Dom's Little Black Book - Underwear Painting (Patreon)

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, I had plans to make up for that. After a nice long hug and a butt grab, I took a seat in the same chair I sat in last time, and tossed a pillow onto the floor, between my legs.

“Kneel,” I ordered, pointing.

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

I stroked his head as we chatted and caught up, letting him rest his head against my thigh. Not long after, I began removing my clothing, once again handing each piece over to Leo, until I was down to only my jockstrap. Leo stared at me as he folded and put each piece away, already drooling at the sight.

Once he was finished and back on his knees, I grabbed him by the head and pulled 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 dick 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. I groaned low 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. The 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. I gripped the back of Leo’s head with both hands as he continued to swallow my cock, pulling him down with a little pressure. Each time he would take me in, I would add just a little bit more, pushing him to move faster and faster. Relaxing his neck, Leo focused on taking my dick without gagging, and handed the direction of his movements over to me.

Before long, I was rapidly fucking Leo’s face onto my cock. I haven’t moved at all from where I’m sitting, though Leo has 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 escaped his throat with every expulsion of my length, forming a chorus of gags, sputters, and groans that was music to my ears.

I pulled Leo off of my lap entirely and examined 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’d had my fill, I released him and allowed him to feast on my dick some more. He moaned as I stretched his lips once again.

For my next move, I stood, Leo’s mouth and body moving with me until he was sitting up on his knees. His nose was pressed into my pubic hair, and I held him down until I felt him struggling a little before allowing 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 away. With both his hands gripped onto my thighs to steady himself, Leo could only focus on keeping his gag reflex suppressed as I stretched his throat to its limit. A steady rhythm of “gluk gluk gluk” filled the room 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 peak, I pulled out all of the way, took my spit-slick cock in hand, and aimed for the boxer briefs.

Leo shouts out a pained “No!” as I painted the boxers with my load. After being worked up for nearly an hour, I coated the underwear with six full shots of my cum. When I was finally finished, 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.

Suckling my head and shaft clean, we sat there a while longer before I got dressed. Before leaving, 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.

My boys better appreciate all the the work I put in for them.