So here is a messed up fantasy I have.
I had been surfing on the internet looking up my normal stuff.
When I run across a website that is dedicated to cross dressers and their admirers.
I met john on the site.  Nice enough guy. Lives roughly 300 miles away from where my wife and I live.
I found out that he is a single guy that lives by him self.  He is a decent looking guy, 40 years old, with a small belly but other than that skinny like me.  He has roughly a 7 inch cut cock.  I also find out that he likes cross dressers even if they are not passable.  We talk for over 3 months and though that all we click.  I don't mean like in mad love kind of click but more of a we can trust each other kind of click.
So finally one night we are talking.  I keep saying how I need a place to dress and it would be great to have that place have a cock to use.  He keeps saying he needs a hole to use and also wishes that hole would clean the place.  Then he says that hole would have to be pretty.
Finally, I say well maybe I could come out there and stay for a few days.
That is how the conversation started.  A plan started to be created.  The plans however had some rules for the whole thing to work out.  As we talked about me coming out there to visit him we first had to talk about how long I would go for, and what of that I could actually get away without raising suspicion from my boss or my wife.

Finally John and I decide on 3 days returning on the third.  Once the length of the stay was decided we decided on when.  As John makes his money from a middle class job, he works in a bank, he really couldn't take the time off.  So we decided on in the middle of the week in March.  Only six months away!  I started getting excited.   A chance to dress!

Then John slams me into full stop.  He say he is okay with me coming to visit but I would have to do work around the house to help cover some of the costs he will lose by me being there.  I quickly cut him off and tell him that once I am settled in I will gladly clean the house, cook the meals, wash clothes, everything around the house.  Then John says well there is one other thing, he asks if we are going to be having sex together?  I say more than probably but I am not promising anything.  Then he says he really hates condoms and asks if there is something we can do about that.  I ask him why he hates condoms and he tells me that he only really hates them because he is allergic to them.  As if I had not used that line on a woman before.  I come up with an idea.  I tell John to get completely checked out, including STD checks, and I would do the same.  When we get the results, that should say we are clean, we will send the results to each other with the oath between us that we will not have sex with anyone else until I get there and if we do all that I tell him I would be okay with no condoms.  John then also mentions to me that he has two friends that might visit while I am there and I would have to be okay with them seeing me but I shouldn't worry as they are cool.
I tell him okay.  John then tells me that he will be working during the day.  So with all the details hammered out John and I both agree.

So I began the web of lies.  I told the wife work is sending me off for a conference.  I got a credit card in my name without the wife knowing.  I started ordering stuff for my trip and sending it to John's house.  I got John's clean bill of health a week after I sent mine to him.

So the trip is only a week away now. John has told me that everything I have ordered has shown up at his house waiting. The plan tickets are ordered. My boss thinks I am going on a family trip. My wife thinks I am going on a business trip. It is when I tell John this that he adds a few other rules. The first rule is that I am not allowed to wear men's clothes at all during my stay and if I do he will kick me out.

The second rule is that while I am there I must call him daddy and I must act like his daughter. If at any point I don't call him daddy or act like via daughter he will punish me and or kick me out. His third rule is that I will have no access to transportation, other than public, while I stay there. I simply agree as I am already in to far to turn back now. The day comes... I pack the suitcase that has my man clothes in the trunk of the car. I kiss the wife good bye and tell her I will call her. Then I drive to John's place. The drive is just under four hours. I get there with no problems. I park at John's three bedroom house. My hand is shaking as I knock on the door. John answers then door. He stands there not saying anything but instead he looks me over from top to bottom. Then tells me to come in. Once John closes the front door he turns to me, "Okay Syndi this is your last chance. You can turn around right now and walk out with no hard feelings." I simply say, "I want to stay daddy." My response pleased him. "Take off all those clothes, give me your wallet and car keys. You can have them back at anytime by asking but if you do the adventure is over and you must leave.". I agree to his terms as I hand my wallet and keys to him.

 Then I stip completely naked and hand him my pile of clothes. When I do his free hand finds its way to my cock. "You will call this your clitty while you are here.", then his hand moves to my asshole "This is your pussy.  I fully expect your pussy to be cleaned out every morning." I blush but just say, "yes daddy I understand." "Good now go make your self pretty your room is the last one on the left" My room was just like any other room in any other house. It has a single bed in one corner a dresser in the opposite corner. There is a door to a private bathroom that has a bathtub/shower combo, a toilet, and a mirror sink with lights. Everything I ordered over the month is laid out on the bed. In the list of the items on the bed is all the clothes that I ordered, an enema bag, breast forms, three wigs, two pairs of shoes, fake nails, and the list continues. I grab the enema bottle, a bottle on Nair, a razor, tweezers, and very scented body wash and head to the bathroom.

I start with the enema and once I had flushed my self out three times with a mixture of water and scented oils. I then tweeze my eye brows as much as I dare. I shave my face as close as I can get. Then with the Nair in hand I stand I set a timer and cover my body in the Nair. I wait the right amount of time needed and then take a shower. Seeing my body, and with feeling my fresh hairless body, turns me on so much my clitty gets hard. Then I shave my pussy down to the skin with the straight razor. Once out of the shower I rub my entire body down with lavender lotion. Completely naked I then pull out the breast forms and read the instructions. I have two choices. I can either place them in the bra I plan to wear or I can glue them to my chest. I decide to go with the glue. The instructions say that the glue is water resistant and should last for about three days. I follow the instructions and after 35 minutes of making sure they look right and waiting for the glue to set I sit up and feel the weight pulling on my chest. I grab a pink see through bra from the pile of clothes and put it on. I also pull out the matching panties, lube, and one of the two butt plugs John provided. Using a syringe with a plastic tip I inject some of the lube into my pussy.

 Then I push the plug into me and then pull on the matching panties. As I sit down to paint my toe nails, baby pink, I can feel the plug push in me. I can't help but moan a little when it does. The plug is one of John's rules. He says I need to keep my pussy clean, lubed, and ready to be used. To make sure my pussy will be ready I must keep a plug in to keep my pussy stretched out. Once my toes are dry I then go into the bathroom with all the makeup and do my face. After I got my face ready I then sit down on the bed and put fake nails on. After I got the nails on I pull out a wig cap and out it on my head making sure it is as tight as I can get it while still being comfortable.

 Looking at the wigs I have a choice of blonde, brown, or red hair. All the wigs are medium length, about shoulder length. I decide on the red wig for the night. I brush the wig out and then place it on my head using bobby pins to attach it to the wig cap. I then style it best as I can. Now comes the best part.. picking out what to wear. I end up picking out a pair of pink stockings, a pink garter belt, a medium length plead skirt, and a small wife beater t-shirt that says daddy's girl on the front.

 I then put on a pair of 3 inch red high heels and some clip on earings. Taking one last look in the mirror I am seeing a roughly middle aged woman looking back. I take a deep breath and walk out into the living room. The next few days are.....