In Conversation with Jenny Elwood

For the second installment of the ‘Conversing with the All Stars’ series, I have chosen a friend of mine from South Africa, Jenny Elwood.  Jenny is a married and  committed transgender person from a fairly traditional background. She has in many respects ‘broken the mould’ and is relatively out in the community.  We have been ‘out and about’ together (the ‘featured image’ is from our trip to the ballet in April 2015) and I really enjoy her take on life.  She has also worked to break down barriers and open society’s eyes to what our community is really like. I thought that her slightly different take on life may be of interest to you and I am happy to present my discussion with her to you.

Daniella Argento (DA): Hi Jenny, thanks for taking part in this interview. To start with, can you please tell us how do you identify?

Jenny Elwood (JE): I am a male to female crossdresser. I am also heterosexual.

DA: Do you not then consider yourself to be transgendered?

JE: As far as I know anyone who engages in some form of cross-(birth) gender expression is considered transgender (which is just an umbrella term) so yes, I suppose I do consider myself to be transgender.

DA: When did you start identifying this way and why?

JE: I have always considered myself a crossdresser, but only became aware of the broader umbrella term from a forum for transgender people. Being called a transvestite or even ‘tranny’ doesn’t  concern me but they are ugly, harsh words, so I prefer crossdresser.

DA: How and when did your crossdressing first manifest?

JE: I started dressing somewhere between the ages of four and five but mostly just underwear. Later I added shoes and dresses. I’ve only been doing the full transformation thing (with make-up and wig) for the last year and a half. I’d be lying if I tried convincing people that it’s not sexual for me personally, but there is a need for (non-sexual) female expression which I can’t fathom.  I’d say it’s about 50/50.

DA: I am interested in you being open about the sexual aspect of crossdressing. People seem to either think that crossdressing is entirely fetishistic or entirely non sexual. I believe that this is something of a false dichotomy and that reality is a bit more nuanced than this. Can you please explain how the sexual aspect manifests for you?  Would you mind giving my readers some insights here?

JE: Okay I will try and be as ‘straight’ about this as I can. Sometimes when I dress it is all sweet symphony. Everything just glides on, tucking goes seamlessly and everything packs into place effortlessly and there is no um … unsightly bulge because, well,  I am not turned on. This is normally when I plan on going out and only a full transformation will do. It is all about making the social transition from male to female. Getting into that female role you have been longing for, for quite some time and just being a woman, you know the type you pass by in the street. You will never meet her, you do not speak to her and you are certainly not about to have sex with her, but  you are her (at least briefly). The stress of getting it ‘right’ in a limited amount of time keeps you honest and you don’t delve into it too much subconsciously. I can only describe it as a deep-seated need to be feminine borne out of the pre-adolescent years before the onset of sexuality.

Around the teenage years a sexual component got added on that I’ve never really been able to shake. I do get sexually aroused by dressing. I especially enjoy the sensuality of the fabrics on my skin and the visual allure of seeing myself in the mirror or the feeling of prancing around in heels.  There are rarely any sexual  fantasies involved, it is mostly about the dressing and getting turned on by that. This is normally limited to those dress sessions when I do not plan on going out and thus do not need a full transformation, a couple of articles will do but I will admit that I have fantasized about being with my wife while dressed en femme.

I do not like to admit it, but whatever our (transgender community’s) misgivings about autogynaephelia are, it does seem to hold true in some cases, notably mine.

DA: You said you identify as heterosexual. Clearly that is an important distinction for you. Does it bother you that some people conflate sexuality and gender expression? How do you deal with this?

JE: I suppose it was (and still is) important to me being regarded heterosexual. I don’t really know why. Maybe it’s just my conservative (Afrikaner) upbringing kicking in. So yes, I also suppose conflating the two does bother me to a certain extent. Maybe I’ve been a bit over-eager sometimes to point this out to people because it seems as if most label you as ‘gay’ when you’re dressed. I have come to realise since that people will think what they want to think and in the end it really doesn’t matter whether they regard me as gay or not, all it does is come over a bit condescending to gay people. What matters is how I consider myself and I don’t see that changing.

DA: What labels do you use and how do you feel about these labels?

JE: ‘Labels’ are just words used to describe things, I’m not for or against it. How else would we communicate?

DA: Many male to female trans people prefer to go by their female name whenever possible. What is your preference?

JE: When I’m presenting female, I prefer to use my female name but if you know me otherwise as well, it really doesn’t matter.

DA: Is there a reason for this preference?

JE: If I look like a girl (in my own head at least!) it kinda’ makes sense to me that I should be called by a girl’s name.

DA: What would you say are the biggest challenges you face on a daily basis?

JE: Maintaining the relationship with my wife and with God to any acceptable degree in my daily life is hard. This thing takes a heavy toll (on both parties) when your wife is less supporting than you would like and believes that you can give crossdressing up and be joyous without it. I am hugely grateful that she sticks around in the belief that this will happen someday. The lack of dressing, and the ongoing negotiations about what is ‘fair’ in terms of dressing time, is never fun.

DA: Can you please explain a bit more about your relationship with your wife? What works, what does not work? Given a second chance, what would you have done differently? Can you give any advice to others who find themselves in this situation? How can the crossdresser make things better or worse in the relationship?

JE: I am probably the last person you should seek advice from on this point unfortunately. I am mostly devoid of diplomatic skills so seem to get everything wrong. Nothing seems to work at this stage and the threat of divorce is hanging palpably in the air.

What I would do differently is to have told her before we got married so that she had the chance to opt out. Women put a high price on honesty, they detest secrets between them and the person they love. It also seriously puts you on the back foot once they do find out (and eventually they will find out). I got caught red handed and as a result I ended up with a 7 year hiatus trying to please the woman I love. Eventually though it gets tough trying to live up to someone else’s standard and I it got to the point that I said I cannot live like this anymore.

The only way to make things better is to have proper communication. Otherwise you can feel the tension build in the house and eventually it will build to breaking point and you will have a big explosion, which is seriously counter-productive. Both parties need to get past their own emotions so things can be discussed in an open, honest and ‘safe’ environment . Both parties really need to communicate and try and understand where the other party is coming from. This means listening more than speaking unfortunately, and it means compromise from both sides. If there’s no compromise that is acceptable to both parties, there probably is no hope either.

DA: How many (and which) of these challenges are directly related to your being a crossdresser?

JE: We argue about a lot of things but if you look closer you’ll find that most are rooted in me being a crossdresser and the fallout from that. My wife despises not being told the full truth, which is fair, but telling the full truth often resulted in a big blowout, so I learned to just tell what was absolutely necessary. This has got a lot better (to her credit) which has led to me being more open about all of it.

DA: That sounds tricky. You are balancing the full truth with a need to know basis. Given the sometimes fluid nature of gender identity How are you sure that today’s full truth isn’t tomorrow’s overstatement (eg today I may feel that I want a boob job, but tomorrow I may be happy to be all man). How do you reconcile this?

JE: My wife has got to the point where she is starting to manage her emotions better and this has resulted in me being more willing to be upfront and not hide things. You are absolutely correct in referring to the fluid nature of being TG. A week ago I was more than willing to consider transitioning if she went through with her threat of divorce. I wanted boobs, bum, hips the full works! Now, a week later, I can’t think of anything more stupid to do and am happy to just be my (male) self. I love her and want to be with her and be a father to the kids, which is not to say that in a week’s time I will not be feeling the (TG) pinch again! I suppose that is why we don’t always tell the full truth of how we feel, because it does seem to shift so wildly.

DA: How ‘out’ are you to work, family and friends?

JE: My wife knows and some of her (trustworthy) friends know since she needed a confidant. My parents know, my father-in-law knows (and we still get along well!) My brother and his wife know and my favourite (female) cousin and her mom know. No one at work or any of my (male) friends know and it will stay that way if I can help it for the foreseeable future. My children  are too young to understand and we do not think that they need the confusion in their development.

DA: How has that process gone for you?

JE: Most took it well. Very little judgment (that I know of) really. The only one that ever speaks about it (with me) is my wife obviously, my cousin and my mom. The others ignore it and never a mention is made.

DA: What advice would you give people embarking on this side of the journey?

JE: I have no advice, everyone must follow their own path but I do know that genetic women absolutely hate secrets and the longer you keep it the bigger the fallout will be.

DA: What are your biggest fears as a crossdresser?

JE: That I will struggle to maintain the balance in future. The need to dress can sometimes become all consuming and then it clouds your thinking to the point where you say to yourself: ‘But if I transition…’

DA: What are your biggest hopes for yourself?

JE: I would still rather prefer to be ‘out’ of the transgender spectrum (and not having transitioned), but I want to be happy (even joyous) without and not depressed, grumpy and borderline suicidal like it was before.

DA: What are your biggest hopes for the transgender community?

JE: It is my fervent wish that nobody was transgender (but in the gender they preferred anyway), the price for all parties is just too high. Stone me if you wish.

DA: How easy is it to earn a living as a transgender person?

JE: I am not out so it is not an issue for me personally. Who is to say they would not work me out subtly if they knew I crossdressed. But as long as it has nothing to do with the quality of your levitra online work, they really have no reason unless they are perfect angels at home as well. If you are considering transition I am sure it is a whole new ball game though.

DA: What advice can you give my readers who may want to look as fabulous as you do?

JE: It takes a bit of time and practice, especially on the makeup side so be patient and do not try and equip yourself with everything overnight; it can be costly. Practice, look up some YouTube videos and get advice if you can.


DA: What do you do to get ready and how long does it take ?

JE: I like to dress fully and go out. I’ve done everything in 40 minutes but if you need to clean up properly and go the whole nine yards in terms of makeup, it has been known to take up to 2 and a half hours! To do a decent enough job about an hour and twenty minutes.

DA: Do you have a daily beauty regime?

JE: I put moisturizer on when I remember.

DA: How would you describe your style?

JE: Frumpy! I try to be elegant and not too showy. I’m not trying to pick men up here, so I prefer to tone it down a bit, let’s say to an office lady look I suppose. I want to look like a well-dressed (real) women.

DA: Where do you get your clothes and shoes?

JE: I buy from any shop that doesn’t kick me out when I ask to try stuff on. Ialways try on before I buy, I am not into wasting money. In my size you can only buy shoes online. I have a number of pairs from a very good online retailer .

DA: Have you ever had problems with getting clothing?

JE: Walk into any clothing shop and two thirds of the stock is female clothing. Easy. Get past your own fear, people don’t care as long as you hand over the money. You grow a thick skin about the odd snigger soon enough.

DA: Have you ever had any negative experiences when out shopping?

JE: Only one shop owner would not let me try something on, so I went to the next shop. That shop has since closed down. I am yet to encounter open animosity when out. I suppose I have just been lucky or people are scared of taking on an Amazon!

DA: Do you shop en femme or not?

JE: I only did it once. Shopping is the same but the outing is great!

DA: What works best for you?

JE: I would love to shop en femme more often but the opportunities are rare. Between work and family there really is very little opportunity to get even halfway dolled up before hitting the mall.

DA: Please give us some examples of some experiences you have had (whether good or bad)?

JE: Not too many either way. In the straight world very few people engage me when they put two and two together. Shop assistants are generally friendly once they overcome their initial bemusement. Sometimes people will ask to be photographed next to the dress wearing telephone pole, but mostly they just stare a bit and then move on. Some will ask some simple questions but luckily not too probing.

DA: What was your first time out like?

JE: I could not get in the car fast enough and through the McDonalds drive-thru and back in the room. My nerves were shot but I was hooked!

DA: That sounds like a fun experience. Please give us some more details.

JE: This was during a two week sabbatical from home and family life in February 2014. I grew ever more absent minded at home where I would just stare blankly into space. My wife grew weary of seeing me being there in the flesh only, so she kicked me out, literally. She told me to only come back in two weeks time: I was told to ‘go and be Jenny and only come back when she’s out of your system’. Well it doesn’t quite work that way, Jenny was born in those two weeks but unfortunately Jenny’s resolve to exist also grew during those two weeks. Initially I just dressed up in the privacy of my motel room but predictably the thought to leave those confines came and I acted upon it. I was still very ill equipped at the time and only had a cheap wig and some very basic make-up with dark glasses covering my eyes, but it did not stop me. Clothes were nothing to write home about, just a basic skirt and blouse with my only pair of shoes at the time: a black pair of 4? pumps and some water balloons to fill the bra.

I also made a day outing to the China Mall where my oversize (mail order) shoes kept falling of my feet. I capped it off by wearing my purple dress to Trouble (where I was welcomed and accepted) on the eve of my return home. I have grown a lot since then in making myself more presentable but nothing beats the nervous energy and ecstatic feelings you experience in those first few forays into the wider world.

DA: What is your favourite thing about living in South Africa? What would you change about South Africa? How would you rate South Africa for transgender people?

JE: South Africa is my home I don’t really know anything else. I would be hard pressed living in a tiny coop, like you have to do in Europe, so I suppose space is my favourite thing. I really dislike the useless  government. I look with (a little bit of) envy at The US and even Australia with their organized trans events and our total lack of anything organized. I’d still like to put together an annual T-ball but it seems there is not enough interest and cost is an issue.

DA: What are your personal dreams and aspirations? How does being a crossdresser help or hinder you?

JE: I hope I can be a better husband and father to my family. I also want to write that book I’ve always wanted to. I started but I am struggling a bit to word my ideas. I am often overwhelmed by this crossdressing thing so I suppose it’s more of a hindrance.

DA: You recently appeared in Huisgenoot magazine. What drove you to do that? Please tell us about the experience and the reaction you received.

JE: It came as a result of being consulted as a reference to an article on someone else. They contacted me afterwards asking if I would be interested in them doing an article on me and the circumstances I find myself in being married with kids and all. My wife agreed so we decided to do it. We met in a coffee shop (in drab) with the journalist and photographer and answered all their questions. That was about it, very low key. They give you no editorial rights so the story came out a bit crooked in the end and in hindsight I probably would not do it again. The only reaction was a lady from Port Elizabeth stating that women wear men’s clothing all the time so let me wear my frocks!

DA: You are a committed Christian. How does that reconcile with your crossdressing? What would your fellow churchgoers say if they knew?

JE: Here is an excerpt of a letter I wrote to a (female) friend who emigrated to Australia. It kind of tells of the struggle I face as a TG Christian on a daily basis:

“I don’t want to question God because He never makes mistakes but I do wonder why it sometimes has to be such a struggle. Why is there such a thing as transgenderism that can lead a person to the point where they are willing to sacrifice everything to try and find peace like Bruce/Caitlyn (sic) Jenner just did? The emphasis is on ‘try and find’ because it is exactly that. Despite how far you go, it will never fully satisfy, because you are trying to fill that little void that God left in all of us with the intention that we fill it with Him, with something temporary and of the Earth. Unless you fill it with God it will leave you hanging on for more and I experience that every day. But… but… there was a time I tried to. At least I think I did. I suppose, in hindsight maybe I did not put enough effort in, that somehow I fell short of the mark. Or maybe I tried too much in my own strength, thinking there was some salvation to be had in ‘deeds’.  As we all know there is none, only mercy. And I pray that God will be merciful when He looks upon me, because any and all strength I had during those 5/7 years that I quit dressing has evaporated. I stick a band-aid on now every 10 days to two weeks to help keep me sane. I have drifted away from God as a result and the semblance of a relationship I had with Him towards the end of the 7th year of ‘suppression’ has all but evaporated. I made some progress in Spiritual Growth at that time but it did not relieve the Gender dysphoria I experienced and it certainly did not help at all in relieving the severe depressive state I had fallen into. Every day was drudgery and I felt like Samson, just blindly stumbling round a grindstone every day of my life desperately hoping, praying that the next day would be better. Just trying to make it through the day in the hopeless belief that the next day would somehow provide some colour, only to find that the ‘need’ (to dress and express this unwanted side of me) had grown stronger. I never considered suicide, I suppose I don’t have the guts for it, but I went to bed many a night thinking it would be okay to not wake up in the morning. That I wouldn’t have to struggle through another day then.

I know that I should be lynched for this, but the honest truth is that I do not trust God to pull me out of transgenderism and make me happy as well. I just want to have peace in myself, is that so much to ask? I know that I never experienced true freedom though. That I never pursued relationship with God enough to really be free as opposed to the suppression I managed to do in those lost years. I don’t know how to get there. I wish somehow I can figure this out, so many have tried their level best to show me, but I keep falling short of the mark.  They tell me to spend time in The Word so I read it. The honest truth is I get bored with it. I read the Bible and get bored with the same stories I’ve heard since childhood. Sacrilege I know!”

The truth is that I remain a committed (but struggling) Christian. It is hard reconciling the two forces, seemingly pulling me in different directions, in my life. But if I were made to choose I would have to go with the saving Grace of my Lord and Saviour Jesus Christ.

Thanks for taking your time to answer the questions. I think this has given my readers an insight into your life, your beliefs and how to reconcile different aspects of one’s character in an ethical and respectful manner.

Here is the link for anyone who missed the first installment of Conversing with the All Stars

Jenny has a blog of her own which can be read here

A note on capitalisation and gender usage: Jenny is a committed Christian and feels that it id important to acknowledge God’s importance with capitals. She also refers to God with male pronouns throughout and she also believes that these pronouns need to be capitalised. It is this blog’s style guide that all pronouns (with the exception of ‘I’) should be lower case. However out of respect for Jenny and as the quote is from her writing I have kept the pronouns as capitals. I have no idea what any god’s gender is (I suspect supernatural beings do not have a gender) but again out of respect for Jenny’s sincere beliefs I have retained the male gender when speaking of God.