So this post is about a challenge that I hope to create soon and more to follow. Looking for mainly women’s feedback on my activity and also any ideas for the future. Some background first but if you like to jump to it scroll down to the line break with **Actual Challenge starts here** .
Wife and I (both 30) have been married for a few years now and generally have an active and healthy sex life, if a bit vanilla. Our normal sex routine follows a fairly standard script: Foreplay with kissing, touching and teasing, maybe oral, and then a few different sex positions. She’ll probably cum once or twice along the way and it typically ends when I cum. Could be a 5-10 min quickie or 30-40 mins depending on the night or our moods. We were both open to expanding a bit and found the Let’s Experiment website to be very useful to help communicate what we both like and new things we want to try. After taking the quiz we actually found there was a few new things on the list to try but were struggling on how to introduce them to our daily sex life. For example she was into having her hands tied and blindfolded during sex, but wasn’t comfortable with me just randomly pulling out some rope in the middle of the session and getting super dominant (at least not the first time). She wanted some time to prep for it mentally. Plus the anticipation and excitement of knowing you’re going to do something new or kinky that night can be a huge turn on in itself.
So our answer to this was ‘Sex Night’. While tons of couples have ‘Date Night’ where you plan a night out in advance: drinks, dinner, maybe a show and then that typically ends in sex when you get home. We decided to up the ante. Each of us wrote out a new thing we wanted to do or try on an index card, secretly folded it, and put them in a bowl. We each wrote out 5 (10 total). On ‘Sex Night’, we will randomly pull out a card that morning and we have to do what’s on the card later that night. Since we took the quiz, we know these are both fantasies we both want to try so no worries about crossing any boundaries. If we both like it, then we can add it into our daily sex mix but we should try it out first here. If one of us didn’t like it, we talk about it and it’s off the list. I won’t go into all our cards (maybe in the comments if people want to know) but so far it has been a big success. Facials, light bondage (hands tied / blindfolds), sexy lingerie, along with some edging and orgasm denial foreplay have all made it into our bedroom now.
—————–**Actual Challenge Starts Here**————–
For the next ‘Sex Night’ I really want to take it to the next level and outside of the house. Some of our things still on the list include being a bit more dominant (to her) and some public acts (flashing /no panties, playing at the movies, etc). **So this is a big idea and would actually span all day. Let me walk you through it and please give me advice!!**
Wife draws the card and it reads ” *DARE CHALLENGE* You will be tasked with completing a series of dares throughout the day. After each successful dare you will be given your next dare to complete. If you complete all dares you will be rewarded, if you refuse to complete a dare or do not complete in the required time you will have failed the dare challenge and be punished. ”
**Reward -** Over the next 3 days I will fuck you however hard or soft, fast or slow … in whatever position .. and as often as you want.
**Punishment -** Over the next 3 days you will receive no sex or any sexual pleasure from me. However you must give me a blowjob whenever I ask for it … wherever I ask for it … and I can finish wherever I want. In your mouth, on your face, on your pussy, etc… If you are horny, you must take care of that yourself.
*DARE 1* – This is the only dare where you will have a choice, and the rest of the dares today depend on what option you choose. In the spare bedroom you will find 2 outfits for you to choose from today. Choose option A or option B, put it on and head to work for the day. Will you choose A) The sexy outfit and conservative lingerie or B) The conservative outfit and sexy lingerie? The choice is yours and your next dare will be sent at 9:30am via text. Choose wisely!! ”
For some background, my wife works in a fairly small, relaxed office. Think “Tech Startup”. There are dudes walking around wearing jeans and graphic T’s, women sometimes wear dresses but jeans and a sweater are more common. So a full blown sexy getup to work would 100% draw attention. It’s also getting pretty cold now so skimpy clothing is probably out. I chose to go with the below options…
**Option A**
Short Pencil skirt with some ankle boots. A fashionable/casual sweater on top. It’s on the sexier side for her office but not unreasonable. Something like this –
https://i.pinimg.com/736x/9f/33/01/9f3301f272434af17c9ea7d5da8d8511–leather-skirt-outfits-black-leather-skirts.jpg . Under that would be a g-string thong and a standard bra. Pretty tame Like This – http://www.tiarashop.eu/1495/sexy-tulle-set-bra-g-string-panties-3031-2015.jpg , and is something I assume a lot of women wear under their clothes anyway.
**Option B**
Is a longer sweater dress. Complete with the stockings and big boots. A more conservative outside appearance looking like this –
https://i.pinimg.com/originals/15/58/fd/1558fdcb9e19030fb84796eb8d295e6e.jpg . Underneath though would be a full lingerie set that I had bought her and she loves. Open cup bra, thong, garter belt, garters, and stockings. Basically this this –
https://www.amiclubwear.com/media/catalog/product/cache/1/image/9df78eab33525d08d6e5fb8d27136e95/c/l/clothing-undergarment-aaa8-9386black.jpg . With this setup, the dress is long enough you wouldn’t be able to tell it’s garters and not just leggings/stockings.
I like giving her the choice of how ‘exposed’ she wants to be for this challenge, or how sexy of underwear she wants to pick, etc.
So fast forward and she gets to her desk at work. This office is fairly open concept too so she’ll be right next to people. This is the Best Picture I can find to describe it –
https://i.pinimg.com/736x/5f/60/aa/5f60aab3d2ade29e2a3bdbc32afc7f92–work-spaces-office-spaces.jpg . Definitely not cubicles. Between 8 and 9:30 I might drop a couple texts asking if she feels sexy in her outfit or if she feels sexy wearing lingerie to work but nobody knows. And now to my big confession **The dares are the same regardless of what option she chose!!** Unfortunately, I didn’t have enough ideas to mix them up so hopefully reddit can help me there. Bonus – If she gets mad at me for a dare, I can spin it on her and say “Well you shouldn’t have picked Option B then!!”. Soooo anyway, 9:30am rolls around and she gets this text:
*DARE 2* – While you are at your desk, I want you to slowly begin to spread your legs apart. Keep spreading them until your dress/skirt starts to slide up your thighs. Do you think your neighbors will notice? When they’re not looking, reach down and pull your thong to the side. Play with your pussy until you’re wet. Do you think they can see you touching yourself? I want you to put your phone under your desk and take a picture of that beautiful pussy for me, WITH THE FLASH ON. Hopefully your neighbors will see the flash and look over to see you sitting there with your legs spread wide open and pussy dripping wet. You have 2 Hours to send me my photo!!
Over the next 2 hours, I’ll send her little texts asking her where my photo is. Teasing her. Is she too nervous to do the dare and would rather I use her mouth whenever I want over the next 3 days as my personal fuck toy? Then assuming I get my photo, I’ll comment on how much I want her pussy. To lick it, fuck it, etc… Then let her know she needs to be outside her office in the lobby at 12pm to receive her next dare … in person .. from me. That should give her a solid hour to get all worked up. Are we doing something outside? He just said he wanted to lick and fuck my pussy … is he going to fuck me outside??? I imagine she’s going to be an anxious/nervous wreck by noon.
*Dare 3* – I’ll text her to come down and meet her in the lobby at noon. I’ll have a brown grocery bag, sealed, in my hand. When she comes down I’ll give her a little kiss and ask if she likes my dare challenge so far. Assuming she’s still game I’ll send her on her way with Dare #3. She must go up to her desk and open the bag (it’s ok to open in public). It’s an empty bag with only a note inside that reads **You have 10 minutes to put your bra and thong in this bag and bring it back to me. Keep your garter belt, garters, and stockings on.** (assuming she has them). It’s a way of being dominant in the “I want your underwear now!” type of way. Hopefully it will 100% turn her on.
So she brings back my present, and I send her on her way the rest of the day telling her she’ll be getting her next dare at 2:30pm. That’s it, no sex, nothing else … I just leave. Hopefully leaving her very sexually frustrated. Of course during the next couple hours I’m texting her reminding her to keep her legs crossed during meetings unless she wants her boss to see her pussy. Asking about her nipples, how hard are they? Can anyone notice she’s now braless? Etc… 2:30pm rolls around and she gets her next dare.
*Dare 4* – I really hope you have been enjoying being naked under your clothes all afternoon. Do you think your coworkers know you have been teasing them? Can they see your hard nipples through your sweater? Well if not, I think we should give them a show of what you’re hiding. I want you to play with your nipples until they are nice and hard (shouldn’t take too long!). Find a nice secluded part of the office, NOT THE BATHROOM, maybe an empty conference room, a balcony, the stairwell? Somewhere where you could be caught. Pull out those tits and hard nipples and send me a photo of you flashing. You have until 5pm to send me my photo.
Obviously this one is probably the riskiest, but I’m guessing she’ll find a way to do it without getting fired. By the end of the day I’m hoping she’s going to be really horny and also be having a good time. At 4:30 or 5 she’ll get my next text for a dare.
*Dare 5* – Good job so far! Only a few more dares to go. Let’s meet for a cocktail to celebrate passing all your dares so far. Meet me at the bar at 6:30. But before you meet me I want you to pick up something. On the way I want you to stop in the adult store near the bar. Spend some time looking and pick out a new vibrator or dildo you like. Have them open the original packaging and put the toy in a discreet bag or your purse and bring it to the bar.
So when she gets to the bar we get a drink. I’ll start by asking about her day, how was work? Normal stuff, and then transition into what she liked and didn’t like about the dares. Spend some time talking, hopefully we’ll have 2 or 3 drinks in us and then I’ll bring up the package and her final dare. I should mention this place is an upscale cocktail bar. Bathrooms are really nice with unisex rooms (not stalls but a full bathroom for 1 person). With large mirrors that span the whole wall and lots of space to move around. You know, the places that have actual towels to dry your hands and not paper.
I’m imagining our conversation would follow something like this:
Me – “So are you going to show me what you bought?”
Her – “You want me to show you here? In the bar?”
Me – “Of course, that’s your dare. You made it this far are you going to fail now?”
Her – “OK……” ::Starts pulling out the bag::
Me – “No, no. I want you to *show* me. Last dare. I dare you to go into the bathroom take off your dress/skirt & sweater and show me playing with your new toy. Take at least 3 pictures when you’re in there and send them to me. You’re not allowed to cum though. If you pass the dare, that’s my job to make you cum for the next 3 days”.
Keep in mind, I already took her thong and bra 7 hours ago so she’ll be completely naked in there. Or well, maybe a garter belt and stockings. Either way really fucking hot. Me sipping my cocktail while I get photos sent to my phone of her fucking herself with a dildo not 15 feet from me …. almost in public. Assuming she passes the dare then I take her home and fuck her silly **However she wants it** since that was the bet. And I’ll be happy to do it!!! If not, well then I get unlimited blowjobs for the next 3 days and I anticipate several facials! Really a win-win for me.
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So that’s it reddit. My main questions on this and why I’m writing my gonewild challenge story…
1) As a women, is this something you would want your bf/husband to plan out for you?
2) Can I improve this? Is there something where you’re like “WHOAH, sweater dress and no bra … are you fucking stupid that’s going to be horribly uncomfortable!” I’m not looking to make this painful or anything, actually the opposite. Trying to make it as fun as possible so she’ll want to do it again.
3) Does anyone have suggestions for other dares or how to improve this challenge?
I hope you enjoyed the idea, and I know it’s not a gonewild story YET, but I promise to provide a follow-up after it happens.
Source: reddit.com/r/gonewildstories/comments/7jepxu/mf_looking_for_advice_on_the_next_gonewild
This isn’t the typical GWS post, but I am intrigued by what you have written and curious where this is going to go. You have my +1.
Looks like A LOT of fun!!!!
Sounds hot, be sure to update us on how it goes.
Sounds hot. Just make sure she’s up for so much activity at work! I work in a busy tech start up space where things are really busy. I’m kinky but so I’m not sure I could do this at work. I’ve sent my fiancĂ© photos the bathroom at work and that was really hot.
Wow, that’s just awesome! Way more imaginative than anything I got up to with my partners; the usual shopping in a skirt without panties, bra-less in public, topless at the beach or in the car. I would imagine that all the planning is half the fun though!!!
One thing I will say though is that I think the whole work scenario is a little risky. Anything from whispers about being the office slut, to unwanted advances and even blackmail, losing her job or worse – legal issues – set the stakes pretty high. I love the idea but I’d probably opt for ‘safer’ scenarios. The beach is great for a bit of exhibitionism, for example.
There’s probably a few opportunities for a dare outside the office, even if you incorporate it into the existing plan. How about having her surreptitiously film herself ‘accidentally’ rubbing her bra-less tits against a stranger on the train or in a crowd, as she makes her way to the bar to meet you? Quickly flashing her pussy on the train? Or she could do all this as you watch on as another anonymous stranger! Is she into a bit of exhibitionism?
My first ‘serious’ girlfriend turned out to be a rabid exhibitionist. Unfortunately I was quite inexperienced at the time and way too scared to indulge in most of her fantasies. She was constantly trying to get me to have sex with her in front of her (female) flatmate, but I was too shy. A few years later I would have jumped at the chance – and begged her flatmate to join in. She also begged me to let her give me a blow job in public, but that never happened.
Late one night after an evening at the pub we stood outside her inner-city place making out. I had some idea why she wasn’t keen to head indoors as she was rubbing my cock through my pants in full view of passers-by (not that there were many at this time of night). At one point a guy walking past stopped to blatantly check us out. She gestured towards him and when I turned around he smiled and nodded. “Would you like to see her tits?” I blurted out, figuring it might be enough of a ‘fix’ to get her indoors. He nodded and stepped towards us with a grin. I started to fiddle with her top but she pushed my hand away and simply pulled her C tits out. He indicated he’d like to feel them and I nodded. After about 20 seconds I said “OK”, pulled her top up, and dragged her to her front door. She was insatiable that night.
At one time another girlfriend’s friend and I would often tease each other (with my GF’s full knowledge and blessing) quite explicitly. She’d catch the bus home late at night during the week and once asked me to write her something to read on the bus. I wrote about one of my fantasies that involved her and gave it to her in a sealed envelope. Later that night she texted me that she had read the story and loved it, and had ended up fingering herself on the bus!!! When I saw her next she handed me the same envelope, re-sealed. When I got home I discovered they were her panties from the bus trip. I ended up returning them a few days later in the same envelope, encrusted with a few loads of my cum.
Not sure if any of that floats your boat?
I like the concept of index card honestly a little long.
Great idea, I’m always open to supporting couples trying to spice things up. Agree with others that maybe GWS isn’t the best place to post this? No clue what subreddit would be better, maybe we can give OP some suggestions?
Initial thought was r/sex but this might be a little too much for them. Any fantasy or fetish places OP could post this to?
I really like your ideas and the effort you’ve already put in it! :)
Maybe you could offer her something like a joker, if she does a dare, but not exactly the way you planned it – as some of the dares at her workplace could turn our pretty bad if the wrong person saw her..
As for other ideas, you could make her wear a plug inside her pussy or ass for some time (don’t know how experienced and interested you are). Or vibrating panties in a bar, where she can feel the vibrations of the slip and of the music, but nobody will hear the sound of the slip. Or you could dare her to almost make herself cum at the bathroom and having to send you a pic of her wet fingers.. Along the way of edging her :)
I wouldn’t do the pic in public with the flash on – it could get really bad at work as already mentioned.. And, depending on her workload, but I wouldnt text her that often – let her text you :D let her wait and dream ;)
But as for everything and always – HAVE FUN and follow your feelings, your gut instincts – you know your girl best and your relationship, so do as you feel :)
I’m looking forward to the update :)