Under My Boss's Authority (Under Him)

The leather creaked softly, the couch coming to feel like a second home. That used to be the office, but things had changed pretty radically since I’d started isolating. Even before finally being told to by the government. Not the first time I was ahead of the curve.

“I have another gift for you,” I said, when the coffee was done.

“What is it?”

“You have to come and see,” I replied, trying to maintain the mystery.

Racing her to the top of the stairs, Vega sat waiting expectantly.

“Close your eyes.”

With a huffing sigh, she obeyed and I went to the secret part of the wardrobe where I kept all the gifts.

It didn’t look like much. A short rectangle, in the same style as the collar box. Bought from the same shop, in fact. They shipped all their merchandise in plain, white boxes. The better to ensure privacy and discretion.

I set the box on her lap, giving her thigh a slight squeeze to let her know that she could open her eyes.

She didn’t bother to ask what it was. Knowing by then that I wouldn’t spoil it and there was only one way to find out. Taking the box in both hands, she slid off the lid. Her expression going from excitement to confusion.

On the red paper inside the box lay a small bottle of lube, which I guess she knew, and a second item that confused her.

“It’s called a butt plug. Now, can you guess where that goes?”

“I-in my butt, I assume?”

“Very good. Yes, that is exactly where it goes, though only with lots of lube and other preparation. Don’t let anyone tell you different, okay?” Even as I said it, though, I felt a pang in my chest.

I didn’t really want to imagine anyone else having conversations like this with my Vega. Even though the contract was only for two weeks, the idea of her with someone else made my stomach churn.

“Okay.”

“Promise me,” I urged, despite the bile rising in my throat at the thought of anyone else’s hands on her.

“I promise.”

“Good. The main use for a butt plug, though it can just be used on its own for fun, is to gently stretch the asshole, getting the receiving partner ready for anal sex.”

“You’re going to…” she squeaked a little, “Put it in my ass?”

“No, not yet. You need practice and preparation before that. I just thought I’d show you how it works so you can start preparing.”

“O-okay.”

“Take off your clothes.”

Nodding quickly, Vega got up off the bed and started to strip. Pants first. Then her shirt. Last to come off were her panties, leaving her standing naked before me, back turned, awaiting further instructions.

I caressed my hands down her arms, Vega relaxing into me with a slow sigh. Leaning in, I kissed and then nuzzled her neck, giving her little licks and bites. It seemed to put her in a much calmer mood.

Taking her by the arms from behind, I guided her onto the bed. Her head down and her ass up, in an ever deeper version of the same position when I’d put her against the wall.

It was subtle. Just the smallest quiver, but I knew she was nervous. I couldn’t really blame her. It was a sensitive thing and she didn’t know what I was going to do. Often, not knowing was worse.

“I’m going to help you get ready,” I said, massaging her ass.

She tensed when I first made contact. But she into the rhythm as I continued to massage her.

“It’s best if you have an orgasm. Helps relax everything. I’m going to lick you, okay?”

“Lick my ass?”

“No, your pussy. If I do it well, which I certainly intend to, the effects will go everywhere.”

“Oh,” She seemed to relax a little more. At least I didn’t see another tremble like before.

Continuing to massage her ass, I got the other hand involved. Moving down to her pussy, spreading, already smelling her gathering excitement.

Spreading her beautiful pussy, I leaned in and tasted her sweet lips. I took it easy on her. Despite what my id might be dictating, it was better to be gentle at such a delicate time. I wanted her to feel good. While getting her ready to feel even better in the future. It was a training session. Even if she didn’t know it.

She started to respond. Gently at first. Some soft moans. Lightly pushing her hips back, so her pussy pressed that much harder against my lapping tongue. Natural and positive responses, telling me she was getting into it. The thought of putting something up her virgin asshole no longer seemed quite so scary.

She started to shake, an orgasm building in her like an earthquake as she got closer. Taking her around the waist for support, I kept going. Bringing her up to and then through the gates of pure joy, her upper body collapsing against the mattress.