Homeless guy gets lucky, so do I

I was driving home from interstate after seeing family for the first time in ages after our COVID lock-down was lifted. I pulled in to a service station in a small town along the way to fill up and get a bite to eat as it was around noon and I was hungry.

To my surprise there was a guy sitting outside the building on an upturned milk crate, with a cardboard sign saying “Need a lift to Canberra”.

He looked to be in his sixties, lean, had a beard and short hair, and was not too bad looking. I stopped and spoke with him, said I could give him a lift. He introduced himself as Jack and I told him my name.

I told Jack I was going to buy a sandwich, and offered to shout him lunch. He settled for the same and I ordered coffee for both of us.

We walked over to a grassy spot behind the building, and sat on the grass in the sunshine to eat. Then we packed his gear in the back of the vehicle and started the four-hour drive towards home.

As I drove, we talked about our lives and learned a bit about each other. He was retired from work and had been in a long-term relationship with a woman who owned a house in the little town where he was living. She had recently died of cancer, and a couple of weeks after her funeral her adult son who Jack didn’t even know existed had turned up at the house and told Jack the house had been left to him in the will, and that Jack needed to get out as the house was going to be put on the market.

Jack had packed up his clothes and a few personal possessions into a large backpack and was hitching to Canberra where there were at least some support services for homeless people.

Four hours later as we neared the southern outskirts of the city, I made a decision. I told Jack I lived alone in my own home in Canberra, and that I had a spare bedroom he could make his own. I said I had a few rules – no smoking or drugs, and cleaning & cooking would be a shared responsibility.

Before Jack had a chance to respond, I continued by saying that he needed to know I was an out gay man, but that didn’t mean I would be trying to get him into my bed. But he needed to be comfortable with my sexuality.

Jack asked me why I would invite him, a stranger, to share my house. I told him I felt it was unjust that I had a whole house to myself while others had nothing, and in addition I would appreciate some quiet company as I’m not cut out to be a hermit.

I suggested we give it a try for a few weeks and then we could review the arrangement to see if it was working out ok for both of us. To cut a long story short, he agreed and twenty minutes later we were home.

Fast forward a few weeks. Things were working out remarkably well. Jack was a half-decent cook and pitched in with the housework, and we were both feeling comfortable about the arrangement. Then one night after we’d shared a bottle of wine over dinner Jack asked me if it was OK to talk about some personal stuff. Which it was.

Jack told me his late partner was the only woman he had ever been close to, and that he hadn’t had sex since she had become unwell over two years ago. He was feeling the need for some relief and wondered if it would spoil our arrangements if we had a mutual jack-off session.

I quickly told Jack I didn’t see a problem and suggested we head for my bedroom. Once there we stripped off and I confessed my preference was to suck his cock. He said that would be a first, so why not, and I proceeded to get him nice and hard, alternately deep-throating him and sucking his nice thick piece of meat as he moaned with pleasure and told me how good my mouth felt on his cock.

I kept up the cock-worship till Jack started to tense up and I quickly buried his cock down my throat as he shot his load into me. I licked and slurped in between catching my breath, and eventually he withdrew his cock from my mouth and said he had never experienced anything like it before. So naturally I replied that he could get more of the same on a regular basis if he wanted it. But, I added, right now I’d like to curl up beside him and relax.

We both dozed off for a little while, then got up and had a shower together. Jack asked if I would like to share my bed for the night; I didn’t hesitate, I wanted to cuddle up with his arm around me, spoon-like. So that’s how we went to sleep.

We woke early and each used the bathroom, and I could see Jack had a partial hard-on. Back in bed he asked me if I liked to kiss, and I replied that I loved it. So we began to kiss, at first tentatively but soon we were wrestling each other’s tongue, and both getting turned on. I slid my hand to Jack’s cock which was rock-hard, and decided to pop the question – would he fuck me?

“Fuck yeah” he groaned, so I threw the covers back, grabbed the lube from my bedside drawer and applied some to Jack’s cock and then put some in my crack. I told him to lie on his back and I straddled him, guiding his manhood into my rear end slowly till I grew comfortable with the entry. I relaxed down and took his full length inside me as he muttered “oh fuck” repeatedly. Then I leaned forward to kiss him while pumping my arse back and forth on his rigid cock. I murmured in his ear that I loved his fit hard body, that his cock felt great in my arse, that he was a stud and I wanted him to fill me with his load. Perhaps too soon he grunted “Take it, take my load” and climaxed inside me.

I have always loved the experience of a man releasing his spunk in my mouth or arse, and to have had both from him in less than 24 hours was a joy. I lay on top of him, gently kissing his neck while we both recovered from our exertions. Eventually his softened cock slid out of me and we headed for the shower to clean up. We shared the shower and he held me close with our mouths locked together, pausing only to tell me he would like to be my stud again soon.

And so it was that two days later we ended up on the bed mid-afternoon, my knees around my ears as he pounded into me. This time Jack took his time to fuck me thoroughly as I begged him to breed me, dominate me, fill me with his seed. Like me, Jack got excited by dirty talk, and we exchanged more smutty talk till eventually, gasping with exertion, he pumped his cum-load into me as I jerked myself to orgasm.

Over the next few weeks I introduced Jack to the pleasure of being rimmed, and then persuaded him to experiment with some piss-play in the shower area. It felt so good to have his hot piss-load splashing over my face, then to be hauled to my feet, spun around, and impaled on his meaty weapon; my arse got pounded relentlessly till he shot a big wad of man-spunk inside me and held me tightly in his strong arms telling me how much he loved fucking me.

Things could only get better.