As the subject title says, who thinks about this sort of thing? By that, I mean, is it only trans people that think about wanting to change their gender and/or are tired of living in the gender role they were born into? I'm sure I've seen a topic about this before, but I'm just not in the mood right now to look for it (if such a topic does indeed exist). I've been thinking about transitioning for a few years now and have cross dressed for as long as I can remember. So by that description alone, does that make me a trans person, or some one whose just a bit "messed up"? There are other elements of things in my life that I find irritating and often make me feel socially awkward, such as wearing men's suits and going to weddings and other formal events. I came to the conclusion a few years ago that I just couldn't stand the sight of men's suits any more. Whether that's just because I've been out of work for a while and have had to go to loads of interviews that lead no where or I just generally dislike the look of them, I'm not 100% sure. Personally, I think it's the latter. I don't like the way they look on me, or their appearance in general. I do, however, really like the look of women's suits, especially those with skirts. There's just something nice about them.
I've also experienced an uncomfortable feeling when in a room full of men, and, in some way, can understand how a woman might feel in the same situation. I feel like the odd one out more times than not. I also think that has caused me to have a harder time looking for work because I don't know how I'd fit in with loads of other men, especially when they're talking about football and other "manly things". I know some women are into football, but the majority I've met, aren't. Either that, or they just don't like talking about the sport when there's loads of men around because men never talk about women's football. Personally, I love to see men and women in the same sports at the same time. Formula E had a couple of women in the first 2 seasons, but then they left. :(
So what do you think? Is it ONLY trans people that think about these sorts of things, or do "normal" (non trans) people think about it, too? I'd like to think it's the former, but with all the crazy thoughts that go through some people's heads these days, it could be either. ;)
Chris
IMHO, I feel that anyone can have these thoughts. For some, it's merely a deep sense of not fitting in. For others, it is the start of a transition. Though I dressed in private off and on much of my life, I NEVER considered myself Trans for the first 38 years of my life. I saw myself (wrongly) as all male yet had most of the thoughts that you mentioned. I only started to see myself as female in the past year and have only just set about transitioning I the last few months. So for a very, very long time I would have fit the mold of non-trans with the thoughts you mentioned FWIW.
It is said that cis people never wonder about their gender. Which means that anyone wondering is trans. I am always leery of using "all" and "none" because there usually are exceptions, but in general the rule seems to hold.
I never considered myself to be trans for most of my life. I wished I could be a girl, and I thought I was just weird. I cross-dressed for a while and thought I was a pervert. Along the way, I wondered (a lot) if I was trans, but I always managed to talk myself out of it. (How messed-up is that, that' I'd rather have been a pervert than trans?)
Eventually I saw the writing on the wall and realized that I'd been trans all along.
It sounds to me like you are probably somewhere on the trans spectrum. You don't have to call yourself that if you don't want to, but if you showed up at our support group, you'd be welcome.
Ask any cis person you know if they ever have or do think about their gender and I bet about 100% would say no...I have asked probably a dozen (family and a few friends)and they all say no, not until you decided to transition and told me, or something similar. Cis people just don't think about this stuff...
If you question your gender then you fit under the Trans umbrella. Where you fit under that umbrella is another story all together.
Liz
You all make very good valid points, thank you for your replies.
Having read some other topics on this forum, both recently and in the past, I think I have discovered something else that I think I can relate to. Some people have mentioned that they think that Testosterone has a negative affect on them, to which I often wonder that about myself. I've suffered from depression numerous times over the years, as I do right now, but it isn't usually always about outside causes, but instead, an internal feeling. I often get letters from my GP asking me to make appointments to go see my doctor, now I'm starting to think I really should consider doing so so that I might be able to explain some of these other feelings and hopefully get somewhere. About a year and a half ago, my doctor referred me to Charring Cross (I still haven't heard from them yet), as she didn't know enough about the particular subject, which is unfortunate, as she is quite a nice doctor. I only hope that I get to speak to another woman as nice as her, as I'd find it near on impossible to speak to a man about this.
Chris
I know the default state of trans-hood trends towards people not knowing they were trans for most of their life and often ending up as lesbians. But, I have always known I was trans or that I wanted to be biologically female. I thought I was and was kicked out of the girl's room in second grade. I got in a lot of trouble cause I kept at it. I eventually relented and made good, but the thoughts were always at the surface. Still, I didn't transition til 30, because I thought being a kinda femmy, weirdo guy was enough. I felt trans, though. Now I don't feel trans enough cause i'm too cis-het if that makes sense. It's kinda funny having been called a ->-bleeped-<- my whole life and now living completely femininely with a BF and a jiggly, sexy body but being considered a cis, heterosexual women.
But, I have heard people say they def would want to try out "being a girl" for a day or two and vice versa. Some people are adamant about not knowing, being someone else is too freaky I guess. I still feel like a freak and I have been on hormones for four years and have a long-term BF whom I love. I'm living in a dream. I never feel trans anymore, though. Now I just feel like a woman. I couldn't detransition if I wanted too. Sorry rambling...
Non-trans can think about it, but most apparently don't devote time and energy to it unless forced by circumstance.
In the same way I've never thought about what it would be like to have any number of medical conditions I've never had and couldn't pronounce the names of. . .
I could think about those but chances are I'm not going to, and not for any period of time unless one of them happens to me or people I care about.
Quote from: ElizabethK on February 20, 2017, 07:19:32 AM
Ask any cis person you know if they ever have or do think about their gender and I bet about 100% would say no...I have asked probably a dozen (family and a few friends)and they all say no, not until you decided to transition and told me, or something similar. Cis people just don't think about this stuff...
If you question your gender then you fit under the Trans umbrella. Where you fit under that umbrella is another story all together.
Liz
I've asked dozens of cis people if they ever thought about their gender, 100% thought I was nuts. The thought about thinking of their gender was totally foreign to them.
I ask a second question: (need to ask this first though, earlier in the conversation the better)
You are walking down a hallway and someone walks around a corner about 15 feet in front of you. What is the first thing you notice? I've had only one or two day gender. It really is the first thing everyone notices but they don't realize it.
I would suggest that many people think about culturally defined gender roles while few of us think, often obsessively, about our gender identity and expression without being part of the transgender world.
We know modern feminism railed against gender roles that defined women as property and men as our overlords for life.
Gender roles that place arbitrary and capricious limits on our ability, talents and aspirations are harmful to every boy who dreams of ballet or every girl who wants to be a mechanic as crude examples.
Anatomy is our physical vessel but need not dictate our dreams or destiny.
I'm sure the idea is not foreign to "cis-gendered" people. I think it's common to at least question your identity once in your life in some way or the other, to wonder what it would be like to be the opposite sex. At it's core as a general question, it's not much different then wondering what life would be like if you made different choices. "What if I was more athletic as a kid?" "What if I had superpowers?" "What if I didn't do this or that" etc. It's easy to wonder how different life would be if you were born differently then you were, and I don't believe that nobody has done that except for members of our general community. The difference is that when WE thought of that, we realized that the idea wasn't as silly as it sounds to somebody else. We realize that it actually is an idea that makes sense and might even answer many other questions that we ask ourselves day to day about our lives.
Quote from: CrystalMatthews0426 on February 20, 2017, 12:49:50 PM
I'm sure the idea is not foreign to "cis-gendered" people. I think it's common to at least question your identity once in your life in some way or the other, to wonder what it would be like to be the opposite sex. At it's core as a general question, it's not much different then wondering what life would be like if you made different choices. "What if I was more athletic as a kid?" "What if I had superpowers?" "What if I didn't do this or that" etc. It's easy to wonder how different life would be if you were born differently then you were, and I don't believe that nobody has done that except for members of our general community. The difference is that when WE thought of that, we realized that the idea wasn't as silly as it sounds to somebody else. We realize that it actually is an idea that makes sense and might even answer many other questions that we ask ourselves day to day about our lives.
Good points and we can simply take a look at all the movies/media where the plot device is some magical happenstance that turns one into the opposite sex temporarily. They are notably comedies because isn't that just so impossibly hilarious? Not so much to us, perhaps, as the butt of the joke?
Quote from: Tessa James on February 20, 2017, 12:59:07 PM
Good points and we can simply take a look at all the movies/media where the plot device is some magical happenstance that turns one into the opposite sex temporarily. They are notably comedies because isn't that just so impossibly hilarious? Not so much to us, perhaps, as the butt of the joke?
One of my favorite variants of this was the 1991 Ellen Barkin movie Switch. For those who are unfamiliar, it is about a ladies man (for lack of a better term) who likes to sleep around and be pretty much a jerk. His three girlfriends conspire to murder him, and God can't decide whether to let him into Heaven or not, so makes him a deal that he can go back to earth, but he has to find just one female who doesn't hate him. The catch is that he is sent back as a beautiful woman. It was a rather cheesy film, but kind of funny. I remember watching it on HBO when I was much younger and thinking how cool it would be to just randomly wake up one day as a woman. I think that might have actually been the beginning of this journey.
Something that distinguishes cis thought patterns from trans though patterns is that a cis person might think:
"I wonder if I'm trans."
"No I don't think so."
"Okay."
The trans version of the same thought is:
"I wonder if I'm trans."
"No I don't think so."
"I wonder if I'm trans."
"Hell, no."
"I wonder if I'm trans."
"No way."
"I wonder if I'm trans."
"No I don't think so."
...
(until)
"Hmm, maybe I am."
If the answer were truly no, we wouldn't keep asking the question.
I only think about my gender because I'm constantly aware how wrong its been my whole life. I wish it wasn't an issue and just let me live in peace.
Leaving the house....check
Car keys.................check
Money....................check
Gender Identity.....check
Cis people would tend to skip the last check, as would most of those who have fully transitioned and living in their desired role.
I hear many people saying "I think they would..."
Here is a challenge...Go and Ask...you are going to be surprised!
I used to "think" of course they thought about this...I was wrong, very wrong...ask 5 average cis people and see how you go.
Liz
I remember way back in the deep dark recesses of my memory Harry Benjamin did a survey/study and found a lot/most people have thoughts of "What would life be like on the other side?" Just a passing thought or random thought experiments.
When it gets more often then hardly ever.... I'll toss you into the TG Universe. Without a big "You are Here" arrow, it is up to you to figure out where in that vast universe between cis-female and cis-male you are currently orbiting
Quote from: Shy on February 20, 2017, 02:54:59 PM
Leaving the house....check
Car keys.................check
Money....................check
Gender Identity.....check
Cis people would tend to skip the last check, as would most of those who have fully transitioned and living in their desired role.
Your last check was Funny to me. This morning before leaving for work, I stopped to make sure I didn't screw up and put on something feminine or jewelry or eyeshadow... By mistake without thinking. Less than two weeks before the check flips the other way!
Quote from: Shy on February 20, 2017, 02:54:59 PM
Leaving the house....check
Car keys.................check
Money....................check
Gender Identity.....check
Cis people would tend to skip the last check, as would most of those who have fully transitioned and living in their desired role.
:D I've gotta start doing this! I keep going out wearing my ladies' watch. It hasn't caused problems yet, but once it's warm enough to wear short sleeved shirts it will. I have to stop and do a gender check before using a public washroom!
Quote from: Denise on February 21, 2017, 07:10:35 AM
Your last check was Funny to me. This morning before leaving for work, I stopped to make sure I didn't screw up and put on something feminine or jewelry or eyeshadow... By mistake without thinking. Less than two weeks before the check flips the other way!
Ha, yes I remember the days forgetting I had makeup on before walking out the door. Now I refuse to leave the house without it. It really is funny how quickly priorities change.
Two weeks and counting, you must be excited. Just be yourself girl, you'll be awesome!
I never think about gender roles. I never did. I'm just me.
I've just always known I was supposed to be female.
My main preoccupation with being trans in how I look. All my dysphoria is centered around my face. [emoji53]
Sent from my iPhone using Tapatalk
Quote from: KathyLauren on February 20, 2017, 01:06:36 PM
Something that distinguishes cis thought patterns from trans though patterns is that a cis person might think:
"I wonder if I'm trans."
"No I don't think so."
"Okay."
The trans version of the same thought is:
"I wonder if I'm trans."
"No I don't think so."
"I wonder if I'm trans."
"Hell, no."
"I wonder if I'm trans."
"No way."
"I wonder if I'm trans."
"No I don't think so."
...
(until)
"Hmm, maybe I am."
If the answer were truly no, we wouldn't keep asking the question.
I absolutely love this example! Its 100% true. When i was questioning my self if i was trans or not, i came across this video on youtube, and the psychiatrist was saying "if youre questioning yourself if youre trans or not, youre most likely trans because cis gendered people dont feel the need to question their gender identity.".
Yep I think plenty of non trans people think about these things. Particularly women and men who can't fit into the macho expectations of society. Ive come onto this forum to just experimenting with the idea of trans as werid as that sounds, becahse I've always wanted to be a guy and hated my female gender role... But that doesn't really have much to do with my body or wanting to transition. So I find it likely that i am just one of those cis people who thinks about these things as you said. I don't have much of a problem with being physicalily female. If you arent trans but you just think about these these things I doesnt make you weird at all. For me of course it's quite easy to go about life dressed completely like a man and doing only male hobbies without sparking much hate. Some confusion, some getting looked down on by real girls, some homophobia, but nothing I can't handle as an adult. And only the occasional person actually thinking I'm trans. i imagine wearing a dress as a biologically male person and not committing fully to a trans identity is a lot harder.
Quote from: AshleyUSMC on February 22, 2017, 05:06:40 AM
I absolutely love this example! Its 100% true. When i was questioning my self if i was trans or not, i came across this video on youtube, and the psychiatrist was saying "if youre questioning yourself if youre trans or not, youre most likely trans because cis gendered people dont feel the need to question their gender identity.".
Yup! I've seen this one in action. Questioning, and denying, questioning, and denying again, the whole "I'm not trans, I just want to try this out" argument. I've seen how it ends, too. ;)
Most folks just never question their gender identity, or realize it could possibly be different from their assigned gender or physicality. That's part of why most people have trouble understanding transgender people. They are faced with us, an "outside context problem" with which they have no experience to extrapolate empathy from, and are confused by our existance.
I strongly suspect that anyone who questions their own gender identity at any time has a transgender component to their makeup.
Who thinks about this sort of thing? Transgender people.
I think about it frequently. Let me tell you about myself. Back when I was a kid, I used to browse through the lingerie section of department store catalogues. I also used to "borrow" my sister's tights and stocking/garter belts. As much as I wanted to wear those things, I was terrified someone would find out. After I reached my late teens, I started buying pantyhose for myself. Later on, I got into full cross dressing for going to fetish parties that happened twice a month. While I have stopped going to those parties, I still wear bra, pantyhose and nail polish every day. I have also long dreamed of having a sex change operation. The woman who helped me with my cross dressing asked if I had considered a sex change. I told her I had many, many times, but thought it was too extreme for me. I also told her, if I had the operation, I'd have to be a lesbian, as I prefer women. At her suggestion, I also had sex with men and enjoyed it, but I definitely prefer women. I have also considered castration and nullification, as I am not 100% happy with being male. So, I am clearly transgender to some degree. I've often wished that one could choose to be male or female when they get up in the morning and have the body to match. :laugh:
Intermittently, for years, I would go to bed and pray to wake up a woman or go to "magical" people/websites and ask them to cast a spell to transform me into a woman. Never worked, then I would bury the thought, at least for a while. Usually when life was going good, but eventually the old thoughts would creep back in and then I would sabotage myself somehow and the cycle would start over. I fought it for decades, but I never thought then that this was what I should do, and even now have my doubts, despite not waking up in the mornings with the "damn I woke up" thought first thing. I couldn't admit it, not even to myself, nor my first two psychiatrists. I really don't know if I can call them that, the first was for one visit when I was a child, and the second was while in the service, and even thought I didn't feel right in my body I told him that I did, and only saw him a coupe times. I might have saved myself a lot of pain had I been truthful to him all those years ago.
@Aresia
Have you done anything to express your feminine side? As I mentioned, I was into cross dressing for a few years and still wear "feminine" items as part of my every day attire. I simply consider a bra and pantyhose to be my standard, daily wear.
As I mentioned, when I was a kid I was terrified someone would find out I wanted to wear lingerie. This was back in the '60s, when such things were simply not mentioned, except in a derogatory manner. These days, kids have so much more freedom in this respect, with parents and professionals helping them to determine which way to go, with dressing and eventually surgery. I recently watched a show on the National Geographic channel about transgender people and wish these things had been available to me when I was young. Incidentally, back then, I didn't want to be a girl. I just wanted to wear stockings, tights etc. It wasn't until my late teens that I started thinking about sex change etc.. What triggered that was a newspaper article I had read, about a couple where the husband had the surgery and became the wife's "sister". Until then, I didn't know such a thing was possible.
Quote from: JamesK on February 26, 2017, 07:43:17 AM
This was back in the '60s, when such things were simply not mentioned, except in a derogatory manner.
The information was out there but the problem was it was very difficult to dig up. In 1963 I knew about John Hopkins and when I started college in 1970 I located every book on transsexualism in the ASU Library. It took a fixation to read anything I could get my hands on for a trace of information but I had one. Now days, it just takes a couple of searches with Google and you can come up with months of reading.
Those things were no doubt covered in a clinical environment, but not in everyday life. Even in a clinical environment, I recall reading about how some were forced into treatment to be "cured".
Yes, a member of our group received shock therapy for extreme depression but Christine Jorgensen was making the talk shows. Much of what I learned early on was in the news paper and magazines where the process of transitioning was explained. About the most off the wall thing I came across was Myra Breckinridge. I started therapy in 1973 and curing me was never mentioned. The therapist didn't have much knowledge about how to treat me but that was because it was all so new. Our group around 1980 had a nerd moment and we estimated the transsexual population to be around 60,000 based off the number of doctors preforming surgery and a guesstimate as to how many had been and were being treated.
Quote from: Shy on February 21, 2017, 10:02:44 AM
Two weeks and counting, you must be excited. Just be yourself girl, you'll be awesome!
Excited is not the emotion I'm feeling. It's relief with a ton of nervousness on the side.
For acquaintances that say congratulations, I smile and say thanks. For real friends I say, "well I didn't hit the lottery, but thanks."
I never thought about it, until I was told I *had* to think about it because the way I acted, dressed, or moved was 'wrong' and 'people were going to judge me.' Suddenly my life became less about being myself, and mostly an awkward juggling act of 'if I do this like this, will my parents be disappointed in me and I'll be considered a freak? Are people going to hurt me?'
I think absolutely everyone thinks about this stuff, otherwise there wouldn't be such rigid societal expectations as to what would be regarded as 'homo' or 'weird' or 'perverse.' Parents wouldn't feel the compulsion to 'enforce' them on their children from a young age. Boys wear blue, girls wear pink. Girls get dolls, boys play with trucks. Any deviation from this must be weeded out and punished, and if they allow it, what does that mean about THEM as a parent or guardian?
OR even for normal hetero types, how long do you look in the change room before someone thinks you're weird? Do you look at all? If you don't look, do people think you're avoiding it because you're insecure and queer?
Whats the proper positioning in the urinals so no one thinks you're a sicko? (There are even books about this, as there actually IS a correct answer supposedly.)
TL;DR everyone thinks about it, whether openly or not, while they may or may not feel discomfort with it as we do.
Quote from: Angela Drakken on February 26, 2017, 12:01:29 PM
I never thought about it, until I was told I *had* to think about it because the way I acted, dressed, or moved was 'wrong' and 'people were going to judge me.' Suddenly my life became less about being myself, and mostly an awkward juggling act of 'if I do this like this, will my parents be disappointed in me and I'll be considered a freak? Are people going to hurt me?'
Angela, I really appreciate that you brought up the phenomenon of gender policing! I totally relate to this description.
Even when I was very young, my gender was policed through restricting options for clothing and play activities; later on, my peers tried to re-enforce my (already forced) masculinity by trying to label me a "->-bleeped-<-." And then, having outmaneuvered the ->-bleeped-<--haters for a while by claiming gay identity, I found that my femininity, cross-dressing, and general unabashed flaminess was policed by many "mainstream" (read: privileged) gays who were attempting to promote a normative gay identity in order to shore up their own feelings that they really were "man enough." (FWIW, I agree that being gay doesn't mean you're not manly, but it's not necessary to reject femmes, flamers, gender non-conforming and trans people in order to do so.)
Now, I am exploring trans identity, and I see that many folks are interested in policing others' genders in the service of building up their own identities and appearances (e.g., accusing people of " ->-bleeped-<-" or making other "you're not trans enough" type of claims). Although I would say I have encountered very little of this here at Susan's--a tribute to this site and the great community here. I can't help but think that the definition of transgender that this site promotes, which has room for those who identify in many different ways (not excluding cross-dressers, or nonbinary people, etc.), has contributed to the welcoming and nonjudgmental atmosphere.
Quote from: JamesK on February 26, 2017, 07:43:17 AM
@Aresia
Have you done anything to express your feminine side? As I mentioned, I was into cross dressing for a few years and still wear "feminine" items as part of my every day attire. I simply consider a bra and pantyhose to be my standard, daily wear.
To be honest...no, I never did any real crossdressing. I did put on my mothers Heels a few times, and got in trouble for it. I was a bit of a coward, so I wouldn't do anything that would get me in trouble if caught. I did look at the magazines/sales adds at the clothing, but it was close enough to puberty that nothing was said about it, I guess it's normal for guys to look? That's probably why I'm still so afraid to tell my family. I did put on women's lingerie a few times, but only with a select few women prior to....relations. My wife has been real helpful in increasing my courage, and will help with my transition, but she is not happy with it, but still loves me.
Quote from: p on February 26, 2017, 01:49:43 PM
Now, I am exploring trans identity, and I see that many folks are interested in policing others' genders in the service of building up their own identities and appearances (e.g., accusing people of " ->-bleeped-<-" or making other "you're not trans enough" type of claims). Although I would say I have encountered very little of this here at Susan's--a tribute to this site and the great community here. I can't help but think that the definition of transgender that this site promotes, which has room for those who identify in many different ways (not excluding cross-dressers, or nonbinary people, etc.), has contributed to the welcoming and nonjudgmental atmosphere.
If you view TOS 9 (https://www.susans.org/forums/index.php/topic,2.0.html) and Standard Terms (https://www.susans.org/forums/index.php/topic,54369.0.html) you will discover the site policy on these matters. As staff, I have strict orders to enforce these rules and if I don't, somebody else will. My powers include placing ban should I encounter somebody well out of bounds. If you find an issue like this in the site, hit the report to moderator button to the right of the post and a staff member
WILL handle the issue. These are the standards that Susan has set for the site from day one and violations aren't permitted.
@Artesia
It's nice that your wife supports you. I don't think my ex would have. While she liked to see me in stockings or pantyhose, she made it clear that's as far as I could go. You can start with small things. For example, go for a manicure and get some coloured polish. It's easy to do and easy to take off when you want. You might also try wearing pantyhose with shorts, gender neutral clothes etc.. It's often the first step that's hardest. Once that's out of the way, it becomes easier as you go. I'd expect you'd have to dress fully as a woman, as part of your transition, so the sooner you start, the better. I'm sure your wife could help.
Another thing, find a shop where men are welcome and see what you can find. I've been fortunate over the years in that I found several shops where I could try on things to buy. Most recently, I've been buying my bras from a bra shop that's happy to have men as customers. In fact, being comfortable with fitting men is a requirement for anyone who wants to work there. Again, your wife may be able to help.
I assume your wife's issues are more with losing a husband, than gaining a girlfriend/wife. I have long been interested in what happens with couples. In some cases it works out well and others it doesn't.
Quote from: Dena on February 26, 2017, 02:11:11 PM
If you view TOS 9 (https://www.susans.org/forums/index.php/topic,2.0.html) and Standard Terms (https://www.susans.org/forums/index.php/topic,54369.0.html) you will discover the site policy on these matters. As staff, I have strict orders to enforce these rules and if I don't, somebody else will. My powers include placing ban should I encounter somebody well out of bounds. If you find an issue like this in the site, hit the report to moderator button to the right of the post and a staff member WILL handle the issue. These are the standards that Susan has set for the site from day one and violations aren't permitted.
I am definitely aware of the TOS and Standard Terms--I believe these policies and definitions are part of why Susan's Place feels so supportive, especially to me as someone at the early stages of questioning my gender. Thanks so much for your important work, Dena!
Quoteare part of why Susan's Place feels so supportive, especially to me as someone at the early stages of questioning my gender
That's why I'm here too. I've had these feelings for many years, but never discussed them with anyone, other than a woman who helped me with cross dressing several (25?) years ago. It's nice to have a place where I we can discuss these things with like minded people. I just want to explore what my options are, including experiences and opinions of others here. I just have no desire to die as an intact male.
I have long known I was trans, but I'm now thinking more and more about doing something about it.
Quote from: JamesK on February 26, 2017, 02:22:11 PM
@Artesia
It's nice that your wife supports you. I don't think my ex would have. While she liked to see me in stockings or pantyhose, she made it clear that's as far as I could go. You can start with small things. For example, go for a manicure and get some coloured polish. It's easy to do and easy to take off when you want. You might also try wearing pantyhose with shorts, gender neutral clothes etc.. It's often the first step that's hardest. Once that's out of the way, it becomes easier as you go. I'd expect you'd have to dress fully as a woman, as part of your transition, so the sooner you start, the better. I'm sure your wife could help.
Another thing, find a shop where men are welcome and see what you can find. I've been fortunate over the years in that I found several shops where I could try on things to buy. Most recently, I've been buying my bras from a bra shop that's happy to have men as customers. In fact, being comfortable with fitting men is a requirement for anyone who wants to work there. Again, your wife may be able to help.
I assume your wife's issues are more with losing a husband, than gaining a girlfriend/wife. I have long been interested in what happens with couples. In some cases it works out well and others it doesn't.
Oh, I thought you meant in the past, sorry. I have always dressed in what I now know was a gender neutral style, jeans and t-shirt. Ties always made me feel like I was choking, even when I was younger. A choker necklace doesn't have that effect. I wear a skirt and women's shirts, at home, on Saturday's and/or Sunday's every week now. I wear a bra and women's underwear any chance I get, but never at work. My Wife doesn't usually notice I'm wearing them until I undress at the end of the day, my Therapist and Doctors say haven't noticed either. I'm thinking of wearing them at work soonish, going down the stairs hurts my fledgling boobs from the bouncing. I wear baggy shirts and am a bit overweight so nobody has noticed so far, at least that they have said. I have a couple pairs of High Heel Shoes, one is a 6" sandal type heel, which is now a hair to big(sad face) the other is a 4.5" heel. I was able to walk in those, with no problems, from the moment I put them on, my first pair was the 6" heel ones. Sorry, I love High Heel Shoes, and I have my eye on a pair of heeled boots, but I can't find them in a size 12 wide or a possibly a touch larger. My sandal heels are size 13 the other pair is a 12 wide, so size 12 is where I look to start but know that it could be larger or smaller depending on he company.