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Showing posts from May, 2025

The Long Weekend: Friday

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The Long Weekend: Thursday

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The Long Weekend: Thursday Continued from:  Detention Wednesday evening:  Preparation for a long weekend Yay, a long weekend ahead - a really long weekend ahead! I was so excited to tell Daddy, and go all the time to Monday morning without wearing anything boy. After last week's semi successful test with putting all my clothes in a suitcase, i went one better and upgraded the cupboard in the spare room with locks, giving me more than enough space to store not just the UGLY boy costumes, but coats, shoes, the lot. I was certain that this time i had secured everything boy like, unlike the suitcase experiment last week where I found my boy coats, and boy shoes after locking up the suitcase. The only issue is it was over 100 hours until monday AM, 107 in fact so i set the timer for 99 hours and 59 mins knowing that in fact at midnight on Sunday / Monday i would already be asleep when the timer ends. With that i headed to bed, excited what I could get up to over 4 whole days und...

Detention

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Detention A spanking session with Lady Jose, organised by Mistress Andrea Continued from: My First Real Spanking Those following the blog will remember back to Mistress Andrea’s gift where i was privileged to have a session set up with a professional disciplinarian, the renowned Lady Jose. Well it was that time again, but this time i was going in blind so to speak.  I trusted both Mistress Andrea and Lady Jose to organise the session, they both knew my limits and such so all I had to do was report at the allotted time, with my designated outfit to Lady Jose’s spanking parlour.    The only clues i had was that my outfit was that of a school girl, and that last time Mistress told me i WOULD be meeting the cane in my next session.   So it was not a surprise when i entered Lady Jose’s parlour that my eyes were greeted by the following scene. Yes, i was going back to school.  Little did I know just how much trouble i would be in or the emotional rollercoaster i...

My First real spanking

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  My first real spanking Previous post: Sisters Continued in the timeline from:  AI lice and the pledge During my time with Sir there was a lot of focus on anal play, enemas and dressing slutty as i outlined in the chapter Sir, but there was also some spanking.  Mainly for punishment and inflicting pain, although i had discovered my masochistic side by then and actually enjoyed that somewhat. Punishing my ovaries was top of the list, my delicate, pointless ovaries were subjugated to a lot of treatment.  Crushed, slapped, dipped in chilli paste and stretched in all sorts of ways.  Spanking was full on, as much as i could take - there was no structure to it other than full on, as much as i could take.   Now, meeting Mistress Andrea showed me that my approach was all wrong - spanking for me was hit hard, hit fast but little did i know the expertise and skill required to build a truly good spanking.  Mistress Andrea has written some amazing blog posts...

Sisters

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  Sisters Continued from: Teachers Pet I promise i will get back to the timeline soon, but I need to post this one first.  It’s important to me to get this out the way, today, on the 1st of May. During the past 204 days since I made my pledge to Mistress Andrea, i have met a number of amazing sissies, either online thanks to my posts or ones that have been referred to me by Mistress Andrea for assessment.  I call them my sissy sisters.   Lena was the first, and taught me alot and all my sissy sisters that followed will have gained from my failings with that french beauty.  To all of you that follow me or chat to me know that your support is my lifeblood, the encouragement and feedback and ideas i get from you all is a massive help and inspiration.  I love getting messages of support, or the ones that give me thanks for being brave and saying i inspire them to be more open with themselves. Now I won’t name them but they cover the globe, from Hawaii to ...