Pizza Delivery

I have been needing to write this for quite some time. It’s not that I’ve been meaning to write this, but I’ve actually been needing to write this. I owe Crossdresser Heaven a great deal. This site provided (and continues to provide) a welcoming and judgment free area that allowed me to do some much needed inward looking. I can’t tell you how many articles I’ve read on here, not quite all of them yet, but I’m working on it. This site is a truly safe place among so many out there that are not. Everyone here is so polite, friendly and helpful and that’s what makes CD Heaven so special and why I have had this need to write this as a way to say thank you to everyone.

I had been dreaming since my teens of one day being able to finally stay dressed as a woman, as myself, for that “whole week.” I had been working up to this. I would go a few days at a time, then something would come up. Someone would need something, or some social obligation would come along. Finally, recently I found the time when I could stay at home and be myself. The problem I ran into is even though I had stocked my pantry and refrigerator well, I tend to get tired of the same food every day fairly quickly. This was at a point when I had not yet gained the courage to completely venture out as myself in the day time, let alone the courage to go somewhere to order something from someone.

I read on the internet about all the weird things that pizza delivery people had been asked to do (some of them are pretty far out there). I had heard some of these stories myself as several of my friends had delivered pizza many years back. They had been asked to pick up beer, cigarettes, and in some cases much more personal effects. The answer from my friends was always dependent on how much the person on the other end was tipping.

I myself had spent much of my adult life in the full service restaurant business. I made my living from tips. I know from my personal experience that I never once cared about how a person looked or what they were wearing. If they came and sat at my table or my bar and were spending money, then I was going to give them my best service. I put these two scenarios together and decided it would be just fine to order pizza.

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So I did order pizza from my usual delivery spot. I never tip like a slouch, but I decided I’d tip extra heavy this time. This was the first time I would ever interact with someone in person while I was dressed. I was pretty nervous about it. It seems almost silly to me now to have been that nervous. I didn’t prepare what I was going to say to him and unfortunately I did say in a very guyish manner “How’s it going?” I would have preferred a bit of a softer expression. But that didn’t really matter.

The reason I really have been needing to share this experience and to combine it with what I personally know about people who make their living earning tips is that the pizza delivery guy probably got a story to tell that day. He may have told a few of his coworkers. He may tell a few friends from time to time. What I can tell you is, the biggest part of his story is how big the tip is. And I guarantee the next time he sees my address come up on the screen he’s going to plow the other drivers out of the way to be the one to deliver here.

I’m not saying a tip has to be that big by any means. But I was nice to the person. I know that’s how he makes his living. I also know that I probably threw him for a little bit of a loop that day. I was going to say I bet he barely thinks back on it, but that’s probably not true. I can think back in my own career to a few special guests that I’ve served. It never was about the money and it certainly wasn’t about what they were wearing, it was always about how nice they were.

I’d say do mind your safety. I ordered from a large reputable chain. But don’t stress too much about who sees you when you are looking fabulous, it might be the best part of their day.


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    I've recently accepted being transgender and am seeing where that journey is going to take me.

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    April (Pacific Princess)
    Active Member

    Nicely told Dani! After you’ve interacted with people en femme a few times you realize they are just people – if you treat them well they will treat you well, and if you’re a customer spending money then that’s what they will see – a customer. Today I went to a wine bar in a nearby town as April, and ended up chatting with the husband and wife owners, as I was enjoying my second glass of petit syrah. It was fun, and I don’t think me dressed was a problem for them at all. As you said now they… Read more »

    7 years ago

    Delivery people no doubt meet all sorts of people in their day-to-day work. The best part of this realisation is that we are simply different to some others. It’s quite likely, though, that if he’s been delivering for a while you might not even be the first CD he’s delivered to.

    Enjoy the pizza and remember who to order from next time. Then pick out your nicest outfit. That’ll be a tip of a different sort for whoever does the delivery.


    melissa moore
    7 years ago

    It is nice too hear great experience and the feeling of being who you really are too share with some in person.

    Maria Young
    Maria Young
    7 years ago

    Oh your story is good Dani honey I have a couple myself but I’ll tell it later hehehe Lol&loL Love Maria

    7 years ago

    When I was a teen working in a drugstore, I had a terrible stuttering problem that had caused me torture in answering the phone. The pharmacy name particularly bothered me since I had difficulty pronouncing the first letter of the store name. Seeing me struggle with this, growing embarrassed and perhaps even red-faced, the pharmacist gave me advice that has followed me through my long life. He said: “People don’t care how you sound (or how you look in the case of the pizza story above). They just want their order fulfilled, nothing else." When I get too worried about… Read more »

    Dot (Donna B)
    7 years ago

    Dani great story. Nice positive experience. Sounds like a nice way to explore interacting with others when dressed. Thank you such a nice story and idea.

    Manager Codille
    Managing Ambassador
    7 years ago

    Having Delivered Pizza when I was younger before kids I will tell you, Damn straight if I saw you address pop up I would swipe the tag.

    More importantly Dani, Congrats on a whole week and first encounters!!!


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