How do I tell her?

[Some1pleasehogtapeme]

Good morning/afternoon/evening to all

So approximately 20 years ago I was at my grandma's house (11 years old at the time) when my gran opened her closet. I was curious as to what the shoes were that had a stiletto heel at the back of the shoe. Ever since that day that I have been hooked on heels!

I promised myself I'd never stop wearing heels when my gran passed away as it was something that would remind me of her and all the amazing times we had together.

Anyway long story short, it's now 2024 and I've never actually told my mother that I wear high heels in secret. I am tempted to just put the shoes on and start walking around the house with them as I've kept this a secret for a very long time now. Is this the wrong way to go about it? Do I discuss it with her first and tell her how the addiction came about? I also have a leather dress and leather skirt. Her eyes might pop out if she sees me wearing that.

Please give me your advice or opinions ASAP! I can't live like this anymore. It is really difficult wear my heels behind a locked door without my mum knowing.

[Shannon SteelSlave]

1st, would leave out the part about how this started, just make up a story that it happened elsewhere.
Without knowing what the stakes are, or what you hope to accomplish by this, I might say, leave a pair of heels somewhere she will see them, "accidentally" misplacing them there. This might allow her to gather the best mood to approach you, instead of you guessing the best time and place to have the talk.
Also, try not to be home when you plan for her to make the discovery. This will give her some time, knowing you are not looking for them.

[Riddle]

This is a rather difficult question. Surprising her in the most dramatic and unexpected way possible is most likely to seriously confuse her, making the situation most awkward, and making the whole topic start under the most negative circumstances possible. Perhaps a gentle approach would be more appropriate and effective.

On the other hand, I have a question that I ask myself before sharing personal information with family members: will this information improve my relationship or will it make the relationship have an awkward element. My sexual activities (solo, self-bondage, estim, etc.) are definitely in the “Do NOT Share” category. Some of my other private details have been shared to the minimum extent required. That sharing demonstrated a level of trust and improved the relationship.

So, high heels and leather female clothing really requires careful consideration, planning, and a delicate touch to start the discussion with your mother. I am estimating your age to be about 30 and believe that your mother shares a dwelling with you. Given that, I am in agreement that your mother currently has the need to know that you have shoes that make a distinctive sound that you would like to wear more often without having to be concerned about your mother’s perception of it. Start there. I would leave the Grandmother details out of the conversation for now at least. After that, try to determine how well that much information was received and then start considering the next step.

Another thing to note, mothers are curious and do not always make their children aware of some information they know. We are not aware of how much information your mother already knows. Please keep this in mind and do not get upset about whatever information she already gathered.

I wish you the best of luck with this and hope this process improves your relationship with your mother. May it grant you the freedom to live your life as you need to live it.

[Riddle]

As for the explanation why, I don’t believe that there is any valid explanation or any requirement for an explanation. It just is! For me, my clothes only feel nice when made of cotton with a relaxed fit. Dress shirts never felt good and ties are currently on my hard limits list. Some men love wearing suits. I don’t.

Why must my clothes be relaxed fit when I require my bondage to be tight, restricting, and inescapable? It just is.

[Shannon SteelSlave]

You may expect her to have questions. She might want to know if you are homosexual. She might want to know if you plan to go out in public dressed. She might want to know if you plan to pursue a traditional relationship. I certainly hope you are just being paranoid and in the end, I hope all of this worry was for nothing.

[Some1pleasehogtapeme]

Without knowing what the stakes are, or what you hope to accomplish by this, I might say, leave a pair of heels somewhere she will see them, "accidentally" misplacing them there. This might allow her to gather the best mood to approach you, instead of you guessing the best time and place to have the talk.
Also, try not to be home when you plan for her to make the discovery. This will give her some time, knowing you are not looking for them.

To be honest, and I completely forgot to about it, many years ago I had a pair of stiletto boots that I had laying at the back of the cupboard which my mum discovered when she was clearing out a storage closet in my room. When she saw them she asked me what they were doing there. I pretended to not know what she was talking about. Also, when she was younger she used to own a pair of quite smart heels that she would wear to smart occasions but I was actually the one who wore them I always wonder how she never noticed the wear and tear on the shoes as I probably walked around the house in them just about everyday back when I was in primary school (I often got home earlier than my mum from school). I always wondered if she secretly knew that I was wearing them as they couldn't just wear and tear by themselves. But then again I ask myself as to why she has never approached me about it. There was also another occasion where I tried to speaking to a young lady who was the daughter of one of my mum's friends on Facebook and she immediately forwarded the message straight to my mum and I got a mouthful from my mum as soon as she found out. There has been quite a few occasions she must have suspected something. Another time when I was very young (probably around the age of 6 or 7, my mum caught me wearing her kitten heels and coat in her room. She even laughed at me and told me she would tell her friends.

Regarding "accidently" misplacing them for her to find out, what if she never approaches me? I wouldn't even know which of 3 pairs of high heels to place in my room with the door open for her to find out. What if I come home and she is raging mad? What if she sarcastically tells me that I left my female shoes out? That will leave me in a world of emotional pain

On the other hand, she might be interested as to why I own the shoes? She might think I'm gay? Which I most certainly am not! What if she tells me to get rid of them? No way I'm getting rid of items that make me feel good about myself.

It's just all very very confusing to me. Perhaps I should just keep the secret to myself even though I am itching to confess the literal skeleton in my closet

[Some1pleasehogtapeme]

You may expect her to have questions. She might want to know if you are homosexual. She might want to know if you plan to go out in public dressed. She might want to know if you plan to pursue a traditional relationship. I certainly hope you are just being paranoid and in the end, I hope all of this worry was for nothing.

The whole reason why I do not persue a relationship with a female is because I am too scared if they find out about my secret and if I had to tell them, they might not like it and would be done with me before the relationship even got started. I am pretty sure the majority of females these days would not want a crossdresser walking around their house in heels. Unless I am very very wrong.

Certainly would not wear any female clothing in public. Ever!

[Shannon SteelSlave]

This is what I thought you were saying : You want to be able to achieve an understanding with your mother that you want to be able to wear your heels outside of your room to walk about the house without ridicule.
I do not believe a desire to wear women's clothing makes you gay, but some people are very cut and dry when it comes to their beliefs.
I am not trying to put ideas in your head, just to help prepare you. This morning, you made it sound like you wanted emergency advice, quickly, as you were about to just literally walk out of your room.
So she caught you before? That can be a good thing, past precedence. I was made to believe you would have no idea of her reaction.

[Shannon SteelSlave]

You may expect her to have questions. She might want to know if you are homosexual. She might want to know if you plan to go out in public dressed. She might want to know if you plan to pursue a traditional relationship. I certainly hope you are just being paranoid and in the end, I hope all of this worry was for nothing.

The whole reason why I do not persue a relationship with a female is because I am too scared if they find out about my secret and if I had to tell them, they might not like it and would be done with me before the relationship even got started. I am pretty sure the majority of females these days would not want a crossdresser walking around their house in heels. Unless I am very very wrong.

Certainly would not wear any female clothing in public. Ever!

Like I said, I am not the one asking the questions. You are not trying to convince me. I just threw out some ideas, based on knowing nothing about your mother or your relationship with her.
Based on what you are saying now, my advice is to just sit down with her and talk to her. Answer her questions, then offer any explanation you feel is necessary. Then hopefully, when you are walking about in heels, there will be no surprise, mocking or judgement.

[Some1pleasehogtapeme]

So, high heels and leather female clothing really requires careful consideration, planning, and a delicate touch to start the discussion with your mother. I am estimating your age to be about 30 and believe that your mother shares a dwelling with you. Given that, I am in agreement that your mother currently has the need to know that you have shoes that make a distinctive sound that you would like to wear more often without having to be concerned about your mother’s perception of it.

I am 31 in 2 days from now so you're just about spot on!

So all I really want to do is wear my block heels around the house. That's all. Currently I can only wear my heels in my room on a carpet floor and is barely even 3 or 4 meters. The stilettos might make it look more weird but the block heels I own are considered much less formal in my opinion.

I think the leather skirt and dress I will probably get very awkward comments or possibly sarcastic comments relating to femininity

[lj]

At the age of 31 the OP is entitled to have whatever kinks he has. His mother is entitled to have hers (or not have any). However, the parent-child relationship rarely includes discussions on sexuality or kink in either direction. This is further complicated by the roles in the house they share - does the OP own a share in the house, play an active part in maintaining the house, as this to some extent governs the consequences of a major fall-out. We also have no idea of how relaxed the mother is regarding sexuality nor her experience.

The OP also confesses to not having pursued any relationships (mentioning girls but that isn't important) and therefore has not had any sexual experience other than in his own mind and cross-dressing solo play. This is not intended to belittle him, just providing a background of experience or the lack of it.

With the lack of experience, the focus is very strongly on cross-dressing, albeit focussed on high heels, and this has become a major stress, made worse by the feeling that his circumstances prevent relief from the stress by "coming out", which may or may not go down well with his mother, adding to the uncertainty and stress. This obviously cannot go on.

The simplest route is to have a discussion with his mother, explain he is a cross-dresser in private, explaining the main kink is a fetish for high heels, and see what reaction follows. The worst case is "get out of my house and never come back" (which is why I wondered about the roles in the house) If the OP has a career and is not financially dependent on his mother, this provides a solution of sorts, he moves out, finds his own place and does what he wants. At the other end of the spectrum, his mother will say that's absolutely fine. In between are a range of conditions, for example "absolutely fine but not in my presence" "anywhere except in the house when I am home" and so on. From experience I would say the average person will not understand cross-dressing and will make all sorts of assumptions, including "you must be gay". A parent is more likely to take that sort of approach, unless they are very broad-minded, as to say "that's fine, dear" could imply they also have kinks and feel they should not admit as such to their child.

Another, and probably better, alternative is for the OP to look for play-parties where he can indulge his kink fully. Here in the UK almost every town has a Munch, which some here will know that Munches are gatherings of fellow kinksters, often in a pub, bar or cafe, usually totally vanilla, just a meeting of like minds. That can lead to friendships, invitations etc and introductions to play parties and events. Or you can search for kink events on the web, contact the organisers for information. I got into the kink world (face-to-face version) via a now defunct website, found the local Munch and went along (very nervous) to be met by a very friendly bunch of people and pointed towards a play-party, which I went to suitably cross-dressed and was made very welcome. As it happens, I was also interested in the BDSM side of kink, and the cross-dressing became a minor part of play-parties and much less of a sexual turn-on. I mention this because the OP might find the cross-dressing becomes less important - or with the right person, part of their relationship. I know several couples who have cross-dressing as a permanent part of their relationship.

I know that entering the kink world seems like a major step, but bear in mind everyone reading this has taken the step of accepting they are kinky, or at least interested. The next steps are no more difficult. I would strongly recommend the OP takes my suggested alternative rather than risk a confrontational discussion. Please, oh please do NOT "leave something for her to find" - that simply gives his mother the opportunity to go through a whole series of alternatives and cause significant stress for her, which will not put her in a mental state to calmly discuss this topic. If the "coming out" discussion route is chosen, take it calmly and explain.

[Some1pleasehogtapeme]

I have spoken to my mum and she understands. Thankfully it went a lot better than I thought it would.

[Kinbaku]

I have spoken to my mum and she understands. Thankfully it went a lot better than I thought it would.

Nice to hear.
Good luck with further discovering your needs.

[lj]

that's great news.

I suspect she may have picked up on your kink from the previous "escapes" (the boots, etc) but not wanted to interfere - difficult cnversations go both ways !

good luck with your kinky future

[Riddle]

Excellent news!