We desperately need to revisit this topic. It hasn't been talked about here in a while. I need to mention two that come to mind.
One, a squeegie guy from the mid-90s, pre-Giuliani having them killed or whatever he did to them. I was waiting in traffic to get to the Lincoln Tunnel when this black god came to my window. Handsome as hell and shirtless. He had an incredibly ripped body with a mouthwatering treasure trail. He climbed on the hood of my car to wash my windows and I could see a bit where that trail led. I jerked off, of course, as he he my windows, and I gave him $5. He saw me JO-ing, and joked that I need to get a girlfriend. Um, yeah, right. I want to suck off your hairy cock, and I need a gf? Whatevs!
A second guy was a homeless black hustler I met on the street near Port Authority last summer. It was a hot day, and he was standing there shirtless. Very thuggish looking. His upper body was just ridiculously hot. I cruised him several times, and he finally took the bait. He followed me down to 38th St. He approached me and said hello. He was just breathtakingly beautiful. We walked for a bit and he told me his hard luck story. I told him he was very attractive. We ducked into a construction site on a side street. I told him that I need to see him totally naked. He pulled down his jeans to reveal a huge piece of meat. He asked if I wanted to suck on it. I told him no. The sight of that against his muscular torso practically made me cream. I JO-ed myself through my pants and thanked him for that. I gave him $20.
This is why they hate us.
Well, I did see a skinny homeless guy on the street today in tight, thin, white pants and no underthings. Anyone looking could clearly have made out the size, shape, and every detail of his unit. Which looked rather extraordinarily thick and heavy. \
Is that satisfactory, OP?
Did he fuck you, Dolores? I mean R2.
It always depresses me when I see a gut who is literally homeless and he still has a hotter body and face than I do. \
God is mean.
Yeah, R4. I''m sure you''d trade a home, food, a job, and all the amenities of life just for a pair of killer cum gutters.
You can get a home, food, a job, and all the amenities of life if you HAVE a pair of killer cum gutters.
I prefer hot serial killers.
I''ll bet Dan Savage and his husbear have plenty of similar stories to tell!
OP there''s no telling what dread diseases you have currently with all this sex you''re having with homeless quadroons.
I just lifted my muumuu Miss OP!\
The treasure underneath is for YOU, BABY!\
Come and give my propers!
This is why they hate us This is why they hate us This is why they hate us
I am not quite sure what constitutes sex in what OP posted, R9.\
Anyway, I was walking home drunk from some bar in the east village in NYC and I was just making it past St. Vincents on w. 13th St. It''s a dark block. There were a handful of homeless guys sprawled out and sleeping on cardboard boxes. It was a hot night and this lean, beared white homeless guy, no more than 40, was laying on his cardboard box stroking on his long fat dick - masturbating, like we all do I guess, before bed. It was rather shocking and hot. He caught me watching him and immediately stopped even though I drunkenly asked him to continue. I felt bad for interrupting what little privacey he had.\
I walked around to the Chase around the corner, took out $100, and left it on his cardboard box. I am way too generous when I am durnk.
Brava #12! The perfect combination of poignant, sad, and disturbing.
"We desperately need to revisit this topic."\
No we don''t.
I sometimes have this lifetime movie type of dream where I pick up a homeless young boy and give him the best future possible by providing him with food, shelter, unconditional love (nothing sexual, it''s a Lifetime Dream Special after all!) and access to a proper school education and everybody is in awe of me being a single gay parent (yes, I manage to adopt him after I deal with his drug addicted excuse of a mom).
I was working as a summer park intern in Chicago and ran into this guy in his 20''s sleeping in my park. Cute, blond, muscled. He had just got out of jail and his wife threw him out. I took him home. Cleaned him up. We had fun sex. Gave him some of my clothes. Took him out to breakfast the next day, gave him $50 for a ticket to his parents and said goodbye. \
A few months later, I don''t know how he got my college address, but he sent me a picture of him with his kids, was divorcing the wife, and a thank you letter for helping him get back on his feet.\
This is why some of them do not hate us and I still jerk off to the memory.
This thread is worthless without pictures.
What a deliciously creepy thread! Please continue.
Yes, nearly 3 years later, I think we need to continue.
Do it, R19.
I was at a party around 2003 and ended up sleeping with the host. We fucked that night and then the next morning we fucked again. In the middle of the morning sex, his buddy, this ex-military guy who had crashed on his couch (as I recall, there were several people, including a chick who'd passed out at his place and were scattered about), came into the bedroom and joined us in a tag-teamed. Dick for days and fucked like a champ. It was quite a fun night/morning. Fast-forward three years and I'm walking down the street on my way to work, when I see this homeless guy shlumped up against a wall. His hair was all grown out, bedraggled beard and wearing an army jacket. It was unmistakably that guy's buddy (I never forget a face). I was so shocked by it that I just kept walking. I wish I had gone back and offered to take him out for a meal or given him a couple bucks, but I was honestly so surprised by it that I wasn't thinking straight. Unfortunately, I never saw him again.
I saw this toothless, dirty homeless guy in front of Home Depot last week. He asked me for $20.00. I told him to bend over and drop his chinos. I ate his hairy, crusty, filthy, track-marked, dingle-berried ass for ten minutes and gave him a crisp $20.00 bill. He turned around and spooged on my glasses. The hottest homeless encounter I ever had. The hepatitis I got is totally worth it.
I picked up a homeless guy once. He was blond and scruffy, not bad looking. Lean and sinewy.
He stripped off, sat back and let me blow him while a porno movie played. He was there for several hours and blew 3 loads. Told me I was a good cocksucker.
I sucked off a filthy homeless guy once. He was passed out under a freeway bridge and I yanked his tattered pants down and went to town. After he blew his load on my face, I realized it was David Hasselhoff passed out after a bender. I was so disgusted I ran away.
"hot homeless guy with beard and shaggy hair
you're young, hot, and homeless. you look to be about 20-25. you have brownish red shaggy hair and a nice beard. i could tell you were homeless because you were eating chips off the ground and you had urine soaked filthy pants on. i've always had a thing for the "starving artist" types and your homeless ruggedness is hot. i have seen you sleeping in one of the bus stops near public square. if you ever steal a laptop or break into a library or someone's home to use their computer, i hope you read this. ~Brittany R. "
"You can get in my bed but not my wallet." I always say that when a hot one begs for money.
I used to get them homeless girlies to straddle my glass coffee table and put on a tasty show fer me. That girl daughter of mine had to clean up the mess the next morning. Really turned her into a sour-puss. She's still a bitter old bitch. LOL.
As a former "hot" homeless guy, OP is not lying. Midtown is full of them. Plus, they know the routine
In my twelve years of DL, this thread is possibly the most befuddling.
I can't even fathom thinking a homeless guy is hot. By definition, they are gross. If someone appears to be homeless, they are dirty and disheveled and strange looking.
If not. I won't think they are homeless.
Are we talking about hot street hustlers? Or panhandlers? There is a difference.
I'm actually the OP of this thread from way back when. I live near an SRO on the UWS, and there are some hot guys who come and go there. In the summertime, they usually hang around shirtless outside the hotel. There's a little deli next door. There's actually one regular there whose attention I'm trying to get. White guy, late 30s, with an incredibly cut, sinewy body with hair in all the right places. I see him roving the neighborhood, and I'm incredibly hot for him and I want to let him know that my hole is available if he wants it.
R23, what did his junk smell like? I need to know!
Where are these hot homeless guys in Midtown? Where do I look? How do I spot them? I'm definitely interested.
A couple years ago, I met a homeless guy in the Ramble in Central Park. Day before St. Patrick's Day, after dark. He was extremely charming, good looking. Very Jack Nicholson. Probably early 40s. We had an amazing conversation. I think we kissed a bunch, too. He fingered my asshole through my briefs. He was straight, but very manipulative. He was wearing about 5 coats. His stories were so incredible and he was so charismatic that I ended up befriending him for a while. Had to cut the cord once I realized he only wanted a place to stay. Not just my place, but my bed. Without me in it.
One of the strangest and saddest experiences I've had in New York City.
His genitals smelled just fine. He had showered that morning at a shelter and had on clean clothes. In fact I sucked 3 loads out of him because he was so "fresh". I would have offered him a shower.
I need a shower after reading some of these stories.
Please, more hot homeless stories!
OP, he climbed on to the hood of your car?
And "of course" you jerked off while he was doing it?
Where am I, and how did I get here?
APT PUPIL features Elias Koteas as a hot homeless guy who gets picked up by Nazi sadist Ian McKellen. McKellen looks out his back window to see Elias Koteas as a deliciously rugged vagrant - bearded, wearing a hat, scarf and a sparkly woman's sweater - rummaging through the trash in search of a good meal. McKellen invites Elias into the house, Elias offers him a BJ, but McKellen stabs him in the back and throws him down the stairs to his basement. When it is later revealed that Elias has survived the knifing, Brad Renfro beats him to death with a shovel while he begs for his life. Good representation of a hot homeless man.
Was it Dr Phil who devoted an episode to men whose kink and as homeless women? They showed their guests approaching cardboard boxes under bridges, crawling into tarpaulin tents, getting their groove on...
Very early in the mornings I always see this hot black muscled homeless guy, about mid 40's, with a torn opened sleeveless worn-out flannel with old loose jeans with broken zipper held up by a an old belt sitting underneath an overpass as I take a morning jog always asking for change. I usually give him a couple dollars. I get horny seeing him. So now when I jog I stop on corner before I pass him at his usual spot and walk by instead only I have my hard dick hanging out flashing him and jack off in front of him under overpass. My loads are so intense and he just watches intently. Then I give him a few dollars and be on my way. Now anticipating my arrivals in the mornings he has his massive hard dick out slowly stroking sitting on ground in usual spot not saying a word as I jack off in front of him letting my cum fly everywhere. This has been going on now about a year. Sometimes we jack each other off too. Great starts to my days. I often see him walking aimlessly around town collecting cans. I even recorded some of these encounters for my own private viewing in case one day I no longer see him.
People are under the false impression that all homeless people are scruffy looking, some have jobs as well but can't afford a decent place to live.. I have known a few hot young guys that were homeless and were clean cut in their appearances. As one of them told me once, "Just because I am homeless doesn't mean I have to look rough".. Younger homeless people do care about their appearance, so those who you are talking about would be the much older ones.
Does Brandon qualify as a "hot homeless guy"?
[quote] Does Brandon qualify as a "hot homeless guy"?
No, because he is actively campaigning not to be homeless. Donate now to prevent a good-looking person from being homeless.
Stay away from the drug users and hustlers who tell you sad sob stories to squeeze out all the money they can get out of you.
Brandon has a job. He doesn't need the cash.
R41 has kind of a Patrick Bateman feel to it for me.
I've told this here before - One day while I was standing waiting for the bus, I see a very muscular man in filthy, filmy, gray sweats that had been cut down to make shorts, coming down the street. No shirt.
As he is walking towards me I can't help but notice his big dick swinging under his shorts. As he gets closer he sees me staring (and I had no will of my own to stop) at his meat and starts to get hard.
When he passed by me I turned and faced the street but as he kept walking he kept looking back. By this time he was rock hard but he kept walking.
I'm watching him and as he passes these two guys standing at the corner - they see his dick and then look up the street to see who he kept turning around to look at and there I was. For some reason (I'd started it!) I felt really embarrassed about it.
I don't misbehave the way I used to, but if it had been a few years earlier, I would have gone after him without giving a second thought to anybody watching as the situation transpired.
Thanks for bumping this thread ...haven't read it all yet, but enjoying the laughs.
R15 with his Pretty Woman Lifetime movie fantasy ...except for the icky adoption.
And R16 ...smell her ...going from working in the park to owning it in the space of a sentence. MY park indeed, Mary.
Off to read more
Right next to my local cruise spot was an abandoned convent,and one night I met two homeless guys who were staying there. One was young,about 25,slim,dark haired and very cute. His friend was about 35,kinda chunky but in a solid way,and as hairy as a chia pet ! We chat and I accept their offer to "hang out" for a while at their squat.
We get there,and to my horror I had to scale a tree to get into a window as it was boarded up. That almost made me do a u turn but horniness prevailed. We get inside,smoke a joint I had, and the skinny guy and I immediately started kissing and groping while the chunky one just watched. I thought maybe hairy guy wasn't as into it as the young one,but he stood up,walked over to us,and immediately started throwing tounge into both our mouths.
Within seconds,we were all naked and the skinny one had a nice respectable piece,but the hairy one,My God,it was like a fire hydrant. Very ,very thick and about 7 inches long. His balls were huge too. There was a pile of moving quilts nearby,and before you could say "Poof" I was laying there face down,chewing on the fire hydrant while the young one ate my ass then slid his dick in.
He fucked me for a good 15 minutes,then switched with hairy guy. I still clearly remember that fat dick trying to slide in,and even though I had just been fucked,it was rough going. Finally,he got it in,then proceeds to pound the shit out of me while holding his hand over my mouth to quiet my screams of ecstasy ! It went on for what felt like hours,but was only probably 10 minutes,then with a massive groan,shoots into my torn up hole.
The whole time he fucked me skinny guy masturbated,and when his friend came he shot his load all over my face. After a while,we all got up,got dressed and left. I went back to the park the next night (of course) and for many there after,but I never saw them again. My hole was sore for a week.It was one of the best fucks I ever had !