Hi All,

It’s Cassandra, that is, current time period Cassandra who’s recounting this. My new dom has been having me write about my teenage exploits. She thought my original draft for part five had too much stuff that wasn’t important so I’m going to skip a bit here and there, with just some highlights mentioned. Anyway, back to the story. If you miss me you can see my running commentary with the occasional message in parenthesis.

XOXO 😉

Cass

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My parents came home from their business trip. As freelance corporate advisors, they traveled a lot. By the time they came home, I was fed, showered, and, most notably, clothed. I got up from the living room couch and greeted them. A perverse thrill went through me knowing they had no idea what I’d done the past couple days or the giant butt plug that was still occupying my ass. The worst part about my parents getting home was that pretending to be an innocent teenager and being a screamer don’t mix.

The next few days were pretty uneventful, at least in terms of getting off. I’d already lost track of how many orgasms I’d had, but I desperately needed more. Unfortunately, my parents had a home office and it was directly under my bedroom. I didn’t want to risk getting myself off while they were home, I was afraid they’d be able to hear me even if I was screaming into a pillow.

On the up side, they’d decided I was finally old enough to get a cell phone. It was one of the newer and fancier models of flip phone, just released the previous fall. It was thin and hot pink. It had a camera built into it, and it even had an extra display screen on the outside.

(If you weren’t alive back in 2005, smartphones wouldn’t be invented for another couple years, cameras had just started being integrated into phones, and flip phones were all the rage.)

I wanted to message people, but my friends’ cell numbers, the ones who had cell numbers, were all written down on a notepad in my room. When I got home, I managed to add all the phone numbers I knew to my new phone.

My parents had had cell phones for years for business and had paid through the nose for unlimited minutes. (Back then, phone plans had a limit to how many total minutes your calls could be, and a predetermined number of texts you could send. Extra minutes were expensive, each extra text message was ten cents. They added up fast.) After Katie had cost them a fortune two years prior by texting nonstop, they’d relented and started paying for unlimited texts too.

I texted my best friend, Mary. Her parents were loaded and they’d all be away on vacation in California for weeks. She and I had been best friends for years. We talked about what boys we thought were cute, I’d been too afraid to tell her about the girls I thought were cute. We’d both been absolutely clueless about boys and sex. We’d made a pact that we’d tell each other if we’d made any progress on that front. Boy oh boy did I have some progress to report.

They were getting back Wednesday night. We made plans to hang out Thursday.

With two days to go. I went about my business.

Katie had been a bit cold towards me since, well, since I’d left her boyfriend folded in half with a dildo in his ass and his own cum all over his face. On Wednesday, dad went to the dentist while mom was out grocery shopping, we had an hour or so home alone and finally had a chance to talk for real.

It was just as I thought, she was really mad at me. But then I learned the extent of it.

Apparently, while being folded over like that for hours, Matt could barely breathe. It was only a few minutes after I’d left the room that he’d realized it. He’d spent an agonizing five hours struggling to breathe, afraid he was going to suffocate.

A (proper) dom/sub relationship was built on trust and respect. She’d left him in my care and I’d nearly killed him. The trust they’d built had been severely damaged, possibly beyond repair. It’d taken everything she could to convince him to stay with her.

I felt awful, truly awful. They had a lot of work to do, but she’d promised him she’d agree to anything if they could try to move past it. I hugged her and, in turn, promised that I’d do anything I could to help make things better between her and Matt since it was my fault.. She smiled darkly at me. “It’s funny you should offer. We have a few things in mind for you to do, chiefly among them, Matt gets your virginity.”

I blinked. I tried to play it cool, like she was asking some great task. I probably should want to save my virginity for someone special. In reality, getting sem-forced to let her boyfriend fuck me just got me wet. (Yes, yes, we could debate all day about if getting fucked in the ass counted as losing one’s virginity. I’m just relaying what Katie said.)

Evidently, I don’t have much of a poker face. Katie rolled her eyes at me. “I knew that wasn’t going to be embarrassing enough for you. There’s other stuff you’re going to have to do. That’s just the start of your punishment. Honestly, Matt’s never really had a taste for being dominant, but he’s really excited at the idea of getting revenge and evening things out. He’s got some brutal, humiliating, and kind of depraved things planned for you.”

I must have looked a little scared because she quickly added “Don’t worry, unlike when you overdid things with him, I’ll be there to make sure you’re not in danger.”

She went back to her room and I went to mine. It was hard to tell what had me more excited, getting fucked by Matt or the prospect of being made to do unknown, humiliating sexual acts. I didn’t realize it at the time, but I was more aroused than I’d ever been. This called for something more than rubbing my clit.

I wasn’t crazy enough to try using the saddle again, yet. I’d hidden the dildo Katie had given me so my mother wouldn’t find it. I’d finally measured it properly, it was six inches long, an inch and a half in diameter.

Actually, I’d finally measured everything properly. I’d overestimated the size of the dildos that could attach to the saddle, I’d thought they were seven inches wrong, they were five and a half inches long and maybe an inch wide. (I guess guys aren’t the only ones who get sizes wrong.) The original butt plug Katie had “given” me was four inches long and inch and a half wide.