Jamie in Trouble

Dear Helga,

I have sent you a couple of photos of a very surprised and embarrassed Jamie for you to publish if you wish, to show the rest of the world what happens to naughty "Boys". Why is Jamie surprised? Well I dressed him in his long forgotten school uniform as a punishment. The reason being he has not yet written an account of what went on at his 18th birthday party that his sister wrote to you about. Let me enlighten you on his being dressed in his long forgotten schoolgirls uniform.

I had been on to Jamie for some time to write to you but he has failed to do so, so I decided to do something about it. I chose Saturday the 1st of August to confront Jamie and put my plan into action. First, I stood over him whilst I made him remove all his body hair assisting him where necessary. When he smooth skinned and hairless I sprang my first surprise on him, I showed him the enema bag and tube, yes , I gave him two enemas so he had a good idea as to what was coming next, and then made him have a long soak in a sweet smelling bubble bath while I prepared his uniform. Before leaving the bathroom I had him assume the right position, bent over, legs apart and I inserted a nice large tight fitting Butt Plug into Jamie as the start of his punishment. Taking him through into the bedroom, he then saw his school uniform laid out on the bed and he looked at me very surprised. First I laced him into his corset and laced him up extra tight, then came the crotch strap which was buckled up tight to keep his offending boy bits pulled back between his legs and crushed up out of the way, as well as putting some lovely pressure on, and keeping his Butt Plug tightly in place. I then left Jamie to finish dressing and to report to me downstairs. He took some time before presenting himself to me with a neat little curtsy.

I inspected his uniform and poked fun of his short gymslip and his regulation navy blue school knickers, (panties) making him feel very embarrassed as I could see his cheeks of his face going red, but it was not those I was interested in. I checked to make sure his crotch strap was still tight and he had not loosened it off, making him jump as the Butt Plug penetrated him deeper when I pulled at it. I explained to Jamie why he was Butt Plugged and dressed in his school uniform, it was as a punishment for not writing and sending you Aunt Helga an account of his feelings on his 18th birthday when he was for the first time Butt Plugged and dressed as a Maid for the first time. I told him he would remain in his school uniform for the rest of the day to do household chores after I had punished him first. Without further ado, I made Jamie assume the position and without let up, I gave him 12 strokes of the old-fashioned rattan school cane. On completion, I could see lovely raised red stripes across Jamie's bottom cheeks, those were the cheeks I wanted glowing red and I could see tears in his eyes. Jamie had not had a good spanking for quite some considerable time and I know he was quite shocked at receiving such a thorough spanking. Nevertheless, without forgetting his training he thanked me and gave me a nice little neat curtsy whilst doing so. Jamie spent the rest of the day doing the chores I found him to do and I know he was a bit embarrassed about wearing those navy blue knickers (panties) again so hated by schoolgirls, because his gymslip was so short he had no choice but to show them when bending over.

Jamie has had a warning that some time in the future I will have him dress in his school uniform and that is the time for him write to you Aunt Helga and he will remain in his uniform until he has done so.

Just say to any other women out there wanting to petticoat a "Boy" try a schoolgirl uniform, it is so humiliating and embarrassing for them especially having to wear girls regulation school knickers.

Sincerely Yours,
Mistress Susan

Jamie in his girls' school uniform Jamie waiting for his spanking
Click to Enlarge

Thank you for your letter Mistress Susan. What another delightful addition to the continuing humiliation of Jamie and of course I look forward to reading about his 18th from his perspective. If he wants to be released from his current schoolgirl punishment, he better get on with it.


Letter 9