Chapter Fourteen

Shenanigans

In his faded jeans, with his shirt untucked and half unbuttoned, the sleeves rolled to his elbows, Alastair looked hotter than I’d even imagined when I’d pictured him here with one of his boy toys.

Being in a formal position of dominance brought out a fascinating and arousing confidence and competence in Alastair that I ate up. He seemed at home, with me at his service in my lacy panties and corset. I’m sure his fuckboys had appreciated it, too, but I knew by now how sweet Alastair could be, how vulnerable and kind and thoughtful he genuinely was. Still, there was something absolutely irresistible about the way he assumed control and went about the business of dominance in a singularly casual and pragmatic way.

I realized I was staring at him in a dreamy way when he cocked his head and said, “What?”

“You’re…you’re more at home here than I expected, Sir.”

“Meaning?”

“You know what you’re doing.”

Alastair only smiled and brought me the kimono.

“You can lower your arms,” he said.

He helped me into the robe and tied the belt in a casual knot.

“There,” he said, and stepped back.

I stood there, feeling beautiful and outrageously feminine in my finery.

“Toby, you look totally fuckable,” Alastair said, eyeing me up and down. “I wish we had your little brown shoes.” He sighed with regret. “Arrange yourself on the settee, please. Look seductive.”

I tried to be graceful as I did my best to lounge in an alluring way on the velvet cushions of the settee.

“With your permission, I’d like to take some photos,” Alastair said.

“Uh…I’m not sure I’m comfortable with that, Sir,” I said, hating to disappoint him. But it was one of the rules I had and maybe I should have put that in my hard limits. I never let anyone take photos of me without my clothes on—or with very minimal clothes on. Basically, in sexual situations. Definitely not in this room.

“All right. Thank you for telling me,” he said. “Can we pretend?”

“Yes, of course, Sir,” I said.

“Thank you. Just pose for me. That’s all.”

Alastair stepped forward to arrange the folds of the kimono. Then he stepped back and stood with his arms crossed as my heart beat frantically and my cock bubbled with anticipation.

He’d barely touched me, and I was dripping like a leaky faucet.

“Mmm, that’s nice. Put your chin in your hand. Yes, like that. Perfect.”

I did my best to model for him, despite the fact that I was a touch away from an orgasm. I smiled and primped and tried to look saucy. Alastair egged me on with encouraging words.

“Okay. Now get on all fours,” he said, tapping his chin with a finger.

I did as he’d asked, going up on the cushions and posing like a good puppy, as if we really were engaged in a photo shoot. Alastair stopped talking and examined me with a frown.

“Stay still,” he said, his voice rough.

I gazed down at the velvet cushions as Alastair moved forward. They sank beneath his weight. The warmth of Alastair’s hand landed softly on my behind as he inhaled a shaky breath.

“Fuck, you’re beautiful,” he said as he drifted his palm over my rear end. He shoved the fabric of the kimono up and over, so that my ass in the white bloomers and garters was there for his pleasure. He gathered the material of the ornate robe in one hand and held it at my waist then pushed the elastic edges of the bloomers up. Then there were fingers running along the garters, touching the skin of my thighs and pushing up under the edges of my panties.

“Fuck, fuck, fuck,” Alastair muttered, as he examined me. “So fucking soft. How are you so goddamn soft?”

I couldn’t answer. I was beyond making words.

“You’re as soft as a girl, Toby, and just as pretty. But you’ve got this,” he murmured, as he slipped his fingers around the front to stroke my balls and up the bottom of my cock. I was hard as a rock, and the panties were wet with my lust.

I thrust against his hand, moaning like the desperate slut I was. I shuddered and whimpered as he touched me.

“So very pretty, baby…just for me.”

I gasped and lowered my chest to the cushions, so that my ass was in the air. He could have it.

“Good girl,” he said, and slapped me with his other hand.

I cried out in surprise and pleasure, and he did it again, his palm landing against my buttock over the thin white cotton and silk with a satisfying thwack.

“Oh fuck,” I said, unable to stop myself. “I’m sorry, Sir,” I whispered.

“Such language from something so pretty and dainty,” he murmured, stroking my cock with the lightest pressure—a deliberate tease. “I should punish you properly for that.”

He withdrew his hand and stood. He came around in front of me and urged me to my knees, holding my hand to help me. Then he sat down on the settee and pulled my upper half across his lap, and I knew what he was going to do.

My eyes went wide as he settled me, adjusting my body so that I was in the position he wanted. Something about being manhandled sent a spike of desire through me, and as my trapped cock bumped his thigh, I thought I might die. I made a desperate sound.

“Good boy, Toby. Just stay there. That’s all you have to do. Oh, and don’t come. It’s not allowed. Only when I say.”

I made a choking sound.

“I know, it’s going to be difficult to control yourself. But good boys and girls wait until their master gives them permission.”

“Yes, Sir,” I whispered, staring at the imperfections in the velvet as Alastair stroked his palm over the panties. “Yes…Master,” I murmured, just to see how it felt.

“Sir will do just fine, Toby.”

I could feel his cock, hard as hell under the soft material of his jeans.

“Yes, Sir.” I pressed my forehead against the cushions, overwhelmed. The physical sensations were one thing, but the mental mindfuck of bending over another man’s lap for a spanking was something else. It was exhilarating and terrifying and embarrassing and humiliating all at once.

“I’m going to spank this pretty bottom now.”

I nodded, unable to speak.

“Good boy. My pretty, pretty boy,” he said, and I squirmed, pressing my cock into his thigh as the first spank came. The shock of it, the sound of it, startled me almost as much as the stab of pleasure that accompanied the pain. I gasped and cursed behind clenched teeth.

He went back and forth between each buttock, laying his hand on me like he owned me, and I fucking loved it. It hurt, sure, but not much. And it felt so…deliciously possessive and corrective and yes, Daddy, I deserve a spanking because I’ve been a naughty, naughty boy and I didn’t even know where my mind was going.

He stopped and rested his hand as I tried to scramble my thoughts back together. I panted hard as the sting spread out and warmed me like a small, cozy fire. If this was how it felt overtop of cotton and silk, I wondered what it would be like on my bare skin.

“Have you ever been spanked before, Toby?” he asked suddenly. I felt like we’d been over this, but I couldn’t remember my name right now, let alone a previous conversation.

“Not like this.”

“Explain.”

It was hard to form a coherent thought, even more difficult to form words. But he’d asked me to elaborate.

I craned my neck to look at him. “You think nobody’s given this ass a quick slap? Of course, they have. But nothing like this.” I swallowed thickly and my cock throbbed. “I’ve never been spanked over anyone’s lap like I was a—”

“A what?”

“A…a bad boy. A naughty boy.”

Alastair huffed a laugh.

“Even when you were a kid?”

“Nope. Thank God, because if it felt like this it would have been really fucking embarrassing.”

He laughed harder.

My breath hitched when he tugged the bloomers down, then slipped his fingers under the waistband of the panties and dragged them to my thighs, exposing my skin to the air.

“Oh fuck,” I whispered.

“Not yet,” he said. “You need to be spanked properly, Toby, so that you’ll learn to watch your language. Such a pretty, sweet femme-boy shouldn’t be cursing like a sailor all the time.”

I hoped he was joking, but I ate it up like wanting to behave was my truest desire. I’d honestly do whatever he said if he kept treating me like this.

“Yes, Da— I mean, Yes, Sir.”

“I beg your pardon?”

“Nothing, Sir,” I said, my face on fire, making me way too hot all over.

“It sounded like you said something else.”

“Nope.”

“Hmm.”

“I’m ready, Sir,” I said, to distract him.

“We’ll talk about that later. For now, I’m going to spank my sweet slut for cursing and being a brat.”

Yes, yes, yes!

“Okay!” I squeaked.

He brought his hand down on my bare ass. I jerked, moaned then cursed, almost at the same time.

“Shit. Sorry. Oh fuck. Goddammit.”

My face burned with embarrassment.

“I’m so sorry, Sir,” I gasped.

He was laughing so hard the vibration went through me.

“It’s okay. Well, it’s not okay, but I understand that this is all very new for you.”

“Thank you, Sir,” I said, breathing hard and wondering when the next spank was coming.

“You have no idea how much I’m enjoying this.”

“I think I do, Sir.” I wiggled myself over where I could feel his cock jutting up against me.

“Fair. But it’s not just that. It’s not just physical.”

“Yes, Sir.”

He stroked the bare skin of my bottom.

“Ready for more?”

“I think so, Sir.”

It turned out that I was not prepared for anything that happened next.

Alastair disciplined like a pro. He went harder than I’d expected, and it was an eye-opener. Gone was the easy, playful technique he’d used when I’d still had my bloomers on.

It hurt. It stung. It became a roar of pain and heat under my skin in a matter of seconds. I was beginning to regret my decision to submit, to be honest, but not enough to use my safeword. Because at the same time that I was suffering and my ass was burning and my skin was screaming, my heart was beating like a drum and my insides were gooey with emotion and lust and the joy of being handled.

I squirmed and tried to get away, thinking I had a chance, because Alastair Kenney was a nice guy. I forgot that in this room, Alastair Kenney was something else.

“Uh-uh. Stay still,” he said, without an ounce of sympathy.

Dammit.

“Yes, Sir. I’ll try.” My voice was weak and shaky. The only part of me showing perseverance was my cock as it shoved at Alastair’s thigh like a firebrand.

“You’re doing great,” Alastair purred, the kindness in his voice contrasting with his current treatment.

Yay me?

“Here, give me your hand.”

I moved the arm that wasn’t confined by Alastair’s body and reached behind me.

Alastair wrapped his fingers around my wrist and bent my arm at the elbow so that it lay across my lower back, effectively keeping me in place. He kept me firmly trapped as he soothed my spanked cheeks with the palm of his hand, crooning soothing words. I dared to think it might be over.

But then he started again—slaps so hard I yelped and begged for leniency.

“Say your safeword if you want me to stop. Do you remember what it is?”

“Yes,” I said, sounding so small and scared.

“Ready for more?”

“Oh, come on. It hurts!”

“It’s supposed to. I thought you’d like it.”

I took a breath. “I do. It’s just…I’m scared. I don’t know how much more I can take.”

“All right. Thank you for being honest with me. We’re almost done, anyway.”

I felt relief at those words, but also a strange disappointment. My cock was hard and leaking, there was a fire in my belly and I liked being held so firmly. The only thing not happy about everything going on was my poor lily ass.

Alastair started spanking again, and I tried to take it. I struggled to be good, but I couldn’t help squirming and begging. Then I realized I was crying—sniffling like a little kid, and I didn’t know what had happened.

He rested his hand on my bottom.

“Toby? You okay?”

“Fine,” I said. My voice trembled, and I couldn’t stop snuffling.

“Are you crying?” He didn’t sound shocked or upset, just curious.

“Maybe?” I admitted.

Yep, I was crying like a little baby over Alastair’s lap. Again, I didn’t hate it. But I kind of hated that I didn’t hate it. What the hell was wrong with me?

And he laughed. He actually laughed, which made me sniffle harder.

“You bastard,” I mumbled.

“You can’t talk to your Dom that way. Didn’t anybody tell you?” he said.

“I’m sorry, Sir. It just…hurts. But…” Sniffle. “That’s not why I’m crying.”

“It isn’t?”

“I don’t think so. I think it’s because…it’s over?”

It was so strange, because I had struggled to get away and now all I wanted was to stay like this forever. I didn’t understand it.

“Oh, honey,” Alastair murmured, cupping my chin with the hand that wasn’t spanking me anymore. “It’s not over.”

I blinked. Sniffle. “What?”

“This part is over, that’s true,” Alastair said, letting my wrist go so I could bring my arm around. “But there’s a whole room of delights to explore.”

I rubbed my face, feeling ridiculous and silly. Alastair helped me stand and placed me between his spread legs as he held both my hands in his. He gazed at me with concern.

“You okay?”

“Yeah. Are you okay?”

He blinked, then laughed. “You know, I don’t know if a sub has ever asked me that before.”

“Huh.”

“Or cared, frankly,” he admitted. “Do you know how stunning you are?”

“Even like this? With the tears and the snot?”

“Especially like this.”

I squinted at him.

“That’s kind of fucked up,” I said.

“Oh, I know. I’m hoping we can be kind of fucked up together,” he said, motioning me closer. “Let’s get these off.”

Alastair helped me out of my bloomers and stockings and peeled the panties the rest of the way off, leaving the corset and robe. Then he stood and took my hand, leading me to the vanity. The stool made a scraping sound on the wood floor as he pulled it farther out and laid the bloomers flat over it.

It felt strange to be only naked from the waist down.

“Sit.”

I stared at the stool. I mean, thank God it had a cushion.

“I…”

“Yeah, it’s gonna hurt. But I want you to do it.”

I took a deep breath. “Yes, Sir.”

“Good girl.”

Well, that helped. I carefully sat my sore ass down, not without a wince and a whimper.

“Does it hurt?” he asked, sounding more curious than concerned. And kind of excited.

Beautiful, adorable, pervert.

“Yes.”

He smiled. “Good. That will add to the experience.”

The experience of what? Was he going to do my makeup?

He went to his knees in front of me.

“Oh,” I said, staring at him and realizing again how fucking attractive he was, especially with flushed cheeks, his curls disheveled and that devilish goatee. He gazed at me for a moment, then placed his palms on my knees. He took a deep breath and slid his hands along my thighs until they landed at my waist where the corset hugged me close, eyeing my standing, leaking cock.

“Oh, fuck,” I said. Then my eyes went wide. “Sorry, Sir. I’m sorry.”

He didn’t say anything. He was staring at my cock like he wanted it so bad it hurt.

“Toby?”

“Yes, Sir?”

“I’m going to suck your pretty cock.”

Okay, then.

“Okay.” It sounded like a sigh.

“But I want you to keep your eyes open and watch the mirror. Don’t look away. I want you to see yourself come undone,” he said, his voice low, measured and hypnotic. “Can you do that for me?”

“I think so, Sir,” I said. I gripped the edge of the stool and my heart pounded.

“Good.”

I stared straight ahead and watched myself in the gold-framed mirror. My cheeks were flushed, glistening from the tears, and my kohl-rimmed eyes were wide with sudden anticipation. I hadn’t expected him to go down on me. The spanking had been strange and exciting and fucking painful, and my throbbing ass was a sexy reminder of it, but I didn’t know what to think about this.

Alastair moved forward, sliding his head into my lap as I watched the reflection in the mirror. His tongue slid up the bottom of my cock and swiped the bubble of moisture from the tip, as my mouth opened on a gasp. Then he did it again.

I tried not to look down at the top of his head, but it was hard. Instead, I focused on the mirror. Watching the wide-eyed femme-boy in the reflection gave me a strange feeling of being simultaneously outside of my body and within it.

Alastair seemingly savored every curve and ridge of my penis with his tongue and lips and teeth, while I held onto the stool and my sanity for dear life, watching my responses in the mirror. The pain of my spanked bottom made the pleasure more nuanced and reminded me of my debasement. Alastair made sweet noises of pleasure as he sucked me, mingling with my gasps and moans to provide a scintillating soundtrack.

“Oh…God…Sir…” I moaned louder. “I’m close, Sir. I’m close.”

He changed his pace and went back to the slow, soft teasing, driving me mad as I waited with my hands on the stool for him to give me permission to come.

It seemed to last forever. I walked a tightrope of desire as Alastair brought me to the brink and back a dozen times. I almost started crying again.

He must have noticed my distress, because he told me I could come, then swallowed me down and sucked like his life depended on getting me off right the fuck now.

I came hard and long, with embarrassing noises. When the shudders and gasps subsided, he pulled off, and caught me as I relaxed into a pile of goo and slack muscles.