. I could barely walk and a big tall redhead girl decided to fireman carry me after a few stumbled steps.

"Just relax baby. I got you."

Exhausted and beaten, I was laid down on a soft colorful bunkbed and fell asleep.