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Chapter 4: Coworkers

True to her word, Marianne spent the weeks after using me like a toy. Her appetite was insatiable — she would cum at least three times every day. Sometimes I would go down on her under her desk, other times she'd ride my cage in a chair until my panties were soaked with her.

And she never unlocked me once.

She had made it seem like the job would require me to be discrete about who I was — that underneath the makeup and dresses and lingerie, I was really a man. But she gave up the truth to almost anyone, my coworkers quickly learning it. And the strangest thing was that none of them seemed surprised by it.

"Can I see it?" asked Jennifer, a blonde woman with glasses and pouty red lips.

"Carly?" Marianne commanded, widening her eyes at me.

I sighed and stood up from my desk, lifting the hem of my tight, short dress. I was wearing sheer panties that day, my cage clearly visible through them. Jennifer bent over and leaned in close. It was an almost-clinical examination. She reached out and pulled my panties down, then grabbed the cage and looked it over, ignoring my gasp and moans. These days I was so horny that just a touch filled me with frustrated pleasure.

"Is this a new model?" Jennifer asked, glancing over at Marianne. "The bars are so much slimmer."

"For better teasing," Marianne explained proudly. "Some new kind of steel makes it even stronger despite how small they are now."

Jennifer shook her head in amazement. "Really nice, Marianne. I've been thinking about getting Toni a new one."

"Oh, you should!" Marianne gushed. "This one is really worth it."

I looked between them, shocked at how casual their conversation was about this. How normal this seemed to be.

"I see her panties are still dry," Jennifer noted. "How long has it been?"

"Just a few weeks," Marianne said. "But the leaking should start soon."

Leaking? I wondered.

"Well, I could use a new secretary too," Jennifer said with a grin, releasing me and pulling my panties back up. "Let me know when you're done with her."

Marianne laughed. "You can get sloppy seconds whenever you want, Jenny. Just let me know."

"Careful, Marianne," Jennifer said, returning Marianne's laugh. "I just might take you up on that."

One afternoon, Marianne called me into her office. I prepared myself to please her, but when I entered, I was surprised to see her sitting at her desk. Normally, she had her skirt hiked up or pants already off. What was going on?

"I'm moving forwards on an important deal," she said, gesturing to a chair for me to sit. "And I need you to prepare for it."

She pushed a box across the desk towards me. I looked at her for permission, and opened it when she nodded. Inside was a pointed black object about the width and length of two fingers, slim at the top before curving out in a wide arc. The base was flared, with a cursive "M" carved into the bottom.

"You may not be allowed to use your sissy cock anymore," she explained as waves of realization washed over me. "But you've got other parts. And now we need to start training them."

A buttplug? I thought, expecting feelings of horror and confusion but finding nervous excitement instead. This is training?

I lifted it out of the box, surprised at its weight.

"You'll need to start wearing that every day," Marianne instructed. "Consider it part of your wardrobe now. A proper sissy like you should be plugged at all times."

A chill ran down my spine. After the lingerie and the clothes and the cage, somehow this felt like a line I couldn't cross. If I did it, I knew I could never turn back. This was my final step into my new life.

To become the sissy I knew I was.

Marianne showed me how to use it, helping me slide it inside. It felt enormous, filling me completely and deliciously. It pressed against a sensitive spot inside of me, settling into place as I straightened and pulled my panties back up. I swelled in my cage. The sensation was overwhelming at first, the gentle pressure of the plug mixing with the hard restraint of the cage. I moaned, my skin suddenly alive with the silkiness of my stockings and the sweetness of my lingerie.

"It feels really good," I gasped as I took a few experimental steps. "It's so big!"

"That's the smallest size," Marianne laughed, leaning back in her chair. "You'll be getting used to much larger ones before we're done."

The idea made me shiver, but I was too distracted by the feelings the plug was sending out to my bodies. My toes tingled, my stomach tightened with every motion. I had never felt anything like it. I could feel pleasure building within me, and wondered if it could give me an orgasm.

If you can, she'll never take that cage off, I thought.

For some reason, it made me harder in my cage. As much as I desperately wanted it removed, wanted to be able to touch myself or have Marianne play with me — as much as I ached for an orgasm, another part of me wanted to stay locked away. The constant arousal had awakened a voice in me that grew louder and louder the longer I stayed in the cage.

It feels nice to be horny like this, it whispered in the back of my head. Cumming is such fleeting pleasure. Don't your stockings feel nicer when you're locked up? Don't people's eyes on you make you feel sexier when you know they can't play with your cock?

I knew it was right, even as I hated the truth.

Doesn't this feel like how you're supposed to be?

Every morning as I slipped in my plug and rifled through my lingerie drawer, my cage dangling between my legs, I thought about who I was now. Locked and plugged and dressed in pretty things. I wore clothes meant to excite Marianne, reveled in the lascivious gazes of my coworkers. I loved every second of it.

Little did I know that Marianne already had plans for me — for me to take my final step and become a sissy, once and for all.