Letter 8
From Leslie

Dear Miss MacDonald,

Congratulations on your excellent 'Petticoat Discipline Monthly'. I always look forward to reading the latest edition. My first experience of being turned into a sissy began at primary school when I was about five or six years old. Although not exactly 'petticoat punishment' (I had done nothing wrong), it certainly felt like it, and was very humiliating.

We had a strict woman teacher, and one day it was decided that the class would dress up as nursery rhyme characters and recite the appropriate verse in front of an audience of our parents. The actual costumes were Victorian interpretations; one boy dressed as Humpty Dumpty wore a suit with an Eton collar.

It was decided that I would be 'Little Boy Blue'. The costumes were kept in a trunk, and when it came to my turn and I saw what I was going to have to wear, I was most unhappy. The reason for my unhappiness was that my costume was a velvet Little Lord Fauntleroy suit, all frilly and feminine.

'Do I have to wear it, Miss?' I protested loudly.

'Yes', replied the teacher angrily.

I obeyed her, as I knew it would be a very big mistake to go against her wishes. She was very strict, and during this period of time (the late 1960s) corporal punishment was freely used. A few years later at the school a boy was spanked with a slipper for swearing.

If I thought that trying on the costume was bad enough, worse was to come. Having to perform in front of a crowd of people whilst dressed in an embarrassing sissy costume was definitely worse.

As I stood in my pale blue Fauntleroy outfit, plastic cow horn dangling from my neck, I became so humiliated that I forgot my lines and made a complete mess of reciting the nursery rhyme. I cannot remember the reaction of the teacher, but I got the feeling she was not pleased.

Not surprisingly perhaps, as I grew up, I would often fantasise about having a strict nanny who would force me to dress in a Little Lord Fauntleroy suit or a Sailor suit. I even secretly wished that I had been brought up in an upper class family during Victorian times, as it would inevitably have meant being put into Sailor suits and so on.

Now, after all these years, I have an 'Auntie'. She doesn't see me as a man in his late 30s, but rather as her 'sissy nephew'. She lives quite a distance away, so I only get to see her once a month or so. When I visit her she makes me wear a pink, plastic PVC nursery print bib when I eat or drink. If I want blackcurrent juice, I must always drink it from a baby's feeding bottle. She also puts a dummy in my mouth and makes me suck it.

My auntie is kind enough to allow me to watch television, but only the programmes which she thinks are suitable for me. So this means watching shows like the 'Teletubbies' or 'The Tweenies' - basically anything babyish. As for outfits, I have several, and they are all very sissy. I have a red check viscose dress, which is very comfortable to wear on warm days. For schoolwear I have a short-sleeved blue blouse, which buttons up on the female side, a navy blue box-pleat skirt, and white ankle socks. A frilly white blouse is sometimes worn with the skirt.

My newest outfit is a black and white patterned dress with puff sleeves and a velvet bodice, and which zips up at the back. I purchased it from a charity shop. I also have a pretty frilly nightie, some pairs of knickers and a pair of 'yachting' shoes which are very comfortable. To complement some of the above outfits I have two wigs, a blonde curly one, and a black 'pageboy' styled one.

Auntie is very strict and will not tolerate any nonsense from me at all. Even if I have been good, she still likes to give me an old-fashioned over-the-knee spanking. Whilst it does not exactly hurt, it is very degrading. Another punishment is to make me stand in the corner, hands behind my back, with my red bottom exposed if I have been spanked.

Despite my punishments I enjoy being with my auntie, as she has plenty of dolls for me to play with, colouring books to fill in, and a teddy bear to cuddle. When she takes her dog for a walk she likes me to go with her. She allows me to put on my normal adult male clothes, but makes me keep my frilly knickers on underneath. Sometimes we go into charity shops and, on my latest visit, managed to pick up a pair of ex-fancy dress knickerbockers, which will eventually become part of a new Little Lord Fauntleroy outfit for me (I used to have one, but sadly it became spoilt).

Visits to Auntie's must be having an influence, as now that my father has gone into a care home and I live alone, I have a lot more freedom to continue dressing as a sissy. Not long ago I spent a glorious night dressed in an Alice in Wonderland dress, complete with white pinafore, wearing my blonde curly wig, and watching television whilst sucking my dummy and drinking juice from a baby's bottle.

I have even begun to shop for 'sissy' items. A visit to my local QD and Poundstretcher stores supplied me with some nice dolls (very cheap), and a big cuddly teddy bear. Charity shops have also supplied me with old editions of 'Barbie' and other children's annuals and books. I am quite happy being a sissy, and a few weeks ago spent a Thursday evening in my dress with the velvet bodice, wearing my black 'pageboy' wig, and contentedly sucking my dummy whilst reading my 'Barbie' annual, playing with my dolls and cuddling my teddy bear.

Speaking of teddy bears, even though I usually wear adult male pyjamas to bed (I have worn a nightie), I still suck my thumb, and cuddle my fluffy white teddy bear Snowy, whilst in bed. When my auntie telephones me, she always tells me to think of her tucking me up into bed before I go to sleep. I am sorry that I have rambled on for so long, but I just wanted to tell you how 'sissification' has made a positive contribution in my life. I enjoy being a sissy, and I am sure that many other men would benefit from being turned into sissies and from being made to appreciate the feminine aspects of life.
Yours sincerely,


This letter arrived in the post, and was typed out very neatly and correctly. Oh, how blessed is the correspondent whose letters require no editing! Leslie, you sound like you are very, very happy and contented as a sissy, but do watch out for some of the older children's annuals - they are much sweeter and more innocent than 'Barbie', whom I find hard, artificial and commercial. When I was a little girl we had proper cuddly baby dolls, not skinny bottle-blonded models.

Your 'Auntie' sounds like she understands the needs of sissies too. Does she have a computer? Please give her my kind regards, and refer her to this site.

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Letter 8