Tales of the Deliveryman

Sounds like this story could be the After Hours of sandwich delivery men.

When I delivered Pizza back in 96-97 I had a few "interesting" deliveries. The most uncomfortable was this one:

I got a delivery in the middle of the afternoon at one of the local strip joints with the charming name of “The Rendezvous”. I usually look forward to them as half the time the strippers would answer the door naked. Unfortunately this was to the hotel above the club. As it was the middle of a very dead afternoon, I had the delivery out to them in only fifteen minutes. I was happy to be early as that frequently resulted in a good tip. After this incident I never wanted to be early again.

I walked up the hotel stairs to the second floor and was greeted by the most disgusting floor in the history of paid shelter. I believe it was gray carpet originally, but now it was a faded multicolour patchwork of stains overlapping each other. I made my way down the hallway and found the correct door. It was already open, and I immediately disliked the sounds emanating from it. I peek around the corner to survey the room. The floor was absolutely wall to wall with empty bottles, the desk, nightstand, and dresser were also covered. You couldn’t tip toe around or through any space on the floor. There were two exceptions; one was a clearing of bottles just large enough to accommodate the native man in the fetal position, dozing. The second was a path from the door straight to the bed. This is was the location of the other two occupants. A second native man was lying on his back in the bed, clothed but moaning. A small native woman was hunched over him with her face in his lap. I retreated from the door horrified. While hiding behind the door frame I tried to plan my next move. Several thoughts clouded my mind; do I interrupt? Do I let them finish? Surely they can’t take that long as they must be expecting me. If I do wait, should I stay in the hallway or go downstairs (I couldn’t go into the bar as I was 17 at the time)? I decide that with them leaving the door open they don’t care if I interrupt them. I knock on the door loudly and stand to the side to pretend I didn’t see anything.

The woman comes to the door and gives me a warm smile showing all three of her remaining teeth. “Wow, I didn’t think you would get here so fast”. I don’t recall my exact reply but I assure you it was some form of tortured high pitched squeak. The woman then begins to pay her bill in QUARTERS. The awkward silence as she counts her change is broken by her companion on the bed who rubs his crotch and drawls in a drunken note “come here baby I’m horny”. She continues to slowly count and I pretend to be oblivious. Upon the man on the bed proclaiming his desires again, I conclude it’s time for my exit. I take the eleven dollars in quarters I’ve collected thus far, mutter to the lady “close enough” and high tail it out of there.

I laugh at it now for several reasons mostly at my young self because, as disgusting as that scene was at the time, I was just so pissed off not to have gotten a tip.

When I used to deliver roasted chicken and assorted other chicken food (the shop was specialized in that stuff) way back in my late teens, I used to be one of the few male delivery boys in the late shift. Since many of us were female, a few particularly bad areas of the town were pretty much my personal territory at night, nobody else would drive there to deliver stuff.

So one night, I get this HUGE order to deliver to pretty much the most infamous gang street in town (not a huge town, but large enough to have a ghetto or two nonetheless), I get over there, and the door of the house is practically under siege by at least a score of guys wearing leather jackets, army pants and/or other stuff marking them as "bad company, avoid or die". And they are right in the middle of robbing some poor guy, whos lying on the street and getting searched for valuables.
Not knowing what to do, I just took my chicken and made it towards the door. One of the guys notices me, stops me and asks in horribly accented german "Hey, wrong door. Whos chicken is that anyway? You got money?" I was pretty scared, stammered the address, at which point his face goes a shade of white, he steps back and calls to his boys to let me pass, cause its "Gregoris hot chicken".
One of the guys even held the door open for me (I had both arms full of chicken food), and they pretty much jumped out of the way.

A few weeks later a friend told me that Gregori is the first name of pretty much THE boss of that street, and he obviously made sure that food delivery wasnt getting delayed on his turf

I ve never had any trouble delivering food in that area, or a different ghetto I worked in a year later, by the way. Seems at least here, the delivery man is off limits for mugging and robbing.

Some decent reads here.
http://tipthepizzaguy.com/stories/