Statepalace
Posts: 185
Joined: 9/20/2007
Status: offline
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I am (was?) that tomboy sub.
Eight months ago I owned two dresses (one had never been worn) and wore dress slacks to work exclusively. Hair was in a bun for convenience, and makeup was limited to foundation if that. I hate jewelry. Jeans and tennis shoes were my standard clothing choices when not at work.
Since mid November I've worn nylons of some form (hose or thigh highs) every day. Every single day that I leave the house. I've been in skirts or a dress daily, with the exception of the three day "omg Orlando is in the 30's" episode last month, or if I'm back in Louisiana helping the parents do physically grungy outdoor work. Even then, I wear pantyhose underneath, as per His instructions.
The transition was so incredibly gradual that there are times I still shake my head at the fact that I schedule shopping into my calendar without breaking out in hives.
He started out by simply saying that He would like to see me in "anything but pants". No orders, no insistence. The whole issue made me so uncomfortable in my own skin that if He had insisted it would have caused problems. The phone calls were what started it, really. He would call me, and proceed to get me hot and bothered, all the while saying "You know, if you were in a dress or a skirt right now you could be touching yourself". I could not, of course, if I were in pants.
It aggravated me no end, and I finally decided to start wearing a skirt once a week. Then it was twice. Now I'm out of skirts. Have to go shopping. Hate shopping. Still hadn't managed to have "skirt day" as I started calling it coincide with a phone call. I even apologize for disappointing Him when He calls to find me in pants, and He make it very, very clear that I did no such thing. And then repeats that message. "You're frustrating yourself wearing pants, not me. I would be very pleased if you wore something else, but you are not disappointing me".
That was a critical part of the whole process. Happy things occurred when I dressed correctly. Everything else was neutral. I meandered over to the "girly side" at my own pace. I really believe that is part of what made the transition stick.
While He didn't ever tell me I had to wear dresses or skirts, He did put some encouragements into place. If I wear something appropriate I have the liberty of masturbating how and when I choose that day. If not, then it's limited to after a certain time of day. Not a huge thing, but just enough to remind me that He would prefer I dress that way. Lol, oh, and during baseball season He tied a Red Sox loss + a day wearing pants to no masturbation at all. I quickly became a fan.
I start "trying on" the idea that maybe, just maybe, I might be able to dress "like a girl" and not look stupid doing it. I watched "What Not to Wear". I went shopping three times a week, just trying stuff on. I didn't buy anything, but I try stuff on. Having to actually buy something would have put too much pressure on the experience.
I begin to look around everywhere I go and look for the women dressed like He wishes I would. Now I'm frustrated with myself, because that wistful tone in His voice when He says "Pants again today? That's too bad..." is making me feel terrible.
New clothing is gradually purchased. Now I need shoes. I have big feet, and I hate shoe shopping. It sucks. I go anyway. I am determined. Finally an entire work week goes by without pants. Then I start (gasp) wearing skirts on the weekend. I suffer the horrible embarrassment of grocery shopping in a dress - voluntarily, because I wanted to see if I could do it. I lived through it. The first time He called and happened to catch me wearing a dress was extraordinarily memorable. I was extremely pleased with myself.
Six months after we met, with me voluntarily wearing "anything but pants" 90% of the time, He institutes a rule about stockings. Rule now, not voluntary clothing choice. By this point though, I am comfortable enough with the idea of me dressing like a girl that such a rule doesn't feel like it would have in May. Back then I would have floundered and felt overwhelmed by it.
Makeup has been increased gradually; nothing outlandish, but mascara and lip gloss are a daily thing now. Sometimes I wear ear rings, although I'm still not a big fan of jewelry. It was a lengthy and costly process (I replaced nearly my entire wardrobe), but for the first time ever I didn't dread going shopping. I look forward to it now, because I have a different thought process to take with me. It's not "I hate this, nothing looks good on me", it is "I hate shopping, but I love wearing things He likes". He did this using only rewards, never punishments. One of the best parts, other than knowing that He likes how I dress, is that for the first time ever I feel competent in the whole "fashion" department.
Self-image is such a large thing that I liken it to turning a freighter. It's not a speed boat, and won't handle like one. It took consistent reinforcement of every little thing I did that was even a baby step in the right direction. If for some reason my Dom and I were to part ways, I would continue to dress in a more feminine manner than I did before. Why? Because I like it now.
The most important part, I think, was that the entire time I felt led, not driven, to this goal.
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And if I cease to desire and remain still,
the empire will be at peace of its own accord
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Force Feminizing a Tomboy - 
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