I just had to write again to tell you what happened last Saturday evening.
I was out with my boyfriend, and Joanne was of course charged with the task of selecting appropriate clothing for me to wear. I could easily do this myself but it is great fun to tease Joanne and sometimes the sight of me in my finery reduces her to tears.
First she must choose my underwear; pretty bra and knickers, and tights or stockings depending on which dress she thinks I would like to wear. So there is also the thinking about it as well as the torment of handing me each item, on her knees. If I disapprove anything she gets the cane. She gets the cane before I leave anyway. Just to be clear I do not allow her to see anything of me that she shouldn't: she has to leave my bra, knickers and tights on the bed while she kneels in the opposite corner looking the other way. Only when I snap my fingers is she permitted to look at me, and what a sight I am even if I say so myself.
Anyway I had been chatting on the phone to Elaine that afternoon and the subject of what to do with Joanne while I'm out on my date came up. Elaine is, as I may have told you, getting very interested in the humiliation of sissy little girl Joanne and she suggested I give her essays to write with titles such as "Why I Dress As A Little Girl" or "My Favourite Sissy Dress" . I thought this a great idea, and so last Saturday while standing over Joanne in my short dress, tan tights, high heels and with my waist-length hair hanging down provocatively, my face beautifully made-up I smiled sweetly and told her she was to write an essay while I was out titled "Why I Dress As A Little Girl". It was to be at least 2,000 words and I would read it on Sunday morning while in bed after my boyfriend had gone home. If I approved it Joanne would be allowed to curtsy to me and kiss my feet and my bottom (through my tights and knickers). If I didn't then she'd get the caning of her life.
I'll just share an extract with you:
"I am sissy Joanne and I love wearing little girls' sissy dresses, petticoats, frilly socks and panties. Ladies' panties, girls' panties and frilly sissy panties, white lacy stockings and my lovely sissy frilly suspender belt. I am a sissy, not a man; I could never satisfy a beautiful lady such as my adored Princess Maria who graciously teases and torments me with her beauty and femininity and who has a handsome real-man boyfriend to give her what she needs. She humiliates me to keep me knowing my place at all times and sometimes in front of her girlfriends, and teenage girls beautiful tormentress Elaine and lovely Susan.
I dress as a little girl because it is only right that as a pathetic excuse for a 'man' I should draw attention to my true station, that of being helpless, useless, sissy and fairy-like in my beautiful frilly girlie frocks. My fairy dress which is so short and white which I have to wear with white tights and white frilly panties makes me such a little sissy girl which is exactly what I deserve. How I look longingly at Princess Maria and the other girls and ladies Elaine and Susan but know that I can never ever do anything except look, curtsy respectfully to them all and wait on them, be humiliated by them and submit to whatever punishments they decree.
I am a sissy, a fairy, a girlie-girl, a faggot and am so lucky to be owned by beautiful Princess Maria and willingly submit to each and every torment she designs, sometimes with the help of beautiful Miss Elaine.....
... I am nervously hoping my humble efforts will be approved by Princess Maria and that I will be allowed the ultimate honour of curtsying to her and being allowed to kiss her pretty feet and her beautiful bottom"
Well, I can tell you that I was actually pleased with what Joanne had written. I made her read it out loud to me and then I arose and dressed before I gave her my verdict: the tension was terrific. I eventually told Joanne I was pleased and I allowed her to curtsy, kiss my feet and my bottom although I did have to tell her off once or twice for getting excited and kissing too furiously. I let her do this for a good ten minutes which I think was very generous of me and then I inspected her little dolly inside her panties. As I expected it had grown which Joanne knows is forbidden but under the circumstances understandable and I was rewarding her after all. So I allowed Joanne onto the bed, gently pulled her panties down and gently stroked her little dolly for a while as an extra treat. For me that is: I love to make Joanne cry and the tantalising gentle stroking of her frustrated little dolly is guaranteed to make her cry. I spent over half an hour bringing her to the brink, stopping, smacking it and then stroking it again. I only stopped when the phone rang: it was Elaine asking how the essay went. I told her if she wanted to call round I'd get Joanne to read it out load to her.
So Joanne's panties were pulled back up and I told her to put on her little fairy dress for Elaine.....
Ps. Just to let you know, I have just given Joanne a really good thrashing with the cane. It was a good job I gagged her. I made her wait while I prepared this email, and for good measure had a nice glass of wine before going up to her. The caning was followed by putting her into her single bed and then I checked the state of her little dolly just to make sure she was behaving. I'm pleased to report she was so I gently stroked the front of her frilly panties which made her sob even more. Tears were running down her face; I almost felt a little bit sorry for her.
Thank you for your letter Maria. Writing essays are great training for sissies, each word reminds them of their predicament and brings shame again when read by their superiors. Hers' was a perfect example that could be followed by sissies wishing to impress their own Mistresses. I'm sure that many readers will also appreciate your teasing the sissy's little dolly while denying her final release, another fine way of showing her that you are in control.