SHY LADY AND SHY GUY
from Jen

Dear Helga,

I'm a little shy as writing to someone on the internet isn't usually my thing so please bear with me. Your website has so much information that is exactly what may help me with my boyfriend. We have been with each other for several years. About 4 years ago Art was diagnosed with gynecomastia which caused swelling of his breast tissue. We looked at all kinds of ways to deal with the condition yet in the end Art's breasts were just part of him. When they grew to a size where he could no longer hide them I bought him a sports bra to help with support. Art wasn't found of wearing anything however it was necessary in my opinion. I don't go braless and I felt Art shouldn't either. Some men don't grow much more than a woman's A cup. Poor Art grew to a B cup within months which meant he had to wear a bra every day. As time went on Art grew more so I decided to have him fitted properly instead of buying bras from Walmart. Art did not want to go with me or have me pick out something very feminine. I promised to have him fitted with something plain yet functional. The girls were just amazing how they helped Art feel comfortable with the process. They explained several men had been at their shop before and it was no big deal for them to help Art too.

Life was a challenge for Art in the summer when he couldn't hide his breasts under a jacket or coat. It was all I could do to help him feel comfortable about himself. Then one day Art was due for a couple of new bras as they had just worn out. We went back to the shop where he was comfortable with the girls. This time I insisted he buy something nicer than the plain bras he wore all the time. Art had been wearing a bra for quite some time so it just made sense to me that he wear something nice. Once again Art put up a fuss until one of the girls talked him into trying a few on for fitment sake. I liked one that had flowers on the cups with a lace trim. It was a bra I would wear if they had my size. Before Art knew it they rang 2 of the bras in and off we went home. Here I was a shy woman with a boyfriend who had to wear a bra what next. Somehow that was changing who we were faster than I thought. The more we looked at the internet the more we both realized Karl wasn't alone as a bra wearing man. One woman who had been married several years wrote that her husband had the same gynecomastia condition. Her husband would not go out of the house in the summer months so she came up with a radical idea. I talked with Karl about it however he was not going to go that route. Well without his knowledge I began to purchase a new wardrobe for him and it wasn't from the men's department. Art had some Asian blood in him so he was thin and fine featured. In my mind there was no reason I couldn't help him look more feminine. With any luck Art would pass enough that we could go out and enjoy the summer. Some of the letters on your website gave me some ideas although would Art let me feminize him?

Weeks later I tried to talk Art into trying on the things I bought for him. The first night he was not interested. The next night the same thing until 4 nights later he agreed. With some makeup and a good wig Art could pass from 10 feet away. It was only when I saw Art before me in a pretty sun dress that I felt it all might be possible. Then of course with the reading I did on your website the thought of Art as my sissymaid became a closer reality. Anyway as the weeks went by Art would allow me to help him look more feminine once or twice a week The wig really helped however Art had a ways to go with learning how to carry himself like a woman. We practiced every few days with Art in heels to help until I thought it was time for a test outside in the real world.

One Sunday afternoon I helped transform Art with some light makeup. We got in the car and before we knew it Art was miles away from home dressed as his feminine self for the first time. He didn't look bad to me at all and in fact he was shocked at what had been done. We drove to a park miles from our home where after some persuading Art finally got out to walk with me. Art's hair blew in the wind just enough for it to look natural. With the women's sunglasses covering his eyes and the bangs covering his forehead art was pretty convincing. As Art walked with me I coached him on what we practiced at home. This was the first time Art wore anything that showed his breasts and cleavage without trying to hide them. I could tell he was scared and embarrassed yet comfortable in his own way. It was also the first time in the last few summers than Art went further than our backyard. As for me, well I kept a lookout for anyone that might have discovered Art. My shyness was visible as Art noticed it as we walked. It was something we both had to do for Art's sake and mine if I was to push him to be my sissymaid someday.

That night when we were at home Art kept his sun dress on at my request we talked about the day. Art was honest as he told me about his fears so far from home dressed as a woman. I asked if he would do it again in a week or two. Art looked at me then himself before he answered maybe. Alright that was a fair answer considering it was his first time. I asked how were the clothes and how did they fit. Notice I didn't say feel. In my mind if the clothes were okay and they fit why wouldn't Art want to wear them again. Art told me most of the clothes felt a little odd to him even though he had seen me wear similar items for years. Art felt in general the clothes looked better on me than him. Well yes that made sense however art admitted later that he looked better than he thought. Somehow he had no vision of himself in a dress. Art was surprised how the dress fit over his breasts. We talked for a while longer before I helped Art get changed. It was a good first time for Art and when he wanted to remove the dress I agreed.

During the next couple of weeks Art wasn't prepared to try again however I did get him to agree to wear some pretty panties I bought for him. Through some convincing I told art that bras and panties were to be paired. If Art would wear panties with his bras he would feel much better about wearing a dress. Art couldn't see how panties would change his mind but he did agree to wear panties. A week later Art was willing to wear a second sun dress I bought him. Once again we walked in the park with Art more comfortable that time. Art asked me if I wanted him to be a woman out of the blue. I said no however I would like to see him wear more women's clothing and not just on Sundays. It was so hard for me to say that to Art as my shy side kept interfering during the week. When I finally got it out Art was surprised with what I said. He also wanted to know why all of a sudden little shy me decided he should wear more women's clothing. I had to think fast which was something I wasn't used to doing on that topic. As I turned to face Art I let him know that since he agreed to wear nicer bras and panties there was a change in him that I quite liked. The change was so nice I wanted to see that side of Art more. Once again Art asked if I wanted him to be a woman. I said no however I wanted him to dress like one every day from now on. That took a lot for me to say as Art looked at me to see if it was a joke. Art was a little taken back by my comment yet not as bad as I thought which told me it was possible.

The next week I went on a spending spree for Art without his knowledge. I liked Art in dresses and no so much slacks or shorts. Somehow he just looked so nice in a dress. If Art had a bigger bum he would have a great female body. I waited for the weekend again since Art expected we would go out on the weekend. It was getting to the point where Art knew what I wanted so he submitted to let me have my way. Before Art went to the closet for one of his dresses I showed him there were a few more. I also bought art a pair of sandals with a moderate heel, better for Art. He was surprised that I bought so much including more panties and stockings for the cooler weather. Art said I wasn't kidding about wearing women's clothing every day. It was my chance to let him know I wasn't kidding at all. I showed him some makeup items that we his instead of using mine. It all went fairly smooth with some minor push back. For me it was good Art didn't get angry or refuse since I wasn't prepared to handle that type of confrontation.

I helped Art get ready once again then in the car we went. Art wanted to try driving in heels which was a good thing. As much as Art was terrified there was a side of him that was happy to be out again. That day I wanted Art to venture into a shopping mall that wasn't very busy by the cars in the lot. Art refused until I showed him there was hardly a sole going in and out of the main doors. Slowly Art got out as I passed him his purse. We walked through the doors with Art holding my hand for a few minutes. As we walked Art let go as he seem to find himself again not to say he wasn't scared inside. I let him know he was doing so well and I was proud of him to take this big step. At the same time I reminded Art to take shorter steps and walk like we practiced. I noticed when Art was scared he walked faster to get to a safe place like the car on previous Sundays. We didn't buy anything or talk to anyone as that was Art's wish.

Back at home that week Art went along with me as he only wore dresses. He had accepted that only women's clothing was best for him and it made me happy too. Art was convinced there was more to come or I wanted him to be a woman. He was close except I didn't admit to any of his suspicions. For now all I wanted was for Art to wear the clothes I bought for him until I was ready to let him know the next stage. I didn't expect Art would love his new clothes however I did expect he would wear them without any fuss. Art learned how to take care of his skin and apply his own makeup every day. The more Art was willing to do the more submissive he became. That also helped me deal with my shy side more than I dreamed possible.

So Helga as you can see I could use some help getting Art to the net stage. I want him to be my sissymaid like some of the women mentioned in the letters on your website. Part of me feels that Art will be angry if I bring it up as though it was my plan all along. How would you spring this on Art yet keep control of the situation?

If you would like to share my letter to you that is fine with me as my way of supporting your website.

Regards,
Jen


Thank you for writing and for your kind words about my site, I am so pleased to hear that you found it helpful in your process to offer your boyfriend the opportunity to become your sissymaid. Thank you as well for allowing me to share your letter with my readers.

I do understand how gynecomastia can effect not only a man's body but his self confidence as well. Your decision to insist he wear a bra was of course proper and appropriate then on to more lacy and silky varieties, slowly moving him in the right direction, really well done. You obviously have the strength and confidence to make your dreams a reality.

Now on to your question, you have him already wearing women's clothes and have been quite successful in convincing him to dress as you say, so he is already following your orders, gentle though they may be, orders none the less. Having a sissymaid is really several things but primarily two, maid and sissy/submissive. You could start with the maid aspect by having him do more housework including hand washing, a nice apron for this wet work just makes sense. Working all day in heels sure would end better with a good foot rub, he does love you and wants to make you happy, him on his knees while you talk about how nice it feels and how happy it makes you etc. etc. Then in the bedroom, be on the top, maybe he cums, maybe not, insist on oral, get him a nightie, no nightie, no sex.

Helga

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