Jackie, What Are You Wearing Today?

I am in my mid-forties. Married for 22 years to an understanding wife. I told her as we got serious in the relationship that I cross-dressed and enjoyed feminine things. She thought about it for about a month before she said, “As long as you never bring it into our bedroom or pretend you are a woman when you go out with me, we will see how it works out.”

Well, it did work out, Jackie has her own ultra-feminine room, a closet full of clothes that constantly change, almost always purchased from a second-hand boutique.

Three days a week our schedules at the hospital afford me a four-hour window of opportunity for Jack to become Jackie. We both get up at together, have a cup of coffee and then she is on the way out the door. Today I decided on a shower (all foamy and freshly feminine body washes), I am permitted to shave my breasts and do it carefully. Then I put on my Victoria’s Secret pink nylon dressing shirt and do my toenails. I laugh because in today’s scenario I can’t see them, but I know they are done. My outfit for the day is already laid out on Jackie’s dresser. We start with the bra. A previously owned by a woman, lightly padded, black Calvin Klein 38-B bra with adorable white lace trim. It fits my left breast perfectly; however, I am asymmetric and I have to use a silicone enhancer to fill the right cup.

Panties, due to health laws in this state, I bought them at Belk. Vanity Fair, size 6 granny panties (full briefs) in black also with lace accents. Due to today’s planned activities, I put a panty liner in them as I am already precumming.

A DKNY heavy-weight tee shirt, size M, with a scoop neckline (also previously worn) is next. Then I am going to add my newest acquisition. A pair of tattered black slim-legged maternity jeans. The tag was cut out, but I held them up to myself in the store. The elastic belly band will give plenty of leeway. I slip into casual strappy sandals. It is time to do the dishes. That is as far as my dressing goes here at the house. Today I added the throw pillow from the couch. I smiled as I passed the full-length mirror. Jackie's pregnant.

I admit that I have been dressed and out with three different ‘makeover artists’. Twice I was so hideous looking that I declined the trip out portion. Once my ‘escort’ took me to a gay bar where I felt like fresh meat in a lion’s cage.

I slip into my yellow Playtex gloves and manually do last night's dishes. Each move makes the underwires in my bra dig and poke, it is no wonder that Nattaly is ripping hers off when she gets in the door. I also vacuumed the carpet. I must fold my own clothes from the laundry basket but that is a small price to pay.

Yes, we sit to pee when dressed. When Nat is red, we use maxi-pads in Jackie's panties (sometimes we use a bit of ‘movie blood’). We play with tampons in various ways, and we never mention anything about being feminine to her as we have had a few serious arguments over how easy it is to be a man vs. being a woman. It went something like this:

 She used the opportunity to vent her frustrations about just how chauvinistic men were.

“They are big into making money off of us females.”

“What do you mean?”

“Well, Jack, like it or not a female spends a fortune on doctors’ visits in her lifetime. First of all, she is more than four times more likely to see a doctor, in the course of a year, than a man. If she has a yeast infection, she must go to the doctor, if she skips a period she goes to the doctor, if she needs B/C pills she goes to the doctor. Now, take into account all of our special plumbing, we get a much higher number of UTIs and add in an average woman’s 3 pregnancies with all the prenatal and postpartum visits. See where I am going with this? Now, add up the thousands of dollars that I will spend on tampons and birth control pills in my lifetime. Then add cosmetics and friggin’ pantyhose that self-destruct on a daily basis. Plus, in addition, the fashion industry is also to blame. What is in this year, is out next year so I have to replace my entire friggin’ wardrobe almost annually, lest I am not “in style” at one of your functions. A man can have three suits, two shirts and buy 3 dozen rubbers for ten bucks and be set for a year. Just walk into that new Superdrug store and count the endless aisle upon aisle of products for women and see if you don’t agree with me.”

She took a deep breath and said she was sorry. That is why it is never brought up, ESPECIALLY at that time of the month.

Ok, we are not super enhanced today so I will go out to check the mailbox. All good, no contact.

During my personal time with Jackie, I allow thirty minutes of time in which I can do what I please. The phones are disabled. I may choose to do nothing, read a book or one of my 1950’s women’s magazines, masturbate, edge, or whatever I choose to do. Today it calls for a partial wardrobe change. So I take off the tee-shirt and bra, I admire the deep bra lines in my skin. I open the top drawer of Jackie's dresser. It contains a huge number of feminine objects. A vaginal diaphragm used by a woman that is sometimes worn in my panties. Old Tampax holders used to discreetly carry them in your purse, from the 60’s. A large collection of vintage douche and contraceptive creams and jellies. Most all have been in intimate contact with a woman. There is a Black Medela bra. It is speckled with drops of milk inside the cup. I carefully put it on and unlatch the cup pulling it down to view. I take my vintage glass breast pump and suction my left breast into it. My right hand is rubbing my jeans for a few minutes. I see the nipple become engorged and turn bright red. Milk for my baby, the right hand creeps into the belly band, finds the rock hard member and finishes it off in my panties.  The panty liner did not contain it.  A nice rich taste as Jackie will eat Jack's cum.

Ten minutes to go, decisions, decisions. Tomorrow is going to be Schoolgirl Day, perhaps a naughty little girl that likes anal…Red plaid skirt, white blouse, red tights that might be ripped by the time we are through with her P-spot playtime. Exercise the pelvic muscles all day today.