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Finding Help With My Crossdressing (Crossdressing Journey Part 4)

Posted Yesterday at 04:23 PM by SissySlutSamantha

Hello Everyone,

I hope your all having a good start to the new year. Over the past few weeks I have been documenting my experience after coming out as a crossdresser to my Fiancee. Its been a tough road and the one thing I've really looked for and needed is some help, help to understand more about myself and why I crossdress. So this week I did just that.

When we have things we don't understand about ourselves we always ask the same question... "why??". For me...
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The isolation blues

Posted 01-13-2021 at 12:52 AM by Butterfly (The Butterfly Effect)

I am a pretty social person, some might even call me a social butterfly. I thrive when I am around MY people. In normal times I would be at my best friends 3 to 4 times a week after work, I would have a social event on Saturday, and maybe lunch or dinner and shopping with my mom. And that is a slow week!

Even during the spring lockdown I was meeting a friend for outdoor, social distanced coffee dates. We also had our cohort, who was my best friends family. So while things had slowed down,
...
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A Butterfly Princess <3
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Why I wish to serve! - Task 11

Posted 01-12-2021 at 01:09 PM by RainbowSky

It's the final day of the trial week. After a very intense few days, and an aching back in tow, Sir set me one very simple task. To write why I wanted to be a sub, what I could bring, why he should choose me essentially. That was it. Just write.

The Report
I believe I am a good submissive as I flourish under instruction and develop skills to please others. I learn from what I do right or wrong as I always want to improve and get better at serving others. I've also wanted to make...
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Playing with pain - Task 10

Posted 01-11-2021 at 01:33 PM by RainbowSky

It's the penultimate day of my trial week. One thing Sir and I have not explored yet together was pain, and my pain threshold, so he decided today was the perfect day.

Task 10
Equipment required
  • Collar
  • Approximately 5m of rope
  • Wooden spoon

The Task
To affix a crotch rope tightly through my collar and connect it to my hair so that my head being tilted back was the most comfortable position to be in and to remain in this way until Sir says.

The report...
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getDare Sweetheart
Posted in A new beginning
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Diaper joke ended up with twist.

Posted 01-10-2021 at 10:15 PM by Kytten

So I got a pack of depends for Christmas the year before last, it was a gag gift but I have started to use them. I find the ones bought leak rather easily and the first time I wore one I peed so much first pee it rolled down my leg.

I continued to wear it over night and was so embarrassed when I had to figure out how to dispose of it discreatly since pee has an aroma and my garbage is right by the laundry room to which I share with my daughter and her family living in her basement suite....
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Could I have done more? - Task 7, 8 and 9.

Posted 01-10-2021 at 12:44 PM by RainbowSky

Sir had a small task for me over night last night and into today which I have to say was pretty bad as it involved disrupting my sleep.

Task 7
Equipment required
  • Ankle Cuffs
  • Wrist cuffs
  • Collar

The Task
To sleep naked overnight with ankles and wrists cuffed and collar on. I will set an alarm for 3am, get up, go to the bathroom and read the list of 41 humiliating words on my body out loud before returning to bed.

The report
I never sleep naked....
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getDare Sweetheart
Posted in A new beginning
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A full day of tasks - Task 5 and Task 6

Posted 01-10-2021 at 10:36 AM by RainbowSky

So we are at a point that brings us pretty much up to speed. This was yesterday and it got very intense.

Task 5
Equipment required
  • Peach Monokini
  • Permanent Marker
  • Stopper/plug gag
  • 4 pegs
  • Heavy books
  • Hood with mouth hole

The Task
The whole day when I are home alone I was to wear my peach monokini. I was instructed to write the words cuntosuarus and pussyflap on my inner thighs starting at my pussy and going towards my knees. Later in the day before my first...
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