This is a tough blog post to make because I know that Deanna may well read my blog and I now have to speak about her. She has indeed decided to blackmail me into crossdressing for Halloween. Now, that does sound a bit worse than it is. I had one of the few friends that I can talk to about this sort of thing (The girl I referred to previously as Oklahoma) tell me, "Let me get this straight, since we've begun talking you've whined to me that crossdressing wasn't exciting without a woman making you do it. Now you want to whine that a woman wants to make you do it?"
When she put it that way, it made a lot of sense to me. I have subsequently discussed it with a couple of dominant women who told me that it probably wasn't pity blackmail, but instead was a safe way for Deanna to play. She had admitted to liking her power over me and college and missed having it.
By the same token, I'm not worried about her doing anything that would get me busted. It does have the effect though of making the dressing up thing exciting and that's kind of cool. Shopping again has me very nervous, but it hasn't been as bad in reality as I've made it in my mind. I did have her keep me under "house arrest" -- my term not hers. She said as long as I had everything I should get used to it and put everything on. She then warned me that she could call me at any moment and if I took to long to send her a picture, she'd know I wasn't wearing my dress. Mission accomplished.
I don't know how long this will continue or if I will eventually post current pictures. I feel like my old pictures give me three layers of security--1. I'm a decade older and I look it 2. I'm crossdressed 3. I put the mask over my face. If I post new pics, I give up a layer of protection. I may do something though. I don't look as good as I once did, but I don't look like an old hag or anything.