Page 124 of Dirty Discipline, Vol. 2

Helena: How did you feel about the toys?

Georgie: Nervous.

Helena: I don't want you to be nervous. Mistress likes to play with her boy's bottom.

Time passed and no response came, I went back to working as I waited for him to process or show me I'd stepped over the line. The pictures he sent me would strengthen my jerk off fantasies. Since his corner time, I hadn't lacked for material.

Finally, another chime signaled another message and I opened it, and nearly came in my panties. He’d tucked his panties under his heavy, hairy balls and his hard cock was on display for me. I swore I could see the fat head glistening with pre-cum. I wanted to praise him for showing me what my presents did to him, but I also wanted to punish him for the same reason—teasing me.

Helena: Did your silky panties make you horny for your Mistress?

Georgie: So soft. Felt so good.

I opened the browser on my computer and logged into the site for my preferred hotel for clients and personal escapes. I made a reservation for Monday night. I knew from our conversations he never worked that night because the place he worked was closed.

I booked a suite, made a special request for dinner and champagne.

Georgie: Mistress?

My delay made him insecure.

Helena: I want to see you. No real names. No identifying info. Just us and a hotel room. One night. No strings if you don't want them.

After hitting send, I set my phone aside to get back to work as I waited for him to think it over. I wanted him to be sure and if he turned me down or didn't show, I'd take advantage of the room and the hotel perks. I finished typing up my opening statements for court the next morning and just as I was about to give up, my phone pinged.

Georgie: What would I have to do?

Helena: I'll send you a special outfit. I want you to wear it for me. You'll just let me take care of you.

Georgie: Okay

I sent the date, time, and address where to be that following Monday. I told him I was at work, but I'd message him when I got home. A moan vibrated my chest as I received one last image of him laying on his back. His big fingers looked as if they were playing with the silk of his pretty panties and his dick rested on the small curve of his lower belly.

How the hell was I going to wait an entire week to get a taste of my sweet, submissive boy?

I couldn't resist one more text before I forced myself back to work.

Helena: Mistress is going to punish you for teasing me. Be careful what you ask for.

His sorry didn't sway me from planning his punishment. I had to believe that when the time came, he'd show up to my room and we'd see about starting the next phase of our relationship. There was only so much trust I could establish with our current path.

One night of owning him wouldn't be enough. As soon as I touched him, I knew that would be it for me. I was self-aware enough that while I'd told myself I was preparing him to be well-informed, I was in actuality teaching him how to be mine. My own secrets needed to be revealed, my claim, my gender identity, and the last was the biggest one.

I was nervous about that, but our semi-anonymous hookup would lessen some of the blow when our paths never crossed again.

I felt my brows draw together at the thought of our first meeting not working out, but it was an outcome I needed to prepare for. I finished up work so that I could get home and have some time to exchange messages or have a video call with my boy. He loved when his Mommy would tell him a bedtime story and I loved watching as his wall disappeared. I could see his sweet face for a few minutes as he relaxed.

Chapter 5

Georgie

It was thirty minutes past the time I was supposed to be at Mistress's hotel room, but I was standing across the street looking through the front of the hotel at the reception desk. This place was one of those ones that I'd have to spend a months’ rent for one night. They probably wouldn't even let me in the door.

I was sick to my stomach. My pretty lingerie was hidden under my usual jeans and t-shirt, and leather jacket. Mistress had told me to give my name as just Georgie at the front desk and they’d give me a key. I pulled my beanie lower over my dark wavy hair and checked both ways before crossing the street.

The doorman opened the door and I stepped through it, I kept my head down all the way to the front desk. "Helena left a key for Georgie."

"Yes, here you go, elevators are to your left and your suite is on the thirtieth floor. Enjoy your stay, sir." That's all the pretty blonde said as I palmed the key, I shoved my hands into my pockets and followed her directions.

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