Page 126 of Dirty Discipline, Vol. 2

"Yes, I used the douche, Mistress. I also brought the cock cage."

"Good boy, if you're very good, I'll give you your other present later after I prepare you for it."

I nearly ran as a knock sounded on the door.

"Easy, boy, I'll take such good care of you. Stay right here, keep your head down and your back to the door."

I nearly cried as her lips brushed mine, almost lovingly, and then her presence was gone. I felt lost and abandoned. She spoke softly behind me, thanked whoever it was and then the door closed. I turned my head to find her pushing a cart with several dome-covered plates and a bucket with a bottle of champagne and also a bottle of wine.

As time passed, she carefully set a dining table, she lit candles and when she took a seat the bottom of her jacket parted to expose her slim legs shown off by the leather. She crossed her legs and leaned back.

"Crawl, my sweet boy."

I should fight her. Tell her that a man doesn't get treated like that, but after years of being clueless as to what was wrong with me, I wanted at least a single night of being owned by my Mistress and Mommy. Each movement brought me closer and I faltered as her jacket opened to expose her small, pebbled nipples on top of subtle, tiny curves. Once I reached her side, I retook my position of submission and she praised me, stroked my hair as she gifted me with a small smile.

I sat there as she began eating and settled in, I waited for her to say something to look at me, but nothing came until she held out a fork with a piece of steak. In silence she fed me, held a wineglass to my lips for me to take small sips. Every once in a while, she shocked me with a kiss or a teasing squeeze to my cock or furry cheeks exposed by my thong.

The front of my panties was wet with pre-cum from her teasing. Her silence gave me too much time to think. Like the times she put me in the corner and only spoke to me to tell me how much time I had. I was trapped somewhere between finding my dream and my ingrained pessimism that she was running some con. Some video would make it to the internet or we had an audience.

"Mistress doesn't like that her boy is looking worried. What has those deep lines between your brows?"

"Are you playing with me?" I'd almost asked if she was fucking with me, but she’d promised a paddle strike for every curse word I spoke.

"Thank you for being honest with me. Last bite, Georgie." She fed me the last bite from our shared plate and had me finish the rest of the wine in the glass. "Clean up our dinner." She ordered and I jumped to obey. "Relationships between Dominants and Submissive, Caregivers and Littles are built on trust. If that doesn't exist between the participants than the Dominant didn't do something right to earn it."

She held up her glass and I filled it with what remained in the bottle, placed the champagne and glasses aside, then stood to push the cart across the room to leave it by the door.

She parted her thighs as I made my way back to her and pointed to the spot between her feet.

"I'm not used to people taking care of me, Mistress."

"I know, and I very much want to rid you of that thinking. If you agree after tonight to be my Submissive and my sweet Little Boy, that will be my first and most important task. Tonight, Mistress is going to not be as strict as normal. I've prepared our bedroom so that Mistress can show you how good she can make you feel. Mistress didn't anticipate how sexy her boy would look in his presents."

"Do you really like me like this? I'm not too big and hairy for them?"

"Never, you're to never be ashamed of your love of soft things. They make you feel good. You love pretty things against that beautiful dick of yours."

I grunted as she leaned forward a bit to cup my cock and give it a few tugs.

"And you've gotten it all wet for Mistress, but before we continue, I must be honest. It's the only way we'll achieve the levels of trust that being mine requires. Don't move."

My throat felt like it was closing and an elephant was sitting on my chest, but I remained still as she stood. She removed her jacket, slowly let it slide off her shoulders and down her arms. My hands fisted with the need to reach out, touch her just for a minute, punishment be damned, but I waited. When I lowered my gaze from her chest to the front of her panties, the hard outline of a cock had me jumping back.

"Ah, I see, Mistress has lost you."

"What are you doing? You just want to laugh at the freak in his panties and shit?"

"Not in the least, I'm a Transgender Woman, I lived as nonbinary for a lot of my life, and in doing so, I am quite happy with my body and my decision to live openly as I am. Whether society agrees with me or not. My ex-wife had a reaction like yours. I didn't want to bring this into the bedroom with us and you should have the choice before I asked you to touch me in return."

I backed up farther even though she didn't come closer. The bulge in her panties had softened. I'd pictured her fucking me, but with a strap-on. I'd imagined all the ways she wanted to play with me. I studied her. Her slim body. Her face was soft and beautiful, now that I paid better attention, she had a feminine yet softly masculine bone structure, but her chest was softened with just the tiniest bit of puffiness where her tits were.

"Georgie, I find you beautiful and sweet, the perfect complement for Mistress and Mommy. I love your hairy body in your sexy slips of silk. I came so hard knowing that my presents turned you on. A horny boy makes me happy. We still have tonight. After we leave this room, we never have to see each other again. You don't know me as more than Helena and I don't know anything other than Georgie. We don't know where each other works or lives. Would you set aside your fears as I have mine and give us just the next few hours? Let a Mistress show you what you should expect from the one you choose in the future."

Before I could answer, she lifted her hand.

"Whether your answer is yes or no, I want you to know I’ve enjoyed spending time with you and I know your insecurities about a Mommy finding you acceptable, but any Mommy would be lucky to have you as their boy."

"Just tonight?

---