From Bradley to Brendalee43

It's about 10 am and I'm finishing my make-up, taking into consideration what my therapist has said many times and my earlier chat session in Lit encouraged me to do. That is to post my story here.

Well actually, my therapist said I should "write a book. It would read like many stories on Literotica.com". I'd never heard of that site until then. But after she said it, I rushed home to check out said site. And it did not let me down. So many stories, some that I could relate to, as fiction as they were. Or is this site where my new friends got their ideas? It doesn't matter, I've had such a time over the last nearly 11 years, I'll share it and find out how it feels to share my story.

There will be several chapters, or "memorable times" that I post. Maybe one a week.

I take one more look at myself in the mirror, a vast improvement to nearly 11 years ago. Not slender, but fairly HWP, 6 foot tall, 160 lbs, nice legs but fake blonde hair. Normally dark brown and curly. I don't have that hourglass figure that would be so nice, but with a push-up half bra corset, Not too bad. I've worn pantyhose for over 12 years, and my wife figured that was the start of what became. I'll get back to that.

Yes, being 6 foot tall makes for a tall woman, and I'm gifted with long legs, and my toes have been painted baby pink since May of 2013, when Claire found my web history.

Claire and I were married 20 years at the time and if you said "vanilla", that sums it up for up till then. She is (was) tiny. Most of her clothes were size 2. Looking at her face, you'd conclude the original porcelain face dolls were copies of her. Very smooth skin, big deep blue eyes, face framed with shoulder length hair and kept perfect. She never wore much make-up. Didn't need to. Her bra cups were A but she'd cheat and get B falsies. Maybe 5 foot tall in heels, but what she lacked in size, she made up for in aggressiveness. She climbed the corporate ladder, could and did outsell anyone in the company she worked for, and brought that personality home. Being that small is what contributed to us never having kids. Just busy aunt and uncle.

It was the first of the year, '13, I was having circulation problems in my legs and the doctor suggested wearing compression hose. Knee highs helped but made my legs look like a mushroom at the knees. I found a version of panty hose with a fly and wore them for a while. It was a thrill. I'd always thought of sneaking Claire's intimate wear on but with the size difference, I doubt I could get her panties on past my calves. But something stirred and I had to try further.

The hose with a fly were about 30 dollars more than women's pantyhose. I being a person of thrift, decided to "save money", get women's and just wrestle them at the urinals. I was hooked!! I'd hurry to put them on, as difficult as they were, and wear them as late into the evening as possible. I also wondered how they'd feel under a dress. But that wasn't going to happen with any clothing here, with her at size 2, me at 6', and at the time, 230 lbs. But I'd soon get to find out.

Claire had a business trip that would take her away 5 days, including the weekend.

I measured myself and set my own work schedule to accommodate a little shopping and make sure my weekend was empty.

After dropping her off at the airport, I stopped by a couple thrift stores and tried to be quick at what I was shopping for. A couple dresses and how about a night gown with lots of ribbons and lace? I found them. And the night gown was pink. I was excited and nervous at the same time. The shoes that were in my size weren't remarkable so I skipped buying some, that time.

Once home, I put them in the washing machine, and hoped nobody surprised me with a visit as I hung them to dry.

I wasn't going to put them on until after work on Friday but temptation took over.

After dinner, I ironed the dresses and put one on. The look was a fat guy in a dress and panty hose. But the feel was sooo good. Something soft about the fabric. And I got to experience sitting to pee. (that memory would become permanent years later)

The next day, I hurried home, got into my dress, ate dinner then spent time surfing the web about cross-dressing. Which led to many other related things. Petticoat discipline, forced feminization, FLR, and so many more. I was reading more those few days than I had read about my business deals. But it got late, I removed the dress and put on the night gown. And couldn't sleep. More web time, more thrills and a pesky bulge in the pantyhose. Gotta take care of that, and my hand got a bit of a workout. I took the pantyhose off so I could take my underwear off, then put the pantyhose back on, only to work hard at falling asleep. Not much luck, and I had to service the bulge again. So my weekend would be. It was raining both days, and I was happily in my dresses and hose.

When Monday came, I sadly put the dresses and nightgown in a clothing donation bin and said my good-bye to a fine weekend. But that didn't stop me from finding every web site about those topics every chance I could get. And every time I put my compression pantyhose on, wished they were a little sexier. I found some! These had the compression I needed but also were sheer and very attractive finish, on females anyways. And once again, less expensive to what I was wearing. When I told Claire I would wear them, she said "nobody cares what texture or color they are when they're never seen anyways". She bought it! And I was lucky enough to have a reason to wear them. Wishing a dress could be "prescription", but be careful what you wish for. You might just get it. And I was about to.

It was well into spring, my business required very little attention at the time and I spent much time cleaning up and trimming the yard, the usual things one does to have the yard in shape for the summer to come. And every time I came inside, would browse my favorite sites, longing to be able to say "I do that". On a Friday night, Claire asked that I get some take-out, a couple bottles of wine and close the drapes, it was a night she didn't want interruptions. I set the table and had things ready.

It turns out, she was offered a promotion, the second in less than a year. And would be the first woman in the company, many branches world wide, with this position. There was no question in my mind she'd be very good at it. And I told her so many times. We had a "usual" Friday night romp in the sheets. VANILLA again but she made it interesting when she got on top and played with my nipples rather hard. Or I should say harder than normal. But it felt great as always.

The next day, things went as usual and I was outside again, getting yard cleaned up. When I came in to get a drink, Claire was on the computer and my heart dropped. She had one of my favorite sites up. Then another, and another. I was frozen even though it was over 70 degrees out. She looked at me, then back at the screen, then asked...."Do you like looking or wish it was you?" The pic was a highly feminized guy in a chastity cage, lifting his skirt to show a bunch of women. A pic I'd opened many times. And she knew it. I didn't lie, just said "It thrills me to the point of pleasuring myself often".

She said "I have enough to think over the next few days. We'll come back to this when my mind settles down, I promise". And she kept that promise.