Page 128 of Dirty Discipline, Vol. 2

I reached for my hurting and hard cock, felt the heat of it in my hand. It was almost painful to touch but I jacked my cock in a cruel pace that matched her working her dick inside me. I started to shout, but she hit that spot again and pounded it until I couldn't breathe or do more than work my dick. Praying to come even as my legs collapsed, she slipped free as I covered the covers under me with cum and then she was back.

"Fuck, boy, you're gonna ruin me for other Subs." She shoved her hand under me, slipped beneath my bra and played with my nipples as she rutted against my ass until she lost her pace as her hips sealed to my ass.

I was gasping for breath and in some part of my mind I felt her leave me, her hands were gentle and her words tender until I found myself with my head on her chest and she was stroking my hair.

"You were so good, so beautiful. Mistress was pleased at how hard you came for her."

I jerked as she softly stroked around my stretched sore hole and she kissed the top of my head. It was the last thing I remember as I listened to her heartbeat and hoped I woke up before her.

Chapter 6

Helena

I'd woken at five a.m. when my alarm went off to alert me I had to get ready for work. When I'd arrived the night before I'd brought an overnight bag so that I wouldn't have to rush my time with Georgie. The bed was empty beside me and the sheets had long gone cold. Expecting it and finding the reality were two different things.

The day went by without the usual good morning text or one when he woke up for work showing his Mistress the perfect shot of his morning hard-on that once belonged to me. His cute little panties tucked under his sac and his t-shirt pushed up over his belly because I said I loved it.

I hadn't thought I'd get attached to someone so fast or grow used to our routine. I'd ignored the contract I'd printed out and his cock cage that I'd packed for our night in case things went the way I'd hoped. As my day progressed, I became shorter tempered than normal. My assistant had threatened to quit five times rather than her usual two.

I called a friend to meet up for dinner because I wasn't ready to go home with nothing to do. My driver dropped me off and I went inside, I smiled as he waved at me from our usual table near the bar. I weaved through the room and ignored the looks that I received. I'd always been pretty and soft, but my height and build usually had people looking at me sideways.

"Helena. It's been too long." Kerrigan stood as I approached the table and I offered him my cheek, then he walked around me to pull out my chair.

It was an ingrained habit in my best friend to cater to women. He made quite a living as an independent Escort before he'd opened his own service. He was sought after for his professionalism and discretion. To anyone else he looked like a successful businessman and he was, but he still took jobs on occasion when someone wanted to spend the evening with a Daddy Dom with no sexual contact. I’d laughed at him whenever he said he was burned out on sex and a cuddle session was more satisfying.

"So, what do I owe for the pleasure after months of you avoiding me?" he asked as he poured me a glass of wine and waved the server away when she approached to take our orders.

"I haven't been avoiding you."

"Just because I no longer require your services, you're still my best friend."

"You know that Caregiver and Little's matching service you suggested?"

"Yes."

"I placed an ad. Negotiated with a few Littles but they were fine with my Mommy Domme, but weren't so open about being my Submissive."

"We've discussed this. Being Little doesn't mean they're submissive."

"Thank you for the lecture, Kerrigan."

"Continue."

I chuckled as I picked up the napkin from the table and spread it across my lap. He'd call me on my delaying technique, but I didn't want to admit I fucked up in some way. I'd always had an overabundance of confidence, some said it bordered on arrogance. Once I'd learned who I was, I lived with an honesty that made people uncomfortable. When I'd decided that I wanted to live as the woman I was, I'd shown up to work in a perfectly tailored pantsuit and expertly applied makeup as if it were any other day.

My reputation and win count made me indispensable to my firm and had even made Partner six months later.

"A little over a month ago, I got a message, a boy wanting to be mine, and there wasn't any information. Just a generic profile that the unsure ones put up." He nodded as I took a sip of my wine, and I smirked at his bratty eye roll. "Patience is a virtue. You should have more."

"Yes, this I know, but I'm out of practice."

"Then he sent me a second message wanting to ask questions. I thought what was the harm in helping out a little first time Little?"

"Did Mistress and Mommy become attached?" His question was asked seriously. He wasn't making fun of me.

"Yes."

"Sorry. If it had worked out, you would be happier than you are."

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