I [20F] have gotten free Doordash multiple times recently in exchange for showing off my body to my delivery guy.
I’m a college gal home for the summer (and COVID). Like many others, I’ve been using Doordash a lot both for safety and convenience. And also like most people, DD in my area leaves the food outside your door for contactless delivery. I’ve used it regularly since I’ve been home and it’s always been normal. That changed about a week and a half a go.
Due to the heat of the summer and because I like being comfy at home, I often hang out in large, flowy tshirts. I usually wear short track shorts or no pants at all, and I go barefoot. Last Monday I ordered food. When it was delivered I went out to the porch in this outfit, still barefoot, to get it. I took a quick glance in the bag as I was picking it up, when I heard a shout of “All good?”
I looked up. The yell had come from a Hispanic guy, probably in his mid-30’s, who was sitting in a car by my curb with the window rolled down. I live in a suburban area with a bunch of cars parked in the street so I hadn’t taken notice of one more.
“Are you the driver?” I called back. He nodded, so I made another check of the of food and gave him a thumbs up. He returned the gesture and drove off. It was a quick and innocent encounter and I didn’t think anything of it.
The very next day I ordered food again and one of my moms had asked me to check the mail while I was stepping out to get the food. It turned out to be the same driver, and he again waited to ask if things were good. I said yes, and began heading down my driveway to the mailbox while he got ready to drive off. Our pavement was boiling so I had to sort of skip/tip toe quickly to avoid burning my feet. As I made my way back to the house I heard him laughingly ask from his car, “Why aren’t you wearing shoes?”
“Too lazy!” I called back, laughing along with him, and he just waved and took off. Again, very innocent.
Things took a turn on Thursday. More food ordered, and when I went to get it I saw the same driver’s car parked but his window was up and he didn’t call out as he had before. There was a glare on his window from the sun so I couldn’t totally see if he was looking at me or just checking his phone for the next order. I went back inside and as I was unpacking my food, I found a sticky note with a handwritten note:
“Happy I can keep delivering to you.” And a phone number.
I thought it was a sweet bit of flirting, and though I knew nothing about the guy I didn’t see the harm in texting him to at least thank him for the note in case he was nervously wondering how his move would go. I shot him a text thanking him and also thanking him for always waiting to make sure my order was right. We spent a bit of time doing the usual introductory stuff. I told him my name and that I was in college. His name is Maxiano and he is 33, he’d just started dashing recently to make some extra money but mainly worked as a cook at a local Mexican restaurant. When he found out the age different he apologized and offered to leave me alone, but I told him I didn’t mind just chatting. I asked him why he’d left the note, and he admitted he thought I was very pretty. I was flattered, but I could tell there was more to it. He was the type of guy who, when texting, would say things like “I wanted to say more but I’m not sure” or “Can I ask you something?” …”Nevermind”. Some guys do it to be coy or mysterious but I could tell Maxiano was just actually nervous and second guessing himself. After some gentle prompting, I finally got him to admit the truth:
“You have very pretty feet, and I have been staying to watch you get your orders to see your feet and legs.”
I know a lot of girls would be creeped out by an older delivery guy saying this to them. And yes, logically I probably should have been too. But I love exhibitionism and I also love feet, so this scenario was a literal fantasy of mine come true! I assured him that I was flattered and not put off by his confession, and told him I’d always be sure to get my orders barefoot whenever he was my dasher. The fact that I was into our little secret arrangement excited Maxiano a lot. He giddily explained how much he admired my feet and how he’d like to rub them and massage them, and I was living for it. We concluded our day of texting with a goodnight, and I was really excited by the new development.
On Saturday, Maxiano texted me in the afternoon to ask if I’d be getting food today since he was out on a shift. I told him I hadn’t planned on it. He offered to pick me something up for free. I did my best to insist against it, telling him I couldn’t accept that and he was out to make money, not spend it on me, but he was extremely stubborn and assured me about a hundred times that he wanted to do it to thank me for not being upset at his confession. The more this went on the better free food sounded, so I finally caved and agreed to let him grab me something cheap from a fast food place. He texted me when he arrived, and I knew I had to repay him somehow for his kindness. When I went out onto the porch this time, I took my time, milling about and lifting my feet to tap my toes on the tile and flash my soles at Maxiano in his car. I even sat on our porch swing, propping one foot up on my knee, and ate a few fries while waving at him. I could see him smiling in his car as he waved back before driving off.
Within minutes, my phone was blowing up with emojis and texts from him thanking me for showing off and complimenting my feet. He told me how sexy I was and that I’d even turned him on.
“Can I say something else?” He asked eventually.
“Sure!” I replied.
“You have a really sexy butt too” he told me.
As my username indicates, I have a nice ass and I’m proud of it, so I was thrilled to hear Maxiano compliment it!
“Thank you! Too bad you delivered on a day when I was wearing shorts. Sometimes I’m not ?”.
After about five minutes of stop-and-start typing, Maxiano finally said: “Would you ever get food on your porch like that?”
“Only for the right driver! ?” I teased back.
“What do I need to do to be the right driver?”
“Keep complimenting me!”
I’d been joking of course, but Maxiano was clearly determined to get the show I’d teased because he lavished me with compliments and practically begged me to accept more food from him the next day so he could watch me again. I was totally down to continue our exhibitionist game, so I didn’t play hard-to-get for too long before agreeing. He had a later shift the next day so he’d bring the food by in the evening.
I had butterflies all day waiting for our little exchange. I had decided what to do to give Maxiano a fun show. When he said he’d dropped the food, I went out in shorts that barely came down to the hem of my long sleep shirt. It was dusk by now and our porch light was on, illuminating me like a spotlight, but I couldn’t see Maxiano through his car window. I knew he was watching though, and I also knew he was probably confused as to why I was wearing shorts after our agreement. I held up a finger to indicate to be patient, and proceeded to turn around and work off my shorts from under my shirt. I let them drop to my ankles, and playfully kicked them away, flaunting my feet as well for Max. I bent down to get the food, knowing that my shirt was pulling up enough to give him a taunting flash of my panty-clad cheeks. I straightened up and checked the food, then reached back and quickly tugged my shirt up to give him a brief, full-on view of my ass in cheeky undies. I then grabbed my shorts and scurried inside, my heart pounding with exhilaration.
Just as before, Maxiano blew up my phone almost instantly. First he just sent about twenty different emojis expressing his elation. Then came a stream of texts: “That was incredible” “So sexy” “I have you stuck in my head” You get the idea. Knowing Max enjoyed it as much as me was honestly a huge turn on. I went to my room and began to play with myself while we continued to text. Max kept thanking me for being a good sport, and said I was the sexiest girl he’d ever seen. As nice as his words were, I wanted to push him further. Though Max was obviously attracted to me, he kept his words very PG-13. He rarely cursed, and most of his texts were about wanting to pamper me and my feet, make me feel good, etc. He didn’t really talk about himself, but I knew he probably had some very dirty thoughts running through his mind. And I wanted to hear them.
“If I ask you something will you be honest with me?” I asked at one point.
“Yes always” he said.
“What did watching me make you want to do? You can tell me, whatever it is. I won’t be upset.”
This time a solid fifteen minutes passed before he answered. I’ll copy/paste his message here:
“To tell you the truth Brooke you made me so turned on. Whenever I see you I feel so hot for you but tonight when I saw you take off your shorts for me and show me that big, beautiful butt I got so hard. ? You are so perfect and have the sexy body that drives me wild’!! I wanted to see that big butt up close and feel it in my hands, feel how soft it is and make it jiggle right by my face. Does it jiggle Brooke? I bet you would shake it so nice for me and let me touch it and kiss it. And then I would put your sexy sexy feet in my lap and rub them and feel them against me. I get so hard picturing your toes and feet in my lap. I want them on every part of me, loving them like they need it.”
Hearing Max talk dirty like this was making me super wet. I rubbed my clit feverishly, pausing to reply:
“I loved showing off for you. It made me feel so sexy and naughty to know you were watching. I’m glad I could put on a good show for you!”
We continued this back and forth, with Max saying much of the same type of things, until he sent: “I want to spread that big white ass and lick your ass and wet pussy and make you creamy for me”. Hearing Max use such naughty, vulgar language put me over the edge. I sank two fingers into my pussy and worked myself hard for a second until I came, waves of pleasure rolling through my body and down my limbs while I imagined Max’s eager face buried in my ass.
I responded by asking when we could do another show. Max wouldn’t have a shift until Thursday (yesterday), so we planned to do it again in the evening.
As the week crept by I’d get random texts from Max. They seemed to waver between asking how I was and other sweet things, and super dirty reminders of how he wanted to suck my toes and spread my cheeks to admire my asshole. It was clear that Max definitely had a thing for voyeurism and oral play. Though he was becoming more comfortable saying naughty things he still never mentioned actual fucking or anything like that. It was all about how he wanted to watch me, admire me, and worship me with his mouth. In a way this made our arrangement even hotter. It felt different and more forbidden, and it was driving me mad with delight and desire.
So yesterday finally came and Max delivered the food as normal. This time I exited with only a skimpy thong beneath my t-shirt. I started with the usual, showing off my feet and lifting my shirt so he could see my booty. Then I slipped off my thong as I’d done with my shorts before, leaving me naked under my shirt. I held up the tiny panties for him to see, then teasingly held them in my teeth while slowly pulling my shirt up once more. I gave him several seconds to admire my bare ass, then cupped my cheeks and jiggled them playfully before letting my shirt drop back down. I waved, blew Max a kiss in his car, and turning to the door I gave my ass a quick little slap before going back inside.
Max was overwhelmed with delight. I wanted to make sure he knew how much I liked making his day, so I asked him if he was home. He said he was and that his shift was over.
“Are you going to jerk off now? ?” I asked.
The typing/stopping started, but I was impatient.
“Don’t be embarrassed. I want you to.”
The typing stopped. I could picture him pulling his cock out, stroking it after it had been aching all day, his eyes glued to my words on his phone screen.
“I want you to jerk off to my jiggly ass that you saw tonight, ok?”
The typing started again. “You have the nicest and fattest ass Brooke baby. I wanted to touch myself all day thinking of you and then seeing you get naked for me. I’m rubbing it now.”
I kept encouraging him, weaving images of my soft soles working his dick in his lap and my booty bouncing for him, all the things I knew would drive him crazy. Sure enough, after just a few minutes he told me he’d finished, and that it had been of the best ones he could remember. He thanked me and fell asleep not long after.
Which brings us to now! What should I do next to entertain Maxiano? ?
Source: reddit.com/r/gonewildstories/comments/hp4dvk/f_im_20_and_ive_been_getting_free_doordash_by
How far away is he when you give him a peek? Maybe a closer view would be appreciated. I’m sure I would appreciate it if I was him!
If you know he’s on his way, leave out a pair of your panties for him. That way he can play with them when he gets home after you put on a show
If he wants to lick you and get you creamy, why not get yourself and your panties creamy before he arrives, then when you go out slip your panties off and leave them for him. Or leave them for him before he arrives, a present for him to enjoy.
Mask on, panties off and let him fulfill his promises to you girl ?
Definitely leave him a pair of panties.
Tell him to keep the food in the car, and you’ll come get it from him. He’ll get to watch that ass walk away after any show you give him
Wow what a story now I want to start doing door dash, well I agree with leaving him wet panties, going to keep checking for updates
So hot, thank you for sharing. If you’re into toys you could put a plug in next time you give him a show… might make him wild to see something in you
How do you get it for free if you have to pay for it before it’s delivered?
True story I had sex in a hammock with masks on. High key recommend.
Leave worn socks for him so he can smell them and cum into them while texting with you about licking and sucking your feet. Btw that story is super hot ??
I hate how envious this makes me. I normally throw more decent clothes on before I run to answer the door, but I might have to stop doing that after reading this.
Is part of the thrill that he’s different than most guys you date? Do you often go for older guys?
Loved your story. There’s a short story you would love, by the English writer Alan Bennett, called “Miss Fozzard Finds Her Feet”. Not explicit at all, but you will be in no doubt. And wonderfully funny in its arch British way. There’s a short movie as well, but I haven’t seen it. Enjoy
You’re the girl I hope to stumble upon when I am doing deliveries.
Ok but like, we wanna see your booty too ? not nude
If you like entertaining max for free, i bet youll love entertaining reddit ?
Have you ever let him touch you at all ?? Like gotten in his car and how comfortable are you with doing that
You do got a nice booty. Definitely had to creep on your profile after that mention ?. Hopefully you like butt play, otherwise it’s a waste!
Had to check your profile after reading this hot story, was not disappointed! I hope you share more booty and feet pics!
This is so hot and playful. You’re a really fun tease!