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One Giant Leap

A first hand account of the first time!

By Amanda J.

I recently drove to a supermarket around six miles from where I live.  After parking the car, I went in, had a quick look round and seeing that they didn’t have what I needed, left the store and drove back home.  I can already hear the cries of ‘so what, I do that every week?’ but please stick with me.

I contribute to Kandi’s Land for two reasons.  The first is because I find writing the posts to be a great way of talking about this side of me in the absence of people to confide with in the real world.  For a closeted CDer, it provides much needed contact with others and deals with much of the isolation I would otherwise feel.  The second reason is because I find my co-contributors inspirational and it’s a ‘club’ I enjoy being a part of.

Kandi is just a force of nature and, even though I could never do even a tenth of what she does (even in my ‘drab’ life) she just proves that life is there to be lived and acceptance is there for the taking.  Jocelyn & Tina prove that lack of opportunity does not mean that when that opportunity comes, we can’t grab it with both hands and enjoy every second.  Lisa’s posts are often like a ‘How to be a CDer’ encyclopedia but, like posts from Dee, Gwen, Trish and all of the other contributors, amazing accounts of acceptance in the outside world.

And then there’s me.  Stuck in the closet looking wistfully at the others’ adventures with more than a tinge of envy.  And if you, dear reader, strongly identify with that last sentence, read on because things are going to start getting interesting.  Which brings me back to my trip to the supermarket.  Over a six decade lifetime, I must have visited supermarkets thousands of times but I can say with 100% certainty that that particular trip was the first I’ve ever made wearing a skirt, high heels and full makeup!  In fact, with the exception of a couple of short walks in my neighbourhood, it was the first time I’ve been anywhere outside the safety of my house dressed in anything other than conventional male clothing.

And I lived to tell the tale!

Going properly into the outside world is something I’ve wanted to do for some time as I’ve realised that all the barriers that were preventing me were of my own making.  When I went out on the aforementioned short walks, I took full advantage of covid conventions to wear a mask and deliberately avoided people, even crossing the road at one point to avoid people who almost certainly could not have cared less if I’d walked right past them.  This time, though, I wanted to mingle!

I was also well aware that time was limited for me as my son would soon leave school and take up residence in his bedroom until he (hopefully) goes to university in the autumn and was starting to feel a mix of the time being right and it being now or never.  Even so, when I got up that particular morning, whilst I’d decided to celebrate my son’s return to school after the Easter break with a bit of she-time, I’d more or less shelved the idea of an outing.  But when I’d got dressed and done my makeup, I realised that I looked as good as I was ever going to without professional help and the decision was made.

I quickly packed a ‘bug out’ bag consisting of male jeans, sweater, shoes and makeup wipes in case of emergency (the guy shoes actually came in very handy when I realised that driving in heels is not easy!), put a few essentials into a handbag, took a deep breath, opened the front door, left the house and got into the car to drive 7 miles to a supermarket – sufficiently far away to make the chance of bumping into someone I knew negligible but near enough not to be out of the house too long if there was some crisis at work I needed to attend to.

I was probably overdressed for a trip to what used to be the UK arm of Wal Mart – black skirt & top, pink blazer, black tights and pumps/courts with a heel of about three inches – but I felt that if I was going to do it, I had to go all in.  The drive was uneventful and I parked in a less crowded part of the car park, got out and straightened my clothing.  Almost straight away, I felt the cool breeze penetrate my tights – a very different feeling to the breeze on bare legs when I’ve worn shorts on holiday but a delicious reminder that this was now for real, not just the fantasy of old.

I walked to the entrance and went in; it’s a big store with a large clothing section so I stopped for a browse without any of the usual concerns I have about going through the rails in my normal male garb.  Then onto the makeup section – I wanted to get mascara but the one I wanted had a security tag and, for a first proper outing, I wasn’t ready to interact with others to get the tag removed.  After a quick wander round, I decided that that was enough excitement for one day so made my way back to the car for another uneventful drive home.

Strange emotions when I got home, bearing in mind that this was my first proper trip out where I have voluntarily mingled with people rather than actively avoided them.  My immediate reaction was that I probably shouldn’t have done it.  Mrs A would be horrified if she knew and because she’s given me such an amazing concession to dress without guilt, I do want to respect her point of view as much as I can.  But over the ensuing hours and days, that got supplanted by a feeling of euphoria and the realisation of how far I’ve come since nervously posting a heavily processed FaceApp image on Flickr four years ago.  What had seemed like an impossible dream was now an uneventful reality.

What I do know with 100% certainty is there are people like me desperate to break free in the world but petrified of the prospect of being out in the big wide world and mingling amongst other people.  I know that with certainty because until recently, I was one of those people.  Now, any one of my co-contributors could give a far better account of being in the big wide world than I ever could but one advantage I have over those ‘old hands’ is that my memories of my first time are much fresher.  So if what I’ve just written on the one hand resonates but on the other evokes a reaction of ‘I could never do that’, let me reassure you that if I could do it, you most definitely can.

The big fear that we all need to come before taking our first steps into the real world is ‘what if someone realises I’m a guy?’.  We obsess about ‘passing’ – being indistinguishable from a genetic female – and here, there’s bad news and good news.   The bad news is that in all probability, someone will realise that you are CD/TG and the more people you encounter, the higher the probability.  Apart from the ravages of testosterone on bodies and faces, your gait, your height, your voice, the size of your hands and so on all conspire against you.

The good news, though, is you can stop worrying about it because it doesn’t actually matter!  The worst case scenario is you’ll ‘pass’ as a trans person – this is the 21st century and you only have to read the posts here on Kandi’s Land to see the amount of acceptance there is in the world.  So be proud to be trans – no one who sees you knows whether you’re transitioning to female or just a CDer having an isolated day out en femme.  And quite frankly, they’ve almost certainly got bigger things to worry about in their own lives than trying to decode you!

But let’s face it, it’s going to be a lot easier if we ’newbies’ don’t draw undue attention to ourselves on our first trip out.  The fundamental thing to remember is that we’re moving from fantasy to reality.  We can live out whatever fantasies we like in the privacy of our own home but we need to be a little more realistic if we want to avoid attention.  I will say at this point that, if you like attention, go for it!  What follows is advice for people like me who are happier not being the centre of attention so here are a few strategies that may help.

1.   Makeup.  You’re definitely going to need some makeup but the general rule is ‘less is more’.  Women who wear a lot of makeup get noticed, particularly if it’s excessive or not applied very well.  Foundation, a little bit of eyeshadow & eyeliner and lipstick goes an awfully long way and application of each of those is relatively easy to master.  Contouring, false eyelashes, winged eyeliner and drawn brows, whilst they can look sensational, take a lot more practice and are easy to screw up so forget them for your first outing.

2.  Outfit.  Dress appropriately for where you’re planning to go.  When selecting your outfit, ask yourself whether you’d expect to see others dressed in the same way at the place you’re planning on going.  I’ve already disclosed what I wore for my outing and I can categorically state that I didn’t see any other woman dressed nearly as smartly.  Does that mean I was overdressed or just a busy businesswoman popping to the shops during her break?  I’ll leave it to you to form your own opinion!

3.  Shoes.  OK, most of us love our heels but let’s face it, there’s a reason why most women save them for special occasions!  Just remember that if you decide to go out in heels and vow that as soon as your feet start to hurt you’ll turn back, your return to base won’t be pain free unless you’ve walked in a circle!  As with outfits, there are many feminine styles for shoes that are flat or have just a low heel but if you absolutely must wear higher heels, make sure you can walk demurely in them for more than a few paces!  And also remember that pavements/sidewalks aren’t as level as your floors at home and many an ankle has come a cropper thanks to the heel supporting it coming out worse from an encounter with uneven ground!

4.  Deportment.   The simple thing to remember is that women tend to take smaller steps with one foot directly in front of the other and with a straight back (not least to counteract the weight of their boobs) so try to do the same.  No matter how good you may look, if there’s one thing that’s going to give the game away if you walk like a workman, policeman or, heaven forbid, a gorilla!

5.  Stay in your comfort zone.  This may sound strange given that I’m advocating taking your first en femme steps in the outside world but you have almost certainly stepped way outside your comfort zone by the mere act of leaving the house in your feminine persona.  That’s plenty to be getting on with!  There’s no rule book that says you have to interact with people, try on clothing, use the ladies’ room, buy a coffee or anything else while you’re out.  Once you’re out and about, just enjoy the experience and do what you feel comfortable doing for as long as you feel comfortable doing it – the more challenging stuff can wait for next time.

6.  Don’t worry about anyone else.  In an area where lots of people are milling around, you will get stared at, particularly if you’re dressed in a more traditionally feminine way than most of the other women in the area.  Of course, someone who looks at you may be wondering ‘is that a man?’ but they may also be thinking ‘she’s attractive’, ‘I like her outfit’ or ‘I wonder where she bought those shoes’.  And as all of us well know, men look at attractively dressed women!  In your day to day life, you will walk past hundreds, if not thousands, of women some of whom will dress in a more masculine way.  Do you examine each one to try to decide what their biological sex is?  Presumably not so it’s a reasonable assumption that most of the people who walk past you won’t either.  But if someone does look your way, you don’t have to look back but, if you do, you can just smile as you walk past.

7.  Be confident.  Yes, stepping into the outside world for the first time can be a scary proposition but it doesn’t have to be.  You have as much right to be there as anyone else and as much right as anyone else to select the outfit you wear & present yourself in a particular way.  Hold your head high as you walk, be proud of who you are and what you are doing and ‘own’ it – you’ve well and truly earned that right.

Above all, be prepared for the whole thing to be a huge anticlimax!  In the build up, you’ll experience all sorts of emotions, your body’s adrenaline pumps will be working overtime, your heart will be thumping like it’s trying to fight its way out and you may well swing between ‘today’s the day’ and ‘no, I can’t go through with it’ several times before you finally take that step over the threshold into the outside world.  But when you do finally pluck up the courage, there’ll be no choirs singing ‘hallelujah’, no round of applause from crowds of adoring fans and no TV crews waiting to interview you about your achievement for the evening news.  It’ll just be a normal day with you wondering why you left it so long and trying to remember what you were worried about.  And if you’re anything like me, you’ll already be thinking about doing it all over again.

But make no bones about it, our first trip into the outside world is a huge achievement.  For me, finally stepping properly into the outside world was probably as big an achievement as Neil Armstrong’s utterance of ‘it’s one small step for man, one giant leap for mankind’ was for him.  But, of course, if rumours are to be believed, the words didn’t come out quite as intended as he was supposed to say ‘it’s one small step for A man,….’

Well that’s the official version anyway but I have it on very good authority that what he was really supposed to say was ‘it’s going to be one small step for a man, one giant leap for A man da’!  Our Neil was quite the prophet back in ’69!

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32 Responses

  1. As a postscript, since I wrote this post I’ve been out on a further two occasions, the first walking through a reasonably busy village centre and the second to another supermarket where I actually bought something, albeit using the self checkouts but both times dressed, or should that be overdressed, similarly to the first time. And I’m still alive!

    But Jocelyn’s post from yesterday is very relevant here. Whilst it’s nice to be dressed in a very feminine way, it can feel a little out of place when everyone else is dressed differently. Of course, we can concoct a mental story that we’re just like any business woman popping out for a sandwich, on our way to church if it’s a Sunday but, as Jocelyn proved in her post, dressing casually in no way diminishes the femininity we project in the same way that we don’t judge other women purely by their clothing.

    There’s still a long way to go as far as I am concerned but the whole thing has been a truly liberating experience.

    1. Amanda,

      While reading your comment here I immediately thought of a song by my fellow Canadian Joni Mitchell “Both Sides Now”.

      The song looks at many things from both sides, and of course “love”. But it is the following stanza that sticks out for me:

      “I’ve looked at life from both sides now
      From win and lose and still somehow
      It’s life’s illusions I recall
      I really don’t know life at all”

      We are all searching for the meaning of life, please keep looking; from both sides.

      Jocelyn

      1. Wise words, Jocelyn. One of the most destructive forces we can have in our life is regret. There’s nothing we can do to change history but if we can look at something and know we’re going to regret doing something, we quite simply shouldn’t do it.

        But if we look at it and realise that we’re going to regret not doing it……

  2. Amanda,
    I am so happy for you. What a day for you! I guess congratulations are in order. But as you said the actual outing was ”uneventful”.

    So what’s the big deal? I love the way you describe the day; from the preparation, to the outside world’s reaction to yourself, to the contrasting emotions when you got back home. It really is a big deal, but on the other hand it was uneventful. And you embraced both sides.

    Thank you for the details of the outing and for your outline of what to do and what not to do. I’m sure you have been very helpful to many who are still trying to decide if they should venture out en femme.

    Hopefully next time you will take a bunch of selfies with all the strangers you meet (tongue in cheek).

    Thank you for sharing this real life adventure with the world. And don’t worry, I won’t tell Mrs A that you are A man da. I love your last paragraph.

    Take care dear friend.

    Jocelyn

    1. Jocelyn, thank you as always for your thoughts and support. I suspect that many who read the posts here are, shall we say, of the slightly older persuasion and the big problem is that many of our worries are those that we picked up several decades ago when being a ‘transvestite’ was a source of either ridicule or speculation that all was not right with us and as a result, we spent decades in denial. In the 21st century, however, there is widespread acceptance of us as individuals even if people have more conservative views regarding the trans movement in general and if our ‘provenance’ is guessed, these days people keep any thoughts to themselves rather than pointing, smirking or stage whispering ‘look, there’s a man in a dress!’.

      There are many like us who are quite happy to stay in the safety of their home and never venture out and that’s absolutely fine. But no one should fear going out if, deep down, that’s what they want to do. And by the time I had my third outing, I couldn’t wait to leave the hotel room where I was staying at the time even though I knew there were several members of the hotel staff in the corridor outside.

      And I think Mrs A would love to hear that I’m ‘A man’, given the significant doubts she’s had with all of this. It’s just the ‘da’ on the end that may cause issues!

  3. Hi Amanda:
    Thanks for a revealing, informative and encouraging post! I find it interesting that you liken leaving the house en femme to a moonshot – that’s exactly the image I had in mind when I went out and about for the first time, and still do especially if I am going to a new place.
    In the current environment, safety may be weighing upon us more than in the past. As we all know you should be aware of your surroundings. I have found it helpful to do a “reconnaissance” before going to a new place. Check it out in drab first – where are the bathrooms, places to park your car, places to eat, good places for photos – things like that. I found it goes a long way to bringing comfort and confidence when you do your outing.
    Always great to hear from you
    Kris

  4. Kris, thank you for your encouragement! To be honest, before I took my ‘one small step’, I often felt that being the 13th person to walk on the moon was a more likely proposition.

    Great advice about doing a ‘recce’ (or doing an ‘Apollo 10’ to keep the space theme up!) before venturing into a new place. Ironically, I’d done this at this particular supermarket several times in the past – not with a view to entering en femme though but rather to buy outfits in my deeply closeted days. Sadly each and every one of them was the victim of a purge at one time or another.

    What I have learned from what I’ve done so far (apart from the reason that women don’t wear heels most of the time) is not to push my luck. I’ve now been out a total of 5 times, the first four of which involved leaving my house fully dressed. I took every precaution I could but I know it’s only a matter of time before my luck would run out so from now on it’s something I’ll avoid and either restrict my outings to times when I’m away from home (not very often) or wear androgynous outfits and park up and do makeup etc. when I’m out of the way.

  5. Well my fairly new and dear friend today’s post is why I was so upset awhile back when you had to cease posting on Kandi’ Land for a while.
    Here I sit, damaged goods, with a recuperative sentence of 12 weeks and unable to fend for myself. My entire world revolving around my smart phone. But, fortunately this all transpired after our “girl’s weekend in Kelowna’. But I am putting together my thoughts on how my post of my latest adventure is going to read. It will have a couple of surprises in it but you, like my self, are going to have to wait.
    Your post is so classic Amanda and just reading it this morning has already brightened my day and made me smile and made me laugh and made my whole out look better, so thank you so much my friend. I’m so happy for you and proud too that you’ve taken that huge step out the door. And I can’t wait to read about each new adventure. You and I have come a long way this past while my friend. Maybe we can connect at next year’s girls weekend. I am hoping to go to Diva Las Vegas in October assuming there’s no surprises when I see the surgeon at the end of July. Keep your fingers crossed for me.

    Love,
    Trish ❤️

    1. Trish, thank you for your kind words. I have to confess that I do rather enjoy putting pen to paper (finger to key?) with these posts and it’s nice to know that they’re appreciated.

      I’m doing things now that I couldn’t have contemplated a year ago and you’ve played a big part in that. Little did I know that, when I read your comments about how the ‘open letter’ had helped you and Mrs Trish, how much they would help a mere three days later. We tread a challenging path (perhaps not as challenging as the one Neil A trod in 1969 although I think the heels would be a bit easier to manage in 1/6 gravity) and the inspiration I draw from you and the others here has helped me more than I can ever put into words.

      Sorry to hear that you’re not firing on all cylinders at the moment but, as requested, I have my fingers and everything else crossed for you!

  6. Amanda,
    The first point is don’t sell yourself short be comparing with others , you know what was involved and the risks you were taking and it’s great to say you dealt with them and lived to tell the tale , that is so important for you .

    I’m sure you don’t need telling that there will be a next time , it is addictive , every step no matter how small validates how you feel inside . Interactions are a little harder , for them to happen means being close enough to someone to be scutinised , that can be very unsettling at first . I’ll never forget the first time my daughter saw me , she stared for several minutes before telling me my makeup was OK . Finding that confidence also brings amusing moments , that is when need to learn to laugh at ourselves , women are more accepting in this respect . Above all don’t be frightened to make mistakes , on one occasion I’d been out to the supermarket in a denim skirt and didn’t realise until I returned home that it was obviously back to front . I haven’t manged to leave the ladies restroom yet with my skirt caught up in my knickers but I came close !!
    I found the whole process of stepping out the door was easier if I had specific jobs to do , it took my mind off how I looked . Not long after I moved into my new home I had so many jobs to do in one day to get it up and running , I’d completely forgotten what I looked like until I returned home , it was a lovely reminder to catch myself in the mirror . I was exhausted but also elated , in one day I’d proved to myself I could truly live this chosen lifestyle .

    1. Teresa, thank you for sharing your thoughts. Regarding comparison with others, there’s a fine line and I’ve been on both sides of it. It’s an ultimately destructive force if it turns into envy or jealousy but it can drive us to push boundaries if we take a more ‘if they can do it, so can I’ standpoint and that was the case here.

      And you’re right about humour, life would be very dull without it.

  7. Oh my goodness Amanda, this post was so timely and fun to read, because it describes almost to a T my own first real outing only two weeks ago! I could hardly believe it when I read your story, the feelings, the emotions the anticlimactic aspect once it was all over were exactly as you’ve so wonderfully described. I tried to keep my head up and smile, watching people to see if there was any reaction. It was in a busy Walmart, just like the supermarket you’ve described, but other than a few second glances, mostly from young men, I saw no one, man, woman or child give a hint that I was somehow standing out, or anything out of the ordinary. I really could hardly believe it and it didn’t take long to get over my apprehension or fear of being called out somehow, even though I was certain that anyone who looked closely could tell without a doubt that I wasn’t a real woman. It was Sunday and I did see several other ladies dressed in similar fashion, nice modest dresses and makeup, so I didn’t feel like I was too overdressed. And like you I used the self checkouts as I didn’t want to have to try and talk to anyone with my somewhat less than feminine sounding voice.

    This was such a big step for me, but similar to you, after it was all over, it seemed pretty simple and not such a big deal after all. I’ve since done it again several times and never had a negative reaction, but I have been stared at a few times, mostly by men. I did basically the same thing the following Sunday and if it works out, I’ll have the chance to do it again next Sunday while I’m still working here in Phoenix.

    I spent the last two Sundays dressed completely en femme all day because I was staying in a hotel room by myself. I ended up doing my shopping, washing my clothes at a laundromat, getting fuel, hanging out at the airport in order to watch British Airways arrive from London, going for a walk in the park, all as a lady. It was really quite a wonderful feeling to be over my fear and to be out in public dressed as a woman. So what if someone read me or called me out? I really don’t care all that much about that either. I’m under no obligation to even respond to it.

    Another thing that also was so relatable is driving in high heels. My pickup is a full size work truck. It may have looked kind of odd to see a lady driving a truck like that but it also has a manual transmission. I wore women’s shoes that weren’t high heels most the day and they were very comfortable. But later when I went over to the airport, I decided to wear my heels, a decision I almost immediately regretted once I started to drive. It was so hard to keep my foot on the clutch and gas and it was quite embarrassing to have the truck die in the middle of an intersection. I took the heels off before going back to my hotel, and drove, not quite barefoot because I was wearing tights, but minus the high heels, driving was a lot easier!

    I really appreciate the pointers and advice you gave about venturing out the first time. I think I was in cloud nine while out and about as a woman and so something I didn’t think too much about was an emergency situation. Next time I’ll definitely be keeping a pair of my male clothes in the vehicle and some makeup wipes, just in case I end up needing to change back quickly for any reason. I did carry my camera around and pretty well documented my adventures, some of which I posted to flickr.

    I so enjoy everything you post and really love and appreciate the kind, motherly influence you’ve had over me. I love the one giant leap analogy, especially because Neil Armstrong is my hero! I look forward to whatever other experiences you’ll share in the future. I just wanted to comment on my experience because it seemed almost identical to yours!
    Thank you!
    Love, Liz

    1. Wow, Liz, that was a comment worthy of being a post in its own right! It sounds like you had an amazing time and I’ve got a bit of catching up to do!

      Sharing first time experiences is so important because most of us are completely alone when we take those first steps. We read the accounts of ‘seasoned pros’ and they give us the inspiration to break free into the outside world. But, as with anything, it’s much easier from the second time onwards – the prospect of the first time can be absolutely terrifying but I hope that people in that position who read the accounts here see that, by taking a few basic precautions and a deep breath, there’s a whole world out there waiting to welcome them.

      The ‘bug out’ bag idea was one I got from a YouTuber called Sydney Lovekiss and I think it’s a great idea, both from a practical sense because we just never know when we may need it, and from the point of view of giving us confidence – a bit like an insurance policy that we hope we’ll never need.

      Thank you also for your kind words. Writing here & exchanging views with other girls is my way of giving back to a community that has given me so much support & encouragement. I think all of us understand the isolation that comes with this particular territory and I just want everyone who reads my ramblings to know that they’re not alone.

      And well done for driving a manual – a rarity for people on your side of the Atlantic, I believe! We now just have to get you onto the left hand side of the road and my work will be done!

  8. Thank you Amanda . As a closeted cross dresser myself , I have dreamed and contemplated my first outing so many times but struggled to summon up the courage. Although my wife knows and accepts me up to a certain point, I don’t know if she would ever entertain the idea of me going out in public and as I have her trust and support, I wouldn’t really want to go behind her back. However, I’m not willing to say to never as I didn’t even think she would let me dress until recently and my children had moved out , so there is hope . I think you described your out perfectly and I’m pretty sure I will feel exactly the same . I hope one day I can share my experience on here . I truly love being able to be part of this community with all you amazing contributors and of course Kandi . Much love to you all 🥰

    1. Chris, thank you for sharing your thoughts. You are absolutely right in your approach to this and I have felt much the same since my wife gave me her blessing to do this back in January. What I didn’t put in the post above is that my wife would be absolutely horrified if she knew that I had left the house fully dressed and this does play on my mind. I could justify it by saying that her agreement was on a strict DADT basis but the question always remains as to whether, in giving her blessing on these terms, she ever envisaged me going out from home in this way and, if she had done, would she still have been prepared to countenance this side of me?

      On the plus side, my wife’s agreement in January was a complete U-turn from her stance in mid 2014 when she issued me with a cease & desist ultimatum. In January, she made the point that she knew that I was doing it behind her back because, as she put it, it never goes away but I suspect that she saw that it wasn’t encroaching on the marriage in any shape or form. Attitudes can soften over time and I hope that you will soon find a way of getting the further concessions you want from your wife.

      1. Thanks Amanda. My wife also gave me the ultimatum many years ago and we came close to going our separate ways. Thankfully we worked our way through it and slowly but surely she realised and understood that it is not something we can just stop. Once my children moved out I was able to have far more freedom as long as I didn’t go overboard! We went shopping for clothes together , which the first few times was nerve wracking for me , I couldn’t believe it was happening and I felt a bit strange trying on dresses and skirts in front of her and asking for opinions! But it’s fun now . My daughter has recently moved back home so my opportunities have been very limited and in some ways that has made my longing to get out even stronger. As we know , the less opportunities we get the stronger the urge . Oh well I will bide my time, build up confidence and courage and enjoy reading other experiences. Kind regards Chris x

        1. Chris, I often say that I post all the gory details of the mistakes I’ve made here so that others don’t make the same mistakes that I did! One of the biggest mistakes I made was with communication with my wife. Several times after I agreed to stop, she asked if I was OK and I just brushed it off saying I was fine. After a while, the questions stopped and it became a subject not to be discussed for over 8 years. My gradual slide down the slippery slope to my old ways has been well documented in my posts here but what I’ve never really delved into is the impact that firstly suppressing what I wanted to do and then doing it in secret had on me and, by association my marriage. I can’t speak for Mrs A of course but after I was relieved of the burden of guilt I could see that I’d built walls around myself and I’d become quite withdrawn up to that point without realising it.

          I guess my question is whether your wife would agree to time away so that you can spread your wings a bit? There’s obviously a great deal of trust between you but if the lack of opportunity is starting to frustrate you, it could be a good way of dealing with it in a way that not only doesn’t directly affect family life but also benefits it in other ways.

  9. Thank you Amanda . As a closeted cross dresser myself , I have dreamed and contemplated my first outing so many times but struggled to summon up the courage. Although my wife knows and accepts me up to a certain point, I don’t know if she would ever entertain the idea of me going out in public and as I have her trust and support, I wouldn’t really want to go behind her back. However, I’m not willing to say to never as I didn’t even think she would let me dress until recently and my children had moved out , so there is hope . I think you described your out perfectly and I’m pretty sure I will feel exactly the same . I hope one day I can share my experience on here . I truly love being able to be part of this community with all you amazing contributors and of course Kandi .

  10. Sorry I’m not sure my my reply came up twice . I’m not the most tech say person but this should not of happened 🤔

  11. Amanda,

    That euphoria you felt after returning from your first big trip outside is such a wonderful feeling, one that will stay with you for a long time. Congrats on getting out girl! You are at the beginning of what may prove to be a very interesting and fulfilling part of your life.

    And don’t worry about overdressing, I do it all the time. As long as you don’t wildly overdo it, there are ways of dressing a little nicer than most women that are tasteful and attractive. I really enjoy dressing up and am often among the better dressed ladies in public. It just feels so good to be dressed nicely and, for me, it greatly increases the feeling of femininity.

    You bring up some good points for ladies to follow with your section on confidence being so very important. I believe confidence plays a much bigger roll in coming across as female in public than many people realize. Yes, the mannerisms, clothes and makeup are all important but a lack of confidence can certainly impact the amount of enjoyment one gets when dressed and out and about.

    Feels great having taken these first steps out, doesn’t it?

    All the best,
    Fiona

    1. Fiona, thank you for your encouragement!

      I have to say that I just loved being out in a dress and heels! Knowing that I could go through the racks of clothes without anyone giving me a second glance was just a great experience, as was looking around and realising that no one was staring (except for one small boy who, mercifully, didn’t say anything!). However, I did find that I had this nagging feeling that the way I was dressed could attract attention even if most didn’t realise what was underneath.

      I think there’s an interesting area to be explored in the ‘middle zone’ so to speak – in other words wearing clothes that are more gender-ambiguous – and that’s what I’d like to try next time. What I’m hoping is that, by feeling that I’m blending in far more, I can normalise the whole thing in my mind so that what I wear going out just feels like an outfit choice rather than the major exercise it is at the moment.

      Regarding confidence, I’m still quite shocked that I managed to muster it up! What I realised a while ago, though, is that the differences between men and women are far smaller than many believe or, to put it another way, the majority of differences are visual – facial, clothing, anatomy etc. – and if we get the visuals right, we’re 99% of the way there. Going overboard with exaggerated feminine mannerisms at best gives no benefit and at worst draws attention to us for the wrong reasons. It was basically that, plus the knowledge that no one else really cares that got me through!

      1. Amanda,
        Your last paragraph makes a good point about men and women being closer in many respects . That was the conclusion I came to just a few weeks after going full time . I was making excuses to do some more tedious , dirty jobs in male mode . Women now take an equal part in all aspects of society , ( Kandi will love this one but sadly the June Cleaver days are gone ) being stuck in the kitchen in a frilly apron is a thing of the past perhaps there’s a good chance you may see a husband dressed as such more than the wife .

        As a postscript I should add that when I moved twenty miles away after my separation my ex assumed I wouldn’t venture back other than the man she knew . I thought hard about this and decided that our separation meant we were free to be us , she no longer had the right to dictate and control my life , I wasn’t controlling her’s in any way . So I returned to my painting group which also allowed me to sound out old friends to see how they felt about the new me . Your comment about confidence rang true at this time but I’m so glad I bit the bullet because I hadn’t lost anyone . I will add I was getting some dreadful Emails from my ex at this time , I tried to understand how she felt but it was still hard to accept that after 45 years living with someone they could turn so abusive . I truly wanted to remain friends with her , what harm was there in that besides we stiil had to consider our children and grandchildren’s needs . We are on resonable terms now but she still can’t face meeting me again as Teresa , despite everything I’ve told her my door is still open to her . I’m sure you’ve read my post on dealing with the children but it’s great that we are there for each other .

  12. Bravo!

    Once we overcome the fear–to use your Neil Armstrong analogy–of the overwhelming weight of gravity holding us back, it’s actually fairly ease to go out. People really don’t notice, or don’t care, or are too busy looking at their phones.

    As I have written, people may know it’s a man in a dress, but they don’t know it’s ME in a dress–and I just want to make sure it’s a pretty dress (my tablet just suggested those words for me, so it knows me well).

    I agree on the makeup; less is better. Easier to get on, easier to take off. And if someone is really close enough to see your makeup, they probably have already figured out you are on the trans spectrum.

    Be bold, overcome the fear, make a plan, make it happen. The one real regret is that it took you this long to do what you’ve been wanting to do for years.

    Then come back here and share YOUR first time story.

    1. Dee, thank you for your words of encouragement. Reading about your adventures every Sunday helped me no end as I mentally prepared for this and I am deeply grateful to you and the others here for sharing your lives in this way. And I love your ‘people may know it’s a man in a dress, but they don’t know it’s ME in a dress’ quote – it should be the mantra for every single one of us.

      It’s very easy to read your & Kandi’s posts and think ‘I could never do that’. But what I’ve come to realise is adding ‘…but what could I do?’ is important. Just one year ago, all of this would have been unthinkable for me but thanks to the inspiration I’ve got here, what once seemed impossible is now nothing to fear.

      And continuing on the theme of drawing inspiration from others, my next big objective is to find a GG friend!

      1. Thanks for the very kind words. I’m glad my posts helped you overcome the gravity of fear.

        For me, after reading other’s posts about going out, my reaction was never “I can’t do that”, it was always, “if they can do it, then why can’t I?”

        Until one day I did go out and have never looked back.

      2. Amanda,
        sometime ago on a forum the debate became heated over the term’s ” want and need ” . In my earlier days I didn’t understand the want but the nagging ” gut feeling ” of need just wouldn’t go away .

        Most of us have been through the heartache of feeling , ” I could never do that !” At the time reading about other trans people felt like being on different planets . I do appreciate the ” what ifs ” going through your mind , I remember my early drives when panic set in after I realised I had nothing to change into if I broke down or was involved in a road accident . People might recognise your car and even when you feel safe by giving yourself some distance there is always a familar face that pops up unexpected . That also raises an important point of being clocked , you have an advantage because you may recognise the other person but for them to recognise you they will only be looking for the man . Not long after I separated I was out as Teresa in a large out of town store when directly in my path was a neighbour I’d known for years from my old home , I looked directly at her and gave her a smile she smiled back and walked by without giving a second glance . in male mode I would stopped and chatted for several minutes .
        Finding a GG friend is not always easy , how do you find someone you can totally trust and what would you base your friendship on ? If you could find a social group you would be on safer ground , having a trans friend places you both in a similar situation , there has to be mutual trust . I’m lucky to have a GG friend , I don’t always enjoy shopping with her because her style isn’t the same as mine but it’s great to go on days out with her . A few weeks ago we took a coach trip to castle Howard , next month we are going down to Southwold in Suffolk and taking in a show .

        1. My concern regarding recognition, unlikely though it is, is not personal. In fact I’m proud of this side of me and whilst it’s not something I choose to broadcast, I would not feel any personal shame if it was ever to become known by those who know me. However, I do need to honour the concession that my wife has given me to continue without issue as long as neither her nor our children ever get to know about it. That puts both a physical obligation not to put myself in a situation where the risks become unreasonably high and a moral obligation to remain within the spirit of what was agreed. Having seen the emotional trauma that my first confession caused her, I’m not prepared to put her in that position again by pushing the boundaries way beyond what she envisaged when we had our conversation in January.

          Regarding GG friends, there are several existing friends that I trust enough both to talk to about this side of me and who I would be happy to see me dressed. However, once again it stretches the boundaries of acceptabilty as far as my DADT arrangement is concerned at this point in time. Of course, viewpoints can change, as can circumstances – they certainly have in the case of my wife and me – but underpinning everything is my determination to as far as possible fulfil the promises I made to my wife when we married. I feel inordinately lucky that I can now do that as well as being able to indulge my feminine side without guilt.

  13. Thank you Amanda, I thoroughly enjoyed reading all the other comments and taking cues from those who have had advanced experience at doing this. I am somewhat familiar with Sydney Lovekiss but I don’t recall the video you mentioned. And being Sunday, I’ve been out at it again and enjoying every moment of it. It just gets easier and easier the more you do it. Today I seemed to notice people looking at me a bit more and if I caught anyone’s eye, they’d usually smile and I would smile back. Maybe it’s just that I’m more comfortable meeting someone else’s gaze now. But still everywhere I went, people just generally mind their own business and pay no attention to the guy in a dress.

    And about driving a manual, they’re not real common here anymore, even in the big trucks, so I think it’s a pretty good anti theft device. Driving one has never been a problem for me until I tried it in high heels though! I dont know how you manage over there where I’ve heard that most the vehicles are manual. But if I tried driving on the left side of the road from the right seat in a manual, I’m sure we would crash and burn. I’m just learning to fly from the right seat of our plane and that’s hard enough, but driving a vehicle from the right seat sounds like another challenge altogether so you’ll have your work cut out trying to teach me that! And one thing I’ll never try doing is to fly a plane with heels on. Try working the rudder pedals that way and you’ll crash for sure. Thank you for humoring me, that’s one thing I love so much about you, is the ability to include humor even in a serious subject. It’s very endearing.
    Love you!
    Liz

    1. Elizabeth,
      I don’t know how you do it, driving on the wrong side of the road on narrow country roads with high hedges. I had an interesting time driving (in heels) in England. Went to a wedding in the middle of the dairy area, almost ran head on into the bride when I took a right hand curve on the right side of the road.

      Amanda,
      I know I never fit in. I (need to) wear 4+ inch (11+ cm) heels all the time, so I usually one of a very few in heels no matter where I go. Heels are not an option for me. I almost never go out en femme, but most, if not all, of what I wear is women’s. Kindness, confidence, and a smile go a long way.

      1. Cali, there’s an important message in what you say. There is no law in either of our countries that dictates that we can only wear clothes labelled for one particular gender and, in fact, women are quite happy to wear what they like, regardless of who it was intended for. Of course, there are many conventions at play but, in the end, the choice of what we wear is ours alone and whilst others may seek to judge, they have no fundamental right to do so.

    2. Liz, well done for getting out and about once again! We’re all converts to the cause of course but I hope that others who have yet to take this step read what you put and understand that, with a few basic precautions, they have nothing to fear.

      And at the risk of being dangerously irrelevant, I’ll just touch on your & Cali’s points about driving on the left! Funnily enough, driving on the ‘wrong’ side of the road is a bit like going out en femme – don’t try to overthink it and just go for it! The only problem I’ve ever had is sitting in the left hand seat, forgetting that I needed to change gear with my right hand not my left and hitting the window winder not the gear lever! And Cali, country lanes are easy – because they’re so narrow, you drive on both sides of the road at the same time.

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