See through dress in the club.......mesh or sheer.
Sexy dares or challenges
- Thread starter tumblrstag
- Start date
This is one of our challenge games - a multi-session “stair-step” challenge, which escalates in daring and complexity. The basic challenge is three sessions, MF as a couple, MFM, as a couple with a second male involved, FM+, incorporating two encounter partners. The extended challenge adds her going solo with each encounter partner, and a finale of her in an MFM with both encounter partners, absent you.
The basic challenge is structured along these lines:
- Session One - one-on-one. In this session, as a couple, focused on her, using a perhaps cliched term, you’ll go “round the world”. Challenge points are scored for each of the following:
1. Mutual masturbation (add one point if you both cum while masturbating for one another.
2. Reciprocal manual stimulation (add one point if she cums, but you don’t)
3. Master-slave oral (i.e. you service her, then she services you)
4. 69-oral (add one point if she cums, but you don’t)
5. Straight fucking - vaginal intercourse (add one point if she cums, but you don’t)
6. Anal sex (add one point if you cum in her ass)
7. Facial or body-shot (add one point if you cum on her tits, pussy, ass or feet, two points if you cum on her face, three points if you clean it up)
- Session Two - two-on-one (MFM). In this session, you will involve a second male in the encounter. The same seven session goals apply, with a twist:
A. She and the encounter partner execute all seven sexual goals, while you watch
B. Your encounter partner watches the two of you execute all seven sexual goals, while he watches
C. You add a traditional double-penetration component, anal-vaginal MFM
D. You add a less traditional double-vaginal, or double-anal penetration MFM component
E. You clean up your cum
F. You clean up his cum
A, and B accumulate a maximum of 14 challenge points. C adds 5 challenge points, D adds 10 challenge points. E adds 2 challenge points, and F adds 5 challenge points.
- Session Three - Three Men and a Lady - FM+. In this session, you’ll involve a second, as well as third male. The same sexual goals apply, with the maximum being your wife will repeat the steps with potentially three men; you, and two encounter partners. The twists in this session leverage the availability of three men:
A. She and the one of the encounter partners execute all seven sexual goals, while you and the third guy watch
B. Your encounter partners watch the two of you execute all seven sexual goals, while they watch
C. You add a traditional double-penetration component, anal-vaginal MFM, plus oral - making her air-tight (add five more points if she’s air-tight)
D. You add a less traditional double-vaginal, or double-anal penetration MFM component (add ten points if the four of you can manage some form of triple penetration, in any combination)
E. You watch her being spit-roasted (oral + either vaginal or anal penetration) by the two men (add five points if you can watch without cumming)
F. You clean up your cum
G. You clean up their cum
- Bonus Sessions Four, Five, and Six - She’s on her own. This is an advanced series of “stretch goals” in the challenge. If you’re both comfortable, the idea is for your wife to engage in solo encounters with each encounter partner independently, and the most advance part of the challenge, an MFM with both men - the twist is you’re not present.
1. Bonus challenge points are awarded if your wife acts independently to set up the date(s), five points for one solo date, ten points for the MFM encounter
2. A twenty point completion bonus for executing all aspects of the multi-session challenge
3. A sixty point maximum bonus if she allows pictures or video, 10-points for capturing the moment for each session.
Of course there are lots of possibilities here, variations of all sorts, from how these sessions are structured, scored, etc.
We prefer to do this over multiple days, so that each session can be preceded by our full sexual preparation ritual, as well as protracting the pleasure. The logistics are also a little easier.
Our reward system has varied, from Monopoly money, actual cash, jewelry, clothing, or other material rewards. I prefer to use actual cash or jewelry - it seems somehow sexier, more erotic, blending a sort of sugar-baby element into the challenge. Wardrobe can vary, ranging from simply naked, to more erotic lingerie or outfits. My favorite is to have KK wear stockings and heels, nothing else.
This challenge incorporates a bit of ritual for us, including the sex prep aspect. We prefer to do this in the same venue for all six sessions, ideally the same hotel suite. There’s an element of chance, in that because I’m the one picking the encounter partners, KK’s getting “luck of the draw,” and the Session Two encounter partner gets to double-dip, so to speak. That lucky guy will enjoy KK’s talents “extra” because of his place in line.
The basic challenge is structured along these lines:
- Session One - one-on-one. In this session, as a couple, focused on her, using a perhaps cliched term, you’ll go “round the world”. Challenge points are scored for each of the following:
1. Mutual masturbation (add one point if you both cum while masturbating for one another.
2. Reciprocal manual stimulation (add one point if she cums, but you don’t)
3. Master-slave oral (i.e. you service her, then she services you)
4. 69-oral (add one point if she cums, but you don’t)
5. Straight fucking - vaginal intercourse (add one point if she cums, but you don’t)
6. Anal sex (add one point if you cum in her ass)
7. Facial or body-shot (add one point if you cum on her tits, pussy, ass or feet, two points if you cum on her face, three points if you clean it up)
- Session Two - two-on-one (MFM). In this session, you will involve a second male in the encounter. The same seven session goals apply, with a twist:
A. She and the encounter partner execute all seven sexual goals, while you watch
B. Your encounter partner watches the two of you execute all seven sexual goals, while he watches
C. You add a traditional double-penetration component, anal-vaginal MFM
D. You add a less traditional double-vaginal, or double-anal penetration MFM component
E. You clean up your cum
F. You clean up his cum
A, and B accumulate a maximum of 14 challenge points. C adds 5 challenge points, D adds 10 challenge points. E adds 2 challenge points, and F adds 5 challenge points.
- Session Three - Three Men and a Lady - FM+. In this session, you’ll involve a second, as well as third male. The same sexual goals apply, with the maximum being your wife will repeat the steps with potentially three men; you, and two encounter partners. The twists in this session leverage the availability of three men:
A. She and the one of the encounter partners execute all seven sexual goals, while you and the third guy watch
B. Your encounter partners watch the two of you execute all seven sexual goals, while they watch
C. You add a traditional double-penetration component, anal-vaginal MFM, plus oral - making her air-tight (add five more points if she’s air-tight)
D. You add a less traditional double-vaginal, or double-anal penetration MFM component (add ten points if the four of you can manage some form of triple penetration, in any combination)
E. You watch her being spit-roasted (oral + either vaginal or anal penetration) by the two men (add five points if you can watch without cumming)
F. You clean up your cum
G. You clean up their cum
- Bonus Sessions Four, Five, and Six - She’s on her own. This is an advanced series of “stretch goals” in the challenge. If you’re both comfortable, the idea is for your wife to engage in solo encounters with each encounter partner independently, and the most advance part of the challenge, an MFM with both men - the twist is you’re not present.
1. Bonus challenge points are awarded if your wife acts independently to set up the date(s), five points for one solo date, ten points for the MFM encounter
2. A twenty point completion bonus for executing all aspects of the multi-session challenge
3. A sixty point maximum bonus if she allows pictures or video, 10-points for capturing the moment for each session.
Of course there are lots of possibilities here, variations of all sorts, from how these sessions are structured, scored, etc.
We prefer to do this over multiple days, so that each session can be preceded by our full sexual preparation ritual, as well as protracting the pleasure. The logistics are also a little easier.
Our reward system has varied, from Monopoly money, actual cash, jewelry, clothing, or other material rewards. I prefer to use actual cash or jewelry - it seems somehow sexier, more erotic, blending a sort of sugar-baby element into the challenge. Wardrobe can vary, ranging from simply naked, to more erotic lingerie or outfits. My favorite is to have KK wear stockings and heels, nothing else.
This challenge incorporates a bit of ritual for us, including the sex prep aspect. We prefer to do this in the same venue for all six sessions, ideally the same hotel suite. There’s an element of chance, in that because I’m the one picking the encounter partners, KK’s getting “luck of the draw,” and the Session Two encounter partner gets to double-dip, so to speak. That lucky guy will enjoy KK’s talents “extra” because of his place in line.
Turbolovers088
Female
Nice..Looks like the two up the back got all frisky too.
Me and my exwife used to play the children's game true dare but with adult variations of course. It started on our first holiday with daring each other to run the corridors naked in the hotel but after she got caught a few times we decided to go for dares outdoors such as flashing, flirting or even both together. We would go out to some night club or dance bars and Jen would get a few drinks down her and she would go to the toilet and come back with thong in hand so I knew she was naked under her dress (she never wore a bra). I would then dare her to dance on her own to see how many guys she could attract. Offers came pretty fast and in great numbers. part of the dare was that she had to feel the guy or guys cocks by dancing provocatively with her back to them and put her hands behind her to feel their cocks. Of course this progressed from there and by the end of the holiday she was going back to their rooms and fucking them while I waited for her to come back and fuck me and fulfill the true part of the game. Other dares was for us to go on clothes optional beaches where she would strip naked and I would pretend to read a book while watching guys looking, some openly wanking while at the base of her sunbed looking into her pussy.
That first holiday was really a precedent to how the rest we went on.
That first holiday was really a precedent to how the rest we went on.
Trev802
Couple
Picklerick
Male
We have standing out of town rules. Pussy shaved and no panties. Each time she gets up or out of the car she must spread her legs and pause for 5 seconds Recently we have added no bra. Love watching the guys enjoy a flash of her cunt.
hotwifeluvr
Male
Me too. But my wife cannot abide the potential for rejection. She would be devastated and it would ruin everything. That's not something that can simply be fixed. It's her nature and she has no desire to be different.
It works for us. Because really, if a guy isn't hungry and bold enough to take the lead in seduction, he's not what we want for this sort of fun anyway.
Demented_Donny
Male
One that I don't challenge my wife to do but she does it on her own accord is she will often pull down the front of her tight pants to show her shaven cunt to strangers and asks them things like, "I'm think of getting a tattoo here what do you think I should put?" another one is "Waxed is better than shaven right? here feel how smooth. no stubble right?" and of course, "it's hot in here blow on it to cool me off."
another thing she will do is purposely not wear panties and a very short tight dress. during conversations in front of someone be sure to do the whole fatal attraction leg cross, or drop something on the floor then bend over to pick it up to expose everything.
simple yet effective things work like this if the man isn't shy, as I have seen them done.
walk up to the guy she likes and simply ask, "have you ever got a blowjob from a complete stranger?" if they say yes then she will say, "then you have experience and this should be easy". if they say no she will say, "lets change that". either way she will head out to their or our car and blow the guy.
she will get men's numbers by walking up to them and asking, "what are you doing tomorrow at 6?" if they say nothing she will say, "don't make plans you will be fucking me." if they have plans she will say, "Shame, I wanted to fuck you." they usually will give her another time or date. sometimes they leave and go to his place right then. either way she gets their digits and gets laid.
Early one Saturday morning, I had been at breakfast with a buddy and he had complained about how boring his life was, which gave me an idea. I got up to visit the restroom and instead I called my wife to tell her that I would be bringing a man home with me in exactly 45 minutes and I wanted her to be waiting for me on the sofa, naked; and she was to pretend that I hadn’t just called her. She was also to have a large towel or robe with her to cover herself with, but she wasn’t to cover her ass, as she walked into our bedroom to get dressed; I also wanted her to dress sexily, but not in anything too revealing when she returned to the living room. She begged me to be able to wear something, as being completely naked at that time was tough for her (later she grew to love it), but I refused to relent.
Almost exactly forty-five minutes later, I opened the door and let my friend in, I pointed to the living room and he walked in and saw my wife on the sofa naked, except for her most expensive black Italian heels, which cost a fortune. She was resting her heels on the coffee table, so her knees were open a few inches, while she held a paperback in her hands. She let out a small "Oops" and she said, while grabbing her towel, “And here I thought I was going to surprise you.”
She got up with the towel in front of her, but not holding it well enough to completely cover her breasts and she introduced herself to my buddy and said to him, “Please excuse me while I change into something less comfortable.”
She walked away towards our bedroom with her ass completely exposed and jiggling nicely with each step in her high heels. Perfect. All of it was perfect. I loved the James Bond type lines she came up with. When she came out, she was wearing the same shoes, but with a very sexy summer dress. No sex, well at least no sex with him. I was super impressed by her boldness, as I wasn't sure she would go through with it, as I wasn't there to edge her on. I loved her lines, which she might have taken from some James Bond movie, such as Thunderball. Still, it was a great time.
She, like most women, thought her ass was monstrously too big, so I was so pleased that she didn't cover her ass as she walked into our bedroom. (Eventually, she grew to accept her ass, as so many men had told her that she had a fine ass.)
For some reason that story reminds me of when we were at a coffee shop and I noted that guy sitting a nearby table was facing us, but holding up a newspaper in an odd fashion. I excused myself to visit the restroom, but instead I went outside the coffee shop to look in the window at him from his side. I was right: he was not reading the paper; instead he was peering up her short skirt. I returned with a sheet of paper that said, “Act naturally and read the rest of this in the restroom.”
The rest explained what the guy was up to and told her to remove her panties before returning to our table and to give him a good show. She did. We had practiced the move many times before; it required that she twist her torso and reach around to gain access to her purse that hung on her chair, one leg straight out, the other bent at the knee, with her legs spreading, exposing a quick flash of her red bush. His newspaper quaked in his hands.
Almost exactly forty-five minutes later, I opened the door and let my friend in, I pointed to the living room and he walked in and saw my wife on the sofa naked, except for her most expensive black Italian heels, which cost a fortune. She was resting her heels on the coffee table, so her knees were open a few inches, while she held a paperback in her hands. She let out a small "Oops" and she said, while grabbing her towel, “And here I thought I was going to surprise you.”
She got up with the towel in front of her, but not holding it well enough to completely cover her breasts and she introduced herself to my buddy and said to him, “Please excuse me while I change into something less comfortable.”
She walked away towards our bedroom with her ass completely exposed and jiggling nicely with each step in her high heels. Perfect. All of it was perfect. I loved the James Bond type lines she came up with. When she came out, she was wearing the same shoes, but with a very sexy summer dress. No sex, well at least no sex with him. I was super impressed by her boldness, as I wasn't sure she would go through with it, as I wasn't there to edge her on. I loved her lines, which she might have taken from some James Bond movie, such as Thunderball. Still, it was a great time.
She, like most women, thought her ass was monstrously too big, so I was so pleased that she didn't cover her ass as she walked into our bedroom. (Eventually, she grew to accept her ass, as so many men had told her that she had a fine ass.)
For some reason that story reminds me of when we were at a coffee shop and I noted that guy sitting a nearby table was facing us, but holding up a newspaper in an odd fashion. I excused myself to visit the restroom, but instead I went outside the coffee shop to look in the window at him from his side. I was right: he was not reading the paper; instead he was peering up her short skirt. I returned with a sheet of paper that said, “Act naturally and read the rest of this in the restroom.”
The rest explained what the guy was up to and told her to remove her panties before returning to our table and to give him a good show. She did. We had practiced the move many times before; it required that she twist her torso and reach around to gain access to her purse that hung on her chair, one leg straight out, the other bent at the knee, with her legs spreading, exposing a quick flash of her red bush. His newspaper quaked in his hands.
I told my wife one day how I would love to see her walking around but naked on our balkony... She said your crazy,no way!
Knowing her I told her she doesnt have guts to do it, challenging her in a way. She got mad, not wanting to talk to me 😅
Next day I'm at work, suddenly I got message from my wife... its a video, her walking but naked on our balcony.. and a message "dont dare me!"
I got so hard! Couldnt belive she would realy do that! I still have that video 😉
Knowing her I told her she doesnt have guts to do it, challenging her in a way. She got mad, not wanting to talk to me 😅
Next day I'm at work, suddenly I got message from my wife... its a video, her walking but naked on our balcony.. and a message "dont dare me!"
I got so hard! Couldnt belive she would realy do that! I still have that video 😉
hotwifeluvr
Male
My wife dresses very sexily, but at the same time modest. The "less is more" approach. And she's very sexy to begin with.
My dare for her is to go braless and/or without panties. To date, she will not. It feels too vulgar to her, or that she'd be throwing herself at men, and she always prefers to be pursued. Which is not a problem, men pursue her!
She has big, pencil eraser nipples that are perpetually erect, and which would be impossible to miss if she were braless. So she feels this would be lewd. To me, it would be sexy as hell and guys would be falling all over themselves to ogle them, probably not even able to hide their ogling.
I argue that it's not really a lot different from when a woman puts her tits on display with a low cut dress and a push-up bra. Especially if they are big. Guys can't help but look at them. And she's calling attention to them, "Look at my big tits!" Yet for some reason, that piece of nipple at the end is so vulgar that even fully covered by fabric, it is lewd? If the entire breast were covered completely except for that nipple, it would be shocking if it were exposed (and sexy, to me!). And in my dare, it's not even exposed. Just not hidden. What about when the outline of a man's penis, or his bulge, is discernible? She agreed that in most cases, that is quite acceptable!
She agrees with the logic, but still can't bring herself to do it. Yet.
My dare for her is to go braless and/or without panties. To date, she will not. It feels too vulgar to her, or that she'd be throwing herself at men, and she always prefers to be pursued. Which is not a problem, men pursue her!
She has big, pencil eraser nipples that are perpetually erect, and which would be impossible to miss if she were braless. So she feels this would be lewd. To me, it would be sexy as hell and guys would be falling all over themselves to ogle them, probably not even able to hide their ogling.
I argue that it's not really a lot different from when a woman puts her tits on display with a low cut dress and a push-up bra. Especially if they are big. Guys can't help but look at them. And she's calling attention to them, "Look at my big tits!" Yet for some reason, that piece of nipple at the end is so vulgar that even fully covered by fabric, it is lewd? If the entire breast were covered completely except for that nipple, it would be shocking if it were exposed (and sexy, to me!). And in my dare, it's not even exposed. Just not hidden. What about when the outline of a man's penis, or his bulge, is discernible? She agreed that in most cases, that is quite acceptable!
She agrees with the logic, but still can't bring herself to do it. Yet.
Davis007
Male
We find dares a lot of fun and play around often.
A few years ago, we were getting ceiling fans and downlights installed at home, in the evening, wife mentioned that the electrician was cute, so I dared her to dress slutty the next day, she put on a short skirt and crop top chemise and distracted him all of next day, once when he was on a ladder, she went and stood with her face next to his cock, nothing more but it was fun.
Some time ago we had been invited to manager's 40th party at his home, and I dared her to go dressed as a teenager, she took up the challenge as it was on Sunday afternoon, a casual affair, but not so casual.
A few years ago, we were getting ceiling fans and downlights installed at home, in the evening, wife mentioned that the electrician was cute, so I dared her to dress slutty the next day, she put on a short skirt and crop top chemise and distracted him all of next day, once when he was on a ladder, she went and stood with her face next to his cock, nothing more but it was fun.
Some time ago we had been invited to manager's 40th party at his home, and I dared her to go dressed as a teenager, she took up the challenge as it was on Sunday afternoon, a casual affair, but not so casual.
cockfoster
Male
Davis007
Male
Once, my first wife and I were in a record store and a female college student walked in wearing overalls with no bra. Mercy! Her tits were tiny, but cute and the side-boob made me instantly hard. My ex didn't own any overalls, but she did before we got home. She only wore it in public without a bra a few times, but it drove me insane with lust when she did—something I would have thought impossible had I been told that overalls could be super sexy.
She grew to love letting men steal peeks of her body. We were obsessed with big numbers, such as the number cocks that had entered her. Well, we also tried to keep a tally of the number of men who had seen her breasts or naked pussy and ass, which was impossible, but fun. Flashing was so much easier than finding extra cocks. She wore special clothing on the weekends, when we went out on exposure trips, say to a renaissance fair or a farmer’s market or flea market. In other words, she wore blouses (or dresses) that allowed her to “accidentally” reveal her braless breasts, as she bent over to look at some item for sale. Our ploy was to make sure she always wore two sets of glasses: a pair of sunglasses on her head, as men have this crazy idea that if they could not see her eyes, she could not see their eyes staring at her cleavage; and pair of reading glasses hooked and snapped over her blouse’s opening, so when she bent over, the weight of the reading glasses pulled her blouse open, revealing her goods. We discovered that V-necks didn’t work as well as high round or straight necks, which dropped open beautifully. But when she stood up, she looked 100% modest.
Showing off her lovely legs was easy, as shorts and miniskirts did a good job. She didn't like to dress too sluty or wear too revealing clothes in public. Instead, she preferred having the plausible deniability going for her. Well, this now you don't see, now you do trick was perfect. Even long dresses could prove effective, as we bought her thin, printed, cotton, peasant dresses from India that looked perfectly proper indoors, but became transparent, when the sun hit her from behind. So, we would walk down an exclusive street in a ritzy town filled with fancy shops at just the right time of day for the sun to be low enough to shoot through her dress, revealing her totally-underclothes-free body under the thin cloth. As she paused in front of the open doorways into the stores, turned, and spoke to me about the treasures inside, the men who got dragged into the stores by their wives looked out the door at my treasure in the outside sun.
Even shopping in the stores was sexually charged. For example, she would always call me over to her dressing room—before she tried on an article of clothing, so I could see her naked breasts or entirely naked body. I always held the door or curtain a tad too open, so others might also look in at her. More than once, I dragged a male friend of ours, who had tagged along with us, over with me, so he could share with me her flashing. Once we were in a woman's clothing store and she showed me a belt she was interested in buying. I told her that she should try it on. She began to wrap it around her waist and I stopped, informing her that I meant in the dressing room. She dutifully went inside and called me over. Inside the booth she was naked, save for her socks and the belt.
She grew to love letting men steal peeks of her body. We were obsessed with big numbers, such as the number cocks that had entered her. Well, we also tried to keep a tally of the number of men who had seen her breasts or naked pussy and ass, which was impossible, but fun. Flashing was so much easier than finding extra cocks. She wore special clothing on the weekends, when we went out on exposure trips, say to a renaissance fair or a farmer’s market or flea market. In other words, she wore blouses (or dresses) that allowed her to “accidentally” reveal her braless breasts, as she bent over to look at some item for sale. Our ploy was to make sure she always wore two sets of glasses: a pair of sunglasses on her head, as men have this crazy idea that if they could not see her eyes, she could not see their eyes staring at her cleavage; and pair of reading glasses hooked and snapped over her blouse’s opening, so when she bent over, the weight of the reading glasses pulled her blouse open, revealing her goods. We discovered that V-necks didn’t work as well as high round or straight necks, which dropped open beautifully. But when she stood up, she looked 100% modest.
Showing off her lovely legs was easy, as shorts and miniskirts did a good job. She didn't like to dress too sluty or wear too revealing clothes in public. Instead, she preferred having the plausible deniability going for her. Well, this now you don't see, now you do trick was perfect. Even long dresses could prove effective, as we bought her thin, printed, cotton, peasant dresses from India that looked perfectly proper indoors, but became transparent, when the sun hit her from behind. So, we would walk down an exclusive street in a ritzy town filled with fancy shops at just the right time of day for the sun to be low enough to shoot through her dress, revealing her totally-underclothes-free body under the thin cloth. As she paused in front of the open doorways into the stores, turned, and spoke to me about the treasures inside, the men who got dragged into the stores by their wives looked out the door at my treasure in the outside sun.
Even shopping in the stores was sexually charged. For example, she would always call me over to her dressing room—before she tried on an article of clothing, so I could see her naked breasts or entirely naked body. I always held the door or curtain a tad too open, so others might also look in at her. More than once, I dragged a male friend of ours, who had tagged along with us, over with me, so he could share with me her flashing. Once we were in a woman's clothing store and she showed me a belt she was interested in buying. I told her that she should try it on. She began to wrap it around her waist and I stopped, informing her that I meant in the dressing room. She dutifully went inside and called me over. Inside the booth she was naked, save for her socks and the belt.
anytime my wife and I travel anywhere alone she rides totally naked or nearly so and gives me roadhead when she gets tied of laying on her arms she will turn over spread her legs and use a vibrator while going down road. we have just recently added that she wears extremely short dresses or skirts and can't hold it down if the wind blows it up,she must also bend at the waist and pickup things that I accidentally on purpose drop. any time that she sits down her feet have to be wider than her shoulders and her knees wider than her feet
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