How I unknowingly backed into crossdressing

So some of you may have seen comments I’ve made on threads stating that my wife doesn't know about my dressing at all. And you’ve probably seen that I qualify that by stating that's not entirely true because she does know about the boy-shorts panties and the girls' cut jeans I wear. But those were her ideas, born out of function so it’s kinda not really crossdressing right. :D

See about a year or so ago she bought some compression-type, spandexy boxer briefs for me because she HATES the cotton boxer briefs I used to wear saying they get stretched and baggy and end up looking like I’m wearing a diaper. But I didn’t like how high the waist band was on the compression shorts so I bought some plain colored boy-short panties (which are low-rise), told her why and showed her what they looked like on. She LOVED how they looked on me. I mean she REALLY loved how they looked on me, if you know what I mean. :o This was way before any thoughts of crossdressing came into my head but… yay me!

So about the girl jeans… after years of complaints about my jeans being baggy and yucky as well one day she insisted we buy some that actually fit. We found some guy’s jeans that were slimmer but again… the waist band was kind of high plus I didn't really like the color of the denim or the style much.

So while at WalMart one evening picking something up for the wife after work, I got the idea to look at the girl’s cut jeans to see what they were like. I took a pair home that I liked, wore them for her and the same result as the panties. She LOVED them. Soooo… that’s how wearing girl jeans happened. Again, this was before any thoughts of crossdressing entered my head but I do remember having some concern (yes, concern which really means kinda freaking out) about how I was now wearing panties and girl jeans and am I technically a crossdresser now. Yet conversely I thought “wow… these girl clothes do make my butt look pretty good.” Meh. I'm not. I'm wearing this stuff for a valid reason. :)

Then there’s my painted toenails. I think I’ve had those for a month. I did them after painting her nails and when I showed her mine she laughed, asked why I painted them and I said I thought it would be funny and it would give her a laugh.

The next morning after she came back from dropping the kid off at school this exchange happened.
Me: Well, the happy toes were fun but I took it all off this morning.
wife: What??? Why? (makes a pouty, sad face)
Me: Well... because, I mean I couldn't keep them painted.
wife: But, but, but...
Me: What are you talkin' about? You wanted me to keep them? Why?
wife: Well... um, I don't kno... I gues... (getting frustrated and stomps her foot) cuz they were pretty!!!

Me: Hm. :straightface:
wife: (pouty face.)
Me: (rips off socks) I still have the happy toes!
wife: squeeeee! We still have happy toes together!

So you see, I’m not really a crossdresser. I mean, you know, wearing boy shorts panties… her idea and out of function. Wearing girl cut jeans… kind of her idea, not really but still out of function. Painted toe nails… well, my idea but functioned to make my wife laugh and she wanted me to keep them.

So all I have to do now is figure out how to make her think wearing a bra and breast forms, hip pads, putting on makeup, wearing heels, a waist cincher, femme jewelry, a wig and perfume is all HER idea and a necessary function!

Any suggestions?

Next step? How about a woman's sleeveless camisole shapewear. I went before posting to see what's available at JCPenny. Maidenform and others make basic shapewear camisoles in black that are not lacy or frilly. They are functional. They should not appear baggy. And, you could pass them off as a nice undergarment to tan your upper body to eliminate the "farmer tan" next spring/summer. With the cooler days of winter approaching (Sorry you live in Texas and not Minnesota) there may be a need for pantyhose to keep you legs warmer. Try the old Joe Nameth football players wear them reasoning. Good luck. I cannot see how you can convince the wife you need a bra unless you start over indulging in mashed potatoes and pasta and develop "man boobs."

cami-tops, cami-tunics and leggings are quite "easy-wear" excusable steps

perhaps also you can say "hell, I like dressing like this can we explore it further?"

Pamela 7 has hit it on the head here.

We started out in a very similar way. A bit here a bit there and painted toenails. All good fun! I realised I wanted to go a bit further and suggested she gave me a makeover for fun and maybe try a dress on to see how I looked. We had a really fun evening.

At the weekend, we went too a bootfair to do a bit of trade and she wandered off to browse. About half hour later, she came back with a bag full of clothes to show me.

Nice stuff I said, it will all look good on you.

No! She said." It will look good on you"

We have never looked back. That was over twenty years ago.

well if tou were not a c/d before --------- it looks like you might be now :D you are lucky to have a wife like that sounds like it has been a lot of fun
hugs phylis anne

Well!
What a way to go. :)

Try womens "T" shirts, just plain colors but with "V" necks and maybe a boat neck. Very comfy and not too femme but functional. Depending on how hairy you are you may have to trim or shave the exposed areas which leads to another subject all together. Welcome to the wonderful world of CDing. Little steps and let her get used to the idea that you have a femme side.

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Originally Posted by aBoyNamedSue

... So all I have to do now is figure out how to make her think wearing a bra and breast forms, hip pads, putting on makeup, wearing heels, a waist cincher, femme jewelry, a wig and perfume is all HER idea and a necessary function!

Any suggestions?

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I can not buy into the notion that you "backed into" cross dressing. The reason is that a non-cross dresser would never go that route of "choosing" women's clothes. You are a cross dresser and therefore the option to wearing women's clothes was open to you.

Now, that aside, my suggestion is to not kid yourself. She will not suggest you wear a bra spontaneously. You are hoping that somehow she will make it ok for you to be a cross dresser without you having to tell her. Just tell her. It's really that easy. Best of luck

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Originally Posted by pamela7

...perhaps also you can say "hell, I like dressing like this can we explore it further?"

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In the circumstances, I think Pam's idea is not half bad... :)

Given your experience with the toes (I have my wife on board with nails but not yet toes... somehow they seem more intimate, IDK.. :confused:) it sounds like you're pushing at an open door... or at least one that isn't deadlocked, reinforced and alarmed.. :)

But there is a difference twixt painted toenails (which can just be a bit 'avant garde' or alternative...) and finessing a tolerance or acceptance of more overtly femulation elements... so take care...

But mainly: Keep Calm & Carry On! :D

Katey x

I think its time to just be honest with it. The fun stuff only goes so far. You don't have to make a big deal about it but maybe just say you want to see how it would feel to get fully dressed.

I too, have the minor things accepted. Painted toenails, shave chest, legs, etc. SO is okay with those things and even kind of like them. But I am pretty sure if I just threw on a pair of panties it would be a totally different scenario.

Maybe, when the mood is right. You can tell your wife: I think it may be fun if you give me a full make over one night; head to toe. If it works out, maybe you can plan to repeat once a month or so. This method eliminates all the painfully slow baby steps, trickery and fooling her and yourself.

Sounds to me like your wife is cool with it so you should figure a way to get her to dress you up. Could open a lot of doors for you.

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Originally Posted by aBoyNamedSue

So you see, I’m not really a crossdresser.

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I see that, yes. :brolleyes:

LOL Sayyidah! Is that reverse phsycology at work?! Way to go girl, ya know as a chic 'we' look younger, try that angle... 😀

I actually did not back into cding it backed into me :) .Or hit me over the head not sure

Thanks for all the responses ladies! Jennie yours actually made me laugh out loud. My post was intended to be very tongue in cheek, very much in a joking manner. Robin knows me a little better than most as we have PM'd a little here and there so i think she may have caught on to my attempt at showing the comedic side of my situation.

Jennifer wins the thread though by saying a non-crossdresser would never have used the idea of buying women's clothes first to resolve the clothing "issues".
I know I made it sound so casual, non-chalant. Truthfully, i was terrified walking the aisles trying to figure out which size might fit right, was anyone looking, am i going to be on People of Walmart. But truth be told I did check out the men's undies to see if there is a low rise option. There were but not as low as the girls undies.

To all you other gals, tanks for the suggestions. I'm afraid I'm not quite ready to come out fully to my wife and am very ok with what I am able to do. I know there are tons of our members here who would kill for the situation I've got and that is not lost on me.

Maybe in time. For now, I'm ok. I took all the nail polish off last night after we got in from taking the boy around scooping up sugary loot. After a month, the polish was looking pretty ragged. But I promised her a few days ago I'd make her toes pretty again so I guess I'll find out if SHE suggests this time I paint them instead of me testing the waters with an "attempt" to make her laugh like I did last time.

You should help her with her makeup, and see where that goes. It could be fun too.

Hahahahaha you have me almost peeing my pantie, your post is by far my favorite on this site. I can't wait until my wife wakes up so Ican show her. My boxers also looked like a nappy or as my wife said a sumo wrestler nappy thing:D so I done the same. I done my nail and was sneeky enough to do my kids so i could claim I was just having fun with the girls. ;)

This next one is my proudest work hahahahaha almost wetting myself thinking about it now. I saved up and so kindly got my wonderful wife a Sunbed just because i am that good of a hubby and not so I could claim my body hair was stopping me from getting an even tan lol hehehehe she spent hours shaving and waxing because i am like a bear. She was cracking up because of my yelps of pain as she waxed if only she knew that I had my arm over my face to hide the look of total bliss on my face and not to hide the tears in my eyes as I told her . all planed before I got such a kind gift but telling her the truth has backfired because now all the fun for her is gone from waxing me. Still was great while it lasted. :)

I have lots of stories like that but sure i have plenty of time to share them.

Now need to get my serious hat on again, sounds to me your wife wants you to crossdress.
I hope this next coment does not offend but maybe she might have a little bi side. My wife came out to me about two months ago and I just laughed at her and told her it was about time she worked that one out, I knew from the second I met her. She told her parents and then she got a bit angry because the reacted the same as me, they laughed and said the knew since she was about 14. She started complaining that if we all knew the we should have told her she was no lol beat the crap out of the 3 of us after that because we could not stop laughing. What a pair we make, on our first date and right up to now she has been pointing out women's butts and boobs too me and she didn't think that she might be bi but the best part is every time I would grunt in agreement but then get so excited at telling her how fabulous their skiny jeans looked or would even go over and ask the women where the got them cloths lol what a pair.

Listen boynamedsue, thank you so very much for this tread ;D i could not sleep tonight but after all this laughing I am knackered. Thanks much much much love

Anton Jon.

Great responses. Your diaper comment was probably right, and I agree with your wife, ewww!

Sayyidah, if the way you wrote it is accurate, it sounds like your wife would be more than tolerant. It sounds like she might enjoy this side of you. I think you have a great opportunity here. Just keep everything on the upbeat, and you'll be enjoying some cool jazz with her.