Street folks/homeless

[Guest]

Had a few experiences that really were hot to me. I actually had taken an uber over to a hotel to meet a top. I was chemically enhanced and wanting more. As I came out and was preparing to get an uber home. I saw all these people just wandering around. I had a backpack so I fit in.  This is a very populated area of homeless or hoogers as I call them (up to to something). I love to show off my ass by wearing a jock and saggy shorts. I was sitting on the end of the concrete when a hot muscular black man approached me. He asked me what I was up to. My reply was nothing good. 

He laughed and referenced my visible jock and said, "I can see that"...we ended up in the woods with his huge piece pounding my hole until he came. Introduced me to others who helped out also. Am I the only perve out there that think this way?

Edited August 23, 2022 by barerobb76
Needed more detail

[ademiakari]

I wish more dudes wanted to fuck me when I was chemically enhanced like that!  

[PromiseYouPullOut]

I haven’t played with any homeless men, but one night I was quite drunk, some crazy homeless woman told me if I gave her five dollars, I could fuck her. We found ourselves a little alleyway, I fucked her, raw, and gave her a huge load of my cum. 

[Barebacker831]

2 hours ago, PromiseYouPullOut said:

I haven’t played with any homeless men, but one night I was quite drunk, some crazy homeless woman told me if I gave her five dollars, I could fuck her. We found ourselves a little alleyway, I fucked her, raw, and gave her a huge load of my cum. 

Hell yeah, that’s really hot

[sedecki]

In 2017 I was at a business conference in St. Louis. After I got done for the day I popped over to Club St. Louis which is a nice bath house in a somewhat sketchy part of town. Had  a nice time playing. Two guys took turns fucking me in a sling. Had a lovely time on the roof patio sharing a joint with a cross-dressing fem bottom. As the night wrapped up I stepped outside at about 1:00 am and planned to call a taxi from there.  Before I could dial a big black guy who looked homeless yelled at me from the street. He was standing under a light pole pointing his finger at me. 

"Hey can I get five dollars from you?"

I said "How big is your cock?"

He pulled down the front of his pants to show off a 9 inch monster as thick as my wrist. I walked down to the street to take a closer look. He flopped it at me a couple of times and grabbed it by the uncut tip and pulled it up in the air. "You like this?"

I nodded and reached out to stroke it. "You fuck?"

"Maybe."

I pointed at the dark space between two buildings across the street. "Lets go over there." As we got into the dark part I got disoriented and slowed down. He bumped into me wrapped an arm around me. Suddenly I figured out I had put myself in some danger, but he was cool and started rubbing his cock against my ass. I slid my pants down and pulled out my poppers and started hitting them. 

"Suck it." 

I dropped to my knees and took his cock in my mouth. It smelled strong and musky. I struggled to get my lips around and slide them up his shaft. I felt his cock start to swell. Salty precum dripped into the back of my throat. I pulled loose and swallowed then stood and hit the poppers again. His fingers rode into my crack which was still lubed from the bath house. He shoved one finger up, then two. I moaned a little and pushed my ass toward him. I felt his big cock head pushing up against my asshole.

"You ready?"

I hit the poppers again and creaked out a "yes." He shoved his cock and the head popped straight in. He paused for a moment then pushed the rest of his cock inside me. The thickness spread my ass too wide and he took my breath when he shoved all the way in. I had to ask him to stop for a second. When he started again we were both in the rhythm. Within a minute I could feel him shooting up my ass. As he pulled out I took his hand and shoved a $20 in it. 

Worth every penny and then some.

 

[20cmcock]

I found a homeless guy at a beat. Massive cock. I started sucking him and offered him my arse. At first he was reluctant because neither of us had condoms, but I kept at him and he decided to fuck me. He told me when he was about to cum and wanted to pull out but i backed him up against a table (we were fucking doggy style) and he couldn't.

I thanked him for his load and went for a walk. On my way back, he was still there and told me he was horny again. The second time he didn't need convincing to fuck raw.

I've been back there a few times since but i haven't found him again.

[Niceroundass]

I have had some GREAT Homeless Men fuck me as they like; I have brought Homeless Men home to my apt to fuck me and there have been occasions where they have actually stayed from 1 day to 3 or 4 days and had thoroughly used me for their pleasure...

However; the best were about the ones that I encountered and di not want to come back to my apt; so some just fucked in alleyway; a couple used to fuck in behind dumpsters behind buildings; some I took to the Bookstore to fuck me or a Bathhouse (at the Bookstore it was pretty hot due to all the others there looking at me with these Men and taking them into the Booth with me - mot times left the door open so they could see....

Of all these there were a few who took me to their encampments and some just did one on one but there were  occasions where it turned into a little group session and I was the Guest Pig Bottom...  And even on more than one occasion I spent the entire night at camp with them..

So if you or anyone would like to chat more about these let me know.....

[Raunchyfag]

I've only been successful once and It was while cruising. I was waiting in the dark when  he came over and stood not far from me. I got close and grabbed his dick which was already rock hard! He smelled a little but nothing crazy. I asked him point blank if he was homeless and he said yes. But by that point  my cunt wanted that rock hard cock ( he was hung too). So I got on my knees and started to suck and I was surprised at how much I liked the taste of his dick! If you're into musk/manly smells/tastes homeless guys are the holy grail. I was instantly hooked. After sucking him for a while he ate my hole and got it nice and wet. After that he started teasing my hole with his dick. If there were any reservations about taking his raw dick they went out the window the moment he started rubbing his fat cock on my hole. Before I could say anything the head popped in and I had the biggest pleasure rush I've had since I was a boy. He fucked me good and hard bent over like a common whore. Fucked me until he got me pregnant and sent me home with his load dripping down my legs. I've been back so many times hoping to run into him again but so far no luck.

[Lily95]

Haven't been lucky to get any men not even homeless men. I dont even know how to tell if they want to fuck me or not 

[Hispnbttmboy81]

On 8/24/2022 at 12:42 PM, Niceroundass said:

I have had some GREAT Homeless Men fuck me as they like; I have brought Homeless Men home to my apt to fuck me and there have been occasions where they have actually stayed from 1 day to 3 or 4 days and had thoroughly used me for their pleasure...

However; the best were about the ones that I encountered and di not want to come back to my apt; so some just fucked in alleyway; a couple used to fuck in behind dumpsters behind buildings; some I took to the Bookstore to fuck me or a Bathhouse (at the Bookstore it was pretty hot due to all the others there looking at me with these Men and taking them into the Booth with me - mot times left the door open so they could see....

Of all these there were a few who took me to their encampments and some just did one on one but there were  occasions where it turned into a little group session and I was the Guest Pig Bottom...  And even on more than one occasion I spent the entire night at camp with them..

So if you or anyone would like to chat more about these let me know.....

How was the camp night with them?

[PiggyNJBttm]

On 8/24/2022 at 3:42 PM, Niceroundass said:

I have had some GREAT Homeless Men fuck me as they like; I have brought Homeless Men home to my apt to fuck me and there have been occasions where they have actually stayed from 1 day to 3 or 4 days and had thoroughly used me for their pleasure...

However; the best were about the ones that I encountered and di not want to come back to my apt; so some just fucked in alleyway; a couple used to fuck in behind dumpsters behind buildings; some I took to the Bookstore to fuck me or a Bathhouse (at the Bookstore it was pretty hot due to all the others there looking at me with these Men and taking them into the Booth with me - mot times left the door open so they could see....

Of all these there were a few who took me to their encampments and some just did one on one but there were  occasions where it turned into a little group session and I was the Guest Pig Bottom...  And even on more than one occasion I spent the entire night at camp with them..

So if you or anyone would like to chat more about these let me know.....

I’d love to hear more about this. HUGE fantasy of mine

[Guest]

On 8/23/2022 at 2:04 AM, barerobb76 said:

Had a few experiences that really were hot to me. I actually had taken an uber over to a hotel to meet a top. I was chemically enhanced and wanting more. As I came out and was preparing to get an uber home. I saw all these people just wandering around. I had a backpack so I fit in.  This is a very populated area of homeless or hoogers as I call them (up to to something). I love to show off my ass by wearing a jock and saggy shorts. I was sitting on the end of the concrete when a hot muscular black man approached me. He asked me what I was up to. My reply was nothing good. 

He laughed and referenced my visible jock and said, "I can see that"...we ended up in the woods with his huge piece pounding my hole until he came. Introduced me to others who helped out also. Am I the only perve out there that think this way?

Fuckin hot story man I've fantasized about doing that for years 

[AlwaysOpen]

Man , some of you guys have me in awe at how you didn't hurl lunch with the homeless guys.  Back in the stone age when I was getting my EMT certification, I had to do 16 hours in an ER working with the doctors and nurses. My first 8 hour stint began with a homeless guy who was drunk and had passed out on the street. I helped transition him from the stretcher to the ER gurney, and just that "aroma" had my gut bubbling.  About 5 minutes later he was hollering for the nurse, so one of them had me follow and we went to see what his problem was. Duh! He was a drunk, had been drinking cheap beer all day, and the rental was about up on some of it.  She went over to a sink area and produced a stainless steel urinal,  came back and handed it to me and told me to help him with it, and she stepped away. Now , the guy had 2 or 3 pairs of stinking pants on and each layer had to be released and peeled back. When his cock was finally exposed, besides being pretty shriveled  and unimpressive, it was uncut. He couldn't see to put the urinal in the right position, so I ended up right above the damned thing using the lip of the urinal to sort of get , flip the head in line to piss down into the  container. About then he skinned it back- and the stench was probably the worst odor you ould imagine. Not only was there smegma all curdled up under there, there was enough stale piss and other things of the street  wafting up and filling the space. I  managed to get the task done, but then had to take the urinal to the slop sink and pour it down, then put the mouth of the urinal over a sprayer that rinsed it out and made it "ready " for the next patient ( this was the early 70's, so the concept of single use was not prevalent ) About a year later, my car got the interior soaked when a thunderstorm blew thru, and of course the windows were all down. About a week of keeping the windows down and parking in the sun as much as possible, and the car seemed dry. But with a funky odor. As I pulled  the floor mats out it got stronger, and as I lifted the floor covering, the wool batting/padding was a fermented , stinking mess. And the smell triggered my memory- that smell of rotting fermented wool padding was the same retching smell of that homeless guys cock. Oh, if only FeBreeze had been invented back then lol

[hntnhole]

I simply don't know how you medical folks can actually manage to function.  My sister is a nurse, and I've heard stuff that would make me hurl from only hearing about it.  If there's a "higher calling" on this planet, it's health care workers.  

[RyaPlays]

I was homeless in Seattle