Underwear Painting

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I smiled as I entered Leo’s apartment for the second time. It was only a couple of days after our last meeting, though, unfortunately, his husband would be unable to join us once again. Lucky for him though, I had plans to make up for that.

After a hug and a butt grab I took a seat and tossed a pillow onto the floor, between my legs. “Kneel,” I ordered, pointing.

“Yes, daddy!” Leo chirped in response, quickly dropping to his knees.

I stroked his head as we chatted and caught up. Soon I begin removing my clothing, again handing them over to him to fold and put away, until I was down to only a jockstrap. Once Leo was back on his knees, I pulled him by the back of the head towards my crotch, his mouth automatically opening to take in as much of my jock-clad cock as he could.

I lazily ran my fingers through his hair as he mouthed at my cock, admiring the level of effort Leo was putting into even this simple task. What a good boy.

“I really wish Stu would have been able to make it,” I mused, referring to Leo’s absent husband. “Gonna have to do something to entice him, I think.”

Leo looked up at me with questioning eyes but said nothing, not wanting his prize to leave his mouth for even a moment.

“Don’t worry pup, I’ve got a plan,” I chuckled and reassured him with a pat. “You just focus on keeping daddy’s cock hard.” And with that I pulled my jock to the side, allowing my hard cock to spring out. Leo swallowed it down to the root without so much as a word, gagging but refusing to let go.

“Mmmmm, good puppy,” I encouraged.

I allowed Leo control at first, spreading my legs wide and allowing him to move his pillow closer. He placed his hands on my thighs as he began bobbing his head up and down the length of my shaft. My voice low, I groaned as I felt him take me all the way in and swallow, thrusting my hips up almost involuntarily.

I leaned back in my chair, eyes closed, focusing on the feeling of the warm mouth enveloping me. I was in no rush, it would be several hours before I needed to be anywhere. Only thing that could make this better would be a second pup working his mouth on my nuts and ass. I made a mental note to arrange that sometime soon.

Once I was thoroughly relaxed I decided it was time to start taking control of the situation. With both hands, I gripped onto the back of Leo’s head. As he continued to swallow my cock, I added pressure to the back, with a little more added oh each push downwards and pull upwards. Relaxing his neck, Leo focused on swallowing my dick without gagging, and relented direction of his movements to me.

Before long I was rapidly fucking Leo’s face down onto my cock. I haven’t moved at all from where I’m sitting, though Leo had moved even closer out of necessity. I relentlessly forced Leo’s mouth to the base of my cock before pulling it up almost to the tip, only to slam it back down immediately. His face was a blur of movement, but from what I could make out he was a spit covered mess. Sounds escape his throat with every expulsion of my length, forming a chorus of gags, sputters, and groans that is music to my ears.

I pulled Leo from my lap entirely and examine his face - sloppy and covered in his own spit and throat slime. His eyes were hazy and unfocused, looking only towards the towering cock that was just plundering his gullet. He weakly attempted to pull his head from my grasp, wanting my cock to resume stretching his throat.

I leaned over and kissed him roughly, all teeth and tongue. Leo melted instantly and only whimpered in response. Such a good boy for me. Once I’ve had my fill, I released him and allowed him to feast some more.

For my next move, I stood, Leo’s mouth and body moving with me until he was sitting up on his knees. His nose is pressed into my pubic hair, and I held him down until I felt him struggling a little before I allow him to breath. Then I gripped him solidly by the head, held him in place, and snapped my hips forward.

Time to REALLY fuck this pup’s face.

Leo’s throat was already opened up, so I felt no resistance as I began pounding his face. With both his hands gripped onto my thighs to steady himself, Leo could only focus on keeping his gag reflex suppressed as I once again stretched his throat to its limit. Just a steady rhythm of “gluk gluk gluk” as I used his mouth.

Looking down I could only see the blur of my crotch meeting his face, over and over and over. Not even stopping so that he could catch his breath, every other minute or so Leo began involuntarily trying to expel me from his mouth. The spasms of his throat felt amazing around my dick. Spit and drool steadily poured from his mouth and onto his stomach and thighs. It took all of his strength not to fight me and let me take what I want.

It almost made me feel bad about what happened next.

As I approached my orgasm, I looked for my folded clothing. Reaching over, I removed an old pair of boxer briefs from my bag, and placed it on the ottoman next to us. With one hand still on his head, I continued to fuck his face and throat with all my might. Then once I reached my limit, I pulled all the way out, grabbed my spit-slick cock, and aimed for the boxer briefs.

I heard a pained “No!” from Leo as I painted the boxers with my load. 5 or 6 streaks of cum, having been worked up for nearly an hour, coated the underwear thoroughly. I shook off any remaining droplets from my cock head before I used a corner of the boxers to dry myself.

I turned back towards Leo, both of us catching our breaths for vastly different reasons. I sat back down and had him move between my legs, head on my lap. I stroked his hair as I spoke to him.

“I know you wanted that load, pup. But that,” I said, pointing to the defiled boxer briefs, “is a gift for Stu.”

Leo let out a whine, but I shushed him before he could say more.

“No. You’ve gotten my cock twice now, you can spare some of my cum for your husband. Now, be a good pup and clean me off,” I guided his head back towards my cock.

We sat there a while longer before I got dressed. Before I left, I gave Leo another kiss, and told him that I expected to hear from Stu about what he thought of the present. He had better not try eating any of my load himself. With a pout, he agreed, and I took my leave.

I sure hope my boys appreciate the work I put in for them.


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