One aspect I enjoy about cross-dressing is attempting to create different female appearances. This is down to a combination of make-up application, wig choice and style of clothing. My choices are driven by mood. Some occasions I really want to glam up and wear short dresses, this is always fun and , I feel, rather daring to attempt when you live as a man. Other times I want to see gif I can pass myself off as female and be believable in terms of appearance.

I find attempting to look female in na convincing way is the challenge I truly thrive on and enjoy the most. This picture is a selfie shot from my most recent cross-dressing opportunity in mid March. It had been three years since I last had a relaxed opportunity to cross-dress (I had a very brief and unsuccessful opportunity back in December…best forgotten!).

I’m aware I have older sagging and far from smooth skin, but then again who in the real world, and I include many beautiful young woman, has skin without texture? Texture is real and so is an aspect one has to work with when applying make-up. My acceptance is I have less than ideal skin on my face and I focus on creating a smoother overall colour tone as the texture, my pores and bumps from years of shaving, exist and are there. I know photo manipulation can smooth skin which I feel looks quite odd! I see pictures in many women magazines (yes, I love reading women magazines) where the faces look like they are made of some strange plastic looking skin…scary! I see this trend is now prevalent on social media photo posts. I think such magazines are probably at the root of image issues many young females seem to be having these days.

I admit, I dreamed of smooth perfect skin but reality is I don’t have it. I’m much hap[per in my cross-dressing now I’ve evolved my mental approach to knowing I have to work with the face I’ve got. I really enjoy applying make-up now and seeing what I can do. I will never master the skin I hope to one day haver but I get a lot of delight and enjoyment from applying make-up and trying out various colours and techniques.

I’ve come to this direction because I am planning a trip out later in the year and you can’t exist in the real world in any other way than working with what you’ve got. This applies to my face, my body, clothing choices my mannerisms and inner projection. My facial skin has texture and I have wrinkles and lines, these are inescapable. I use make-up to change the focus on my face. By that I mean I play up what are(hopefully) my best areas and try to minimise the less than ideal areas. I have rubbish lips, there is not much I can do to them without ending up looking like a full on drag queen. I play these down. I use my eyes as my main emphasis so concentrate my efforts on eyebrows, eyeliner, shadow and mascara. I’m hoping if I make my eyes the main focus my other failings won’t be as noticeable.

In terms of clothing, I’ve modified my dress choices for the planned real world trip out. Female friends advised me on this. They suggested, rather unanimously to my surprise, I should wear midi dresses with a scoop or v-neckline. Being a crossdresser this was a departure from the faved mini dresses and body con styles. I followed their advice and the first time I wore one of the midi style dresses it felt incredible! It proved to be a style that made me feel more feminine than ever before. I loved the fabrics, I adored the way it swished around my freshly shaved legs, the feel of the whole dress was unbelievable. When I sat down and the split draped and revealed my legs I was ecstatic. This impacted on me more than I can articulate. I have a few midi dresses now and I am looking forward to wearing them in the future.

Although the full dress is not visible in this selfie I was feeling so alive wearing it and the make-up. I adored, loved, was delighted, truly in heaven appearing as a woman and felt great emotional fulfilment. I felt my nerves easier and my confidence increase and though I always felt terrified over going out in public (my last time was back in May 2017) I felt a new level of comfort within me. Now, I can’t wait!

Tags:   transvestite mature transvestite cros female impersonator female illusion female alter ego female portrayal transgender transsexual wig makeup dressing up as a woman

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In the words of a Led Zeppelin song “Been a long, lonely, lonely, lonely time”…

It really has! Apart from a very brief, literally a three hours and not very successful, cross-dressing session in December I have not cross-dressed as a woman for three years. My last proper session took place in March 2020 just before the Covid lockdown came into effect. There has been no opportunities since then (apart from the brief December attempt) to truly relax and enjoy my time cross-dressing and delighting in being my female alter-ego.

An opportunity finally presented itself in the third week of March and after retrieving all my female clothing, shoes, wigs and make-up I discovered three years of less than ideal storage in a cold shed meant nothing, apart from the shoes, was in a ready to wear state. Most of my make-up was long out of useable date. Not the best of starts. On top of that, strangely seeing as I had waited so long to cross-dress again, I found my mood and motivation was not as enthusiastic as normal. I was feeling lethargy and almost decided not to bother.

I rallied somewhat, and being home alone for a few days was able to openly launder all my dresses, tops and female underwear and freshen up my wigs. A female friend kindly shopped on my behalf to get fresh make-up and new pairs of tights (pantyhose). I set about shaving off all my body hair (which had grown a lot in the last three years!) and began prepping for applying make-up and dressing in female clothing.

A whole day was gone by the time I had washed, dried and ironed my dresses and tops and I felt too tired to go any further. The next day never happened as I had a short notice call to work and that ended that days opportunity. The day after I decided to cross-dress but found my motivation lacking. I did go ahead and soon realised over the last three years I had not only aged a few years but I had also put on weight. This was visibly noticeable around my chin. I have quite a weak chin for a man, which I like as it usually is better for my female look, but the extra weight was not good to become aware of. My facial features had filled out and I had more lines and saggy skin.

I know you can’t escape aging skin but I was disappointed I had put on weight more than I realised. I was quite unwell during the last three years and physical exercise wasn’t possible for nearly two years. Also, I worked from home during the last three years and the job was sedentary. It was only getting back into a dress I realised just how far I had let things slip.

The outcome of this was I am now back on healthier lifestyle and taking regular exercise. I have started to see my weight reduce now. I’ve resolved to avoid going as thin as I was before the pandemic. I was somewhat obsessed with trying to get a slim girly figure. People now tell me they thought I looked too skinny. I think a happy mid area between my skinny days and my current weight will be better and healthier. I’m not going bonkers with loads of exercise and manic dieting, I’m literally just walking a lot more, moving a lot more in general and have reduced the amount of chocolate and cakes I eat. It’s what I call a comfortable process of weight reduction.

Back onto my cross-dressing, the weight reduction is important to me but of more concern to me was my surprise at the lack of motivation to dress when I’ve been dreaming of doing so for the last three years. The December session was too rushed and highly unrewarding, I feel this may have had a negative effect on me.

To be accomplished at cross-dressing, I feel if I were able to practice more regularly I could maybe start to achieve a reasonable female appearance. The long gaps between my cross-dressing restrict my abilities to progress in the art of female illusion. I also have an emotional aspect in that I enjoy my time appearing as a woman. I have a transsexual aspect to me and the cross-dressing fulfils this desire within me. I only began cross-dressing back in November 2000 at the age of forty one. This is now the twenty third year for me but in all those years I have had at least six of them when I have not been able to cross-dress at all. I prioritise my family and need to work ahead of my cross-dressing so it is always the first thing I have to abstain from if things crop up I have to attend to.

I call my cross-dressing my luxury indulgence, as that’s really what it has become for me. I know I need to express this part of myself and I always look forward to having an opportunity. The last three years though have caused a significant loss in this part of me. As I applied, rather ineptly, make-up I became aware of my ageing and increased weight all too easily. My vanity took a bashing! Fortunately, I have retained some shape to my figure despite the weight increase so I was relieved about that. My face is not getting any better with age, I am now sixty four, but I think that’s a reality we all encounter.

Despite not feeling as motivated as I had anticipated, I was pleased I pushed on. I was very disappointed with how hopeless I was at applying my make-up, especially my eye make-up and lipstick. I did get a buzz from wearing make-up once more though and I loved wearing a dress again. The wig was a delight to wear, as ever for me, and the final wee thrill came as I stepped into my high heels with freshly shaved legs. I was genuinely delighted but my plans to record the whole experience went completely awry! I tried taking a few pictures and recording a few videos but I just wasn’t quite into it enough to focus on doing that.

I did take a small number of selfies and managed a couple of videos but I felt I was covering subjects I’ve talked about in previous videos. I was disappointed with my appearance, I feel I have done better in the past. The three year absence from cross-dressing was very apparent to me.

I am, much to my relief, finding my enthusiasm starting to build again. The less than successful session in March has rekindled my desire to cross-dress again. I am hoping to have another opportunity in the late summer. I intend to do better and get more from it next time. I think I need a new challenge as I’ve not really progressed over the last ten years. I’m in a bit of a rut with it my efforts to look female.

I did try and change things a bit in March by wearing heavier make-up and choosing an animal print dress. It was rather good fun to attempt a different look. I wore a lot of foundation, a lot of eyeliner and mascara and used a dark bold coloured lip stain. It may not be that obvious in the picture, but it was a departure for me to try this kind of appearance. It added a bit of spice to the session to dare try it!

The picture I’m posting is in the genre of that classic selfie shot using one’s reflection from the mirror. I’ve never done well attempting this but I thought I would try it. I did enjoy wearing the dress and was surprised how the heavier eye make-up rather infused me with an adventurous buzz…all I needed was a party to go to and engage in a bit of flirtatious behaviour.

Tags:   transvestite crossdress tgirl gurl impersonator drag queen female impersonator female illusion female alter ego female portrayal transsexual Woman Pretty Feminine Natural

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My most recent cross-dressing session, 21 March 2023, while enjoyable was not too successful in terms of creating a reasonable looking female appearance . It was a combination of not having cross-dressed for three years, being completely out of practice, a high degree of impatience to become my female alter-ego and, to my surprise a feeling of lethargy was dampening my motivation.

I did push on and was pleased I had. The results were not great though compared to previous occasions but I did gain some reward from the experience. I am obsessed with trying to look female facially and I’m prone, somewhat masochistic I suppose, to taking close-up selfies to see if I can look feminine in any way. I see this as the big challenge as a male to female cross-dresser; probably, my biggest obsession!

It’s because I dream of looking feminine and love imagining I’m a woman. I’m forever experimenting with make-up and eyebrow plucking but ultimately I can’t really escape my male face. I enjoy the challenge though.

I have previously mused on how I like to create a back story for my female portrayals. I feel this gives my female guise some substance and it’s something I can draw on to be the woman I’m presenting as.In my early days I was acutely aware I was a man dressed up as a woman. These days I try to be the woman and suppress my male self. As I’m, well, can only be described as a mature cross-dresser, my back story reflects my age. I created the scenario in which Helene is a divorced woman with grown up children who has had it with men and found she is more at ease with other women and becoming aware she has a lesbian side to her. This is more to add a bit of edge, a slightly slicer vibe to the persona. Helene is also a professional woman running her own business and feels confident and at ease when she wears skirt suits, heels and make-up. She feels she can work confidently dressed this way in her business dealings. She is trying to avoid the overdone make-up looks of plumped overdrawn lips, heavy contouring and false eyelashes. Instead she is (hoping) she can convey herself in a feminine and natural way by more discrete make-up and classic tasteful clothing choices. It’s all fantasy but good fun and actually does help me become the woman when I cross-dress.

Maybe people will think it’s weird I do this but it helps me to feel real as a woman. Maybe, if I was a woman this could have been how it was in reality, who knows! All I know is I love become female (albeit it in reality me dressing up and setting free my suppressed self) and I enjoy my time as a woman. I genuinely believe, mainly because I am keen to pass myself off as being a woman) that having a back story will give me confidence for my planned venture out as Helene this summer. I want to be able to visit galleries, interact with people, go to cafes and see if I can be perceived as female. I’m hoping, dreaming really, no-one will realise I’m a man…as you can see, my fantasies can delude me!

I’m aware I have a few things that are favourable to my dream, I’m not very tall and many women are taller than me, I’m delighted about this. I’m aware I was fortunate enough to have nice legs. I am very willing to pluck my eyebrows and have them more feminine in their style, I have no qualms about shaving off all my body hair for a smoother appearance and I love tucking away my male genitals. I always feel delighted when they are out of the way, most men would be horrified by that but I love it! Knowing I can then wear real female lingeries helps me feel more female within myself.

I have a few lace-front wigs now which I can glue on. This is a confidence booster as in windy conditions your hair can blow about and so move like real hair and your hairline looks natural…exciting! I say exciting as the very rare occasions I have ventured out as a woman (not many at all) I loved the sensation of walking in a dress and feeling the air move around my shaved legs, it was a sensational experience.

That heightened sensation of walking in a dress and wearing make-up did boot my confidence considerably. Female friends have told me how uncertain clothing and make-up application they too feel increased confidence. Being a man is quite drab by comparison.

I’m posting yet another picture because this week my desire to cross-dress is truly powerful and as usual I have no opportunity to do so. Despite this, I find the desire and just recalling previous times I dressed as a woman is creating a somewhat intoxicating feeling within me. I’m still pinching myself that I have been cross-dressing for just over twenty years. Knowing I had the desire and acted upon it it is rewarding and it is always an exciting thing to do. I love everything about women and I have no regrets I have spent time wearing make-up, lingerie, dresses and heels. There is a lot more to being a woman than the superficial aspects I’ve just listed but it is an incredible thing to experience. Also, I find time as a woman is incredibly liberating and I feel emotionally free and far more confident. I feel I’m more alive as Helene, I adore cross-dressing!

Tags:   mature transvestite transvestite female impersonator transsexual T-girl T-gurl TG trans drag queen tranny crossdress

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It has now been six months since I was last able to cross-dress as a woman and right now…I am rather desperate to do it again! I’m not sure if I will get another opportunity this year but I am hoping one presents itself, fingers crossed. This morning I found myself wanting to put on my make-up, paint my nails and wear a dress. I Ama man but I really love to present as a woman and I always adore wearing dresses. They just feel amazing. As is my norm in these situations, I browse through the pictures I took from previous cross-dressing sessions and enjoy the warm memories.

In my last two session (December 2022 annd March 2023) I had completely got into long midi dresses in a floaty fabric that I delighted on wearing and feeling the fabric caress my freshly shaved legs. I also loved the lower cut neckline and enjoyed having shaved off my chest hair. I did somewhat get a bit whimsical tin dreaming of being feminine for real. I would love soft smooth feminine skin and wish my face was more feminine but I can only work with what I’ve got. I do enjoy the challenge and transformation of attempting to look female and I won’t deny, once I’m cross-dressed in my dresses, make-up, wig and heels I feel truly alive and have a confidence and contentment I never experience as a man. I love being a woman!

I absolutely loved wearing this dress, the colours were lovely and definitely made me feel feminine. I chose my blonde wig to complete the look though I wasn’t convinced I had chosen the right colour of nail varnish. I think something less vivid would have been more convincing and realistic in my attempt at female illusion. I still loved every minute of being a woman for a few hours. Just recalling the memory is filling me with inner joy and excitement that I actually did this. I am so delighted I free this aspect of myself and experience it, albeit on a temporary basis. It’s so fulfilling in so many ways.

Tags:   transvestite transgender transsexual T-girl tranny transvestism crossdress crossdresser crossdressing man as woman man in dress Male to female makeup dressing up as a woman drag female impersonator Female impersonation female illusion female portrayal female alter ego wig

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I’ve had very few opportunities to cross-dress in recent years with only three fleeting opportunities since March 2020. I miss cross-dressing and I’m aware my make-up application very much out of practice now. Today I had a very brief opportunity present itself and so I went for it. The preparation time ate into my available time as it took awhile to shave my legs, chest and arms and pluck my eyebrows but I loved how it felt as I started to apply my make-up.

I love women’s shirts and I have a few I had yet to wear. The shirt I’m wearing in this picture is one I’ve been particularly keen on and I thought it would go well with my blonde wig and a denim skirt and wedge sandals. Summer may have passed but I was dreaming of heading out for a visit to a cafe and gallery wearing his ensemble.

I struggled with my lipstick and realised I had run out of my favoured eyeliner pencil. The one I used is a bit smudgy and it was a frustrating. I had also run out of my favourite mascara so again, I used another I had in my make-up bag. I had no timer to paint my nails, I missed that and no time to wear perfume either, I wasn’t quite able to become the woman I wanted to be but after seven months of waiting since my last (al too brief) previous session I did what I could.

I did record some musings on video but I was more into the moment rather than saying anything coherent or work listening to but I had a nice time and regretfully had to return to being a man all too soon.

One day I will venture out in this outfit and spend time out in the world as the woman I like to become. I need to make that happen as I’m now age sixty four and I’m not getting any younger

Tags:   transvestite trans transgender tranny crossdress crossdresser crossdressing Male to female men who dress as women female impersonator Female impersonation female illusion female portrayal female alter ego drag drag queen transsexual trannie transvestism wig swap gender gender illusion

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