Tales from the Street

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A newly homeless man gets an eye opening experience.
1.7k words
4.22
21.9k
28

Part 1 of the 4 part series

Updated 06/08/2023
Created 04/14/2018
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This will be an ongoing short story series of TRUE STORIES about my life on the streets. I will post them as I get them written. The first of which (this one) contains non-consensual male on male sex. If that bothers you, DO NOT READ.

For those who wanted to know what happened to Houston (because you felt sorry for him), [RE: BOYS AVENUE], I've given it some thought and worked out his love story and am slowly writing that in between the Street stories.

*****

"Are you hungry?" the handsome Latino man who introduced himself as Teardrop asked me, rising from the concrete bench, where he found me, under Travis Park's memorial for the Confederate dead, "Come on, I'll take you to La Villita. It's just peanut butter sandwiches, but it's food. I just need to make a quick pit stop first."

I was homeless, doing a bad job of surviving on the streets of San Antonio, Texas for the past two weeks. I was broke, beyond exhausted from no more than a few bouts of sleep on park benches before the Park Rangers would wake me and tell me I couldn't sleep there. Furthermore, I was physically weak from lack of food. I hadn't had anything to eat since my first day in town.

I saw Teardrop a few days earlier in that same park, and again at a bus stop in front of the main branch of the Public Library, where I spent most of my time trying not to fall asleep, occasionally failing. He waved to me both times, trying to get my attention, but my embarrassment over my situation overwhelmed me, and I stupidly ignored him. When he saw me again, trying to warm the Autumn night's chill from my bones in the morning sun, he approached me and introduced himself.

I rose and followed him out of the park and followed him, my mouth watering with the thought of food, my stomach cramping from the lack of it.

He was about an inch or two taller than my five-foot-nine inches, and had a sturdier, stronger build. He was wearing faded blue jeans that bulged suggestively in all the right places with a white tee under a dark denim shirt. Having lost some weight, and not wearing a belt, I was doing good to keep my pants pulled up. His black hair was slicked back, away from his big dark brown eyes. There was a tear drop tattooed beneath his left eye.

We descended to the Riverwalk, down a flight of concrete stairs, and made our way south, into a less frequented section of the Riverwalk I didn't realize existed. We crossed the river at the dam, then continued until we came to a bridge. On one side of the bridge was a staircase that led back up to the street level that was lined with a bed of densely growing of shrubs, flowers and other plants.

"I stashed something under the stairs," he explained, "Come inside with me, so you don't attract any unwanted attention."

I watched as Teardrop disappeared into a narrow opening in the shrubs, between a pillar that supported the stairs and the tall wall of the bridge's foundation. I followed him in, emerging into a dark cave like area that slanted sharply downward with the fall of the stairs above.

Once inside the little artificial cave, Teardrop attacked me, pushing me face first into the bare dirt. At first, I didn't understand what was happening. I was so tired, I couldn't have put up much of a fight. Teardrop was bigger and stronger than I was, even before I was starved. It was when I felt my pants being tugged down that I realized what was happening.

I was twenty-two years old and had only had sex once. Out of pure frustration, I gave my virginity to a forty-five-year-old man I met at a flea market, two years prior. He sold me a sarape, and I gave him my phone number. The night he came over was a dismal disaster. He had about four inches of dick, with which he repeatedly pulled out and rammed back into my virgin ass over and over again. It was such a painful, unpleasant experience that I wondered if I would ever try getting fucked again. Now I was going to be fucked by a virtual stranger.

Teardrop held my face to the cold, bare earth with a hand braced against my neck. Fear shook through me, but there was nothing I could do to change my situation. I felt him move above me, releasing his hold on me to line up his cock.

I heard him spit, then felt his fingers wet my ass hole. I felt him shift his weight, lining his cock up with my sphincter. With one thrust, he pushed into me, sending a shockwave of ripping pain through my lower abdomen. I cried out but didn't recognize the sound that came out of me. Teardrop wrapped his hand around my mouth to silence me, shifting his body forward. The entirety of his weight now pinning me down.

"Be quiet!" he whispered menacingly into my ear as he began thrusting his cock in and out of the deep recesses of my ass. I closed my eyes and tried to relax, giving myself up to his manipulation to try to relieve the pain. There was no point in fighting him anymore. He was inside me, and he was going to have his way. I lay there, my ass throbbing with his every thrust.

But then the pain subsided and all I felt was the thickness of his manhood filling my ass. I became aware that my own dick was hard, like he was forcing me to erection. I grew more and more excited as his fucking pushed me deeper and deeper into a pleasure I had only read about in gay magazines. I loved him for making me feel that pleasure so completely. I hated him for forcing himself on me. I grew conflicted with every thrust. My ass was so full of his cock, his strong body dominating mine. I was swept away in an almost orgasmic wave of pleasure I had never experienced before, and my body was screaming out for more.

I placed one of my hands on the hand he held over my mouth, pressing my fingers between his. He relaxed his grip on my mouth, then released it, lacing our fingers together. I moaned in my mounting pleasure.

"You like that?" he asked in a broken whisper, thrusting his cock into me hard. I could hear surprise in his voice.

"Fuck yes," I managed to say, my voice not much more than a croak, "Please, don't stop."

He pulled himself above me, bracing his weight on his hands as he continued to fuck me. No longer in the rush of a man just trying to bust a nut, he took his time probing my ass, stroking long and deep, ramming into me hard. I was in bliss, completely invested in what he was doing to my body.

Teardrop continued to pound away at my ass and my body was responding in near orgasmic bliss. My body burned with a wildfire that I felt in every pore of my skin. I was so wrecked with what his cock was doing to my ass that I almost whimpered when he thrust into me one last time, spilling his seed deep into me. My sensitive hole felt every spasm of his cock as he shot his load. After a moment of recovery, he fucked me softly a little while longer.

Afterward, he nuzzled his head against mine for a moment. "I'm sorry," he whispered in my ear before pulling himself off me, and out of me. I just lay there, feeling empty without his cock inside me, and conflicted about what had just happened.

I watched him get his backpack from the lower portion of the stairs and realized he was leaving- he was leaving me alone to fend for myself. Regardless of what had just transpired between us, I was still hungry and exhausted. I needed his help if I was going to survive. I crawled to my knees, trying to pull my pants up. He rushed past me, on his way out.

"Wait!" I called to him as he approached the entrance way, "Please don't leave me here."

He hesitated, then looked at me as I struggled to find my footing. My legs were weak and wobbly.

"I'm not going to survive on my own." I pleaded with him, "I don't know what to do, or where to go. Please, I'll do whatever you want, just don't leave me here alone."

He stared at me for a long moment. My hard on was still visible, jutting out above the top of my pants, leaving me feeling exposed and even more pathetic than I already felt. In that moment I hated myself for being made so vulnerable and needy.

He took a few steps, closing the distance between us. Extending his hand, he rubbed his index finger over the top of my piss slit. A long string of pre-cum stretched between his finger and the head of my dick.

"Come on," he told me, helping me to my feet. After I pulled up my pants, he brushed the dirt from my clothes. "Let's get out of here." He handed me my backpack, and we left the little enclosure as if nothing had happened. "I think we should go to Miss Winnie's. We can get something to eat there, and then you can get a shower and a change of clothes."

We walked together for a while in silence, giving me time to process what had just happened. My cock was still hard for most of the walk back. I didn't know if I should be angry at him for forcing me to have sex with him or hate myself for enjoying it so damned much.

Either way, he rescued me. He spent the day helping me navigate homelessness, showing me where to go to find services, and what services they offered. He left me at the city shelter, then walked out of my life forever.

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4 Comments
AnonymousAnonymousabout 5 years ago
Rape does not become enjoyable

Sorry - but if you say you enjoyed it, its not rape. And no one enjoys it at first.

AnonymousAnonymousabout 6 years ago
Streets of London

This brings back many mixed feelings. Shame, arousal, confusion... My first experience of sex whilst homeless was the first time I was raped. I too became aroused and begged my attacker not to leave me. He took me to Holland Park and passed me to another man. Three men ejaculated in my arse that night and one more made me suck him.

AnonymousAnonymousabout 6 years ago
love r]this story

i was in this mans shoe when i was 18 . the same thing happen to me i was on the streets and a guy pick me up . i was cold wet and hungry he took me to his place and got me out of the wet close and i was nude he gave me a blanket and some food i inhaled the food then he rape me by the time he was done i was fuck good and beg for more

dan1957dan1957about 6 years ago
Love the true life story

Good for us all to read about a true street story. First he raped, and then help to save you from death

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