Beggar at the No-Tell Motel

Sometimes I like to rent a cheap motel room in town. I like the cheap ones because they tend to have lower standards for “acceptable” behavior. Some of my greatest adventures have involved getting a room and exposing myself, or inviting a stranger in for some fun. 

Recently, I had a room and was sitting in it with the door ajar. I was wearing a robe, but I’d left it open and was sitting in a chair by the window. I saw a figure walk past my door and looked up in time to see a slim white guy with shaggy brown hair pause by my doorway. He raised his hand and knocked lightly on the door. I called out, “Yeah?” and he pushed the door open and took a step inside.

“I’m sorry to bother you sir, I’m trying to get a room here tonight but I’m short on cash. Is there any way you could spare 10-20 bucks?” I noticed that the entire time he spoke, his eyes never left my exposed cock. It’s almost like he was talking directly to my dick. That was all the encouragement I needed. 

 “Would 20 bucks help you?” I asked innocently.

His slim face lit up with a genuine smile. “Sir, that would be great, I’d really appreciate it!”

I began to casually stroke my dick as I continued, “Sure thing. I’ll help you out, but you’re going to have to help me out too.”

“What do you mean?” he asked nervously.

I laughed at his attempt to play dumb. “You know exactly what I mean. I’ll help you out with 20 bucks, but I’m going to need you to help me with some head. You any good at sucking dick?”

His eyes widened and he swallowed hard. He stood staring for a few seconds before answering. “I--I guess...I’ve only ever done it when I was locked up.”

Both my ears and my dick perked up at the mention of prison. If someone else had already turned him out, this would be easier than I’d anticipated. “Oh yeah? Someone made you his punk?”

He flinched at the word “punk,” but nodded his head in affirmation. “My cellie used to make me suck his dick every morning after he got up. Sometimes he’d fuck me after lights-out, but it was mostly just sucking his dick.”

He was still standing in the doorway, so I gestured for him to come closer. “Why don’t you close that door and show me what you learned in prison?”

As he shut the door, I stood to close the curtains. I sat down on the bed with my legs spread and watched as he nervously walked over to me. He got down on his knees and hesitantly took my hard dick in his hand. He looked at it for a couple of seconds, then slowly lowered his head. He gently licked the tip before taking the entire head in his mouth. The velvety warmth of his mouth made my dick throb. He wasn’t the world’s best dicksucker, but he’d obviously spent a lot of time on his knees. Easing his face off my dick, I told him to take his clothes off. “I want to look at your body while you suck me off.” He stood and began to strip while I played with my hardon. His body was nice: long, lean legs covered in a golden brown fleece; an average (soft) dick with thick curly pubes; and a thin chest with light chest hair and two tattoos that looked homemade in nature. I caressed his chest, stopping to pinch one of his light pink nipples. He gasped as I twisted his tit, but he stood there and took it. Someone had indeed taught him well. 

With his clothes on the floor beside him, I guided him back to my dick. He dropped back to his knees and took up his work again. I put one hand on the back of his head, and pushed his face further down my cock. He gagged and tried to take his mouth off me, but I just pushed harder. He wasn’t good at deep-throating, and the sound of his gags filled the motel room. When I had his nose buried in my pubes, I held him in place, ignoring his muffled protests. His hands flailed at my waist as he tried to free himself from my grasp. He let out a loud retch and I knew he was about to throw up. I took my hand off his head, since I didn’t want him puking in my lap. Still gagging, he turned away from me. In this position I was treated to the sight of his furry asshole and decided I wanted more than some head. 

I hopped up and got into a kneeling position behind him. He was busy trying not to vomit, so he didn’t notice right away that I’d moved. When he felt the head of my dick touch his exposed asshole, he jumped a foot. He tried to turn and look at me, but I reached forward and grabbed him by the back of the neck, forcing his head down against the carpet. I spit into my free hand, roughly rubbing it into his puckered brown eye. 

“C’mon man, please don’t do this!” he implored, but I wasn't feeling very compassionate just then.

“What’s wrong? You said your cellie fucked you too. If you can’t give me good head, I’ll just have to get my rocks off another way. It’s not like you’re a virgin anyway.”

With my hand still on his neck, I pushed my engorged cock into his asshole. He whimpered and clawed at the carpet while I took my pleasure. “Is this how your cellie gave it to you? Or was he rough?” I asked as I began to thrust harder. I could feel his sphincter squeezing my member as I drove it deep inside him. I could tell it was hurting him, and it just turned me on all the more. 

“Fuck yeah! You’re really earning that $20 tonight, huh? You like that dick, faggot? Is my dick bigger than your cellie’s?” He didn’t answer me, but I really didn’t need him to. Talking to him like that wasn’t about his answers. The humiliation that seemed to roll off him in waves was the point, and it was delicious. 

After a few minutes of intense pummeling, I felt his body go slack. He was still whining, so I knew he wasn’t passed out. I guess he’d finally submitted to the fucking he was getting. Knowing that I had his compliance, I pulled him to his feet and sat him on the edge of the bed. I lifted his legs onto my shoulders, and pushed my way back into his anal canal. As much fun as I had shoving his face into the cheap motel carpeting, this was even hotter. In this position, I could watch the expressions on his face as I violated him. He grimaced as I plunged my cock into him until our pubes were brushing against each other. Over and over, I pulled my dick almost all the way out, only to drive it all the way in. With each stroke, his face turned redder and his humiliation more complete. 

I felt my balls churning, and knew I was about to shoot my load. With one last decisive thrust, I pulled  my dick out of his abused asshole and sprayed my load on him. Most of my jizz landed on his crotch and chest, but one shot landed on his chin, covering his scraggly chin hair. I stood over him, enjoying the tear I saw rolling toward his ear. I grabbed my pants off the floor and reached into the pocket, pulling out a twenty dollar bill. “I’m a man of my word, and you definitely earned this money.” He reached for it, but instead of handing it to him, I used it to wipe some of my spooge off his balls. Then I stuck it to his forehead. I don’t know what made me do that, but the look of dejection on his face almost made me cum again. As he rose from the bed and got dressed, I slapped his skinny ass. “I’ll be here two more nights. If you need some more money, stop by and gimme some more pussy.”

He pulled the door shut behind him as he walked out and I figured I’d never hear from him again. And I didn’t--until the next night when he knocked on my door again. Guess he needed the money.