Why I am an Accidental Dresser

My story is not like any I have read here so far but I havent read every post on this vast thread as yet so there may be others that can relate or started dressing the same way I did.

I am a straight man and never felt confused about my gender or even thought about wearing female clothing.
I have always spoiled my girlfriend who then became my fiance who now I am not sure where we are at.
Every Birthday, Valentines Day, Christmas, Pay Bonus or Whatever was just a great excuse for me to buy my girl some cute, sexy, comfortable lingerie. I probably spent thousands over the years and she always gave the most excited smile and a big hug & said thank you so I really thought she liked it.
About 23 months ago I started to realise that she had hardly worn any of the Lingerie I had bought her and it started to worry me. When I asked about it she said "No its lovely I just havent had the chance yet"
She would say "You pick out something & I will wear it for you" but it was usually onl on for moments before she lured me in to bed & it was thrown on the floor again.
I finaly decided to confront her about it but in a really sensitive and understanding way.
She said it just wasnt practical or comfortable some of the things I bought her and she didnt feel she could wear it out anywear. This confused me because I THOUGHT: This stuff is made for women so how could it be uncomfortable. It will be under her clothes so no one will see it but I will know its there.
I pressed the issue further and really pushed her to explain her answer cause in my mind it didnt make sense.
She then said the following and I remember it word for word "OK, look hun I cant explain a feeling if you have never felt it you just wont get it. Here how about I dress you in some of the things you expect me to wear and we go out for dinner. Then perhaps you will understand what I mean. I do love everything you have bought but you will see what I mean about not being practical"
I didnt blink or smile or get excited I just said OK its a deal and she started to pull some things out of the drawers and throw together a lingerie outfit for me to wear under my normal clothes to dinner that night.
She dressed me in a black corset & pulled it pretty tight, she pulled a pair of black thigh high stockings up my legs and attached them to the corset. She then proceeded to pull a pair of black ruffled panties up my legs and that was where it got difficult. When I say difficult I mean hard, ROCK HARD in fact and I had trouble fitting in to them. we both had a laugh about it and one thing led to another and we didnt end up leaving the house that night at all, or the bedroom for that matter. It was probably the most intimate and open we had been in a long time and we had so much fun and it felt naughty and good.

That weekend I decided I told her we would stick to her original plan of going out for the evening with me dressed under my clothes because it didnt really work out the first time but I needed to make a few changes first.
She agreed that I hadnt really kept my end of the bargain so she would like me to do that so I really understood what she meant. My main complaint on the first go was how every time I moved the corset or the silicon bands in the stocking tops seemed to rip out a lump of hair so I decided to use some Sensitive Skin Hair Removal Creme that we picked up from the shops and make my whole body totaly hairless. That in itself was a very different feeling and I enjoyed the cool breeze against my skin & the fact that I seemed to dry in no time after the shower.
I got dresseed again as per last time and determined not to get arroused (thinking of everything possible to turn me off) I was finaly dressed and we went out to dinner, then to a movie, then to a bar for a couple of drinks & then for coffee and desert. We talked over coffee and she was honestly stunned that I had lasted so long without complaining about a single thing but I honestly felt comfortable and confidant & even a bit naughty and sexy.
We returned home and instead of undressing me she wanted to lay there with me and run her hands all over my lingerie clad body and turn me on till I could take no more and we again made more noise than our neighbours were used to. I woke up the next morning still wearing the corset so I slipped on the ruffled frilly panties and went to make crepes for breakfast in bed for my fiance. I really did not feel at all uncomfortable.

Anyway months of her dressing me up and playing with me in various lingerie items and just dressing me up to sit around the house or daring me to wear certain items of lingerie under my clothes when we went out to see friends went by and it was all going well. One night I surprised her by covering the bed in rose petals & lying there in what I considered the sexiest lingerie outfit but she looked irritated & not happy at all.
She walked straight out of the room and said "Please take that off and put on some of your own clothes, im really not in the mood"
Nothing more was said & weeks went by where we went back to our normal relationship & normal sex life but I now felt like something was missing.
One night I just naturally slipped a short satin nightie over my head, slipped on the matching panties and climbed in to bed with her. She asked what I was doing & I explained that if she wasnt going to enjoy the thousands of dollars of lingerie & nighties I had bought her then I would. I found it comfortable and felt nice in the silky nightie and liked the way my bum felt in the panties.
Next morning she got up and left without a word and went out for the whole day.
She came home the next morning and appologised to me & agreed that I should wear them if they made me feel good & that she also thought I looked very good and sexy in the lingerie I had intended for her and that she would do my corset up for me on a daily basis if I wished because she knew how much I liked to wear them.

It was ok again for about 2 months and then she moved back in with her mum. She thought she needed a break from us. She took everything she owned with her but she left ALL the lingerie I had bought her and even some of her own underwear and a few pairs of tights & some dresses.

That was 7 months ago and occasionaly she comes around to just dress me up and play with me like I am her doll or something but I really like it so I certainly wouldnt complain. Some times I am already dressed up and sitting on the lounge watching a movie or TV when she turns up un announced and she just cuddles up to me and might stay over. The engagement isnt off but its really not working very well.
She was over here doing my makeup a month or two ago which she had only just recently started doing after dresing me up from head to toe in a full fem outfit and as she applied lipstick to my lips she got a wicked smile on her face and said how sexy my lips would look (edited out)
I got offended and laughed at first but then was a bit hurt and offended and told her the only place I wanted to put my lips was on hers and that I was rupulsed by the idea of a man coming anywhere near me with his bits all hanging out. Again she said sorry and we kissed and cuddled and fell asleep together but its pretty rocky at the moment.
I wish I had never agreed to getting dressed that first time and I wish I had just bundled up the lot when she said she didnt like it & throw it all out. But I also wish I had discovered wearing all this earlier in life and had thought to try it in my teen years. I wish I could just dress like this everywhere I go.

Thats my story so far of how it all started for me & where I am right now. I wish I had never started but I know I will never stop. Its a blessing and a curse all in one.

Sorry its so long winded I just reaslly nedded to get that off my chest and I have not been able to talk to anyone about it. Its been eating me alive & now that I got that out I really feel like a weight has been lifted. At least for now anyway.

Thanks all for making this site possible. It really is a blessing.

You two need to talk about this x rated comment in particular. Is it just some "dirty talk" that she thought would get you off or is there more there? Overall, it seems that communication is lacking. You're not talking about why she likes x and not y. You have to open up and get it all out. There is no cure like conversation.

First, let me say your, "Story", sounds like something out of a CD fantasy novel. Maybe, only because u haven't put enuff of your personal feelings in there for me to identify with? When I started, I had plenty of conflicting issues to work thru! Still do, 17 years later. U haven't mentioned even one! Unless u count the obvious one that would likely come up with your SO?

Because I'm much like the man in your story. A straight man with NO gender issues until I reached my 50's and tried on ladies things for the first time. Before then, it never even occurred to me to try them on. Altho, I had plenty of opportunities.

I dress "accidentally" myself. Accidentally on purpose that is. ;):battingeyelashes::)

Maybe she needs to feel pretty and sexy also that why it's sometimes better to leav the dressing out of the bedroom

Kate I guess my name isn't really correct as I am very deliberate about what I wear now.
It's more a case of accidentally got hooked on the look feel and smell of all things feminine and now I can't stop. Or don't want to stop or a bit of both really

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Originally Posted by docrobbysherry

First, let me say your, "Story", sounds like something out of a CD fantasy novel. Maybe, only because u haven't put enuff of your personal feelings in there for me to identify with?

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I agree... AccidentalDresser, I think we'd all much rather read your own personal experiences even if they're a lot less glamorous.

Sure sounds like a "Sandy Thomas" story. If it's true, it sounds like marriage is not in the near future. She is a little passive/aggressive about all this. No real advice here.

Sounds more like someones fantasy put into words. I agree we would rather hear about you.

Sounds like fetish play overload to me. Not really a foundation for a lasting relationship.

I sensed in some of the responses that it was wondered how true is this story. I tend to work on the innocent principle that if a person chooses to write at length in this way then it does represent reality. I guess I would make two major observations. Firstly, practically how difficult it is to buy lingerie for women. We are essentially buying clothes we want the other person to wear when in fact they have to wear it and it may not suit their comfort or needs. I do not have a huge range of feminine clothes but I do know that there are some panties that I can wear all day in comfort and almost not realise I am wearing them and there are others that just do not sit comfortably and I am glad to get off. You can repeat that comment for almost every item I guess. The other point is that I supect that when men buy lingerie for a woman there is often an unconscious desire being enacted that the items are for them. The items intrigue us. They arouse senses in ways that heavier duty male underwear does not. You found that when you were dressed it is hugely erotic, and that is quite appealing.
I cannot get inside the head of your partner, all sorts of other things might be going on. However what is clear is that in an established relationship something changed, quite a major thing. What most of us would say who have opened up to our partners is that the reaction is very diverse. I suspect that the major reason for not being open is a fear of not knowing what the reaction might be? You should also consider how things have changed for you, you are not the same person, that can be more than a bit scary.
What has held me together more comfortably than shame and the fear of discovery that pervaded my life for many years is a need for personal honesty. Understanding yourself takes time and often needs to be talked out with others. Perhaps also your partner needs to think about her integrity and needs to engage in a dialogue with you about your joint and separate needs.
The one thing I am sure that all of us would say is that we wish you well.

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Originally Posted by Michelle James

Sounds more like someones fantasy put into words. I agree we would rather hear about you.

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Not far off from my personal fantasy. Only difference is I'm already married!

As far as Accidental is concerned, it really reads like the relationship is over and she's just using you for occasional enjoyment. If you're not seeing your fiance on a regular (basically, daily) basis and the reason isn't geography or a non-common work schedule (like a hospital-based doctor or firefighter), that's a problem that needs addressing (no pun intended).

It does sound like a Sandy Thomas novel, but the part about the GG finding it kinda cute at first but getting fed up with it and leaving has a ring of reality to it.

In many ways, you are right, it is a shame you discovered a desire to dress. If this relationship does not work out (not likely it will), it may cause problems for all subsequent relationships and you may even be rejected completely for it.

I wouldn't take her comment about your lips too seriously. She was either just teasing you playfully, or she was upset with you and just wanted to get your goat.

First of all - thanks for sharing that AD... don't worry about some folks uncertainty regarding veracity - we've had some classics here that have fooled people for long time... if it's important to you to share, that's fine; everyone has that right... :)

Simply - there isn't anything that speaks of transgenderism to me in this. Doesn't mean that's bad or wrong; just means to me that your crossdressing is heavily on the fetish side of things currently, rather than anything regarding expression of gender... I believe it's widely accepted that while 'fetish' used to be regarded as a bit of sexual thing with bad connotations, it's now seen as a normal and healthy pursuit... So go enjoy it as long as you can... it may shift over time, and then you end up like some of us agonising over whether to go out, what hair colour to have... seriously, you're probably better off... :D

Katey x

Thanks Katey. As for those who say it reads like a fantasy????
Not sure how turning your life upside down and losing your fiance then being left to pay both halves of the rent on your own is much of a fantasy but whatever tickles your fancy.
I will admit that it started out as a bit of a fetish but now I feel different when I am dressed. I dont get turned on by it any more. I kind of feel safe & comfortable when I am dressed and like I am not the same me that screwed everything up.
After reading my story back for myself I came to realise something. I had been giving her gifts for years that were more aimed at my pleasure (in seeing her dressed & all sexy cat walk Victoria Secret Model kinda way) I wasnt actually doing something that was purely for her enjoyment even though I thought or told myself it was. There were other gifts though, not just the lingerie. I also surprised her with nice dinners and even a weekend away for her and a friend of hers. I think I may have already screwed things up long before the initial incident happened.
I can assure you that this is unfortunately very real and I have to live with it. Not really a fantasy or fun in any way.
Worst part for me now is that I am so used to lounging around the house dressed however I please and I really need to take in a boarder or flat mate to help share the rent and bills so I will have to hide away in my room when dressed up cause I am not really wanting to share that side of myself with anyone yet.
My story is almost the reverse of some of yours because I started off being openly encouraged to dress (even though it was just suposed to be to prove a point) then as my interests grew hers fell away. Now instead of being more open it looks like I will have to start hiding it away.
As for the lack of emotion in my post as someone mentioned. I kept taking bits out and removing the emotion cause I didnt want to tell a sob story. Just wanted to state the facts. If I had left in the emotion you would all probably just have finished reading it now. Its already too long as it is.

Anyway I should not be typing tonight, my spelling must be atrocious too. Its Friday night before a long weekend here (Australia Day on Monday) and I have had a few drinks too many and that usally spells didsaster for my typing skills.
I will end there fort now & resume when I am more capable of stringing 2 words together.
Thsnks to all those who were kind and encouraging.
Where is the spell check in Firefox.

Australia huh?

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My story is almost the reverse of some of yours

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OK, now I get it! ;)