Chapter 18: Third Hole Training

Another day, another note. I arrived at work at my usual early time, looking forward with great anticipation to the note I expected to find at my desk. As usual, I was not disappointed, as a note and a pair of panties sat in my desk. I was really curious as I pondered why panties would be on my desk. I grabbed the letter and read it.

Annie-girl, I assume you are curious why I would leave panties on your desk. Especially considering you are not to wear them anymore. Well if you open your desk, I think you will begin to understand why I have left them for you.

Look now!!!

I quit reading the letter and opened my drawer. What I found was a small, black plug, that I knew from my brief earlier experimentation was a butt plug. I returned to the letter.

This is a butt plug. It is the first of three you will wear in the next week. Also, in the drawer is lubrication, I highly recommend you use it before inserting the toy in your ass. You will wear this toy in your ass from the time I arrive until the time you have eaten my cunt and I am done with you for the day. Since you have a major presentation this afternoon, I would highly recommend that you get it in your white ass soon and walk around with it as much as possible, so you can get used to it. Because you have never walked around with a plug in your heinie before, you may wear panties today (Would hate to have it fall out during your presentation).

If you need help with putting the plug in your own ass, I should be at work by quarter to eight and will be more than willing to assist my slut.

Ms. Audree

I looked at the plug. It wasn't that big, about the same size as the one I had used a while ago with an online Mistress. So I knew it would fit, although it had been a while since I had put anything in my ass, and I sure wasn't comfortable about walking around with it in my ass.

I reached for the lubricant and gave a generous coat to the plug. I lifted up my skirt and put some lube at my anal entrance as well. As I struggled and attempted to get into a position to put the toy in my ass, I heard my door handle turn. I quickly sat at my desk, as if working. Ms. Audree walked in and closed the door. My face must have shown the panic, "Struggling with today's task, Annie-girl?"

"No, Ms, Audree. I was just putting it in as instructed when you walked in and I panicked."

"Do you want my help, Annie-girl?"

"Yes, Ms. Audree, I would be very grateful."

Ms. Audree walked to my desk and I handed her the already lubed toy. She instructed, taking the toy, "Bend over, Annie-girl." I sat up and bent over my desk. I felt her soft hands lift up my skirt and her hands pull apart my ass cheeks. Although slightly humiliated, I had become so accustomed to being vulnerable and at the mercy of my black assistant that this just seemed like a natural progression. I felt the toy go between my ass cheeks and after a brief pause I felt it slowly slip into my ass. A slight burn shot through me as the toy filled my rectum. Ms. Audree gave a playful slap on my ass before pulling my skirt back down for me. "Let's get to work, Annie-girl. Today's presentation is fucking big." She tossed me the panties and suggested I put them on; I quickly pulled slid them up my legs.

The rest of the morning went by fast, and I was on my feet for most of it and desperately trying to get used to the toy in my butt. Although I never got completely used to the feeling of walking around with a toy up my butt, it became more manageable and relatively tolerable by the time of the big meeting. The meeting went off without a hitch and I figured we were only a few drinks and some schmoozing away from closing the deal. We were to meet next week for a supper meeting to go over the final details of the deal. The group decided to go out for drinks to celebrate the success and I looked at Ms. Audree, who gave me a subtle nod approving my participation.

There were eight of us who left together and ended up at the Irish Pub. I gave a little yelp when I sat down, having not properly sat down at the right angle for the plug. Ms. Audree gave a knowing smile and sat beside me. Under the table, her hand sat on my leg, just resting there, a potential tease. One drink became two, which became three and more. Soon we were all getting pretty intoxicated.

When only four of us remained, including Penelope and her gay assistant Markus, Ms. Audree swerved the conversation towards sex. A tingle teased my cunt as the prediction that Penelope would succumb to Ms. Audree's charm flashed in my head. Ms. Audree, reading my mind, moved her hand under my skirt, teasing my pussy from outside of my slightly damp underwear. Ms. Audree started harmlessly, asking Penelope, "So when do you plan to have children?"

Penelope, a few drinks in, became way more frank than her work-self, answered, "I'd have to have sex to get pregnant."

We all laughed, but Ms. Audree used it as an opening, "So you don't have sex often?"

"I honestly can't remember the last time I had a real cock in me," Penelope answered, clearly drunker than I thought. I don't think I had ever heard her swear in the few years I had known her and her first one was 'cock'.

Ms. Audree, leading her prey to the sexual slaughter, said, "Oh, so you're bi. That makes sense. I thought I noticed you checking me out."

Penelope spit drink out of her mouth, clearly shocked by the statement. "Excuse me," she said, her words slightly slurred.