Starting the Transformation

Don't have much time to write today but will put a little blurb down. I have started recently with the assistance of someone on here to transform myself into the chaste sissy slut I would like to be.

This part of my life is very exciting as I don't know where it's going to take me. I don't know how much of my masculine side (which I do like) will survive and how much of a proper sissy will emerge.

I begin today writing in what I hope will come to be a fairly lengthy and interesting journal, I wish I had something more interesting right now, but I must go. I hope to add some details and some thoughts tonight after work.

 

I think that this is somewhat of a good starting point. I feel sometimes that my masculinity interferes sometimes with my sissy desires. It's a very confusing time for me as I do enjoy my masculine side. I guess the best way to put it is that I am two faced in that I enjoy my masculinity at times and at times I enjoy being a sissy.

I don't know yet which of these attitudes will prevail. In a way this is more of an experiment as well as a journey. I can take the time to learn more about myself and where I am going right now.

 

Wow it's been a bit of time since I last updated this journal. My schedule seems to have that affect sometimes. Since the last time I wrote here I have had a release, I was told that I may take a release last weekend if I wanted....originally I had planned on not taking a release and just to do a milking, but I got weak and ended up going to far. The worst part of that is knowing my self-power is so weak.....it does make me wish at times that I COULD lock myself up and send off the key.

At the request of.....hrm not sure what title is appropriate here...I have been trying to introduce my wife slowly into a sissy maid life. I haven't been dressing and mostly it has been a maid function. At first I was to start doing things such as pull our her chair, open her door, hold her things, etc. And it worked very well, my wife got to the point of expecting these things done. Now we can't go anywhere for the most part without me doing it. A while back we went out and she stood outside the car after I got in, I had to get out, go around and open her door. So I think that mission was a success and it has made me better for it.

The other half was to slowly pick up more chores around the house. This is killer to me, I don't really mind doing the chores it's just I'm always tired. I work 12 hour shifts on the ambulance, on my days off I work 12 hour shifts in some hospital, I get maybe one day off every week or every two weeks depending not to mention the time I spend studying while I'm not at work or at the hospital. I have started doing more than what I was doing before...but it has been a battle with myself to do them, I suspect this will be an easier task once I finish school next summer/fall and can have the time.

I still have not worn any feminine clothing as I lost all of mine in an unfortunate accident (the closet where my feminine clothing was stored as well as some of our winter clothing had a pipe burst and the nasty water ruined everything). I have not replaced anything, mainly due to the holiday season, I have picked out a nice set of lacy panties and a couple matching bras but I still can't get them yet. I would also like to find a nice wig (I have short buzzed hair...military style for my job) to compliment my facial structure. Maybe once I can get a nice outfit together with some hair I can focus on this strange strange world of makeup. I have no idea where to start.

I am happy I made this post at this moment. The biggest thing the release did to me was kill my drive. For two days after I wanted nothing to do with this, I knew that I did but again there was a part of me that just was happy to have had the release and be done with it. So I guess happy and proud that I could come back (stupid schedule) and keep working at this.

 

Today I went shopping for the holidays. Part of my goal was to get my wife a gift of some perfume as she really hasn't had any other than body sprays. I decided that I would take a trip to Sephora and let my eyes wander to other products while I was there.

A little backstory of why this is significant to me. I find GREAT humiliation and embarressment into just walking into a panty section. I have only brought myself to the point of being able to stop and shop for panties/products a couple times. One example was I went to Victoria Secret to find something for my wife. As I was walking aruond the only thing I could think was that everyone was watching me. As I kept walking and finding things and thinking "oh wow that's cute I want that for me" I eventually got really embarressed and beelined out of the store without purchasing anything.

So tonight I go in and fairly quickly I'm approached and we go through the process of finding a fragrance. I pretend to be a typical guy shopping for his wife. At last we finally found something, while walking to the counter I decided to be a little brave. I ask him about makeup for my 'wife' (ie me). I tell him we are about the same skin tone and she has slightly sensitive skin (which I do).

He stops, so I stop, he leans in close and lowers his voice. "Hunny, I think you would look good in a......." I taper off that part because I don't remember what he said. My face was beet red, my ears were burning and buzzing, and I was obvious put in my place. I'm not even sure if what I quoted above is correct. He laughed to ease the tension a bit and handed me his card and asked me to come see him after the holidays when it was a bit less busy for advice.

This was a huge step for me, something I hope will be the start of getting over this humiliation of just walking past the pantie aisle.

 

I've spent the better part of today exploring various websites to start rebuilding my wardrobe and honestly this day can't end fast enough. I've picked out several pairs of panties, a couple bras, and maybe some other items. I'm really excited and can't wait to get some of these items. My plan right now is to try and replace my mens underclothing, enough so that I have enough to match my current mens wardrobe. Then I want to lock my mens stuff up and mail my key off for someone to hold until they feel I can have the key back or never send it back. That makes my heart race just thinking about it.

One thing I WOULD like to find that I'm not having any luck with is a decent wig. For one my hair cannot be grown long, I must keep it short (think military boot camp buzzed) for my job. I could grow it as long as my ears but no further, so I'd rather just keep it buzzed/shaved and wear a wig on top of that for now. I just don't know where to start, what's a good color for me, a good style. Can I buy just a regular style and do different things with it or do I need to buy a style for every time I want to change it. I don't know who are reputable, what kind to get, storage, etc etc etc. I'm lost :> But I will keep searching and maybe I can find some help here as well

One other thing I've found that I want to get is the nJoy Pure wand, I've heard GREAT things about it for milking and I'm getting tired of working with my heart wand thing and a makeshift handle. I did order an aneros but I got screwed by Extreme Restraints (AGAIN) so I will no longer be ordering from them. Look forward to placing my orders tonight/tomorrow and getting all these goodies in! My next goal is a plug that I can wear long term. I've already posted about my issue with plugs and their bases. Was looking at one of these WMCBP, but they're so expensive for the larger sizes

I want to keep pace with the tasks that are assigned to me, but I just get excited and am ready to move forward with the next step. I know transformation takes time but I just want to dive right in!:character0100:

 

I like the ideas for going far away. The only problem with that is I'd have to drive an hour or so to get to the point where I might not be recognized. I know people in all areas of the city

I know I need to work on that apprehension and the thought of going in a store, finding things in my size and trying them on is both scary and exciting. I think it's one thing for me to go buy a 'sexy' bra. But buying a utility bra or other 'everyday' bra for me seems like an "OMG they know, why would a guy buy his wife an everyday bra."

I would like to maybe sometime find someone or get the chance to be forced into a situation like that. The embarressment is again, both scary and exciting

I don't know if I could go into a store to find a wig style to fit me :> I want one but that's the worst part about buying online. I have no clue what style would look good on me.

 

Thank you for the links and information. I shouldn't worry but I do, all the time =/

I am very excited though, I ordered everything I said I would, can't wait for it to get here.

 

Today! My panties came in the mail...wow that was fast. I was in the living room watching Dexter when a knock came to the door. I was expecting a gift anyways from an online secret santa exchange so I thought nothing of it when my wife went to open the door. She came back giggling "Got a christmas present for me?"

:confused0068:

"Ummm yea, was supposed to be a suprise, sorry. Let me put htat away, not gonna get it on christmas now, gotta wait till your birthday."

Eek, so I put the panties away until she left for work (about 15 minutes ago). I just tried them all on and they all fit PERFECTLY. So now I know the exact size I wear for this particular brand (sold by a boutique that I could visit to try and get over that hump).

I have on right now the pink and white stripped pair. Now to get a few more and I can think about going 24/7. Tomorrow will be my first day going to work with panties on, we'll see how it works out. I'm very nervous and scared but excited all the same. Now to see if I can go through with locking up all my male underwear for a period of time to prevent me from cheating :>

 

Yes after discussion last night I am in need of some 'utility' panties to wear to work. Unfortunately I do not have those so I slept in my panties last night and went back to my mens boxer briefs. The funny thing is talking with other females at work, we were comparing what kind of underwear is the best to wear with our uniforms. The most common response from them was mens boxer briefs. The next most common was boyshorts.

I can't completely throw away my mens clothing for the sake of my wife (for right now) but in the meantime there is the option of locking it up in something. I'm at work again for two days so once again will begin the great search of various places and plans and such :>

 

No, I do not plan to use that as an excuse, just something I found interesting. I will probably get a few pairs of 'utility cotton boyshorts' to wear to work. No sense in destroying my pretty stuff on the job.

A strange feeling since I started doing this though, every day I have continued to wear my mens stuff I feel wrong. Starting this up has been an almost freeing experience for me. I have never felt that I would go all the way (part of me does wish to do that) I do still enjoy my male half when it's around. I feel......right....when I am feminized.