Quite a while ago, I discussed the fact that I rarely have dreams related to cross-dressing. Until recently, I rarely had dreams at all, or if I did I simply could never remember them. Even when I know I have had a dream, my memory of the details is fleeting. It’s like the dreams are scribbled in chalk onto a brick wall, and as soon as I wake up it starts to rain… slowly washing the details away so they don’t get confused with reality.
I have always felt it was a shame that I had such a poor memory of my dreams. I think it would be very interesting to over-analyze the dreams to see what fears, desires, and loves are represented. My friend Pat had suggested that I keep a dream-log/diary to help prevent the dreams from fading away and I began to do so. Still, I had so few dreams or memories of them, that there was almost nothing to write in my little notebook. Then I had a slight change of medicines, and the dream-factory went into production.
So now recently I have had many vivid dreams. Some have been ultra-personal and others have been a bit risque, so I will keep those to myself. Most of them are not related to cross-dressing, but some of them have been and I thought I would detail those a bit in this post. These are in the order that they occurred, but they were not necessarily back-to-back occurrences:
Dream One –
I woke alone and realized I had slept quite late into the morning. I got dressed in my standard “Bob” gear, and proceeded to go downstairs to see where the family was and to get a cup of coffee. As I walked through the house I kept stopping in various rooms to look at some things. I stopped in the library to examine the various books left open on one of the tables and then stopped in the gallery to examine a beautiful painting adorning the wall opposite the great window. (I suppose I should add that we don’t have a library, nor a gallery with a great window, but it seemed like it was my home as I always knew it)
After a few minutes I heard sounds coming from the kitchen and decided to greet the family. As I walked in, one of my children said “dad’s finally awake” and my wife turned away from the stove and said “good morning”. I was about to respond when I froze in my tracks. My wife was head-to-toe decked out in one of my Valerie outfits…. cream colored silk blouse, navy blue skirt, 3.5” heels, and a lovely set of pearls. Over the skirt was one of my aprons, protecting her (my) skirt as she cooked breakfast. She looked at me strangely and asked me “what’s wrong?”. I said something to the effect of “I have just not seen you in that outfit before”. She replied that she had found several outfits like this in the closet and they obviously had to be hers, so she decided to wear it. My daughter stated she didn’t like the outfit and it seemed like something you would see in an old movie.
At that point I remember getting a plate handed to me, but the rest is fuzzy. Then I woke up. Not exactly a cross-dressing dream, but one that gave me shivers since I previously hadn’t dreamed very much. Strangely enough, I don’t recall liking the outfit on my wife, although I always assumed I would like my wife dressed in a Valerie-type style. Also, we are not the same size (unfortunately) but the outfit seemed to fit her as if it was tailor made for her.
Dream Two –
I once again awoke in my bed alone, and proceeded to get dressed. This time around I put on a blue/white polka-dotted dress with blue heels. I checked my hair and make-up in the mirror and they were perfect (even though I don’t think I had put any on after waking) and proceeded to go down stairs.
I walked into the kitchen and found no one there. I proceeded out into the living room and there were my children. All looked up and gave me a strange look. I recall sensing panic as I realized I was dressed as Valerie in front of my children, who had never seen me dressed. My oldest called out “Mom, you had better come in here” and I started to run away. Before I realized it, I was going between two houses in my neighborhood looking for a place to hide. A door opened and an ex-girlfriend yelled for me to come inside. I ran in and she said they wouldn’t look for me at her house. (This ex does not live anywhere close to me and I can’t say I even recognized the house.)
The ex looked me up and down and said “I knew it all along”. The she said something to the effect of she liked me this way better anyway. She then stated we were late and needed to get going. We walked out to her car and drove quite a distance to a building I didn’t recognize. We got out of the car and we walked into the lobby of an office building. She then said “I’ll see you after work, and have a good day”. Then she disappeared into an elevator. I didn’t know where I was, had no car, no phone, no purse or wallet. I just remember feeling stranded and helpless. I don’t remember much else and woke up soon after.
Dream Three –
Both my wife and I were getting ready to go out. She was wearing tight jeans, a sweater that showed off her curves well and some boots with a modest heel. I was wearing a typical Valerie dress with a full skirt and heels, but this dress was really low cut and I had some impressive cleavage showing. I was doing my make up and she said that I looked really pretty (not something my wife would say to Valerie). As she finished, she said she would wait for me downstairs. I finished up and grabbed my purse and headed downstairs to meet her.
I don’t remember anything about being downstairs or any interaction with my wife at this point. My next recollection is sitting with her in a movie theater. I tried to recall what movie we were seeing, but all I can remember is there were horses on the screen. That’s all I could piece together.
My next memory is being at the entrance of a bar, and the doorman asking us both for our ID. I have not been asked for ID for many years, and was a bit surprised. My wife handed her ID to the doorman who said “thank you ma’am” and then he looked at me. I remember being a bit nervous about this whole process and my wife said something about hurrying up. I reached into my purse and found my ID, and was pleased that it had my name as Valerie South and the picture was also of me in Val mode. He also said “thank you ma’am” to me and we went inside.
We were sitting at a table and already had a couple of drinks in front of us, when a man asked my wife to dance. She said no and explained she was married, and the man left. A short while later he returned and then asked me to dance. Like my wife, I started to explain that I was married and not interested. My wife interrupted and said “you’re not married”. Then she looked at me and whispered “you don’t want to look out of place” even though I am sure I already did. (actually, the way she said it I would have to think he would have heard her also). Then she said in a normal voice “one dance won’t kill you”. In a bit of a panic I was being led out to the dance floor. I remember feeling scared and a little upset that my wife pushed me into this, and I turned to look back at her to signal I needed help getting out of this. Instead of watching what was happening to me, she was gathering her things and walked right out of the bar. More panic and I suddenly woke up. I tried to remember if I followed her or what happened, but I think I was immediately conscious as soon as she had left.
I did not enjoy this dream. It wasn’t quite a nightmare, but the sense of panic, fear, vulnerability and sense of abandonment was truly unsettling.
Dream Four –
I was at work and in full “Bob-mode”. I was in some sort of training or seminar setting. There were presenters rambling on about some work related material and I couldn’t begin to tell you any of that detail. Charts were being flashed on screens and I remember not recognizing most of the people present. One of the presenters asked a question and the majority of the people raised their hands to indicate their agreement with the statement. I didn’t know whether or not to raise my hand, since I didn’t know the question. I remember thinking I had better pay attention before I get into some trouble with my superiors.
So with a renewed sense of focus I continued on listening more intently. One of the female presenters then asked the group “So how many of you here are cross-dressers?” Without hesitation I raised my hand, only to find I was the only one (at least who admitted it) and I immediately felt I had made a mistake in admitting it. One of the other presenters then started to make some notes and kept looking up at me periodically. I put my hand down and looked around at the faces of the other attendees. Most looked either amused or that they could care less about anything going on in the seminar. I woke up quickly after that.
I barely consider this to be cross-dressing related, but I did raise my hand when asked. Shorter dream, but I spent a lot of time wondering what this might say about me and my real life mindset.
Dream Five:
I was busy cleaning up the house and my wife was asking me to move some things around in preparation for some guests. It was my house, but there was a lot of clutter and several pieces of furniture that were not something I had ever seen before, but like in a few of my other dreams, it seemed so normal that I didn’t question it until reviewing the dream later. Anyway, when the room was set to my wife’s approval, she disappeared to get changed and asked me to keep an eye on the food in the kitchen.
I went into the kitchen and the only thing I could find were some store bought, prepackaged, mass-produced, over-processed, chemical crap snacks that my wife detests. But I kept an eye on them until she returned. Having changed into a really beautiful dress, she came back into the kitchen, and said thanks for the help and she was really feeling rushed getting it all together. I had no idea what the whole event was and after seeing her in the dress, asked if I needed to change into something a little bit nicer. She said I needn’t bother since it was only for her and her friends. Fair enough I thought, and went into another room to do something.
A short while later I heard guests arrive and recognized several of my wife’s friends and coworkers voices. A little while after that, my wife called out for me and asked me to come into the room where they were meeting. I went in and found they were having one of the typical “Mary Kay” cosmetic parties, where the rep comes and tries to sell you and all your friends their beauty wares, giving the hostess many discounts and freebies for arranging the captive audience. I did not recognize the “Mary Kay” lady and as soon as I entered the room she looked at me and said “perfect, she’ll do fine”. I asked what did they need, and was told they needed a blank slate on which to apply some makeup and show some techniques, and my wife had volunteered me to be the demonstration subject.
I don’t remember great detail of the makeup application process (dammit!) but once done I was amazed at the face looking at me in the mirror. Totally feminine and beautiful and honestly looked nothing like me when done up in Val mode. Several of the ladies said that if she could make me look that good, then they wanted all the makeup she had used for the demonstration. I told my wife I would like her to get it also, but she said she had already bought some different items. I told her to get these specific items for me and she looked at me strangely and said “whatever for?” as if she had no idea about my femme side. With a room full of her friends and coworkers present, I was in no position to explain or justify my desire for the makeup to my wife. Feeling disappointed and somewhat hopeless, I woke up soon after (with no makeup on).
Dream Six –
I was sitting at my desk and nothing seemed out of the ordinary, until I was called into my bosses office. I got up and started to make my way to her office and as I walked I recognized the clicking sound of heels on the tile floor. Sure enough I was wearing a very tall set of heels instead of my “Bob” work shoes. The shoes were hideous really… orange with big flowers stuck on them at the toe. I looked around to see who might have noticed and nobody was giving me or my ugly heels a second look.
When I arrived at my bosses office, she told me to come inside and have a seat. I did so, and instinctively crossed my legs leaving one shoe in plain sight. She commented that I had great taste in shoes and then walked out from behind her desk to show me that she was wearing an identical pair. She asked if I had also bought the matching purse, and I had no idea. I told her “I don’t think so”. She then went to a closet and retrieved a cardboard box that was a similar orange color and had a big flower stuck to it. She then handed it to me.
I opened the box to look at the purse inside but found it was just a box containing her personal items. She then became very angry and said it is very rude to look inside a woman’s purse without permission and that I should know that. (In case I am not being clear here, the box was the purse… even uglier than the shoes.) She told me that she would be sure to let my wife know about my rudeness and that I had better get back to work.
I left her office and attempted to walk back to my office, but I couldn’t find it. I kept going down hallways and everywhere I turned was unfamiliar. I was totally lost. I was looking for anyone so I could ask for directions, but couldn’t find anyone. At some point in the wandering process, the office building had transformed into a hospital… long sterile corridors. The hallways were empty and the clicking sound of my ugly orange heels was very loud. I continued to walk around aimlessly until I woke up.
Dream Seven:
I was sitting with my wife in our living room. We were watching television and there was a wedding program on. My wife asked me if I was disappointed about being in two weddings this year, but having to wear suits. I told her I was, but that there was no other option. She then asked me if I wanted to be a bridesmaid at her wedding. For some reason I never questioned the “her wedding” portion of the question and just immediately said yes! She told me she was excited and very please I had said yes.
She then pulled out some photographs of the dresses she had been considering, and they were all ridiculously full skirted (even for me) southern-belle type dresses. Even Scarlet O’Hara herself would have had trouble navigating a church aisle in these beauties.
Not as full as they were in the dream, but you get the idea…
She told me they were custom made and I would have to get measured with the other girls. I don’t remember acknowledging this but the idea excited me. She said they would also be taking measurements for my bikini and sandals (huh?? but again I didn’t question it).
After we looked through the dresses, she said she had to find out if I was allowed to be her bridesmaid before we do anything else. She explained she had a meeting with the mayor of our town later that day and would find out for sure. She left the room and I heard the phone ring. I started to look for the phone and woke up to the sound my phone ringing.
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So there you go, seven of my recent cross-dressing related dreams. As of the time that I finally finished this up I have already had three more, so it is showing no signs of letting up thus far. I spent quite a bit of time writing these dreams down and rereading my notes. Several times going through this exercise I would find another detail that I had forgotten and would expand my notes. What I wrote in this post about each dream is just a condensed summary, or this post would have gone on forever. Presented here are the basics.
I am not sure exactly what this might tell me about myself, or if it just more mental gibberish pouring out of Valerie’s subconscious. I do have some theories and some ideas of what may have contributed to some parts of the dreams. However, I know that I can never be absolutely sure of any of it.
I will say this, if nothing else this whole dream exercise has been very enjoyable so far. The dream diary suggestion has been key to me pulling this off (thanks Pat!). I have been able to remember details for much longer than ever before. Not all the dreams have been wonderful, but I go through the same process anyway. If you have never done this before, I highly recommend it to each of you. It is personally rewarding and a definitely insightful. The only down-side to it all is that now I have something else that need to keep hidden from the world and need to be careful I don’t leave it where it can be found by the wrong people…
“Dream on, dream on, dream on… Dream until your dreams come true”
-ValS
So Very Deep (In The Closet) 
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