chapter 5

Though I couldn't see Kaylee, I kept her commissary filled with plenty of money to buy snacks. Four months into her trial, I knew I would see her for the last time before she headed to prison. I hadn't seen her in over a month and a half. This was her sentencing hearing.
She waddled in there at least twenty pounds heavier than the previous time I'd seen her. She had gotten so chunky. Her ass had swelled to where one could easily see it poking through her turquoise jail pants. A faint outline of a tubby belly was becoming visible as well. And her face had grown even chubbier.
I was sure that everyone in the courtroom could see my penis. It was as hard as it had ever been.
It didn't go away until I heard that she was sentenced to five years in prison and five years of probation.
Oh, and my plan! No, it wasn't to keep her commissary full. That's just common sense. I decided to apply for a job at the women's prison which she was sentenced to!

When I got hired, I thought I had made a terrible mistake. I hadn't talked to Kaylee for months. The only interaction between us was awkward glances within the courtroom. I longed for her to complain to me about how fat she is getting. Unfortunately the prison had me working in a wing that she was not in.
But it was definitely no mistake. I would catch glimpses of her every once in a while at dining hall. Watching her shove sandwiches and cornbread down her throat was so hot. I could tell she was comfort eating. I figured she thought she had the time to let herself go before getting back in shape in time for her release.
I also saw her at rec occasionally. While other women were playing basketball or walking the track, she was sitting on a bench chatting with other women. And the women were all plump! This made me incredibly excited. Still, she had no idea that I worked there. I hadn't been there long enough for me to feel casual about striking up a conversation with an inmate who I knew personally.

Then came the day, about three months into my employment, that she noticed me. I felt a tap on my right shoulder and immediately turned around ready to slap a hoe... when I realized that it was Kaylee. I hadn't seen her in a few weeks, and the difference was astounding. She was fat.
"Oh damn! I almost didn't recognize you!" I said.
"Well, me either! What the fuck, how long have you worked here? Are you stalking me?" She smiled.
"No, I just want to be here for you."
She looked at me with a twinkle in her eyes. I knew right then and there that I had to find a way to get a job on her cell block. She looked dick-deprived and down to fuck.

Two long years went by. I still was seeing her about once or twice a month at the rec yard or the dining hall. I watched her eat, we shared brief conversations, she winked at me, I watched her sit on the benches outside. I watched her once flat stomach begin to bulge over her loose grey prison shirt. Her green pants filled with her ass and thighs. One day, I noticed that her pants were fitting looser. She had to get bigger ones, as she clearly had not lost any weight.
Another day, I saw her running. I smiled at her and she stopped, out of breath. "What??!" she cried.
"Oh nothing, I just had never seen you run before. Well, not here."
"You realize how bad this shit hurts? It still hurts to walk, let alone run. I'll be fucked up for the rest of my life, Ian. I just can't deal with getting this fat. I feel obese!" Kaylee patted her stomach. She then lifted up her shirt. I felt blood rush into my penis as she squeezed her rolls of fat as they remained steadily moving up and down while she gasped for air.
I began gasping for air as well.
"You said they let you exercise in prison, and that I'd lose weight. I mean, I guess you're right. But it hurts. It's like I forgot how to be active and fit. You probably think I'm just a fat lard now..."
"Oh no! I think you're sexier than you've ever been in your life," I replied.
"Shut up!" she said. She looked angry. And then she stormed off, half limping and half jogging.
She probably thought I was lying. But then I got a job on her cell block, finally.
I was able to strut past her cell any time I pleased. I even had the key to it. My urges against temptation were completely futile. The first night I worked there, I fucked the shit out of her. I opened up her cell door while my coworker was asleep in the day room. I was the only one there except for the security guys watching the cameras. But I figured they were asleep too.
"How do you handle such a lack of sex?" I asked, being the expert at one-liners.
She didn't say a word before ripping my belt off and proceeding to ***. I grabbed her chubby cheeks and squeezed her double chin. I felt a third chin forming as I ejaculated.
She swallowed every drop.
I didn't go soft, so I immediately tore off her prison clothes. Her vagina was so tight, as it hadn't been touched in years. And her belly had gone from having that vertical line down the middle to having a horizontal crevice separating two pudgy layers of belly fat. I came again without pulling out.
I was so enticed by how large her breasts had gotten. Gone were her C cups, these were double Ds! They had lost much of their perk. When she said up, they sagged almost down to her belly button. As I fucked her missionary as she sat on the prison bench, I watched them bounce gracefully up and down, smacking into her fat face.
I felt the cellulite on her ass and thighs with my palms and the cold bench of her prison cell on the backs of my hands. I thought about all the times she sat there snacking, and how all of that caused her to transform into the BBW she is today. I jizzed again.
I felt her chubby hands run down my shoulders and onto my arms. I knew what she wanted: she wanted me to pick her up like guys used to. So I tried. With all of my might, I picked up her 220 pound frame and struggled with her weight. I used the wall for support and held her up with my hands on her chunky thighs. The cellulite was like a grip; it made the task much easier. Fatigue came to me before my ejaculate, so I set her down on the bench and flipped her over.
I came almost instantly as I watched the stretch marks and cellulite on her butt cheeks jiggle. I grabbed them and pictured what they once were-- in those yoga pants. So tiny, tight, and tan. Now, her ass was nothing but fat and it was so pale from enforced lack of sunlight.

I hope the camera guy continues to sleep. I want to continue this until she is so obese she can hardly move about her cramped cell.