My Favorite Whore

One morning, I woke up early and was feeling restless. I drove to the part of town where most of the homeless population hang out, looking for some strange. As I cruised through the parking lot of the local Big Box store, I noticed a guy walk into the alley behind the store. He was in his mid-late 20’s, with overgrown blonde hair and a thick midsection. I pulled behind the store in my car, and could see him at a dumpster, rifling through the bags. I could smell the desperation coming off him from a distance. 

“Find anything interesting?” I called out to him. He gave a shit-eating grin and said he hadn’t. I waved him over to my car and he ambled in my direction. He was friendly as hell, grinning up a storm and calling me “brother.” While he talked, I worked my hard dick out of the leg of my basketball shorts. When he leaned far enough into my open car window to see inside, I held my dick straight up and stroked it for him. He did a double take then let out a low whistle. “Daaaamn, brother! You got a big ole dick, huh?” He glanced around, then grabbed his crotch lewdly. It looked like he had a proper handful in there, too. “Can I see yours?” I asked. He looked around again, then pulled down the waistband of his shorts, showing off his thick dick. There was a halo of sandy brown pubes crowning his thick shaft and a light purple head peeked out from his generous foreskin.  

We were a little out in the open, so I didn’t want to linger there, both of us with our dicks out. Knowing it would push me over the edge, I reached out and grabbed his thick cock. I stroked it with my left hand while I jacked my own dick with my right. In seconds, I was shooting thick ropes of cum onto my shirt. “Damn, that was hot.” he gasped as he tucked his dick back into his shorts. “I’ve fooled around with guys before. You ever got some time, we should hang out…” He winked suggestively as he said “hang out.” He told me his name was David, I promised to keep an eye out for him.

The next time I saw David, he was standing on the median of a busy road holding up a cardboard sign. I had a few extra bucks, so I circled the block and worked up a nice stiff boner. As I approached the intersection where I’d seen him, I rolled down my window and held a few dollars up where he could see it. As he leaned forward to take the money, he spotted my hard dick then looked up at my face and recognized me. “Hey man! I recognize that big dick of yours!” That began something of a ritual: any time I had a few extra dollars, and some extra time, I’d look for him panhandling and flash him. It was the perfect situation for both of us. I got a willing participant in my exhibitionist exploits, and he made a few bucks just for watching me jerk off at the light. 

One weekend I was staying at the No-Tell Motel, and I spotted David walking past my open door. I was only wearing boxers (and was sporting a massive erection), but I ran to the door and called his name just as he was about to turn a corner. He greeted me like an old friend, “Hey man what’s up!” He walked back to me and stepped into my room. “Feels weird not seeing you in your car. Didn’t realize how tall you are!” he joked. I grinned broadly and asked if he was trying to make some money. He shrugged and answered, “Shit, always man. We can do some stuff, but if you want to fuck me, we’re gonna have to go back to my room. The only way I get fucked is while I’m eating my girl’s pussy. Is that cool?” I’d been in threesomes before, so that didn’t phase me. If he needed to eat some pussy in order to be okay giving some up, that was just fine by me. 

He went back to his room to shower and tell his old lady what was up. Meanwhile I went to the ATM to make sure I had enough cash for the night’s adventures. 

Thirty minutes later, I was knocking on his door with a throbbing boner in my pants. David answered the door wearing only a towel, sporting wet hair and smelling of freshly-applied soap. Over his shoulder, I could see his “girl”: a dumpy, middle-aged woman with badly dyed hair. She had the jerkiness and absentminded jaw movements that suggested addiction. She nodded in my direction, seemingly unbothered by the prospect of watching her boyfriend getting fucked. He introduced us, but I didn’t give a shit about her, so I don’t remember what her name was. For now, I’ll call her “Methany.”

Methany watched impassively as he took the towel from around his waist and began to play with his thick dick with his right hand. With his left, he reached out and began massaging my crotch. Eager to get things underway, I unbuckled my belt and opened my pants. My hard dick sprang out and David grasped it roughly, jerking it in rhythm with his own masturbation. While he tugged on my cock, Methany came over to the bed and began undressing. When she was down to her panties and bra, she laid down on the bed. David reached over and grabbed a bottle of lube from a duffel bag sitting on the floor. After pouring some onto his hand and rubbing it into the crack of his ass, he reached back and lubed up my dick. When my dick was sufficiently slick, he lined the tip up with his asshole and guided me into him. At the same time, he leaned forward and began to gently lick Methany’s pussy. With his face buried in her pussy, David moaned as my cock slid fully into his asshole. She writhed with pleasure as David began to rock back and forth to the rhythm of my fucking. Her moans were echoes of David’s as we all began to get into the act of sex. As I pulled my dick almost completely out of David’s anus, his tongue was plumbing the depths of Methany’s cunt. I thrust the full length of my dick into him, and he moaned loudly, which caused Methany to buck her hips and whimper. I started fucking his ass with increasing aggresion, and he started talking into her pussy. “Mmm…baby…your pussy tastes so good…I wish you could feel this dick inside you…he’s so fucking BIG…” Hearing him talking dirty while I fucked him turned me on, and I started moving my hips like a hydraulic pump. In….out….in…out… My dick felt like a machine: just a steel bar, smoothly sliding in and out of his asshole. 

After about ten minutes, I felt his sphincter tighten as he yelled into Methany’s cunt, “Oh fuuuuuck! I’m gonna cum!” David’s asshole gave my dick a velvety squeeze as he shot his load onto the bed. He raised his head from her pussy and gasped, “Holy shit! You made me cum! I ain’t never cum from getting fucked!” He struggled to catch his breath as I continued to plow his anal cavity. The fluttering of his anal muscles pushed me over the edge and I leaned into the fucking. “Don’t cum inside me!” he yelled, just as I felt myself going over the edge. “Fuck you, take my cum, whore!” I responded. With that, I blasted four shots of hot cum into his ass. “Dammit man! I told you not to cum in me!” he spat. “You’ll be alright” I replied. “Not like you’re some shy virgin.”