Sissy Jolene

13th April 2018

Sissy Jolene was having text sessions but yesterday decided to try a phone session instead which was great fun for Me because I wanted another shopping trip.

First stop was Debenhams where he was instructed to find some deliciously sexy panties and make a meal out of it. Running her fingers around the lace and gusset and holding them against him. It didn’t take long to find the perfect pair. Sexy hold up stockings were next on the list which were quickly found and I got a real buzz out of hearing her at the check out.



Then it was off to Tesco for some mascara and a bra. Jolene had only ever worn a bra once before and when asked her size came up with 30/32, luckily for her I knew better and told her to find a 36C, it took a while but she got there in the end.

Finally she found some mascara and went off to pay. She has never worn mascara either so has watched a few Youtube videos and will be having a try tonight.

I think that her transformation is coming along nicely, don’t you?



9th April 2018

Sissy Jolene is another new sissy that has been enjoying text sessions.

She has a selection of cute panties but I felt that she needed more and as she was going out shopping I decided that we should work in some new panties.

Jolene’s first stop was a supermarket where she found a few packs that were suitable and sent Me photos of them in her shopping trolley. I wanted to make the trip a little more humiliating so she was instructed to find the most sexy pair that she could and hold them up against herself for the photo.

Jolene went to a department store for this and felt that all eyes were on her as she held the panties that she had chosen up against her, she could even hear a few comments. I am sure that her sissy face was a red as a beetroot but she confessed that her sissy clit was twitching!


When she got home she got to model them for Me and, I think they suit her, don’t you?

Today she is going out again and has been instructed to get some slutty red lipstick.

I am going to have plenty of fun with this sissy!



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One Comment

  1. Sissy Jolene

    First off I would like to thank you Mistress for giving me the courage to pick up some sexy panties and tights in a humiliating and nerve wrecking fashion. Lol.

    I loved every minute of this shopping trip that Mistress planned for me. No matter how nervous and humiliating this task was I still got aroused as my clitty was proof of that, wouldn’t stop twitching.

    Yes, there was times that I thought this is getting too much with people staring, smirking and making comments that made me go red in the face with embarrassment.
    The most humiliating part of this task was when Mistress instructed me to put a pair of fancy panties against myself and take a photo.

    I went to the counter to pay for my new panties and tights and it was all the girl could do to try and not laugh while my face I’m sure was getting redder at this stage.

    Although i was nervous and it was a humiliating task I can honestly say I loved and enjoyed every minute of it.

    I would say by the time I was leaving people started to realize what a right sissy I was.
    Thank you Mistress for an amazing shopping trip.

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