Delivery Boy

After my experience on the nature trail, something had changed in me. I no longer felt uncertain about my sexuality. Whilst I didn't consider myself gay, I knew that no conventional straight experience could ever excite me nearly as much as my last two encounters had. Though they had been relatively tame and no actual sex had been involved, I knew deep down that I needed to push myself further and see what I was capable of. Little did I know I would get my chance sooner than I thought.

At the time I was working as a delivery driver at local takeaway. It helped pay the bills and it was the only work I was able to fit around my university schedule. It was easy work and almost all of our regulars tipped well. All except one guy.

This particular customer was a guy named Paul. He lived in a very wealthy part of the neighbourhood in a giant modern house and never paid a cent over the cost of his food. He was your typical middle aged finance worker type. A bit over weight, greying hair and the kind of attitude that made it clear he thought everybody was beneath him.

Whenever I delivered to him he always insisted that I call his phone to announce my arrival so that he could buzz me though his security gate, making sure to drag out the phone call in some kind of weird power-play. Once I got up there he'd make some big fuss about the food being late (it never was), and use that as an excuse to not tip. To make things worse, he always requested me specifically as the driver, like he had some strange vendetta against me. None of the other drivers wanted to deal with him so that was fine by them.

On this particular night we were a few minutes from closing up the shop. It had been a long shift and I was ready to clock of and head home. I was just about ready to leave when the phone rang. My manager took the call and once he hung up told me that we had one last delivery. No surprise, it was Paul. I was a pretty annoyed at the lateness of the call and that my manager had accepted the delivery, but he told me that he'd prepaid with credit card so I wouldn't need to come back to the store to cash out, I could just take it on my way home. Seeing no way out I sat back while the kitchen staff put together his order.

Once it was ready I made my way out to the back parking lot preparing myself for the same standard ordeal that comes with delivering to him. That was when my phone buzzed in my pocket. Taking it out to look at the screen I saw a message displayed.

"How'd you like to make a tip for once?", the message read.

I was momentarily confused before realising that this message must have come from Paul. Of course he had my number, he made me call him from my phone every time that I delivered to him, but he had never messaged me before. I didn't think anything of it at that moment. Customers occasionally made the odd request for us to pick up something from the shops for them; milk, a packet of cigarettes or something of the like. It's something I was always happy to do as they usually tipped generously for the service. Bearing this in mind I typed out my reply.

"Sure, what do you need?", and hit send.

Climbing in my car, I started making my way towards his street knowing I'd pass a few shops as I got closer. Then the second text buzzed in my pocket. I parked my car to the side of the road, pulled my phone out and opened Paul's message.

"How much you earn will depend on what you're willing to do", it read.

I had no idea what to make of this. Why doesn't he just tell me what on earth he wants?

I wrote back my reply, "What do you mean? Do you need to pick something up?"

His next few messages came through quickly, one after the other. I could see the little icon showing he was typing so I just sat there and watched them flash across my screen.

"No", his first message read. "In fact I need you to drop something off."

Then came the message that made my heart stop in my chest. "When you arrive at my door, I want you standing there with the food, and NOTHING else."

He let that message hang in the air for a moment before continuing. "I want you butt naked on my door step like a good little delivery bitch. Then you will earn your tip. If you can't do that then don't bother coming. If you can, then get here now. The gate is unlocked."

And just like that, my heart was pounding again. I had never considered in a million years that this was what he had in mind. Images started racing through my head. Images of me walking up the long winding steps to his front door. Walking up naked.

It didn't take me long to make my decision. This is what I had been yearning for, this excitement, and it was in my grasp. I decided that I wouldn't reply. Maybe he would think that I was refusing his offer. He would soon find out how wrong he was.

Pulling out from the curb I accelerated towards his street. I a few short minutes I was parking my car opposite his front gate. True to his word, I could see that it was slightly ajar.

Paul's house, like every house on his side of the street, sat at the top of a steep slope. At street level there was a hight concrete wall, broken only by a single pedestrian gate set in the middle. Once through the gate you were faced with a long winding set of stairs that snaked their way up the slope towards his front door that sat on the left side of the house. The front face of the house was made up almost entirely of glass, giving anyone inside an unobstructed view over the tops of the houses across the street.

It was at the bottom of these stairs that I found myself. Closing the gate behind me I heard it softly latch, locking into place. I steadied my breathing and prepared myself for what I was about to do. I gently lowered the bag of food that I was carrying to the floor. Looking up at the winding staircase ahead of me I realised that as I walked up the first flight I would be above the level of the concrete wall for the remaining two flights. It was fairly well lit and this would give anyone who happened to glance up that way a clear and unobstructed view of me. The sensible thing would be to wait until I was at the top and around the corner before undressing. But I wasn't feeling sensible in that moment.

Not wanting to give myself the chance to second guess my decision, I quickly shed my clothes. In a few short seconds I was standing completely stark naked at the base of the stairs. Bundling up my clothes in a pile, I tossed them into the nearby bushes. I let the sensation wash over me for a minute. I could feel the cool night air dancing across my skin, raising goose bumps across my body. I ran my hands over my completely smooth crotch, feeling my little cock and balls bounce a little as I brushed them.

Deciding that I had waited long enough, I picked up the food bag and made my way up the stairs. Each step forward took me higher above the wall and into the line of sight of the street below. I wondered what someone would think if they passed by and looked up to see my pale naked body climbing the stairs.

As I climbed higher I started to wonder to myself how I should be standing when he opened the door. Should I be covering myself? Should I stand with my hands behind my back? Should I kneel? I felt a sudden twinge in my cock as I thought of the that last one.

Before long I found my self at the top of the steps and as always, slightly out of breath. Taking a moment to catch my breath, telling myself that it was already too late to back out, I reached out and knocked twice.

Holding my breath with anticipation I realised I could hear my own heart pounding in my chest. Any second now the door would swing open and this man would be faced with me standing there completely naked on his doorstep. With a sudden surge of adrenaline I heard the latch turning on the other side of the door before it slowly swung open, bathing me in light.

The look on Paul's face was initially one of surprise, but this was quickly wiped and replaced with a deep and lecherous leer.

"Well fuck me. I didn't think you'd actually do it", he sneered. He let that hang in the air for a second before continuing, "Well, better get you inside and take a proper look then."

Opening the door wider, he beckoned for me to enter. I stepped in slowly, feeling the cold marble against my bare feet. Instinctively looking around for somewhere to place the food I hear him say behind me, "Just put that down on the floor. Doesn't matter where."

I obediently complied, making sure to bend at the waist while I lowed the food bag, causing my little cock and balls to momentarily hang between my legs. Standing straight I turned to face him. I realised that my legs were trembling slightly with a mix of nerves and anticipation, and judging by the look on his face this amused him greatly. He was staring intently at my body, drinking in every inch. His eyes traced a path down from my face, along my chest, pausing briefly to smirk at my tiny hairless cock, before finishing at my bare feet.

"So", he said, slowly pacing across his floor staring at me, "You've decided to take me up on my offer. I had't expected to you to be so compliant. I've gotten tired of seeing you here every week fully dressed. It's nice to see you wearing something more appropriate for a little delivery bitch." He looked into my eyes long and hard before asking, "You are a bitch...aren't you?"

Knowing that there was only one answer that he wanted to hear, I lowered my eyes and meekly replied, "Yes Sir."

"Good. That's what I thought," he chuckled. "Come this way, I want to show you what I have in store for you."

Without another word he turned towards the hallway behind him and walked through to the living room at the front of the house. I followed behind, my bare feet making a slight padding noise on the cold marble.

The room was a large open space with the far wall taken up completely by floor to ceiling windows. We were high enough on the slope that nobody would be able to get a clear view though the windows, but it still made me feel incredibly exposed. In the centre of the room was a low coffee table, and what was sitting upon it almost made my heart stop for the second time that night.

Laid out in a neat row were four objects, each with a corresponding amount of money in front of them. The implication was very clear. The first object on the left was a marker pen, and in front of it a single five dollar bill. The second was a small vibrator, about six inches long and smooth. In front of the vibrator lay three twenty dollar bills. Next to that was a full sized dildo. It looked to be about eight inches long as was the kind that looked like it was cast from the real thing, fully detailed right down to the balls. In front of that lay four fifty dollar bills.

But it was the last item that had drawn my attention. Sitting on it's side next to a stack of fifty dollar bills was a full sized rubber arm with a fist at the end. I had seen pictures of these kind of sex toys online but never in person. It was truly horrifying to image a person willing forcing that into themselves.

Paul's voice broke the silence. "In case you haven't worked it out already", he said to me, "It should be pretty obvious what I would like from you. Whatever item you pick from here will be going inside you tonight. Once I'm satisfied with the result you can collect your tip. Understood?"

I nodded meekly in response, unable to answer with my heart now pounding in my throat. I realised that the nerves and anticipation of what was about to happen had caused my already tiny cock to shrivel pathetically. The amused leer on Paul's face made it very clear that he had noticed also.

"So, what will it be?", he asked.

I took a trembling step towards the table, considering my options. I knew straight away that I could rule out the marker pen. The small amount of money was clearly made to put me off that option. I also knew that there was no way on earth that I could handle the fist. That left the dildo and vibrator. I had only ever put a single finger of my own in my ass, and apart from two experiences with a stranger's thumb nothing larger had ever gone in there. I thought to myself that the dildo might be biting off more than I could chew and the vibrator would be a safe bet. At this point I was so lost in the experience that I didn't even care about the money.

Making my choice, I turned towards Paul lowering my eyes. "I'll take the second one Sir."

He paused for a long moment before responding. "You know bitch, if you don't challenge yourself you'll never find out what you're truly capable of. Let's go with option three shall we?" His tone made it abundantly clear that this was not a question. Looking again at the vulgar dildo sitting on the coffee table, I took a deep breath to slow my heart rate and replied, "Yes Sir."

"I thought so," he sneered. "Oh I almost forgot, you'll be wearing these." Digging into his pocket he pulled out a set of wrist cuffs and dangled them in front of my eyes. They were basically two leather straps fastened by velcro and joined together by a small chain. "I do like watching little bitches squirm with their hands tied."

This was quickly spiralling out of control...and I could not have been more excited. Without a word I turned my back to him, placed my hands behind me and dropped to my knees. Kneeling on the cold marble with my ass cheeks pressing onto my heels I could feel them part slightly. Shifting my position a small amount, I moved my legs apart opening my cheeks further. I heard Paul move closer behind me as he bent over to fasten the cuffs around my wrists.

After checking that they were secure he walked around and knelt down in front of me. "Now I need to ask you," he said, "have you ever had anything this big inside you before?"

"No Sir," I replied.

This drew a smile to his face. "Well then," he said, "I think I may need to loosen you up a little first. Put your face down."

Obediently, I lowered my face forward until my forehead was pressed against the cold floor. With my hands tied behind my back this caused my ass to stick up in the air, wantonly presenting my asshole to the room. He moved around behind me and I heard the soft noise of a bottle being uncapped. With a sudden jolt I felt a cold liquid dripping between my cheeks. He was putting lube on my ass!

Tracing his rough finger slowly around my puckered asshole, Paul slowly started massaging the lube into me. I was just beginning to enjoy the sensation of him caressing my most private parts when he suddenly broke my trance by driving his finger deep inside me. I let out a surprised scream which only caused him to laugh.

"That was just a finger boy", he chuckled to me. "Just wait until you feel what comes next."

The sensation of having his finger deep inside me was completely different to the times I had fingered myself. He was pushing his finger hard into my asshole, forcing the lube deep inside me. As he pulled out I felt him line two fingers up against my anus. I didn't have time to prepare myself for the further intrusion before he was forcing his way back inside me. Trying not to scream this time I let out a deep grunt and scrunched up my face against the pain. This seemed to amuse him even more.

Finally deciding that I was sufficiently lubricated, he pulled his fingers out and walked over to the table. Picking up the dildo, he sat it upright in front of me and started smearing lube along the shaft and tip. I was transfixed starting at the thing. I could not believe I was about to let him put that thing inside my virgin ass. Almost seeming to read my mind, Paul looked up and made eye contact with me. "Oh don't worry bitch," he said, "I'm not going to force this in you. You are. Stand up and come over here."

Getting back onto my feet from the position I was in was no easy feat. With my hands still bound behind my back I had to awkwardly wriggle my way onto my knees before rising to my feet. My legs were trembling more than ever as I made the few short steps towards him. My little cock was almost fully erect from the attention that he had been giving me, and a thin strand of precum was dripping from the tip.

Standing up and stepping away from the upright dildo, now glistening with lube from top to bottom, Paul gestured for me to stand over it. "You're going to lower yourself down on that now," he said. "I want to see how deep you can get that thing inside of you. And when it's as deep as it can go, I want you to go further. Then you're going to bounce up and down on it until I tell you to stop. Understood?"

I nodded meekly, unable to form the words needed to reply. Letting Paul take me by the shoulders and guide me, I positioned myself over the tip of the dildo and began to squat down. With my legs still trembling it was difficult to lower myself exactly over it, so I was quietly glad for Paul's hands still on my shoulders helping to line me up.

Squatting a little lower, I felt the sensitive skin of my anus touch the lube soaked tip of the dildo. Clenching my jaw, I began to slowly lower myself down. I had never had anything remotely close to this size enter my asshole before, and I could feel the intense pressure building as the tip of the cock pressed against my opening. I took a deep breath and as I exhaled I tried to relax my self, hoping that my asshole would also would relax to accept this foreign object.

I slowly rubbed back and forth along the tip, feeling the hard rubber pressing against me, slowly opening me a little wider with each thrust. Just as I was starting to feel the tip push past my sphincter, Paul it seemed had grown impatient.

"Get on with it bitch!" he yelled, at the same time he pushed down hard on both of my shoulders. I was immediately forced down the length of the shaft. In one swift motion I felt the tip of the cock push through my opening and plunge deep inside me. I felt my asshole pulled open wider than it had ever been as it opened to accept the full length of the dildo. As my ass cheeks met with the cold marble floor, the entire shaft now buried inside me I let out a scream of mingled agony and pleasure.

For a moment I was seeing stars. The pain quickly gave way to a deep satisfying feeling unlike anything I had ever felt before. As my head began to clear I realised that Paul was laughing at me. The shame I was feeling was like nothing I had ever felt before. I was but naked, squatting down in front of this bastard with a dildo buried in my ass. All for his amusement while he stood there fully dressed. And most of all...I was enjoying it.

Without fully realising that I was doing it, I began rocking up and down on the dildo. The sensation of the shaft sliding in and out of my stretched asshole was unbelievable. Each time I lifted myself up and lowered back down I pushed up a little higher, until eventually I was bouncing up and down on top of it. The base of the dildo was suctioned to the floor keeping it in place, allowing me to fuck myself freely in this wanton display.

Paul had been standing in front of me leering as a slowly picked up the pace and I could see the bulge growing in his pants. Clearly enjoying the scene in front of him, he reached down and undid his belt buckle. Not wanting to break the hypnotic trance that I had found myself in, I kept working myself up and down on the shaft beneath me and he slowly let his pants down and pulled out his cock.

Seeing his shaft spring out of his pants in it's full glory, I was immediately frozen in place. His cock looked to be about 10 inches and thick, and he was rock hard. He was neatly trimmed around the base and his balls were shaved smooth. Staring up at his shaft as he stood over me, I became aware of the dildo in my ass again. Only now it felt much smaller.

"Have you ever sucked a dick before bitch?" he asked.