‘Cross-dressing sissy’ is very much a work in progress and it has required compromises from both of us. Actually, the cross-dressing part has been the easiest for her to accept. Once she got over the shock and was reassured that I’m not gay, cross-dressing has continued to evolve at a pace I think we’ve both been comfortable with. Her first husband announced that he played for the other team six weeks after their baby was born. So it’s understandable why she was skittish.

It’s the sissy part of the equation that has been the most difficult for her to accept and has caused the most conflict. She really is a ‘mum’ in the truest sense of the word. She likes having a clean and tidy house and gets pleasure from getting everything just right. She loves to cook. She sews…she’s even sewed some of my girly clothes. Her nature is to be nurturing and caring. She makes chicken noodle soup (from scratch) when ever anyone is sick, she helped heal a 28 year rift between my mother and I, she’s kind and gentle and if either of her husbands had have been different men she would have loved to have raised a house full of kids.

In her perfect world we would be equals in every way. It is not in her nature to dominate me, but the sissy in me craves to be dominated. I do not believe she can bring herself to think of me as a sissy. Even activities that I think of as acts of submission; brushing and braiding her hair, filing her feet, massaging her hands, painting her nails, shaving her pussy, doing more housework then the average Joe, I’m sure she thinks of as just her good fortune at having a very attentive husband.

I’ve emailed her links to blogs written by women I think have been in a similar situation to her and if she reads them she doesn’t mention it. I’ve bought books that I hoped would encourage and reassure her that gather dust on her book shelf. Her rare half-hearted attempts are done out of obligation and leave me cold.

It would be a simple thing to say, “if you loved me you would do this for me and enjoy it.” But I know that that’s unfair. I’m asking her to be something she is not. It’s not her fault that I know her so well that I know when she’s faking it. So, for the most part I’ve stopped asking. But of course she also knows when I am faking it and knows that I am denying part of who I am. She feels like she is stopping me from exploring who I might become. She also knows that I would do anything for her. I think she probably feels guilty about not being able to do this and I feel guilty for wanting something that she can’t give and on and on it goes. Part of the problem is I don’t have a clear idea of where I want this to go. I can say I’d like to try this or that, but have no idea of where I’d like us to end up. I think the journey for me is more important then the destination. That must make it even more difficult for ♀.

We do try to bridge the gap with trash talk during love making and ♀ is very good at talking dirty. (she’d make a fantastic phone sex operator.) I went back to work Jan2, but ♀ didn’t go back until Jan 3. Before I left she asked me to call her when I was done because she wanted to get up and make me breakfast. I told her there wouldn’t be much on and did she really want to get up at 5 am on her last day off? She assured me she did and I came home to eggs benny and the love of my life.

After we went to bed and started getting each other excited, she told me she was very disappointed with me. She’d been nice enough to let me wear her new red dress, but I hadn’t hung it up properly and she’d found it in a heap on the closet floor. The rest of the clothes I’d borrowed were piled up on her dresser. She threatened not to let me borrow her clothes anymore and talked about all the things I would need to do for mommy to make it up to her. The entire time we were making love she described how she would turn me over her knee and spank me with a wooden spoon until I was crying like the weak little sissy I am. How my little red ass would be so sore I wouldn’t be able to sit down for a week. How I’d only be able to wear the softest of nighties and the next day she’d bend me over the back of the couch and fuck my still stinging bum with the strap-on. I think that’s about the time I came. She came shortly after and insisted that I lick her clean so there is hope. And for now that hope and a good imagination is enough. Click here for sisssy pic

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I think I was about 12 or 13 the last time my old man used the belt on me, though I don’t remember the event. I do remember the last time my mother threatened to use corporal punishment. I was probably about 11 years old and was fighting with my sister. She was three years younger and still feared my mother (i think she still does). Anyway, my mother yelled at us from another part of the house to stop fighting. I continued to do what ever it was I was doing to torment my sister. More yelling was followed by the rattling of the cutlery drawer, but I didn’t stop. Finally my mother burst into the bedroom brandishing the dreaded wooden spoon. She smacked it down on a stool for dramatic effect and it broke off in her hand. There she stood with an angry look on her face and holding a little wooden handle. I did what any cheeky 11 year old in the same situation would do.

I laughed.