Chapter 21 #2

Some of my tension eased. “You sure know how to sweet-talk a guy.”

“Only you,” he said, pressing another kiss to my lips.

I let him guide me to the bed, his hands gentle as he positioned me on my back.

“Spread your legs a bit,” he instructed, his voice low and soothing.

I complied, but a nervous laugh escaped me as he reached for the nightstand drawer.

Harley took out a bottle of lube, flipping the cap open with practiced ease. He squeezed a generous amount onto his fingers, way more than I expected.

“Whoa there,” I said, propping myself up on my elbows. “That looks like enough to slide a whale through a keyhole.”

He rolled his eyes, but his smile remained patient. “There’s no such thing as too much lube your first time. The key to making this good for you is proper preparation.”

“So I’ve heard,” I muttered, falling back against the pillows. “But considering your dick is basically the Titanic, and I’m an iceberg that’s never been hit before, maybe you’re right and we need the entire bottle.”

Harley laughed, warming the lube between his fingers. “Relax. My dick won’t sink you.”

“That’s what the captain of the ship said right before it sank,” I retorted, but my joke fell flat as Harley’s slick fingers teased my hole.

“We’re taking this slow so you can relax.”

I tensed as his slick finger circled my entrance.

“Breathe. I promise I won’t do anything you’re not ready for.”

I took a deep breath, forcing myself to relax. “Don’t worry. I’m okay.”

He maintained the gentle pressure without pushing in. “Tell me if anything hurts or feels uncomfortable.”

His finger continued its circular motion, raising chills on my skin. His other hand returned to my cock, creating a rhythm that made it easier to focus on the sensations rather than my nerves.

Harley maintained eye contact as he eased in a finger. The pressure was foreign but not painful.

“You’re doing great.” His voice was thick with something that sounded like reverence. “How does it feel?”

“Like I’m getting a prostate exam.”

He snorted in amusement. “Sexy.”

“At least it doesn’t hurt, though.”

“Good.” He paused to let me adjust. “You’re doing amazing, Ryker.”

I snorted, masking my vulnerability with humor. “For what? Lying here while you do all the work? The bar for ‘amazing’ is so low it must be in Hell.”

“No, letting someone in like this takes courage,” he replied, his gaze soft with affection.

“Yeah, well, your finger isn’t exactly the part I’m worried about.”

His laughter sounded warm and rich. “We’ll get there. One step at a time.”

The strange pressure gave way to something more interesting. Not quite pleasure yet, but a sensation that made me curious for more.

“How’s this?” he asked, curling his finger.

It sent an unexpected jolt through me, making my hips buck. “Holy shit! What was that?”

“That would be your prostate. I take it you approve?”

“That’s so much sexier than when the doctor does it in the movies.” All my earlier nervousness forgotten, I demanded, “Do it again.”

He obliged, repeating the motion with more deliberate pressure this time.

My cock twitched in his hand, drawing a moan from deep in my chest. “Okay, I’m starting to get it now.”

“Get what?” Harley asked.

“Why people do this.”

He continued to stroke that spot with careful precision. The dual sensations of his hand on my cock and his finger inside me were creating a building pressure that felt unlike anything I’d experienced before.

“I’m adding another finger. Tell me if it’s too much.”

I nodded again, bracing myself for discomfort that didn’t come. The additional stretch was noticeable but not painful, especially with the obscene amount of lube he’d used. The pressure increased, but so did the pleasure, as he found that spot again with more accuracy.

“You’re doing so well, Ryker.”

“Again with the praise. All I’m doing is lying here. I’m not performing brain surgery or climbing Mount Everest.”

“Don’t minimize this. It’s a big deal, Ryker.”

I had to look away from his sincere gaze. “If you say so.”

“I do say so.” He kissed my hip bone. “And I’m proud of you.”

“You have to stop,” I groaned, covering my face with my arm. “You’re making this weird.”

“Weirder than your Titanic analogy?” He scissored his fingers as a test.

My arm fell away from my face. “Point taken.”

Harley’s movements were methodical and patient. “How are you feeling?”

“Fine so far.”

He poured more lube with his free hand. “Ready for more?”

“As ready as I can be.” I watched as he dispensed more of the slick substance. “At this rate, we should buy stock in lube companies.”

The addition of a third finger brought a more noticeable stretch with a slight burn. He stilled when I tensed, his other hand still stroking my cock to distract me.

“Breathe through it,” he instructed. “It’ll pass soon.” True to his word, the discomfort faded, replaced by growing used to the fullness.

“Better?”

I shifted my hips to test. “Yeah, it’s okay.”

Harley’s fingers prepared me with a thoroughness that both frustrated and reassured me. Combined with his other hand working my cock, I raced to my peak faster than I expected.

“Harley,” I warned, my voice tight. “If you keep this up, I’m gonna—”

“That’s the idea,” he interrupted with a wicked smile. “I want you to come like this first. It’ll make what comes next easier.”

Before I could protest, he curled his fingers against my prostate while tightening his grip on my cock. The dual assault sent me careening over the edge as I came with a shudder.

Harley worked me through it, his movements gentle but relentless until I was left boneless and panting.

“Holy shit,” I breathed, staring at the ceiling in a daze. “That was wow.”

“And we’re only getting started.” He withdrew his fingers. “How do you feel?”

I took a moment to assess, surprised by the answer I found. “Different, but in a good way.”

The smile that spread across Harley’s face was equal parts tender and triumphant. “That’s what I like to hear. But are you sure about this?” Harley asked as he held up a condom. “We can stop right now if you want.”

“After all that prep work?” I arched an eyebrow at him. “That would be like studying for finals all semester and then sleeping through the exam. I’m not backing out now.”

His lips quirked into a smile as he tore open the foil packet with his teeth. “Just checking.”

I watched, mesmerized, as he rolled the condom over his significant length. The sight flooded me with a mixture of anticipation and nervousness. I couldn’t believe he went for the lube again. “Seriously? More? You could fill an Olympic-sized swimming pool with how much you’ve used.”

“Your ass will thank me later.” He positioned himself between my legs, his expression softening as he looked down at me. “We’re going to take this inch by inch, okay? If it hurts too much at any point, we stop. No questions asked.”

I nodded.

His hands stroked my thighs to comfort me. “I need you to promise me you’ll tell me to stop if that’s what you need. I’ll never forgive myself if I hurt you.”

His sincerity made it impossible to deflect with humor. I tried to sound more confident than I felt. “I promise I’ll tell you.”

“Lift your hips a bit.” He slid a pillow underneath me. “This will make the angle more comfortable.”

I followed his directions, taking a deep breath as he positioned himself. “Okay,” I said, meeting his eyes. “I’m ready.”

Harley moved between my thighs, one hand guiding himself to my entrance. The blunt pressure of his tip penetrating my hole made me forget every word in the English language except “holy” and “fuck.” Despite all the preparation, I couldn’t help tensing as he eased forward with excruciating patience.

My eyes widened at the first glimpse of pressure. “I’m being split in half!”

“Sorry, I’ll stop.”

“Hang on. Give me a second to get used to having my ass spread this wide open. It feels like you’re shoving a watermelon through a cocktail straw.”

He bit his lip, trying not to laugh at my description. “Take your time.”

After some deep breaths, the initial shock subsided, replaced by a fullness that wasn’t unpleasant. “Fuck, how are you this huge? I can’t believe any part of you fits in there.” His girth was so thick I could barely breathe.

He stifled a laugh. “Remember to relax. Tensing up will only make it harder.”

“That’s easy for you to say when you don’t have a massive dick up your ass.” In spite of my protests, I forced my muscles to unclench. The fullness, the stretch, the intimacy of having Harley buried intimately overwhelmed me. “You’re fully in now, right?”

Harley’s lips twitched. “Actually, I’m not even halfway.”

My jaw went slack. “You’re joking!”

“Afraid not,” he replied, sliding in another inch with careful precision.

My hands clutched at the sheets. “How does it keep going? How is that even possible?”

Harley’s expression turned cocky, a smirk playing at his lips. “Believe it, snookums.” He slid in farther, and to my surprise, my body responded by pushing down against him to draw him deeper.

A whimper escaped me that sounded more pleasurable than uncomfortable. “This is absurd,” I groaned. “You’re like the Mary Poppins bag of dicks. It shouldn’t be physically possible to fit that much inside me.”

“I’m almost halfway there.”

“Almost halfway?” I asked, my voice cracking in shock. “You’re telling me there’s more? You’ve got to be kidding me!”

Harley snickered. “Sorry, no jokes. There’s plenty more where that came from.”

“What the fuck? This is like one of those magic scarves that clowns pull out of their sleeves. It keeps coming and coming.”

“We’ll get to the coming.” Harley pushed in another inch.

The stretch intensified, making me hiss through clenched teeth. “Hold up, hold up.” My hands flew to his hips to stop his movement. “Time-out. Give me a minute.”

The humor vanished from his face, replaced by immediate concern. “Do you want me to pull out?”

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