Pizza guy/room service stories
 

I was a pizza delivery driver when I was in my late teens/early 20s. I never knew what I was going to see when the door opened. Especially late at night. I lost count of how many women opened the door while wrapped (or barely wrapped) in a towel. I remember one who was wearing a button-down shirt that wasn't buttoned. Seeing a bare set of breasts was a trophy delivery.

My girlfriend recently started providing the pizza guy with a visual tip when he delivers. She suggested being topless after I ordered food a few weeks ago. I suggested her walking out of the bathroom like she didn't know he was here so we went with that. I made sure I stood to the side of the doorway so the driver had a clear view into the kitchen. She walked in as I was slowly getting the money out of my wallet while facing the driver. I could tell she was there by the look on his face. I then heard her ask what I wanted to drink as she reached up into the cabinet. Her 38DDs on full display. I could tell he was looking by me as I gave him the money.

The second time wasn't as obvious. She was just putting lotion on her legs while wearing a nightgown/no panties while sitting at the kitchen table. We're going to order from a different place next time. I suggested she be the one who pays the driver.

Back in college I had just started a job as a barback at a resort hotel in the hills. Two women that would be now called cougars late 30's, were leaving just after last call but before 0200 asked for a couple of bottles of premium champagne. We had no more in the bar so the bartender charged them and said I would bring it up before two O'clock. I came back to the bar with two bottles and iced up a couple buckets and was ready to take the stuff up, when one of the cocktail servers says she'll clock me out on her way out if I get stuck. I ended up staying til about six in the morning. I pumped five loads into these two gals in that time. That night I learned a few new tricks. Both gals were married wearing rings. They honed many skills for me that night.

Two of my best stories about being a pizza guy are -

A girl in her early 20s answered the door. She was average/attractive wearing a tank top with bra and shorts. I could tell there were other people there. She was smiling/laughing like I just missed a good joke. I told her the total then handled her the pizzas. She handed them to someone one else then counted out the money. Handed me that then said "if you want your tip you have to get it yourself" them bent over a little while pulling her top out. I was kind of hesitant at first. I never had that happen so I didn't know if I was being set up for something. Then I went for it. Fished around inside her for at least 10-15 seconds. There were ones and coins in there. As far as I know, I got them all! She closed the door when I was done. I heard someone say "he has a hard on" as I was walking back to the car. She was right.

Another time I had a delivery to a girl that was a few years younger than me. I was 21 or 22 and she was 18. I found her attractive as soon as I saw her. We talked during the transaction and for a few minutes later. I found she went to the same high school that I did and we had a few mutual friends. I had more deliveries in the car so I had to get going. She suggested I stop by after work so I did that. Headbangers ball was on MTV (yeah, this is going way back) so it must have been around midnight. She didn't want me to get caught by her parents so I had to climb in the bedroom window (first floor of a 3 story house). That was a good night!!! I'd love to say I banged her for hours but she was very tight and wet and felt sooooo good. It was over in minutes after I slid inside her. We saw each other once in awhile before she went away to college.

Just think, the experiences you provide to people will be their "I remember when" stories 20 years from now.

I thought we'd only be doing something like this while we are away so I was surprised when my girlfriend suggested it while at my house. It's been two times with the same company so we'll go with a different one next time. Don't want to take away from the excitement/shock factor. Funny thing is, I ordered a pizza for myself a few days ago. Got the guy who delivered the first time. He kind of looked disappointed. Like he didn't get his special present from Santa. Instead of standing on the side of the doorway near the stairs, he was in the middle and seemed to be scanning the kitchen.

Another thing we have talked about is her laying in the backyard topless around the time Fed Ex/UPS would deliver in the Summer. We occasionally have things delivered from Lowes. Another opportunity there.

We were at a hotel in Vancouver, my wife wanted to get a massage before dinner, so I set one up for her in the room. A little disappointed when a woman arrived with a portable massage table, although she was very hot, so not too bad. My wife had just taken a shower, so she was nude under her robe, the masseuse asked her if she would prefer to be d****d, my wife declined. So the woman was heating up her oils, washing her hands, I helped my nude wife get on the table.

I picked up my laptop, sat at the desk and tried to get online, but the ethernet was dead. So I called the front desk, they said they would notify IT and they would call me back. Meanwhile my wife is spread eagle nude enjoying her massage and there is a knock on the door, I open it a crack, it's the hotel IT guy, I asked him if he could come back in an hour, but my wife spoke up, "let him in, it's OK".

So this young guy walks in immediately sees my wife from the ass end, his eyes are locked, like he didn't know what to do, until I asked him about the web access. He snapped out of it and went over to the desk, he fiddled around with it a bit, replaced a cable, he was standing behind me while I tested, but his eyes were on my wife. I think he was almost disappointed his job was done and he had to leave.

My wife
 

Over the years my wife has always worn see thru shirts for deliveries and room service. Some shirts are more like thin lace and are completely see thru. She must have done this 100 times or so over the last 15 years. All delivery drivers and pizza guys seem to love it. Room service in Vegas has been really good with the guys usually staring to get a better look. One time she walked out of the bathroom to get back into bed topless while the room service guy was in the room.

A few years ago I finally convinced her to do topless pizza delivery. We were out back while she was tanning and we decided to order a pizza. I said she should just answer the door in her bikini bottoms like she forgot to put a top on. She reluctantly agreed and it took her a minute or two to work up the courage to answer the door. She swung the door open, took the pizza and signed the ticket, all very casual like someone would normally. The pizza guy looked shocked and was looking around behind him to see if anyone else could see what he was seeing. She slowly signed the ticket and handed back to him. He seemed to love it. I was out on the back porch and recorded the whole thing. It was great!!

Now I need to convince her to do topless room service.

Mrs. HedoRocks
 

Not sure if external links are ok here? (MOD: Delete if not allowed).

My wife did a hotel delivery in a thong and opened button down shirt on a dare from me. This is a quick video of it. You'll notice her second time by you can clearly see her tits out. That was pretty exciting! :D

https://www.erome.com/a/u9KaZrh7

Nice one. Thanks!

That's hot!
 

That's f*cking hot! I'd l9ve to be that delivery guy! :eek:

Thanks guys! Can't wait to get this COVID crap over with so we can do some more!!!

Love this dare. I've got to get my wife to do this.

Yeah, you can say that aloud! We had many short trips planned to do some showing off, then covid and lockdowns happened...:mad:

What does "d****d" mean?

d- r- a- p- e- d

This site replaces any 4 letters (indicating involuntary sex) - begins with r and ends with w - with asterisks. No matter the context. Not real smart, but that's the way it is.

DR

We had another pizza adventure last night. She would usually be in the background when the pizza is delivered. This time I told her it was her turn to pay. She wear a sex, low cut lace nightgown. The design of it allowed the girls to be propped up a little while also giving them an easy way to escape. The driver did something different this time, he went to the front door. Better for this situation because the stairs go straight to the door so he had a perfect view. My girlfriend was on the phone and also didn't expect to use that door so she wasn't ready. The plan was for to take the money out of my wallet which would provide a few extra seconds of visual entertainment for the driver. Seeing that everything was rushed when he got there, she didn't have time to adjust herself was also a good thing. I noticed the areola on her left breast was exposed. The driver was one step down so he was at a good height to see. She ended up getting money out of her pocketbook on the couch. I guess bending over to do that gave that breast a chance to escape. She gave him the money and asked for a few dollars back while he made small talk with her. From my angle, I could clearly see her breast on full display so the driver got a tit for a tip.

I'm thinking we should step this up soon. Maybe have the driver step in for something. And see if it turns into something else.

Room Service
 

Love your pizza dare story Massguy70

Ive always attempted the ex to do the same but the best i can do to convince her the room service. We were at a resort and had her wear a swimsuit coverup with just a bottom. It was clearly see through.

It must a be resort vibe, it was the only time i can convince her.

We haven't really explored this too far due to safety and privacy concerns, but I'll certainly be pushing this on our next holiday.

We lived in an apartment in a busy city for a while, so my one story comes from there. It was a brand new apartment at the time, so it had been built to the latest standards and also to cover the reality that our country doesn't see too much sun over the course of a year. This meant that in our short period of summer, our apartment would get silly hot (like 28-30c indoors).

It wasn't unusual for us to be sat in our underwear. One evening we ordered pizza and it was my wifes 'turn' to answer the door. I thought nothing of it as she got up and walked to the door, because she would pass our bedroom and main bathroom on the way - plenty of opportunity to cover.

So as I say, I wasn't really paying much attention. She walks back in holding pizza and nonchalantly says "I don't think he was expecting to see that much skin...".

Confused, I turn away from the TV and look at her and slowly realise what had just happened. I probably got too excited... "What happened?!" "What did he say?!" "Did he check you out?!?!?!".

She said he was pretty speechless but was beaming and she found it funny that he was trying to maintain eye contact but his eyes kept wandering down.

:D

Just saw this from a FB friend who works in a hotel:

So I go to take this guest an item this morning to my surprise (delight) she comes to the door with no shirt on tatas out and in her well nothing, she answers the door I'm like hello

Someone asked what happened next and her replied:

nothing I went on about my business, I see this often in my years in hospitality

And another friend posted this in the comments:

Brother, I took a PT job delivering pizza for papa John's and every other day or so I always get this order for this one hotel at this certain room and the young lady that answers the door is wrapped in a towel and it seems as though this towel gets shorter, the last time I delivered her pizza she dropped her money and the wind caught it and blew it back into the room, she turns around and bent over showing all of her glory. I was like damn it man, this is so unfair. Lol

We ordered pizza before our first trip to a LS club last night. Earlier in the day I suggested her getting some half shirts or maybe making cutting a couple of her t-shirts. We did that to one of them. It is made of a thin cotton that kind of curled over a little after being cut. I did good on the first try. The shirt ends just below her 38DDs with her arms down. You know what happens when she puts her arms up. So that's what she worn to answer the door. One step up from the driver and she had her left arm up to hold the screen door open so they were hanging right in front of his face. Accidentally of course! She said he was like a cat that was mesmerized by a ball on a string. He fumbled with the money while making change. It was a good transaction.

We've done this a few times with the same pizza company. Time to goto the next one in the rotation.

In all the years at a pizza store, the most I ever got to see was a brief nipple flash from a lady in a dressing gown, and someone answering the door in (just?) a towel..

why do people *insist* on having showers, after ordering food? :-))

Still the closest I have got my wife to do something like this was a time at a hotel we ordered room service. When the delivery came to the door she hid in the bathroom. She just couldn't bring herself to go through with it.

I do have a related story about pizza delivery from many years ago. Two of my wife's brothers lived in an apartment together. One of the brothers had a somewhat wild girlfriend at the time. They would have her answer the door naked when the pizza guy got there and they claimed they would get free pizza about 30% of the time. The other brother was dating my future sister in law at this time and they all swear she never answered the door naked.

This is a weird one , I was dating my gf at the time and I would go over most weekends, we the father had a display case on the wall that had a few old cameras and a new camcorder, that always was weird I thought, so after a while they went away and I had a peek at the camcorder, it was always connected to power, I knew how these worked so just removed the tape and while gf was in bath ( had a good 45 mins ) I put it in, there was the perfect shot of the door I rewound to see her mother walking towards the camera with a pizza naked.

So I fast rewound and caught her in a towel walking to the door after hitting record, she checked her hair and was waiting, 2 mins later the door bell went she looked at the camera and said honey this time. she opened the door and a black lad, I knew him was there she smiled and said glad its u Tony and let the towel fall, he smiled and said me too as I had to pay a guy to swap orders,she took the pizza and put it down bending over, he was a typical. ale was hard and he adjusted his cock she turned and said here let me, she pulled him out and pulled hi inside she shut the door and pushed him against the door, ( she knew the door mat was the only area a body could be see by the camera).

He said what about the family she pressed her fingers to his lips and said he's not left work yet, she said its finally great to see you cock. she knelt down and looked it over, she pulled back the forskin and said does that hurt, he said omg no, she said its so hard and much bigger than my husbands. poor lad couldn't hold on much more of her slowly walking him he came huge load over her face she said oh oh he pulled up and said he was sorry she smiled and said that's ok next time, he said he's going in to the army in September she said well we have a month, he left and she walked to the camera and said mmmmmm as she turned off the camera.

Another pizza guy got a visual tip, or should I say "tit" last night. We went with a different place so we wouldn't get the same drivers we've had in the past. She wore a black lingerie top that she's used for other things. That one is my favorite. Her nipples were just on the edge of being exposed when she opened the door. The driver could see about a quarter of her areolas at first. He gave her the box then she turned to put it on the table and get the money. She pulled her top down a little so one of her nipples were exposed when she turned back to him to pay. I was sitting off to the side so I could only see her. I started to get the feeling that it was taking longer to make change than usual. What would have been about 10 seconds was at least 30. He gave her the change then she handed him a tip. His thank you was more like "Thank YOU!". She told me he was fumbling with his money when he was trying to make change then dropped the bills on the side porch so he had to pick them up.

This pic is from a few months ago. Same top and pretty much the same view he got.

Sorry, you can’t stay
 

Nothing quite so hot as some of these.

Was my bachelors party and at my apartment. Not much in the way of furniture yet. Drinking, food, and a stripper they ordered. She was pretty hot, fantastic ass and big tits. Late 80’s so she also had a wonderful thick triangle of fur.

She was dancing for us, and I ordered some pizzas since we ate everything before too long.

Apparently, she was more than a stripper and she let me know what else was paid for. Totally naked except for her high heels. I told her I wasn’t ready to fuck, I was pretty drunk. She said she was paid, so someone could. She said who is the biggest? They all said they were. She tells them to line up. 4 guys do it, and pull their pants down to have her judge. Crazy as hell, they are standing and a naked stripper/call girl judging. I luckily didn’t join them. I wouldn’t have won anyway, one guy easily was bigger.

Just then, the doorbell rings. Pizza guy. I answer and as he hands me the pizzas he can’t believe his eyes. Full view of the competition. I say “bachelor party”. I then said “you can stay if pizza is free”. He tells me he can’t do that. I pay him, and close the door in his face.

Wasn’t letting some stranger stay and watch anything for free. At least he got a story to tell everyone back at the shop.

Later the guy who won the contest fucked the stripper in a bedroom, she didn’t let anyone watch, and then she left. Oh well.

. My cousins batchelor party they hired a 70 something old lady that could get the tassels going in opposite directions. Ha ha, I was thinking late 80’s as in age not the decade when I started reading this. 😂

Room Service
 

Years ago I had a very hot girlfriend who was an exhibitionist tease. One of our favorite scenes would be when coming back to our hotel room after a late night out. She'd be dressed in a sexy dress and high heels, and as we got off on our floor I'd 'command' her to take off her dress and hand it to me. If she was wearing panties, I'd confiscate those too. Just watching her take her dress off in public like that was HOT! Then we'd walk down the hallway to our room, she in front of me as I'd watch her sexy bare ass slightly jiggle with every step in those high heels. I'd always HOPE that at just the right time someone would open the door and catch her bottomless (sometimes I'd take her bra, sometimes not), but it very rarely happened. One time after we got back to the room, we ordered room service and I decided that because she was so naughty and walked down the hall so shamelessly naked, that she deserved a spanking! We ordered room service and then I had her over my lap for a little 'funishment' spanking. I've spanked most all my girlfriends' lovely bum cheeks but this girl especially enjoyed it. So after some spanking fun, she stayed in the heels and bra she was in, with her cute reddened bum proudly on display. HOT! When our food arrived, she went into the bathroom and closed the door, and I let the guy in. As he was setting up our food (and we had planned this), she flushed the toilet, then slightly opened the door and allowed it to swing open half-way and then took up her position by the mirror. Facing the mirror and wearing just her high heels and bra and a smile, she picked up the hairbrush and started combing her hair in the mirror while having a small peek via the mirror of the opened door. She stayed like that for the 'big reveal' moment when the guy finished setting up and was leaving the room and 100% couldn't miss seeing her wonderfully fully bare, freshly-spanked rear end just mooning him as he exited. For some reason I found that SO SO HOT, to know he saw her cute ass, and could surmise that she just got spanked. HOT HOT HOT She said her heart was pounding in her chest out of fear, nerves and excitement and it made us both super horny.

Since the beginning of the pandemic my wife and I have been ordering food from restaurants about once a week, sometimes picking it up at curbside or having it delivered. About two months ago we ordered pizza and wings to be delivered and left on the table on our front porch. This restaurant calls when they drop off your food and then leave. We got the call and my wife thinking the delivery man had left went outside to get the food wearing a very short and very sheer nightie that you can very easily see her big saggy tits , huge nipples and her hairy pussy through. She opened the door walked outside and the delivery man was standing on the porch on her phone about two feet from her. She said he just stared at her she thanked him for the food and came back inside and told me about it. She was very embarrassed about him seeing her, I personally loved it and hope it happens again sometime. I hope he took a picture since he had his phone in his hand but I'm thinking he probably didn't. Incidentally she hasn't ordered food from this restaurant since. She said the guy was probably mid twenties.

I was a pizza guy in my late teens/early 20s. A lot of people ordered a 2 liter bottle of soda with their food. The main thing that I did to get a good view if the woman was wearing a shirt that might provide one was hand her the food then put the bottle on the floor. And yeah, thinking about that now, I wouldn't want someone to put my soda on the floor. Anyway, that worked great! She'd pick it up when she came back to the door and I'd get a nice down blouse. I even told new drivers to do that when I trained them.

As for my experiences, I got plenty of down blouse views, many in nightgowns, of course there were many women wearing a towel but none dropped it. One woman came to the door wearing a guy's button up dress shirt that wasn't buttoned. It hung open to give me a great view of her huge breasts as she bent over the table counting the money. I then noticed a guy laying on the couch she they were probably one of us. A group of girls around my age at the time ordered pizza. The one that opened the door handed me the bills then said "If you want the change, you'll have to get it yourself" as she pointed to her bikini top. I made sure I got every coin! I heard them laughing as I walked away and someone said "he probably has a hard on". She was right! I would have taken that further but I didn't know if there were guys inside and I was being set up. My best one was delivering to a cute girl wearing a sexy outfit on a Friday night. We talked for a few minutes then she invited me to come back after work. I climbed in her bedroom window when I went back. We fucked while Headbangers Ball was on in the background. She was a memorable fuck. Tight and wet. She felt great!!! I saw her a few times before she went to college.

Awesome story! Was she still horny after you'd finished eating? Has she done anything else like that?
My wife has never done the pizza/delivery nude stunt, but hopefully one day...

Soon
 

I know in the near future I’ll be able to contribute a story of this happening. We have been in flirty talks recently or playfully teasing her about revealing a bit more while on vacations- Chances are we are never going to see the people again, but just possibly the hotel/resort staff on return trips. The little to no clothing around the hotel/resort stays in happening always, and we have been pushing the boundaries of exposure more and more.

Our biggest no-go is to do it while at home due to the uneasy feeling of a guy (or girl) possibly returning off the clock and doing creepy shit, or pointing out our actual home to others to make it known. We’d like it far and away and all in good fun.

I haven't been with many women who are into doing this stuff. My ex-wife dressed kind of provocative when we met (she was 20). She usually dressed from casual to sexy. I got her into doing some flashing but it was few and far between. I think she just did it because it turned me on. I dated a woman who talked a good game but never really followed through. I think she liked the fantasy of what could happen. My current wife busted into this scene like the Kool-Aid Man! She really enjoys it. We don't mind doing things like this at home but I can understand why some people rather not.

almost
 

a year ago we were out of town staying in a motel my wife agreed to wear a certain shirt for me when I ordered a pizza. Needless to say she was very nervous I placed the money on a table which was at back of room(that way she couldn't just open door and go) My chance to see my wife in action had come.
Delivery guy calls phone and lets me know they can't come to the room:mad::mad: Do you think he missed a good look at breasts

He did! Hopefully there are other pizza nights!

We ordered pizza a few days ago. My wife was busy with some work stuff so she didn’t wear anything revealing for the delivery. She later said it felt strange to do the transaction the old fashion way.

Wife
 

We have done the hotel room service with my wife in very see thru tops (like netting tops). The guy never says anything and acts like they don’t notice. Many times she has done this with pizza delivery and one time even topless. The guy looked shocked and kept looking around to see if anyone else was looking.

An earlier post talked about ordering room service and leaving the bathroom door open with her topless inside. We have done this probably ten times and I am sure they see her in the mirror on the way out. One guy even looked into the bathroom directly at her topless and they made eye contact.

We are going to Vegas soon so I will try to get her to do it topless. Not sure of the reaction we will get and hope to not get in trouble. I will try to get some photos of this. Any tips anyone has would be appreciated!

Its vegas!!! U will not get in any trouble

For the experiences at home, she worked around topless in view of the driver the first time we did it (I got the door), she's either had a boob totally fall out of a nightgown top, nipples partially exposed in the same top or both of them totally hanging out the bottom of a half shirt as she reached up to hold the door open. The drivers just looked but didn't really say anything. The last driver who saw nipples dropped his money on the porch and was fumbling with it as he made change. And he said thank YOU before he turned to leave. That was her most rewarding experience. I order from a different pizza company most times so they can be rotated. Don't want to use the same one all the time and have it be expected. A few months between each, possibly new faces each time and always looks like an accident. I doubt we'll get a call asking that she wear more clothes of the police showing up because a driver complained. I'm going to suggest she open the door while topless at some point. Either at home or while we are away. Is that considered disorderly or something? From the stories I've read, it's more common for people to do that while they are on vacation.