challenging the gf/wife....how to?

[morpho]

I had seen many entries on very similar cases on members of this and other forums, telling an experience in where they were asked and/or challenged (sarcastically) to wear high heels in order to see how it feels the pain and the level of difficulty that theoretically we men normally ignore. My wife in some occasions, when she complained about the pain derived from wearing high heels, replied to me that i should know that it is indeed a challenge, "you should wear once to see how it feels" and in all the cases i was prey of the fear or shyness in order to follow up the sarcastic comment/challenge. As I read more and more people here, had similar experiences, my question here is how can we play the reverse psychology in order to get our selves on a winner situation where our wife /gf etc, can approve at least once to wear heels with them? I know it will be useless if this is done once as a challenge to defeat, but how then I can turn it into an activity we may do together repeatedly? any advise? thanks

[Romulus]

I would remind her that she once told you that "you should wear them to see how it feels", the next time she is in heels. There is a perfect opportunity for you to climb on, "ok let me have them" if they are your size, if not you are in a great position to go shoe shopping for hh's with your wife for this little experiment!

[jwhite44]

I'd think the first step is determine if your SO's challenge is genuine, or if it's her just expressing frustration. Even thought shey says, "you should try it...", she may not really want to see you in any type of heels.

A more genuine challenge would mean she'd feel better with her wearing heels, if she senses that you have an understanding of what it's like. If you think she's open to this, then you could try to offer the challenge yourself: "If I try to wear some heels for {period of time}, would you wear your heels to {event}?"

Period of time could be a few as a few hours at home, to wearing them out with her while you shop together. The event could be a dinner date you have planned for her, where there's a special pair of heels you'd like her to wear. If you're just trying to get her to wear heels more regularly, then it could be, "If I wear a pair of heels out to the mall with you, will you wear yours more often?"

If she's still onboard, then you need to decide what type of heel is appropriate. If you want her to wear say 4" pumps, then you you might have to get a pair of pumps yourself. I would think that you agreeing to wear them say all day Sat or Sun in the house might satisify the challenge. If tell her you'd be willing to wear them out in public immediate, she might be thrown off a little by that.

If you want her to wear just any heels more often, then a heeled ankle boot is a great choice (something like this http://www.naturalizer.com/Shopping/ProductDetails.aspx?p=EC0224309). In larger sizes the heel is over 3", I think high enough for her to think, "yeah, that's a high heel", yet not too high that even in public, you couldn't manage. It's also a pretty discrete looking boot. Worn with a longer length pair of jeans, few if any others would know you're wearing high heel shoes. That's probably a good point to stress to her - if she's not that fond of wearing heels, I'd guess she'd be even less so of her partner doing it.

For the actual shoes/boots, you can either just say either, "Pick something that fits me, and I'll wear them for you", or, "If I have to go out in public, let me find something that isn't too obvious or feminine (the link above being a good example)".

If you decide to give this a try, let us know how it goes.

[Histiletto]

First of all, you are in a relationship with a special person, who similarly reveres and cares for you. What is her attitude about wearing high heels most of the time? Are they like diamonds or are they things that men want women to wear as far as she is concerned? Also, has she ever expressed her view to you about men wearing heels and does she have any idea of your desire? Things like these need to be understood before entering such an agreement. Once the challenge has been met, will you continue to wear the heels she chose for you around her regularly, occasionly, or will your heels have to sit in the closet to be worn in secret without her knowledge as oppose to staying trustworthy and getting rid of them? This situation could be negotiated as long as you both thoroughly communicate all of the factors while determining the best decisions. Being that it is her challenge to help you understand how she feels in wearing the heels she has on, your empathetic responce to accept the challenge should expect to follow her terms. However, she has to be willing to help you choose a similar style, that was the ignition of the challenge, in your size with the same slope to keep the field of play equal. Any other style with a lesser slope, would be seen as a cop-out or the same style of heels with a greater slope would seem to be boasting, especially should you wear them with out having any problems, which could cause a bit of jealousy and contention. There should also be a period of preparation and familiarization so that you have some experience wearing the heels she has helped you to choose for the challenge.

[SomeGuy]

If you want her to wear just any heels more often, then a heeled ankle boot is a great choice (something like this http://www.naturalizer.com/Shopping/ProductDetails.aspx?p=EC0224309).

Very nice. Thanks for the link.

[jwhite44]

I'm not sure you should initiall offer tomatch your SO one for one, both for wearing time and for height (not that some people here wouldn't want to!). As long as you're pretending to wear (try to wear) the heels for her, then you may not want to appear to be too eager. In this case, prorating your heel involvement compared to her I think is a perfectly acceptable compromise. Time is pretty easy. You can say, "I'll wear heels {once a week, once a month} if you wear yours regularly." The amount of time would depend on how often she wears hers: - if you want her to wear hers daily, then once a week or on the weekend would be good - if she'd only wear hers on the weekend, maybe one night a week that you go out, then once a month is a good amount. What I think wouldn't be a good ratio is if she says she'll wear hers once a month, but you say I'll wear mine every weekend. That actually makes you the primary heel wearer, and I think will set off some red flags pretty quickly. The heel height is a second factor you need to account for. If part of the challenge is to get her to wear 4" heels when you go out with her, I wouldn't assume you need to show her you can wear 4" heels first (at not initially). While she may not have worn high heels all her life, assuming she has worn heels, she'd have years, perhaps decades, of having worn heels. That's experience that you can't be expected to pick up in a weekend or two. How you'd want to play that is up to you. If you want her to wear 4" heels out, then you could say, "How about if I wear 3", is that good enough? (if you don't want to go up to 4")" Now, if you'd want to wear the same height as her, you could stretch it out, saying, "I need a month at 2", a month at 3", before I can get up to 4". That might be better for you, since it gives you an excuse on why you need to wear them more often. It also allows you to wear higher heights, maybe get her to wear higher heights if she agrees to match you inch for inch. In any case, you'd want to make sure your interest and enthusiam for heels appears to be more help her wear high heels more, than for you to wear them.

[JNR]

I'm not sure you should initiall offer tomatch your SO one for one, both for wearing time and for height (not that some people here wouldn't want to!). As long as you're pretending to wear (try to wear) the heels for her, then you may not want to appear to be too eager. In this case, prorating your heel involvement compared to her I think is a perfectly acceptable compromise.

Time is pretty easy. You can say, "I'll wear heels {once a week, once a month} if you wear yours regularly." The amount of time would depend on how often she wears hers:

- if you want her to wear hers daily, then once a week or on the weekend would be good

- if she'd only wear hers on the weekend, maybe one night a week that you go out, then once a month is a good amount.

What I think wouldn't be a good ratio is if she says she'll wear hers once a month, but you say I'll wear mine every weekend. That actually makes you the primary heel wearer, and I think will set off some red flags pretty quickly.

The heel height is a second factor you need to account for. If part of the challenge is to get her to wear 4" heels when you go out with her, I wouldn't assume you need to show her you can wear 4" heels first (at not initially). While she may not have worn high heels all her life, assuming she has worn heels, she'd have years, perhaps decades, of having worn heels. That's experience that you can't be expected to pick up in a weekend or two.

How you'd want to play that is up to you. If you want her to wear 4" heels out, then you could say, "How about if I wear 3", is that good enough? (if you don't want to go up to 4")" Now, if you'd want to wear the same height as her, you could stretch it out, saying, "I need a month at 2", a month at 3", before I can get up to 4". That might be better for you, since it gives you an excuse on why you need to wear them more often. It also allows you to wear higher heights, maybe get her to wear higher heights if she agrees to match you inch for inch.

In any case, you'd want to make sure your interest and enthusiam for heels appears to be more help her wear high heels more, than for you to wear them.

This scenario is way to complicated.

"KISS" The next time the opportunity arises, just tell her that you like heels and would be happy if you could wear them. If she's not OK with that or you "rip it" completely apart, then so be it.

Quit over analyzing the situation. JUST GET ON WITH IT, MAN!

[yozz]

This scenario is way to complicated.

"KISS" The next time the opportunity arises, just tell her that you like heels and would be happy if you could wear them. If she's not OK with that or you "rip it" completely apart, then so be it.

Quit over analyzing the situation. JUST GET ON WITH IT, MAN!

I agree completely.

All those complicated scenario's assume that the other is completely

stupid and doesn't see that you are hiding something.

Assume that your SO can think, for Christs sake.

Or did you select her for being "sweet and dumb"?

Y.

[Majo]

I totally agree with you, jwhite44. In my case, most of the complaints were due to frustration. And she knows she can't challenge me with in the matter. She'll loose as my heels are usually higher than hers.

[roniheels]

Morpho ...

I don't know how this is going to play out for you but I wish you and your wife the best of luck. I am seeing a woman now who really does not like wearing high heels (except to weddings, church, formal affairs, etc.) and she even sells them for a living, but does not mind me wearing high heels, even in public. She is a pretty and sexy woman and looks even prettier and sexier when she wears high heels. I have even told her this, but after she wears high heels for a while, she is very quick to take them off and will even walk around in her stocking feet or barefooted as opposed to wearing them. I am now resigned to the fact that I will savor the moments when she wears high heels and enjoy the view and I'll let her keep complementing me and encouraging me to wear high heels when I am with her. This probably doesn't help you, but I wish you both the best.

[morpho]

thanks to all, I think all of you have a point, and i agree that the most important thing is to have decided a response when it will happen, period, this is similar to all things in life, if i rush it or i force it it wont go well 100%, so even if the process could be complicated or not the best thing is to have the game set for the moment when she challenge to play. the shoes given in the link are cool, maybe the best for give a start, i remember i did some alteration to a my casual man ankle boot and increased the high of the heel to 2 inches it almost looked like that one, but with a wide heel and a man shoe shape, maybe a look for special orthopedic shoe, anyway she did like it as i look taller, i have no idea how she will react if i come home with a ladies pair of shoes (regardless the high of the heel or the look if is too neutral or too feminine) maybe she will laugh or she will hate it and start to guess about my cd values, haha I am still debating whether i come with a pair by my self or i ask her to choose a pair for me when i see a clearance of my size. Other is to tell her is a kinky thing i read, to put on red 5inch high heel pumps,

[The Shark]

Yeah, my GF has challenged me too whenever I happen to be shoe shopping with her. Of course, I'd love her to get more high heels, but she always complains about how they hurt when she tries them on (she's a nurse & is used to wearing sneakers all day at work, so of course any heel will feel uncomfortable to her). But yes, she has challenged me a couple of times - the last occasion was when we were at a DSW shoe store & she was trying on some various heels. I told her that I would try on a pair at some point. She wanted me to try on some heels right then & there, but I chickened out because the store was quite crowded and I didn't want to be on display while trying on heels. There was another time that we were out shopping later one night, just going to a Target store for some things. As we pulled into the parking lot, there was another shoe store next to the Target & my GF asked me if I wanted to go shoe shopping. At that point I was just tired & wanted to get our stuff at Target & get home, so I kind of blew it off & said no (which I sort of regret). So now I'm waiting for the next "challenge opportunity" to happen - it'll probably be the next time I go shoe shopping w/ my girl. I'll start picking out some heels for her & she'll likely throw down the challenge again. But next time, I WILL accept her challenge - but I'll say that she has to buy me a pair & I will put them on at home. So I'm hoping that this will be the start of us wearing heels together, at least at home. I'll use the opportunity for her to get me something I don't already have (maybe some high-heeled clogs or ankle boots that I can wear with jeans?).

[jwhite44]

... i have no idea how she will react if i come home with a ladies pair of shoes (regardless the high of the heel or the look if is too neutral or too feminine) maybe she will laugh or she will hate it and start to guess about my cd values, haha

I am still debating whether i come with a pair by my self or i ask her to choose a pair for me when i see a clearance of my size...

A few ways to look at it. First, you need to decide if you tell her, if you'd say, "I'd like to wear women's shoes", or, "I've worn women shoes." Either way, unless she passes out, or leaves the room, and some point I think, "what type of shoes?" is going to come up.

I don't you should have her pick out a pair for you. If you're proclaiming to be into women's shoes, then you ought to either have an idea of what you like, if not already have your own pair. At this point, you can help reduce the shock by picking a more unisex looking shoe. If the assumption of your wife is that your a straight guy, telling up right up front that you like want to wear 4" pink sandals (even if you do) can be a heck of a shock to her, and probably something that she doesn't need to deal with immediately. So start out a bit more conservative; if she's accepting of it, you can always start to stretch the boundaries later on.

[jwhite44]

...So now I'm waiting for the next "challenge opportunity" to happen - it'll probably be the next time I go shoe shopping w/ my girl...

Hopefully there will be a next one. The fact that you already "chickened out" twice, she may think you're really not interested, and not bother asking you again.

Fingers crossed that I'm wrong...

[The Shark]

Hopefully there will be a next one. The fact that you already "chickened out" twice, she may think you're really not interested, and not bother asking you again.

Fingers crossed that I'm wrong...

Yeah, me too...

But I'm sure that there will be a next time. I've promised to buy her a pair of Kenneth Cole pumps soon. And once in a while while we're out shopping for other stuff, we'll stop in the shoe stores. No matter what kind of shoes she's after, we always look through the heels (for her). Sometimes we'll look for what we call "playtime" shoes that have higher heels (4"-5"), sometimes with platforms. She'll ask me to pick out a few different pairs for her that I like & she'll try them on. A lot of the time she'll complain about how uncomfortable they are, so we don't always buy them . But this is usually when she'll challenge me to put on some heels to see what it feels like. As I said, I'll take her up on the offer - but I'll tell her that we'll have to buy a pair & I'll put them on at home.

[jwhite44]

.. but I'll tell her that we'll have to buy a pair & I'll put them on at home.

No shame (in my opinion) in buying a a few different sizes, so you can try them home there, and see which one fits best. Of course, this tends to make more sense when you're buying alone (sales person might infer you're not sure which size to buy). Not as good a story if she's there with you.

To be honest though, since she'll be with you, just slipping your foot into a shoe (to see if it fits) shouldn't be that big a deal. Walking around in them is a different matter.

[Sparky088]

Yeah, my GF has challenged me too whenever I happen to be shoe shopping with her. Of course, I'd love her to get more high heels, but she always complains about how they hurt when she tries them on (she's a nurse & is used to wearing sneakers all day at work, so of course any heel will feel uncomfortable to her).

But yes, she has challenged me a couple of times -

I bring this up ONLY because of the business I'm in.....you really need to expect your "opponent" to be at least as smart as you..... By this I mean, you say "GF" this probably means she has been to your digs many times. Are you sure that she doesn't already know that you wear heels??? Maybe she is just baiting you and it is time to come "out of the closet".

Anyway food for thought.

[crotchboots-m]

my wife knows better...she doesnt want to encourage my decadent behavior. but back to women and there grievances about wearing heels...ive never seen anyone with a gun to their head making them do it. if they dont like them...dont wear them

[morpho]

thanks all for your ideas and opinions, some posts are really interesting while others are a little out from what i was expecting, no offense crotch boot-m , we are actually taking baby steps here, and we hope to reach your level one day, why not you tell us if it ever been in the past an experience similar to this and how you dealed with it. The point i am trying to analyze here is to touch the wife or gf from the side of the challenge to wear heels together and how to do it smoothly and natural, and what would be the cons if they will start to know you are into heels and do not approve. very simple On another thing, i would like to jump on the shark experiences, what do you think she will say if you come home with two pair of black classic pumps 4inch heigh for you two. do you think she will take it in a bad way after she already challenged? I am kind of preparing a moment where i will come with these two pairs and tell to mine, hey you lets see who walks better a guy or a girl? i would love to see you on thses ones more often, so i bought mine to support you... something like that. in fact the response by jwhite44 is actually help full you are righ what if she decides for me in order to analize my intentions, women are women, they will always keep playing these little games, i gave it a though and i think is better to come up with the proposal after declining an open challenge that may or may not serious on that moment, and maybe just testing.

[jwhite44]

Morpho, there's no perfect answer, since no one else exactly knows the situation with you wife (including perhaps you!). Hopefully you'll get a number of responses to your posts. If you're lucky, there might be an outright consensus on what to do. More likely though, you might see a little tidbit of advice in each which seems best, which you collectively massage into your best course of action. That's at least what I get out most websites I participate in. As always, keep us apprised of how things go.

[trevor]

hi morpho- just to let you know this is exactly how it started for me. my wife always wears high heels and stockings etc. because she knows how much i like it when she dresses like this both in and out of bed. she says she doesnt mind because she feels sexy when she dresses like this. she has always worn 4 inch pumps and on occassion 5 inch pumps. we go to las vegas like 3 times a year where she usually really sexes it up with the 5 inch heels when we go out at night. about 6 years ago at the end of the night she said her feet were a little sore so i made a comment it cant be that hard to walk in those shoes. she says id like to see you walk in them. i said they wont fit but id like to try and see what it feels like. this was my opening and i took it. i didnt say another word about it. when we got home i went on the computer and found a pair of 5 inch pumps at electrique boutique in a size 12 for like 19.00. i didnt tell her i was ordering them. i wanted to find something cheap. when ups delivered them she says what did you order. i then told her that she said she wanted me to see what it was like to wear 5 inch pumps so here they are. i said i found them for 19.00 so for the fun of it i ordered them. i told her ill put them in the closet and some night when weve had a few drinks well have a few laughs. that was the end of it untill one night we stayed home and ordered chineese food and had quite a few drinks which really was the key here. she was definetly feeling no pain. i told her im going to go upstairs and put the shoes on and see what its like. i went upstairs and decided im really going to go for it. i put a pair of her pantyhose on and i have a silk type robe which i tied and wore the heels down stairs. i says what do you think. then she says your wearing pantyhose and i said my legs looked funny with just the heels so i put the pantyhose on to make my legs look better. she says actually it looks kind of sexy and then she says if your going to wear pantyhose you should shave your legs. dont forget she was feeling pretty good. dont worry i was going to take advantage of that statement sometime in the future but again just let that statement go untill i get the opportunity and i will tell her that she is the one that told me to shave my legs when i wear pantyhose. today 6 years later about once a month we stay home and order chineese food and she makes some drinks and i get dressed up later and wear a tight skirt 5 inch heels and pantyhose and she also dresses up and it makes for a fun evening. on halloween about 3 years ago i pushed the envelope again and went up stairs and put on a wig that my wife wears sometimes in las vegas with the full make up and whole outfit. when i came down stairs she says wow what is this? i said i figured its halloween so i felt like doing something crazy. once again she had some drinks in her so she just went with it and she went upstairs and put a real hot outfit on and what a great night. this halloween we went to las vegas and i dressed up as a complete woman with a very short sexy dress and 5 inch new platform high heel pumps and we went to studio 54 at the mgm both nights. you have no idea the planning i did for this. lets just say it was the most ultimate experience of my life and it all started with where you are right now. good luck

[morpho]

I love your story trevor, i think is very authentic and of course doable, i will use it as a go by, lets see if something good happens, but i must admit, it totally depends on the type of personality of our wives, so for you it give it a boost as your wife is big fan of the heels etc, Also it depends on the booze and the occasion, so i will see if it will happen one day, as you say one step at the time so i wont show wrong signs. Out of having only fun is the reason.... thanks again for your story.

[jay jay]

Hi there. As I said else where it started with me with my ex 2 1/2 years ago when we had to dress uo for teh Rocky Horror show and i was dressed up high heels and all. Got divored and met my current wife.. I Remarked to her once of how would she feel if I try on her high heels. She thought that is was funny but i can try them. That was the end of it we go out and we buy shoes together, as we wear the same size a UK 8, at the moment she tries them on and well considder them bought. Between us we have about 55 pairs of different types of high heels and boots.. The other day we went to the movies and walked past this shop that had some Pleaser HHs in the window, I remarked that I would love a pair of the 5" platform shoes. We walked on and about 10 mins later she said lets go back and see what they got, well needless to say she bought me a pair of PleasersIindulge 543 with a 5" heel. ( Had to go to a 12 US) I must say they are the most comfortable heels that i got and try to wear them ( at home at the moment) as much as possible

[legzG]

We were at a shpping centre a couple of weeks ago and we saw a fabulous pair of shoes with a 5.5" heel and elastic strapps over the foot. I loved the look of the shoes so much, we decided to buy them. She was sceptical about my abilities to handle such high heeled sandals. Needless to say they were very confortable. I didn't battle to walk in them at all.

[trevor]

morpho-. let me just say one thing. even though i would like to do the dress up thing more often i dont want to push it because i dont want to ruin a good thing. one mistake and this thing could take a wrong turn. you have to be carefull. one of the other big things was after this started i would show her on the internet how there are alot of wives and husbands doing this type of thing just to spice up their marriages. i would read to her some of the articles that would say that many women find it kind of sexy to see their husbands dressed in lingerie and heels. good luck. i hope you get that opportunity

[jwhite44]

Definitely makes sense to take things slow and cautiously if you aren't sure how she'll react.

[legzG]

These are my new heels I wrote about earlier this week. By the way I proved I can handle the heel height. I am enjoying them so much!! Cheers LegzG

[jwhite44]

These are my new heels I wrote about earlier this week....

These shoes: a fabulous pair of shoes with a 5.5" heel and elastic strapps over the foot... ??

If so, very nice.

[The Shark]

Well the day has finally arrived!! In one of my earlier posts, I mentioned how my GF has challenged me on a few occasions to wear heels & see what it feels like (even though I already have done it, shoe doesn't know it) . I have told her that I would try it, but I won't put them on in the store - we have to buy a pair & bring them home. Last month she chalenged me again, but her friend was in town & staying with us, so I just blew it off. Just earlier this week, we were having some fun texting each other & I said that I'd love to see her wearing ONLY a sexy pair of heels - so we agreed that it's time to get her another pair of "fun" shoes. During the course of conversation, she remarked about how uncomfortable heels are to wear - I replied saying they can't all be that bad. So once again, she issued the challenge to me - and I gladly accepted! So we agreed that when we get her a new pair of sexy heels, that we're also going to get a pair for me too! Tomorrow is our shopping day, and I can't wait to get another pair of heels and wear them for her! I'm really hoping that this will become something new in which I start wearing heels with her, which will also let me build up a nice collection of shoes! Now the big question is... what kind of heels to get? I've got the pair in my avatar.

[hh4evr1]

You could get the same as her as part of her challenge.