Streets to Sheets E4 | Is the homeless guy playing me?

Everyone is over the age of 18

Continued directly from the last story…Read from the beginning here!

Recap: Wilson is a man of routine. He goes to work, grabs lunch at the sub shop, and heads home alone. One day, he decides to strike up a conversation with the handsome homeless Carter stationed outside the store, and it turns out Carter isn’t shy if it means he can stay somewhere warm and safe.

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I didn't do anything else with Carter once I got him off. I was still horny, of course, after having rimmed his sweaty crack until completion. However, he seemed to be totally depleted of energy afterwards. Carter made an effort to touch me too, but I could tell his eyes were drooping and the energy wasn't there anymore. I let him go to bed and he sleepily put his underwear back on before going to my brother’s old room. 

And that was that for that night. I went to bed satisfied but not satisfied at the same time.

“Hey big man, I’m going to take off.” I was in a half-asleep state when his voice came from my bedroom door.

“I can drop you off,” I say as I scratch my overnight stubblem, willing my eyelids to be less sticky.

“Don't worry about me. Thank you so much again. Catch you later, ok? Thanks a lot.” 

I felt like I caught just a glimpse of his black hair because he closed my bedroom door right after his last word. I hope I at least smiled at him. For a guy that’s spending time on the streets, he’s unexpectedly nice. 

Reflecting on the experience kept me awake, so I decided to get up. Carter made the bed before he left, and if it wasn't for the faint smell of him, it's almost like he was never there. 

I lean in and take a deep inhale from the pillow. It’s really too bad a young guy like him ended up in such a situation.

I went to work as normal and looked forward to my lunch break. In the back of my mind, I wondered if it was a bad idea to go to my usual sub spot. Will I keep bringing Carter home each night? 

Is that what he wants?

Is that what I want? 

By the time the clock's small hand reached 12, I knew I was going to do it, at least for today. I mean, where else would I go anyway?

I was imagining all morning what I would say when I saw Carter, and so I felt almost disorientated when he wasn't there in his usual spot. 

I linger with my hand on the door’s handle, looking at the cardboard where he usually sits on a  tattered blanket. Another person comes up behind me, and I enter the store. I put my order in on self-pilot mode, staring behind the cashier to look out the window. 

Where did he go? 

Is he avoiding me?

What did I do?

“Here you go.” The worker has an exasperated look on his face as he extends the sandwich closer to me. I think he's been holding out his arm for a while. I take it, thank him, and leave. 

Where is he? I look around the streets. There are other unhoused people hanging out on the curb, and I wonder if they knew Carter. Should I ask them?

“And then my rents kicked me out…” I snap my head around to locate the sound, and see Carter walking back up to his spot with a blanket around his shoulders and a sandwich in his hands. 

And beside him? An older lady. The type that looks like they push their dog in a stroller.

My feet took me there, and my mouth started talking before my brain came back into control. 

“What is this?” I ask, interrupting their conversation. 

“Oh, Wilson. Big man. This is…” Carter's green eyes are full of surprise while he looks between me and the lady. 

“So you use the same scam with everyone?” I can feel myself crushing the sub in my hand. 

“Excuse me??” The lady says with shock in her voice. She clutches her purse and feels inside for her things. Reassured that she still has her wallet, she scurries away without looking back. 

“Dude!” His shoulders slump as he watches his target run away. I unclench my fist on the sandwich, and then turn to leave too. “Wilson! Hey! Wilson!”

He jogs up next to me and I keep walking briskly without looking at him, turning into the first alley I see for a shortcut back to the office. 

“Yo, big man! What's your deal?” He stops at the entrance of the alley and our distance grows. “What'd I do?! Wilson!”

I turn around to face him, although I'm not sure what I wanted to say. Obviously, I’m pissed, but I don't blame him at the same time. I blame myself really, for being so stupid. 

Of course I’m not the only one.

Of course I’m not the first one he did this with. Of course I’m not the last one.

“Is it cause I didn't…” He looks behind him as if to check if anyone is passing by. Then, he closes the distance between us and asks, “Is it cause I didn't get ya off?” 

“No.” 

“Okay. I get it. Yeah, you caught me. It's a routine I do to get off the streets for a night or two. I'm sorry,” Carter says before looking down. “I don't have… it's all I can do.” 

“I know.” Like I said, I know that he has to do what he has to do to survive. But still…

“It never lasts more than 2 nights. So I thought you were done with me.” He looks at me briefly with his sad green eyes before looking away again. “Anyway, I apologize. I know what it looks like. I didn’t steal anything, I promise. You can check my pockets.” 

“It's…” I shake my head. I feel guilty, because I have wondered if he would steal anything. 

“Did you want me to get you off? I don't like to owe anybody anything. I’m not asking to stay tonight or nuthin’.”

“It's fine.” I shake my head again. “I'm sorry. I ruined your plan.” 

“I wasn't so sure if it was going well anyway,” Carter says with a small smile. “Got a sandwich though.” He holds it up in an apologetic manner. “Do you want it?” He points to my crushed sub. 

“No, keep it.” I can't believe he could even think about being generous right now. It just makes me feel more like a giant dick, to be honest. 

“Then, let me get you off,” he says seriously. Carter puts down the blanket and neatly folds it before kneeling on it. 

“Carter…”

“I want to. Do you want to?” He looks up at me. 

This doesn't look like an alley where a lot of people go down, but still…

“I wanted to last night, but you made me really tired,” Carter says with another smile. “No one comes down this way, I promise.” 

It's like he’s giving me permission to say yes. The blood rushed to my groin, reminding me I haven't gotten off two nights in a row after servicing the handsome man kneeling in front of me.

“Ok,” I whisper. He unbuttons my work pants and pulls them down to my ankles. His hands grope my growing cock over my boxer shorts. 

“Big man is big after all.” Carter reached into the underwear slit and I pulse against his grip. “I'm going to suck it.” 

“Ok.” My voice trembled. “Oh fuck…” My cock gets exposed to the cold outside air for a second before getting engulfed into his warm mouth. I look forward into the bright street opening ahead of me, wondering if anyone was going to catch us.

Carter pulls my sore balls out of my slit too and strokes them lightly while he blows me. 

“Fuck…” I groan as he deepthroats me. I think he can tell that I can’t take too much. Having sex in public for the first time ever is exciting me a little too much, let alone having a two day load pent up inside me. 

“You can cum in my mouth.” Carter hums. The mention of the word ‘cum’ pushes me to my limit. Some people pass the alley’s entrance, without looking in our direction.

“Ah…ahh….” I grip onto his black hair, pushing up his unkempt bangs so he looks up at me. His piercing eyes stare back at me, with my rigid cock at his lips.

“Do you want to cum in my mouth or on my face?” He asked, his lips touching my cock tip as they formed the words. 

He said cum again. 

He said cum again!

FUCK!

“Ah!” I shoot onto his nose. “Oh! OH!” I moan loudly as he grabs the base of my cock to pump it. “OH!” My load is thick, coming out first in heavy deposits onto his cheek.

This is what it’s like when it’s been two days, I guess.

“Ah!” Carter pumps me hard, and I spurt onto this weathered jacket.

He keeps stroking until I guide his mouth back on it. There, he deepthroats me, letting me finish my climax inside him. 

“Oh…oh…oh…” Any residual angry feeling I had towards Carter exits me and he swallows it. 

“Are we even now, big man?” He wipes his face with his sleeve. 

“You didn't need to do that.” I quickly pull up my pants while watching for people again. 

“I wanted to. But are we good now?” Carter’s sleeve is stained with my cum. He’s going to smell like me until his next wash.

“Yeah.” I breathe deeply once I get my belt buckled back up. “Hey, come stay with me tonight. I'll wash that for you.”