One little victory

1 Jan 2011

SO…. this business of not holding back…

My cousin invited me to go out with her and her friends for NYE. The plan was dinner at Ruth’s Chris rape house, I mean, steak house (fucking retardedly expensive place), and then we got a table at The Depot.

But first…

You know a little bit about my fondness for heels and stockings… that’s an important bit of subtext. I’ll try not to bore you with too much history. Basically, that is a fetish I’ve had since I was a kid, and for all of my youth, teens, and 20’s, it was one of my deepest darkest secrets. I feared that no woman would ever accept me for it. I felt a huge amount of shame, too, given the slightly deviant nature of it. I even tried to “quit” on many occasions, many years ago, but ultimately, I could not deny that I just love how it feels. A few years ago, I had some experiences that were an impetus for me to start being more open about it. I had some really great experiences with telling various girlfriends / female friends about it. After a while I realised that most of them thought it was either a) very sexy, and a fun thing to play with in bed, or b) just pretty cool, insofar as it made me unique. Either way, it was always, all good.

Anyway, you have encountered me at a point in my life where I’m kind of halfway open about it. I don’t tell everyone, but I am still fairly free about it. Silly as it may sound, I used to fantasise…like, literally, masturbate, to, thoughts of going out “dressed up” in heels and hose. Something about it really pushed my buttons.

(a lot of people have a question at this point that I’ll just answer for you right off… I have zero interest in the whole full on cross dressing thing… I’m very happy to be a guy. I just happen to have an extended palate of sensual pleasures that I enjoy. I’ve got a buddy who is into the whole 9 yards… wigs, makeup, bra, fake boobs, etc etc etc… and I don’t get it. It’s all good, but yeah… not for me. I never want to “be a woman”… I just love being ME. )

I’ve gone out dressed up for Halloween for a few years now, and though that’s slightly nerve racking, it’s not really that big of a deal. Everything is on the table for Halloween. Nothing is too crazy or wierd, so people don’t really think much about what you show up in. I took it up a notch a few weeks ago… my friend was hosting a “Sexy Santa and Stockings” party at The Hotel. I showed up in my usual black heels, hose, black pinstripe booty shorts, black dress shirt thing, with a santa hat on… ya know, just to keep with the theme 😉 I was more nervous about that, because I was going out on a limb more, as the occasion had far less pretext for really far out ‘costumes’. I was nervous to get out of the car, but once I put one leg out of the car door, and started climbing out, I was IN, and I was loving it. The whole night, I got 1 of 2 kinds of reactions from people:

1. No reaction whatsoever. Maybe they didn’t notice, maybe they ignored me, who knows.

2. People LOVED it.

Guys and girls thought it was awesome. In particular, there was a very cute coctail server there who kept making eye contact with me the whole night, and eventually, she came up to me, opened a conversation, and proceeded to tell me how sexy my legs are. At one point, the hostess of the night, an incredibly beautiful bombshell named Jaclyn, wanted a pic with me. She knelt on the floor, groping my leg, feeling me up, for the photo.

I spent so many of my formative years self crucifying on the cross of certainty that women would totally reject me. This personal history made these (and other) encounters super salient and uniquely gratifying.

I felt compelled to take it to yet another level. I had long wanted to go out on New Year’s Eve dressed up… and this year seemed like a great time to do it. If I didn’t do it, I’d be holding back, right?

I decided to dress up to go out with Melissa (cousin) and her friends. She is dating a guy I went to high school with, which introduced a tad bit of home town insecurity into the mix, but I knew I would regret giving into such a petty thing. We got to the restaurant and started meeting members of her group in the lobby. It was kind of a surreal thing to be standing in a very conservative, formal environment, dressed in a very counter-culture way… kind of like jumping into a rather cold pool on a hot day… you definitely want to be in that pool – it feels DAMN GOOD, but there is a little bit of immersion shock for the first few seconds.

I just connected to my inner eccentric artist rock star, and proceeded to own it.

Lesson #1: When you fully own something, 99% of people will either get out of your way, or get behind you.

A very hot blonde girl walked in and greeted my cousin. She looked me up and down, smiled and said, “YOU look like a fun guy!” I hugged her in greeting, ,and said into her ear, “I definitely am”.

It was ON.

We sat together at dinner, and during the course of that incredibly slow meal, we got to know each other. There was definitely chemistry between us, and we had a really good intellectual / spiritual connection going on. After dinner, we made our way to the club. It’s also worth mentioning here that she is married. Very unhappily married. She and her husband have separate bedrooms. She openly pines away for a divorce. He rues the day when the divorce actually happens. She “doesn’t get out much”, though she looks like she should. She’s hot! Furthermore, she has never been to The Depot before. Not sure if she’s ever been to a really big dance party at a good club before, for that matter.

Lesson #2: Listen to your intuition, it’s pretty smart. I had a feeling that if I would go out dressed up, like I wanted to, I would meet an awesome girl. Seems counter-intuitive, I know. Dress like a freak, meet a hot girl. Bingo. Go figure.

This I do know… had I just gone out in my normal man attire, I would have been practically invisible, and we probably never would have hit it off.

A bit more pretext before I share the next detail. I was really uptight growing up, and in my 20’s. I remember one time my (then) wife was trying to be playful with me, and wanted me to do a little shake-my-ass kind of dance thing for 2 seconds, just to be funny. She was bribing me with sex. This is how uptight I was… I couldn’t’ do it. I went into the living room and turned on MTV, watching people dance, trying to create a plan for exactly what moves I would make. In the mean time, she is in the bedroom incredulously asking “Are you serious?? and totally (and rightfully) losing any last shred of attraction she ever had for me. Yes, I used to operate the Jensen Diamond Mine, right in my very own rectum.

Back to the story…

I grabbed my new friend by the hand, led her down the stairs away from our group at the VIP table, and into the swarming, dense mass of celebrating dancers, and proceeded to dance with her. I’m not a good dancer, but I have learned that it really doesn’t matter. Its about letting the music move you and just enjoying the moment… and many moments we did enjoy. She kept remarking how much fun I was, how much she wished she was single, and made frequent innuendos as to how aroused she was. I was regularly approached by beautiful girls that I know from being a regular fixture in the clubs via my photography gig. I knew the promoter and greeted him. All of this social connectedness made me look like *the shit*. I’m just calling a spade a spade, here folks. Oh wait, that’s because I am THE SHIT. 😀 When the stroke of midnight came, the temptation to make out was really thick, we looked at each other in a very knowing way, doing the calculus of her marital status and the implications of such an indiscretion. She grabbed me and kissed me on the cheek several times, and I responded in kind. I figured that respecting the ring at that point would be a good thing. As a sexually frustrated reflex, I muttered into her ear, “If only you were single…..”

We spent a good long while on the dance floor, dancing very close, grinding, grasping, touching, teasing, talking and laughing. I had only 2 small beers the whole time at the club, and never felt a buzz… everything I was doing was 100% me, in control, 100% authentic.

Around 1:30, the group left the club, and we all called it a night. She got back in her car and returned to her dispassionate “marriage”. I went home totally sober and completely invigorated, basking in the unique gratification that comes only from having FULLY lived that night, nothing authentic held back.

Lesson #3: Ruth’s Chris Steak House is a horrific waste of money. Those 4″ black heels were an excellent investment.

So I met a girl. I dressed weird. I danced and had 2 beers. Small things, for sure…. as they often say, God is in the details. 🙂

  1. I’m pretty impressed by how successful you are with hosiery and the girls.

    It’s important for all of us to remember that people from all cross-sections of society are open to this. I’ve met conservatives who never seemed to care when I wore shorts and hosiery. It was as if I were dressed in pants.

    Hosiery Advocate

    1. Thanks! It never fails to delight me when I get great reactions from girls when I go out dressed up. It may suffice to say that though it’s a bit more “risky”, the payoff is far, far greater.

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