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Would you ever fuck with a homeless person?


Sharp-edge

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Just come back from a week in the US. First city was Washington. I have put an advert out on BBRT, a young black guy answers and says he is interested. We chat a bit, and agree to meet in my hotel.

I meet him in the lobby, he has a sports bag and 2 large bags with him. Going up in the lift I comment on the bags. He admits that he is currently couch surfing. Big alarm bells are going off in my head. We are at my room at this point. We go in strip, he takes my poppers, big hit, and promtly eats my arse for ages, and then breeds me. Not the best fuck I have ever had, but not half bad one either.

He cums quickly, so I offer him a shower. Now he goes in there and must have been a good 15 minutes at least. Comes out and takes 10 more minutes to get dressed. I wanted out as I had things I needed to do. But apart from the time taken to clean up, he was charming. Said he was hoping to find something soon. If I had known he was homeless before. I would not have met him, but whilst I think there were some issues there,  he got upset that whe n he gave his name, I did not immediately give mine,  he was a nice guy. I really hope he has got himself some place to live.

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On 8/28/2023 at 12:23 PM, 120DaysofSodom said:

I was smoking with a homeless dude that was always in the alley behind my apartment and ended up letting him fuck me out there. When my ex boyfriend and I lived together, lots of times I would use the excuse that im tossing trash in the dumpster and having a cigarette and id go down to the alley or the sketchy dark laundry room and let the homeless crackhead fuck me. Id guess he fucked me probably 15 or 20 times before we moved to a different place. He was gross but it was a hot fantasy to cheat on my boyfriend with a homeless crackhead so I let it happen over and over.

Damn thats hot Would have loved to partake

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  • 1 month later...

Just this past week thins Gypsy looking kid with blonde dreads comes up to me at the gas station and asks for $10. I give it to him and told him “the only reason I’m giving this to you is because you’re cute.” He responds “oh I’m straight.”

I come out of the gas station and he asks me if I have a couple more dollars. I say “gay guys get a full tank, straight guys get $10.” I get in my car and drive off. 
 

I don’t feel bad or like I was taking advantage of him. Putting aside the fact that I don’t believe a young Gypsy drifter kid with blonde hair has never naked with another guy, I felt I was generous enough giving him $10. Anything else was going to cost him. 

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13 hours ago, BlackDude said:

Just this past week thins Gypsy looking kid with blonde dreads comes up to me at the gas station and asks for $10. I give it to him and told him “the only reason I’m giving this to you is because you’re cute.” He responds “oh I’m straight.”

I come out of the gas station and he asks me if I have a couple more dollars. I say “gay guys get a full tank, straight guys get $10.” I get in my car and drive off. 
 

I don’t feel bad or like I was taking advantage of him. Putting aside the fact that I don’t believe a young Gypsy drifter kid with blonde hair has never naked with another guy, I felt I was generous enough giving him $10. Anything else was going to cost him. 

Agreed, you were kind enough to give him $10.00.  Then he suddenly asks again, after making the  remark "Oh, I'm straight.

I would think the majority of people would have ignored his plea for the $10,  Your feelings that you were generous are spot on.   He was trying to "play" you, the fact that he asked for additional cash leaves me at a loss for words.  Did he think you were a walking ATM machine?  Glad you just drove off.

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  • 2 weeks later...

One of the best cocks I've ever had was a homeless young man from our city mission. I encountered him at a local park in the bathroom and was VERY pleasantly surprised by his BBC. He was a shower and a grower. 7 or 8 inches flaccid and 10 inches hard. SO MUCH FUN deepthroating him. 

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On 1/12/2024 at 8:55 AM, ellentonboy said:

Agreed, you were kind enough to give him $10.00.  Then he suddenly asks again, after making the  remark "Oh, I'm straight.

I would think the majority of people would have ignored his plea for the $10,  Your feelings that you were generous are spot on.   He was trying to "play" you, the fact that he asked for additional cash leaves me at a loss for words.  Did he think you were a walking ATM machine?  Glad you just drove off.

Depends where ur at. Believe it or not this is a common way to get picked up in Ottawa. They hit on you, they show Interest. But as soon as you Bring up gay... They assure you they are straight... And they move away. 

Then they linger for like 5 minutes confused why you don't follow them

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yeah i get fucked by homeless men all the time. its amazing how easy it is to get them to fuck my fem little body. i even have a few regulars and they help me find other homeless guys willing to fuck a t-girl. usually, they do me in a park or an alley when its warm or a public restroom when its cold/rainy. I just got fucked by a couple of my favourites yesterday in the mall. we all went into the handicapped stall and they took turns back and forth for about 10-15 minutes (they wanted to give me big loads.

the first time it happened a guy who had been using me and passing me around in a porntheatre (another place i have been fucked by lots of homeless guys) brought me to a downtown park at like 6am (he had me walk there in just bootie shorts and shoes, and had me get on my knees a few times to suck his cock on the way, including at a stoplight at a big intersection while a few cars drove by then took off my shorts (no underwear) and fucked me in the park while a homeless man and a woman stood there watching. after he came in my ass he offered me to the man and said “wanna use this faggots hole? it’s nice”. that man fucked a load into me then he had me get on my knees and jack off while they both pissed on me/in my mouth and told me to cum before they finished pissing. the woman loved it.
 

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  • 3 weeks later...

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..

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I probably posted this before, but I probably would not. I'm WAY too polite to ask someone to leave. Once they told me they were homeless, I think I could be easily manipulated.  Call is a "character flaw", but I have a real problem telling people to get out of my house.

 

 Excuse me for my due responses. but I had sex with someone who had just been released from a hospital.  I, along with my BF, met him at an ABS.  We messed around a little at the ABS and started walking back to our car.  Somewhere in the conversation the subject of "So where do we drop you off afterwards" emerged, and that's when the conversation went "south".

You know, I do have empathy, and maybe that is a character flaw.  But, in the end, we had to tell him no, and I drove away from the ABS feeling VERY guilty.

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