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The Homeless Guys

"Homeless guys can be great lovers..."

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After finishing school I got a job in a large and successful warehouse as their computer expert. Fortunately, I was paid an above average salary because of my considerable computer knowledge. Being a geek in high school had really paid off. I was average looking and measured five-foot-nine inches tall. I weighed about one hundred and forty-five pounds and had an attractive physique. No, I didn’t wear geeky spectacles and my vision was very good. I was no stud but had a slightly above average seven-inch circumcised cock. People did not stop and stare at me in awe, but being nineteen years of age was certainly an advantage.

When I moved to the small city where I was employed, I was greatly relieved to finally get away from my family. I could now embrace my homosexuality with no qualms. The small apartment that I rented was very private and extremely well situated. After starting my new job, the ensuing ten months of my sex life was almost non-existent. One evening, however, my life changed significantly. While purchasing a porn DVD in the Adult bookstore near my home, I was asked if I wanted to visit the cinema. I had no idea what the person behind the counter was talking about, but inquisitively I paid the required amount and entered this den of iniquity.

The back section was rather seedy, and there were two cinemas. More accurately put, they were television rooms. Both rooms had flat screen televisions and a dozen or so chairs for viewing. One was for straight porn and the other played gay porn. There were several cubicles for private viewing. At the far end of this compound, there were another four larger glory hole cubicles. To the one side of these cubicles, there were stairs leading up to a platform located behind the booths. I climbed the stairs and observed a fairly good looking man standing in front of the furthest glory hole.

I immediately descended the stairs and entered the cubicle that he was facing. I was presented with an uncut cock that I instantly started to suck upon. Being no oral expert I did my very best. He bent down after a while and told me to keep my head still so that he could face-fuck me. I obliged, and he started thrusting rapidly. As I relaxed the process became quite enjoyable. With supreme concentration, I was eventually able to accommodate his entire dick, in my mouth. I heard him instruct me to use my tongue, to which I complied. Shortly after, he shot his load into my mouth. The taste was quite pleasant, and once finished he pulled his pants up and left immediately.

After my initiation into oral sex, I milled around for about thirty minutes. There was no further action. The other two patrons I encountered simply did not do it for me. I left elated, if somewhat disappointed. After my initial visit, my routine at the bookstore was restricted to two visits a week. I would visit for an hour or so on Wednesday evenings and would spend about two hours at the establishment, late on a Saturday afternoon.

The visits, following my initial outing, were a lot more interesting at the bookstore. I really loved the glory hole section, and that is where I spent most of my time. I even had a scene in one of the one-on-one cubicles, and sadly have to admit that my cherry was taken by an unremarkable man. But at least, I had finally had anal sex. Thankfully he was quite gentle, and I was initiated in a pleasant way.

After leaving the bookstore at around seven one Saturday evening, I met Harry. He sat a half a block away from the bookstore. He was a homeless man and sat on the ground with his back propped up against a shop window. He was holding a cute little dog, and as I knelt a small way from him the little dog ran over. When I patted the dog, Harry asked me if I had enjoyed my visit to the bookstore. I smiled and said that it hadn’t been too bad. Harry then asked me if I lived nearby, to which I nodded yes. He asked me if I had some food to spare, as he was rather hungry. I will never understand why, but I invited him to follow me home.

He did so with his dog and a fairly large duffel bag. Harry was about six-foot tall and fairly clean-looking. He was forty-five years old, and not too bad on the eye. While walking to the apartment he mentioned that he could do with a shower, if I would allow it. I replied, “That won’t be a problem.” When we arrived at the apartment I gave the dog a bowl of titbits, and I then plated up some leftovers for Harry. As he ate I took note of his hands. They were a little grubby, but his nails were short and fairly clean. He removed his cap revealing a full head of mouse-brown hair. His hair was clipped quite short, and he had two-day old stubble. His teeth looked to be in good condition.

Harry told me that he visited a homeless shelter on Mondays, and Thursdays, to shower and shave. They also supplied him with a meal on those two days. When he finished eating I offered to do his washing for him, and he accepted gracefully. I told him to strip, and give me everything that needed to be washed. Naked, he was a sexy and well-proportioned man. Harry had a reasonable amount body hair and a substantial uncut cock. I placed all his clothing in my washer/dryer, and set it on the required four-hour cycle. I informed him he could stay the night, and that I would iron his clothing early the next morning. Harry sat on a towel on the sofa, as we sipped our beers, and smoked.

At around nine p.m. we headed for bed after I had placed a small blanket on the ground for the dog to sleep on. Before getting into bed, Harry asked if he should shower first. I replied that I would prefer him to do so in the morning. As we lay in bed I got a good whiff of his body odour. It wasn’t hectic, but strong and masculine. He eventually moved on top of me and pushed my legs apart with his knees. He really enjoyed kissing and was very good at it. He ground his cock into me as we made out for the next ten minutes. After nibbling on my ear he told me to turn onto my stomach. As he lifted his body, I changed position, before he lowered himself back onto me. His cock slid up and down my crevice for the next few minutes. I could feel my crack becoming slippery, as his cock oozed copious amounts of pre-cum between my cheeks.

Harry then lifted his hips and started inserting his cock into me. He was a lot bigger than the first guy who had fucked me, and the pain was fairly intense. He took his time, however, and eventually went balls-deep in my hole. Rhythmically, he started thrusting into me while licking my neck, and ears. The rough stubble on his face was driving me crazy. He pulled both my arms up on either side of my head and started caressing my arms with his rough hands. I had never experienced anything as erotic as this, in my entire life. He kept varying his pace and fucked me for thirty glorious minutes. When he emptied his load into me, I had cum twice. We were both very sweaty when he got off me, and I suggested we go to the lounge and have another beer. He was very happy with my suggestion.

Returning to bed a while later, Harry got straight on top of me and resumed our lovemaking. This time, however, I was on my back. When he again inserted his dick into me, it felt twice the size it had before. After five minutes I had adapted to my anal intruder, and with my legs wrapped around him, enjoyed my second fucking. Before cumming, Harry pulled his cock out of me and moved his hips up to my mouth before unloading. Once round two was finished, we were in dreamland within five minutes.

The following morning I awoke and went to the bathroom to douche. Returning to the bed I observed Harry on top of the continental quilt. I walked over and kissed him, before lifting his left arm and cleaning his armpit. The right armpit followed to sighs from Harry. I then moved down to his genitals and washed them with my tongue. Tugging on his tight foreskin, I release its prisoner. His cock-head was very funky and obviously saw the light of day very seldom. Having never rimmed anyone before, I decided to explore this practice as well. When Harry pulled his legs back I winced at the pungent smell emanating from his crack, but dove right in and started licking voraciously.

Once finished, Harry hopped off the bed pulling me into the doggy position, before fucking me at the edge of the bed. Overexcited as he was, his entry was quick and painful. His powerful hands, however, made it clear that escape was not an option. After a while, he lifted my torso and started caressing my body as he continued fucking me. Ultimately pushing me onto my stomach he leaned on straight arms and started thrusting into me urgently. Minutes later he shot his load into my backside.

While Harry showered and shaved, I made breakfast. I had also given him a new toothbrush from one of my many spares, having seen the one that he had used the previous evening. The old toothbrush looked like it had reached its sell-by date, a year earlier. After breakfast I ironed all his clothing, and have to say that once dressed and shaved, Harry looked very respectable. I asked him if he wanted to stay for lunch, but he regrettably had an engagement.

Apparently, a buddy of his named Willie had been beaten up that week and was in a hospital. Already missing four teeth, Willie had gotten another four knocked out. As if that wasn’t bad enough, while in hospital four of Willie’s rotten back teeth were also extracted. Laughing, Harry said that he was pleased about this in a way because Willie had breath that could raise the living dead. “Hopefully,” Harry said, “the extractions have sorted that problem out.”

Harry told me that Willie was a really great guy and that I would like him a lot. Politely, I said that I would love to meet him. Before leaving I gave Harry some money, five packets of cigarettes, and a packet of sandwiches for later. He also asked if he would see me the following Saturday. Smiling and said that I would like that very much. Once gone, I was very pleased with my reckless decision the previous evening, and would definitely look out for him the following Saturday.

The following Wednesday evening at the bookstore was a good one. I met a guy a year older than me called Tommy. I introduced myself as Warren, after which we chatted for a while. It was really strange to engage someone in this place of total anonymity. Tommy was taller than me, and about thirty pounds overweight. He had a cute face and lovely demeanour. He lived with his parents and was shit-scared of them finding out that he was gay. Ultimately, we moved to one of the cubicles and undressed. He was quite hairy and had a cut cock that was almost identical to mine.

Tommy was very loving and adored fondling and kissing. Being versatile he loved giving and receiving, and I finally got to penetrate someone else. The kissing never ceased throughout our encounter. We flip-flopped for half an hour, before shooting our loads into each other’s mouths. Once done he asked me if he would see me again the following week. I answered that I would definitely be back the following Wednesday. Spent, we left the bookstore and went our separate ways. As I walked home smiling, I knew that he could become a habit with me.

On Saturday, I half-heartedly went to the bookstore. I was far more interested in seeing Harry after my visit. I milled around before sucking a guy off through a glory-hole, and after the required time had passed, left hoping like hell that Harry would be waiting. As I left the bookstore I was delighted to see him in the same location as the previous week. He was accompanied by a tall lanky guy, which I surmised was the buddy he had spoken about. It appeared that my politeness had been taken literally.

Where it took some time to realize that Harry was a homeless man, with Willie it was totally obvious. With his missing teeth, his mouth looked like an old graveyard with several missing tombstones. He was unattractive, with huge prominent ears, and a large nose. Willie had wispy blond hair that was almost white and a ruddy complexion. His flimsy beard was slightly darker than his hair and had a reddish tinge. His eyes were light brown with a hint of green, and he stood six-foot-two tall. Willie had a wiry body, with enormous hands and feet. His clothing was really grubby and there were holes in his pants and shirt. The trainers on his feet were skanky.

When Harry asked if Willie could tag along I almost bailed. His shit-faced smile and look of anticipation, however, made me relent. Willie also had a duffel bag, albeit smaller than Harry’s, and we presently left in the direction of my home. After arriving I fed the dog Harry’s titbits and plated up two dishes for Harry and Willie. Before sitting down at the table I asked them to strip, so I could do their washing.

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The clothes they were wearing and the contents of the duffel bags were soon being washed, as they sat on hand towels at the dining table, eating and enjoying a beer.

When Willie stripped I observed that his body was very pale. He was almost hairless except for tufts of hair under his arms, and above his crotch. His feet and hands were really attractive but were in need of a scrubbing. He wore size thirteen shoes. His cock was like no other I had ever seen, nor would ever see again. It was extremely pale and almost translucent. There were prominent blue veins crisscrossing his entire dick. As I later learned, his cock was nine inches long and had a very pronounced upward curve. When erect the tip of his cock touched his body above his belly button. His dick tapered from a very thick base to a fairly small head. The dick-head, under a very long foreskin, was totally indiscernible. The extra skin that hung off the end of his cock looked like a wrinkled dried fruit.

Willie had the strangest balls I had ever seen. The actual balls were not particularly large, but his scrotum hung halfway down his legs. His balls were also very pale with blue veins.

After dinner, we sat in the lounge, smoking and drinking beer. Willie had an infantile sense of humour, and one couldn’t help laughing as he joked and chuckled. After a while, Willie asked me if I didn’t feel a bit overdressed for the occasion. Laughing, I left the room before returning naked, joining them in the lounge. I sat on the couch, opposite the guys who occupied the two chairs. Shortly, Willie got up and joined me on the couch. Willie then put his arm around my neck and moved closer to me. I was rather pleased I had not met him a week earlier because his breath wasn’t exactly fragrant. With the hum of his body odour enveloping us, he swiftly placed his mouth over mine and started to kiss me.

Willie’s penetrating tongue was long and thick, as he surveyed my mouth. The gaps between his teeth felt strange, as my tongue played around his mouth. Soon he had me flat on my back in the middle of the couch, before assuming a sixty-nine position on top of me. His cock smelt of urine as it danced above my face. As he entered my mouth, I was amazed at how easily his curved cock slid down my throat. Before long, he was balls-deep in my mouth. As he sucked on my cock I felt my legs being lifted and then felt the unmistakable prodding of another cock pushing at my manhole. I was in heaven and I prayed that this would continue all night.

I was enjoying my very first threesome, and I had hit the jackpot. After five minutes when Willie tried to get off me, presumably to swap places with Harry, I clung on to his backside with all my might. I heard him tell Harry that they had better retain their current station. A short while later Willie came down my throat, as I shot my load into his mouth. As he got off me Harry continued fucking my backside, before unloading into me soon after.

We all resumed our seats after grabbing another beer. Both men now needed to piss, and I wasn’t about to allow another milestone in my sexual education go to waste. I told them I wanted them to piss on me, and down my throat. Both men smiled broadly as we moved to the shower. When we got into the shower, Harry moved up first. As I knelt before him he started pissing all over me, and soon I was drinking his golden nectar straight from the tap. Willie watched entranced before stepping up, and spraying me through his rumpled foreskin. I also swallowed some of his delicious yellow sap.

Before leaving the shower I offered to clean both their butt-holes. Willie went first, and this was quite an ordeal for me. I was so horny at that point however that it did not matter. Harry followed, and his butt was far less hectic. We returned to the lounge for a smoke and a drink.

They had continually mentioned Alf during the evening. When I asked about him, I was told that he would definitely not be into our scene. According to them, he was a bit homophobic. Jokingly they said, that he was the third member of the, ‘Three Stooges,’ as they called themselves. They hung out together and looked out for one another.

When we went to bed that evening, I was initially fucked by Willie. His cock was unbelievable, and his curve totally pulverized my prostate. I shot two loads without even touching my cock. Stink Willie gave me the best fuck I had ever had, and I thanked goodness I had invited him along. After Willie came in me Harry took over. We all fell asleep afterward, with me in the middle of the two.

Early the next morning Willie shook me awake and told me to follow him to the lounge. I lay on the floor with him on top of me, again in the sixty-nine position. With my head slightly raised on a cushion, he pissed down my throat in installments as my right hand controlled the flow. Every time I needed to breathe he would lift up, so I could inhale fresh oxygen. Once the pissing finished he started face-fucking me. Once again his exaggerated thrusting allowed me plenty of oxygen. I begged him to not come for as long as possible, and he did not disappoint. Our session lasted for half an hour.

Afterward, I licked his armpits clean and gave him another butt cleaning. Horny again, he placed me on my back, before lifting my legs and inserting his cock into my backside. He moved on top of me and slowly fucked me. He kissed and he licked my ears, as I sucked on his fingers. I was in heaven as he licked all over my face. After he came we fell asleep, before Harry awoke us a while later.

After breakfast, I did their ironing while they showered. They stayed for lunch and left mid-afternoon. I gave both of them money for the week, and five packets of cigarettes each. I also packed a parcel of sandwiches for later that evening. Willie even got a complimentary toothbrush.

The following week, Tommy and I again enjoyed our flip-flop session at the bookstore. On Saturday Harry and Willie again visited, and we followed the same ritual as before. This weekly routine continued for the next three weeks. During this period I bought Willie and Harry new trainers, four pairs of socks, three new shirts, as well as a pair of jeans for each of them. They were looking more and more respectable. I also bought hair clippers and took to becoming their hairdresser.

When I exited the bookstore on the following Saturday, I was surprised to see only Willie waiting for me. I learned that Harry’s brother had tracked him down, and had invited him to live with their family. They had built a flat for him on their property, and we're hoping that they could rehabilitate him into the normal world again. I had really come to like this man and his little dog and was very sad to lose contact with them. On the other hand, I hoped that this new development would work out for him.

Willie and I had a wonderful time that evening, and he only left late the following afternoon. Over the next two weeks, I also saw him more regularly, as he started coming directly to my home.

When Willie arrived at my home the following Saturday with Alf, I was rather taken aback. I decided to relax about it, and go with the flow. Alf was about five-foot-ten inches tall and had a dark complexion. He was handsome but very rough looking. He had a stocky build, with dark black shoulder length hair, and a longish black beard. His clothes were rather ragged, and he seemed a bit scummy. Both guys had their duffel bags with them, and when I asked the guys for their clothes, Alf undressed very reluctantly. He had a masculine body and was powerfully built. His feet and hands were rather broad but dirty. All in all, he was fucking hot!

Alf was hairy and had a very thick cock that was incredibly fat in the middle, tapering off to either end. It must have been seven to eight inches soft, with a foreskin that completely covered the head. His dick was very dark and surrounded by a forest of black hair. His balls were huge, and would not have been out of place on a bull. He had tattoos on his upper arms, chest, and back. With their washing going, I plated up their food. They sat on hand towels at the dining table as always, drinking and eating.

After dinner, I asked Alf if he wanted a haircut and a beard trim. He shrugged and said, “Whatever.” As he sat in the kitchen I went to work, using a number-four clipper attachment on his head and beard. After that, Alf had a long shower while I did the dishes, after cleaning up all his hair. When Alf emerged from the bathroom, he looked magnificent. He had really given himself a good scrubbing. His hands and feet were clean, and his new hairstyle and beard looked fantastic. When Willie and I applauded, I saw him smile for the very first time.

We had a few more beers before retiring to bed. I had made up a bed for Alf on my large couch, and as he snuggled in Willie and I left for the bedroom. The sex with Willie was incredible as usual, and after an hour of fucking, we fell asleep.

The following morning the breakfast ritual was followed by ironing, as always. Both guys stayed for lunch, and I went all out. By four p.m. they were on their way, with smokes, money, and leftovers. I saw Willie on Monday and Tuesday that week, and on Wednesday, I enjoyed another flip-flop session with Tommy.

I did not see Willie on either Thursday or Friday, and on Saturday as I left the bookstore, he was also not in his usual spot. The following week I did not see Willie at all. I did not visit the bookstore on Wednesday evening as normal, because of my growing concern over Willie’s absence.

On Saturday I sat in the bookstore watching a porn movie and counting down the minutes till seven p.m. I was totally disinterested in any action whatsoever. At seven, as I walked out of the bookstore I prayed that I would see Willie. As I approached our usual spot I saw Alf standing there with a sullen face. When I asked about Willie, he shrugged and started crying. Willie was dead. He had been killed by some thugs the previous week. Willie was prone to getting into fights, hence all the missing teeth. A bunch of hooligans had attacked him the previous Wednesday when Willie intervened while they were harassing some girl. They brutally assaulted him, and he had died two days later in hospital.

Alf had only found out about the incident the previous day. There were no willing witnesses, and Alf was sure they would get away with it. Alf and I stood there crying like two babies. He placed his arm around my shoulder and offered to walk me home. When we arrived at my place I invited Alf to spend the night. I plated up the food that I had made in anticipation of Willie’s visit. Having not eaten in twenty-four hours, Alf got stuck in. I couldn’t eat, and fetched two beers and sat with him. He ate in the nude, with the washer/dryer in full cry. After dinner, we sat and spoke for an hour or two. He regaled me with Willie and Harry stories, as we laughed and cried. I made his bed on the couch and departed for my bedroom.

Sunday morning I made breakfast while Alf showered. After breakfast, I did the ironing. During lunch, Alf asked me if I could get him a job at the warehouse where I worked because he was tired of his present existence. I promised that I would ask my boss to interview him. We ate leftovers for dinner that evening. After a few beers and smokes, we went to bed at nine. As I lay in bed thinking about all that had happened over the past several weeks, Alf entered my room and got into bed with me. He gave me a hug before we fell asleep. No other physical contact took place.

On Monday I left my spare set of house keys with Alf, so he could come and go as he pleased. I spoke to my boss who agreed to interview Alf, on Tuesday. At lunch time I went shopping and bought Alf four new shirts, two pairs of jeans, two pairs of trainers, six underpants, and six pairs of socks. When I arrived home Alf was sitting on the couch. As I handed over my purchases he asked me if I had lost my mind. I informed him that he had to be properly dressed if he was serious about his interview the following day. He was elated, and once again I saw his beautiful smile. We ate dinner at seven and got into my bed by nine. I got another hug before we drifted off.

Alf got the job the following day. That evening I told him that he could stay with me, for as long as he needed to. When he asked me why I was doing all of this for him, I said that it was what Harry and Willie would have expected of me. He reminded me that he wasn’t gay. With a naughty smile, I joked, “That’s a real pity because I would really love to suck that beautiful cock of yours.” He observed me for a long while. Slowly he started pulling his zipper down.

 

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Written by Tuppie
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