Help From The Homeless

“I’m gay,” I declared to my parents.

They looked horrified as they took a second to process the news.

“How do you know?” My dad argued, “Have you ever had sex with a man?”

“No, but I—” 

“Then you’re not gay, you’re just having one of those adolescent rebellious phases,” my dad reasoned. “Being a teenager can be confusing but don’t worry, this ‘gay’ feeling of yours will pass.” 

“This isn’t a—”

“I’ll introduce you to some of my friends’ daughters,” my mom chimed in worriedly. “My friend Stacy’s daughter is your age and is very pretty and super sweet. I’ll call Stacy and have her set ya’ll up,” she got up to grab her phone.

“Arrghh,” I grumbled and stormed out the door. I had to get out of the house. There was no use in arguing, they never listen. Why don’t they just treat me like an adult for once?

I stepped out into the cold brisk air. The sun was setting and it was autumn in Tennessee. I was wearing a hoodie and jeans and hadn’t prepared to go walking at this time, but I just had to get out. I walked at a swift pace, both in frustration and to warm up. 

Why don’t they ever listen? What would it take for them to listen? 

I had been walking aimlessly for some time when I realized I was almost near the alleyway where I get catcalled on the way home from school. I don’t walk that way home from school every time, but when I want to take a shortcut, I walk down this alleyway and there’s a homeless man that lives there next to the dumpster. If he’s sitting outside of his tent, he always catcalls me with a new compliment. Sometimes I avoid the alley because he creeps me out but sometimes it’s nice to hear a compliment, even if it’s from a homeless guy in his 40s. Despite being gay, I’ve never been desperate enough to take him up on his bold advances. But today I was fed up, if my parents thought that the only way to know you’re gay was to have gay sex then so be it.    

I marched down the alleyway for once hoping to see my creepy admirer. To my luck, there he was, sitting on the pavement in his usual thick gray jacket, black beanie, baggy jeans, and bulky tan work boots. 

He perked up with a grin as soon as he saw me. “Hey cutie, lemme get in that booty,” he said amusing himself.

I stopped and took a deep breath before deciding to be probably the only person. 

I shrugged at him, “Okay,” I said and strolled toward him. 

His eyes widened in surprise. I was probably the only person his catcalls had worked on. He looked me up and down like a predator eying his prey, “How old you is?”

“I just turned 18,” I replied innocently. 

His smile widened and his eyes lit up like he’d struck gold. “You ever been with a man before?”

“No, but I want to,” I said eyeing him up and down. 

“Really?” He said with a hint of doubt in his voice, thinking it was too good to be true. “If that’s true, come suck my dick then,” he said unbuckling his pants right there in the open.

As he started to pull out his dick, I froze. I was unsure if I was ready to actually go through with this. I looked around, even more nervous for first time having sex to be in public. Even though the alleyway was empty and we were blocked from the street view by the dumpster and his tent, what if a cop drove by?

“C-can we go in your tent?” I asked shyly, the blind confidence I had earlier was gone.

He sucked his teeth as zipped his pants back up, doubting I’d go through with it, but figured he’d give me a shot. “Sure baby,” he grabbed my hand and led me into his tent. 

The tent had blankets strung across the floor in one section which I assumed was his bed. His kitchen appliances and canned food were in an unorganized mound in one corner. And clothes and other miscellaneous items were piled in another corner. 

He laid down along the blankets and immediately began taking off his shoes and pants. He pulled down his pants to reveal his decent-sized cock already fully erect. I imagine he doesn’t get cute young boys wanting to have sex with him often. 

He gave me a smug smile, “Suck it.”

This is it, I thought. This is what I wanted. I slowly laid down in front of his cock. As I got closer, I smelled the musky scent of his cock and balls, but I also smelled the putrid scent of his odor, he likely hadn’t showered in days. As I got even closer, I noticed his dick was speckled with dirt and grime. It was gross but if I wanted to have sex with a man and end the debate over my sexuality, this was the quickest way I knew how. I grabbed his cock and stroked it, half to buy me some time so I could build up my courage and half to rub off any of the dirt. 

After a few strokes, he stopped me and said, “That feels good, but I asked you to suck it.” I think he could sense my apprehension and could tell I needed a push. 

“Yeah?” I said nervously, moving my face within inches of his cock. 

“Yeah baby, I wanna feel your mouth on my cock.”

I took a deep breath then lowered my head and allowed his dick to enter my mouth. His dick slid across my tongue and he let out a moan of approval. I felt the warm sinewy skin of his penis rub the roof of my mouth and my lips enclosed around thick rod. With his dick in my mouth, I felt at home, everything felt right like I was supposed to have dick in my mouth. All doubt washed away and I gained confidence with each bob of my head on his cock.

His dick did taste extra salty from the sweat and whatever else was on his dick but to me it was just added flavor. I tried to stuff his entire dick down my throat but could only make it 3 quarters of the way. I moved to his balls and swallowed them in my mouth. They were hairy and wrinkly, but I loved the feeling their texture on my tongue. I played with them in my mouth and sucked them like my favorite candy. I’d been sucking on his balls for a while before he slapped his dick on my forward as indication for me to suck his dick again. I gladly moved back to his dick and slid my tongue up and down its entirety. 

When he felt I’d done enough sucking, he told me to undress. I took off my shirt but before I took off my pants he told me, “Turn around and undress for me with some sexiness.”

I didn’t know what undressing with sexiness meant but I turned around and slowly pulled down my pants and leaned over as I did it. My hairy untouched hole was directly in his sight. 

He licked his lips, “Mmm what a pretty ass. Come sit on my face.”

I walked over and kneeled on either side of his head to sit his face like he ordered. 

His tongue flicked across my anus. I hadn’t expected to have sex today so I hadn’t cleaned my ass. But he didn’t care and cleaned my ass for me, licking my ass all over. A new sensation of bliss swept over me as he stuck his tongue up my ass and licked my insides. I closed my eyes and stroked my rock-hard cock. This was the most sexual pleasure I’d experienced. 

“Now sit on my dick,” he ordered next. 

This is what I was the most scared of because I’d never had anything in my ass and feared it would be painful. But I obeyed his orders and moved over to his dick. He spat on his hand and stroked his cock as lubrication—no premium lube here. I lowered my ass until his tip pressed against my anus. Once his dick popped its head into my anus, it was pure bliss. But as I lowered myself further, the pain began. I stopped then tried again but my asshole felt like it was burning fiercer with every inch that entered my ass. 
I yelped in pain and shot up. “I can’t do this. I’ll suck you your cock as much as you want but I can’t take it in my ass.”

“What do you mean?” He said, with an obvious look of irratation across his face. He caught himself and calmed down, “You know what? Sure, just suck my cock.”

I sighed in relief that that he was understanding. I knelt down and stuck his cock in my mouth again. But as soon as I did, he jammed my head on his cock, leaving me no time to gag. Before I knew it his whole cock was down my throat. My eyes watered as I gargled and panicked for air. He ignored my pleas and gave my throat a few thrusts for good measure before he let me back up for air. 

I gasped to regain my breath. “See? You can do a lot of things if you push through pain and difficulty!” He said with a crazed look, “Let me show you another example!” 

He pushed me flat on the ground and laid on top of me. I squirmed under his weight but couldn’t move. He spat on his dick and stuck it in my ass. Then he slowly slid it deeper and deeper in my ass. 

“Stop stop stop!” I screeched in pain, but he didn’t listen. His dick sank deeper into my ass until it hit a wall. He pulled out spat on his cock again then reentered my asshole. His dick forced its way through my tight walls. I screamed louder, hoping someone would walk by and help. But it was nighttime in an empty alleyway, no one was coming. 

Finally, he stopped. But to my amazement, it was because his entire dick was in my ass. Although my ass was on fire, I was actually quite proud. Apparently, he was excited as well l because he pulled out his cock to spit on it again then proceeded to pummel my ass without mercy.   

“You know how long it’s been since I had an ass like yours?” He said as his balls slapped against my ass. “You thought you could just tempt me with it and walk away? Oh no baby, this ass is mine now. This ass is mine now.”

I moaned between thrusts. My ass was aching, but bursts of pleasure peeked through the pain and made it worthwhile.

He slowed down and switch to long deep thrusts. “Don’t ever come into my home and tell me no.” He slowly pulled out, only to slam his full cock in my ass with speed, then repeated the process. “While you in my house, this is my ass.”

I grunted with every thrust. It felt good, but I couldn’t tell if he was actually mad at me or just talking dirty. I wanted to apologize if he was still angry. 

“I’m sorry for not trusting you at first, you—” he slammed his dick in my ass. “I’m glad you didn’t listen to me, You were right, your dick feels this feels good.

“Sorry? You think I give a fuck about a ‘sorry’?” He picked up speed again and pounded my ass like a jackhammer. “Shut up and take this dick.”

He heaved and I moaned and grabbed the blanket for stability as he battered my ass. 

“Take this dick! Take this dick! Ahhh!” He hollered as his body quivered. Then warm liquid shot up my ass. He shuddered but didn’t skip a beat and kept penetrating my ass. When the last shudder and squirt of semen was finished, he pulled out and laid on his back next to me. He closed his eyes and gasped for air, clearly tired. This was probably the most physical exertion he’s had in months. 

I laid there as well processing what had happened. After a few minutes, I rolled over and looked at him and he had apparently passed out straight into a nap. Not wanting to lay there and figure out what would happen when he got up, I got dressed and walked out of the tent.

A smile spread across my face as I realized I’d done it, despite it being difficult to walk home with my ass still aching. But I was proud of the soreness in my ass and even the semen in it too. 

When I got home, I opened the door to see my parents sitting on the couch watching a movie. They didn’t even care that I’d left or where I’d gone. 

“Mom… Dad… I’m gay. I just had gay sex, and I liked it,” I said with a goofy grin. 

Both of my parents’ jaws dropped simultaneously and they sat there to stunned to speak. 

That worked for me. I walked up the stairs to my room triumphant.