I love the work you do on your website and thank you for sharing so much of the petticoat lifestyle. My ex husband was not interested in any lifestyles other than his own. When he passed away I like many widows I vowed to stay single however after a few years it wasn't for me. I began seeing a few men however no sparks leading to relationships occurred. A girlfriend mentioned alternative lifestyles which lead me to learn about petticoating. I didn't have a man in my life however enjoyed reading about those women who did and the lives they live with their sissymaids.
One day while shopping I bumped into Chris leaving the women's department. He picked up my bag for me when I noticed he had cleavage. That is right Helga I mean real cleavage that made me kind of jealous not having much up top. One thing led to another after a coffee with weeks later us seeing each other weekly. Chris shared his life with me and how having breasts left him a lonely man. It took me a few weeks to get used to Chris having breasts and bigger than mine. Well Helga here we are months later with Chris and I living together in my house. He is a real sweet man and always wanting to help me.
It was just last weekend after reading a few letters for July on your website when I thought maybe Chris might enjoy living with me as my sissymaid. Like many other women I wanted to start slow if there was going to be a chance. I bought Chris a few pairs of panties in all colors asking him to start wearing them instead of boxers. He looked at me funny when I went on to say boxers and bras didn't work for me. Chris now wears panties and sleeps in the same nighties I own.
I bought Chris some razors to shave his legs and underarms which he uses without too much trouble. Last night I asked Chris if having breasts ever caused him to think more feminine or want to dress more feminine other than his bras. He looked at me blushing letting me know he once tried on a dress but then put it back thinking it was wrong. Chris asked me why I wanted to know which led me to admit he might look nice in a dress if it was the right style.
We started talking about women's clothing styles and colors that might look very nice on him. Chris wanted to know if I wanted him to dress like a woman at home or outside too. Putting the question back to Chris I asked what would he prefer as he hesitated. I let him know it was possible to make him look more feminine with makeup so we could go outside if he wanted. Politely he let me know it was okay to buy him a dress and he would try it. I clapped letting Chris know I appreciated him wanting to experience his feminine side with me. He asked me how often would I like to see him in a dress opening the doors Helga. I went on to let Chris know it would be nice if he always wore women's clothing whether a dress or a pretty blouse and skirt. He looked at me with a 'really' look on his face when I continued to let Chris know I thought he wanted to do this for many years.
Looking into his eyes I asked if he wanted to be more feminine and wear dresses and skirts. Chris blushing away admitted it would be nice to give it a try not every having anyone ask him it before. So Helga I suggested to Chris we go shopping over the next few days to find a look we both liked. He continued to blush then asked did I mean he was going to wear like high heels too. I thought wow he sure has a lot of questions.
Chris was interested so I let him know it would be best if I bought him everything he would need to look and feel like a women so yes high heels too. Helga while I am sitting her typing away Chris is looking at a few websites I gave him for dresses and shoes. I can't imagine how Chris lived all these years with women's breasts and wearing just a bra when he could have been some woman's sissymaid by now.
You can see it in his eyes he wants to share his feminine side and with me even suggesting we try it his eyes opened up. How often do you find men who are more feminine than the picture they paint? With some luck Chris will agree to be my sissymaid and if not I will apply pressure to make it happen.
How nice to hear from you Carolyn and thank you so much for your kind words about my site. Living the petticoated lifestyle can be a very rewarding way to live. So sorry for your loss, my husband passed a number of years ago. The upside for having a sissymaid is amazing and wonderful, a whole new way to live.
How fascinating that he has breasts, though you didn't say how that came to be, I assume it is due to gynecomastia. In any case, he has them and it would seem better for him to embrace his condition and dress appropriately. Good start with the panties, that is the simplest and really most effective way. I imagine he has had the desire to wear dresses since his breasts started to develop.
Men quite often have the inner desire to embrace their feminine side but society holds them back, he seems to have needed your acceptance, approval and encouragement. Of course the next logical step is to become your sissymaid and anything I can do to help you with that, of course I would be delighted to do so. Readers please stay tuned as this new relationship starts to develop.