Any Locations Suggested?
 

We've gotten the bowling, furniture shopping, shoe shopping, movies, I was also thinking maybe like an Art Museum...

An art museum could be great- I've seen some amazing shows at them. And how about a place like Home Depot or other big box hardware center- lots of solo guys to entertain. Garden centers work also- lots of excuses to bend over!

I love my wife. I ended up telling her my plans for this evening and she is completely with this idea. We even worked out a second day of activities. I found an artist who wanted a nude model for a painting, so she's going to pose for that. I'm also taking her to a secluded state park (I found it on google maps, it only has 4 parking spots and it is in the middle of nowhere) for us to have a nude hike/picnic. We also took out the handcuff/paddling idea, but with the second night, we're going to order from the same place the second night, just to see what happens. I'm just super thrilled that she's completely willing to not even bring one outfit for her to wear the entire weekend.

Kram314
 

Hope you enjoyed yourself! Let us know how it went!

OK So here's a full timeline I'm thinking about - Keep in mind it will be chilly out.

1-First dress in a peacoat rain jacket (Hangs just below the ass) with nothing underneath. When babysitter gets there (Around 1:00 in the afternoon).
2-Stop several times on the way to our destination and make her go into stores (Furniture etc...) in this coat. Unbutton one button per stop.
3-Get to a hotel with a lounge and pool - order room service while we get ready. Clothing is not allowed while answering door. I will be in the bathroom with tip money. She must come get it from me once the food is delivered then walk back to the delivery boy.
4-Dress for drinks at the bar (Sheer white buttondown shirt with black open cup bran beeath) and pencil skirt, She must go down and sit next to men at the bar. I will text her at various times from across the bar with instructions (Unbotton another button, buy someone a drink, remove your panties and place them in your purse making sure someone sees you, etc...) All of the time there she will have a remote vibrator inserted with me controlling it.
5-I'll buy her a drink and hit on her and get her to go to my room.
6-Go out for dinner Outfit can either remain, or we can change it haven't decided.
7-Get back to hotel. Remove top in elevator. Must walk to room topless.
8-Change into swimwear and go to hotel pool. Her swimwear is to be sheer gauze or wicked weasel type.
9-Give blowjob at hotel pool. Be sure to cum on her forehead. Walk back to room leaving cum on her forehead and dripping down her face. Towel can cover her lower half, however bikini top should be showing and sheer.
10-Get back to room and finally have sex, Order room service for the morning.
11-IN morning answer room service while she remains on bed masturbating. Do not stop until room service boy has left.
12-Put peacoat with nothing underneath back on and head home.

The only, but CRITICAL element missing is photo or video documentation of all your very adventurous steps!

Several years ago my wife and I went to a small town vacation area. There was a late night convenience store we stopped at the beginning of our week there. It was staffed by a teenage boy who basically ignored me but was smitten with my wife. My wife flirted with him a little then we left. Driving away we both laughed about the clerk. Over the week we returned to the store a couple times and again saw the same clerk. It was later in the evening and we were the only customers. One visit my wife undid a couple buttons on her blouse. Another visit she took her bra off before going in the store and was wearing a knit top. Each time the clerk couldn't help but stare at my wife as he took care of her. At the end of the week we stopped at the store one last time. This time my wife gave me a blow job before going in and had me come on her face with some dripping on her shirt. She went in the store with cum on her. The look on the young clerks face was priceless. Maybe you and your wife could have some fun at a convenience store?

New Spot Discovered
 

So I just found a local liquor store that has a bar connected to it. There is essentially a fence between the bar and the store. If my wife was sitting at a chair with no panties on....everyone that came in to the liquor store would literally be looking right up her skirt at eye level. I definitely think this spot needs to be added to our evening.

Update
 

Ok. Anthr idea. She gets to hotel room. There are 3 garment bags. 1 labeled wild child, one labeled vixen, one labeled socialite. Each bag contains a different outfit, and a different date for the evening.

Wild child is a super tiny denim skirt, maybe a night at a dive bar, strip club etc.....
Vixen is a bustier or club outfit and an evening at a club or Lounge
Socialite is a nice dress and limo ride to a fancy rstrnt.

All outfits will be sheer topped with no bra or short skirted with no panties.

I will plan more specifics and multiple stops for each date at a later date.

The Date
 

OK it's set - First We will leave the house with her dressed in nothing but a Trench coat. Instead of driving we will take the train to the city (THis should give plenty of opportunities for people to get a flimpse.... We will get to the hotel where I will check into the room while she remains at the hotel bar. I will set up several cameras in the room for documentation.

I will send her to the room where there will be 3 garment bags and a note that says "Pick your date".
Bag one will have a label reading the following "Well Kept MILF - Hot well kept women are sexy. This date includes a shopping spree and a beautiful dinner out. Inside this bag are the clothes you will shop in, I will then buy you an outfit of my choosing for our date this evening....remember the more a woman gets.....the more she needs to give"

Bag 2 will have a label reading "Wild and Trashy - This date will include a wild night, short skirts, dive bars, and budweiser.....sex in the ally is not off limits tonight"

Bag 3 - "Runway Ready - Trendy bars, tiny clothes, and Martini's....what will you need to do to get to the top?"

I'll then leave the room telling her to get ready, and that she is not to wear any clothing...even when answering the door, and that I will spot check her. Of course I will then send several room service folks up to deliver wine, and food.

I think instead of the trenchcoat home, I will go with a workout type look...maybe slightly sheer white stretch pants and a sheer t-shirt. this way she's at least comfortable on the way home.

She decided
 

My options were a little different but she went with "sl*tty date". The envelope read: "ass cheeks hanging out, tight tank top with no bra, beers, and strip clubs. You'll be expected to suck dick, go to strip clubs, and say yes to everything.......". Should be fun!!