Giorgio (Vigilance 1)

I cried out. It stung so fucking bad. “Hurts. God, that hurts.”

“You’re a good boy. You can take your punishment.”

He brought the belt down on the end of the plug. The force of the slap made it vibrate inside me, pressing against my prostate. I gasped, overtaken by the intensity of the pleasure that pulsed through me. Giorgio slapped my ass again, and I couldn’t tell pain from pleasure. He kept going, bringing the belt down several more times, sometimes on my ass and sometimes on the end of the plug. I writhed, trapped between pain and pleasure. I tried to rub my cock against my bent legs, needing friction so badly. “Please. Please, I need…”

He slapped my ass with the belt harder than he had before. The pain brought tears to my eyes.

“Oh God, I can’t—”

“You can. You want to be good for me, don’t you?”

I did. “Yes. Please I… I can take it.”

“I know you can, baby. Three more and we’re done.” He gave them to me in quick succession. My ass burned, and I could barely breathe by the time he dropped the belt and began working the plug in and out.

“You’re so damn beautiful,” he gasped, his breathing nearly as ragged as mine.

“Th-thank you.”

“You did so good.” He pulled the plug all the way out. “It’s time for you to have my cock now, then I’ll put this back in you and make you come so fucking hard.”

Without the plug I felt empty. My ass ached as Giorgio stripped out of his clothes. When he finally drove into me, it felt so good, so right. No one had ever seemed to fit me like he did.

I wrapped my arms around him and pulled him down to kiss me. I tugged on his nipple rings, and he groaned against my mouth and fucked me with his tongue as he worked his hips, driving into me in rough thrusts.

He gripped my cock, stroking me. I was close. So close. I whimpered when he let go.

“It’s time for more.”

I tensed, worried it would hurt too much. He ran a finger down my shaft, making me shudder. “You’ve got to relax so you can take this. I know you can do it.”

He took hold of the plug and pulled it out almost all the way. When he pushed back in with the plug and his cock, the stretch was unbelievable. It hurt enough to make me cry, but I didn’t want him to stop because it was good too. So good.

“Easy, princess. Just breathe. You can do it. I’ve stretched you out before. You’ve come close to taking my whole hand. I know you can do this.”

“I want to. Please. Don’t stop. I want it.”

“I know, baby.”

He made shallow strokes, slowly pushing more of himself and the dildo into me.

Before long, the pain lessened, and pleasure grew until it was so intense I thought I could die from it.

“Touch yourself,” Giorgio commanded. “I want you to come.”

I wrapped my hand around my cock and worked myself with fast, furious strokes. Every time he pushed into me, his cock and the dildo pressed against my prostate and lit up my entire body. I was so close.

“Giorgio. Fuck. Giorgio, I love you.”

Cum shot from me so forcefully it hit my chin and landed on my chest. I kept working myself until I was spent. Giorgio pulled out his cock and the dildo. When he pushed back in, it was only him inside me.

“Come in me. Please. I need you.”

“I’m here for you,” he said brushing my sweaty hair from my forehead. “I love you, and I’m here to give you everything you need.”

“You are. You do.” He drove into me again and came. I didn’t think I would ever stop loving the feeling of his hot spunk inside me.

When he was done, he kissed me softly. “Are you okay?”

I stared at him, trying to remember how to speak.

“Lane? Tell me you’re all right.”

“I am. That was fucking amazing.”

I winced when he pulled out and pushed my knees up to examine me. He touched my ass so gently. “You’re okay. Lie here, and I’ll clean you.”

I shifted a little, and his cum ran from me, faster than ever with me so stretched out. “Wow, that’s messy.”

“And fucking hot.”

He cleaned us up, then pulled me into his arms.

“I was so mad the day X called me, wanting me to babysit some twenty-one-year-old who had a stalker.

“I bet you were.”

“I told him that wasn’t what Vigilance was about, and he told me the client was his son. He had a feeling there was more to this case than just an over eager ex-boyfriend.”

“I’m still not sure how I feel about him,” I said, “but he has good instincts.”

“And now I know that was the luckiest day of my life.”