…with boughs of holly


It’s my second Christmas here on So Very Deep, and so it’s also my second opportunity to wish you all a Merry Christmas (or Happy Christmas, depending where you are)! Just like last year, and every year really, I want to wish everyone peace and good fortune in your lives and with your loved ones.

In the spirit of the season, take the opportunity to do something kind for someone that you don’t know. It doesn’t have to be something major, just something that you wouldn’t do in your everyday life. Go above and beyond your normal generosity. Make a point to do it. Pay for someone’s meal, offer to help someone in need out in some way, etc. Don’t overthink it, an opportunity will present itself and you will know this is your chance. Just do it and you can cuss me later.

The point is I always feel that people have the power to generate a positive spirit and it becomes infectious, and right now the world could use some extra goodness!

So once again I will leave you with some fabulous Christmas images, Valerie South style!


Love you all,






Casa Susanna


By now, most of you know some of the main things that make Valerie South tick. Unless you are new to So Very Deep, everyone knows that 1) I am a cross-dresser 2) I love 1950’s fashions and vintage items, and 3) I constantly search for (and collect) vintage/1950’s photographs and images of women and clothes… many that I feature in my posts.

When you combine all of these things and add in the power of the internet, it’s no surprise that I regularly happen upon references to ‘Casa Susanna’. I decided that it was time that I further immortalize the Casa in my blog, and introduce everyone to the support group I was meant to be a part of, but somehow missed by about 60 years.

In the 1950s through the early 1960’s, Casa Susanna became one of the first retreats for transvestites. It was located in Hunter, New York, which can be found in the Catskill mountains of New York state. Located on a 150 acre property, Casa Susanna consisted of a main house, surrounded by several bungalows/cabins. These bungalows were originally let out to summer vacationers (think Dirty Dancing maybe?) and occasionally to some hunters and other groups in the off-season. As the location began to lose favor with those summer patrons, that is when the “ladies” began to visit most weekends.

In an era when gender roles were extremely narrowly defined, Casa Susanna provided many cross-dressers and trans* persons a safe place to escape to. A place rarely found in the time period, that allowed them to express themselves without the negative pressures of 1950’s/60’s mentality. I love the time period, but as we know there was little to no tolerance for any flexibility in the gender binary.

Casa Susanna was run by one Susanna Valenti, who’s wife coincidentally ran a wig store on 5th Avenue in Manhattan. It was through the store that the ladies began to find each other and eventually found their way to Casa Susanna. Others found Casa Susanna through a home-made magazine called “Transvestia”, which was founded and mainly written by one of the initial visitors to Casa Susanna, known as Virginia. Susanna reportedly also contributed articles to “Transvestia”.

Besides Susanna Valenti ( a court translator) and her wife Maria (wig store owner) , we now know the main group of regular visitors to Casa Susanna included a professional pilot (Felicity), a businessman (Cynthia), an accountant (Gail), a librarian and editor (Sandy), a pharmacologist (Virginia – founder of “Transvestia”), and a newspaper publisher (Fiona).

Casa Susanna largely stayed a secret for years, and after shutting down in the early 60’s remained hush-hush, with the former members keeping knowledge of Casa Susanna to themselves. Then, sometime in the early 2000’s, an antiques dealer named Robert Swope came upon a box at a flea market in Manhattan. The box was full of pictures taken of the ladies at Casa Susanna and he ended up publishing them in a book around 2005.

Much of the inside story of Casa Susanna remains secretive, but after the publishing of the book of photos, several former members came forward to tell some stories. Most remained anonymous, but told similar of similar experiences… just being able to dress up and do normal things such a cooking, playing games, and sitting around talking with others of similar mindsets.

I may not have all the facts perfectly straight, as the photos are much easier to come by than the history and story of Casa Susanna. I keep looking deeper for more details because I am fascinated by the entire existence of Casa Susanna and the ladies who visited during its heyday. I will leave you with some of the images to peruse. I can’t help but feel that I missed out on this experience. Sometime in the future I may find myself traveling through the Catskills, dressed as Valerie, just to pay homage to these ladies.






Not all vintage things are glamorous and each new year we (hopefully) get better


It’s no secret that this cross-dresser has a predilection for things both feminine and vintage, especially from the 1950’s era. From clothes to make-up I love the look from that time and it has a big influence on all things Valerie.

In a recent conversation with a wife of a cross-dresser I have known for quite awhile, she commented that there was very little she found appealing about the era and was genuinely glad she wasn’t born into it. Her main issue was the general repression women were subjected to, and the extreme lack of opportunity.

Honestly I agree whole-heartedly with her assessment of the era for women. I love the idea of being a 1950’s housewife, but that is purely my choice. I might feel differently if it was automatically forced upon me solely because of my gender. I guess it’s similar (to a degree) to how much I hate the idea that I can’t wear the dresses and make-up I would like to because I was born a male. Gender shouldn’t limit any of us or force anyone into a predetermined role… then, now or in the future.

Many cross-dressers feel they have an insight into the world of women that the average guy will never ever have. I am one of those CDs. I understand why women do some of the things they do and like some of the things they like, while many of my guy friends shake their heads and complain that women are just crazy and unpredictable.

So with that insight or just enlightened feminine awareness, I am frequently reminded of the less than ideal situation many women found themselves in during my beloved 1950’s. I spend quite a bit of time exploring the era through archives and images, and some of the things I find are not so pleasant. Nowhere is it more evident than in some of the advertising from that period. So after that recent conversation and since we are now ushering in another new year (i.e. moving forward and making progress), I thought it would be worthwhile to share some of those images I have come across. These are not necessarily all from the 1950’s, but you will get the idea:

That'll teach her!!

That’ll teach her!!

Yes, we know they're all stupid, but it is still illegal.

Yes, we know they’re all stupid, but it is still illegal.

So that's why the beautiful ones always smell so bad.

So that’s why the beautiful ones always smell so bad.

Good thing he's able to figure this out for her!

Good thing he’s able to figure this out for her!

Don't do it for yourself, do it for your husband!

Don’t do it for yourself, do it for your husband!

Well, she does project well but...

Well, she does project well but…

"...I'm bound to bungle up the budget." That attitude would make me feel a bit "punk" also.

“…I’m bound to bungle up the budget.” That attitude would make me feel a bit “punk” also.

Yes! A wife is always to blame!

Yes! A wife is always to blame!

"You seem to thrive on cooking, cleaning, and dusting..." LOL!

“You seem to thrive on cooking, cleaning, and dusting…” LOL!

"Gran Prix Enterprises" Coincidence? I don't think so. And why is the men's version a dollar more??

“Gran Prix Enterprises” Coincidence? I don’t think so. And why is the men’s version a dollar more??

Damn right she should question herself!

Damn right she should question herself!

If these don't show her it's a man's world I just don't know what will.

If these don’t show her it’s a man’s world, I just don’t know what will.

So... that's what wives are for... Love that smile!

So… that’s what wives are for… Love that smile!

So there are a few things from yesteryear that I am not a fan of, this attitude and advertising being a big one…

So anyway, Happy New Year to you! I, for one, am looking forward to this new year and all the potential it brings!


No tea party and fourteen other thoughts


It had only been about 10 months since I was able to be completely Valerie last, but it felt like a lifetime. I was finally able to put that streak to rest this last Thursday and Friday and become completely Val, and it was so much needed for my sanity. My body and soul back in sync as much as is possible, in a way not many people will ever understand.

It had not been easy to pull off. Getting time off work, time without my lovely family encroaching in the increasingly rare free time, seemed to be repeatedly out of reach. But once I was able to become fully Valerie, my world centered itself and an extreme sense of peace returned to me. It is completely therapeutic for me. I think all men should give it a try at least once in their life, although I realize only a special few us will love it like I do.

Body hair gone, nails painted, make-up done, body reshaped (as much as humanly possible), and the poof of a petticoat in full bloom. Life is good, and the smile on my face is back! I can only describe it as being “born again” (excuse the blasphemy). The closet is small and confining and getting to be Valerie for a little while IS THAT LIBERATING!

But in between all the “I feel so good” moments (of which there were many), there were several moments of reality that are worth mentioning. None of these things are worth a complete post to explore, but are more like little observations while venturing into the femme’ plane of existence that co-exists along side my reality. Here are Val’s 15 little things:

  1. In the weeks and days leading up to my days of dressing up, I get genuinely excited. I don’t mean just looking forward to it, I mean kid at Christmas sort of excitement. It starts to consume me. I get giddy. It is sort of bizarre. I don’t think I really get this excited about anything in life like I do when there is a visit from Valerie on the horizon. How funny!

  2. On the day of Valerie’s visit, excitement almost becomes irritation. It seems like things begin to drag on and I just can’t finally get to femme up. This time it was my daughter dragging her feet and announcing she was going to be leaving the house later than usual. I am not proud of it, but I really felt like she needed to get her act together and get the heck out! LOL! I wasn’t that bad really, but I was pushing to get her moving so that I could begin to transform. This is just my typical reaction as the excitement begins to explode.

  3. As I get older, my eyesight is getting worse. This year it seems to have deteriorated to a noticeable new low. Getting done up with worsening eyes was tough this time around, from shaving legs in the shower to doing eye make-up. This is the first time I have ever thought about possibly getting contacts. I’ve got reading glasses, but I think I may be getting beyond that now. Bummer…

  4. Remember those false eye lashes I decided to try out this year? Probably not. But I will be forgetting them going forward. I did give it a shot this time around, but they are just not for me. Between the difficulty of gluing on the lashes and my worsening eyesight (see comment #3) this did not go so well. Way too much work for me to realistically add this to my Val repertoire, not too mention the look is just far too “drag queen” once those babies are on. They were fun to play with, but the experiment is over.

  5. My latest wig is great. It is a much better quality than any I have owned before it it shows. When it comes to wigs, I do think you do get what you pay for. I still think I look like my mom and that gives me some other issues to deal with, but the overall look is great and I am pleased. I guess I am my mother’s daughter.

  6. I bought some eye make-up to try to get the professional “smokey eyed” look. Unlike the false eyelashes, this experiment went well. The look came out well and it definitely will become my regular look for the foreseeable future.

  7. My iPhone is a pain the arse to use when I’m equipped with long red nails. I love the look, but typing a text was a challenge for sure. It gives me an appreciation to the ladies out there that have mastered the talent of living with claws. Yes, I’m jealous.

  8. I have lost quite a bit of weight over the last year, and the effect on my waistline was pleasing. I had much more of the wasp waist effect than I anticipated and spent too much time admiring it. Now I want even more, and I’m not sure that is a good thing. Then again, yes it is.

  9. The bad part of losing the weight is that my wardrobe is affected. My favorite black 1950’s vintage dress no longer fits well, and that makes me a bit sad. Vintage outfits of this sort are not easy to come by, especially in my size (even though it is smaller now) and the clothes are not cheap. This is the unfortunate consequence of getting healthier. If I could just go out to a vintage shop and buy some more outfits then I would, but it’s just not that easy when existing in the closet. This will only get worse as I have more success in losing weight.

  10. We have a newer dog/puppy that is not used to seeing Valerie, and it “freaked” her out for sure! This was somewhat amusing and once I spoke you could see the dots begin to get connected in her eyes. She was still a little uneasy around Valerie, and seemed to keep an eye on me quite a bit. Our older dog gave me a quick look and just turned away as if to say “oh, we’re back to this again are we?”. The animal reactions are entertaining.

  11. As several of us have mentioned on various occasions, I spent a ridiculous amount of time looking at myself in mirrors. Partly because I was pleased with the look I achieved, and partly because to a degree I feel like it is really me looking back. I could chase this much, much deeper, but for this post let’s just say I repeatedly made use of every mirror I could find (and smiled a lot).

  12. I had hoped to spend some time talking with my wife while dressed up, but her work situation required her to go into the office on short notice. I just wanted to sit and have a cup of coffee, tea, or wine with her and have a bit of girl talk, but it was not to be. Hopefully it wasn’t just an excuse on her part. I don’t think it was, but it may have been. It is just nice to have a little bit of human contact when dressed, when your cross-dressing world is confined to the closet. Hopefully we will be able to do this soon. It would mean the world to me.

  13. My male self doesn’t smoke, but Valerie does once in awhile. I went outside to a secluded spot at the rear of my house and had a smoke. Didn’t really enjoy the cigarette, but did enjoy putting on my coat, grabbing my purse, and going outside for a moment. One of the most enjoyable parts of the smoke break was the fact that there was quite a bit of construction work going on at the house next to me. They couldn’t see me, but it did give me a strange feeling to think there were manly men doing manly construction things right next door to me while I was in a beautiful dressy outfit, sashaying about. Clearly felt like a sissy.

  14. The going outside and the issue of losing weight gave me a renewed interest in trying to find a myself a modern outfit and possibly venturing out a bit. This is something I would like to bring up with my wife if we do ever get to have the little girl talk session/tea party. Several recent posts and conversations have put my mind into this train of thought again. Kind of scary.

  15. Last but not least, B-A-L-A-N-C-E! Seems almost cliché to say it so often, but I always come out of a dressing opportunity feeling so whole and balanced. If I could bottle this feeling and save it for later, I definitely would. When life and work stress hit you square in the forehead, and bottle of Valerie’s finest would go a long way to keeping me sane.

So there you have it, 15 points of rambling thoughts. It has already been a few days since getting to dress and enjoy being Valerie completely, and it leaves me wanting more. I am already trying to get another opportunity arranged as soon as possible, before the winter gets away from me.

Being hairless and under-dressing is nice, but it is no substitute to the full blown dressing experience, and I need more.

Until next time…


Modern vintage… beautiful!


I have been traveling a lot lately, and haven’t had much time to read, write or post anything for awhile. But I am now back at home and after some “catch-up” time will soon be able to fall back into my routine of life.

What my travels did allow for was some very interesting conversations with different people from around the world, and their take on life, sexuality and gender was NOT what I was expecting it to be. I found out a few other interesting things as well. I will organize my thoughts on the topics (best that I can, anyway) and post on it soon.

What I did stumble across while away was a great picture of Mila Kunis. You all may know her as Jackie on “That 70’s Show”, or the voice of Meg Griffin in “Family Guy” or even the girlfriend of Ashton Kutcher. What I will always think of her for going forward is this classically inspired Dior advertisement she had done back in 2012.

I always thought she was cute/pretty, but never down-right hot as many guys have proclaimed over the years. But in this picture I do find her to be beautiful! I’m sure it’s the 50’s/60’s vibe that she has that won me over, but I love it.


Usually it’s the classic Hollywood starlets of the 50’s that I both want to look like and find attractive. The modern ladies of Tinsel Town are pretty, but don’t affect me like the classic ladies I reference in many of my posts. Maybe it is as much, or maybe even more, about the clothes and images of the times that attracts me to a woman as it is the woman herself. That is, presentation and personality more than just physical beauty alone.

Anyway, this got a little deeper than I really wanted to go in this post. I just wanted to share the photo and let you see more of what beauty is in my eyes. I hope to see more modern ladies in photo shoots like this. Class never goes out of style!

Let me add… I know I could never get my wife to start to dressing like this, just not who she is. She is a modern beauty and truly my soul mate. Actually, 50’s style aside, I still I own many more skirts and dresses than she does (like 20:1)… and I’m OK with that!


Just a little in the middle


One of the things I have struggled with as a cross-dresser over the years is body weight. I have been up and down for a variety of reasons, but this time I think I am finally headed the right way.

Way back when I first started dressing in my mother’s skirts and blouses, there was a point where my growing male body fit perfectly into her things. The waist sizes, the shoulders, and even the shoe sizes all worked out right. Those were some great times, as I had literally had access to a full female wardrobe. Unfortunately genetics decided to put an end to this as I began to outgrow almost all dimensions of my mother’s things. Sadly, I came to the realization that I needed my own female things, or I would end up ruining my mothers.

One thing I have always been very good at is gaining weight. Actually, it might just be my greatest talent. I love to eat all kinds of foods and that pleasure is only matched by my love of all kinds of beers/ales. With this in mind, I was able to effortlessly put on weight.

Don’t get me wrong, I didn’t really want to gain weight… it just happened. The older I get, there more effortless it became. Now to be totally honest, at one point I liked the weight gain, because my whole physique became soft and round. Even though I was plus sized, there was nothing powerful or muscular about my build. My adams apple was completely obscured (not really very big anyway) and I was able to create some impressive cleavage using a boob belt. All these things helped me to feel exceedingly feminine, but only to a point.

Being brutally honest, I didn’t like being fat. I enjoyed the cleavage, but there was really little else good about being big. I topped out at about 260 lbs (118 kgs or 18 stone, 8 lbs).

I didn’t feel great, couldn’t keep up with the kids in anything, and probably wasn’t too healthy. Any of these realities should have been enough of a reason to make a change in my lifestyle, but they didn’t… at least not by themselves.

I could (and did) get women’s clothes in larger sizes, but they weren’t the feminine articles I really wanted. Once I had come to the conclusion that the fashions of the 1950’s were where my heart was, I started focusing on those vintage skirts and dresses. The problem is that women in the 1950’s were smaller on the average. Most of the items I found and fell in love with were simply too small for my larger frame. It was the desire to get my hands on more of the real vintage fashions that pushed me to lose some weight (sad but true).

So I have been at it now for about eight months, and to date I am down about 55 lbs (25 kgs or 3 stone, 13 lbs). I do feel much better and I am losing dress sizes! I am seeing a much greater selection of vintage items available in my range, but I know there will be even more as I continue to lose more weight. I actually get excited when I weight in and see I have lost some more weight and know that means the selection of vintage clothing is increasing conversely.


One thing that has not escaped my attention is that most of women wearing the fashion I prefer (full skirts and petticoats) have that iconic “wasp waist” look that at this point I could only dream of having. Tight tops, tiny waists, and full, poufy skirts are so enticing to me. That 50’s hourglass silhouette… it is the look I really want, but once again genetics will be working against me. Guys, even ones in great shape, just don’t achieve Barbie doll thin waists.

Betty Brosmer... the original living Barbia Doll.

Betty Brosmer… the original living Barbia Doll.

Truth is most women didn’t achieve those wasp waists without some assistance, namely the corset. So now I am infatuated with the idea of getting a corset and beginning to train my waist down several inches smaller than what I could achieve through normal means. I have just started reading and researching the subject of “waist training” and I have a lot to learn, but I am truly enamored with the idea of wearing a tight laced corset.

This would be the type worn just at the waist, not right up to the breast or under-breast. So far I know that to be truly effective in training, they need to be worn at least 12-14 hours a day (i.e.) almost every waking moment. The idea of wearing one to work is not so ideal, especially when feigning a masculine existence! So I am thinking of wearing one at all times, outside of work and mostly at night. I haven’t quite figured this all out yet, but I gather for some reason wearing a corset at night while sleeping is much less effective. Figures!

Another thing I have considered and not yet figured out how to handle is my wife. I’m pretty sure she will not be in favor of the corset plan. Once I have a bit more understanding, I will have to explore the idea with her. Just based on experience, I am sure she will think I have fallen a little farther down into the rabbit hole and oppose the idea. But we shall see. Of course I still would have to hide it from everyone else in my personal life, and that would still be a challenge. The good news is it should be easier under all the winter clothing that will soon be coming out of the closet, even if I am not.

After writing this, I took a minute to think about the corset idea and all that Valerie has become. Once again I have taken the cross-dressing to a new level (or would like to). Again, I have to wonder… just where will it end?


Moving Valerie ahead a few years

Wow, the future is exciting!

Wow, the future is exciting!

For a cross-dresser that has time-travelled to the present from the 1950s, I am remarkably tech-savvy! For a normal person in the year 2014, I am just so-so when it comes to the modern world. Valerie is just not a girl of the future, but I am getting better!

It’s not that I don’t work with computers and tech gadgets; it’s just that my interests lay in older, vintage, classic things so I don’t tend to explore these modern marvels like some others do. That’s the main reason my wife will not let me help decorate anything in our home, because she’s afraid that we would be living in a 1950’s replica. I have told her repeatedly that while I like those things it doesn’t mean that I would decorate the house like that, but she doesn’t believe me. Once again, she’s right. I wouldn’t be able to help myself and that’s exactly what she would end up with…

One of the things I do when surfing the internet or reading other blogs is read about older vintage things, or explore vintage (mostly 1950’s) pictures and images. I have hundreds of pictures and when I finally finish a blog post, I may spend an hour or so trying to come up with the perfect image to go with my topic. Sometimes it’s completely obvious and other times it may be just a little inside knowledge as to why I select the image I did. Regardless, I hope others enjoy seeing them as much as I like collecting and selecting them.

So while I am a bit slow in getting around to all these tech and social media things (like WordPress, for instance), I am making progress. However, the more I discover, the more I realize that I can use these for exploring vintage things! Look out! My available spare time has just taken a huge hit!

Specifically I am talking about two phenomenons that you will probably roll your eyes at and think “Those old things?? Where has she been???” (you all know the answer to that) I am talking about Pinterest and Etsy! Both are a vintage cross-dressers dream! Since my recent holiday, I have spent hours wandering through these apps/sites gawking at the images I can collect and items I can buy!

These are fantastic! Why didn’t anyone tell me what I was missing?? …oh, yeah… I am stuck deep in a closet and don’t get to discuss such things with other people. What was I thinking??

Truth is both of these gems have given me the opportunity to be Valerie in my day-to-day life. I can sit and peruse vintage purses, shoes, dresses, jewelry, accessories, house-wares, etc., etc. to my femme hearts content, while I am sitting at the tractor pull (kidding about the tractor pull). I can search through virtual store fronts for an actual vintage or replica dress that would make both June and Grace proud. I haven’t bought anything yet, but just window (monitor?) shopping a bit while my mind is fully Valerie is such a wonderful outlet!

I just sit and smile as I look at these wonderful things. So much that I keep getting asked what is making me smile. Besides my wife, I can’t really tell anyone but it must be apparent I am enjoying something quite nice.

On the dark side, these apps/websites are also very addictive. Now I have to consciously avoid looking into them at every waking hour and can’t allow it to become a complete distraction. Initially, I was definitely in a cyber pink fog, but as the newness wore off, I have learned to contain myself a bit.

Another thing that concerns me is the more I get into these apps, the more connected I become. These are definitely forms of social media. You can share your pins on Pinterest and follow sellers on Etsy. While not as social as say Facebook, they are still connecting dots, and that is a concern for someone resigned to living a cross-dressing existence in the closet. Probably just more paranoia on my part, but it does cross my mind.

I have thought about having a Facebook account for my femme persona. However, without pictures (which I’m not doing) can it really be beneficial? Not sure I would get anything out of it that I don’t already get from my discussion forums and my blog. I could “like” someone checking in at a Starbucks, or wish them an online happy birthday! But in the end I think it would just suck up too much of my free time, and connect me a little too much for my own comfort.

But WordPress, eBay, Pinterest, and Etsy are here to stay in my world… at least for the time being. Well, until I discover something equally wonderful?? Truth is, it may take a while to get me to move to anything else. If you haven’t noticed, I tend to be slow (stuck) when it comes to moving to the future! 😉