Story - How I Got Lucky At Work As A RedMart Delivery Person

[Asta5x]

Hi everyone my name is Ben and I’m in my late 30s currently. This story happened around mid 2023 so roughly 1 year ago, I lost my job during the post covid-19 period in 2022 after which I tried out different kind of gag jobs while looking for my next permanent employment. After more than a year of attending interviews while working at the same time ended without success I gave up. In the same period, I have tried out driving PHV, doing food delivery and delivering parcel before eventually sticking to my choice of doing RedMart delivery which I felt was the best option out of the above.


The delivery zone which was assigned to me is the Bedok – Eunos area, conveniently for myself I also happened to stay around this area, another good thing is that once you are assigned a delivery zone normally it doesn’t change on a daily basis unless there are shortages of manpower in certain zone and they needed backup.

Anyway, most of you may know doing gag jobs let you meet all kind of people both good and bad ones and it is during my work as a RedMart delivery personnel I met Jocelyn. I remembered the first time I met Jocelyn it was just another routine day for me, since we are always in the same area there are some regular customers whom I can remember after delivering to them several times, however when planning my route for that day I can identify this was a new address which I haven’t make any delivery before.


When I pulled my truck over at Jocelyn’s address it was a HDB block nested in an old estate within Bedok, however Jocelyn’s unit was easily recognizable as it was a corner unit and you can tell from the main gate it was a newly renovated unit among the stretch of old and rundown units of her neighbors. Jocelyn’s booked delivery timeslot was in the morning and I recalled it was probably the first or second delivery I had made that day.


I buzzed the doorbell but no one answered, I then started slowly unloading Jocelyn’s purchase, it was a big order consisting of several bulky and heavy items and I was thinking it’s going to be troublesome if no one is at home with so many stuff. Luckily halfway I was unloading suddenly someone opened the door and greeted me, I looked up and standing infront of me was Jocelyn.


Jocelyn is probably in her late 20s or early 30s, she looked like your typical milf next door with big round eyes and long copper colored hair. Jocelyn isn’t someone you will rate as pretty but definitely pleasant looking enough. I remembered that morning her hair was tied into a messy ponytail, she was wearing a spaghetti top paired with a pair of sexy cotton short showing off her long and smooth legs, I could see a bit of her cleavage showing through the spaghetti top as well.


Jocelyn apologized to me she did not open the door earlier as she was washing up when I rang the doorbell as evidenced by the small spots of wet stains on her top. I smiled at her and told her its fine at least someone is at home to receive the order. Jocelyn smiled back at me and began carrying those items I have unloaded back into her unit, usually if the owner had opened the main door before I unload the items, I would try to unload them into their unit but for this time as I had already unloaded some of the items outside the door Jocelyn started carrying them in herself.


As Jocelyn was trying to bring the items back into her house this was the moment I caught her bending down with her full cleavage in plain sight. My immediate reaction was to look away but as I continued to unload the rest of her purchase, I was carefully peeping at her at the same time and it seemed that Jocelyn wasn’t aware of what was happening. Although it was also true that she doesn’t have the luxury to cover her chest with her hand while bending down as some of the stuffs were too heavy for her even with both hands or maybe she felt safe and confident enough with the padded spaghetti top even though she clearly wasn’t wearing a bra.


Anyway, this wasn’t the first time something like this had happened to me although on this occasion it is definitely one that lasted the longest and most steamy while others are just like 1-2 seconds of downblouse or upskirt, I just thought to myself this is one of the extra perks that comes along with this job so why not continue to look since Jocelyn was still busy with herself, I continued to stare at her chest even after I had finished unloading all her items hoping I could catch a glimpse of her nipple.


However, that did not happen as Jocelyn snapped me out of the moment and called out to me to help her with the 10kg bag of rice which I happily obliged. As I moved closer to Jocelyn, I’ve gotten the chance to look at her boobs up close which I determined to be around B to C cup size, her boobs also appeared to be incredibly smooth and soft, I could also smell a very nice fragrance coming from her. All these were starting to make me feel horny and I could feel a stir in my pants, as I was getting an erection gradually.


I told myself to calm down before I do anything stupid or illegal, I tried to hide my erection from Jocelyn’s view and quickly help her to move the rest of the stuff into her house to which she thanked me profusely and commented that I was very helpful unlike some of the other delivery person she had met in the past. I replied her that I appreciate her kind words and it I was just doing part of my job as I took my leave.


When I got back to the truck, I knew I had to get my erection off if not I wouldn’t be able to continue working, I hopped to the back of the truck and started masturbating to the images of Jocelyn which were still fresh in my mind, I imagined myself slipping my hands into her cleavage and caress her soft boobs before pulling down her spaghetti top and suck on them, as I was feeling horny I cummed rather quickly.


For the rest of that day I tried to focus on my work but it was impossible not to think of what happened this morning with Jocelyn and for the next few weeks I was praying everyday for Jocelyn to make a new order and my prayer was finally answered when I saw her address popup as part of the delivery route planning one morning…











To be continued…….......

[TheDriverGuy]

Camping here

[mensammy]

yah.. continue..please

[scuderia88]

Bro, you are super lucky and I am sure you don’t wish to leave your new job.

[TuNguyen]

Camping for updates too!

[Polar.Bear]

Pitch tent

[Rickey]

Thread title suggests it's going to be exciting...TS, i m jealous...i want to help u deliver to Joselyn's unit, can ??

[inlandtaipan]

waiting for more updates

[Jands]

Nice......keep it coming!

[kirk18]

Originally Posted by Rickey

Thread title suggests it's going to be exciting...TS, i m jealous...i want to help u deliver to Joselyn's unit, can ??

Waiting for her to bend?

[Rickey]

Originally Posted by kirk18

Waiting for her to bend?

Or squat

[Asta5x]

Once the route planning was done, I wanted to rush off to make the first delivery to Jocelyn so I could see her again but I had thought that maybe someone else might be at home if I reached earlier than the previous time. Considering that possibility I went ahead and did some other deliveries first before heading to Jocelyn’s house at roughly the same time as previously.


However, this time I came prepared and had come up with a different plan, as expected her gate and door was closed when I reached her unit this gave me the opportunity to unload all her purchase outside of the house. Once I was done unloading, I buzzed the doorbell and pretended to be busy shifting the boxes while waiting and hoping it would be Jocelyn who will open the door.


Ever since that day I saw Jocelyn’s cleavage while she was bending over, I had come out with a plan to secretly snap some photos of her doing the same thing. I was getting nervous and my heartbeat was beating faster and faster as I heard the sound of footsteps approaching the door and fortunately it was Jocelyn who opened the door.


After opening the door Jocelyn smiled and greeted at me, I looked up at her and acted as though I just finished unloading her stuff and greeted back at her gleefully trying to appear as normal as possible. Immediately I took a look at Jocelyn and I was in luck again as she was wearing a similar outfit the first time I saw her but this time this spaghetti top seems even more worn out and loose.


As Jocelyn opened her metal gate I quickly took out my handphone from my pocket and informed her I need to take some pictures as proof of delivery which she nodded her head in acknowledgment before bending down to inspect her purchase. Once again Jocelyn’s cleavage was in full view and in that few seconds I snapped as many photos as I can after which I hurriedly put away my phone as I was afraid of Jocelyn being suspicious or worst get caught in the act by her.


Me: Everything is here miss, no item that was last minute out of stock.

Jocelyn: oh ok. That’s good thank you…


I had another few seconds of good look at Jocelyn’s chest as I informed her everything is in order. Once I informed her, Jocelyn began bring the stuff into her house, as she was doing that she bended down with her back facing me and I could catch glimpses of her perky butt cheek while she lowered the stuff onto the floor. At that moment I almost wanted to take out my phone again to snap more photos of Jocelyn but as she was moving too much it would be difficult to take a clear shot so in the end I deemed it was not worth the risk.


After roughly a minute or so Jocelyn have managed to bring most of the stuff except the bulky and heavy one this was the que for me to move on to part 2 of my plan…


Me: Miss do you need help?

Jocelyn: I think so…but I thought you need to go already?

Me: the next delivery is just nearby only so I have time…I know these are quite heavy…

Jocelyn: okok…then thank you!


I carried the remaining items into the house and stacked them near the entrance of the door. I scanned the house and definitely it was a newly renovated unit and more importantly it seemed that no one else is at home…


Me: Miss…is there any one to help you bring all these stuff to the storeroom or something? I don’t think you are leaving them here right?

Jocelyn: err…….

Me: I can help bring them into the storeroom also…

Jocelyn: huh? Don’t need la…you have helped a lot already!

Me: its ok…why not I just help you with the heavy ones…then the lighter one you can sort them out yourself later…

Jocelyn: erm…mmm…okok…really thanks a lot~

Me: Ok these 3 heavy one…is it put them all in the storeroom or?

Jocelyn: yes need to put them in the storeroom…follow me the storeroom is there…


I carried one of heavy item and followed behind Jocelyn, the storeroom is located at the end of the living room, it’s a common layout for older HDB flat. I glanced around the house while I’m in there, it was nicely renovated and done up tastefully and more importantly looking for details who might Jocelyn be staying with. I don’t see any wedding or couple pictures in the living room but Jocelyn is most definitely married because I saw slipper and shoes in man sizes most probably belonging to her husband.


Jocelyn opened the door to the storeroom which was pretty compact and filled with all sort of stuffs but they were arranged neatly both on the rack and the floor, while Jocelyn was standing inside the storeroom figuring out where best to put the new purchases I placed the first item down and told her I will bring the remaining two items over first.


Once that was done Jocelyn signaled to me to come in with the first item, I was expecting her to step outside so I couldn’t believe my luck when she asked me to come in! Even when I was outside I could tell there was barely enough space for two persons to stand in there, when I entered I had skin contact with Jocelyn as our shoulders were basically rubbing against each other, being so close to her I could smell the sweet scent coming from her body again.


It was really hard to maneuver in such a confined space so I took the opportunity and purposely brushed myself against Jocelyn’s arms and legs more than necessary when I was unloading the first and second item. And seeing that Jocelyn did not try to leave the room or said anything even after what I did, it makes me even more excited. Instinctively I suggested to Jocelyn to put the last item on the rack behind her…


Me: this last carton the 24 cans of coke can put on the rack behind you I think…just need to move those things away then will have space…

Jocelyn: this one?

Me: no one more the one above your head.

Jocelyn: ohh…ok…can…lets put it there then…


Next, Jocelyn tried to shift away whatever that was blocking the space to one side but was struggling with it so I stepped behind her and extended my right over her shoulder and helped her push together. I’m not a very tall guy only about a head taller than Jocelyn but that was enough to give me the perfect view of staring down her boobs from behind while I assisted her. Shortly after I could feel my cock which was already slightly harden erected more in my pants.


While I was pushing the stuff in to get them into the corner I also pushed my hip against Jocelyn’s butt, this whole action only lasted about five to ten seconds but I’m sure she could have felt something grinding against her butt and that make me a little nervous as I’m unsure of how she will react.


Jocelyn: ah…thanks…its quite heavy~

Me: no problem I go bring in the coke now.


Fortunately Jocelyn did not said anything, I grinned to myself as she was also still not stepping out of the storeroom, I was getting quite horny by now which also makes me a little bolder as well. I grabbed the carton of coke and quickly position myself behind Jocelyn again, she turned her back towards me again and offered to help which I happily accepted.


I was wearing a loose pants that day so I could see my own erected cock pointing outwards and the shorts that Jocelyn was wearing was pretty tight making her perky ass cheeks very obvious, I pressed my cock in between her ass cheeks as I took my time lifting the carton of coke over her head, I tried to distract Jocelyn by jokingly telling her not to move if not the whole carton of coke might fall on her head…


Me: Miss…don’t move ah…later the whole carton drop on your head…

Jocelyn: WEI~~~ becareful! Don’t scare me leh~~

Me: HAHA…won’t la…its on your right now come help to hold and push inside.

Me: ok let push it in further to the side so next time got space…

Jocelyn: okok~~


Once the carton of coke was secured on the rack I did not use much strength anymore, this help bought myself a few more seconds to grind on Jocelyn’s ass, sniff her hair and look at her delicious cleavage. I stopped what I was doing after Jocelyn turned around and told me it was done and we chatted for awhile before I left…


Jocelyn: ok done! Thanks a lot!

Me: you are welcome…you thank me a lot of time this morning liao

Jocelyn: of course! You did not need to do all this but luckily you helped, I confirm cannot do it myself…

Me: As I said it’s just part of my job and if I can help I will…by the way you bought quite a lot of stuff…previously also quite a lot so I don’t think you stay alone right?

Jocelyn: ohh…no la…I stay with my husband but he do shift work so he is not around now…

Me: ohh…good la at least he can help next time.

Jocelyn: errr…actually I try not to disturb him when he is back from work because usually he’s very tired that’s why I always arrange for delivery when he is not at home.

Me: wah…Miss you are a very caring and understanding wife!

Jocelyn: haha…my name is Jocelyn…but I think you already know right? What’s your name?

Me: yup I know your name already since it’s in the delivery address haha. my name is Ben nice to meet you Jocelyn~



After our brief chat I took my leave and Jocelyn offered me a can of coke as a thank for my assistance. Once I left the house I rushed back to the truck and masturbated to the scenarios between myself and Jocelyn again to satisfy my urge. It was super busy for the rest of the day and it was not until at night when I’m home I remembered about the photos I took of Jocelyn and luckily some of the photos turned out ok and I wasted no time cumming again on her photos as I anticipate the next delivery to Jocelyn’s home again…




To be continued……............

[kirk18]

Originally Posted by Rickey

Or squat

If she doesn't wear panties .....