Toby

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-foot-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 was 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 home and sponge off his biological mother once more, I was outside the gallery watering my garden in the late afternoon as Toby walked in my direction from across the road and he 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 before. I then 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 then 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 apprehensively asked.

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 you, you little cunt,’ I thought. ‘If you want to play games, then I’m going to teach you a fuckin’ lesson.’

Next, after impishly arranging my thoughts, I Eventually responded, “Actually, I have a better idea.”

Toby then gave me a quizzical look, before I continued. “Why don’t we double the stakes,” I suggested before pausing to give my reply its full gravitas.

“Let’s make it one hundred bucks... You will still get your blowjob, but then I also get to fuck your arse.”

“No fucking way, bro,” he shot back totally flustered.

I didn’t reply, but just got up casually and walked over to the chest of drawers where I kept my cash. After returning with a crisp one hundred dollar bill, I placed the money on the coffee table between us. Toby fixedly stared at it with his eyes in turmoil. After 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 ‘It’s your move, bro,’ look on my face. Toby was literally sweating as 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 also given me an incredible hard-on. As toby commenced swallowing hard, he arose and began moving his weight from one to the other foot. I could see that Toby was completely perplexed.

I then casually picked up my bottle of beer up off the table and took a leisurely swig.

When Toby began scratching his head anxiously, he uncomfortably asked, “So… where… where do you want to fuck me?” He stammered and gulped.

“Here. Right here, over the couch,” I stated casually, before getting up and walking to the front door. After turning the open sign to closed, I bolted the door prior returning to the lounge via my bedroom and again sat down in the lounge with a shitfaced grin.

“I’ve never done this before,” he stated worriedly. To which I just shrugged nonchalantly in reply.

After a pause, I decided to stick the knife in, “Toby, it’s your move. Are you in, or out?” I asked in an even tone.

“Please don’t hurt me,” he whimpered.

“Don’t worry bro, I’ve got lube,” I replied reassuringly, showing him the tube I had collected en route back to the lounge.

Gingerly, he removed his pants and boxers before slowly bending over the back of the sofa.

As I took up station behind him I said, “Just relax dude, the tenser you are, the worse it will be.”

After applying lube to my cock and to his arse, I spoke again. “Spread them.” Toby’s hands then moved behind him, pulling his cheeks apart to reveal the prettiest pink virgin pucker I had ever seen.

‘Fuck,’ I thought, ‘I’m really going to enjoy this.’

I leisurely slid my cock up and down between his cheeks for a short while, before placing the head of my dick at his hole and gently began my insertion. As he tensed up I gave his arse a gentle slap.

“Relax, Toby,” I reminded him. When I again began to push, Toby uttered sounds of discomfort. Unperturbed, I kept up my infiltration.

“Please get this over with,” he begged.

‘Fuck you,’ I thought, ‘I’m going to take as long as I like.’

Once all in, I paused, allowing him to time to adjust. When his moans quietened down, I measuredly began rocking to and fro. Toby’s arse was fucking stunning and the sight of his manhole compressing my knob was awesome. I had never felt anything so tight around my cock before. As my momentum intensified, my hands caressed his back and the sides of his torso. The sounds from him had also changed and I got a strong feeling that he was actually getting into the scene.

Next, after leaning over him my hands moved to his nipples before I softly began to tweak them.

As I sensed his growing pleasure my hands moved ever downwards, first rubbing his bellybutton, then onto his pubic area. With delight, I discovered that Toby was rock-hard. The bulge that I had always keenly observed also did not disappoint. Toby had a substantial uncut dick, which felt silky to the touch. I began to wank him slowly, to approving groans from him.

“Should I stop?” I asked mischievously.

“No,” he whimpered, in a scarcely audible voice.

“Do you want me to fuck you harder?” I asked, tormenting him further.

“Yes,” he shamefully whispered.

Raising my torso, I clamped onto his hips and began to fuck him meaningfully. Toby then began to grunt and tug on his dick as my thrusting intensified.

“Do you want it even harder?” I taunted him.

“Fuck yes,” he now grunted shamelessly.

As I manically pummelled his butt, Toby’s body began to shudder as he exclaimed that he was about to cum. Shortly afterward, I erupted into him.

Once we were done he stood up and looked at me sheepishly. I could see the turmoil in his eyes and wondered how he would deal with what had just happened. He took his money and left immediately, without any further verbal exchange.

The following afternoon, after I had closed the gallery for the day there was a knock at my door. Toby stood there looking very uncomfortable.

“Would you like to come in?” I asked, before he nodded his head.

If I thought that I was about to get a freebie, I was sadly mistaken. After he asked about the next hundred bucks, I retrieved the cash from my drawer. In an instant, he stripped and presented his arse to me as he had done the previous day. This time, I upped the ante by slapping his arse hard before I fucked him. The little whore loved it and begged me to hit him harder. I willingly complied and gave him a solid spanking. As his arse went from pink to bright red, I became incredibly turned-on.

With lube, I now commenced spearing his manhole, as the little slut grunted and gasped his approval. Toby began to wriggle his butt so excitedly that I had a hard time staying plugged into him. A few minutes later, we shot our loads simultaneously as he yelped like a bitch in heat.

On Toby’s final visit, I showed him a thick handmade leather dog collar that I sold in the gallery. He looked at it for several seconds and then nodded hornily before bending over the sofa. As I began to smack his arse, Toby almost convulsed with lust.

“Do you want it harder you fucking slut?” I growled.

“Yes, hit me harder, beat the shit out of me,” he replied.

I really laid into him, to roars of approval as he gripped manically onto the back of the sofa. On this occasion, our session lasted far longer than the previous ones. I commenced alternating between fucking him and spanking him. After pulling my knob out of him I would then beat his arse for a minute or two, before rough fucking him again. Toby was in heaven and when we finally came, he was howling with pleasure.

The blowjob suggestion, which had sparked our interactions didn’t ever happen. I was a little sorry about that because Toby had a beautiful cock. The money that I had spent, however, was well worth it! I also made a mental note to begin saving for Toby’s next visit.