Wednesday, February 27, 2019

More Crossdressing Goals

Another response from this site:

The dream for me is to make the most of whatever occasions I have and the time I am able to allot on each occasion, be it an evening, a whole day, weekend, etc. it hasn't been as frequent for me as I would like, but as long as I can get the most out of my time as Hollie, I feel like I would be living the dream.

Ideal circumstances for me would involve time to myself, which happens a lot when I travel or when my wife & daughter travel. For me, crossdressing in and of itself is a personal thing that I can't always share with my family (which is ok), but I would enjoy sharing with you all and others like us. It's not always easy for me to explain, but I hope it makes sense.

Wednesday, February 20, 2019

Goals in Crossdressing

Another response from this discussion:

My fantasies of strolling dressed in to a college classroom and eventually a workplace setting are growing ever-stronger. As my preparation time (sans showering) decreases to 45-90 minutes, I'm starting to realize the viability of dressing up on a daily basis for a workplace/learning environment.

My "Classy" female wardrobe isn't really conducive for at-home lounging, and as such I prefer to relax in my guy clothes, but I'm starting to reach the opinion that if I could, I'd go out dressed 80-90% of the time. I could even be crazy enough to throw on heels and makeup for a quick run to the store, unless that falls into the 10-20% of the time I don't crossdress. Eventually when I have a girlfriend or wife there are a few events that I'll prefer to throw in a suit and "present" as a straight couple, and despite my mother's acceptance, the rest of my family prefers to ignore it (the second best thing!), so family events would probably be guy-mode.

Monday, February 18, 2019

Secret Sissy

About two weeks ago, Mistress Lola gave me the following instructions:

I want you to put together your dream outfit for me. Not something that you already own - I want you to scour the internet and find the most perfect outfit that Dani could wear. Money and size are no concerns, so think big and think bold. Then send me all the components of the outfit and be ready for phase 2

As instructed, one week later, I sent her the following:

Let's start from the skin out, with this lovely set of undies, including a retro "bullet bra":

...and a pair of nice white hosiery:

The dress is pink and floral and described as a "wiggle dress":

The shoes are pink as well and bedecked with bows, as befits a sissy:

A new wig:

And a hat to top it all off:

Mistress approved of my choices and then surprised me with an e-mail that included a trance induction and the following hypnotic suggestion:

When you wake up
and as soon as you get dressed
You are going to see yourself
feel yourself
experience yourself
in your dream outfit
You will be wearing the bullet bra
the pink panties
the sexy stockings
You will be wearing the wiggle dress
and the pretty shoes
You will feel yourself in the wig
and wearing the hat
You will be able to see and feel this all day long
In every detail
From the moment you finish getting dressed
Until the moment you go to sleep
You'll be wearing your dream outfit
and the next day
you will write up your thoughts on the day for your blog
Like a good girl
Now when I count to 3
You will wake up
Fully programmed for your day of being a sexy sissy

Yesterday, I experienced that trance-induced program. Here is the report:

6:30 AM Got up, did my usual morning routine (adjusted the heat, took my meds). Then I got dressed. I was disappointed, though. I expected to feel each piece of male attire turn into part of my "ultimate" outfit as I put it on. But I was fully dressed in underwear, socks, long-sleeved t-shirt and jeans...and nothing. Then I realized--I was NOT fully dressed. My shoes were downstairs. I wondered what would happen when I put them on.

7:30 AM After doing my morning computer work, including writing the above entry, I went downstairs. I put on my shoes and then it all happened. As I slipped on the shoes, it felt as if I were sliding into a pair of heels...the heels I had chosen. At the same time, I felt the constriction of the bra around my chest and the weight of Mistress's Magic Mammaries. I felt the cotton briefs become the satin panties and my socks turn into the white nylons. I looked in the mirror in the living room...yes, outwardly, I was still in my male clothes, but I felt the lingerie, the figure-hugging dress, the wig, and even the makeup. I didn't feel as though I were wearing the hat--perhaps because I was not wearing a masculine one.

I went to make coffee for my wife, all the time feeling as though I were walking in the heels. I went back up stairs and found that I was going up them as I would in heels--with just my toes on each step. And when I went back down, I walked as I would have in heels, my feet turned to the side, so that toe and heel were both solidly on the step.

8:00 AM I went outside to pick up the newspaper. I felt my skirt blow around my knees and could swear I felt a breeze across my legs. Back inside, I made breakfast, still moving in a feminine manner. I stopped to look in the mirror again, and was compelled to run my hands over my "breasts" and down over my hips. I was moving, to some extent, as a woman would.

8:30 AM Breakfast over, I had to make a run to the laundromat to pick up the wash we had dropped off yesterday. I got into the car as I would have in a skirt--sitting down and then swinging my legs into the car. I've driven in heels a few times...and this felt very much the same.

9:00 AM Just finishing the last few entries. I feel the tension in my calves caused by the heels as I sit at my desk...and I feel the tingling arousal as I realize my secret sissy sensations.

2:00 PM The rest of the morning was uneventful, just a lazy Sunday enjoying the girlish feelings. But at about 1:00 PM my wife and I went to our local unisex place for haircuts. I, of course, had the extra frisson of having my hair done by a very attractive young lady while I imagined she could see what I was experiencing: My bob-length red hair, my sexy dress, my cute pink heels with the bows. I have long had salon fantasies; this came close to achieving them, at least in my trance-induced state.

11:00 PM The remainder of the day was without incident, although I continued to know I was "dressed". I found that I was caressing my body when alone, even tweaking my nipples. I was indulging this fantasy--secretly girlish, even if only in my own mind. Bedtime came and I changed to my pajamas, wishing they could be a sexy nightgown.

Monday, 6:30 AM
I awoke a few minutes ago and the spell was definitely broken. Back to being just my male self, in thoroughly masculine attire.

I now await Mistress Lola's reaction.

Wednesday, February 13, 2019

Goals in Crossdressing

For the next few weeks, we'll be looking at answers to this question on this website:

What are your overarching goals or desires with crossdressing?

I am not even sure right now how I feel about the word "cross dresser" I think I prefer transgender maybe non binary or even gender queer. My ideal scenario would be to be able to dress whenever I pleased. Which would most likely be like it is now 3-4 times a week. However, I rarely dress the entire day and I would like to. I would like to be able to dress dress femme as easily as I dress as a guy on a daily basis with no special attention to it being me "dressing up" I would also like to work on getting a better figure so I can wear cuter clothes haha. But overall I have been really happy with my situation. My girlfriend is accepting as of now and I am pretty damn femme despite by manly appearance haha. Shaved legs, a pedi, blah guess my future goals would be to integrate being my femme self more openly and for longer periods of time. Although I can tell I would probably want to do it more and more if given the chance......

Wednesday, February 6, 2019

To Tell or Not?

Some thoughts on a question that always plagues the straight cross-dresser in a relationship: wife knows about my crossdressing. Now that’s not to say I told her on our first date, I am definitly not advocating that. I’ll tell you my story and maybe that will help you out.

Read the full post here.