I was nervous as I sat on the bed. I had never done anal before, not really. Some men online had directed me to finger my ass or push skinny objects in it, but I’d never really fucked it. The first older man I’d met with had tried, ramming his cock against my virgin ass, but he’d just wanted to use and hurt me and didn’t care how. He had gotten the tip in and I had wailed, and he stopped, returning to fucking my pussy. My ass had hurt badly after that. Now Jack wanted to break it in, to take it as he had taken me.

We’d met a few times before and it was a new year, cold and crisp. Spring was still a bit away. He’d been educating me, expanding my horizons. He’d had me pick my safewords out and I had decided to keep them simple. He wanted to push me and I wanted to be abused, so I just used “Yellow” for caution/ease up, “Red” to stop whatever he was doing and check on me, and “Black” was a full “stop everything” command. I hadn’t used them yet and I was anxious as fuck to do so. He’d gotten on me for that as well. Communication was to be absolute, with no exceptions. Anything was fine as long as communication was clear and honest, he’d said. I didn’t want to be abandoned or rejected. I had learned about aftercare from him, but I hadn’t remotely forgotten the crash I’d had after my first hookup had all but kicked me out. Nor had I forgotten what my dad had done to me.

I stood up and threw on the clothes he’d set aside for me. He had talked about role-playing, but we weren’t there yet. It still felt a bit silly to me. I put on the clothes - a cheap denim skirt, a red Walmart thong, and a ratty too-big halter top. He said makeup would be fun, but not to worry about it. I looked like a girl from someone’s old idea of trailer trash. I walked out to see him getting supplies together and he smiled at me. That made me smile as well as I twirled around.

“Do I look ok?” I asked, uncertain.

“You look like a cheap skank,” he said, still smiling, eyeing my frame up and down. I hated I only had a couple of hours here. Then I’d have to return home, drown in misery, and wish I was someone else again. He patted my ass and pointed to everything.

“I’m explaining it this time, but I won’t always. We have lube and will be using a lot of it. The little vib there is to help open you up a bit. Towels, well, that shit stains,” he said, only half joking. He held my chin firmly, which just made me melt, and told me to get back in the bedroom.

He came in and grabbed my hair, pulling me over by the closet to the mirror. He balled my hair tightly in his hand and pointed at the mirror.

“I want you to understand something Sammie. See that? That isn’t you,” he said as he pointed at my reflection. “That is a cunt. Just a trailer park piece of shit. Fix that in your stupid little mind, ok?” he said, jerking my hair back hard. I nodded, shaking as he shoved me forward towards the mirror and told me to stay. I did, watching him in the mirror move behind me. He picked up the lube and returned to me.

“Hands on the wall, cunt. Face the mirror. Look at the stupid trailer trash there. She’s just a stupid fucking thing no one wants. The only reason she hasn’t failed out of school is that she’s fucking the teachers. Just a whore,” he said. He lubed his fingers heavily and I grunted as I felt cold against my asshole.

“Spread your legs and look at her. Tell me, how does this feel?” he said as he pushed and prodded, working his middle finger in my ass. I whimpered, shaking. He slowly pumped the finger back and forth. “How does it feel?”

“It ... it feels ok Sir,” I said. And it did. It was tight, but it felt uncomfortable. Even more uncomfortable was watching myself in the mirror. Seeing my every grunt and shudder was difficult.

“That’s all? I don’t fucking think so. It’s more than that. I don’t want you to use your safewords. Not unless you really need to. This might scare you, but you need to know this. Feel this.” And with that, he shoved in his index finger, eliciting a cry from me. I shook hard as he barely forced it into my tight ass. I watched the girl in the mirror start to cry. I felt dirty. I was still fully clothed and yet I felt violated.

“Tell me, do you feel like a woman right now?” he said as he shoved the fingers deeper. “Do you feel sexy? In control? Powerful?” he said, hooking his fingers and lifting me up a bit. “Look in the mirror and tell me how you fucking feel.” I cried a bit more, shaking bad.

“I feel cheap. Dirty,” was all I could barely say before starting to sob a bit. He leaned forward and kissed the back of my head. Then he pulled out his fingers, wiping them on my denim skirt. I felt the absence almost as much as I had felt the presence of his fingers. He gripped my hair and pulled me over to the bed where he’d laid out the towels.