Sugar Daddy (Patreon)

I've been posting tumblr archive stories and ones based on inspiration photos for the past few weeks, but this one has a different source material. VIP members, check out the short video on the Discord server that I filmed to go with this story.

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“You’ve got to be kidding me? Mason, I thought you ended things with him.”

“I did… until I didn’t.”

“This is too much- you know it is. You have to end things. How is the money good enough to-”

“I will give you $5000.”

I had my hand on my friend’s door, ready to go, when that stopped me in my tracks.

“You’re willing to go to your bank and pay me just to get me to make a video for him?”

“No. That wouldn’t come from my bank- he’s paying that today for just this video.”

“I need details. Now”

As I dropped my jacket and headed over to my friend’s couch, he filled up two glasses of wine almost to the brim before joining me. As the liquid disappeared in our glasses, I found out every detail about my best friend’s sugar daddy. One of Mason’s coworkers had connected him with the mystery man. He’d been on the receiving end of his adoration for the past few months, but he was getting married.

“He told me that he’d saved up enough for his dream wedding and honeymoon, and he had to get out of there. I told him that I would do something similar, but I’ve gotten hooked.”

“How much have you made?”

“In the past two weeks? I haven’t added it all up yet.”

“How much Mason?”

“Over 7,000 dollars.” That number had me chug the rest of my wine. “And this video will net me five more, but it will open up another realm of possibilities.”

“How can someone send this much money to a random man without seeing his cock first?”

“I’ve always had a dildo in my boxers for everything, but he says today is the day. I either send the video, or I’m cut off.”

“What’s in it for me?”

“Half. I will give you half of every video you film.”

“Wine.”

He didn’t hesitate at all before filling me up. By the time it was empty again, we’d worked out a plan. Mason and I had similar body types, but there was one difference.

We’d been college roommates, and when we’d found out that we were both gay, we gave ourselves one night to hook up with each other to test out the waters. We luckily realized we were better as friends, but that was after seeing each other both completely naked and exposed. That’s when I realized that his confidence didn’t come from what was between his legs…

“Okay, let’s do this.”

Mason went to grab his camera from his room as I began to pull off layers of clothing. I’d commented earlier that his apartment seemed warmer than normal, and now I knew why- he’d prepared it for me to be almost naked.

Stepping out of his room, he was holding up one of his shirts, a pair of white boxers, and a camera.

“You ready?”

“Just set the camera up so I can get this done with.”

He just nodded- he knew our friendship was about to go further than it ever had before. Even further than that night in our dorm room over a decade ago. As he set up the camera on the tripod, I walked behind him and changed into the outfit that felt warm. I realized now that he’d probably been wearing it earlier when he filmed his last video for his sugar daddy. Pushing that thought out of my head, I walked over to the wall in front of his camera and leaned against it, already starting to get hard a bit from the sheer eroticism of what was about to happen.

“Okay, so you’ll press record and then walk away while I beat off?”

Looking up at me from the camera, Mason just shook his head.

“Ian, I have to be here while you film. He likes it when I’m verbal so I’m going to be talking and making noise as you, uh, jerk off.”

I’d already resigned myself to the fact that my best friend was about to see and edit a video of me jerking off, but this felt way more intimate. This was too much.

“Five. Thousand. Dollars.”

Unfortunately for me, I was just as cheap of a whore as Mason was. So, I just nodded my head and got into action. As the red light turned on, I began rubbing my chest and palming my cock through the borrowed boxer shorts. He was standing about three feet behind the camera, the same distance that I was in front of it. As my cock, now fully hard, pressed against the thin material encasing it, Mason started moaning behind the camera. I knew that he was just putting it on, but it started working me up, and I had to close my eyes to block him out. Closing my eyes also prevented me from seeing his face once I pulled those boxers down to the ground.

I was standing there, half-naked for a man that I hadn’t and wouldn’t ever meet. I was jerking off my thick cock as my best friend started talking dirty as if he were me.

“Yeah, you like that, daddy? You like it when I pump my cock for you? You like finally getting to see the man that you’ve been turning on all week?”

This was a side of him that I’d never seen before, and I peeked one eye open to see that he was staring right at my dick. I rationalized that he was just making sure that he knew what to comment on as he filmed, but as he licked his lips, I wondered if maybe there was more to this. Maybe he wasn’t just faking for the camera…

“You like knowing that I’m yours, Daddy? I’m your little plaything.”

As my cheeks reddened, I tried to tell me myself that it was from the heat. Yeah, that was it. It definitely wasn’t that this dirty talk, which wasn’t even intended for me, was working. I’d been embarrassed about this situation since it started- hell, since he first told me once I walked in! Now though… now it seemed different. The energy in the room had changed.

Mason hadn’t even looked up to notice whether I was seeing him paw at his own crotch- he was still glued to my dick as it glided back in forth in my hand.

“What’s that daddy? You want me to slap my cock for you?”

We finally made eye contact at that comment, and he just shrugged his shoulders, one hand still over his bulge which was bigger than it had been before.

“I know you like that, so let me slap my cock for you.”

I tried to shake my head, but he just held up his five fingers which reminded me why I was doing this. Pulling my hand away from my cock, I reached down with the other and swatted at my cock. I was too hard for this, and pain radiated through my chest. I did it one more time, and again, I was banishing another thought from my head as I contemplated whether I liked that or not.

“That’s all I can do right now daddy, or else I’ll blow my load too early. I’m still saving that for later- it will all be worth it.”

As the red light blinked off, I immediately reached down to pull up my shorts before remembering that my clothes were across the room. Heading over to them, I pulled on my jeans before I could even soften up, stuffing my dick painfully into them as I pulled up the zipper.

“We’ll talk later, right?”

Mason’s voice was back to normal now, the breathy lust already retreating. I tried to say something, but I couldn’t. I just walked out the door still wearing his shirt, and I pulled my jacket over it outside. It wasn’t until I was already driving down the road back to my place that I let myself really think about what I’d just done. The experience, the money… and the feelings about Mason that still had my cock hard even though I was miles away from him.