Ever Been Fucked By A Homeless Guy?

[joethomas]

Two major firsts for me in the past few days: Fucked by a porn star a few days ago, and last night fucked by a homeless guy.

I'd just pulled into an almost-empty parking lot of a local gay bar in a somewhat sketchy part of town when a really young black male (i'd guess early 20s) started walking out of a shadow near a tree-line and toward me as I got out of my car. I should've been more startled, because this lot has been known to have a mix of coked-up johns and muggers hanging out late at night. But this guy seemed friendly, and the fact that he was cute and covering what appeared to be a lean, well-toned body got my interest.

He approached and immediately made conversation, asked how I was doing and if I was up for partying. Lucky for him I'd developed a slight buzz from my previous stop meeting friends, but this time I was flying solo for a quick nightcap and feeling adventurous -- he said he was up for anything I needed, and after i hesitated for a couple of seconds, he stripped off his shirt as we stood in the parking lot, reached for my hand and guided it across his muscular, hairless chest, then down his rock-hard abs to a slight treasure trail below his naval. He was cute enough in the face, but the upper body was spectacular. That was all the convincing I needed, so we headed back to my place about 10 minutes away (and I insisted he kept his shirt off during the drive).

In making chit-chat (and using a free hand to reach over and fondle his chest and abs) along the way, I find out that he has no car, no job, no home and no money. He said he doesn't even have a hometown or family to stay with. He said he's just traveling through for the night and hoping to hop a bus to the next city the next day if he has the cash. I realized he was looking for a donation, and once we got home and he dropped his pants, I was more than happy to pass along a few bucks. His dick was perfectly curved, easily 8 1/2 inches and good thickness. He was hard after about 15 seconds of me sucking him, then he tells me to get on my stomach, grabs the lube off my night stand and he's inside me almost immediately.

We never discussed status or whether I played safe, but he felt amazing, and I couldn't object.

He fucks me on my stomach for a few minutes, then flips me over and puts my legs over his shoulders and finishes off a load inside me within about 5 minutes. It feels amazing, and I couldn't bring myself to ask status or anything else.

I head back to drop him off in the parking lot, hand him the cash that I had in my wallet (about $50) and ask if there's any way to stay in touch in case he passes through again. He said he would love to have fun again, and he thanked me for the cash, but he has no phone and hasn't checked his Facebook page in about 6 months. So if it happens again, it'll be another chance encounter.

Edited August 21, 2014 by joethomas

[bbzh]

Two major firsts for me in the past few days: Fucked by a porn star a few days ago, and last night fucked by a homeless guy.

I'd just pulled into an almost-empty parking lot of a local gay bar in a somewhat sketchy part of town when a really young black male (i'd guess early 20s) started walking out of a shadow near a tree-line and toward me as I got out of my car. I should've been more startled, because this lot has been known to have a mix of coked-up johns and muggers hanging out late at night. But this guy seemed friendly, and the fact that he was cute and covering what appeared to be a lean, well-toned body got my interest.

He approached and immediately made conversation, asked how I was doing and if I was up for partying. Lucky for him I'd developed a slight buzz from my previous stop meeting friends, but this time I was flying solo for a quick nightcap and feeling adventurous -- he said he was up for anything I needed, and after i hesitated for a couple of seconds, he stripped off his shirt as we stood in the parking lot, reached for my hand and guided it across his muscular, hairless chest, then down his rock-hard abs to a slight treasure trail below his naval. He was cute enough in the face, but the upper body was spectacular. That was all the convincing I needed, so we headed back to my place about 10 minutes away (and I insisted he kept his shirt off during the drive).

In making chit-chat (and using a free hand to reach over and fondle his chest and abs) along the way, I find out that he has no car, no job, no home and no money. He said he doesn't even have a hometown or family to stay with. He said he's just traveling through for the night and hoping to hop a bus to the next city the next day if he has the cash. I realized he was looking for a donation, and once we got home and he dropped his pants, I was more than happy to pass along a few bucks. His dick was perfectly curved, easily 8 1/2 inches and good thickness. He was hard after about 15 seconds of me sucking him, then he tells me to get on my stomach, grabs the lube off my night stand and he's inside me almost immediately.

We never discussed status or whether I played safe, but he felt amazing, and I couldn't object.

He fucks me on my stomach for a few minutes, then flips me over and puts my legs over his shoulders and finishes off a load inside me within about 5 minutes. It feels amazing, and I couldn't bring myself to ask status or anything else.

I head back to drop him off in the parking lot, hand him the cash that I had in my wallet (about $50) and ask if there's any way to stay in touch in case he passes through again. He said he would love to have fun again, and he thanked me for the cash, but he has no phone and hasn't checked his Facebook page in about 6 months. So if it happens again, it'll be another chance encounter.

He might be homeless but my gut tells me he might be a hustler. Hot story nevertheless. 

[joethomas]

He might be homeless but my gut tells me he might be a hustler. Hot story nevertheless.

Quite possible, but I was pretty convinced he was homeless and living day to day on the streets. And he never actually asked for money, but the sex was hot enough that I was happy to pass along a few bucks.

[Guest SBBOY]

Any recent encounters?

[cumpletion]

I found this one guy on scatboi com and really liked the way he looked (former military) and sent a message. He replied every once in a while until I finally saw a message come in while I was online. I asked him to come over it took quite a while. Later he told me he's homeless and walked over that day. I met him a few times, he was a very hot guy and yes, I gave him cash every time. Not really paying him

Edited October 29, 2014 by cumpletion

[Guest outdatedaccount]

I've often wondered if guys have brought a homeless guy with them to my glory hole to unload in my ass.  I get guys that show at the same time every once in a while.  It's really hot when one guy finishes fucking and you feel another cock slide into your dripping hole and add more cum.   I'd never really know unless they were really pungent.

[TCPig]

I often get used by a very perverted Top, One of his favourite things he likes to do with me is to take me to a selcuded aleey late at night were a number of old homeless men hang out. He makes me strip naked and get on my knees and suck the mens cocks. Once I have got their cocks hard he offers them $10 each to fuck my ass RAW. A couple of the old guys are hung like horses and jump at the chance to fuck anything. So,metimes when there are 7 or 8 men there it takes hours for then to all fuck my sore ass hole.

The TOP likes to video them fucking me.

Last time he paid one old guy $50 to fist my ass. The next visit he is going to offer the money to anyoneone who will fist me.

[DirtyBruin]

I've seen some homeless men - big beards, grubby clothes, HOT and powerful man musk - that I'd have happily gotten fucked by and taken loads from if I'd known a way to get the idea across... and then figure out where to do the deed.

[jankoslave]

that seems to be very hot and really degrading 

will try that tooo

[Top-Secret]

this is an interesting blog "Fucked by a Homeless man" hmmm ! , me being a Top (i guess this doesn't apply) . One thing I can say , is that I don't feel a homeless man is any different from guys who live in houses (except they can't bath as often as the rest of us). I personally can't have sex with anyone that's not clean . if i ever did meet a homeless man who I'm attracted too , then I would invite him over to shower AND THEN I WOULD FUCK THE DOG SHIT OUT OF HIM !  

[Guest breedinghole]

i was fucked by a homeless guy once, in a park where i had met some random guy from craigslist who wanted to pound my hole in public, it was night time & i was so caught up in enjoying the dick i was riding i didnt notice to guy walk up on us. he asked if wanted to take another dick & the guy fucking me then told him my cunt was all his after he finished. a few minutes later he was busting his nut inside me & as soon as he pulled out of my hole the homeless guy shoved his bare dick inside me, he smelled pretty bad but i was so turned on by the situation i just let him fuck my ass too. he ended up only lasted a few minutes but he was jackhammering into my cunt hard & fast & combined with how much of a slut i felt like, i ended up cumming myself from just his dick pounding my ass... always wanted to do it again ever since, the sheer sluttiness of letting a homeless man breed my ass turns me on so much...

Hot being a cumdump for a dirty homeless.

[RenzzoRenne]

I  would like that, but I  don´t have the little chance.

[SanFranBear]

i have been fucked by homeless men and gave them cash. sometimes have seen some that look horny. offered them cash and they gave me their load.

anyone else in san Francisco into homeless?

[Guest]

As a horny freshman home from college in the summer, I picked up a homeless guy on the street and paid him 20 bucks. He was a Latin kid who didn't speak much English, maybe an undocumented Mexican, and he looked and smelled like he'd been on the street for some time.

 

The idea of taking his dirty cock up my ass in an open space got me rock hard as I drove us to the top floor of a deserted public garage. He wouldn't kiss, but he had a huge uncut dick with cheese that I sucked like a hungry whore. He was hard instantly, and I sat on his unlubed dick in one motion and enjoyed the mix of intense pain and pleasure. Unfortunately, he shot pretty quickly, so I paid him his 20 bucks and dropped him off a block away. It was a huge load of cum and blood that seeped through my underwear and jeans into the seat cover.

 

That was almost 35 years ago, before AIDS was even in the news. To this day, I jack off thinking about taking his load.

[blackbbutt]

Was partied up with three Brits on vacation who thought it would be cool to see a black guy get fucked. They offered extra favors if I took cock from whoever they found. One came back with a scrawny guy jonesing for a fix of H. I remember he looked like he was straight off the street. Turns out he was, but I was so fucking horny

 

Took a while to get him horned up but he was desperate and I was still fucking horny He told me later that he was straight but that he loved th blow job and the fuck because he hadn't had sex in a couple of years. The Brits tossed us out of their room after he came in me.

 

He kept me partied up for the next day and a half figuring it was an easy way to pay for his next fix(es). I remember several guys fucking me or watching him try to fuck me, so I guess it worked out for him.

Edited January 25, 2015 by blackbbutt