Hustler Got Hustled-All Night Long

I was staying at the No-Tell Motel again, looking for some trouble to get into. And by “trouble,” I mean some poor bastard down on his luck and desperate for cash. After checking into my room, I walked to the gas station next door for some beer and snacks. On my way out of the gas station, I saw a guy loitering outside. The motel was located in a part of town known for sketchy behavior, and he had the vibe of someone either buying/selling drugs, or looking for some ass. He was a 20-something, light-skinned Black guy with a thick afro and a thicc body. I could tell from the prolonged eye contact we made that something about me caught his attention. 

I asked him if he knew where I could buy some weed and his eyes lit up. “Yeah, I got you. Just give me your money, I’ll go get it, and I’ll bring it back to you.” I know I look young, but I know a hustle when I see one. Too many times before, I’ve given my money to someone who disappeared, so I knew better. Instead of calling him on his bullshit, I decided to have some fun.

I told him I had to go back to the room for my cash, and suggested he come with me while I retrieved it. While we walked next door, he asked me if I was looking for some “company.” I lied and told him no, but my dick was growing in my shorts, excited by the mere thought of using his boy pussy like a toy. 

When we got back to my room, I stalled, pretending to be looking for my money in my suitcase. I had my back to him, and when I turned back around, he’d pulled his limp dick out of his shorts. Even soft, it had a fat fleshy head, and looked like it would be a decent-sized grower. But I really wasn’t that interested in dicks. At least, not his. 

“I’m trying to get to know you better. I’ll go get the weed and come back, and we can get down.” I almost laughed at him, thinking, “Oh, I’m going to have some fun alright. Not sure how a good a time you’re going to have though…”

I stepped forward and gently took his dickhead in my hand. He jumped a little, and it was a huge “tell.” He might be bold enough to whip his dick out, but he clearly wasn’t really into this. Even better.

“How about this,” I said. “Why don’t I just give you $20, and you suck my dick?”

I guess he figured I’d be sucking his dick, and his eyes got big as he contemplated being on his knees in front of me. “Uhhh...you don’t want any weed? It would be even hotter if we had some weed. Then we could really get to know each other.”

I have to admit: I admired his focus on the goal, but I was just as focused. And my focus wasn’t on weed, it was on his round caramel-colored ass. We went back and forth a few times, him trying to talk me into giving him some money for weed, and me trying to give him money for sex. Finally, he realized he wasn’t going to be able to hustle me, and he made his move. He moved toward the door, saying he had to go. Just before he got to the door, he grabbed my laptop and tried to run out. He got the door to the room open, but I caught up with him before he could make it across the threshold. Instead of grabbing at him, I pushed him-hard. I caught him square in the middle of his back, propelling him into the opening door. His forehead hit the edge of the door, and he slumped to the floor, unconscious. I pulled him further into the room and shut the door. I took the sash from my robe and tied his wrists tightly together, then dragged him over to the bed and dropped him onto it. 

I pulled his shorts off of him, delighting in the sight of his furry ass. He was still out cold, so I had full use of his body. He was laying on his stomach, and I tilted his head to the side for access to his full lips. I slid my hard dick into his slack mouth, reveling in the feeling of warmth. I casually fucked his face for a few minutes before he woke up. 

“Mmmf! Mmmmmmffff!” his muffled cries rang in my ears, only serving to arouse me more. In an effort to get me to stop, he bit my dick, and I pulled it from his mouth and slapped him harshly. “That’s okay, faggot. You have another hole that doesn’t have any teeth. That one should feel better…”

The realization dawned in his eyes as he came to terms with the fact that I was about to fuck him like a $5 whore. I grabbed a bottle of lube from my suitcase and poured a liberal amount onto the crack of his ass. I clapped his cheeks together: partly to spread the lube into his ass and partly to watch his ass meat jiggle. He started to yell, so I picked his underwear up off the bed and shoved them in his mouth.

I worked the lube into his musky ass, then abruptly stuck a finger in. The walls of his ass gripped my finger mightily. I worked his asshole, adding another finger as I felt his sphincter loosening. I slid a third finger into his boy pussy, and his cries became more urgent. I was tempted to add a fourth finger but my dick was jealous and throbbing, eager for the feel of his tight asshole. Pulling my fingers from his ass, I straddled him and positioned myself for a fuck that neither one of us would soon forget.

“You ever been fucked like a prison faggot, boy?” He writhed and thrashed, but the sash around his wrists held fast. He tried to clench his ass cheeks, but the amount of lube I’d poured on him made that a wasted effort. The head of my dick slid past his clenched ass and pushed against his puckered asshole. We both gasped as my dick breached his asshole: him from the pain of penetration, me from the grip his brown-eye had on my cock.

I started off slow and steady, driving the full length of my erection into his ass before pulling it nearly out. He continued to struggle, but I could feel his asshole relaxing more and more. “Yeah, that pussy’s blooming like a rose. That’s it, open up and let Daddy’s dick in that sweet cunt.”

He managed to spit his underwear out of his mouth and started talking shit to me. It didn't bother me at all: I like my boys a little feisty. “Fuck you man! I ain’t no fucking faggot! You’re the faggot!!”

“You sure about that?” I taunted. “You’re the one who had my dick in his mouth earlier, now you’re taking it up the ass like a champ. I bet this isn’t your first time, is it, boy? I bet you’ve turned some tricks in your time. Yeah, I can tell: this pussy has had some cocks before.”

He started to say something else, but I was bored with the back and forth. I shoved his drawers back into his mouth, and grabbed a handful of his thick afro. My hips moved faster as I picked up the pace. As I approached climax, I leaned close to his ear and hissed, “I was going to just get some head and send you on your way. But with a pussy this sweet, I think I’ll hold on to you for a while. I’m gonna fuck you all night--every time my dick gets hard, it’s going in your ass. By the time you leave this room, you’re going to have my cum dripping out of your cunt. Take that fucking load, you whore!” With that, my dick twitched deep in his ass and fired off five shots of hot jizz. He trembled involuntarily as I pulled my cock out of his warm hole. I gently caressed his ass, then slapped it lightly, saying, “You’d better get some rest while you can, whore. You’re in for a long, rough night.” 

Before daybreak, I’d left three loads in his ass and two down his throat. True to my word, when he walked (bow-legged) out of the room just before sunrise, I could see a dark damp spot on the back of his shorts. It might have been my imagination, but I swear it seemed to get bigger with each wide-legged step he took across the parking lot.