I'm an active reader of ways to spice up my life with husband Jim having only been married for a few years now. We are both in 40's having been married before I found Jim to be a sweetheart compared to the pig before him. One of the qualities I like the most about Jim is his willingness to try anything at least once instead of the typical male not wanting to do anything that impacted his macho world. The two of us are very playful with joking around or daring one another to do something out of each others comfort zone.
Anyways as I mentioned reading online stories or visiting the questionable websites is something I enjoy. Seeing men dress in their wives lingerie or fully cross dress has interested me for some time although I was careful not to tell Jim. Learning from experience if most men had an idea their wives might want them to try on panties as an example they would run or at least get all mouthy about not wearing that stuff, are you kidding. So having that in mind I thought maybe I could test Jim knowing that he isn't the kind of man that would get all bent out of shape. I waited for the right opportunity one night while getting ready for bed by throwing my panties at him. My previous husband wouldn't touch my panties unless ripping off for sex. Jim caught my panties asking what was he supposed to do with them. Jokingly I dared him to try them on with a smile. Jim looked at me then looked at my panties. He dropped his jockeys then put on my panties.
Well Helga not only was I surprised but had other ideas in my head all of a sudden. I whistled at Jim while he pranced around acting nutty. He was about to take them off when I asked if he would wear them to bed with another smile from me. We ended up fooling around but after I begged him to sleep in my panties. Helga that was the beginning, a few months ago with me wanting Jim to wear panties more often until now that is all he wears for me. One thing I noticed falling in line with some of me reading that Jim became more thoughtful and helpful to me. Now he didn't know it was the panties doing it but I did.
We still played the dare game which is when I got him to try on a bra. That night he slept on one of my old bras until I got around to buying him one of his own. Every Saturday night I would add something else like pantyhose then she would have to sleep in them I dared Jim to shave his legs which he reluctantly did, giving me clues. This continued with me taking Jim shopping not so much for him however I always bought him something for dare night. Helga I even dared Jim to wear a bra, panties and pantyhose shopping with me for the promise of great sex that night. To sweeten the dare Jim had to fill the cups of the bra before we went shopping. Jim wasn't too sure about that idea but went along with it.
A few weeks ago with me wanting to go further after reading some of the letters on your website I took Jim shopping like usual. This time we stopped at a second hand clothing store that sold women's clothes and shoes on consignment as well as other inventory. Now Jim was a good sport to go shopping however he didn't always pay attention which was a good thing. I spotted a couple pair of shoes in Jim's size that I dropped in the cart then moved over to the dress isle. It took a while to find something nice so when Jim went to the bathroom I picked that dress, a pretty white see through blouse and a black skirt before Jim got back. By now the cart was filling up when I spotted a rack of nurses uniforms. I asked Jim if he wanted to go warm up the car as I was almost finished which was music to his ears.
Looking at the uniforms I realized they were maid uniforms with the hotel name on them. Helga I wanted to talk to you about petticoat training and sissymaids first but had to grab one of those uniforms so I did. That night after dinner we were joking around when Jim dared me to give him a blowjob in the kitchen. Jim's dares were mostly sex related however mine were feminizing him. I gave him his blowjob with a condition that my dare was going to be two parts. Jim was already wearing the bra I bought for him, panties and pantyhose so he was ready. I dared Jim to wear what was on our bed which was the dress I bought and the high heels. Jim feeling pretty good after having a blowjob went to the bedroom with me behind him.
He looked at me saying no way Doreen that is cheating. I looked at Jim asking if he was wimping out after all the dares we shared. Reluctantly he took off his shirt and pants revealing his bra and panties. I helped Jim with the dress that zipped up the back and his heels. Jim was having troubles in the heels for a moment as we went to watch TV together. He wanted to take it off but I wouldn't have anything to do with it pointing just because his blowjob didn't last was no reason for him to give up on my dare so fast. The next morning being a Sunday I laid the blouse and skirt on the bed along with clean panties, his bra, pantyhose and heels. Jim was in the shower while I went to start breakfast. When the water stopped I waited as this was the test if Jim would get dressed without me saying anything or a dare.
Jim was quiet but like in a sales negotiation the first one that speaks is the loser. It took a while then Jim walked in the kitchen asking he was supposed to wear this as I turned around. I responded with a wow you look very nice Jim and it all fits nicely too. Jim only said on thing which was you owe me Doreen. I figured as much that was coming. Since then Helga Jim goes to work in panties, a bra (without filer) and pantyhose. On the weekend he wears with his dress or blouse and skirt as well as his heels. I bought him a couple of nightgowns to sleep in as well. Jim keeps his legs shaved without me reminding him.
So Helga now that you can see the life of Doreen and Jim what do you think of Jim becoming a sissymaid? I haven't shown him the maid uniform yet. As far as Jim knows I like him dressing in women's clothes so he does it for me. The whole ordeal has had an impact on him in that he is so polite and caring now. He was always a good man but now even more so. I feel confident he will wear a maid uniform or sissy dress for me when I ask. Helga I would also like to play with chastity if you recommend it. My idea is to have Jim become my sissymaid most of the time however want him and my best friend and lover too.
What do you think? Do all wives have to take the very dominant approach or can it be fun too? When I say fun that is as long as Jim obeys me.
Thank you for your letter Doreen. How delightful to hear from you and I am so happy to see that you are petticoating your husband, I would be delighted to help however I can. As you can imagine I support him becoming your sissymaid though this, like all of the fun to come, is up to you. Chastity is also a good thing to do, control the penis you control the man.
There is no reason he can't be all that you desire, sissymaid, husband, friend and lover, though when he is in sissymaid mode he should be the real thing I feel, that is feminine and obedient. Not all of it has to be done by dominating as you yourself have him wearing panties and other items full time, so no reason that can't continue and should he balk then, well, you could always think of another, perhaps stronger approach.