Hobo Henry

Henry was referred to as Hobo Henry. The nickname was a misnomer and had been given to him unkindly, because of his long hair and a scruffy appearance. Henry was the odd-jobber in our small town. He was slender and stood just over six-foot-tall. Henry was forty-two years old and had a pleasant face and expressive eyes. He had a loping gait and always looked like the most relaxed human being when he passed you by, seeming not to have a care in the world. He lived in a shack, devoid of all the amenities that we all take for granted in our daily lives.

About two months after I moved to the town, Henry popped into my gallery and formally introduced himself. He was very knowledgeable about the town’s history and the flora of the surrounding area. He used one of the local plants when bathing and assured me it was better than any soap one could buy. As he was leaving after an hour long visit, he told me that I made the best coffee he had ever tasted. Although I saw him every three to four weeks after that, he was never a nuisance and only visited for an hour or so.

After a while Henry took to hugging me before and after his visits, telling me that I was one of the few townsfolk who treated him like a person. Scruffy as he was he wasn’t dirty. I never recall him ever smelling bad, or being grimy. From our regular chats I also got the impression that Henry was highly sexed, after he told me that he masturbated at least four times a day. Another thing I noticed about him was that he had a very impressive lump in the front of his threadbare baggy trousers.

Henry was not a regular at the town’s pub, and I only recall bumping into him there on one occasion. I later learned that he had to control his drinking, because of a stroppy streak that could surface when he over-imbibed. I was also informed by one of the locals that he had formerly had an on-off relationship with a woman that lived in the town, but that this affiliation had finally ended. Apparently, he had become overzealous with her one evening when she had spurned his advances, and now had a restraining order against him.

One Saturday evening, after living in the town for close to a year, my doorbell rang at around eleven p.m. Not expecting anyone I was surprised by the interruption. Henry had been in a fight and had asked a Good Samaritan from our town to drop him off at my home, hoping that I would have an antiseptic emulsion for him. He had a puffy eye, a few abrasions on his face and a cut on his lip. His shirt was also speckled with blood. I invited him in and suggested he disrobe and take a shower, before I disinfected his battle scars. He wasn’t totally drunk, but had obviously had a few.

Adhering to my request he followed me to the shower before I helped him undress. Once naked I got a look at his dick. Henry’s cock wasn’t the thickest I had seen in town, but it was very definitely the longest. He had an ample foreskin that hung at least two inches off the tip of his knob when flaccid. I was memorised by his long snake as it swayed in tandem with his floppy balls as he washed himself.

After showering, I assisted him towelling off. There were two ugly bruises on his back that looked as if someone had put the boot in. Once done, I applied the antiseptic ointment and plasters to all his cuts, before advising him to move to the bedroom so that I could apply an anti-inflammatory cream to his back. I pulled the duvet cover off the bed and asked him to lie on his stomach. Henry groaned approvingly, as I lightly sat on his butt and began to massage his back. I took my time and really gave him a solid working-over.

After ten minutes, I lifted off him and asked him to turn onto his back, so I could check for bruises on his stomach and chest. Somewhat hesitantly he complied. When his erect knob flopped onto his stomach once he had turned, I was stunned, because Henry’s dick extended well past his belly-button. In fact, he had one of the most magnificent cocks I had ever seen.

Sitting on his upper thighs I then began to massage his torso to continued groans of approval from him. As I rubbed him I noticed a pool of pre-cum begin to form on his stomach at the tip of his foreskin. The flow of liquid from his cock was incessant, and I constantly added some of his juice to the balm that I was applying to his body. Henry stared at me with his hands behind his head. He had an unmistakable horny look in his eyes. Having been given what I assumed was a green light I finally got off the bed and undressed, before getting back on and placing my face at his crotch. As I licked his cock and balls the sounds emanating from him became guttural. His long foreskin totally fascinated me, as it slid back and forth over his moist and odorous dick-head.

I then began the arduous task of attempting to swallow his entire dick. It took a good few minutes, but I did manage to accommodate him balls-deep. When I lifted my head to breathe Henry had a total look of wonder on his face. I then again began the downward journey as pre-cum and drool oozed from my mouth. Before I could complete my journey on this occasion, however, his rough hands clasped the back of my head, before he speared his entire cock down my throat once more. He literally started growling with lust as I had to fight for oxygen, while face-fucking me vigorously.

As he announced that he was about to cum, I pulled my head upwards with all my might, so I could taste his delicious spunk as it spurted into my mouth. After savouring his gelatinous spunk, I let him invade my throat one last time.

When I lay next to him on the bed after our session, we both chuckled mischievously.

A few minutes later, Henry leaned over and kissed me passionately, before his tongue excavated my mouth. As our lips remained locked Henry slowly moved his body on top of me, clasping my head in his powerful hands. After a while, Henry lifted his head he asked if he could fuck me. When I turned over he began rubbing his cock between my cheeks in preparation for his anal invasion. Henry’s abundance of natural lubrication soon made his cock feel slicker than a grease pole and when his dick started its insistent incursion, it felt like his shlong was never-ending as he corked my arse solidly. When he eventually bottomed-out, it felt like three-quarters of my abdomen was bloated with his cock. Henry now began rocking his hips in a slow and deliberate rhythm.

I was blown away by the desire that Henry displayed toward me. This wasn’t like some opportunistic fuck, but like two people enraptured in the throes of passion. My neck was kissed and licked as his passion escalated. Unlike the other men in town and for that matter, most men I had ever met, Henry took his time, relishing every second of his pleasure.

For the next thirty minutes, Henry steadily thrust into me as his hips swayed my body and I had never before, experienced this level of pleasure while having sex. Eventually, Henry lifted his torso onto straight arms and commenced picking up his pace. Gasping with horniness, he plunged into me repeatedly as he finally unloaded. I had already ejaculated with excitement a few minutes earlier, shooting an enormous torrent of cum all over my sheet. Henry was without doubt, the best fuck I had ever had.

Early the following morning, we had sex again before he left.

I did not see Henry again until Tuesday evening, when he popped around at nine p.m. After a cup of coffee he asked if would give him another massage, because his body was still hurting. Naturally, I did, and he again spent the night. As I had originally suspected, Henry was very highly sexed and he kept me very busy that evening.

Henry now began popping in almost daily. One night, Henry surprised by asking if I would consider the possibility of him moving in with me. I was worried about what the villagers would make of this but fortunately, I had a couch in my lounge that converted into a bed. In case gossip, I decided that I would point this fact out to one in the village. Furthermore, I was certain that nobody would believe that Henry and I were having sex and therefore, I agreed to his request.

A few weeks after he moved in with me, I was constantly complimented on Henry’s improved appearance and my kind-heartedness towards him.

Regrettably, some of my night visiting fuck-buddies from the village stopped calling on me because of my fulltime boarder.

But with Henry being the top dog in the sex department, this was not such an ordeal for me.