When the judge made the final pronouncement of divorce, I had to fight back tears. I knew it was coming, had seen the writing on the wall for a while…but I still wish it wouldn’t have had to happen. The final settlement was good (much too good according to my lawyer)... no matter what happened I would never want for anything in my life. I held back my tears as I had been hoping to continue to live as man(ish) and wife, but I didn’t despair too much because our deepest relationship would never be over…after all, no mistress would willingly give up their most beloved slave girl.

My girlfriend grabbed me in a fierce hug right in the middle of the courtroom, followed by a very passionate kiss. I could hear a few mutters from people who had come for my wife’s moral support (as if she needed any) when they witnessed the exchange. To outward appearance, I was basically a kept husband who had lived off of his wife’s money for years…essentially a male gold digger. If they knew the truth they would be even more shocked.

It all started a couple of years ago, when my wife came home early (for her) after a doctor’s appointment. I didn’t know it at the time, but her morning had been a chaotic wreck due to issues with a distributor or some such. Compounding on that, she had been to the doctor for a routine check up and found that not only was she showing early signs of heart disease, but she also had extremely high blood pressure. So she came home frazzled…completely stressed from her day, to find me prancing around the house in her lingerie.

I still remember that moment. Imagine me, standing there. Deer in the headlights look in my eyes as my wife walks in the room. My mind instantly exploding in a series of horrified thoughts. Divorce…humiliation…rejection. I expected anger or revulsion. I expected scorn or contempt. I didn’t expect laughter. It started as almost an insane uncontrollable giggling, and she just couldn’t seem to help herself. Soon tears were running down her face as she laughed uncontrollably…and I felt so small. I was in my most vulnerable, most deeply hidden form of expression…and she was mocking me.

I remember the regret in my voice as I dejectedly told her I would pack a bag and get a hotel room until we could settle things. I didn’t expect her fierce hug as she grabbed me and refused to let me go. She told me she wasn’t laughing at me…she was just so stressed and seeing me like this just gave her a much needed release. She proceeded to drag me rather forcefully to the bed and show me just how much more stress she needed to work off. It was that night, that beautiful night of sex our newlywed selves would have envied, that spelled the beginning of the end for our marriage.

—

A few years ago…

Tonight is going to be a good night I find myself thinking. I have the house all to myself and for the first time in a couple of weeks I feel like it’s safe to let my feminine side out. I feel a slight tremor of guilt as I rummage through my wife’s clothing looking for a sexy outfit to wear. I don’t know if you would consider her slightly large for a woman, or me petite for a man…but we are close enough in relative size for her clothing to fit me (even if a bit snug in some areas). Since my wife told me not to expect her until late this evening, I have plenty of time to really immerse myself.

I consider this my marital Moby Dick…you know that one big whale of a secret nearly every married person has…the one that has a very good chance of destroying the life you have. Some people have hidden affairs, drug abuse issues, health problems…me, I have a fetish for wearing women’s clothing. No thats not quite right…I have a fetish for transforming myself into a beautiful, graceful, sexy goddess for a few hours at a time.

Sometimes all I can manage is a pair of soft silk panties under my work suit, or a quick make up job so I can see my more beautiful alter ego in the mirror. Two or three times a month, when I know my wife is going to be out for extended periods of time, I can do the whole head to toe goddess look…and really feel beautiful for an hour or two.

If someone were to ask, I would say I am at most bi-curious. I have on occasion wondered what it would be like to be with another man, but overall I much prefer a beautiful woman. In pretty much any opportunity for company (sexual or non) given the choice I will always choose a woman over a man…so while I would not ever rule out sex with a guy, I doubt it will ever present itself as the preferred option.

I can’t help but feel excited at the moment..I was so pumped I actually snuck out of work a half hour early just so I could have more time. Now, a bubble bath later (smelling faintly of roses) and my arms and legs coated in a lightly femininely scented lotion I am ready to transform myself in all my glory.

I quickly apply my makeup with practiced skill, while my toenails dry from the light coating of red nail polish. I can’t help but marvel at my image in the mirror as my face transforms from a average looking man to a sexy looking lady. I love the way the makeup feels against my skin as I apply it. There was a time when I would just slather it on until I looked like a really cheap hooker or a clown…but now I just apply light, artistic amounts that accentuate instead of overwhelming. The lipstick I use is a very light shade of red that give my lips a glossy look without the bright red I used to go with.

I put on my wig, transforming my hair from short, dark brown to long straight raven black hair. I really like this wig, its long silky smooth hair reminds me of some Asian or Native American women.

Now comes my favorite part of all, I pull on a pair of thigh length stockings…black colored nylons with a red lace rim around the top. I love the silky feel of them against my skin, it is by far my favorite guilty pleasure. It takes another 10 to 15 minutes of primping and prepping before I am satisfied every thing is in place (thankfully I have virtually no body hair to really slow things down).

I quickly slip on a sexy black and red outfit that always excites me when my wife wears it. It takes a bit to get the top right since all I have to fill the bust is a pair of balled up socks (I am too chicken shit to actually go buy falsies…plus where would I hide them). Finally I slip my feet into a pair of sexy black heels to complete things.

I stand in front of the full length mirror and primp and pose. I absolutely love dressing like this. I wish I had the courage to go out in the world looking like this…if anyone saw me like this they would think I was my own sister or cousin, very few people would see ME beneath the glamorous figure I represent in this outfit. God I sometimes wish I had the courage to show the world this ME…or even the lesser required to let my wife see this side of me. The only people (that I know of) who know this side of me are my parents who caught me out when I was still in high school, and while my mom sometimes gives me tips…my relationship with my dad has been rather awkward ever since.

I can’t help but relish my look in the mirror…I absolutely love this time when I can let my sexy best out for a walk.

I was so caught up in the sense of freedom…in the exhilaration I always feel when I wear women’s clothing that I failed to hear the sound of the door as my wife entered the house. So lost in my inner world that I didn’t hear the sound of her walking up the stairs. There was no way I could miss the surprised gasp followed by a shocked exclamation of “OH MY GOD!”