The Homeless Man

This was a moment in my life I was, at first, not so proud of. Some guys I knew got together at a hotel and partied. We got drunk, and on a dare, I was told to seduce a homeless guy near the hotel (we could see him from our room) and bring him back him and suck his dick. He was a stocky black man, so I was definitely attracted to him. Afterwards I felt guilty about using his unfortunate situation, but we eventually we got to be friends.

After completing my second year of college, a couple of friends and I decided to get a hotel room and party. They were guys that I occasionally fucked around with when I visited the city on weekends. Craig was a black, chubby guy who was versatile and Stan was a top black chub who was an offensive lineman for a local semi-pro football time. We'd meet periodically and have a 3-some with Stan being the alpha and always taking the lead. It was also a time in which I drank heavily and discovered how much it lowered my inhibitions, which is good and bad.

We played "truth or dare" with shots involved and the more it went on, the drunker we got and the more adventurous it became. Craig dared me to go outside and bring a homeless guy up to the room to blow him. After an outright refusal from me, I eventually broke down and decided to do it. It was extremely hot outside so my hope was that the homeless guy could be talked into coming for a few beers and the air conditioning.

I went outside and noticed he was talking to a couple of other guys, so I waited to hope I could get him alone. Soon my window of opportunity opened. As he sat alone on a bench, I joined him and started some small talk. He introduced himself as Earl and was very friendly. When I offered to join me and some friend for a cold beer, he gladly accepted. Probably recognizing him, I got a few strange stares from the hotel personnel in the lobby but no one said anything.

Once in the room I introduced him to my buddies and we sat around drinking some more, but the topic of sex hadn't come up yet. Earl, Stan and Craig were getting along very well, lots of laughter and stories but I was more focused on how I would get him to let me suck his dick and was unable to enjoy the conversation.

Finally, Stan brought up the topic. "James, don't you have a request to make?" he asked, looking at my slyly.

I wasn't ready to respond to the question and remained silent. So Stan took over, as he usually does. "My buddy," Stan said as he got up and placed his large hand on Earl's shoulder. "James here has a real skill that he wants to try on you."

"Yeah?" he looked up. "What's that?" he said, looking at Stan, then at me. I was so embarrassed.

"Yeah James," said Stan, "What is it that you want to do?"

Not knowing what else to do, I just blurted out, "I'd like to suck your dick," then awaited his response, which came surprisingly quick.

"You want to suck my dick?" he asked, astonished. "Do you all know he's a faggot?"

"Yeah," we do, said Stan. Craig nodded in agreement.

"Show me," Earl said, shifting uneasily in his char.

"No problem," said Stan, lowering his shorts, exposing his genitals. I went over to him and got on my knees, taking his cock in my mouth as I had often done before. Stan had a very average cut dick both in girth and length, but I had the hots for him so bad that anything he did with it was a pleasure for me. Craig then took out his dick, very similar to Stan's, and stood next to Stan so I took turns blowing them both in front of Earl.

"You convinced?" asked Stan.

"Well, it's just us in the room, why not?" said Earl as he got up. When he joined us, he pulled down his pants and badly stained underwear. His cock was much larger than normal but there was a foul odor that Stan quickly addressed.

"Whoa man, you're going to have to wash your ass first. Not to be disrespectful but you stank." I always admired Stan's ability to be direct and get instant results. I think it helped with him being about six-foot seven inches tall and about three hundred fifty pounds of solid man.

"Oh okay, I'll shower up," Earl said, becoming more enthusiastic. Much to our relief, he went into the bathroom to clean up.

"Thank you," said Craig to Stan, which I dittoed, standing up.

"You see that fucker's dick? Goddamn!" said Stan, removing the rest of his clothes. "Which one of you all going to take it up your arse?" Craig looked my direction as a hint.

"James it is," said Stan laughing, laying on the bed. "Which means you better give me some before you become loosebooty. My dick's half his size." The three of us had been together several times so we knew what our roles were. Stan was always the top who on occasion would suck dick while Craig was fully versatile, but preferred being the top, although his dick sucking and ass eating skills were fantastic.

I got between Stan's big legs, "You know how much I love all your body," I said kissing his beautifully full lips.

"Show me how much you love your daddy," he said seductively. Stan was about 10 years older than me but definitely had that "daddy" presence which I found irresistible. I kissed, licked and gently bit his thick neck which, being his sensitive spot, always drove him crazy. "Oh fuck!" he yelled out, grabbing the sides of the mattress with his large arms. I then licked his armpits, taking in the intoxicating man scents before I moved to suck his nipples which stood on large areolas. His chest was very smooth which felt good as I let my tongue travel across it, down his belly until I reached his beautiful tightly curled pubic hairs which I ran my tongue across.

"Is that good daddy?" I asked. "Ready for me to put your cock in my mouth?" Stan liked it when I was slightly fem and devoted to giving him pleasure, so I often fell into that role with little effort.

"Lick my balls first sweetheart," he said. Sexually, Stan always assigned me womanish roles. As I licked his balls and rolled them into my mouth I felt Craig get behind my and spread my cheeks, then the probing of his tongue which he did so well. "Alright baby, give me some of that hot mouth," hummed Stan. His cock was rock hard and velvety smooth, just like the rest of his body.

As I was sucking his cock, Earl came into the room wearing just a towel. "You all got any whiskey here. I need to get more drunk if I'm going to do this."

"Give the man some whisky, love," said Stan to me. "You do know no one is making you do this," said Stan to Earl.

As I got up to get the whiskey from the cabinet I noticed Earl looking at my bare ass. "Ice, or not?" I asked. "No ice, and fill that glass up," he said. Luckily it was a short glass, so I filled it three-quarters of the way. I handed it to him on the way to get back in bed with Stan, who has Craig laying at his side sucking his nipples.

Still wearing his towel, Earl sat down on a chair close to the bed, watching as both Craig and I now shared Stan's cock and balls. After awhile he got up and stood next to us, playing with his cock under the towel.

"Looks like the man could use some action," Stan said, taking my head and guiding it towards Earl. I positioned myself on the bed so that I could suck Earl. He opened his towel and stood by me, his half hard cock inches from my mouth. It was very thick and veiny. His pubes were mostly gray and surrounded his groin. I reached and played with his ball sack which hung heavy, then gently pulling him to me so that his cock could go into my mouth. As soon my mouth engulfed him, he started moaning and his member growing in length and width. It still felt somewhat soft, allowing me to adjust to its thickness.

I felt the bed shaking as Craig climbed on top of Stan to ride him. I felt Stan's hand playing with my ass, then give it a good slap. "How's it feel Earl?" he asked?

"Feels good, damn good," he said with obvious satisfaction. "How's that ass feel?"

"Fucking amazing. You ever fuck a dude?"

"Nah man, I don't do that gay shit." Had I not had a mouthful of cock I would have laughed at the irony.

"Dude! Look who's blowing you!" Stan said in disbelief.

"That don't mean I'm gay," Earl said, his cock now a good ten inches.

"That's your business, man," said Earl, who proceeded to put Craig in the doggie position and began fucking him. "Buttfucking a dude is pretty damn amazing. You should try it." I was always amazed how Stan could carry a casual conversation while in the middle of sex. His ability to stay rock hard for hours and make his bottom feel good made me think about him often.

But the man whose cock I had in my mouth wasn't so bad either. I looked up at him and found myself getting more turned on. By the gray hair that covered his belly and chest I guessed that he was about 65 years old, perhaps younger when a difficult life was taken into consideration. His groin area was very hairy and mostly gray and a bit funky despite the presence of a soapy smell as well. His legs were slight bowed and thick.

"You two can have the bed," said Stan as he and Craig stopped fucking and got up, retreating to the living room portion of the hotel suite, leaving Earl and I alone.

"Sounds good to me," said Earl, "was getting tired of standing."

I stood up, his beard tickling my face. "You should have said something." I laid on the bed, waiting to see how he would join me.

"Move down," he said, indicating that he wanted me to slide towards the foot of the bed. Unsure as to what his plans were, I did as he told, then was surprised when he positioned himself over my face. I opened my mouth and he slid his cock in and started face fucking me, a bold move considering he seemed hesitant about doing anything that was 'gay." I reached up and tweaked his nipples which elicited a moan.

Then I felt the bed shake and my legs lifted but didn't know if it was Craig or Stan not only because their cocks are similar, but also because I had a furry belly resting on my face. I felt a pillow being placed under my ass, then the penetration and subsequent fucking.

Earl pulled out of my mouth and stood at the edge of the bed as he watched Craig fuck me. I looked to see Stan come back in the room, stand behind Craig and mount him, creating an anal train. Within minutes Craig shot his load in my ass, pulled out and was immediately replaced by Stan who also pounded his spunk in my ass.

"Your turn," said Stan to Earl, slapping me on the butt as he went into the bathroom. I looked to see that Earl's cock was fully erect, perfect for fucking.

"If you say so," said Earl, moving behind me. I sensed that he was more interested than he was letting on, based on the hardness of his cock and lack of hesitation when he got in position behind me. I felt the wide girth of Earl's cock spread me open, but he entered with ease.

"How's that ass feel?" asked Craig.

"Damn good," said Earl slow stroking me. "So wet." The more he fucked me the more Earl got into it. He finally pounded a load into me while I was on my belly and he had me a good head lock, collapsing onto me while we both caught our breaths.

While still on top of me, he fell asleep within minutes, loudly snoring. As was always the case Stan would sleep in the bed with me while Craig took the couch, which meant Earl had to leave. Luckily Stan handled it with tact and firmness as he led Earl to the door.

Wearing just his underwear he got into bed with me. I loved laying my head on his meaty chest while he stroked my hair while watching TV. Most nights I would get under the covers and take his soft penis into my mouth until he fell asleep. He would usually be the first to wake up, pulling me onto his hard cock and fucking me until he got his nut, then shower, dress and go home. Sometimes Craig and I would get another round in after Stan left and that morning was no different.

Earl and I eventually became friends and met at least one a month after that. He was in and out of jobs, mostly because of his drinking problem. After a few years he disappeared from my life. I had fallen deeply in love with Stan, but he never was able to return it. After marrying a woman, I never heard from him again. Craig and I also grew apart. But those couple of years spent in the hotel room provided great memories.