I decided to see how dead the rabbit hole is and actively engage with the feminine as much as possible to find where the bottom is. I am sure this is something we have all wondered about our crossdressing and would like to know how deep that hole goes. This is a simple enough thing to do and we have two options. Start small and work up, add a little bit each time until we find out limits. Start huge and work backwards, toss out the boxers and live as a woman and scale it back until we find the happy middle ground. Either way will work, but I find the depth of this particular rabbit hole is always changing so both are likely required.
I think there are two major things holding us back from finding the bottom. The first is social acceptance of crossdressing. That is a society wide issue that will take time to work through so I am not going to go into it as much. The other limiting aspect is the fear that we may find we are transgendered and want to become a woman. While this is possible it is unlikely unless you have always felt like a woman and feel the desire to be one. I can tell you that I for one have no deep desire to become a woman permanently. Offer me a pill that could turn me into a woman with a reverse pill of course I would take it, why wouldn’t I want to spend a month or so as a woman? Offer me pill to turn me into a woman with no chance of going back and I would put some thought into it and then not take it. So while it possible jumping into the rabbit hole could end up with you taking hormones and going under the knife it is highly unlikely. But even if that is where it ends up then the worst case scenario is that you then know about yourself and can make adjustments to live your life as happily as possible. So this is a no loose situation.
As such a few months back I decided to take a step into the unknown and push the envelope of what I was comfortable with. I decided to feminize my life to the greatest extremes I was willing. The reason why is simple, I just need to know if I can take it? So what did I do?
I altered my visual appearance nothing permanent mind you. It is winter so I have dedicated myself to keeping my toe nails painted and varying the colours every two weeks for the winter. I actually have enjoyed this as I get a nice little feminine reminder every time I look down and my bare feet. The second aspect is keeping my body hair under control. While I don’t need to keep my entire body cleanly shaven, after all women don’t keep their legs clean all winter, I have been keeping my chest clear. This is visual as when I wear a women’s top the hair shows and sort of ruins the illusion. I don’t miss my hair but I hate shaving, I have a beard because I hate shaving my face (Yes a 6’3″ crossdresser with a beard and shaved chest deal with it) so maybe some waxing is in my future.
I set goals to keep me on track and budget. I decided to keep my crossdressing expenses under control by linking them how often I do it. I downloaded a goal tracking app on my phone and set 2 goals initially. Wear panties for an hour a day and wear a bra for an hour a day. Every 20 days I get $20 for each goal met, so $40 every two and a half weeks which goes into my “femme fund” which is my budget for crossdressing. This actually has worked out as it turned crossdressing into a bit of a game and keeps costs down. The first 4 or 5 days are no big deal to miss but once you get further in you really don’t want to reset. It also means crossdressing is kept on budget as it is really easy to spend too much on the other half of the wardrobe. I also moved my panties into my underwear drawer and sorted my boxers down to a five day work week selection. I didn’t totally ditch them I just sorted them out to a weeks supply of the good ones and then put those in a container in my underwear drawer. This meant that every time I went to put on underwear I had fewer options in boxers than in panties and I would wear panties more often as my daily underwear.
I then set a third goal, panties all day everyday. I decided to just wear panties and set my men’s underwear aside and see how long I could last. This is more of the head first down the hole option. I have made it a couple weeks before but this time I also attached my goal setting and reward system to it. Since this is riskier I decided up the reward. $25 for the first 25 days and then $50 for the next 25 and hold it there. This means that if I miss a day I have to get another 50 to get to that higher bracket again. Now that I am just over 50 days in how do I feel about panties? I don’t think about it too much, they are just my underwear. I enjoy getting up in the morning and picking out the right feminine undergarment that will be my little secret for the rest of the day and the occasional reminder here and there. I could say the panties are prettier but in all honesty I rarely wore cheap crappy boxers, underwear is right next to your most sensitive parts so you should always have good underwear. Do I miss boxers? Every once and awhile and they are just sitting there and would take 30 seconds to get to the top of the pile and slip them on. I have them for when we go to visit family or something where our dirty laundry may be more noticeable.
Next thing for me to add some feminine flair to my life was getting a purse, well a satchel, and a women’s wallet. Men’s clothing has pockets but I decided to try out a “purse” and see where it took me. I picked it up in august and used it diligently until late October. Why did I stop? because it got cold and I moved to my winter coats (it does hit -40 here so I have some good coats) and winter coats are functional as anything with all of the pockets and my satchel just doesn’t match well with my winter coats. The wallet I have kept. It is a basic folding wallet with a few card slots and a change area and is made from felt. I found it for 2 for $15 at a gas station on a trip so I got one black and one pink (the femme fund is in the pink one). This actually worked out as my cash stays flat and my change is not everywhere.
The last thing I did was set out a few Jess days. These are days where from when I get up to when I got to bed I am wearing just women’s clothing with breasts. I don’t need to wear make up or anything else just all women’s clothing for just a normal day. There doesn’t need to be a fancy day out or meal just living a day as a woman. I highly recommend setting aside some time to just live in women’s clothes. Maybe a morning every two weeks or a whole weekend. It’s nice just to have some normal women’s clothes on and just do normal things. It is like a vacation in your closet.
That is where I am currently on my actively engaging with exploring the rabbit hole that is my life. What is the result? My spouse says I’m happier and more easy going so that is good. My crossdressing is defiantly more than just the clothes but I am not interested in hormones (If I could get just enough to loose the chest hair maybe) nor am I looking at getting my outie turned into an innie. I am willing to keep searching this rabbit hole and am not sure where it leads. My next goal is to get into better shape so I can look better in my clothes, all of them, and a pair of yoga pants, sports bra, tank top, and some random equipment is all I need to get started. As for everyone else obviously this is going to vary for each person but I do suggest pushing the limits of your comfort zone. It is much like working out you should be a bit sore after a good workout not in pain, push the limits a bit and see where it takes you.
As always I enjoy your thoughts and comments.