
One night in, probably 2005(?) I got to dress in drag for a party. Complete with makeup... and that shit was hot. I think it is safe to say that since that moment, I've held a small, but growing desire to wear that type of outfit again.
Women are lucky... if they're feeling down or sad - they can spruce up with makeup. A little eyeliner, some blush, a little lipstick... bam. All the tiredness is gone. Men - we have to look good with soap, poorly managed beards, and... that's about it.
This weekend Lady Bourbon and I tried something new... She went to the store and picked me out a nice top and some very nice satin panties to match the skirt she gave me. We went out to dinner in normal, gender approved clothing... with the exception of the purple, satin panties I wore under my jeans... They felt amazing.
We sat in our small town, eating, drinking, and being a normal couple... as is expected here. And only the two of us knew. It was very... refreshing? Sexy? New? Exciting? All of the above? Yes. All of the above.
![]() |
Not me... |
So - yeah. Then we went home and I went upstairs, changed my clothes, put on some eyeliner, and came back down.
Well - apparently it isn't just me who thinks it's sexy. Lady Bourbon was pretty fucking turned on at the sight of me in snug, satin panties which leave little to the imagination - especially when I'm sporting a hard on. She was wet before I touched her and my cock felt like it was going to explode... What? It was hot. She is hot. I was all about getting up on her stuff...
We made out... she pleasured herself on the couch while I fucked her mouth... Then she bent me over and... again - post for another time...
Point is - it was really hot.
Until...
This is when 40 years of conflict clashes together and I suddenly get very nervous that Lady Bourbon thinks less of me... or that "something is wrong with me." - it was fleeting, but it was enough to cause a slight short circuit in the fun I was having in the moment. And that what sucks... I was really enjoying myself. I was really having a good time. I really liked how I looked and felt... but all of the Army shit and macho bullshit I've been force-fed came rushing in.
Let's time travel shall we?


Hello, repression. Angry much?

And so here we are... I came of age watching women in their underwear put on makeup and look happy and feel good. It stuck with me. Now, at 40, if I want to make myself look "pretty" I can trim my beard and fix my hair... but that's about it.
And it kills me that men wearing makeup is pretty much a guaranteed way to end up in jail in most of Rural America... and I'm not doing that shit again.
Just kidding. I've never been in jail.
So, yeah... world. Here's my thing. I don't want to be Eddie Izzard. I don't want to wear dresses all the time... And I don't have his charisma...
But sometimes - I just want to feel... pretty. I want to do more than just trim the beard and fix my hair. I want to wear underwear from time to time that isn't utilitarian in design.
Is that so wrong? Is something wrong with me for that?
So what? So what if I want to wear eyeliner? What if I want to wear sexy panties under my clothes and watch Lady Bourbon admire my neatly stuffed package? It's fun. I like it. I want to do it again... I want to do it more... But I have this deep-seated fear that she thinks less of me. I know she doesn't, but it's called an irrational fear for a reason. But I love her... and I'm 99.9% certain she feels the same way. She'll probably comment on this post if I know her... or she'll just wait until I'm home, smack me upside the back of my head and say "I love you, you goofy asshole." At least I hope.
These are the thoughts I've not shared with her... or anyone. Ever. I've seen people come clean with their partners about hidden desires to only watch it end in flames as a result... And that frightens me more than anything really.
Lady Bourbon here. I love you, you goofy asshole. We'll do it again the next night we're kid-less... but next time, I'll do your eyeliner. ;-)
ReplyDeleteDeal!
Delete