Misty Helps the Homeless!

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Misty Helps the Homeless!
Misty Helps the Homeless!
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Year: 2024
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Five short stories about Misty’s encounters with nasty homeless men who fuck her holes with their smelly, dirty cocks.
Misty Chikan
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My name is Misty, and I’m currently in college. I was waiting for my roommate to get home. Julie was a stunning dark-haired girl and I was lucky to get her as a roommate. I was very sex free, and it turns out she was even more sex free than I was. Julie was the first girl I ever fucked. After a few nights together and a few drinks, she told me she was bisexual. After a few more drinks, I soon found myself naked between her legs.

After that, we would fuck each other weekly. We even used toys on each to help us experiment. We also encouraged each other to try new things and meet new people. My first time trying anal was because she told me to try it.

We also had a betting system going. When one of us asked for a favor or got helped out in any way, they would need to do a forfeit. These forfeits could be anything we wanted, and we normally used them for our pleasure. The last one she owed me, I made her make out with a fat girl who was trying to hit on me. That ended with Julie getting fingered for a bit before she could get away. That meant the forfeit that I now owed her would be a bad one.

“Creeps out again,” Julie said as she walked into the room.

“He’s out every night,” I told her.

The creep was a homeless man who stayed in an alley opposite our block of dorms. He was harmless, we think, but he did like to grab his cock and offer any of the girls a good time when they walked past.

“Did he offer you a good time?” I asked.

“You know he did,” she replied.

“Maybe if someone took him up on his offer, he would stop asking so much,” I said.

“You are offering?” she asked.

“No way,” I told her.

“You do owe me a forfeit,” she said.

“Not that though,” I said.

She got a sly smile on her face as she made her way to her bed. “Your forfeit is to go outside, and if he asks you for a good time, you offer him a blowjob,” she said.

“No way,” I said.

“You know the rules. You can’t say no.”

“But this is too much.”

“He might not say anything to you, and that will be it.”

“And what if he does?”

“Well, then, it’s only a blowjob.”

“He will be all dirty. And he might be dangerous.”

“He will be dirty, but I will be here, and I can come help you if he tries anything.”

I went quiet and thought about it for a minute. I could go out there, and the old homeless man might not say anything, and it would be over. I then thought about if he said yes, I would have to go down the alley and suck his homeless cock. For some reason I felt myself get wet thinking about that.

“I will make you pay for this,” I told her.

“Worth it,” she laughed.

“I will call you and you stay on the phone. If the creep tries anything, you come running,” I told her.

She agreed and sat by the window so that she could watch. I got up and checked my reflection in the mirror. My dirty blonde hair was already in a ponytail, and my slim, toned body was hidden in some sweats. I left the room and made my way down.

*****

Once I was outside, I called Julie. “You best get used to fucking fat phugly girls with stinky pussies,” I told her as I placed my phone in my pocket.

The street outside was lit, and I could see the guy at the edge of the alley. He was fairly old, maybe mid-60s, and he might have been OK-looking if cleaned up. He spent most of his night with a bottle of vodka so that he might have been on the streets due to alcohol, or he went to drink afterward. I crossed the street and walked closer to him.

“Fancy a good time?” he asked as I got close.

One hand grabbed at his groin.

“Maybe,” I told him.

He seemed stunned to hear that kind of reply. He froze for a second, and I thought I might be able to get away with doing nothing.

“What do you have in mind?” he asked, dashing my hopes.

“A blowjob,” I told him.

“You want to suck my cock?” he asked.

“Yes,” I said.

Again he hesitated before he motioned me to follow him down the alley. I shot Julie a look up at the window. She smiled down at me. I followed the old guy down the alley and made my way to the small nook where he had his bed made up. There were some lights down the alley, and I could see pretty well. Inside the nook was a pile of blankets he used as a bed.

“Why do you want to give me a blowjob?” he asked, standing to one side to let me in.

“My friend dared me,” I told him honestly.

“Oh,” he said, shocked. “You don’t have to do it.”

“You don’t want a blowjob?” I asked him.

“I did not say that,” he said.

He was wearing an old button up shirt with the bottom few buttons missing. He had a pair of faded jeans on, which he started to unzip. The light was good enough down here that I could see everything clearly. When he was fully unzipped, he looked at me, and when I said nothing, he pushed his jeans down. He had no underwear on, and his semi-hard cock flopped out. He grabbed it and stroked it as I watched him. With a few tugs, he got it fully hard.

“Wow, that’s a big cock,” I told him.

It was a big cock, maybe over nine inches thick. It had a large tip and thick veins. The old man’s balls were also large and heavy. He had a thick bush of pubes, by far the hairiest cock I had seen. The cock itself looked clean enough.

“Thanks,” he said, still unsure about what was happening.

I was a fan of massive cocks, so the site of it turned me on even more. The fact that I was about to give a random homeless man a blowjob in an alley had already turned me on. I got to my knees on top of the blankets and leaned in with my mouth open. As I took the tip of his cock in my mouth, I felt him relax.

“Ah fuck,” he muttered.

“What?” I asked him, taking his tip out of my mouth.

“I thought you were trying to play a trick on me,” he said.

“The only trick will be the ones with my mouth,” I told him cheekily.

With that I leaned in and took the tip back in my mouth. Even though it looked clean, it had a slightly dirty taste. As I sucked it, I must have cleaned it as the taste faded. I enjoyed giving blowjobs and sucking on big cocks was the best. This was one of the biggest I had sucked, and I was loving it. The old man was living it as well as he leaned back against the wall for support and gazed down at me. As I sucked his big old homeless cock like a real whore. I reached up and used one of my hands to work his shaft and the other to play with his big balls. Then felt as heavy as they looked, and he groaned softly as I squeezed them.

As he enjoyed it more, he reached down to hold the top of my head. He then started to thrust as I blew him slightly. When I did not react he held my head a bit firmer and pushed a bit harder. Again, I let him do what he wanted. I had a weakness for big cocks and for guys that like to use them to take control. Him slowly starting to face fuck me, and me dripping wet.

“Let me see your tits,” he said as he looked down at me with half his cock in my mouth.

By this point I was so turned on I would have done anything he wanted. I pulled back and let his cock go with a pop. I only had my jumper on with no bra. I pulled it off in one to reveal my slim and toned body and perky C-cup boobs.

“Fuck I’ve not seen a pair of tits in ages,” he muttered as he stared at my exposed breasts.

I gave them a squeeze for him before I went back to sucking his cock. As I did, he leaned down so that he could grab my boobs for himself and squeeze them.

“I forgot how good they feel,” he laughed as he gave my nipple a pinch.

Being topless in an alley, sucking homeless old cock, only turned me on more, and I started to make the blowjob extra sloppy. I soon had drool running down my chin, dripping onto my boobs. I stopped as I heard talking coming from the street. The nook we were in was close to the street, and I could hear people talking as they got close.

“We could cut down the alley. It’s quicker,” I heard a male voice say.

I started to panic. If these people walked a few steps down the alley, they would be able to see me topless on my knees, clearly sucking an old homeless man’s cock. I moved back, going for my jumper. The man grabbed the back of my head and stopped me. I looked up at him as he shook his head. I settled back down on my knees. As I did, he used his free hand to grab his cock and point it at my mouth. He used the grip on my head to pull me forward and slowly forced his cock into my mouth. He slowly fucked my mouth as we heard the couple carry on speaking.

“That’s the alley that old homeless creep sleeps in,” I heard a female voice say.

That creep was currently fucking my face. The sounds from that seemed to echo down the alley.

“He won’t try anything with me here,” the guy said.

“Nah, I would rather not see him,” she said.

With that, I heard their footsteps fade away. I relaxed as they left. The old man used that to force more of his cock into my throat. The noise coming from my mouth increased as he fucked my face hard and deeper. I gave him full control, and he used me for his pleasure. He fucked me like that for a while before he slowed down a bit. When he did slow, it was because his cock tensed up, and I felt him getting ready to cum. He slowed down more as I felt the first spurt hit the back of my throat. I swallowed as he came, and he filled my mouth to the point where some spilled out and down my chin. It felt like I had swallowed a cup full before he stopped cumming. He carried on slowly fucking my mouth until he started to go soft. He pulled out and slumped back against the wall.

“Thank you for that,” he said.

“You’re welcome,” I told him. I meant it as well, as I enjoyed it almost as much as he had.

“I’m Bob,” he said.

“I’m Misty.”

I put my jumper back on and left him half-dazed in the alley. I looked up as I left and saw Julie looking down at me. I pulled my phone out of my pocket and saw that I had been sucking his cock for over half an hour. My pussy was so wet I could feel it on my thighs as I walked back to my dorm room.

*****

“That sounded so fucking hot,” Julie said as I walked in.

I wasted no time a kissed her, shoving my tongue in her mouth. I could still taste Bob’s cum, so I knew that she could taste it as I kissed her. As we kissed, we stripped each other’s clothes off. Once we were naked, I pushed her onto the bed, and I straddled her face backward. I sat down and pushed my pussy down onto her mouth. Her tongue went straight to work, and it felt amazing. I sat and enjoyed it for a few minutes before I leaned down and put my face between her legs. Her pussy was almost as wet as mine.

I was so turned on that I came after just a few minutes. I let out a loud moan into Julie’s pussy as I did. She slowed down her licking but did not stop. My orgasm faded, and yet I felt another begin to build. I licked her pussy harder, and she slowly worked her speed up to match mine. Her legs began to squeeze my head, and I knew that she was close. I licked harder, and I felt her cum.

As she came, she pulled my pussy down onto her mouth and licked hard as she rode her orgasm. This made me have my second orgasm in minutes. This one was so hard my vision went black as I collapsed down onto Julie. I lay there exhausted as she slowly stroked my thighs and ass.

When stirred, I turned around and cuddled Julie. We fell asleep, still naked and covered in each other’s juices. That night I dreamed of big cocks and alleyways.

*****

It had been just over a week since I had given the old homeless guy Bob a blowjob. All I had thought about this past week was his large cock sliding down my throat. I had avoided walking past him as I didn’t think I could resist if he offered. I knew it was gross to give a homeless old man blowjob in an alleyway, but it was also so fucking hot.

Today, I had no choice but to walk past the alley. I needed to get to a class, and I was running late and could not go the long way around. As I left my building and walked down the road, he must have seen me as he popped out of the alley just as I got there.

“Hey, beautiful,” he said.

“Hi, Bob,” I said quietly.

“Fancy another go?” he asked as he grabbed at his groin. “I gotta nice big load for you to swallow.”

I felt my pussy quiver at the thought. “I can’t. I’m late for class,” I replied.

“What about later?” he asked, taking my lack of a no as a yes.

“Only if you shave it and clean it,” I told him.

I knew I was going to be back here later. Might as well see if I could get it presented better.

“Deal,” he said quickly.

I think he was shocked to have me semi-agree.

*****

I spent my classes all day thinking about sucking that cock in the alleyway, and I was shocked. My classes finished, and I headed to the gym for a workout. I put on my workout clothes, which were a tight tank top and yoga pants, and began my workout. I loved being in the gym; most of the people in here, boys and girls, were very fit. I would often come here to get turned on before going back to my room and fucking Julie or please myself.

I stayed at the gym until it got dark. I was going to shower there as those showers were better than the dorm ones. But I thought it best not to if the guy really had done as I asked. I had decided that if he did not, I would leave, but I also know that I probably would still suck him off.

I left the gym and started on my way home. The gym was only a fifteen-minute walk from my dorm. As I got close, I saw that he was standing at the edge of the alley, waiting for me. A few people were walking nearby, so I waited before going over to him. Once the area was clear, I walked over.

“Hey, I’ve been waiting for you,” he said.

“I bet you have,” I replied with a smile.

“I’ve done as asked,” he said as he pulled the top of his trousers down to show off his freshly shaved pubes.

“Good,” I told him.

At this point, I had been thinking about his cock all day, and I would have sucked it no matter what. He turned and walked into the alley. I followed him. He stood back in his little nook, and I got in and stood in front of him. He nodded to the floor, and I got the hint and got to my knees.

“You here for a bet again?” he asked.

“No,” I told him.

“Then why are you here?” he asked.

I did not answer as I did not want to admit why to him.

“Well, I know why,” he said as he slowly started to pull down his trousers. “You can’t resist my cock,” he stopped just as he started to show his cock. “Admit it,” he told me, stopping with his cock only half showing.

My mouth was open slightly as I watched. “I can’t stop thinking about it,” I admitted to old Bob.

“Good girl,” he said, smiling.

That made me blush, and I could feel my cheeks go red. Bob pulled his trouser the rest of the way down, and his large cock flipped up. It was already hard to make me admit I was crazy about his big old cock. With it being freshly shaved it looked even bigger than before. I felt my pussy tingle just looking at it.

“As good as you remember?” he asked.

“Better,” I told him.

“Now, put your hands behind your back,” he ordered. I looked up at him, a bit surprised. He was not this forceful before. I did as he asked anyway. “Good girl, now open that mouth and look at me,” he ordered again.

I did as asked and looked up at him. I opened my mouth and stuck my tongue out to make my mouth even more inviting.

“What did I do to get such an eager little college cock slut?” he asked.

As he did, he reached down with one hand to grab the back of my ponytail. The other hand grips his cock at the base. He pulled me forward a little as he pushed his cock towards me. He let the tip touch my tongue and held it there for a second. I kept looking him in the eye as pushed his cock into my mouth, stretching my lips open. He used half of his cock to slowly fuck my mouth. He did it slowly for a few minutes before speeding up a little and going a bit deeper.

My chin was soon dripping from my spit as he carried on fucking my mouth. He had let go of his cock, and now both hands gripped my head. Be held it still as he forced more of his cock down my throat. He got to the point where he started to make me gag. My eyes started to water as he held his cock deep in my throat. My chin was wet from spit, and now my cheeks were wet from my tears. He pulled his cock fully from my mouth. My spit still connected it to my lips.

“Did you enjoy that?” Bob asked, looking down at me with his large wet cock hanging over my face.

“Yes,” I replied breathlessly.

“Why don’t you take over then,” he said.

I did as I was asked and reached up to grip his cock. It was wet from spit, and I used that to stroke it. I lifted his cock up as I, stroked it and leaned in to suck his balls. They were just as big and heavy as last time. I could barely get one in my mouth, and I licked and sucked on them. He moaned as I did and let one hand rest on the top of my head. When his balls were wetter than his cock I moved back and licked my way up his shaft to the tip of his cock.

“Take off that top,” he told me as I just got the tip in my mouth.

I pulled back and lifted my top off over my head. I was not wearing a bra because the top acted as one when working out. My tits now exposed, he reached down and played with them. I kneeled there and let him play with them before he straightened and motioned for me to keep sucking his cock. The alley was soon filled with the wet sucking noise of me worshipping his old cock. I stroked it as I sucked it, taking his cock as deep as I could. I sucked his cock like this for a few minutes before he pulled back.

“Turn around,” he ordered. I knew where this was going to lead, but I was so turned on I would have done anything at this point.

I turned around and faced the other wall.

“Bend over,” he ordered next.

I got into all fours for him, giving him a view of my ass in my tight pants. I felt him get on his knees behind me. His hands went to my waist and pulled my pants and thong down together. I felt the air hit my glistening pussy.

“Fuck you’re wet,” he said as his fingers rubbed my pussy.

I just moaned as he did. I felt him shift, and then I felt his cock rub against my pussy. I moaned again.

“What do you want?” Bob asked.

“Fuck me,” I moaned back.

With that, he pushed forward, and his wet old homeless cock easily entered my soaking pussy. I had to try not to moan as his large cock stretched me out. I had never had a cock this size fuck me. He fucked me slowly and let me get used to him inside me. Once he felt like I was ready, he increased his pace. This time, the alley was filled with the sounds of slapping flesh and my low moans.

After a few minutes of fucking he slowed down. I could hear talking and realized people were walking near the alley. If someone came down, they would see me naked, getting fucked doggy by a homeless man old enough to be my grandpa. Again, this turned me on more for some reason, but I was relieved when I heard him walking past and not coming down. As he fucked me, his hands explored my body, grabbing my tits and giving my ass a few slaps and squeezes.

I was getting close to an orgasm when I felt something wet hit my ass. I realized that Bob had spat on me. His thumb moved the spit down to my asshole. Before I could do anything, his thumb pushed into my ass. Just as he did, the extra sensation made my orgasm explode. He kept fucking me and thumbing my ass as it washed over me, and I had to bite down on his blankets to stop screaming.

The orgasm was so intense I lost vision for a second. When I finally came back around, Bob slowed down and stopped. He pulled out and stood back up. I somehow managed to find the strength to get back to my knees and face him. He wasted no time in grabbing my head and forcing my mouth back onto his cock. He fucked my face even harder this time, and I could taste my pussy juices on it. I felt him tense up, and he pushed his cock in as deep as he could. His jizz hit the back of my throat, and I swallowed it as it did. He held me there as a river of jizz went down my throat. Finally, he stopped cumming, and he gave my mouth a few last pumps before letting his cock flop out.

“Fuck you’re amazing,” he said as he gazed down at my naked body.

“So is your cock,” I laughed back.

“Can I have your thong?” he asked. “As a memory of this.”

I could see no reason why not, so I slipped my thong the rest of the way off and handed it to him. He thanked me as he placed them in his pocket. I got myself dressed and left the alleyway.

*****

When I got back to the dorm, Julie was not there. I showered and passed out as soon as I got into bed.

After that night, I did not see the old guy again down the alleyway. I even checked one night to find all his stuff was gone. About three months later, when I was walking home one night, I heard a voice from some bushes in a vacant lot.

“Hey, wanna have some fun, cutie?” the voice said.

Bob,’ I thought and headed toward it. I entered the lot and went behind some bushes to find an old man stroking a huge cock. It wasn’t Bob.

“Sorry, I thought you were someone else?” I said, readying myself to run.

“Come on, suck my cock for me,” he said, stroking his circumcised meat.

This cock was huge and thick, but it looked dirty. As did those hairy balls hanging down so low. The man must have been at least seventy.

“That’s gross,” I said, but I couldn’t take my eyes off that big cock.

“Come on, I got a lot of smegma down there,” he said and leered. “Come and taste my cock cheese.”

Not long after, I found myself in the corner of a dirty vacant lot, naked on my knees as this nasty old homeless man forced my head down his large, smegma-ridden cock. I sucked his cock like that until I had eaten every nasty gram of smegma (and there was a lot) and then swallowed every drop of his jizz after he face-fucked me for twenty minutes solid. Then I licked his balls and asshole clean, too, just for good measure.

We sat back and spoke some afterward, and he shared a joint and some booze with me. I stayed naked with my face a mess as we did. It was not long before he was hard again, and he fucked my cunt hard before he pulled out and came for a second time down my throat.

After, I said, “I better be going.”

“I ain’t done with you yet.  Do you wanna do something really dirty?”

“Yeah,” I moaned.  “I love it dirty.”

“Then get on your hands and knees, slut.”

I complied and presented my rear to the old homeless man.  He spat on his fingers several times and worked his finger into my asshole.  I squirmed and squealed, but I took it and didn’t complain or resist.  This goes on for a while.  The man finally gets it so two fingers can slide in and out without too much resistance.  At that point, the old homeless man judges it’s about as wet as possible.  He spat on his fingers one last time, pushed them back into my ass, and banged them in and out a few more times.  I squeal louder, and my soft whimpers turn to louder moans.  But I wasn’t telling him to stop and was pushing back when he stuck his fingers in my tight shitter.

The old homeless man pulled his fingers out, spat in his hand a few times, and rubbed his saliva all over his cock.  He does that about a half dozen times.  By then, he knew it would be now or never, and he pushed the head of his cock into my anus.  I gasped loudly, sucking in the air with a mild shrieking sound.  The old homeless man pumped it slowly, pushing in a little deeper with short, gentle strokes.  By now, I was crying as it was painful.

“What’s wrong, girl,” the old homeless man said harshly.  “Never had a cock up the ass before?”

“No, you’re the first,” I said through clenched teeth.  “I’ve had fingers but never a cock.”

“So, I’m busting your anal cherry,” he said with pride.  “That’ll teach you for letting a dirty old man like me have his wicked way with you.”

“Just go easy.  Let me get used to it.  Your cock is big.”

She’s little, and the old homeless man is large.  Her asshole is small and tight, and the old homeless man’s cock is big and super hard.  They’re not a good match, especially with no lube.  The old man eventually pushed his cock into my asshole.  He let it lie so I could get accustomed to it and slowly started pumping it in and out.  Not long strokes, just short little ones.  The man probably would’ve cum right about then.  My ass is so tight, and he’s so horny.  He has his big old cock up the ass of a college girl.  It’s mind-blowing.

Eventually, he can draw it back a few inches and push it back in, pulling it in and out quicker.  By then, I was moaning and gasping every time he pushed inside me.  When I pushed back, between the moans, I let out a kind of ‘Oomph’ sound, like somebody taking a stomach punch, except there was a pleasurable, erotic note.  It’s painful for me, but it’s also clear I like it too.

Soon, it gets to the point where the old homeless man can’t take it anymore.  This college girl’s ass is so tight, and he’s so horny, and those oomph sounds are the most erotic noises he’s ever heard.  He felt ready to climax, so the old man sped a little and pushed in deeper.  After a few more balls-deep thrusts, he arched back, involuntarily shoving his whole cock into my asshole, and exploded.

Ah … God … Fuck…” he moaned as he ejaculated in my bowels.

The man falls on top of me, pushing me into the dirt.  When he recovered from his intense climax, he pushed off me, and I felt his cock slide out of my burning asshole.

“Oh, great, would ya look at that,” he said harshly.  I turn my head to see him staring at his cock, which appears covered in my shit and possibly some blood.  “I can’t go around with my old cock looking like this.”  The old homeless man gazed at me and grinned.  “Get over here and suck it all clean, you dirty little slut.”

“Gross,” I said with a sneer.

“Come on. You are all that smegma and licked my asshole, so this is nothing.  Do it.”  I got to my knees and crawled toward him.  “God, they broke the mold when they made you, girl,” he said, impressed by my stamina.  “Come on, lick it clean.  Make it nice and shiny for me.”

I grabbed his dirty cock and licked the shit, semen, and blood off it.  The taste was awful, but I endured it.  It didn’t take long for me to make it clean.

“And my balls, too,” he ordered.  I licked his sweaty balls as well.  “Clean my ass again.”

I obediently licked his asshole for about five minutes.

“One more thing before you go.  Open your mouth and keep it open.”

I sat back on my knees, wondering what he had planned.  When I opened my mouth wide, the old homeless man grabbed his cock and started pissing in it.  The shock makes me jump and, unfortunately, swallow a whole mouthful.  I closed my mouth and shut my eyes as the old homeless man kept pissing on my face.  Then he laughed loudly and started aiming his stream at all parts of my body.  I was drenched in his nasty piss.  My hair drips with it.  I was coughing, feeling as if I was about to vomit.  The old homeless man grabbed his pants and put them back on.  He stood and stared at me for a moment.

“You said you wanted it dirty.  I hope that was dirty enough for you.”

“Yes, sir,” I said, head bowed.

“It was an honor to take your anal cherry.  I guess that means you’ll never forget me.”

“No, I won’t.”

“Are you gonna tell on me?” he asked, a flash of concern over his face.

I shook my head.  “No, your secret is safe with me.”

“Good,” he said, his shoulders sagging some.  “Come back when you want me to tap that ass one more time.”

“OK,” I said.

He quietly dressed, grabbed his stuff, and left.  I was alone.  I put my clothes on and headed home. I desperately needed a shower.

 

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*This eBook contains adults-only taboo erotica. All human characters in this story involved in any sexual behavior or acts are over eighteen. Any similarities to real people or real-life situations are purely coincidental and unintended. This eBook is 100% fiction, none of this ever happened in real life. The taboo themes of this story are fine for sexual fantasy, but only a fool would do them in real life. Do not try this at home. This disclaimer voids GW Enterprises Publishing Company against any claim that our stories have been a motivation for criminal activity. You are responsible for your actions. Thank you for reading this free sample.

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