Voluntarily Blackmailed By My Master

A woman meets her ex-lover. He proposes a somewhat guilt-free option to her for sleeping with him again.

I hadn’t seen him in a while. He was my first. First and only. A few months ago we decided to call it quits. That wasn’t the first time we tried to do it. More like the seventh. Ninth, maybe?

He and his cock were still living rent-free in my head. I soon learned that I had lived in his head too.

We met, overcame the initial awkwardness of such moments and then got to talking. He was single. I was single. He’d improved his job. So did I. The normal pleasantries of ex-lovers in their late twenties.

Then he dropped a small bomb.

“I still have the pictures and the videos”, he said. “What would you do to make sure that they don’t leak…?”

He looked at me playfully. He could make things sound serious and completely unserious at the same time. I didn’t know where this would go.

“I’d do anything”, I playfully said as well. He looked me in the eyes for a short while and a little smirk appeared on his face. A familiar one that would show when he knew he had me. When the line between serious and unserious shifted more towards the serious side.

He leaned in a little closer and started to speak softly. He used the words he knew I couldn’t resist.

“Of course an innocent and well-behaved girl like you would never do such a thing herself. But when a man forces her into it, she cannot blame herself, right?”

I nodded.

“And she must at least be a little bit flattered that a man would be willing to go to such lengths in order to get her to sleep with him, right?”

I nodded again, slightly cursing the fact that he knew exactly which buttons to push.

“So what might such a girl do in order to make sure nothing gets leaked without it interfering with her life too much..?”

There it was. He crossed the line completely. He was now serious. I both couldn’t believe it, but also wasn’t surprised. Oddly enough, I wasn’t scared that he would actually leak things. I knew he cared about me too much for that. Sometimes he was just driven by lust and I - the little slut he trained - became the target of that drive.

“Such a girl would need clear rules and boundaries”, I countered. When he asked what those were, I told him to propose something since he was the one creating the mess he was putting me in.

“Fair enough”, he said and he leaned back. He thought for a while as he stared out the window. Then he leaned back in.

“You know there’s a safe word, right? Say it, or just tell me to stop, and I will.”

“I know”, I said. “But you’re not the only one who has a track record of making bad decisions based on lust.”

“Good”, he said. “I just want you to know we’re playing here.”

He continued. “We see each other 12 times a year. Could be once a month, could be a different spread. All of them at least a little special. We block 24 hours in our agendas for each moment.”

He thought a little more. “That’s all I have.”

“It seems like you thought about this already”, I countered. “Maybe a little”, he admitted as the smirk re-appeared on his face. “It’s hard not to think about a good girl like you.”

I had to blush and then got annoyed at myself for blushing at such a statement.

“Alright”, I said. “But what do we do if one of us gets a real partner. Like for life?”

“We reconsider”, he said. “I don’t want this arrangement to be a burden to your life. I want you to enjoy it too.”

I nodded. Leaned back and thought for a while. At least I acted like I did because on the inside I was already thinking about his cock inside me.

“How fucking dare he,” I thought to myself. “To wander back into my life and make such a horrible proposal to basically blackmail me, but making it sound all nice?”

But it did sound nice. He kinda allowed me to make a bad decision guilt-free because he was "forcing" me to with his blackmail.

“And are 12 bad decisions per year really that bad?”, I caught myself thinking. I was already trying to argue my way into bed with him.

He noticed my internal conflict and assured me he had the same. He told me how often he’d wanted to delete the images and forget about me. “But I can’t”, he said. “I can’t be with you, but I can’t stop trying to sleep with you either.”

Then he gave me his phone and unlocked the hidden images. There I was. The memories depicted became crystal clear in my head again.

“Delete them if you want”, he told me. “It’s your call, and it will keep being your call.”

I looked at them. Kept looking. Then I gave him his phone back without a deleting a thing.

“How dare you blackmail me like this, mister. You’ve really, really put me in such a terrible spot…”

His smirk got even bigger.

“I’ll get the bill. Let’s get out of here.”