Several months after I opened my gallery in a small town, I met Mannie’s son. Mannie owned the shop across the road. Mannie and his wife Shirley had both been married before, and Toby was Mannie’s son from a former marriage. Toby was twenty-six years old and about six feet tall. Facially, he did not resemble his dad at all. Mannie was sixty years old, a fact I was aware of having attended his birthday party a month before. For a guy of his age, Mannie was rather good-looking and I could not help thinking, that he must have been a handsome man when he was younger.
Toby wasn’t ugly, but had three facial features that were somewhat unattractive. Firstly, he had been in an accident years earlier and had an indentation on his left temple. Secondly, his mouth curved downwards at either end, giving him a sour demeanour. The third negative was that his teeth weren’t in the greatest condition and were somewhat chipped and uneven. On the plus side, however, he always wore tracksuit pants and the bulge in the front always looked very promising.
According to Shirley, Toby was a total slob. It was abundantly clear that Shirley did not like him and didn’t want him in her house. When Toby visited, therefore, he stayed in the cottage behind their garage. Shirley mentioned in confidence that their weekly maid had refused to clean Toby’s room because he was just too slovenly. She further went on to say that Toby was a total bum who could never hold down a job for more than a few months. She joked that Toby had gone through more jobs than I had changed underwear in my life. With all these negatives, however, there was something rather sexy about Toby.
During a six-week-long visit, again between jobs, Toby initially treated me very circumspectly, obviously cognisant of the fact that I am gay. Towards the end of his stay, however, his demeanour seemed to warm considerably. A few days before Toby ended his stay, presumably to return and sponge off his biological mother once more, I was outside the gallery watering my garden in the late afternoon. Toby walked in my direction from across the road and engaged me in conversation. After finishing my chore and as I was about to enter my house to start preparing dinner, he stated that he had never been into the gallery. I informed him that he was welcome to take a look.
After a cursory glance around the walls, I offered him a beer, which he gladly accepted. As we sat across from one another in the lounge indulging in general chitchat, he seemed to become rather edgy. Toby then told me that he would be leaving in a few days and amazed me by asking if I would lend him fifty bucks. He assured me that he would repay the loan a few months later when he again visited. I explained that I never lent money, simple as that! After a short while, as he became ever more fidgety, he made an astonishing suggestion.
“You’re gay, right,” he affirmed.
“Yes,” I replied, bewildered.
“Well, would you give me fifty bucks… if I let you suck my dick?” He asked, nervously.
I glared at him for a minute, watching his level of discomfort arise. A million thoughts raced through my mind. I was irritated but unbelievably intrigued. ‘Fuck this cunt,’ I thought. ‘If he wants to play games, I’m going to teach him a lesson.’
Eventually, I responded. “Okay, I’ll suck you off… but I have a better idea,” I stated, somewhat impishly.
Toby then gave me a quizzical look. “Let’s double the stakes,” I answered, pausing to give my reply its full gravitas. “Let’s make it One hundred bucks. You still get your blowjob, but then I get to fuck your arse.”
“No fucking way, bro,” he shot back.
I didn’t reply, but just got up casually and walked over to the chest of drawers where I kept my money. After returning with a crisp one hundred dollar bill, I placed the money on the coffee table before me. Toby fixedly stared at it with his eyes in turmoil. Returning his gaze to me he had a look of disbelief on his face. As he again focussed on the money, his anxious knuckles went white as he clamped onto his knees. I remained silent for a while, before going for the jugular.
“Of course, if we both enjoy it, there’s another hundred bucks awaiting you tomorrow,” I said, matter-of-factly.
His expression now became totally frantic. The mercenary little fuck’s mind was working overtime. With my hands behind my head, I sat back, with a ‘your move, bro,’ look on my face. Toby was literally sweating and his eyes began to flicker. The bewilderment was totally delightful and deserving. I also have to admit that the prospect of fucking a virgin arse, had given me an incredible hard-on. Swallowing hard, he arose and began moving his weight from one to the other leg. Toby was completely perplexed.
I picked up my bottle of beer up off the table and took a leisurely swig. Toby began scratching his head anxiously. “Where… where do you want to fuck me?” He stammered.
“Here. Right here, over the couch,” I stated casually, before getting up and walking to the front door.