Letter 7
A SISSY PAGEBOY EXPERIENCE
From Simon 
Dear Miss Susan,

Firstly, many thanks for such an excellent website and particularly the Christmas 2001 Annual.  It was one of my best Christmas presents, and has given me many hours' enjoyable reading.

I was particularly caught by the story "A Pretty Little Pageboy" by Hamish, which brought some sweet childhood memories flooding back.   I should explain that I am married and, whilst not subject to full petticoat discipline, nevertheless I am submissive to my wife, who dictates what I wear and who often puts me in silk shirts or frilly panties - just to show who is in charge.

You were quite correct in your comments at the end of Hamish's letter, in that many women take the opportunity to dress pageboys in a manner that will impose some discipline on an otherwise unruly child.  When I was 10, a half-sister of my mother's got married and asked my mother if I would like to be a page at the wedding. Without asking me, my mother eagerly agreed, saying I would love to.  I sensed that she was just enthralled at the prospect of my being dressed up.

Shortly after, my mother and aunt discussed what I should wear for the wedding and how I would react if "really dressed up".  My aunt described the bridesmaids' dresses - there were to be four, two teenage cousins of mine and two younger ones who were the daughters of friends of my auntie.  They were to wear cream silk dresses with pale blue sashes and trim - chosen from pictures in a bridal magazine.  My aunt mentioned that she would like me in an outfit to match - she showed my mother some pictures of the type of outfit she wanted - a frilled blouse, with a ruffled neck and cuffs, a blue sash, and cream satin knickerbockers.  My mother was worried I'd not like it, but my aunt was most insistent, saying that I would not dare to misbehave when dressed up.  How right she was.

I suffered several trips to the dressmaker over the coming weeks and was mortified as my outfit took shape - a silk blouse having the frills added, and being measured for the knickerbockers in full few of the giggling teenage bridesmaids.  Finally the complete outfit was put on me and I just stood and did exactly as I was told, turning around and trying to hide my utter embarrassment.

If the making of the outfit was bad, then the day of the wedding was worse.  Having arrived at the house where the bridal party were changing, I cringed at the sight of my outfit hanging neatly over a wardrobe door, next to the full, frilly and pretty bridesmaids' frocks, and I shuddered with embarrassment.  I was then dressed by my delighted mother and the teenage bridesmaids, and was further mortified when a pair of cotton knickers and silk tights, identical to those of the little bridesmaids, were produced, and I was made to sit in a chair while they were pulled over my legs.

With the full outfit on I stared in the mirror seeking a pretty, sissy little boy looking back.  I was terrified someone who knew me would see me at the wedding.  Then the grown-ups left to help the bride finalise her preparations, and I was left with the four bridesmaids, who teased me and made me carry the hems of their dresses "as practice for later".  I just felt completely vanquished and compelled to do as I was told.

Eventually we arrived at the church and I had to stand outside whilst all the guests admired me and took photographs, all saying how nice I looked.  I was so glad to get inside the church where I knew none of my friends would see me.  I was so well behaved, always doing as the older bridesmaids told me, and sometimes being pushed and forcibly stood where I was supposed to.  So many guests congratulated my mother on how well behaved I had been.

By later in the day, I was actually enjoying wearing my sissy outfit and happily played with the younger bridesmaids in their pretty full frocks.  I even enjoyed being teased by some girls from my school who happened to pass the garden where we were playing.
The experience of being a pageboy made me really appreciative of the effect sissy clothes can have on a boy's behaviour.

My wife was not slow to pick up on this when, during preparations for our own wedding, my auntie recalled her own, and the most obedient pageboy she had had attend her.  Jokingly they talked about dressing me up once more and my wife sensed my slight embarrassment and acceptance of the suggestion.  Following this my wife became firmer with me, and started to take the lead in telling me what to wear - firstly a silky dressing gown of here own, and then a pair of frilly panties which she bought me when we visited Marks and Spencers.  Now I have some silky pyjamas that I am made to wear around the house at weekends and a silk blouse that I am often taken out in - always with frilled panties.  We have a wonderful relationship, and I revel in the submissive role.
You were so right - pageboy training is a fine introduction to the art of petticoat or sissy training.

Simon

It sounds like you looked wonderful, and the girls certainly had a lot of fun with their docile, satin-clad pageboy. And how thoughtful of your mother and aunt to dress you in little girls' knickers under your beautiful pageboy's knickerbockers! Yes, being a really pretty pageboy is an excellent introduction to the fine art of petticoat training, and your wife obviously appreciated this fully. And as you have experienced the result is a really wonderful marriage. Thank you for your letter, which I hope will be an inspiration to my lady readers especially.
Susan

Return to Table of Contents

Letter 8