Member Experiences

So many of my members and friends experience both joyful and disastrous incidents in their crossdressing and explorations of trans life and gender fluidity. In response to several requests for a page my members can use to talk about these I have created this page of members experiences. Feel free to tell your story.

We all have different paths on this journey. Some are positive and some less so, however I do believe that by sharing our stories we are able to learn from each other. Much of my path is covered in this page. Here I am giving you an opportunity to read others stories and post your own. Please keep content respectful and tasteful, as this seems to be one reason my site is so successful. I am thrilled that you are part of that success.

Don’t forget, you can still enjoy and post stories in My First Time – which details how many of us came to be here. There’s many examples of how we first came to experience our journey into gender explorations there.

To post a story you will need to be a member and logged in. This is easy. If you’re not already a member just register here – http://FionaDobson.com/register – and then log in here – http://FionaDobson.com/login

If you are looking for a more direct form of community and don’t have one locally, you may find my Elite Whatsapp Group is right for you. You can find details HERE.

Then simply use the comments section below.

A word of caution. Make a note of your password and do not attempt to change it.

🙂

Fiona

  • http://FionaDobson.com

28 Replies to “Member Experiences”

  1. I recently told my wife that I’m crossdresser we had played around before but I came to her as one who couldn’t resist the urge anymore. She is still processing but has expressed her willingness to help me. What a relief it’s all thanks to Fiona and her website she encouraged me to talk with my wife and not hide anymore. I will be here for a very long time if I can be of help to anyone please let me know. No more shame

    1. Can i just say total full respect to you and never feel ashamed of being your true self. A choice or a step in the right direction is a progression to a more openly free and progressive future. Also this site has also given me clarity and affirmed that its totally ok to personally be my true self. It’s scary but worth it in the end. X

    2. Great to hear you’re getting some acceptance. I’ve been crossdressing on and off for years but my wife saw a photo on my phone of my legs and feet wearing stockings and high heels. She didn’t understand why I wanted to dress up but said I could do what I like but she doesn’t want anything to do with it. Disappointed but I have accepted it is a part of me and will have to keep it separate.

    3. I had my sister in law chatting with me crossdressing staff. She convinced me to give her some money so she could buy me some girly staff. She bought for me a load of things. Then she convinced me to put on, take photos and then send them to her. I did that for at least 2-3 months. To the moment she is still supportive and likes to try slutty clothes on me.

  2. It was when I was 25, and at that time, I didn’t have a girlfriend, and masturbating wouldn’t cut it anymore. I wanted to feel the touch of women, And for some reason, I was grabbing my mom’s satin panties, and OMG, what a great feeling it was, the softness, cooling sensation, and the looks. Then thank God to Amazon, and leaving alone, my fun started.

  3. I can remember with my sister’s Barbie head at age 9 as well as dressing in some of my mom’s and sister clothes as a teenager. I also went to work dressed as a woman back in 2001. I have also done some female things like having my eyebrows waxed or my nails and a pedicure.

    1. One of my dreams is to have a girlfriend/ gurlfriend/ ts friend to do my nails, wax my eyebrows, and do makeup. I wish I could go on vacation for a week out of the country and wholly transform myself into a woman. Somewhere that no one knows me

  4. I don’t remember exactly when my first time was. I know I was a teenager, maybe 15-16, something like that. I took some of my mother’s clothes out of her drawers. Nylons at first. Eventually I found she had a basque… that was quite eye opening. Of course she caught me with her nylons at least once. I don’t know exactly what she thought, but I at least remember I didn’t get into trouble, but we also never talked about it again. That was not the last time I tried dressing. It scared me for awhile, but didn’t discourage.

  5. Unfortunately, I remember my first time. Both my parents worked so after school I would go to my neighbors house for him to watch me till they were home. He worked the grave yard shift so was home. His very petite wife worked afternoons and was rarely home (and left him a month later). Everything was fine and he let me watch whatever I wanted (I was 11). He complimented me constantly on how “pretty” I was and how girls would kill for my eyelashes. He started offering me candy if I would wear some of his wife’s clothing as he thought I would look so good in it. She was petite and I was tall so her clothes fit me. It started with a dress than silky pantyhose and finally her silky panties and teddies and gowns. Of course all of this aroused him and soon he was molesting me and while part of me knew it was wrong, he was the only adult who paid any attention to me so the affection was enjoyable. As things progressed he actually started making me rub his groin or hump against me. When he finally came, he would feel ashamed and get mad at me for “making him make soil her clothes” and he would throw me and lock me in the closet still dressed and wet with him ejaculate until he calmed down. He was a big man and would threaten me if I ever told. I started to dread going home after school and would get off several stops early on the bus and go as slow as I could to get home hoping my mom would get back in time. This went on for almost a year till my father was reassigned and we moved away. The experience both haunted me and enticed me so I started stealing my mother’s lingerie and have been a crossdresser ever since. Luckily, therapy eventually helped me deal with it and separate the desire to dress from the shame of my childhood, but sometimes it still creeps in. Sorry for the trauma, but good to finally write it down and admit it to anyone other than my therapist.

  6. Recently made myself publicly known as a trans woman. Admittedly hand picked who I’ve told and the rest have seen for themselves.

    After several years privately in the safe space of my home living as female. All relationships I’ve had have known who I am but always a looming concern that I’d be outed be a scorned ex looking to cause a stur. I recommend self reflection and not to run until you’ve learned to walk or in other words if it’s becoming overwhelming plause and take a moment to compose yourself.

    Last year I knew that the dream had potential to become reality that it can happen, I can be my true self, I can be the woman that I was supposed to be born as. By the end of the year I was desperate to find the words telling me that’s OK it’s allowed even. Like many I’ve come across so many closed minds on such matters to be left with the idea that going against what is considered social norms were wrong. This site as many may agree was the key to making me a reality. Relationships past and present knew my true self but not family.

    On Dec 31st 2021 I read a post by Fiona that gave me the ability to articulate perfectly how to tell my mother. Not only that but reaffirmed what I believed I already knew, I’m not doing or being anything wrong and that social norms in my view is wrong and what needs to change allowing people to be their true selves and stop repressing and preventing people from being held under an illustration that who they are is wrong.

    People are diverse and shouldn’t feel ashamed but proud that they are unique. Embrace who you are and own it is what I say and suggest. Anyway so told my mother and at a steady pace moved forward in a way that always moving forward never needing to do any u-turns. Set personal realistic goal socially.

    First step (early January) was telling people and create a safe environment even test the water so I know what kind of reaction or unkind reaction to expect at my local bar. Second step (late January) make true on my words. So began finally presenting as female but at a low level so for example hat with long wig leading people I’ve not directly told to ask questions, usually “i didn’t know you had long hair” the answer i gave was this “i dont and I’m transitioning mtf.”

    I did have a back up answer to people who I was unsure of and didn’t need to use thankfully which was “there’s a lot you don’t know about me”. Third step (early February) tastefully totally present as female. Ok but that’s just at the bar. Fourth step (mid-late February) present as female wherever I go til the end of the month. Yep scary but somehow it was working. Got overwhelmed, in a good way but needed to ground myself so I was doing a lot of processing when at home cos if I told myself a year ago at this point or even 6 months ago that I’d be presenting as female even just for one day I wouldn’t have believed even myself, not only is this the goal but felt like a dream to the extent that I felt like I was in a dream hence the self reflection and grounding myself.

    Fifth step (March) now grounded. I did part of February presenting as female in public but it was a trial meaning if I had to or if I got too much I could allow myself to step back, after all I had no idea what the unknown had in store for me. Told myself move forward slowly to prevent having to step back. Didn’t need to step back just ground myself when at home. Now March ok new goal- the whole month but this time the trial is over and disallowing the option to step back. Live fully as female only. After grounding myself in February that goal didn’t overwhelm me.

    It’s now mid April the idea of presenting other than female makes me feel sick to be honest. Therefore all male clothes are gone only kept what is unisex or what can be upscaled into feminine clothes. I did say to myself I was gonna take it slow and in the scale of things to come i actually have. Just to step out the door as the real me who I should have been born and always lived as was massive and the hardest thing I think I’ve ever done. Was it worth the risks? Totally.

    I’m feeling more complete? Yes but only more complete – not fully yet. I’m getting by but most importantly I’m going in the right direction for where I feel I should be and want to be. Still a long way to go. Someone said they have forgotten how I used to look which is also good. This is me now and always will be (and always was) I pushed my comfort zone and to say I don’t regret it is an understatement.

    I posted this to share and hope this can be of help to someone, I confess I don’t know why or how it worked out this way for me and never ever thought it would or even could. All I can say is try and be the most honest truest person you can be not only to others but to yourself, no one can take the true you away from you and no one has the right to even try. Where possible be you and stay true xXx

    1. Your story is amazing . The slow month by month description showed your vulnerability. The anxiety well described… I’d like to know more about the first time… as you went home… walking in the door realizing you had no reason to look back or change back to the person you were. How that freedom felt…. ❤

  7. Hi. Just a follow up on previous post that i hope helps people. For years I knew who I was. Couldn’t articulate correctly how to express who I am until found this site. 2021 I knew I had to try and and shifted gears to make this happen. 2021 was preparing with imagination? Meaning I tried to visualise it happening in reality to the best of my ability. However 2022 walking it in reality is slightly different.

    Things i didn’t consider til I walked the walk. Here is some things I didn’t anticipate and found some solutions to that may help. The following tips are my personal experience and solutions in did to compensate. -Shaving, beards/facial hair that is. Women in general don’t require a shave. Transfemenine and men who don’t want a beard shave and then there’s that cut off point from beard to head hair we use the razor and cut a nice neat line. Again women in general don’t need to shave, therefore they don’t have that neat line cut off. My tip- shave under and allow the side of hair to grow over creating a “whisp” effect. Not only that if you wear a wig by doing this and grow the sides of your hair you’ll create a blend from natural hair and the join of the cap of the wig at the sides. If the wig matches your natural hair color it will create a near seamless blend. This works best if you wear a shorter length wig and 1-2 months of hair growth you should get that blend. Also a shorter wig doesn’t tangle. A cute bob cut looks great. A layered wig looks as good as a bob and will meet the blend better and quicker. As your natural hair grows then go longer length wig maintaining that natural looking blend. Longer wigs- harder to maintain- shorter life span. Constantly tangling? Reason is wigs are manufactured and each hair is same length. Naturally grown hair breaks therefore not same length and tangles less. By layering a long wig can minimise this and you can keep the same length and look and will give your wig a bit more life span. Wig partings- look un-naturally too neat. A careful pluck of the parting line to look less neat and looks more natural. Wig slips? Many wigs are adjustable however if you go too tight to prevent it slipping the back of wig gets gathered/bulky and slightly out of shape. A silicon band can minimise slipping and allow you to not have to adjust as tight minimising the gather at the back. These are a few things that I came across stepping out after initial planning that I failed to anticipate.

    I hope it is of help to those who recognise these issues or if thinking of transitioning could be worth considering. At this point I could say thats it take care etc. However something took me by surprise in my own personal journey and this is a page to share such things. When I first came out as a trans woman i could have took the advice of a trans woman friend. She said grade one your hair with hair clippers and that will grip your wig better. Now this is a tip that works for her and like many is dependent on wigs due to total hair. However I have only recided at the front of my hair and yes wigs were also my solution and wigs changed everything. If it wasn’t obtaining a natural looking wig I’d probably never found a way to see a way to transition. My opinion was my wig is covering my hair so why not just let it grow, no one can see it under the wig, why put all your eggs in one basket by cutting it off with clippers, how ever unlikely something could come about and need my natural hair. Did i ever. The silicon band was the unexpected key. A girl I met recently suffers with Alopecia and changed everything. The way she deals with it and chooses to stylise herself was amazing and truly inspirational. A shift in perspective came. Yoga workout headbands. Covers the front. So no more back story I now do the following- I didn’t cut off my hair as I said and let it grow and now it was just long enough to do this and I’ll continue growing it. So it’s now my own hair on display. Silicon band holding my clip on bangs in position (which like wigs matches the color of my natural hair) unpicked the hair clip part as it’s being held by silicon band and can create a bump which is minor but better without. Then to cover the silicon it’s topped off with the yoga headband which is also held in place by silicon band.

    This course change was totally unexpected but thank god I didn’t cut my hair off. Bangs are optional but better with. I intend to grow my hair so I can have a high ponytail. And yes I’ll probably look like a yoga instructor by the time I’m complete. But in my opinion that’s a good look. I share in the hope this could be of help allowing someone create themselves. Total admiration and respect to you all – be you, stay true xXx El

  8. Hi all.
    The woman within me is called Sarah.
    She has only ever existed in the mirror. There is a huge reluctance on my part to let her out.
    Fear mostly.
    As I take these tentative steps, I’m embracing any advice on offer.

    1. Hi Sarah. The mirror can be a reality. Let yourself out. Maybe not yet??? But if never, you’ll never know what could have been or could be. Baby steps are still a forward direction. Personal I’m shocked by the positive responses I received by showing the word my true self and regret not stepping out sooner. Yet all paths are different and only you know when is right. I hope you take at least a baby step or more and allow as much as you’re ready for to embrace a future for yourself. I do suggest spend some time preparing yourself firsthand and if/when you decide your ready… own it. As for fear, I don’t know your area and just maybe others like you could advise you on what to expect. If not before try going to an LGBTQ+ bar and meet others who could help you gain better advice. Also a good stepping stone technique to go there as who you wanna become and gain confidence. Maybe take a bag of clothing to change into if you feel safer doing things this way.
      Hope this is helpful. Been there sweetie and hope it works out for you. I’ve wrote a bit before and if you’ve not read it maybe glance over it. Could have something useful for you there. X

  9. My first time was when I was 4; for some reason i had no socks and my mum made me wear my sister’s white knee high girlie socks. They felt wonderful and this launched me on my journey. A year later my sister thought it would be fun to dress me up as her little sister. I made unconvincing protests and loved every minute of it. It’s hard to know why we do what we do, but I am not ashamed or embarrassed by it and fortunately I have a very understanding wife. I now fully dress most days, but always wear lacy underwear, even when presenting my male self. I just don’t have the confidence to come out to the world at large…..things to come.

  10. I am new to the crossdressing scene. Nobody yet knows, but I plan to tell people in time.

    I have secretly been interested in crossdressing for years. I found this website and have signed up to be on of Auntie Kittie’s Good Girls. I can’t wait to start my journey

  11. Hello Fiona and other ladies,
    Does any one know of CD friendly and welcoming to first timer bars/cafes in the greater Brussels area?
    Any suggestions would be really appreciated. I want to go out soon, but of course, the first time needs to be to a safe place. I will of course report back (if) when it happens.
    Ciao darlings
    Christine

  12. Hello Ladies, I have just joined Fiona’s Premium Program and I want to comment on my experience with task1. I already keep my dresses, wigs, hosiery organized, and in fact I have small bag with makeup, a skirt, top, pantyhose and flats – it is what I keep ready for when I have a makeover booked. But the part of the task that I found most powerful was the suggestion to “take a moment and think of someone desiring you”. I got dressed last night and thought about that.

    Imagining someone being aroused by looking at me got thinking about why I dress feminine. To keep it simple, I think I dress en femme because I want to feel and look like a beautiful, sexy woman. And what better validation is there than a man, or another transwoman, or whomever thinking you are sexy?

    When I first started dressing I was afraid to look at men when dressed, and I was extremely self-conscience when they looked at me. This was probably the residual impact of the homophobic atmosphere I was raised in. But over time, I started to love the looks and the compliments and the suggestive comments.

    I liked the task because I believe being desired is one of the greatest outcomes when you put in the effort to look feminine and beautiful

    Kendra

  13. Hello again girls,

    I now want to comment on Premium Program task 2. I have previous experience buying panties and hosiery of course – but I usually buy them on line, or I buy them in a department store when I am also buying men’s briefs and socks – so the clerk will think the panties are for my spouse. Having been given the task of buying panties in person, this time I went in and bought a three-pack of black panties and a three pack of coloured panties. I didn’t buy anything else. The clerk did not say a word, and despite my anxiety – it was a non-event.

    I am assuming the point of the task is to become braver about our femininity, and it did feel somewhat liberating to realize I don’t have to buy a pair of men’s briefs every time I buy a pair of panties.

    Another part of the task is to imagine someone with you when you put on panties, pantyhose, and other feminine things. I love that part of the task – imagining being desired for one’s femininity is very intoxicating, very satisfying.

    Kendra

  14. Hello Girls,

    I just came from my first yoga class so I thought I would report on task 3 of the premium program. It was a community centre class and most of the participants were women in their 40s and 50s. I did not feel completely comfortable, in part because yoga is new to me, and in part because most of the women were quite friendly with each other. Thus I felt like an outsider.

    But the exercises, stretches and positions themselves were amazing. It was uncomfortable, but the stretching of my hips, hamstrings and lower back felt wonderful. I felt more mobile and alive after the exercise and since I am an older crossdresser who still plays sports – I am going to stick with yoga and maybe find a higher end class. Girls, in addition to whatever benefits it has for expressing your feminine side, it is just good for your body and mind.

    I didn’t spend a lot of time observing the other women and how they moved during class, because I found it challenging enough to simply attempt all the positions. But I absolutely noticed some very attractive women in very attractive yoga pants, and I did fantasize about buying some. I just wore shorts and t-shirt – but I will how it goes – maybe one day I will try to find androgynous yoga pants to wear. Once I get more comfortable I believe I will be better able to see how yoga can improve one’s femininity as well as one’s flexibility.

    I also want to comment on a couple of other suggestions by Fiona. Yesterday I used a feminine vanilla scented body wash in the shower and put a touch of Dermablend foundation on my face despite the fact I was going to be in masculine mode all day. I have not previously tried to do anything androgynous and although using a vanilla body wash and wearing undetectable foundation does not sound like a big deal, this is first time I have ever combined masculine and feminine presentation. I regularly wear tights under my masculine clothes, particularly in the cold weather, but there is no risk of “being caught”. No one mentioned either the foundation or the feminine scent – but I was keenly aware all day that they might have.

    It was an interesting experience, and this is a very enjoyable ride.

    Thanks Fiona

  15. OK , here is my Story…

    I have loved all things Feminine for as long as I can remember.
    I first noticed I loved girly things when I was very young and enjoyed playing with Paper dolls and changing their outfits. I thought it was magical and the pieces of paper were so beautiful.

    Years went by and once at a high school Party at some girl’s house I found myself in the laundry room next to a basket of clean panties, so I took a couple of pair (sorry I know) and shoved them in my Pocket. I quickly said my goodbyes and stopped in a store to slide into the restroom to try them on. They were simple cotton yellow panties with delicate white lace. They felt glorious. I kept those panties for a while slipping them on at night when I went to bed while living at my parents’ house.

    Fast Forward many years, I found that my professional career had me traveling for work that would result in evenings and some weekends alone in a hotel. This was around the time the internet came into its own. That is when I discovered the term “Crossdressing”. After researching I discovered that I wasn’t the only male that had this desire to wear Silky lacy things. I decided to go to a local store (of course out of town) and purchase some items. I remember how nervous I was, butterflies filled my body.
    Eventually, I bought tops and hose, but never an outfit, just a mismatch assortment of clothing. I had so many different items I had to buy a separate bag to travel with. I had a wig, breast forms, make up all sorts of stuff. But I was never happy with my appearance and one evening on my arrival back home, I stopped at a dumpster and tossed it in and was done with this silly thing…

    A few years later, I couldn’t fight that urge and while on a trip bought some silky panties and camisole. This time not so nervous. The cycle started again, and I ended up leaving the items in the hotel trash being done with this silly thing. But the desire for feminine clothing remained.

    Fast forward to the present. While scrolling through Tumblr, I saw a post about Fiona Dobson.com and started reading. It was a relief to read the information there. It was a like a new world opened for me. I knew the store I needed to visit to find clothes to fit me (I’m a big gurl), got detailed measurements and ordered the cutest super soft sweatpants and top. It fills wonderful. I also bought a button up dress that I am wearing as I type this.

    I consider myself a male that enjoys wearing women’s clothing. I am married for 25 years with 2 grown boys. I am not gay (whatever that means), but I have enjoyed the touch of a man, and I did enjoy it! Does that make me Bi? Probably but who cares, I don’t. I still just dress for myself when alone on a business trip and may always. But we will see.

    If you read this whole thing, Thank you.
    I could write a novel about this journey I have been on.
    This is the first time I have told this story to anyone and needed to get it out.

    -Samantha

Leave a Reply