There he was again. A lot of the time when I walk the few blocks to get my weekend morning espresso, he hits me up. My neighborhood is full of panhandlers.
"Dooya havuh quarter?" Since I'd go broke if I handed out money every time I was asked, and since I less frequently have cash on hand nowadays, I've always said no. He's always, dejectedly but without sarcasm, said thank you and kept walking. Talk about old school...just a quarter...most ask for a dollar or more. This time all I had was cash. I had left my wallet at home.
I thought about it hard for several seconds. He was a tall but pretty skinny, redheaded Viking, later 20s, grubby, looked like he's seen the inside of a prison, and had a slow, west coast speech and demeanor...I'd bet on Portland or Seattle.
Summoning my courage, I inhaled then exhaled through my nose, "Yeah, I've got ten bucks for you, but what's in it for me?"
"Wut?"
"I've got ten bucks for you if you let me suck your dick." Damn, I was nervous...he easily could have kicked my ass...my stomach was in knots...and I was feeling ill.
He slowly looked from side to side...likely checking to see if anyone was around. There were plenty of people walking about, but none close enough to hear our conversation.
"Wut thuh fuck?"
I reached into my pocket. Actually I had twenty-one bucks and change. "Dude, this is yours if you cum in my mouth in that alley over there."
His eyes got some fire in them...his posture got rigid...and he tilted his head back as if to look me up and down. Ok, I thought this is where I was gonna get punched in the face. The punch never came...nor did he look me up and down...he just stared at me with a pissed off look on his face.
I was trembling. "Seriously dude, follow me over there and this cash and my mouth are yours." My voice was quavering...I was having second thoughts...but I was also getting a boner. I started walking to the alley.
I turned to my left into the alley without ever looking back. It was a short dead end alley that serviced two commercial buildings on both sides. There were no windows...just a few back doors and a couple of dumpsters. It was lightly snowing and there were a couple inches on the ground. The dumpsters were on the left up against the building behind them. I walked past the first one...went behind it...stood with my back against the wall...and waited. He would have been able to see my head over the dumpster. I looked to the right to see if he was coming...and I waited...my mouth got dry as hell...and I was shaking. This scene was over the top...did I really want to suck his dick this bad? Yeah. I did.
He rounded the corner...saw me...and my head sprang forward. Then he walked up to me. Without a word I dropped to my knees and looked up a him. He looked around again. If anyone would have passed, all they would have seen was his head above the dumpster...and probably would have thought he was just taking a piss. He just stood there...towering all tall, redheaded, and Viking-like in front of me. His hands were balled into fists and he looked mad. He just stood there looking down at me. I figured he wasn't going to do anything but stand there, so I reached up and opened his jeans. He didn't say a word and he didn't stop me. I tugged his jeans down a little...it wasn't difficult as he was pretty thin...and I pulled his boxers down just so his dick and nuts were hanging out over them.
I didn't take much time checking him out...but I his cut dick was pale and veiny...his nuts were furry as was his not too wild bush...the color matched the hair on his head. I opened and sucked his cock into my mouth. He wasn't very clean...but it was within acceptable limits...barely. He was soft but slowly began to bone up as I continued to suck. Damn, my mouth was getting fuller and fuller. I pulled off to get a look. His dick wasn't very big...I mean it wasn't very long...which surprised me due my assumptions of tall, skinny, redheaded Vikings...as if I had any before that day...but damn that son of a bitch was fat. That was a nice surprise.
I went back down on him...but kept my eyes open...because who knows what could have happened...he just continued to stand there motionless...and his fists were still balled. It was almost as if he wasn't gonna enjoy this no matter what...he was just gonna get paid twenty-one by a cocksucker in an alley. But he had to have been enjoying it...anyone with a cock that hard and fat just had to have been. I pulled off to look at it again...yup...it was probably one of the fattest cocks I've had in my mouth...and had a hard, upward curve to it. The shaft was still pale and veiny...but his spit shiny head was crimson and as angry looking as he was.
I went back down on him again...and took him to the root...but he wasn't long enough to take in my throat...although my mouth sure was opened wide. I had my nose in his bush...but had to pull back...he was just a little too musky...although I'll admit it was almost like taking a hit of poppers. I kept sucking up and down on his dick...and I saw his hands move...startled I looked up. He placed his hands against the wall above his head...and he began to pump my mouth. Yeah...this son of a bitch was enjoying it. I held still and let him pump my mouth. He wasn't rough...but rhythmic...almost methodical. He continued to pump for about another minute...and then his belly began to quiver...it began to buck. I looked up and his arms were still forward and above his head. I couldn't see them but I assumed his palms were still pressed against the wall...his head was thrown back...and although I couldn't see them either...I'd imagine his eyes were closed.
He stopped his pumping but his belly was contracting and contracting...and then it happened...he shot and shot and shot a warm, salty load in my mouth. I swallowed...got up...stuck the cash in his hand...and got the fuck out of there.