Dear Auntie Helga,
I recently came across your website and was thrilled to find other transvestites and sissies whose wives have encouraged them to become maids. I have been cross dressing with my wife's approval and participation for about 30 years and during my early years there were quite a few outings with me dressed as a woman. I never really passed as a female, I merely got away with it as there were no scary or frightening confrontations whether we were shopping or just walking along but I was teased a few times and taunted by men. My emotions were like a roller coaster, fear, shame and humiliation but also joy and wonderfully feminine feelings and sensations such as the gentle tug of my garters on my stocking tops and the feeling of my skirt brushing against the back of my knees all topped off by the distinct sound of our high heels clicking in unison on the pavement but I'm getting ahead of myself here.
My cross dressing began as bedroom fun with me in panties and stockings and a little too much wine but it was harmless fun and in no way was it my wife's intention to feminize me. To this day neither of us remembers whose idea it was but wearing her panties and stockings at bedtime became routine and added some spice and naughtiness to our sex life. I do remember after the first few times sheepishly asking if I could wear her panties and depending on her mood she would pick a few pairs for me to choose from, usually pink, lavender or yellow with pretty lace accents or cute bows. I felt so ashamed of myself as she handed me her panties but I knew what was to come once I put them on.
She would also hand me either pantyhose or stockings and garter belt and I'd slip into those too and from there it was lights out and the foreplay began. This happened a half dozen times or so and always ended blissfully for both of us. We had discovered something that was fun but a huge secret we could not share. One evening I yet again asked if I could wear her panties to which she replied I should have my own and eventually we shopped for panties for me as well as stockings.
From here I often wore my pretty things under my male clothing when we were out running errands and such. There were times I'd come home from work to find new panties or stockings neatly placed on the bed and things really took off when there was a lovely lavender baby doll and negligee set placed on my pillow for my birthday. That night she took lead in bed, something she had almost never done and a week or so later I had the matching bra too.
At some point not long after she mentioned the hairy legs and chest spoiled the look and I agreed suggesting I get rid of it The feelings of being in my prettiest things were incredibly sensual and that first night was pure magic. Being silky smooth was a big step and moved from bedroom fun to near daily life. My wife's acceptance and participation now had me wanting to experience much more and my feminine wardrobe began to grow. Some of it were her suggestions but most were mine, she always got the final say and still does. High heels, dresses, skirts and blouses began fill my closet and I had my own lingerie drawer full of lovely things, cute panties, pretty bras and slips and lots of stockings. I was a fully feminized transvestite now although I had not yet heard that term and I could hardly wait to get home from work to get some "girl time".
Meanwhile my wife's encouragement was driving me to abandon many male oriented activities I did so that I could stay home and be dressed in her presence and she didn't mind this at all, it meant no more pub after work or weekends away with the boys fishing or working on cars. But something was missing, despite my fears and all logic I yearned to experience my new found feminine side in public. I wanted to know what it was like to walk more than the length of my living room in high heels before having to turn back. I knew I wouldn't pass as a woman very well or at all but I didn't care, I knew other transvestites did this sort of thing and the more I thought about it the more obsessed I became. We had long conversations about this, my wife wasn't opposed but worried about my safety and was willing to step out with me. We came up with several plans and in the meantime she practised doing makeup on me and getting a suitable wig.
My very first outing was merely a walk after dark on quiet streets not too far from home. What I remember most as we left she handed me a purse saying I'd need this and showed me how to put the strap across my shoulder, it was the finishing touch and I truly felt like a woman. I carried it with pride, a symbol of my coming out so to speak. There would be more outings and each one more daring that the last. In all we've had more than ten and less than twenty outings over the years. We've been to restaurants and shopped for lingerie, shoes and clothes and have had wonderful experiences and even a few compliments from sales ladies knowing full well I was a transvestite.
One time however we were followed by a couple of young men with backward facing baseball caps calling me a sissy. I didn't like being taunted but I definitely felt like a sissy being too afraid to tell them to leave me alone. Here I was enjoying walking in high heels only to find out the hard way you can't hurry up in them. My wife by now had had enough and was just about to confront them when they gave up and rounded the next corner. Normally it is the man who protects his woman, here the woman was ready to protect her sissy. How ironic!
Fast forward many years and my wife was looking at patterns in a fabric shop to make Halloween costumes and she pulled out one that was a French maid's dress. She giggled saying that I already did the dishes while dressed and proceeded to put it back commenting that I'd probably be too embarrassed to wear it. She was right of course, I did enjoy doing the dishes and other housework while dressed and she had even made me a few aprons to keep my dresses and blouses clean while at the sink. I immediately got the feeling she'd be okay with me wearing a maid's dress and I really didn't care if I'd be embarrassed. It was a deliciously sexy outfit and I knew it would be a very sissy thing to wear and I was more than willing to wear it. I told her if she made it I would wear it and with a devious twinkle in her eye she said it might be a lot of fun.
At the time it was not intended for me to wear for Halloween but those plans quickly changed. We then picked the shiny black sort of satin finish fabric and the fabric for the petticoat along with narrow white lace for the hem of my dress as well as the neckline and trim on the sleeves and some white fabric for the little apron. On the way home I felt like a kid at Christmas, I couldn't wait for her to make me my dress. A week or so later neatly laid out on the bed was my gorgeous French maid's dress splayed out with the cute little apron tied in place. I couldn't wait to get into it and after my shower and quick leg shave I chose my black under wired bra, black lace panties and black stockings and garter belt. As I dressed I became rather hard and who wouldn't? I stepped into my ankle strap black heels and presented myself to my wife who was seated in the living room.
She began to giggle and I must have turned a hundred shades of red. I never felt so humiliated in her presence before but being in such an adorably sissy dress had me on cloud nine. I just stood there while she examined me and told me to turn around and model my dress for her and I obediently complied. Her giggles continued almost with tears in her eyes and I knew how amusing this must be for her and all I could think of to do was to curtsy. It was a terrible attempt and her giggles turned to laughter saying if I was going to be her maid I'd have to learn to do better. Meanwhile I had almost exploded in my panties and I would have been humiliated to no end had that happened, these were incredibly sissy experiences and it was difficult to control myself. When her giggles and laughter subsided I attempted another curtsy and thanked her for my dress adding that she now had a maid. Over time I learned to curtsy and the humiliation of being in my maid's dress in front of her has diminished greatly from that first time but it's still there sometimes when I curtsy.
But back to the reasons we were shopping for patterns for Halloween costumes. Our local pub used to host costume parties every Halloween and there was always a sizeable cash prize for best costume. I had been tempted a couple of times to wear one of my nicer outfits and my wife was more than encouraging so the idea was to find something suitable for me. Seeing the pattern for the maid's outfit and my wife's positive reaction I became very excited about the possibility of me wearing it for Halloween and not just for doing the dishes in. Once I began wearing it of course I very much wanted to go to the Halloween party as my wife's maid, it wasn't about winning any money but about being seen in something so cute and sexy. As always my wife was 100% behind me and she happily agreed.
As the day approached and the evening drew near we got into our costumes, she a witch and me as her maid. I chose my under wired black lace bra and matching panties, black pantyhose and my ankle strap heels and once in my dress I put on my little apron. As the clock ticked closer to when we had to leave I began to get nervous and have second thoughts. My shaved legs and ability to walk effortlessly in high heels would have had people we know knowing this wasn't my first time and I was afraid of being humiliated and laughed at. My wife sensed my apprehension and asked if I still wanted to do this saying we didn't have to go if I wasn't comfortable. I wanted to go but just couldn't and I felt terrible for spoiling her fun and with that she gave me a hug and I nearly bust into tears. I ended up not wearing anything feminine and it has bothered me ever since, I failed at being her sissy when I so much wanted to do this for her.
There have been times when I have been at the sink doing the dishes when she has come up from behind to fix the bow I have tied at the back of my apron much the same way a woman fixes her husband's tie. To me it's a sign she is pleased with my efforts and a further encouragement to be her maid. It was during one of these times adjusting the bow on my apron when she lifted the back of my dress exposing my panties and gave me a sharp smack on my bottom. This was a first and I turned and asked what that was for, with a twinkle in her eye and a slight smile she replied, "Just because". While she has not taken this much further her firm hand has me on edge when she approaches from behind because I never know if she's in her devious mood. It's not really a spanking but a reminder of who is in charge. Neither of us knew so many years ago that those first panties I wore would result in where we are now but I have found my place as an obedient maid and a submissive sissy whose calling was inevitable, I can't thank my lovely wife enough.
Thank you for your letter Jennifer. How delightful that your wife not only approves but participates as well, that is somewhat unique and you are very fortunate. What started as an experiment has now turned into a lifestyle and I'm sure she appreciates the help around the house and you get to wear the pretty clothes.