The Fairer Sex and Cross Dressing

I was reminded of long buried memory this past weekend. The weekend first:

My wife and I were sharing a cottage with some friends celebrating a birthday and I was the only rooster in the hen house. 5 women and I were shaking off cobwebs with coffee and generally loafing around at the start of a long day, not mustering the energy for much. Two women, curled on a couch were flipping through a Vogue and gushed at the picture of the nice strappy gladiators with killer heels.

“nice”, says I, walking by.
“they'd look great on you” says women #1
“I do have the ankles for them …”
“hell yes. These and a nice short skirt, oh yeah, we could have some fun dressing you up…”

Well, you know where this goes. Absolutely nowhere. In this case in any event.

The memory however goes back to high school, and I suspect that Halloween enabled the whole caper. Myself and a best friend managed to find ourselves in a home untroubled by adult supervision with a couple of girl friends, couches and a bottle of lemon gin or some other social lubricant.

The girls had mustered the nerve to make or rent Playboy Bunny outfits, were foolish enough to share the news, and contrary to the sound advice of mothers everywhere were convinced to slither into them for an early private audience. This, in and of itself was a “bucket list” moment. Black sheers, tall sandals, and form fitting bodices yielding an epic upward effect on youngish breasts not needing much help for starters.

A grand time was had.

At some point, a conversation along the same lines as my recent experience happened. Hushed conspiratorial, enticements and giggling endearments …

“you would look so cute, both of you… wouldn’t they?
“oh yeah, and we dressed up for you … fair is fair … right?”

Knowing my desires well, I put up a little fight, but my buddy who was less hung up on things in general grabbed a bunny and vanished behind a slammed door in a heartbeat. It wasn’t long before I was cotton-tailed, short of breath and entirely short-circuited in my overloaded brain. Any attempt to summon up accurate detail about what happened next would be pure speculation, and not worthy of my respect for you, dear reader.

I have had more than a handful of experiences where a woman or a budding young thing wielded this tease, parts innocent and parts provocative, and wondered whether this is a more common desire, more commonly acted out than we know. I wonder whether this class of conversational probe is intended to find out something good or great about the guy trapped in her gaze. I hope that the sessions of exploratory dressing that I was fortunate enough to stumble into were … well, “good for you too” you know, and whether it is a theme that these curious girls returned to later in life.

I hope so. I had a terrific time in the bunny hutch, and if I had more nerve, would likely have gone on an all carrot diet to stay there for a while. Daylight frightened me back into my warren though, but thoughtful always of pretty captivity.

In closing today then, for those select and respected women reading this post, here is a question:

Did you ever dare or engineer a guy into a dress? Go ahead, don’t be shy, and leave a comment. Or better yet, just go and have some fun with your guy. It may be a little awkward, but a part of him will thank you.

Happy dressing, and happy everything else.