When Millie took the kids and left me, I really started going downhill. I had been drinking before, (that's why she left) but now I was pouring it down. Stumbling around all day in a drunken stupor, tripping over everything.
First, of course, I lost my job. Then I couldn't pay the rent and they kicked me out of the apartment. So there I was, a street person, one of the homeless, carrying my few belongings in a shopping bag. I would go down into the subway trains, pushing through the crowded cars, "Help. Help a homeless person get a meal. I'm so hungry. I haven't eaten today. God bless you, sir. God bless you ma'am." But whatever I collected usually didn't go for food. It went for cheap red wine, which was the only thing I could afford now to keep myself perpetually in this warm haze.
Sleeping was the worst part. The men's shelter cost one dollar a night, and I didn't always have that dollar. I would end up having to sleep in a dark alley. At least there were usually garbage cans in the alley, where I could forage for scraps of disposed food. Tonight was going to be one of those nights. I didn't have a dollar and I was looking for a nice, quiet, out-of-the-way, far-from-the-world alley where I could hunker down and sleep in peace. Without fear of getting beaten or arrested.
I found my alley, and stumbled towards the back of it, drinking the last dregs from my wine bottle. "Yesh, I'll shleep here," I drunkenly babbled to myself. I could barely stand now, but while weaving from side to side, I found some old newspapers and spread them on the cement. I lay down on the paper, and pulled my old blanket from my shopping bag, throwing it over me. Everything was spinning around, warm and cozy. It was almost like being in another world. People who don't drink are missing out , I thought. How much better this sweet fog was than being married, having a family, working in a boring job, etc. etc. etc. I started to drift off into slumberland when I heard feet shuffling down the long alley in my direction. It was another tramp like me. Another bum. Just as drunk as I was. I watched him approach through half closed eyes. He came up next to me and stared at me.
"Hiya ," he greeted me. "Thish izh a good alley to shleep in." He barely got the words out of his alcoholic mouth. "Do you mind if I crashshsh here wit ya." I turned over on my side and put my arms over my head, trying not to acknowledge his presence. He was a wiry thin compact guy with uncut uncombed blond hair flying in every direction. If he had been cleaned up and fed, he probably would have been good looking, like I used to be when I was clean and fed. He had a blond moustache and beard, and except for the two he was missing, his teeth were pretty good. "Do you mind if I shleep here wit ya?: He asked again. I still didn't answer, but that didn't deter him. He flopped down heavily at my side. After a few minutes, he pulled out a bottle from his own shopping bag. "I shtill got a little wine left. Ya want a sssip?" That got my attention. I turned and took the bottle from him, put it to my mouth and swigged as much as I could get down in one big swallow, before he took the bottle back. I wiped my arm across my mouth, and turned back to lie down facing away from him, still not saying a word. I heard him empty the bottle and roll it away down the dark alley. Then I could tell he was stretching out by my side. "Ish a little cold out here tonight. Ya mind if I share your blanket? " I didn't answer again, so he just lifted one side and crawled in, wrapping his end behind his back and under his body. I wasn't left with a lot of covering.
"You took my whole blanket," I complained angrily.
"Nah. Jussht a little bit. Here. Shcrunch up next to me. We'll both keep warm." He pulled me against him and pressed himself against my back. It was getting warmer, but his beard was tickling the back of my neck. Then I felt a hard thrusting lump at my behind, and I knew what that was, but I couldn't believe it. I could never get a hard-on when I was drunk. Another reason my wife had split. But this guy didn't seem to have that problem. I felt him rotating his hips on my behind, rubbing his meat against my rear end. It felt strangely pleasant. It was the first physical contact I had had in many months. I didn't want to lead him on when I had no intention of doing anything, but I couldn't resist rotating my ass against his hard dick.
I heard his breath catch in his throat. He was getting excited. I laughed maliciously. I'd just work him up into a good lather and then say no. What a joke on him. Poor stupid drunk. Then I felt his top arm go around my hip, pulling me against his body. Fine. Let him get real worked up. I laughed.
Finally I felt his hand reach down and start to unhook my belt. I thought maybe now might be a good time to stop. "uh uh. No," I breathed and tried to pull his hand off my waist. He hung on tightly. "No." I said more firmly and attempted to pull away. He wasn't going to let me.
"I thought you were gonna be a nishe guy. A good buddy. Kind of help a buddy out. Kind of help a horny buddy out, okay?" he said turning his statement into a plea.
"No," I insisted.
Suddenly he rolled me flat on my back, crawled above me and slammed his open hand across my face. "You fuckin' little tease. You fucking lousy little tease." His hand came slamming down again.
My eyes were tearing. "Shtop," I said trying to shield my face with my arms. He pulled my arms down and began slapping me right and left, left and right. I was screaming. "Shtop. Shtop."
"Lower your fuckin' pantsh and get on your belly," he ordered. I decided it would be prudent to obey.
When I was on my belly with my bare ass facing up, I felt him lift the blanket and lower his own trousers. He was lying on my back now, with his prominent ironhard cock pressing against my soft flesh.
"Pull open your cheeks," he commanded. "I want to see the nice little hole. Come on, you fuckin' cunt. Pull 'em open. He didn't sound so drunk now. The sex urge was sobering him up. I separated my ass cheeks with my hands, and he looked down, studying it.
"Oh, yeah. There'zh the nishe little hole. There it izh." He lovingly rubbed his long index finger against my puckered opening, stroking it back and forth. Then he spit on his finger, and moved it back to my hole. He took out his finger and spit again. In a flash I felt the finger back inside.
He was gradually working it in, sticking that finger in the forbidden place where no man had ever gone before. A whole new world in there. He might be feeling the thrill of exploration, but I was feeling a slight discomfort, that is to say, a pain in my ass. I groaned. Even my alcoholic haze was not shielding me from this violation. It had been a short reprieve.
"You're hurting me," I cried. He didn't answer. But he did take his finger out if only for a moment. Then he spat again a couple of times, and now I thought I felt two fingers entering me.
"What a tight little cunt you have, honey. I just can't wait till I feel that nice hot little pussy wrapping itself around my dick and squeezing it. You're gonna do that for me, honey, aren't you? You're gonna wrap that nice hot pussy around my dick and squeeze it?"
Suddenly I felt the tip of that dick replacing his finger at the entrance of my hole. I heard him spitting a lot, and felt the movement of his hand as he spread the saliva on his hot poker which was now resting on my ass cheeks. I could feel it getting really wet. Then he lifted himself a little and aimed it down at my opening and pushed, pushed. Oh my god. It hurt. It hurt. And he was forcing it in further, down my dry passage, scraping my insides. Hurting me. Pushing. Pushing. Oh, my god. It hurt. It hurt. The thing was monstrous and he was spearing my ass with it. Then he lay down flat on my back, and I could feel his beard whiskers again tickling the back of my neck. The pressure eased for a second and then he gave one final shove all the way down. "AAAARRRGGGHHH," I screamed. His balls hit mine, and also rubbed against my tender ass cheeks.
"Shut up, you bastard. We'll have every bum in the neighborhood here wanting to get in on the action. I wanna enjoy this all night long. I haven't had a good piece of ass in a long time." His body began a subtle motion on top of mine. He was fucking me. His cock was moving around inside my asshole, feeling its way around. He began to nuzzle his lips on my neck. "Squeeze it for me, honey. Squeeze that pussy around my big dick. Oh, yeah! Oh,yeah. Like that. That's it. Love Jimmy's big dick in your ass." So his name was Jimmy, and I was starting to love it. All of you knew I was going to say that, didn't you? Why is it so hard not to love a cock after it's in your ass, even though you didn't want it there in the first place? The pain had long since departed, and it felt soo-----well, you know how a big cock feels working its way around your pussy. "Oh, Jimmy," I moaned. "Jimmy."
Suddenly there were footsteps in the alley. I turned my head to the side and there were three more tattered hoboes standing there watching us in amazement.
"Look, " one of them said. "The bum is fucking another bum."
"He's fucking the bum's bum," the next one said and laughed. They all laughed. "And look at that nice bum on the bum. I haven't had a good bum for a while. I wanna be the bum who gets that bum next. Hey fellas," The first one called. "We heard a little commotion in the alley so we came down to see what was going on. You got room for three more bums over there?"