Chapter 19: We Have a "Talk"

"We have to talk."

The words most hated by men all over the country.

"Okay," I said, worried now. Janice was sitting on the sofa in the living room, and I was sitting on her lap. Janice had one hand up my skirt and it was devilishly stroking my penis. I was being hugged by the other as it reached around and squeezed my breast forms.

My god I was hard! With all her teasing and humiliation, Janice had kept me on edge throughout dinner. She even made me eat more of her special "glazed" carrots, only this time directly from her pussy as I knelt before her under the table.

And if that weren't enough, as I was doing the dishes she surprised me from behind. Pushing me over the counter, she lifted my skirt, pulled down my panties, and then slipped a small greased vibrator up my ass. This was the first time my ass had ever been penetrated.

I nearly came right then.

And then she turned it on.

I sank to my knees, right there in the kitchen. But before I could stroke myself to climax, Janice grabbed my wrists and forced them together behind my back, leaving my aching penis to push futily against the gentle silk chiffon of the dress.

She then lifted me up and commanded me to finish the dishes. Reaching between my ass cheeks, she turned the vibrator back a notch, to "intermittent".

And now, dishes done, we were on the couch together, and she wanted to 'talk'.

Talk was the last thing I wanted right now.

Bzzzzzzz. "Unh" I moaned, as it went off again.

"Sweet, isn't it?" Janice said, smiling.

"Uhhhh ... yes," I gasped.

"Good, that will get things off on the right foot. Remember I said how my department was now in order?"

"Yes!"

"Well, now we need to talk about where we go from here."

"Yes, please," I said. Would I finally be able to get my old job back? Rachael at work was strongly hinting that I would need to decide very soon.

"At first I was feeling bad that I had forced all of this on you, I mean, I know that you like to dress up, and I really did need your absolute attention and obedience to get through this difficult time, and so I just put two and two together. But all along, I was feeling sorry for having been so selfish about the whole situation."

I gave Janice a big hug, "Oh sweetie, that's all right, I was glad to help."

"But that was earlier," Janice continued. "Now, after tonight, and feeling this," she gave my penis another squeeze, "I'm wondering if this hasn't been just as good for you as it was for me."

"What do you mean?" I asked, worried.

Releasing my penis, Janice placed a hand lightly on my leg, stroking it.

"Tell me this, do you enjoy dressing up as a woman? Be honest."

"Uh..." I hesitated. I don't believe I ever actually admitted this to Janice directly. But after all that we'd been through ... and of course I didn't want to go all the way back to wearing just men's clothing...

I gulped, and told the truth. "Yes," I admitted. "I do enjoy dressing up as a woman. I ... I ... I enjoy it very much."

Janice gave me a kiss on the cheek. "I thought so. Now, let's play a game. Do you want to play a game?"

"What kind of game?"

"No! No questions. Just answer me yes or no. Do you want to play a game? But wait, if you say 'yes', you have to agree to my rules."

I thought back to all of the previous 'games' I'd played with Janice. Every single one of which I lost.

Janice traced a finger over the lace of my stockings.

Bzzzzzzz, the vibrator buzzed to life.

"Unh!" I said, squirming. "Yes, okay! I'll play."

"You'll play by my rules, whatever they are?"

Bzzzzz the vibrator continued to wriggle delightfully in my anus.

"Yes! I'll play by your rules." Bzt Finally, the vibrations stopped.

"Excellent! Okay, here are the rules. I'm going to ask you questions."

"Questions? What kind of questions?"

"Personal, difficult questions. Delicious questions. Humiliating questions. You'll like them."

"Okay..." I began to worry.

"And you have to answer every question."

"What's the catch?" I asked, getting even more worried.

Janice smiled at me. "Here's the catch. As long as your penis is hard..." Janice placed her hand gently on the noticeable bulge in my skirt and gave it a gentle squeeze.

"As long as it is hard..."

"Right, as long as it is hard, you must answer yes."

"I have to answer 'yes' to what?"

"Silly, you must answer yes to all my questions. That's all the rules. You must answer yes to all my questions as long as your penis is hard. Okay, do you understand?"

"Yes."

"Exactly!" Janice grinned. "You've already got it. Okay, let's start with an easy one. Do you like dressing up as a woman?"

"Yes," I said, adjusting my bra strap a bit.

"Do you like licking my pussy?"

"Yes."

"Do you like kissing my asshole?"

"Yes," I began to squirm. These questions were making me uncomfortably hard.

"Do you like the idea of having to wear women's underwear for the rest of your life?"

This time I paused a second before answering. "Yes..." I said slowly.

"Do you like the feeling of being trapped in women's clothing? Trapped and unable to get out of it?"

I gulped. "Yes," I whispered.