Five Minute Fuck - In the Alley

A glance, a nod then he smiles back at me.

I walk towards the restroom in back then past it. The backdoor is unlocked as they usually are in places like this. Turning the handle to the wooden door and the steel security door then out to the alley. The mature man in white t-shirt and black jeans emerges from the door a minute later. He walks up to me with that same smile he flashed. I'd guess we are about the same age. I'm in town for a couple days for a business meeting but was hoping to find someone for just tonight.

Against the wall, I press his body. My right hand pulls open the fly on his black jeans. The muscled man flexes his biceps as he feels my hand grip his fat semi-erect cock. It's only then he looks at me and says, "the name is Mike, by the way." I feel him twitch as I wrap fingers about him and pull. Almost immediately, I feel Mike grow in my hand. Leaning in, I push my face to his. My beard, his goatee, our lips - we mash and I take his mouth. Tongue pushes past his lips and I kiss hard. My hand strokes, feeling his shaft grow rigid as I jerk him in the alley.

The pad of my thumb presses his balls then pushes against his dick as I stroke him. My thumb rubbing his frenulum with each stroke and I soon feel his dick drooling over my fingers. This just makes me kiss him harder. I feel his tongue against mine as they roll in his mouth. Exhales through his nose as I pin him to the brick wall and use his dick - for my fun and his pleasure. I can feel him pushing against my hand, jerking himself against my strokes as I kiss. I break the kiss and cradle his head against me with my left hand. His short hair feels good on my hand as he moans into my chest.

Fast now, stroking fast and hard as I pull and push on his dick. He moans out with a surprisingly soft voice as he cums. I stroke him and pump his milk all over his belly as he shoots and drools. When satisfied, my hand smooths his semen all over his smooth belly and groin so it will dry in place. He finally looks up at me, "my place is only a few minutes walk." I take stock of him having just met him in the bar twenty minutes earlier. "I'll put on something pretty ... if you're into that sort of thing." I having a raging hard-on but I'm not getting off in the alley. I tell him to button up and lead the way.

##

We walk a few blocks, mostly in silence other than Mike making small talk, perhaps nervous small talk. Climbing a few stairs to the outside door then the elevator to the third floor. "There's beer in the fridge - help yourself." I look around the clean, sparsely decorated apartment and pull out a beer. When the light down the hall goes out, I look towards the doorway while sucking on the beer. Mike returns wearing white. He has changed into bra, panty and stockings all in white. He looks and smiles, "sometimes my friends call me Cassidy. I hope you don't mind." I take one more swig of beer, sitting the half-empty bottle on the counter and walk over to him.

I put my hands on his waist and kiss him. It's more gentle than the alley, but just as sincere. "I don't mind at all, Cassidy ... you look rather hot just now. And damn, so fucking fit too." His hands press my forearms then slides down to unbuckle and unzip me. My hard cock stands against my neatly trimmed pubes. His right hand takes me and strokes a few times before settling to his knees. I watch and smile, looking down as the handsome man settles in front of me and takes my cock against his lips. His head tilts and he peppers my shaft and balls with little kisses. His left hand feels my balls by rubbing them with his palm. I feel his fingertips pressing my taint as his warm mouth takes my head.

Warm and wet, his lips and tongue paint my mushroom with saliva. His fingers continue to massage my balls and taint as his mouth pleasures. My feet slide open a little wider and Cassidy damn near crawls in between them. The tip of his middle finger presses my anus as he begins to take more of my cock in his mouth. Deeper he goes with each push, I feel his lips pulling on my shaft as his tongue plays on my head. His finger begins to rub little circles on my pucker eliciting a moan from my lips. The pretty man is one skilled cocksucker, I surmise. I feel his lips sliding down my shaft and my head tapping the back of his mouth. His fingertip pressing inside my butthole just as his lips grip my base.

Up and down he begins to suck and stroke me with his mouth. I feel myself beginning to throb in his mouth and know I won't last much longer. I resist the urge to pump, letting this sexy crossdresser do the pleasure of sucking me off. When his finger reaches the second knuckle inside me, I'm oozing precum down his throat. Cassidy pumps his mouth up and down my shaft and presses down around me as he feels it. I cum hard. I grip the back of his head, feeling his closely cropped hair on my palm as I shoot my load. I feel him wanting to lift and I let him. He grabs my cock and paints my next shot all over his mustache and goatee. Creaming his face with my semen as he swallows what I gave him previously.

Finally he stands and uses his fingers to smear my load over his lips before swallowing the residual. He walks over and gets himself a beer before bringing the rest of mine back to me. "How long before you reload, handsome?" His left hand brushes his hip then butt, in case I didn't know what he had in mind.

"I'll need a few ... you know what it's like getting older," saying with a wink. Cassidy greeted the wink with a smile and a soft kiss. I pulled off my shirt and socks to get undressed as we talked casually for a few minutes. By the time the beer was gone, Cassidy takes my hand and walks me down the hallway to his bedroom. The sheets are already turned down and lube is sitting on the bedside table. He shrugs, "just in case ... I was hoping you'd end up here." We kiss a bit and I feel myself rising up once more. This night is turning out so much better than I had hoped when I left my hotel room uptown.

I help Cassidy on to the bed, getting him on his knees and hands after slipping off his white panty. I take a look at his firm ass framed by the stocking suspenders and let out a low whistle. I slap his cheeks ... firmly, but playfully and Cassidy gives me a playful moan. Pulling his cheeks apart, I lean in and kiss his pucker to feel him give me a wiggle. I tongue him while reaching between his legs to play with his dick. My tongue probes and Cassidy groans in response. I rub some lube on my hands to warm it a little then press it to his anus and smear it over my head. I'm nearly hard but feeling way past ready to fuck this prime piece of man-ass.

I slide between his stockinged legs and press myself against him. I hold my cock and tap his ass a couple times playfully before pressing my head to him. Cassidy lifts his head and looks back at me. I give a grunt and a push and feel my head pop inside him. I push again and Cassidy groans to not stop there. My hands take hold of his hips and I push. I begin to push and pull, feeling his tight ring gripping my shaft as I move. In and out of this tight, sexy ass I begin to move. I scoot a little closer on my knees and find myself buried in his butt. Cassidy's head jerks upwards at the sensation then drops between his shoulders. I fuck Cassidy. I feel his tight ring pulling on my shaft. The second time always takes longer and I enjoy the sensation of his asshole.

Rocking and fucking we go for the next few minutes. I talk dirty to him, telling him how sexy he looks dressed like he is. I tell him how tight his hole is even though I know he's a slut. I can feel him getting off on my words when he clinches me of ruts back towards my groin. My cock is hard and my balls are heavy as they swing with each thrust. My fingers dig into his hips as I rut deep and shoot my load. I can feel my cream flowing into him and the sensation is amazing. I fuck a few more times before I fall on top of him. I'm panting. He's panting. After a few minutes, I push myself up and out.

I get dressed as he rolls over and watches me do so. His cock is hard and by now his asshole is oozing my creampie. I lean over and kiss his mouth ... "I can let myself out. You were great, Cassidy ... Mike ... "