Daring Date Ideas
 

So I told my wife Saturday morning that I had an awesome dream about her. I had dreamt that she offerred to be my slave for the day. Basically whatever I told her to wear or do she had to do. To my amazement she said "That sounds kind of hot, I'll do that as long as we go somewhere that nobody knows me".

So!!! Our Anniversary is coming up in October and she said she'd get a sitter for the kids and that will be my gift.

So between me and the rest of the crew on OCC we have a few months to decide on just what my date night itinerary will include.

All ideas are welcome.

My initial thoughts so far....
Tight sheer shirt with no bra
Remote vibrator - Perhaps she's required to give it to a stranger and have them use it
Extremely Short skirt with no panties(I really feel that I either need to go short skirt or no bra sheer shirt but not both....)
Adult bookstore sex or rest area sex with people watching
Start date at shopping mall and buy outfit there
Bowling with extremely short skirt
Go somewhere touristy and have people take our picture with sheer shirt on

Any other ideas?

That's a good list- they all sound like fun! Suggestions might depend on how daring your wife has been in the past- can you fill us in? I would suggest a button down blouse with several buttons undone- enough to give a great view of her tits. No bra, of course. maybe lunch or dinner out so she can let the waiter admire the view? They are also usually happy to take a photo or two, especially if the view has been good.

Valet parking, in her short skirt/no panties? Furniture shopping? The tourist idea is fun; I have a friend who does that often with great success. Give us an idea of what she's done before; that might get even better ideas-

Some additional info
 

Furniture shopping....that could be a fun one....

We took a road trip about a year ago. She wore a gauze peasant shirt with no bra. We stopped at 4 or 5 bars along the way for drinks as well as the rest areas and a walmart. Once she had a drink or 2, she seemed to enjoy herself.

The shirt was very sheer.

Another time she wore a tank with the sides cut out and a short denim skirt. No bra, no panties. We spent the day at a park went for lunch, and a large flea market etc... her boobs literally fell out the sides of the top a few times.

This one will be in the fall so will likely be indoor activities for the most part....

Start Slow and do more as the night goes on.
 

I think the thrill is the waiting and knowing what is coming, I like the idea of shopping for the clothes at a mall and have her model them in the store. You can even have her leave the curtain open a little if the room has a curtain or find a reason to open the door and hand her something while changing, exposing her to the store. The bowling alley idea rocks but I would have her wear bikini panties not a thong but slightly sheer. As the night goes on get more and more of her exposed, maybe end the night at an amateur night at a strip club. Also let people take pics all night and don't cover her face. The chance of ever seeing the pics is slim but the thrill is not knowing who has seen them.:cool:

Some more ideas
 

So I am officially obsessed with this now. So here's another outfit I came up with. Since it'll be fall. I'm thinking Nice jeans tight but a bit dressy, brown leather boots (Like riding boots), and a ultra thin turtleneck sweater (I think they call it mohair). Usually my wife wears a tank or cami under it because it's so sheer.

One thought was to go to like an art or autumn festival for the day in that outfit, then to dinner on the way home.

One way to enhance the short skirt thing is to have her wear hold-up thigh high stockings. That way, even if she's not fully exposed, there'll be lots of times when she'll be showing or flashing a stocking top which will definitely attract attention.

The adult shop sex thing is cool too, especially if the video preview areas have glory holes... ;)

I'm working on some similar exhibitionism things for my wife as well. Our thinking overlaps considerably!

One thing I'm working on: Jeans/pants that have the crotch seam slit open. The pants should be tight enough to be form fitting but not so tight as to be "open" at casual glance. I'm hoping to take her out to dinner and dancing and have access to her wetness on the crowded dancefloor relatively unnoticed.

She might have to wear a long, untucked shirt or jacket to conceal her availablity when standing, dancing or walking but this presents other opportunities. Like something sheer under that.

The idea is to present her with the cover to *appear* respectable but to provide lots of opportunity for lewdness. She'll only go for such things if it's not blatantly exhibitionistic.

Good luck and keep us posted!!!

Another fun clothing item is a skirt or dress with buttons. If the buttons are in the front, she's got control over how much she's showing but if the buttons are in the back, you do.. ;)

An interesting way to do this is to have lower buttons buttoned but one or two in a crucial area unbuttoned like they "accidentally" came loose.....

This is awesome
 

Glad you are all so into this.

I also love the cupless bra's. They look great under a sheer white button down. At a glance it looks like every other lady with a slightly sheer shirt but wearing a bra.....but then you notice the nipples on full display.

Another idea I came up with was to go less obvious on the sheer outfit, but have her wear one of those chokers that say Tease, or Sexy. Not sure where that takes this, but - I'm just brainstorming.

.... a gold ankle bracelet with a dangle that says "S L U T" is good too...

I recently got a similar deal with my wife. She suggested that I pack her bags, so she doesn't know which outfits I pack for when we go out. She also agreed to a nude car ride, as soon as we leave the city proper (neighbors and all). My plan is to only pack shoes for her. She'll wear some cover up thing during the car ride. I'll have her turn on our camera and video herself, then I'll have her throw the coverup out the window while she's recording. Only then will I inform her that he suitcase contains nothing else for her to wear at all. After we get to the hotel, she'll do a nude delivery dare. She'll be handcuffed and I will have just finished paddling her bottom, so it will be very obvious she just got spanked. The money will also be on the floor behind her, I'm going to make her face away as she gets the money, all while handcuffed, mind you. After the delivery dare we'll go skinny dipping, well, she'll go skinny dipping. I'm going to try to keep us outside for a couple hours and get us as far away from the safety of the hotel that is reasonable. Hopefully we can stumble upon a bar with a counter facing the beach. Fun stuff. I'll definitely have documentation for me, but I'll see what I can do about sharing some pics/movies.

I've got a couple ideas saved up myself. If you're going to a touristy location you'll have plenty of opportunities to get your fill. I personally think a sundress with no bra or panties is the best bang for your buck. You should look for a place that does henna tattoos, usually at beaches but could be elsewhere, and pick your wife a design. She probably wont think twice about it until the designer asks her if she could pull her skirt up a bit to start. I've attached an example pic. She'll then be forced to either admit she can't because she isn't wearing panties or be very close to being exposed. I personally like chance scenarios rather than blatant exhibition. I also think roller coasters have tons of untapped potential. ;)

Ive taken my wife’s panties off and then asked her to go to the local bar. We have stayed for a few drinks before returning home. She now wants to get really drunk one night take me out and then take off her thong or bra in the toilets before handing it to me, along with a quick flash

Once, my wife removed her panties while sitting at a bar, then placed them on the bar so the bartender could see them. Most times though, she doesn't have panties on to begin with!

Daring date ideas
 

This is an awesome thread, this is what I like as well. My wife and I have tried several of these suggestions. To add some ideas:
Wifey sometimes gets onto the back seat and masturbates when we take long drives.
I like it when she wears a pair of jeans and unbuttons he blouse so that he boobs are exposed slightly so that I can see them. Once we sat at a restaurant and one of the passing ladies almost walked into someone when she saw my wife was exposed.
We offer go to a movie theatre where my wife opens he blouse and or lifte her skirt. I usually slip my hand between het legs , and try to do it so that the other people don't notice.

She often rubs me while we are watching the movie.
Quite exciting

I should have been as lucky, hope you enjoyed the show as much as I would have with my wifey......

heres a thought
 

take pics of her and post em' here?

Progress...
 

I love the whole pizza dare idea. Then maybe I can video it. I'm not sure about tying her up, as much as just have her answer the door nude, or maybe topless. I also love the short skirt, no panty shoe store idea. Maybe just spend a few hours shoe shopping etc....

I also was thinking about trying to find a bar that had an upper level overlooking a lower level....and have her wear the skirt there showing everyone below the goods. Maybe even have her sit alone and "pick her up" after an hour of watching her get hit on.

I do love the idea of telling her that I packed her bag, and then getting to a hotel room getting her naked and her not knowing what I have for her to wear. I'm not thrilled with the idea of her completely naked, nor will she enjoy thaat, but I could go a litttle more risque if she has to get changed at a hotel instead of leaving the house already "dressed"

Keep the ideas coming.

Like this...

Attachment 4098452

When she got dressed in the miniskirt, you should make a picture from the back and show it to her, so she sees that she's not 'on display'.
Of cause you have to use a higher position to make the picture.
It will make her more confident and more dating, I experienced this too.

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!!

Adult book store tease
 

About 2 weeks ago my boyfriend and I went to an adult book/vidoe store late on a Friday night. I was wearing a short schoolgirl skirt, no panties, heels, and a white extremely thin top that tied up around my neck without a bra. I walked in about 5 minutes before he did so it appeared as though I was alone. I browsed a bit looking for older men that might enjoy a real peek. I usually look for the men in the dvd section for barely legal titles. This store is set up that the shelves are like a maze, so extra privacy when browsing. My bf then came in and was just looking around, but stayed within view or just round the corner. There was this older guy, maybe in his 60's looking through the section for voyeurism. I gently bumped into him and said excuse me, he replied "wow, it was my pleasure, no need to appologize". So I knew he was immediately interested, I noticed him staring from the corner of my eye and following me round each turn of the shelving. I reached last section in the back, the lights were slightly dimmer then the rest of the store. By listening to his breathing, I could tell he was about to round the corner, so I quickly loosened the tie around my neck so my top was sagging just barely covering my tits, and my nipples were very erect from the cold temp in the store, and I spread my legs a bit and bent over as if I were looking at dvd's on bottom shelf. I saw him stop about 2 ft away, so I stood up and stepped next to him, he was facing the shelf and i turned to face him, then I leaned in front of him, brushing my right nipple against his hand as I leaned down across him to the bottom shelf. I felt his erection against me side, so I gently leaned against it, without hesitation he slid his left hand across my back and down my ass then cupped my pussy. As I stood up he pulled back his hand but not without sliding a finger a little deeper. I just looked at him then stepped in front of him and pushed back against his cock....he grabbed my tits and pinched my nipples whispering that I shouldn't tease a man like this. So I reached back and squeezed his cock asking him if he wanted to show me how to undo the tease and get him off. After driving his fingers into me a few times he then followed me to my car where my bf was waiting. The man stopped, but I assured him it was ok. I bent over the hood of my car and he rammed my wetness again and again with his fingers. I handed him a rubber and spread wider, without any talking he riped it open, rolled it down, and fucked me from behind right there in the parking lot while my bf watched. Don't worry, I got off long before he did, actually as he fingered me in the store.

This was the first time we ever did something like this. I mean we are a lifestyle couple and all, but picking up a total stranger was new and way HOT!

Update
 

OK So I sent her 3 options for outfits and she chose.

I took a denim skirt and cut it in half up the sides taking about an inch of fabric from each side.......then I used grmets and white ribbon and laced up the sides.....now you can see that she's wearing no panties underneath....and it makes her legs look even longer.

She will also wear a black open cup bra and a sheer plaid shirt.

I've also added a dare element. She can't go home until she reaches 21 points.

Base Dare = 1 Point, Upgraded Dare = 2, Super = 3. Example: Base Dare - When in the bathroom take a picture of your boobs and send it to me. Upgrade - Take the picture in th mirror and not in the stall. Super - Do it in the mens room.

Anyone who has good dare ideas let me know.

Some More of the Dares
 

1-Flash me your boob at the bar
1B Let me touch your boob at the bar
1C Let someone else touch your boob at the bar.

Insert a remote vibrator and give me the remote
Tell someone else that I have the remote
Give someone else the remote

Things to do.
 

We've done a few things along this line.

We went to an adult book store with her in a sheer top with a jacket covering her as she went in.
While looking around, She took off the jacket and handed it to me. She moved away from me & I watched as men checked out her breasts. I had her unbutton her top over a 10-15 minute period. Finally she would reach for DVD's & her top would open completely & she would not cover herself.

While out of town we went to a strip club that had amature night. I entered her and she danced 3 numbers. The first ended with her topless in only panties. The second number ended with her completely naked. The third number she danced totally naked and opened herself to all the men sitting at the stage.

Went to a adult book store, she was naked in the car. I handcuffed her arms behind the seat and parked near the door in the light so anyone going in or out would see her. I went inside leaving her exposed in the car. I watched as men saw her and then came in the store. I asked if they saw her & what they thought.

Took her to an ABS and had her strip outside the car and put her clothes in the trunk and then get in the car naked. Waited until there were men to watch her do this. We did this several times during the evening at three different locations. We would arrive with her naked, she would get out of the car, go back to the trunk and dress. We would go in and check the place out then we would lgo out and she would strip again before we left. There were men who would drive up, stop and watch her strip and then park after she had gotten in the car with me.

Another time in an ABS she wore a sheer top and asked cashier to show her several pieces of nipple jewery and then asked if she could try some pieces on. She opened her top, and put on various loops and hoops on her nipples and then asked cashier and other men watching how they looked. Also asked cashier to show her how various nipple clamps worked and asked him to put them on her nipples for her. She said some of them were way too tight and hurt & she had him remove them quickly. She also looked at clit clamps & talked to him about how they worked. She teased him saying that she bet he would like to see her try them on too. She didn't because he said he would get in trouble if she exposed herself in front of everyone. She said she would have probably done it if I had asked to do it & if the cashier had asked too. As it was, probably 20 men saw her bare breasts that night.

quick shot of her breasts
 

Here is what they all saw.
It was fun watching him put the clamps on her nipples.

sundress
 

I like the idea of wearing a short sundress that buttons all the way down the front. with nothing underneath, of course. Challenge her to open more and more buttons from the top and also from the bottom. Wear it to different settings - bars, malls, shoe store.

Some other Ideas I was Going to try
 

I am going to dare her to take her shirt off in the car and go through the drive through. I am going to dare her to go to an adult store and watch videos in the booths with the door open and while masturbating, I am going to dare her to let me finger her at the bar.....any other suggestions are welcome.

daring date ideas
 

One suggestion might be to have her get a tattoo in a private place while totally nude... The other man thing, (tattooist) always spices up a date...

The Date
 

Is in 3 weeks. I've gotten the shirt, I've gotten the skirt (And cut 3 inches off the bottom). I went with an open bust bra instead of no bra at all.....just kind of adds to the sexiess.

I have about 4 or 5 more dares to come up with. I have some basics: do a shot, get someone to buy you a shot, etc...

I also have: Base Blow me in the car in the parking lot, Level 1 - blow me on the hood of the car in the parking lot, level 2 - Let me fuck you on the hood of the car in the parking lot

Keep the ideas coming....

I've added several photo dares as well.....Base: Pose for a photo in front of 5 Bars. Level 1 - Flash your tits in each photo. Level 2 Flash your pussy in each photo.

went bowling without undies
 

Hubby and i have always dared eachother to do things a lil risky so i have a thousand things i could share but one example was on a lil weekend getaway without kids there was a bowling alley just down the street from our hotel..well after several stops at some bars he comes up with the stupid idea to go bowling..well wearing a jean skirt i told him i really wasn't dressed for bowling..that and the fact that i (so does he) suck at bowling.But giving me that smile i know whats coming next....yep..he dared me to do it without my thong,so we got our shoes and our balls and i retreated to the ladies room to remove my undies...Thank god the place wasn't busy or i probably wouldn't have done it but ended up bowling 2 games and had a ball..I think what made it even more intresting was when hubby had to go pee i told him he had to take his off too..Just watching him in a pair of loose fitting shorts bowling with a constant hardon made it more fun.pretty sure the only others that even noticed were an older couple sitting 50 ft away because everytime i'd bowl she would turn around and watch me bowl too..