www.BoundAnna.com

I am 40 year old guy, my wife (mistress) has me crossdress on occasion and likes to humiliate once in a while.

So tomorrow I am to leave on a top that is about an 8 hour drive.
Mistress has setup a scenario for me to complete.

She wants me dressed in a black leather mini skirt, a black mesh blouse (very see-through) stockings and heels.
Under will be red thong panties and a red bra. I am to drive, where I will have to make at least one stop for gas, and then check into the hotel.

All of my guy clothes are locked inside my suitcase with a combo lock, once I check in, I can call her to get the combo.

She also wants me to drink a bottle of water every hour so that I would have to make more stops.

She also has put instructions inside the suitcase for other scenarios, dares and tasks. I already know that I am to video a scene as she told me the camera is packed, along with a bag of toys.

The bag consists of writs and ankle cuffs, a paddle, a whip, an open mouth gag, a couple of dildos, misc rope, clips, clamps and such. Maybe I'll post some of the other things she has me do.

Sounds like fun! Be sure to let us know how it went.

So, back from the business trip. It was a bit longer than expected, and my wife had more things for me to do. First , when I left I was fully dressed, pink bra and thong, black stockings and garter with a black skirt that was well above the knees. She had me wear a black mesh blouse and black high heels. The car was almost on empty which a gas stop right away. Wasn't too bad as there no other cars getting gas, the walk into the store had just one guy and he didn't even look. I drank plenty of water and had to stop at a rest area. Couple of chuckles from a guy that held the door open for me on my way in to the ladies room. Then met a woman as I was leaving. Second gas stop had a lot more people around, didn't notice anyone staring though. The hotel check in went smooth, girl at the desk gave me a big smile and comment on my top. In the hotel lobby I wa app rocked by a couple, they knew who I was and said they were to accompany me to the room where I was to provide a blowjob. Once we were in the room, she had me sit in front of the chair, and tied my ankles to the back legs of the chair, and my wrists to the front legs. The guy then sat down, and pulled my head onto his dick. For about 15 minutes he rammed my face finely exploding down my throat. She untied me and they left. A few minutes later, my wife called, asked if everything was going ok, then said that I would be receiving an email with the next task.

She should have put leather hasp cuffs on your ankles and then joined them with a chain, about. foot long. Combination padlocks. Consider that they would to be seen by anyone behind a counter, such as gas station or motel. But would you dare walk into a restaurant that way?

Off to a good start! Can't wait to hear the about the next task!

Wow! It's just wonderful! Now it's my dream) Long crossdressed trip with a car, with mistress on phone (or hides in a car), who deal me a humiliating quests!
I guess, here is 2 important conditions:
1) For everybody peoples must see what i traveling alone.
2) I can not use excuses like "for a bet", "loose the bet", "it's order", etc.

By the way, your mistress sent you orders like "spend a day in the water park dressed in a girls swimsuit" or something like that?