Drop and Give Me 50

Chapter 22: The Box

We finished breakfast, cleared the table, and washed the dishes. It was all just normal stuff. What you do in the morning. But it felt very “couple”ish. Not in a bad way. But in a “is-this-really-happening” sort of way. And with a guy. A guy I knew. A guy I had fucked. A guy who had fucked me. A guy who knew I liked it, and he liked it too. I was relieved to come clean about Dr. Grant and about my condition. The honesty and the sharing were evidence of a deepening trust between us. My thoughts were going way down the rabbit hole, and Brent snapped me out of it.

Brent: (Yelling from across the house) Found it!

Me: Not another Grumpy bomb! NOOOOOOOO.

Brent: No silly. The box.

Me: The what?

Brent: The box. From the video. It wasn’t hard to find. It was in plain sight in the corner of the closet.

Me: Oh dear god. What have we here?

Brent: Wait, wait. Put that back. Let me take a picture.

Me: Yeah. I think they expected the DVDs to be out of order, but I’m not sure they were expecting us to dig through this.

Brent went to get his phone and returned to document the contents of the box before we started unloading it.

Me: You need to remember to erase those pictures before we leave. Can you imagine if someone was swiping through your pictures and found this? Or the porn stash?

Brent: I never leave a trail.

Me: Good man!

Brent: Remember how reluctant I was about getting fucked?

Me: Well, you didn’t protest much last night.

Brent: True. I was a bit shocked, but I really liked it.

Me: Maybe you are a big bottom.

Brent: Two days ago, I would have taken that as an insult. After yesterday, I will take it as an extreme compliment.

Me: You do have the cutest ass on the planet. And my dick was loving every second of it out by the pool.

Brent: Do you think you could use some of these on me. I mean, you would have to go really slow. But I want to try. I just want to see what it feels like. Isn’t that the whole point of the weekend, to figure out what we like and what we don’t?

Me: I will consider it my supreme mission to shove as much stuff up your ass as possible until all curiosity is fully satisfied.

Brent: Well, let’s not get too crazy. But this one seems to be the smallest one in the box. Can we start here?

Me: Sure.

I found the black rubber sheet Dr. Grant had used in the video. I propped Brent’s ass up with a pillow, unfolded the sheet, and placed it under Brent’s ass just as was done to Darren. Brent’s ass was perfect. I started licking it as if trying to glue all the hairs down. Without the fear of the sounds drifting to the neighbor’s backyard, Brent moaned with unrestrained pleasure. I warmed up his ass with my index finger and slowly tickled his prostate. His eyes were shut, and he was drifting into a sexual trance. I advanced to two, and then three fingers. His ass was opening up nicely.

When I thought he was ready, I slathered the dildo with copious amounts of lube.

Me: Ready?

Without even opening his eyes, he just quickly nodded. I placed a small amount of pressure up against his hole with the tip of the dildo. The resistance was greater than I was expecting.

Me: Relax. Deep breath. I’m going to push through.

I put some muscle into it. And after a couple of unsuccessful thrusts, it broke through rather abruptly.

Brent: FUCK!!!

Me: You OK?

Brent: Yeah, just hold it still.

Me: This might have been the smallest one, but it’s still pretty big.

Brent: OK. OK. Slow.

I pumped a few more squirts of lube on the dildo for good measure. Very carefully, I twisted and pressed until it was slowly going in. Brent exhaled deeply but never gave an indication to stop. It felt like it took forever but it finally bottomed out at the ball-shaped base. I held the palm of my right hand on over the suction cup and provided just enough resistance to keep the dildo from slipping out. I leaned over and starting sucking Brent’s dick which was dripping with pre-cum. I tugged at his low-hanging balls with my left. The fullness of his ass, the pressure on his balls, and the suction on his dick was giving him a triple pleasure.

Brent: Go easy. But can you fuck me with that thing?

Me: Sure. Just let me know if I’m going too fast.

Brent raised his arms and put them behind his head as if to say, “I’m all yours and turning over control.” Maybe we had learned more from that “10” video than we thought. His two-day beard and his bushy pits perfectly matched his furry ass. I stood up, let go of his balls, and used both hands to precisely guide the dildo with smooth stokes in and out of his ass. The motion elicited tense but pleasurable grunts and breathing from Brent, and after a while, it was clear he was mastering his craft. He stopped clinching down and finally relaxed. The pressure required was noticeably lessened. I took this as a sign he was ready for a more aggressive fuck. I didn’t speed up so much as I just started slamming it in more aggressively followed by a slow retraction. With each thrust, he let out a pained but happy “ohh.” When I would slow the pace, I could see a smile emerge on his face. Much like the face fuck he put me through last night, he was finding his own endurance sport. Instead of his throat, it was his ass. That beautiful harry ass was born to be a power bottom. He opened his eyes as if to communicate, “Look ma. No hands!”

I decided it was time to put his ass to a real test. I turned up the speed and started punching his hole with that dildo as if I were throwing a fastball. There was no mercy. It was slamming in and out of him at rapid speed. I was wrecking his hole. His screams were deafening. His head was thrashing side to side. His breathing was deep and rapid. His body started to convulse in rhythm with the fuck. I didn’t let up. I pressed on with abandon waiting for a sign to slow up or stop that never came.

Brent lifted his head up and let out a blood-curdling scream just at the moment his dick shot wad after wad of cum all over his face with some of it sailing directly in his wide-open mouth. I immediately stopped the fuck waiting to be sure he wasn’t going to have a heart attack. As he caught his breath, I slowly pulled the dildo out of his ass which drooled with a small river of pink lube. I couldn’t kiss him because he was still breathing so heavily, and I didn’t want to lay on top of him because his chest was still heaving. But I straddled him and mirrored his smile with one of my own. He was catatonic with pleasure, unable to do anything but gulp oxygen to recovered from the adventure. I just enjoyed my front row seat at the show. And what a show it was.

Wordlessly, we managed to get up off the bed and make our way to the shower. I turned on the water. Brent sat on the floor as if weak in the knees. I joined him and wrapped my body around him from behind hugging him as the water poured over us. I dared not say it, but at that moment, I knew I was in love.