from Sharon

Dear Helga,

Two years ago in one evening my husband Peter and I were getting ready to go out. When I picked a pair of opaque tights out of my lingerie drawer. I noticed immediately that they had been worn. I knew that as they were stretched and I only purchased them the day before. I just thought my daughter had borrowed them as she often uses my things. Although I thought she should not have returned the tights and kept them for herself as its different from borrowing a dress as she often does. Anyway I forgot all about it until the week after when I noticed two pairs of my knickers were missing.

I asked my daughter Michele, who was 17 at the time, if she had used anything from my knicker drawer. I explained to her about my strange findings. She then said 'mum now you have mentioned it I think someones been wearing my stockings and one of my nighties was put back in my bed in a different place than I would have put it back in'.

Alarm bells then started to ring for both of us. So after checking all our wardrobes and drawers we did work out that a lot more of our clothes were missing but we couldn't be exact to the full amount. Michele then said 'we have a cross dresser sneaking about and I think it is our son Jackson' who was 18 at the time. But I did not want to believe this. Only the day before we had Steven round who is a family friend and was so close to us. We just let him come and go as he pleases. He is also as slim as myself and Michele so I just decided it must have been him.

I explained all this to my sister Michele. She advised that we confront him or just ban him from the house. My sister came round and we phoned Steven. I told him that I had something for him. After a hour had passed we thought he must have realized we were on to him. Then he turned up with some pizzas. I went straight to the point took him to our bedroom. I showed him my underwear drawer and asked him what he would like to wear. Looking at me horrified but more confused he just yelled 'sorry whats this'? Michele told him to do as he is told or everyone will know what he as been up to. I said 'you like dressing as a girl so get dressed as one'. My sister than stripped him naked while I put him in a bra and knickers and the worn pair of tights and a dress. Quickly slapped him some makeup on.Then threw him out of house for him to make is own way home dressed like it.

We agreed not to tell anyone else just in case it was someone else. I told my daughter that its all now sorted. Unfortunately only a few days later Michele had been carefully checking all her clothes - she noticed again that more of her skirts and knickers were stolen from her room. She threatened to contact the police. We then decided to search Jackson's room. Nothing was found in his wardrobe or drawers. I gave up. Then she pulled the wardrobe away from the wall. To our shock their were 4 pairs of my knickers, 1 of my bras, 1 of my red dresses, a pair of black tights, 1 pair of my high heals and 1 top and 3 skirts belonging to his sister. Even some lipstick and mascara.

I begged her to let me address this sensitive problem. But I also knew I had to act fast. I did some research on the Internet and found that it is quite common. I phoned a lady who belonged to a support group that supported this subject. I then softened my approach to cross dressers. The lady changed my mind. Up to then I just thought they were weird and we were just going to dress him up the same as Steven then ridicule him. I learned that he has an overwhelming desire to change into female attire. She convinced me I had to approach him in a very sensitive and supporting way. So I told Michele to give me a few hours the following day to see to him alone.

He got up the next morning late after everyone else had gone out. When he came down I gave him breakfast then I said to him don't you get fed up with wearing trousers all the time?. He just ignored me. I then asked if he would like to try on something different to trousers or shorts. He then laughed 'do you mean like what you wear mum'. 'Oh yes I replied'. I showed him the support group about cross dressing. 'Why are you showing me this mum' he panicked. 'Well I know you have these urges darling' I answered. 'Shut up what are you talking about', he panicked.

I then told Jackson about the clothes he had hidden behind his wardrobe. Initially he denied it and accused his sister of planting the offending clothes there. I hugged him and kissed him and said 'darling you must stop fighting these urges and let me dress you as a lady. Just me and you together I fully understand it now and the first step is to let me dress you as a girl'.

He was very nervous so I stripped him slowly with compliments and support. When I got to his trouser belt he pleaded with a 'no no mum please no I'm begging you'. I then asked him whats underneath. He did not answer so I unzipped his front then I could see he was wearing a pair of my floral patterned knickers. 'Shh that is OK darling' I reassured him. Removed his trousers left him just with that pair of my knickers on. I told him that if I gave him is own female clothes that he would no longer steal or have to borrow ours. I then let him put back on his normal clothes. Over my underwear.

I then took him out shopping to a the local M&S store. When we walked in he went to the men's section. I told him to follow me to the ladies. He said 'Mum I can't do this'. I firmly advised him that he had no choice. At the lingerie section I asked him if he preferred a knickers and bra set or a laced camisole best. He was too embarrassed to answer. So I picked both then held them up to him and said 'we will take them both'.

He did start getting some dirty looks from other customers. I picked several more all different colors. I told him they were his size. And we will be purchasing them, I then asked him which stockings or tights is he going to chose. He let me pick several again his size so I told him to hold them while we go to look at the dresses. I told him he is a size 10. He now realized that he is better picking something as I speak louder when he does not. He chose a PER UNA floral lace shift dress and a M&S collection red and another blue frock. I then made him pick some skirts and blouses. He had selected 2 pairs of ladies trousers with the blouses but I made him change the trousers for skirts. We then chose 2 pairs of shoes 1 ladies low heals and a pair of high heals. I then picked a woman's coat for him. I told him at this point that he will have to try the entire trolley on in the changing room. The lady manager noticed how terrified he was and offered us a place in the staff only area away from other customers.

All the time we were looking at all the ladies clothes and we were near female staff or customers he tried pretending they were for someone else. By saying 'do you think she will like these'. I could tell by the looks on their faces that they did not believe a word of it and knew we were shopping for him. The female staff were normal to him but when he wasn't looking they looked at me with a broad smile. But I then decided he had already suffered too much embarrassment and took him home after purchasing all the clothes, well I decided he had been punished enough. So I did not exploit him anymore in this way.

When we arrived back home I asked him if he was excited he admitted to being nervous. So to calm him down I drew all the curtains and lit several candles to give it that calming and romantic setting. I then very slowly stripped him until he was naked. Then I placed all the pretty girls attire we had bought plus the clothes he had stolen from us (apart from what we made Steve go home in) neatly near him.

'Now darling just relax take a deep breath and relax I softly ordered.' 'No please Mum I cant do this'. He panicked. 'You know you have to darling'. I then began to whisper to him slowly 'you are a young woman you are my pretty girl' several times. Then I placed him in some soft very Lacey knickers. Still whispering how special he is. Then while doing the same again and advised him to look into my eyes I fitted him into the matching bra. 'good girl' I complimented him. At this point he seemed to be in a trance. I picked up the beautiful red dress, told him to keep looking into my eyes. Obeying me at every move he held his arms out. I slipped the frock onto him from above. Then tied the ribbons. 'That wasn't too hard was it darling'.

'You look wonderful'. I again complimented. Then I sat him down and very slowly glided some opaque tights up his legs. Then stood him up and kept going until they were covering his knickers. I also ran my hands up his legs several times. Still obeying my every move and fixed to my eyes as though he was hypnotized. I put the high heals on him. Then placed some padding into the cups of his bra. 'Now listen to me you are no longer my Son'. 'No you are more than that now '. 'Now you are my new very special daughter'. I added. 'Yes mother I am now'. Was her sheepish response 'Your name is now Janet darling'. I ordered.

She then stood up to walk round the room in her new shoes dressed fully in the female attire. When Suddenly she could hear someone coming towards the front door. She asked if she could hide. I told her that she doesn't need to hide as she is simply a lady dressed as she should be.

Just then the door opened and in came my mother. She started a conversation with me about local news. Then said 'Janet you are quiet'. At this point she realized her grandma knew all about her. 'You look lovely in your dress, tights and high heals', she complimented. 'Thank you', she replied. 'So you have become a girl now have you'. She also told us that we will not regret it.

Ever since my father passed away she as had a bad experience with men and has come to the conclusion that they are all pathetic. And she always seams to prefer men and boys as inferior females anyway. She has even always called men's trousers, leggings their underwear- knickers , their socks- stockings and their shirts blouses. When men wear summer shorts and vest she calls it a bikini. She has often squirted perfume on men & boys when she as caught them off guard. So she welcomes my former Son coming over to our side.

She took Janet over to the sink and washed and styled her hair to give it a nice lady look. She then got her makeup bag out and spent over an hour on Janet until she looked very convincing as a pretty young woman what she now is. Just before she had finished Michelle came home.

She went upstairs. Janet again started panicking and asked us if she knew. We declined to answer. Then a few minutes later. My daughter came down stairs with several bags taking them all to a van. When I looked out the van driver was my sister their Auntie Michele. I did not know what they were doing. Then they both came in went back upstairs and both came down with several more large bags. Then Janet said 'Oh no they have been in my room I can tell by the noise they have made'. 'They are taking my things I need to stop them', she cried. 'My mum grabbed hold of her sat her back down and told her that she is now going to paint her nails. While she were doing this she said 'don't worry dear they are only getting rid of your disgusting past'. 'You did not need to secretly steal other peoples clothes and hide them. If you had come to me I would have gladly dressed you as a girl at my home and you could have kept it a secret as long as you liked. But I'm sure I'm going to like you much more as a granddaughter' As she had finished her nails Michele walked in and said to Janet 'Hello you're my new sister' and kissed her.

She took her by the hand to Janet's room. She discovered none of her old boring male clothes were there. All removed. She then gave her most of the clothes she had stolen plus many more what Michele no longer wanted. All the wear we had just purchased would also be added to it all. 'Where have you taken all my clothes', she asked her. Her Grandma told her that she no longer needs them anymore as she has got enough proper ladies.

A few days later my mother took Janet shopping in her car while I was at work. (This was against my advice). She told her she would buy her some clothes from some charity shops what ever she wanted. Janet foolishly then had false hopes she hoped she would allow her to replenish some of her trousers and shirts. She had plenty of makeup on and a nice dress so she did look convincing as a young woman. When they entered the charity shop she started looking at the jeans and trousers. Her gran told her that she is looking in the wrong section and moved her to the ladies area. She then talked her into picking several more dresses, skirts and blouses. Janet foolishly thought her gran would help her with discretion .But when my mum picked up the first dress she asked her if she liked it. She was too afraid to answer as she then could only speak with a male voice. Mother asked her if the cat had got her tongue. She made her look at everything that was Janet's size in a very enthusiastic and very ordering way.

The shop manager thought it is odd at her age 18. Mother just explained to her that she is so nervous because her granddaughter had never worn dresses or any makeup before. Mother just kept ordering her about until nearly half a wardrobe was in her hands then she asked her to pick some more lingerie and hosiery. Then all a sudden the young sales lady who was about the same age as her who were helping Janet and was working so close to her noticed that Janet was a young male. She noticed when she began to sob. The young lady looked at her with a confused and astonished look.

The older shop manager calmed her down took her somewhere more private. She even asked her if her mother was controlling her. As my mum looks quite young for her age. The sales lady then tried to keep my mum in the shop while the manager attempted to comfort my new daughter in a back staff room. However mum soon overcame the young lady entered the back private room and said 'Darling why are you crying you don't have to cry'. The manager then said 'we know she is really a young man'. She then asked Janet if she is OK or even if she wanted any help. Mother just had to look at Janet and Janet said 'no I'm OK now'. In a male voice. Mother then dried her face reapplied all her makeup then made her try on all the new clothes what they had chosen. Mother then paid for the clothes and said 'Its time she grew up and became the woman she is supposed to be and learn to speak properly'. 'And dress properly'. By that she meant like a female.

But then afterwards I began to think what have I done. She only wanted to be a part time cross-dresser. I asked Michele if she would reconsider and bring back some of the old clothes. But both Michele's and mother said they didn't think it is a good idea having a cross-dresser sneaking about. So they decided between us to keep Janet as Janet a woman permanently. I was in the minority. But after what he/she had done. Stealing our stuff the way she did I could not intervene. She was also worried how her father my Peter would take all this as he would be definitely be dead against it. I told her not to worry about him and I promised to sort him out.

When I informed him of the situation he was quite alarmed and disappointed with his Son /daughter. I then strictly ordered my husband to fully support her when he meets his new daughter and tells her how amazing she is or I will bring the girls round and have him dressed the same. So needless to say he accepted and kept to his word. At the time I reassured Janet that it would only be for a short while. However 2 years later she is still living as the lady Janet.

In the next few months our daughter Michelle is moving out to live with a friend. So I'm considering letting Janet live as both Jackson and Janet. I might let her have both rooms so she can have a female & male room. Then she can change freely from one to the other. This is what she wants.

But she spends much of her time at auntie Michele's home and my mother's place. They will probably still have enough influence on her to keep her as my wonderful daughter Janet. So we may keep her as Janet for a few years longer yet. She is still strictly forbidden from wearing any male clothes. With all the deportment training they have given her over the last 2 years she behaves much more like a lady and now has a convincing female voice so it may be for the best if she is kept this way.

Another problem I have is that my mother has given all this female dominance in our family too much thought. Yes the last few weeks she has asked if me and her can dress my husband up. Well up to now I have said no. I just don't believe in enforced cross dressing to someone just to humiliate them for the sake of it. My children don't want this. But after reading from your special website it has greatly softened my opposition to it. Just yesterday sister and my mother showed me 2 prom dresses along with all the lingerie and high heals that would fit my Peter. They want to take him to a friends fancy dress in town. I honestly think they just want to do it to prove that they can. They want to take their dominance to the next level.

Well I have thought again about it and I have decided to give my Mother and Michele a chance. On this fancy dress night I am going to arrange that when they arrive with the clothes and makeup to doll him up that only Peter will be in. I'll make sure our children are occupied else where. I don't know if they will be successful in stripping him then dressing him up to the nines. Then taking him out. I guess that if he lets them get into his head or doesn't defend himself until its too late they will.

If they manage their evil secret plan next week they will phone me and I will join them at the venue. If they only manage to dress him but are unable to get him out. I will arrive and help them take him. Because to me if they manage to dress and doll him up I will accept the ladies have won.

Kind regards,


Thank you for your letter Sharon. What a delightful introduction to femininity for your son, I especially appreciate your gentle introduction to the sensual nature of dressing. Involvement from your daughter, sister and mother will be so helpful going forward. Please do let us know how things are going for your husband as well.


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Letter 3