Page 121 of Dirty Discipline, Vol. 2

Helena

Hi, Mommy. I want to be your boy. - Georgie

I read the message a dozen times on the matching service for Caregivers and Littles, Dominants and submissives. There was nothing on his profile except the basics. No picture of a cute Little Boy to entice the receiver. It wasn't the first profile I'd ever seen where there wasn't a lot there. Usually just someone wanting a one-off, but my profile clearly said looking for a full-time Little Boy/Submissive for Age Play and Domestic Discipline relationship. I needed someone who wanted a Mistress and Mommy, I spent nearly a decade married to a woman who couldn't stand me except for the salary I brought home and told me I could fuck any man or woman I wanted as long as she didn't have to deal with it.

Just what a spouse wanted to hear. That fucking the person you professed to love was so disgusting that it made them ill.

I was heading for thirty-six on my next birthday. A year ago, I'd started gender affirming care to begin my transition, but hadn't gone beyond that. My cock was still thick and got plenty of use with the use of occasional meds if I couldn’t get or stay hard. I was just getting tired of using my hand. I enjoyed my sex life too much to give up the ability to fuck a tight ass or pussy when I wanted.

I had no shame in my body or what I did with it. Two adults engaged in a consensual sexual and/or romantic relationship shouldn't feel burdened by societies rules. That's why I wanted to find myself a partner who could be all the things I needed, submissive slut and sweet boy.

A pop up alert caught my attention. TattooedBoy4Mommy. I refreshed my screen.

I don't know what the hell I'm doing. Can I ask some questions? - Georgie

I smiled as I read the message. An innocent Little Boy who had no idea what he was doing. I opened the instant message app for the site. I shifted in my chair and let my fingers move over the keys.

Mistress_H: Hello, Georgie. Did you want to know how to be a good boy for Mommy or just want to pick a Mommy's brain? Is this your first time?

I clicked on send and picked up my glass of wine. A little box saying the Georgie was typing caught my attention. I made myself at home and ignored the stack of files that needed my attention.

TattooedBoy4Mommy: Yes. First time. I don't know who to ask.

Mistress_H: Well, I guess I could be nice to a sweet boy and answer all his questions. What would you like to know first?

TattooedBoy4Mommy: What are Littles supposed to look like?

Mistress_H: There's no right way to be a Little. That's for a Caregiver and their Little to discuss. Is that why you don't have a picture?

TattooedBoy4Mommy: Yes.

There was a lot in that single word. I sympathized and understood if he felt insecure especially if he was new to all this.

Mistress_H: I'm positive that you're perfect and that any Mommy would be lucky to have a sweet boy named Georgie.

He kept firing questions at me and I answered each one the best I could. What I needed was different from other Mommy Dommes out there. My Dominant tendencies were a twenty-four-seven, Mommy in our playroom and Mistress all the other time. He'd defer to me in everything, have dinner waiting on the table and knelt beside my seat at the head of the table. I'd own him.

That wasn't for an innocent newcomer who had no idea what he'd be signing up for with me, but I could steer him a bit and make sure he made smart choices in a future Mommy. My computer clock said it was coming up on three a.m. and I felt bad that I'd kept the boy up so late.

Mistress_H: It's way past time for sweet boys to be tucked into bed. I kept you up too late. I apologize. I need to be up in three hours for work.

Several minutes passed before I saw he was typing again.

TattooedBoy4Mommy: Can I message you again sometime?

Mistress_H: Of course. I'll be slow to answer during the day, but I'll answer as soon as I get home. Goodnight and be a good boy and get all your rest.

He typed out a quick goodnight and I closed out my browser. I pushed up from my desk chair. I stretched my stiff muscles from sitting for so long. As I made my way upstairs to my bedroom I wondered if I'd hear from him again. I hoped so because I'd enjoyed his questions, he was curious about how to do it right and safely. Newbies usually jumped in and ended up in a bad situation.

I bet Georgie would be the sweetest Little for the right person.

I stripped off my t-shirt and pajama bottoms, gave my fat cock a couple rough strokes. I teased my slit and I rubbed my hand across my chest to tease my small pebbled nipples. I was a solid A-cup and for my tall, slender frame I was happy with them. With a groan, I stretched out on bed. I didn't have time to jack off. I was already not going to get enough sleep.

I'd grown up in a household where Body and Sex positivity was frowned upon, our bodies and needs a sin. It had taken a few years into college for me to shed that mindset and I came into my own. I'd lived as Nonbinary or Gender Nonconforming, wearing pretty dresses and lingerie outside my professional setting and the moment that happened, my wife had stopped wanting to sleep with me. She didn't want her husband in a dress bending her over and fucking her. She'd called me disgusting and I'd turned bitter as she'd stopped viewing me as her Master and had taken her sexual games elsewhere.

I turned over and hugged a pillow to my chest, attempting to turn my brain off for at least a few hours of sleep. Tomorrow was going to suck but I had to admit it was worth it. The other messages I'd gotten had bored me after a few minutes since they were so easily ready to submit without conversation or rules. I was a demanding Mistress and a gentle Mommy, I just needed to finally find the one who would fit for both sides for me.

My last thought as I made myself sleep was if sweet Georgie had listened and was getting his rest.

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