Interactive Crossdresser...Dare Me Ch. 04

So just to give a small amount of background, besides taking dares from people and performing them, although I don't write about a lot of them, I post ads online using this name, Porsche Karu, seeking men who are looking for a cross-dresser.

I get some reply's but they never work out into an encounter. Until one guy, when he first emailed me he was staying at a hotel in town but I couldn't get time for what he wanted but he told me he would be back in town in a few weeks and told me where he was staying and what room number even.

The hotel was on my side of town and we emailed back and forth during the following weeks; I told him I had fantasies of being used as a prostitute and he loved it and told me there would be $1000 in it for me to meet up with him but I had to follow his rules, and his rules exactly.

So the day arrives that I'm supposed to meet him at his hotel, he told me 8:30 to 9:00pm to be there at, and he would send me a first email earlier in the day, before noon.

I'm still very nervous and reluctant to meet him so I begin around 11 in the morning to get ready, and when I mean get ready I mean to start the margaritas, tequila will take the edge off for sure.

So at 11, after showering, and shaving my body perfectly hairless, I started the blender and started tipping back the margaritas, awaiting his email to start this adventure into prostitution I suppose. It would really be nice to get $1000, I'm just very skeptical of what I have to do, but after emailing back and forth for weeks he seems legitimate.

I'm walking around, naked, well into my second margarita and I still hadn't heard from him, so I thought that I would at least go start applying all my makeup so I can get it perfect.

Well before I get a chance to start, I hear a ding from my computer for an email. I run to the computer to check and sure enough there it is from Gus, the email I'm waiting for.

I pull it up, the subject line says, "your challenge."

That subject is intriguing, so I start to read and realize I won't be getting ready now, I will just tell what the email says, then what happens next.

The Email

Hi Porsche,

So the day finally arrives and I'm so excited, I hope you are too and I hope you're ready for my challenge, it's not going to be easy but I think you will have a lot of fun and enjoyment today and tonight if you go through with everything. Remember, to win the $1000 you must go through with everything the way I say.

So here is a list of the rules.

1.You must wear jeans, boxers, a t-shirt, and sandals when you leave the house and you can't get "dressed" or ready at your house, the only items you can take are your wig and your breast forms.

2.You will go shopping for each women's item that you will be wearing today, your outfit needs to be a sexy skirt and sexy top.

3.Once you buy an item you have to wear it and not take it off.

4.Only one item per store, bra and panties are considered a single item as they need to be a matching set.

5.Garter belt and stockings are required and can be considered one item.

6.Every item you wish to buy has to be tried on in the store.

7.At least one item has to be bought in a women's only store. i.e. Victoria's Secret, Fredricks, Charlotte Russe, Tiger Lily, you get the idea, and yes it has to be tried on there.

8.When you try something on, you must take a picture of yourself and send it to me on your phone, then wait for me to reply.

9.You will also email me on your phone what store you are going into before you go into it.

10.All receipts have to be saved and presented to me for repayment, that will not be part of the $1000.

11.Once you buy an item, you then have to wear it, and not take it back off, before putting on your bra, you must affix your breasts, your wig must not go on until immediately after your make-up is applied.

12.Your nails, hands and feet must be professionally done at one store, your make-up must be professionally done at another store.

13.Any man who attempts contact, or engages you in any way, you give him a note that you write, the note must say, "I lost my voice, but I love to suck cock and would love sucking your cock if you want me to."

14.Your first stop must be a porn shop, buy an anal plug of your choice, it must be one that can stay in your hole all day, leave and put it inside of you out in your vehicle.

15.After you are completely dressed, go shopping as a woman and buy a sexy dress, bra, panties, garter belt and stockings, and another pair of heels if you wish, and don't forget some jewelry and perfume. Don't forget to try on the dress.

When you're all done shopping then come to my hotel room, around 8:30 pm, I can't wait to see you.

-Mac