[T]aking [M]y FWB's PIVirginity | 2016

A few days after our previous encounter, we met up at my place again. My roommates were both awake, but they were kind enough to give us some privacy as we retreated to my room. He set up the VCR and put in Chicago as I packed a bowl and sat back on the pillows. He cuddled up to me, rested his knee on my hip, and we got comfy.

As the Cell Block Tango faded, his hand reached down into my pajama pants and started rubbing me. I lightly scratched his back, then rubbed his strong shoulders. I barely pushed on his neck when his head found my crotch. He pulled back my foreskin and started on my head, sucking vigorously at first. With one hand, he pumped my shaft while sucking. He started to suck more gently, then lowered his mouth down my dick. Slowly, steadily, he took the whole thing in his mouth, his chin resting on my balls for a long, breathtaking moment. Then he came back up and resumed jacking and sucking me.

His one hand stopped pumping me and reached around to fondle my balls. I moaned for him, a little louder when his hand kept reaching backward. He teased my taint, stroking up and down, before finally caressing my asshole with one finger. That was the last push I needed, and I came for a solid fifteen seconds. Enthusiastically, he swallowed it all down, licked up a bit left behind, and cuddled back onto me. I kissed him as Queen Latifah finished up her number, and I took a while to recover for round two.

Now, he had specified that there would be no oral sex on him, and that he didn't feel comfortable letting anyone play with his cock yet, so I took it slow. I stroked his supple hip, tracing the line between his side and his belly, then along the top of his thigh and back up, until he was gyrating his hips up at my hand. Slowly, my hand ventured to the inside of his thigh, then swept across his mound, then back down to tease his outer lips as I trailed my fingertips back up. I never touched his cock, but I did keep threatening to. His breathing quickened as I continued to tease him. Finally, he grabbed my wrist and thrust up onto my fingers, riding them as they drew slow, lingering circles.

His hips kept bucking up at my hand, and each time my hand reached farther back and into him; he was soaking wet for me. As he thrust upward, my middle finger ran its full length on his cock, and reached up inside, then retreated as his hips relaxed back onto the bed. We kept this up a good five minutes before he kissed me deeply, then asked if I had a condom. I got on my knees and made him roll it down my dick before climbing on top of him.

Though he hadn't been fucked by a live dick before, his past partners had taken him with strapons, so he knew how this next part worked. His knees came up to his chest, his hand went to my cock, and his hips swiveled up to take me inside. I thrust slowly, carefully, letting him open up to me as I entered him. Once I bottomed out, he decided he was done with that, bucking up onto my cock from below. We picked up the pace, fucking furiously. He moaned as I picked up his hips and aimed my head at his Gspot. As I kept thrusting, I traced my thumb around his lips and back toward his asshole, pressing my thumb on the wall between his two holes. He gasped, grabbed my hips, and came against my cock.

I slowed down, drawing out of him, until only the head was still inside him, then slowly drew back in. I kept up a slow and shallow thrusting until he came down from his first orgasm, then sped up and thrust harder and faster into him. He gave out a low, long moan, and tensed up against me again, pulling my hips up against him. I enveloped him in my arms, kissed him, then whispered in his ear to flip over.

He stuck his ass in the air, and I reached down to stroke him as his hips ground back at me. In one fluid motion, I pulled him onto my cock and pushed all the way into him. I leaned over, held his chin in one hand, and whispered into his ear, "You're the most fuckable boy I know." I leaned back and grasped his hips, I giving short and shallow thrusts into him, picking up speed as his moaning got louder. I leaned back and used the leverage with his hips to rock against him, fucking faster and faster. My thumb caressed his taint again, and I told him I was close. My hands hooked around his hips as I bucked deep into him, coming for the second time that night.

We both collapsed on the bed, kissed each other softly, and held each other as Roxie and Velma started their last number.