Page 123 of Dirty Discipline, Vol. 2

"Yes, Mommy."

I waited for her to say something else, but it was silent except for her soft breathing. She counted my time down every ten minutes. I wanted to see her. Not have this be one way. Did she like the way I looked? You couldn't tell from a stranger's voice what they were thinking. I hated silence. My brain always went places it shouldn't. Fear at being exposed for what I was. Outed as some freak who wanted a Mommy to love and correct me.

"Ten more minutes."

I didn't cut off my frustrated huff in time.

"Should I add more time?"

"No, Mommy, I'm sorry." My knees ached and my thighs were starting to cramp. I didn't have to assume this position often and the bare floors were chilled under my already fucked up knees. I stared at the black screen with the video call timer counting up and impatiently waited for my punishment to end.

"Punishment is up. You may stand but Mommy wants to see your cute outfit in a better light. I won't demand to see your face, I know you still don't trust me. I was so proud that you let me see as much as you did. Now, show me."

I picked up the phone and kept it no higher than my neck, then tipped it a bit to show her my body. The cotton perfectly cupped my dick but it also showed off the way the shirt stretched over the curve of my belly. I wished I was slimmer so the clothes would fit me better.

"I love a hairy Boy and Submissive. Beautiful." At her tone I almost lifted the camera too high but stopped in time. The black of my screen suddenly centered on the center of her chest exposed by the part in a robe. Just like in the picture on her profile her tits were tiny. "I thought my sweet boy deserved a reward for taking his punishment. You didn't have to." The fabric shifted to expose just the edge of a dark nipple. "Now, I want you to take your phone and lay down in bed. What kind of bedtime story do you want?"

I told her to choose as I stretched out on my too small twin bed and again propped the phone where it wouldn't show my face. I focused on her pale chest and counted her breaths as I listened to her tell me a story.

"Get a PO Box, I want to send you a present."

In the back of my brain, I think I remembered her telling me goodnight and to disconnect. I was too sleepy to remember, I curled under the covers and as I slipped to sleep, I wondered if she'd tell me another story sometime.

Chapter 4

Helena

My day was dragging more than usual. I had court that morning and a client had called as they were being interrogated. I was quite content with my sometimes moral ambiguity. My rules were I didn't defend rapists or anyone with violence against women and children, but other than that I took any case offered. My life was down to work, business dinners and the occasional social engagement, and home to my empty bed.

I was getting impatient to see my sweet boy in real life. Messages. Video calls. It wasn't enough for me, but he kept himself hidden from me. I understood that he wasn't ready to completely trust me yet. I wasn't happy about it, but I respected his wishes. He still wouldn't let me see what he looked like. Although, when he'd fallen asleep when I told him a bedtime story, he'd moved enough that his face showed. I knew he was self-conscious about his needs so I hadn’t brought that he’d exposed himself to his attention.

He looked to be older than me but that could just be the life he lived. There were several prison tattoos I'd noticed from my days in the Public Defender’s Office before I'd moved to the private sector for a significant pay increase, I still did the occasional pro bono work.

I tossed my phone aside and a small light blinked telling me I had notifications. Only one caught my attention, it informed me my boy had picked up his package I'd sent him. I was good about sizes and hoped he liked the pretties I'd sent him to wear for me. Inside was a note with my personal number on it but told him to only use it if he was comfortable doing so.

I still couldn't claim him, yet that didn't mean I didn't want to spoil him. I also sent him things to judge his willingness to let his Mistress fuck him. Several plugs in varying sizes and a chastity device I would require him to wear when he wasn't with me. While I liked to push my Submissive to their limits and beyond, I hated that I had the compulsion to test Georgie. The second I pushed too far, I sensed he'd run. We'd only been corresponding a month, nowhere near enough time to develop the trust I'd require from him.

If he didn't contact me after he saw what I sent then I'd move on, but over our weeks of conversation, bedtime stories and his corner time, something inside me no longer wanted to help him prepare for someone else.

I waved at a few people leaving for the evening. Yet I still had some work to do and no real reason to go home. I groaned loudly as my phone beeped and hoped it wasn't a client wanting to ruin my evening.

I picked up my phone and unlocked it with my fingerprint. Excitement built as I noticed a text from a strange number. I clicked on it and several photos loaded.

Goddamn.

Georgie was wearing the pink lacy bra, silk thongs, garter belt and stockings I sent him. The pictures were taken from every angle and I squeezed my cock as I stared at his muscled ass exposed by the thong. His powerful chest muscles filled the cups of the bra and I could see the hard little nipples under the fabric.

A single message followed the pictures. Thank you, Mistress.

Helena: You look so beautiful. Do you like your presents?

While I waited for him to respond I studied every detail of the images and was disappointed that I couldn't see if he was smiling or not.

Georgie: I've never had anything that fit. I love them. You sent me too much.

Helena: I wanted to spoil you a bit.

Georgie: You sent toys.

---