Page 49 of Dates & Mistakes


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“I’ve never done this before.”

“Do you want me to stop?”

He shook his head.

“Do you like it?” I asked.

He nodded.

“Tell me,” I said.

I ran my fingertips gently up and down his length and felt the moist tip wetting the cotton. “You’re leaking already,” I murmured. “And you’re so hard. You’re enjoying this, aren’t you?”

He shut his eyes, nodding.

“Use your words, Leo,” I said.

This time, he shook his head. I let go of him, and his eyes snapped open, mouth wide as if he were about to complain.

“I’m serious,” I said. “I’ll only touch you if you tell me to.”

Hesitation came over his face, then faded away. “Please,” he whispered.

“Please, what?”

“Please…Winnie?”

I chuckled. “I meant, what do you want me to do?”

“Touch me.”

“Where?”

He shook one knee in irritation, but his cheeks turned scarlet. “Please touch my cock.”

“Do you want to take your jocks off?”

He scrambled to push them off so quickly that, in any other circumstances, I would’ve laughed at the cuteness, but now, I was distracted by the sight of him. His cock was so hard, laying almost flat against his lower belly, flushed head pointing at his belly button.

I carefully curled my fist around his length, and Leo made a noise. Despite his shyness, he was extremely responsive. Once I’d stroked off a guy who watched me like I was explaining how to file taxes. Leo’s eyes were wide and captivated like he was witnessing real-life magic.

“C-can you...”

I blinked innocently up at him. “Can I what?”

“Winnie, I hate you.” His cheeks were flushed.

“If you hate me, don’t ask me for favours.”

“It’s not a favour. You’re enjoying this too.”

“How are you so certain?” I tightened my grip. “Are you just that irresistible?”

Leo blushed. “N-no. You…” he gestured at the tent in my pants.

I bit down a smile. “What do you want me to do?”

“A little faster? Please?”