Making plans

I have been talking with my wife and there are several trips that we both will be taking separately. Many of these trips will also be without our daughter. So I will have several days by myself to dress however I'd like for as long as I like. I'm kind of excited about it. The trips are a few months off and so I think I'll have some time to get some new items. Here's my wish list in no apparent order.

• Dress AND/OR pants with a top.
• Shoes - heels preferably, but maybe just a kitten heel. I'm already 6 feet tall, I don't need to be Amazonian.
• Nail supplies - emory board, color or French manicure, polish remover.
  
• Make-up - foundation, blush, lip stick/gloss plus liner, eye liner and shadow.
  
• Night-gown or other sleeping clothes.
• wig

I don't think I'll be able to pull off getting all of this stuff. There's a trip at the end of July that they will be taking for a full week and so I might be able to get this stuff by then. But most of those bullet points will cost about $50 each. $300 is some serious cake. Especially considering it's for secret use.

Essentially, I am beginning to think about going out in public. In the one time I dressed up as much as I can, it was a lot of fun, particularly walking in front of the open windows. I've got the body for it and felt very feminine while walking around. Quite a little rush. The other good thing is that in a flowy dress, the difficulties I have with tucking are not so apparent. So, I think that with some practice I could get the make-up looking pretty good. Get an attractive, but not too flashy, outfit (pants/jeans and a basic top). Slap on a wig and go for a walk about. I think I have a decent sense whether or not I'd pass or not. On Crossdressers.com it's easy to see that there are some tell-tell signs of a dude. But there are also some amazing transformations. Guys that definitely pass as a woman. And as I've been noticing people more, I look for the more masculine looking women and try to pin-point what it is about them that makes them still look like a woman. I can look at these people and see them as a guy, but there is still something that makes them feminine. But I think this might be a trick my brain is playing on me.

At any rate, based on how well I think I could pass, I'll decide where I'd like to try it out. If I pass great, then I'll go out during the day for sure. To the mall or grocery store. Might even go out to eat. If I barely pass, then most that will happen is that I might walk down the side walk at the outdoor shopping center at dusk or night. Or go get some gas in the car. Little anonymous trips like that.

There are many times that women look more manly. One is when they are working out. Extreme endurance athletes look very manly when they are exercising. So I've also thought about buying some workout clothes and going for a run. I've also thought about working out in the hotel weight room. The good part about workingout would be that I could probably get by with wearing a hat and buying just a pony-tail wig that would stick out the back. This could also work to hide my face a bit. the problem I see with this is that my veins BULGE when I workout or go for a run. I've definitely never seen a woman with veins like mine. Manly for sure.

It's definitely fun to think about.

New underdressings

So yesterday I found I had a little extra time. So I hurried off to a Nordstrom Rack. I was a little disappointed in selection of underwear. I was expecting to grab a pack of thongs and a kind of booty-short/thong that I've seen a friend wear before. But their selection was only so-so. Also, the store was packed. I don't mind buying women's underwear or clothes, but I have a limited tolerance for really searching through all of the racks. It's pretty easy to be a guy looking for a thong if you're shopping for your wife. But after searching for too long, it seems like it's just weird. I get a lot more looks looking for underwear than I do if I'm shopping for a dress shirt.

At any rate, I came away with a new thong, which turned out to be a bit too large (bought a medium but evidently need a small). And a pair of hip hugger booty-shorts. I was thinking this last pair would be a bit more high cut. Instead it just looks more like a 1970's era bikini bottom. Ultimately not complaining because they feel great to wear (wearing them now), but just a tad pissed because they weren't exactly what I was looking for. I guess it's all part of the process.

Am I gay?

Short answer: No

Long answer: I have no romantic or love attraction to any other guy I have ever met. I've never thought about a specific guy in a sexual way.

That being said, I have thought about dressing up and going out and picking up a guy. Actually the picking up part is really just a conversation and then taking him in to the bathroom or something and giving him a blow job. I've actually thought about that quite a bit. I know guys are almost always up for a blow job and so, assuming I could dress and pass as an attractive woman, then I'm pretty sure I could convince a guy to let me blow him.

I've also thought about dressing up with my wife and the two of us going out and picking up a couple of guys. I kind of have this thing about being cuckolded. So I'd watch (as a female) while the other two guys fucked my wife, and then I could finish them off. This gets more in to my fetishes though.

So thinking about all of that, I still am not gay. However, I guess I clearly have a homosexual interest. That is, I have homosexual fantasies. But I consider someone to be homosexual as someone who not only has sex with the same sex but also seeks a relationship, i.e. love, with them.

It's a semantic issue. But I stand by it.

The 'art' and frustration of tucking

This really got to me on Friday. I have difficulty with the whole tucking thing. So the thing that you usually do is to push your balls up underneath the skin that is over the top of the pubic bone (the place from where they originally descended). With a little practice and getting accustomed to how initally weird that feels, they go pretty willingly up there. Then you pull the penis down and through, either use the scrotal skin to wrap around the penis, which leaves a very nice vaginal look, or just tape everything in place. The force then pretty much keeps the balls up in place. However, my problem is that I'm a pretty skinny guy with rather large balls. When I push them up in place, I have little fat tissue so my balls stand out pretty obviously. And when I sit down, it increases the amount of force on them and I can feel that something is not quite right.

I came up with a new way, which I'll probably detail in another post, that seems to work but takes a while to get set up. But works for my situation quite nicely. On Friday I tried to get this in place again and just couldn't do it. The skin around is pretty sensitive now from taping so I have to figure out another way to get things to stay in place.

At any rate, it was quite frustrating. Figuring out a good tuck is essential to get the look and feel I'm going for when I dress or underdress. Anything less just feels weird and kind of ruins the mood.

Introduction

So I’m sitting here at my desk at work. I’m a very happily married man with a daughter. I have a job that I absolutely love and is quickly becoming a successful career. I also have my genitalia tucked in between my legs, a pair of control top mid-thigh pantyhose on and two additional sheer pair on over that, all packaged nicely underneath my clothes. Part of me is saying “what the hell are you doing”. And another part of me is wishing I had a pair of panties, a skirt and high heels on.

I’ve always been attracted and drawn to the female form. I can remember being 6 or 7 years old and, after watching Annie on TV, going to bed that night and pretending to be Annie. Doing my first ‘tuck’ and imaging being a girl. I know this could not have been sexual in nature because, well, I was maybe 7 years old. But I can remember vividly how strangely comforting pretending to be a girl actually was.

That theme continued throughout my life and as I went through puberty that theme became much more sexual in nature. But even though there is clearly a sexual ‘thing’ to it, it is also very a-sexual, that is, the way I feel is so much deeper than an orgasm.

A few months ago, I was again, sitting at my desk fully tucked and ‘hosed’. And I started thinking about what it would be like to actually dress the full part. A real tuck with panties. An actual bra and breasts. Shaved arms, legs, etc… Then I started thinking, what would it be like to then go out in to public dressed like that. Walk through a mall or go to the store. Well, that bounced around in my head for a few more months and so here I am. Starting/wanting to slowly meet this truly feminine side of me.

I’m here to just share that feeling a bit and to explore this side of me. I don’t really see this being anything more than a fetish for me, but it’s certainly one that I love. However, I hesitate to call it a fetish because I know for many people it is so much more than that.

So, that’s who I am and what this blog is about. I post a bit over at crossdressers.com and have gained a lot of information from the girls over there. But there are somethings and experiences that seem more suited for a blog rather than a message board/forum.