A Wish to be The Maid

More wishes Come True!!!

Once they got back to Christine's house she asked Jemima to make them coffee as she sat in the lounge, amused at seeing him getting used to walking in his unaccustomed tight skirt. He returned, presenting the coffee with a neat bob, to her delight.

"Sit down Jemima, let's have a talk before you start work," Christine said kindly. "Now, be completely honest, did you find that experience exciting, sexy, humiliating, frightening - how would you sum it up?"

Jeremy thought for a few seconds then shrugged. "All of those really. At times I just wanted it to stop, at other times it was incredibly sexy - and, yes, I was frightened all the time."

Christine regarded him carefully. "Did you think I was being cruel to you?"

"Yes, I did." He paused. "But that was very sexy really, I don't know, just being in your power was weirdly exciting."

"Would you like to do it again?"

"I'd be terrified - but I don't really have a choice do I? I've agreed to your conditions so I must do whatever you ask."

Christine smiled. "Yes, but I'd like to make what we do together enjoyable for both of us. Now I know you've said that you enjoyed parts of that experience, and I must say that I enjoyed all of it, particularly when I teased and embarrassed you, that made me feel very sexy indeed, as you'll find out soon! But apart from me deliberately making things awkward for you, which was all part of the fun, what did you find a real problem?"

"Well, I suppose the fact that just about everyone could see that I was a man trying on women's clothes and then leaving the store wearing them was the most difficult thing. I've fantasised about situations like that many times but the reality.......well........??

Christine regarded him thoughtfully. "Look, you are a biological man, a very well built, handsome man, I enjoy certain parts of your masculinity and I don't think that I would want that part of you to disappear." She paused. "But I," she continued, "and I think you, get a real kick out of putting you in situations where it is obvious that you are a petticoated man, under the control of a dominant woman and I want that to continue - don't you?" He nodded slowly. "But there will be situations where I would like you to appear in public presenting as a woman, business events, holidays ..........I don't think that you could ever pass close inspection as a woman but with work I think you could certainly pass to the casual observer, how would you feel about that?"

"What sort of thing have you in mind."

"Well, a nice hairdo, professional make up, some artificial curves to help your body shape.....all would help. I, of course, will continue to train and guide you to achieve a more feminine appearance and manner. I think that once you get more confident that will help you to behave naturally and avoid unwanted attention." She regarded him firmly. "Because, make no mistake, I will be requiring you to leave the house fairly often, either with me or, eventually, on your own. We both, very clearly enjoy the buzz of exposing you in public. So are you prepared to work with me to achieve that?"

He nodded slowly. "Yes, of course." He gulped eventually. "But as you say you don't think I will ever pass close inspection as a woman, I'm not really clear what my role is to be."

Christine smiled and thought for a while "That's a very good question. Like you, I've never done anything like this before and we must almost learn together what works and what doesn't. My view, I suppose, is that when we are out in public I would like us to appear to the casual observer as lady friends, not particularly attracting much attention." She paused and thought further. "When we are in social company, either here or elsewhere, I would like people to see you as a heterosexual crossdressed male, my lover and companion. Here, in the house, of course, you will be my submissive crossdressed employee, PA, Housemaid, maidservant, whatever position you are filling at the time. Does that answer your question?"