Jason and the Abandoned House

There are a few places in town where homeless guys hang out. It’s usually wooded areas, or places where they can expect not to be hassled by the police. One such place is an abandoned house a mile or so from where I live. It’s been empty for years, and I’ve noticed some evidence of squatters as I’ve passed the place. Recently I ventured in through an unlocked back door and stumbled onto a goldmine. 

As I walked across the threshold, I was greeted by the smell of moldy carpeting and rot. I moved through the ruined living room, past the kitchen, and down the hallway. The first bedroom door was closed so I kept exploring. The other bedrooms were open and empty, and I headed back to the first one I’d passed. As I leaned close to the door, I could hear the faint sounds of snores coming from inside. I held my breath as I eased open the door, and saw a mattress on the bare floor, surrounded by empty beer cans and junk food wrappers. In the middle of the mattress was a thin-framed man, laying facedown and sound asleep. Though I couldn’t see his face, I knew him right away: Jason.

I only knew his name because I’d seen his picture in the paper after he was arrested for panhandling. But I had seen him plenty of other times. He was a 20-something Asian guy with a lean tan body and full lips that I was dying to seep wrapped around my cock. He was homeless, and I’d always see him in the places the homeless hang out in my city: the McDonald’s locations that didn’t mind people loitering; the library; on the bus. Basically, any place that a person could hang out without being expected to spend money was someplace I’d likely run into Jason. I’d also seen him standing in the median of a major highway, holding a cardboard sign and begging for money. Every time I saw him, I’d think, “Enough money, I bet he’d do anything…”

It was midday, and hot as hell, so he was wearing only baggy basketball shorts and a tank top. His tan skin had the sheen of slight perspiration, and all I wanted in that moment was to lick him and taste the saltiness of it. I crept slowly up to the mattress, but before I made any moves, I wanted to see how deeply he was sleeping. I’d need at least a few seconds of sound sleep to do what I planned to do. I cleared my throat loudly and asked, “Hey man, you okay?” I figured if that woke him up, I could pretend to just be a concerned passerby. But he slumbered on. Score. I eased my own shorts down to my ankles, and started playing with my dick. In no time at all, I was hard as a rock and ready for some fun. I knelt by the foot of the mattress and grasped the bottom of his shorts. As quickly and smoothly as possible, I pulled them down and off of him. The boxers he had on beneath them were pulled slightly down as well, and I was treated to the sight of about three inches of ass crack, and the smoothest ass I’ve ever seen. My dick throbbed, like it knew what was coming and it couldn’t wait to dive in. 

One more swift tug and his boxers joined his shorts on the floor. With his entire ass exposed, I could see wiry black hairs peeking out of his crack. The musky smell of his sweaty ass filled my nostrils and turned me on so much I felt dizzy. As much as I wanted to run my hands up and down his smooth legs, I couldn’t risk waking him up before I had to chance to fuck him. I leaned over his prone body and spit into the crack of his ass--he still didn’t stir. Then I spit on my own dick, getting it primed for some exploration. I gently moved into position, straddling him and lining up the head of my dick with his spitty ass crack. I pushed my dick into his sweaty ass, hoping for enough time to at least get the tip in before he awoke. Just as my mushroom tip popped past his sphincter, he moaned and tried to sit up. I quickly pressed my upper body against his, pinning him to the mattress. I slipped my left arm around his upper body--pinning his arms to his sides--and clamped my right hand over his mouth to keep him quiet. I’m not sure if it was the dick in his ass, or the feeling of another man holding him down, but he woke up pretty quickly after that. I guess getting violated by a stranger will do that.

He tried resisting, but I had him bound pretty good. I had his upper body pinned with the weight of mine, and my dick in his ass kept him in place. He wriggled and writhed, but he wasn’t going anywhere. He let out a few low grunts as he tried to escape my grasp, but I let him know it wasn’t going to do any good. 

“You can fight all you want, but that just turns me on. I love raping little faggots like you.”

I saw his eyes widen as he processed my words, and it turned me on to no end. I forced the length of my engorged cock into his ass, reveling in the tightness of his sphincter. He squealed against the hand I had over his mouth, wordlessly protesting the invasion of my dick. 

The harder I fucked him, the more he fought me. He strained against the arm I had around him, struggling mightily to get from beneath me. But I had him pinned good, and I wasn’t going to stop until I dumped my load in his sweet boy pussy. I could feel our sweat mixing as I pushed myself inside of him. I knew I wasn’t going to be able to hold out for long.

“You like that dick, Jason?” I heard him gasp as I said his name, and he tried to twist his head to see who was deflowering him. I still had my hand over his mouth, so it was easy to keep him facing forward.

“That’s right, I know all about you. I see you all the time begging for money. You should thank me: now that you know you can take a dick, you can start turning tricks now. You’re going to be the most popular whore in this city. Guys will be lined up for a turn in this pussy!”

He let out a muffled whine as he submitted to the ass pounding I was giving him. Just hearing his tortured cry was enough to send me over the edge into bliss. 

“Fuck yeah! Take my cum, slut. I’m gonna make a proper faggot out of you!” With that, I fired off five shots of fresh jizz into his anal canal. Realizing it was over, he whimpered and went limp. I leaned close to his ear and whispered, “I’ll be keeping an eye out for you, boy. Next time, I’m gonna put you on your knees and make you suck my dick. You’d like that wouldn’t you? On your knees like a whore, drinking Daddy’s cum?” I kissed him gently on the cheek and told him to count to 100 before he got up. Before walking out of the house, I pulled out my cell phone and got a picture of the cum that was starting to drip out of his abused hole. Nothing like a souvenir from a good time.