Page 53 of Dates & Mistakes


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Slowly, I rubbed my leg against him, and it got to a point where Leo had to stop kissing me just so he could catch his breath, and I would’ve been lying if his ragged exhales didn’t boost my ego.

“Do you want me to suck you off again?” I whispered.

His chest shifted with a sharp inhale, but to my surprise, he didn’t nod. He didn’t say yes, either. Instead, he rolled me over so I was on my back and slid himself on top of me. He was heavy, but not painfully so, and soon, the weight of him disappeared as he held himself up on his hands on either side of my head, knees on either side of my thighs. He rutted against me like an animal in heat, and I was still expecting him to take me on my offer when he lowered his head to kiss me.

And kissed me and kissed me and kissed me, still clumsy, our noses bumping, his tongue sliding against mine. His humping movements were similarly graceless, and as time went on and his breath became heavier, his body became jerky and erratic.

His erection rubbed up against mine, and despite the layers of clothing between us, I felt the electric slide of him as if he were naked. His movements became more and more frantic until his hips suddenly stilled, shoulders shuddering, as he panted into my mouth.

Wetness seeped through his shorts to my own pyjama pants, and my cock stiffened even more than it already had, wanting release more than anything. After the orgasm had finished racking through Leo, he carefully dropped to the side of me, face up, so he wouldn’t stain my bedding with cum. I’d probably have to wash it and my sheets anyway sex.

Leo mumbled something.

“Huh?” I asked.

“I ruined your shorts. I’ll wash them.”

“It’s okay,” I said.

“No,” he said firmly. “I’m washing them.” Suddenly, he covered his face with his hands and let out a long groan.

My stomach seized. Oh god. Was Leo having post-nut regret?

“You let me borrow your clothes, and I came in them,” Leo said, his voice muffled by his hands. “And I came so quickly. I’m like a…a horny teenager.”

“You are a teenager,” I reminded him.

“I’m turning twenty soon,” he said, peeling his hands off his face to give me a look.

“Don’t be embarrassed,” I said. “It was fucking hot.”

“Really?”

Was he genuinely that oblivious to his own appeal? Or was he fishing for compliments again?

“Do you think my boner was stabbing you for the hell of it?” I asked.

Leo reached over and brushed my groin. My lips parted at the sudden unexpectedness, and I realised this was the first time Leo had touched me there. But as soon as the touch came, he snatched his fingers away.

“D-do you want me to…” He didn’t look me in the eye.

“It’s nice of you to offer,” I said, “but it’s okay.” There was no way I would make an unwilling man get me off just because he felt a polite obligation to offer.

“Are you sure?”

I nodded. “Do you want to shower?” It couldn’t be comfortable for him to wear shorts dirtied with drying cum.

“Okay,” he said. “Just a quick one. To wash myself off.” He pushed himself out of bed and grabbed the same towel he’d used last night before disappearing into the bathroom. I opened the blinds, filling the room with daylight. For a Saturday morning, the streets were already busy, with a tram travelling past a nearby street, depositing and picking up crowds of people that, from up here, looked like clusters of ants.

I’d just turned the kettle on when Leo came out, dressed in the same clothes as the day before. His pyjamas were balled in up in a roll he clutched in one hand.

“I don’t have any coffee,” I told him apologetically, “but I have instant matcha lattes and tea if you want it. Help yourself.” I gestured to the plastic hamper I used for my laundry. “You can throw those in there,” I said, referring to the pyjamas.

“I told you I’d wash them,” he said.

“Okay. I’m gonna head in for a shower. I won’t be long.”

For the second time in twelve hours, I killed my boner with cold water. I took my time washing off the remnants of sex and sleep from my body, and I stepped out of the bathroom, wondering what drink Leo had gone with.