On Monday Mistress and I went out to happy hour with one of her friends. I am currently not drinking so I just had water. Mistress and her friend proceeded to drink and gossip. I felt something at the time, but it didn't really click until last night. I was essentially her chauffeur. I have fantasized about Mistress making me dress up and taking a group of women out on the town. I wouldn't join them, I would just be there to drive them around and get them home safely. I also fantasize about Mistress controlling my food and drink when we go out. Now she didn't say I couldn't drink, but it was easy for my mind to make the leap. Over the next month of me not drinking I can see Mistress making me feel more like her servant when we do out than an equal partner. Hot!
I am having to dive deeper into my feminine closet. It scares me yet excites me. I am trying to be safe and deniable with what I wear, but Mistress has added a challenge of not allowing me to wear the same thing in the same week. In my opinion that leaves it a little too safe for me. I will wear my 7 safest outfits each week. Instead, I imagine having to wear every item at least once prior to being able to start over on my wardrobe. Once I wear it, it goes into a hamper until I've worn everything. That would mean I would be in some pretty skimpy/slutty dresses for a few days. The thought makes me shudder. I also think of being required to wear additional items like bras, breast forms, wigs, and high heels. That would be the right kind of mean.
Also, I wore three different feminine items under my male clothes while at work this week. A pair of control top pantyhose, a pair of heavy duty pink leggings and a body shaper. All of them kept my cock squished down and made me feel very constricted. Mistress said "it's good for you". I can't agree more.
Lastly, I feel that I have failed a couple times this week. The requirement is that I have to be dressed femme within 30 minutes of coming home. I failed twice. Once on Wednesday when I got home from work, and yesterday after we ran a morning errand. In both cases I continued to be dressed in my male clothes for well over an hour. To make matters worse, yesterday I had items to put on about 20 feet away from me. I believe the failure occurred due to me wanting to maintain that last little bit of control as well as me fighting some internal insecurities. Even this morning I had to overcome this problem. We have some company coming over this morning. I intended to wear my male clothes until they left. Instead I sucked it up and put on some pink yoga pants and a feminine sweatshirt. I will change clothes 10 minutes before they get here, but I will be wearing feminine items under my male clothes. Regardless I feel there should be consequences for failing. I really, really want to do as I'm told 100% and need to be held accountable to make this work.